DESCRIPTION AGRICULTURAL/HORTICULTURAL INSECTICIDE AND METHOD FOR USING THE
SAME
Technical Field The present invention relates to compounds represented by-formula (1), insecticides containing the compounds as active ingredients, a method for producing the insecticides, and a method for using the insecticides.
Background Art PCT Japanese Translation Patent Publication No. 11-511442 discloses salicylic compounds similar to compounds of the present invention. However, compounds represented by formula (1) of the present invention do not have a salicylic skeleton, and the compounds disclosed in the above publication are clearly outside the scope of claims of the present invention.
Publication No. WO2003-22806 discloses compounds as production intermediates similar to the compounds of the present invention, but it does not disclose an activity to insects. Also, the compounds disclosed in the publication are clearly outside the scope of claims of the present invention.
J. Org. Chem. 142 (1966) discloses compounds as production intermediates similar to the compounds of the present invention, but it does not disclose an activity to insects. Also, the compounds disclosed in the publication are clearly outside the scope of claims of the present invention.

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J. Am. Chem. Soc. 6382 (2000) discloses compounds as production intermediates similar to the compounds of the present invention, but it does not disclose an activity to insects. Also, the compounds disclosed in the publication are clearly outside the scope of claims of the present invention.
Disclosure of Invention
An object of the present invention is to provide insecticides having high effectiveness.
As a result of intensive research for achieving the object, the inventors found that the compounds of the present invention are novel compounds not disclosed in any document and have an excellent insecticidal effect, and the compounds can be used as new insecticides. It is also found that intermediates in production of the compounds of the present invention are not disclosed in any document and are useful production intermediates. The present invention has been achieved based on these findings. The present invention provides compounds represented by the following formulae:
[1] Compounds represented by formula (1)
Gi
Rz\ A /Ri 2 N Gj
A2 A1 (D
wherein Ai, A2, A3, and A4 independently represent a carbon atom, a nitrogen atom, or an oxidized nitrogen atom; Rx represents a C1-C6

3
alkyl group which may be substituted, a phenyl group which may be substituted, or a heterocyclic group which may be substituted; R2 and R3 independently represent a hydrogen atom, a C1-C4 alkyl group which may be substituted, or a C1-C4 alkylcarbonyl group which may be substituted; Gx, G2, and G3 independently represent an oxygen atom or a sulfur atom; Xs may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C4 alkyl group which may be substituted, or an amino group which may be substituted; n represents an.integer of 0 to 4; Q represents a phenyl group which may be substituted, anaphthyl group which may be substituted, a tetrahydronaphthyl group which may be substituted, or a heterocyclic group which may be substituted.
[2] Compounds represented by formula (1) wherein Ai, A2, A3, • and A4 independently represent a carbon atom, a nitrogen atom, or an oxidized nitrogen atom; Ri represents the following: a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a phenyl group,
a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C3

4
cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, a naphthyl group,
a substituted naphthyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group,
a heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group,

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or a.tetrazolyl group),
a substituted heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group) having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group,
(wherein Ei represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, or a C3-C4 haloalkynylene group; R4 represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group, a C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group,

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a C3-C8 halocycloalkyl group, a phenyl group,
a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, a naphthyl group,
a substituted naphthyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group,
a heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a

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furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group), or
a substituted heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a.tetrahydrofuryl group, a thienyl'groupr a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group) having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group), and
Zi represents -0-, -S-, -SO-, -S02-, -C(=0)-, -C(=0)0-, -0C(=0)-, -N(R5)-, -C(=0)N(R5)-, or -N(R5)C(=0)- (R5 represents a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group, a C1-C4

8
haloalkylcarbonyl group, or a C1-C4 alkoxycarbonyl group)), or -E2-R6
(wherein E2 represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, or a C3-C4 haloalkynylene group, and R6 represents a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a cyano group, a nitro group, a hydroxyl group, a phenyl group,
a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, a naphthyl group,
a substituted naphthyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6

9
haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group,
a heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group), or
a substituted heterocyclic group (which represents a pyridyl group, a pyridine~N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group) having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6

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haloalkylsulfinyl group, a C1-C6 alkylsulfonyi group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group);
R2 and R3 independently represent a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group, or a C1-C4 haloalkylcarbonyl group; Gi, G2/ and G3 independently represent an oxygen atom or a sulfur atom; Xs may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C4 alkylsulfinyl group, a C1-C4 haloalkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C1-C4 haloalkylsulfonyl group, a cyano group, a nitro group, an amino group, or an amino group which may be substituted by a C1-C4 alkyl group; n represents an integer of 0 to 4; Q represents a phenyl group,
a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a Cl-C6 haloalkylsulfonyl group, a C1-C6 haloalkylsulfonyloxy group, a

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C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a phenyl group, a substituted phenyl group (which may have the same or different substituents selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group/ a C1-C6 haloalkylsulfonyl group, a C1-C6 haloalkylsulfonyloxy, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group), a thienyl group, and a substituted thienyl group (which may have the same or different substituents selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 haloalkylsulfonyloxy, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group),
a naphthyl group,
a substituted naphthyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may

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be substituted by at least one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a Cl-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group, a heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group), a substituted heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group) having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group, a tetrahydronaphthyl group, or

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a substituted tetrahydronaphthyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group (excluding a case (1) in which Q represents 3,4-dichlorophenyl when Rl represents a methyl group, a case (2) in which Q represents an unsubstituted phenyl group when Rl represents an ethyl group, and a case (3) in which Q represents an unsubstituted pyridyl group when Rl represents an unsubstituted phenyl group).
[3] Compounds represented by formula (2)
A-^A, (2) Hal
wherein Alr A2, A3, A4, Rlr R2, R3, Gi, G2, G3, X, and n each represent the same as in formula [1], and Hal represents a halogen atom.
[4] Compounds represented by formula (3)

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N
A^A, (3)
wherein Ai, A2, A3, A4, R3, G3, X, n and Q each represent the same as in formula [1].
[5] Compounds represented by formula (4)
AT^A, (4)
wherein Ai, A2, A3, A4, Rz, R3, G3, X, and n each represent the same as in formula [1], and Q represents a group represented by formula (1-2) or (1-3):
'5 .[ r3
(wherein Yi, Y2, Y4, and Ys may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6' alkylthio group, a C1-C6 haloalkylthio' group, a Cl-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6
alkylsulfonyl group, a C.1-C6 haloalkylsulfonyl group, a pentafluorosulfanyl group, a cyano group, or a nitro group, and Y3 ■ represents a C\-C$ haloalkyl group, a Ci-C6' haloalkoxy group, a Ci~C6 haloalkyl group which may be substituted by at least on hydroxy! group, a Ci-C6 haloalkylthio group,' a Ca-C6-haloalkylsulfinyl group, a Ci-C6 haloalkylsulfonyl ■ •

group, or a pentafluorosulfanyl group, but excluding a case that both of Y| and Y5 represent a hydrogen atom)
(wherein Y6, Y7, and Y9 may be the same or different and each
represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a
C1-C6- haioalkyl--- group-,—a-Gl-G6-a-lkoxy group, a C1-C6 haloalkoxy •■
group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a Cl-
C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6
alkylsulfonyl group, a pentafluorosulfanyl group, a cyano group,
or a nitro group, and Ye represents a C1-C6 haioalkyl group, a Cl-
C6 haloalkoxy group, a C1-C6 haioalkyl group which may be
substituted by at least one hydroxyl group, a C1-C6 haloalkylthio
group, a C1-C6 haloalkylsulfinyl group, a C1-C6 haloalkylsulfonyl group, or a pentafluorosulfanyl group, but excluding a case that both of Y6 and Yg
represent a hydrogen atom).
[6] A method for producing the above-described compounds in [1] comprising reacting the compounds represented in [3] by formula (2) with compounds represented by formula (5):
'v*S (5)
wherein R3 and Q each represent the same as in [1] .
[7] A method for producing the above-described compounds in
[1] comprising reacting the compounds represented in [4] by
formula (3) with compounds represented by formula (6} : H-G,-R, (6)

16
wherein Ri and G2 each represent the same as in [1] .
[8] A method for producing the above-described compounds in [1] comprising reacting the compounds represented in [5] by . formula (4) with compounds represented by formula (7) :
wherein Rl7 Glr and G2 each represent the same as in [1] . [9] Aniline derivatives represented by formula (8):
Rg y / J10
Y12 (0)m
wherein R7 .represents a C1-C6 haloalkyl group, Yio, Yu, Y12, and Y13 may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C6 alkyl.group, a C1-C6 haloalkyl group,, a Cl-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 .
haloalkylsulfinyl group, a Cx-C6 alkylsulfonyl group, a Cx-Cs haloalkylsulfonyl group, a pentafluorosulfanyl group, a cyano
. group, or a nitro group, and R8 and R9 independently represent a hydrogen atom, a C1-C4 alkyl group, a m-nitrobenzoyl group,
■or a substituted,m-nitrobenzoyl group, and m represets 0, 1 or
[10] Aniline derivatives represented by formula (9) :
^12 . Y14 N ^L Y
11 |
Y17 (^ R10
Y„ ■
wherein R10 represents a C1-C6 haloalkyl group which may be

17
substituted by at least one hydroxy! group, Yj.4, Y15, YXGr and Yn • may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group,'a C1-C6 haloalkyl group, a Cl-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6■alkylthio group, •a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6
haloalkylsulfinyl group, a d-C6 alkylsulfonyl group, a d-C6 haloalkylsulfonyl. group, a pentafluorosulfanyl group, a cyano group, or a nitro group, and R1X and R12 independently represent a hydrogen atom,a d-C4 alkyl group, a m-nitrobenzoyl group, or a substituted m=nitrobenzoyl'.group.
[11] An insecticide comprising any one of the compounds in . [1] or [2] as an active ingredient.
[12] A method for using a chemical comprising treating a useful crop or soil with an effective, amount of any one of the •compounds [1] or [2], for protecting the useful crop from harmful organisms.
[13] A method for preventing pests comprising using the compound [1] or [2] and at least one insecticide and/or fungicide in combination.
■ The compounds of the present invention exhibit an excellent preventive effect as insecticides in low dosages, and also exhibit an excellent preventive effect when being used in combination with another insecticide, an acaricide,. a nematocide, a fungicide, a herbicide, a plant growth regulator, or a biological pesticide.
Best Mode for Carrying Out the Invention In the definitions of formula (1) of the present invention,

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the term "halogen atom" means a fluorine atom, a chlorine, atom, a bromine atom, or an iodine atom. The characters "n-", "i-", "s-", and "t-" mean "normal", "iso", "secondary", and "tertiary", respectively. With respect to the expression "Ca-Cb (a and b each represent an integer of 1 or more)", for example, "C1-C6" means that the number of carbon atoms is 1 to 6, "C3-C8" means that the number of carbon atoms is 3 to 8, and "C1-C4" means that the number of carbon atoms is 1 to 4.
In the definitions of the formulae such as formula (1) of the present invention, the used terms have the following meanings:
The term "an alkyl group which may be substituted" means a straight, branched or cyclic alkyl group which may be substituted by the same or different groups selected from a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a Cl-C6 haloalkylsulfonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl group, a C1-C6 alkylcarbonyloxy, a C1-C6 haloalkylcarbonyloxy group, an amino group, a C1-C6 alkylamino group, a di-Cl-C6 alkylamino group, a phenyl group which may be substituted, a phenylcarbonyl group which may be substituted, a phenylamino group which may be substituted, and a heterocyclic group which may be substituted.
The term "an alkylcarbonyl group which may be substituted" means a straight, branched or cyclic alkylcarbonyl group which may

19
be substituted by the same or different groups selected from a hydrogen atom, a halogen atom, a hyriroxyl group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a Cl-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl group, a C1-C6 alkylcarbonyloxy, a C1-C6 haloalkylcarbonyloxy group, an amino group, a C1-C6 alkylamino group, a di-Cl-C6 alkylamino group, a phenyl group which may be substituted, a phenylcarbonyl group which may be substituted, a phenylamino group which may be substituted, and a heterocyclic group which may be substituted. The term "a phenyl group which may be substituted" means a phenyl group which may be substituted by the same or different groups selected from a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl group, a C1-C6 alkylcarbonyloxy, a C1-C6 haloalkylcarbonyloxy group, an amino group, a C1-C6 alkylamino group, a di-Cl-C6 alkylamino group, a phenyl group which may be substituted, a phenylcarbonyl group which may be substituted, a phenylamino group which may be substituted, and a heterocyclic group which may be

20
substituted.
The term "a naphthyl group which may be substituted" means a naphthyl group which may be substituted by the same or different groups selected from a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 alkylcarbonyl group,.a C1-C6 haloalkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl group, a C1-C6 alkylcarbonyloxy, a C1-C6 haloalkylcarbonyloxy group, an amino group, a C1-C6 alkylamino group, a di-Cl-C6 alkylamino group, a phenyl group which may be substituted, a phenylcarbonyl group which may be substituted, a phenylamino group which may be substituted, and a heterocyclic group which may be substituted.
The term "a tetrahydronaphthyl group which may be substituted" means a tetrahydronaphthyl group which may be substituted by the same or different groups selected from a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a Cl-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl group, a C1-C6 alkylcarbonyloxy, a C1-C6 haloalkylcarbonyloxy group, an amino

21
group, a C1-C6 alkylamino group, a di-Cl-C6 alkylamino group, a phenyl group which may be substituted, a phenylcarbonyl group which may be substituted, a phenylarnino group which may be substituted, and a heterocyclic group which may be substituted.
The term "a heterocyclic group which may be substituted" means a heterocyclic group which may be substituted by the same or different groups selected from a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl group, a C1-C6 alkylcarbonyloxy, a C1-C6 haloalkylcarbonyloxy group, an amino group, a C1-C6 alkylamino group, a di-Cl-C6 alkylamino group, a phenyl group which may be substituted, a phenylcarbonyl group which may be substituted, a phenylarnino group which may be substituted, and a heterocyclic group which may be substituted.
The term "a C1-C6 alkyl group" means a straight or branched alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, n-pentyl, 2-pentyl, neopentyl, 4-methyl-2-pentyl, n-hexyl, or 3-methyl-n-pentyl. The term "a C1-C6 haloalkyl group" means a straight or branched alkyl group having 1 to 6 carbon atoms and substituted by one or more halogen atoms which may be the same or different, such as trifluoromethyl, pentafluoroethyl, heptafluoro-n-propyl,

22
heptafluoro-i-propyl, 2,2-difluoroethyl, 2,2-dichloroethyl, 1,3-difluoro-2-propyl, 1,3-dichloro-2-propyl, l-chloro-3-fluoro-2-propyl, l,l,l-trifluoro-2-propyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 3,3,3-trifluoro-n-propyl, 4,4,4-trifluoro-n-butyl, 1,1,1,3,3,3-hexafluoro-2-propyl, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propyl, 1,1,1,3,3,3-hexafluoro-2-bromo-2-propyl, 1,1,2,3,3,3-hexafluoro-2-chloro-n-propyl, 1,1,2,3,3,3-hexafluoro-2-bromo-n-propyl, 1,1,2,3,3,3-hexafluoro-1-brbmo-2-propyl, 2,2,3,3,3-pentafluoro-n-propyl, 3,3,4,4,4-pentafluoro-2-butyl, nonafluoro-n-butyl, nonafluoro-2-butyl, -2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 3-fluoro-n-propyl, 3-chloro-n-propyl, or 3-bromo-n-propyl.
The term "a C2-C6 alkenyl group" means an alkenyl group having 2 to 6 carbon atoms and a double bond in its carbon chain, such as vinyl, allyl, 2-butenyl, or 3-butenyl. The term "a C2-C6 haloalkenyl group" means a straight or branched alkenyl group having 2 to 6 carbon atoms and a double bond in its carbon chain and substituted by one or more halogen atoms which may be the same or different, such as 3,3-difluoro-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 2,3-dibromo-2-propenyl, 4,4-difluoro-3-butenyl, or 3,4,4-tribromo-3-butenyl.
The term "a C2-C6 alkynyl group" means an alkynyl group having 2 to 6 carbon atoms and a triple bond in its carbon chain, such as propargyl, l-butyne-3-yl, or l-butyne-3-methyl-3-yl. The term "a C2-C6 haloalkenyl group" means a straight or branched alkyenyl group having 2 to 6 carbon atoms and a triple bond in its carbon chain and substituted by one or more halogen atoms which

23
may be the same or different.
The term "a C3-C8 cycloalkyl group" means a cycloalkyl group having 3 to 8 carbon atoms and a cyclic structure, such as cyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, or 4-methylcyclohexyl. The term "a C3-C8 halocycloalkyl group" means a cycloalkyl group having 3 to 8 carbon atoms and a cyclic structure and substituted by one or more halogen atoms which may be the same or different, such as 2,2,3,3-tetrafluorocyclobutyl, 2-chlorocyclohexyl, or 4-chlorocyclohexyl. The term "a C1-C6 alkoxy group" means a straight or branched alkoxy group having 1 to 6 carbon atoms, such as methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butoxy, s-butoxy, i-butoxy, or t-butoxy. The term "a C1-C6 haloalkoxy group" means a straight or branched haloalkoxy group having 1 to 6 carbon atoms and substituted by one or more halogen atoms which may be the same or different, such as trifluoromethoxy, pentafluoroethoxy, heptafluoro-n-propyloxy, heptafluoro-i-propyloxy, 1,1,1,3,3,3-hexafluoro-2-propyloxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy, or 3-fluoro-n-propyloxy.
The term "a C1-C6 alkylthio group" means a straight or branched alkylthio group having 1 to 6 carbon atoms, such as methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, s-butylthio, or t-butylthio. The term "a C1-C6 haloalkylthio group" means a straight or branched alkylthio group having 1 to 6 carbon atoms and substituted by one or more halogen atoms which may be the same or different, such as trifluoromethylthio,

24
pentafluoroethylthio, 2,2,2-trifluoroethylthio, heptafluoro-n-propylthio, heptafluoro-i-propylthio, nonafluoro-n-butylthio, or nonafluoro-2-butylthio.
The term "a C1-C6 alkylsulfinyl group" means a straight or branched alkylsulfinyl group having 1 to 6 carbon atoms, such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, s-butylsulfinyl, or t-butylsulfinyl. The term "a C1-C6 haloalkylsulfinyl group" means a straight or branched alkylsulfinyl group having 1 to 6 carbon atoms and substituted by one or more halogen atoms which may be the same or different, such as trifluoromethylsulfinyl, pentafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, heptafluoro-n-propylsulfinyl, heptafluoro-i-propylsulfinyl, nonafluoro-n-butylsulfinyl, or nonafluoro-2-butylsulfinyl.
The term "a C1-C6 alkylsulfonyl group" means a straight or branched alkylsulfonyl group having 1 to 6 carbon atoms, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, s-butylsulfonyl, or t-butylsulfonyl. The term "a C1-C6 haloalkylsulfonyl group" means a straight or branched alkylsulfonyl group having 1 to 6 carbon atoms and substituted by one or more halogen atoms which may be the same or different, such as trifluoromethylsulfonyl, pentafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro-i-propylsulfonyl, nonafluoro-n-butylsulfonyl, or nonafluoro-2-butylsulfonyl.
The term "a C1-C4 alkylcarbonyl group" means a straight, branched, or cyclic alkylcarbonyl group having 1 to 4 carbon atoms,

25
such as acetyl, propionyl, isopropylcarbonyl, or
cyclopropylcarbonyl. The term "a C1-C4 haloalkylcarbonyi group" means a straight or branched alkylcarbonyl group having 1 to 4 carbon atoms and substituted by one or more halogen atoms which may be the same or different, such as trifluoroacetyl, pentafluoropropionyl, trichloroacetyl, chloroacetyl, bromoacetyl, or 3-chloropropionyl.
The term "a C1-C4 alkoxycarbonyl group" means a straight or branched alkoxycarbonyl group having 1 to 4 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, or isopropyloxycarbonyl.
The term "a C1-C4 alkylcarbonyloxy group" means a straight or branched alkylcarbonyloxy group having 1 to 4 carbon atoms, such as acetoxy or propionyloxy. The term "a C1-C4 alkylsulfonyloxy group" means a straight or branched alkylsulfonyloxy group having 1 to 4 carbon atoms, such as methylsulfonyloxy. The term "a C1-C4 haloalkylsulfonyloxy group" means a straight or branched alkylsulfonyloxy group having 1 to 4 carbon atoms and substituted by one or more halogen atoms which may be the same or different, such as trifluoromethylsulfonyloxy or pentafluoroethylsulfonyloxy.
The term "a C1-C4 alkylene group" means a straight or branched alkylene group having 1 to 4 carbon atoms, such as methylene, ethylene, propylene, dimethylmethylene, or isobutylene. The term "a C2-C4 alkenylene group" means a straight or branched alkenylene group having 2 to 4 carbon atoms and a double bond in its carbon chain. The term "a C3-C4 alkynylene group" means a straight or branched alkynylene having 3 to 4 carbon atoms and a triple bond in its carbon chain. The term "a C1-C4 haloalkylene

26
group" means a straight or branched alkylene group having 1 to 4 carbon atoms and substituted by one or more halogen atoms which may be the same or different, such as chloromethylene, chloroethylene, dichloromethylene, or difluoromethylene.
The term "a C2-C4 haloalkenylene group" means a straight or branched alkynylene having 2 to 4 carbon atoms and a double bond in its carbon chain, and substituted by one or more halogen atoms which may be the same or different. The term "a C3-C4 haloalkynylene group" means a straight or branched alkynylene group having 3 to 4 carbon atoms and a triple bond in its carbon chain, and substituted by one or more halogen atoms which may be the same or different.
The term "a C1-C6 haloalkyl group which may be substituted by one ore more hydroxyl groups" means a straight or branched alkyl group having 1 to 6 carbon atoms and one or more hydroxyl groups in its carbon chain, and substituted by one or more halogen atoms which may be the same or different, such as 1,2,2,2-tetrafluoro-l-hydroxyethyl, 1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl, 1,1,1,3,3,4,4,4-octafluoro-2-hydroxy-2-butyl, 1,2,2,3,3,4,4,4-octaf luoro-1-hydroxy^-n-butyl, or 1, 3-dichloro-l, 1,3, 3-tetraf luoro-2-hydroxy-2-propyl.
The term "a substituted m-nitrobenzoyl group" means a m-nitrobenzoyl group having one or more substituents, such as 2-fluoro-3-nitrobenzoyl, 4-fluoro-3-nitrobenzoyl, 2-fluoro-5-nitrobenzoyl, or 4-chloro-3-nitrobenzoyl.
The compounds represented by formula (1) of the present invention may contain at least one asymmetric carbon atom or

27
asymmetric center and thus have at least two types of optical isomers. The present invention includes the optical isomers and mixtures thereof at any proportions. The compounds represented by formula (1) of the present invention may contain at least two types of geometric isomers derived from carbon-carbon double bonds in the structural formulae. The present invention also includes the geometric isomers and mixtures thereof at any proportions.
Preferred examples of the substituents or atoms in the compounds represented by the formulae such as formula (1) of the present invention include the following:
Preferably, Rx is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, a C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, -E!-Zi-R4 (wherein Ei represents C1-C4 alkylene, C2-C4 alkenylene, C3-C4 alkynylene, C1-C4 haloalkylene, C2-C4 haloalkenylene, or C3-C4 haloalkynylene, R4 represents a hydrogen atom, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, or C2-C6 haloalkynyl, and Zi represents -0-, -S-, -SO-, or -S02-) , or -E2-Re (wherein E2 represents C1-C4 alkyl, C2-C4 alkenyl, C3-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, or C3-C4 haloalkynyl, and R6 represents C3-C8 cycloalkyl, C3-C8 halocycloalkyl, cyano, nitro, hydroxyl, phenyl, substituted phenyl having one or more substituents which may be the same or different and which are selected from halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, cyano, nitro, hydroxyl, C1-C4 alkylcarbonyl,

28
C1-C4 haloalkylcarbonyl, C1-C4 alkylcarbonyloxy, and C1-C4 alkoxycarbonyl, pyridyl, or substituted pyridyl having one or more substituents selected from halogen, C1-C6 haloalkyl, and C1-C6 haloalkoxy). More preferably, Rx is C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, -E1-Z1.-R4 (wherein Ei represents C1-C4 alkylene or C1-C4 haloalkylene, R4 represents Cl-C6 alkyl or C1-C6 haloalkyl, and Zi represents -0-, -S-, -SO-, or -S02-) , or -E2-R6 (wherein E2 represents C1-C4 alkyl, R6 represents C3-C8 cycloalkyl, cyano, substituted phenyl having one or more substituents which may be the same or different and which are selected from halogen, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, cyano, and nitro, pyridyl, substituted pyridyl having one or more substituents selected from halogen, C1-C6 haloalkyl, and C1-C6 haloalkoxy, thienyl, or tetrahydrofuryl).
Preferably, R2 and R3 are independently hydrogen or C1-C4 alkyl, and more preferably hydrogen, methyl, or ethyl.
Preferably, d, G2, and G3 are independently oxygen or sulfur, and more preferably oxygen.
Preferably, X is hydrogen, halogen or trifluoromethyl, and more preferably hydrogen or fluorine. Preferably, n is 0 or 1.
Preferably, Q is phenyl, substituted phenyl having one or more substituents selected from halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 aikoxy, C1-C6 haloalkoxy, C1-C6 haloalkyl which may be substituted by one or more hydroxyl groups, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl,

C1-C6 alkylsuifonyi, pentafluorosulfanyl, cyano, and nitro,
pyridyl, or substituted pyridyl having one or more substituents
selected from halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy,
C1-C6 haloalkoxy, C1--C6 haloalkyl which may be substituted by one
or more hydroxyl groups, C1-C6 alkylthio, C1-C6 haloalkylthio, Cl-
C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsuifonyi,
C1-C6 haloalkylsulfonyl, pentafluorosulfanyl, cyano, and nitro.
More preferably,-Q-is-substituted phenyl or-substituted pyridyl
represented by formula (1-2) or (1-3) . In the formula, preferably,
Y, and Y5 are independently hydrogen, C1-C4 alkyl, halogen, or methylthio, and excluding a case that both of Y| and Y5 represent a hydrogen atom.
Preferably, Y2 and Y4 are each hydrogen.
Preferably, Y3 is C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 haloalkyl which may be substituted by one or more hydroxyl groups, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, or pentafluorosulfanyl. More preferably, Y3 is C1-C6 haloalkyl, C1-C6 haloalkyl which may be substituted by one or more hydroxyl group, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, or C1-C6 haloalkylsulfonyl.
Preferably, Y6 and Y9 are independently hydrogen, C1-C4 alkyl, halogen, or methylthio, and excluding a case that both of Y6 and Y9 represent a hydrogen atom.
Preferably, Y7 is hydrogen.
Preferably, Y3 is C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6
haloalkyl which may be substituted by one or more hydroxyl groups, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, or pentafluorosulfanyl. More preferably, Y3 is

C1-C6 haloalkyl or C1-C6 ha.loalkoxy.
Preferably, Hal is chlorine.
Preferably, R7 is C1-C6 haloalkyl, and more preferably R7 is
C1-C6 alkyi substituted by fluorine, such as pentafluoroethyl,
heptafluoro-n-propyl, heptafluoroisopropyl, nonafluoro-n-butyl, or
nonafluoro-2-butyl. Preferably, Yj0 and Y]3 are independently hydrogen, CI-C4 alkyi, hydrogen, or methylthio, and excluding a case that both of Yio and Y13 represent a hydrogen atom. More preferably, Y|0 and Y13 are each chlorine, bromine, or methyl.
Preferably, Yu and Yi2 are each hydrogen.
Preferably, Rg and R9 are each hydrogen, CI-C4 alkyi,m-nitrobenzoyl, or 2-fluoro-3-
nitrobenzoyl, excluding a case that both of Rg and R9
represent C1-C4 alkyi, m-nitrobenzoyl, or 2-fluoro-3-nitrobenzoyI.
Preferably, m is 0, 1, or 2.
Preferably, Ri0 is 1,2,2,2-tetrafluoro-l-hydroxyethyl, l,l,l,3,3,3-hexafluoro-2-hydroxy-2-propyl, 1,1,1,3,3,4,4,4-octafluoro-2-hydroxy-2-butyl, 1,2,2, 3, 3, 4, 4, 4-octafluoro-l-hydroxy-n-butyl, or 1,3-dichloro-l,1,3,3-tetrafluoro-2-hydroxy-2-propyl, and more preferably, Rio is 1,1,1, 3, 3, 3-hexafluoro-2-hydroxy-2-propyl.
Preferably, Y14 and Yn are independently hydrogen. C1-C4 alkyi, halogen, or methythio, and excluding a case that both of Y|4 and Y17 represent a hydrogen atom. More preferably, none of Y14 and Yn represents a hydrogen atom.
Preferably, Yx5 and Yie are each hydrogen.
Preferably, Rn and R12 are each hydrogen, C1-C4 alkyi, m-
— 1Q -

nilrobenzoyl, or 2-fluoro-3-nitrobenzoyl, and excluding a case that both of R,, and R,2 represent CI-C4 alky!, m-nitrobenzoyl, or2-nuoro-3- nitrobenzoyl.
Representative processes for producing the compounds of the present invention will be described below. Although the compounds of the present invention can be produced according to the methods, the production processes are not limited to the processes
described below. ■•-—
An embodiment of the representative processes for producing the compounds of the present invention is Production Method 1 (in the formula, Ri, R3, Gi, G2, (X)n, and 0 represent the same as described above).
Production Method 1
?' Gl
NOz 0.R3NH NC, NH2 a\^ HM-V*1
(10) (12) (13) °
(14)
l-(i) . Formula (10) -> Formula (12)
A m-nitrobenzoyl chloride derivative represented by formula (10) is reacted with an aromatic amine derivative represented by formula (11) in an appropriate solvent to produce a benzamide derivative represented by formula (12). In this step, an appropriate base can also be used. As the solvent, any solvent which does not significantly inhibit the progress of reaction can be used. Examples of the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons

32
such as dichloromethane, chloroform, and carbon tetrachloride; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; ketones such as acetone, methyl isobutyl ketone, and cyclohexanone; amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can be used alone or in a mixture of two ore more kinds. Examples of the base include organic bases such as triethylamine, tri-n-butylamine, pyridine, and 4-dimethylaminopyridine; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; carbonates such as sodium hydrogen carbonate and potassium carbonate; phosphates such as dipotassium hydrogen phosphate and trisodium phosphate; alkali metal hydrides such as sodium hydride; and alkali metal alcoholates such as sodium methoxide and sodium ethoxide. The base may be used in an appropriate amount in the range of molar equivalents of 0.01 to 5 times the amount of the compound represented by formula (10). The reaction temperature may be appropriately determined in the range of -20°C to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours. The m-nitrobenzoyl chloride derivative represented by formula (10) can be easily produced from a m-nitrobenzoic acid derivative by a conventional method using a halogenating agent. Examples of the halogenating agent include thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride, and

33
phosphorus trichloride. In a process for producing the compound represented by formula (12) using the m-nitrobenzoic acid derivative and the compound represented by formula (11) without using a halogenating agent, 1-hydroxybenzotriazole functioning as an additive, and N,N'-dicyclohexyl carbodiimide functioning as a condensing agent can be used according to the technique disclosed in, for example, Chem. Ber. p. 788 (1970). Other examples of the condensing agent include l-ethyl-3-(3-dimethylaminopropyl) carbodiimide and 1,1'-carbonyl-bis-lH-imidazole. Alternatively, the compound represented by formula (12) can be produced by a mixed acid anhydride technique using a chloroformic acid ester according to the technique disclosed in J. Am. Chem. Soc. p. 5012 (1967). Examples of the chloroformic acid ester include isobutyl chloroformate and isopropyl chloroformate'. Instead of the chloroformic acid ester, diethylacetyl chloride or trimethylacetyl chloride can be used. In the technique using the condensing agent and the mixed acid anhydride technique, the solvent, the reaction temperature, and the reaction time are not limited to those disclosed in the above documents, and an inert solvent which does not inhibit the progress of reaction may be appropriately used. Also, the reaction temperature and the reaction time may be appropriately selected according to the progress of reaction.
l-(ii) Formula (12) -> Formula (13)
The benzamide derivative having a nitro group represented by formula (12) can be converted to a benzamide derivative having an amino group represented by formula (13) by reduction reaction.

34
Examples of a technique for the reduction reaction include a technique using hydrogenation and a technique using tin(II) chloride (anhydride). In the former technique, reaction can be performed in a hydrogen atmosphere in the presence of a catalyst in a proper solvent under normal pressure or high pressure. Examples of the catalyst include palladium catalysts such as palladium-carbon, nickel catalysts such as Raney nickel, cobalt catalysts, ruthenium catalysts, rhodium catalysts, and platinum . catalysts. Examples of the solvent include water, alcohols such as methanol and ethanol; aromatic hydrocarbons such as benzene and toluene; chained or cyclic ethers such as ethers, dioxane, and tetrahydrofuran; and esters such as ethyl acetate. The reaction temperature may be appropriately determined in the range of -20°C to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours. As a result, the compound represented by formula (13) can be produced. In the latter technique, the conditions are not limited, and the compound represented by formula (13) can be produced under the conditions described in, for example, Organic Syntheses, Coll. Vol. Ill, p. 453.
l-(iii) Formula (13) -> Formula (14)
The benzamide derivative having a amino group represented by formula (13) is reacted with a compound represented by formula (7) (for example, a chloroformic ester, a chlorothioformic ester, or a chlorodiformic thioester) in a proper solvent to produce a compound represented by formula (14) of the present invention. In

35
this step, an appropriate base can also be used. As the solvent, any solvent which does not significantly inhibit the progress of reaction can be used. Examples of the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and 1, 2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; ketones such as acetone, methyl isobutyl ketone, and cyclohexanone; amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can be used alone or in a mixture of two ore more kinds. Examples of the base include organic bases such as triethylamine, tri-n-butylamine, pyridine, and 4-dimethylaminopyridine; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; carbonates such as sodium hydrogen carbonate and potassium carbonate; phosphates such as dipotassium hydrogen- phosphate and trisodium phosphate; alkali metal hydrides such as sodium hydride; and alkali metal alcoholates such as sodium methoxide and sodium ethoxide. The base may be used in an appropriate amount in the range of molar equivalents of 0.01 to 5 times the amount of the compound represented by formula (13). The reaction temperature may be appropriately determined in the range of -20°C to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours.

36
A compound represented by formula (16) of the present invention can be produced by Production Method 2 (in the formula, Ri, R3, G2, (X)n, and Q represent the same as described above) using a 3-isocyanatobenzoly chloride represented by formula (15) as a starting material, an alcohol represented by formula (6), a thiol, and an aromatic amine represented by formula (11) according to the technique disclosed in J. Org. Chem., p. 142 (1966).
Production Method 2
o
NCO H-G2-R, QR3NH HN^Gf
X (6) (ID fA, R-
(15) O
(16)
In this step, a solvent can be used. As the solvent, any solvent other than the solvents described in the above document can be used as long as it does not significantly inhibit the progress of reaction. Examples of the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; chained or cyclic ethers such as dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; ketones such as acetone, methyl isobutyl ketone, and cyclohexanone; amides.such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidaEolidinone. These solvents can be used alone or in a mixture of two ore more kinds. Also, a base may be added for accelerating

37
the reaction. Examples of the base other than those disclosed in the above document include organic bases such as triethylamine, pyridine, and 4-dimethylaminopyridine; and inorganic bases such as potassium carbonate. The base may be used in an appropriate amount in the range of molar equivalents of 0.01 to 5 times the amount of the compound represented by formula (15). The reaction temperature may be appropriately determined in the range of -20°C to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours.
A thioamide compound can be produced from a compound represented by formula (17) using a Lawson reagent according Production Method 3 (in the formula, Rlr R2, R3, Gi, G2, (X)n, and Q represent the same as described above).
Production Method 3
Lawesson's G, Qi
«-&& J==L- «A£ -^—w- A-%
0 s s
(17) (18) (19)
3-(i) Formula (17) -» Formula (18)
The reaction can be performed under the conditions described in Synthesis, p. 463 (1993) and Synthesis, p. 829 (1984), but the conditions such as a solvent are not limited to those described in these documents.

38
3-(ii) Formula (18) -> Formula (19) "
A' compound represented by formula (19) of the present invention can be produced using a compound represented by formula (7) (for example, a chloroformic ester or a chlorothioformic ester) under the conditions properly selected from the reaction conditions described above in the step l-(iii) of Production Method 1.
A chloropyridinecarboxylic acid can be used as a starting material. For example, a compound represented by formula (23) can be produced from a chloropyridinecarboxylic acid represented by formula (20) according to Production Method 4 (in the .formula, Rlr ^•2r R-3f Qy Gi, and G2 represent the same as described above) .
Production Method 4
G • Gi
CI QR.NH ■ CI . H^ ci^Gr^ ^yV*1
I ' /-en A^ Animation I „, J
•rS - n ? - fS- ?3 _J5 ^ A ?3
l^k ^S^Q A^O^ fUL,N.n
° O O
(20) (21) (22) (23)
4-(i) Formula (20) -» Formula (21)
A compound represented by formula (20) is halogenated in the presence or absence of an inert solvent and then reacted with an
aromatic amine represented by formula (11) to produce-a compound
represented by formula (21). As the solvent usable in the
halogenation step, any solvent .which does not significantly
inhibit the progress of reaction can be used-. Examples- of the
solvent include aromatic hydrocarbons such as benzene, toluene,

39
and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; ketones such as acetone, methyl isobutyl ketone, and cyclohexanone; amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can be used alone or in a mixture of two ore more kinds. Examples of a halogenating agent include thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride, and phosphorus trichloride. The amount of the halogenating agent used may be appropriately determined in the range of molar equivalents of 1 to 10 times the amount of the compound represented by formula (20). Also, N,N-dimethylformamide may be added as an auxiliary for accelerating the reaction. The reaction temperature may be appropriately determined in the range of -20°C to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours. As the solvent usable in the amidation step, any solvent which does not significantly inhibit the progress of reaction can be used. Examples of the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; ketones such as acetone, methyl

40
isobutyl ketone, and cyclohexanone; amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can be used alone or in a mixture of two ore more kinds. Also, a base may be added for accelerating the progress of reaction. Examples of the base include organic bases such as triethylamine, pyridine, 4-dimethylaminopyridine; and inorganic bases such as potassium carbonate. The amount of the base used may be appropriately determined in the range of molar equivalents of 0.01 to 5 times the amount of the compound represented by formula (11). The reaction temperature may be appropriately determined in the range of -20°C to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours.
A process for producing a compound represented by formula (21) from a compound represented by formula (20) and a compound represented by formula (11) without using a halogenating agent is presented by a process according to the technique disclosed in, for example, Chem. Ber., p. 788 (1970) where 1-hydroxybenzotriazole as an additive and N,N'-dicyclohexyl carbodiimide as a condensing agent are used, respectively. Other examples of the condensing agent include l-ethyl-3-(3-dimethylaminopropyl) carbodiimide, and 1,1'-carbonyl-bis-lH-imidazole. The compound represented by formula (21) can also be produced by a mixed acid anhydride technique using a chloroformic ester according to the technique disclosed in J. Am. Chem. Soc, p.

41
5012 (1967). Examples of a chloroformic ester include isobutyl chloroformate and isopropyl chloroformate. A compound other than a chloroformic ester, for example, diethylacetyl chloride or trimethylacetyl chloride, can also be used. In the technique using the condensing agent and the mixed acid anhydride technique, the solvent, the reaction temperatures, and the reaction times are not limited to those disclosed in the above documents, and an inert solvent which does not significantly inhibit the progress of reaction may be appropriately used. Also, the reaction temperature and the reaction time may be appropriately selected according to the progress of reaction.
4-(ii) Formula (21) -> Formula (22)
A compound represented by formula (22) can be produced by amination with ammonia according to the conditions described in, for example, J. Org. Chem., p. 280(1958). The conditions such as the reaction solvent are not limited to those disclosed in the above document, and an inert solvent which does not significantly inhibit the progress of reaction may be appropriately used. Also, the reaction temperature and the reaction time may be appropriately selected according to the progress of reaction. As an aminating agent, methylamine or ethylamine can be used instead of ammonia.
4-(iii) Formula (22) -» Formula (23)
A compound represented by formula (23) of the present invention can be produced by using a compound represented by

42
formula (7) (for example, a chloroformic ester or a chlorothioformic ester) under the conditions appropriately selected from the reaction conditions described above in the step l-(iii) of Production Method 1.
Even when another nitrogen-containing aromatic carboxylic acid such as 4-chloropyridine-2-carboxlic acid or 6-chloropyridine-2-carboxylic acid is selected as a starting material, the compound of the present invention can be produced according to Production Method 4. In the use of the former starting material, a compound represented by formula (1) wherein Ai is a nitrogen atom, and A2, A3, and A4 are each a carbon atom can be produced. In the use of the latter starting material, a compound represented by formula (1) wherein Ai, A2, and A3 are each a carbon atom, and A4 is a nitrogen atom can be produced.
The compound represented by formula (23) is reacted with an appropriate oxidizing agent to produce a corresponding pyridine-N-oxide derivative according to the conditions disclosed in, for example, J. Org. Chem., p. 8576 (1999). Examples of the oxidizing agent include organic peroxy acids such as m-chloroperoxybenzoic acid; sodium metaperiodate; hydrogen peroxide; ozone; selenium dioxide, chromic acid; dinitrogen tetraoxide; acyl nitrate; iodine; bromine; N-bromosuccinimide; iodosylb'enzene; and t-butyl hypochlorite. The solvent used in this step is not limited to those disclosed in the above document, and any solvent which does not significantly inhibit the progress of reaction may be used. The solvents can be used alone or in a mixture of one or more kinds. In particular, a polar solvent is preferred. The reaction

43
temperature may be appropriately determined in the range of -20CC to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours.
A compound represented by formula (27) of the present invention can be produced from a easily available m-aminobenzoic ester derivative presented by formula (24) according to Production Method 5 (in the formula, Rlr R2, R3, d, G2, (X)n, and Q represent the same as described above, and R represents a lower alkyl group).
Production Method 5
NH cArR< sArFhd i • ^ArRi OR,™ ^HK^
»A°-°—-As—-A-~w A%
o o o o
(24) (25) (26) (27)
5-(i) Formula (24) -+ Formula (25)
A compound represented by formula (25) can be produced by using a compound represented by formula (7) (for example, a chloroformic ester or a chlorothioformic ester) under the conditions appropriately selected from the reaction conditions described above in the step l-(iii) of Production Method 1.
5-(ii) Formula (25) -» Formula (26)
A compound represented formula (2 6) can be produced by hydrolysis with an alkali metal hydroxide such as sodium hydroxide

44
or potassium hydroxide, an alkali earth metal hydroxide such as calcium hydroxide, or an inorganic acid such as hydrochloric acid or sulfuric acid according to a conventional technique.
5-(iii) Formula (26) ->• Formula (27)
A compound represented by formula (27) of the present invention can be produced by condensation reaction under appropriate conditions according to the technique described above in the step 4-(i) of Production Method 4. Among the techniques described in the step 4-(i), in the technique using a halogenating agent, the compound represented by formula (27) can be produced through a compound represented by formula (2): Gi
A-^A, (2)
Hal
(wherein Alf A2, A3, A4, Gi, G2, G3, (X)n, and Hal each represent the same as described above). The halogenation step and the amidation step can be performed under reaction conditions according to the technique described above in the step 4-(i). The compound represented by formula (27) of the present invention can be produced from a m-aminobenzoic acid ester represented by formula (28) according to Production Method 6 below (in the formula, Rx, R2, R3, Gi, G2, (X)n, and Q each represent the same as described above, R represents a lower alkyl group, and L represents a functional group having leaving ability, such as halogen, methanesulfonyloxy, or trifluoromethanesulfonyloxy).

45 Production Method 6
According
f1 Gi G, to G
NH2 CI^V^' HN^G^1 Rz-L ^NWA-/R, Production ^ J./^
A (7) X <3°) X Method 5 1 2
0 o H S
(28) • (29) (25) (27)
6-(i) Formula (28) -» Formula (29)
A compound represented formula (29) can be produced by the technique described above in the step l-(iii) of Production Method 1 using a compound represented by formula (7) (for example, a chloroformic ester or a chlorothioformic ester) under appropriate conditions.
6-(ii) Formula (29) '->• Formula (25)
In this step, examples of a compound represented by formula
(30) include alkyl halides such as methyl iodide and ethyl iodide; toluenesulfonic esters; methanesulfonic esters; and alkylating agents such as dimethyl sulfate. As a solvent, any solvent which does not significantly inhibit the progress of reaction can be used. Examples of the solvent include aromatic hydrocarbozis such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; ketones such as acetone, methyl isobutyl ketone, and cyclohexanone; amides such as dimethylformamide and

46
dimethylacetamide; nitriles such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can be used alone or in a mixture of two ore more kinds. Also, a base may be added for accelerating the progress of reaction. Examples of the base include organic bases such as triethylamine, pyridine, and 4-dimethylaminopyridine; inorganic bases such as potassium carbonate, sodium hydroxide, and potassium hydroxide; and alkali metal hydrides such as sodium hydride. The amount of the base used may be appropriately determined in the range- of molar equivalents of 0.01 to 5 times the amount of the compound represented by formula (29) . The reaction temperature may be appropriately determined in the range of -20°C to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours.
6-(iii) Formula (25) -> Formula (27)
A compound represented by formula (27) of the present invention can be produced by the techniques described above in the steps 5-(ii) and 5-(iii) of Production Method 5 under appropriate conditions.
A compound represented by formula (31) of the present invention can be produced according to Production Method 7 (in the formula, Ai, A2, A3, A4, Ri, R3, G2, G3, and (X)n each represent the same as described above).
Production Method 7

47
oon A=' ?< + H_G2_R' - ™ (^ Ra
^^ (6) ^"tAX
(3) (31)
In this step, an appropriate solvent may be used. As the solvent, any solvent which does not significantly inhibit the progress of reaction can be used. Examples of the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; ketones such as acetone, methyl isobutyl ketone, and cyclohexanone; amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can be used alone or in a mixture of two ore more kinds. Also, an appropriate base may be used. Examples of the base include organic bases such as triethylamine, tri-n-butylamine, pyridine, 4-dimethylaminopyridine; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; carbonates such as sodium hydrogen carbonate and potassium carbonate; alkali metal hydrides such as sodium hydride; and alkali metal alcoholates such as sodium methoxide and sodium ethoxide. The amount of the base used may be appropriately determined in the range of molar equivalents of .0.01 to 5 times the amount of the compound represented by formula (6). The

48
reaction temperature may be appropriately determined in the range of -20°C to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours.
An isocyanate compound represented by formula (3) can be produced by Production Method 8 (in the formula, Ai, A2, A3, A4, G3, R3, (X)n, and Q each represent the same as described above) using a m-aminobenzamide derivative or a m-aminopyridinecarboxamide derivative represented by formula (32) as a starting material.
Production Method 8
NH2 \T
Af^A, AT^A.
Wn^V3 -nnk,^
(32) (3)
In this step, reaction can be performed by using phosgene according to the technique described in Organic Syntheses, Coll., Vol. II, p. 453. An isocyanate compound represented by formula (3) can also be produced by using a phosgene dimmer, triphosgene, or oxalyl chloride instead of phosgene. In this step, an appropriate solvent may be used. As the solvent, any solvent which does not significantly inhibit the progress of reaction can be used. Examples of the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters such as ethyl

49
acetate and butyl acetate; ketones such as acetone, methyl isobutyl ketone, and cyclohexanone; amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can be used alone or in a mixture of two ore more kinds. The reaction temperature may be appropriately determined in the range of -20°C to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours.
' An isocyanate compound represented by formula (3) can also be produced by Production Method 9 (in the formula, Ai, A2, A3, A4, G3, R.3, (X)n, and Q each represent the same as described above) utilizing Curtius rearrangement reaction with an isophthaloyl chloride derivative represented by formula (33) used as a starting material according to the technique described in Macromolecules, p. 104.6 (1998) .
Production Method 9
O^CI 1)R'-OH V°H if
T 2)QR,NH (11) 1 Nar^ ■ A^AA
PQn-Ahi' —: w-afr- 1 G *" ™^JL&
A3^fif^^a 3^ "Esterolysis '^'y 3 Curtius rearrangement 4 I
O R3" Q R3 Q
(33) (34) (3)
In this step, an appropriate solvent may be used. As the solvent, any solvent which does not significantly inhibit the progress of reaction can be used. Examples of the solvent include

50
aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; ketones such as acetone, methyl isobutyl ketone, and cyclohexanone; amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone'. These solvents can be used alone or in a mixture of two ore more kinds. The reaction temperature may be appropriately determined in the range of -20°C to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours. In producing a compound represented formula (34), ethanol, propanol, or benzyl alcohol can be used as an alcohol. In esterolysis, hydrolysis or catalytic hydrogen reduction can be performed by a conventional technique.
An aniline derivative represented by formula (39) can be produced by using an aminothiophenol derivative as a starting material according Production Method 10 (in the formula, R7, Yn, Y12, and m each represent the same as described above, Yio and Yi3 each represent a hydrogen atom or a halogen atom except a case in which both groups are hydrogen atoms as far as this Method is concerned, Y10a and Yi3a each represent a hydrogen atom, a halogen atom, or a methyl group as far as this Method is concerned, and one of Y10a and Yi3a necessarily represents a methyl group) .

51 Production Method 10
Y Y v ' . ■ Y„ (0)m
(35) (37) (38) (39)
Methylation
r
Y1oa Oxidation Y1ca
H2N\>^/Yii ■ -2- •yV'Yi 1
Y« Y„ (0)m
(38-2) (39-2)
10- (i) . Formula (35) -* Formula (37)
A compound represented by formula (38) can be produced by reaction of aminothiophenol represented by formula (35) with a haloalkyl iodide represented by formula (36) according to the method described in J, Fluorine Chem., p.. 207 (1994) .
Examples of a haloalkyl iodide represented by formula (36) Include trifluoromethyl iodide, pentafluoroethyl iodide, heptafluoro-n-propyl iodide, heptafluoroisopropyl iodide,
manofluoro-n-butyl iodide, and nonafluoro-2-butyl iodide. The . amount of-the haloalkyl iodide used may be .appropriately determined in the range of molar equivalents of 1 to 10 times the amount of the compound.represented formula (35). The solvent used in this step is not limited to those described in the above document, and any solvent which does not significantly inhibit the progress of reaction can be used as the solvent. Examples of.the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane,

52
chloroform, and carbon tetrachloride; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; ketones such as acetone, methyl isobutyl ketone, and cyclohexanone; amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone and hexamethylphosphoric triamide. These solvents can be used alone or in a mixture of two ore more kinds. In particular, a polar solvent is preferred. The reaction temperature may be appropriately determined in the range of -20°C to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours.
10- (ii) Formula (37) -> Formula (38)
A compound represented by formula (38) can be produced by using an appropriate halogenating agent according to the technique described in, for example, Synth. Commun., p. 1261 (1989). Examples of the halogenating agent include chlorine, bromine, iodine, N-chlorosuccinimde, N-bromosuccinimide, and N-iodosuccinimide. The amount of the halogenating agent used may be appropriately determined in the range of molar equivalents of 1 to 10 times the amount of the compound represented formula (37). The number of equivalents of the halogenating agent used can be appropriately determined so that only Y10 or Yi3 is a halogen atom. In this step, an appropriate solvent may be used. The solvent

53
used is not limited to those described in the above document, and any solvent which does not significantly inhibit the progress of reaction can be used as the solvent. Examples of the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; ketones such as acetone, methyl isobutyl ketone, and cyclohexanone; amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone and hexamethylphosphoric triamide. These solvents can be used alone or in a mixture of two ore more kinds. In particular, a polar solvent is preferred. The reaction temperature may be appropriately determined in the range of -20°C to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours.
lO-(iii) Formula (38) -> Formula (39)
A compound represented by formula (39) can be produced by using an appropriate oxidizing agent according to the technique described in, for example, Tetrahedron Lett., p. 4955 (1994). Examples of the oxidizing agent include organic peroxy acids such as m-chloroperoxybenzoic acid; sodium metaperiodate; hydrogen peroxide; ozone; selenium dioxide, chromic acid; dinitrogen

54
tetraoxide; acyl nitrate; iodine; bromine; N-bromosuccinimide; iodosylbenzene; and t-butyl hypochlorite. The solvent used in this step is not limited to those disclosed in the above document, and any solvent which does not significantly inhibit the progress of reaction may be used. The solvents can be used alone or in a mixture of one or more kinds. In particular, a polar solvent is preferred. The reaction temperature may be appropriately determined in the range of -20°C to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours.
10-(iv) Formula (38) -> Formula (38-2)
A compound represented by formula (38-2) (wherein R7, Yu, Yi2, and m each represent the same as described above, Yioa and Y13a each represent a hydrogen atom, a halogen atom, or a methyl group as far as this step is concerned, and one of Yi0a and Y13a necessarily represents a methyl group) can be produced from the compound represented by formula (38) using an appropriate methylating agent. This step can be performed according to the technique described in, for example, Tetrahedron. Lett., p. 6237 (2000).
10-(v) Formula (38-2) ->• Formula (39-2)
A compound represented by formula (39-2) (wherein R7, Yn, Y12, and m each represent the same as described above, Yioa and Yi3a both represent a methyl group or one of Y10a and Yi3a represents a methyl group and the other represents a halogen atom as far as this step is concerned) can be produced according to the technique descried'

55
above in the step lO-(iii) of Production Method 10.
The compounds represented by formula (1), (3), (4), and (8) can be produced from aniline derivatives represented by formula (38), (39), (38-2) and (39-2) according to any one Method appropriately selected from Production Methods 1 to 9.
The compound represented by formula (39) can also be produced from an aminothiophenol represented by formula (40) according to Production Method 11 (in the formula, R7, Y10, Yn, Yi2, Yi3, and m . each represent the same as described above).
Production Method 11
Y Y
v I R 10 Oxidation 10
HN X Y (36) ^W" fyX^
13 |12 Y12 Y12 (O)m
(40)2 (38) (39)
Reaction with a haloalkyl iodide and subsequent oxidation can be performed according to Production Method 10. The compounds represented by formula (1), (3), (4), and (8) can be produced from aniline derivatives represented by formula (41) and (42) according to any one Method appropriately selected from Production Methods 1 to 9.
A compound represented by formula (9) can also be produced from an aniline derivative represented by formula (41) and used as a starting material according to Production Method 12 (in the formula, R10, Rn, R12, Y14, Y15, Y16, and Y17 each represent the same as described above).

56 Production Method 12
R„ Y , Perfluorinated aldehyde or D v
I " \U ^ 12 |14
Kn I perfluorinated ketone Rn |7 ^T
vY v-V^"..
Y16 Y
16 I 16
(41) (9)
A compound represented by formula (9) can be produced by-using an appropriate perfluorinated aldehyde or perfluorinated ketone according to the technique described in, for example, J. Am. . Chem. Soc, p. 2410 (1965) and J. Org. Chem. , p. 1001 (1965). Examples of the perfluorinated aldehyde or perfluorinated ketone include hexafluoroacetone and perfluoro-2-butanone. In this step, an appropriate solvent can be used. The solvent used in this step is not limited to those disclosed in the above documents, and any solvent which does not significantly inhibit the progress of reaction may be used. The solvents can be used alone or in a mixture of one or more kinds. The reaction temperature may be appropriately determined in the range of -20°C to 200°C, and the reaction time may be appropriately determined in the range of several minutes to 96 hours.
The compounds represented by formula (1), (3), and (4) can be produced from an aniline derivative represented by formula (9) according to any one properly selected from Production Methods 1 to 9.
In all the production Methods, the compounds may be isolated from the reaction systems after reactions according to a normal technique. However, the compounds can be optionally purified by an operation such as recrystallization, column chromatography,

57
distillation, or the like. Alternatively, the compounds may be
used in next reaction steps without being isolated from the
reaction systems.
Although typical examples of the compounds represented by
formula (1) and used as active ingredients of insecticides of the
present invention are shown in Tables 1 to 5, the present
invention is not limited to these examples.
Although typical examples of the compounds represented by
formula (4) are shown in Tables 6 to 8, the present invention is not limited to these examples.
In the tables, "n-" denotes normal, "Me" denotes a methyl group, "Et" denotes an ethyl group; "n-Pr" denotes a normal propyl group, "i-Pr, denotes an isopropyl group, "n-Bu" denotes a normal butyl group, "i-Bu" denotes an isobutyl group, "s-Bu" denotes a secondary butyl group, "t-Bu" denotes a tertiary butyl group, "H" denotes a hydrogen atom, "0" denotes an oxygen atom, "S" denotes a sulfur atom, "C" denotes a carbon atom, "N" denotes a nitrogen atom, "F" denotes a fluorine atom, "CI" denotes a chlorine atom, "Br" denotes a bromine atom, "I" denotes an iodine atom, "CF3" denotes a trifluoromethy group, "MeO" denotes a methoxy group, "NH2" denotes an amino group, "MeNH" denotes a methylamino group, and "Me2N" denotes a dimethylamino group.

58
Table 1(1)
O
HNA0/Rl
d^o °-A)
Q
Compound No. fy Q
1 Me 2-methyl-4-heptafluoroisopropylphenyl
2 Et 2-methyl-4-heptafluoroisopropylphenyl
3 i-Pr 2-methyl-4-heptafluoroisopropylphenyl
4 • n-Bu 2-methyl-4-heptafluoroisopropylphenyl
5 i-Bu 2-methyl-4-heptaf luoroisopropylphenyl
6 s-Bu 2-methyl-4-heptaf luoroisopropylphenyl
7 t-Bu 2 -me thyl-4-heptaf luoroisopropylphenyl
8 neopentyl 2-methyl-4-heptaf luoroisopropylphenyl
9 3,3-dimethyl-n-butyl 2-me thyl-4-heptaf luoroisopropylphenyl
10 2-ethyl-n-hexyl 2-methyl-4-heptaf luoroisopropylphenyl
11 vinyl 2-me thyl-4-heptaf luoroisopropylphenyl
12 allyl 2-me thyl-4-heptaf luoroisopropylphenyl
13 ■ 2-isopropyl-5-methylcyclohexyl 2-methyl-4-heptaf luoroisopropylphenyl
14 benzyl 2-me thyl-4-heptaf luoroisopropylphenyl
15 3-cyanobenzyl 2 -me thyl-4-heptaf luoroisopropylphenyl
16 4-cyanobenzyl 2-me thyl-4-heptaf luoroisopropylphenyl
17 2-roethoxyethyl 2-methyl-4-heptaf luoroisopropylphenyl
18 chloromethyl 2-methyl-4-heptaf luoroisopropylphenyl
19 2-chloroethyl 2-me thyl-4-heptaf luoroisopropylphenyl
20 2,2,2-trichloroethyl 2-me thyl-4-heptaf luoroisopropylphenyl
21 1,2,2,2-tetrachloroethyl 2-me thyl-4-heptaf luoroisopropylphenyl
22 l,l-dimethyl-2,2,2-trichloroethyl 2-me thyl-4-heptaf luoroisopropylphenyl
23 3-trifluoromethylphenyl 2-methyl-4-heptaf luoroisopropylphenyl
24 4-methylphenyl 2-methyl-4-heptafluoroisopropylphenyl
25 4-chlorophenyl 2 -me thyl-4-heptaf luoroisopropylphenyl
26 cyclobutyl 2 -methyl-4-heptaf luoroisopropylphenyl
27 cyclopentyl '' 2-me thyl-4-heptaf luoroisopropylphenyl
28 2-cyanoethyl 2-me thyl-4-heptaf luoroisopropylphenyl
29 2-(ethylthio) ethyl 2-methyl-4-heptafluoroisopropylphenyl
30 2- (ethylsulfinyl) ethyl 2-methyl-4-heptafluoroisopropylphenyl

59
Table 1(2)
Compound No. R.! Q
31 2- (ethylsulfonyl) ethyl 2-me thyl-4-heptafluoroisopropylphenyl
3_2 2-fluoroethyl 2-methyl-4-heptafluoroisopropylphenyl
33 2,2-difluoroethyl 2-methyl-4-heptafluoroisopropylphenyl
34 2,2,2-trifluoroethyl 2-me thyl-4-heptafluoroisopropylphenyl
35 1, 3-dif luoro-2-propyl 2-methyl-4-heptafluoroisopropylphenyl
36 l-chloro-3-£luoro-2-propyl 2-methyl-4-heptafluoroisopropylphenyl
37 l-methyl-2,2,2-trifluoro-2-propyl 2-methyl-4-heptafluoroisopropylphenyl
38 3,3,3-trifluoro-n-propyl 2-methyl-4-heptafluoroisopropylphenyl
39 3,3,4,4,4-pentafluoro-2-butyl 2-methyl-4-heptafluoroisopropylphenyl
40 4,4, 4-trifluoro-n-butyl 2-methyl-4-hepta£luoroisopropylphenyl
41 2,2,3,3-tetrafluorocyclobutyl 2-methyl-4-heptafluoroisopropylphenyl
42 2,2-dichloroethyl 2-methyl-4-heptafluoroisopropylphenyl
43 1,3-dichloro-2-propyl 2-methyl-4-heptafluoroisopropylphenyl
44 3-chloro-n-propyl 2-methyl-4-heptafluoroisopropylphenyl
45 3,3,3-trichloro-n-propyl 2-methyl-4-heptafluoroisopropylphenyl
46 2-bromqethyl 2-metfayl-4-heptafluoroisopropylphenyl
47 2, 2,2-tribromoethyl 2-methyl-4-heptafluoroisopropylphenyl
48 2-iodoethyl 2-methyl-4-heptafluoroisopropylphenyl
49 tetrahydrofuran-3-yl 2-methyl-4-heptafluoroisopropylphenyl
50 (furan-2-yl) methyl 2-methyl-4-heptafluoroisopropylphenyl
51 (furan-3-yl) methyl 2-methyl-4-heptafluoroisopropylphenyl
52 , (tetrahydrofuran-2-yl)methyl 2-methyl-4-heptafluoroisopropylphenyl
53 (tetrahydrofuran-3-yl) methyl j 2-methyl-4-heptafluoroisopropylphenyl
54 (thiophen-2-yl) methyl 2-me thyl-4-heptafluoroisopropylphenyl
55 (thiophen-3-yl) methyl 2-methyl-4-heptafluoroisopropylphenyl
56 (pyridin-2-yl)methyl 2-methyl-4-heptafluoroisopropylphenyl
57 (pyridin-3-yl) methyl 2-methyl-4-heptafluoroisopropylphenyl
58 (6-chloropyridin-3-yl) methyl 2-methyl-4-heptafluoroisopropylphenyl
59 Me 2, 6-dimethyl-4-heptafluoroisopropylphenyl
60 Et 2,6-dimethyl-4-heptaf luoroisopropylphenyl

60
Table 1(3)
Compound No. Rx Q
61 n-Pr 2, 6-dimethy.I-4-heptaf luoroisopropylphenyl
62 i-Pr 2, 6-dimethyl-4-heptafluoroisopropylphenyi
63 n-Bu 2,6-dimethyl-4-heptafluoroisopropylphenyl
64 i-Bu 2, 6-dimethyl-4-heptafluoroisopropylphenyl
65 s-Bu 2,6-dimethyl-4-heptafluoroisopropylphenyl
66 t-Bu 2, 6-dimethyl-4-heptaf luoroisopropylphenyl
67 neopentyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
68 1, 2-dimethyl-n-propyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
69 1 -methyl-n-butyl 2, 6-dtmethyl-4-heptafluoroisopropylphenyl
70 1, 3-dimethyl-n-butyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
71 3,3-dimethyl-n-butyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
72 cyclopentylmethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
73 1-phenylethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
74 2-phenylethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
75 vinyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
7 6 allyl 2,6-dimethyl-4-heptafluoroisopropylphenyl ,
77 propargyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
78 cyclobutyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
79 cyclopentyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
80 cyclohexyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
81 benzyl 2(6-dimethyl-4-heptafluoroisopropylphenyl
82 4-methylbenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
83 4-trifluoromethylbenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
84 3-cyanobenzyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
85 4-cyanobenzyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
86 2-fluorobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
87 3-fluorobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
88 4-fluorobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
89 2-chlorobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
90 3-chlorobenzyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl

61 Table 1(4)
Compound Mo. p^ Q
91 4-chlorobenzyl 2, 6-dimethyl-4-beptafluoroisopropylphenyl
92 4-nitrobenzyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
93 4-roethoxycarbonylben2yl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
94 2-hydroxyethyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
95 2-methoxyethyl 2, 6-dimethyl-4-heptaf luoroisopropylphenyl
96 2-ethoxyethyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
97 2-isopropyloxyethyl 2, 6-dimethyl-4-heptaf luoroisopropylphenyl
98 2-benzyloxyethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
99 3-ethoxy-n-propyl ■■ 2, 6-dimethyl-^4-heptafluoroisopropylphenyl
100 ethoxycarbonylmethyl 2,6-dimethyl-4-heptaf luoroisopropylphenyl
101 l-(methoxycarbonyl) ethyl 2, 6-dimethyl-4-heptaf luoroisopropylphenyl
102 l-(ethoxycarbonyl) ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
103 3-oxo-n-butyl 2,6-dimethyl-4-heptaf luoroisopropylphenyl
104 2-acetoxyethyl 2, 6-dimethyl-4-heptaf luoroisopropylphenyl
105 cyanomethyl 2, 6-dimethyl-4-heptaf luoroisopropylphenyl
106 2-cyanoethyl 2,6-dimethyl-4-heptaf luoroisopropylphenyl ,
107 3-cyano-n-propyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
108 2-(methylthio)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
109 2-(ethylthio)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
110 2-(isopropylthio)ethyl 2,6-dimethyl-4-heptaf luoroisopropylphenyl
111 l-methyl-2-(methylthio) ethyl 2, 6-dimethyl-4-heptaf luoroisopropylphenyl
112 ,2-(ethylsulfinyl)ethyl 2,6-dimethyl-4-heptaf luoroisopropylphenyl
113 2- (ethylsulfonyl) ethyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
114 3- (methylthio) -n-prbpyl 2, 6-diiaethyl-4-heptaf luoroisopropylphenyl
115 3-(ethylthio)-n-propyl 2,6-dimethyl-4-heptaf luoroisopropylphenyl
116 2-fluoroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
. in 2,2-difluoroethyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
118 2,2,2-trifluoroethyl r_ 2, 6-dimethyl-4-hepta£luoroisopropylphenyl
119 l,3-difluoro-2-propyl 2,6-dlmethyl-4-heptafluoroisopropylphenyl
120 1 -chloro-3-f luoro-2-propyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl

62 Table 1(5)
Compound No. pvl Q
121 l-methyl-2,2, 2-trifluoroethyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
122 1,1,1, 3, 3, 3-hexafluoro-2-propyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
123 3, 3, 3-trifluoro-n-propyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
124 2, 2, 3,3,3-pentafluoro-n-propyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
125 3,3,4,4, 4-pentafluoro-2-butyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
126 4,4, 4-tifluoro-n-butyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
127 2,2,3,3-tetrafluorocyclobutyl 2, 6-dxmethyl-4-heptafluoroisopropylphenyl
128 chloromethyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
129 trichloromethyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
130 2-chloroethyl 2, 6-dimetfayl-4-heptafluoroisopropylphenyl
131 2,2-dichloroethyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
132 2,2,2-trichloroethyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
133 1, 2, 2, 2-tetrachloroethyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
134 l,3-dichloro-2-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
135 1, l-dimethyl-2,2, 2-trichloroethyl 2, 6-diniethyl-4-heptaf luoroisopropylphenyl
136 3-chloro-n-propyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
137 2-bromoethyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
138 2,2,2-tribromoethyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
139 3-broroo-n-propyl 2, 6-diroethyl-4-heptafluoroisopropylphenyl
140 2-iodoethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
141 2- (acetylamino) ethyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
142 2- (dimethylamino) ethyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
143 2- (ethylamino) ethyl 2, 6-diroethyl-4-heptafluoroisopropylphenyl
144 methylaminocarbonylethyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
145 phenyl . 2,6-diroethyl-4-heptaf luoroisopropylphenyl
146 - 4-methylphenyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
147 3-trifluoromethylphenyl 2, 6-dimethyl-4-heptailuoroisopropylphenyl
148 4-chlorophenyl 2, 6-dimethyl-4-heptailuoroisopropylphenyl
149" naphthyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
150 Pyridine-2-yl 2,6-dimethyl-4-heptafluoroisopropylphenyl

63 Table 1(6)
Compound No. Ri Q
151 pyridine-3-yl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
J-52 pyridine-4-yl 2, 6-tiimethyl-4-heptafluoroisopropylphenyl
153 tetrahydrofuran-2-yl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
154 tetrahydrofuran-3-yl 2,6-dimethyl-4-heptafluoroisopropylphenyl
155 (furan-2-yl) methyl 2, 6-dimethyl-4-heptailuoroisopropylphenyl
156 (furan-3-yl)methyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
157 (tetrahydrofuran-2-yl)methyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
158 (tetrahydrofuran-3-yl)methyl 2,6-dimethyl-4-heptarluoroisopropylphenyl
159 (thiophen-2-yl)methyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
160 (thiophen-3-yl)methyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
161 (pyridin-2-yl) methyl 2,6-dimethyl-4~heptafluoroisopropylphenyl
162 (pyridin-3-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
163 (6-chloropyridin-3-yl)methyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
lg. M 2-methyl-6-isopropyl-4-heptafluoro
isopropylphenyl
]fil. ■Pt 2-methyl-6-isopropyl-4-heptafluoro
isopropylphenyl
166 i-Pr 4-heptafluoroisopropylphenyl
167 i-Pr 3-methyl-4-heptafluoroisopropylphenyl
168 i-Pr 2-ethyl-4-heptafluoroisopropylphenyl
169 i-Pr 2-propyl-4-heptafluoroisopropylphenyl
170 i-Pr 3-methoxy-4-heptafluoroisopropylphenyl
171 i-Pr 3-chloro-4-heptafluoroisopropylphenyl
172 i-Pr 2,3-dimethyl-4-heptafluoroisopropylphenyl
173 i-Pr 2,5-dimethyl-4-heptafluoroisopropylphenyl
174 i-Pr 2, 6-diethyl-4-heptafluoroisopropylphenyl
175 i-Pr 2-ethyl-6-methyl-4-heptafluoroisopropylphenyl ~ \ 2-methyl-6-isopropyl-4-heptafluoroisopropyl
176 ^2f phenyl
177 i-Pr 2-methoxy-6-methyl-4-heptafluoroisopropylphenyl
178 i-Pr 2-methyl-6-phenyl4-heptafluoroisopropylphenyl
179 i-Pr 2-chloro-5-methyl-4-heptafluoroisopropylphenyl
180 i-Pr 2-chloro-6-ethyl-4-heptafluoroisopropylphenyl

64
Table 1(7)
Compound No. Rj Q
,g, i-Pr 2-chloro-6-n-propyl-4-heptafluoroisopropyl
phenyl
182 i-Pr 2-chloro-5-methoxy-4-heptafluoroisopropylphenyl
,„, ._ 2,3~dimethyl-6-chloro-4-heptafluoroisopropyl
phenyl
.„. . 2-chloro-3, 6-dirnethyl-4-heptafluoroisopropyl
phenyl
lfi. . 2-methyl-3-chloromethyl-6-chloro~4-heptafluoro
isopropylphenyl
, „,_ . „ 2-methyl-3-iodo-6-chloro-4-heptafluoro
186 i-Pr * . , . ,
i s opropylphenyl
187 2,2,2-trichloroethyl 4-heptafluoroisopropylphenyl
188 2,2,2-trichloroethyl 3-methyl-4-heptafluoroisopropylphenyl
189 2,2,2-trichloroethyl 2-ethyl-4-heptafluoroisopropylphenyl
190 2,2,2-trichloroethyl 2-propyl-4-hepta£luoroisopropylphenyl
191 2,2,2-trichloroethyl 3-methoxy-4-heptafluoroisopropylphenyl
192 2,2,2-trichloroethyl -, 2-chloro-4-heptafluoroisopropylphenyl
193 2,2,2-trichloroethyl 3-chloro-4-heptafluoroisopropylphenyl
194 2,2,2-trichloroethyl . 2,3-dimethyl-4-heptafluoroisopropylphenyl
195 2,2,2-trichloroethyl 2,5-dimethyl-4-heptafluoroisopropylphenyl
196 2,2,2-trichloroethyl 2,6-diethyl-4-heptafluoroisopropylphenyl
197 2,2,2-trichloroethyl 2-ethyl-6-methyl-4-heptafluoroisopropylphenyl
... _ 0 , . . .. ... 2-methyl-6-isopropyl-4-heptafluoro
198 2,2,2-trichloroethyl J . , v. ■,
isopropylphenyl
199 2,2,2-trichloroethyl 2-methoxy-6-methyl-4-heptafluoroisopropylphenyl
200 2,2,2-trichloroethyl 2-methyl-6-phenyl-4-heptafluoroisopropylphenyl
201 2,2,2-trichloroethyl 2-hydroxy-6-znethyl^-heptafluor0isoPropyl
202 2,2,2-trichloroethyl 2-chloro-5-methyl-4-heptafluoroisopropylphenyl
203 2,2,2-trichloroethyl 2-methyl-3-amino-4-heptafluoroisopropylphenyl
7T~ „-„..., .. . 2-methyl-3-t-butoxycarbonylamino-4-heptafluoro
204 2,2,2-trichloroethyl 2 . . ' ,
'_ isopropylphenyl
205 2,2,2-trichloroethyl 2-chloro-6-ethyl-4-heptafluoroisopropylphenyl
206 2,2,2-trichloroethyl 2-bromo-6-ethyl-4-heptafluoroisopropylphenyl
207 2,2,2-trichloroethyl 2-ethyl-6-iodo-4-heptafluoroisopropylphenyl
„„„ o -, n *. ■ ,.-, ..w -i 2-chloro-6-n-propyl-4-heptafluoro
208 2,2,2-trichloroethyl isopropylphenyl
209 2,2,2-trichloroethyl 2-bromo-6-n-Propyl-4-heptafluoro
_ J isopropylphenyl
_,„ n n n ^ • ..-I ^ ■> 2-bromo-6-n-butyl-4-heptafluoro
210 1 2,2,2-trichloroethyl | isopropylphenyl

65
Table 1(8)
Compound No. Rj Q
211 2,2,2-trichloroethyl 2-chloro-5-methoxy-4-heptaflUoro * I isopropylphenyl
212 2,2,2-trichloroethyl 2-bron.o-6-methylthio-4-heptafluoro isopropylphenyl
213 2,2, 2-trichloroethyl 2, 6-dichloro-4-heptafluoroisopropylphenyl
214 2,2,2-trichloroethyl 2,3-dimethyl-6-chloro-4-heptafluoro isopropylphenyl
215 2,2,2-trichloroethyl 2-chloro-3,6-dimethyl-4-heptafluoro _ l s opr opylphenyl
216 2,2,2-trichloroethyl 2-methyl-3-chloromethyl-6-chloro-4-heptafluoro i isopropylphenyl
„._ n o -» J. • i-i .-i-i 2-methyl-3,6-dichloro-4-heptafluoro
217 2,2,2-trichloroethyl ' . , ,_ ,
isopropylphenyl
_,„ _ _ _ _ . , , .. , 2-methyl-3-bromo-6-chloro-4-heptafluoro
218 2,2,2-trichloroethyl J . , ,_ -,
isopropylphenyl
_,„ _ n _ . . . . .. , 2-methyl-3-iodo-6-chloro-4-heptafluoro
219 2,2,2-trichloroethyl J . , ,_ ,
isopropylphenyl
__,_ ooni.-i.-i ^^i 2-mfithyl-3-amino-6-chloro-4-heptafluoro
220 2,2,2-trichloroethyl * . , ^ ,
isopropylphenyl
._, -,-,-, 4. -^i -, 2-bromo-6-n-butyl-4-heptafluoro
221 3,3,3-tnfluoro-n-propyl . J, . f
isopropylphenyl
222 i-Pr 2-chloro-6-methyl-4-tri£luoronifithylphenyl
223 i-Pr 2, 6-dichloro-4-1rif luoromethylphenyl
224 i-Pr 2-bromo-4, 6-bis (trifluoromethyl)phenyl
225 i-Pr 2,6-dimethyl-4-heptafluoro-n-propylphenyl
226 i-Pr 2,6-dimethyl-4-nonafluoro-n-butylphenyl
227 2,2,2-trichloroethyl 4-trifluorome thylphenyl
228 2,2,2-trichloroethyl 2-chloro-6-methyl-4-trifluorome thylphenyl
229 2,2,2-trichloroethyl 2-bromo-6-chloro-4-trifluorome thylphenyl
230 2,2,2-trichloroethyl 2, 6-dichloro-4-trifluoromethylphenyl
231 2,2,2-trichloroethyl 2-chloro4, 6-bistrifluoromethylphenyl
232 2,2,2-trichloroethyl 2-bromo-4,6-bistrif luoromethylphenyl
233 2,2,2-trichloroethyl 2, 6-dimethyl-4-heptafluoro-n-propylphenyl
234 2,2,2-trichloroethyl 2, 6-dJunethyl-4-nonafluoro-n-butylphenyl
235 2,2,2-trichloroethyl 2,3, 5, 6-tetrafluoro-4-trifluoromethylphenyl
236 2,2,2-trichloroethyl 2,6-dibromo-4-pentafluoroethylphenyl
237 3,3,3-trifluoro-n-propyl 2,6-dibromo-4-pentafluoroethylphenyl
238 3,3,3-trifluoro-n-propyl 2-bronio6-chloro-4-trif luoromethylphenyl
239 Et 2,4-bis (trifluoromethyl)phenyl
240 i-Pr 2,4-bis (trifluoromethyl) phenyl

66 Table 1(9)
Compound No. Ri Q
241 vinyl 2, 4-bis (trifluoromethyl)phenyl
242 cyclopentyl 2, 4-bis (trifluoromethyl)phenyl
243 2-chloroethyl 2, 4-bis(trifluoromethyl)phenyl
244 2-cyanoethyl 2,4-bis(trifluoromethyl)phenyl
245 2, 2-difluoroethyl 2, 4-bis (trifluoromethyl)phenyl
246 2,2-dichloroethyl 2,4-bis (trifluoromethyl)phenyl
247 " 2,2, 2-trichloroethyl 2, 4-bis (trifluoromethyl) phenyl
248 2,2,2-tribromoethyl 2,4-bis (trifluoromethyl) phenyl
249 3,3,3-trifluoro-n-propyl 2,4-bis (trifluoromethyl)phenyl
250 2, 2,3,3,3-pentafluoro-n-propyl 2, 4-bis (trifluoromethyl)phenyl
251 4-cyanobenzyl 2, 4-bis (trifluoromethyl) phenyl '
252 (6-chloropyridin-3-yl)methyl 2, 4-bis (trifluoromethyl)phenyl
253 i-Pr 2, 6-diroethyl-4- (nonaf luoro-2-butyl) phenyl
254 2,2-difluoroethyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl
255 1, 3-dif luoro-2-propyl 2, 6-dimethyl-4- (nonafluoro-2-butyl)phenyl
256 2,2,2-trifluoroethyl 2, 6-dimethyl-4- (nonafluoro-2-butyl)phenyl
257 2, 2, 2-trichloroethyl 2, 6-dimethyl-4- (noanfluoro-2-butyl) phenyl
258 l-methyl-2, 2,2-trifluoroethyl 2, 6-dimethyl-4- (nonafluoro-2-butyl(phenyl
259 3, 3,3-trifluoro-n-propyl 2, 6-dimethyl-4- (nonafluoro-2-butyl)phenyl
260 Et 2, 6-dimethyl-4- (nonafluoro-2-butyl)phenyl
261 vinyl 2, 6-dimethyl-4- (nonaf luoro-2-butyl) phenyl
262 propargyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl
263 cyclobutyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl
264 cyclopentyl 2, 6-dimethyl-4- (nonaf luoro-2-butyl) phenyl
265 benzyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl
266 3-cyanobenzyl 2, 6-dimethyl-4- (nonafluoro-2-butyl)phenyl
267 4-cyanobenzyl 2, 6-dimethyl-4- (nonaf luoro-2-butyl) phenyl
26B 3-chlorobenzyl 2, 6-diinethyl-4- (nonaf luoro-2-butyl) phenyl
269 2-methoxyethyl 2, 6-dimethyl-4- (nonafluoro-2-butyl)phenyl
270 | 2-cyanoethyl 2,6-dimethyl-4- (nonaf luoro-2-rjutyl) phenyl

67 Table 1(10)
Compound No. P-i Q
271 2- (methylthio) ethyl 2, S-dimethyl-4- (nonafluoro-2-butyl)phenyl
272 2-(ethylthio)ethyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl
273 l-methyl-2-(methylthio)ethyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl
274 2-(ethylsulfinyl)ethyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl
275 2-(ethylsulfonyl)ethyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl
276 2-fluoroethyl 2,G-dimethyl-4-(nonafluoro-2-butyl)phenyl
277 l-chloro-3-fluoro-2-propyl 2, 6-dimethyl-4- (nonaf luoro-2-butyl)phenyl
278 2,2,3,3,3-pentafluoro-n-propyl 2,6-dimethyl-4- (nonafluoro-2-butyl)phenyl
279 3,3,4, 4, 4-pentafluoro-2-butyl 2,6-dimethyl-4- (nonaf luoro-2-butyl) phenyl
280 4, 4, 4-trifluoro-n-butyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl
281 2,2,3, 3-tetrafluorocyclobutyl 2, 6-dimethyl-4- (nonaf luoro-2-butyl) phenyl
282 2-chloroethyl 2, 6-dimethyl-4- (nonaf lupro-2-butyl)phenyl
283 2,2-dichloroethyl 2, 6-dimethyl-4- (nonaf luoro-2-butyl) phenyl
284 l,3-dichloro-2-propyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl
285 3-chloro-n-propyl . 2, 6-dimethyl-4-(nonafluoro-2-butyl)phenyl
286 2-bromoethyl 2, 6-dimethyl-4- (nonaf luoro-2-butyl) phenyl
287 2,2, 2-tribromoethyl 2, 6-dijnethyl-4- (nonafluoro-2-butyl)phenyl
288 3-bromo-n-propyl 2, 6-dimethyl-4-(nonafluoro-2-butyl)phenyl
289 2-iodoethyl 2, 6-dimethyl-4- (nonaf luoro-2-butyl) phenyl
290 tetrahydrofuran-3-yl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl
291 (f uran-2-yl) methyl 2,6-dimethyl-4- (nonaf luoro-2-butyl) phenyl
292 (f uran-3-yl) methyl 2, 6-dimethyl-4- (nonaf luoro-2-butyl) phenyl
293 (tetrahydrofuran-2-yl)methyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl
294 (tetrahydrofuran-3-yl)methyl 2,6-dimethyl-4- (nonaf luoro-2-butyl) phenyl
295 (thiophen-2-yl)methyl 2, 6-dxmethyl-4- (nonafluoro-2-butyl)phenyl
296 (thiopheh-3-yl)methyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl
297 (pyridin-2-yl)methyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl
298 (pyridin-3-yl)methyl 2, 6-dimethyl-4- (nonafluoro-2-butyl)phenyl
299 (6-chloropyridin-3-yl)methyl 2,6-dimethyl-4- (nonaf luoro-2-butyl) phenyl
300 2, 2,2-trichloroethyl 2, 6-dlchloro-4- (trifluoromethylthio)phenyl

68
Table 1(11)
Compound No. Ri Q
301 2,2, 2-trichloroethyl 2, 6-dichloro-4-(trifluoromethylsulfonyl)phenyl
302 Et 2, 6-dimethyl-4-pentafluoroethylphenyl
303 i-Pr 2, 6-dimethyl-4-pentaf luoroethylphenyl
304 propargyl 2,6-dimethyl-4-pentaf luoroethylphenyl
305 cyclobutyl 2,6-dimethyl-4~pentafluoroethylphenyl
306 cyclopentyl 2,6-dimethyl-4-pentafluoroethylphenyl
307 benzyl 2,6-dimethyl-4-pentafluoroethylphenyl
308 3-cyanobenzyl 2, 6-dimethyl-4-pentafluoroethylphenyl
309 4-cyanobenzyl 2,6-dimethyl-4-pentafluoroethylphenyl
310 3-chlorobenzyl 2, 6-dimethyl-4-pentafluoroethylphenyl
311 2-methoxyethyl 2, 6-dimethyl-4 -pentaf luoroethylphenyl
312 2-cyanoethyl 2,6-dimethyl-4-pentaf luoroethylphenyl
313 2- (methylthio) ethyl 2, 6-dimethyl-4-pentafluoroethylphenyl
314 2- (ethylthio) ethyl 2, 6-dimethyl-4-pentaf luoroethylphenyl
315 l-inethyl2- (methylthio) ethyl 2, 6-dimethyl-4-pentafluoroethylphenyl
316 2- (ethylsulfinyl) ethyl 2, 6-dimethyl-4-pentafluoroethylpheny 1
317 2-(ethylsulfonyl)ethyl 2,6-dimethyl-4-pentafluoroethylphenyl
318 2-fluoroethyl 2,6-dlmethyl-4-pentaf luoroethylphenyl
319 2,2-difluoroethyl 2,6-dimethyl-4-pentaf luoroethylphenyl
320 2,2, 2-trif luoroe thy 1 2, 6-dimethyl-4-pentafluoroethylphenyl

69 Table 1(12)
Compound No. P.j Q
321 1,3-difluoro-2-propyl 2, 6-dimethyl-4-pentafluoroethylphenyl
322 l-chloro-3-fluoro-2-propyl 2, 6-dimethyl-4-pentafluoroethylphenyl
323 l-methyl-2,2,2-trifluoroethyl 2, 6-dimethyl-4-pentafluoroethylphenyl
324 3, 3, 3-trif luoro-n-propyl 2, 6-dimethyl-4-pentafluoroethylphenyl
325 2,2,3, 3,3-pentafluoro-n-propyl 2, 6-dimethyl-4-pentafluoroethylphenyl
326 3,3,4,4,4-pentafluoro-2-butyl 2,6-dimethyl-4-pentafluoroethylphenyl
327 4, 4, 4-trif luoro-n-butyl 2, 6-dimethyl-4-pentaf luoroethylphenyl
328 2,2,3, 3-tetrafluorocyclobutyl 2, 6-dimethyl-4-pentafluoroethylphenyl ^_
329 2-chloroethyl 2,6-dimethyl-4-pentafluoroethylphenyl
330 2,2-dichloroethyl 2, 6-dimethyl-4-pentafluoroethylphenyl
331 2,2,2-trichloroethyl 2, 6-dimethyl-4-pentafluoroethylphenyl
332 1, 3-dichloro-2-propyl 2, 6-dimethyl-4-pentafluoroethylphenyl
333 3-chloro-n-propyl 2, 6-dlmethyl-4-pentafluoroethylphenyl
334 2-bromoethyl 2,6-dimethyl-4-pentarluoroethylphenyl
335 2, 2, 2-tribromoethyl 2, 6-dimethyl-4-pentafluoroethylphenyl
336 3-bromo-n-propyl 2, 6-dimethyl-4-pentafluoroethylphenyl
337 2-iodoethyl 2, 6-dimethyl-4-pentafluoroethylphenyl
338 tetrahydrofuran-3-yl 2, 6-dimethyl-4-pentafluoroethylphenyl
339 (furan-2-yl)methyl 2, 6-dimethyl-4-pentafluoroethylphenyl
340 [ (furan-3-yl)methyl 2, 6-dimethyl-4-pentafluoroethylphenyl

70 Table 1(13)
Compound No. Rj. Q
341 (tetrahydrofuran-2-yl)methyl 2, 6-dimethyl-4-pentafluoroethylphenyl
342 (tetrahydrofuran-3-yl)methyl 2, 6-dimethyl-4-pentafluoroethylphenyl
343 (thiophen-2-yl)methyl 2, 6-dimethyl-4-pentafluoroethylphenyl
344 (thiophen-3-yl)methyl 2, 6-diitiethyl-4-pentafluoroethylphenyl
345 (pyridin-2-yl)methyl 2, 6-dimethyl-4-pentafluoroethylphenyl
346 (pyridin-3-yl)methyl 2, 6-dimethyl-4-pentafluoroethylphenyl
347 (6-chloropyridin-3-yl) methyl 2,6-dimethyl-4-pentafluoroethylphenyl
_„_ ., 2,6-dimethyl-4-(2-bromo-l,1,2,3,3,3-hexafluoro
348 Me J , / .' '
-isopropyl) phenyl
,„. ~ 2, 6-dimethyl-4-(2-bromo-l,1,2,3,3,3-hexafluoro
34y Et . ... . -
-isopropyl)phenyl
. 2,6-dimethyl-4-(2-bromo-l,1,2,3,3,3-hexafluoro
-isopropyl)phenyl
„„, , 2,6-dimethyl-4-(2-bromo-l,1,2,3,3,3-hexafluoro
351 propargyl J \ i, ,_ i
r c ^J -isopropyl) phenyl
-_„ ■. 1. j. -i 2, 6-dimethyl-4-(2-bromo-l, 1,2, 3,3, 3-hexafluoro
352 cyclobutyl J . ... .
_ -isopropyl) phenyl
_.-_, , ,_ , 2,6-dimethyl-4-(2-bromo-l, 1,2,3,3,3-hexafluoro
353 cyclopentyl J . ,.' .
J * -isopropyl) phenyl
... _, . , 2,6-dimethyl-4-(2-bromo-l, 1,2,3,3,3-hexafluoro
354 3-cyanobenzyl J \ 1,1.-,
_ _ -isopropyl) phenyl
_,.,. . . , 2,6-dimethyl-4-(2-bromo-l, 1,2,3,3,3-hexafluoro
355 4-cyanobenzyl * ,,' ' ,
-isopropyl) phenyl
_,„ ., ., 2, 6-dimethyl-4-(2-bromo-l,1,2,3,3,3-hexafluoro
356 3-chlorobenzyl J . . ' .,
_ -1 s opropyl) phenyl
_,,„ - ,_. , 2,6-dimethyl-4-(2-bromo-l,1,2,3,3,3-hexafluoro
357 2-methoxyethyl J \ .. . ,
J J -isopropyDphenyl
.. 2,6-dimethyl-4-(2-bromo-l,1,2,3,3,3-hexafluoro
_ _ -i sopropyl) ph enyl
TTT „ . .. ... . . .. . 2,6-dimethyl-4-(2-bromo-l,1,2,3,3,3-hexafluoro
359 2-(methylthio)ethyl J .' ' ' '
J J -isopropyl) phenyl
ITT „ , .. . _ . . .. . 2, 6-dimethyl-4-(2-bromo-l,1,2,3,3,3-hexafluoro
360 2-(ethylthio)ethyl J . ,, .,
J J -isopropyl) phenyl

71 Table 1(14)
Compound No. Rj Q
361 l-methyl-2- (methylthio) ethyl I 2' 6-dimethyl-4- (2-bromo-l, 1, 2,3,3,3-hexafluoro
| -isopropyl) phenyl
362 2-(ethylsulfinyl)ethyl 2'6-di»ethyl-4-(2-bromo-l,1,2,3 3,3-hexafluoro
| -isopropyl) phenyl
,,-, _ . ., , ,. . . .. . 2,6-dimethyl-4-(2-bromo-l, 1,2,3,3,3-hexafluoro
363 2-(ethylsulfonyl)ethyl ■* . ,,', ' '
_ -isopropyl) phenyl
364 2-fluoroethyl 2,6-dimethyl-4-(2-bromo-l,1,2,3,3,3-hexafluoro
-isopropyl) phenyl
,,c _ _ ..,. .. , 2,6-dimethyl-4- (2-bromo-l, 1,2,3,3,3-hexafluoro
365 2,2-difluoroethyl J . '. ,
-isopropyl) phenyl
,,_, _ _ _ . . _. ... , 2,6-dimethyl-4- (2-bromo-l, 1,2,3,3,3-hexafluoro
366 2,2,2-trifluoroethyl 2 . ,,' '
-isopropyl) phenyl
,„ , , ,._. _ , 2,6-dimethyl-4-(2-bromo-l, 1,2,3,3,3-hexafluoro
367 l,3-difluoro-2-propyl . „.,_■,
-isopropyl) phenyl
,.„ , ., , _, „ , 2,6-dimethyl-4-(2-bromo-l,1,2, 3,3, 3-hexafluoro
368 l-chloro-3-fluoro-2-propyl J . ,i J ,
-isopropyl) phenyl
,„ . .. . 0 - _ . . ,. .. , 2,6-dimethyl-4-(2-bromo-l, 1,2,3,3,3-hexafluoro
369 l-methyl-2,2,2-trifluoroethyl . ,. J ■.
-isopropyl) phenyl
,-,„ , - , . . _. , 2, 6-dimethyl-4-(2-bromo-l, 1,2, 3, 3, 3-hexafluoro
370 3,3,3-trifluoro-n-propyl J . ,,' ,
-isopropyl) phenyl
,-,, ___,,, . _. . 2,6-dimethyl-4-(2-bromo-l, 1,2,3,3,3-hexafluoro
371 2,2,3,3,3-pentafluoro-n-propyl J . ,,' ,
r -isopropyl) phenyl
,_.,, -i -, „ „ „ 4.^1 ov.^-1 2,6-dimethyl-4-(2-bromo-l, 1,2,3,3,3-hexafluoro
372 3,3,4,4,4-pentafluoro-2-butyl J . ,.*_•,
-is opropyl) phenyl
-._, „ . . . . ,, . . , 2, 6-dimethyl-4-(2-bromo-l, 1,2,3,3,3-hexafluoro
373 4,4,4-t«fluoro-n-butyl * . , %.,
' -isopropyl) phenyl
-,-,„ __.,,..., ,1.4.1 2, 6-dimethyl-4-(2-bromo-l, 1,2,3,3,3-hexafluoro
374 2,2,3,3-tetrafluorocyclobutyl 3 . .. .,
' -isopropyl) phenyl
,-,_ _ .. ... 2,6-dimethyl-4-(2-bromo-l, 1,2,3,3,3-hexafluoro
375 2-chloroethyl J . ■.. J ,
-isopropyl) phenyl
.,.,,. __..., .. n 2,6-dimethyl-4-(2-bromo-l, 1,2,3,3,3-hexafluoro
376 2,2-cb.chloroethyl J . ,,' ,
-isopropyl) phenyl
377 2,2,2-trichloroethyl 2'6-dimethyl-4-(2-bromo-l 12,3 3, 3-hexafluoro
-isopropyl) phenyl
__- , ., ,. .. _ , 2,6-dimethyl-4-(2-bromo-l, 1,2,3,3,3-hexafluoro
378 1,3-dichloro-2-propyl J . ,. J -
-isopropyl) phenyl
„,, , ., , 2, 6-dimethyl-4-(2-bromo-l, 1,2, 3, 3, 3-hexafluoro
379 3-chloro-n-propyl * . ,. . ,
r ^J -isopropyl) phenyl
„„ „ . ,_. , 2,6-dimethyl-4-(2-bromo-l, 1,2,3,3,3-hexafluoro
380 2-bromoethyl * . , .' .'
_ -isopropyl) phenyl

72 Table 1(15)
Compound No. Rj Q
,0, ., _ - _ .. ,.1.1 2, 6-dimethyl-4-(2-bromo-l, 1, 2, 3, 3, 3-hexafluoro
381 2,2, 2-tnbromoethyl " . , ' '
-isopropyl)phenyl
,00 -, v, i 2, 6-dimethyl-4-(2-bromo-l, 1, 2,3,3,3-hexafluoro
332 3-bromo-n-propyl J . ,„' ,
-isopropyl) phenyl
,g3 2-i od t-h 1 2, S-dimethyl-4-(2-bromo-l, 1,2, 3, 3, 3-hexafluoro
-isopropyl) phenyl
,0/, . . . , „ , , 2, 6-dimethyl-4-(2-bromo-l, 1,2,3, 3, 3-hexafluoro
384 tetrahydrofuran-3-yl J . , . , ,
-isopropyl) phenyl
,„,. ,. _ ,. ., , 2, 6-dimethyl-4-(2-bromo-l, 1,2,3,3, 3-hexafluoro
385 (furan-2-yl)methyl * . , / . ,
-isopropyl) phenyl
-„, ,, , ,. ,. , 2,6-dimethyl-4-(2-bromo-l, 1,2,3,3,3-hexafluoro
386 (furan-3-yl)methyl * . , . . ,
-isopropyl) phenyl
-,„-, ,,. ^ ,. . , „ i, ... i 2, 6-dimethy 1-4- (2-bromo-l, 1,2,3,3,3-hexafluoro
387 tetrahydrofuran-2-yl)methyl J . , . .,
| _ J J -isopropyl) phenyl
,„o ,4. .. i. j * r, i, ,-u i 2, 6-dimethyl-4-(2-bromo-l, 1,2,3,3,3-hexafluoro
388 (tetrahydrofuran-3-yl)methyl J . ,/»_■.
_ -isopropyl) phenyl
,„„ ,,. . . _ ,, ,_. , 2,6-dimethyl-4-(2-bromo-l, 1,2,3,3,3-hexafluoro
389 (thiophen-2-yl)methyl J . .. ' '
* _ -isopropyl) phenyl
,-„ ,... . , ,. .. , 2, 6-dimethyl-4-(2-bromo-l, 1,2,3, 3,-3-hexafluoro
390 (thiophen-3-yl)methyl J . ,.' ,
r _ _ -isopropyl) phenyl
,„, , ... _ , . ., , ' 2,6-dimethyl-4- (2-bromo-l, 1,2,3,3,3-hexafluoro
391 pyndin-2-yl) methyl J . ,.' ,
_ -isopropyl) phenyl
,„_ , ... ., ,, .. , 2,6-dimethyl-4- (2-bromo-l, 1,2,3,3,3-hexafluoro
392 pyridin-3-yl methyl J . ,.' '
_ _ -isopropyl) phenyl
,„-, ,, ., . .. - i, .. , 2,6-dimethyl-4-(2-bromo-l, 1,2,3,3,3-hexafluoro
393 (6-chloropyridin-3-yl)methyl J . ,. . '
] _ _ _ -isopropyl) phenyl
394 Et 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
395 i-Pr 2,6-dichloro-4- (heptafluoro-n-propylthio)phenyl
396 vinyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
397 propargyl 2, 6-dichloro-4- (heptafluoro-n-propylthio)phenyl
398 cyclobutyl 2,6-dichloro-4- (heptafluoro-n-propylthio) phenyl
399 cyclopentyl 2, 6-dichloro-4- (heptafluoro-n-propylthio)phenyl
400 benzyl 2, 6-dichloro-4- (heptafluoro-n-propylthio)phenyl

73 Table 1(16)
Compound No. Rt Q
401 3-cyanobenzyl 2, 6-dichlor'o-4- (heptafluoro-n-propylthio)phenyl
402 4-cyanobenzyl 2, 6-dichloro-4-(heptafluoro-n-propylthio)phenyl

403 3-chlorobenzyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
404 2-methoxyethyl 2, 6-dichloro-4-(heptafluoro-n-propylthio)phenyl
405 2-cyanoethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
406 2-(methylthio)ethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
407 2-(ethylthio)ethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
408 l-methyl-2-(methylthio)ethyl 2, 6-dichloro-4-(heptafluoro-n-propylthio)phenyl
409 2-(ethylsulfinyl)ethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
410 2-(ethylsulfonyl)ethyl 2, 6-dichloro-4-(heptafluoro-n-propylthio)phenyl
411 2-fluoroethyl 2, 6-dichloro-4-(heptafluoro-n-propylthio)phenyl
412 2,2-difluoroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
413 2,2,2-trifluoroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
414 1,3-difluoro-2-propyl 2,6-dichloro4-(heptafluoro-n-propylthio)phenyl
415 l-chloro-3-fluoro-2-propyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
416 l-methyl-2,2, 2-trifluoroethyl 2, 6-dichloro-4- (heptafluoro-n-propylthio) phenyl
417 3,3,3-trifluoro-n-propyl 2, 6-dichloro-4-(heptafluoro-n-propylthio)phenyl
418 2,2,3,3,3-pentafluoro-n-propyl 2, 6-dichloro-4-(heptafluoro-n-propylthio)phenyl
419 3,3, 4,4, 4-pentafluoro-2-butyl 2, 6-dichloro-4- (heptafluoro-n-propylthio)phenyl
420 4,4, 4-trifluoro-n-butyl 2, 6-dichloro-4- (heptafluoro-n-propylthio)phenyl

14
Table 1(17)
Compound No. Rj Q
421 2,2,3, 3-tetrafluorocyclobutyl 2, 6-dichloro-4- (heptafluoro-n-propylthio)phenyl
422 2-chloroethyl 2, 6-dichloro-4- (heptafluoro-n-propylthio)phenyl
423 2,2-dichloroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
424 2,2, 2-trichloroethyl 2, 6-dichloro-4- (heptafluoro-n-propylthio)phenyl
425 1, 3-dichloro-2-propyl 2, 6-dichloro-4- (heptafluoro-n-propylthio)phenyl
426 3-chloro-n-propyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
427 2-bromoethyl 2, 6-dichloro-4- (heptaf luoro-n-propylthio)phenyl
428 2,2,2-tribromoethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
429 3-bromo-n-propyl 2, 6-dichloro-4- (heptafluoro-n-propylthio)phenyl
430 2-iodoethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
431 tetrahydrofuran-3-yl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
432 (furan-2-yl)methyl 2, 6-dichloro-4-(heptafluoro-n-propylthio)phenyl
433 (furan-3-yl)methyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl

434 (tetrahydrofuran-2-yl)methyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
435 (tetrahydrofuran-3-yl)methyl 2, 6-dichloro-4-(heptafluoro-n-propylthio)phenyl

436 (thiophen-2-yl)methyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
437 (thiophen-3-yl)methyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 438 (pyridin-2-yl)methyl 2, 6-dichloro-4- (heptafluoro-n-propylthio)phenyl
439 (pyridin-3-yl)methyl 2, 6-dichloro-4- (heptafluoro-n-propylthio) phenyl
440 (6-chloropyridin-3-yl)methyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl

75
Table 1(18)
Compound Mo. Ri Q
441 Et 2,6-dibromo-4-(trifluoroinathylthio)phenyl
442 i-Pr 2,6-dibromo-4-(trifluoromethylthio)phenyl
443 vinyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
444 propargyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
445 cyclobutyl 2,6-dibramo-4-(trifluoromethylthio)phenyl
446 cyclopentyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
447 benzyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
448 3-cyanobenzyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
449 4-cyanobenzyl 2,G-dibromo-4-(trifluoromethylthio)phenyl

450 3-chlorobenzyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
451 2-methoxyethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
452 2-cyanoethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
453 2-(methylthio)ethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
454 2-(ethylthio)ethyl 2, 6-dibromo-4-(trifluoromethylthio)phenyl
455 l-methyl-2-(methylthio)ethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
456 2-(ethylsulfinyl)ethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
457 2-(ethylsulfonyl)ethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
458 ' 2-fluoroethyl 2, 6-dibromo-4-(trifluoromethylthio)phenyl
459 2,2-difluoroethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
| 4 60 2,2,2-trifluoroethyl 2, 6-dibromo-4-(trifluoromethylthio)phenyl

76
Table 1(19)
Compound No. R] Q
461 1, 3-difluoro-2-propyl 2, 6-dibromo-4- (trif luoromethylthio) phenyl
462 l-chloro-3-fluoro-2-propyl 2, 6-dibromo-4-(trifluoromethylthio)phenyl
463 l-methyl-2,2,2-trifluoroethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
464. 3,3, 3-trifluoro-n-propyl 2, 6-dibromo-4- (trifluoromethylthio) phenyl
465 2,2,3,3,3-pentafluoro-n-propyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
466 3,3,4,4, 4-pentafluoro-2-butyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
467 4,4,4-trifluoro-n-butyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
468 2,2,3,3-tetrafluorocyclobutyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
469 2-chloroethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
470 2,2-dichloroethyl 2, 6-dibromo-4- (trifluoromethylthio)phenyl
471 2,2,2-trichloroethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
472 l,3-dichloro-2-propyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
473 3-chloro-n-propyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
474 2-bromoethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
475 2,2,2-tribromoethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
476 3-bromo-n7propyl 2, 6-dibromo-4- (trifluoromethylthio) phenyl
477 2-iodoethyl 2, 6-dibromo-4- (trifluoromethylthio)phenyl
478 tetrahydrofuran-3-yl 2,6-dibromo-4- (trifluoromethylthio)phenyl
479 (furan-2-yl)methyl 2, 6-dibromo-4- (trifluoromethylthio)phenyl
480 (furan-3-yl)methyl 2,6-dibromo-4-(trifluoromethylthio)phenyl

77
Table 1(20)
Compound No. Rj Q
481 (tetrahydrofuran-2-yl)methyl 2, 6-dibromo-4- (trifluoromethylthio)phenyl
482 (tetrahydrofuran-3-yl)methyl 2, 6-dibromo-4-(trifluoromethylthio)phenyl

483 (thiophen-2-yl)methyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
484 (thiophen-3-yl)methyl 2, 6-dibromo-4- (trifluoromethylthio)phenyl
485 (pyridin-2-yl) methyl 2,6-dibromo-4-(trifluoromethylthio)phenyl
486 (pyridin-3-yl)methyl 2, 6-dibromo-4-(trifluoromethylthio)phenyl
487 (6-chloropyridin-3-yl)methyl 2, 6-dibromo-4-(trifluoromethylthio)phenyl
488 Et 2, 6-dibromo-4- (trifluoromethylsulfonyl)phenyl
489 i-Pr 2,6-dibromo-4- (trifluoromethylsulfonyl)phenyl
490 vinyl 2, 6-dibromo-4- (trifluoromethylsulfonyl)phenyl
491 propargyl 2,6-dibromo-4- (trifluoromethylsulfonyl)phenyl
492 cyclobutyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
493 cyclopentyl 2, 6-dibromo-4- (trifluoromethylsulfonyl)phenyl
494 benzyl 2, 6-dibromo-4- (trifluoromethylsulfonyl)phenyl
495 3-cyanobenzyl 2, 6-dibromo-4-7 (trifluoromethylsulfonyl)phenyl
496 ^_ 4-cyanobenzyl 2, 6-dibromo-4- (trifluoromethylsulfonyl)phenyl
497 3-chlorobenzyl 2,6-dibromo-4-(trifluoromethylsulfonyl) phenyl
498 2-methoxyethyl 2,6-dibromo-4-(trifluoromethylsulfonyl) phenyl 499 2-cyanoethyl 2, 6-dibromo-4- (trifluoromethylsulfonyl)phenyl
500 2-(methylthio)ethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl

78
Table 1(21)
Compound No. Ri Q
501 2-(ethylthio)ethyl 2, 6-dibromo-4- (trifluoromethylsulfonyl) phenyl
502 l-methyl-2-(raethylthio) ethyl 2, 6-dibromo-4-(trifluoromethylsulfonyl)phenyl
503 2-(ethylsulfinyl)ethyl 2, 6-dibromo-4- (trifluoromethylsulfonyl)phenyl
504 2-(ethylsulfonyl)ethyl 2, 6-dibromo-4- (trifluororaethylsulfonyl)phenyl
505 2-fluoroethyl 2, 6-dibromo-4-(trifluoromethylsulfonyl)phenyl
506 2,2-difluoroethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
507 2,2, 2-trifluoroethyl 2, 6-dibromo-4- (trifluoroTnethylsulfonyl)phenyl
508 l,3-difluoro-2-propyl 2, 6-dibromo-4- (trifluoromethylsulfonyl)phenyl
509 l-chloro-3-fluoro-2-propyl 2,6-dibronio-4-(trifluoromethylsulfonyl)phenyl
510 l-methyl-2, 2,2-trifluoroethyl 2, 6-dibromo-4-(trifluoromethylsulfonyl)phenyl
511 3,3,3-trifluoro-n-propyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
512 2,2,3,3, 3-pentafluoro-n-propyl 2, 6-dibromo-4- (trifluoromethylsulfonyl) phenyl
513 3, 3, 4, 4,4-pentafluoro-2-butyl 2, 6-dibromo-4- (trifluoromethylsulfonyl)phenyl
514 4,4, 4-trifluoro-n-butyl 2, 6-dibromo-4- (trifluoromethylsulfonyl)phenyl
515 2, 2,3,3-tetrafluorocyclobutyl 2, 6-dibromo-4-(trifluoromethylsulfonyl)phenyl
516 2-chloroethyl 2, 6-dibromo-4- (trifluoromethylsulfonyl)phenyl
517 2,2-dichloroethyl 2, 6-dibromo-4-(trifluoromethylsulfonyl)phenyl
518 2,2,2-trichloroethyl 2, 6-dibromo-4- (trifluoromethylsulfonyl)phenyl
519 1,3-dichloro-2-propyl 2, 6-dibromo-4- (trifluoromethylsulfonyl)phenyl
520 3-chloro-n-propyl 2, 6-dibromo-4- (trifluoromethylsulfonyl) phenyl

79
Table 1(22)
Compound No. Ri Q
521 2-bromoethyl 2, 6-dibromo-4- (trifluoromethylsulfonyl) phenyl
522 2,2, 2-tribromoethyl 2, 6-dibromo-4- (trifluoromethylsulfonyl) phenyl
523 3-bromo-n-propyl 2, 6-dibromo-4- (trifluoromethylsulfonyl) phenyl
524 2-iodoethyl 2, 6-dibromo-4- (trifluoromethylsulfonyl) phenyl
525 tetrahydrofuran-3-yl 2,6-dibromo-4-(trifluoromethylsulfonyl) phenyl
526 (furan-2-yl)methyl 2, 6-dibromo-4-(trifluoromethylsulfonyl) phenyl
527 (furan-3-yl)methyl 2, 6-dibromo-4-(trifluoromethylsulfonyl)phenyl

528 (tetrahydrofuran-2-yl)methyl 2, 6-dibromo-4-(trifluoromethylsulfonyl)phenyl
529 (tetrahydrofuran-3-yl)methyl 2,6-dibromo-4- (trifluoromethylsulfonyl)phenyl
530 (thiophen-2-yl)methyl 2, 6-dibromo-4- (trifluoromethylsulfonyl) phenyl
531 (thiophen-3-yl)methyl 2, G-dibromo-4- (trifluoromethylsulfonyl) phenyl
532 (pyridin-2-yl)methyl 2, 6-dibromo-4- (trifluoromethylsulfonyl)phenyl
533 (pyridin-3-yl)methyl 2, 6-dibromo-4- (trifluoromethylsulfonyl)phenyl
534 (6-chloropyridin-3-yl)methyl 2, 6-dibromo-4- (trifluoromethylsulfonyl) phenyl
535 Et 2, 6-dibromo-4-(pentafluoroethylthio) phenyl
536 i-Pr 2,6-dibromo-4-(pentafluoroethylthio)phenyl
537 vinyl 2, 6-dibromo-4-(pentafluoroethylthio)phenyl
538 propargyl 2, 6-dibromo-4-(pentafluoroethylthio) phenyl
539 cyclobutyl 2,6-dibromo-4- (pentafluoroethylthio) phenyl
| 540 | cyclopentyl | 2,6-dibromo-4- (pentafluoroethylthio)phenyl

80
Table 1(23)
Compound No. R; Q
541 benzyl 2, 6-dibromo-4- (pentafluoroethylthio) phenyl
542 3-cyanobenzyl 2, 6-dibromo-4- (pentafluoroethylthio)phenyl
543 4-cyanobenzyl 2, 6-dibromo-4- (pentafluoroethylthio)phenyl

544 3-chlorobenzyl 2, 6-dibromo-4- (pentafluoroethylthio) phenyl
545 2-methoxyethyl 2, 6-dibromo-4-(pentafluoroethylthio)phenyl
546 2-cyanoethyl 2, 6-dibromo-4-(pentafluoroethylthio)phenyl
547 2- (methylthio) ethyl 2, 6-dibromo-4- (pentafluoroethylthio)phenyl
548 2-(ethylthio) ethyl 2, G-dibromo-4-(pentafluoroethylthio) phenyl
549 l-methyl-2- (methylthio) ethyl 2, 6-dibromo-4- (pentafluoroethylthio) phenyl
550 2-(ethylsulfinyl)ethyl 2,S-dibromo-4-(pentafluoroethylthio) phenyl
551 2-(ethylsulfonyl)ethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
552 2-fluoroethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
553 2,2-difluoroethyl 2, 6-dibromo-4-(pentafluoroethylthio)phenyl
554 2, 2,2-trifluoroethyl 2,G-dibromo-4-(pentafluoroethylthio)phenyl
555 1, 3-difluoro-2-propyl 2, 6-dibromo-4-(pentafluoroethylthio)phenyl
556 l-chloro-3-fluoro-2-propyl 2, 6-dibromo-4-(pentafluoroethylthio) phenyl
557 l-methyl-2,2,2-trifluoroethyl 2, 6-dibromo-4- (pentafluoroethylthio)phenyl
558 3,3,3-trifluoro-n-propyl 2, 6-dibromo-4- (pentafluoroethylthio)phenyl
559 2,2,3,3,3-pentafluoro-n-propyl 2, 6-dibromo-4- (pentafluoroethylthio) phenyl
560 3,3, 4, 4, 4-pentafluoro-2-butyl 2, 6-dibromo-4- (pentafluoroethylthio)phenyl

81 Table 1(24)
Compound No. Ri Q
561 4,4,4-trifluoro-n-butyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
562 2,2,3,3-tetrafluorocyclobutyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
563 2-chloroethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
564 2,2-dichloroethyl 2, 6-dibromo-4- (pentafluoroethylthio)phenyl
565 2,2,2-trichloroethyl 2,6-dibromo-4- (pentafluoroethylthio)phenyl
566 1,3-dichloro-2 -propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
567 3-chloro-n-propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
568 2-bromoethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
569 2,2,2-tribromoethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
570 3-bromo-n-propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
571 2-iodoethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
572 tetrahydrofuran-3-yl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
573 (furan-2-yl)methyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
574 (furan-3-yl)methyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl
575 (tetrahydrofuran-2-yl)methyl 2, 6-dibromo-4-(pentafluoroethylthio)phenyl
576 (tetrahydrofuran-3-yl)methyl 2, 6-dibromo-4- (pentafluoroethylthio)phenyl
577 (thiophen-2-yl)methyl 2, 6-dibromo-4- (pentafluoroethylthio) phenyl
578 (thiophen-3-yl)methyl 2, 6-dibromo-4- (pentafluoroethylthio)phenyl
579 (pyridin-2-yl)methyl 2, 6-dibromo-4- (pentafluoroethylthio)phenyl
I 580 (pyridin-3-yl)methyl 2, 6-dibromo-4- (pentafluoroethylthio)phenyl

82
Table 1(25)
Compound No. Rj Q
581 (6-chloropyridin-3-yl)methyl 2, 6-dibromo-4- (pentafluoroethylthio) phenyl
582 Et 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
583 i-Pr 2, 6-dibromo-4-(heptafluoro-n-propylthio)phenyl
584 vinyl 2, 6-dibromo-4- (heptafluoro-n-propylthio)phenyl
585 propargyl 2, 6-dibromo-4-(heptafluoro-n-propylthio)phenyl
586 cyclobutyl 2, 6-dibronK>-4- (heptafluoro-n-propylthio)phenyl
587 cyclopentyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
588 benzyl 2, 6-dibrorno-4- (heptafluoro-n-propylthio)phenyl
589 3-cyanobenzyl 2, 6-dibromo-4- (heptafluoro-n-propylthio)phenyl
590 4-cyanobenzyl 2, 6-dibromo-4- (heptafluoro-n-propylthio)phenyl
591 3-chlorobenzyl 2, 6-dibromo-4-(heptafluoro-n-propylthio)phenyl
592 2-methoxyethyl 2, 6-dibromo-4-(heptafluoro-n-propylthio)phenyl
593 2-cyanoethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
594 2-(methylthio)ethyl 2,6-dibronio-4- (heptafluoro-n-propylthio) phenyl
595 2- (ethylthio) ethyl 2, 6-dibromo-4- (heptafluoro-n-propylthio) phenyl
596 l-methyl-2- (methylthio) ethyl - 2, 6-dibromo-4- (heptafluoro-n-propylthio)phenyl
597 ■ 2-(ethylsulfinyl)ethyl 2, 6-dibromo-4-(heptafluoro-n-propylthio)phenyl
598 2-(ethylsulfonyl)ethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
599 2-fluor'oethyl 2, 6-dibromo-4- (heptafluoro-n-propylthio)phenyl
600 2,2-difluoroethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl

83
Table 1(26)
Compound No. Ri Q
601 2,2,2-trifluoroethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
602 1,3-difluoro-2-propyl 2, 6-dibromo-4-(heptafluoro-n-propylthip)phenyl
603 l-chloro-3-fluoro-2-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
604 1-methyl-2,2,2-trifluoroethyl 2, 6-dibromo-4-(heptafluoro-n-propylthio)phenyl
605 3,3,3-trifluoro-n-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
606 2,2,3,3,3-pentafluoro-n-propyl 2, 6-dibromo-4-(heptafluoro-n-propylthio)phenyl
607 3,3,4,4,4-pentafluoro-2-butyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
608 4,4,4-trifluoro-n-butyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
609 2,2,3,3-tetrafluorocyclobutyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
610 2-chloroethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
611 2,2-dichloroethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
612 2,2,2-trichloroethyl 2,6-dibroroo-4-(heptafluoro-n-propylthio)phenyl
613 1,3-dichloro-2-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
614 3-chloro-n-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
615 2-broraoethyl 2,6-dibromo-4-(heptafluord-n-propylthio)phenyl
616 2,2,2-tribromoethyl 2, 6-dibromo-4- (heptafluoro-n-propylthio)phenyl
617 3-bromo-n-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
618 2-iodoethyl 2, 6-dibromo-4-(heptafluoro-n-propylthio)phenyl
619 tetrahydrofuran-3-yl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
620 (furan-2-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl

84 Table 1(27)
Compound No. R, Q
621 (furan-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propylthio) phenyl
622 (tetrahydrofuran-2-yl)methyl 2, 6-dibromo-4-(heptafluoro-n-propylthio)phenyl
623 (tetrahydrofuran-3-yl)methyl 2, 6-dibromo-4-(heptafluoro-n-propylthio)phenyl
624 (thiophen-2-yl)methyl 2, 6-dibromo-4- (heptafluoro-n-propylthio)phenyl
625 (thiophen-3-yl)methyl 2, 6-dibromo-4-(heptafluoro-n-propylthio)phenyl
626 (pyridin-2-yl)methyl 2, 6-dibromo-4- (heptafluoro-n-propylthio) phenyl
627 (pyridin-3-yl) methyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
628 (6-chloropyridin-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propylthio) phenyl
629 Et 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
630 i-Pr 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
631 vinyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
632 propargyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
633 cyclobutyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
634 cyclopentyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
635 benzyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
636 3-cyanobenzyl 2, 6-dibromo-4-(heptafluoroisopropylthio)phenyl
637 4-cyanobenzyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl

638 3-chlorobenzyl 2, 6-dibromo-4-(heptafluoroisopropylthio)phenyl
639 2-methoxyethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
640 2-cyanoethyl | 2,6L;dibromo-4- (heptafluoroisopropylthio)phenyl

85
Table 1(28)
Compound No. Ri Q
641 2-(methylthio)ethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
642 2-(ethylthio)ethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
643 l-methyl-2- (methylthio)ethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
644 2-(ethylsulfinyl)ethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
645 2-(ethylsulfonyl)ethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
646 2-fluoroethyl 2, 6-dibrc>mo-4-(heptafluoroisopropylthio)phenyl
647 2,2-difluoroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
648 2,2,2-trifluoroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
649 l,3-difluoro-2-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
650 l-chloro-3-fluoro-2-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
651 l-methyl-2,2,2-trifluoroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
652 3,3,3-trifluoro-n-propyl 2, 6-dibromo-4-(heptafluoroisopropylthio)phenyl
653 2,2,3,3,3-pentafluoro-n-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
654 3,3,4,4,4-pentafluoro-2-butyl 2, 6-dibromo-4-(heptafluoroisopropylthio)phenyl
655 4,4,4-trifluoro-n-butyl 2, 6-dibromo-4-(heptafluoroisopropylthio)phenyl
656 2,2,3,3-tetrafluorocyclobutyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
657 2-chloroethyl 2,6-dibromo-4-(heptafluoroisbpropylthio)phenyl
658 2,2-dichloroethyl 2,6-dibrorao-4-(heptafluoroisopropylthio)phenyl
659 2,2,2-trichloroethyl 2, 6-dibromo-4-(heptafluoroisopropylthio[phenyl
660 1,3-dichloro-2-propyl 2, 6-dibromo-4-(heptafluoroisopropylthio)phenyl

86
Table 1(29)
Compound Mo. Ri Q
661 3-chloro-n-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
662 2-bromoethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
663 2,2, 2-tribromoethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
■ 664 3-bromo-n-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
665 2-iodoethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
666 tetrahydrofuran-3-yl 2, 6-dibromo-4-(heptafluoroisopropylthio)phenyl
667 (furan-2-yl)methyl 2, 6-dibromo-4- (heptafluoroisopropylthio) phenyl
668 (furan-3-yl)methyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
669 (tetrahydrofuran-2-yl)methyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
670 (tetrahydrofuran-3-yl)methyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl

671 (thiophen-2-yl)methyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
672 (thiophen-3-yl)methyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
673 (pyridin-2-yl)methyl 2, 6-dibromo-4-(heptafluoroisopropylthio)phenyl
674 (pyridin-3-yl)methyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
675 (6-chloropyridin-3-yl)methyl 2, 6-dibromo-4-(heptafluoroisopropylthio)phenyl
2, 6-dibromo-4-(heptafluoro-n-propyl
sulfinyl)phenyl
. 2,6-dibromo-4-(heptafluoro-n-propyl
sulfinyl)phenyl
2,6-dibromo-4-(heptafluoro-n-propyl
sul finyl) phenyl
2,6-dibromo-4-(heptafluoro-n-propyl
P P 9y sulfinyl) phenyl
. , . . , 2,6-dibromo-4-(heptafluoro-n-propyl
680 cyclobutyl ■,*•,, u i
* * sulfinyl) phenyl

87 Table 1(30)
Compound No. Rx Q
,„, , ^ , 2, 6-dibromo-4-(heptafluoro-n-propyl
681 cyclopentyl , ..' f, . , t- t-jr
sulf myl) phenyl
._„ . . 2,6-dibromo-4-(heptafluoro-n-propyl
sulfinyl)phenyl
___ ., . , 2,6-dibromo-4-(heptaf luoro-n-propyl
683 3-cyanobenzyl ,.... f, . , ^ "
sulf myl) phenyl
... , 2,6-dibromo-4-(heptafluoro-n-propyl
684 4-cyanobenzyl ,.*■;,,_, en
sulfinyl) phenyl
685 3-chlorobenzyl 2;6-dibromo-4-(heptafluoro-n-propyl
\ sulf inyl) phenyl
... „ ... .. , 2,6-dibromo-4-(heptafluoro-n-propyl
686 2-methoxyethyl , _.f, .
J sulf inyl) phenyl
.... - .. . 2,6-dibromo-4-(heptafluoro-n-propyl
687 2-cyanoethyl ■,*•;, v. n
_ sulf inyl) phenyl
,„„ _ . .. ,-.. . . .. , 2,6-dibromo-4-(heptaf luoro-n-propyl
688 2-(methylthio) ethyl , .;, v. ,
J sul f myl) phenyl
.„„ . . ... ... . % ., , 2,6-dibromo-4-(heptafluoro-n-propyl
689 2-(ethylthio)ethyl , ..f. . ,
. J sulf myl) phenyl
,.,,„ . .. , „ , .. .... , .. . 2,6-dibromo-4-(heptafluoro-n-propyl
690 l-methyl-2-(methylthio) ethyl sulf inyl) phenyl
„,,.!,..,, _. , 2,6-dibromo-4-(hep'tafluoro-n-propyl
691 2-(ethylsulfinyl)ethyl sulf inyl) phenyl
,„„ ., ,...,. n, t. , 2/6-dibromo-4-(heptafluoro-n-propyl
692 2-(ethylsul£onyl)ethyl sulf inyl) phenyl
,„_ _ ... ... , 2,6-dibronio-4-(heptafluoro-n-propyl
693 2-fluoroethyl . sulf iny^ phenyl
_„, _ „ ...-, ... 2,6-dibromo-4-(heptafluoro-n-propyl
694 2,2-difluoroethyl sulf inyl) phenyl
... „__..., .. , 2,6-dibromo-4- (heptafluoro-n-propyl
695 2,2,2-tnfluoroethyl sulfinyl)phenyl
696 l,3-difluoro-2-propyl 2,6-dibromo-4-(heptafluoro-n-propyl
[ r c* sulfinyl) phenyl
,„., , . , , ,. _ . 2,6-dibromo-4-(heptafluoro-n-propyl
697 l-chloro-3-fluoro-2-propyl . . ,. . ' .
r " sulfinyl) phenyl .
,„„ , .. , _ _ „ . ... ... 2,6-dibromo-4-r (heptaf luoro-n-propyl
698 l-methyl-2,2,2-tnf luoroethyl sulf inyl) phenyl
.„„ -,-,-,,. .c, , 2,6-dibromo-4-(heptafluoro-n-propyl
699 3,3,3-tnf luoro-n-propyl sulf inyl) phenyl
„ „ , , , ... . 2,6-dibromo-4-(heptafluoro-n-propyl
700 | 2,2,3,3,3-pentafluoro-n-propyl | sulf inyl) phenyl

88
Table 1(31) _____1
Compound No. Ri Q
' ~ " 2,6-dibromo-4-(heptafluoro-n-propyl
701 3,3,4,4,4-pentafluoro-2-butyl sulfinyl)phenyl
, 2, 6-dibromo-4-(heptafluoro-n-propyl
702 4,4,4-tnfluoro-n-butyl sulfinyl)phenyl
„„.,., ,_ _, ,,_,_•, 2,6-dibromo-4-(heptaf luoro-n-propyl
703 2,2,3,3-tetrafluorocyclobutyl sulfinyl) phenyl
„„, _ ., . , 2,6-dibromo-4-(heptafluoro-n-propyl
704 2-chloroethyl sulfinyl) phenyl
,„„ „ „ ,. t, . ^. , 2,6-dibromo-4-(heptafluoro-n-propyl
705 2,2-dichloroethyl sulfinyl) phenyl
,„, ,, ,, ^ *_ . L, ^L , 2,6-dibromo-4-(heptafluoro-n-propyl
706 2,2,2-tnchloroethyl sulfinyl) phenyl
707 1, 3-dichloro-2-propyl 2' ^^^; (heptaf luoro-n-propyl
[ r r sulfinyl) phenyl
_,_„ _ . , , 2,6-dibromo-4-(heptafluoro-n-propyl
708 3-chloro-n-propyl , ^. f\ .
sulfinyl) phenyl
_„„ „ . .. , 2,6-dibromo-4-(heptafluoro-n-propyl
709 2-bromoethyl ,_..;,,_•,
sulfinyl) phenyl
_,„ ooo^.-^ i.wT 2,6-dibromo-4-(heptafluoro-n-propyl
710 2,2,2-tnbromoethyl , ,.,, u ■■ *'«'•'
J sulfinyl) phenyl
_,, , . , 2,6-dibromo-4-(heptafluoro-n-propyl
711 3-bromo-n-propyl , . t\ . r "
sul f inyl) phenyl
712 2-iodoethyl 2,6-dibromo-4-(heptafluoro-n-propyl
sulfinyl) phenyl
.,,, 4.4-v.j^ r, -, 2,6-dibromo-4-(heptafluoro-n-propyl
713 tetrahydrofuran-3-yl ,_*.,.,_,
; sul f my 1) phenyl
714 (furan-2-Yl)methyl 2, 6-dibromo-4-(heptafluoro-n-propyl sulfinyl) phenyl
715 (furaiv-3-yl) methyl 2,S-dibromo-^-(heptafluoro-n-propyl ; sulfinyl) phenyl
_,, /4. ,_ . . - „ ,. j.. , 2,6-dibromo-4- (heptafluoro-n-propyl
716 (tetrahydrofuran-2-yl)methyl „';.,, r " sulfinyl) phenyl
717 (tetrahydrofuran-3-yUmethyl 2' 6-dibromo-4- (heptafluoro-n-propyl sul f inyl) phenyl

718 (thiophen-2-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl _ sulfinyl) phenyl
719 (thiophen-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl _ sul f inyl) phenyl
720 (pyridin-2-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl
I I sulfinyl) phenyl

89
Table 1(32)
Compound No. Ri Q
~7. I | T-! 2,6-dibromo-4- (heptafluoro-n-propyl
721 (pyncUn-3-yl) methyl sulfinyl)phenyl
,. ., . ,. , ., ., . 2,6-dibromo-4-(heptafluoro-n-propyl
722 (S-chloropyndm-S-yDmethyl sulfinyl) phenyl
2, 6-dibromo-4-(heptafluoro-n-propyl
723 ^ ; sulfonyl) phenyl
. 2,6-dibromo-4-(heptafluoro-n-propyl
sulfonyl) phenyl
~~ 2,6-dibromo-4-(heptafluoro-n-propyl
^ sulfonyl) phenyl
„, , 2,6-dibromo-4-(heptafluoro-n-propyl
726 propargyl sulfonyl) phenyl
_,„_, , . ^ , 2, 6-dibromo-4- (heptafluoro-n-propyl
727 cyclobutyl sulfonyl) phenyl
728 cyclopentyl 2, e-dibron^-(heptafluoro-n-propyl
. J sulfonyl) phenyl
_,„„ . 2,6-dibromo-4-(heptafluoro-n-propyl
729 benzyl , f. ,
_ sulfonyl) phenyl
.,.,„ . . _ . 2,6-dibramo-4-(heptafluoro-n-propyl
730 3-cyanobenzyl ,_ f. .. ,
sulfonyl) phenyl
.,.,, „ , 2,6-dibromo-4-(heptafluoro-n-propyl
731 4-cyanobenzyl , . f. . . r "
sulfonyl) phenyl
732 3-chlorobenzyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl) phenyl
733 2-methoxyethyl 2'6-dibromo-4-(heptafluoro-n-propyl sulfonyl) phenyl
734 2-cyanoethyl 2,e-dibromo-4-(heptafluoro-n-propyl
_ sulfonyl) phenyl
735 2-(methylthio)ethyl 2, 6-ttironK>-4-(heptafluoro-n-propyl sul f onyl) phenyl
736 2-(ethylthio)ethyl 2, S-dibromoM-(heptafluoro-n-propyl sulfonyl) phenyl
737 l-methyl-2- (methylthio) ethyl 2' e-clibromo-4- (heptafluoro-n-propyl '
_ sulfonyl) phenyl
738 2-tethylsulfinyllethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl) phenyl
739 2-(ethylSulfonyl)ethyl 2, 6-dibroino-4-(heptafluoro-n-propyl
_ sulfonyl) phenyl ___
740 2-fluoroethyl 2,6-dibromo-4-(heptafluoro-n-propyl
| I sulfonyl) phenyl

90 Table 1(33)
Compound No. Ri ' Q
~ „ „ .. _, 77~ 2,6-dibromo-4- (heptafluoro-n-propyl
741 2,2-difluoroethyl ,, ,, .. ,,
' -_ sulfonyl) phenyl
777. -, o o i. ■*, 4.1. i 2,6-dibromo-4-(heptafluoro-n-propyl
742 2,2,2-tnfluoroethyl sulfonyl) phenyl
743 l,3-difluoro-2-propyl 2,6-dibromo-4-(heptafluoro-n-propyl
' ^ " : sulfonyl) phenyl
.... , ., _, ., „ , 2,6-&Lbromo-4-(heptafluoro-n-propyl
744 l-chloro-3-fluoro-2-propyl ,* ;. v. i
^ sulfonyl) phenyl
-,.? , 4.^ i ^ o o 4. ■ 4:1 4-v. 1 2,6-dibromo-4-(heptafluoro-n-propyl
745 l-methyl-2,2, 2-trrfluoroethyl sulfonyl) phenyl
746 3,3,3-trifluoro-n-ProPyl 2, e-dibromo-^-(heptaf luoro-n-prbpyl
F sulfonyl) phenyl
„.-, _„.,,., . -, , 2,6-dibromo-4-(heptafluoro-n-propyl
747 2,2, 3,3,3-pentafluoro-n-propyl sulfonyl)phenyl
748 3,3,4,4,4-Pentafluoro-2-butyl 2'6-dibromo-4- (heptafluoro-n-propyl
'•'•*■ ' sulfonyl) phenyl
_,.„ ,...._ ,. .. , 2,6-dibromo-4- (heptaf luoro-n-propyl
749 4,4,4-tro.fluoro-n-butyl , . f. , , r "
sulfonyl) phenyl
750 2,2,3,3Ttetrafluorocyclobutyl 2' €^Uma^^^^0'^'^rapyl
751 2-chloroethyl . 2' ^iihcmo~A- (heptafluoro-n-propyl
_ sulfonyl) phenyl
752 2,2-dichloroethyl 2,6-dibromo-4-(heptaf luoro-n-propyl
sulfonyl) phenyl
753 2,2,2-trichlqroethyl 2, e-dibromo^-(heptafluoro-n-propyl
sulfonyl) phenyl
754 l,3-dichloro-2-proPyl 2,6-dibromo-4-(heptafluoro-n-propyl
' r rj ■ sul fonyl) phenyl
755 3-chloro-n-propyl 2,6-dibronvo-4-(heptafluoro-n-propyl
sul f onyl) phenyl
756 2-brcmoethyl 2,6-dibromo-4-(heptaf luoro-n-propyl
sulfonyl) phenyl
757 2,2,2-tribromoethyl 2,6-dibrQmo-4-(heptafluoro-n-propyl
sulfonyl) phenyl
758 3-bromo-n-propyl 2,6-dibromo-4-(heptafluoro-n-propyl
. sulfonyl) phenyl
759 2-iodoethyl 2' 6-dibromo-4- (heptaf luoro-n-propyl
sulfonyl) phenyl
760 tetrahydrofuran-3-yl 2,6-dibromo-4-(heptaf luoro-n-propyl
I ( sulfonyl) phenyl

91
Table 1(34)
Compound No. Ri Q
„ , , ,_, , 2,6-dibromo-4- (heptaf luoro-n-propyl
761 (furan-2-yl) methyl sulfonyl)phenyl
7 62 (furan-3-yl)methyl 2, 6-dibroino-4-(heptafluoro-n-propyl
J J sul fonyl) phenyl
~ ,_ „ . , , „ .. .. , 2,6-dibromo-4-(heptafluoro-n-propyl
763 (tetrahydrofuran-2-yl)methyl sulfonyl) phenyl
,,-„ ,t _ i. j * r, i. -i. i 2,6-dibromo-4-(heptafluoro-n-propyl
764 (tetrahydrofuran-3-yl)methyl sulfonyl) phenyl
_-. ... . . . ,. .. , 2,6-dibromo-4-(heptafluoro-n-propyl
765 (_ophen-2-yl) methyl sulfonyl) phenyl
766 (thiophen-3-yl)methyl 2, 6-dibr_-4-(heptafluoro-n-propyl
y * J sulfonyl) phenyl
,,_ , ... „ ., ,., 2,6-dibromo-4-(heptaf luoro-n-propyl
767 (pyridm-2-yl)methyl , . ;. . , "
_ J J sulfonyl) phenyl
-,rn , ... , ,. .. , 2,6-dibromo-4-(heptafluoro-n-propyl
768 pyrxdm-3-yl)methyl ,,! ;. . , r rj
J J sul fonyl) phenyl
_,,.„ ,. ,, ., ., ., , 2,6-dibromo-4-(heptaf luoro-n-propyl
769 (6-chloropyridin-3-yl methyl , . ;, . "
_ _ J J sulfonyl) phenyl
770 2, 2,2-trichloroethyl 2-methyl-4-(heptafluoro-n-propylthio) phenyl
771 Et 2, 6-dimethyl-4- (heptafluoro-n-propylthio)phenyl
772 i-Pr 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
773 propargyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
774 ■ cyclobutyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio)phenyl
775 cyclopentyl 2, 6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
776 benzyl 2, 6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
777 3-cyanobenzyl 2, 6-dimethyl-4- (heptafluoro-n-propylthlo)phenyl
778 4-cyanobenzyl 2,6-dimethyl-4- (heptafluoro-n-propylthio) phenyl
779 3-chlorobenzyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio)phenyl
780 2-methoxyethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl

92
Table 1 (35) __^
Compound No. Ri Q
781 2-cyanoethyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio) phenyl
732 2- (methylthio) ethyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio)phenyl
783 2- (ethylthio) ethyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio)phenyl
784 l-methyl-2- (methylthio) ethyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio)phenyl
785 2-(ethylsulfinyl)ethyl 2,6-dimethyl-4- (heptafluoro-n-propylthio)phenyl
78S 2-(ethylsulfonyl)ethyl 2,6-dimethyl-4- (heptafluoro-n-propylthio)phenyl
787 2-fluoroethyl 2,6-dimethyl-4- (heptafluoro-n-propylthio) phenyl
788 2,2-difluoroethyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio)phenyl
789 2,2,2-trifluoroethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
790 1,3-difluoro-2-propyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio)phenyl ]
791 l-chloro-3-fluoro-2-propyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio)phenyl
792 l-methyl-2,2,2-trifluoroethyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio)phenyl
793 3,3,3-trifluoro-n-propyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio)phenyl
794 2, 2, 3, 3,3-pentafluoro-n-propyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio)phenyl
795 3,3,4,4, 4-pentafluoro-2-butyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio)phenyl
796 4,4,4-trifluoro-n-butyl 2,6-dimethyl-4-(heptafluoro-n-propylthio) phenyl
797 2,2,3,3-tetraflubrocyclobutyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio)phenyl
798 2-chloroethyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio)phenyl
799 2,2-dichloroethyl 2, 6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
800 J 2,2,2-trichloroethyl | 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl

93
Table 1(36)
Compound No. fy Q
801 1,3-dichloro-2-propyl 2, 6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
802 3-chloro-n-propyl 2, 6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
803 2-bromoethyl 2, 6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
804 2,2, 2-tribromoethyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio) phenyl
805 3-bromo-n-propyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
806 2-iodoethyl 2, 6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
807 tetrahydrofuran-3-yl 2, 6-dimethyl-4- (heptafluoro-n-propylthio)phenyl
808 (furan-2-yl) methyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
809 (furan-3-yl) methyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
810 (tetrahydrofuran-2-yl)methyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio) phenyl
811 (tetrahydrofuran-3-yl)methyl 2, 6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
812 (thiophen-2-yl)methyl 2, 6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
813 (thiophen-3-yl)methyl 2, 6-dimethyl-4-(heptafluoro-n-propylthio) phenyl
814 (pyridin-2-yl)methyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio)phenyl
815 (pyridin-3-yl)methyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio) phenyl
816 (6-chloropyridin-3-yl)methyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio) phenyl
817 3,3,3-trifluoro-n-propyl 2- (n-butyl) -6-chloro-4-heptafluoroisopropylphenyl
818 3,3,3-trifluoro-n-propyl 2- (n-butyl) -4-heptafluoroisopropyl-6-iodophenyl
819 3,3,3-trifluoro-n-propyl 2-bromo-6-(2-butyl)-4-heptafluoroisopropylphenyl
820 i-Pr 2-methyl-4-trif luoromethoxyphenyl

94
Table 1(37)
Compound No. Ri Q
821 i-Pr 2-trifluoromethyl-4-isopropylphenyl
822 i-Pr . 3,5-bistrifJ.uoroiriethylphenyl
823 i-Pr 2,3,4-trif luorophenyl
824 i-Pr 2-heptaf luoroisopropyl-3,5-dimethylphenyl
825 i-Pr 2,4-dichloro-6-methylphenyl
826 i-Pr 2-chloro-4,6-dimethylphenyl
827 i-Pr 2,6-dimethyl-4~chlorophenyl
828 i-Pr 2, 6-dime tiiyl-4-bromophenyl
829 i-Pr 2,6-dimethyl-4-iodophenyl
830 i-Pr 2, 6-dimethyl-4- (phenyl) phenyl
831 i-Pr 2,6-dimethyl-4- (2-methylphenyl) phenyl
832 i-Pr 2,6-dimethyl-4- (3-methylphenyl) phenyl
833 i-Pr 2,6-dime thyl-4 - (4 -methylphenyl) phenyl
834 i-Pr 2, 6-dime thyl-4-(2-methoxyphenyl) phenyl
835 i-Pr 2,6-dimethyl-4- (3-methoxyphenyl) phenyl
836 i-Pr 2, 6-dimethyl-4-(4-methoxyphenyl)phenyl
837 i-Pr 2,6-dimethyl-4-(4-ethoxyphenyl) phenyl
838 . i-Pr 2, 6-dimethyl-4- (4-methylthiophenyl) phenyl
839 i-Pr 2,6-dimethyl-4- (2-f luorophenyl) phenyl
840 i-Pr 2, 6-dimethyl-4- (3-fluorophenyl)phenyl

95 Table 1(38)
Compound No. Ri Q
841 i-Pr 2, 6-dimethyl-4-(4-fluorophenyl)phenyl
842 i-Pr 2-bromo-4-isopropyl-6-methylphenyl
343 i-Pr 2-chloro-4-cyano-6-mathylphenyl
844 i-Pr 2-chloro-4-trifluoromethoxy-6-methylphenyl
845 i-Pr 2-chloro-4-isopropyl-6-trifluoromethylphenyl
846 i-Pr pentafluorophenyl
847 2,2,2-trichloroethyl 4-cyclohexylphenyl
848 2, 2,2-trichloroethyl 2-trifluoromethylphenyl
849 2, 2,2-trichloroethyl 4-(trifluoromethylthio)phenyl
850 2,2,2-trichloroethyl 4- (trifluoromethylsulf onyl) phenyl
851 2,2,2-trichloroethyl 4- (heptafluoro-n-propylthio) phenyl
852 2, 2,2-trichloroethyl 4-(heptafluoro-n-propylsulfinyl)phenyl
853 2, 2,2-trichloroethyl 4- (heptafluoroisopropylthio) phenyl
854 2,2,2-trichloroethyl 2- (n-butyl) -6-chloro-4-heptafluoroisopropylphenyl
855 2,2,2-trichloroethyl 2- (n-butyl) -4-heptafluoroisQpropyl-6-iodophenyl
856 2,2,2-trichloroethyl 2-bromo-6-(2-butyl) -4-heptafluoroisopropylphenyl
857 2,2,2-trichloroethyl 2- (2-butyl) -4-heptafluoroisopropylphenyl
858 2,2,2-trichloroethyl 2-methyl-4-trifluoromethoxyphenyl
859 2,2,2-trichloroethyl 2-methyl-4- (2,2,2-trifluoroethoxy) phenyl
8 60 2,2,2-trichloroethyl 2-methyl-4- (trif luoromethylsulf onyloxy) phenyl

96
Table 1(39)
Compound No. Ri 0
861 2, 2, 2-trichloroethyl 2-methyl-4-chlorophenyl
862 2,2,2-trichloroethyl 2-trifluoromethyl-4-isopropylphenyl
863 2,2,2-trichloroethyl 2,5-bistrifluoromethylphenyl
864 2,2,2-trichloroethyl 3,5-bistrifluoromethylphenyl
865 2,2,2-trichloroethyl 2-trifluoromethyl-4-chlorophenyl
866 2,2,2-trichloroethyl 2-chloro-6-trifluoromethylphenyl
867 2,2,2-trichloroethyl 2-trifluoromethyl-4-iodophenyl
868 2,2,2-trichloroethyl 2-trifluoromethoxy-4-bromophenyl
869 2,2,2-trichloroethyl 2,3,4-trif luorophenyl
870 2,2,2-trichloroethyl 2-heptafluoroisopropyl-3,5-dimethylphenyl
„-,, „ ., „ . . ,_, ,. , 2,5-dimethyl-4-trifluoromethane
871 2,2,2-trichloroethyl , i , t ,
' sul f onyloxyphenyl
„-,_ . . _ ^ . . . ... 2,6-dimethyl-4-(bis (trifluoromethyl)
872 2,2,2-trichloroethyl ,_ * ._._,,. , ' hydroxymethyl) phenyl
873 2,2,2-trichloroethyl 2'6-dimethyl-4-(bis(cnlorodifluoromethyl) hydr oxyme thyl) phenyl
874 2, 2,2-trichloroethyl 2, 6-diinethyl-4-cyanothiophenyl
875 2,2,2-trichloroethyl 2, 6-dimethyl-4-chlorophenyl
876 2,2,2-trichloroethyl 2-chloro-4,6-dimethylphenyl
877 2,2,2-trichloroethyl 2, 6-dimethyl-4-bromophenyl
878 2,2,2-trichloroethyl 2, 6-dimethyl-4-iodophenyl
879 2,2,2-trichloroethyl 2, 6-dimethyl-4- (phenyl)phenyl
880 2,2,2-trichloroethyl | 2,6-dimethyl-4-(2-roethylphenyl)phenyl

97 Table 1(40)
Compound No. Ri Q
881 2,2,2-trichloroethyl 2,6-dimethyl-4- (3-methylphenyl)phenyl
882 2,2,2-trichloroethyl 2, 6-dimethyl-4- (4-methylphenyl)phenyl
883 2,2, 2-trichlordethyl 2, 6-dimethyl-4- (2-methoxyphenyl)phenyl
884 2,2, 2-trichloroethyl 2, 6-dimethyl-4- (3-methoxyphenyl)phenyl
885 2,2,2-trichloroethyl 2,6-dimethyl-4- (4-methoxyphenyl)phenyl
886 2,2,2-trichloroethyl 2,6-dimethyl-4- (4-ethoxyphenyl)phenyl
887 2,2, 2-trichloroethyl 2, 6-dimethyl-4- (4-methylthiophenyl)phenyl
888 2,2,2-trichloroethyl 2, 6-dimethyl-4-(2-fluorophenyl)phenyl
889 2,2,2-trichloroethyl 2,6-dimethyl-4- (3-fluorophenyl) phenyl
890 2,2,2-trichloroethyl 2, 6-dimethyl-4- (4-fluorophenyl) phenyl
891 2,2,2-trichloroethyl 2, 6-dimethyl-4- (3, 4-difluorophenyl)phenyl
892 2, 2, 2-trichloroethyl 2, 6-dimethyl-4- (3-methyl-4-fluorophenyl)phenyl
893 2,2,2-trichloroethyl 2, 6-dimethyl-4- (fu.ran-3-yl)phenyl
894 2,2, 2-trichloroethyl 2, 6-dimethyl-4- (thiophene-2-yl) phenyl
. 895 2,2,2-trichloroethyl 2, 6-dimethyl-4- (thiophene-3-yl)phenyl
896 2,2,2-trichloroethyl 2,4-dichloro-6-methylphenyl
897 2,2,2-trichloroethyl 2,4-dichloro-6-trif luoromethylphenyl
898 2,2, 2-trichloroethyl 2,6-dichloro-4- (heptafluoroisopropylthio) phenyl
899 2,2,2-trichloroethyl 2' 6-dichloro-4-(heptafluoroisopropyl
sulfonyl) phenyl
900 2,2,2-trichloroethyl 2, 6-dichloro-4-pentafluorosulfanylphenyl

98
Table 1(41)
Compound No. Ri Q
901 2,2,2-trichloroethyl 2,6-dibromo-4-cyclohexylphenyl
902 2,2,2-trichloroethyl 2,4-dibromo~6-trifluoromethylphenyl
903 2, 2,2-trichloroethyl 2, 6-dibromo-4-(nonafluoro-n-butylthio)phenyl
904 2,2,2-trichloroethyl 2-chloro-4-hydroxy-6-methylphenyl
905 2,2,2 -trichloroethyl 2-chloro-4-trifluoromethoxy-6-methylphenyl
M 2,2,2-trichloroethyl 2-chloro-4-((2,2,2-trichloroethoxy)carbonyloxy)
-6-methylphenyl
907 2,2,2-trichloroethyl 2-chloro-4-cyano-6-methylphenyl
908 2,2,2-trichloroethyl 2-chloro-4-iodo-6-methylphenyl
909 2,2,2-trichloroethyl 2-bromo-4-isopropyl-6-inethylphenyl
910 2,2,2-trichloroethyl 2-bromo-4-hydroxy-6-me thylphe ny1
911 2,2,2-trichloroethyl 2-chloro-4-isopropyl-6-trifluoromethylphenyl
912 2,2,2-trichloroethyl 2-bromo-4-((2,2,2-trichloroethoxy)carbonyloxy)
' - 6-methylphenyl
913 2,2,2-trichloroethyl 2-chloro-4-bromo-6-trifluoromethylphenyl
. 914 2,2,2-trichloroethyl 2-bromo-4-isopropyl-6-trifluoromethyIphenyl
915 2,2,2-trichloroethyl • 2-bromo-4-chloro-6-trifluoromethylphenyl
916 2,2,2-trichloroethyl pentafluorophenyl
917 2-chloroethyl 2,6-dimethyl-4-iodophenyl
„,„ ,,,..., . 2,6-dimethyl-4-(l,l,l,3/3,3-hexafluoro2-
918 3,3,3-trifluoro-n-propyl . J. ' _ \ , ,_
hydroxy-2-propyl) phenyl
919 3,3, 3-trifluoro-n-propyl 2, 6-dichloro-4-pentafluorosulfanylphenyl
920 i-Pr | 2-methyl-4-heptafluoroisopropyl-l-naphthyl

99
Table 1 (42)
Compound No. Ri Q
q. . 4-heptafluoroisopropyl-5,6,7,8-
X tetrahydro-1-naphthyl
„2? . 2-chloro-4-heptafluoroisopropyl-5,6,7,8-
~ tetrahydro-1-naphthyl
923 i-Pr l-methyl-3-trifluoromethylpyrazol-5-yl
924 i-Pr l-methyl-3-trifluoromethyl-4-chloropyrazol-5-yl
925 i-Pr l-methyl-3-trifluoromethyl-4-bromopyrazol-5-yl
g2fi . l-methyl-3-trifluoromethyl-4-methoxy
carbonylpyrazol-5-yl
927 i-Pr 2-chloro-4-methylpyridin-5-yl
928 i-Pr 2-bromo4-methyl-.6-chloropyridin-3-yl
g2g ._ 2-(l,l,l,3,3,3-hexafluoroisopropyloxy)
pyridin-5-yl '
g3Q ipr 2-(l,l,l,3,3,3-hexafluoroisopropyloxy)
-4 -me thylpyridin-5-yl
_31 ._ 2-brorao-6-(l,l,l,3,3,3-hexafluoro
. isopropyloxy) pyridin-3-yl
g32 . 2,4-dimethyl-6-(l,l,l,3,3/3-hexafluoro
isopropyloxy)pyridin-3-yl
933 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropyl-1-naphthyl
9^ 2,2,2-trichloroethyl 4-heptafluoroisopropyl-5, 6,7, 8-
tetrahydro-1-naphthyl
mc o » n <. • 1.1 ^u i 2-chloro-4-heptafluoroisopropy^
935 2,2,2-trichloroethyl ■=*■-,«,,_*. I.J -. Z^ i
' _ 5, 6, 7,8-tetrahydro-l-naphthyl
936 2,2,2-trichloroethyl l-methyl-3-trifluoromethylpyrazol-5-yl
937 2,2,2-trichloroethyl l-methyl-3-trifluoromethyl-4-chloropyrazol-5-yl
938 2,2,2-trichloroethyl l-methyl-3-trifluoromethyl-4-bromopyrazol-5-yl
939 "^ 2,2,2-trichloroethyl l-methyl-3-trifluoromethyl-4-methoxy
carbonylpyrazol-5-yl
940 2,2,2-trichloroethyl 1- (3-chloropyridine-2-yl) -3-bromopyra2ol-5-yl

100
Table 1(43)
Compound
No. ^ ^________
„.n ., . ., . • ., .... l-(3-chloropyridin-2-yl)-3-bromo
941 2,2,2-tnchloroethyl -4-chloropyrazol-5-yl
942 2,2,2-trichloroethyl 2-heptafluoroisopropyl-4-methylpyridin-5-yl
„., _ . _ . . ., ... , 2-(l,l,l,3,3,3-hexafluoro
943 2,2,2-tnchloroethyl . ' , ... . ,
' lsopropyloxy) pyrj.dJ.n-5-yl
... - _ - . . . , ... 2-(l,l,l,3,3,3-hexafluoroisopropyloxy)
944 2,2,2-tnchloroethyl „ *.u ■. ■_■• c i
-4-methylpyridin-5-yl
945 2,2, 2-trichloroethyl 2-chloro-4-methylpyridin-5-yl
946 2,2,2-trichloroethyl 3-chloro-5-trifluoromethylpyridin-2-yl
947 2,2,2-trichloroethyl 2-bromo-4-methyl-6-chloropyridin-3-yl
... _ _ . . . ., .... 2-bromo-6-(l, 1,1,3,3,3-hexafluoro
948 2,2,2-tnchloroethyl . ' ' ' . _. ,
■_ isopropyloxy) pyri.dj.n-3-yl
949 2,2, 2-trichloroethyl 2, 6-dichloro-4- (trifluoromethylsulfinyl)phenyl
950 2,2, 2-trichloroethyl 2, 6-dibrpmo-4- (trifluoromethylsulfinyl)phenyl
951 2,2,2-trichloroethyl 2,6-dichloro-4-(pentafluoroethylsulfinyl)phenyl
. . 952 2,2, 2-trichloroethyl 2, 6-dibromo-4- (pentafluoroethylsulfinyl)phenyl
953 2,2, 2-trichloroethyl 2, 6-dichloro-4-(pentafluoroethylsulfonyl)phenyl
954 2,2,2-trichloroethyl 2,6-dibromo-4-(pentafluoroethylsulfonyl)phenyl
... _ _ . . . . , .. _ 2,6-dichloro-4-(heptafluoro-n-propyl
955 2,2,2-tnchloroethyl , ' ,, . ,
sulfmyl) phenyl
... _ . . . . ., .. . 2,6-dibromo-4-(heptafluoro-n-propyl
956 2,2,2-tnchloroethyl f, v ei
' sulflnyl) phenyl
957 2,2,2-trichloroethyl 2-chloro-6-methyl-4- (nonaf luoro-2 -butyl) phenyl
958 2,2,2-trichloroethyl 2-bromo-6-methyl-4-(nonafluoro-2-butyl) phenyl
959 2,2,2-trichloroethyl 2-iodo-6-methyl-4- (nonafluoro-2-butyl) phenyl
960 2,2, 2-trichloroethyl 2, 6-dichloro-4- (nonaf luoro-2-butyl) phenyl

101 Table 1(44)
Compound No. R> Q
. 961 2, 2,2-trichloroethyl 2, 6-dibromo-4- (nonafluoro-2-butyl)phenyl
962 2,2, 2-trichloroethyl 2, 6-dimethyl-4-pentafluoroethylphenyl
963 2,2,2-trichloroethyl 2,6-dichloro-4-pentafluoroethylphenyl 9^ 2,2,2-trichloroethyl 2, 6-dimethyl-4-(pentafluoroethylthio)
~ 2,2, 2-trichloroethyl 2, 6-dimethyl-4-(pe^tafluoroethylsulfinyl)
9^6 2,2, 2-trichloroethyl 2, e-dimethyl-4- (pe^afluoroethylsulfonyl)
9^ 2,2, 2-trichloroethyl 2, 6-dichloro-4-(pentafluoroethylthio)
phenyl
... . 2-chloro-4-methyl-6-(l,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl
.,.„ , , ,_ . 2-chloro-4-methyl-6-(l, 1,1,3,3, 3-hexafluoro
969 cyclobutyl J , ,•_,., ■.
isopropyloxy) pyndin-3-yl
_-,_ . . , 2-chloro-4-methyl-6-(l,l,1,3,3,3-hexafluoro
970 cyclopentyl . J , \ -l,- ■> ■,
isopropyloxy) pyridin-3-yl
„.,, . . , 2-chloro4-methyl-6-(1,1,1,3,3,3-hexafluoro
971 4-cyanobenzyl . ■" ,,'.', ,
. _ -isopropyloxy) pyridm-3-yl
„^_ _ .. ... 2-chloro-4-methyl-6-(l,1,1,3,3,3-hexafluoro
972 2-methoxyethyl . ' , ,•_,■, ,
■ isopropyloxy) pyridin-3-yl
„_- „ .. , 2-chloro-4-methyl-6-(l,1,1,3,3,3-hexafluoro
973 2-cyanoethyl . Jr, . ■!• , ,
isopropyloxy) pyricb.n-3-yl
-.,, „ , .. , _. . .. , 2-chloro-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
974 2-(methylthio)ethyl . J , , ■_,. 4 , isopropyloxy) pyridin-3-yl
975 2-(ethylthio)ethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy) pyndin-3-yl
„-,_ , j. , r, , .. .., . , ., , 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
976 l-methyl-2-(methylthio)ethyl . J , ,-',■■> ■,
_ isopropyloxy) pyridin-3-yl
977 2-(ethylsulfinyl)ethyl 2-chloro-4-methyl-6-(1,1,1,3,3 3-hexafluoro J isopropyloxy) pyridin-3-yl
978 2-(ethylsulfonyl)ethyl 2-chloro-4-methyl-6-(1,1,1 3,3 3-hexafluoro isopropyloxy) pyridin-3-yl
979 2-fluoroethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
_ isopropyloxy) pyridin-3-yl
980 2,2-difluoroethyl 2-chloro-4-methyl-6-(l, 1,1,3, 3 3-hexafluoro
| _ [ isopropyloxy) pyridin-3-yl

102
Table 1(45)
Compound No. Ri Q
ao, ., . . .. .., „. . 2-chloro-4-n,ethyl-6-(1,1,1,3,3,3-hexafluoro
981 2,2,2-tnfluoroethyl . J , ...... -,
j isopropyloxy) pyridm-3-yl
ZZ, , , ,.,, I ~ I 2-chloro~4-methyl-6- (1,1,1,3,3,3-hexafluoro
982 1,3-difluoro-2-propyl . J , '.'.' ,
isopropyloxy) pyndin-3-yl
... , ,, , _, _ , 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
983 l-chloro-3-fluoro-2-propyl . J. > •_■• 4 i
c CJ isopropyloxy) pyndm-3-yl
... , .. , - _ . . .., „. , 2-chloro-4-methyl-6-(l,1,1,3,3,3-hexafluoro
984 l-methyl-2,2,2-trifluoroethyl . J , , -j- -, ■,
_ isopropyloxy) pyridin-3-yl
.... , , , . ... , 2-chloro-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
985 3,3,3-tnfluoro-n-propyl . , , -j- i •■
r J isopropyloxy) pyridin-3-yl
no, -,-,,,-, 4. *, , 2-chloro-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
986 2,2,3,3,3-pentafluoro-n-propyl . , , ._,- i ,
r J isopropyloxy) pyridm-3-yl
oo-i -,-,*.« 4-4=1 i i. 4. i 2-chloro-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
987 3,3,4,4,4-pentafluoro-2-butyl . , , ... i ,
_ _ isopropyloxy) pyridin-3-yl
ooo „ A A 4. -*i w 4- , 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
988 4,4,4-trifluoro-n-butyl . J , ' .'. ' ,
isopropyloxy) pyridin-3-yl
... oo-.-,4.4.4=-, -,,..-•, 2-chloro-4-methy 1-6-(1,1,1,3,3,3-hexafluoro
989 2,2,3,3-tetrafluorocyclobutyl . , ■ • j. , i
' ; _ _ isopropyloxy) pyridin-3-yl
... 0 ., .., 2-chlorq-4-methyl-6-(1,1,1,3,3,3-hexafluoro
990 2-chloroethyl . .J , ,-_,., ,
_ isopropyloxy) pyridin-3-yl
.... „ _ .. ., .. , 2-chloro-4-methyl-6-(l,l, 1,3,3,3-hexafluoro
991 2,2-dichloroethyl . ,•,•_,■-, ,
_ isopropyloxy) pyridin-3-yl
992 2,2,2-trichloroethyl 2-chloro-4-methyl-6-(1,1,13,3 3-hexafluoro
isopropyloxy) pyridin-3-yl
... . , .. ., _ . 2-chloro-4-methyl-6-(l,1,1,3,3;3-hexafluoro
993 1,3-dichloro-2-propyl . , , •_,- i ,
isopropyloxy) pyridin-3-yl
... , ., , 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
994 3-chloro-n-propyl . 1 , . ■•■ U ,
J isopropyloxy) pyridin-3-yl
... _ . .., 2-chloro-4-inethyl-6-(l, 1,1,3,3,3-hexafluoro
995 2-bromoethyl . J , ,...-. ,
_ isopropyloxy) pyridin-3-yl
.., . . . . .. .. , 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
996 2,2,2-tribromoethyl . , , -j- -, i
isopropyloxy) pyridin-3-yl
... , . , 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
997 3-bromo-n-propyl . •* , \ ■!,- ■> i
J isopropyloxy) pyridin-3-yl
99g 2-iodoethyl 2-chloro-4-methyl-6-(l,l,1,3,3,3-hexafluoro
isopropyloxy) pyridin-3-yl
... 4. 4. ^ j 4= -, , 2-chloro-4-methyl-6-(l,l, 1,3,3,3-hexafluoro
999 tetrahydrofuran-3-yl . J , , .L. i ,
; isopropyloxy) pyridin-3-yl
.... ,. _ .. .. , 2-chloro-4-methyl-6-(l,1,1,3,3,3-hexafluoro
1000 (furan-2-yl)methyl . * , . ... L ,
isopropyloxy pyridin-3-yl

103 Table 1(46)
Compound No. R[ Q
,nni ., „ .. ,., 2-chloro-4-methyl-6-(1,1,1,3, 3, 3-hexafluoro
1001 (furan-3-yl)methyl . , , -j- -> ■,
isopropyloxy) pyridin-3-yl
nnn-i ,4- 1. u J c -, ■,, J.I. •. 2-chloro-4-methyl-6- (1,1,1,3,3,3-hexafluoro
1002 (tetrahydrofuran-2-yl)methyl . J , .... 1 ,
_ _ isopropyloxy) pyndm-3-yl
,„,,-, .. . . , , ^i.^i., 2-chloro-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
1003 (tetrahydrofuran-3-yl)methyl . 3 . , ... ' ,
isopropyloxy) pyndin-3 -yl
.... ,... . _ ,. .. , 2-chloro-4-methyl-6-(l, 1,1,3, 3, 3-hexafluoro
1004 (thiophen-2-yl methyl . ' , . ... L •■
isopropyloxy) pyndin-3-yl
mnc ,4-v.- v r> ■. % i_,_ ■, 2-chloro-4-methyl-6- (1,1,1,3,3,3-hexafluoro
1005 (thxophen-3-yl) methyl . J, ,.'.' ,
isopropyloxy) pyndin-3-yl
.„_, , ... _ _, .. ; 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1006 (pyndin-2-yl) methyl . ' , . ... L ,
isopropyloxy) pyridin-3-yl
._„„ , ... -. , , ., , 2-chloro-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
1007 (pyridin-3-yl)methyl . ' , .._,.-, ,
_ J isopropyloxy) pyridin-3-yl
..._ ,, . , . .. , ,. ^. . 2-chloro-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
1008 (6-chloropyridin-3-yl)methyl . J , ' .'. ' ,
_ isopropyloxy) pyridin-3-yl
loog _ 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
,_. isopropyloxy) pyridin-3-yl
lnin _p 2-bromo-4-methyl-6-(l,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl •
1011 . . 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
_ isopropyloxy) pyridin-3-yl
.„,„ , 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1012 propargyl . ,/._.--,,
isopropyloxy) pyndin-3ryl
, „,-, 11.^, 2-bromo-4-methyl-6-(1,1,1,3, 3,3-hexafluoro
1013 cyclobutyl . J . . ... , ,
isopropyloxy) pyridin-3-yl
.„. . . . , 2-bromo-4-methyl-6-(l,1,1,3,3,3-hexafluoro
1014 cyclopentyl . J , , ... , , .
isopropyloxy) pyridin-3-yl
, „, c , , 2-bronio-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
1015 benzyl . J , , ... , .
isopropyloxy) pyridin-3-yl
, „,, _, , 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1016 3-cyanobenzyl . •* , ,...-, ,
isopropyloxy) pyridin-3-yl
.„,-, . . 2-bramo-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
1017 4-cyanobenzyl . J , ,...-, ,
_ isopropyloxy) pyridin-3-yl
.... ., ., . , 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1018 3-chlorobenzyl . ' , \ ... , ,
_ isopropyloxy) pyridin-3-yl
,.._ ■ -i 1.1. 1.1. i 2-brorao-4-methyl-6-(i, 1,1,3,3,3-hexafluoro
1019 2-methoxyethyl . J , . .' . ' ,
J isopropyloxy) pyridm-3-yl
.__„ _ .. , 2-bromo-4-methyl-6-(l,1,1,3,3,3-hexafluoro
1020 2-cyanoethyl . ■" , . ... , .
isopropyloxy) pyridin-3-yl

104
Table 1(47)
Compound No. Ri. Q
~~ ~, _.,_.. . _. , 2-bromo-4-methvl-6-(l, 1,1,3,3,3-hexafluoro
1021 2- methylthio ethyl . - . , ... ^ ,
J isopropyloxy) pyndin-3-yl
7ZT-, o , 4-v •■.._■ i -v i 2-bromo-4-methyl-6-(1,1,1,3,3, 3-hexafluoro
1022 2- ethvlthio)ethyl , . •_•-,-,
- J isopropyloxy) pyndin-3-yl
77TZ , „•,-,,_!. -,^- > ._ ■. 2-bromo-4-methy_-6-(l, 1,1,3,3,3-hexafluoro
1023 l-methyl-2-(methylthio) ethyl . * , ,..,•-, ,
_ J J isopropyloxy) pyndin-3-yl
,„-„ „ , _. , 1t. , , _. , 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1024 2- ethylsulfinyl)ethyl . , , • _,. % ,
isopropyloxy) pyridin-3-yl
n„.c - , ., , ,. ,. ., , 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1025 2-(ethylsulfonyl)ethyl . , , ._,■ ■, ,
isopropyloxy) pyridan-3-yl
1026 . 2-fluoroethyl 2-bromo-4-n_thyl-6-(1 1,1,3,3,3-hexafluoro
_ isopropyloxy) pyndin-3-yl
1027 2, 2-difluoroethyl 2-bromp-4-n_thyl-6- (1,1,1 3,3 3-hexafluoro
isopropyloxy) pyridin-3-yl
1028 2, 2,2-trifluoroethyl 2-bro_-4 _thyl-6- (1,1,1,3, 3, 3-hexafluoro
isopropyloxy) pyridin-3-yl
.„„. , _, ,._, _ _ , 2-bromo-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
1029 l,3-difluoro-2-propyl . * , . . . • , ,
' ; isopropyloxy) pyridin-3-yl
, „-,„ , ., -, JT, „ , 2-bromo-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
1030 l-chloro-3-fluoro-2-propyl • . , , _. -,
rj isopropyloxy) pyridin-3-yl
,„-,, , 4.u i -, o o 4. -ti 1.1. ■. 2-bromo-4-methyl-6- (1,1,1,3,3,3-hexafluoro
1031 l-methyl-2,2,2-trifluoroethyl . J , . .' . ' ,
_ isopropyloxy) pyridin-3-yl
,_,_ , ., , . . ,, . 2-bromo-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
1032 3,3,3-trifluoro-n-propyl . , , ... -,
' isopropyloxy) pyridin-3-yl
, n-,, „ _ , ., -, 4. _, , 2-bromo-4-raethyl-6-( 1,1,1,3,3,3-hexafluoro
1033 2,2,3,3,3-pentafluoro-n-propyl . , . ._. - ,
_ isopropyloxy) pyridm-3-yl
,_.. -, -, * * A 4-*i 01-4.1 2-bromo-4-niethyl-6-(l, 1,1,3,3,3-hexafluoro
1034 3,3,4,4,4-pentafluoro-2-butyl . J , , ... ' ,
_ isopropyloxy) pyridin-3-yl
._._ . . „ , . ,, . . , ' 2-bromo-4-methyl-6-(l,1,1,3,3,3-hexafluoro
1035 4,4,4-trifluoro-n-butyl . * , , ... ' ,
_ isopropyloxy) pyridin-3-yl
._,, _-.,_...,- T^.4., 2-bramo-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
1036 2,2,3,3-tetrafluorocyclobutyl . • •* , ' .'. ' ,
isopropyloxy) pyridin-3-yl
1037 2-chloroethyl 2-brorao-4-n_thyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy) pyridin-3-yl
1038 2,2-dichloroethyl 2-bro_D-«-__iyl-6- (1,1,1,3,3, 3-hexafluoro
isopropyloxy) pyridin-3-yl
1039 2,2,2-trichloroethyl 2-br_-4-._thyl-6-(l 1,1,3, 3, 3-hexafluoro
isopropyloxy) pyridin-3-yl
1040 1, 3-dichloro-2-proPyl 2 „_-4 „_yl-6- (1,1,1,3,3,3-hexafluoro
( [ isopropyloxy) pyndin-3-yl

105
Table 1(48) ___^
Compound No. Ri Q
~~ ~ ~ " 2-bromo-4-methyl-6-(1,1, 1, 3, 3, 3-hexafluoro
1041 3-chloro-n-propyl . * .' . - .
isopropyloxy) pyndm-3 -yl
,. „ 7~T .. , I 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1042 2-bromoethyl . , , •,,• -> ,
isopropyloxy) pyndin-3-yl
7771 _ _ „ _ .. .. . 2-bromo-4-methyl-6-( 1,1,1,3,3,3-hexafluoro
1043 2,2,2-tnbromoethyl . , , -j- ■, -,
isopropyloxy) pyndin-3-yl
„„„„ , , , 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1044 3-bromo-n-proDyl . , . ' . ' ,
_____ isopropyloxy) pyndin-3-yl
1045 2-iodoethyl 2-bromo-4-methyl-6-(1,1,1,3, 3 3-hexafluoro
_ isopropyloxy) pyridin-3-yl
,-., ^ _. _ j - -, , 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1046 tetrahydrofuran-3-yl . J , .' ' . ' ,
isopropyloxy) pyridin-3-yl
,„„-, ,* T i , 4.T. , 2-bromo-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
1047 furan-2-yl)methyl . J , . ... _ n
isopropyloxy) pyridm-3-yl
,-.. ,_ , ., ._ . 2-bromo-4-methyl-6-(l, 1,1,3, 3,3-hexafluoro
1048 (furan-3-yl)methyl . J , . . .. , ,
isopropyloxy) pyridin-3-yl
,_.„ ,_ . . j , - ,. _. , 2-bromo-4-methyl-6-(l, 1,1,3, 3,3-hexafluoro
1049 (tetrahydrofuran-2-yl)methyl . J , ....-, ,
. isopropyloxy) pyndin-3-yl
, „_„ • _ , . ' -,i, tl , 2-bromd-4-methyl-6-(l, 1,1,3,3, 3-hexafluoro
1050 (tetrahydrofuran-3-yl)methyl . J , . ' . ' ,
_ isopropyloxy) pyridin-3-yl
,„C1 .... . _ ,. _. ', 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1051 (thiophen-2-yl methyl . ,,._>.-,,
_ isopropyloxy) pyridin-3-yl
,._„ ,_.. . , ,. _. , 2-bromo-4-methyl-6-(l, 1,1, 3,3,3-hexafluoro
1052 (thiophen-3-yl)methyl . J , . ... ' ,
isopropyloxy) pyridm-3-yl
n._. , ... _ .. ... 2^bromo-4-methyl-6-(1,1,1,3,3, 3-hexafluoro
1053 (pyndin-2-yl) methyl . J l ... ' ,
_ isopropyloxy) pyridin-3-yl
,„,,, . ... _ ., ... 2-bromo-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
1054 (pyridin-3-yl) methyl . J , , ... , ,
_ isopropyloxy) pyridin-3-yl
,„cc ,, ., ... -. .. ... 2-bromo-4-methyl-6-(l,1,1,3,3,3-hexafluoro
1055 6-chloropy«din-3-yl) methyl . J ,..'.' ,
_ isopropyloxy) pyridin-3-yl
in,fi . _ 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy) pyridin-3-yl
.Q57 i-Pr 2-iodo-4-methyl-6-(1,1,1,3,3, 3-hexafluoro
. isopropyloxy) pyridin-3-yl
.... . . 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
iifjo vinyl , .....
isopropyloxy) pyndin-3-yl
1059 propargyl 2-iodo-4-methyl-6-(l, 1,1, 3,3, 3-hexafluoro
isopropyloxy) pyridin-3-yl
1060 cyclobutyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
| | isopropyloxy) pyridin-3-yl

106
Table 1(49)
Compound No. Ri Q
,„,„ , ^ , 2-iodo-4-methyl-6- (1,1,1,3,3,3-hexafluoro
1061 cvclopentyl . ■" . : ... _ ,
J isopropyloxy) pyndin-3-yl
, „„ ~ " 1 2-iodo-4-methyl-6- (1,1,1,3,3,3-hexafluoro
1062 benzyl J , ' '_,' ' ,
_ isopropyloxy) pyndin-3-yl
,.„ , , , 2-iodo-4-methyl-6-(l,l, 1,3,3,3-hexafluoro
1063 3-cyanobenzyl . J , ' ... ' .
isopropyloxy) pyndin-3-yl
~~, , T ] 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1064 4-cyanobenzyl . J , ,'_,'-,,
isopropyloxy) pyndin-3-yl
,.„ . .. , . 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1065 3-chlorobenzyl . J ■,,'_,'-, ,
isopropyloxy) pyndin-3-yl
,„,, _. „. , 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1066 2-methoxyethyl . 2 , : ... ' ,
J isopropyloxy) pyndin-3-yl
,.__. _ ., . 2-iodo-4-methyl-6-(l,1,1,3,3,3-hexafluoro
1067 2-cyanoethyl . J ■,,'_,'-, •,
isopropyloxy) pyridm-3-yl
,„.. n , .. .... . .. , 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1068 2-(methylthio ethyl . J , ' .' , ,
isopropyloxy) pyridin-3-yl
1069 2-(ethylthio)ethyl 2.iodo-4-methyl-6-(l 1,1,3,3,3-hexafluoro
isopropyloxy) pyridin-3-yl
-.r.-™ i -..I. T o / 4-u ,»v i .-v -i 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1070 l-methyl-2-(methylthio) ethyl . •* ,,'.'-, ,
_ isopropyloxy) pyridin-3-yl
,„-,, _ , ^. , ... .,,_., 2-iodo-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
1071 2-(ethylsulfinyl)ethyl . J ,,.'.., ,
isopropyloxy) pyndin-3-yl
.__. _ , ., , ._ .. .. n 2-iodo-4-methyl-6- (1,1,1,3,3,3-hexafluoro
1072 2- (ethylsulfonyl)ethyl . J ,,..._ ,
isopropyloxy) pyridin-3-yl
1073 2-fluoroethyl 2-iodo-4-methyl-6-(1 1,1,3,3,3-hexafluoro
isopropyloxy) pyridin-3-yl
,„-,, „ o j-*! ..v. i 2-iodo-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
1074 2,2-difluoroethyl . J , . ' . ' ,
; isopropyloxy) pyridin-3-yl
1075 2,2,2-trifluoroethyl 2-iodo-4-methyl-6-(1 1,1,3,3,3-hexafluoro
' _ isopropyloxy) pyridin-3-yl
,„^, . , .... „ , 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1076 l,3-difluoro-2-propyl . J ,;..._ ,
•_ isopropyloxy) pyridin-3-yl
,„-,., , ., -, -, „ . • 2-iodo-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
1077 l-chloro-3-fluoro-2-propyl . J ,'.'.' ,
isopropyloxy) pyridin-3-yl
1078 l-methyl-2,2,2-trifluoroethyl 2-iodo-4-mfithyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy) pyridin-3-yl
n„_„ ,,,.... , 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1079 3,3,3-trifluoro-n-propyl . J ,....- ,
' isopropyloxy) pyridin-3-yl
.„„„ ,, - , , , ,_ 4r. , 2-iodo-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
1080 2,2,3,3,3-pentafluoro-n-propyl . J ,,...' ,
| _ | isopropyloxy) pyridin-3-yl

107
Table 1(50)
Compound No. Ri Q
T777 -,-,„„„ m TTT^ 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1081 3,3,4,4,4-pentafluoro-2-butyl . ,,'_,'-, ,
I r _ isopropyloxy) pyridm-3-yl
,.„. . . . _ .„. , ,_ , 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1082 4, 4,4-trifluoro-n-butyl . J , ' ' .. , ,
isopropyloxy) pyridin-3-yl
7777 I __,,.. 77 , . . . 2-iodo-4-methyl-6-(l,l,l,3,3,3-hexafluoro
1083 2,2,3,3-tetrafluorocyclobutyl . ' '_■• , T
[ isopropyloxy) pyndin-3-yl
,_0. -, ., .. , 2-iodo-4-inethyl-6-(l,l,l,3,3,3-hexafluoro
1084 2-chloroethyl . J , ' ... - .
isopropyloxy) pyridin-3-yl
1085 2,2-dichloroethyl 2-i«xto-4-«thy1-6-(1, 1,1,3,3, 3-hexafluoro
isopropyloxy) pyndin-3-yl
1086 2,2, 2-trichloroethyl 2-iodo-4-methyl-6- <1> 1,1, 3,3, 3-hexafluoro
' isopropyloxy) pyridin-3-yl
nno-, ,,..., _ , 2-iodo-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
1087 1,3-dichloro-2-propyl . J . _,' -, -,
; r isopropyloxy) pyridm-3-yl
,noo , ,, , 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1088 3-chloro-n-propyl . 1 ,'..', ,
isopropyloxy) pyridin-3-yl
,„nn _ . .. , 2-iodo-4-nethyl-6-(l,l,l,3,3,3-hexaxluoro
1089 2-bromoethyl . , ' . '. \ ,
isopropyloxy) pyridin-3-yl
1090 2,2,2-tribromoethyl 2-iodo-4-methyl-6-(l 1,1,?, 3,3-hexafluoro
isopropyloxy) pyndin-3-yl
._-., , . , 2-iodo-4-methyl-6-(l,l,1,3,3,3-hexafluoro
1091 3-bromo-n-propyl . ,.'_,'■» ,
isopropyloxy) pyridm-3-yl
1092 2-iodoethyl 2-iodo-4-methyl-6-(l,1,1,3,3,3-hexafluoro
isopropyloxy) pyridin-3-yl
,.„, „ . . . . , , 2-iodo-4-roethyl-6-(1,1,1,3,3,3-hexafluoro
1093 tetrahydrofuran-3-yl . * ,.'.., ,
isopropyloxy) pyndin-3-yl
,„,,„ ,- -, , . .. , 2-iodo-4-roethyl-6-(1,1,1,3,3,3-hexafluoro
1094 (furan-2-yl methyl . J . ' ... ' ,
isopropyloxy) pyridin-3-yl
..._ ,_ ., ,. ,_. . 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1095 (furan-3-yl methyl . J „:'.., ,
isopropyloxy) pyridin-3-yl
1r,„, ,t ,. v. j « ni> ^>.-i 2-iodo-4-methyl-6- (1,1,1,3,3,3-hexafluoro
1096 (tetrahydrofuran-2-yl)methyl . J ,...', ,
. isopropyloxy) pyridm-3-yl
,,,„-, ,. . . . _ , ,. .. , 2-iodo-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
1097 tetrahydrofuran-3-yl)methyl . J ,....- ,
isopropyloxy) pyridin-3-yl
1098 (thiophen-2-yl) methyl 2-iodo-4-«Sthyl-6- (1,1,1,3,3,3-hexafluoro isopropyloxy) pyridin-3-yl
1099 (thiophen-3-yl)methyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro _ isopropyloxy) pyridin-3-yl
1100 (pyridin-2-yl)methyl 2-iodo-4-methyl-6-(l 1,1,3,3,3-hexafluoro
j _ [ isopropyloxy) pyridin-3-yl (

108
Table 1(51) ____^
Compound No. FU Q
,,_, " 7~. I T. Z i 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro .
1101 (pyndin-3-yl metnvl . J ,:'.-, ,
_ isopropyloxy) pyridxn-3-yl
nlnr, ,r .. ... , ,. _. , 2-iodo-4-methyl-6- (1,1,1,3,3,3-hexafluoro
1102 (6-chloropyndin-3-vl)methvl . J , ; ... , ,
- - isopropyloxy) pyndin-3-yl
Q3 2, 4-dimethyl-6- (1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl
11Q4 ._pr 2, 4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl
, ,„, . . 2, 4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
1105 vinyl . J , , ... -, ,
V isopropyloxy) pyndin-3-yl
„., . 2, 4-dimethyl^ 6- (1,1,1,3, 3, 3-hexafluoro
1106 propargyl . J , , ... , ,
isopropyloxy) pyndin-3-yl
,,„., , . . , 2, 4-dimethyl-6-(1,1,1,3, 3, 3-hexafluoro
1107 cyclobutyl . , . ... ., ,
isopropyloxy) pyridin-3-yl
n.no , ' . , 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
1108 cyclopentyl . J , , ... _ ,
isopropyloxy) pyridin-3 -yl
-log . , 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy) pyridin-3-yl
,,,,>■ , . , 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
1110 3-cyanobenzyl . ' ,/._,..,■,
■ isopropyloxy)pyridin-3-yl
1lnl . . , 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
1111 4-cyanobenzyl . J ,,/,.,,
isopropyloxy) pyridin-3 -yl
,,,_ , .. . . 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
1112 3-chlorobenzyl . J ,'.,._,
isopropyloxy) pyridin-3-yl
..... ,, .. ... 2,4-dimethyl-6- (1,1,1,3,3,3-hexafluoro
1113 2-methoxyethyl . J ,'.,.„,
isopropyloxy) pyridin-3-yl
1114 2-cyanoethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
[__. isopropyloxy) pyridin-3-yl
1115 2- (methylthio) ethyl 2' ^diinethyl-6- (1,1,1,3,3,3-hexafluoro isopropyloxy) pyndin-3-yl
1116 2- (ethylthio) ethyl 2' «-di«thyl-6- (1,1,1,3,.3,3-hexafluoro _ _ isopropyloxy) pyridin-3 -yl
,..-, , .. , „ , .. .., . . ... , 2,4-dimethyl-6-(1.1,1,3,3,3-hexafluoro
1117 1-methyl-2- (methylthio) ethyl . J „'._,..,,
isopropyloxy) pyridin-3-yl
1118 2- (ethylsulfinyl) ethyl 2' «-di«thyl-6- {1,1,1,3,3,3-hexafluoro _ isopropyloxy) pyridin-3-yl
1119 2- (ethylsulfonyl)ethyl 2' «~di«thyl-&-(1,1,1,3,3,3-he.xafluoro isopropyloxy) pyridm-3-yl
1120 2-fluoroethyl 2, 4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
| _ I isopropyloxy) pyridin-3-yl

109
Table 1(52)
Compound No. Ri Q
T~~ _ 0 ..„ ~~ 2,4-dimethyl-6- (1,1,1,3,3,3-hexaf luoro
1121 2,2-difluoroethyl . J •, , • _,• o i
' isopropyloxy) pyndin-3-yl
,,-- ^ „ -, 4. • -■, .,_ , 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
1122 2,2,2-tnrluoroethyl . * ,,-_,-,,
' isopropyloxy) pyndin-3-yl
, „„■, , ., . .^, _ , 2,4-dimethyl~6-(1,1,1,3, 3, 3-hexafluoro
1123 1,3-difluoro-2-propyl . * , , • _,- -> ,
' c rj isopropyloxy) pyridin-3-yl
110- , v., ■, „ -, , 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
1124 l-chloro-3-fluoro-2-propyl . * , ' ... _ ,
22 isopropyloxy) pyndin-3-yl
, ,-,c , 4.w -i o o o 4. ■*, tv , 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
1125 l-methyl-2,2,2-tnfluoroethyl . J , ' ... -, ,
_ isopropyloxy) pyridm-3-yl
,,,, , -, , .. ■„ , 2, 4-dimethyl-6-(l, 1,1,3,3,3-hexafluoro
1126 3,3.3-tnfluoro-n-propyl . ^ , ' ...' ,
_ " isopropyloxy) pyndin-3-yl
,,~, -, - -, -, -> 4. 4=, ■, 2,4-dimethyl-6-(l,l,l, 3,3,3-hexaf luoro
1127 2,2,3,3,3-pentafluoro-n-propyl . * , . ■ _,. o ,
r rj isopropyloxy) pyndin-3-yl
i,-,o ->-,„„„ 4. 4:-, it-.-. 2, 4-dimethyl-6- (1,1,1, 3, 3, 3-hexaf luoro
1128 3,3,4,4,4-pentafluoro-2-butyl . J , . ... , ,
' _ isopropyloxy) pyridin-3-yl
,no„ „„...., , . , 2,4-dimethyl-6-(l, 1,1,3,3,3-hexafluoro
1129 4, 4,4-tnfluoro-n-butyl J , ' ... ., ,
isopropyloxy) pyridm-3-yl
nl™ ooo,*.*.*! Tv.4., 2,4-dimethyl-6-(l,1,1,3,3,3-hexafluoro
1130 2,2,3,3-tetrafluorocyclobutyl . J , . . .. -, •,
' _ isopropyloxy) pyridin-3-yl
1131 2-chloroethyl 2,4-dimethyl-6-(l, 1 1,3 3,3-hexafluoro
isopropyloxy) pyridin-3-yl
1132 2,2-dichloroethyl 2'4-dimethyl-6-(1,1 1,3,3,3-hexafluoro
isopropyloxy) pyridin-3-yl .
1133 2,2,2-trichloroethyl 2'4-dimethyl-6-(1,1,1,33,3-hexafluoro
isopropyloxy) pyridin-3-yl
,,,, , , ,. ., _ , 2,4-dimethyl-6- (1,1,1,3,3,3-hexafluoro
1134 l,3-dichloro-2-propyl * , , ... , ,
isopropyloxy) pyridin-3-yl
,,,, , ., , 2,4-dimethyl-6- (1,1,1,3,3,3-hexafluoro
1135 3-chloron-propyl . J ,,...-,
isopropyloxy) pyridin-3-yl
1136 ' 2-bromoethyl 2,4-dimethyl-6-(1,1,1,3 3,3-hexafluoro
isopropyloxy) pyridin-3-yl
1137 2,2,2-tribromoethyl 2,4-dimethyl-6- (1,1,1,3,3,3-hexafluoro
isopropyloxy) pyridm-3-yl
1138 3-brorao-n-propyl 2' 4-dimethyl-6- (1,1 1,3,3,3-hexafluoro
isopropyloxy) pyridin-3-yl
u39 2-iodoethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
_ isopropyloxy) pyridin-3-yl
1140 tetrahydrofuran-3-yl 2' «-<"«thyl-6-(1,1,1, 3, 3, 3-hexafluoro
| | isopropyloxy) pyridin-3-yl

110
Table 1(53)
Compound n
Ho.
.,., If 0 .. _u . 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
1141 (furan-2-yl)methyl , . ... ,, ,
_ * isopropyloxy) pyridin-3-yl
„„_ ,f -, ,, VK , 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
1142 (furan-3-yl methyl J , ■ ,,• -, ■,
_ isopropyloxy) pyndin-3-yl
TTTT ,_ _ . . , „ ,. _. , 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
1143 (tetrahydrofuran-2-yl)methyl . J , , .j. -, ,
_ isopropyloxy) pyndin-3-yl
.... .. . . . . , ., .. . 2,4-dimethyl-6-(1,1,1,3, 3,3-hexafluoro
1144 (tetrahydrofuran-3-yl) methyl J , . ... -, ,
isopropyloxy) pyridin-3-yl
,,„_ ... . . _ , . ., , 2,4-dimethyl-6-(l, 1,1,3,3,3-hexafluoro
1145 (thiophen-2-yl methyl . * , , ... , .
_ isopropyloxy) pyridxn-3-yl
,.,,,,- ,..,_. , , , ,.. , 2,4-dimethyl-6-(l, 1,1,3,3,3-hexafluoro
1146 (thiophen-3-yl methyl . J , , ... , ,
isopropyloxy) pyridin-3-yl
.,„_ , „ ,. ,. , 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
1147 (pyridin-2-yl)methyl J , , ... ., ,
_ isopropyloxy) pyridin-3-yl
, ,„„ . ._,.,,. ^v. , 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
1148 (pyndin-3-yl methyl J , , .... , •,
_ _ isopropyloxy) pyridin-3-yl
,,.. ,. ., ... -, ,, .. . 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
1149 6-chloropyndin-3-yl) methyl 3 , / ... „ ,
_ isopropyloxy) pyridin-3-yl
n,-0 2-bromo-4-methyl-6-(heptafluoro
. \ isopropyl) pyridih-3-yl
lnc;l . 2-bronvo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl
..,._ . , 2-brorao-4-methyl-6-(heptafluoro
1152 vinyl . / ._,-%,,
isopropyl) pyridin-3-yl
..,.- , 2-bromo-4-methyl-6-(heptafluoro
1153 propargyl . / ..-%,,
isopropyl) pyridin-3-yl
,.r. . . ^ . 2-bromo-4-methyl-6-(heptafluoro
1154 cyclobutyl . , / . .. *1 ,
isopropyl) pyridin-3-yl
,1C. ■,..■, 2-bromo-4-methyl-6-(heptafluoro
1155 cyclopentyl . ,,* . .\ *1 ,
isopropyl) pyridin-3-yl
1156 b ] 2-bromo-4-methyl-6-(heptafluoro
_ isopropyl) pyridin-3-yl
1157 3-cyanobenzyl 2-bromo-4-methyl-6-(heptafiuoro isopropyl) pyridin-3-yl
1158 4-cyanobenzyl 2-bromo-4-methyl-6-(heptafluoro isopropyl) pyridin-3-yl
1159 3-chlorobenzyl 2-bromo-4-methyl-6-(heptafluoro
_ isopropyl) pyridin-3-yl
1160 2-methoxyethyl 2-bromo-4-methyl-6-(heptafluoro
| I isopropyl) pyridm-3-yl

Ill
Table 1(54) ___^
Compound No. Ri Q
,, ., „ .. , 2-bromo-4-methyl6-(heptafluoro
1161 2-cyanoethyl . ,, ... _ ,
_ isopropyl) pyridin-3-yl
TTT^ -, , _,. n-v. ■<•->. ■, 2-bromo-4-methyl-6-(heptafluoro
1162 2- (methylthio) ethyl . ,, _i- , ,
J isopropyl) pyndin-3-yl
,,., _ , ., ,.. . . .. , 2-bromo-4-methyl-6-(heptafluoro
1163 2- ethylthio ethyl , / . .. *1 .
J J isopropyl) pyndin-3-yl
, .,.„ , .. , „ , .. 14_, . . .. , 2-bromo-4-methyl-6-(heptafluoro
1164 l-methyl-2-(methylthio) ethyl . , / . .. *1 .
_ isopropyl) pyridin-3-yl
,,,,- o / ..v. -i !*■ 11 tv ■, 2-bromo-4-methyl-6-(heptafluoro
1165 2- ethylsulfinyl)ethyl . , / . .. *1 .
_ isopropyl) pyridin-3-yl
..,.,. „ , .. , . , i>4.., 2-bromo-4-methyl-6-(heptafluoro
1166 2-(ethylsulfonyl)ethyl . , .■* ... \, .
J J J isopropyl) pyridin-3-yl
,, ^_, _ „ ,, , 2-brorao-4-methyl-6-(heptafluoro
1167 2-fluoroethyl . , / . ,. *1 .
isopropyl) pyridin-3-yl
.,_- „ _ .... ... 2-brorao-4-methyl-6-(heptafluoro
1168 2,2-difluoroethyl . , / ._,. *L ,
isopropyl) pyridin-3-yl
, ,,„ _ „ „ 4. . ^, 4. , 2-bromo-4-methyl-6-(heptafluoro
1169 2,2,2-trifluoroethyl . , / ... %. .
._ isopropyl) pyridin-3-yl
,,-,- , , .... _ , 2-bromo-4-methyl-6-.(heptafluoro
1170 l,3-difluoro-2-propyl . , ,J . '. *1 ,
isopropyl) pyridin-3-yl
.,_., . ., , ... „ . 2-bromo-4-methyl-6-(heptafluoro
1171 l-chloro-3-fluoro-2-propyl . , / . .. *1 ,
isopropyl) pyridin-3-yl
,no t x.u i o o o 4. -fi ...--, 2-bromo-4-methyl-6- (heptafluoro
1172 l-methyl-2,2,2-trifluoroethyl . , ,J .'.*!,
isopropyl) pyridin-3-yl
,,_,, , , , . ._, , 2-bromo-4-methyl-6-(heptafluoro
1173 3,3,3-trifluoro-n-propyl . , / . ,. *1 ,
isopropyl) pyridin-3-yl
,,_. -, o o •. r. «-£i -i 2-bromo-4-methyl-6-(heptafluoro
1174 2,2,3,3,3-pentafluoro-n-propyl . , / . _,. *1 , r r rj isopropyl) pyridin-3-yl
1175 3,3,4,4,4-pentafluoro-2-butyl 2-bromo-4-methyl-6-(heptafluoro _ isopropyl) pyridin-3-yl
.._- . . » ^ ■ *■, W4.T 2-bromo-4-methyl-6-(heptaf luoro
1176 4,4,4-trifluoro-n-butyl . , / .,.'_,,
_ isopropyl) pyridin-3-yl
1177 2,2,3,3-tetrafluorocyclobutyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl) pyridin-3-yl
1178 2-chloroethyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl) pyridin-3-yl
1179 2,2-dichloroethyl 2-bromo-4-methyl-6-(heptafluoro
_ isopropyl) pyridin-3-yl
1180 2,2,2-trichloroethyl 2-bromo-4-methyl-6-(heptafluoro
_J _ | isopropyl )pyridin-3-yl

112
Table 1 (55)
Compound No. Ri Q
,,., , ., ,. ., _ , 2-bromo-4-methyl-6-(heptafluoro
1181 l,3-dichloro-2-propyl . -_,• -> ,
' c CJ isopropyl )pyndin-3-yl
,, „,, , ., •, 2-bromo-4-methyl-6-(heptafluoro
1182 3-chloro-n-propyl , / ■ J- -> ,
c isopropyl )pyndin-3-yl
,,„.,- „ . „ , 2-bromo-4-methyl-6-(heptafluoro
1183 2-bromoethyl . .. . .. , ,
_ isopropyl) pyndin-3-yl
nlo. n o -> t -i. ^i-i 2-bromo-4-methyl-G-(heptafluoro
1184 2,2,2-tnbromoethyl . ,,3 . .. , .
' isopropyl) pyndm-3-yl
, ,„_ _ , , 2-bromo-4-methyl-6-(heptafluoro
1185 3-bromo-n-propyl . ,, . .. \, .
isopropyl) pyndin-3-yl
,,.. _ . . . .. ., 2-bromo-4-methyl-6-(heptafluoro
1186 2-iodoethyl . , / ._,.,,
isopropyl) pyri.din-3-yl
,,.-, . ,_ . . . , . 2-bromo-4-inethyl-6-(heptafluoro
1187 tetrahydrofuran-3-yl . ,, . .. %, ,
isopropyl)pyridin-3-yl
, ,_„ ,. _ , , ... , 2-bromo-4-inethyl-6-(heptafluoro
1188 furan-2-yl methyl . , / . .. %, .
isopropyl) pyridin-3-yl
1non .. , ,. .. n 2-bromo-4-methyl-6-(heptafluoro
1189 furan-3-yl methyl . , / . .. , ,
isopropyl) pyridin-3-yl
, ,„„ ,. . . . . „ n, .. , 2-bromo-4-methyl-6-(heptafluoro
1190 tetrahydrofuran-2-yl)methyl ,,'•_,.%, ,
_ isopropyl) pyndin-3-yl
Tim /.- .. u J * -. i > ..>. i 2-bromo-4-methyl-6-(heptafluoro
1191 (tetrahydrofuran-3-yl)methyl . . , / ...%,,
isopropyl) pyridin-3-yl
, ,„~ .... . o , > <-v. 1 2-bromo-4-methyl-6-(heptafluoro
1192 (thiophen-2-yl)methyl . , / ._,.*!,
_ _ isopropyl) pyridin-3-yl
,,„, ... . . ., , . 4.1. , 2-bromo-4-methyl-6-(heptafluoro
1193 (thiophen-3-yl methyl , / .'.*,,
_ isopropyl) pyridin-3-yl
nnn. , ... „ ,. _. , 2-bromo-4-methyl-6-(heptafluoro
1194 (pyridin-2-yl)methyl . , / . . ,. *1 ,
_ J isopropyl) pyridin-3-yl ;
,,„, , . .. _ ,. _. , 2-bromo-4-methyl-6-(heptafluoro
1195 (pyridin-3-yl)methyl . , / . ,\ K, ,
_ J isopropyl) pyridin-3-yl
,,„, ... ., ... -,,. j.. , 2-bromo-4-methyl-6-(heptafluoro
1196 (6-chloropyridin-3-yl)methyl . , / . .. *1 ,
_ isopropyl) pyridin-3-yl
1197 Et 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1198 i-Pr 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1199 vinyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1200 propargyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl

113 Table 1(56)
Compound No. Rj Q
1201 cyclobutyl 2-chloro-6-methyl-4-heptafTuoroisopropylphenyl
1202 cyclopentyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1203 benzyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1204 3-cyanobenzyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1205 4-cyanobenzyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl

1206 3-chlorobenzyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1207 2-methoxyethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1208 2-cyanoethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1209 2-(methylthio)ethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1210 2-(ethylthio)ethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1211 l-methyl-2- (methylthio) ethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1212 2- (ethylsulfinyl)ethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1213 2- (ethylsulfonyl) ethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1214 2-fluoroethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1215 2,2-dif luoroethyl 2-chloro-6-methyl-4-heptafluproisopropylphenyl
1216 2,2,2-trifluoroethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1217 1,3-difluoro-2-propyl 2-chloro-6-ntethyl-4-heptafluorois6propylphenyl
1218 l-chloro3-fluoro-2-propyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1219 l-methyl-2,2,2-trifluoroethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
[ 1220 3,3,3-trifluoro-n-propyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl

114
Table 1(57) ' ' .
Compound No. Ri Q
1221 2,2,3,3, 3-pentafluoro-n-propyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1222 3,3,4,4,4-pentafluoro-2-butyl 2-chloro-6-methyl-4-heptaf luoroisopropylphenyl
1223 4,4,4-trifluoro-n-butyl 2-chloro-6-methyl-4-heptaf luoroisopropylphenyl
1224 2,2,3,3-tetrafluorocyclobutyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1225 2-chloroethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
122G 2,2-dichloroethyl 2-chloro-6-methyl-4-heptaf luoroisopropylphenyl
1227 2,2,2-trichloroethyl 2 -chloro-6-methyl-4-heptaf luoroisopropylphenyl
1228 1,3-dichloro-2-propyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1229 3-chloro-n-propyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1230 2-bromoethyl 2-chloro-6-raethyl-4-heptaf luoroisopropylphenyl
1231 2,2,2-tribromoethyl 2-chloro-6-methyl-4-heptaf luoroisopropylphenyl
1232 3-bromo-n-propyl 2-chloro-6-methyl-4-heptaf luoroisopropylphenyl
1233 2-iodoethyl 2-chloro- 6-methyl- 4-heptaf luoroi sopropylphenyl
1234 tetrahydrofuran-3-yl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1235 (furan-2-yl) methyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1236 (furan-3-yl) methyl 2-chloro-6-methyl-4-heptaf luoroisopropylphenyl
1237 (te trahydrof uran-2 ~yl) methyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1238 (tetrahydrofuran-3-yl)methyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1239 (thiophen-2-yl) methyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1240 (thiophen-3-yl) methyl 2-chloro-6-raethyl-4-heptaf luoroisopropylphenyl

115
Table 1(58)
Compound No. Ri Q
1241 (pyriciin-2-yl) methyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1242 (pyridin-3-yl)methyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1243 (6-chloropyridin-3-yl)methyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1244 Et 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1245 i-Pr 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1246 vinyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1247 propargyl 2-brorao-G-methyl-4-heptafluoroisopropylphenyl
1248 cyclobutyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1249 cyclopentyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1250 benzyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1251 3-cyanobenzyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1252 4-cyanobenzyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1253 3-chlorobenzyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1254 2-methoxyethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1255 2-cyanoethyl 2-bromo-6-7methyl-4-heptaf3.uoroisopropylphenyl
1256 : 2- (methylthio) ethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1257 2- (ethylthio) ethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1258 l-methyl-2- (methylthio) ethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1259 2- (ethylsulfinyl) ethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
[ 1260 2-(ethylsulfonyl)ethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl

116
Table 1(59)
Compound No. Ri Q
1261 2-fluoroethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1262 2,2-difluoroethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1263 2,2,2-trifluoroethyl 2-bromo-6-methyl-4-hepta fluoroisopropylphenyl
1264 l,3-difluoro-2-propyl 2-bromo-6-methyl-4-heptafluoroi5opropylphenyl
1265 l-chloro-3-fluoro-2-propyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1266 1-methyl-2,2,2-trifluoroethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1267 3,3,3-trifluoro-n-propyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1268 2,2,3,3,3-pentafluoro-n-propyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1269 3,3,4,4,4-pentafluoro-2-butyl 2-brorao-6-methyl-4-heptafluoroisopropylphenyl
1270 4,4,4-trifluoro-n-butyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1271 2,2, 3, 3-tetrafluorocyclobutyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1272 2-chloroethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1273 2,2-dichloroethyl 2-bromo-6-methyl-4-heptaf luoroisopropylphenyl
1274 2,2,2-trichloroethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1275 1,3-dichloro-2-propyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1276 3-chIoro-n-propyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1277 2-bromoethyl 2-bromo-6J-methyl-4-heptafluoroisopropylphenyl
1278 2,2,2-tribromoethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1279 3-bromo-n-propyl 2-bromo-6-methyl-4-heptaf luoroisopropylphenyl
1280 | 2-iodoethyl 2 -bromo- 6-methyi- 4 -hepta fluor ois opr opylphenyl

117
Table 1(60)
Compound No. Ri Q
1281 tetrahydrofuran-3-yl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1282 (furan-2-yl)methyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1283 (furan-3-yl)methyl 2-bromo-6-methyl-4-heptafluor6isopropylphenyl

1284 (tetrahydrofuran-2-yl)methyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1285 {tetrahydrofuran-3-yl)methyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl

1286 (thiophen-2-yl) methyl. 2-bramo-6-methyl-4-heptafluoroisopropylphenyl
1287 (thiophen-3-yl)methyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1288 (pyridin-2-yl) methyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1289 (pyridin-3-yl)methyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1290 (6-chloropyridin-3-yl) methyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl
1291 Et 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1292 i-Pr 2-iodo-6-methyl-4-heptafTuoroisopropylphenyl
1293 vinyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1294 propargyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1295 cyclobutyl 2-iodo,-6-methyl-4-heptafluoroisopropylphenyl
1296 cyclopentyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1297 benzyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1298 3-cyanobenzyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1299 4-cyanobenzyl 2-iodo-6-methyl-4-heptaf luoroisopropylphenyl
1300 3-chlorobenzyl 2-iodo- 6-methyl-4-heptaf luoroisopropylphenyl

118 Table 1(61)
Compound No. Rt Q
1301 2-methoxyethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1302 2-cyanoethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1303 2-(methylthio)ethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1304 2-(ethylthio)ethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1305 l-methyl-2- (methylthio) ethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1306 2- (ethylsulfinyl) ethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1307 2-(ethylsulfonyl)ethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1308 2-fluoroethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1309 2,2-difluoroethyl 2-iodo-6-methyl-4-heptaf luoroisopropylphenyl
1310 2,2,2-trif luoroethyl 2-iodo-6-methyl-4-heptaf luoroisopropylphenyl
1311 1,3-difluoro-2 -propyl 2 -iodo- 6-methyl - 4 -hepta f luoroi sopr opylphenyl
1312 l-chloro-3-fluoro-2-propyl 2-iodo-6-methyl-4-heptaf luoroisopropylphenyl
1313 l-methyl-2,2,2-trif luoroethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1314 3,3, 3-trifluoro-n-propyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1315 2,2,3,3,3-pentafluoro-n-propyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1316 3,3,4,4,4-pentaf luoro-2-butyl 2 -iodo- 6-methyl-4 -heptaf luoroisopropylphenyl
1317 4,4,4-trifluoro-n-butyl 2-iodo-6-roethyl-4-heptafluoroisopropylphenyl
1318 2,2,3,3-tetrafluorocyclobutyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1319 2-chloroethyl 2-iodo-6-inethyl-4-heptafluoroisopropylphenyl
1320 2,2-dichloroethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl

119
Table 1(62)
Compound No. Ri Q
1321 2,2,2-trichloroethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1322 1,3-dichloro-2-propyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1323 3-chloro-n-propyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1324 2-bromoethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1325 2,2,2-tribromoethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1326 . 3-bromo-n-propyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1327 2-iodoethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1328 tetrahydrofuran-3-yl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1329 (furan-2-yl) methyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1330 (f uran-3-yl) methyl 2 -iodo-6-methyl-4-heptaf luoroisopropylphenyl
1331 (tetrahydrofuran-2-yl) methyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1332 (tetrahydrofuran-3-yl) methyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1333 (thiophen-2-yl) methyl 2 -iodo-6-methyl-4-heptaf luoroisopropylphenyl
1334 (thiophen-3-yl)methyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1335 (pyridin-2-yl)methyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl
1336 (pyridin-3 -yl) methyl 2-iodo-6-methyl-4-heptaf luoroisopropylphenyl
1337 (6-chloropyridin-3-yl) methyl 2-iodo-6-methyl-4-heptaf luoroisopropylphenyl
.,,„ _ 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl
.,,q . _ 2-iodo-6-n-propyl-4-hepta fluoro
isopropylphenyl
1340 vinyl 2-iodo-6-n-propyl-4-heptafluoro
I isopropylphenyl

120
Table 1(63) ___
Compound No. Ri Q
,_,„., , 2-iodo-6-n-propyl-4-heptafluoro
1341 propargvl . ^ r'. , ,
isopropylphenyl
.,.„ . . . , 2-iodo-6-n-propyl-4-heptafluoro
1342 cyclobutvl r rj r-
- isopropylphenyl
,.,,,_, ,_ . 2-iodo-6-n-propyl-4-heptafluoro
1343 cyclopentyl * " , f
J r isopropylphenyl
, _.. , 2-iodo-6-n-propyl-4-heptafluoro
1344 benzyl . r , , ,
_ isopropylphenyl
..,„,_ ., . 2-iodo-6-n-propyl-4-heptafluoro
1345 3-cyanobenzyl r " . f
isopropylphenyl
.-,,r „ , 2-iodo-6-n-propyl-4-heptafluoro
1346 4-cyanobenzyl . * ". , t;
_ _ isopropylphenyl
._._, . ., _ 2-iodo-6-n-propyl-4-heptafluoro
1347 3-chlorobenzyl . ^ ", , ,
isopropylphenyl
,,„0 _ „. , 2-iodo-6-n-propyl-4-heptafluoro
1348 2-methoxyethyl ^ rjr, , f
isopropylphenyl
.,.. „ J. , 2-iodo-6~n-propyl-4-heptafluoro
1349 2-cyanoethyl . r , . ;
isopropylphenyl
.,c„ „ , .. ,... . . .. . 2-iodo-6-n-propyl-4-heptafluoro
1350 2- (methylthio) ethyl r " . t"
isopropylphenyl
nci -, , ^.i. -H.U- . .-v. i 2-iodo-6-n-propyl-4-heptafluoro
1351 2- (ethylthio) ethyl r ", , ,
_ I s opropylphenyl
.,., . *.u •■ o / ^u -n-v • i ^.1. i 2-iodo-6-n-propyl-4-heptafluoro
1352 l-methyl-2-(methylthio)ethyl r , . t;
_ isopropylphenyl
■nc-, -, , ^.i. i -,.= • i, ^.i. ■■ 2-iodo-6-n-propyl-4-heptafluoro
1353 2-(ethylsulfmyl)ethyl . * , . ,
_ _ isopropylphenyl
.,,-„ _ , ., , , , . . .. ., , 2-iodo-6-n-propyl-4-heptafluoro
1354 2-(ethylsulfonyl)ethyl * . r rjr, . ,
_ _ isopropylphenyl
1355 2-fluoroethyl 2-iodo-6-n-proPyl-4-heptafluoro
isopropylphenyl
1356 2,2-difluoroethyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl
Tjc-i n i •> 4. -ci ..I. n 2-iodo-6-n-propyl-4-heptafluoro
1357 2,2,2-tnfluoroethyl r ", . , _ isopropylphenyl
1358 l,3-difluoro-2-proPyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl
men 1 1.1 -i 4j-i o ■■ 2-iodo-6-n-propyl-4-heptafluoro
1359 l-chloro3-fluoro-2-propyl . ^ " . ;
l s opropylphenyl
n-.cn . ., n _ - _ . . _, ... 2-iodo-6-n-propyl-4-heptafluoro
1360 l-methyl-2,2,2-trifluoroethyl ^ ", . %
I j _ _ I isopropylphenyl

121
Table 1 (64) ____^
Compound No. Ri Q
,,., ,_,.... , 2-iodo-6-n-propyl-4-heptafluoro
1361 3,3,3-tnrluoro-n-propyl • •, u ,
r c isopropylphenyl
,-,,.., ., _ ., , , ^ ., , 2-iodo-6-n-propyl-4-heptafluoro
1362 2,2,3,3,3-pentarluoro-n-propyl . r ", . ,
r r ^ isopropylphenyl
.,,_, , , „ „ „ t ., n i. 4. ! 2-iodo-6-n-propyl-4-heptafluoro
1363 3,3,4,4,4-pentafluoro-2-butyl . r , , ,
___ _ j isopropylphenyl
.,.,.„ „ . . . ... . . , 2-iodo-6-n-propyl-4-heptafluoro
1364 4, 4,4-tnfluoro-n-butyl • , u T
; _ isopropylphenyl
.,„ ., ., •, -, 4- ,. 4=1 , >_ 4. i 2-iodo-6-n-propyl-4-heptafluoro
1365 2,2,3,3-tetrafluorocyclobutyl . r , . f
' _ isopropylphenyl
,,,, „ ., .... 2-iodo-6-n-propyl-4-heptafluoro
1366 2-chloroethyl r ". . ,
isopropylphenyl
,-,„ ., _ .. ., ... , 2-iodo-6-n-propyl-4-heptafluoro
1367 2,2-dichloroethyl . r " . ;
. isopropylphenyl
.,,„ -, T o 4. • i-i 4.1. i 2-iodo-6-n-propyl-4-heptafluoro
1368 2, 2,2-tnchloroethyl . r , ,_ f
i s opr opylphenyl
.,„ , , .. ., „ , 2-iodo-6-n-propyl-4-heptafluoro
1369 l,3-dichloro-2-propyl , , ;
isopropylphenyl
,,_- , .. , 2-iodo-6-n-propyl-4-heptafluoro
1370 3-chloro-n-propyl , «. ,
isopropylphenyl
1371 2-bromoethyl 2-iodo-6-n-propyl-4-heptaflUoro
isopropylphenyl
,-,T-, o -i o 4. -v. 4.1.1 2-iodo-6-n-propyl-4-heptafluoro
1372 2,2,2-tribromoethyl r rj, . f
isopropylphenyl
..,-,, , , , 2-iodo-6-n-propyl-4-heptafluoro
1373 3-bromo-n-propyl , ^ ;
isopropylphenyl
1374 2-iodoethyl 2-iodo-6-n-propyl-4-heptafluoro
isopropylphenyl
1375 tetrahydrofuran-3-yl 2-iodo-6-n-propyl-4-heptafluoro
,_ _ isopropylphenyl
1376 (furan-2-yl)methyl 2-iodo-6-n-proPyl-4-heptafluoro
l s opropylphenyl
,-,.,-, l4= -. .. .. , 2-iodo-6-n-propyl-4-heptafluoro
1377 (furan-3-yl)methyl v "„ , f
isopropylphenyl
1378 (tetrahydrofuran-2ryl)methyl 2-iodo-6:n-proPyl-4-heptafluoro
l s opropylphenyl
i-n„ ,4. 4_ . , , , ,. .. , 2-iodo-6-n-propyl-4-heptafluoro
1379 (tetrahydrofuran-3-yl)methyl ^ " ,_ ;
l s opr opylphenyl
.,.„ .... . _ .. 4, . 2-iodo-6-n-propyl-4-heptafluoro
1380 (thiophen-2-yl)methyl . ^ " ,_ f
J I l s opr opylphenyl

122 Table 1(65)
Compound
No. 2! Q
.... .... . , . , .. . 2-iodo-6-n-propyl-4-heptafluoro
1381 thiophen-3-yl)methyl . r r , , ;
2 _ isopropylphenyl
,-,00 , ... 0 ,. .. , 2-iodo-6-n-propyl-4-heptafluoro
1382 pyndin-2-yl)methyl . r ", , f
J J isopropylphenyl
n-,0-, , ... , ., ,_, , 2-iodo-6-n-propyl~4-heptafluoro
1383 pyndin-3-yl) methyl . r " . f
_ isopropylphenyl
,-„. ., ., . ,, .. , 2-iodo-6-n-propyl-4-heptafluoro
1384 (6-chloropyndin-3-yl methyl . ^ " . f
_ isopropylphenyl

123
Table 2(1)
O
HNA0/Rl
y&"-
X, HNL
4 Q
Xi X2 X3 X4 Ri Q
No. • _^_______
1385 "iiTTTT 2,2,2-trichloroethyl 2-«ethyl-4-heptefluoroisqptopyl
1386 M7W7 ITr 2,6-dimethy-4-heptafluoroisopropyl
phenyl
ino-i .. r, „ „ o o 1 .. ■ v.n .... 1 2,6-dimethyl-4-heptafluoroisopropyl
1387 Me H H H 2,2,2-trichloroethyl J hi
^^ ~~ ~ ~ ~ 2,6-dimethyl-4-heptafluoroisopropyl
phenyl
1389 F "7 "7 H i-Pr 2,6-dimethyl-4-heptafluoroisopropyl phenyl
1390 F777 vinyl 2,6-dimethyl~4-heptafluoroisopropyl phenyl
1391 F H H H propargyl 2,6-diiaethyl-4-^afluoroisoPropyl
1392 7~7~77 cyclobutyl 2,6-dimethyl-4-heptafluoroisoPropyl phenyl
1393 F H H H cyclopentyl 2,6-dimethyl-4-heptafluoroisopropyl J ^ phenyl
1394 F H H H benzyl 2, 6-diinethyl-4-heptafluoroisoProPyl phenyl
1395 F H H H 3-cyanobenzyl 2,6-difl>ethyl-4-^tafluoroisqprppyl
1396 777^ 4-cyanobenzyl 2,6-din,ethyl-4-heptafluoroisoProPyl phenyl
1397 F H H H 3-chlorobenzyl 2,6~dimethyl-4-heptafluoroisopropyl phenyl
1398 F H H H 2-methoxyethyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl
1399 F H H H 2-cyanoethyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl
1400 F H H H 2-(methylthio)ethyl 2, e-dimethyl^-heptafluoroisopropyl
11)11 _ I phenyl

124 Table 2(2)
Compound I „ P f~ T~ I I I
N"o_ X, X, X3 X, Rl Q
1401 F H H H 2-(ethylthi)ethyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
1402 F H H H l-methyl-2^(methylthio)- 2, 6-dmethyl-4-heptafluoroisopropylphenyl
1403 F H H H 2-(ethylsulfinyl)ethyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
1404 F H H H 2-(ethylsulfonyl)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1405 F H H H 2-fluoroethyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
1406 F H H H 2,2-difluoroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1407 F H H H 2,2,2-trifluoroethyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
1408 F H H H 1,3-difluoro-2-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1409 F H H H l-chloro-3-fluoro-2- 2,6-dimethyl-4-heptafluoroisopropylphenyl
1410 F H H H l-»ethyl-2,2,2-tnfluoro 2,6-dimethyl-4-heptafluoroisopropylphenyl ethyl _
1411 F H H H 3,3,3-trifluoro-n-propyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
1412 F H H H 2,2,3,3,3-pentafluoro-n- 2,6-dimethyl-4-heptafluoroisopropylphenyl
1413 F H H H 3,3,4,4,4^entafluoro-2- 2,6-diraethyl-4-heptafluoroisopropylphenyl
1414 F H H H 4,4,4-trifluoro-n-butyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
1415 F H H H 2,2,3,3-tetrafluoro 6-dimethyl-4-heptafluoroisopropylphenyl cyclobutyl
1416 F H H H 2-chloroethyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
1417 F H H H 2,2-dichloroethyl 2,6-dimethyl-4-heptaf luoroisopropylphenyl
1418 F H H H 2,2,2-trichloroethyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
1419 F H H H l,3-dichloro-2-propyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
1420 F H H H 3-chloro-n-propyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl |

125
Table 2 (3)
Compound I I I I ~ I ~
No AI X2 X3 X, R[ Q
1421 F H H H 2-bromoethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1422 F H H H 2,2,2-tribromoethyl 2, 6-dlmethyl-4-heptafluoroisopropylphenyl
1423 F H H H 3-bromo-n-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1424 F H H H 2-idoethyl 2, 6-dimethyl-4-heptafluoroisopropylphenyl
1425 F H H H tetrahydrofuran-3-yl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1426 F H H H (furan-2-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1427 F H H H (furan-3-yl)methyl 2,6-dimethyl-4-heptaf luoroisopropylphenyl
1428 F H H H (tetrahydrofuran-2- 2,6-dimethyl-4-heptafluoroisopropylphenyl
yl) methyl
1429 F H H H (tetrahydrofuran-3- 2,6-dimethyl-4-heptafluoroisopropylphenyl
1430 F H H H (thiophen-2-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1431 F H H H (thiophen-3-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1432 F H H H (pyridin-2-yl)methyl 2,6-dimethyl-4-heptaf luoroisopropylphenyl
1433- F H H H (pyridin-3-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1434 F H H H (6-chloropyridin-3- 2,6-dimethyl-4-heptafluoroisopropylphenyl yl) methyl __
1435 F H H H Et 2,6-dimethyl-4- (nonafluoro-2-butyl) phenyl
1436 F H H H i-Pr 2,6-dimethyl-4- (nonafluoro-2-butyl) phenyl
1437 F H H H vinyl 2, 6-dimethyl-4- (nonaf luoro-2-butyl) phenyl
1438 F H H H propargyl 2,6-dimethyl-4- (nonaf luoro-2-butyl) phenyl
1439 F H H H cyclobutyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl
1440 F H H H cyclopentyl 2,6-dimethyl-4- (nonaf luoro-2-butyl) phenyl

126 Table 2(4)
Compound „ „ |~ |~~i
^0 *i *2 X3 X< Rl Q
144! F H H H benzyl 2, 6-dimethyl-4-(nonafluoro2-butyl)
phenyl
1442 F H I H H 3-cyanobenzyl 2, 6-dimethyl-4-(nonafluoro2-butyl) phenyl
1443 F H H H 4-cyanobenzyl 2, 6-dimethyl-4-(nonafluoro2-butyl) phenyl
1444 F H H H 3-chlorobenzyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl
1445 F H H H 2-methoxyethyl 2, 6-dimethyl-4-(nonafluoro2-butyl) _ phenyl
, „„, in „ ,. „ _ ,_. , 2,6-dimethyl-4-(nonafluoro2-butyl)
1446 F H H H 2-cyanoethyl J J
phenyl
1447 F H H H 2- (methylthio) ethyl 2,6-dimethyl-4^nonafluoro2-butyl)
1448 rWl 2-(ethylthio)ethyl 2,6-dimethyl-4-(nonafluoro2-butyl)
J J phenyl
,„.„ „ „ „ „ , ,. , - , ,_,_ , ,. . , ^.. , 2, 6-dimethyi-4-(nonafluoro2-butyl)
1449 F H H H l-methyl-2- (methylthio) ethyl hi
,.c„ _ ,. „ .. _ , .. , ,-• ,, ,, , 2,6-dimethyl-4-(nonafluoro2-butyl)
1450 F H H H 2-(ethylsulfinyl)ethyl hi
1451 rVT~ii 2-(ethylsulfonyl)ethyl 2,6-dimethyl-4-monafluoro2-butyl)
1452 rV~~ii 2-fluoroethyl 2, 6-dijnethyl-4- 2,6-dimethyl-4-heptafluoroisopropylphenyl (methylthio) ethyl J_
1403 F H H H 2-(ethylsulfinyl)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1404 F H J H H 2-(ethylsulfonyl)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl ]

128
Table 2(6)
Compound II I I ~ 1 ~
No x ^
1481 F H H H (6-chloropyridin-3-yl) 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl
1482 F H H__J Et 2, 6-dichloro-4-(heptafluoro-n-propylthio)phenyl
1483 F H H H i-Pr 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
1484 F H H H vinyl 2, 6-dichloro-4- (heptaf luoro-n-propylthio) phenyl
1485 F H H H cyclobutyl 2, 6-dichloro-4- (heptaf luoro-n-propylthio) phenyl
1486 F H H H cyclopentyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
1487 F H H H 3-cyanobenzyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
1488 F H H H 4-cyanobenzyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
1489 F H H H 2-cyanoethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
1490 F H H H 2-(methylthio)ethyl 2, 6-dichloro-4-(heptafluoro-n-propylthio)phenyl I 1491 F H H H 2- (ethylthio) ethyl 2,6-dichloro-4- (heptaf luoro-n-propylthio) phenyl
1492 F H H H l-methyl-2-(methylthio) 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
ethyl
1493 F H H H 2-(ethylsulfinyl)ethyl 2,6-djchloro-4-(heptafluoro-n-propylthio)phenyl
1494 F H H H 2-fluoroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
1495 F H H H 2, 2-difluoroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
1496 F H H H 2,2,2-trifluoroethyl 2, 6-dichloro-4-(heptafluoro-n-propylthio)phenyl
1497 F H H H 1,3-difluoro-2-propyl 2,6-dichloro-4-(heptafluoro-n-propylthio) phenyl
1498 F H H H l-chloro-3-fluoro-2- 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl propyl
1499 F H H H l-methyl-2,2,2- 6-dichloro-4-(heptafluoro-n-propylthio) phenyl trxf luoroethyl
1500 F H H H 3,3,3-trifluoro-n-propyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl

129
Table 2(7)
Compound „ ,, I
NfQ_ Xi X2 X3 X, Ri Q
1501 F H H H ' '""' ' ^ 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
1502 F H H H 4,4,4-trifluoro-n-butyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
1503 F H H H 2,2,3,3-tetrafluorocyclo 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
1504 F H H H . 2-chloroethyl 2,6-dichloro-4- (heptafluoro-n-propylthio) phenyl
1505 F H H H 2,2-dichloroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
1506 F H H H 2,2,2-trichloroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
1507 F H H H 1,3-dichloro-2-propyl 2,6-dichloro-4- (heptafluoro-n-propylthio)phenyl
1508 F H H H 3-chloro-n-propyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
1509 F H H H 2-bromoethyl 2, '6-dichloro-4- (heptafluoro-n-propylthio)phenyl
1510 F H H H 3-bromo-n-propyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
1511 F H H H 2-iodoethyl 2, 6-dichloro-4-(heptafluoro-n-propylthio)phenyl
1512 F H H H (6-chloropyridin-3-yl) 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl methyl
1513 F H H H Et 2,6-dibromo-4-(trifluoromethylsulfonyl) phenyl
1514 F H H H i-Pr 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
' 1515 F H H H vinyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
1516 F H H H cyclobutyl 2, 6-dibromo-4-(trifluoromethylsulfonyl)phenyl
1517 F H H H cyclopentyl 2,6-dibromo-4- (trifluoromethylsulfonyl)phenyl
1518 F H H H 3-cyanobenzyl 2,6-dibromo-4- (trifluoromethylsulfonyl) phenyl
1519 F H H H 4-cyanobenzyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
1520 F H H H J 2-cyanoethyl 2,6-dibromo-4- (trifluoromethylsulfonyl) phenyl

130 Table 2(8)
Compound 1 1 No_ *i *2 -*3 X, Rt Q
1521 F H H H 2- (methylthio) ethyl 2, 6-dibromo-4- (trifluoromethylsulfonyl)phenyl
1522 F H H H 2- (ethylthio) ethyl 2, 6-dibromo-4- (trifluoromethylsulfonyl) phenyl
1523 F H H H 1-methyl-2Hmethylthio) 2, 6-dibromo-4-(trifluoromethylsulfonyl)phenyl
1524 F H H H 2- (ethylsulfinyl) ethyl 2, 6-dibromo-4- (trifluoromethylsulfonyl)phenyl
1525 F H H H 2-fluoroethyl 2, 6-dibromo-4-( trifluoromethylsulfonyl (phenyl
1526 F H H H 2,2-difluoroethyl 2, 6-dibromo-4-(trifluoromethylsulfonyl)phenyl
1527 F H H H 2,2,2-trifluoroethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
1528 F H H H 1, 3-difluoro-2-propyl 2, 6-dibromo-4- (trifluoromethylsulfonyl)phenyl
1529 F H H H l-chloro-3-fluoro-2-propyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
1530 F H H H l-methyl-2/2,2-tnfluoro 2, 6-dibromo-4-(trifluoromethylsulfonyl)phenyl ethyl
1531 F H H H 3,3,3-trifluoro-n-propyl 2, 6-dibromo-4-(trifluoromethylsulfonyl)phenyl
1532 F H H H 2,2,3,3,3-pentafluoro-n- 6-dibromo-4-(trifluoromethylsulfonyl)phenyl propyl ___^
1533 F H H H 4,4,4-trifluoro-n-butyl 2, 6-dibromo-4-(trifluoromethylsulfonyl)phenyl
1534 F H H H 2,2,3,3-tetrafluorocyclo 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
butyl -
1535 F H H H 2-chloroethyl 2,6-dibromo-4- (trifluoromethylsulfonyl) phenyl
1536 F H H H 2,2-dichloroethyl 2,6-dibromo-4- (trifluoromethylsuj-fonyl) phenyl
1537 F H H H 2,2,2-trichloroethyl 2,6-dibromo-4- (trifluoromethylsulfonyl)phenyl
1538 F H H H l,3-dichloro-2-propyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
1539 F H H H 3-chloro-n-propyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl
1540 F H H H 2-bromoethyl 2,6-dibromo-4- (trifluoromethylsulfonyl)phenyl

131 Table 2(9)
Compound I ., T~~ T~~ |~~ T I
jf0 *i X2 X3 X, R4 Q
1541 F_ H K H 3-bromo-n-propyl 2, 6-dibromo-4- (trifluoromethylsulfonyl)phenyl
1542 F H H H 2-iodoethyl 2, 6-dibro jx' 1 Ri I Q
1601 F H H H 3-chloro-n-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio) phenyl
1602 F H H H 2-bromoethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
1603 F H H H 3-brom.o-n-propyl 2,6-dibtomo-4- (heptafluoro-n-propylthio) phenyl
1604 F H H H 2-iodoethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
1605 F H H H (6-chloropyridm-3-yl) ■ 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl methyl
1606 F H H H Et 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1607 F H H H i-Pr 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1608 F H H H vinyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1609 F H H H cyclobutyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1610 F H H H cyclopentyl 2, 6-dibromo-4-(heptafluoroisopropylthio)phenyl
1611 F H H H 3-cyanobenzyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1612 F__ H H H 4-cyanobenzyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1613 F H H H 2-cyanoethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1614 F H H H 2-(methylthio)ethyl 2, 6-dibromo-4- (heptafluoroisopropylthio) phenyl
1615 F H H H 2-(ethylthio)ethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1616 F H H H l-methyl-2HmethylthLO) 2,6-dibromo-4-(heptafluoroisopropylthio) phenyl
1617 F H H H 2-(ethylsulfinyl)ethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1618 F H H H 2-fluoroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1619 F^ H H H 2, 2-difluoroethyl 2, 6-dibromo-4- (heptafluoroisopropylthio) phenyl
1620 F^ H H H 2, 2,2-trifluoroethyl 2, 6-dibromo-4- (heptafluoroisopropylthio) phenyl

135
Table 2(13)
Cor™d I x, I x_ I X3 | x. ' * I Q
1621 F H H H l,3-difluoro-2-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1622 F H H H l-chloro-3-fluoro2-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1623 F H H H l-methyl-2,2,2-trifluoro 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
ethyl ^ ____
1624 F H H H 3,3,3-trifluoro-n-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1625 F H H H 2,2,3,3,3-pentafluoro-n- 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl __ propyl
1626 F H H H 4,4,4-trifluoro-n-butyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1627 F H H H 2,2,3,3-tetrafluorocyclo 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1628 F H H H 2-chloroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1629 F H H _H 2,2-dichloroethyl 2, 6-dibromo-4- (heptafluoroisopropylthio) phenyl
1630 F H H _H 2,2,2-trichloroethyl 2, 6-dibromo-4- (heptafluoroisopropylthio) phenyl
1631 F H H H l,3-dichloro-2-propyl 2,6-dibroroo-4-(heptafluoroisopropylthio)phenyl
1632 F H H H 3-chloro-n-propyl 2, 6-dibromo-4- (heptafluoroisopropylthio) phenyl
1633 F H H H 2-bromoethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1634 F H H H 3-bromo-n-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1635 F H H H 2-iodoethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl
1636 F H H H (6-chloropyridm-3-yl) 2,6-dibromo-4-(heptafluoroisopropylthio) phenyl
1637 F H H H Et 2,6-dimethyl-4- (heptaf luoro-n-propylthio) phenyl
1638 F H H H i-Pr 2, 6-dimethyl-4- (heptafluoro-n-propylthio) phenyl
1639 F H H H vinyl 2,6-dimethyl-4-(heptafluoro-n-propylthio) phenyl
| 1640 [ F H H | H cyclobutyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl

136 Table 2(14)
Compound I TT VZ\T, ' I I r>
No. * [ X* | x' A< R- Q
1641 F K H H cyclopentyl 2,6-di.methyl-4-(heptafluoro-n-propylthio)phenyl
1642 F H H H 3-cyanobenzyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
1643 F H H H 4-cyanobenzyl 2,6-dimethyl-4- (heptafluoro-n-propylthio) phenyl
1644 F H H H 2-cyanoethyl 2,6-dimethyl-4- (heptafluoro-n-propylthio) phenyl
1645 F H H H 2- (methylthio) ethyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio) phenyl
1646 F H H H 2-(ethylthio)ethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
1647 F H H H l-methyl-2-friethylthio) 2,6-dimethyl-4- (heptafluoro-n-propylthio) phenyl
1648 F H H H 2-(ethylsulfinyl)ethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
1649 F H H H 2-fluoroethyl 2,6-dimethyl-4- (heptafluoro-n-propylthio) phenyl
1650 F H H H 2,2-difluoroethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
1651 F H H H 2,2,2-trifluoroethyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio) phenyl
1652 F H H H 1,3-difluoro-2-propyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
1653 F H H H l-chloro-3-fluoro-2-propyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
1654 ■ F H H H l-methyl-2,2, 2-trifluoro 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
1655 F _ H H H 3,3,3-trifluoro-n-propyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
1656 F H H H 2,2,3,3,3-pentafluoro-n- 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
1657 F H H H 4,4,4-trifluoro-n-butyl 2,6-dimethyl-4- (heptafluoro-n-propylthio) phenyl
1658 F H H H 2,2,3,3-tetrafluorocyclo 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
1659 F H H H 2-chloroethyl 2,6-dimethyl-4- (heptafluoro-n-propylthio) phenyl
1660 | F | H J H j H 2,2-dichloroethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl

137
Table 2(15)
cToomd 1x* h Hx* [ I Q ~
1661 F H H H 2, 2, 2-trichloroethyl 2, 6-dimethyl-4- (heptafluoro-n-propylthio) phenyl
1662 F H R H 1,3-dichloro-2-propyl 2,6-diroethyl-4-(heptafluoro-n-propylthio)phenyl
1663 F H H H 3-chloro-n-propyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
1664 F H H H 2-bromoethyl 2, 6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
1665 F H H H 3-bromo-n-propyl 2, 6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
1666 F H H H 2-iodoethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl
1667 F H H H (6-chloropyridin-3- 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl yl) methyl _
1668 F H H H 2,2,2-trichloroethyl 2, 6-dichloro-4- (trifluoromethylsulfinyl)phenyl
1669 F H H H 2,2,2-trichloroethyl 2,6-dibromo-4-(trifluoromethylsulfinyl)phenyl
1670 F H H H 2,2,2-trichloroethyl 2,6-dichloro-4-(pentafluoroethylsulfinyl)phenyl
1671 F H H H 2,2,2-trichloroethyl ' 2,6-dibromo-4-(pentafluoroethylsulfinyl)phenyl
1672 F H H H 2,2,2-trichloroethyl 2,6-dichloro-4-(pentafluoroethylsulfonyl)phenyl
1673 F H H H 2,2,2-trichloroethyl 2,6-dibromp-4-(pentafluoroethylsulfonyl)phenyl
1674 T"W^ 2,2,2-trichloroethyl 2' ^^°^^£^^^^yl
1675 TW1 2,2,2-trichloroethyl 2,6-dibromo-4- (heptafluoro-n-propyl ' sul f myl) phenyl
1676 F H H H 2,2,2-trichloroethyl 2-chloro-6-methyl-4-(nonafluoro-2-butyl) phenyl
1677 F H H H 2,2,2-trichloroethyl 2-bromo-6-methyl-4- (nonafluoro-2-butyl) phenyl
1678 F H H H 2,2,2-trichloroethyl 2-iodo-6-methyl-4-(nonafluoro-2-butyl)phenyl
1679 F H H H 2,2,2-trichloroethyl 2,6-dichloro-4-(nonafluoro-2-butyl)phenyl
1680 F H H H 2,2,2-trichloroethyl 2,6-dibromo-4-(nonafluoro-2-butyl) phenyl

138 Table 2(16)
Compound I „ |~ „ I Y I ~ I T
Ho. A1 2 3 4 ' Q
liroi I ~ ~ ~ ~~ I 2-chloro-4-methyl-6-(1, 1,1,3,3,3-hexaf luoro
I obi F H H H Et ■ , , ■ , • ^ -i
isopropyloxy) pyno.in-3-yl
•168' ~F W~~H H i^Pr 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
~_ . isopropyloxy) pyridin-3-yl
1683 F H H H vinyl 2-chloro-4-methyl-6-(1,1,1,3,3 3-hexafluoro
_ isopropyloxy) pyndin-3-yl
ieo„ c ■, w »- ! 2-chloro-4-methyl-6- (1,1,1,3,3,3-hexafluoro
1684 F H H H cyclobutyl , . . .. , ,
J__ * isopropyloxy) pyndin-3-yl
1CQC. _. „ „ . , 2-chloro-4-inethyl-6-(1,1,1,3,3,3-hexafluoro
1685 F H H H cyclopentyl . , , . .. , ..
J c ■* isopropyloxy) pyridm-3-yl
,„, ~T~ „ „ ~Z I I i 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1686 F H H H 3-cyanobenzyl , . •,,. , ■,
J_ 2 isopropyloxy) pyndiri-3-yl
,„n _ „ . 2-chloro-4-methyl-6- (1,1,1,3,3,3-hexafluoro
1687 F H H H 4-cyanobenzyl , , ... , ,,
_ J isopropyloxy) pyridin-3-yl
ncoD u ^ ZT~, 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1688 F H H H 2-cyanoethyl . 2 , . . ,. , ,
_ _ isopropyloxy) pyridin-3-yl
icon ^ u „ u , , ,. ,,.. . , „. . 2-chloro-4-methyl-6- (1,1,1,3,3,3-hexafluoro
1689 F H H H 2- (methylthio)ethyl ■',...._. J J isopropyloxy) pyndin-;.-yl
1690 F H H H 2-(ethylthio)ethyl 2Tehidro-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
J J isopropyloxy) pyndin-j-yl
1CQ1 „ „ „ „ l-methyl-2-(methylthio) 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
lOjl r H n n .. , . , . ■ *■ -i i
ethyl isopropyloxy) pyridin-3-yl
Tcm c- n u u o , «.i. , w -n -i. i 2-chloro-4-methyl-6- (1,1,1,3,3,3-hexafluoro
1692 F H H H 2- ethylsulfinyl)ethyl , \ •_,• -, n J J J isopropyloxy) pyridm-3-yl
1693 F H H H 2-fluoroethyl 2-chloro-4-methyl-6-(1,1,1,3,3 3-hexafluoro isopropyloxy) pyridin-3-yl
,,». „ „ „ ,, _ ,.„ ., , 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1694 F H H H 2,2-difluoroethyl . J , . ... , , ' _ isopropyloxy) pyridin-3-yl
1695 F H H H 2,2,2-trifluoroethyl 2-chloro-4-methyl-6-(1,1,1,3,3 3-hexafluoro isopropyloxy) pyndin-3-yl
ncoc *• u v u i r, J-*! o i 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1696 F H H H l,3-difluoro-2-propyl . , , • _,• -> ■,
' J isopropyloxy) pyridin-3-yl
icm r. u u u i ui o jri o i 2-chloro-4-methyl-6-(l,1,1,3,3,3-hexafluoro
1697 F H H H l-chloro-3-fluoro-2-propyl J , , ... 1 ,
J isopropyloxy) pyridin-3-yl
,,.. „ „ „ ' l-methyl-2,2,2-trifluoro 2-chloro-4-methyl-6-(l,1,1,3,3,3-hexafluoro
ethyl isopropyloxy) pyridin-3-yl
ICQQ r-uuu ■* ■> ■> ^ ■ *i i 2-chloro-4-methyl-6- (1,1,1,3,3,3-hexaf luoro
1699 F H H H 3,3,3-trifluoro-n-propyl . J , ' . .. ' ,
r isopropyloxy) pyridm-3-yl
1700 F H H 2,2,3,3,3-pentafluoro-n- 2-chloro-4-methyl-6-(l,1,1,3,3,3-hexafluoro
I I [ I I propyl isopropyloxy) pyridin-3-yl

139 Table 2(17)
Compound | I I I " ■ "
No. 1
7^ Z 7, 7 7, 7TTT~T^ I i I 2-chloro-4-methyl-6- (1,1,1,3,3,3-hexafluoro
1701 F H H H 4,4,4-trifluoro-n-butyl . J . . ... , ,
^ isopropyloxy) pyndin-3-yl
1?02 F H H H 2,2,3,3-tetrafluoro 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
, cyclobutyl isopropyloxy) pyridin-3-yl
nm ii T v.i <-K ! 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1703 F H H H 2-chloroethyl . , . ,. , , _ isopropyloxy) pyndm-3-yl
1704 F H H H 2,2-dichloroethyl 2-chloro-4-methyl-6-(1,1,1,3,3 3-hexafluoro
' isopropyloxy) pyndin-3-yl
nnc „ u ,,,,..,,. vv, , 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1705 F H H H 2,2,2-trichloroethyl , , , . ,. , ,
_ * isopropyloxy) pyridin-3-yl
i-inc =. i ? J- ui -, , 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1706 F H H H l,3-dichloro-2-propyl J . . ... , ,
' r rj isopropyloxy) pyridin-3-yl
n„T „ „ „ u , ., , 2-chloro-4-methyl-6- (1,1,1,3,3,3-hexafluoro
1707 F H H H 3-chloro-n-propyl . . , n
y " isopropyloxy) pyridin-3-yl
nno „ _. .. , 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1708 F H H H 2-bromoethyl . , , , .
isopropyloxy) pyridm-3-yl
nnQ „ „ „ „ , . , 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1709 F H H H 3-bromo-n-propyl J , .. ■ _,-,■, r rj . isopropyloxy) pyridm-3-yl
1710 F H H H 2-iodoethyl 2-chloro-4-methyl-6-(l,1,1,3,3 3-hexafluoro _ isopropyloxy) pyridin-3-yl
nn „ „ „ „ (6-chloropyridin-3-yl) 2-chloro-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
methyl isopropyloxy) pyridin-3-yl
1712 F H H H Et 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy) pyridin-3-yl
,-,,., „ „ „ „ . „ 2-bromo-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
XflJ t n n n l-Fr . . - . .,._.,
isopropyloxy)pyridin-3-yl
,,,. _ . 2-bromo-4-methyl-6-(l, 1,1,3,3, 3-hexafluoro
1714 F H H H vinyl . J , , ... ' , isopropyloxy) pyridin-3-yl
1715 F H H H cyclobutyl 2-bromo-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
• _ isopropyloxy) pyridin-3-yl
,,,, _ „ ,, „ , . , 2-bromo-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
1716 F H H H cyclopentyl J , ....-, ,
isopropyloxy) pyridin-3-yl
nn c.uuu r, i-i 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1717 F H H H 3-cyanobenzyl . J , , ' . ' ,
isopropyloxy) pyridin-3-yl
nno _ „ ,. „ „ , 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1718 F H H H 4-cyanobenzyl J . ' ... ' . _ isopropyloxy) pyndm-3-yl
1719 F H H H 2-cyanoethyl 2-bromo-4-methyl-6-(1 1,1,3,3 3-hexafluoro _ _ isopropyloxy) pyridin~3-yl
1720 F H H H 2-(methylthio)ethyl 2-bromo-4-methyl-6-(l 1,1,3,3 3-hexafluoro
I | I [ I [ isopropyloxy) pyndin-3-yl

140
Table 2(18)
Compound | ,, | X; | ^ | ^ | Ri | ' ~
7^-, Z „ Z n , ^ ,tt. , ^ , I 2-bromo-4-methyl-6- (1,1,1,3,3,3-hexaf luoro
nZl F H H H 2-(ethylthio ethyl . . . . .. -, ,,,
J J isopropyloxy) pyndin-3~yl
7 l-methyl-2-(msthylthio) 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
ethyl isopropyloxy) pyridin-3-yl
-,-,,.-, „ „ „ „ „ , _. ...... ,. _. . 2-bromo-4-methyl~6-(1,1,1,3,3,3-hexafluoro
1723 F H H H 2-(ethylsulfinyl)ethyl , , . .. , ,
* 3 J isopropyloxy) pyndin-3-yl
T,-}A v u u "u -> f, tt , 2-bromo-4-methyl-6- (1,1,1,3,3,3-hexaf luoro
1724 F H H H 2-fluoroethyl . , , -JOT
__^ isopropyloxy) pyndin-3-yl
mc !. -, n ,,•*, „.. i 2-bromo-4-methyl-6-(l,l,l,3,3,3-hexafluoro
1725 F H H H 2,2-difluoroethyl , . ... , .
' * isopropyloxy) pyridm-3-yl
,.,.,, „ „ „ „ _ „ _ . . ,, ... 2-bromo-4-methyl-6-( 1,1,1,3,3,3-hexaf luoro
1726 F H H H 2,2,2-trifluoroethyl ■> ,„ _-,i ■ „ -> ,i
J isopropyloxy) pyndin-3-yl
,,0, „ „ „ „ , , ..-, „ , 2-bromo-4-methyl-6~(1,1,1,3, 3,3-hexafluoro
1727 F H H H 1,3-difluoro-2-propyl . J . . ■ .. -. ,
' ^ ^3 isopropyloxy) pyridin-3-yl
,,,. ,, „ „ „ . .. , ., _ , 2-bromo-4-methyl-6-(l,l,l,3,3,3-hexafluoro
1728 F H H H l-chloro-3-fluoro-2~propyl . J , . ... , ,
F *J isopropyloxy) pyridm-3-yl
172g l-methyl-2,2,2-trifluoro 2-brorao-4-methyl-6-(1,1,1,3,3,3-hexafluoro
ethyl isopropyloxy) pyridin-3-yl
mn ,, -, -, , _ .*, , 2-bromo-4-methyl-6-(1,1,1,3, 3,3-hexafluoro
1730 F H H H 3,3,3-trifluoro-n-propyl . , . .. , ,
_J_ y yj isopropyloxy) pyridin-3-yl
..,,., „ 2,2,3,3,3-pentafluoro-n- 2-bromo-4-methyl-6-(l,1,1,3,3,3-hexafluoro
1/jJ.tnnn , . II-J.-IT
propyl isopropyloxy) pyridin-3-yl
,™ „ „ „ „ . . . . .., . . , 2-bromo-4-methyl-6-(l,l,l,3,3,3-hexafluoro
1732 F H H H 4,4,4-trifluoro-n-butyl . J , . ......
_ isopropyloxy) pyridin-3-yl
1733 2,2,3,3-tetrafluoro 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
cyclobutyl isopropyloxy) pyridin-3-yl
,,,, „ „ „ ,. .. , 2-bromo-4-methyl-6-(1,1,1,3,3, 3-hexafluoro
1734 F H H H 2-chloroethyl J , , . .. _, .
J_ isopropyloxy) pyridm-3-yl
,-,„,- _ „ „ „ OOJ-UI ^UT 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1735 F H H H 2,2-dichloroethyl . J , , ■ _■•-,,
' * isopropyloxy) pyridin-3-yl
n-,, r u „ „ 00-.4.-V1 ,-u-i 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1736 F H H H 2,2,2-trichloroethyl J , . , ,
_ isopropyloxy) pyridin-3-yl
,„. _ ,. . ^ .. .. „ . 2-bromo-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
1737 F H H H l,3-dichloro-2 -propyl ' , ,_,•-,-,
[ r rj isopropyloxy) pyridin-3-yl
,„. „ „ „ -, .. n 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1738 F H H H 3-chloro-n-propyl . J , . , ,
r J isopropyloxy) pyridm-3-yl
,,,„ „ „ „ „ _. .. , 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1739 F H H H 2-bromoethyl J , . . ,. _ .
isopropyloxy) pyridm-3-yl
._.. _ - . , 2-bromo-4-methyl-6-(l,1,1,3,3,3-hexafluoro
1740 F H H H 3-bromo-n-propyl J , , ■_,-,-,
L__1__I__L_J isopropyloxy) pyridin-3-yl

141
Table 2(19)
CTo°Und 1 * 1 * I x, k 1 F, 1 Q
1741 r777" 2-iodoeth^ 2-bromo-4-methyl-6-(1 1,1,3,3 3-hexafluoro ~
^ isopropyloxy) pyndm-3-yi
17 _ (6-chloropyridin-3-yl) 2-bromo-4-methyl-6-(1,1, 1, 3, 3, 3-hexafluoro
methyl isopropyloxy) pyridin-3-yl
2-iodo-4-methyl-6-(1,1,1,3,3, 3-hexafluoro
isopropyloxy) pyndm-3-yl
,-,,. _ . „ 2-iodo-4~niethyl-6-(1,1,1,3,3,3-hexafluoro
1744 F H H H i-Pr , , •_,• -, ■>
isopropyloxy)pyndin-3-yl
ni5 „ . 2-iodo-4-methyl-6- (1,1,1,3,3,3-hexafluoro
1745 F H H H vinyl . , ... ., ,
isopropyloxy) pyndin-3-yl
„,, „ , , ^ , 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1746 F H H H cyclobutyl . . . . .. , ,
_ isopropyloxy) pyridin-3-yl
.-,.., _ ■, ^ , 2-iodo-4-methyl-6-(l,l, 1,3,3,3-hexafluoro
1747 F H H H cyclopentyl . -',...,,
J * J isopropyloxy) pyridm-3-yl
,-,.„ „ , . . 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1748 F H H H 3-cyanobenzyl J . . ... , ,
_ * isopropyloxy) pyridm-3-yl
■,->„□ „ . x. , 2-iodo-4-methyl-6- (1,1,1,3,3,3-hexafluoro
1749 F H H H 4-cyanobenzyl . J , ; ... , ,
_ * . isopropyloxy) pyndin-3-yl
,-,tn „ „ .. . 2-iodo-4-methyl-6- (1,1,1,3,3,3-hexafluoro
1750 F H H H 2-cyanoethyl . , , ■_,• •, ,
•* isopropyloxy) pyridin-3-yl
nti ,, , , t, 14, . . ... , 2-iodo-4-methyl-6- (1,1,1,3,3,3-hexafluoro
1751 F H H H 2-(methylthio ethyl a . , ... , , J J isopropyloxy) pyridin-3-yl
1752 F H H H 2-(ethylthio) ethyl 2-iodo-4-tnethyl-fr- (1,1,1,3,3,3-hexafluoro J isopropyloxy) pyndm-3-yl
1753 p l-methyl-2-(methylthio) 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro ethyl isopropyloxy) pyridin-3-yl
nci c u t, o o , 4.x. i i«- ,> 4-v. i 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1754 F H H H 2-(ethylsulfmyl) ethyl . * ,;'.-, , ~ J isopropyloxy) pyridm-3-yl
1755 F H H H 2-fluoroethyl 2-iodo-4-methyi-6-(1,1,1,3,3,3-hexafluoro isopropyloxy) pyridm-3-yl
1756 F H H H 2,2-difluoroethyl 2-iodo-4-«thyl-6- (1,1,1,3,3,3-hexafluoro
' isopropyloxy) pyridin-3-yl
1757 F H H H 2,2,2-trifluoroethyl 2-iodo-4-methyl-6-(1 1,1,3,3,3-hexafluoro
' isopropyloxy) pyridm-3-yl
TTCQ ,-. •, -. -,*•, -, i 2-iodo-4-methyl-6- (1,1,1,3,3,3-hexafluoro
1758 F H H H 1,3-difluoro-2-propyl . 2 , , ■ _,' -, ,
e isopropyloxy) pyndin-3-yl
nco u ti „ i v.i -> *i - ■, 2-iodo-4-methyl-6- (1,1,1,3,3,3-hexafluoro
1759 F H H H l-chloro-3-fluoro-2-propyl J ,,._,., , r isopropyloxy) pyridin-3-yl
1760 F H H l-methyl-2,2,2-trifluoro 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
[ I ethyl isopropyloxy) pyridin-3-yl

142
Table 2(20) ____^
cXundhHx'H RI 1 Q
1761 rWl 3,3,3-trifluoro-n-propyl 2-iodc-4-methyl-6- (1 1,1,3,3,3-hexaf luoro
r rj isopropyloxy) pynam-3-yl
17g2 ~ ~~~ ~ 2,2,3,3,3-pentafluoro-n- 2-iodo-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
propyl isopropyloxy 1 pyridin-3-yl __
,.,,, ~ ~ ~ ~ .„._.„ , . , 2-iodo-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
1763 F H H H 4,4, 4-tnfluoro-n-butyl . J . . ... , ,
' isopropyloxy) pyndin-3-yl
17g F H H H 2,2,3,3-tetrafluoro 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
cyclobutyl isopropyloxy) pyridin-3-yl
1765 F H H H 2-chloroethyl 2-iodo-4-«thyl-6- (1,1,1,3,3,3-hexafluoro
isopropyloxy) pyndin-3-yl
„« ~lT~^r u u o n A- >,-, 4-v. ! 2-iodo-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
1766 F H H H 2,2-dlchloroethyl . . . . ,. , ,
' J_ isopropyloxy) pyndin-3-yl
,-,,-, 0 „ „ „ , _ , t . ., „., 2-iodo-4-methyl-6-(l,1,1,3,3,3-hexafluoro
1767 F H H H 2,2,2-trichloroethyl . J , •_>• -> ,
2 isopropyloxy) pyridin-3-yl
nco c „ „ i -, ,,• V1 o , 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1768 F H H H 1,3-dichloro-2-propyl . J , . ... , ,
[ J isopropyloxy) pyridin-3-yl
,,,. _ „ „ , ., , 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1769 F H H H 3-chloro-n-propyl J ,,...., n
r rj isopropyloxy) pyridxn-3-yl
T-,™ „ , . .. , 2-iodo-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
1770 F H H H 2-bromoethyl . J , ; ... -, ,
^ _ isopropyloxy) pyndm-3-yl
i-m „ -, . , 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro
1771 F H H H 3-bromo-n-propyl * . ... -, n
r J isopropyloxy) pyridin-3-yl
1772 V H H H 2-iodoethyl 2-iodo-4:methyl-6-(1 1,13,3,3-hexafluoro
• isopropyloxy) pyridm-3-yl
1773 H (6-chloropyridin-3-yl) 2-iodo-4-methyl-6-(l, 1,1,3,3,3-hexafluoro
methyl isopropyloxy) pyridin-3-yl
i-77/i p u H H ir,- 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy)pyridin-3-yl
•mq p u H u < w 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
isopropyloxy) pyricb.n-3-yl
1776 F H H H vinyl 2,4-dimethyl-6-(1,1, 1,3,3,3-hexafluoro isopropyloxy) pyridin-3-yl
1777 F H H H cyclobutyl 2,4-dimethyl-6-(l, 1 1,3,3,3-hexafluoro isopropyloxy) pyridm-3-yl
1778 F H H H cyclopentyl 2,4-dimethyl-6-(l,l 1,3 3,3-hexafluoro isopropyloxy) pyndin-3-yl
„,. _ ., , 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
1779 F H H H 3-cyanobenzyl ' J ,'.'_,,
isopropyloxy) pyridin-3-yl
non c . ,_ •. 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
1780 F H H H 4-cyanobenzyl ' .. J ,..',.,
II isopropyloxy) pyridm-3-yl

143
Table 2(21)
CONo°Und U U I x, I x< | KL [ o
■ 1781 I F ~7W 2-cyanoethyl 2,4-dimethyl-6- (1,1 1,3 3,3-hexafluoro
_ * isopropyloxy) pyndin- 3 -yl
,,„, ~ " Z ~ ~ «.. .... . . „. , 2,4-dimethyl-6-(l,1,1,3,3,3-hexafluoro
1782 F H H H 2-(methylthio)ethyl . , . . .. , ,
J J isopropyloxy) pyndin-3-yl
n„ „ „ ~ T~ n , *-v i-v.- , ^ , 2,4-dimethyl-6- (1,1,1,3,3,3-hexafluoro
1783 F H H H 2-(ethylthio ethyl , . ... , ,
J * isopropyloxy) pyndm-3-yl
TIOA cut, „ , «.u , - , ... ltu. , <_u , 2,4-dimethyl-6-(1,1,1,3, 3, 3-hexafluoro
1184 F H H H l-methyl-2- (methylthio) ethyl isopropyloxy) pyridin-3-yl
not r. „ u „ o , 4-v. -, ■,*• i, -u -, 2,4-dimethyl-6-(1,1,1,3,3, 3-hexafluoro
1785 F H H H 2- (ethylsulfmyl)ethyl . J . ,-.,•-,,
■* J i J isopropyloxy) pyndm-3-yl
noc r. T u T „ ,. .. , ~ 2, 4-dimethyl-6-(1,1,1,3,3, 3-hexafluoro
1786 F H H H 2-fluoroethyl J . . .,.-..
_ isopropyloxy) pyndm-3-yl
n en ~~I u Z 7" TTTTi IT"! 2,4-dimethyl-6-(l,l,l,3,3,3-hexafluoro
1787 F H H H 2,2-difluoroethyl isopropyloxy) pyridin-3-yl
1788 F H H H 2,2,2-trifluoroethyl 2,4-dimethyl-6-(1,1 1,3,3,3-hexafluoro
_ _ isopropyloxy) pyridm-3-yl
noQ r. , -, j•*, \ i 2,4-dimethyl-6-(l,1,1,3,3,3-hexafluoro
1789 F H H H 1,3-difluoro-2-propyl . . , , ,
' r *2 isopropyloxy) pyridin-3-yl
nan r. ■,,.■, -i «i o i 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
1790 F H H H l-chloro-3-fluoro-2-propyl . , . . .. , , ^ ^J isopropyloxy) pyridin-3-yl
1791 F H H l-methyl-2,2,2-trifluoro 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro ethyl isopropyloxy) pyridin-3-yl
TJO-3 r. a t, , , , t ... , 2,4-dimethyl-6- (1,1,1,3,3,3-hexafluoro
1792 F H H H 3,3,3-trifluoro-n-propyl J ' .... ,,
J isopropyloxy) pyridin-3-yl
17g3 F H H H 2,2,3,3,3-pentafluoro-n- 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
propyl isopropyloxy) pyridin-3-yl
,,.. _ „ „ „ „ . . . .,, , <_ , 2,4-dimethyl-6-{1,1,1, 3,3, 3-hexafluoro
1794 F H H H 4,4,4-trifluoro-n-butyl . . /•_,■-, ,
' * isopropyloxy) pyridin-3-yl
17g5 F H H H 2,2,3,3-tetrafluoro 2,4-diinethyl-6-(l, 1,1,3,3,3-hexafluoro
cyclobutyi isopropyloxy) pyridin-3-yl
1796 F H H H 2-chloroethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy) pyridm-3-yl
1797 F H H H 2,2-dichloroethyl 2,4-dimethyl-6-(l,l 1,3 3,3-hexafluoro
' isopropyloxy) pyridin-3-yl
1798 F H H H 2,2,2-trichloroethyl 2,4-diinethyl-6-(1,1,1,3,3,3-hexafluoro
_ isopropyloxy) pyridm-3-yl
T-JQQ c- i r, J- v.i o •, 2,4-dimethyl-6- (1,1,1,3,3,3-hexafluoro
1799 F H H H 1,3-dichloro-2-propyl . 2 ,,■.-,■,
' c isopropyloxy) pyridm-3-yl
,.„„ _ „ „ „ , .. , 2,4-dimethyl-6-(l, 1,1,3,3,3-hexafluoro
1800 F H H H 3-chloro-n-propyl . J ,.._,.,,
( isopropyloxy) pyridin-3-yl

144
Table 2(22)
Compound I I I II " I
No.
TTZi Z _ _ _ TT ZT", 2,4-dimethyl-6-(l, 1,1,3,3,3-hexafluoro
1801 F H H H 2-bromoethyl . J , , ... , ,
_ xsopropyloxy) pyridm-3-yl
lon-> r u u u -5 K I 2' 4-dimethyl-6- (1,1,1,3,3,3-hexafluoro
1802 F H H H 3-bromo-n-propyl ' , . ■ _,■-> ,
r rJ xsopropyloxy) pyridm-3-yl
1803 F H H H 2-iodoethyl 2, 4-dimethyl-6-(l, 1,1,3 3,3-hexafluoro
xsopropyloxy) pyndm-3-yl
1804 F H H H (6-chloropyridin-3-yl) 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro
methyl isopropyloxy) pyridin-3-yl
1805 F H H H Et 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl
1806 F H H H i-Pr 2-bromo-4-methyl-6-(heptafluoro
isopropyl)pyridin-3-yl
1807 F H H H vinyl 2-bromo-4-methyl-6-(heptafluoro
isopropyl) pyrxdin-3-yl
lono c u u u ■, v- *. i 2-bromo-4-methyl-6-(heptafluoro
1808 F H H H cyclobutyl . / . .. _,
isopropyl) pyndin-3-yl
■tona c- u u u T .- i 2-bromo-4-methyl-6-(heptafluoro
1809 F H H H cyclopentyl . , / ._._-,
isopropyl) pyridin-3-yl
,.,„ „ „ , . . 2-bromo-4-methyl-6-(heptafluoro
1810 F H H H 3-cyanobenzyl ■■ ,, •-)• %, ,
isopropyl) pyridin-3-yl ■
ion „ . _ 2-bromo-4-methyl-6-(heptafluoro
1811 F H H H 4-cyanobenzyl ,/ ... *1 ,
isopropyl) pyridin-3-yl
it,.,., _ „ „ „ - .. . 2-bromo-4-methyl-6- (heptafluoro
1812 F H H H 2-cyanoethyl , / . .. *1
isopropyl)pyriain-3-yl
mn ^ u u u o > 4.u i ^u ■ < 4.w i 2-bromo-4-methyl-6-(heptafluoro
1813 F H H H 2-(methylthio) ethyl , / . ' *1 ,
■ isopropyl) pyridm-3-yl
1814 F H H H 2-(ethylthio)ethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl) pyridin-3-yl
1815 F H H H l-methyl-2-(methylthio) 2-bromo-4-methyl-6-(heptafluoro
ethyl isopropyl) pyridin-3-yl
1816 F H H H 2-(ethvlsulfinyl)ethyl 2-bromo-4-iaethyl-6-(heptafluoro _ isopropyl) pyridin-3-yl
1817 F H H H 2-fluoroethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl )pyridin-3-yl
1818 F H H H 2,2-difluoroethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl) pyridin-3-yl
im a c- u t, u o->-it-*i ^-ti 2-bromo-4-methyl-6-(heptafluoro
1819 F H H H 2,2,2-tnfluoroethyl , ,J .,.*!,
isopropyl) pyridin-3-yl
1820 F H H H l,3-difluoro-2-propyl 2-bromo-4-methyl-6-(heptafluoro
I I I I I I isopropyl )pyridin-3-yl

145
Table 2(23)
Compound | ^ x I I x I ~ | "
No. |
nD_. „ „ „ „ " ~ _ ., ~ " 2-bromo-4-methyl-6-(heptafluoro
1821 F H H H l-chloro-3-fluoro-2-propyl ,, J- ■> i
r vl isopropyl) pyridin-3-yl
, „„„ . , , . „, , 2-bromo-4-methyl-6-(heptafluoro
1822 F H H H l-methyl-2,2,2-tnfluoroethyl isopropyl )Pyridin-3-yl
1823 F H H T| 3,3,3-trifluoro-n-propyl 2-bro_-4~methyl-6-(heptafluoro
_J_ ^ KJ isopropyl) pyridin-3-yl
,.,. - _ , _, , _ ., n 2-bromo-4-methyl-6-(heptafluoro
1824 F H H H 2,2,3,3,3-pentafluoro-n-propyl . ,, ...%,.
' ' • ' ** f " isopropyl)pyridin-3-yl
TOOC r. ,. ,. /■ *. ■.=■> _ ^ •. 2-bromo-4-methyl-6-(heptafluoro
1825 F H H H 4,4,4-trifluoro-n-butyl ,. ... , ,
'_J_ *_ isopropyl) py r idm-3 -yl
,.,, _ „ „ „ , o -a , _ t «, i v. 4. n 2-bromo—methyl-6-(heptafluoro
1826 F ^__^ H 2,2,3,3-tetrafluorocyclobutyl isopropyl) pyridin-3-yl
1827 F H H H 2-chloroethyl 2-bromo-4-methyl-6-(heptafluoro
_ isopropyl) pyridin-3-yl
,„. „ _ _ .. . , .. , 2-bromo-4-methyl-6-(heptafluoro
1828 F H H H 2,2-dichloroethyl , . ... , .
' _ isopropyl i pyridin-3-yl
.... _ „ „ „ _ _ „ . . . , .. , 2-bromo-4-methyl-6-(heptafluoro
1829 F H H H 2.2,2-trichloroethyl ,. . ,. , ,
* isopropyl) pyndin-3-yl
noon . t. » „ „ i o -.• v.i o ■. 2-bromo-4-methyl-6-(heptafluoro
1830 F H H H l,3-dichloro-2-propyl . , . . .. , ,
r ^J isopropyl) pyridin-3-yl
,.„ „ „ „ „ , ,. , 2-bromo-4-methyl-6- (heptafluoro
1831 F H H H 3-chloro-n-propyl . ,, . ,. , .
r rj isopropyl) pyridm-3-yl
,„-,,, _ _ . .. , 2-bromo-4-methyl-6-(heptafluoro
1832 F H H H 2-bromoethyl . , , ■ J • r. i
isopropyl) pyndin-3-yl
.„_, _ _ . , 2-bromo-4-methyl-6-(heptafluoro
1833 F H H H 3-bromo-n-propyl , , . ,. %, ,
r ^J isopropyl) pyridin-3-yl
, 0,„ _ -,_,_■, 2-bromo-4-methyl-6-(heptafluoro
1834 F H H H 2-lodoethyl . . / ... *1 ,
_ isopropyl) pyridm-3 -yl
.„,,- „ , ,. ., • _,--,,,_, 2-bromo-4-raethyl-6-(heptafluoro
1835 F H H H (6-chloropyridin-3-yl)methyl isopropyl)pyridin-3-yl
1836 F H H H Et ' 2-chloro:6-methyl-4- heptafluOroisopropylphenyl
1837 F H H H i-Px „ 2-chloro-6-_thyl-4- heptafluOroisopropylphenyl
.... _ „ . . 2-chloro-6-methyl-4-
1838 F H H H vinyl ,___■, , L.
heptafluOroisopropylphenyl
,„. _, , , . . 2-chloro-6-methyl-4-
1839 F H H H cyclobutyl . ,_ _, . J, ,
_ heptafluOroisopropylphenyl
To.r, r, i ^ -i 2-chloro-6-tnethyl-4-
1840 F H H H cyclopentyl . ^ _, , ,
| | | | I I heptaf luo roi s op r opylpheny 1

146
Table 2(24)
Compound I I I I ~ I -
No.
777, I ~ 7 ~ T ~ ~ 2-chloro-6-methyl-4-heptafluoroisopropyl
1841 F H H H 3-cyanobenzyl J phenyl
7777 Z ~ ~ ~ " T ~ 2-chloro-6-methyl-4-heptafluoroisopropyl
1842 F H H H 4-cyanobenzyl phenyl
,.., „ ~7. Z Z I I7~7 2-chloro-6-methyl-4-heptafluoroisopropyl
1843 F H H H 2-cyanoethyl * phenyl
1844 ^VVl 2-(methylthio)ethyl 2-chloro-6-methyl-4-heptafluoroisoProPyl
1845 F~VV7 2-lethylthiOethyl 2-chl0ro-6-methyl-4-hePtafluoroisopropyl 10„, _ ~7J T ~ l-methyl-2-(methylthio) 2-chloro-6-methyl-4-heptafluoroisopropyl
xo4b c n ri n , , ,
ethyl phenyl
1847 F H H H 2-(ethylsulfinyl)ethyl 2-chloro-6-methyl-4-heptafluoroisopropyl
1848 r771 2-fluoroethyl 2-chloro-6-methyl-4-heptafluoroiSopropyl
1849 r TV 7 2,2-difluoroethyl 2-chloro-6-methyl-4-heptafluoroisopropyl
1850 TVV7 2,2,2-trifluoroethyl 2-chloro-6-methyl-4-heptafluoroiSoproPyl
,„, „ , , ..„ I T 2-chloro-6-methyl-4-heptafluoroisopropyl
1851 F H H H 1,3-difluoro-2-propyl hi
1oco ^ ~7 77 , ., I " 2-chloro-6-methyl-4-heptafluoroisopropyl
1852 F H H H l-chloro-3-fluoro-2-propyl hi
.„,.., „ l-methyl-2,2,2- 2-chloro-6-methyl-4-heptafluoroisopropyl
IOJJ tnnn .„,, , ,
tnfluoroethyl phenyl
ioc/1 r-uut, , , , t .„ , 2-chloro-6-methyl-4-heptafluoroisopropyl
1854 F H H H 3,3,3-trifluoro-n-propyl hi
,.„ _ „ „ „ 2,2,3,3,3-pentafluoro-n- 2-chloro-6-methyl-4-heptafluoroisopropyl
J.oD^> r n H H , , ,
propyl phenyl
IOCC r. „ « ,r » ,. .. ^ -.ci ^ .. i 2-chloro-6-methyl-4-heptafluoroisopropyl
1856 F H H H 4,4,4-trifluoro-n-butyl J . , "
phenyl
.QCT c, „ „ „ 2,2,3,3-tetrafluoro 2-chloro-6-methyl-4-heptafluoroisopropyl
cyclobutyl phenyl
1858 F H H H 2-chloroethyl 2-chloro-6-methyl-4-heptafluoroisoPropyl phenyl
1859 F H H H 2,2-dichloroethyl 2-chloro-6-methyl-4-heptafluoroisoPropyl phenyl
1860 F H H H 2,2,2-trichloroethyl 2-chloro-6-Inethyl-4-heptafluoroisopropyl
[ | | | I ' I phenyl

147
Table 2(25)
cTund 1 x>-1x* 1x* 1x<1 R* 1 Q ~
1861 F H H H 1,3-dichloro-2-propyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1862 F H H H 3-chloro-n-propyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1863 F H H H 2-bromoethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1864 F H H H 3-bromo-n-propyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1865 F H H H 2-iodoethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl
1866 F H H H (6-chloropyridin-3-yl) 2-chloro-6-methyl-4-heptafluoroisopropylphenyl methyl _
1867 ~V ~~ H K 2-iodo-6-n-proPyl-4-heptafluoro
l s opropylphenyl
1868 F H H H i-Pr 2-iodo-6-n-proPyl-4-heptafluoro
isopropylphenyl
' 1869 F H H H vinyl 2-iodo-6-n-prppyl-4-heptafluoro
_ isopropylphenyl
io-,n r, ■, ■_ ^ T 2-iodo-6-n-propyl-4-heptafluoro
1870 F H H H cyclobutyl ■, ,_ ;
isopropylphenyl
IQTI ~ „ o „ i .. i 2-iodo-6-n-propyl-4-heptafluoro
1871 F H H H cyclopentyl ■> ,_ f
J ^ isopropylphenyl
1In, _ „ „ „ , , . 2-iodo-6-n-propyl-4-heptafluoro
1872 F H H H 3-cyanobenzyl . , . f
isopropylphenyl
,»,, „ „ „ . , 2-iodo-6-n-propyl-4-heptafluoro
1873 F H H H 4-cyanobenzyl . r rj. . ,
_ isopropylphenyl
,„,. „ ,, „ ., _ .. , 2-iodo-6-n-propyl-4-heptafluoro
1874 F H H . H 2-cyanoethyl r rl. , f
isopropylphenyl
,.,, _ „ „ „ _ , ^. .... . .. . 2-iodo-6-n-propyl-4-heptafluoro
1875 F H H H 2-(methylthio) ethyl c CJ, , ; isopropylphenyl
1876 F H H H 2-(ethylthio)ethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl
i ai-i TT u v u l-methyl-2- (methylthio) 2-iodo-6-n-propyl-4-heptaf luoro
ethyl isopropylphenyl
•IO-IO - i, i, u o , ■.!. ■, -,.= • ■, , *.,. ■, 2-iodo-6-n-propyl-4-heptafluoro
1878 F H H H 2-(ethylsulfinyl)ethyl . r rJ, . f 2 J isopropylphenyl
1879 F H H H 2-fluoroethyl 2-iodo-6:n-propyl-4-hePtafluoro _ isopropylphenyl
1880 F H H H 2,2-difluoroethyl 2-iodo-6-n-propyl-4-heptafluoro
I I I I I ( isopropylphenyl

148
Table 2(26)
COTo°Und U 1 x, U 1 x, 1 R. 1 Q
1881 7~~~H 2,2,2-trifluoroethvl 2-iodo-6-n-propyl-4-heptafluoro
' ■* isopropylphenyl
, „ . , 2-iodo-6-n-propyl-4-heptafluoro
1882 F H H H l,3-difluoro-2-propyl ■ i v, ■>
r " j. sopropylphenyl
1M, _ " ~ T~Z o i 2-iodo-6-n-propyl-4-heptafluoro
1883 F H H H l-chloro-3-fluoro-2-propyl . , . ,
r " i sopropylphenyl
,OQ. _ l-methyl-2,2,2-trifluoro 2-iodo-6-n-propyl-4-heptafluoro
loo** cnnn ,, , IT_T
ethyl isopropylphenyl
,„„ _ ,,,.... , 2-iodo-6-n-propyl-4-heptafluoro
1885 F H H H 3,3,3-tnfluoro-n-Propyl isopropylphenyl
1QQC „ 2,2,3,3,3-pentafluoro-n- 2-iodo-6-n-propyl-4-heptafluoro
looo tnnn , . -i i_ ■*
propyl isopropylphenyl
loo-, ^ „ „ ,, , . . ^ ■*, ^ x. •, 2-iodo-6-n-propyl-4-heptafluoro
1837 F H H H 4,4,4-tnfluoro-n-butyl isopropylphenyl
noOQ -.„„., 2,2,3,3-tetrafluoro 2-iodo-6-n-propyl-4-heptafluoro
cyclobutyl isopropylphenyl
1889 F H H H 2-chloroethyl 2-iodo-6:n-propyl-4-heptafluoro
isopropylphenyl
1890 V H V H 2,2-dichloroethyl 2-iodo-6:n-propyl-4-heptafluoro isopropylphenyl
1891 V H H H 2,2,2-trichloroethyl ' 2-iodo-6:n-propyl-4-heptafluoro _ isopropylphenyl
,.., „ •, -, j- v., o ■, 2-iodo-6-n-propyl-4-heptafluoro
1892 F H H H l,3-dichloro-2-propyl r , . ,
rj isopropylphenyl
,M, „ _ ,, , 2-iodo-6-n-propyl-4-heptafluoro
1893 F H H H 3-chloro-n-propyl . , . f isopropylphenyl
1894 F H H H 2-broaoethyl 2-iodo-6:n-propyl-4-heptafluoro _ isopropylphenyl
none ^ a ,t „ -, i. ■, 2-iodo-6-n-propyl-4^heptafluoro
1895 F H H H 3-bromo-n-propyl r vi i- isopropylphenyl
1896 F H H H 2-iodoethyl 2-i0do-6-n-proPyl-4-heptafluor0
isopropylphenyl
,.., _ „ ,, „ , _ ., . .. .. ,, ., , 2-iodo-6-n-propyl-4-heptafluoro
1897 F H H H (6-chloropyndin-3-yl)methyl . r , , _ '__ isopropylphenyl
1898 CI H H H i-Pr 2-methyl-4-heptafluoroisopropylphenyl
1899 CI H H H 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl
1900 CI H H H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl

• 149 Table 2(27)
-Compound I Xl I x I x I x, | Rl I Q
1901 CI H H H 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1902 CI H H H 2,2,2-trichloroethyl 2,4-bistrifluoromethylphenyl
1903 CI ~ H H 2,2,2-trichloroethyl 2-(1,1,1,3 3,3-hexafluoroisopropyloxy, ' _ . -4-methylpyridin-5-yl
1904 Br H H H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl
1905 Br H H H 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl

1906 F F H H 2,2,2-trichloroethyl 2-methyl-4-heptaf luoroisopropylphenyl
1907 F F H H 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1908 F_ F F H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl
1909 H_ Me H H i-Pr 2-methyl-4-heptaf luoroisopropylphenyl
1910 H Me H H 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl
1911 H Me H H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl I 1912 H Me H H 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1913 H MeO H H i-Pr 2-methyl-4-heptafluoroisopropylphenyl
1914 H MeO H H 2,2,2-trichloroethyl 2-me thyl-4-heptaf luoroisopropylphenyl
1915 H F H H i-Pr 2-methyl-4-heptafluoroisopropylphenyl
1916 H F H H 2,2,2-trichloroethyl 2 -methyl - 4 -hepta f luorois opropylphenyl
1917 H F H H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl
1918 H F H H 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1919 H CI H H i-Pr 2-methyl-4-heptafluoroisopropylphenyl
1920 H CI H H 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl

150
Table 2(28)
Compound I I I I | ~ ~
No. Xt A2 Xj X< ^ ~
1921 H CI H H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl
1922 H CI H H 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1923 H H Me H 2,2,2-trichloroethyl 2,6-dimethyl-4~heptafluoroisopropylphenyl
1924 H H CF3 H i-Pr 2-methyl-4-heptafluoroisopropylphenyl
1925 H H CF3 H 2,2,2-trichloroethyl 2-methyl-4-heptafluoroi5opropylphenyl
1926 H H CF3 H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl
1927 H H CF3 H 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1928 H H NH2 H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl
1929 H H MejN H 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1930 H H H Me i-Pr 2-methyl-4-heptaf luoroisopropylphenyl
1931 H H H Me 2,2,2-trichloroethyl 2-me thyl-4-heptaf luoroisopropylphenyl
1932 H H H Me i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl
1933 H H H Me 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1934 H H H F i-Pr 2 -methyl-4-heptaf luoroisopropylphenyl
1935 H H H F 2,2,2-trichloroethyl 2-methyl-4-heptaf luoroisopropylphenyl
1936 H H H F i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl
1937 H H H F 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1938 H H H CI i-Pr 2-methyl-4-heptaf luoroisopropylphenyl
1939 H H H CI 2,2,2-trichloroethyl 2-methyl-4-heptaf luoroisopropylphenyl
| 1940 H H H CI i-Pr | 2,6-dimethyl-4-heptaf luoroisopropylphenyl

151 Table 2 (continued)
Compound I I I I I " | 7
Ai X2 X3 X4 Rx U
1941 H H H CI 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl
1942 H H H Br i-Pr 2-rnethyl-4-heptafluoroisopropylphenyl
1943 H H H Br 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl
1944 H H H I 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl
1945 H H H I i-Pr 2,6-dirnethyl-4-heptafluoroisopropylpheayl
1946 H H H I t-Bu 2-methyl-4-heptafluoroisopropylphenyl
1947 [ H H H I 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl ~| •

152
Table 3
O
R7^ A /Ri 2 NO
^YV*1 (I-C)
^ T T
X4 N_
4 / Q R3
Compound | Xl | X2 | X3 | X) | Ri | Rl | Rj | Q ~~
1948 7~^ H H 2,2,2-trichloro ~ ~ 2,6-dibromo-4-■ (heptafluoro
_ ethyl n-prop.ylthio) phenyl ^___
1949 H H H H 2,2,2-trichloro fl Mg 2-methyl-4-heptafluoroisopropyl
ethyl phenyl
1950 H H H H i-Pr H Me 2,6-dimethyl-4-hePtafluoroisopropyl
phenyl
,„,. „ „ „ „ 2,2,2-trichloro „ „ 2,6-dimethyl-4-heptafluoroisopropyl
xyoX n n n H . , , n Me , ,
ethyl phenyl
2-me thyl-6-chloro~4-
1952 H H H H i-Pr H Me heptafluoroisopropyl
phenyl
_,,... 2-methyl-6-chloro-4-
1953 H H H H A ^-tricruoro H Me heptafluoroisopropyl
_ phenyl
1954 H H H H i-Pr H Me 2-methyl-6-bromo-4-heptafluoroisoproPyl
• phenyl
1955 H H 2,2,2-trichloro 2-methyl-6-bromo-4-heptafluoroisopropyl
ethyl . phenyl
,„,-, „ „ „ „ 2,2,2-trichloro „ _. 2,6-dimethyl-4-heptafluoroisopropyl
J.3JD n n ri n H c.t . .,
ethyl phenyl
I(1„ „ „ „ „ 2,2,2-trichloro rT . 2,6-dimethyl-4-heptafluoroisopropyl
lyD/ n n n n H JL—Fr L _
ethyl phenyl
,ai-0 „ „ „ ., 2,2,2-trichloro ., „ 2,6-dimethyl-4-heptafluoroisopropyl
JLyoo n n ri n Me n * ,
.- ___^_ _^^__ ■. phenyl
nQ[-Q _ „ ., 2,2,2-trichloro w „ 2,6-dimethyl-4-heptafluoroisopropyl
lyoy r ri ri n ^, , Me n ^ ,
ethyl . phenyl
1960 H H MeNH H i-Pr Me H 2,6-dimethyl-4-heptafluoroisopropyl
I | | | | [ | | phenyl

153
Table 4
G1
HhAGrRi
«v ™
Q
Compound No. Gi G2 G3 Ri Q
1961 O S 0 Me 2,6-dJ.methyl-4-heptafluoroisopropylphenyl
1962 0 S 0 Et 2, 6-dJ.methyl-4-heptafluoroisopropylphenyl
1963 0 O S iPr 2,6-dimethyl-4-heptafluoroisopropylphenyl
1964 0 O S 2,2,2-trichloro 2,6-dimethyl-4-heptafluoroisopropylphenyl

154
Table 5(1)
O
R,^ A /Ri ^ N O
A^A, (1-E)
A-AfY°
H%
Compound Ai fl2 A3 A, Ri R2 Q
No.
1965 N C C C i-Pr H 2-methyl-4-heptafluoroisopropylphenyl
1966 N C C C 2,2,2-trichloroethyl H 2-methyl-4-heptafluoroisopropylphenyl
1967 N C C C i-Pr H 2,6-dimethyl-4-heptafluoroisopropyl
phenyl
1968 N C C C 2,2,2-trichloroethyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl
1969 N ' C ' C C 2-chloroethyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl
1970 N C C C H 2,6-dimethyl-4-heptafluoroisopropyl
_ phenyl
1971 N C C C H 2,6-dimethyl-4-heptafluoroisopropyl
phenyl
1972 N ~~C C~~ C H 2,6-dimethyl-4-heptafluoroisopropyl _ phenyl
1973 NCGC lbtl H 2, 6-dimethyl-4-heptafluoroisopropyl _ _ phenyl .
1974 NCCC 1 t 1 H2,6-dimethyl-4-heptafluoroisopropyl CyC °pen y phenyl
1975 NCCC hi H 2,6-dimethyl-4-heptafluoroisopropyl _ _ phenyl
1976 NCCC hi H2,6-dimethyl-4-heptafluoroisopropyl _ _ phenyl
1977 NCCC „_ . . H 2,6~dimethyl-4-heptafluoroisopropyl _ phenyl
.1978 NCCC 2_(methylthio)etnyl H 2, 6-^methyl-4-tep^afluoroisopropyl
1979 N c""^ C~" 2-(ethvlthio)ethvl 5 2,6-dimethyl-4-heptafluoroisopropyl -* * phenyl
1980 NCCC l-methyl-2- H 2, 6-dimethyl-4-heptafluoroisopropyl I (methylthio) ethyl phenyl

155
Table 5(2)
Compound ?.i A, A3 A4 Rt R2 J Q
No. _^
1981 N C C C .,, ^ ,-,.= •■,■_. , H 2,6-dimethyl-4-heptafluoroisopropyl
2-(ethylsulfinyl)etnyl y phenyl
1982 N C C C „ ,, ~~.' K 2,6-dimethyl-4-heptafluoroisopropyl
2-fluoroethyl u i
I phenyl
1S83 N C C C 2-ri'fl th H 2, 6-dimethyl-4-heptafluoroisopropyl
' _ phenyl
1984 N C C C „ „ -, ^ -^ ._,-•, H 2,6-dimethyl-4-heptafluoroisopropyl 2,2,2-tnfluoroethyl phenyl
1985 NCCC ,,.,.,=, o ■, H 2,6-dimethyl-4-heptafluoroisopropyl l,3-difluoro-2-propyl | phenyl
1986 NCCC l-chloro-3-fluoro-2- H 2,6-dimethyl-4-heptafluoroisopropyl . propyl phenyl
1987 NCCC l-methyl-2,2,2-trifluoro H 2,6-dimethyl-4-heptafluoroisopropyl ethyl phenyl
1988 NCCC ,,,„..„ , H 2,6-dimethyl-4-heptafluoroisopropyl
3,3,3-trifluoro-n-propyl u T
_ c " phenyl
1989 NCCC 2,2,3,3,3-pentafluoro-n- H 2,6-dimethyl-4-heptafluoroisopropyl . propyl phenyl
1990 N C C C . , .. . ... ,__■, H 2,6-dimethyl-4-heptafluoroisopropyl
4,4,4-trifluoro-n-butyl i_ ,
■_ J phenyl
1991 N ~C C C 2,2,3,3-tetrafluoro H 2,6-dimethyl-4-heptafluoroisopropyl cyclobutyl phenyl
1992 NCCC hloroeth 1 H 2,6-dimethyl-4-heptafluoroisopropyl '_ _ phenyl
1993 NCCC hloro-2- o 1 H 2,6-dimethyl-4-heptafluoroisopropyl
' ■ ' p py phenyl
1994 NCCC , ., ,' H 2,6-dimethyl-4-heptafluoroisopropyl
3-chloro-n-propyl ' v. n
r J phenyl
1995 NCCC H 2,6-dimethyl-4-heptafluoroisopropyl _ phenyl
1996 NCCC H 2,6-dimethyl-4-heptafluoroisopropyl
y phenyl
1997 NCCC H 2,6-dimethyl-4-heptafluoroisopropyl _ phenyl
1998 NCCC (6-chloropyridin-3-yl) H~ 2,6-dimethyl-4-heptafluoroisopropyl methyl phenyl
1999 NCCC H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl
2000 NCCC H 2,6-dimethyl-4-(nonafluoro-2-butyl)
I I _. phenyl

156 Table 5(3)
Compound P.i A2 A3 A4 Rj R2 Q
Ho. __
2001 N C C C . , H 2,6-dimethyl-4-(nonafluoro-2-butyl)
vinyl , ,
' phenyl
2002 ~N C C C TTTT^ i H 2,6-dimethyl-4-(nonafluoro-2-butyl)
cyclobutyl phenyl
2003 N C C C ,. , H 2,6-dimethyl-4-(nonafluoro-2-butyl) cyclopentyl phenyl
2004 N C C I C „ H 2,6-dimethyl-4-(nonafluoro-2-butyl)
3-cyanobenzyl . , .
* _ phenyl
2005 ~N C C C ~ " " H 2,6-dimethyl-4-(nonafluoro-2-butyl)
4-cyanobenzyl
2006 N C C C I ~~ H 2,6-dimethyl-4-{nonafluoro-2-butyl) 2-cyanoethyl phenyl
2007 N C C C , , iU ,tw, , tv , H 2,6-dimethyl-4-(nonafluoro-2-butyl)
2-(methylthio)ethyl hi
2008 N C C C _ , lL ,_.. . _. . H 2,6-dimethyl-4- (nonafluoro-2-butyl) 2-(ethylthlo)ethyl | phenyl __
2009 N C C C l-methyl-2- (methylthio) H 2,6-dimethyl-4-(nonafluoro-2-butyl) . ethyl ; phenyl
2010 NCCC _ , „. , ... , , ^. , H 2,6-dimethyl-4-(nonafluoro-2-butyl)
2-(ethylsulfinyl)ethyl J phenyl
2011 N-~C C C „ „ ~~\ H 2,6-dimethyl-4- (nonafluoro-2-butyl)
2-fluoroethyl J , .
_ phenyl
2012 N ~~C C C „ _ .._, ~\ H 2,6-dimethyl-4-(nonafluoro-2-butyl) 2,2-dxfluoroethyl phenyl
2013 N C C C 2,2,2-trifluoroethyl H 2,6-dimethyl-4-(nonafluoro-2-butyl)
2014 N C C C ~77 ^ ~, H 2,6-dimethyl-4- (nonafluoro-2-butyl) l,3-difluoro-2-proPyl ^ phenyl
2015 ~N C C C " ~ _ „ ~ " H 2,6~dimethyl-4-(nonafluoro-2-butyl)
l-chloro-3-fluoro-2-propyl hi
2016 N C C C l-methyl-2,2,2-trifluoro H 2,6-diroethyl-4-(nonafluoro-2-butyl) ethyl phenyl
2017 NCCC , , , _ ..*, , H 2,6-dimethyl-4-(nonafluoro-2-butyl) 3,3,3-tnfluoro-n-propyl | pnenyl
2018 NCCC 2,2,3,3,3-pentafluoro-n- H 2, 6-dimethyl-4-(nonafluoro-2-butyl) propyl phenyl
2019 NCCC , . . ^ ■*■, ,, _ ■, H 2,6-diniethyl-4-(nonafluoro-2-butyl)
4,4, 4-trifluoro-n-butyl hi
2020 N C~~C C 2,2,3,3-tetrafluoro H 2,6-dimethyl-4- (nonafluoro-2-butyl)
cyclobutyl phenyl

157 Table 5(4)
Compound A; A2 | A3 A~] R^ RT~ Q
No.
,.,, „ _ _ I „ . .. „. , „ 2,6-dimethyl-4-(nonafluoro-2-butyl)
2021 N C C C 2-chloroethyl H h vl
,m, „ _ _ _ __,... .. . „ 2,6-dimethyl-4-(nonafluoro-2-butylj
2022 N C C C 2,2-dlchloroethyl H hi
,„„ „ _ . _ _ . . ,. .. , „ 2,6-dimethyl-4-(nonafluoro-2-butyl)
2023 N C C C 2,2,2-trichloroethyl H h vl
,„.. „ ~ ~ „ .,,.,,, I i „ 2,6-dimethyl-4-(nonafluoro-2-butyl)
2024 N C C C l,3-dichloro-2-propyl H , -,
' r rj phenyl
,.,, „ , ., , „ 2,6-dimethyl-4-(nonafluoro-2-butyl)
2025 N C C C 3-chloro-n-propyl H J . .
* rJ phenyl
,mc „. „ _ . .. . „ 2,6-dimethyl-4-(nonafluoro-2-butyl)
2026 N C C C 2-bromoethyl H hi
,„„ ,. ... , „ 2,6-dimethyl-4-(nonafluoro-2-butyl)
2027 N C C C 3-bromo-n-propyl H . ,
r ^J phenyl
2028 N T"T~C 2-iodoethyl JT 2, e-dimethyl-4-(nonafluoro-2-butyl)
phenyl
2029 N (6-chloropyridin-3-yl) 2,6-dimethyl-4-(nonafluoro-2-butyl) methyl . phenyl , ,
2030 N C C C Et H 2, 6-dibromo-4-(heptafluoro-n- propylthio)phenyl
2031 N C C ~C Z*r H~ 2, 6-dibromo-4-(heptafluoro-n- propylthio)phenyl
2032 N C C C vinyl H 2,6-dibromo-4-(heptafluoro-n- _ propylthio) phenyl
omV xi n r- r- T w. 4. i u 2, 6-dibromo-4-(heptafluoro-n-
2033 N C C C cyclobutyl H , _ . .r.
propylthio) phenyl
,.,, ., _ , ,_ -, „ 2,6-dibromo4-(heptafluoro-n-
2034 N C C C cyclopentyl H , .. . , .
* J propylthio) phenyl
nmc »T -, ^ „ 2,6-dibromo-4-(heptafluoro-n-
2035 N C C C 3-Cyanobenzyl H ,.. . .r.
_ propylthio) phenyl
nmc », „ „ ^ - i_ ., 2,6-dibromo-4-(heptafluoro-n-
2036 N C C C 4-cyanobenzyl H , .. ., r.
_ _ propylthio) phenyl
,„„ ». _ _ _ _ .. , „ 2,6-dibromo-4-(heptafluoro-n-
2037 N C C C 2-cyanoethyl H -i4-i.-ii.-i
_ propylthio) phenyl
,.,. .. „ „ _ -, , 4.^ -, 4.^ ■ , 4.^ ■■ ., 2,6-dibromo-4-(heptafluoro-n-
2038 N C C C 2-(methylthio)ethyl H ..... , . ,
■* ■* propylthio) phenyl
2039 N C C C 2-(ethylthio)ethyl T~ 2,6-dibromo-4-(heptafluoro-n-
J J propylthio) phenyl
2040 N C 1-methyl-2-(methylthio) 2,6-dibromo4-(heptafluoro-n-
I | ethyl propylthio) phenyl

158
Table 5(5) ____^
Compound A, A2 A3 A; Ri R2 Q
No.
.,„„, „, t ,,„.,. ^ , ,, 2,6-dibromo-4-(heptafluoro-n-
2041 N C C C 2-(ethylsulfinyl)ethyL H propylthio)phenyl
2042 N C C C 2-fluoroethyl H 2,6-dibromo-4-(heptafluoro-n-
■ _ propylthio) phenyl
™,IT> ,, o o J*-, ,.,. ■, ,, 2,6-dibromo-4-(heptafluoro-n-
2043 N C C C 2,2-difluoroethyl H ,... . .r, .
[ _ propylthio) phenyl
-,,-,,.„ „ o -, -. ,_ • ^ ^ ■, „ 2,6-dibromo-4-(heptafluoro-n-
2044 N C C C 2,2,2-tnfluoroethyl H , ' , . .
_ propylthio) phenyl
-m,ic x, i -. J-*, o i r, 2,6-dibromo-4-(heptafluoro-n-
2045 N C C C l,3-dlfluoro-2-propyl H , .. . .*\. .
[ r rl propylthio) phenyl
-,r,„,r •, ■_, r, .=■, o ■, „ 2,6-dibromo-4- (heptafluoro-n-
2046 N C C C l-chloro-3-fluoro-2-propyl H , .. . .*\ ,
c " | propylthio) phenyl
7047 M l-methyl-2,2,2-trifluoro 2,6-dibromo-4-(heptafluoro-n-
ethyl propylthio) phenyl
™*o ,., ->-.-,,_•.*, , „ 2,6-dibromo-4-(heptafluoro-n-
2048 N C C C 3,3,3-tnfluoro-n-propyl H , _ .. *\. .
r CJ propylthio) phenyl
2049 c 2,2,3,3,3-pentafluoro-n- 2,6-dibromo-4-(heptafluoro-n-
propyl propylthio) phenyl
,„c„ „ „ „ „ ~ .,...■ *■> ^ i. , ,. 2,6-dibromo-4-(heptafluoro-n-
2050 N C C C 4,4,4-trifluoro-n-butyl H ... . , . , _ propylthio) phenyl
2051 N 2,2,3,3-tetrafluoro 2,6-dibromo-4-(heptafluoro-n- cyclobutyl propylthio) phenyl
2052 N C C C 2-chloroethyl "IT 2,6-dibromo-4-(heptafluoro-n- propylthio) phenyl
,nc, _ -i o J-'UI *... •> r, 2,6-dibromo-4- (heptafluoro-n-
2053 N C C C 2,2-dichloroethyl H .,_.. ,* propylthio) phenyl
,„,, _ _ 0 _ . . .. .. . „ 2,6-dibromo-4-(heptafluoro-n-
2054 N C C C 2,2,2-trichloroethyl H ,„. ,r.
' propylthio) phenyl
,„„ _, , , .. ., _ , „ 2,6-dibromo-4-(heptafluoro-n-
2055 N C C C l,3-dichloro-2-propyl H ,,_,..,_,
propylthio) phenyl
nn i-i ■. „ 2,6-dibromo-4-(heptafluoro-n-
2056 N C C C 3-chloro-n-propyl H ' _ , ..r, ,
propylthio) phenyl
,„„ _ „ . ,, . „ 2,6-dibromo-4- (heptafluoro-n-
2057 N C C C 2-bromoethyl H ,._.,,_,
propylthio) phenyl
->nco ^ -. w , „ 2,6-dibromo-4-(heptafluoro-n-
2058 N C C C 3-bromo-n-propyl H ,.. ..r. . propylthio) phenyl
2059 N C C C 2-iodoethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio) phenyl
2060 C (6-chloropyridin-3-yl) 2,6-dibromo-4-(heptafluoro-n-
methyl propylthio) phenyl

159 Table 5(6)
Compound Ai ft2 A3 A- R^ R2 Q~
Mo.
,n,, . , . . . „ „ 2, 6-dxinethyl-4-heptafluoro
2061 N-oxide C C C l-Pr H . , , ,
| isopropylphenyl
,„,, „ . . „ _ . _ . . ., .. , ,, 2,6-dimethyl-4-heptafluoro
2062 N-oxide C C C 2,2,2-trichloroethyl H ■, w , ' _ 1 s opropylphenyl
2063 N-oxide C C C Et ~T~ 2,6-dimethyl-4-hePtafluoro xsopropylphenyl
,„,, . , „ _ _ . „ 2, 6-dxmethyl-4-heptafluoro
2064 N-oxxde C C C vinyl H . •* , . ,
xsopropylphenyl
„„,, „ . . _ , . ^ , 2,6-dimethyl-4-heptafluoro
2065 N-oxxde C C C cyclobutyl H , , ,
■* _ xsopropylphenyl
,„,, „ ,_ . „ 2, 6-dimethyl-4-heptafluoro
2066 N-oxide C C C cyclopentyl H ' . , r ,
J ^ J xsopropyl phenyl
inr-, „■_■„„„ -> „ 2,6-dimethyl-4-heptafluoro
2067 N-oxide C C C 3-cyanobenzyl H , . .
J J xsopropylphenyl
.... . , . „ 2,6-dimethyl-4-heptafluoro
2068 N-oxide C C C 4-cyanobenzyl H , . ,
' J isopropylphenyl
.... „•_,„„„ ^ *.,_■, „ 2,6-dimethyl-4-heptafluoro
2069 N-oxide C C C 2-cyanoethyl H J , . ,
J J isopropylphenyl
"2070 N-oxide TTT 2-(methyxthxo)ethyl ~Y ^ ™£^$%£°°™
2071 N-oxxde C C C 2-(ethylthlo„thyl H ^^^^ST"
.„„ . , . . , , 2,6-dimethyl-4-heptafluoro
2072 N-oxide C C C l-methyl-2-(methylthio)ethyl H isopropylphenyl
„„., . ,.-,,, 2,6-dimethyl-4-heptafluoro
2073 N-oxide C C C 2-(ethylsulfinyl) ethyl H isopropylphenyl
.„„ . , , , 2,6-dxmethyl-4-heptafluoro
2074 N-oxide C C C 2-flooroethyl H isopropylphenyl
„„ . , __.,,,, 2,6-diraethyl-4-heptafluoro
2075 N-oxide C C C 2,2-difluoroethyl H isopropylphenyl
. , , , 2,6-dxmethyl-4-heptafluoro
2076 N-oxxde C C C 2,2,2-trxfluoroethyl H isopropylphenyl
2. 6-dxmethyl-4-heptafluoro
2077 N-oxxde C C^ J 1, 3-dxfluoro-2-propyl H isopropylphenyl
.,„.,„ . , ,_,.,.=,,,, ., 2, 6-dxmethyl-4-heptafluoro
2078 N-oxxde C C C l-chloro-3-fluoro-2-propyl H isopropylphenyl
. , , , 2,6-dxmethyl-4-heptafluoro
2079 N-oxxde C C C l-methyl-2,2,2-trxfluoroethyl H isopropylphenyl
. . . „ , 2,6-dxmethyl-4-heptafluoro
2080 | N-oxxde | C | C | C | 3,3,3-trxfluoro-n-propyl | H | isopropylphenyl

160 Table 5(7)
Compound ' Aj, A2 A3 A, R, R^ 1 Q
No.
2081 N-oxidp C c c 2, 2, 3, 3,3-pentafluoro-n- 2,6-dimethyl-4-heptafluoro
~ propyl isopropylphenyl
2082 N-oxide C C C 4,4,4-trifluoro-n-butyl H 2,6-dimethyl-4-heptafluoro _ isopropylphenyl
2083 N-oxide C C C 2,2,3,3-tetrafiuoro 2,6-dimethyl-4-heptafluoro cyclobutyl isopropylphenyl
2084 N-oxide C C C 2-chloroethyl H 2,6-diinethyl-4-heptafluoEO _ isopropylphenyl
2085 N-oxide C C C 2,2-dichloroethyl H 2,6-diinethyl-4-heptafluoro _ isopropylphenyl
,„., ., . . „ _ _ ,-,_■• ^, o , ,, 2,6-dimethyl-4-heptafluoro
2086 N-oxide C C C 1,3-dichloro-2-propyl H J . . ^ .
' isopropylphenyl
,„„ . . ., ., , „ 2,6-dimethyl-4-heptafluoro
2087 N-oxide C C C 3-chloro-n-propyl H . ,1.1
isopropylphenyl
™oo «, ^ ,_ ^ ■, .. 2, 6-dimethyl-4-heptafluoro
2088 N-oxide C C C 2-bromoethyl H . , , ■,
_ isopropylphenyl
*,noa ■_, -> >_ -i ,, 2,6-dimethyl-4-heptafluoro
2089 N-oxide C C C 3-bromo-n-propyl H TUT
; . r J isopropylphenyl
-K™ „ „ „ „ „ • , ^ , 2,6-dimethyl-4-heptafluoro
2090 N-oxide C C C 2-iodoethyl H ■, v T _ I isopropylphenyl
2091 N-oxide C C C (6-chloroPyridin-3-yl) ~ 2,6-diii«thyl-4-heptafluoro methyl isopropylphenyl
_„„_ . , „ 2, 6-dimethyl-4-(nonafluoro-2-
2092 N-oxide C C C Et H . ■*_ . . , ,
. butyl) phenyl
„„„„ . , . 2,6-dimethyl-4-(nonafluoro-2-
2093 N-oxide C C C l-Pr H , * n , . ,
butyl)phenyl
„„„. . , . , 2,6-dimethyl-4-(nonafluoro-2-
2094 N-oxide C C C vinyl H butyl) phenyl
, , 2,6-dimethyl-4-{nonafluoro-2-
2095 N-oxide C C C cyclobutyl H butyl) phenyl
„„„, . , ,_ , „ 2,6-dimethyl-4-(nonafluoro-2-
2096 N-oxide C C^^C cyclopentyl H butyl) phenyl
_, 2,6-dimethyl-4-(nonafluoro-2-
2097 N-oxide C C C 3-cyanobenzyl H butyl) phenyl
„ '. ~ " , , 2,6-diraethyl-4-(nonaf luoro-2-
2098 N-oxide C C C 4-cyanobenzyl H butyl) phenyl
„ . , , 2,6-dimethyl-4-(nonafluoro-2-
2099 N-oxide C c c 2-cyanoethyl H butyl) phenyl
„ . „ ,,,,., ^ , „ 2,6-dimethyl-4-(nonafluoro-2-
2100 N-oxide C C C 2-(methylthio) ethyl H butyl)phenyl |

161 Table 5(8)
Compound A7 I A2 Ik-. ' A4 [ R[ 1 R^ Q
No.
Tim v, ^. ,-. „ -, , ^ , ^,_ ■ , ^ ■, ,. 2, 6-dimethyl-4-(nonafluoro-2-
2101 N-oxide C C C 2-(ethylthiol ethyl H b t 1) h 1
oirn ., . , _ „ „ l-methyl-2-(methylthio) I ~ 2, 6-dimethyl-4-(nonafluoro-2-
2102 N-oxide C C C ^, H . . , . . ,
ethyl butyl) phenyl
,,„, „ . . _ _ _ . , ., , ... n. .. , It 2,6-dimethyl-4-(nonafluoro-2-
2103 N-oxide C C C 2-(ethylsulfinyl)ethyl H J
„„. »-•_,„„„ ^ ^, ,_,_■, „ 2,6-dimethyl-4-(nonafluoro-2-
2104 N-oxide C C C 2-fluoroethyl H . \ ,, , ,
butyl) phenyl
oint „, r- o o J-^T *.i. ! „ 2,6-dimethyl-4-(nonafluoro-2-
2105 N-oxide C C C 2,2-difluoroethyl H h t 1) h 1
iinc ., ^ „ ,- o o o ^ • — *.._■, „ 2,6-dimethyl-4-(nonafluoro-2-
2106 N-oxide C C C 2,2,2-tnfluoroethyl H . J. ,, ' ,
_ * butyl) phenyl
oim ., „ , -, ,-^-, -, , „ 2, 6-dimethyl-4-(nonafluoro-2-
2107 N-oxide C C C l,3-difluoro-2-propyl H butyl) phenyl
,,„„ „ , ., _ „ , , ., 2,6-dimethyl-4-(nonafluoro-2-
2108 N-oxide C C C l-chloro-3-fluoro-2-propyl H . . .
Tino ~ 77 _ ~~~ ~ l-methyl-2,2,2-trifluoro „ 2, 6-dimethyl-4-(nonafluoro-2-
2109 N-oxide C C C ' , , H , ,_ ,, , ,
ethyl butyl) phenyl
-> n n i, -j „ r. ,-. -, -> -> ». ■ *■, i 7, 2,6-dimethyl-4- (honafluoro-2-
2110 ■ N-oxide C C C 3,3,3-tnfluoro-n-propyl H butyl) phenyl
_lln ~7 77 ~ 7. 7. 2,2,3,3,3-pentafluoro-n- „ 2,6-dimethyl-4-(nonafluoro-2-
2111 N-oxide C C C propyl « butyl) phenyl
->•,■,-, ., -o „ „ „ . . , ^ -^ ,_*., „ 2,6-dimethyl-4-(nonafluoro-2-
2112 N-oxide C C C 4,4,4-tnfluoro-n-butyl H butyl)phenyl
77777 ~ 77 ~ ~ ~ 2,2,3,3-tetrafluoro ~ 2,6-dimethyl-4-(nonafluoro-2-
2113 N-oxide C C C -,,_*., H v. ,«.,,n„i,™ i
cyclobutyl butyl) phenyl
_,, . . , „ _ ., .. , „ 2,6-dimethyl-4-(nonafluoro-2-
2114 N-oxide C C C 2-chloroethyl H butyl) phenyl
„,,^ ] „ „ ,. , , ,_,_ , „ 2,6-dimethyl-4-(nonafluoro-2-
2115 N-oxide C C C 2,2-dichloroethyl H butyl)phenyl
„ „ „ '. ' " " 2,6-dimethyl-4-(nonafluoro-2-
2116 N-oxide C C C 2,2,2-tnchloroethyl H butyl) phenyl
~ ~ ~ ~ ~ I 2,6-dimethyl-4-(nonafluoro-2-
2117 N-oxide C C C 1,3-dichloro-2-propyl H butyl)phenyl
7 ~ " 2,6-dimethyl-4-(nonafluoro-2-
2118 N-oxide C C C 3-chloro-n-propyl H butyl)phenyl
7771 7 ~7 „ 2,6-dimethyl-4-(nonafluoro-2-
2119 N-oxide C C C 2-bromoethyl H butyl) phenyl
„ „ „ , , 2,6-diraethyl-4-(nonafluoro-2-
2120 | N-oxide j C | C | C | 3-bromo-n-propyl | H | butyl) phenyl

162 Table 5(9)
Compound Ai A2 A3 A4 Rx R2 Q
No.
„,„, ., ~ ' " I 2,6-dimethyl-4-(nonafluoro-2-
2121 N-oxide C C C 2-iodoethyl H ' , * . . ' .
^ butyl) phenyl
_,_- (6-chloropyridin-3-yl) 2,6-dimethyl-4-(nonafluoro-2-
methyl butyl) phenyl
,,,, _. „ 2,6-dibromo-4-(heptafluoro-n-
2123 N-oxide C C C Et H ,.. . . , .
propylthio) phenyl
_._„ „ . , ~~ ~ ~ ~~ ~ 2,6-dibromo-4-(heptafluoro-n-
2124 N-oxide C C C l-Pr H ... . . . .
propylthio)phenyl
-,n-,c . „ 2,6-dibromo-4-(heptafluoro-n-
2125 N-oxide C C C vinyl H ,... .r. .
J propylthio) phenyl
_,.. „ , . __ , „ 2,6-dibromo-4-(heptafluoro-n-
2126 N-oxide C C C cyclobutyl H . _.. .r. .
* * propylthio) phenyl
on-7 v, -i ^ ! u 2,6-dibromo-4-(heptafluoro-n-
2127 N-oxide C C C cyclopentyl H . __,. . . .
J r 3 propylthio) phenyl
T-ITO x, ■_■ r. r. r. r, v. i t, 2> 6-dibromo-4- (heptaf luoro-n-
2128 N-oxide C C C 3-cyanobenzyl H ,_. . .r.
J propylthio) phenyl
ono j „ •■ „ 2,6-dibromo-4-(heptafluoro-n-
2129 N-oxide C C C 4-cyanobenzyl H ... . .r, .
_ propylthio) phenyl
„,. „ „ ____ , „ 2,6-dibromo-4-(heptafluoro-n-
2130 N-oxide C C C 2-cyanoethyl H ' ._. . , -. .
_ _ propylthio) phenyl
->m »T -J r- r- r- •> < ^u i ^u ■ . <-v. i u 2' 6-dibromo-4- (heptaf luoro-n-
2131 N-oxide C C C 2-(methylthio) ethyl H ,... . , .
J J propylthio) phenyl
-n-an x, ^ „ „ -, , ^,_ ,^t- , ^x. ■, „ 2,6-dibromo-4-(heptafluoro-n-
2132 N-oxide C C C 2-(ethylthio) ethyl H ' .__.. .r.
propylthio) phenyl
~,,, „ _ _ _ l-methyl-2-(methylthio) „ 2,6-dibromo-4-(heptafluoro-n-
2133 N-oxide C C C ^x. , H ■,,_,_ • , x.
ethyl propylthio) phenyl
-,,-!,. „, -J „ - „ .» ,._,_■,,.*..,, x.x. , „ 2,6-dibromo-4- (heptafluoro-n-
2134 N-oxide C C C 2- (ethylsulfinyl) ethyl H ' .....r. .
J ■* J propylthio) phenyl
one r. n *i ._■- ■, r, 2,6-dibromo-4-(heptafluoro-n-
2135 N-oxide C C C 2-fluoroethyl H ... . , .
propylthio) phenyl
,- • , „ ^ ^. j.^, ^,_ ■, „ 2,6-dibromo-4-(heptafluoro-n-
2136 N-oxide C C C 2,2-difluoroethyl H ' .__.. ^,
propylthio) phenyl
Tim x, -J ^ „ ^. o -, - _ -^i ^x. , „ 2,6-dibromo-4-(heptaf luoro-n-
2137 N-oxide C C C 2,2,2-trifluoroethyl H n ., . .r, .
' propylthio) phenyl
„,0 „ ■ , r. ,* ^ -i T J-*T o -i u 2,6-dibromo-4-(heptafluoro-n-
2138 N-oxide C C C 1,3-difluoro-2-propyl H .... . .r. ,
r ^J propylthio) phenyl
,„„ x, -j , v., r, *, i •, n 2,6-dibromo-4-(heptafluoro-n-
2139 N-oxide C C C l-chloro-3-fluoro-2-propyl H .... , , .
r " propylthio) phenyl
7^0 N-oxide C C^ C l-methyl-2,2 2-trifluoro ~ 2,6-dibromo-4-(heptafluoro-n-
| | | I I ethyl | | propylthio) phenyl )

163 Table 5(10)
Compound Aj A; Aj A, I R^ i R, j Q
No. '
„., XT -J /- -I n ^> i. -fi i ,, 2,6-dibromo-4-(heptafluoro-n-
2141 N-oxide C C C 3,3,3-trifluoro-n-propyl H . ,..,r.
__] rj propylthio) phenyl
-,.„., . , _ „ _ 2,2,3,3,3-pentafluoro-n- „ 2,6-dibromo-4-(heptafluoro-n-
2142 N-oxide CCC //»/*- H ,,_..,.■,
propyl propylthio) phenyl
11/n ., ■ _■ „ ^ r. . , » ^ ■ *■. ^ ^ t .. 2, 6-dibromo-4-(heptafluoro-n-
2143 H-oxide CCC 4,4,4-tnfluoro-n-butyl H . * , . .
propylthio) phenyl
2144 N-oxide CCC 2,2,3,3-tetrafluoro 2,6-dibromo-4-(heptafluoro-n-
cyclobutyl propylthio) phenyl
IT Ad r~ o u.i ^v ■, „ 2,6-dibromo-4-(heptafluoro-n-
2145 N-oxide CCC 2-chloroethyl H ,,. . ,r. .
propylthio) phenyl
it AC KT ^ r- r. r- -i -i j • v.i tu i „ 2,6-dibromo-4- (heptafluoro-n-
2146 N-oxide CCC 2,2-dichloroethyl H . „. . . , ,
' _ propylthio) phenyl
-,,.-, ., „ „ „ o A o ^ ■ ._■, ^,_ , ,, 2,6-dibromo-4-(heptafluoro-n-
2147 N-oxide CCC 2,2,2-trichloroethyl H .... , . .
_l_ * propylthio) phenyl
OI/IQ „ r~ i -, _,• v., -> -i „ 2, 6-dibromo-4-(heptafluoro-n-
2148 N-oxide CCC 1,3-dichloro-2-propyl H . .. . . , .
' r ^J propylthio) phenyl
_,„„ „.,„„„ -, , , ■, . 2, 6-dibromb-4-(heptafluoro-n-
2149 N-oxide CCC 3-chloro-n-propyl H ' ... . ,r. .
r " propyl thio) phenyl
,,,. ~ ~ ~ ~ ~ 77 .. , „ 2,6-dibromo-4-(heptafluoro-n-
2150 N-oxide C c C 2-bromoethyl H propylthio) phenyl
_,.. „ , , , „ 2,6-dibromo-4-(heptafluoro-n-
2151 N-oxide C c C 3-bromo-n-propyl H propylthio) phenyl
o,cn », ^ —> • ., _v ■, „ 2,6-dibromo-4-(heptafluoro-n-
2152 N-oxide C C C 2-iodoethyl H propylthio) phenyl
.2153 N-oxide C C C-: (S-chloropyridin-3-yl) „ 2,6-dibromo-4-(heptafluoro-n-
methyl propylthio) phenyl
2-methyl-4-
2154 ^ N C C 1-Pr " hepta f luoroi sopropylphenyl
, , , 2-methyl-4-
2155 C W C_ C 2,2,2-trichloroethyl H heptaauorois^ropylphenyl
2, 6-dimethyl-4-heptafluoro
2156 c N C_ C__ ^ H isopropylphenyl
2, 6-dimethyl-4-heptafluoro
2157 C N f C 2,2,2-trichloroethyl H isopropylPhenyl
2-methyl-4-heptafluoro
2158 c C » f i-Pr H isopropylphenyl
2-methyl-4-heptafluoro
2159 c C I C 2,2,2-trichloroethyl H isopropylphenyl
2, 6-dimethyl-4-heptafluoro
2160 1 c 1 C 1 N j C I XSH 1 " I isopropylphenyl

164 Table 5(11)
Compound hL A, A3 A, Ri R2 Q
Wo. '
,,,, _ „ ., _ _ . . ., _. , „ 2,6-dimethyl-4-heptafluoro
2161 C C N C 2,2,2-trichloroethyl H -,1.1 isopropylphenyl
2162 C C C N i-Pr H 2-n.ethyl-4-heptafluoro isopropylphenyl
2163 C C C N 2,2,2-trichloroethyl T~ 2-methyl-4-heptaflu0ro j ' isopropylphenyl
2164 C C C N i-Pr H 2,6-dmethyl-4-heptafluor0 isopropylphenyl
„„ _ „ . _ _ . . ., .. , „ 2,6-dimethyl-4-heptafluoro
2165 C C C N 2,2,2-trichloroethyl H ■ ■, 1. -i
' isopropylphenyl
,,„ . „ „ 2,6-dimethyl-4-heptafluoro
2166 C C C N-oxide i-Pr H . ■* . . ^ .
isopropylphenyl
mr-, „ ~ „ x, „ ,. - ^ ■ ,., ._,_ , „ 2,6-dimethyl-4-heptafluoro
2167 C C C N-oxide 2,2,2-trichloroethyl H . ■,*.■,
J isopropylphenyl
2168 ~n C C C 2,2,2-trichloroethyl ^T 2' 6-di™ethyl-4-hePtafluoro
I I I I isopropylphenyl

165
Table 6(1) NH2
Compound No. R3 Yi Y2 Yj Y, Ys
1^1 H Me H heptafluoro-n-propyl H Me
1-2 H H H heptafluoroisopropyl H H
1^3 H H Me heptafluoroisopropyl H H
1-4 H H MeO heptafluoroisopropyl H H
1-5 H H CI heptafluoroisopropyl H H
1-6 H Me H heptafluoroisopropyl H H
1^7 H Me H heptaf luoroi sopropyl H Me
IH3 H Mte H heptafluoroisopropyl H phenyl
1-9 H Me H heptafluoroisopropyl Me H
1-10 H Me Me heptafluoroisopropyl H H
1-11 H Me Me heptafluoroisopropyl H CI
1-12 . H Me I heptafluoroisopropyl H CI
• 1-13 Me M<2 H heptafluoroisopropyl H Me
1-14 i-Pr Me H heptafluoroisopropyl H Me
1-15 H Et , H heptafluoroisopropyl H H
1-16 H Et H heptafluoroisopropyl H_ Me
1-17 H Et H heptafluoroisopropyl H Et
1-18 H Et H heptafluoroisopropyl H I
1-19 H n-Pr H hepta f luoroi sopropyl H H
1-20 H i-Pr H heptafluoroisopropyl H Me
1-21 H MeO H heptafluoroisopropyl H Me
1-22 H CI H heptafluoroisopropyl _H Et
1-23 H CI H heptafluoroisopropyl Me H
1-24 I H CI H heptafluoroisopropyl MeO H
1-25 I H Cl Me heptafluoroisopropyl H Me

166 Table 6(2)
Compound Mo. R2 Yi Y; Yj Y« Ys
1-26 H Br H heptafluoroisopropyl H Me
1-27 H Er H heptafluoroisopropyl H Et
1-28 H Br H heptafluoroisopropyl H n-Pr
1-29 H Br H heptafluoroisopropyl H n-Bu
1-30 H Br Me heptafluoroisopropyl H_^ Me
1-31 H I H heptafluoroisopropyl H Me
1-32 H I H heptafluoroisopropyl H n-Pr
1-33 H Me H nonafluoro-n-butyl H Me
1-34 H Me H nonafluoro-2-butyl H Me
1-35 H H H trifluoromethylthio H H
1-36 H Br H_ trifluoromethylthio H Br
1-37 H H H trifluoromethylsulfonyl H H
1-38 H Br; H trifluoromethylsulfonyl H Br
1-39 H Me H 2,2, 2-trifluoroethoxy H H
1-40 H H H heptafluoroisopropyl thio H H
1-41 H CI H heptafluoroisopropyl thio H CI
1-42 H B± H heptafluoroisopropylthio H Br
1-43 H CI H heptafluoro-n-propylthio H CI
1-44 H Br H heptafluoro-n-propylthio H Br
1-45 H CI H heptafluoroisopropylsulfonyl H CI
1-46 H B£ H nonafluoro-n-butyl thio H Br
1-47 H Br H pentafluoroethylthio H Br
1-48 H B£ H heptafluoro-n-propylsulfinyl H Br
1-49 Me Me H heptafluoro-n-propylthio H Me
I 1-50 I Me Br^ H heptafluoro-n-propylthio H Br

167
Table 7
NH2
JLiL/O (4-B)
Xj/yy Yi
'S *3
Compound No. Xt Xj X3 X, Yk Yj Y5
1-51 Me H H H Me heptafluoroisopropyl H
1-52 Me H H H Me heptafluoroisopropyl Me
1-53 H Me H H Me hepta f luoroisopropyl H
1-54 H Me H H Me heptafluoroisopropyl Me
1-55 H H H Me Me heptafluoroisopropyl H
1-56 H H H Me Me heptafluoroisopropyl Me
1-59 F H H H Me heptafluoroisopropyl Me
1-60 F H H H Me heptaf luoroisopropyl thio Me
1-61 H F H H Me heptafluoroisopropyl Me
1-62 H H H F Me heptafluoroisopropyl H
1-63 H H H F Me heptafluoroisopropyl Me
1-64 CI H H H Me heptafluoroisopropyl H
1-65 CI H H H Me hepta f luoroisopropyl Me
1-66 H CI H H Me heptafluoroisopropyl H
1-67 H CI H H Me hepta f luor oi s opropyl Me
1-68 H H H CI Me heptafluoroisopropyl H
1-69 H H H CI Me hepta f luoroi s opropyl Me
1-70 Br H H H Me heptafluoroisopropyl Me
1-71 H H H Br Me heptafluoroisopropyl H
1-72 H I H H Me heptafluoroisopropyl H
1-73 H H H I Me heptafluoroisopropyl H
1-74 H H H I Me heptafluoroisopropyl Me
1-75 H H CF3 ■ H Me heptafluoroisopropyl H
1-76 _H H CF3 H Me heptafluoroisopropyl Me
1-77 H MeO H H Me heptafluoroisopropyl H
1-78 H H NH2 H Me heptafluoroisopropyl H
1-79 H H NH2 H Me heptafluoroisopropyl Me
1-80 CI CI H CI Me heptafluoroisopropyl | H

168
Table 8
NH2
X4 HN^
4 Q
Compound No. Xi X2 X3 X, Q
1-81 H H H H 2-methyl-4-heptafluoroisopropyl-l-naphthyl
1-82 H H H H 4-heptaf luoroisopropyl-5, 6,7,8-tetrahydro-l-naphthyl
1-83 H H H H 2-chloro-4-heptafluoroisopropyl-5, 6, 7,8-tetrahydro-l-naphthyl
1-84 H H H H 2- ((1,1,1,3,3, 3-hexafluoro2-propyloxy)pyridin-5-yl
1-85 . CI H H H 2- (1,1,1, 3,3, 3-hexafluoro-2-propyloxy) -4-methylpyridin-5-yl
T 0, „ „ „ „ 2-bromo-4-methyl-6-(l,l,l,3,3,3-hexafluoro
-2-propyloxy)pyridin-3-yl

169
Table 9 shows the physical properties of the compounds represented by formulae (1) and (4) of the present invention. This table also shows 1H-NMR shift values obtained by using tetramethylsilane as an internal reference material, and chloroform-d as a solvent.

170
Table 9(1)
Compound
No. ]H-NMR(CDCl3,ppm)
3 5 1.30(6H,d,J=6.3Hz), 2.41(3H,s), 5.00-5.05(lH,m), 6.92(lH,s), 7.40-
7.61(5H,m), 7.93(lH,s), 8.01(lH,s), 8.21(1H,d,J=8.8Hz)
S 0.96(3H,t,J=7.3Hz), 1.38-1.47(2H,m), 1.63-1.71(2H,m), 2.41(3H,s),
4 4.19(2H,t,J=6.6Hz), 6.83(lH,s), 7.42-7.62(5H,m), 7.83(lH,s),
8.00(lH,s), 8.25(lH,d,J=8.5Hz)
5 0.98(6H,d,J=6.8Hz), 1.94-2.05(lH,m), 2.42(3H,s),
5 3.98(2H,d,J=6.6Hz), 6.81(lH,s), 7.44-7.52(3H,m), 7.55-7.61(2H,m),
7.85(lH,s), 8.01(lH,s), 8.25(1H,d,J=8.6Hz)
5 0.96(3H, t, J=7.6Hz), 1.29(3H, d, J=6.1Hz), 1.58-1.73(2H, m),
6 2.42(3H, s), 4.83-4.92(lH, m), 6.72(1H, s), 7.42-7.61(5H, m),
7.79(1H, s), 8.0K1H, s), 8.26(1H, d, J=8.5Hz)
7 8l.53(9H,s), 2.41(3H,s), 6.66(lH,s), 7.40-7.59(5H,m), 7.80(lH,s),
7.98(1H,d,J=l.7Hz), 8.23(1H,d,J=8.8Hz)
5 0.98(9H, s), 2.41(3H, s), 3.89(2H, s), 6.94(1H, s), 7.41-7.50(3H,
8 m), 7.54-7.57(lH, m), 7.62(1H, d, J=8.1Hz), 7.86(1H, s), 8.02(1H,
s), 8.24(1H, d, J=8.8Hz)
5 0.97(9H, s), 1.62(2H, t, J=7.6Hz), 2.41(3H, s), 4.25(2H, t,
9 J=7.6Hz), 6.79(1H, br), 7.42-7.51(3H, m), 7.54-7.57 (1H, m), 7.61(1H,
d), 7.82(1H, s), 7.99(1H, s), 8.24(1H, d, J=8.5Hz)
5 0.90(3H,t,J=7.3Hz), 0.91(3H,t,J=7.3Hz), 1.26-1.41(8H,m), 1.55-1Q 1.65(lH,m), 2.40(3H, s), 4.10(2H,t,J=5.4Hz), 7.01(lH,s), 7.40-
7.50(3H,m), 7.55(lH,d,J=7.8Hz), 7.62(1H,d,J=7.8Hz), 7.91(lH,s), 8.01
(lH,s), 8.21(lH,d,J=8.5Hz)
5 2.42(3H,s), 4.55(lH,dd,J=1.7Hz, 6.3Hz), 4.83(lH,dd,J=1.7Hz, ,, 13.9Hz), 7.29(lH,dd, J=6.3Hz, 13.9Hz), 7.42-7.50(3H,m), 7.61-
7.63(lH,m), 7.77(lH,d,J=7.8Hz), 8.08(lH,s), 8.15(1H,d,J=7.8Hz), 8.30
(!H,s), 8.92(lH,br-s)
5 2.42(3H, s), 4.68-4.70(2H, m) , 5.27-5.31(1H, m), 5.35-5.41(1H, m),
12 5.93-6.03UH, m), 6.83(1H, br), 7 . 44-7. 52 (3H, m) , 7 . 55-7 . 63 (2H, m) ,
7.79(1H, br), 8.00(1H, s), 8.26(1H, d, J=8.8Hz)
5 0.82(3H, d, J=7.1Hz), 0.84-0.99(7H, m), 1.02-1.12(2H, m), 1.36-
13 1.42(1H, m), 1.50-1.59(1H, m), 1.68-1.72(2H, m), 1.94-1.99(1H, m),
2.1K1H, d, J = 1.7Hz), 2.42(3H, s), 4.65-4.72 (1H, m) , 6.74(1H, s) ,
7.42-7.62(5H, m), 7.80(1H, s), 8.02(1H, s), 8.25(1H, d, J=8.5Hz)
14 5 2.38(3H,s), 5.19(2H,s), 7.19(lH,s), 7.32-7.61(10H,m), 7.91{lH,s),
8.00(lH,s), 8.18(lH,d,J=8.5Hz)
16 5 2.34 (3H, s), 5.27(2H, s), 6.96 (1H, br-s), 7.40-7.58 (6H, m),
7.63-7.69 (3H, m), 7.79 (1H, s), 8.00 (1H, s), 8.25 (1H, d, J=8.8Hz)
5 2.33(3H, s), 3.34(3H, s), 3.57-3.61 (2H, ra), 4.26-4.32 (2H, m),
17 7.13(1H, s), 7.32-7.42(3H, m), 7.46-7.53(2H, m) , 7.83(1H, s),
7.9K1H, d, J = 1.7Hz), 8.13(1H, d, J=8.5Hz)
5 2.42(3H,s), 5.83(2H,s), 7.16(1H,br-s), 7.43-7.52(3H,m),
18 7.61(lH,d,J=8.1Hz), 7.68(lH,d,J=8.1Hz), 7.82(lH,s), 8.03(lH,s),
|8.25(1H, d, J=8.5Hz)

171
Table 9(2) Compound
No. ^-NMRCCDCL^ppm)
5 2.42(3H,s), 5.83(2H,s), 7.16(lH,br-s), 7.43-7.52(3H,m),
!8 7.61(lH,d,J=8.1Hz), 7.68(lH,d,J=8.1Hz), 7.82(lH,s), 8.03(lH,s),
8.25(lH,d,J=8.5Hz)
5 2.40(3H, s), 3.74(2H, t, J=5.6Hz), 4.44(2H, t, J=5.6Hz), 7.19(1H,
19 s), 7.42-7.50(3H, m), 7.55-7.58(1H, m), 7.63(1H, d, J=7.6Hz),
7.88(1H/ s), 8.01(1H, s), 8.22(1H, d, J=8.8Hz)
20 5 2.40(3H,s), 4.83(2H,s), 7.42-7.49(3H,m), 7.58-7.61(lH,m), 7.67-
7.69(2H,m), 7.98(lH,s), 8.06(lH,s), 8.19(lH,d,J=8.5Hz)
21 5 2.43{3H, s), 6.90(1H, s), 7.22(1H, br-s), 7.47-7.54(3H, m), 7.64-
7.68(2H, m), 7.78(1H, s), 8.06(1H, s), 8.26(1H, d, J = 8.8Hz)
22 5 2.01(6H,s), 2.42(3H,s), 6.95(lH,br), 7.44-7.52(3H,m), 7.57-
7.62(2H,m), 7.80(lH,s), 8.02(lH,s), 8.24(1H,d,J=8.5Hz)
93 5 2.41{3H,s), 7.23-7.29(lH,m), 7.40-7.55(7H,m), 7.61-7.64(lH,m),
_ 7.72(lH,d,J=8.3Hz), 7.78(lH,s), 8.07(lH,s), 8,26(1H, d,J=8.8Hz)
5 2.36(3H,s), 2.40(3H,s), 7.05-7.09(2H,m), 7.15(lH,s),
24 7.20(2H,d,J=8.1Hz), 7.47-7.52 (3H,m), 7.60-7.63(lH,m), 7.66-
7.68(lH,m), 7.79(lH,s), 8.07(lH,s), 8.25(lH,d,J=8.8Hz)
5 2.41(3H,s), 7.12-7.17(2H,m), 7.32-7.38(2H,m), 7.42-7.48(3H,m),
25 7.64(lH,d,J= 7.8Hz), 7.82(1H,d,J=7.8Hz), 7.99(lH,d,J=8.5Hz),
8.06(lH,d,J=8.5Hz), 8.51(lH,s), 9.52(lH,s)
59 5 2.32(6H, s), 3.79(3H, s), 6.92(1H, br-s), 7.34(2H, s), 7.43(1H, t,
J=7.8Hz), 7.52-7.62(3H, m), 8.00(1H, s)
8 1.33(3H, t, J = 7.1Hz), 2.33(6H, s), 4.24(2H, q, J=7.1Hz),
60 6,80(1H, s), 7.35(2H, s), 7.44(1H, t, J=7.8Hz), 7.46(1H, s), 7.52-
7.6K2H, m), 8.02(1H, s)
5 0.99(3H, t, J=7.3Hz), 1.71(2H, m), 2.34(6H, s), 4.14(2H, t,
61 J=6.9Hz), 6.79(1H, s), 7.35(2H, s) , 7.41-7.47<2H, m), 7.59-7.61(2H,
m), 8.02(1H, s)
5 1.31(6H, d, J=6.3Hz), 2.33(6H, s), 5.03(1H, septet, J=6.3Hz),
62 6.74(1H, s), 7.35(2H, s), 7.43(1H, t, J=8.1Hz), 7.52(1H, s), 7.56-
7.61(2H, m), 8.03(1H, s)
5 0.96(3H, t, J=7.3Hz), 1.38-1.48(2H, m) , 1.61-1.71(2H, m), 2.34(6H,
63 S), 4.19(2H, t, J=6.9Hz), 6.76(1H, s), 7.35(2H, s), 7.42-7.46(2H,
m), 7.58-7.6K2H, m), 8.02(1H, s)
5 0.98(6H, d, J=6.8Hz), 1.94-2.04(1H, m), 2.34(6H, s), 3.97(2H, d,
64 J=6.6Hz), 6.79(1H, s), 7.35(2H, s), 7.42-7.47(2H, m), 7.59-7.61(2H,
|m) , 8.02(1H, s)

172
Table 9(3)
Compound
No. ^-NMRtCDCl^ppm)
66 5 1.53(9H, s), 2.34(6H, s), 6.62(1H, s), 7.35(2H, s), 7.38-7.45(2H,
m), 7.51-7.60(2H, m), 8.02(1H, s)
5 0.99(9H, s), 2.34(6H, s), 3.90{2H, s), 6.79(1H, s) , 7.35(2H, s),
67 7.43(1H, br-s), 7.46(1H, t, J = 8.1Hz), 7.59-7.63(2H, m), 8.03(1H,
sj
8 0.95(3H, d, J=6.8Hz), 0.96(3H, d, J=6.8Hz), 1.24(3H, d, J=6.3Hz),
68 1.81-1.89(1H, m), 2.34(6H, s), 4.75(1H, quint, J=6.3Hz), 6.77(1H,
s), 7.35(2H, s), 7.44(1H, t, J=8.1Hz), 7.54-7.62(3H, m), 8.05(1H, s)
5 0.94(3H, t, J=7.3Hz), 1.29(3H, d, J=6.3Hz), 1.32-1.45(2H, m),
69 1.46-1.58(1H, m), 1.61-1.70 (1H, m), 2.35(6H, s), 4.93(1H, sett.,
J=6.3Hz), 6.73(1H, s), 7.35(2H, s), 7.42-7.47(1H, m), 7.51(1H, s),
7.56-7.62(2H, m), 8.05(1H, s)
5 0.93(3H, d, J = 6.6Hz), 0.94(3H, d, J = 6.6Hz), 1.29(3H, d, J =
70 6.3Hz), 1.31-1.37(1H, m), 1.57-1.75(2H, m), 2.34(6H, s), 4.96-
5.05(1H, m), 6.70(1H, s), 7.35(2H, s), 7.42-7.46(2H, m), 7.57-
7.61(2H, m), 8.04(1H, s)
8 0.97(9H, s), 1.62(2H, t, J=7.6Hz), 2.34(6H, s), 4.25(2H, t,
71 J=7.6Hz), 6.73(1H, s), 7.35(2H, s), 7.43-7.47(2H, m), 7.59-7.61(2H,
m), 8.02(1H, s)
8 1.27-1.34(2H, m), 1.50-1.66(4H, m), 1.74-1.83(2H, m), 2.18-
72 2.32(1H, m), 2.34(6H, s) , 4.07(2H, d, J=7.1Hz), 6.79(1H, s),
7.35(2H, s), 7.43-7.51(2H, m), 7.58-7.62(2H, m), 8.03(1H, s)
8 1.62 (3H, d, J=6.6Hz), 2.33 (6H, s), 5.90 (1H, q, J=6.6Hz), 6.82
73 (1H, br-s), 7.28-7.45 (9H, m), 7.56 (1H, d, J=8.1Hz), 7.60 (1H, d,
J=7.6Hz), 8.02 (1H, br-s) ^___
8 2.34 (6H, s), 3.02 (2H, t, J=7.1Hz), 4.42 (2H, t, J=7.1Hz), 6.74
74 (1H, br-s), 7.23-7.27 (2H, m), 7.31-7.35 (5H, m), 7.41-7.47 (2H, m),
7.58-7.62 (2H, m), 7.99 (1H, br-s)
8 2.34(6H, s), 4.58(1H, dd, J=2.0Hz, 6.3Hz), 4.87(1H, dd, J=2.0Hz,
75 13.9Hz), 7.00(1H, s), 7.25(1H, dd, J=6.3Hz, 13.9Hz), 7.35(2H, s),
7.47(1H, t, J=7.8Hz), 7.55(1H, s), 7. 63-7.65 (2H, in), 8.03(1H, s)
8 2.34(6H, s), 4.68-4.70(2H, m), 5.26-5.31 (1H, m), 5.35-5.41(1H, m),
76 5.92-6.02(lH, m), 6.84(1H, s), 7.35(2H, s), 7.42-7.47(2H, m) , 7.60-
7.62(2H, m), 8.02(1H, s)
8 2.33(6H, s), 2.53(1H, t, J=1.4Hz), 4.79(2H, d, J=1.4Hz), 6.97(1H,
77 br-s), 7.35(2H, s), 7.44(1H, t, J=8.1Hz), 7.51(1H, s), 7.59-7.63(2H,
m), 8.02(1H, s)
8 1.60-1.70 (1H, m), 1.78-1.86 (1H, m), 2.07-2.18 (2H, m), 2.33 (6H,
78 s), 2.35-2.43 (2H, m), 5.00-5.08 (1H, m), 6.80 (1H, s), 7.35 (2H,
s), 7.41-7.46 (1H, m), 7.53-7.62 (3H, m), 8.03 (1H, s)
79 8 1.68-1.80(6H, m), 1.86-1.94(2H, ra), 2.34(6H, s), 5.20-5.23(1H, m),
6.72(1H, s), 7.35(2H, s), 7.42-7.62(4H, m), 8.04(1H, s)
31 8 2.32(6H, s), 5.22(2H, s), 6.87(1H, s), 7.34(2H, s), 7.36-7.45(7H,
|m) , 7.57-7.61(2H, m) , 8.01(1H, s)

173
Table 9(4)
Compound
No. lH-NMR(CDCl3,ppm)
5 2.33 (9H, s), 5.18 (2H, s) , 6.83 (1H, br-s), 7.14-7.20 (3H, m),
82 7.31 (1H, d, J=7.8Hz), 7.35 (2H, s), 7.44 (2H, t, J=7.8Hz), 7.52-
7.62 (2H, m), 8.01 (1H, br-s) '
83 5 2.34 (6H, s), 5.28 (2H, s), 6.90 (1H, br-s), 7.35 (2H, s), 7.43-
7.54 (4H, m), 7.61-7.66 (4H, m), 8.01 (1H, s)
g4 5 2.34 (6H, s), 5.24 (2H, s), 6.92 (1H, br-s), 7.35-7.52 (4H, m),
7.63-7.81 (6H, m), 8.02 (1H, s)
85 5 2.34 (6H, s), 5.27 (2H, s), 6.97 (1H, br-s), 7.35 (2H, s), 7.45-
7.52 (4H, m), 7.61-7.69 (4H, m), 8.01 (1H, s)
8g 5 2.34(6H, s), 5.34(2H, s), 6.90(1H, br), 7.28-7.30 (3H, m) , 7.35(2H,
s), 7.39-7.49QH, m), 7 . 59-7 . 64 (2H, m), 8.04(1H, m)
go 5 2.33(6H, s), 5.18(2H, s), 6.92(1H, s), 7.22-7.34(5H, m), 7.40-
7.47(3H, m), 7.59-7.63(2H, m), 8.02(1H, s)
91 5 2.33(6H, s), 5.18(2H, s), 6.86(1H, s), 7.29-7.38(6H, m), 7.43-
7.47(2H, m), 7.60-7.62(2H, m), 8.01(1H, s)
5 2.34 (6H, s), 5.32 (2H, s), 6.92 (1H, br-s), 7.36 (2H, s), 7.42
92 (1H, s), 7.48 (1H, t, J=7.8Hz), 7.58 (2H, d, J=9.0Hz), 7.62-7.66
(2H, m), 8.01 (1H, s), 8.25 (2H, d, J=9.0Hz)
5 2.35 (6H, s), 3.93 (3H, s), 5.28 (2H, s), 6.88 (1H, br-s), 7.36
93 (2H, s), 7.41 (1H, s), 7.45-7.49 (4H, m), 7.63 (2H, d, J=6.8Hz),
8.02 (1H, s), 8.05 (1H, d, J = 6.8Hz)
5 2.32 (6H, s), 2.62 (1H, br), 3.87 (2H, t, J=4.4Hz), 4.29-4.32
94 (2H, m), 7.26 (1H, s), 7.34 (2H, s), 7.42 (1H, t, J=8.1Hz), 7.54-
7.61 (2H, m), 7.77 (1H, s), 8.00 (1H, s)
5 2.31(6H, s), 3.41(3H, s), 3.64-3.66(2H, m), 4.32-4.35(2H, m),
95 7.14(1H, s), 7.34(2H, s) , 7.40(1H, t, J=7.8Hz), 7.55-7.60(2H, m),
7.67(1H, s), 8.00(1H, s)
5 1.23(3H, t, J = 6.8Hz), 2.29(6H, s), 3.56(2H, q, J=6.8Hz), 3.67-
96 3.70(2H, m), 4.31-4.34(2H, m), 7.26(1H, s), 7.33(2H, s), 7.38-
7.40(1H/ m), 7.52-7.60(2H, m), 7.83(1H, s), 8.00(1H, s)
5 1.18(6H, d, J=6.1Hz), 2.29(6H, s), 3.63-3.69(3H, m), 4.30-4.32(2H,
97 m), 7.26(1H, s), 7.33(2H, s), 7.38(1H, t, J=7.8Hz), 7.56-7.60(2H,
m), 7.82(1H, s) , 8.00(1H, s)
5 2.28 (6H, s), 3.70-3.73 [2H, m), 4.33-4.36 (2H, m), 4.57 (2H, s),
98 7.23-7.39 (9H, m), 7.53 (1H, d, J=7.8Hz), 7.58 (1H, d, J=7.8Hz),
7.87 (1H, s), 7.99 (1H, s)
5 1.20 (3H, t, J=8.1Hz), 1.95-2.00 (2H, m), 2.35 (6H, s), 3.47-3.57
99 (4H, m), 4.30 (2H, t, J=6.6Hz), 6.78 (1H, s), 7.35 (2H, s), 7.46
|(2H, t, J=7.8Hz), 7.61 (2H, d, J=7.8Hz), 8.02 (1H, s)

174
Table 9(5) Compound
No. lH-NMR (CDCI3, ppm)
5 1.30(3H, t, J=7.3Hz), 2.34(6H, s) , 4.26(2H, q, J=7.3Hz), 4.72(2H,
100 s), 7.35(2H, s), 7.36-7.40(lH, m), 7.52-7.60(3H, m), 7.77-7.79(1H,
m), 7.90(1H, br-s)
5 1.56(3H, d, J=7.3Hz), 2.33(6H, s) , 3.79(3H, s) , 5.18(1H, q,
101 J=7.3Hz), 7.21(1H, br), 7.35(2H, s), 7.41(1H, t, J=7.8Hz), 7.55-
7.62(3H, m), 7.98(1H, s)
5 1.29(3H, t, J=6.8Hz), 1.55(3H, d, J=6.8Hz), 2.34(6H, s), 4.23(2H,
102 q, J=6.8Hz), 5.16(1H, q, J=6.8Hz), 7.24(1H, br), 7.35(2H, s),
7.41(1H, t, J=7.8Hz), 7.55-7.62(3H, m), 7.96(1H, s)
5 2.2K3H, s), 2.34(6H, s), 2.84(2H, t, J=6.1Hz), 4.46(2H, t,
103 J=6.1Hz), 6.9K1H, br-s), 7.35(2H, s) , 7.43(1H, t, J=7.8Hz), 7.52-
7.70(3H, m), 8.01(1H, s)
104 5 2.10(3H, s), 2.34(6H, s), 4.33-4.42 (4H, m), 6.97(1H, br-s),
7.35(2H, s), 7.45(1H, t, J=7.8Hz), 7.57-7.64(3H, m), 8.01(1H, s)
5 2.33(6H, s), 2.78(2H, t, J=6.3Hz), 4.40(2H, t, J=6.3Hz), 7.12(1H,
106 br), 7.35(2H, s), 7.45(1H, t, J=7.8Hz), 7.60-7.65(3H, ra), 8.01(1H,
s)
5 2.17(3H, s), 2.34(6H, s), 2.80(2H, t, J=6.6Hz), 4.37(2H, t,
108 J=6.6Hz), 6.84{1H, br-s), "7.35(2H, s), 7.43-7.52 (2H, m) , 7.58-
7.63(2H, m), 8.02(1H, s)
5 1.25-1.3K3H, m) , 2.33(6H, s) , 2. 57-2. 64 (2H, m), 2 . 81-2 . 85 (2H, m) ,
109 4.32-4.38(2H, m), 6.92(1H, s), 7.35(2H, s), 7.42-7.49(1H, m), 7.58-
7.63(3H, m), 8.03(1H, s) _
5 1.28(6H, d, J=6.6Hz), 2.34(6H, s), 2.84(2H, t, J=7.1Hz), 2.94-
110 3.04(1H, m), 4.34(2H, t, J=7.1Hz), 6.88(1H, s), 7.35(2H, s), 7.42-
7.49(1H, m), 7.52-7.64(3H, m), 8.02(1H, s)
5 1.40(3H, d, J=6.1Hz), 2.17(3H, s), 2.34(6H, s) , 2.67(1H, dd, J=6.1Hz, 13.7Hz), 2.77(1H, dd, J=6.1Hz, 13.7Hz), 5.08(1H, sextett., J=6.1Hz), 6.80(1H, s), 7.35(2H, s), 7.45(1H, t, J=7.8Hz), 7.52(1H,
s), 7.57-7.63(2H, m), 8.04(1H, s)
5 1.24-1.37 (3H, m), 2.35 (6H, s), 2.26-2.31 (2H, m), 2.98-3.06 (2H,
112 m), 4.67-4.76 (2H, m), 7.35 (3H, s), 7.45 (2H, t, J=7.8Hz), 7.55-
7.74 (2H, m), 8.08 (1H, br-s)
5 1.36-1.43 (3H, m), 2.35 (6H, s), 3.04-3.10 (2H, m), 3.37 (2H, t,
113 J=5.9Hz), 4.68-4.73 (2H, m), 7.00 (1H, br-s), 7.35 (2H, s), 7.46
(2H, t, J=7.8Hz), 7.55-7.70 (2H, m) , 8.02-8.07 (1H, m)
5 2.35(6H, s), 4.45(2H, dt, J=28.3Hz, 4.0Hz), 4.66(2H, dt, J=47.3Hz,
116 4.0Hz), 6.88(1H, br-s), 7.36(2H, s), 7.46-7.50(2H, m), 7.59-7.65(2H,
m), 8.02(1H, s)
5 2.34(6H, s), 4.38(2H, dt, J=3.9Hz, 13.6Hz), 6.00(1H, tt, J=3.9Hz,
117 47.3Hz), 7.05(1H, br-s), 7.35(2H, s), 7.47(1H, t, J=7.8Hz), 7.57-
7.66(3H, m), 8.01(1H, s)
113 5 2.33(6H, s), 4.57(2H, q, J=8.3Hz), 7.09(1H, br), 7.35(2H, s),
|7.45-7.50(2H, m), 7.61-7.66(2H, m) , 8.01(1H, s)

175
Table 9(6)
Compound
Mo. ^-NMRtCDCJ^ppm)
119 5 2.35(6H, s), 4.61-4.75(4H, m), 5.18-5.31(1H, m) , 6.98(1H, br-s),
7.36(2H, s), 7.45-7.52(2H, m), 7.58-7.66(2H, m), 8.03(1H, s)
5 2.35(6H, s), 3.75-3.83(2H, m), 4.46-4.80(2H, m) , 5.19-5.24(1H, m) ,
120 6.97(1H, br-s), 7.36(2H, s), 7.36-7.48(2H, m), 7.60-7.66(2H, m),
8.03(1H, s)
(DMSO-d6) 5 1.48 (3H, d, J=6.6Hz), 2.35 (6H, s), 5.35 (1H, septet,
121 J=6.6Hz), 7.33 (2H, s), 7.42 (1H, t, J=7.8Hz), 7.68 (1H, d,
J=7.8Hz), 7.76 (1H, d, J=7.8Hz), 8.11 (1H, s), 8.76 (1H, s), 9.26
(1H, s)
(CDCl3+DMSO-ds) 5 2.35(6H, s), 5.87(1H, septet, J=6.3Hz), 7.33(2H,
122 s), 7.44(1H, t, J=8.1Hz), 7.71-7.78(2H, m), 8.17(1H, s), 8.97(1H,
s), 10.19(1H, s)
5 2.34{6H, s), 2.48-2.59(2H, m), 4.42(2H, t, J=6.3Hz), 6.93(1K, br-
123 s), 7.35(2H, s), 7.46(1H, t, J=7.8Hz), 7.57-7.64(3H, m), 8.01{1H,
br-s)
124 5 2.35(6H, s), 4.67(2H, t, J=13.2Hz), 6.98(1H, br-s), 7.29(2H, s),
7.36(1H, s), 7.50(1H, t, J=7.8Hz), 7.65-7.67(2H, m), 8.01(1H, s)
5 1.51(3H, d, J=6.4Hz), 2.35(6H, s), 5.49-5.50(1H, m), 6.90(1H, br-
125 s), 7.36(2H, s), 7.44(1H, br-s), 7.50(1H, t, J=7.8Hz), 7.62-7.67(2H,
m), 8.02(1H, s)
5 1.95-2.05(2H, m), 2.22-2.27(2H, m) , 2.35(6H, s), 4.26(2H, t,
126 J=6.4Hz), 6.81(1H, s), 7.36(2H, s), 7.45-7.49 (2H, m), 7.61-7.63(2H,
m), 8.02(1H, s)
5 2.35(6H, s), 2.61-2.65(1H, m), 2.9-3.1(lH, m), 5.2-5.3(lH, m),
127 7.0K1H, br-s), 7.36(2H, s), 7 . 45-7 . 52 (2H, m), 7 . 62-7 . 68 (2H, m),
8.0K1H, s)
12g 5 2.34(6H, s), 5.84(2H, s), 7.03(1H, s), 7.36(2H, s), 7.44-7.52(2H, m), 7.65-7.67(2H, m), 8.04(1H, s)
„g 5 2.36{6H, s), 7.33(2H, s), 7.40-7.46(1H, m), 7.65(1H, d, J=7.8Hz), 7.90(1H, d, J=7.8Hz), 7.95(1H, d, J=1.7Hz), 8.55(1H, s), 9.07(1H, s)
130 5 2.35(6H, s), 3.74-3.77(2H, ra), 4.44-4.47(2H, m), 6.87(1H, br) ,
7.36(2H, s), 7.43-7.52(2H, m), 7.59-7.64(2H, m), 8.02(1H, s)
5 2.32(6H, s), 4.53(2H, d, J=5.9Hz), 5.90(1H, t, J=5.9Hz), 7.1K1H,
131 br-s), 7.35(2H, s), 7.45(1H, t, J=8.1Hz), 7.60-7.64(3H, m), 8.01(1H,
br-s)
132 5 2.33(6H, s), 4.84(2H, s), 7.29(1H, br), 7.35(2H, s), 7.47(1H, t, J
= 7.8Hz), 7.58(1H, s), 7.64-7.66(2H, m), 8.04(1H, s)
133 5 2.35(6H, s), 6.90(1H, s) , 7.17(1H, br) , 7.36(2H, s), 7.42(1H, s),
|7.50-7.54(1H, m), 7.66-7.71(2H, m), 8.06(1H, s) (

176
Table 9(7) [Compound
No- ^-NMEMCDCl^ppm)
5 2.35(6H, s), 3.83(4H, d, J=5.1Hz), 5.22(1H, quint, J=5.1Hz),
134 6.93(1H, s), 7.36{2H, s), 7.43(1H, s), 7.48(1H, t, J=7.8Hz), 7.60-
7.66(2H, m), 8.03(1H, s)
135 5 2.01(6H, s), 2.35(6H, s), 6.88(1H, br), 7.36(2H, s), 7.43-7.52(2H,
m), 7.58-7.65(2H, m), 8.03(1H, s)
5 2.17{2H, quint, J=6.3Hz), 2.34(6H, s), 3.66(2H, t, J=6.3Hz),
136 4.36(2H, t, J=6.3Hz), 6.83{1H, s), 7.35(2H, s), 7.43-7.48 (1H, m),
7.52(1H, s), 7.59-7.63(2H, m), 8.02(1H, s)
137 5 2.35(6H, s), 3.59(2H, t, J=5.9Hz), 4.'51(2H, t, J=5.9Hz), 6.86(1H,
br), 7.36(2H, s), 7.43-7.52(2H, m), 7.60-7.64(2H, m), 8.02(1H, s)
13g 5 2.34(6H, s), 5.03(2H, s), 7.15(1H, br), 7.35(2H, s), 7.47-7.54(2H,
m), 7.64-7.69(2H, m), 8.06(1H, s)
5 2.25(2H, quint, J=6.1Hz), 2.34(6H, s), 3.51(2H,.t, J=6.1Hz),
139 4.35(2H, t, J=6.1Hz), 6.83(1H, s), 7.35(2H, s), 7.46(1H, t,
J=8.1Hz), 7.54(1H, s), 7.58-7.64(2H, m), 8.02(1H, s)
140 5 2.34(6H, s), 3.34-3.39(2H, m) , 4.42-4.47(2H, m), 6.91-6.99(1H,
br), 7.35(2H, s), 7.43-7.49(1H, m), 7.56-7.64(3H, m), 8.03(1H, s)
(DMSO-dg) 5 1.82(3H, s), 2.28(6H, s), 3.33(2H, q, J=5.9Hz), 4.11(2H,
141 t, J=5.9Hz), 7.44(2H, s), 7.46(1H, d, J=7.8Hz), 7.62-7.69(2H, m),
8.04(1H, t, J=5.9Hz), 8.09(1H, s), 9.90(1H, s), 9.93(1H, s)
5 2.34(6H, s), 2.36(3H, s), 7.05-7.08 (2H, m) , 7.17-7.20(2H, m),
146 7.33(2H, s), 7.43(1H, t, J=7.8Hz), 7.68(1H, d, J=7.8Hz), 7.80(1H, d,
J=7.8Hz), 8.17 (1H, s), 8.67(1H, s), 9.29(1H, s)
147 5 2.35(6H, s), 7.33(2H, s) , 7.41-7.57(5H,'m), 7.72(1H, d, J=7.8Hz),
7.82(1H, d, J=7.8Hz), 8.18(1H, s), 9.01(1H, s) , 9.73(1H, s)
5 2.35(6H, s), 7.13-7.18(2H, m), 7.32-7.37(4H, m) , 7.41-7.45(1H, m),
148 7.70(1H, d, J=7.6Hz), 7.8K1H, d, J=7.6Hz), 8.16(1H, s), 9.04(1H,
s), 9.69(1H, s)
5 2.34(6H, s), 7.32(2H, s), 7.33-7.36(1H, m), 7.42-7.52(3H, m),
149 7.65(1H, d, J=2.4Hz), 7.70(1H, d, J=7.8Hz), 7.80-7.88(4H, m),
8.20(1H, s), 8.76(1H, s), 9.48(1H, s)
5 2.08-2.14 (1H, m), 2.18-2.30 (1H, m), 2.35 (6H, s) , 3.86-4.01 (4H,
154 m), 5.37-5.39 (1H, m), 6.87 (1H, br-s), 7.35 (2H, s), 7.46 (2H, t,
J=7.6Hz), 7.58-7.63 (2H, m), 8.01 (1H, s)
5 2.34 (6H, s), 5.18 (2H, s) , 6.38 (1H, d, J=3.2Hz), 6.48 (1H, d,
155 J=3.2Hz), 6.83 (1H, br-s), 7.35 (2H, s), 7.43-7.47 (3H, m), 7.57-
7.63 (2H, m), 8.01 (1H, s)
5 2.34 (6H, s), 5.10 (2H, s), 6.48 (1H, s), 6.79 (1H, br-s), 7.35
156 (2H, s), 7.39-7.47 (3H, in), 7.53 (1H, s), 7.59-7.63 (2H, m), 8.01
|(1H, br-s)

177
Table 9(8) Compound
No- lH-NMR(CDCl3,ppni)
5 1.58-1.67 (1H, m), 1.93-1.95 (2H, m), 2.01-2.09 (1H, m), 2.34 (6H, s),
157 3.78-3.93 (2H, m), 4.06-4.23 (2H, m), 4.31 (1H, dd, J=3.2Hz, 11.2Hz), 6.95
(1H, br-s), 7.35 (2H, s), 7.45 (2H, t, J=7.8Hz), 7.50-7.56 (1H, m) , 7.63
(1H, d, J=7.1Hz), 8.04 (1H, s)
5 1.66-1.73 (1H, m), 2.05-2.13 (1H, m), 2.34 (6H, s), 2.60-2.70 (1H, m) ,
158 3.64-3.68 (1H, m), 3.73-3.79 (1H, m), 3.85-3.92 (2H, m), 4.09-4.15 (2H, m) ,
6.87 (1H, br-s), 7.35 (2H, s), 7.46 <2H, t, J=7.8Hz), 7.61-7.66 (2H, m) ,
8.01 (1H, br-s)
5 2.34 (6H, s), 5.38 (2H, s), 6.83 (1H, br-s), 6.98-7.02 (1H, m), 7.16 (1H,
159 d, J=2.9Hz), 7.34-7.36 (3H, m), 7.43-7.47 (2H, m), 7.59-7.63 (2H, m) , 8.01
(1H, s)
160 5 2.34 (6H, s), 5.23 (2H, s), 6.83 (1H, br-s), 7.14 (1H, d, J=5.1Hz), 7.33-
7.37 (4H, m), 7.45 (2H, t, J=7.8Hz), 7.61-7.64 (2H, m) , 8.02 (1H, s)
5 2.32 (6H, s), 5.34 (2H, s), 7.24-7.28 (2H, m), 7.35 (2H, s) , 7.39 (1H, d,
161 J=7.8Hz), 7.43 (1H, d, J=7.8Hz), 7.55 (1H, s), 7.61 (2H, t, J=7.8Hz), 7.73
(1H, dt, J=1.7Hz, 7.8Hz), 8.03 (1H, s), 8.61 (1H, br-s)
162 5 2.36 (6H, s), 5.36 (2H, s), 6.37 (1H, br-s), 6.70 (1H, s), 7.31-7.39 (4H,
m), 7.73-7.82 (4H, m), 8.58-8.61 (1H, m), 8.72 (1H, d, J=2.0Hz)
163 5 2.34 (6H, s), 5.22 (2H, s), 6.89 (1H, br-s), 7.35-7.49 (5H, m), 7.62 (2H,
d, J= 7.3Hz), 7.72-7.77 (1H, m), 8.00 (1H, br-s), 8.45 (1H, d, J=2.4Hz)
51.23 (6H, d, J=6.8Hz), 2.34 (3H, s), 3.18 (1H, septet, J=6.8Hz), 3.81 (3H,
164 s), 6.84 (1H, s), 7.36 (1H, s), 7.42 (1H, s), 7.46 (1H, t, J=7.8Hz), 7.56-
7.63 (3H, m), 8.01 (1H, s)
51.22 (6H, d, J=6.8Hz), 1.33 (3H, t, J=7.3Hz), 2.33 (3H, s), 3.17 (1H,
165 septet, J=6.8Hz), 4.24 (2H, q, J=7.3Hz), 6.80 (1H, s), 7.35 (1H, s), 7.41
(1H, s), 7.44 (1H, t, J=7.8Hz), 7.58-7.62 (3H, m), 8.02 (1H, s)
5 1.32(6H, d, J=6.1Hz), 5.03(1H, septet, J=6.1Hz), 6.71(1H, s), 7.40-
166 7.44(1H, m) , 7.54(1H, d, J=2.0Hz), 7.56(1H, d, J=2.0Hz), 7.60(2H, d,
J=8.8Hz), 7.80(2H, d, J=8.8Hz), 7.98(1H, s), 8.03(1H, s)
lg7 51.32 (6H, d, J=6.1Hz), 2.53 (3H, d, J=8.8Hz), 5.04 (1H, septet, J=6.1Hz),
6.71 (1H, br-s), 7.41-7.65 (6H, m) , 7.95-7.97 (2H, m)
5 1.32(6H, d, J=6.1Hz), 1.33(3H, t, J=7.6Hz), 2.74(2H, q, J=7.6Hz),
168 5.04(1H, septet, J=6.1Hz), 6.70(1H, s), 7.43-7.56(4H, m), 7.60(1H, d,
J=8.1Hz), 7.86(1H, s), 8.00(1H, s), 8.27(1H, d, J=8.5Hz)
5 1.02(3H, t, J=7.3Hz), 1.32(6H, d, J=6.3Hz), 1.67-1.77(2H, m), 2.70(2H, t,
169 J=7.3Hz), 5.03(1H, septet, J=6.3Hz), 6.72(1H, s), 7.43-7.60(5H, m) ,
7.89(1H, s), 8.03(1H, s), 8.29(1H, d, J=8.5Hz)
51.32 (6H, d, J=6.4Hz), 3.89 (3H, s), 5.04 (1H, septet, J=6.4Hz), 6.73 (1H,
170 br s), 7.05-7.08 (1H, in), 7.42-7.46 (1H, m) , 7.51-7.58 (3H, m) , 7.80 (1H,
s), 8.00 (1H, s), 8.15 (1H, s)
51.32 (6H, d, J=6.4Hz), 5.03 (1H, septet, J=6.4Hz), 6.75 (lH,.s), 7.28-7.47
171 (2H, m), 7.52-7.58 (2H, m), 7.72-7.75 (1H, m), 7.92 (1H, s), 8.00 (1H, s),
[8.37 (1H, s)

178 Table 9(9)
Compound
No- ^-NMRtCDCljrppm)
51.31 (6H, d, J=6.3Hz), 2.30 (3H, s), 2.47 (3H, d, J=5.9Hz), 5.01-5.09 (1H,
172 m), 6.72 (1H, br-s), 7.40-7.47 (2H, m), 7.56-7.60 (2H, m), 7.77 (1H, d,
J=8.6Hz), 7.83 (1H, br-s), 8.00 (1H, br-s)
8 1.31 (6H, d, J=6.1Hz), 2.35 (3H, s), 2.52 (3H, d, J=9.0Hz), 4.99-5.09 (1H,
173 m), 6.71 (1H, br-s), 7.30 (1H, br-s), 7.44 (1H, t, J=7.8Hz), 7.52-7.57 (1H,
m), 7.61 (1H, d, J=7.8Hz), 7.72 (1H, s), 7.98 (1H, s), 8.06 (1H, s)
5 1.23(6H, t, J=7.6Hz), 1.32(6H, d, J=6.1Hz), 2.69(4H, q, J=7.6Hz), 5.03(1H,
174 septet, J=6.1Hz), 6.70(1H, s), 7.38(2H, s), 7.42-7.47(2H, m), 7.58-7.62(2H,
m), 8.0K1H, s)
5 1.22(3H, t, J=7.6Hz), 1.31(6H, d, J=6.3Hz), 2.34(3H, s), 2.69(2H, q,
175 J=7.6Hz), 5.03(1H, septet, J=6.3Hz), 6.70(1H, s), 7.37(2H, s), 7.42-7.47(2H,
m), 7.58-7.61(2H, m), 8.02(1H, s)
51.22 <6H, d, J=6.8Hz), 1.31 (6H, d, J=6.3Hz), 2.33 (3H, s), 3.17 (1H, septet,
176 J=6.8Hz), 5.03 (1H, septet, J=6.3Hz), 6.76 (1H, s), 7.35 (1H, s), 7.41 (1H,
s), 7.44 (1H, t, J=8.1Hz), 7.56-7.62 (3H, m) , 8.03 (1H, s) "
5 1.32(6H, d, J=6.1Hz), 2.35(3H, s), 3.85(3H, s), 5.04(1H, septet, J=6.1Hz),
• 177 6.67(1H, s), 6.96(1H, s), 7.13(1H, s), 7.44(1H, t, J=8.1Hz), 7.59-7.65(3H, m) ,
7.96(1H, s)
178 5 1.30(6H, d, J=6.1Hz), 2.42(3H, s), 5.00(1H, septet, J=6.1Hz), 6.63(1H, s),
7.27-7.41(8H, m), 7.45(1H, s), 7.53(1H, s), 7.58(1H, d, J=7.8Hz), 7.74(1H, s)
51.31 (6H, d, J=6.1Hz), 2.61 (3H, d, J=6.3Hz), 5.05 (1H, septet, J=6.1Hz),
179 6.76 (1H, br s), 7.45-7.58 (3H, m), 7.70 (1H, d, J=8.1Hz), 7.96 (1H, t,
J=1.8Hz), 8.56-8.58 (1H, m), 8.70 (1H, br s)
lg0 5 1.24(3H, t, J=7.6Hz), 1.31{6H, d, J=6.3Hz), 2.75(2H, q, J=7.6Hz), 5.03(1H,
septet, J=6.3Hz), 6.74(1H, s), 7.42-7.47 (2H, m), 7.57-7.67(4H, m), 8.02(1H, s)
5 0.93(3H, t, J=7.3Hz), 1.32{6H, d, J=6.1Hz), 1.63-1.71(2H, m), 2.70(2H, t,
181 J=7.6Hz), 5.04(1H, septet, J=6.1Hz), 6.72(1H, s), 7.44-7.48(2H, m) , 7.57-
7.63QH, m), 7.68(1H, s), 8.02(1H, s)
51.32 (6H, d, J=6.4Hz), 3.92 (3H, s), 5.06 (1H, septet, J=6.4Hz), 6.73 (1H,
182 s), 7.46-7.50 (1H, m), 7.55-7.60 (2H, m), 7.69 (1H, d, J=7.8Hz), 7.96 (1H, s) ,
8.48 (1H, d, J=1.2Hz), 8.58 (1H, s)
51.31 (6H, d, J=6.2Hz), 2.30 (3H, s), 2.44 (3H, d, J=6.4Hz), 5.01-5.05 (1H,
183 m), 6.72 (1H, br-s), 7.44-7.48 (2H, m), 7.61-7.62 (2H, m), 7.78 (1H, s) , 8.03
(1H, br-s)
5 1.32 (6H, d, J=6.1Hz), 2.35 (3H, s), 2.58 (3H, d, J=6.8Hz), 5.01-5.07 (1H,
184 m), 6.68 (1H, br-s), 7.35 (1H, s), 7.46 (1H, t, J=7.8Hz), 7.61-7.65 (2H, m) ,
7.72 (1H, s), 8.01 (1H, s)
51.31 <6H, d, J=6.4Hz), 2.49 (3H, s), 4.77 (2H, br-s), 5.06 (1H, sept,
185 J=6.4Hz), 6.73 (1H, br-s), 7.44-7.49 (1H, m), 7.55 (1H, s), 7.61-7.63 (2H, m),
7.81 (1H, s), 8.05 (1H, br-s)
186 51.32 (6H, d, J=6.4Hz), 2.61 (3H, s), 5.05 (1H, septet), 6.73 (1H, br-s),
[7.44-7.48 (2H, m), 7.57-7.64 (2H, m), 7.95 (1H, br-s), 8.06 (1H, br-s)

179
Table 9(10)
Compound
No. 1H-NMR(CDCl3,ppin) .
187 5 4.84(2H, s), 7.28(1H, br), 7.45(1H, t, J=8.1Hz), 7.59-7.65(4H, m) ,
7.81(2H, d, J=8.5Hz), 7.99(1H, s), 8.17(1H, s)
188 5 2.53 (3H, d, J=8.8Hz), 4.85 (2H, s), 7.15 (1H, br s), 7.45-7.65
(6H, m), 8.00-8.02 (2H, m)
5 1.34(3H, t, J=7.6Hz), 2.75(2H, q, J=7.6Hz), 4.85(2H, s), 7.10(1H,
189 S), 7.47-7.52(3H, m), 7.59-7.66(2H, m), 7.87(1H, s) , 8.05(1H, s) ,
8.27(1H, d, J=8.8Hz)
5 1.02(3H, t, J=7.3Hz), 1.67-1.77 (2H, m), 2.70(2H, t, J=7.6Hz),
190 4.85(2H, s), 7.10(1H, br-s), 7.44-7.52(3H, m) , 7.59-7.65 (2H, m) ,
7.88(1H, s), 8.07(1H/ s) , 8.30(1H, d, J=8.5Hz)
53.89 (3H, s), 4.85 (2H, s), 7.06 (1H, dd, J=8.5Hz, 2.0Hz), 7.18
191 (1H, br s), 7.46-7.54 (2H, m) , 7.61-7.63 (2H, m), 7.79-7.80 (1H, m) ,
8.01 (1H, s), 8.10 (1H, s)
192 54.86(2H,s), 7.09(lH,br.), 7.43-7.79(5H,m), 8.03(lH,br.),
8.56(lH,br), 8. 76(1H, d, J=8 . 8Hz)
193 54.86 (2H, s), 7.16 (1H, brs), 7.47-7.74 (5H, m), 7.93 (1H, s),
_ 8.02 (1H, s), 8.23 (1H, s)
5 2.30 (3H, s), 2.47 (3H, d, J=6.0Hz), 4.85 (2H, s), 7.12 (1H, br-
194 s), 7.42 (1H, d, J=9.0Hz), 7.49 (1H, t, J=8.1Hz), 7.62-7.67 (2H, m),
7.78-7.81 (2H, m), 8.03 (1H, br-s)
5 2.35 (3H, s), 2.52 (3H, d, J=8.8Hz), 4.86 (2H, s) , 7.05 (1H, br-
195 s), 7.31 (1H, s), 7.50 (1H, t, J=7.8Hz), 7.60-7.67 (2H, m), 7.71
(1H, s), 8.03 (1H, s), 8.07 (1H, s)
5 1.23(6H, t, J=7.6Hz), 2.70(4H, q, J=7.6Hz), 4.85(2H, s), 7.03(1H,
196 br), 7.39(3H, s), 7.50(1H, t, J=8.1Hz), 7.65(1H, d, J=8.1Hz),
7.69(1H, br-s), 8.04(1H, s)
5 1.23(3H, t, J=7.6Hz), 2.35(3H, s), 2.69(2H, q, J=7.6Hz), 4.85(2H,
197 s), 7.05(1H, br), 7.37(2H, s), 7.42(1H, s), 7.50(1H, t, J=7.8Hz),
7.64-7.66(2H, m) , 8.04(1H, s)
51.23 (6H, d, J=6.8Hz), 2.34 (3H, s), 3.17 (1H, septet, J=6.8Hz),
198 4.85 (2H, s), 7.18 (1H, br-s), 7.36 (1H, s), 7.42 (1H, s), 7.49 (1H,
t, J=8.1Hz), 7.55 (1H, s), 7.65-7.67 (2H, m), 8.05 (1H, s)
gg 5 2.36(3H, s), 3.86(3H, s), 4.85(2H, s), 6.96(1H, s), 7.01(1H, br),
7.14(1H, s), 7.49(1H, t, J=8.1Hz), 7.64-7.68(3H, m), 7.99(1H, s)
2Q0 5 2.43(3H, s), 4.83(2H, s), 6.99(1H, br), 7.33-7.42(8H, m), 7.45(1H,
s), 7.54(1H, s), 7.64(1H, d, J=6.3Hz), 7.78(1H, s)
5 2.47(3H,s), 4.86(2H,s), 7.06(lH,s), 7.11(1H,br.), 7.24-7 .27(lH,m),
201 7.53(lH,t,J=7.3Hz), 7.66(2H,t,J=7.3Hz), 7.95(lH,s), 8.17(lH,s),
|8.85(lH,s)

180
Table 9(11)
Compound
Ho. 'H-NMRtCDCl^ppm)
51.57 (3H, s), 4.86 (2H, s) , 7.10 (1H, br s), 7.52 (2H, t, J=7.8Hz),
202 7.63-7.65 (1H, m), 7.72-7.74 (1H, m) , 8.03(1H, br-s), 8.57-8.59 (1H,
m), 8.70 (1H, br s)
5 2.10 (3H, s), 4.84 (2H, s), 7.11 (1H, d, J=8.8Hz), 7.18-7.22 (2H,
203 m), 7.47 (1H, t, J=7.8Hz), 7.61 (1H, d, J=7.8Hz), 7.65 (1H, d,
J=7.8Hz), 7.80 (1H, br-s), 8.00 (1H, br-s)
51.50 (9H, s), 2.29 (3H, s), 4.85 (2H, s), 6.46 (1H, br-s), 7.20
204 (1H, br-s), 7.45-7.49 (2H, m) , 7.50 (1H, d, J=7.3Hz), 7.65 (1H, d,
J=7.3Hz), 7.88 (1H, br-s), 7.99 (1H, br-s), 8.19 (1H, d, J=8.8Hz)
5 1.26(3H, t, J=7.6Hz), 2.76(2H, q, J=7.6Hz), 4.85(2H, s), 7.06(1H,
205 br), 7.47-7.53(2H, m), 7.58-7.61(2H, m), 7.67-7.69(2H, m), 8.05(1H,
s)
5 1.25(3H, t, J=7.3Hz), 2.77(2H, q, J=7.3Hz), 4.85(2H, s), 7.06(1H,
206 br), 7.49-7.53(2H, m), 7.62(1H, s), 7.68-7.70(2H, m), 7.74(1H, s),
8.06(1H, s)
207 5 1.24(3H, t, J=7.3Hz), 2.77(2H, q, J=7.3Hz), 4.86(2H, s) , 7.07(1H,
br), 7.50-7.58(3H, m), 7.70-7.72(2H, m), 7.96(1H, s), 8.07(1H, s)
5 0.93(3H, t, J=7.3Hz), 1.63-1.69(2H, m), 2.70(2H, t, J=7.6Hz),
208 4.85(2H, s), 7.10(1H, s), 7.45(1H, s), 7.49-7.52(1H, m) , 7.53(1H,
s), 7.58-7.69(3H, m), 8.04(1H, s)
5 0.93(3H, t, J=7.3Hz), 1.61-1.70(2H, m) , 2.71(2H, t, J=7.3Hz),
209 4.85(2H, s), 7.10(1H, br-s), 7. 48-7.53(2H, m), 7.63(1H, s), 7.67-
7.70(2H, m), 7.74(1H, d, J=2.0Hz), 8.05(1H, s)
5 0.90(3H, t, J=7.3Hz), 1.28-1.38(2H, m), 1.56-1.64(2H, m) , 2.73(2H,
210 t, J=7.8Hz), 4.85(2H, s), 7.06UH, br-s), 7.49-7.53(2H, m) , 7.60(1H,
s), 7.67-7.74QH, m) , 8.04(1H, s)
53.93 (3H, s), 4.86 (2H, s), 7.13 (1H, br s), 7.53 (1H, t, J=8Hz),
211 7.61-7.65 (2H, m), 7.71 (1H, d, J=8Hz) , 8.04 (1H, s) , 8.48 (1H, d,
J=1.2Hz), 8.58 (1H, s)
22 5 2.47(3H, s), 4.85(2H, s), 7.08(1H, br-s), 7.40(1H, s), 7.51(1H, t,
J=7.8Hz), 7.63{1H, s), 7.67-7.71(3H, m), 8.03(1H, s)
213 54.86(2H,s), 7.06(1H, br.), 7.52(1H,t,J=7.8Hz) , 7. 67-7.71(3H,m),
7.67(2H,s), 8.05(lH,s)
214 5 2.26 (3H, s), 2.45 (3H, d, J=6.4Hz), 4.86 (2H, s), 7.08 (1H, br-
s), 7.49-7.53 (2H, m), 7.69-7.75 (3H, m) , 8.05 (1H, br-s)
5 2.35 (3H, s), 2.58 (3H, d, J=6.6Hz), 4.85 (2H, s), 7.08 (1H, br-
215 s), 7.35 (1H, s), 7.51 (1H, t, J=8.1Hz), 7.68 (2H, d, J=8.1Hz), 7.73
(1H, s), 8.04 (1H, s)
5 2.50 (3H, s), 4.77 (2H, br-s), 4.86 (2H, s) , 7.12 (1H, br-s),
216 7.51-7.56 (2H, m), 7.69 (2H, d, J=7.3Hz), 8.84 (1H, s) , 8.08 (1H,
|br-s) ' (

181
Table 9(12)
Compound
Mo. *H-NMR(CDCl3,ppm)
5 2.43 (3H, s), 4.86 (2H, s) , 7.12 (1H, br-s), 7.51 (1H, t, 217 J=7.9Hz), 7.57 (1H, br-s), 7.69 (1H, d, J=7.9Hz), 7.76 (1H, br-s),
7.86 (1H, br-s), 8.08 (1H, br-s)
21g 5 2.51 (3H, s), 4.86 (2H, s), 7.00 (1H, br-s), 7.50-7.55 (2H, m),
7.68-7.70 (2H, m), 7.87 (1H, br-s), 8.08 (1H, br-s)
5 2.62 (3H, s), 4.86 (2H, s), 7.00 (1H, br-s), 7.47 (1H, s), 7.52
219 (1H, t, J=7.8Hz), 7.68-7.70 (2H, m) , 7.89 (1H, br-s), 8.07 (1H, br-
s)
5 2.12 (3H, s), 4.50 (2H, br-s), 4.86 (2H, s), 7.14 (1H, br-s), 7.29
220 (1H, br-s), 7.51 (1H, t, J=7.8Hz), 7.68-7.70 (2H, m), 7.77 (1H, br-
s), 8.04 (1H, br-s)
5 0.90(3H, t, J=7.3Hz), 1.28-1.37(2H, m), 1.55-1.63(2H, m), 2.48-
221 2.60(2H, m), 2.73(2H, t, J=7.8Hz), 4.43(2H, t, J=6.3Hz), 6.85(1H,
s), 7.46-7.50(2H, m), 7.60-7.68(3H, m), 7.73(1H, d, J=1.5Hz),
8.00(1H, s)
51.32 (6H, d, J=6.3Hz), 2.39 (3H, s), 5-04 (1H, septet, J=6.3Hz),
222 6.71 (1H, s), 7.43-7.47 (2H, m), 7.57-7.64 (3H, ra), 7.73 (1H, s),
8.04 (1H, s)
5 1.32(6H, d, J=6.3Hz), 5.03(1H, septet, J=6.3Hz), 7.41(1H, t,
223 J=8.1Hz), 7.63-7.68(1H, m), 7.67(2H, s), 7.75(1H, d, J=7.6Hz),
8.00(1H, s), 8.06(1H, t, J=1.7Hz), 8.93(1H, s)
(DMSO-d6)8 1.31(6H, d, J=6.3Hz), 5.03(1H, septet, J=6.3Hz), 7.41(1H,.
224 t, J=8.1Hz), 7:64(1H, d, J=8.1Hz), 7.79(1H, d, J=8.1Hz), 7.93(1H,
s), 8.0CM1H, s), 8.15(1H, s), 8.26(1H, s) , 9.36(1H, s)
5 1.3K6H, d, J=6.3Hz), 2.34 (6H, s), 5.03(1H, septet, J=6.3Hz),
225 6.73(1H, s), 7.33(2H, s), 7.44(1H, t, J=7.8Hz), 7.53-7.62(3H, m),
8.05(1H, s)
5 1.3K6H, d, J=6.3Hz), 2.33(6H, s), 5.02(1H, septet, J=6.3Hz),
226 6.75(1H, s), 7.33(2H, s), 7.43(1H, t, J=7.8Hz), 7.52-7.61(3H, m),
8.04(1H, s)
227 8 4.84(2H, s), 7.24(1H, s), 7.45(1H, t, J=7.8Hz), 7.59-7.62(4H, m),
7.77(2H, d, J=8.8Hz), 7.99(1H, s), 8.16(1H, s)
228 5 2.39 (3H, s), 4.85 (2H, s), 7.11 (1H, br-s), 7.47-7.52 (2H, m),
7.58 (1H, s), 7.67-7.70 (2H, m), 7.73 (1H, s), 8.06 (1H, s)
229 (DMSO-d6) 5 4.86(2H, s), 7.45(1H, t, J=7.8Hz), 7.72(1H, s), 7.73(1H,
d, J=7.8Hz), 7.83-7.84(2H, m), 8.14(1H, s), 9.27(1H, s), 9.34(1H, s)
(DMSO-d6) 5 4.86(2H, s), 7.44(1H, t, J=8.1Hz), 7.67(1H, s), 7.68(1H,
230 S), 7.71-7.74(1H, m), 7.85(1H, d, J=7.3Hz), 8.15{1H, s), 9.31(1H,
s), 9.41(1H, br-s)
231 (DMSO-d6) 8 4.96(2H, s) , 7.51(1H, t, J=7.8Hz), 7.65-7.73(2H, m) ,
|8.13(1H, s), 8.15(1H, s), 8.49(1H, s), 10.41(1H, s), 10.58(1H, s)

182
Table 9(13) __^
Compound
No. 1H-NMR(CDCl3fppiti)
(DMSO-dg) 5 4.86(2H, s) , 7.45(1H, t, J=7.8Hz), 7.70(1H, d, J=7.8Hz),
232 7.88(1H, d, J=7.8Hz), 7.94(1H, s), 8-08(lH, s), 8.16(1H, s) ,
9.33(1H, s), 9.42(1H, s)
233 5 2.34(6H, s), 4.85(2H, s), 7.10(1H, br), 7.34(2H, s), 7.47-7.51(2H,
m), 7.65-7.68(2H, m), 8.06(1H, s)
234 5 2.34(6H, s), 4.85(2H, s), 7.10(1H, br), 7.35(2H, s), 7.47-7.52(2H,
m), 7.65-7. 68(2H, m), 8.05(1H, s)
235 5 4.84(2H, s), 7.17(1H, br-s), 7.49(1H, t, J=7.8Hz), 7.63(1H, d,
J=7.8Hz), 7.67(1H, d, J=7.8Hz), 7.94(1H, 5), 8.Q7(1H, s)
236 5 4.85(2H, s), 7.14(1H, s), 7.51(1H, t, J=7.8Hz), 7.68-7.73 (2H, m),
7.83(1H, s), 7.86(2H, s), 8.07(1H, s)
237 5 2.48-2.60(2H, m), 4.43(2H, t, J=6.3Hz), 6.90{1H, s), 7.48(1H, t,
J=7.8Hz), 7.63-7.69(2H, m), 7.86(3H, s), 8.03(1H, s)
(DMSO-d6) 5 2.50-2.61(2H, m), 4.41(2H, t, J=6.3Hz), 7.43(1H, t,
238 J=7.8Hz), 7.70(1H, d, J=7.8Hz), 7.71(1H, s), 7.80-7.84(2H, m) ,
8.06(1H, s), 8.82(1H, s), 9.26(1H, s)
5 1.34(3H, t, J=7.3Hz), 4.26(2H, q, J=7.3Hz), 6.77(1H, br-s), 7.46-
239 7.53(2H, m), 7.70(1H, brd, J=7.3Hz), 7.86-7.94(3H, ra), 8.39(1H, s),
8.71 (1H, d, J=8.8Hz)
5 1.32(6H, d, J=6.3Hz), 5.06(1H, septet, J=6.3Hz), 6.74(1H, s),
240 7.45-7.52(2H, m), 7.70(1H, d, J=7.3Hz), 7.86-7.94(3H, m), 8.40(1H,
s), 8.71 (1H, d, J=8.8Hz)
5 4.58(1H, dd, J=2.0Hz, 5.8Hz), 4.85(1H, dd, J=2.0Hz, 4.2Hz),
241 7.06(1H, br-s), 7.30(1H, d, J=6.4Hz), 7.49-7.57{2H, m), 7.74(1H, d,
J=7.8Hz), 7.87(1H, d, J=7.8Hz), 7.91(1H, s), 7.99(1H, s), 8.40(1H,
s), 8.71(1H, d, J=8.8Hz)
81.62-1.70(2H, m), 1.71-1.87(4H, ra), 1.89-1.96(2H, m), 5.22-5.26(1H,
242 m), 6.72(1H, s), 7.45-7.51(2H, m), 7.70(1H, brd, J=7.3Hz), 7.86-
7.93(3H, m), 8.34(1H, s), 8.70(1H, d, J=8.8Hz)
5 3.76(2H, t, J=5.4Hz), 4.47(2H, t, J=5.4Hz), 6.97(1H, br-s), 7.47-
243 . 7.56(2H, m), 7.69(1H, d, J=7.8Hz), 7.86-7.91(2H, m), 7.97(1H, s),
8.39(1H, s), 8.71(1H, d, J-8.8Hz)
5 2.82(2H, t, J=6.3Hz), 4.41(2H, t, J=6.3Hz), 7.46(1H, t, J=7.8Hz),
244 7.54-7.57(lH, m) , 7.81(1H, d, J=8.3Hz), 7.88(1H, d, J=8.8Hz),
7.91(1H, s), 8.10(1H, s), 8.56-8.63(2H, m), 9.55(1H, br-s)
54.40(2H, dt, J=3.9Hz, 14.1Hz), 6.04(1H, tt, J=3.9Hz, 55.3Hz), 7.43-
245 7.48(1H, m), 7.55{1H, d, J=7.8Hz), 7.80(1H, d, J=7.3Hz), 7.86(1H, d,
J=8.8Hz), 7.91(1H, s), 8.07(1H, s), 8.53(1H, s), 8.64(1H, d,
J=8.8Hz), 9.42(1H, s)
54.56{2H, d, J=5.9Hz), 5.92(1H, t, J=5.9Hz), 6.97(1H, br-s), 7.49-
246 7.57(2H, m), 7.69(1H, d, J=7.3Hz), 7.87-7.92(2H, m), 7.98(1H, s),
[8.39(1H, s), 8.7K1H, d, J=8.8Hz)

183
Table 9(14)
Compound
No. JH-NMR(CDCl3,ppm)
5 4.86(2H, s), 7.15CLH, br-s), 7.50-7.59 (2H, m) , 7.72(1H, d,
247 J=7.8Hz), 7.86-7.92(2H, m), 8.02{1H, s), 8.40{1H, s), 8.71(1H, d,
J=8.8Hz)
55.05(2H, s), 7.09(1H, br-s), 7.51-7.59(2H, m), 7.73(1H, d,
248 J=7.8Hz), 7.88(1H, d, J=8.3Hz), 7.92(1H, s), 8.03(1H, s), 8.39(1H,
s), 8.72(1H, d, J=8.8Hz) __
5 2.49-2.60(2H, m), 4.44(2H, t, J=6.3Hz), 6.86(1H, br-s), 7.48-■ 249 7.56(2H, m) , 7.69(1H, d, J=6.3Hz), 7.88(1H, d, J=8.8Hz), 7.92(1H,
s), 7.96(1H, s), 8.39(1H, s), 8.71(1H, d, J=8.8Hz)
54.68(2H, t, J=13.2Hz), 708(1H, br-s), 7.50-7.59(2H, m), 7.70(1H,
250 br-d, J=7.3Hz), 7.87-7.92(2H, m), 8.00(1H, s), 8.39(1H, s), 8.71(1H,
d, J=8.7Hz)
55.29(2H, s), 6.92(1H, br-s), 7.47-7.55(4H, m), 7.65-7.70(3H, m),
251 7.87(1H, d, J=8.8Hz), 7.92(1H, s), 7.97(1H, s), 8.38(1H, br-s),
8.71(1H, d, J=8.8Hz)
55.23{2H, s), 6.82(1H, br-s), 7.37(1H, d, J=8.3Hz), 7.50-7.53(2H,
252 m), 1.6 {lii, m) , 7.75 (1H, dd, J=2.4Hz, 8.3Hz), 7 .87-7. 96 (3H, m),
8.38(1H, br-s), 8.47(1H, d, J=2.4Hz), 8.72(1H, d, J=8.3Hz)
5 1.3K6H, d, J=6.3Hz), 2.33(6H, s), 5.02(1H, septet, J=6.3Hz),
253 6.75(1H, br-s), 7.33(2H, s), 7.43(1H, t, J=7.8Hz), 7.54-7.61(3H, m),
8.04(1H, s)
5 2.34(6H, s), 4.39(2H, dt, J=3.9Hz, 13.6Hz), 6.01(1H, tt, J=3.9Hz,
254 54.6Hz), 6.98(1H, s), 7.34(2H, s), 7.46-7.50(2H, m), 7.60-7.66(2H,
m) , 8.02(1H, s)
5 2.34 (6H, s), 4.61-4.66 (2H, m), 4.71-4.77 (2H, m) , 5.18-5.30 (1H,
255 m), 7.12 (1H, s), 7.34 (2H, s), 7.45-7.50 (1H, m) , 7.52-7.66 (2H,
m), 7.76-7.84 (1H, m), 8.04 (1H, s)
25g 5 2.34(6H, s), 4.58(2H, q, J=8.3Hz), 7.02(1H, s), 7.34(2H, s), 7.45-7.51(2H, m), 7.62-7.67(2H, m) , 8.02(1H, s)
257 5 2.34(6H, s), 4.85(2H, s), 7.10(1H, br), 7.34(2H, s), 7.47-7.51(2H, m), 7.63-7.67 (2H, m), 8.05(1H, s)
25g 51.48(3H, d, J=6.8Hz), 2.34(6H, s), 5.30-5.36(1H, m) , 6.95(1H, br-
s), 7.30(2H, s), 7.46-7.51(2H, m), 7.60-7.67(2H, m) , 8.03(1H, br-s)
25g 5 2.35(6H, s), 2.49-2.59(2H, m), 4.42(2H, t, J=6.3Hz), 6.85(1H, br-
s), 7.34(2H, s), 7.45-7.49(2H, m), 7.60-7.65(2H, m) , 8.02(1H, br-s)
300 5 4.85(2H, s), 7.10(1H, br), 7.50(1H, t, J=7.8Hz), 7.68-7.71 (3H, m),
7.72(2H, s), 8.04(1H, s)
3Q1 5 4.85(2H, s), 7.08(1H, br), 7.51-7.55(1H, m), 7.69-7.72(2H, m),
|7.84(1H, s), 8.06(2H, s) , 8.10(1H, s) J

184
Table 9(15)
Compound
No. ^-NMRtCDCl^ppm)
33 5 2.29(6H, s), 4.85(2H, s), 7.11-7.19(3H, m) , 7.39(1H, s), 7.49(1H,
t, J=7.9Hz), 7.66-7.73(2H, m), 8.00 (1H, s)
348 5 2.35(6H, s), 3.81(3H, s), 6.80(1H, br) , 7.36(2H, s), 7.44-7.63(4H,
m), 8.02(1H, s)
377 5 2.36(6H, s), 4.85(2H, s), 7.09(1H, s), 7.37(2H, s), 7.44(1H, s),
7.50(1H/ t, J=8.3Hz), 7.67(2H, d, J=7.3Hz), 8.05 (1H, s)
424 54.85(2H, s), 7.10(1H, s), 7.51(1H, t, J=7.8Hz), 7.69-7.70(3H, m),
7.73(2H, s), 8.05(1H, s)
464 5 2.47-2.59(2H, in), 4.41(2H, t, J=6.3Hz), 6.96(1H, br-s), 7.46(1H,
t, J=7.8Hz), 7.63-7.67(2H, m), 7.83(1H, s), 7.91(2H, s), 8.00(1H, s)
471 5 4.85(2H, s), 7.13(1H, br-s), 7.50(1H, t, J=7.8Hz), 7.68-7.74(3H,
m), 7.92(2H, s), 8.04(1H, s)
(DMSO-d6) 5 2.67-2.78(2H, m), 4.34(2H, t, J=5.9Hz), 7.50(1H, t,
511 J=7.8Hz), 7.68-7.73(2H, m), 8.13(1H, s), 8.52(2H, s), 10.02(1H, s),
10.77(1H, s)
518 (DMSO-d6) 5 4.96(2H, s), 7.52(1H, t, J=7.8Hz), 7.71-7.75(2H, m), 8.16(1H, s), 8.5K2H, s), 10.42(1H, s), 10.79(1H, s)
565 84.86(2H, s), 7.00(1H, br-s), 7.52(1H, t, J=8.3Hz), 7.70-7.73(3H, m), 7.93(2H, s), 8.06(1H, s)
605 5 2.49-2.60(2H, m) , 4.43(2H, t, J=6.3Hz), 6.82(1H, s), 7.49(1H, t, J=7.8Hz), 7.66-7.68(3H, m), 7.94(2H, s), 8.01(1H, s)
612 54.86(2H, s), 7.45(1H, t, J=7.8Hz), 7.72(1H, d, J=7.8Hz), 7.94(1H, br-s), 7.93(2H, s), 8.13(1H, s), 9.02(1H, s), 9.17(1H, s)
659 54.86(2H, s), 7.06(1H, s), 7.51(1H, t, J=7.8Hz), 7.68-7.71(3H, m),
7.93(2H, s), 8.06(1H, s)
706 54.84(2H, s), 7.40(1H, br-s), 7.48(1H, t, J=7.8Hz), 7.67-7.75(2H,
m), 8.00(1H, s), 8.09(2H, s), 8.24(1H, s)
770 5 2.39(3H, s), 4.86(2H, s), 7.00(1H, br-s), 7.48-7.67(5H, m),
7.79(1H, s), 8.04(1H, s), 8.24(1H, d, J=8.8Hz)
800 5 2.31(6H, s), 4.85(2H, s), 7.11(1H, br-s), 7.43(2H, s), 7.47-
I |7.53(2H, m) , 7.66(1H, s), 7.67 (1H, s) , 8.05(1H, s)

185
Table 9(16)
Compound
No. Hi-NMRtCDCJ^ppm)
80.89(3H, t, J=7.3Hz), 1.24-1.37{2H, m), 1.55-1.63(2H, m), 2.47-2.59(2H, m) ,
817 2.70(2H, t, J=7.8Hz), 4.42(2H, t, J=5.9Hz), 6.96(1H, br-s), 7.43-7.47(2H, m) ,
7.57(1H, d, J=1.5Hz), 7.62-7.64(2H, m), 7.74(1H, s), 8.00(1H, s)
50.86(3H, t, J=7.3Hz), 1.24-1.33(2H, m), 1.49-1.57(2H, m), 2.45-2.56(2H, m) ,
818 2.67(2H, t, J=7.8Hz), 4.38(2H, t, J=6.3Hz), 7.15(1H, s), 7.39(1H, t,
J=7.8Hz), 7.48(1H, s), 7.62-7.64(2H, m), 7.88(1H, s) , 7.93(1H, d, J=2.0Hz),
8.01(1H, s)
5 0.81(3H, t, J=7.3Hz), 1.25(3H, d, J=6.8Hz), 1.53-1.64(2H, m), 2 . 49-2.60(2H,
819 m), 2.92-3.0K1H, m) , 4.43(2H, t, J=5.9Hz), 6.87(1H, br) , 7.46-7.51 (2H, m) ,
7.62-7.67QH, m), 7.74(1H, d, J=1.5Hz), 8.01(1H, s)
51.32(6H,d,J=6.3Hz), 2.36(3H,s), 5.01-5.07(lH,m), 6.69(lH,s), 7.11-
820 7.13(2H,m), 7.44(1H,t,J=8.3Hz), 7.55-7.59(2H,m), 7.68(1H,br-s),
7.95(lH,d,J=8.3Hz), 7.99(lH,s) ______
5 1.27(6H, d, J=6.8Hz), 1.31(6H, d, J=6.3Hz), 2.96(1H, septet, J=6.8Hz),
821 5.05(1H, septet, J=6.3Hz), 6.79(1H, s), 7.42-7.52(4H, m), 7.72(1H, d,
J=7.8Hz), 7.86(1H, t, J=2.0Hz), 8.14(1H, s), 8.21(1H, d, J=8.3Hz)
822 5 1.33(6H,d,J=6.6Hz), 5.01-5.09(lH,m), 6.73(lH,s), 7 . 41-7 .52 (2H,rn), 7.57-
7.60(lH,m), 7.65(lH,s), 8.05(lH,s), 8.20(2H,s), 8.35(lH,s)
5 1.32(6H, d, J=6.3Hz), 5.04 (1H, septet, J=6.3Hz), 6.7-0 (1H, br-s), 6.98-
823 7.06(1H, m), 7.45{1H, t, J=7.8Hz), 7.53-7.55(1H, m), 7.62(1H, d, J=8.8Hz),
7.94(2H, s), 8.07-8.14(lH, m)
51.32 (6H, d, J=6.1Hz), 2.46 (3H, s), 2.54 (3H, d, J=15Hz), 5.04 (1H, septet,
824 J=6.1Hz), 6.72 (1H, s) , 7.40-7.44 (2H, m), 7.51-7.56 (3H, m), 7.94 (1H, s),
7.97 (1H, s)
5 1.31 (6H,. d, J=6.3Hz), 2.30(3H, s) , 5.03(1H, septet, J=6.3Hz), 6.72(1H, s),
825 7.20(1H, d, J=2.2Hz), 7.32(1H, d, J=2.2Hz), 7.43(1H, t, J=7.8Hz), 7.59-
7.62(3H, m), 8.00(1H, s)
51.31 (6H, d, J=6.3Hz), 2.28 (3H, s), 2.31 (3H, s), 5.03 (1H, septet,
826 J=6.3Hz), 6.71 (1H, br-s), 7.01 (1H, s), 7.13 (1H, s), 7.43 (1H, t, J=7.8Hz),
7.61-7.63 (3H, m), 7.97 (1H, s)
5 1.31(6H, d, J=6.1Hz), 2.25(6H, s), 5.03(1H, septet, J=6.1Hz), 6.70(1H, br-
827 S), 7.26(2H, s), 7.38(1H, br-s), 7.43(1H, t, J=7.8Hz), 7.55-7.61(2H, m) ,
8.01(1H, s)
828 5 1.31(6H, d, J=6.3Hz), 2.24(6H, s), 5.02(1H, septet, J=6.3Hz), 6.71(1H, br-
s), 7.26(2H, s), 7.39-7.44(2H, m), 7.55-7.60(2H, m), 8.00(1H, s)
51.31 (6H, d, J=6.4Hz), 2.23 (6H, s), 5.03 (1H, septet, J=6.4Hz), 6.69 (1H,
829 br-s), 7.37 (1H, br-s), 7.43 (1H, t, J=7.8Hz), 7.48 (2H, s), 7.55-7.61 (2H,
m), 8.01 (1H, br-s)
830 51.32 (6H, d, J=6.3Hz), 2.35 (6H, s) , 5.04 (1H, septet, J=6.3Hz), 6.72 (1H,
s), 7.32-7.36 (3H, m), 7.41-7.46 (4H, m), 7.56-7.63 (4H, m), 8.00 (1H, s)
51.32 (6H, d, J=6Hz), 2.30 (3H, s) , 2.32 (6H, s), 5.04 (1H, septet, J=6Hz),
831 6.73 (1H, s), 7.08 (2H, s), 7.22-7.26 (4H, m) , 7.43-7.48 (2H, in), 7.61-7.63
|(2H, m), 8.01 (1H, s)

186
Table 9(17) .
Compound
No. LH-NMR(CDCl3,ppin)
51.32(6H, d, J=6Hz), 2.31(6H, s), 2.42(3H, s), 5.04(1H, septet, J=6Hz),
832 6.71(1H, s), 7.16(1H, d, J=8Hz), 7.30-7.59(7H, m), 7.62(2H, t, J=8Hz),
8.0K1H, s)
51.3K6H, d, J=6Hz), 2.33(6H, s), 2.49(3H, s), 5,03(1H, septet, J=6Hz) ,
833 6.73(1H, s), 7 .12-7 . 25 (2H, m), 7.32(2H, s), 7.42-7.52(4H, in), 7. 59-7 . 63 (2H,
m), 7.99(1H, s)
51.32(6H, d, J=6Hz), 2.32(6H, s), 3.80(3H, s), 5.04(1H, septet, J=6Hz),
834 6.73(1H, s), 6.97(1H, d, J=8Hz), 7.02{1H, t, J=7Hz), 7.27{2H, s), 7.30{2H, d,
J=7Hz), 7.34-7.46(2H, m) , 7.60-7.63(2H, m), 7.95(1H, s)
5l.32(6H, d, J=7Hz), 2.34(6H, s), 3.87(3H, s), 5.04(1H, septet, J=7Hz),
835 6.72(1H, s), 6.88-6.91(1H, m), 7.11(1H, t, J=2Hz), 7.16(1H, td, J=8Hz, 1Hz),
7.33-7.37(3H, m), 7.43-7.50(2H, m), 7.59-7.64(2H, m), 8.01(1H, s)
51.32(6H, d, J=7Hz), 2.33(6H, s), 3.85(3H, s), 5.04(1H, septet, J=7Hz),
836 6.73(1H, br-s), 6.96(2H, d, J=9Hz), 7.29(2H, s), 7.42-7.52(4H, m), 7.60-
7.63(2H, m), 8.00(1H, s)
51.32 <6H, d, J=6Hz), 1.44 (3H, t, J=7Hz), 2.33 (6H, s), 4.08 (2H, q, J=7Hz),
837 5.04 (1H, septet, J=6Hz), 6.72 (1H, s), 6.94-6.97 (2H, m), 7.29 (2H, s),
7.42-7.52 (4H, m), 7.61-7.63 (2H, m), 7.99 (1H, s)
838 51.31 (6H, d, J=6Hz), 2.34 (6H, s), 2.53 (3H, s), 5.04 (1H, septet, J=6Hz),
6.72 (1H, s), 7.31-7.65 (10H, m), 8.00 (1H, s).
839 51.31 (6H, d, J-6.3HZ), 2.34 (6H, s), 5.04 (1H, septet, J=6.3Hz), 6.72 (1H,
s), 7.12-7.32 (5H, m), 7.41-7.48 (3H, m), 7.61-7.63 (2H, m), 7.99 (1H, s)
840 51.32(6H, d, J=7Hz), 2.34(6H, s), 5.03(1H, septet, J=7Hz), 6.74(1H, br s),
7.01-7.05(1H, m), 7.28-7.64(9H, m), 8.02(1H, s)
841 51.31 {6H, d, J=7Hz), 2.34 (6H, s), 5.04 (1H, septet, J=7Hz), 6.73 (1H, s) ,
7.11 (2H, t, J=9Hz), 7.28 (2H, s), 7.42-7.63 (6H, m) , 8.01 (1H, s)
51.24 (6H, d, J=6.8Hz), 1.31 (6H, d, J=6.3Hz), 2.32 (3H, s), 2.86 (1H,
842 septet, J=6.8Hz), 5.03 (1H, septet, J=6.3Hz), 6.74 (1H, s), 7.08 <1H, s) ,
7.33 (1H, d, J=2.0Hz), 7.43 (1H, t, J=7.8Hz), 7.61-7.65 (3H, m), 7.96 (1H, s)
51.32 (6H, d, J=6.3Hz), 2.37 (3H, s), 5.03 (1H, septet, J=6.3Hz), 6.74 (1H,
843 s), 7.46 (1H, t, J=7.8Hz), 7.51-7.57 (2H, ni) , 7.61-7.65 (2H, m), 7.90 (1H,
s), 8.08 (1H, s)
5 1.32(6H, d, J=6.3Hz), 2.35(3H, s), 5.03(1H, septet, J=6.3Hz), 6.72(1H, s),
844 7.09(1H, s), 7.21(1H, d, J=2.2Hz), 7.44(1H, t,J=8.1Hz), 7.52-7.61{3H, m),
8.02(1H, s)
5 1.29(6H, d, J=6.8Hz), 1.31(6H, d, J=6.3Hz), 2.98(1H, septet, J=6.8Hz),
845 5.04(1H, septet, J=6.3Hz), 6.70{1H, s), 7.42-7.48(2H, m), 7.56-7.67{4H, m) ,
7.92(1H, s)
846 5 1.32(6H, d, J=6.3Hz), 5.03(1H, septet, J=6.3Hz), 6.75(1H, br-s), 7.41-
I [7.51(2H, m), 7.62-7.65(lH, m) , 7.91(1H, br-s), 8.08(1H, s)

187
Table 9(18)
Compound
No- 'H-NMRtCDC^ppm) .
(DMSO-d6) § 1.24-1.44(5H, m) , 1.68-1.80(5H, m) , 2.46-2.50 (1H, m),
847 4.97(2H, s), 7.19(2H, d, J=8.8Hz), 7.47(1H, t, J=7.8Hz), 7.60-
7.70(4H, m), 8.04(1H, s), 10.19(1H, s), 10.37(1H, s)
5 4.84(2H, s), 7.29{1H, d, J=7.8Hz), 7.35(1H, br-s), 7.48(1H, t,
848 J=7.8Hz), 7.56-7.67(3H, m), 7.75(1H, d, J=7.3Hz), 7.97(1H, s),
8.23(1H, s), 8.37(1H, d, J=7.8Hz)
849 5 4.85(2H, s), 7.12(1H, br-s), 7.47(1H, t, J=7.8Hz), 7.59-7.67(4H,
n), 7.72-7.75(2H, m), 7.99(1H, s) , 8.03(1H, s)
(DMSO-d6) 5 4.87(2H, s), 7.43(1H, t, J=7.8Hz), 7.65(1H, d, J=7.8Hz),
850 7.82UH, d, J=7.8Hz), 7.96(2H, d, J=8.8Hz), 8.07(1H, s) , 8.18-
8.22(2H, m), 9.66(1H, br), 10.51(1H, s)
54.85(2H, s), 6.67(1H, br-s), 7.47(1H, t, J=7.8Hz), 7.60-7.64(2H,
851 m), 7.65(2H, d, J=8.8Hz), 7.74(2H, d, J=8.8Hz), 7.98(1H, s),
8.00(1H, s)
54.86(2H, s), 7.09(1H, br-s), 7.48-7.53(1H, in), 7.61-7.65(2H, m),
852 7.81(2H, d, J=8.8Hz), 7.95(2H, d, J=8.8Hz), 7.95-8.04(1H, m) ,
8.14(1H, s)
50.90(3H, t, J=7.3Hz), 1.28-1.38(2H, m), 1.56-1.65(2H, m) , 2.72(2H,
854 t, J=7.8Hz), 4.85(2H, s), 7.14(1H, br-s), 7.45(1H, s), 7.50(1H, t,
J=7.8Hz), 7.58(1H, d, J=1.5Hz), 7.66-7.68(3H, m), 8.04(1H, s)
5 0.88(3H, t, J=7.3Hz), 1.24-1.35(2H, m), 1.52-1.60(2H, m), 2.70(2H,
855 t, J=7.8Hz), 4.84{2H, s), 7.27(1H, s), 7.46-7.50(2H, m) , 7.67-
7.69(2H, m), 7.76(1H, s), 7.94(1H, d, J=1.5Hz), 8.06(1H, s)
5 0.81(3H, t, J=7.3Hz), 1.25(3H, d, J=5.9Hz), 1.55-1.65(2H, m),
856 2.91-3.0K1H, m) , 4.85(2H, s) , 7.14(1H, br), 7 .50-7 .53 (2H, m) , 7.61-
7.77(4H, in), 8.05(1H, s)
50.90(3H, t, J=7.3Hz), 1.31(3H, d, J=6.8Hz), 1.63-1.74(2H, m), 2.82-
g57 2.91(1H, in), 4.85(2H, s) , 7.22(1H, s) , 7.47-7 .53 (3H, m) , 7.58-
7.62(1H, m), 7.66(1H, d,J=8.3Hz), 7.93(1H, s), 8.05(1H, s), 8.13-
8.15(1H, m)
858 5 2.36{3H,s), 4.85(2H,s), 7.11-7.14(3H,m), 7.49(1H,t,J=8.3Hz), 7.61-
7.69(3H,m), 7.95(lH,d,J=8.3Hz), 8.02(lH,s)
5 2.31 (3H, s), 4.34 (2H, q, J=7.8Hz), 4.84 (2H, s), 6.80-6.86 (2H,
859 m), 7.16 (1H, br-s), 7.47 (1H, t, J=7.8Hz), 7.60-7.72 (4H, m), 7.99
(1H, br-s)
860 5 2.39(3H,s), 4.85(2H,s), 7.09-8.14(9H,m)
861 5 2.31(3H/s), 4.84(2H,s), 7.17(lH,br), 7.20-7.23(2H,m),
7.47(lH,t,J=8.1), 7.58- 7.67(3H,m), 7.84-7.87 (lH,m) , 8.00(lH,s)
5 1.27(6H, d, J=6.8Hz), 2.97(1H, septet, J=6.8Hz), 4.85(2H, s),
862 7.18(1H, br), 7.46-7.51(3H, m), 7.57(1H, dd, J=1.5Hz, 7.8Hz),
|7.74(1H, d, J=7.8Hz), 7.94(1H, s), 8.14(1H, s), 8.2K1H, d, J=8.3Hz)

188 Table 9(19)
Compound
NO- 'H-NMRtCDCl^ppm)
863 54.87(2H,s), 7.51-8.01(8H,m), 8.86(lH,s)
864 5 4.87(2H,s), 7.08(lH,br.), 7.49-7.58(4H,m), 8.07(lH,br.),
8.20(3H,s)
5 4.86(2H, s), 7.08(1H, br-s), 7.48-7.60(3H, m), 7.64(1H, d,
865 J=2.4Hz), 7.72(1H, d, J=7.3Hz), 7.98UH, s) , 8.18(1H, s), 8.39(1H,
d, J=8.8Hz)
g66 5 4.85(2H, s), 7.06(1H, br), 7.41-7.51 (2H, m), 7.60(1H, s), 7.65-
7.74(4H, m), 7.97(1H, s)
g67 54.86 (2H, s), 7.10 (1H, br-s), 7.48-7.57 (2H, m), 7.71 (1H, d,
J=8.3Hz), 7.90-7.97 (3H, m), 8.19 (1H, br-s), 8.22 (1H, d, J=8.8Hz)
868 5 4.85(2H, s), 7.12(1H, br-s), 7.46-7.56(4H, m), 7.71(1H, d,
■ J=7.8Hz), 7.99(1H, s), 8.14(1H, s) , 8.48(1H, d, J=8.8Hz) .
5 4.84(2H, s), 6.97-7.05(lH, m), 7.22(1H, br-s), 7.48 (1H, t,
869 J=7.8Hz), 7.59(1H, d, J=7.8Hz), 7.69(1H, d, J=7.8Hz), 7.96(1H, s),
7.98(1H, s), 8.05-8.12(1H, m)
870 5 2.46 (3H, s), 2.55 (3H, d, J=14Hz), 4.86 (2H, s), 7.13 (1H, br s),
7.40 (1H, s), 7.46-7.62 (4H, m), 7.88 (1H, s), 7.99 (1H, s)
871 5 2.34(3H,s), 2.38(3H,s), 4.85(2H,s), 6.97-8.03(8H,m)
g72 5 2.31(6H, s), 3.99(1H, s), 4.85(2H, s), 7.15(1H, br-s), 7.45-7.51
(4H, m), 7.64-7.66(2H, m), 8.01(1H, s)
873 5 2.34(6H, s), 3.74(1H, s), 4.85(2H, s), 7.08(1H, br-s), 7.48(1H,
s), 7.49(2H, s), 7.52{1H, s), 7.65-7.67(2H, m), 8.04(1H, s)
874 5 2.30(6H, s), 4.87(2H,s), 7.08(lH,br), 7.49-7.58(4H,m),
8.07(lH,br), 8.20(3H,s)
875 5 2.25(6H, s), 4.85(2H, s), 7.07(1H, br), 7.12(2H, s), 7.36(1H, br-
s), 7.48(1H, t, J=7.8Hz), 7.64-7.66(2H, m), 8.02(1H, s)
5 2.28 (3H, s), 2.31 (3H, s), 4.84 (2H, s) , 7.00 (1H, s) , 7.12 (1H,
876 s), 7.18 (1H, br), 7.47 (1H, t, J=7.8Hz), 7.60 (1H, s) , 7.66-7.68
(2H, m), 7.99 (1H, s)
g77 5 2.19(6H, s), 4.82{2H, s), 7.22(2H, s), 7.41(1H, t, J=8.1Hz),
|7.48(1H, br) , 7.61-7.66(3H, m), 7.99(1H, s) j

189
Table 9(20)
!
Compound {
No. ^-NMRtCDCl^ppm)
878 S 2.22 (6H, s), 4.84 (2H, s), 7.13 (1H, br-s), 7.39 (1H, s), 7.45-
7.49 (3H, m), 7.64-7.65 (2H, m), 8.01 (1H, br-s)
g7g 5 2.35 (6H, s), 4.85 (2H, s), 7.09 (1H, s), 7.32-7.69 (11H, m), 8.02
(1H, s)
5 2.30 (3H, s), 2.32 (6H, s), 4.85 (2H, s), 7.09 (2H, s), 7.13 (1H,
880 s), 7.21-7.27 (4H, m), 7.46-7.51 (2H, m), 7.68 (2H, d, J=7Hz), 8.03
(1H, s)
881 5 2.34(6H, s), 2.42(3H, s), 4.85(2H, s), 7.12-7.23(2H, m) , 7.29-
7.39(4H, m), 7.47-7.52(2H, m) , 7.68(2H, d, J=7Hz), 8.03(1H, s)
5 2.34(6H, s), 2.40(3H, s), 4.85(2H, s), 7.13(1H, d, J=4Hz), 7.23-
882 7.26(2H, m) , 7.30(2H, s) , 7. 33-7.50 (4H, in), 7.67(2H, d, J=8Hz) ,
8.02(1H, s)
5 2.32(6H, s), 3.8K3H, s), 4.85(2H, s), 6.97-7.04 (2H, m) , 7.10(1H,
883 brs), 7.28(2H, s), 7.30-7.34(2H, m), 7.42(1H, s), 7.49(1H, t,
J=8Hz), 7.66-7.70(2H, m), 7.99(1H, s)
5 2.35(6H, s), ,3-88(3H, s), 4.85(2H, s), 6.89-6.91(1H, m), 7.10-
884 7.18(3H, m) , 7.33-7.37(3H, m), 7.47-7.52(2H, m), 7.68(2H, d, J=7Hz),
8.03(1H, s)
5 2.33{6H, s), 3.86(3H, s), 4.85(2H, s), 6.96(2H, d, J=9Hz),
885 7.14(1H, brs), 7.30(2H, s), 7.47-7.53(4H, m), 7.68(2H, d, J=7Hz),
8.02(1H, s)
51.44 (3H, t, J=7Hz), 2.33 (6H, s), 4.08 (2H, q, J=7Hz), 4.85 (2H,
886 s), 6.95 (2H, d, J=9Hz), 7.13 (1H, s), 7.30 (2H, s), 7.45-7.52 (4H,
m), 7.68 (2H, d, J=7Hz) , 8.01 (1H, s)
887 5 2.33 (6H, s), 2.53 (3H, s), 4.84 (2H, s), 7.14 (1H, s), 7.30-7.38
(4H, m), 7.46-7.57 (4H, m), 7.67 (2H, d, J=6Hz), 8.02(1H, s)
888 5 2.34 (6H, s), 4.85 (2H, s), 7.10-7.34 (6H, m), 7.41-7.52 (3H, m),
7.68 (2H, d, J=8Hz), 8.02 (1H, s)
88g 5 2.34(6H,. s), 4.85(2H, s), 7.01-7.06(1H, m) , 7.16(1H, brs), 7.25-
7.50(8H, m), 7.68(1H, d, J=8Hz), 8.03(1H, s)
8go 5 2.33 (6H, s), 4.85 (2H, s), 7.09-7.15 (3H, m), 7.29 (2H, s), 7.46-
7.55 (4H, m), 7.67-7.69 (2H, m), 8.03 (1H, s)
g91 5 2.34(6H, s), 4.85(2H, s), 7.09(1H, brs), 7.18-7.30(4H, m), 7.34-
7.51(3H, m), 7.67-7.69(2H, m), 8.04(1H, s)
g92 5 2.30(9H, s), 4.85(2H, s), 7.05(1H, t, J=8.8Hz), 7.14(1H, br s),
|7.28(2H, s), 7.32-7.51(4H, m), 7.67-7.69(2H, m), 8.03(1H, s) (

190
Table 9(21)
Compound
Mo. ^-NMR (CDCl3, ppra)
5 2.3K6H, s), 4.85(2H, s), 6.69(1H, s) , 7.09(1H, br-s) , 7.25(2H,
893 S), 7.41(1H, s), 7.47-7.51 (2H, m) , 7.66-7.68(2H, m), 7.72(1H, s),
8.02(1H, s)
5 2.30(6H, s), 4.84(2H, s), 7.07-7.09 (1H, m), 7.25(1H), 7.27-
894 7.29(1H, m), 7.36(2H, s), 7.36(2H, s), 7.45-7.50(2H, m), 7.65-
7.67(2H, m), 8.02(1H, s)
895 5 2.32(6H, s), 4.85(2H, s), 7.18(1H, s), 7.35-7.50(7H, m) , 7.67(2H,
d, J=6.8Hz), 8.02CLH, s) __
5 2.3K3H, s), 4.85(2H, s), 7.10(1H, br) , 7.20(1H, d, J=2.2Hz),
896 7.32(1H, d, J=2.2Hz), 7.49(1H, t, J=7.8Hz), 7.57{1H, s) , 7.66-
7.68(2H, m), 8.02(1H, s)
(DMSO-d6) 5 4.85(2H, s), 7.44(1H, t, J=7.8Hz), 7.63-7.68(2H, m),
897 7.72(1H, d, J=2.4Hz), 7.84(1H, s), 8.06(1H, s), 8.80(1H, s),
9.09(1H, s)
898 54.85(2H, s), 7.00(1H, br-s), 7.51(1H, t, J=8.3Hz), 7.69-7.72(5H,
m) , 8.05(1H, s)
8gg 54.86(2H, s), 7.00(1H, br-s), 7.53{1H, t, J=7.8Hz), 7.67-7.73(2H,
m), 7.92(1H, s), 8.05(2H, s), 8.11(1H, s)
goo (DMSO-d6) 8 4.98(2H, s), 7.52(1H, t, J=7.8Hz), 7.70-7.75 (2H, m),
8.17(1H, s), 8.3K2H, s), 10.42(1H, s), 10.63(1H, s)
(DMSO-d6) 8 1.24-1.47(5H, m), 1.66-1.80(5H, m), 2.54-2.60(1H, m),
901 4.96(2H, s), 7.48(1H, t, J=7.8Hz), 7.60(2H, s), 7.67-7.71(2H, m),
8.11(1H, s), 10.24(1H, s), 10.37(1H, s)
(DMSO-d6) 8 4.86(2H, s), 7.44(1H, t, J=7.8Hz), 7.67(1H, d, J=7.8Hz),
902 7.82(1H, d, J=2.0Hz), 7.85(1H, s), 8.05(1H, d, J=2.0Hz), 8.06(1H, d,
J=7.8Hz)y 9.04(1H, s), 9.27(1H, s)
g03 54.86(2H, s), 7.00(1H, br-s), 7.51(1H, t, J=7.8Hz), 7.70(2H, d,
J=7.8Hz), 7.75(1H, s), 7.94(2H, s), 8.06(1H, s)
5 2.20(3H,s), 4.85(2H,s), 6.60{lH,d,J=2.4Hz), 7.17(1H,br.),
904 7.50(lH,t,J=7.8Hz), 7.54(lH,s), 7.59(lH,s), 7.69(1H,d,J=7.8Hz),
7.72(lH,br), 8.03(lH,s)
5 2.36(3H, s), 4.85(2H, s), 7.08(1H, br-s), 7.10(1H, s), 7.22-
905 7.23(1H, ra), 7.50(1H, t, J=8.1Hz), 7.59(1H, s), 7.67-7.69 (2H, m),
8.04(1H, s)
5 2.36(3H,s), 4.86(2H,s), 4.88(2H,s), 7.04(lH,br.),
906 7.12(lH,d,J=2.4Hz), 7.27(lH,s), 7.50(1H, t,J=7.8Hz), 7.56(lH,s),
7.67-7.70(2H,m), 8.02(lH,s)
90? 5 2.38 (3H, s), 4.85 (2H, s), 7.14 (1H, br), 7.49-7.53 (2H, m),
[7.62-7.70 (3H, m) , 7.85 (1H, s), 8.09 (1H, s)

191
Table 9(22)
JCompound J
No. ^-NMTKCDC^ppm) __
90g 5 2.28 (3H, s), 4.84 (2H, s), 7.11 (1H, br-s), 7.48 (1H, t, J=7.8Hz), 7.55
(1H, s), 7.59 (1H, s), 7.64-7.68 (3H, m), 8.01 (1H, br-s)
51.24 (6H, d, J=6.8Hz), 2.33 (3H, s) , 2.86 (1H, septet, J=6.8Hz), 4.85 (2H,
909 S), 7.09 (1H, s), 7.16 (1H, br), 7.33 (1H, d, J=2.0Hz), 7.48 (1H, t, J=7.8Hz)
7.60 (1H, s), 7.67-7.69 (2H, m), 8.00 (1H, s)
910 5 2.23(3H,s), 4.86(2H,s), 6.51(lH,s), 6.78(lH,d,J=2.4Hz), 7.15(lH,br.),
7.49(lH,br.), 7 .51(1H, t, J=7.8), 7.56(lH,s), 7.71(lH,d,J=6.8Hz), 8.05(lH,s)
5 1.29(6H, d, J=7.3Hz), 2.98(1H, septet, J=7.3Hz), 4.85(2H, s) , 7.10(1H, br),
911 7.47-7.52(2H, m) , 7'. 56-7.58 (2H, m) , 7.65(1H, d, J=7.3Hz), 7.72(1H, br) ,
7.96CLH, s)
5 2.37(3H,s), 4.85(2H,s), 4.88(2H,s), 7.06(lH,br), 7.16(1H,d,J=2.4Hz),
912 7.43(lH,d,J=2.4Hz), 7.50(1H, t, =7.8Hz), 7.56(lH,s), 7.68(lH,s), 7.70(lH,s),
8.03(lH,s) ; .
(DMSO-dg) 5 4.96(2H, s), 7.49(1H, t, J=7.8Hz), 7.64(1H, d, J=7.8Hz), 7.71(1H,
913 d, J=7.8Hz), 8.02(1H, d, J=2.0Hz), 8.10(1H, s), 8.30(1H, d, J=2.0Hz),
10.34(1H, s), 10.38(1H, s)
(DMSO-d6) 5 1.29(6H, d, J=6.8Hz), 2.99(1H, septet, J=6.8Hz), 4.86(2H, s),
914 7.42(1H, t, J=7.8Hz), 7.52(1H, d, J=1.5Hz), 7.68(1H, d, J=7.8Hz), 7.74(1H, d,
J=1.5Hz), 7.85(1H, d, J=7.8Hz), 8.09(1H, s), 9.27(1H, s), 9.66(1H, s)
gi5 5 4.85(2H, s), 7.04(1H, br), 7.47-7.55 (2H, m), 7.63-7.70(3H, m), 7.90(1H, d,
J=1.5Hz), 7.99(1H, s)
916 (DMSO-d6) 5 4.86(2H, s), 7.43(1H, t, J=7.8Hz), 7.70(1H, d, J=7.8Hz), 7.84(1H,
d, J=7.8Hz), 8.10(1H, s), 9.46(1H, br-s), 9.73(1H, br-s)
5 2.22 (6H, s), 3.79 (2H, t, J=5.4Hz), 4.42 (2H, t, J=5.4Hz), 7.37 (1H, t,
917 J=7.8Hz), 7.44 (2H, s), 7.63 (1H, d, J=7.8Hz), 7.71 (1H, d, J=7.8Hz), 8.12
(1H, br-s), 9.37 (1H, s), 9.60 (1H, br-s)
gi8 5 2.34(6H, s), 2.53-2.56(2H, m), 4.43(2H, t, J=6.3Hz), 6.80(1H, br-s),
7.41(1H, s), 7.47(2H, s), 7.50(1H, s), 7.62-7.64(2H, m), 7.9(1H, s)
gig (DMSO-d6) 5 2.66-2.78(2H, m), 4.34(2H, t, J=5.9Hz), 7.49(1H, t, J=7.8Hz),
7.66-7.72(2H, m), 8.12(1H, s), 8.30(2H, s), 10.00(1H, s), 10.60(1H, s)
5 1.32 (6H, d, J=6.1Hz), 2.51 (3H, s), 5.01-5.07 (1H, m), 6.72 (1H, br-s),
920 7.50 (1H, t, J=7.8Hz), 7.54-7.57 (2H, m), 7.64 (1H, d, J=8.1Hz), 7.71 (2H, d,
J=7.3Hz), 7.85 (1H, s), 8.01-8.03 (1H, m), 8.13 (1H, s), 8.45-8.48 (1H, m)
51.32 (6H, d, J=6.1Hz), 1.74-1.77 (2H, m) , 1.84-1.87 (2H, m), 2.74 (2H, t,
g21 J=6.4Hz), 3.02 (2H, q, J=6.4Hz), 5.04 (1H, septet, J=6.1Hz), 6.73 (1H, br s),
7.42-7.46 (2H, m), 7.52-7.55 (1H, m), 7.62 (1H, br s, J=8Hz), 7.76 (1H, br s),
7.96 (1H, br s), 8.03-8.06 (1H, m)
51.31 (6H, d, J=6.4Hz), 1.68-1.76 (4H, m), 2.81 (2H, t, J=5.7Hz), 2.99 (2H, q,
922 J=6.1Hz), 5.03 (1H, septet, J=6.4Hz), 6.73 (1H, br-s), 7.43-7.47 (2H, m) ,
J7.59-7.64 (3H, m) , 8.03 (1H, s) _j

192
Table 9(23) Compound
No- _-HMR(CDCl3,ppn.)
51.31 (6H, d, J=6.4Hz), 3.83 (3H, s), 5.02 (1H, septet, J=6.4Hz), 6.55 (1H, s), 6.7g
923 (1H, br-s), 7.41-7.50 (2H, m), 7.57 (1H, d, J=7.8Hz), 8.03 (1H, br-s) , 8.08 (1H, br-
s)
924 51.32 (6H, d, J=6.3Hz), 3.86 (3H, s), 5.04 (1H, septet, J=6.3Hz), 6.72 (1H, br-s),
7.45-7.53 (2H, m), 7.63 (1H, d, J=7.3Hz), 7.80 (1H, br-s), 8.14 (1H, br-s)
925 51.32 (6H, d, J=5.9Hz), 3.89 (3H, s), 5.04 (1H, septet, J=5.9Hz), 6.72 (1H, s),
7.47-7.50 (2H, m), 7.70 (1H, d, J=8.3Hz), 7.90 (1H, br-s), 8.14 (1H, br-s)
92g 51.32 (6H, d, J=6.1Hz), 3.88 (3H, s), 3.93 (3H, s), 5.04 (1H, septet), 6.78 (1H, br-
s), 7.47 (1H, br-s), 7.64-7.68 (2H, m), 8.05 (1H, br-s), 9.40 (1H, br-s)
51.33 (6H, d, J=5.9Hz), 2.34 (3H, s), 5.02 (1H, septet, J=5.9Hz), 6.74 (1H, br-s),
(927 7.24 (1H, s), 7.44 (1H, t, J=7.8Hz), 7.49-7.52 (1H, m), 7.58-7.60 (1H, m), 7.82 (1H,
- br-s), 8.07 (1H, br-s), 8.71(1H, s)
928 51.31 (6H, d, J=6.4Hz), 2.35 (3H, s), 5.01-5.07 (1H, m) , 6.74 (1H, br-s), 7.25 (1H,
s), 7.46 (1H, t, J=7.8Hz), 7.58-7.63 (2H, m), 7.68 (1H, br-s), 8.07 (1H, br-s)
51.32 (6H, d, J=5.9Hz), 5.03 (1H, septet, J=5.9Hz), 6.52 (1H, septet, J=6.3Hz), 6.71
929 (1H, br-s), 6.99 (1H, d, J=8.8Hz), 7.43 (1H, t, J=7.8Hz), 7.51-7.58 (2H, m) , 7.92
(1H, br-s), 8.01 (1H, br-s), 8.14 (1H, dd, J=8.8Hz, 2.4Hz), 8.34 (1H, d, J=2.4Hz)
51.32 (6H, d, J=5.9Hz), 2.33 (3H, s), 5.50 (1H, septet, J=5.9Hz), 6.53 (1H, septet,
930 J=6.4Hz), 6.74 (1H, br-s), 6.87 (1H, s), 7.43 (1H, t, J=7.8Hz), 7.54-7.58 (2H, m) ,
7.64 (1H, br-s), 8.04 (1H, br-s), 8.37 (1H, s) I
51.32 (6H, d, J=6.3Hz), 5.05 (1H, septet, J=6.3Hz), 6.30 (1H, septet, J=6.3Hz), 6.69
931 (1H, br-s), 7.01 (1H, d, J=8.8Hz), 7.47 (1H, t, J=7.8Hz), 7.56 (1H, dd, J=7.8Hz,
1.5Hz), 7.68 (1H, d, J=7.8Hz), 7.98 (1H, br-s), 8.27 (1H, br-s), 8.82 (1H, d,
J=8.8Hz)
51.32 (6H, d, J=6.4Hz), 2.29 (3H, s), 2.41 (3H, s), 5.04 (1H, septet, J=6.4Hz), 6.58
932 (1H, septet, J=6.4Hz), 6.72 (2H, s), 7.37-7.46 (2H, m), 7.53-7.57 (1H, m), 7.60 (1H,
d, J^7.8Hz), 8.05 (1H, br-s)
5 2.49 (3H, s), 4.85 (2H, s), 7.16 (1H, br-s), 7.48-7.57 (3H, s), 7.70 (2H, s), 7.76
933 (1H, d, J=7.6Hz), 7.92 (1H, s), 8.00 (1H, dd, J=3.4Hz, 6.8Hz), 8.13 (1H, s), 8.47
(1H, dd, J=3.4Hz, 6.8Hz)
; 51.75-1.79 (2H, m), 1.84-1.87 (2H, m), 2.74 (2H, t, J=6.4Hz), 3.02 (2H, q, J=6.4Hz),
934 4.85 (2H, s), 7.13 (1H, br s), 7.41-7.51 (2H, m), 7.59-7.69 (2H, m), 7.76 (1H, br
s), 8.00 (1H, br s), 8.06 (1H, br d, J=8.5Hz)
g35 51.65-1.76 (4H, m), 2.81 (2H, t, J=6.1Hz), 2.99 (2H, q, J=6.4Hz)', 4.85 (2H, s) , 7.10
(1H, br-s), 7.48-7.52 (2H, m), 7.59 (1H, s), 7.67-7.69 (2H, m), 8.04 (1H, s)
g36 53.86 (3H, s), 4.85 (2H, s), 6.58 (1H, s), 7.10 (1H, br-s), 7.51 (1H, t, J=7.8Hz),
7.60 (1H, d, J =7.8Hz), 7.65 (1H, d, J=7.8Hz), 7.84 (1H, br-s), 8.10 (1H, br-s)
937 53.85 (3H, s), 4.85 (2H, s), 7.16 (1H, br-s), 7.51 (1H, t, J=7.9Hz), 7.62 (1H, d,
|J=7.9Hz), 7.68 (1H, d, J=7.9Hz), 7.85 (1H, br-s), 8.12 (1H, br-s)

193
Table 9(24)
Compound
No. Hi-NMRtCDCJ^ppm)
938 53.87 (3H, s), 4.85 (2H, s), 7.21 (1H, br-s), 7.51 (1H, t, J=8.3Hz), 7.61
(1H, d, J=8.3Hz), 7.68 (1H, d, J=8.3Hz), 7.92 (1H, br-s), 8.13 (1H, br-s)
939 53.89 (3H, s), 3.94 (3H, s), 4.86 (2H, s), 7.20 (1H, br-s), 7.52 (1H, t,
J=7.8Hz), 7.70-7.73 (2H, m), 8.09 (1H, br-s), 9.44 (1H, s)
54.87 (2H, s), 7.07-7.11 (2H, m) , 7.31-7.34 (1H, m), 7.47-7.52 (2H, m),
940 7.67-7.69 (1H, m), 8.01 (1H, dd, J=8.0Hz, 1.4Hz), 8.19 (1H, br-s), 8.58-
8.60 (1H, m), 11.3 (1H, br-s)
54.84 (2H, s), 7.19 (1H, br-s), 7.33 (1H, dd, J=8.3Hz, 4.8Hz), 7.44 (1H,
941 t, J=8.3Hz), 7.58-7.59 (2H, m) , 7.94-7.97 (2H, m), 8.44 (1H, dd, J=4.8Hz,
1.4Hz), 9.14 (1H, br-s)
5 2.44 (3H, s), 4.86 (2H, s), 7.11 (1H, br-s), 7.52 (1H, t, J=7.8Hz), 7.59
942 (1H, d, J=2.9Hz), 7.63-7.65 (2H, m), 7.76 (1H, s) , 8.09 (1H, s), 9.23
(1H, s)
54.85 (2H, s), 6.52 (1H, septet, J=6.3Hz), 6.99 (1H, d, J=8.8Hz), 7.07
943 (1H, br-s), 7.48 (1H, t, J=8.3Hz), 7.61-7.62 (2H, m), 7.86 (1H, s), 8.02
(1H, s), 8.15 (1H, dd, J=8.8Hz, 2.5Hz), 8.33 (1H, d, J=2.5Hz)
5 2.35 (3H, s) , 4.85 (2H, s), 6.55 (1H, septet, J=6.4Hz), 6.89 (1H, s),
944 7.08 (1H, br-s), 7.49 (1H, t, J=7.8Hz), 7.59 (1H, s), 7.63 (2H, d,
J=8.3Hz), 8.05 (1H, s), 8.40 (1H, s)
5 2.34 (3H, s), 4.85 (2H, s), 7.17 (1H, br-s), 7.22-7.26 (1H, m), 7.49
945 (1H, t, J=7.8Hz), 7.60-7.66 (2H, m), 7.75 (1H, br-s), 8.07 (1H, br-s),
8.73 (1H, br-s)
54.86 (2H, s), 7.13 (1H, br-s), 7.52 (1H, t, J=8.3Hz), 7.67 (1H, d,
946 J=8.3Hz), 7.74 (1H, d, J=8.3Hz), 8.02 (1H, s), 8.05 (1H, s), 8.66 (1H,
s), 8.70 (1H, br-s)
947 5 2.36 (3H, s), 5.05 (2H, s), 7.16 (1H, br-s), 7.25 (1H, s), 7.51 (1H, t,
J=7.8Hz), 7.68-7.70 (3H, m), 8.08 (1H, br-s)
54.86 (2H, s), 6.30 (1H, septet, J=6.4Hz), 7.00 (1H, d, J=8.8Hz), 7.04
948 (1H, br-s), 7.52 (1H, t, J=7.8Hz), 7.63 (1H, dd, J=7.8Hz, 1.5Hz), 7.70
(1H, d, J=7.8Hz), 8.04 (1H, br-s), 8.27 (1H, br-s), 8.83 (1H, d, J=8.8Hz)
gg2 5 2.37 (3H, s), 4.85 (2H, s), 6.33 (1H, septet, J=5.8Hz), 6.87 (1H, s),
7.05 (1H, br-s), 7-49-7.53 (2H, m), 7.66-7.68 (2H, m), 8.05 (1H, s)
51.33 (6H, d, J=6.4Hz), 2.37 (3H, s), 5.04 (1H, septet, J=6.4Hz), 6.34
1010 (1H, septet, J=6.4Hz), 6.72 (1H, br-s), 6.88 (1H, s) , 7.45 (1H, t,
J=7.8Hz), 7.58-7.64 (3H, m), 8.05 (1H, s)
5 2.38 (3H, s), 4.86 (2H, s), 6.34 <1H, septet), 6.89 (1H, s), 7.09 (1H,
1039 br-s), 7.51 (1H, t, J=7.8Hz), 7.57 (1H, br-s), 7.66 (1H, br-s), 7.68 (1H,
d, J=7.8Hz), 8.07 (1H, s)
1086 5 2.37 (3H, s), 4.85 (2H, s), 6.33 (1H, septet, J=5.8Hz), 6.87 (1H, s),
[7.05 (1H, br-s), 7.49-7.53 (2H, m), 7.66-7.68 (2H, m), 8.05 (1H, s) '

194
Table 9(25)
Compound
No- 1H-NMR(CDCI3,ppm)
51.32 (6H, d, J=6.4Hz), 2.29 (3H, s) , 2.41 (3H, s), 5.04 (1H,
1104 septet, J=6.4Hz), 6.58 (1H, septet, J=6.4Hz), 6.72 (2H, s), 7.37-
7.46 (2H, m), 7.53-7.57 (1H, m), 7.60 (1H, d, J=7.8Hz), 8.05 (1H,
br-s)
1180 5 2.46 (3H, s), 4.86 (2H, s), 7.11 (1H, s), 7.51-7.86 (5H, m), 8.10
(1H, br-s)
5 1.31(6H, d, J=6.3Hz), 2.40(3H, s), 5.03(1H, septet, J=6.3Hz), : 1198 6.72(1H, s), 7.42-7.47(2H, m) , 7.56(1H, s), 7.60-7.63(2H, m) ,
7.74(1H, s), 8.03(1H, s)
1227 5 2.4K3H, s), 4.85(2H, s) , 7.05(1H, br), 7.44(1H, s), 7.51(1H, t,
J=8.1Hz), 7.57(1H, s), 7.67-7.70(3H, m), 8.05(1H, s)
5 1.3K6H, d, J=6.1Hz), 2.42(3H, s) , 5.04(1H, septet, J=6.1Hz), 1245 6.71(1H, s), 7.45(1H, d, J=8.1Hz), 7.48(1H, s), 7.61-7..64(2H, m),
7.72-7.74(2H, m) , 8.04(1H, s) -
1274 5 2.43(3H, s), 4.86(2H, s), 7.08(1H, br), 7.48-7.53(2H, m), 7.68-
7.73(4H, m), 8.06(1H, s)
5 1.32(6H, d, J=6.3Hz), 2.42(3H, s), 5.04(1H, septet, J=6.3Hz),
1292 6.72(1H, s), 7 . 44-7 . 52 (2H, m), 7 . 62-7 . 66 (3H, m) , 7.93(1H, s)',
8.04(1H, s)
1321 5 2.43(3H, s), 4.86(2H, s), 7.08(1H, br), 7.50-7.54(2H, m), 7.63(1H, s), 7.70-7.72{2H, m) , 7.94(1H, s), 8.08(1H, s)
5 0.87(3H, t, J=7.3Hz), 1.53-1.63(2H, m) , 2.44-2.56(2H, m), 2.64(2H, 1361 tr J=7-8Hz>' 4.38(2H, t, J=6.3Hz), 7.16(1H, s), 7.38(1H, t,
J=7.8Hz), 7.48(1H, s), 7.61-7.64(2H, ra), 7.91-7.94(2H, m) , 8.00(1H,
s)
5 0.93(3H, t, J=7.3Hz), 1.59-1.69(2H, m), 2.71(2H, t, J=7.8Hz),
1368 4.86(2H, s), 7.11(1H, br), 7.49-7.54(2H, ra), 7.62(1H, s), 7.69-
7.72(2H, m), 7.96(1H, d, J=1.5Hz), 8.07(1H, s)
5 2.35(3H, s), 2.44(3H, s), 4.86(2H, s), 6.74(1H, s), 7.34-7.38(3H,
1385 m), 7.46(1H, s), 7.52(1H, d, J=8.8Hz), 7.89(1H, s), 8.35(1H, d,
J=8.8Hz)
5 1.32(6H, d, J=6.3Hz), 2.40(6H, s), 2.41(3H, s), 5.03(1H, septet,
1386 J=6.3Hz), 6.46(1H, br-s), 7.15(1H, s), 7.28-7.37(4H, m), 7.95(1H, d,
J=8.3Hz)
1387 5 2.40(6H, s), 2.45(3H, s), 4.86(2H, s), 6.80(1H, br), 7.16(1H, s),
7.32~7.42(4H, m), 7.85(1H, br)
5l.35(3H, t, J=7.3Hz), 2.36(6H, s), 4.28(2H, q, J=7.3Hz), 6.91 (1H,
1388 s), 7.29 (1H, t, J=8.3Hz), 7.37 (2H, s), 7.74-7.79 (2H, m), 8.32
(1H, br-d, J=5.9Hz)
51.34 (6H, d, J=6.3Hz), 2.36 (6H, s) , 5.07 (1H, septet, J=6.3Hz),
1389 6.86 (1H, br-s), 7.30 (1H, t, J=8.1Hz), 7.37 (2H, s) , 7.72-7.79 (2H,
I pi) , 8.32 (1H, br) ' (

195
Table 9(26)
Compound
. NCK ^-NMRjCDCi.rPpm)
5 2.37(6H, s), 4.70(4H, dt, J=2.0Hz, 46.8Hz), 5.28(1H, tt, J=4.4Hz,
1408 24.9Hz), 7.08(1H, br-s), 7.33(1H, t, J=8.3Hz), 7.37(2H, s), 7.76(1H,
d, J=12.2Hz), 7.8K1H, dt, J=1.4Hz, 7.8Hz), 8.29(1H, br-s)
5 2.37(6H, s), 2.51-2.62(2H, m) , 4.46(2H, t, J=6.4Hz), 6.97(1H, br-1411 s), 7.32(1H, t, J=8.3Hz), 7.37(2H, s), 7.74-7.82(2H, m), 8.28(1H,
br-s)
1416 5 2.37(6H, s), 3.76-3.79(2H, m) , 4.49(2H, t, J=5.4Hz), 7.02(1H, br),
' 7.32(1H, t, J=7.8Hz), 7.37(2H, s), 7.74-7.81(2H, m), 8.30(1H, br)
1418 5 2.37 (6H, s), 4.88 (2H, s), 7.21 (1H, br), 7.32-7.37 (3H, m) ,
7.76-7.85 (2H, m), 8.31 (1H, br)
5 2.36(6H, s), 3.60(2H, t, J=5.9Hz), 4.54(2H, t, J=5.9Hz), 7.03(1H,
1421 br), 7.32(1H, t, J=7.8Hz), 7.37(2H, s), 7.76-7.81(2H, m), 8.29(1H,
br)
51.35(3H, t, J=7.3Hz), 2.36(6H, s), 4.29(2H, q, J=7.3Hz), 6.89(1H,
1435 br-s), 7.30(1H, t, J=7.8Hz), 7.35(2H, s), 7.74-7.78(2H, m), 8.32(1H,
br-s)
5 2.33(6H, s), 4.70(4H, ddd, J=48.8Hz, 2.4Hz, 4.3Hz), 5.28(1H, tt,
1455 J=20.0, 4.3Hz), 7.08(1H, br-s), 7.32(1H, d, J=8.3Hz), 7.35(2H, s),
7.75-7.83(2H, m), 8.29(1H, br-s)
5 2.36(6H, s), 2.51-2.62(2H, m), 4.47(2H, t, J=6.3Hz), 6.95(1H, br-
1458 s), 7.32(1H, t, J=7.3Hz), 7.35(2H, s), 7.74-7.82(2H, m) , 8.29(1H,
br-s)
5 2.36(6H, s), 3.77(2H, t, J=5.4Hz), 4.49(2H, t, J=5.4Hz), 7.03(1H, 1463 br), 7.31(1H, t, J=8.3Hz), 7.35(2H, s), 7.76-7.80(2H, m) , 8.29(1H,
brj
1465 5 2.36(6H, s), 4.88(2H, s), 7.18(1H, br), 7.35(1H, t, J=8.3Hz), 7.36(2H, s), 7.75-7.85(2H, m), 8.31{1H, br)
5 1.33(6H, d, J=6.3Hz), 2.37(3H, s), 5.05(1H, septet, J=6.3Hz),
1898 7.21(1H, br-s), 7.32(1H, d, J=6.6Hz), 7.39(1H, t, J=8.1Hz), 7.46(1H,
s), 7.50-7.53(2H, m), 8.30-8.36(2H, m)
18gg 5 2.38(3H, s), 4.87(2H, s), 7.40-7.51(5H, m), 7.62(1H, s), 8.27-
8.30(2H, m)
1900 5l.34(6H, d, J=6.1Hz), 2.41(6H, s), 5.05(1H, septet, J=6.1Hz),
7.22-7.26(2H, m), 7.31-7.40(4H, m), 8.33(1H, dd, J=1.5Hz, 8.1Hz)
ig01 5 2.40(6H, s), 4.88(2H, s), 7.29(1H, s), 7.37(2H, s), 7.38-7.43(2H,
m) , 7.50(1H, s), 8.28(1H, d, J=6.8Hz)
lg02 5 4.88(2H, s), 7.39(1H, dd, J=1.5Hz, 7.3Hz), 7.44-7.51(2H, m), 7.88-
|7.92(2H, m), 8.03(1H, s), 8.36(1H, d, J=8.3Hz), 8.70(1H, d, J=8.3Hz)

196 Table 9(27)
Compound
No. ^-NMRtCDCl^ppm)
1903 5 2.37 (3H, s), 4.88 (2H, s), 6.55 (1H, septet, J=6.3Hz), 6.90 (1H,
s), 7.32 (1H, s), 7.41-7.48 (3H, m) , 8.31 (1H, br-s), 8.49 (1H, s)
5 1.34(6H, d, J=6.3Hz), 2.44(6H, s), 5.05{1H, septet, J=6.3Hz),
1904 7.13(1H, s), 7.25-7.28(2H, m), 7.37(2H, s), 7.41(1H, t, J=8.3Hz),
8.31(1H, dd, J=1.5Hz, 8.3Hz) _______
lg05 5 2.44(6H, s), 4.88(2H, s), 7.15(1H, br), 7.33-7.37(3H, m), 7.43-
7.53(2H, m), 8.25(1H, d, J=8.3Hz)
lg06 5 2.40(3H,s), 4.86(2H,s), 7.05-7.10(2H,m), 7.47(lH,s),
7.53(lH,d,J=8.8Hz), 7.58(lH,br), 8.22(lH,br), 8.28(1H,d,J=8.8Hz).
1907 5 2.40(6H,s), 4.86(2H,s), 7.00-7.11(3H,m), 7.37(2H,s), 8.18(lH,br)
ig08 5 1.33(6H,d, J=6.3Hz), 2.'39(6H,s), 5. 04 (1H, septet, J=6. 3Hz),
6.81(lH,br), 7.30(lH,br), 7.37(2H,s), 8.23(lH,br)
5 1.33(6H, d, J=6.1Hz), 2.34(3H, s), 2.42(3H, s), 5.05(1H, septet,
1909 J=6.1Hz), '6.46(1H, br), 7.30(1H, d, J=8.1Hz), 7.45(1H, s), 7.49(1H,
d, J=8.5Hz), 7.60(1H, dd, J= 1.7Hz, 8.1Hz), 7.83(1H, s), 8.27(1H,
d, J=8.5Hz), 8.46(1H, br)
5 2.39(3H, s), 2.42(3H, s), 4.86(2H, s), 6.77(1H, br), 7.35(1H, d,
1910 J=8.1Hz), 7.46(1H, s), 7.50(1H, d, J=8.8Hz), 7.65(1H, dd, J=2.0Hz,
8.1Hz), 7.80(1H, s), 8.27(1H, d, J=8.8Hz), 8.36(1H, br)
5 1.33(6H, d, J=6.3Hz), 2.34(9H, s), 5.04(1H, septet, J=6.3Hz),
1911 6.48(1H, br-s), 7.31(1H, d, J=7.8Hz), 7.34(2H, s), 7.55(1H, s),
7.64(1H, dd, J=1.5Hz, 7.8Hz), 8.46(1H, s)
1912 5 2.34(6H, s), 2.40(3H, s), 4.86(2H, s), 6.78(1H, br), 7.34-7.36(3H,
m), 7.50(1H, s), 7.69(1H, dd, J=1.5Hz, 7.8Hz), 8.36(1H, s)
51.32(6H,d,J=6.3Hz), 2.43(3H,s),3.96(3H,s), 5.05(1H, sept.,J=6.3Hz),
1913 6.98(lH,d,J=8.5Hz), 7.24(lH,s), 7.44(1H,s), 7.49(lH,d,J=8.5Hz),
7.71{lH,dd,J=2.2Hz, 8.5Hz), 7.82(lH,s), 8.25(1H,d,J=8.5Hz),
8.68(lH,s)
5 2.43(3H,s), 4.00(3H,s), 4.87(2H,s), 7.02(1H,d,J=8.5Hz),
1914 7.45(lH,s), 7.50(lH,d, J=8.5Hz), 7.54(lH,s), 7.74-7.79(2H,m),
8.28(lH,d,J=8.5Hz), 8.66(lH,s)
5 l.'33(6H, d, J=6.3Hz), 2.42(3H, s) , 5.00-5.10 (1H, m) , 6.91(1H, br) ,
1915 7.20(1H, dd, J=8.5Hz, 10.5Hz), 7.46(1H, s), 7.49(1H, d, J=8.8Hz),
7.62-7.66(lH, m), 7.82(1H, s), 8.20(1H, d, J=8.8Hz), 8.71(1H, d,
J=6.1Hz)
5 2.46(3H, s), 4.87(2H, s), 7.23-7.29(2H, m), 7.47(1H, s), 7.51(1H,
1916 d, J=8.8Hz), 7.68-7.73(lH, m), 7.78(1H, s), 8.23(1H, d, J=8.5Hz),
8.68(1H, d, J=6.1Hz)
5 1.33(6H, d, J=6.3Hz), 2.34(6H, s), 5.04(1H, septet, J=6.3Hz),
1917 6.9K1H, s), 7.20(1H, dd, J=8.5Hz, 10.5Hz), 7.35(2H, s) , 7.56 (1H,
|s), 7.66-7.70(lH, m), 8.71(1H, br-d, J=6.6Hz)

197
Table 9(28)
Compound
No. ^-NMRtCDCJ^ppm)
1918 8 2.34(6H, s), 4.87(2H, s), 7.22(1H, dd, J=8.8Hz, 10.5Hz), 7.32(2H,
s), 7.75-7.79(lH, m) , 7.87(1H, s) , 8.56(1H, s), 8.63(1H, br)
81.34(6H,d,J=6.3Hz), 2.43(3H,s), 5.06(1H,septet,J=6.3Hz),
1919 7.21tlH,s), 7.46(lH,s), 7.49- 7.52(2H,ra), 7 . 61 (1H, dd, J=2 .2Hz,
8.5Hz), 7.82(lH,s), 8.24(lH,d,J=8.5Hz), 8.78(1H,d,J=2.2Hz)
5 2.43(3H,s), 4.88(2H,s), 7.47(lH,s), 7.50-7.57(3H,m),
1920 7.66(lH,dd,J=2.0Hz, 8.3Hz), 7.78(lH,s), 8.26(1H,d,J=8.3Hz),
8.72(lH,s)
5 1.34(6H, d, J=6.1Hz), 2.34(6H, s), 5.05(1H, septet, J=6.1Hz),
1921 7.23(1H, s), 7.'35(2H, s) , 7.51(1H, d, J=8.3Hz), 7. 63-7. 69 (2H, m) ,
8.76(1H, s)
1922 5 2.35(6H, s), 4.88(2H, s), 7.36(2H, s), 7.50(1H, br) , 7.53-7.59(2H,
m), 7.70(1H, dd, J=2.0Hz, 8.3Hz), 8.72(1H, s)
1923 5 2.35(6H, s), 2.45(3H, s), 4.84(2H, s), 7.00(1H, br) , 7.36(2H, s) ,
7.4K1H, s), 7.48(2H, s) , 7.83(1H, s)
5 1.33(6H, d, J=6.1Hz), 2.46(3H, s), 5.05(1H, septet, J=6.1Hz),
1924 6.89(1H, br-s), 7.48(1H, s), 7.51(1H, d, J=9.1Hz), 7.79(2H, s),
7.89(1H, s), 8.18(1H, d, J=9.1Hz), 8.19(1H, s)
5 2.43(3H, s), 4.86(2H, s), 7.31(1H, br-s), 7.49(1H, s), 7.52(1H, d,
1925 J=8.8Hz), 7.78(1H, s), 7.85(1H, s), 7.94(1H, s), 8.18(1H, d,
J=8.8Hz), 8.24(1H, s)
5 1.32(6H, d, J=6.1Hz), 2.34(6H, s), 5.04 (1H, septet, J=6.1Hz),
1926 6.87(1H, s), 7.36(2H, s), 7.50(1H, s), 7.83(1H, s), 7.90(1H, s),
8.20(1H, s)
1927 5 2.35(6H, s), 4.86(2H, s), 7.26(1H, s), 7.37(2H, s), 7.48(1H, s),
7.89(1H, s), 7.97(1H, s>, 8.24(1H, s)
Sl.31(6H,d,J=6.3Hz), 2.33(6H,s), 3.89(2H,br.), 4.97-5.04(lH,m),
1928 6.59(lH,s), 6.92(lH,s), 7.02(lH,s), 7.23-7.26(lH,m), 7.34(2H,s),
7.39(lH,br)
1929 5 2.35(6H,s), 3.04(6H,s), 4.84(2H,s), 6.94(2H,br), 7.04(lH,s),
7.30(lH,s), 7.349(2H,s), 7.404(lH,s)
5 1.30(6H, d, J=6.3Hz), 2.37(3H, s), 2.48(3H, s), 5.02(1H, septet,
1930 J=6.3Hz), 6.57(1H, s), 7.20-7.28(2H, m) , 7.44(2H, s), 7.50(1H, d,
J=8.3Hz), 7.76(1H, s), 8.28(1H, d, J=9.1Hz)
5 2.39(3H, s), 2.48(3H, s), 4.84(2H, s), 7.22(1H, d, J=8.3Hz), 7.44-
1931 7.54(3H, m), 7.80(1H, s), 8.13(1H, d, J=8.1Hz), 8.20(1H, s),
9.04(1H, s)
1932 8 1.30(6H, d, J=6.1Hz), 2.39(6H, s), 2.48(3H, s), 5.02(1H, septet,
|J=6.1Hz), 6.63(1H, s), 7.19-7.25(3H, m), 7.36(2H, s), 7.81(1H, s)

1.98
Table 9(29) Compound
NO- 1H-NMR(CDCl3,ppm)
1933 5 2.40(6H, s), 2.50(3H, s) , 4.84(2H, s), 7.01(1H, br-s), 7.18(1H,
s), 7.24-7.27(1H, m), 7.31-7.34(1H, m) ( 7.37(2H, s), 7.82(1H, s)
5 1.31(6H, d, J=6.1Hz), 2.41(3H, s), 5.04(1H, septet, J=6.1Hz), lg34 6.69(1H, s), 7.16-7.2K1H, m) , 7.46{1H, s), 7.5(1H, d, J=8.8Hz),
7.88(1H, dd, J=2.9Hz, 6.6Hz), 7.96(1H, br), 8.40(1H, d,- J=8.8Hz),
8.57 (1H, d, J=17.6Hz) __
5 2.42(3H, s), 4.84(2H, s), 7.04(1H, br), 7.20-7.27(1H,' m) , 7.46(1H,
1935 s), 7.51(1H, d, J=8.5Hz), 7.94(1H, br), 8.01(1H, dd, J=2.9Hz,
6.6Hz), 8.40(1H, d, J=8.5Hz), 8.57(1H, br-d, J=17.6Hz)
5 1.31(6H, d, J=6.3Hz), 2.35(6H, s), 5.02(1H, septet, J=6.3Hz),
1936 6.70(1H, s), 7.19(1H, dd, J=9.0Hz, 11.2Hz), 7.36(2H, s), 7.83(1H,
dd, J=2.9Hz, 6.6Hz), 7.99(1H, br), 8.01(1H, d, J=5.1Hz)
1937 5 2.36(6H, s), 4.84(2H, s), 7.10(1H, br-s), 7.21-7.26(1H, m),
7.36(2H, s), 7.94-8.03(3H, m)
5 1.31(6H, d, J=6.3Hz), 2.41(3H, s), 5.03(1H, septet, J=6.3Hz),
1938 6.68(1H, s), 7.40(1H, d, J=8.8Hz), 7.46(1H, s), 7.51(1H, d,
J=8.5Hz), 7.67(1H, d, J=8.5Hz), 7.78 (1H, d, J=2.7Hz), 8.06(1H, s),
8.32(1H, d, J=8.8Hz)
5 2.42(3H, s), 4.84(2H, s), 7.38(1H, d, J=8.8Hz), 7.45-7.49 (2H, m)',
1939 7.72(1H, d, J=7.3Hz), 7.93(1H, s), 8.17(1H, d, J=8.5Hz), 8.52(1H,
s), 9.43(1H, s) .
5 1.31(6H, d, J=6.1Hz), 2.40(6H, s), 5.03(1H, septet, J=6.1Hz),
1940 6.70(1H, s), 7.36{2H, s), 7.41(1H, d, J=8.8Hz), 1. 63-7.66(2H, m),
7.75(1H, d, J=2.7Hz)
ig41 5 2.40(6H, s), 4.84(2H, s), 7.08(1H, br) , 7.37(2H, s), 7.46(1H, d, J=8.8Hz), 7.64-7.70(2H, m), 7.82{1H, d, J=2.7Hz)
1942 5l.31(6H,d,J=6.3Hz), 2.41(3H,s), 4.97-5.07(lH,m), 6.70(lH,s), 7.45-
7.58(4H,ra), 7.72-7.75(2H,m), 8.30(lH,d, J=8.8Hz)
.5 2.44(3H,s), 4.85(2H,s), 7.43-7.47(2H,m), 7.54(1H,d,J=8.5Hz),
1943 7.61(lH,d,J=8.5Hz), 7.86(lH,s), 7.99(1H,d,J=8.1Hz), 9.09(lH,s),
9.89(lH,s)
5 2.43(3H,s), 4.84(2H,s), 7.36(lH,s), 7.44(lH,s),
1944 7.47(lH,d,J=8.5Hz), 7.79(2H,d,J=8.5Hz), 8.08(1H, d,J=8.5Hz),
8.62(lH,s), 9.65(lH,s)
5 1.31(6H, d, J=6.3Hz), 2.45(6H, s), 5.03(1H, septet, J=6.3Hz),
1945 6.66(1H, s), 7.16-7.21(2H, m), 7.36(2H, s), 7.76(1H, s), 7.82(1H,
dd, J=2.7Hz, 8.8Hz)
5l.52(9H,s), 2.41(3H,s), 6.58(lH,s), 7.19(1H, dd, J=2.7Hz, 8.5Hz),
1946 7.41(lH,s), 7.45(lH,s), 7.51(lH,d,J=7.1Hz), 7.69(lH,s),
7.79(1H,d,J=8.5Hz), 8.30(1H,d,J=8.5Hz)
5 2.44(3H, s), 2-.45(3H, s) , 4.83(2H, d, J=1.7Hz), 7.00(1H, br) ,
1947 7.07-7.27(2H, m), 7.36(2H, s), 7.74-7.77(1H, d, J=10.3Hz), 7.86(1H,
[dd, J=8.5Hz, 10.3Hz)

199
Table 9(30)
Compound
No. 1H-NMR(CDCl3,ppm)
194g 53.45(3H, s), 4.80.2H, s), 7.53-7.57 (2H, m), 7.68.1H, s), 7.82.1K,
d, J=7.8Hz), 7.93-7.95(3H, m)
194g 5 2.30(3H, s), 3.41(3H, s), 4.77(2H, s), 6.77(1H, s), 6.95-7.00(1H,
m), 7.07-7.16(2H, m), 7.29-7.41(4H, m)
5 1.26(6H, d, J = 5.9Hz), 2.28{6H, s), 3.33(3H, s) , 4.96{1H, septet,
1950 J=5.9Hz), 6.47(1H, s), 6.88(1H, d, J=7.8Hz), 7.04(1H, t, J=7.8Hz),
7.21(2H, s), 7.23-7.47(2H, m)
5 2.29(6H, s), 3.34(3H, s), 4.77(2H, s), 6.81(1H, br), 6.99(1H, d,
1951 J=7.8Hz), 7.10(1H, t, J=7.8Hz), 7.22(2H, s), 7.24-7.26(1H, m),
7.42.1H, s)
5 1.26(6H, d, J=6.3Hz), 2.34(3H, s), 3.34(3H, s), 4.97(1H, septet,
1954 J=6.3Hz), 6.46(1H, s), 6.99(1H, d, J=7.8Hz), 7.07(1H, t, J=7.8Hz),
7.28-7.31 (2H, m), 7.40-7.44(1H, m), 7.62 (1H, s)
1955 5 2.35(3H, s), 3.36.3H, s), 4.77(2H, s), 7.02-7.13(3H, m), 7.29-
7.37(2H, m), 7.44-7.52(1H, m), 7.62(1H, s)
5 1.26(3H, t, J=7.3Hz), 2.29(6H, s), 3.86(2H, q, J=7.3Hz), 4.76(2K,
1956 s), 6.86(1H, br), 6.92-6.95(1H, m), 7.08(1H, t, J=8.1Hz), 7.22(2H,
s), 7.23-7.30(lH, m), 7.38(1H, t, J=2.0Hz)
5 1.46(6H, d, J=6.3Hz), 2.07(6H, s), 4.77(2H, s), 5.40.1H, septet,
1957 J=6.3Hz), 6.78(1H, br), 6.98.1H, d, J=7.8Hz), 7.14-7.19 (1H, m),
7.17(2H, s), 7.29.1H, s), 7.46(1H, d, J=7.8Hz)
lg58 5 2.34 (6H, s), 3.45 (3H, s), 4.80 (2H, s), 7.36 (2H, s), 7.50-7.56
(3H, m), 7.78 (1H, d, J=6.1Hz), 7.90 (1H, s)
(DMSO-d6) 8 2.32 (6H, s), 3.30 (3H, s), 4.86 (2H, s) , 6.83 (1H, t,
1959 J=7.4Hz), 7.40 (1H, t, J=7.4Hz), 7.44 (2H, s), 7.67 (1H, t,
J=7.4Hz), 10.05 (1H, s)
5l.29(6H,d,J=6.3Hz), 2.35(6H,s), 3.35(3H,s), 3.38(3H,s), 4.97-
1960 5.03{lH,m), 7.36(2H,s), 7.58(lH,s), 7.76(lH,s), 7.84(lH,s),
8.56(lH,s)
(DMSO-dg) 5 2.28(6H, s)„ 2.33(3H, s), 7.44.2H, s), 7.48(1H, t, J
1961 =7.8Hz), 7.66-7.75(2H, m), 8.11.1H, t, J=2.0Hz), 9.96(1H, s),
10.56(1H, s)
(DMSO-d6) 51.34 (3H, t, J=7.3Hz), 2.34 (6H, s), 2.96 (2H, q,
1962 J=7.3Hz), 7.33 (2H, s), 7.41 (1H, t, J=7.8Hz), 7.67 (1H, d,
J=7.8Hz), 7.83-7.85 (1H, m), 8.11 (1H, d, J=2.0Hz), 8.79 (1H, s),'
9.58 (1H, s)
1963 5 1.32(6H,d,J=6.6Hz), 2.37(6H,s), 5.00-5.06(lH,m), 6.69(lH,s), 7.35-
7.65(5H,m), 8.09(lH,s), 8.72(lH,s)
lg64 5 2.37(6H,s), 4.85(2H,s), 7.07(lH,br.), 7.39(2H,s),
|7.45(lH,t,J=8.1Hz), 7.61-7.68(2H,m), 8.11(lH,s), 8.69(lH,s)

200
Table 9(31) Compound
No. 1H-NMR(CDCl3,ppm)
51.34 (6H, d, J=6.3Hz), 2.34 (6H, s), 5.09 (1H, septet, J=6.3Hz),
1967 7.29 (1H, br-s), 7.35 (2H, s), 7.91 (1H, t, J=7.8Hz), 7.97 (1H, d,
J=7.8Hz), 8.21 (1H, d, J=7.8Hz), 9.19 (1H, br-s)
5 2.35 (6H, s), 4.89 (2H, s), 7.36 (2H, s), 7.63(lH,br-s),7.97 (1H,
1968 dd, J=8.3Hz, 7.6Hz), 8.05 (1H, d, J=7.6Hz), 8.21 (1H, d, J=8.3Hz),
9.17 (1H, br-s)
5 2.35 (6H, s), 3.77-3.80 (2H, m), 4.48-4.52 (2H, m), 7.36 (2H, s),
1969 7.46 (1H, br-s), 7.94 (1H, t, J=7.8Hz), 8.02 (1H, dd, J=7.8Hz,
1.0Hz), 8.19 (1H, dd, J=7.8Hz, 1.0Hz), 9.17 (1H, br-s)
51.36 (6H, d, J=6.4Hz), 2.52 (6H, s), 5.07-5.14 (1H, m), 7.36 (2H,
2061 S), 7.56 (1H, t, J=8.2Hz), 8.15 (1H, dd, J=8.2Hz, 1.9Hz), 8.44 (1H,
dd, J=8.2Hz, 1.9Hz), 9.45 (1H, br-s), 12.9 (1H, br-s)
5 2.37 (6H, s), 4.91 (2H, s), 7.36 (2H, s), 7.61 (1H, t, J=8.3Hz),
2062 8.23 (1H, dd, J=8.3Hz, 1.9Hz), 8.45 (1H, dd, J=8.3Hz, 1.9Hz), 9.81
(1H, br-s), 12.7 (1H, br-s)
2157 5 2.36 (6H, s), 4.90 (2H, s), 7.38 (2H, s), 7.52-7.60 (2H, m), 8.44
(1H, s), 8.56 (1H, d, J=5.4Hz), 8.58 (1H, br-s)
51.33 (6H, d, J=5.8Hz), 2.35 (6H, s), 5.03-5.07 (1H, m), 7.06 (1H,
2164 S), 7.35 (2H, s), 7.93 (1H, d, J=2.4Hz), 7.95 (1H, d, J=5.9Hz,
2.4Hz), 8.49 (1H, d, J=5.9Hz), 9.58 (1H, br-s)
(DMSO-dg) 5 2.26 (6H, s), 5.02 (2H, s), 7.43 (2H, s),-7.75 (1H, dd,
2165 J=5.4Hz, 2.0Hz), 8.31 (1H, d, J=2.0Hz), 8.60 (1H, d, J=5.4Hz), 10.41
(1H, br-s), 10.92 (1H, br-s)
(DMSO-d6) 5 2.36 (6H, s), 4.90 (2H, s), 7.34 (2H, s), 7.94 (1H, dd,
2167 J=c7.3Hz, 3.4Hz), 8.31 (1H, d, J=7.3Hz), 8.60 (1H, d, J=3.4Hz), 10.90
(1H, br-s), 13.65 (1H, br-s)
(DMSO-d6) 5 2.30(6H, s), 3.61(3H, s), 5.03(2H, s), 7.47(2H, s),
2168 7.92(1H, d, J=7.6Hz), 7.98(1H, d, J=7.6Hz), 8.08(1H, t, J=7.6Hz),
|l0.18(lH, s)

201
Table 9(32) Compound
No. ''H-NMK (CDCI3, ppm)
I_1 5 2.34(6H, s), 3.87(2H, br-s), 6.86-6.89(1H, m) , 7.21-7.30 (3H, m) ,
7.33(2H, s), 7.39(1H, s)
5 3.87(2H, br), 6.84-7.00(1H, m) , 7.14-7.17(1H, m), 7.20(1H, t,
1-2 J=2.0Hz), 7.24-7.28(lH, m), 7.60(2H, d, J=8.8Hz), 7.78(2H, d,
J=8.8Hz), 7.90(1H, br-s)
I_3 5 2.51 (3H, d, J=8.8Hz), 3.86 (2H, br-s), 6.83-8.68 (1H, m) , 7.13-
7.25 (3H, m), 7.26-7.63 (3H, ra) , 7.90 (1H, br-s)
53.87 (2H, br-s), 3.89 (3H, s), 6.86-6.88 (1H, m), 6.99 (1H, dd, J
1-4 =8.6Hz, 2.0Hz), 7.15-7.20 (2H, m), 7.27 (1H, t, J=7.8Hz), 7.51 (1H,
d, J=8.6Hz), 7.83 (1H, s), 7.93 (1H, s)
z_5 53.89 (2H, br-s), 6.86-6.89 (1H, m), 7.12-7.30 (3H, m) , 7.52-7.59
(2H, m), 7.76-7.93 (2H, in)
5 2.43(3H, s), 3.83(2H,br), 6.85-6.88(lH,m), 7.14-7.17(lH,m), 7.21-
1-6 7.29(2H,m), 7.45(1H, s), 7.49(1H, d,J=8.8Hz), 7.76(lH,br),
8.27(lH,d,J=8.8Hz)
1-7 5 2.34(6H, s), 3.87(2H, br), 6.86-6.89(1H, m), 7.20-7.35(6H, m)
5 2.42(3H, s), 3.79(2H, br-s), 6.80(1H, dd, J=2.2Hz, 7.8Hz),
1-8 6.90(1H, d, J=7.8Hz), 7.05(1H, s), 7.15(1H, t, J=7.8Hz), 7.26-
7.44(7H, m), 7.53(1H, s)
5 2.33 (3H, s), 2.52 (3H, d, J=8.8Hz), 3.89 (2H, br-s), 6.86-6.89
1-9 (1H, m), 7.14-7.16 (1H, m), 7.22 (1H, s), 7.28-7.30 (2H, m), 7.65
(1H, br-s), 8.11 (1H, s)
5 2.28 (3H, s), 2.46 (3H, d, J=6.1Hz), 3.88 (2H, br-s), 6.84-6.89
1-10 (1H, m), 7.15-7.19 (1H, m), 7.23-7.29 (2H, m), 7.41 (1H, d,
J=9.1Hz), 7.73 (1H, br-s), 7.81 (1H, d, J=9.1Hz)
12 5 2.60 (3H, s), 3.92 (2H, br-s), 6.89-6.92 (1H, m), 7.24-7.32 (3H,
ra), T.46 (1H, s), 7.76 (1H, br-s)
__13 5 2.27(6H, s), 3.3K3H, s), 6. 40-6.43 (1H, m), 6.54-6.58 (1H, m) ,
6.71(1H, t, J=2.0Hz), 6.76-6.86(lH, m), 7.22(2H, s)
__14 5 1.45(6H, d, J=6.3Hz), 2.07(6H, s), 3.53(2H, br), 5.37(1H, septet,
J=6.3Hz), 6.56-6.63(3H, m), 6.96(1H, t, J=7.8Hz), 7.16(2H, s)
5 1.32(3H, t, J=7.6Hz), 2.72(2H, q, J=7.6Hz), 3.88(2H, br), 6.85-
1-15 6.89(1H, m), 7.13-7.14(1H, m), 7.22-7.30 (2H, ra), 7.46(1H, s),
7.50(1H, d, J=8.8Hz), 7.80(1H, br-s), 8.29(1H, d, J=8.8Hz)
I_16 5 1.17(3H, t, J=7.6Hz), 2.28(3H, s), 2.65(2H, q, J=7.6Hz), 3.85(2H,
|br-s), 6.82-6.85(1H, m), 7.21-7.23 (3H, m), 7.34(2H, s), 7.64(1H, s)

202
Table 9(33) __^
Compound
No. ^-NMRtCDCJ^ppm)
I_17 5 1.22(6H, t, J=7.6Hz), 2.69(4H, q, J=7.6Hz), 3.86(2H, br-s), 6.86-
6.89(1H, m), 7.15-7.36(4H, m), 7.38(2H, s)
5l.23(3H, t, J=7.3Hz), 2.76(2H, q, J=7.3Hz), 3.88 (2H, br-s), 6.88-
1-18 6.9K1H, m), 7.26-7.32 (3H, m), 7.50(1H, s), 7.53(1H, s) , 7.95(1H, d,
J=1.5Hz)
5 1.00(3H, t, J=7.3Hz), 1.65-1.75(2H, m), 2.67(2H, t, J=7.3Hz),
1-19 3.89(2H, br), 6.84-6.88(1H, m), 7.11-7.29(3H, m), 7.43(1H, s),
7.49(1H, d, J=8.5Hz), 7.85(1H, br-s), 8.27(1H, d, J=7.8Hz)
51.22 (6H, d, J=6.8Hz), 2.32 (3H, s), 3.17 (1H, septet, J=6.8Hz),
1-20 3.87 (2H, br-s), 6.85-6.93 (1H, m) , 7.20-7.29 (3H, in), 7.35 (1H, s),
7.40-7.45 (2H, m) ■
I_21 5 2.35(3H, s), 3.85(5H, s), 6.85-6.89(1H, m) , 6.95(1H, s), 7.13(1H,
s), 7.23-7.30(3H, m), 7.62(1H, s)
I_22 5 1.25(3H, t, J=7.6Hz), 2.76(2H, q, J=7.6Hz), 3.88(2H, br-s), 6.87-
6.9K1H, m), 7.24-7.3K3H, m), 7.47.1H, s), 7.55(1H, s) , 7.57(1H, s)
I_23 5 2.62 (3H, d, J=6.4Hz), 3.91 (2H, br-s), 6.89 (1H, d, J=8.0Hz),
7.20-7.32 (4H, m), 7.49 (1H, d, J=9.0Hz), 8.58-8.60 (1H, in)
I_24 53.91 (2H, br-s), 3.92 (3H, s), 6.89-6.92 (1H, m) , 7.21-7.33 (3H,
m), 7.59 (1H, d, J=1.2Hz), 8.50 (1H, s), 8.54 (1H, s)
I_25 5 2.35 (3H, s), 2.57 (3H, d, J=6.8Hz), 3.88 (2H, br-s), 6.88-6.91
(1H, m), 7.25-7.34 (4H, m), 7.67 (1H, s)
I_26 5 2.4K3H, s), 3.88(2H, br-s), 6. 87-6. 91 (1H, m), 7 .25-7.31 (3H, m) ,
7.47.1H, s), 7.65(1H, s), 7.72(1H, s)
5 1.23(3H, t, J=7.3Hz), 2.74(2H, q, J=7.3Hz), 3.87(2H, br-s), 6.86-
1-27 6.9K1H, m), 7.25-7.31 (3H, in), 7.50(1H, s), 7.59(1H, s), 7.73(1H, d,
J=1.5Hz)
(DMSO-d6) 8 0.84(3H, t, J=7.3Hz), 1.48-1.58(2H, m), 2.66(2H, t,
1-28 J=7.3Hz), 5.36(2H, br-s), 6.77.1H, dd, J=1.0Hz, 7.8Hz), 7.10-
7.19QH. m), 7.59(1H, s), 7.80(1H, s) , 10.03(1H, s)
5 0.90(3H, t, J=7.3Hz), 1.25-1.37(2H, m) , 1.55-1.63(2H, m), 2.72(2H,
1-29 t, J=7.8Hz), 3.89(2H, br), 6.87-6.91(1H, m), 7.24-7.31 (3H, m) ,
7.48(1H, s), 7.55(1H, s), 7.73(1H, d, J=1.5Hz)
I_30 5 2.39(3H,s), 2.66(3H,d,J=6.9Hz), 7.43(lH,s), 7.75-7.79(2H,m),
8.33(lH,d,J=8.3Hz), 8.48(1H,d,J=8.3Hz), 8.80(lH,s)
I_31 5 2.4K3H, s), 3.88(2H, s) , 6. 86-6. 91 (1H, m), 7.28-7.32 (3H, m),
I [7.49.1H, s), 7.58(1H, s), 7.93(1H, d, J=1.2Hz)

203
Table 9(34)
Compound
No. ^-NMRtCDC^ppm)
5 0.9K3H, t, J=7.3Hz), 1.58-1.67(2H, m) , 2.69(2H, t, J=7.8Hz),
1-32 3.88(2H, br-s), 6.87-6.90(1H, m), 7.26-7.31(3H, m), 7.50(1H, s),
7.54(1H, s), 7.95(1H, d, J=2.0Hz) "
I_33 5 2.33(6H, s), 3.87(2H, br-s), 6-86-6.89(1H, m), 7.21-7.29(3H, m) ,
7.34(2H, s), 7.52(1H, s)
I_34 5 2.32(6H, s), 3.86(2H, br-s), 6.85-6.88(1H, m), 7.20-7.28 (3H, m),
7.33(2H, s), 7.60(1H, s)
I_35 5 3.86(2H, br), 6.84-6.87(1H, in), 7.13-7.28(3H, m), 7.63-7.64(2H,
m), 7.70-7.74(2H, m), 7.91(1H, br-s)
I_36 5 3.99(2H, br-s), 6.85-6.88(1H, m), 7.23-7.34(3H, m), 7.91(2H, s),
8.69(1H, s)
I_37 5 3.91(2H, br), 6.88-6.91(1H, m), 7.15-7.21(2H, m), 7.29(1H, t,
J=7.8Hz), 7-94-7. 98 (2H, m), ,8.. 03 (2H, d, J=8.8Hz), 8.1K1H, s)
I_38 (DMSO-d6) 8 5.39(2H, br-s), 6.77-6.80(1H, m), 7.12-7.19(3H, m),
8.49(2H, s), 10.53(1H, s)
(DMSO-d6) 5 2.30(3H, s), 4.32(2H, br-s), 4.39(2H, q, J=8.3Hz), 6.79-
1-39 6.86(3H, m), 7.18-7.27(2H, m), 7.45(1H, d, J=8.8Hz), 7.56(1H, s),
8.91 (1H, br-s)
53.87(2H, br-s), 6.85-6.88(1H, m), 7.14(1H, dd, J=9.3Hz, 1.0Hz),
1-40 7.19(1H, t, J=2.0Hz), 7.27(1H, t, J=7.9Hz), 7.64(2H, d, J=8.7Hz),
7.71(2H, d, J=8.7Hz), 7.86(1H, s)
I_42 53.88(2H, s), 6.90(1H, d, J=6.8Hz), 7.23-7.32(3H, m) , 7.60(1H, s),
7.92(2H, s)
I_43 53.89(2H, br-s), 6.90(1H, dt, J=2.5Hz, 6.3Hz), 7.25-7.32(3H, m),
7.59(1H, s), 7.72(2H, s)
I_44 53.89(2H, br-s), 6.90(1H, dt, J=2.5Hz, 6.4Hz), 7.28-7.30(3H, m),
7.60(1H, s), 7-93(2H, s)
I_45 53.92(2H, s), 6.92(1H, dt, J=1.5Hz, 7.3Hz), 7.23-7.30 (3H, m),
7.79(1H, s), 8.04(2H, s) '
I_4g 53.89(2H, br-s), 6.90(1H, dd, J=2.4Hz, 4.9Hz), 7.23-7.32(3H, m),
7.6K1H, s), 7.93(2H, s)
I_47 S3.88(2H, br-s), 6.90(1H, d, J=6.3Hz), 7.23-7.32(3H, m), 7.62(1H,
I |s), 7.92(2H, s) '

204
Table 9(35)
Compound
No. ^-NMRtCDCJ^ppm)
I_48 56.90-6.94(lH, m), 7.28-7.33(3H, m), 7.73(1H, s) , 8.02(1H, s) ,
8.25(1H, s)
I_49 5 2.31(6H, s), 2.90(3H, s), 6.81(1H, dd, J=1.9Hz, 7.8Hz), 7.15-
7.18(2H, m) , 7.30(1H, t, J=7.8Hz), 7.42(1H, s), 7.52(2H, s)
I_50 5 2.91(3H, s), 6.82-6.85(lH, m), 7.21-7.23(2H, m), 7.32(1H, t,
J=7.8Hz), 7.64(1H, s), 7.93(2H, s)
5 2.29(3H,s), 2.34(3H,s), 3.82(2H,br), 6.81(lH,d,J=8.1Hz),
1-51 6.92(lH,d,J=8.1Hz), 7.11 (1H, t,J=7.8Hz), 7.41-7.44(2H,m),
7.50(1H,d,J=8.3Hz), 8.36(1H,d,J=8.3Hz)
5 2.23(3H, s), 2.39(3H, s) , 3.82(2H, br), 7.10-7.16(2H, m), 7.24(1H,
1-53 d, J=1.7Hz), 7.44{1H, s), 7.49(1H, d, J=8.1Hz), 7.73(1H, s),
8.30(1H, d, J=8.8Hz)
5 2.34(3H, s), 2.40(3H, s), 3.70(2H, br), 6.72(1H, dd, J=2.4Hz,
1-55 8.1Hz), 6.83(1H, d, J=2.4Hz), 7.07(1H, d, J=8.1Hz), 7.36(1H, s),
7:44(1H, s), 7.50(1H, d, J=8.5Hz), 8.30(1H, d, J=8.5Hz)
5 2.38(6H, s), 2.42(3H, s), 3.70(2H, br), 6.72(1H, dd, J=2.4Hz,
1-56 8.1Hz), 6.89(1H, d, J=2.4Hz), 7.05(1H, s), 7.07(1H, d, J=8.1Hz),
7.36(2H, s)
I_5g 5 2.37 (6H, s), 3.90 (2H, br-s), 6.96-7.01 (1H, m), 7.10 (1H, t, J=7.8Hz), 7.36 (2H, s), 7.43-7.47 (1H, m), 7.86 (1H, d, J=13.2Hz)
I_g0 5 2.33(6H, s), 6.99(1H, dt, JKL.5HZ, 7.8Hz), 7.10(1H, t, J=7.8Hz), 7.43(2H, s), 7.46(1H, d, >>7.8Hz), 7.84(1H, d, oN13.2Hz)
I_gl 5 2.33(6H, s), 3.93(2H, s) , 7.05-7.14(1H, m), 7.17-7.21(1H, m),
7.3K1H, s), 7.35(2H, s), 7.37-7.40 (1H, m)
I_g2 5 2.40(3H, s), 3.77(2H, br), 6.79-6.83(1H, m), 6.97-7.03(1H, m),
7.44-7.51(3H, m), 8.42(1H, d, J=8.8Hz), 8.60(1H, br-d, J=18.8Hz)
5 2.35(6H, s), 3.74(2H, br-s), 6.77-6.83 (1H, m), 7.0K1H, dd,
1-63 J=8.8Hz, 11.7Hz), 7.35(2H, s) , 7.42(1H, dd, J=2.9Hz, 6.6Hz),
8.0K1H, d, J=15.6Hz) ■ . ■
5 2.38(3H, s), 4.27(2H, br), 6.89(1H, dd, J=1.5Hz, 8.1Hz), 7.05(1H,
1-64 d, J=8.8Hz), 7.18(1H, t, J=8.1Hz), 7.45(1H, s), 7.51(1H, d,
|J=8.1Hz), 7.60(1H, s), 8.34(1H, d, J=8.8Hz)

205
Table 9(36)
Compound
No. ^-NMRtCDCl^ppra)
5 2.40(6H, s), 4.27(2H, br-s), 6.88(1H, dd, J=1.5Hz, 7.8Hz),
1-65 7.03(1H, dd, J=1.5Hz, 7.8Hz), 7.16(1H, t, J=7.8Hz), 7.29(1H, s),
7.36(2H, s)
5 2.39(3H,s), 4.27(2H,br), 7.08 (1H,dd,J=2.2Hz, 8.3Hz), 7.32-
1-66 7.36(2H,m), 7.45(lH,s), 7.50(1H,d,J=8.5Hz), 7.68(lH,s),
8.24(lH,d,J=8.5Hz)
I_67 5 2.33(6H, s), 4.27(2H, br-s), 7.15(1H, d, J=8.1Hz), 7.35-7.38(5H,
m)
5 2.4K3H, s), 3.87(2H, br), 6.73(1H, dd, J=2.9Hz, 8.5Hz), 7.18(1H,
1-68 d, J=2.9Hz), 7.21(1H, d, J=8.8Hz), 7.45(1H, s), 7.50(1H, d,
J=8.8Hz), 8.12(1H, s), 8.34(1H, d, J=8.5Hz)
I_69 5 2.39(6H, s), 3.85(2H, br-s), 6.72(1H, dd, J=2.7Hz, 8.5Hz),
' 7.15(1H, d, J=2.7Hz), 7.22(1H, d, J=8.5Hz), 7.36(2H, s) , 7.66(1H, s)
I_70 5 2.43(6H, s), 4.34(2H, br), 6.86(1H, dd, J=1.5Hz, 8.3Hz), 6.96(1H,
dd, J=1.5Hz, 8.3Hz), 7.13(1H, s), 7.19(1H, t, J=8.3Hz), 7.36(2H, s)
5 2.41(3H,s), 3.87(2H,br), 6.66(1H,dd,J=2. 9Hz, 8.5Hz),
1-71 7.03(lH,d,J=2.9Hz), 7.38(1H, d,J=8.5Hz), 7.45(lH,s),
7.50(lH,d,J=8.5Hz), 7.75(lH,br-s), 8.33(1H, d, J=8.5Hz)
5 2.40(3H, s), 3.94(2H, br), 7.05-7.16(2H, m), 7.36(1H, dd, J=2.2Hz,
1-72 8.5Hz), 7.45(1H, s), 7.50(1H, d, J=9.0Hz), 7.66(1H, s), 8.24(1H, d,
J=9.0Hz)
5 2.41(3H,s), 3.88(2H,br-s), 6.54(lH,dd,J=2.9Hz, 8.5Hz),
1-73 6.88(lH,d,J=2.9Hz), 7.37 (lH,s), 7.45(lH,s), 7.52(lH,d,J=8.3Hz),
7. 61 (1H, d, J=8 . 3Hz), 8 ■ 32 (1H, d, J=8 . 5Hz)
I_74 5 2.44(6H, s), 3.86(2H, br-s), 6.52(1H, dd, J=2.9Hz, 8.5Hz),
6.91(1H, d, J=2.9Hz), 7.12(1H, s), 7.35(2H, s), 7.62(1H, d, J-8.5Hz)
I_75 5 2.38(3H, s), 4.39(2H, s), 7.06(1H, s), 7.40(1H, d, J=1.7Hz), 7.43-
7.50(3H, m), 7.90(lH, d, J=9.1Hz), 8.73(1H, s)
I_76 5 2.27{6H, s), 4.09(2H, br-s), 7.08(1H, s), 7.33(2H, s), 7.37(1H,
s), 7.43(1H, s), 7.83(1H, s)
5 2.39(3H,s), 2.93(3H,s), 3.95(2H,br), 6.84(lH,d,J=8.3Hz), 7.21-
1-77 7.27(2H,m), 7.44 (lH,s), 7.48(1H,d,J=8.5Hz) , 7.69(lH,s),
8.28(lH,d,J=8.5Hz)
I_79 5 2.33(6H,s), 3.76(4H,br), 6.19(1H,d,J=2.0Hz) , 6.60(2H,d,J=2.OHz) ,
7.34(lH,br), 7.52(2H,s)
I_80 5 2.38(3H,s), 4.65(2H,s), 7.26(lH,s), 7.34(lH,s), 7.47(lH,s),
|7.52(lH,d, J=8.5Hz), 8.20 (1H, d, J=8 . 5Hz) (

206
Table 9(37)
Compound
Nfo. ^-NMRtCDC^ppm)
5 2.50 (3H, s), 3.90 (2H, s), 6.91-6.94 (1H, m), 7.27-7.35 (3H, m),
1-81 7.48-7.57 (2H, m), 7.70 (1H, s), 7.75 (1H, s), 8.01-8.04 (1H, m),
8.45-8.48 (1H, m)
51.74-1.78 (2H, m), 1.82-1.88 (2H, m), 2.72 (2H, t, J=6.0Hz), 3.01
I_82 (2H, q, J=6.0Hz), 3.88 (2H, br-s), 6.85-6.88 (1H, m), 7.14-7.16 (1H,
m), 7.22-7.29 (2H, m), 7.42 (1H, d, J=8.6Hz), 7.70 (1H, br-s), 8.10
(1H, d, J=9.0Hz)
51.71-1,79 (4H, m), 2.81 (2H, t, J=6.1Hz), 2.99 (2H, q, J=6.3Hz),
1-83 3.87 (2H, br-s), 6.87-6.90 (1H, m), 7.24-7.29 (3H, m), 7.47-7.52
(2H, m)
53.87 (2H, br-s), 6.51 (1H, septet, J=6.3Hz), 6.85-6.88 (1H, m) ,
I_84 6.99 (1H, d, J=8.7Hz), 7.15 (1H, d, J=7.3Hz), 7.20 (1H, t, J=2.0Hz),
7.25-7.29 (1H, m), 7.75 (1H, br-s), 8.15 (1H, dd, J=8.7Hz, 2.4Hz),
' 8.30 (1H, d, J=2.4Hz)
5 2.37(3H, s), 4.27(2H, br-s), 6.55(1H, septet, J=6.3Hz), 6.88-
1-85 6.91(2H, m), 7.06(1H, dd, J=7.3Hz, 1.5Hz), 7.18(1H, t, J=7.3Hz),
7.37(1H, br-s), 8.50(1H, br-s)
I_86 5 2.37(3H, s), 3.88(2H, br-s), 6.34{1H, septet, J=6.3Hz), 6.88(1H,
|s), 6.89-6.9K1H, m), 7.23-7.31 (3H, m), 7.47(1H, br-s)

207
The insecticides containing the compounds represented by formula (1) of the present invention as active ingredients are suitable for preventing insect pests such agricultural, horticultural and stored grain insect pests which are noxious to paddy rice, fruit trees, vegetables, other crops and flowing plants, sanitary pests, or nematodes. For example, the insecticides have strong insecticidal activity on the following insect pests: Lepidoptera such as cotton caterpillar (Diaphania indica), oriental tea tortrix (Homona magnanima), cabbage webworm (Hellulla undalis), summer fruit tortrix(Adoxophyes orana fasciata), smaller tea tortrix (Adoxophyes sp.), apple tortrix (Archips fuscocupreanus), peach fruit moth (Carposina niponensis), Manchurian fruit moth (Grapholita inopinata), oriental fruit moth (Grapholita molesta), soybean pod borer (Leguminivora glycinivorella), mulberry leafroller (Olethreutes mori), citrus leafminer (Phyllocnistis citrella), persimmon fruit moth (Stathmopoda masinissa), tea leafroller (Caloptilia theivora), Caloptilia sp. (Caloptilia zachrysa), apple leafminer (Phyllonorycter ringoniella), pear barkminer (Spulerrina astaurota), small citrus dog (Papilio xuthus), common cabbage worm (Pieris rapae crucivora), tabacco budworm (Heliothis armigera), codling moth (Lapsey resia pomonella), diamondback moth (Plutella xylostella), apple fruit moth (Argyresthia conjugella), peach fruit moth (Carposina niponensis), rice stem borer (Chilo suppressalis), rice leafroller (Cnaphalocrocis irtedinalis), tabacco moth (Ephestia eluteila), mulberry pyralid (Glyphodes pyloalis), paddy borer (Scirpophaga incertulas), rice skipper (Parnara

208
guttata) , rice armyworrn (Pseudaletia separata) , pink borer (Sesamia inferens), cabbage armyworrn (Mamestra brassicae), common cutworm (Spodoptera litura), beet armyworrn (Spodoptera exigua), black cutworm (Agrotis ipsilon), turnip moth (Agrotis segetum), beet semi-looper (Autographa nigrisigna), and cabbage looper (Trichoplusia ni); hemiptera such as aster leafHopper (Macrosteles fascifrons), green rice leafHopper (Nephotettix cincticeps), brown rice planthopper (Nilaparvata lugens), small brown planthopper (Laodelphax striatellus), whitebacked rice planthopper (Sogatella furcifera), citrus psylla (Diaphorina citri), grape whitefly (Aleurolobus taonabae), silverleaf whitefly (Bermisia argentifolii), sweetpotato whitefly (Bemisia tabaci), greenHouse whitefly (Trialeurodes vaporariorum), turnip aphid (Lipaphis erysimi), cotton aphid (Aphis gossypii), apple aphid (Aphis Citricola), green peach aphid (Myzus persicae), Indian wax scale (Ceroplastes ceriferus), Comstock mealybug (Pseudococcus Comstocki), Japanese mealybug (Planococcus kraunhiae), cottony citrus scale (Pulvinaria aurantii), camphor scale (Pseudaonidia duplex), San Jose scale (Comstockaspis perniciosa), arrowHead scale (Unaspis yanonensis), brownwinged green bug (Plautia Stall), and brown marmorated stink bug (Halyomorpha mista); Coleoptera such as soybean beetle (Anomala rufocuprea), Japanese beetle (Popillia japonica), cigarette beetle (Lasioderma serricorne), powderpost beetle (Lyctusbrunneus) , twenty-eight-spotted ladybird (Epilachna vigintioctopunctata), adzuki been weevil (Callosobruchus chinensis), vegetable weevil (Listroderes costirostris), maize weevil (Sitophilus zeamais), boll weevil

209
(Anthonomus gradis gradis), rice water weevil (Lissorhoptrus oryzophilus), cucurbit leaf beetle (Aulacophora femoralis) , rice leaf beetle' (Oulema oryzae), striped flea beetle (Phyllotreta striolata), pine shoot beetle (Tomicus piniperda), Colorado potato beetle (Leptinotarsa decemlineata), Mexican bean beetle (Epilachna varivestis), corn rootworm (Diabrotica sp.), yellowspotted longicorn beetle (Psacothea hilaris), and whitespotted longicorn beetle (Anoplophora malasiaca); Diptera such as melon fly (Dacus(Bactrocera) dorsalis), rice leafminer (Agromyza oryzae), onion maggot (Delia antiqua), seedcorn maggot (Delia platura), soybean pod gall midge (Asphondylia sp.), house fly (Musca domestica), garden pea leafminer (Chromatomyia horticola), legume leafminer (Liriomyza trifolii), bryony leafminer (Liriomyza
bryoniae) , and common house mosquito (Culex pipiens 'pirpjrens'f; <^—■
Nematoda such as coffee root-lesion nematode (Pratylenchus coffeae), root-lesion nematode (Pratylenchus sp.), potato cyst nematode (Globodera rostochiensis), root-knot nematode (Meloidogyne sp.), citrus nematode (Tylemchulus semipenetrans) , nematode (Aphelenchus avenae), and chrysanthemum foliar nematode (Aphelenchoides ritzemabosi); Thysanoptera such as melon thrips (Thrips palmi), western flower thrips (Frankliniella occidentalis), yellow tea thrips (Scirtothrips dorsalis), honeysuckle thrips (Thrips flavus), and onion thrips (Thrips tabaci); Orthoptera such as German cockroach (Blattella germanica), American cockroach (Periplaneta americana), and rice grasshopper (Oxya yezoensis).
The insecticides containing the compounds represented by-formula (1) of the present invention as active ingredients have a

210
significant preventive effect on the above-described insect pests noxious to lowland crops, dry field crops, fruit trees, vegetables, other crops, and flowering plants. The effect as the insecticides of the present invention can be achieved by treating paddy water, foliages or soil of paddy fields, dry fields, fruit trees, vegetables, other crops, or flowering plants before the breeding of noxious insects or at the time of obervation of the breeding of noxious insects at the predicted breeding season of noxious insects.
The insecticides of the present invention are generally formed into formulations suitable for use according to a normal method for formulating agricultural/Horticultural pesticides. Namely, a compound represented by formula (1) may be mixed with an appropriate inert carrier, and if required, an auxiliary at a proper proportion, and the resultant mixture is subjected to dissolution, separation, suspension, mixing, impregnation, adsorption or adhesion to form a suitable formulation such as a suspension, an emulsion, a liquid drug, a wettable powder, a granule, a dusting powder, or a tablet. As the inert carrier used in the present invention, either a solid or a liquid may be used. Examples of a material usable as the solid carrier include soybean flour, grain flour, wood flour, bark flour, sawing flour, tobacco stalk flour, walnut sHell flour, bran, cellulose powder, a residue after plant extraction, a synthetic polymer such as a synthetic resin powder, clay (for example, kaoline, bentonite, or acid white clay), talc (for example, talc or pyrophyllite), silica (for example, diatomite, silica powder, mica, white carbon (synthetic

211
high-dispersion silicate referred to as "hydrous silicate fine powder" or "hydrous silicate", some products containing calcium silicate as main components)), activated carbon, sulfur powder, pumice, calcined diatomite, brick powder, fly ash, sand, inorganic mineral powders such as calcium carbonate and calcium phosphate, chemical fertilizers such as ammonium sulfate, ammonium phosphate, ammonoium nitrate, urea, and ammonium chloride, and compost. These carriers are used alone or in a mixture of at least two kinds.
As a material usable as the liquid carrier, a material having a solvent ability or a material having no solvent ability but having an ability to disperse an active ingredient compound with the aid of an auxiliary is selected. Typical examples of the liquid carrier are given below, and these examples can be used alone or in a mixture of two more kinds. Examples of the liquid carrier include water, alcohols (for example, methanol, ethanol, isopropanol, butanol, and ethylene glycol); ketones (for example, acetone, methylethyl ketone, methyl isobutyl ketone, diisobutyl ketone, and cyclohexanone); ethers (for example, diethyl ether, dioxane, cellosolve, diisopropyl ether, and tetrahydrofuran); aliphatic hydrocarbons (for example, kerosine and mineral oil); aromatic hydrocarbons (for example, benzene, toluene, xylene, solvent naphtha, and alkylnaphthalene); halogenated hydrocarbons (for example, dichloromethane, chloroform, carbon tetrachloride, and chlorobenzene); esters (for example, ethyl acetate, butyl acetate, ethyl propionate, diisobutyl phthalate, dibutyl phthalate, and dioctyl phthalate) ; amides (for example, dimethylformarnide,

212
diethylformamide, and dimethylacetamide); and nitriles (for example, acetonitrile).
Typical examples of other auxiliaries are given below, and these examples are used alone or in combination according to purposes. The auxiliary is not necessarily used. For example, a ' surfactant is used for emulsifying, dispersing, solubilizing and/or wetting the active ingredient compound. Examples of the surfactant include
polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene higher fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylaryl sulfonate, naphthalenesulfonate, lignin-sulfonate, higher alcohol sulfates. Examples of other auxiliaries used for stabilizing dispersion of the active ingredient compound, and tackifying and/or bonding the active ingredient compound are given below. Examples of such auxiliaries include casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose, gum arabic, polyvinyl alcohol, wood turpentine, bran oil, bentonite, xanthan gum, and lignin-sulfonate.
Another auxiliary for improving fluidity of a solid product can also be used. Examples of such an auxiliary include wax, stearates, and alkyl phosphates. Also, an auxiliary such as a naphthalenesulfonic acid condensate or condensed phosphate, can be used as a deflocculant for a suspending product. Furthermore, an auxiliary such as silicone oil can be used as a defoaming agent.
The compounds represented by formula (1) of the present invention are stable to light, heat and oxidation. However, an

213
appropriate amount of an antioxidant or an ultraviolet absorber, for example, a phenol derivative such as BHT (2,6-di-t-butyl-4-methyl phenol) or BHA (butylated hydroxyanisole), a bisphenol derivative, an arylamine such as phenyl-a-naphthylamine, phenyl-[3-naphthylamine, or a condensate of phenetidine and acetone, or a benzophenone compound, may be added as a stabilizer to produce compositions having a stable effect.
When a compound represented by formula (1) of the present invention is used as an active ingredient, generally, the amount thereof used in a dust is 0.5% by weight to 20% by weight, the amount in an emulsion is 5% by weight to 50% by weight, the amount in a wettable powder is 10% by weight to 90% by weight, the amount in a granule is 0.1% by weight to 20% by weight, and the amount in a flowable formulation is 10% by weight to 90% by weight. With respect to the amount of the carrier in a formulation, the amount in a dust is 60% by weight to 99% by weight, the amount in an emulsion is 40% by weight to 95% by weight, the amount in a wettable powder is 10% by weight to 90% by weight, the amount in a granule is 80% by weight to 99% by weight, and the amount in a flowable formulation is 10% by weight to 90% by weight. With respect to the amount of the auxiliary in a formulation, the amount in a dust is 0.1% by weight to 20% by weight, the amount in an emulsion is 1% by weight to 20% by weight, the amount in a wettable powder is 0.1% by weight to 20% by weight, the amount in a granule is 0.1% by weight to 20% by weight, and the amount in a flowable formulation is 0.1% by weight to 20% by weight.
In order to prevent various noxious insects, the compound of

214
the present invention is directly used or properly diluted with water or suspended in water, and an effective amount thereof for preventing pests is applied to crops in which the breeding of the noxious insects is predicted, or a place where the breeding of the noxious insects is undesirable. The amount of the compound used depends upon the various factors, for example, the purpose, the object insects, the growth conditions of crops, the breeding tendency of insects, weather, environmental conditions, formulations, application methods, application places, and application times. However, the content of the active ingredient used is generally 0.0001 ppm to 5000 ppm, and preferably 0.01 ppm to 1000 ppm. The amount of the active ingredient per 10a is generally 1 g to 300 g.
An insecticide containing as an active ingredient the compounds represented by formula (1) of the present invention may be singly used for preventing insect pests such agricultural, horticultural or stored grain insect pests which are noxious to paddy rice, fruit trees, vegetables, other crops and flowering plants, sanitary pests, or nematodes. In order to further obtain an excellent preventive effect on various noxious insects which simultaneously occur, at least one of other insecticides and/or fungicides may be combined with the compounds represented by formula (1) of the present invention.
Examples of such insecticides which can be combined with the compounds represented by formula (1) of the present invention include synthetic pyrethroid insecticides such as allethrin, tetramethrin, resmethrin, phenothrin, furamethrin, permethrin,

215
cypermethrin, deltamethrin, cyhalothrin, cyfiuthrin, fenpropathrin, tralomethrin, cycloprothrin, flucythrinate, fluvalinate, acrinathrin, tefluthrin, bifenthrin, empenthrin, beta-cyfluthrin, zeta-cypermethrin, and fenvalerate, and various isomers thereof and pyrethrum extracts; organophosphate insecticides such as DDVP, cyanophos, fenthion, fenitrothion, tetrachlorvinphos, dimethylvinphos, propaphos, methylparathion, temephos, phoxim, acephate, isofenphos, salithion, DEP, EPN, ethion, mecarbam, pyridafenthion, diazinon, pirimiphos-methyl, etrimfos, isoxathion, quinalphos, chlorpyrifos-methyl, chlorpyrifos, phosalone, phosmet, methidathion, oxydeprofos, vamidothian, malathion, phenthoate, dimethoate, formothion, thiometon, ethylthiometon, phorate, terbufos, profenofos, prothiofos, sulprofos, pyraclofos, monocrotophos, haled, fosthiazate, and cadusafos; carbamate insecticides such as NAC, MTMC, MIPC, BPMC, XMC, PHC, MPMC, ethiofencarb, bendiocarb, pirimicarb, carbosulfan, benfuracarb, methomyl, oxamyl, and aldicarb; arylpropylether insecticides such as etofenprox and halfenprox; silylether insecticides such as silafluofen; insecticidal natural products such as nicotine-sulfate, polynactin complex, abamectin, milbemectin, and BT agents; insecticides such as, cartap, thiocyclam, bensultap, diflubenzuron, chlorfluazuron, • teflubenzuron, triflumuron, flufenoxuron, flucycloxuron, hexaflumuron, fluazuron, imidacloprid, nitenpyram, acetamiprid, dinotefuran, pymetrozine, fipronil, buprofezin, fenoxycarb, pyriproxyfen, methoprene, hydroprene, kinoprene, diafenthiuron, triazamate, tebufenozide, and endosulfan; acaricides such as dicofol, chlorobenzilate,

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bromopropylate, tetradifon, CPCBS, BPPS, chinomethionate, amitraz, benzoximate, hexythiazox, fenbutatin oxide, cyhexatin, dienochlor, clofentezine, pyridaben, fenpyroximate, fenazaquin, and tebufenpyrad; and other insecticides such as novaluron, noviflumuron, emamectin benzoate, clothianidin, thiacloprid, thiamethoxam, flupyrazofos, acequinocyl, bifenazate, chromafenozide, etoxazole, fluacrypyrim, flufenzine, halofenozide, indoxacarb, methoxyfenozide, spirodiclofen, tolfenpyrad, gamma-cyhalothrin, ethiprole, amidoflumet, bistrifluron, flonicamid, flubrocythrinate, flufenerim, pyridalyl, pyrimidifen, spinosad, and spiromesifen.
Examples of fungicides which can be combined with the compounds represented by formula (1) of the present invention include azole fungicides such as triadimefon, hexaconazole, propiconazole, ipconazole, prochloraz, and triflumizole; pyrimidine fungicides such as pyrifenox and fenarimol; anilinopyrimidine fungicides such as mepanipyrim and cyprodinil; acylalanine fungicides such as metalaxyl, oxadixyl, and benalaxyl; benzimidazole fungicides such as thiophanate-methyl and benomyl; dithiocarbamate fungicids such as mancozeb, propineb, zineb, and metiram; organochlorine fungicides such as
tetrachloroisophthalonitrile; carboxamide fungicides such as carpropamid and ethaboxam; morpholine fungicides such as dirnethomorph; strobilurin fungicides such as azoxystrobin, kresoxim-methyl, metominostrobin, orysastrobin, fluoxastrobin, trifloxystrobin, dimoxystrobin, pyraclostrobin, and picoxystrobin; dicarboxyimide fungicides such as iprodione and procymidone; soil-

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applied fungicides such as flusulfamide, dazomet, methyl isothiocyanate, and chloropicrin; copper fungicides such as basic copper chloride, basic copper sulfate, copper nonylphenol sulfonate, oxine-copper, and DBEDC; inorganic fungicides such as sulfur and zinc sulfate; organophosphate fungicides such as edifenphos, tolclofos-methyl, and fosetyl-aluminum; melanin biosynthesis inhibitors such as phthalide, tricyclazole, pyroquilon, and diclocymet; antibiotics such as kasugamycin, validamycin, and polyoxins; fungicidal natural products such as repe seed oil; and other fungicides such as benthiavalicarb-isopropyl, iprovalicarb, cyflufenamid, fenhexamid, quinoxyfen, spiroxamine, diflumetorim, metrafenone, picobenzamid, proquinazid, silthiofam, oxypoconazole, famoxadone, cyazofamid, fenamidone, furametpyr, zoxamide, boscalid, tiadinil, simeconazole, chlorothalonil, cymoxanil, captan, dithianon, fluazinam, folpet, dichlofluanid,
{RS}-N-[2-(1,3-dimethylbutyl)thiophen-3-yl]-1-methyl-3-trifluoromethyl-lH-pyrazole-4-carboxamide (penthiopyrad; ISO proposed), oxycarboxin, mepronil, flutolanil, triforine, oxolinic acid, probenazole, acibenzolar-S-methyl, isoprothiolane, ferimzone, diclomezine, pencycuron, fluoroimide, chinomethionate, iminoctadine-triacetate, and iminoctadine-albesilate.
When the compounds represented by formula (1) of the present invention are combined with at lease one type of other insecticide and/or fungicide, mixed compositions of the compounds represented by formula (1) and other insecticides and/or fungicides may be used, or the compounds represented by formula (1) may be mixed

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with other insecticides and/or fungicides during agricultural treatment.
Besides the above-described insecticides and fungicides, the compounds represented by formula (1) may be mixed with a herbicide, a fertilizer, an ameliorant, a plant protective such as a plant growth regulator, or resources to form multipurpose compositions having superior efficiency or compositions from which an additive ■ effect or a synergistic effect can be expected.
Although representative examples of the present invention will be described below, the present invention is not limited to these examples.
Example 1
(1-1) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
3-nitrobenzamide
To a solution prepared by adding 20.0 g of 2,6-dimethyl-4-heptafluoroisopropylaniline and 11.0 g of pyridine to 100 ml of tetrahydrofuran and then stirring the resultant mixture at room temperature was dropwise added a solution of 13.0 g of 3-nitrobenzoyl chloride in 20 ml of tetrahydrofuran. After the resultant mixture was stirred at room temperature for 10 hours, ethyl acetate and water were added to the reaction solution. Then, a separating operation was performed, and an organic layer was separated and then dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was washed with a n-hexane-diisopropyl

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ether solvent mixture to obtain 26.0 g (yield 85%) of the title compound as a white solid.
^-NMR (CDC13, ppm) 5 2.33 (6H, s) , 7.37 (2H, s) , 7.68 (1H, s), 7.72 (1H, t, J=8.1Hz), 8.28 (1H, d, J=8.1Hz), 8.44 (1H, dd, J=1.2Hz, 8.1Hz), 8.75 (1H, t, J=1.2Hz)
(1-2) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide
To a solution prepared by adding 0.9.0 g of N- (2, 6-dimethyl-4-heptafluoroisopropyl)phenyl 3-nitrobenzamide and 1.56 g of tin chloride anhydride to 25 ml of ethanol and stirring the resultant mixture at room temperature was added 2 ml of cone, hydrochloric acid. The resultant mixture was then stirred under heating at 60°C for 1 hour. After the temperature was returned to room temperature, the reaction solution was poured into water and then neutralized with potassium carbonate. Then, ethyl acetate was added to the reaction solution,- and insoluble materials were filtered off. Then, an organic layer was separated and then dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was washed with hexane to obtain 0.44 g (yield 53%) of the title compound as a white solid.
1H-NMR (CDCI3, ppm) 5 2.34 (6H, s) , 3.87 (2H, broad), 6.86-6.89 (1H, m), 7.20-7.35 (6H, m)
(1-3) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl

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3-(2-chloroethoxycarbonylamino)benzamide (Compound No. 130)
To a solution prepared by adding 0.20 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide and 0.08 g of pyridine to 5 ml of tetrahydrofuran and stirring the resultant mixture at room temperature was dropwise added a solution of 0.07 g of 2-chloroethyl chloroformate in 1 ml of tetrahydrofuran. After the resultant mixture was stirred for 2 hours, ethyl acetate and water were added to the reaction solution. Then, a separating operation was performed, and an organic layer was separated and then dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane : ethyl acetate =4:1) to obtain 0.23 g (yield 91%) of the title compound as a white solid.
^-NMR (CDC13, ppm) 5 2.35 (6H, s), 3.74-3.77 (2H, m) , 4.44-4.47 (2H, m), 6.87 (1H, broad), 7.36 (2H, s), 7.43-7.52 (2H, m), 7.59-7.64 (2H, m), 8.02 (1H, s)
The compounds shown in Table 6 can be produced as production intermediates useful for producing the compounds represented by formula (1) of the present invention according to the processes described in Examples 1-1 and 1-2.
Example 2
Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-
(ethylthiocarbonylamino)benzamide (Compound No. 1962)
To a solution prepared by adding 0.25 g of N-(2,6-dimethyl-4-

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heptafluoroisopropyl)phenyl 3-aminobenzamide produced in (1-2) of Example 1 and 0.06 g of pyridine to 5 ml of tetrahydrofuran and then stirring the resultant mixture at room temperature was dropwise added a solution of 0.08 g of ethyl chlorothioformate in 1 ml of tetrahydrofuran. After the resultant mixture was stirred for 2 hours, ethyl acetate and water were added to the reaction solution. Then, a separating operation was performed, and an organic layer was separated and then dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was washed with hexane to obtain 0.27 g (yield 89%) of the title compound as a white solid.
1H-NMR (CDCl3+DMSO-d6, ppm) 5 1.34 (3H, t, J=7.3 Hz), 2.34 (6H, s) , 2.96 (2H, q, J=7.3 Hz), 7.33 (2H, s) , 7.41 (1H, t, J=7.8. Hz), 7.67 (1H, d, J=7.8Hz), 7.83-7.85 (1H, m), 8.11 (1H, d, J=2. 0 Hz), 8.79 (1H, s), 9.58 (1H, s)
Example 3
Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-[(4-
cyanobenzyl)oxycarbonylamino]benzamide (Compound No. 85)
To a solution prepared by adding 0.30 g 3-isocyanatobenzoyl chloride to 10 ml of ether and then stirring the resultant mixture at 2°C was dropwise added, over 5 minutes at a temperature kept at 2°C, a solution of 0.23 g of 4-cyanobenzyl alcohol and 0.32 g of tri-n-butylamine in 5 ml of ether. After the resultant mixture was stirred at 2°C for 2 hours, the temperature was returned to

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room temperature, and then a solution of 0.49 g of 2,6-dimethyl-4-heptafluoroisopropylaniline in 5 ml of ether was dropwise added to the mixture, followed by stirring at room temperature for 3 hours. Then, ethyl acetate was added to the reaction solution, and the reaction solution was washed with water twice. Then, an organic layer was dried with' anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane : ethyl acetate = 2:1 to 1:1) to obtain 0.50 g (yield 40%) of the title compound as an oily material..
XH-NMR (CDC1, ppm) 5 2.34 (6H, s), 5.27 (2H, s), 6.97 (1H, broad-s), 7.35 (2H, s), 7.45-7.52 (4H, m), 7.61-7.69 (4H, m), 8.01 (1H, s) Similarly, N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-[(6-chloropyridine-3-yl)methoxycarbonylamino]benzamide (Compound No. 163) was produced by using 2-chloro-5-hydroxymethylpyridine. 1H-NMR (CDC13, ppm) 5 2.34 (6H,s), 5.22 (2H, s) , 6.89 (1H, broad-s), 7.35-7.49 (5H, m), 7.62 (2H, d, J=7.3 Hz), 7.72-7.77 (1H, m), 8.00 (1H, broad-s), 8.45 (1H, d, J=2.4 Hz)
N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-[(tetrahydrofuran-3-yl)methoxycarbonylamino]benzamide (Compound No. 158) was produced by the same process as described above using 3-hydroxymethyltetrahydrofuran except that the solvent was changed to tetrahydrofuran.
^-NMR (CDC13/ ppm) 5 1.66-1.73 (1H, m) , 2.05-2.13 (1H, m) , 2.34 (6H, s), 2.60-2.70 (1H, m) , 3.64-3.68 (1H, m) , 3.73-3.79 (1H, m) , 3.85-3.92 (2H, m), 4.09-4.15 (2H, m) , 6.87 (1H, broad-s), 7.35

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(2H,s), 7.46 (2H, t, J=7.8 Hz), 7.61-7.66 (2H, m), 8.01 (1H, broad-s)
Example 4
(4-1) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
3-aminobenzthioamide
To 10 ml of toluene were added 0.35 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide produced in Example
(1-2) and 0.19 g of Lawesson's reagent. Then, the resultant mixture was stirred under heating at a reflux temperature for 6 hours. The reaction solution was concentrated under reduced pressure, and the solvent was distilled off. The residue was purified by silica gel column chromatography (eluent; hexane : ethyl acetate =3:1) to obtain 0.07 g (yield 20%) of the title compound.
^-NMR (CDC13, ppm) 8 2.36 (6H, s) , 3.87 (2H, broad-s), 6.84-6.87 (1H, m), 7.18-7.24 (2H, m), 7.33 (1H, s), 7.39 (2H, s), 8.56 (1H, broad-s)
(4-2) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(2,2,2-trichloroethoxycarbonylamino)benzthioamide (Compound No. 1964)
To a solution prepared by adding 0.07g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzthioamide and 0.03 g of pyridine to 5 ml of tetrahydrofuran and then stirring the resultant mixture at room temperature was dropwise added a solution of 0.05 g of 2,2,2-trichloroethyl chloroformate in 1 ml

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of tetrahydrofuran. After the resultant mixture was stirred 2 hours, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer-was separated and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane : ethyl acetate =4:1) to obtain 0.09 g (yield 90%) of the title compound as a white solid. ^-NMRfCDCla, ppm) 5 2.37 (6H, s) , 4.85 (2H, s) , 7.07 (1H, broad), 7.39 (2H, s), 7.45 (1H, t, J=8.1 Hz), 7.61-7.68 (2H, m), 8.11 (1H, s), 8.69(1H, s)
Example 5
(5-1) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
6-chloropyridine-2-carboxamide
First, to a solution prepared by adding 2.36 g of 6-chloropyridine-2-carboxylic acid and 5 droplets of N,N-dimethylformamide to 30 ml of toluene was added 2.14 g of thionyl chloride, and then the resultant mixture was stirred under heating at 80°C for 2 hours. Then, the solvent was distilled off under reduced pressure, and the residue was dissolved in 10 ml of tetrahydrofuran. The resultant solution was added dropwise, at room temperature, to a solution obtained by adding 3.83 g of 2,6-dimethyl-4-heptafluoroisopropylaniline and 1.28 g of pyridine to 20 ml of tetrahydrofuran, followed by stirring for 5 hours. Then, ethyl acetate and water were added to the reaction solution, and a

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separating operation was performed. Then, an organic layer .was separated and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was.collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane : ethyl acetate =4:1) to obtain 3.90 g (yield 67%) of the title compound as a solid. 1H-NMR(CDC13, ppm) 5 2.36 (6H, s) , 7.36 (2H, s) , 7.56 (1H, dd, J=1.0Hz, 8.1Hz), 7.88 (1H, dd, J=7.6Hz, 8.1Hz), 8.23 (1H, dd, J=1.0Hz, 7.6Hz), 9.27 (1H, broad-s)
(5-2) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
6-aminopyridine-2-carboxamide
In a 200 ml autoclave were charged 3.08 g of N-(2,6-dimethyl-
4-heptafluoroisopropyl)phenyl 6-chloropyridien-2-carboxamide, 30 ml of 28% ammonia water, 0.20 g of cupper sulfate, and 70 ml of methanol, and the resultant mixture was stirred under heating at
150°C for 2 hours. After the mixture was cooled to room temperature, ammonia was distilled off at 60°C under atmospheric pressure, and methanol was distilled off under reduced pressure. Then, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated and dried with anhydrous sodium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane : ethyl acetate = 3:2 to 2:3) to

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obtain 2.90 g (yield 98%) of the title compound as a oily material. 1H-NMR (CDC13, ppm) 6 2.35 (6H, s), 4.57 (2H, broad-s), 6.69-6.74 (1H, m), 7.34 (2H, s) , 7.62-7.66 (2H, m) , 9.39 (1H, broad-s)
(5-3) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-(2,2,2-trichloroethoxycarbonylamino)pyridine-2-carboxamide (Compound No. 1968)
To a solution prepared by adding 0.15 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-aminopyridine-2-carboxamide and 0.06 g of pyridine to 5 ml of tetrahydrofuran and stirring the resultant mixture at room temperature was dropwise added a solution of 0.085 g of 2,2,2-trichloroethyl chloroformate in 1 ml of tetrahydrofuran. After the resultant mixture was stirred for 2 hours, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane : ethyl acetate = 10:1) to obtain 0,. 13 g (yield 61%) of the title compound as a white solid. XH-NMR (CDC13/ ppm) 8 2.35 (6H, s) , 4.89 (2H, s) , 7.36 (2H, s) , 7.63 (1H, broad-s), 7.97 (1H, dd, J=7.6 Hz, 8.3Hz), 8.05 (1H, d, J=7.6 Hz), 8.21 (1H, d, J=8.3 Hz), 9.17 (1H, broad-s)
(5-4) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-(2,2,2-trichloroethoxycarbonylamino)pyridine-N-oxide-2-

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carboxamide (Compound No. 2062)
To 10 ml of benzene was added 0.26 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6- (2,2,2-
trichloroethoxycarbonylamino)pyridine-2-carboxamide produced in Example 5-3, and then the resultant mixture was stirred. Then, 0.08 g of m-chloroperbenzoic acid was added to the mixture at room temperature. After the resultant mixture was stirred at 70°C for 1 hour, 0.2 g of m-chloroperbenzoic acid was further added to the mixture, followed by stirring at 70°C for 7 hours. Then, the mixture was diluted with ethyl acetate, and an organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate three times and dried with anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane : ethyl acetate = 10:1) to obtain 0.11 g (yield 41%) of the title compound as an amorphous material.
XH-NMR (CDC13, ppm) 5 2.37 (6H, s), 4.91 (2H, s), 7.36 (2H, s) , 7.61 (1H, t, J=8.3 Hz), 8.23 (1H, dd, J=8.3 Hz, 1.9 Hz), 8.45 (1H, dd, J=8.3 Hz, 1.9 Hz), 9.81 (1H, broad-s) , 12.70 (1H, broad-s)
(5-5) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
6-(methylamino)pyridine-2-carboxamide
N-(2, 6-dimethyl-4-heptafluoroisopropyl)phenyl 6-
(methylamino)pyridine-2-carboxamide was produced by using N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-chloropyridine-2-carboxamide produced in Example 5-1 and a methylamine aqueous solution as reaction materials according to the process described.

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in Example 5-2.
Hl-NMR (DMSO-d6/ ppm) 5 2.30 (6H, s) , 2.92 (3H, s) , 6.71 (1H, d, J=8.3Hz), 6.85 (1H, d, J=4.9Hz), 7.22 (1H, d, J=7.0Hz), 7.44 (2H, s), 7.55 (1H, dd, J=7.0Hz, 8.3Hz), 10.05 (1H, s)
(5-6) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-[N-(2,2,2-trichloroethoxycarbonyl)-N-methylamino]pyridine-2-carboxamide (Compound No. 2168)
N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-[N-(2,2,2-trichloroethoxycarbonyl)-N-methylamino]pyridine-2-carboxamide was produced by using N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-(methylamino)pyridine-2-carboxamide produced in Example 5-5 as a starting material according to the process described in Example 5-3.
1H-NMR(DMSO-d6, ppm) 5 2.30 (6H, s) , 3.61 (3H, s) , 5.03 (2H, s) , 7.47 (2H, s), 7.92 (1H, d, J=7.6Hz), 7.98 (1H, d, J=7.6Hz), 8.08 (1H, t, J=7.6Hz), 10.18 (1H, s)
Example 6
(6-1) Production of ethyl 3-(2,2,2-trichloroethoxycarbonylarrd.no) benzoate
To a solution prepared by adding 1.0 g of ethyl m-aminobenzoate and 0.72 g of pyridine to 10 ml of tetrahydrofuran and stirring the resultant mixture at room temperature was dropwise added a solution of 1.55 g of 2,2,2-trichloroethyl chloroformate in 5 ml of tetrahydrofuran. After the resultant mixture was stirred for 2 hours, ethyl acetate and water were

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added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was washed with hexane to obtain 1.89 g (yield 91%) of the title compound. H-I-NMR (CDC13, ppm) 6 1.40 (3H, t, J=7.3Hz), 4.38 (2H, q, J=7.3Hz), 4.84 (2H, s), 6.96 (1H, broad-s), 7.43 (1H, t, J=7.8Hz), 7.76-7.82 (2H, m), 7.99 (1H, t, J=2.0Hz)
(6-2) Production of ethyl 3-[N-methyl-N-(2, 2, 2-trichloroethoxycarbonyl)amino]benzoate
To a suspension of 0.14 g of 60% sodium hydride in 5 ml of tetrahydrofuran was dropwise added a'solution of 1.0 g of ethyl 3-(2, 2, 2-trichloroethoxycarbonylamino)benzoate in 5 ml of tetrahydrofuran, and the resultant mixture was stirred at room temperature. Then, a solution of 0.45 g of dimethyl sulfate in 5 ml of tetrahydrofuran was dropwise added, and the resultant mixture was stirred at room temperature for 3 hours. After water was added to the mixture, the mixture was subjected to extraction with ethyl acetate, and an organic layer was washed twice with water and dried with anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane : ethyl acetate =4:1) to obtain 0.84 g (yield 79%) of the title compound as an oily material. 1H-NMR (CDCI3, ppm) 5 1.40 (3H, t, J=7.1Hz), 3.41 (3H, s) , 4.39 (2H,

230
q, J=7.1Hz), 4.77 (2H,s), 7.43-7.52 (2H, m) , 7.93-8.01 (2H, m)
(6-3) Production of 3-[N-methyl-N-(2, 2,2-trichloroethoxycarbonyl)amino]benzoic acid
To 5 ml of ethanol were added 0.5 g of ethyl 3-[N-methyl-N-
(2,2,2-trichloroethoxycarbonyl)amino]benzoate and a IN sodium hydroxide aqueous solution, and the resultant mixture was stirred at room temperature for 1.5 hours. After the reaction solution was controlled to pH 3 by dropwise adding IN hydrochloric acid, ethyl acetate was added to the reaction solution, and an organic layer was separated. The organic layer was washed with water twice and washed with a saturated saline solution once, and then dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 0.45 g (yield 98%) of the title compound as a solid.
XH-NMR (CDC13, ppm) 5 3.43 (3H, s) , 4.79 (2H, s) , 7.41-7.60 (2H, m) , 7.93-8.05 (2H, m)
(6-4) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-[N'-methyl-N'-(2,2,2-trichloroethoxycarbonyl)amino]benzamide
(Compound No. 1958)
A solution of 0.30 g of 3-[N-methyl-N-(2,2,2-trichloroethoxycarbonyl)amino]benzoic acid and 0.07 g of N-methylmorpholine in 5 ml of tetrahydrofuran was stirred under cooling at -15°C. A solution of 0.09 g of isopropyl chloroformate in 5 ml of tetrahydrofuran was dropwise added to the solution, and then a solution of 0.20 g of 2,6-dimethyl-4-

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heptafluoroisopropylaniline in 5 ml of tetrahyclrofuran was dropwise added to the resultant mixture. Then, the resultant mixture was stirred at -15°C for 1 hour and. at room temperature for 24 hours. After the temperature was returned to room temperature, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was washed with water twice and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane : ethyl acetate = 4:1 to 2:1) to obtain'0.05 g (yield 5%) of the title compound as an oily material. ^-NMR (CDC13, ppm) 8 2.34 (6H, s) , 3.45 (3H, s) , 4.80 (2H, s) , 7.36 (2H, s), 7.50-7.56 (3H, m), 7.78 (1H, d, J=6.1Hz), 7.90(1H, s)
Example 7
(7-1) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
2-iodo-5-aminobenzamide
To a solution prepared by adding 0.70 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide produced in Example 1-2 to 8 ml of N,N-dimethylformamide and then stirring the resultant mixture in an iced water bath was dropwise added a solution of 0.39 g of N-iodosuccinimide in 2 ml of N,N-dimethylformamide. After the dropwise addition, the temperature was returned to room temperature, and then mixture was further stirred for 3 hours. Then, ethyl acetate and water were added to the reaction solution, and a separating operation was performed.

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Then, an organic layer was separated and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane : ethyl acetate =3:2) to obtain 0.67 g (yield 73%) of the title compound as a solid. ^-NMR (CDC13, ppm) 8 2.44 (6H, s), 3.86 (2H, broad-s), 6.52 (1H, dd, J=2.9Hz, 8.5Hz), 6.91 (1H, d, J=2.9Hz), 7.12 (1H, s), 7.35 (2H, s), 7.62 (1H, d, J=8.5Hz)
(7-2) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 2-iodo-5-'(isopropyloxycarbonylamino) benzamide (Compound No. 1945)
To a'solution obtained by adding 0.20 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 2-iodo-5-aminobenzamide and 0.06 g of pyridine to 5 ml of tetrahydrofuran and then stirring the mixture at room temperature was dropwise added a solution of 0.05 g of isopropyl chloroformate in 1 ml of tetrahydrofuran. After reaction for 2 hours, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane : ethyl acetate =4:1) to obtain 0.22 g (yield 96%) of the title compound as a solid.
^-NMR (CDCI3, ppm) 5 1.31 (6H, d, J=6.3Hz), 2.45 (6H, s), 5.03 (1H, septet, J=6.3Hz), 6.66 (1H, s), 7.16-7.21 (2H, m), 7.36 (2H, s), 7.76 (1H, s), 7.82 (1H, dd, J=2.7Hz, 8.8Hz)

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Example 8
(8-1) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl
2-chloro-3-nitrobenzamide
First, to a solution prepared by adding 2.50 g of 2-chloro-3-
nitrobenzoic acid and 5 droplets of N,N-dimethylformamide to 30 ml
of toluene was added 1.62 g of thionyl chloride, and the resultant mixture was stirred under heating at 80°C for 2 hours. Then, the
solvent was distilled off under reduced pressure, and the residue was dissolved in 10 ml of tetrahydrofuran. The resultant solution was dropwise added to a solution of 3.24 g of 2,6-dimethyl-4-heptafluoroisopropylaniline and 1.77 g of pyridine in 20 ml of tetrahydrofuran at room temperature, and the mixture was stirred for 5 hours. Then, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane : ethyl acetate =4:1) to obtain 3.38 g (yield 64%) of the title compound as a solid. ^-NMR (CDC13, ppm) 5 2.42 (6H, s) , 7.34 (1H, s) , 7.37 (1H, s) , 7.55 (1H, t, J=7.8Hz), 7.80 (1H, dd, J=1.5Hz, 7.8Hz), 7.86 (1H, dd, J=1.5Hz, 7.8Hz), 9.58 (lH,s)
(8-2) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 2-fluoro~3-nitrobenzamide

234
To 25 ml of N/N-dimethylforrnamide dried with molecular sieve -were added 2.35 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 2-chloro-3-nitrobenzamide and 0.87 g of potassium fluoride (spray-dried) , and the resultant mixture was stirred under heating at 150°C for 3 hours. After the temperature was returned to room temperature, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated, washed with water twice, and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane : ethyl acetate =4:1) to obtain 1.02 g (yield 45%) of the title-compound as a solid.
XH-NMR (CDC13, ppm) 8 2.37 (6H, s) , 7.39 (2H, s) , 7.48-7.53 (1H, m) , 7.87 (1H, d, J=11.5Hz), 8.23-8.28 (1H, m), 8.42-8.46 (1H, m)
(8-3) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 2-fluoro-3-aminobenzamide
The title compound was produced by using N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 2-fluoro-3-nitrobenzamide produced in Example 8-2 as a starting material according to the same process as in Example 1-2 (yield 72%).
2H-NMR (CDCI3, ppm) 5 2.37 (6H, s), 3.90 (2H, broad-s), 6.96-7.01 (1H, m), 7.10 (1H, t, J=7.8Hz), 7.36 (2H, s), 7.43-7.47 (1H, m), 7.86 (1H, d, J=13.2Hz)

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(8-4) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 2-fluoro-3-(isopropyloxycarbonylamino)benzamide (Compound No.
1389)
The title compound was produced by using N-(2,6-dimethyl-4-
heptafluoroisopropyl)phenyl 2—fluoro-3-aminobenzamide produced in
Example 8-3 as a starting material according to the same process
as in Example 7-2 (yield 72%).
XH-NMR (CDC13, ppm) 5 1.34 (6H, d, J=6.3Hz), 2.36 (6H,s), 5.07 (1H,
septet, J=6.3Hz), 6.86 (1H, broad-s), 7.30 (1H, t, J=8.1Hz), 7.37
(2H, s), 7.72-7.79 (2H, m), 8.32 (1H, broad)
Example 9
(9-1) Production of 3-[ (2,2,2-trichloroethoxy)carbonylamino]benzoic acid
To an aqueous solution (200 ml) of 8.22 g of m-aminobenzoic acid and 4.8 g of sodium hydroxide was dropwise added 25.0 g of 2,2,2-trichloroethyl chloroformate at room temperature. During the dropwise addition, the reaction solution was controlled to pH 10 or more by appropriately adding a IN sodium hydroxide aqueous solution. After the reaction, the solution was controlled to pH 1 by adding IN hydrochloric acid, and the precipitates were collected by filtration. The resultant crude crystals were dried and then washed with a ethyl acetate/n-hexane mixed solvent to obtain 16.2 g (yield 87%) of the title compound as a solid. XH-NMR (DMSO-d6, ppm) 5 4.85 (2H, s) , 7.38 (1H, d, J=7.8Hz), 7.75 (1H, d, J=7.8Hz), 7.79-7.80 (1H, m) , 8.14 (1H, s) , 9.02 (1H, s)

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(9-2) Production of 3-[(2,2,2-trichloroethoxy)carbonylamino]benzoyl chloride
To a toluene solution (10 ml) of 1.0 g of 3-[(2,2,2-trichloroethoxy)carbonylamino]benzoic acid produced in Example 9-1 was added 2 ml of thionyl chloride, and the resultant mixture was stirred at 100°C. The solvent was distilled off under reduced pressure, and the residue was dissolved in toluene. The solvent was again distilled off under reduced pressure to obtain 1.0 g (yield 95%) of the title compound as a solid.
^-NMR (CDC13, ppm) 5 4.86 (2H, s) , 7.00 (1H, broad-s), 7.51 (1H, t, J=7.8Hz), 7.84 (1H, d, J=7.8Hz), 7.88 (1H, d, J=7.8Hz), 8.16 (1H,
s>
(9-3) Production of N-(2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 3-[(2,2,2-trichloroethoxy)carbonylamino]benzamide (Compound No. 257) First, to a solution prepared by adding 0.34 g of 2,6-dimethyl-4-(nonafluoro-2-butyl)aniline and 0.09 g of pyridine to 5 ml of tetrahydrofuran and stirring the resultant mixture at room temperature was added 0.33 g of 3-[(2,2,2-
trichloroethoxy)carbonylamino]benzoyl chloride produced in Example 9-2. After reaction for 5 hours, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane : ethyl acetate =

237
4:1) to obtain 0.45 g (yield 71%) of the title compound as a solid. XH-NMR {CDC13, ppm) 6 2.34 (6H, s) , 4.85 (2H, s) , 7.10 (1H, s), 7.34 (2H, s), 7.47-7.51 (2H, m) , 7.63-7.67 (2H, m), 8.05 (1H, s)
The following compounds were produced according to the processes described in Examples 9-1 and 9-2. 3- (ethoxycarbonylami.no) benzoyl chloride 3-(isopropylpropyloxycarbonylamino)benzoyl chloride 3-[(cyclobutyloxy)carbonylamino]benzoyl chloride 3-[(cyclopentyloxy)carbonylamino]benzoyl chloride 3-[(3-cyanobenzyloxy)carbonylamino]benzoyl chloride 3-[(4-cyanobenzyloxy)carbonylamino]benzoyl chloride 3-[(2-cyanoethoxy)carbonylamino]benzoyl chloride 3-[(2-methylthioethoxy)carbonylamino]benzoyl chloride 3-f(2-ethylthioethoxy)carbonylamino]benzoyl chloride 3-[(2-ethylsulfinylethoxy)carbonylamino]benzoyl chloride 3-[(2-fluoroethoxy)carbonylamino]benzoyl chloride 3-[(2, 2-difluoroethoxy)carbonylamino]benzoyl chloride 3-[(2,2, 2-trifluoroethoxy)carbonylamino]benzoyl chloride 3-[(1, 3-difluoro-2-propyloxy)carbonylamino]benzoyl chloride 3-[(l-chloro-3-fluoro-2-propyloxy)carbonylamino]benzoyl chloride 3-[(3, 3,3-trifluoro-n-propyloxy)carbonylamino]benzoyl chloride 3-[(2,2,3,3,3-pentafluoro-n-propyloxy)carbonylamino]benzoyl chloride
3-[(4, 4,4-trifluoro-n-butyloxy)carbonylamino]benzoyl chloride 3-[(2,2,3,3-tetrafluorocyclobutyloxy)carbonylamino]benzoyl chloride 3-[(2-chloroethoxy)carbonylamino]benzoyl chloride

238
3-[(2, 2-dichloroethoxy)carbonylamino]benzoyl chloride
3-[(1,3-dichloro-2-propyloxy)carbonylamino]benzoyl chloride
3-[(3-chloro-n-propyloxy)carbonylamino]benzoyl chloride
3- [ (2-bromoethoxy) carbonylamino] benzvoyl chloride
3-[(3-bromo-n-propyloxy)carbonylamino]benzoyl chloride
3-[(2-iodoethoxy)carbonylamino]benzoyl chloride
3-[(6-chloropyridine-3-yl)methoxycarbonylamino]benzoyl chloride
Example 10
(10-1) Production of N-(2,4-bistrifluoromethylphenyl) 3-
isocyanatobenzamide
To a 1,4-dioxane solution (20 ml) of 0.57 g of phosgene dimmer was added a 1,4-dioxane solution (5 ml) of 2.0 g of N-(2,4-bistrifluoromethylphenyl) 3-aminobenzamide (produced by using 2,4-bistrifluoromethylaniline as a starting material according to the process described in Example 1-2), and the resultant mixture was stirred at 60°C for 3 hours. Then, the solvent was distilled off under reduced pressure, and the residue was dissolved in 10 ml of 1,4-dioxane. Then, the solvent was again distilled off under reduced pressure. The product was washed with n-hexane and filtered off to obtain 1.54 g (yield 72%) of the title compound. XH-NMR (CDC13, ppm) 5 7.33-7.36 (1H, m) , 7.51 (1H, t, J=7.8Hz), 7.62-7.65 (2H, m) , 7.88-7.92 (2H, m), 8.31 (1H, broad-s), 8.70 (1H, d, J=8.8Hz)
(10-2) Production of N-(2,4-bistrifluoromethylphenyl) 3-[(2,2,3,3,3-pentafluoro-n-propyloxy)carbonylamino]benzamide

239
(Compound No. 250)
First, to an anhydrous tetrahydrofuran solution (15ml) of 0.5 g of N-(2,4-bistrifluoromethylphenyl) 3-isocyanatobenzamide produced in Example 10-1.were added 0.40 g of 2,2,3,3,3-pentafluoro-n-propanol and 0.13 g of triethylamine, and the resultant mixture was stirred at room temperature for 5 hours. The mixture was diluted with ethyl acetate (20 ml), and an organic layer was washed with a IN sodium hydroxide aqueous solution and IN hydrochloric acid. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane : ethyl acetate =4:1) to obtain 0.49 g (yield 70%) of the title compound.
^-NMR (CDC13, ppm) 5 4.68 (2H, t, J=13.2Hz), 7.08 (1H, broad-s) , 7.50-7.59 (2H, m), 7.70 (1H, broad-s), 7.87-7.92 (2H, m) , 8.00 (1H, s), 8.39 (lH,s), 8.71 (1H, d, J=8.8Hz)
Example 11
(11-1) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(benzyloxycarbonyl)benzamide
A mixture of 3.24 g of benzyl alcohol and 2.85 g of pyridine was dropwise added to a tetrahydrofuran solution (60 ml) of 6.09 g of isophthaloyl chloride at room temperature. After the resultant mixture was stirred for 2 hours, a tetrahydrofuran solution (10 ml) of 2,6-dimethyl-4-heptafluoroisopropylaniline was added to the mixture in an ice bath, followed by stirring at room temperature for 2 hours. The reaction solution was diluted with ethyl acetate (50 ml), and an organic layer was washed with IN hydrochloric acid.

240
The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane : ethyl acetate =9:1) to obtain 9.5 g (yield 60%) of the title compound as an amorphous material.
^-NMR (CDC13, ppm) 5 2.33 (6H, s) , 5.41 (2H,s), 7.34-7.48 (7H,m), 7.56 (lH,s), 7.61 (1H, t, J=7.8Hz), 8.17 (1H, t, J=7.8Hz), 8.28 (1H, d, J=7.8Hz), 8.57 (1H, s)
(11-2) Production of 3-[(2,6-dimethyl-4-heptafluoroisopropylphenyl)aminocarbonyl]benzoic acid
Catalytic hydrogen reduction was performed at normal pressure by using a methanol solution (20 ml) of 2.0 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(benzyloxycarbonyl)benzamide produced in Example 11-1 and 0.2 g of 10% palladium-carbon (wet, 50% product) to produce 1.59 g (yield 96%) of the title compound as a solid.
^-NMR (CDCI3, ppm) 8 2.36 (6H,s), 7.37 (2H,s), 7.59 (lH,s), 7.67 (1H, t, J=7.8Hz), 8.23 (1H, d, J=7.8Hz), 8.32 (1H, d, J=7.8Hz), 8.62 (1H, s)
(11-3) Production of N-(2,6-dimethyl-4-
heptafluoroisopropylphenyl) 3-isocyanatobenzamide \3 /
First, to an acetone solution (25 ml) of 1.4 g of -[(2,6- <==
dimethyl-4-heptafluoroisopropylphenyl)aminocarbonyl]benzoic acid produced in Example 11-2 and 0.38 g of triethylamine was added 0.44 g of ethyl chloroformate in an iced water bath, and the resultant mixture was stirred at room temperature for 1 hour.

241
Then, an aqueous solution (10 ml) of 0.32 g of sodium azide was added to the mixture, followed by stirring at room temperature for 2 hours. The reaction solution was poured into iced water (150 ml), and the precipitates were extracted with ethyl acetate (50 ml) and then dried with anhydrous magnesium sulfate. After anhydrous magnesium sulfate was filtered off, toluene (50 ml) was added to the filtrate, and the low-boiling-point solvent was distilled off by heating to 110°C using a Dean and Stark tube. After the end of gas generation was confirmed, the temperature was returned to room temperature, and then the residual solvent was distilled off under reduced pressure to obtain 1.23 g (yield 88%) of the title compound as a solid.
XH-NMR (CDC13, ppm) 8 2.35 (6H, s), 7.32 (1H, d, J=7.8Hz), 7.37 (2H,s), 7.39 (lH,s), 7.49 (1H, t, J=7.8Hz), 7.67 (lH,s), 7.72 (1H, d, J=7.8Hz)
(11-4) Production of N-(2,6-dimethyl-4-
heptafluoroisopropylphenyl) 3-[(l-chloro-3-trifluoromethyl-2-propyl)oxycarbonylamino]benzamide (Compound No. 120)
The title compound was produced by using N-(2,6-dimethyl-4-heptafluoroisopropylphenyl) 3-isocyanatobenzamide produced in Example 11-3 according to the process described in Example 10-2. ^-NMR (CDCI3, ppm) 5 2.35 (6H, s) , 3.75-3.83 (2H, m) , 4.46-4.80 (2H, m), 5.19-5.24 (lH,m), 6.97 (1H, broad~s), 7.36 (2H, s), 7.36-7.48 (2H, m), 7.60-7.66 (2H, m), 8.03 (1H, s)
The following compounds were produced according to the processes described in Examples 10 and 11.

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N-2, 6-dimethyl-4-(nonafluoro-2-butyl)phenyl 3-isocyanatobenzamide
N-2, 6-dinaethyl-4- [ (heptafluoro-n-propyl) thio]phenyl 3-
isocyanatobenzamide
N-2,6-dibromo-4-[(heptafluoro-n-propyl)thio]phenyl 3-
isocyanatobenzamide
N-2,6-dichloro-4-[(heptafluoro-n-propyl)thio]phenyl 3-
isocyanatobenzamide
N-2, 6-dimethyl-4-[(heptafluoroisopropyl)thio]phenyl 3-
isocyanatobenzamide
N-2,6-dibromo-4-[(heptafluoroisopropyl)thio]phenyl 3-
isocyanatobenzamide
N-2,6-dichloro-4-[(heptafluoroisopropyl)thio]phenyl 3-
isocyanatobenzamide
N-2,6-dimethyl-4-[(nonafluoro-2-butyl)thio]phenyl 3-
isocyanatobenzamide
N-2, 6-dibromo-4-[(nonafluoro-2-butyl)thio]phenyl 3-
isocyanatobenzamide
N-2,6-dichloro-4-[(nonafluoro-2-butyl)thio]phenyl 3-
isocyanatobenzamide
N-2, 6-dimethyl-4-[(heptafluoro-n-propyl)sulfinyl]phenyl 3-
isocyanatobenzamide
N-2,6-dibromo-4-[(heptafluoro-n-propyl)sulfinyl]phenyl 3-
isocyanatobenzamide
N-2,6-dichloro-4-[(heptafluoro-n-propyl)sulfinyl]phenyl 3-
isocyanatobenzamide
N-2,6-dimethyl-4-[(heptafluoro-n-propyl)sulfonyl]phenyl 3-
isocyanatobenzamide

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N-2,6-dibromo-4-[(heptafluoro-n-propyl)sulfonyl]phenyl 3-
isocyanatobenzamide
N-2,6-dichloro-4-[(heptafluoro-n-propyl)sulfonyl]phenyl 3-
isocyanatobenzamide
Example 12
(12-1) Production of 4-(heptafluoro-n-propylthio)aniline
To an acetonitrile solution (20 ml) of 4-aminothiophenol
(1.25 g, 9.98 mmol) and triethylamine (1.11 g, 11.0 mmol) was added 1-iodoheptafluoro-n-propane (5.91 g, 19.9 mmol), and the resultant mixture was stirred at room temperature for 3 hours. The mixture was diluted with ether, and washed with a IN sodium hydroxide aqueous solution. Then, the product was purified by silica gel column chromatography (eluent; hexane : ethyl acetate = 4:1) to obtain 1.85 g (yield 63%) of the title compound. ;H-NMR (CDC13, ppm) 5 3..95 (2H, s) , 6.66 (2H, d, J=8.8Hz), 7.40 (2H, d, J=8.8Hz)
(12-2) Production of 2,6-dibromo-4-(heptafluoro-n-propyl thio)aniline
First, to a solution of 0.77 g of 4-(heptafluoro-n-propylthio)aniline produced in Example 12-1 in 15 ml of N,N-dimethylformamide was added 0.98 g of N-bromosuccinimide. After the resultant mixture was stirred at 60°C for 2 hours, ether and water were added to the mixture. Then, an organic layer was separated, washed with water twice and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced

244
pressure. The residue was purified by silica gel column chromatography (eluent; hexane : ethyl acetate =9:1) to obtain 1.19 g (yield 100%) of the title compound as a red oily material. ^-NMR (CDC13, ppm) 5 4.98 (2H, broad-s), 7.66 (2H, s)
(12-3) Production of N-{2,6-dibromo-4-(heptafluoro-n-
propylthio)}phenyl 3-nitrobenzamide
To a solution prepared by adding 1.08 g of 2, 6-dibromo-4-
(heptafluoro-n-propylthio)aniline produced in Example 12-2 and 0.4 g of pyridine to 20 ml of tetrahydrofuran and stirring the resultant mixture at room temperature was dropwise added a solution of 0.55 g of 3-nitrobenzoyl chloride in 20 ml of tetrahydrofuran. After the resultant mixture was stirred at room temperature for 10 hours, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane : ethyl acetate = 4:1) to obtain 0.86 g (yield 48%) of the title compound as a white solid.
XH-NMR (CDCI3, ppm) 5 7.73 (1H, s, J=7.8Hz, 7.77 (1H, t, J=7.8Hz), 7.96 (2H, s), 8.31 (1H, s), 8.47-8.50 (1H, ra), 8.79 (1H, t, J=2". 0Hz)
(12-4) Production of N-{2,6-dibromo-4-(heptafluoro-n-

245
propylthio)}phenyl 3-aminobenzamide
To a solution prepared by adding 0.97 g of N-{2,6-dibromo-4-
(heptafluoro-n-propylthio)Iphenyl 3-nitrobenzamide produced in Example 12-3 and 0.95 g of tin(II) chloride (anhydrous) to 20 ml of ethanol and stirring the resultant mixture at room temperature was added 2 ml of cone, hydrochloric acid, and the resultant mixture was stirred under heating at 60°C for 1 hour. After the temperature was returned to room temperature, the reaction solution was poured into water, and the solution was neutralized with potassium carbonate. Then, ethyl acetate was added to the solution, and insoluble materials were filtered off. Then, an organic layer was separated and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was washed with hexane to obtain 0.75 g (yield 81%) of the title compound as a white solid. 1H-NMR (CDC13, ppm) 5 3.89 (2H, broad-s), 6.90 (1H, dt, J=2.5Hz, 6.4Hz), 7.28-7.30 (3H, m), 7.60 (1H, s) , 7.93 (2H, s)
(12-5) Production of N-{2,6-dibromo-4-(heptafluoro-n-propylthio) }phenyl 3-(2,2,2-trichloroethoxycarbonylamino)benzamide
(Compound No. 612)
To a solution prepared by adding 0.10 g of N-{2,6-dibromo-4-
(heptafluoro-n-propylthio)Iphenyl 3-aminobenzamide and 0.02 g of pyridine to 5 ml of tetrahydrofuran and stirring the resultant mixture at room temperature was dropwise added a solution of 0.04 g of 2,2,2-trichloroethyl chloroformate in 1 ml of tetrahydrofuran.

246
After reaction for 2 hours, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane : ethyl acetate = 4:1) to obtain 0.11 g (yield 84%) of the title compound as a solid. ^H-NMR (CDC13, ppm) 5 4.86 (2H, s), 7.45 (1H, t, J=7.8Hz), 7.72 (1H, d, J=7.8Hz), 7.93 (2H, s), 7.94 (1H, broad-s), 8.13 (1H, s) , 9.02 (1H, s), 9.17 (1H, s)
(12-6) Production of N-{2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)}phenyl 3-nitrobenzamide and N-{2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)Jphenyl 3-nitrobenzamide
A solution prepared by adding 0.5 g of N-{2,6-dibromo-4-(heptafluoro-n-propylthio)}phenyl 3-nitrobenzamide to 15 ml of chloroform was stirred at room temperature, and 0.5 g of m-chloroperbenzoic acid was added to the mixture. After the resultant mixture was stirred at room temperature for 1 week, an aqueous solution of sodium hydrogen sulfite was added to the mixture, followed by stirring. Then, an organic layer was separated and washed with a IN sodium hydroxide aqueous solution and saturated saline water. Then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane : ethyl acetate =4:1) to obtain 0.21 g of N-({2, 6-dibromo-4-(heptafluoro-n-

247
propylsulfinyl)}phenyl 3-nitrobenzamide and 0.12 g of N-{2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)}phenyl 3-nitrobenzamide as solids.
(sulfinyl compound) XH-NMR (CDC13, ppm) 5 7.76-7.82 (2H, m) , 8.06 (1H, s), 8.29 (1H, s), 8.33-8.35 (1H, m) , 8.49-8.53 (1H, m), 8.81 (1H, s)
(12-7) Production of 2, 6-dimethyl-4-(heptafluoro-n-propylthio)aniline
To 20 ml of DMF were added 3.0 g (1.3 mmol) of 2,6-dibromo-4-heptafluoro-n-propylthioaniline, 3.0 g (21.9 mmol) of potassium carbonate, 0.75 g (0.65 mmol) of tetrakis(triphenylphosphine) palladium, and 0.17 g (1.3 mmol) of trimethylboroxine, and the resultant mixture was stirred at 135°C for 6 hours. After the reaction solution was cooled to room temperature, insoluble materials were filtered off with cerite. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; n-hexane : ethyl acetate = 12:1 to 4:1) to obtain 1.17 g (yield 55%) of the title compound as an oily material.
Hi-NMR (CDCI3, ppm) 5 2.17 (6H,s), 3.86 (2H, broad-s), 7.22 (2H, s) The following aniline derivatives can be produced according
to the processes described in Examples 12-1, 12-2, 12-6, and 12-7.
2-methyl-4-(pentafluoroethylthio)aniline
2-methyl-4-(heptafluoro-n-propylthio)aniline
XH-NMR (CDCI3, ppm) 8 2.16 (3H, s), 3.90 (2H, broad-s), 6.65 (1H, d,
J=8.3Hz), 7.28-7.31 (2H, m)

248
2-bromo-4-(heptafluoro-n-propylthio)aniline
XH-NMR (CDCI3, ppm) 5 4.44 (2H, broad-s), 6.75 (1H, d, J=8.8Hz),
7.36 (1H, dd, J=2.0Hz, 8.8Hz), 7.69 (1H, d, J=2.0Hz)
2-methyl-4-(heptafluoroisopropylthio)aniline
2-methyl-4-(nonafluoro-n-butylthio)aniline
2-methyl-4-(pentafluoroethylsulfinyl)aniline
2-methyl-4-(heptafluoro-n-propylsulfinyl)aniline
2-methyl-4-(heptafluoroisopropylsulfinyl)aniline
2-methyl-4-(nonafluoro-n-butylsulfinyl)aniline
2-methyl-4-(pentafluoroethylsulfonyl)aniline
2-methyl-4-(heptafluoro-n-propylsulfonyl)aniline
2-methyl-4-(heptafluoroisopropylsulfonyl)aniline
2-methyl-4-(nonafluoro-n-butylsulfonyl)aniline
2,6-dichloro-4-(pentafluoroethylthio)aniline
2,6-dibromo-4-(pentafluoroethylthio)aniline
N-{2,6-dibromo-4-(pentafluoroethylthio)}phenyl 3-nitrobenzamide
XH-NMR (CDCI3, ppm) 5 7.73 (lH,s), 7.77 (1H, t, J=7.8Hz), 7.96 (2H,
s), 8.32 (1H, d, J=7.8Hz), 8.47-8.50 (1H, m) , 8.80 (1H, t,
J=2.0Hz)
2,6-dimethyl-4- (pentafluoroethylthio)aniline
2,6-dichloro-4-(heptafluoro-n-propylthio)aniline
XH-NMR (CDCI3, ppm) 5 4.82 (2H, broad-s), 7.48 (2H, s)
N-{2,6-dichloro-4-(heptafluoro-n-propylthio)}phenyl 3-
nitrobenzamide
^-NMR (CDCI3, ppm) 5 7.70 (1H, s) , 7.76 (2H, s) , 7.77 (1H, t,
J=7.8Hz), 8.31 (1H, d, J=7.8Hz), 8.48 (IK, d, J=7.8Hz), 8.78 (1H,
t, J=2.0Hz)

249
2,6-dibromo-4-(heptafluoro-n-propylthio)aniline
Hi-NMR (CDCI3, ppm) 5 4.93 (2H, broad-s) , 7.66 (2H, s)
2, 6-dimethyl-4-(heptafluoro-n-propylthio)aniline
XH-NMR (CDCI3, ppm) 5 2.17 (6H, s) , 3.86 (2H, broad-s), 7.22 (2H,
s)
N-{2,6-dichloro-4-(heptafluoro-n-propylthio)}phenyl 2-chloro-3-
nitrobenzamide
^-NMR (CDC13, ppm) 5 2.39 (6H, s) , 7.30 (1H, s) , 7.46 (2H, s) ,
7.57 (1H, t, J=7.8Hz), 7.90 (1H, d, J=7.8Hz), 7.91 (1H, d,
J=7.8Hz)
2-bromo-4-(heptafluoro-n-propyl)thio-6-methylaniline
1H-NMR (CDCI3, ppm) 5 2.22 (3H, s) , 4.40 (2H, broad-s), 7.27 (1H,
s), 7.60 (1H, d, J=2.0Hz)
2,6-dichloro-4-(heptafluoroisopropylthio)aniline
2H-NMR (CDCI3, ppm) 5 6.40 (2H, s) , 7.52 (2H, s)
2,6-dibromo-4-(heptafluoroisopropylthio)aniline
N-{2,6-dichloro-4-(heptafluoroisopropylthio)}phenyl 3-
nitrobenzamide
XH-NMR (CDCI3, ppm) 5 7.73 (1H, s) , 7.76 (1H, t, J=7.8Hz), 7.95 (2H,
s), 8.31 (1H, d, J=7.8Hz), 8.48 (1H, d, J=7.8Hz), 8.79 (1H, t,
J=1.5Hz)
2,6-dimethyl-4-(heptafluoroisopropylthio)aniline
2, 6-dichloro-4-(nonafluoro-n-butylthio)aniline
2,6-dibromo-4-(nonafluoro-n-butylthio)aniline
N-{2,6-dichloro-4-(nonafluoro-n-butylthio)Iphenyl 3-nitrobenzamide
XH-NMR (CDC13/ ppm) 5 7.76 (lH,s), 7.77 (1H, t, J=8.3Hz), 7.96 (2H,
s), 8.32 (1H, d, J=8.3Hz), 8.48 (1H, d, J=8.3Hz), 8.80 (1H, t,

250
J=2.0Hz)
2, 6-dimethyl-4-(nonafluoro-n-butylthio)aniline
2,6-dichloro-4-(pentafluoroethylsulfinyl)aniline
2, 6-dibromo-4~(pentafluoroethylsulfinyl)aniline
2,6-dimethyl-4-(pentafluoroethylsulfinyl)aniline
2, 6-dichloro-4-(heptafluoro-n-propylsulfinyl)aniline
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)aniline
N-{2,6-dichloro-4-(heptafluoro-n-propylsulfinyl)}phenyl 3-
nitrobenzamide
1H-NMR (CDC13, ppm) 6 7.76-7.82 (2H, m) , 8.06 (1H, s) , 8.29 (1H, s) ,
8.33-8.35 (1H, m) , 8.49-8.53 (1H, m), 8.81(1H, s)
2,6-dimethyl-4-(heptafluoro-n-propylsulfinyl)aniline
2, 6-dichloro-4-(heptafluoroisopropylsulfinyl)aniline
2, 6-dibromo-4-(heptafluoroisopropylsulfinyl)aniline
2, 6-dimethyl-4-(heptafluoroisopropylsulfinyl)aniline
2, 6-dichloro-4-(nonafluoro-n-butylsulfinyl)aniline
2,6-dibromo-4-(nonafluoro-n-butylsulfinyl)aniline
2,6-dimethyl-4-(nonafluoro-n-butylsulfinyl)aniline
2,6-dichloro-4-(pentafluoroethylsulfonyl)aniline
2,6-dibromo-4-(pentafluoroethylsulfonyl)aniline
2, 6-dimethyl-4-(pentafluoroethylsulfonyl)aniline
2, 6-dichloro-4-(heptafluoro-n-propylsulfonyl)aniline
2, 6-dibromo-4-(heptafluoro-n-propylsulfonyl)aniline
2,6-dimethyl-4-(heptafluoro-n-propylsulfonyl)aniline
2,6-dichloro-4-(heptafluoroisopropylsulfonyl)aniline
N-{2,6-dichloro-4-(heptafluoroisopropylsulfonyl)}phenyl 3-
nitrobenzamide

251
2H-NMR (CDCI3, ppm) 5 7.79 (1H, t, J=7.8Hz), 7.98 (1H, s), 8.07 ' (2H,
s), 8.33 (1H, d, J=7.8Hz)/ 8.51 (1H, d, J=7.8Hz), 8.81 (1H, t,
J=2.0Hz)
2,6-dibromo-4-(heptafluoroisopropylsulfonyl)aniline
2,6-dimethyl-4-(heptafluoroisopropylsulfonyl)aniline
2,6-dichloro-4-(nonafluoro-n-butylsulfonyl)aniline
2,6-dibromo-4-(nonafluoro-n-butylsulfonyl)aniline
2,6-dimethyl-4-(nonafluoro-n-butylsulfonyl)aniline
Example 13
(13-1) Production of 2,6-dimethyl-4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl)aniline
A mixture of 2.42 g of 2, 6-dimethylaniline, 7.35 g of hexafluoroacetone hydrate, and 0.04 g of p-toluenesulfonic acid monohydrate was stirred under heating at 100°C for 5 hours. After the temperature was returned to room temperature, the mixture was diluted with ethyl acetate and washed with a IN sodium hydroxide aqueous solution. Then, the solvent was distilled off under reduced pressure, and the precipitated crude crystals were washed with a n-hexane-ethyl acetate mixed solvent to obtain 4.47 g (yield 78%) of the title compound as a solid.
^-NMR (CDCI3, ppm) 5 2.20 (6H, s), 3.26 (1H, broad-s) , 3.76 (2H, broad-s), 7.25 (2H, s)
(13-2) Production of N-[2,6-dimethyl-4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl)]phenyl 3-(2,2,2-trichloroethoxycarbonylamino)benzamide (Compound No. 872)

252
The title compound was produced as an amorphous material by using 2,6-dimethyl-4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl)aniline produced in Example 13-1 as a starting material according to the process described in Example 9-3 (yield 92%). LH-NMR (CDC13, ppm) 5 2.31 (6H, s) , 3.99 (1H, s) , 4.85 (2H, s) , 7.15 (1H, broad-s), 7.45-7.51 (4H, m), 7.64-7.66 (2H, m), 8.01 (1H, s)
Formulation examples containing the compounds represented by formula (1) of the present invention as active ingredients are shown below, however the present invention is not limited to these examples. In each of the formulation examples, "part(s)" represents "part(s) by weight".
Formulation Example 1
A mixture of 20 parts of a compound represented by formula
(1) of the present invention, 10 parts of Sorpol 355S (surfactant produced by Toho CHemical Industry Co., Ltd.), and.70 parts of xylene was uniformly stirred to produce an emulsion.
Formulation Example 2
A mixture of 10 parts of a compound represented by formula
(1) of the present invention, 2 parts of sodium
alkylnaphthalenesulfonate, 1 part of sodium lignin-sulfonate, 5 parts of white carbon, and 82 parts of diatomite was uniformly stirred to produce a wettable powder.

253
Formulation Example 3
A mixture of 0.3 parts of a compound represented by formula
(1) of the present invention and 0.3 parts of white carbon was uniformly stirred, and 99.2 parts of clay and 0.2 parts of Driless A (produced by Sankyo Co., Ltd.) were added to the mixture. The resultant mixture was uniformly ground to produce a dust.
Formulation Example 4
A mixture of 2 parts of a compound represented by formula (1) of.the present invention, 2 parts of white carbon, 2 parts of sodium lignin-sulfonate, and 94 parts of bentonite was uniformly ground, and then water was added to the mixture. The resultant mixture was kneaded, granulated and then dried to produce granules.
Formulation Example 5
A mixture of 20 parts of a compound represented by formula
(1) of the present invention and 5 parts of a 20% aqueous solution of polyvinyl alcohol was sufficiently stirred, and then 75 parts of a 0.8% aqueous solution of xanthane gum was added to the mixture. Then, the resultant mixture was again stirred to produce a flowable agent.
Test examples for making clear that the compounds represented by formula (1) of the present invention have excellent insecticidal activity are shown below, however the present invention is not limited to these examples.
Test Example 1 Insecticidal test for common cutworm (Spodoptera

254
litura)
A cabbage leaf piece was immersed in a solution prepared by diluting a test compound to a predetermined concentration for 30 seconds, and then dried in air. Then, the cabbage leaf piece was placed in a polyethylene cup of 7 cm-size in which 2nd-instar larvae of common cutworm were placed. The cup was allowed to stand in a thermostatic chamber at 25°C. Three days after, the numbers of living and dead larvae were counted. The test was carried out in two replications each containing five larvae.
As a result, at a concentration of 1000 ppm, a mortality of
70% or more was exhibited by Compounds Nos. 20, 59, 60, 62, 64, 66,
75, 78, 79, 81, 83, 84, 85, 90, 91, 92, 106, 108, 109, 111, 112,
116, 117, 118, 119, 120, 121, 123, 124, 125, 126, 127, 130, 131,
132, 134, 135, 136, 137, 138, 139, 140, 155, 156, 161, 163, 165,
174, 175, 176, 180, 181, 184, 186, 189, 190, 192, 196, 197, 198,
205, 206, 207, 208, 209, 210, 212, 213, 215, 216, 217, 218, 219,
220, 221, 224, 225, 228, 229, 230, 231, 232, 233, 234, 235, 236,
237, 241, 246, 247, 248, 250, 251, 252, 253, 254, 255, 256, 257,
258, 259, 300, 301, 348, 377, 424, 464, 471, 511, 518, 565, 605,
612, 659, 706, 770, 800, 817, 818, 819, 854, 855, 856, 857, 843,
844, 846, 847, 864, 867, 872, 873, 878, 890, 891, 892, 898, 899,
900, 902, 903, 905, 913, 915, 916, 919, 920, 922, 932, 933, 944,
948, 992, 1010, 1039, 1086, 1104, 1180, 1198, 1227, 1245, 1274,
1292, 1321, 1361, 1368, 1388, 1389, 1408, 1411, 1416, 1418, 1421,
1435, 1455, 1458, 1463, 1465, 1903, 1906, 1907, 1922, 1923, 1924,
1925, 1926, 1929, 1931, 1932, 1935, 1939, 1941, 1942, 1943, 1944,
1945, 1947, 1948, 1950, 1951, 1952, 1953, 1954, 1955, 1956, 1958,

255
1959, 1963, 1964, 1967, 1963, 1969, 2061, 2062, 2164, 2165, and 2168.
Test Example 2 Insecticidal test for diamondback moth (Plutella xylostella)
A cabbage leaf pieces was immersed in a solution prepared by diluting a test compound to a predetermined concentration for 30 seconds, and then dried in air. Then, the leaf piece was placed in a polyethylene cup of 7 cm-size in which 2nd-instar larvae of common cutworm were placed. The cup was allowed to stand in a thermostatic chamber at 25°C. Three days after, the numbers of living and dead larvae were counted. The test was carried out in two replications each containing five larvae.
As a result, at a concentration of 1000 ppm, a mortality of 70% or more was exhibited by Compounds Nos. 3, 5, 7, 8, 20, 59, 60, 62, 66, 75, 77, 78, 79, 80, 84, 85, 92, 94, 95, 96, 99, 101, 103, 104, 106, 108, 109, 110, 111, 112, 113, 116, 117, 118, 119, 120, 121, 123, 126, 127, 130, 131, 132, 134, 136, 137, 138, 139, 140, 141, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 168, 171, 174, 175, 176, 180, 181, 183, 184, 186, 190, 192, 196, 197, 198, 201, 203, 204, 205, 206, 207, 208, 209, 212, 213, 214, 215, 217, 218, 219, 220, 221, 223, 224, 228, 229, 230, 231, 232, 233, 234, 235, 236, 237, 238, 246, 247, 248, 249, 250, 252, 253, 254, 255, 256, 257, 258, 259, 300, 301, 348, 377, 424, 464, 471, 511, 518, 565, 605, 612, 659, 706, 800, 817, 818, 819, 820, 829, 858, 863, 865, 867, 868, 871, 872, 873, 878, 896, 897, 898, 899, 900, 902, 908, 913, 915, 919, 920, 922, 930, 932, 933, 936, 939, 941, 942,

256
943, 944, 945, 947, 948, 992, 1010, 1039, 1086, 1104, 1180, 1227,
1245, 1274, 1292, 1321, 1361,' 1368, 1388, 1389, 1408, 1411, 1416,
1418, 1421, 1435, 1455, 1458, 1463, 1465, 1903, 1906, 1907, 1916,
1923, 1926, 1928, 1929, 1931, 1933, 1939, 1945, 1947, 1950, 1951,
1952, 1953, 1954, 1955, 1956, 1958, 1959, 1963, 1964, 1967, 1968,
1969, 2061, 2062, 2164, 2165, 2167, and 2168.
Test Example 3 Insecticidal test for small brown planthopper
(Laodelphax striatellus)
An acetone solution prepared by diluting a test compound to a predetermined concentration was sprayed on rice seedlings, and the rice seedlings were dried in air. Ten small brown planthoppers and an original chemical were used for the test. The rice seedlings were allowed to stand in a thermostatic chamber at 25°C. Six days after, the number of living insects was examined, and three days after, the number of dead insects was examined. The test was carried out one replication containing ten insects.
As a result, at a concentration of 1000 ppm, a mortality of 70% or more was exhibited by Compounds Nos. 108, 127, 184, 196, 197, 205, 209, 212, 215, 1321, 1361, 1368, 1408, 1411, 1416, 1435, 1455, 1458, 1463, 1958, 1959, and 1968.

WE CLAIM:
1. An aniline compound represented by formula (4):
A/^A (4)
wherein Ai, A2, A3, and A4 independently represent a carbon atom, a nitrogen atom, or an oxidized nitrogen atom; R2 and R3 independently represent a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group, or a C1-C4 haloalkylcarbonyl group; G3 represents an oxygen atom or a sulfur atom; Xs may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C4 alkylsulfinyl group, a C1-C4 haloalkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C1-C4 haloalkylsulfonyl group, a cyano group, a nitro group, or an amino group which may be substituted by a C1-C4 alkyl group; n represents an integer of 0 to 4; and Q is a substituent represented by formula (1-2) or (1-3):
(wherein Yi, Y2, Y4, and Y5 may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a pentafluorosulfanyl group, a cyano group, or a nitro group, and Y3 represents a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted

by at least one hydroxyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, a C1-C6 haloalkylsulfonyl group, or a pentafluorosulfanyl group, but excluding a case that both of Yi and Y5 represents]] a hydrogen atom);
Y9^N*N8
(wherein Y6, Y7, and Y9 may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a pentafluorosulfanyl group, a cyano group, or a nitro group, and Yg represents a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, a C1-C6 haloalkylsulfonyl group, or a pentafluorosulfanyl group, but excluding a case that both of Y6 and Y9 represent[[s]] a hydrogen atom).
Dated this on April 27,2012. fU^^V^ M^p^"
[DR. ANUSHRI GUPTA]
OF REMFRY & SAGAR
ATTORNEY FOR THE APPLICANT^]