Technical Field
[0001] The present invention relates to a novel isoxazoline-substituted benzamide compound and the salt thereof, and a pesticide characterized by containing the compound as an active ingredient. The pesticide in the present invention means a pest controlling agent applied for harmful arthropods in agricultural and horticultural field or livestock farming and hygienic field (endo-parasiticides and ecto-parasiticides for mammals or birds as domestic animals or pets, or hygienic pest- or unpleasant pest-controlling agents for domestic or business use). In addition, agricultural chemicals in the present invention mean insecticides, acaricides (miticides), nematicides, herbicides and fungicides, and the like.
Background Art
[0002] Conventionally, as to isoxazoline-substituted benzoic acid amide compounds, the followings are known: a report of synthesis by use of solid phase synthesis of 4-(5-methyl-5-substituted pyrrolyl-4,5-dihydroisoxazole-3-yl) benzoic acid amide derivatives (see, Non-patent Document 1); 4-(5-pyridyl-4,5-dihydroisoxazole-3-yl) benzoic acid amide derivatives have matrix metalloprotease and TNF-α inhibition activity, or the like, and can be used as an anti-inflammatory agent or a chondro-protective agent (see, Patent Document 1); 4-(5-substituted carbamoylmethyl-4,5-dihydroisoxazole-3-yl) benzoic acid amide derivatives, 3-(5-substituted carbamoylmethyl-5-substituted alkyl-4,5-dihydroisoxazole-3-yl) benzoic acid amide derivatives and 4-(5-substituted carbamoylmethyl-4,5-dthydroisoxazole-3-yl) benzamidine derivatives have platelet glycoprotein llb/llla fibrinogen receptor complex competitive activity or factor Xa inhibition activity or the like, and can be used as a thrombolysis agent or a therapeutic agent of thronbo-embolic disorder (see, for example Patent Documents 2-5), etc. In addition, it is known that other specific substituted isoxazoline compound can be used as a production intermediate of HIV protease inhibitors, or production intermediate of insecticides (see, for example Patent Documents 6 and 7). However, there is no disclosure on 4-(5-substituted-5-substituted aryl-
substituted aryl-
1
4,5-dihydroisoxazole-3-y[)benzoic acid amide compounds according to the present
invention, and further the usefulness thereof as a pesticide is not known at all.
[0003] On the other hand, as to 3-(4-substituted phenyl)-4,5-dihydroisoxazole
derivatives, 5-substituted alkyl-3,5-bis substituted phenyl-4,5-dihydroisoxazole
derivatives (see, Patent Document 7), 3-alkoxyphenyl-5-substituted-5-phenyl-4,5-
dihydroisoxazole derivatives (see, Patent Document 8), 3-alkoxyphenyl-5-
substituted alkyl-5-substituted carbamoyl-4,5-dihydroisoxazole derivatives (see,
Patent Document 9), 3-(4-halophenyl)-5-substituted-5-substituted phenyl-4,5-
dihydroisoxazole derivatives (see, Patent Documents 10 and Non-patent Document
2), and 3-(4-nitrophenyl)-5-substituted -5-substituted phenyl-4,5-dihydroisoxazole
derivatives (see, patent Document 11 and Non-patent Document 3), etc. are known.
However, 5-substituted alkyl-3,5-bis substituted phenyl-4,5-dihydroisoxazole
derivatives that can be used as a production intermediate of the pesticides according
to the present invention are not described in any documents and thus novel
compounds.
[0004] Further, as to 4-hydroxyiminomethyl benzoic acid amide derivatives, 4-
hydroxyiminomethyl-N,N-dimethyl benzoic acid amide (see, Non-patent Document
4), 4-hydroxyiminomethyl benzoyl piperidine derivatives (see, Patent Documents
and 13), 4-hydroxyiminomethyl-N-bicycloalkyl benzoic acid amide derivatives (see,
Patent Document 14), and 6-(hydroxyiminomethyl) pyridine-2-carboxamide
derivatives (see, Non-patent Document 5), etc. are known. However, 4-
hydroxyiminomethyl benzoic acid amide derivatives that can be used as a
production intermediate of the pesticides according to the present invention are not
described in any documents and thus novel compounds. [0005] In addition, as to
haloalkenylbenzene derivatives, substituted 3,3,3-trifluoro-2-propenylbenzene
derivatives (see, Non-patent Documents 6-8), etc. are known. However, specific
substituted haloalkenylbenzene derivatives that can
ibe used as a production intermediate of the pesticides according to the present
invention are not described in any documents and thus novel compounds.
Patent Document 1: WO 01/070673 Pamphlet
Patent Document 2: WO 96/038426 Pamphlet
Patent Document 3: WO 97/023212 Pamphlet
Patent Document 4: WO 95/014683 Pamphlet
Patent Document 5: WO 97/048395 Pamphlet
Patent Document 6: WO 99/014210 Pamphlet
Patent Document 7: WO 04/018410 Pamphiet
Patent Document 8: WO 95/024398 Pamphlet
Patent Document 9: WO 98/057937 Pamphlet
Patent Document 10: EP 0455052 A1 (1991)
Patent Document 11: WO 2004/018410 Pamphlet
Patent Document 12: WO 95/019773 Pamphlet
Patent Document 13: WO 00/066558 Pamphlet
Patent Document 14: WO 97/000853 Pamphlet
Non-patent Document 1: J. Comb. Chem., vol. 6, p. 142 (2004)
Non-patent Document 2: Synth. Commun., vol. 33, p. 4163 (2003)
Non-patent Document 3: Australian J. Chem., vol. 32, p. 1487 (1979)
Non-patent Document 4: J. Chem. Soc. Perkin Trans, 1, p. 643 (1979)
Non-patent Document 5: J. Org. Chem., vol. 35, p. 841 (1970)
Non-patent Document 6: J. Org. Chem., vol. 24, p. 238 (1959)
Non-patent Document 7: J. Am. Chem. Soc., vol. 101, p. 357 (1979)
Non-patent Document 8: Bull. Chem. Soc. Jpn., vol. 69, p. 3273 (1996)
Disclosure of Invention
Problems to be solved by the invention
[0006] Recently, pests acquire resistance by the use of pesticides such as
insecticides or fungicides over long term, and thus control by the insecticides or
fungicides that have been conventionally used becomes difficult. In addition, a part
of known pesticides has a high toxicity, or some of them start to disturb native
ecosystems due to long-term persistency. Under the circumstances, it is expected
all the time to develop a novel pesticide having a low toxicity and a low persistency.
Means for solving the problems
[0007] The inventors have eagerly investigated in order to solve the
above-mentioned problems, and as a result of it, they found that novel
isoxazoline- substituted benzamide compounds of formula (I) are extremely useful
compounds having excellent pest controlling activity, particularly insecticidal activity
and acaricidal activity, and having little adverse affect on non-targeted beings such
as mammals, fishes and useful insects, etc. Thus, the present invention has been
accomplished.
[0008] That is, the present invention relates to the following aspects (1) to (15):
(1) An isoxazoline-substituted benzamide compound of formula (1) or a salt
thereof:
(1)
wherein A1, A2and A3 independently of one
another are carbon atom or nitrogen atom,
G is benzene ring, nitrogen-containing 6-membered aromatic heterocyclic ring, furan
ring, thiophene ring, or 5-membered aromatic heterocyclic ring containing two or
more hetero atoms selected from oxygen atom, sulfur atom and nitrogen atom, W is
oxygen atom or sulfur atom,
X is halogen atom, cyano, nitro, azido, -SCN, -SF5, C1C6alkyl, C1C6alkyl arbitrarily
substituted with R4, C3-C8cycloalkyl, C3-C8cycloalkyl arbitrarily substituted with R4, C2-
C6alkenyl, C2-C6alkenyl arbitrarily substituted with R4, C3-C8cycloalkenyl, C3-
Cghalocycloalkenyl, C2-C6alkynyl, C2-C6alkynyl arbitrarily substituted with R4, -OH, -
OR5, -OSO2R5, -SH, -S(0)rR6, -N(R7)R6, -N=CHOR8, -N=C(R9)OR8, -CHO, -C(O)R9, -
C(O)OR9, -C(O)SR9, -C(0)NHR10, -C(0)N(R10)R9, -C(S)OR9, -C(S)SR9, -C(S)NHR10, -
C(S)N(R10)R9, -CH=NOR11, -C(R9)=NOR11, -S(O)2OR9, -S(O)2NHR10, -S(O)2N(R10)R9, -
Si(R13)(R14)R12, phenyl, phenyl substituted with (Z)p1, D-1 to D-60 or E-1 to E-49, when m
is 2, 3, 4 or 5, each X may be identical with or different from each other,
further, when two Xs are adjacent, the adjacent two Xs may form 5-membered or 6-
membered ring together with carbon atoms to which the two Xs are bonded by
forming -CH2CH2CH2-, -CH2CH20-, -CH2OCH2-, -OCH2O-, -CH2CH2S-, -CH2SCH2-, -
CH2CH2N(R15)-, -CH2N(R15)CH2-, -CH2CH2CH2CH2-, -CH2CH2CH2O -CH2CH2OCH2-, -
CH2OCH20-, -OCH2CH2O-, -OCH2CH2S-, -CH2CH=CH-, -OCH=CH-, -SCH=CH-, -
N(R15)CH=CH-, -OCH=N-, -SCH=N-, -,-N(R15)CH=N-, -N(R15)N=CH-, -CH=CHCH=CH-
, -OCH2CH=CH-, -N=CHCH=CH-, -N=CHCH=N- or -N=CHN=CH-, in this case,
hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily
substituted with Z, further when the hydrogen atoms are substituted with two or
more Zs at the same time, each Z may be identical with or
different from each other,
Y is halogen atom, cyano, nitro, azido, -SCN, -SF5, C1C6alkyl, C1C6alkyl arbitrarily
substituted with R4, C3-C8cycloalkyl, C3-C8cycloalkyl arbitrarily substituted with R4, -OH,
-OR5, -OSO2R5, -SH, -S(0)rR5, -NHR7, -N(R7)R6, -N=CHOR8, -N=C(R9)OR8, -C(O)NHR10, -
C(0)N(R10)R9, -C(S)NHR10, -C(S)N(R10)R9, -Si(R13)(R14)R12, phenyl, phenyl substituted with
(Z)p1, D-1 to D-60 or E-1 to E-49, when n is 2, 3 or 4, each Y may be identical with or
different from each other,
further, when two Ys are adjacent, the adjacent two Ys may form 5-membered or 6-
membered ring together with carbon atoms to which the two Ys are bonded by
forming -CH2CH2CH2-, -CH2CH2O-, -CH2OCH2-, -OCH2O-, -CH2CH2S-, -CH2SCH2-, -
SCH2S-, -CH2CH2CH2CH2-, -CH2CH2CH2O-, -CH2CH2OCH2-, -CH2OCH2O-, -OCH2CH20-, -
OCH2CH2S-, -SCH2CH2S-, -OCH=N- or -SCH=N-, in this case, hydrogen atoms
bonded to each carbon atom forming the ring may be arbitrarily substituted with Z,
further when the hydrogen atoms are substituted with two or more Zs at the same
time, each Z may be identical with or different from each other, R1 and R2
independently of each other are hydrogen atom, cyano, C1-C12alkyl, C1 C12alkyl
arbitrarily substituted with R16, C3-C12cycloalkyl, C3-C12cycloalkyl arbitrarily substituted
with R16, C3-C12alkenyl, C3-C12alkenyl arbitrarily substituted with R16, C3-C12cycloalkenyl,
C3-C12halocycloalkenyl, C3-C12alkynyl, C3-C12alkynyl arbitrarily substituted with R16,-SR9, -
S(O)2R=C(R19b)R19a, -C(0)R9, -C(O)OR9, -C(O)SR9, -C(O)N(R10)R9, -C(S)OR9, 9, -SN(R18)R17,
-S(O)2N(R10)R9, -OH, -OR19, -NHR20, -N(R20)R19, -N=CHR19b, -N-C(S)SR9, -C(S)N(R10)R9, -
C(=NR11)OR9, -C(=NR11)SR9, -C(=NR11)N(R10)R9, phenyl, phenyl substituted with (Z)p1, D-
1 to D-4, D-6 to D-13, D-15 to D-23, D-25 to D-37, D-39, D-40, D-42, D-45 to D-60, E-
3 to E-9, E-23 to E-28, E-30, E-31, E-34 or E-45, or R1 and R2 together form
=C(R2a)R1a, and further R1 and R2 together may form 3- to 8-membered ring together
with the nitrogen atom bonding them by forming C2-C7 alkylene chain, in this case,
the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and
may be arbitrarily substituted with halogen atom, C1-C6alkyl, CrC6haloalkyl,
CrC6alkoxy (CVC^alkyl, CrC6alkoxy, formyl, CrC6alkylcarbonyl, CrC6haloalkylcarbonyl
or CrC6alkoxycarbonyl, R1a and R2a independently of each other are C1-C12alkyl,
CrC12haloalkyl, C3-C12cycloalkyl, C3-C12alkenyl, C3-C12haloalkenyl, C3-C12alkynyl, C3-
C12haloalkynyl, -SR9, -OR9, -N(R10)R9, phenyl, phenyl substituted with (Z)p1, or R1a and R2a
together may form 5- or 6-membered ring together with the carbon atom bonding
them by forming C4 or C5 alkylene chain or C4 or C5 alkenylene chain, in this case, the
alkylene chain and the alkenylene chain may contain one to three oxygen atoms,
sulfur atoms or nitrogen atoms, and may be arbitrarily substituted with halogen atom,
C1C6alkyl, C1C6haloalkyl, C1C6alkoxy, C1C6haloalkoxy, (C1C6alkylthio or C1
C6haloalkylthio,
R3 is halogen atom, cyano, CC6alkyl, CC6alkyl arbitrarily substituted with R4, C3-
C8cycloalkyl, C3-C8cycloalkyl arbitrarily substituted with R4, C3-C6alkenyl, C2-C6alkenyl
arbitrarily substituted with R4, C3-C6alkynyl, C2-C6alkynyl arbitrarily substituted with R4,-
OR5, -S(O)rR5, -N(R10)R9, -CHO, -C(0)R9, -C(O)OR9, -C(0)SR9, -C(0)NHR10, -
C(0)N(R10)R9, -C(S)OR9, -C(S)SR9, -C(S)NHR10, -C(S)N(R10)R9, -CH=NOR11, -
C(R9)=NOR11, -Si(R13)(R14)R12, -P(O)(OR21)2, phenyl, phenyl substituted with (Z)p1, D-1 to
D-60 or E-1 to E-49, D-1 to D-60 are aromatic heterocyclic rings of the following
formulae, respectively
D-57 D-58 D-59 D-60
Z is halogen atom, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C4alkoxy C1-C4alkyl,
C1-C4haloalkoxy C1-C4alkyl, C1C4alkylthio C1C4alkyl, C1C4haloalkylthio C1-C4alkyl,
valkylsulfinyl C1-C4alkyl, vhaloalkylsulfinyl C1-C4alkyl, C1-C4alkylsulfonyl C1-C4alkyl,
vhaloalkylsulfonylC1-C4alkyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, -OH, C1-C6alkoxy,
C1-C6haloalkoxy, C1-C6alkylsulfonyloxy, C1-C6haloalkylsulfonyloxy, C1-C6alkylthio,
C1-C6haloalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-
C6haloalkylsulfonyl, -NH2, C1-C6alkylamino, di(C1-C6alkyl)amino, C1-
C6alkoxycarbonyl,C1-C6haloalkoxycarbonyl, -C(O)NH2, C1-C6alkylaminocarbonyl,
di(C1-C6alkyl)aminocarbonyl, -C(S)NH2, -S(0)2NH2, C1-C6alkylaminosulfonyl, di(C1-
C6alkyl)aminosulfonyl, phenyl or phenyl arbitrarily substituted with halogen atom,
when p1, p2, p3 or p4 is an integer of 2 or more, each Z may be identical with or
different from each other,
further, when two Zs are adjacent, the adjacent two Zs may form 5-membered or
membered ring together with carbon atoms to which the two Zs are bonded by
forming -CH2CH2CH2-, -CH2CH20-, -CH2OCH2-, -OCH2O-, -CH2CH2S-, -CH2SCH2-, -
CH2CH2CH2CH2-, -CH2CH2CH20-, -CH2CH2OCH2-, -CH2OCH2O-, -OCH2CH20-, -
CH2CH2CH2S-, -OCH2CH2S- or-CH=CH-CH=CH-, in this case, hydrogen atoms
bonded to each carbon atom forming the ring may be arbitrarily substituted with
halogen atom, C1-C4alkyl or C1-C4haloalkyl, E-1 to E-49 are saturated heterocyclic
rings of the following formulae, repectively
R4 is halogen atom, cyano, C3-C8cycloalkyl, C3-C8halocycloalkyl, -OH, -OR5, -SH,
-S(O)rR5, -N(R10)R9, -N(R10)CHO, -N(R10)C(O)R9, -N(R10)C(0)OR9, -N(R10)C(O)SR9, -
N(R10)C(S)OR9, -N(R10)C(S)SR9, -N(R10)S(0)2R9, -C(O)OR9, -C(O)N(R10)R9, -
Si(R13)(R14)R12, phenyl, phenyl substituted with (Z)p1, D-1 to D-60 or E-1 to E-49, R5 is
C1-C6alkyl,C1-C6alkyl arbitrarily substituted with R24, C3-C8cycloalkyl, C3-C8cycloalkyl
arbitrarily substituted with R24, C2-C6alkenyl, C2-C6alkenyl arbitrarily substituted with R24,
C3-C8cycloalkenyl, C3-C8halocycloalkenyl, C3-C6alkynyl, C3-C6alkynyl arbitrarily
substituted with R24, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-6 to D-
R^
15 to D-23, D-25 to D-35, D-39, D-40, D-42, D-45 to D-60, E-3 to E-9, E-23 to E-31,
E-34 or E-45,
R6 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C4alkoxy C1-C4alkyl,
C1-C4alkylthio C1-C4alkyl, phenythio C1-C4alkyl, phenylthio C1-C4alkyl substituted
with
(Z)p1,cyano C1-C6alkyt, C1-C6alkoxycarbonyl C1-C4alkyl, C1-C6alkylaminocarbonyl C1
C4alkyl, di(C1-C6alkyl)aminocarbony C1-C4alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl
substituted with (Z)p1, C1-C4alkyl substituted with any one of D-1 to D-60, C1-C4alkyl
substituted with any one of E-1 to E-49, C3-C6cycloalkyl, C3-C6alkenyl, C3-
C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, -OH, C1-C6alkylcarbonyloxy, C1
C6alkylthio, C1-C6haloalkylthio, phenylthio, phenylthio substituted with (Z)p1, -
SN(R18)R17, -S(O)2R9, -S(0)2N(R10)R9, -CHO, -C(O)R9, -C(O)OR9, -C(O)SR9, -C(O)NHR10, -
C(O)N(R10)R9, -C(S)OR9, -C(S)SR9, -C(S)NHR10, -C(S)N(R10)R9, -C(O)C(O)R9, -
C(O)C(O)OR9, -P(O)(OR21)2 or -P(S)(OR21)2, R7 is hydrogen atom, C1-C6alkyl, C1-
C6haloa!kyl, C3-C8cycloalkylC1-C6alkyl, C1 C4alkoxy C1-C4alkyl,C1-C4 alkylthio C1-
C4alkyl, C3-C8cycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-
C6haloalkynyl, -CHO, C1-C6alkylcarbonyl, C1 C6haloalkylcarbonyl or C1-
C6alkoxycarbonyl, or R7 together with R6 may form 3- to 7-membered ring with the
bonding nitrogen atom by forming C2-C6alkylene chain, in this case, the alkylene
chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be
arbitrarily substituted with halogen atom,C1-C6alkyl or Cr C6haloalkyl,
R8 is C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl, phenyl or phenyl substituted with (Z)p1, R9
isC1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C6alkoxy C1-C4alkyl, C1-
C6haloalkoxy C1-C4alkyl, C1-C6alkylthioC1-C4alkyl, C1-C6haloalkylthioC1-C4Ikyl,
cyano C1-C6alkyl, phenyl C1-C4Ikyl, phenyl C1-C4alkyl substituted with (Z)p1, C1-
C4alkyl substituted with any one of D-1 to D-60, CrC4alkyl substituted with any one of
E-1 to E-49, Cg-Cgcycloalkyl, C3-C8halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-
C6alkynyl, C3-C6haloalkynyl, phenyl, phenyl substituted with (Z)p1, D-1 to D-60 or E-1 to
E-49,
R10 is hydrogen atom, CrCealkyl, C1-C6haloalkyl, C3-C6cycloalkyl CrC4alkyl, Cr C6alkoxy
C1-C4a!kyl, C1-C6alkylthio CrC4alkyl, cyanoC1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl, R10
together with R9 may form 3- to 7-membered ring with the atom bonding them by
forming C2-C6alkylene chain, in this case, the alkylene chain may contain one oxygen
atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen
atom, C1-C6alkyl, C1-C6alkoxy, formyl, C1-C6alkylcarbonyl or C1-C6alkoxycarbonyl,
R11 is hydrogen atom, C1-C6alkyl,C1-C6haloalkyl, phenyl C1-C4alkyl, phenyl C1
C4alkyl substituted with (Z)p1, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-
C6haloalkynyl, phenyl or phenyl that may be substituted with (Z)p1, R11 together with
R9 may form 5- to 7-membered ring with the atom bonding them by forming C2-
C4alkylene chain, in this case, the alkylene chain may contain one oxygen atom,
sulfur atom or nitrogen atom, and may be arbitrarily substituted with halogen atom or
C1-C6alkyl,
R12 isC1-C6alkyl, C1-C6haloalkyl, phenyl or phenyl substituted with (Z)p1,
R13 and R14 independently of each other are C1-C6alkyl or C1-C6haloalkyl,
R15 is hydrogen atom, C1-C6alkyl,C1-C6haloalkyl, C1-C6alkoxycarbonyl C1-C4alkyl,
C1-C6Chaloalkoxycarbonyl C1-C4alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl
substituted
with (Z)P1, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl C1-
C6alkoxy, C1-C6alkoxycarbonyl, C1-C6haloalkoxycarbonyl, phenyl or phenyl
substituted with (Z)p1,
further, in case where Z is present in an adjacent position of R15, the adjacent R15
and Zay form 6-membered ring together with the atom bonding them by forming
-CH2CH2 mCH2CH2-, -CH=CH-CH=CH-, -N=CH-CH=CH-, -CH=N-CH=CH-, -CH=CHN=
CH- or -CH=CH-CH=N-, in this case, hydrogen atoms bonded to each carbon
atom forming the ring may be arbitrarily substituted with halogen atom, C1-C4alkyl or
R16 is halogen atom, cyano, nitro, C3-C8cycloalkyl, C3-C8halocycloalkyl, -OR25, -N(R26)R25,
-SH, -S(0)rR27, -SO2NHR29, -SO2N(R29)R28, -CHO, -C(O)R28, -C(0)OH, -C(0)OR28, -C(O)SR28,
-C(O)NHR29, -C(0)N(R29)R28, -C(S)NHR29, -C(S)N(R29)R28, -C(0)C(0)OR28, -C(R31)=NOH, -
C(R31)=NOR30, -C(=NR31)OR30, -C(=NR31)SR30, -C(=NR31)N(R29)R30, -C(=NOR31)NHR29, -
C(=NOR31)N(R29)R30, -Si(R13)(R14)R12, -P(0)(OR21)2, -P(S)(OR21)2, -P(phenyl)2,-
P(O)(phenyl)2) phenyl, phenyl substituted with (Z)p1, D-1 to D-60, E-1 to E-49 or M-1 to
M-22,
M-1 to M-22 are partially saturated heterocyclic rings of the following formulae,
respectively
R17 is C1-C12alkyl, C1-C12haloalkyl, C1-C12alkoxy C1-C12alkyl, cyano C1-C12alkyl,
C12alkoxycarbonyl C1-C12Ikyl, phenyl CrC4alkyl, phenyl CrC4alkyl substituted with
(Z)p1, C3-C12alkenyl, C3-C12haloalkenyl, C3-C12alkynyl, C3-C12haloalkynyl, C1
C12alkylcarbonyl, C1-C12alkoxycarbonyl, -C(0)ON=C(CH3)SCH3, -
C(O)ON=C(SCH3)C(O)N(CH3)2, phenyl or phenyl substituted with (Z)p1, R18 isC1-
C12alkyl, C1-C12haloalkyl, C1-C12alkoxy C1-C12alkyl, cyanoC1-C12alkyl,
(Z)P5 (Z)22v P5
C1-C12alkoxycarbonyl C1-C12alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with
(Z)p1, C3-C12alkenyl, C3-C12haloalkenyl, C3-C12alkynyl, C3-C12haloalkynyl, phenyl or phenyl
substituted with (Z)p1, or R18 together with R17 may form 5- to 8-membered ring with the
nitrogen atom bonding them by forming C4-C7alkylene chain, in this case, the
alkylene chain may contain one oxygen atom or sulfur atom, and may be arbitrarily
substituted with C1-C4alkyl orC1-C4alkoxy,
R19 is hydrogen atom, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R16, C3-
C6cycloalkyl, C3-C8halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-
C6haloalkynyl, -CHO, -C(O)R28, -C(O)OR28, -C(0)SR28, -C(0)NHR29, -C(O)N(R29)R28, -
C(S)NHR29, -C(S)N(R29)R28, -S(O)2R28, -S(O)2NHR29, -S(O)2N(R29)R28, -P(O)(OR21)2, -
P(S)(OR21)2, phenyl, phenyl substituted with (Z)p1, D-1 to D-13, D-15 to D-25, D-30 to
D-37, D-39, D-40, D-42, D-45 to D-60, E-5, E-7, E-9, E-24, E-25, E-27, E-28, E-30
orE-31,
R19a is C1-C6alkyl, C1-C6haloalkyl,C1-C4alkoxy C1-C4alkyl,C1-C4alkylthio C1-C4alkyl, C1-
C4alkylsulfonyl Valkyl, C1-C4alkoxycarbonylC1-C4alkyl, phenylC1-C4alkyl, phenylC1-
C4alkyl substituted with (Z)p1, C3-C6cycloalkyl, phenyl, phenyl substituted with (Z)P1, D-1
to D-60 or E-1 to E-49,
R19b is hydrogen atom orC1-C6alkyl, or R19a together with R19b may form 4- to 6-
membered ring with the carbon atom bonding them by forming C3-C5alkylene chain, in
this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen
atom, and may be arbitrarily substituted with C1-C6alkyl, formyl, C1-C6alkylcarbonyl
or C1-C6alkoxycarbonyl,
R20 is hydrogen atom,C1-C6alkyl, C1-C6haloalkyl, C1-C4alkoxy C1-C4alkyl, C1-
C4haloalkoxyC1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C1-C4haloalkylthio C1-C4alkyl, C1-
C4alkylsulfonyl C1-C4alkyl,C1-C4haloalkylsulfonylC1-C4alkyl, cyano C1-C6alkyl, C1-
C4alkoxycarbonyl C1-C4alkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl, C3-
C6haloalkynyl, -CHO, -C(O)R9, -C(O)OR9, -C(O)SR9, -C(S)OR9, -C(S)SR9, C1-
C6alkylsulfonyl or C1-C6haloalkylsulfonyl, R21 is C1-C6alkyl or C1-C6haloalkyl,
R22 is halogen atom, cyano, C1-C6alkyl, C1-C6haloalkyl, hydroxy C1-C6alkyl, C1-
C4alkoxy C1-C4alkyl, C1-C4alkoxycarbonyl C1-C4alkyl, C1-C6alkoxy, C1-C6alkylthio,
C1-C6alkylamino, di(C1-C4alkyl)amino, C1-C6alkoxycarbonyl, phenyl or phenyl
substituted with (Z)p1, when q1, q2, q3 or q4 is an integer of 2 or more, each R22 may
be identical with or different from each other, further in case where two R22s are
present on the same carbon atom, the two R22s together may form oxo, thioxo, imino,
C1-C6alkylimino, C1-C6alkoxyimino orC1-C6alkylidene,
R23 is hydrogen atom, C1-C6alkyl,C1-C6alkyl substituted with R32, C3-C6cycloalkyl, C3-
C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, -OH, benzyloxy, -CHO, -C(O)R33, -C(0)OR33, -
C(O)SR33, -C(0)NHR34, -C(O)N(R34)R33, -C(S)NHR34, -C(S)N(R34)R33, -S(0)2R33, -
P(O)(OR21)2, -P(S)(OR21)2, phenyl, phenyl substituted with (Z)p1 or D-5, R24 is halogen
atom, cyano, C3-C8cycloalkyl, C3-C8halocycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-
C6alkylthio, C1-C6haloalkylthio, C1-C6alkylsulfonyl, C C6haloalkylsulfonyl, C1-
C6alkylamino, di(C1-C6alky)amino, -CHO, C1-C6alkylcarbonyl, C^Cehaloalkylcarbonyl,
C1-C6alkoxycarbonyl, C1-C6haloalkoxycarbonyl, -CH=NOR11, -C(R9)=NOR11, phenyl,
phenyl substituted with (Z)p1, D-1 to D-60 or E-1 to E-49, R25 is hydrogen atom, C1-
C8alkyl, C1-C8alkyl arbitrarily substituted with R32, C3-C8cycloalkyl, C3-C8cycloalkyl
arbitrarily substituted with R32, C3-C8alkenyl, C3-C8alkenyl arbitrarily substituted with R32,
C3-C8alkynyl, C3-C8alkynyl arbitrarily substituted with R32, -CHO, -C(0)R33, -C(O)OR33, -
C(O)SR33, -C(O)NHR34, -C(0)N(R34)R33, -C(O)C(O)R33, -C(O)C(0)OR33, -C(S)R33, -
C(S)OR33, -C(S)SR33, -C(S)NHR34, -C(S)N(R34)R33, -S(0)2R33, -S(O)2N(R34)R33, -Si(R13)(R14)R12,
-P(O)(OR21)2, -P(S)(OR21)2, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-6 to D-
13, D-15 to D-23, D-25 to D-37, D-39, D-40, D-42, D-45 to D-60, E-3 to E-9, E-23
toE-31,E-34orE-45,
R26 is hydrogen atom, CrC6alkyl, CrC6haloalkyl, CrC4alkoxy CrC4alkyl, Cr C4alkylthio
CrC4alkyl, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6alkynyl orCrC6alkoxy, or R26 together with
R25 may form 3- to 6-membered ring with the nitrogen atom bonding them by forming
C2-C5alkylene chain, in this case, the alkylene chain may one contain oxygen atom,
sulfur atom or nitrogen atom, and may be substituted with halogen atom, CrC6alkyl,
CrC6haloalkyl, CrC6alkoxy, phenyl, phenyl substituted with (Z)p1, oxo orthioxo,
R27is CrC8alkyl, CrC8alkyl arbitrarily substituted with R32, C3-C8cycloalkyl, C3-
C8cycloalkyl arbitrarily substituted with R32, C3-C8alkenyl, C3-C8alkenyl arbitrarily
substituted with R32, C3-C8alkynyl, C3-C8alkynyl arbitrarily substituted with R32, -SH, C1-
C6alkylthio, C1-C6haloalkylthio, phenylthio, phenylthio substituted with (Z)p1, -CHO, -
C(0)R33, -C(0)OR33, -C(O)SR33, -C(O)NHR34, -C(O)N(R34)R33, -C(O)C(O)R33, -
C(0)C(0)OR33, -C(S)R33, -C(S)OR33, -C(S)SR33, -C(S)NHR34, -C(S)N(R34)R33, -P(0)(OR21)2,
-P(S)(OR21)2, phenyl, phenyl substituted with (Z)p1, D-18, D-21, D-25, D-30 to D-35, D-
47, D-50, D-51, E-3 to E-9, E-23 to E-31, E-34 or E-45, R28 is C1-C6alkyl, C1-C6alkyl
arbitrarily substituted with R32, C3-C8cycloalkyl, C3-
C6Cycloalkyl arbitrarily substituted with R32, C2-C6alkenyl C3-C8cycloalkyl, C2-
C6haloalkenyl C3-C8cycloalkyl, C2-C8alkenyl, C2-C8alkenyl arbitrarily substituted with R32,
C2-C8alkynyl, C2-C8alkynyl arbitrarily substituted with R32, phenyl, phenyl substituted
with (Z)p1, D-1 to D-60 or E-1 to E-49,
R29 is hydrogen atom, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R32, C3-
C6alkeny3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, phenyl or phenyl substituted
with (Z)p1, or R29 together with by forming C2-C5alkylene chain, in this case, the
alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may
be arbitrarily substituR28 may form 3- to 6-membered ring with the nitrogen atom
bonding themted with halogen atom, C1-C6alkyl, C1-C6alkoxy, formyl, C1-
C6alkylcarbonyl,C1-C6alkoxycarbonyl, phenyl or phenyl substituted with (Z)p1, R30 is
C3-C8alkyl, C3-C8alkyl arbitrarily substituted with R32, C3-C8cycloalkyl, C3-C8alkenyl, C3-
C8alkenyl arbitrarily substituted with R32, C3-C8alkynyl, C3-C8alkynyl arbitrarily substituted
with R32,
R31 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-
C6alkoxy C1-C4alkyl, C1-C6haloalkoxy C1-C4alkyl, C1-C6alkylthio C1-C4alkyl, C1-
C6haloalkylthioC1-C44alkyl, C1-C6alkylsulfonyl C1-C4alkyl, C1-C6haloalkylsulfonyl
C1-C4alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1 C3-C6cycloalkyl,
phenyl or phenyl substituted with (Z)p1, or R31 together with R30 may form 5- to 7-
membered ring with the atom bonding them by forming C2-C4alkylene chain, in this
case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen
atom, and may be arbitrarily substituted with halogen atom or C1-C6alkyl, R32 is
halogen atom, cyano, nitro, C3-C8cycloalkyl, C3-C8halocycloalkyl, -OH, -OR33, -OC(O)R33,
-OC(O)OR33, -OC(0)NHR33, -OC(O)N(R34)R33, -OC(S)NHR33, -OCXSWR34^33, -SH, -
S(0)rR33, -SC(0)R33, -SC(O)OR33, -SC(0)NHR33, -SC(0)N(R34)R33, -SC(S)NHR33, -
SC(S)N(R34)R33, -NHR34, -N(R34)R33, -N(R34)CHO, -N(R34)C(0)R33, -N(R34)C(0)OR33, -
N(R34)C(O)NHR33, -N(R34)C(O)N(R34)R33, -N(R34)C(S)NHR33, -N(R34)C(S)N(R34)R33, -CHO, -
C(O)R33, -C(O)OR33, -C(O)SR33, -C(0)NHR34, -C(0)N(R34)R33, -C(O)C(0)OR33, -CH=NOR11,
-C(R9)=NOR11, -Si(R13)(R14)R12, -P(0)(OR21)2, -P(S)(OR21)2, -P(phenyl)2, -P(0)(phenyl)2,
phenyl, phenyl substituted with (Z)p1, D-1 to D-60 or E-1 to E-49,
R33 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C3-C6halocycloalkyl C1-
C4alkyl, C1-C4alkoxy C1-C4alky, C1-C4C1-C4haloalkoxy C1-C4alky, C1-C4 alkylthio
C1-C4alkyl, C1-C4haloalkylthio C1-C4alkyl, C1-C4alkylsulfonyl C1-C4alkyl C1-
C4haloalkylsufonyl C1-C4aIkyl, cyano C1-C6alkyl, C1-C6alkylcarbonyl C1-C4aIkyl, C1-
C6haloalkylcarbonyl C1-C4alkyl, C1-C6alkoxycarbonyl C1-C4alkyl,
C6alkyl)aminocarbonyl C1-C4alkyl, tri(C1-C4alkyl)silyl C1-C4alkyl, phenyl C1-
C4alkyl,
phenyl C1-C4alkyl substituted with (Z)p1, C1-C4alkyl substituted with any one of D-1 to
D-60, C1-C4alkyl substituted with any one of E-1 to E-49, C3-C6cycloalkyl, C3-
C6halocycloalkyl, C2-C6alkenyl C3-C8cycloalkyl, C2-C6haloalkenyl C3-C8cycloalkyl, C2-
C8alkenyl, C2-C8haloalkenyl, C3-C8cycloalkenyl, C3-C8halocycloalkenyl, C2-C8alkynyl,
C2-C8haloalkynyl, phenyl, phenyl substituted with (Z)p1, D-1 to D-60 or E-1 to E-49,
R34 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C3-C8cycloalkyl, C3-C6alkenyl, C3-
C6alkynyl, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl,C1-C6alkoxycarbonyl, C1-
C6haloalkoxycarbonyl, phenoxycarbonyl, phenoxycarbonyl substituted with (Z)p1,
phenylcarbonyl, phenylcarbonyl substituted with (Z)p1, C1-C6alkylsulfonyl, Cr
C6haloalkylsulfonyl, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-6 to D-13, D-
15 to D-23, D-25 to D-37, D-39, D-40, D-42, D-45 to D-60, E-3 to E-9, E-23 to E-31,
E-34 or E-45, or R34 together with R33 may form 3- to 6-membered ring with the
nitrogen atom bonding them by forming C2-C5alkylene chain, in this case, the
alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may
be arbitrarily substituted with halogen atom, C1-C6alkyI, C1-C6alkedoxy, formyl, C1-
C6alkylcarbonyl, C1-C6alkoxycarbonyl, phenyl or phenyl substitut with (Z)p1,
m is an integer of 0 to 5,
n is an integer of 0 to 4,
p1 is an integer of 1 to 5,
p2 is an integer of 0 to 4,
p3 is an integer of 0 to 3,
p4 is an integer of 0 to 2,
p5 is an integer of 0 or 1,
q1 is an integer of 0 to 3,
q2 is an integer of 0 to 5,
q3 is an integer of 0 to 7,
q4 is an integer of 0 to 9,
r is an integer of 0 to 2, and
t is an integer of 0 or 1.
(2) The isoxazoline-substituted benzamide compound or the salt thereof as set
forth in (1), wherein
G is an aromatic 6-membered ring shown in any one of G-1 to G-10 or an aromatic
5-membered ring shown in any one of G-11 to G-25
X is halogen atom, cyano, nitro, -SF5, C1-C6alkyl, C1-C6alkyl arbitrarily substituted
with R4, C3-C8cycloalkyl, C3-C8cycloalkyl arbitrarily substituted with R4, C2-C6alkenyl, C2-
C6alkenyl arbitrarily substituted with R4, C2-C6alkynyl, C2-C6alkynyl arbitrarily
substituted with R4, -OH, -OR5, -OSO2R5, -S(O)rR5, -N(R7)R6, -C(0)OR9, -C(O)SR9, -
C(0)NHR10, -C(O)N(R10)R9, -C(S)OR9, -C(S)SR9, -C(S)NHR10, -C(S)N(R10)R9,
-CH=NOR11, -C(R9)=NOR11, -S(O)2NHR10, -S(O)2N(R10)R9,
-Si(R13)(R14)R12, phenyl, phenyl substituted with (Z)p1, D-1 to D-60 or E-1 to E-49,
when m is an integer of 2 or more, each X may be identical with or different from
each other,
further, when two Xs are adjacent, the adjacent two Xs may form 5-membered or 6-
membered ring together with carbo2O-, -CH2OCH2-, -OCH2O-, -CH2CH2S-, -CH2SCH2-,
-CH2CH2CH2CH2-, -CH2CH2Cn atoms to which the two Xs are bonded by
forming -CH2CH2CH2-, -CH2CHH2O-, -CH2CH2OCH2-, -CH2OCH2O-, -OCH2CH2O-,
-OCH2CH2S- or -CH=CHCH=CH-, in this case, hydrogen atoms bonded to each
carbon atom forming the ring may be arbitrarily substituted with halogen atom, Cr
C4alkyl or C1-C4haloalkyl,
Y is halogen atom, cyano, nitro, CrC6alkyl, C1-C6alkyl arbitrarily substituted with R4,
-OR5, -OS02R5, -S(O)rR5, -NHR7, -N(R7)R6, -N=CHOR8, -N=C(R9)OR8, -C(O)NHR10,
-C(O)N(R10)R9, -C(S)NHR10, -C(S)N(R10)R9, phenyl, phenyl substituted with (Z)p1, D-1
to D-24, D-30 to D-38, D-43 to D-52 or D-53, when n is an integer of 2 or more, each
Y may be identical with or different from each other,
further, when two Ys are adjacent, the adjacent two Ys may form 5-membered or 6-
membered ring together with carbon atoms to which the two Ys are bonded by
forming -CH2CH2CH2-, -CH2CH2O-, -CH2OCH2-, -OCH2O-, -CH2CH2CH2CH2-,
-CH2CH2CH2O-, -CH2CH2OCH2-, -CH2OCH20-, -OCH2CH20-, -OCH=N- or -SCH=N-,
in this case, hydrogen atoms bonded to each carbon atom forming the ring may be
arbitrarily substituted with halogen atom, C1-C4alkyl or C1-C4haloalkyl,
R1 is C1-C8alkyl, C1-C8alkyl arbitrarily substituted with R16, C3-C8cycloalkyl, C3-
C8halocycloalkyl, C3-C8alkenyl, C3-C8haloalkenyl, phenyl C3-C6alkenyl, phenyl C3-
C6alkenyl substituted with (Z)p1, C3-C8alkynyl, C3-C8haloalkynyl, phenyl C3-C6alkynyl,
phenyl C3-C8alkynyl substituted with (Z)p1, CrC6alkoxy, -N(R20)R19, -N=CHR19b,
-N=C(R19b)R19a, -C(O)N(R10)R9, -C(S)N(R10)R9, -C(=NR11)OR9, -C(=NR11)SR9,
-C(=NR11)N(R10)R9, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-6 to D-13, D-
15 to D-23, D-26, D-27, D-29 to D-37, D-39, D-40, D-42, D-45 to D-58, E-4 to E-9,
E-23 to E-28, E-30, E-31, E-34 or E-45,
R2is hydrogen atom, C1-C8alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-
C4alkoxy C1-C4alkyl, C1-C4haloalkoxy C1-C4alkyl, benzyloxy C1-C4alkyl, C1-
C4alkylthio
C1-C4alkyl, C1-C4haloalkylthioC1-C4alkyl, C1-C4alkylsulfonyl C1-C4alkyl, C1-
C4haloalkylsulfonyl C1-C4alkyl, phenylthio C1-C4alkyl, phenylthio C1-C44alkyl
substituted with (Z)p1, cyano C1-C6alkyl, nitro C1-C8alkyl, C1-C4Ikylcarbonyl C1-
C4alkyl, C1-C4alkoxycarbony C1-C4alkyl, C3-C6cycloalkyl, C3-C6alkenyl, C3-
C6haloalkenyl, C3-C6alkynyl, -SR9, -S(O)2R9, -SN(R18)R17, -OH, -OR19, -NHR20,
-N(R20)R19, -N=CHR19b, -N=C(R19b)R19a, -C(0)R9, -C(O)OR9, -C(O)SR9, -C(S)OR9,
-C(S)SR9, phenyl, phenyl substituted with (Z)p1,
or R1 and R2 together form =C(R2a)R1a, and further R1 and R2 together may form 3- to
7-membered ring together with the nitrogen atom bonding them by forming C2 to C6
alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur
atom or nitrogen atom, and may be arbitrarily substituted with C1-C6alkyl, formyl, C1-
C6alkylcarbonyl or C1-C6alkoxycarbonyl,
R1a and R2a together may form 5- or 6-membered ring together with the carbon atom
bonding them by forming C4 or C5 alkylene chain or C4 or C5 alkenylene chain, in this
case, the alkylene chain and the alkenylene chain may contain one to three oxygen
atoms, sulfur atoms or nitrogen atoms, and may be arbitrarily substituted with
halogen atom or CrC6alkyl,
R3 is cyano, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4, C3-C8cycloalkyl, C3-
C8halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl,
-OR5, -S(O)rR5, -N(R10)R9, -C(O)OR9, -C(O)SR9, -C(O)NHR10,
-C(O)N(R10)R9, -C(S)OR9, -C(S)SR9, -C(S)NHR10, -C(S)N(R10)R9, -CH=NOR11,
-C(R9)=NOR11, -Si(R13)(R14)R12, phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D8-
to D-13, D-15 to D-23, D-25 to D-37, D-39, D-40, D-42, D-45 to D-60 or E-4 to E-7,
E-23 to E27 or E-28,
R4 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, -OH, -OR5, -
S(O)rR5, -N(R10)R9, -N(R10)C(0)R9, -N(R10)C(0)OR9, -N(R10)C(O)SR9,
-N(R10)C(S)OR9, -N(R10)C(S)SR9, -N(R10)S(O)2R9, -Si(R13)(R14)R12, phenyl, phenyl
substituted with (Z)p1, D-1 to D-5, D-8 to D-38, D-41, D-43, D-44-, D-47 to D-52 or D-
53,
R5 is C1-C6alkyl, C1-C6haloalkyl, C3-C8haloalkoxy C3-C8haloalkyl, C3-C8cycloalkyl, C3-
C8halocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl,
phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-7, D-9, D-15 to D-23, D-30 to D-
35, D-47 to D-53, E-3 to E-9, E-23 to E-27 or E-28,
R6 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C4aIkoxy C1-C4alkyl,
C1-C4alkylthio C1-C4alkyI, -S(O)2R9, -CHO, -C(O)R9, -C(O)OR9, -C(O)SR9, -C(S)OR9
or -C(S)SR9,
R7 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl or C3-C6alkynyl,
R8 is C1-C6alkyl,
R9 is C1-C6alkyl,C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C6alkoxy CrC4alkyl,
C1-C6alkylthio C1-C4alkyl, cyano C1-C6alkyl, phenyl CrC4alkyl, phenyl Chalkyl,
substituted with (Z)p1, C3-C8cycloalkyl, C3-C8halocycloalkyl, C3-C6alkenyl, C3-
C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, phenyl, phenyl substituted with (Z)p1,
D-1 to D-4, D-6 to D-35, D-38, D-47 to D-54 or D-55,
R10 is hydrogen atom orC1-C6alkyl, or R10 together with R9may form 5- to 7-
membered ring with the nitrogen atom bonding them by forming C4-C6alkylene chain,
in this case, the alkylene chain may contain one oxygen atom or sulfur atom,
R11 is C1-C6alkyl, C1-C6haloalkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted
with (Z)p1, phenyl or phenyl substituted with (Z)p1, or R11 together with R9 may form 5-
or 6-membered ring with the atom bonding them by forming C2-C3alkylene chain, in
this case, the alkylene chain may be arbitrarily substituted with C1-C6alkyl,
R12 is C1-C6alkyl, phenyl or phenyl substituted with (Z)p1,
R13 and R14 independently of each other are C1-C6alkyl,
R15 is C1-C6alkyl,C1-C6haloalkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted
with (Z)p1, phenyl or phenyl substituted with (Z)p1,
R16 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, -OR25, -N(R26)R25,
-SH, -S(O)rR27, -SO2NHR29, -SO2N(R29)R28, -CHO, -C(0)R28, -C(0)OR28, -C(O)NHR29,
-C(O)N(R29)R28, -C(O)N(R29)OR28, -C(S)NHR29, -C(S)N(R29)R28, -C(R31)=NOH,
-C(R31)=NOR30, -C(=NR31)OR30, -C(=NR31)SR30, -C(=NR31)N(R29)R30,
-C(=NOR31)NHR29, -C(=NOR31)N(R29)R30, -Si(R13)(R14)R12, phenyl, phenyl substituted
with (Z)P1, D-1 to D-60, E-1 to E-49 or M-1 to M-22,
R17 is C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C6alkoxycarbonyl C1-C4alkyl, phenyl C1-
C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1 or C1-C6alkoxycarbonyl,
R18 isC1-C6alkyl, phenyl C1-C4alkyl or phenyl C1-C4alkylsubstituted with (Z)p1, or R18
together with R17 may form 5- or 6-membered ring with the nitrogen atom bonding
them by forming C4-C5alkylene chain, in this case, the alkylene chain may contain
one oxygen atom or sulfur atom, and may be arbitrarily substituted with methyl or
methoxy,
R19 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R16, C3-C6cycloalkyl, C3-
C6halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, -CHO, -C(O)R28,
-C(0)OR28, -C(O)NHR29, -C(O)N(R29)R28, -C(S)NHR29, -C(S)N(R29)R28, -S(O)2R28,
-S(O)2NHR29, -S(0)2N(R29)R28, phenyl, phenyl substituted with (Z)p1, D-1 to D-13, D-
15 to D-25, D-30 to D-37, D-39, D-40, D-42, D-45 to D-60, E-5, E-7, E-9, E-24, E-25,
E-27, E-28,E-30orE-31,
R19a is C1-C6alkyl,C1-C6haloalkyl, C3-C6cycloalkyl, phenyl, phenyl substituted with
(Z)p1, D-1 to D-4, D-8 to D-10, D-15 to D-23, D-47 to D-55, E-4 to E-7, E-23 to E-27 or
E-28,
R19b is hydrogen atom or C1-C6alkyl, or R19a together with R19bmay form 5- or 6-
membered ring with the carbon atom bonding them by forming C4-C5alkylene chain, in
this case, the alkylene chain may contain one oxygen atom or sulfur atom, R20 is
hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C1-C4alkoxy C1-C4alkyl, Cr C4alkylthio
C1-C4alkyl, cyano C1-C6alkyl, C1-C4aIkoxycarbonyl C1-C4alkyl, C2-C6alkenyl, C3-
C6alkynyl, -CHO, -C(O)R9, -C(O)OR9, -C(O)SR9, -C(S)OR9, -C(S)SR9 or C1-
C6alkylsulfonyl,
R22 is halogen atom, cyano, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, Cr
C6alkoxycarbonyl, -C(O)NH2 or -C(S)NH2, when q1, q2, q3 or q4 is an integer of 2 or
more, each R22 may be identical with or different from each other, further in case
where two R22s are present on the same carbon atom, the two R22s together may form
oxo, thioxo, C1-C6alkylimino, C1-C6alkylimino, C1-C6alkoxyimino or C1-C6alkylidene,
R23 is hydrogen atom, C1-C6alkyl,C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R32,
C3-C6cycloalkyl, C3-C6alkenyl, C3-C6alkynyl, -OH, benzyloxy, -CHO, -C(O)R33, -
C(O)OR33, -C(O)SR33, -C(O)NHR34, -C(0)N(R34)R33, -S(0)2R33, phenyl, phenyl substituted
with (Z)p1 or D-5,
R25 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C1-C4alkoxy C1-C6alkyl, C1-
C4alkylthio C1-C4alkyl, cyano C1-C6alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl
substituted with (Z)p1, C3-C6alkenyl, C3-C6alkynyl, -CHO, -C(O)R33, -C(O)OR33, -C(0)SR33, -
C(0)NHR34, -C(O)N(R34)R33, -C(S)R33, -C(S)OR33, -C(S)SR33, -C(S)NHR34, -C(S)N(R34)R33,
-S(O)2R33, -S(0)2N(R34)R33, di( C1-C6alky)phosphoryl, di(C1-C6alkyl)thiophosphoryl, tri(C1-
C4alkyl)silyl, phenyl or phenyl substituted with
(Z)P1,
R26is hydrogen atom, C1-C6alkyl, C3-C6alkenyl, C3-C6alkynyl or C1-C6alkoxy, or R26
together with R25 may form 4- to 6-membered ring with the nitrogen atom bonding
them by forming C3-C5alkylene chain, in this case, the alkylene chain may contain
one oxygen atom, sulfur atom or nitrogen atom, and may substituted with C1-
C6alkyl,
oxo or thioxo,
R27 is C1-C6alklyl, C1-C6haloalkyl, hydroxy C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-
C4alkylthio C1-C4alkyl, C1-C4alkylcarbonyl C1-C4alkyl, C1-C4alkoxycarbonyl C1-
C4alkyl, di(C1-C4alkyl)aminocarbonyl C1-C4alkyl, tri(C1-C4alkyl)silyl C1-C4alkyl, phenyl
C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-C6alkenyl, C3-C6alkynyl, C1-
C6alkylcarbonyl, C1-C6alkylthio, phenylthio, phenylthio substituted with (Z)p1l
-C(0)NHR34, -C(O)N(RM)R33, -C(S)NHR34, -C(S)N(R34)R33, phenyl, phenyl
substituted with (Z)p1, D-21, D-35, D-47 or D-50,c
R28 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R32, C3-C6ycloalkyl, C3-
C6halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl,
phenyl, phenyl substituted with (Z)p1, D-1 to D-60 or E-1 to E-49,
R29 is hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl,
cyano C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl, or R29 together with R28 may form 3-
to 6-membered ring with the nitrogen atom bonding them by forming C2-C5alkylene
chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom,
R30 is C1-C6alkyl, C1-C4alkoxyC1-C4alkyl, C1-C4alkylthioC1-C4alkyl, C3-C6cycloalkyl
C1-C4alkyl, tri(C1-C6alkyl)silyl C1-C4alkyl, phenyl C1-C4alkyl, phenylC1-C4alkyl
substituted with (Z)p1, C3-C8alkenyl, C3-C8haloalkenyl, C3-C8alkynyl or C3-
C8haloalkynyl,
R31 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl or C3-C6cycloalkyl, or R31 together
with R30 may form 5- or 6-membered ring with the atom bonding them by forming
C2-C3alkylene chain, in this case, the alkylene chain may be arbitrarily substituted
with C1-C6alkyl,
R32 is halogen atom, cyano, C3-C8cycloalkyl, C3-C8halocycloalkyl, -OR33, -OC(O)R33,
-OC(0)NHR33, -OC(O)N(R34)R33, -S(0)rR33, -SC(O)R33, -SC(O)NHR33,
-SC(O)N(R34)R33, -N(R34)CHO, -N(R34)C(O)R33, -N(R34)C(0)OR33, -C(O)OR33,
-C(O)NHR34, -C(O)N(R34)R33, phenyl, phenyl substituted with (Z)p1, D-1 to D-60 or E-
1 to E-49,
R33 is C1-C6alkyl, C1-C6aloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C4alkoxy C1-C4alkyl,
C1-C4haloalkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C1-C4haloalkylthio C1-
C4alkyl,
CrC4alkylsulfonyl C1-C4alkyl, C1-C4haloalkylsulfonyl C1-C4alkyl, cyano C1-C6alkyl,
phenyl C1-C4alkyl, phenyl C1-C4aIkyl substituted with (Z)p1, C3-C6cycloalkyl, C3-
C6halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, phenyl, phenyl
substituted with (Z)p1, D-1 to D-4, D-8 to D-13, D-15 to D-18, D-21, D-29 to D-37, D-
47 to D-55, E-5, E-7, E-9, E-24, E-25, E-27, E-28, E-30, E-31or E-34,
R34 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl or C3-C6alkynyl, or R34
together with R33 may form 3- to 6-membered ring with the nitrogen atom bonding
them by forming C2-C5alkylene chain, in this case, the alkylene chain may contain
one oxygen atom or sulfur atom.
(3) The isoxazoline-substituted benzamide compound or the salt thereof as set
forth in (2), wherein
G is G-1, G-3, G-4, G-13, G-14, G-17, G-18, G-20, G-21 orG-22, X is halogen
atom, cyano, nitro, -SF5l CrC6alkyl, CrC6alkyl arbitrarily substituted with R4, C3-
C8cycloalkyl, C3-C8halocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-
C6haloalkynyl, -OR6, -OSO2R5, -S(O)rR5, -C(O)OR9, -C(O)SR9, -C(S)OR9, -C(S)SR9, -
C(S)NHR10, -C(S)N(R10)R9, -CH=NOR11, -C(R9)=NOR11, -Si(R13)(R14)R12, E-10, E-12, E-
18, E-32, E-35 or E-43, when m is 2 or 3, each X may be identical with or different from
each other,
further, when two Xs are adjacent, the adjacent two Xs may form 5-membered or 6-
membered ring together with carbon atoms to which the two Xs are bonded by
forming -CF2OCF2-, -OCF20-, -CF2OCF2O- or -OCF2CF2O-, Y is halogen atom, cyano,
nitro,C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4, -OR5, -OSO2R5, -S(O)rR5, -
NHR7, -N(R7)R6, -N=C(R9)OR8, -C(O)NH2 or -C(S)NH2, when n is 2 or 3, each Y may be
identical with or different from each other, R1 is C3-C8alkyl, C1-C6alkyl arbitrarily
substituted with R16, C3-C8cycloalkyl, C3-C8halocycloalkyl, C3-C8alkenyl, C3-
C8haloalkenyl, C3-C8alkynyl, C3-C8haloalkynyl, -N(R20)R19, -C(O)N(R10)R9, -C(S)N(R10)R9,
phenyl substituted with (Z)p1, D-8 to D-13, D-15 to D-18, D-21 to D-23, D-26, D-27, D-29
to D-37, D-39, D-40, D-42, D-45 to D-58, E-5, E-7, E-8, E-9, E-24, E-25, E-27, E-
E-30, E-31 or E-34, R2 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C1-C4alkoxy
CrC4alkyl, C1-C4alkylthio C1-C4alkyl, cyano C1-C6alkyl, C3-C6cycloalkyl, C3-C6alkenyl, C3-
C6alkynyl, -OH, C1-C6alkoxy, C1-C6alkylcarbonyloxy, C1-C6alkoxycarbonyloxy, C1-
C6alkylsulfonyloxy, C1-C6haloalkylthio, phenylthio, phenylthio substituted with (Z)p1,
C1-C6alkylsulfonyl, -SN(R18)R17, -NHR20, -N=CHR19b, -N=C(R19b)R19a, -C(O)R9, -C(O)OR9, -
C(O)SR9, -C(S)OR9 or -C(S)SR9, or R2 together with R1 may form 3- to 7-membered
ring with the nitrogen atom bonding them by forming C2-C6alkylene chain, in this
case, the alkylene chain may contain one oxygen atom or sulfur atom, R3 is C1-
C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C3-C6halocycloalkyl C1-C4alkyl,
C1-C4alkoxy C1-C4alkyl, C1-C4haloalkoxyC1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C1-
C4alkylsulfinyl C1-C4aIkyl, C1-C4alkylsulfonyl C1-C4alkyl, C1-C4haloalkylthio C1-
C4alkyl, C1-C4haloalkylsulfinyl C1-C4aIkyl,C1-C4haloalkylsulfonyl C1-C4alkyl, cyano
CrC6alkyl, C1-C4alkoxy C1-C4haloalkyl, C1-C4haloalkoxy C1-C4haloalkyl,C1-
C4alkylthio C1-C4haloalkyl, C1-C4alkylsulfinyl C1-C4haloalkyl, C1-C4aIkylsulfony C1-
C4haloalkyl, C1-C4haloalkylthio C1-C4haloalkyl, C1-C4haloalkylsulfinyl C1-C4haloalkyl,
C1-C4haloalkylsulfonyl C1-C4haloalkyl, cyano C1-C6haloalkyl, C3-C8cycloalkyl, C3-
25
C8halocycloalkyl, E-4 to E-7, E-23 to E-27 or E-28,
R4 is halogen atom, cyano, -OH, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-
C6haloalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-
C6haloalkylsulfonyl or tri(C1-C6alkyl)silyl,
R5 is C1-C6alkyl,C1-C6haloalkyl, C1-C3haloalkoxy C1-C3haloalkyl, C3-C8cycloalkyl, C3-
C8halocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, E-4
to E-9, E-23 to E-27 or E-28,
R6 is C1-C6alkyl, C1-C6haloalkyl, -S(O)2R9, -CHO, -C(O)R9, -C(O)OR9, -C(O)SR9,
-C(S)OR9 or -C(S)SR9,
R7 is hydrogen atom, C1-C6alkyl or C1-C6haloalkyl,
R9 is C1-C6alkyl, C1-C6chaloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C6alkoxy C1-
C4alkyl,
C1-C6alkylthio C1-C4alkyl, cyano C1-C6alkyl, phenyl C1-C4alkyl, C3-C8cycloalkyl, C3-
Cghalocycloalkyl, C3-C6alkenyl or C3-C6alkynyl,
R10 is hydrogen atom or C1-C6alkyl, or R10 together with R9 may form 5- or 6-
membered ring with the nitrogen atom bonding them by forming C4 or C5alkylene
chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom,
R11 is C1-C6alkyl or C1-C6haloalkyl, or R11 together with R9 may form 5- or 6-
membered ring with the atom bonding them by forming C2 or C3alkylene chain, in this
case, the alkylene chain may be arbitrarily substituted with C1-C6alkyl,
R15 is C1-C6alkyl or C1-C6haloalkyl,
R16 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, -OR25, -N(R26)R25,
-S(O)rR27, -S02NHR29, -S02N(R29)R28, -CHO, -C(O)R28, -C(O)OR28, -C(O)NHR29,
-C(O)N(R29)R28, -C(0)N(R29)OR28, -C(S)NHR29, -C(S)N(R29)R28, -C(R31)=NOH,
-C(R31)=NOR30, -C(=NR31)OR30, -C(=NR31)SR30, -C(=NR31)N(R29)R30, -
C(=NOR31)NHR29, -C(=NOR31)N(R29)R30, phenyl, phenyl substituted with (Z)p1, D-1 to
D-4, D-8 to D-42, D-47 to D-55, E-4 to E-12, E-14, E-16 to E-19, E-21 to E-23, E-26
to E-35, E-40 to E-45, E-48, M-2, M-3, M-5, M-8 to M-10, M-14, M-15 or M-16,
R17 is C1-C6alkyl, C1-C6alkoxycarbonyl C1-C4alkyl or C1-C6alkoxycarbonyl,
R18 is C1-C6alkyl or benzyl,
R19 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cyclaolakyl C1-C6alkyl, phenyl C1-C6alkyl,
phenyl C1-C6alkyl substituted with (Z)p1l C3-C6cycloalkyl, C3-C6alkenyl, C3-
Cehaloalkenyl, C3-C6alkynyl, -C(O)R28, -C(O)OR28, -C(O)NHR29, -C(O)N(R29)R28,
-C(S)NHR29, -C(S)N(R29)R28, C1-C6alkylsulfonyl,C1-C6haloalkylsulfonyl,
phenylsulfonyl, phenylsulfonyl substituted with (Z)p1, phenyl, phenyl substituted with
(Z)p1, D-1 to D-4, D-18, D-21, D-25, D-30 to D-35, D-47 to D-55 or D-56,
26
R19a is C1-C6alkyl,
R19b is hydrogen atom or C1-C6alkyl,
R20 is hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl,
cyano C1-C6alkyl, C3-C6alkenyl, C3-C6alkynyl, -CHO,C1-C6alkylcarbonyl, C1-
C6haloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6haloalkoxycarbonyl orC1-
C6alkylsulfonyl,
R22 is C1-C4alkyl or C1-C4haloa!kyl, or two R22s present on the same carbon atom
may together form oxo, or thioxo,
R23 is hydrogen atom, C1-C6alkyl, -CHO, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl,
C1-C6alkoxycarbonyl, C1-C6alkylsulfonyl or C1-C6haloalkylsulfonyl,
R25 is hydrogen atom, C1-C6alkyl, (C1-C6haloalkyl, -C(0)R33, -C(O)OR33, -C(O)SR33,
-C(O)NHR34, -C(0)N(R34)R33, -C(S)R33, -C(S)OR33, -C(S)SR33, -C(S)NHR34,
-C(S)N(R34)R33, -S(O)2R33, -S(O)2N(R34)R33, di(CrC6alkyl)thiophosphoryl, phenyl or
phenyl substituted with (Z)p1,
R26 is hydrogen atom or C1-C6alkyl, or R26 together with R25 may form 4- to 6-
membered ring with the nitrogen atom bonding them by forming C3-C5alkylene chain,
in this case, the alkylene chain may contain one oxygen atom, sulfur atom or
nitrogen atom, and may be substituted with C1-C6alkyl, oxo or thioxo,
R27 is C1-C6alkyl, C1-C6haloalkyl, tri( C1-C4alkyl)silyl C1-C4alkyl, C1-C6alkylthio,
-C(O)NHR34, -C(O)(R34)R33, -C(S)NHR34, -C(S)N(R34)R33, phenyl, phenyl
substituted with (Z)p1, D-47 or D-50,
R28 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R32, C3-C6cycloalkyl, C3-
C6halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl,
phenyl or phenyl substituted with (Z)p1,
R29 is hydrogen atom, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl, or R29 together with
R28 may form 3- to 6-membered ring with the nitrogen atom bonding them by forming
C2-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom
or sulfur atom,
R30 isC1-C6alkyl, C3-C6cycloalkyl C1-C4alkyl, phenyl C1-C4 alkyl, phenyl C1-C4alkyl
substituted with (Z)p1, C3-C8alkenyl or C3-C8alkynyl,
R31 is hydrogen atom or C1-C6alkyl, or R31 together with R30 may form 5- or 6-
membered ring with the atom bonding them by forming C2 or C3alkylene chain, in this
case, the alkylene chain may be arbitrarily substituted with C1-C6alkyl,
R32 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C4alkoxy,C1-
C4haloalkoxy, valkylthio, C1-C4haloalkylthio, C1-C4alkoxycarbonyl, -C(O)NH2, C1-
C4alkylaminocarbonyl, di(C1-C4alkyl)aminocarbonyl, phenyl or phenyl substituted
with (Z)P1,
R33 is C1-C6alkyl, C1-C6haloalkyl, C1-C4alkoxyC1-C4alkyl, C1-C4alkylthio C1-C4alkyl,
C1-C4alkylsulfonyl C1-C4alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with
(Z)p1, C3-C6cycloalkyl, C3-C6halocycloalkyl, C3-C6alkenyl, C3-C6alkynyl, phenyl or
phenyl substituted with (Z)p1,
R34 is hydrogen atom or C1-C6alkyl,
m is an integer of 1 to 3,
n is an integer of 0 to 2,
q2 is an integer of 0 to 3,
q3 is an integer of 0 to 2, and
q4 is an integer of 0 to 2.
(4) The isoxazoline-substituted benzamide compound or the salt thereof as set
forth in (3), wherein
A1 is carbon atom or nitrogen atom,
A2 and A3 are carbon atom,
GisG-1,
X is halogen atom, cyano, nitro, -SF5,C1-C6alkyl, CrC6alkyl arbitrarily substituted
with R4, C3-C8cycloalkyl, C3-C8halocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-
C6alkynyl, C2-C6haloalkynyl, -OR5, -OSO2R5, -S(O)rR5 or tri(C1-C6alkyl)silyl, when m
is 2 or 3, each X may be identical with or different from each other,
further, when two Xs are adjacent, the adjacent two Xs may form 5-membered or 6-
membered ring together with carbon atoms to which the two Xs are bonded by
forming -CF2OCF2-, -OCF20-, -CF2OCF20- or -OCF2CF2O-,
Y is halogen atom, cyano, nitro,C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4,
-OR5, -OS02R5, -S(O)rR5, -NHR7, -N(R7)R6, -C(0)NH2 or -C(S)NH2, when n is 2 or 3,
each Y may be identical with or different from each other,
R1 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R16, C3-C6cycloalkyl, C3-
C6halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl,
-N(R20)R19, -C(0)N(R10)R9, -C(S)N(R10)R9, phenyl substituted with (Z)p1, D-8, D-10,
D-11, D-13, D-15, D-17, D-18, D-21 to D-23, D-26, D-27, D-29 to D-37, D-39, D-40,
D-42, D-45, D-47, D-48, D-50, D-51, D-53, D-54, D-56, D-58, E-5, E-7 orE-9,
R2 is hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4Ikylthio C1-C4alkyl,
cyano C1-C6alkyl, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6alkynyl, -OH, C1
C6alkylcarbonyloxy, C1-C6alkylsulfonyloxy, -NH2, -C(O)R9, -C(O)OR9, -C(O)SR9,
-C(S)OR9 or -C(S)SR9,
R3 is C1-C6haloalkyl, C1-C4alkoxy C1-C4haloalkyl, C1-C4haloalkoxy C1-
C4haloalkyl,
C1-C4alkylthio C1-C4haloalkyl, C1-C4haloalkylthio C1-C4haloalkyl, cyano C1-
C6haloalkyl or C3-C8halocycloalkyl,
R4 is halogen atom, cyano, -OH, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-
C6haloalkylthio, C1-C6alkylsulfinyl, 4haloalkyl, cyano C1-
C6haloalkyl or C3-C8halocycloalkyl,
R4 is halogen atom, cyano, -OH, C1-C6alkoxC1-C6haloalkylsulfmyl, C1-C6alkylsulfonyl,
Cr
C6haloalkylsulfonyl or tri(C1-C6alkyl)silyl,
R5 is C1-C6alkyl,C1-C6haloalkyl, C1-C3haloalkoxy C1-C3haloalkyl, C3-C8cycloalkyl, C3-
Cghalocycloalkyl, C2-C6alkenyl, C2-C6Chaloalkenyl, C3-C6alkynyl or C3-C6haloalkynyl,
R6 is C1-C6alkyl, C1-C6haloalkyl, -CHO, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl,
C3-C6cycloalkylcarbonyl, C3-C6halocycloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-
C6haloalkoxycarbonyl, C1-C6alkylthiocarbonyl, C1-C6alkoxythiocarbonyl, C1-
C6alkyldithiocarbonyl, C1-C6alkylsulfonyl or C1-C6haloalkylsulfonyl,
R7 is hydrogen atom or C1-C6alkyl,
R9 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl,C1-C6alkoxy C1-C4alkyl,
C1-C6alkylthio C1-C4alkyl, cyano C1-C6alkyl, C3-C8cycloalkyl, C3-C6alkenyl or C3-
C6alkynyl,
R16 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, -OR25, -N(R26)R25,
-S(0)rR27, -S02NHR29, -S02N(R29)R28, -C(O)R28, -C(0)OR28, -C(0)NHR29,
-C(O)N(R29)R28, -C(O)N(R29)OR28, -C(S)NHR29, -C(S)N(R29)R28, -C(R31)=NOH,
-C(R31)=NOR30, -C(=NR31)OR30, -C(=NR31)SR30, phenyl, phenyl substituted with (Z)p1,
D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 to E-12, E-18, E-19, E-32, E-35, E-43,
M-2, M-3, M-5, M-8, M-9 or M-10,
R19 is C1-C6haloalkyl, C3-C6cycloalkyl, -C(O)R28, -C(O)OR28, -C(O)NHR29,
-C(O)N(R29)R28, -C(S)NHR29, -C(S)N(R29)R28, phenyl, phenyl substituted with (Z)p1,
D-3, D-4, D-21, D-47, D-50, D-51, D-53 or D-54,
R20 is hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl,
cyano C1-C6alkyl, C3-C6alkenyl, C3-C6alkynyl, -CHO,C1-C6alkylcarbonyl, C1-
C6alkoxycarbonyl or C1-C6alkylsulfonyl,
R25 is C1-C6alkyl, C1-C6haloalkyl,C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl, C1-
C6alkylaminocarbonyl, di(C1-C6alkyl)aminocarbonyl or C1-C6alkylsulfonyl,
R26 is hydrogen atom orC1-C6alkyl,
R27 is C1-C6alkyl, C1-C6haloalkyl or tri(C1-C4alkyl)silyl C1-C4alkyl,
R28 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, valkoxy C1-C4
C1-C4Ikylthio C1-C4alky, cyano C1-C6alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl
substituted with (Z)p1, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl,
phenyl or phenyl substituted with (Z)p1,
R29 is hydrogen atom, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl,
R30 is C1-C6alkyl or C3-C6cycloalkyl C1-C4alkyl,
R31 is hydrogen atom or C1-C6alkyl, or R31 together with R30 may form 5- or 6-
membered ring with the atom bonding them by forming C2 or C3alkylene chain.
(5) The isoxazoline-substituted benzamide compound or the salt thereof as set
forth in (4), wherein
X is halogen atom, cyano, nitro, -SF5,C1-C6alkylC1-C6haloalkyl, hydroxy C1-
C6haloalkyl, C1-C6alkoxy C1-C6haloalkyl, C1-C6haloalkoxy C1-C6haloalkyl, C3-
C8halocycloalkyl, -OR5, -OSO2R6 or -S(0)rR5, when m is 2 or 3, each X may be
identical with or different from each other,
Y is halogen atom, cyano, nitro, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-
C4haloalkoxy, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkylsulfonyl, C1-
C6haloalkylsulfonyl, -NHR7 or -N(R7)R6,
R1 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R16, C3-C6cycloalkyl, C3-
C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, -N(R20)R19, D-8, D-10, D-13, D-15, D-18,
D-21, D-34, D-35, D-50 or D-51,
R2 is hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, cyano C1-C6alkyl, C3-
C6alkynyl, -C(O)R9 or-C(O)OR9,
R3 is C1-C6haloalkyl or C3-C8halocycloalkyl,
R5 is C1-C6alkyl, C1-C6haloalkyl or C1-C4haloalkoxy C1-C4haloalkyl,
R6 is C1-C6alkyl, -CHO, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-
C6alkoxycarbonyl, C1-C6alkylthiocarbonyl, C1-C6alkoxythiocarbonyl, C1-
C6alkyldithiocarbonyl, C1-C6alkylsulfonyl or C1-C6haloalkylsulfonyl,
R9 is (C1-C6alkyl, C1-C6alkoxy C1-C4alkyl, C1-C6alkylthio C1-C4alkyl, C3-C8cycloalkyl,
C3-C6alkenyl or C3-C6alkynyl,
R16 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C6alkoxy, C1-
C6haloalkoxy, C1-C6alkylthio,C1-C6haloalkylthio, C1-C6alkylsulfinyl, Cr
C6haloalkylsulfinyl,C1-C6alkylsulfonyl,C1-C6haloalkylsulfonyl, C1-C6alkylcarbonyl,
-C(0)OR28, -C(O)NHR29, -C(O)N(R29)R28, -C(S)NH2, -C(R31)=NOH, -C(R31)=NOR30,
phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 to
E-7, E-10, E-11 orE-32,
R19 is C1-C6haloalkyl, -C(O)R28, -C(O)OR28, phenyl, phenyl substituted with (Z)p1, D-3,
D-4, D-21, D-47, D-50, D-51, D-53 or D-54,
30
R20 is hydrogen atom or C1-
R28 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C3-C6cycloalkyl, C3-
C6alkenyl or C3-C6alkynyl,
R29 is hydrogen atom or C1-C6alkyl,
R30 is C1-C6alkyl,
R31 is hydrogen atom or C1-C6alkyl, and
n is an integer of 0 or 1 .
(6) 3,5-Bis (substituted aryl) substituted isoxazoline compound of formula (2) or a
salt thereof:
wherein
A1 is carbon atom or nitrogen atom,
X1 is halogen atom, -SF5, C1-C6haloalkyl, hydroxy C1-C6hoalkyl, C1-C6alkoxyC1-
C6haloalkyl,C1-C6haloalkoxy C1-C6haloalkyl, C3-C8halocycalloalkyl, C1-C6haloalkoxy,
C1-C3haloalkoxy C1-C3haloalkoxy, C1-C6haloalkylthio,C1-C6haloalkylsulfinyl or C1-
C6haloalkylsulfonyl,
X2 is halogen atom, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, -OR5, -OS02R5 or -
S(O)rR5, when m1 is 2, each X2 may be identical with or different from each other,
Y is halogen atom, cyano, nitro, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-
C4haloalkoxy, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkylsulfonyl,C1-
C6haloalkylsulfonyl, -NHR7 or -N(R7)R6,
R3 is C1-C6haloalkyl or C3-C8halocycloalkyl,
R5 is C1-C6alkyl or C1-C6haloalkyl,
R6 is C1-C6alkyl, -CHO, valkylcarbonyl, C1-C6haloalkylcarbonyl, C1-
C6alkoxycarbonyl, C1-C6alkylthiocarbonyl, C1-C6alkoxythiocarbonyl, C1-
C6alkyldithiocarbonyl, C1-C6alkylsulfonyl or C1-C6haloalkylsulfonyl,
R7 is hydrogen atom or C1-C6alkyl,
R is halogen atom, cyano, nitro, -NH2, halosulfonyloxy, C1-C6alkylsulfonyloxy, C1-
C6haloalkylsulfonyloxy, phenylsulfonyloxy, phenylsulfonyloxy substituted with (Z)p1 or
-C(0)Ra,
Ra is halogen atom, -OH, C1-C6alkoxy, 1-pyrazolyl, 1-imidazolyl or 1-triazolyl,
Z is halogen atom, C1-C6alkyl or C1-C6haloalkyl, when p1 is an integer of 2 or more,
each Z may be identical with or different from each other,
m1 is an integer of 0 to 2,
n is an integer of 0 or 1,
p1 is an integer of 1 or 5, and
r is an integer of 0 to 2.
(7) 3,5-Bis (substituted aryl) substituted isoxazoline compound or the salt thereof
as set forth in (6), wherein
(a) in case where R is halosulfonyloxy,C1-C6haloalkylsulfonyloxy, phenylsulfonyloxy
or phenylsulfonyloxy substituted with (Z)p1, Y is halogen atom, cyano, nitro, C1-
C6alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C6alkylthio, C1-
C6haloalkylthio, C1-C6alkylsulfonyl orC1-C6haloalkylsulfonyl,
(b) in case where R is -C(O)Ra, Y is cyano, nitro, C1-C6alkyl, C1-C4haloalkyl, C1-
C6haloalkylthio or C1-C6haloalkylsulfonyl,
(c) in case where, R is halogen atom, cyano, nitro or -NH2, Y is cyano, C1-C6alkyl,
C1-C6haloalkyl, C1-C6haloalkylthio or (C1-C6haloalkylsulfonyl.
(8) 4-Hydroxyiminomethyl substitu6ted benzamide compound of formula (3) or
a
salt thereof:
wherein
A1 is carbon atom or nitrogen atom,
J is hydrogen atom or halogen atom,
W is oxygen atom or sulfur atom,
Y is halogen atom, cyano, nitro,C1-C6Ikyl, C1-C4haloalkyl, C1-C4alkoxy, C1-
C4haloalkoxy,C1-C6alkylsulfonyl,C1-C6haloalkylsulfonyl or -N(R7)R6,
R1 is C1-C6alkyl, C1-C6alkyl, arbitrarily substituted with R16, C3-C6cycloalkyl, C3-
C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, -N(R20)R19, D-8, D-10, D-13, D-15, D-18,
D-21, D-34, D-35, D-50 or D-51,
R2 is hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, cyano C1-C6alkyl, C3-
32
C6alkynyl, -C(O)R9 or -C(O)OR9,
R6 is -CHO, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-
C6alkylthiocarbonyl, C1-C6alkoxythiocarbonyl, C1-C6alkyldithiocarbonyl, C1-
C6alkylsulfonyl or C1-C6haloalkylsulfonyl,
R7 is hydrogen atom or C1-C6alkyl,
R9 is C1-C6alkyl, C1-C6alkoxy C1-C4alkyl, C1-C6alkylthio C1-C4alkyl, C3-C8cycloalkyl,
C3-C6alkenyl or C3-C6alkynyl,
R16 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl,C1-C6alkoxy, C1-
C6haloalkoxy, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl,C1-C6alkylcarbonyl,
-C(O)OR28, -C(O)NHR29, -C(O)N(R29)R28, -C(S)NH2, -C(R31)=NOH, -C(R31)=NOR30,
phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 to
E-7, E-10, E-11 orE-32,
D-1 to D-4, D-8 to D-38, D-47 to D-54 and D-55 are aromatic heterocyclic rings of the
following formulae, respectively,
Z is halogen atom, cyano, nitro,C1-C6alkyl, C1-C6haloalkyl,C1-C6alkoxy, C1-
C6haloalkoxy, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl,C1-C6alkoxycarbonyl,
-C(0)NH2,C1-C6alkylaminocarbonyl, di(C1-C6alkyl)aminocarbonyl, -C(S)NH2,
-S(O)2NH2l C1-C6alkylaminosulfonyl or di(C1-C6alky)aminosulfonyl, when p1, p2, p3
or p4 is an integer of 2 or more, each Z may be identical with or different from each
other,
R15 is C1-C6alkyl, phenyl or phenyl substituted with (Z)p1,
E-4, E-5, E-10, E-11 or E-32 is a saturated heterocyclic ring of the following
formulae, respectively
2\ ro22\ ro22)q2 (R )q2
O
O O ' O'
Jq3
E-4 E-5 E-10 E-11 E-32
R19 is (C1-C6haloalkyl, -C(O)R28, -C(O)OR28, phenyl, phenyl substituted with (Z)p1, D-3,
D-4, D-21, D-47, D-50, D-51, D-53 or D-54, R20
is hydrogen atom or C1-C6alkyl, R22 is C1-
C4alkyl,
R28 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C3-C6cycloalkyl, C3-
35
(Z)p3 (Z)p3
o o
)
C6alkenyl or C3-C6alkynyl,
R29 is hydrogen atom or C1-C6alkyl,
R30 isC1-C6alkyl,
R31 is C1-C6alkyl,
n is an integer of 0 or 1, with a proviso that n is 1 when R1 and R2 are methyl at the
same time,
p1 is an integer of 1 to 5,
p2 is an integer of 0 to 4,
p3 is an integer of 0 to 3,
p4 is an integer of 0 to 2,
p5 is an integer of 0 or 1,
q2 is an integer of 0 to 3, and
q3 is an integer of 0 to 2
(9) 4-Hydroxyiminomethyl substituted benzamide compound or the salt thereof as
set forth in (8), wherein
R1 is C1-C6alkyl arbitrarily substituted with R16, C3-C6cycloalkyl, C3-C6alkenyl, C3-
C6haloalkenyl, C3-C6alkynyl, -N(R20)R19, D-8, D-10, D-13, D-15, D-18, D-21, D-34, D-35,
D-50 or D-51,
R16 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C6alkoxy, C1-
C6haloalkoxy,C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, -C(O)OR28, -C(O)NHR29,
C(O)N(R29)R28, -C(S)NH2, -C(R31)=NOH, -C(R31)=NOR30, D-1 to D-4, D-8 to D-38, D-47 to
D-55, E-4, E-5, E-10, E-11 or E-32.
(10) Substituted alkenylbenzene compound of formula (4):
(4)
wherein
X1 is halogen atom, -SF5, C1-C6haloalkyl, hydroxy C1-
C6haloalkyl, C1-C6alkoxy C1-
C6haloalkyl, C1-C6haloalkoxy C1-C6haloalkyl, C3-C8halocycloalkyl,
C1-C6haloalkoxy,
C1-C3haloalkoxy C1-C3haloalkoxy, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl or C1-
C6haloalkylsulfonyl,
X3 is hydrogen atom, halogen atom, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, -OR5,
-OSO2R5 or -S(O)rR5,
36
X4 is hydrogen atom, halogen atom, cyano, nitro, C1-C6alkyl, -OH, C1-C6alkoxy or
C1-C6haloalkoxy,
R3 is C1-C6alkyl that is arbitrarily substituted with two or more arbitrarily halogen
atoms, or C3-C8halocycloalkyl with a proviso that in case where X1 is fluorine atom,
chlorine atom or -CF3 and both X3 and X4 are hydrogen atom, in case where both X1
and X3 are fluorine atom, and X4 is hydrogen atom, and in case where both X1 and X3
are -CF3, and X4 is hydrogen atom, R3 is -CHF2, -CHFCI, -CHFBr, -CHCI2, -CF2CI, -
CF2Br, -CF2I, -CFCI2, -CFCIBr, -CFBr2, -CCI3, C2-C6haloalkyl or C3-C8halocycloalkyl, R5
isC1-C6alkyl or C1-C6haloalkyl, r is an integer of 0 to 2.
(11) The substituted alkenylbenzene compound as set forth in (10), wherein
X1 is halogen atom, -SF5 C1-C6haloalkyl, C1-C6haloalkoxy, C1-C6haloalkylthio, C1-
C6haloalkylsulfinyl or C1-C6haloalkylsulfonyl,
X3 is hydrogen atom, halogen atom, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-
C6alkoxy, C1-C6haloalkoxy,C1-C6alkylthio or C1-C6haloalkylthio,
X4 is hydrogen atom, halogen atom, cyano, nitro, methyl, -OH, C1-C4alkoxy or
C1-
C4haloalkoxy,
R3 is -CHF2) -CF3, -CF2CI, -CF2Br or -CF2CF3, with a proviso that in case where X1 is
fluorine atom, chlorine atom or -CF3 and both X3 and X4 are hydrogen atom, in case
where both X1 and X3 are fluorine atom, and X4 is hydrogen atom, and in case where
both X1 and X3 are -CF3, and X4 is hydrogen atom, R3 is -CHF2, -CF2CI, -CF2Br or
-CF2CF3.
(12) A pesticide containing as an active ingredient one or more selected from
isoxazoline-substituted benzamide compound and the salt thereof as set forth in (1)
to (5).
(13) An agrochemical containing as an active ingredient one or more selected from
isoxazoline-substituted benzamide compound and the salt thereof as set forth in (1)
to (5).
(14) An endo- or ecto-parasiticide for mammals or birds containing as an active
ingredient one or more selected from isoxazoline-substituted benzamide compound
and the salt thereof as set forth in (1) to (5).
(15) An insecticide or acaricide containing as an active ingredient one or more
selected from isoxazoline-substituted benzamide compound and the salt thereof as
set forth in (1) to (5).
Effect of the Invention
[0009] The compound according to the present invention has an excellent
insecticidal and acaricidal activity for many agricultural insect pests, spider mites,
endo- or ecto-parasiticide for mammals or birds, and exerts a control effect sufficient
for pest insects that acquire resistance against exiting insecticides. Further, the
compound has little adverse affect on mammals, fishes and beneficial insects, and
has a low persistency and a low impact on the environment. Therefore, the present
invention can provide a useful and novel pesticide.
Best Mode for carrying out the Invention
[0010] Active compounds used as the pesticide in the present invention are
generally the compounds of formulae (1) to (5) mentioned above, and the
compounds of formulae (6) to (11) mentioned above are novel production
intermediates used for the production of these active compounds. These
intermediates contain specific compounds themselves having control activity against
specific pests that can be used as a control agent for the pest. [0011] In the
compounds included in the present invention, some compounds have geometrical
isomers of E-form and Z-form depending on the kind of substituents. The present
invention includes these E-forms, Z-forms and mixtures containing E-form and Zform
in an arbitrary proportion. In addition, the compounds included in the present
invention have optically active forms resulting from the presence of 1 or more
asymmetric carbon atoms, and the present invention includes all optically active
forms or racemates. Further, in the compounds of formula (1) according to the
present invention, some compounds wherein R2 is hydrogen atom are present in
tautomer, and the present invention includes these structures, R3 O-N
H
[0012] The compounds included in the present invention can be converted to
acid addition salts for example salts of hydrohalide acid such as hydrofluoric acid,
hydrochloric acid, hydrobromic acid, hydriodic acid or the like, salts of inorganic
acids such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid or
the like, salts of sulfonic acid such as methansulfonic acid, ethansulfonic acid,
trufluoromethansulfonic acid, benzene sulfonic acid, p-toluene sulfonic acid or the
like, salts of carboxylic acid such as formic acid, acetic acid, propionic acid,
trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid,
succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid,
citric acid or the like, or salts of amino acid such as glutamic acid, aspartic acid or the
like, according to a conventional method.
[0013] The compounds included in the present invention can be converted to
matal salts for example salts of alkali metal such as lithium, sodium, potassium, salts
of alkaline earth metal such as calcium, barium, magnesium, or salts of aluminum,
according to a conventional method.
[0014] Hereinafter, concrete examples of each substituent shown in the
specification are described. In the specification, "n-" means normal, "i-" means iso,
"s-" means secondary, and "t-" means tertiary, and "Ph" means phenyl. [0015]
Halogen atom in the compounds of the present invention includes flurorine atom,
chlorine atom, bromine atom and iodine atom. In the interim, the indication of
"halo" in the specification also means these halogen atoms. [0016] In the
specification, the indication of "Ca-Cbalkyl" means straight-chain or branched-chain
hydrocarbon groups having carbon atom number of a to b, and includes for example
methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, n-pentyl, 1-
methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-
dimethylpropyl, neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl,
4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-
dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-
trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-l-methylpropyl, 1-ethyl-2-methylpropyl,
heptyl, 5-methylhexyl, 2-ethylpentyl, octyl, 2-ethylhexyl, nonyl, 2-methyloctyl, decyl,
2-methylnonyl, undecyl, 2-methyldecyl, dodecyl and the like. It is selected from the
scope of the indicated carbon atom number.
[0017] In the specification, the indication of "Ca-Cbhaloalkyl" means straight-chain
or branched-chain hydrocarbon groups having carbon atom number of a to b that a
hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily
substituted with a halogen atom (halogen atoms). In this case, if it is substituted
with two or more halogen atoms, these halogen atoms may be identical with or
different from each other. Concrete examples thereof are for example fluoromethyl,
chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl,
trichloromethyl, bromodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl,
2,2-difluoroethyl, 2-chloro-2-fluoroethyl, 2,2-dichloroethyl, 2-bromo-2-fluoroethyl, 2-
bromo-2-chloroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-
fluoroethyl, 2,2,2-trichloroethyl, 2-bromo-2,2-difluoroethyl, 2-bromo-2-chloro-2-
fluoroethyl, 2-bromo-2,2-dichloroethyl, pentafluoroethyl, 2-fluoropropyl, 2-
chloropropyl, 2-bromopropyl, 2,3-dichloropropyl, 2,3-dibromopropyl, 3,3,3-
trifluoropropyl, 3-bromo-3,3-difluoropropyl, 2,2,3,3-tetrafluoropropyl, 2-chloro-3,3,3-
trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, 2,2,2-trifluoro-1-trifluoromethylethyl,
heptafluoropropyl, 1,2,2,2-tetrafluoro-l-trifluoromethylethyl, 2,2,3,3,4,4-
hexafluorobutyl, 2,2,3,4,4,4-hexafluorobutyl, 2,2,3,3,4,4,4-heptafluorobutyl,
nonafluorobutyl, 5-chloro-2,2,3,4,4,5,5-heptafluoropentyl, and the like. It is selected
from the scope of the indicated carbon atom number.
[0018] In the specification, the indication of "hydroxy Ca-Cbalkyl" means straightchain
or branched-chain alkyl groups having carbon atom number of a to b that a
hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily
substituted with a hydroxy group (hydroxy groups). Concrete examples thereof are
for example hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxypropyl, 3-
hydroxypropyl, 2-hydroxybutyl, and the like. It is selected from the scope of the
indicated carbon atom number.
[0019] In the specification, the indication of "cyano Ca-Cbalkyl" means straightchain
or branched-chain alkyl groups having carbon atom number of a to b that a
hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily
substituted with a cyano group (cyano groups). Concrete examples thereof are for
example cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 2-cyanopropyl, 3-cyanopropyl,
2-cyanobutyl, and the like. It is selected from the scope of the indicated carbon
atom number.
[0020] In the specification, the indication of "Ca-Cbcycloalkyl" means cyclic
hydrocarbon groups having carbon atom number of a to b, and can form 3-
membered to 6-membered single ring or conjugated ring structure. In addition,
each ring may be arbitrarily substituted alkyl group in the scope of the indicated
carbon atom number. Concrete examples thereof are for example cyclopropyl, 1-
methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,2,3,3-
tetramethylcyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-
methylcyclopentyl, cyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl,
4-methylcyclohexyl, bicyclo[2.2.1]heptan-2-yl and the like. It is selected from the
scope of the indicated carbon atom number.
[0021] In the specification, the indication of "Ca-Cbhalocycloalkyl" means cyclic
hydrocarbon groups having carbon atom number of a to b that a hydrogen atom
(hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with a
halogen atom (halogen atoms), and can form 3-membered to 6-membered single
ring or conjugated ring structure. In addition, each ring may be arbitrarily
substituted alkyl group in the scope of the indicated carbon atom number. The
substitution for halogen atom may be in the ring structure moiety, the side chain
moiety or both of them. Further, if it is substituted with two or more halogen atoms,
these halogen atoms may be identical with or different from each other. Concrete
examples thereof are for example 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl,
2,2-difluoro-1-methylcyclopropyl, 2,2-dichloro-1-methylcyclopropyl, 2,2-dibromo-1-
methylcyclopropyl, 2,2-dichloro-3,3-dimethylcyclopropyl,
2,2,3,3-tetrafluorocyclobutyl, 2-trifluoromethylcyclohexyl, 3-trifluoromethylcyclohexyl,
4-trifluoromethylcyclohexyl and the like. It is selected from the scope of the
indicated carbon atom number.
[0022] In the specification, the indication of "Ca-Cbalkenyl" means straight-chain
or branched-chain unsaturated hydrocarbon groups having carbon atom number of a
to b and having 1 or more double bonds. Concrete examples thereof are for
example vinyl, 1-propenyl, 1-methylethenyl, 2-propenyl, 2-butenyl, 1-methyl-2-
propenyl, 2-methyl-2-propenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 2-hexenyl, 2-
methyl-2-pentenyl, 2,4-dimethyl-2,6-heptadienyl, 3,7-dimethyl-2,6-octadienyl, and
the like. It is selected from the scope of the indicated carbon atom number. [0023]
In the specification, the indication of "Ca-Cbhalolkenyl" means straight-chain or
branched-chain unsaturated hydrocarbon groups having carbon atom number of a
to b and having 1 or more double bonds, which a hydrogen atom (hydrogen atoms)
bonded to carbon atom is (are) arbitrarily substituted with a halogen atom (halogen
atoms). In this case, if it is substituted with two or more halogen atoms, these
halogen atoms may be identical with or different from each other. Concrete
examples thereof are for example 2,2-dichlorovinyl, 2-fluoro-2-propenyl, 2-chloro-2-
propenyl, 2-bromo-2-propenyl, 3-bromo-2-propenyl, 3,3-difluoro-2-propenyl, 2,3-
dichloro-2-propenyl, 3,3-dichloro-2-propenyl, 2,3-dibromo-2-propenyl, 2,3,3-trifluoro-
2-propenyl, 1-trifluoromethylvinyl, 2,3,3-trichloro-2-propenyl, 2-bromo-2-butenyl, 3-
bromo-2-methyl-2-propenyl,
4,4-difluoro-3-butenyl, 3,4,4-trifluoro-3-butenyl, 3-chioro-4,4,4-trmuoro-ii-Duienyi, and
the like. It is selected from the scope of the indicated carbon atom number. [0024]
In the specification, the indication of "Ca-Cbcycloalkenyl" means cyclic unsaturated
hydrocarbon groups having carbon atom number of a to b and having 1 or more
double bonds, and can form 3-membered to 6-membered single ring or conjugated
ring structure. In addition, each ring may be arbitrarily substituted alkyl group in the
scope of the indicated carbon atom number, and further the double bond may be
either endo- or exo-form. Concrete examples thereof are for example 2-
cyclopenten-1-yl, 3-cyclopenten-1-yl, 2-cyclohexen-1-yl, 3-cyclohexen-1-yl, bicyclo
[2.2.1]-5-hepten-2-yl and the like. It is selected from the scope of the indicated
carbon atom number.
[0025] In the specification, the indication of "Ca-Cbhaloycloalkenyl" means cyclic
unsaturated hydrocarbon groups having carbon atom number of a to b and having 1
or more double bonds, which a hydrogen atom (hydrogen atoms) bonded to carbon
atom is (are) arbitrarily substituted with a halogen atom (halogen atoms), and can
form 3-membered to 6-membered single ring or conjugated ring structure. In
addition, each ring may be arbitrarily substituted alkyl group in the scope of the
indicated carbon atom number, and further the double bond may be either endo- or
exo-form. The substitution for halogen atom may be in the ring structure moiety, the
side chain moiety or both of them. Further, if it is substituted with two or more
halogen atoms, these halogen atoms may be identical with or different from each
other. Concrete examples thereof are for example 2-chlorobicyclo [2.2.1 ]-5-hepten-
2-yl and the like. It is selected from the scope of the indicated carbon atom
number.
[0026] In the specification, the indication of "Ca-Cbalkynyl" means straight-chain
or branched-chain unsaturated hydrocarbon groups having carbon atom number of a
to b and having 1 or more triple bonds. Concrete examples thereof are for example
ethynyl, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl, 2-butynyl, 2-pentynyl, 1-methyl-
2-butynyl, 2-hexynyl, and the like. It is selected from the scope of the indicated
carbon atom number.
[0027] In the specification, the indication of "Ca-Cbhalolkynyl" means straight-chain
or branched-chain unsaturated hydrocarbon groups having carbon atom number of a
to b and having 1 or more triple bonds, which a hydrogen atom (hydrogen atoms)
bonded to carbon atom is (are) arbitrarily substituted with a halogen atom (halogen
atoms). In this case, if it is substituted with two or more
halogen atoms, these halogen atoms may be identical with or different from each
other. Concrete examples thereof are for example 2-chloroethynyl, 2-o-2-propynyl,
and the
like. It is selected from the scope of the indicated carbon atom number.
[0028] In the specification, the indication of "Ca-Cbabromoethynyl,
2-iodoethynyl, 3-chloro-2-propynyl, 3-bromo-2-propynyl, 3-iodlkoxy" means alkyl-Ogroups
wherein the alkyl has carbon atom number of a to b, and includes for example
methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butyloxy, s-butyloxy, i-butyloxy,
t-butyloxy, n-pentyloxy, n-hexyloxy and the like. It is selected from the scope of the
indicated carbon atom number.
[0029] In the specification, the indication of "Ca-Cbhaloalkoxy" means
haloalkyl-O- groups wherein the haloalkyl has carbon atom number of a to b, and
includes for example difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy,
bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy,
1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, 2-bromo-
1,1,2-trifluoroethoxy, 2,2-dichloro-1,1,2-trifluoroethoxy, pentafluoroethoxy,
2,2,2-trichloro-1,1-difluoroethoxy, 2-bromo-1,1,2,2-tetrafluoroethoxy,
2,2,3,3-tetrafluoropropyloxy, 1,1,2,3,3,3-hexafluoropropyloxy, 2,2,2-trifluoro-
1-trifluoromethylethoxy, heptafluoropropyloxy, 2-bromo-
1,1,2,3,3,3-hexafluoropropyloxy, and the like. It is selected from the scope of the
indicated carbon atom number.
[0030] In the specification, the indication of "Ca-Cbalkenyloxy" means alkenyl-
O- groups wherein the alkenyl has carbon atom number of a to b, and includes for
example 2-propenyloxy, 2-butenyloxy, 2-methyl-2-peopenyloxy, 3-methyl-
2-butenyloxy, and the like. It is selected from the scope of the indicated carbon
atom number.
[0031] In the specification, the indication of "Ca-Cbhaloalkenyloxy" means
haloalkenyl-O- groups wherein the haloalkenyl has carbon atom number of a to b,
and includes for example 2-chloro-2-propenyl, 3-chloro-2-propenyl, 3,3-difluoro-
2-propenyl, 3,3-dichloro-2-propenyl, 2,3,3-trifluoro-2-propenyl, and the like. It is
selected from the scope of the indicated carbon atom number.
[0032] In the specification, the indication of "Ca-Cbalkylthio" means alkyl-
S- groups wherein the alkyl has carbon atom number of a to b, and includes for
example methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, s-butylthio,
i-butylthio, t-butylthio, n-pentylthio, n-hexylthio and the like. It is selected from the
scope of the indicated carbon atom number.
[0033] In the specification, the indication of "Ca-Cbhaloalkylthio" means
haloalkyl-S- groups wherein the haloalkyl has carbon atom number of a to b, and
includes for example difluoromethylthio, trifluoromethylthio, bromodifluoromethylthio,
2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 1,1,2-trifluoro-2-chloroethylthio,
pentafluoroethylthio, 2-bromo-1,1,2,2-tetrafluoroethylthio, heptafluoropropylthio,
1,2,2,2-tetrafluoro-1-trifluoromethylthio, 1,2,2,2-tetrafluoro-1-trifluoroethylthio,
nonafluorobutylthio, and the like. It is selected from the scope of the indicated
carbon atom number.
[0034] In the specification, the indication of "Ca-Cbalkylsulfinyl" means
alkyl-S(O)- groups wherein the alkyl has carbon atom number of a to b, and includes
for example methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl,
n-butylsulfinyl, s-butylsulfinyl, i-butylsulfinyl, t-butylsulfinyl, and the like. It is
selected from the scope of the indicated carbon atom number.
[0035] In the specification, the indication of "Ca-Cbhaloalkylsulfinyl" means
haloalkyl-S(O)- groups wherein the haloalkyl has carbon atom number of a to b, and
includes for example difluoromethylsulfinyl, trifluoromethylsulfinyl,
bromodifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2-bromo-
1,1,2,2-tetrafluoroethylsulfinyl, 1,2,2,2-tetrafluoro-1-trifluoromethylethylsulfinyl,
nonafluorobutylsulfinyl, and the like. It is selected from the scope of the indicated
carbon atom number.
[0036] In the specification, the indication of "Ca-Cbalkylsulfonyl" means
alkyl-S02- groups wherein the alkyl has carbon atom number of a to b, and includes
for example methanesulfonyl, ethanesulfonyl, n-propylsulfonyl, i-propylsulfonyl,
n-butylsulfonyl, s-butylsulfonyl, i-butylsulfonyl, t-butylsulfonyl, n-pentylsulfonyl,
n-hexylsulfonyl, and the like. It is selected from the scope of the indicated carbon
atom number.
[0037] In the specification, the indication of "Ca-Cbhaloalkylsulfonyl" means
haloalkyl-S02- groups wherein the haloalkyl has carbon atom number of a to b, and
includes for example difluoromethanesulfonyl, trifluoromethanesulfonyl,
chlorodifluoromethanesulfonyl, bromodifluoromethanesulfonyl,
2,2,2-trifluoroethanesulfonyl, 1,1,2,2-tetrafluoroethanesulfonyl, 1,1,2-trifluoro-
2-chloroethanesulfonyl, and the like. It is selected from the scope of the indicated
carbon atom number.
[0038] In the specification, the indication of "Ca-Cbalkylamino" means amino
groups, which either hydrogen atom is substituted with the above-mentioned alkyl
44
group having carbon atom number of a to b, and includes for example methylamino,
ethylamino, n-propylamino, i-propylamino, n-butylamino, i-butylamino, t-butylamino,
and the like. It is selected from the scope of the indicated carbon atom number.
[0039] In the specification, the indication of "di(Ca-Cbalkyl)amino" means amino
groups, which both hydrogen atoms are substituted with the above-mentioned alkyl
groups having carbon atom number of a to b that may be identical with or different
from each other, and includes for example dimethylamino, ethyl(methyl)amino,
diethylamino, n-propyl(methyl)amino, i-propyl(methyl)amino, di(n-propyl)amino, nbutyl(
methyl)amino, i-butyl(methyl)amino, t-butyl(methyl)amino, and the like. It is
selected from the scope of the indicated carbon atom number. [0040] In the
specification, the indication of "Ca-Cbalkylcarbonyl" means alkyl-C(0)- groups
wherein the alkyl has carbon atom number of a to b, and includes for example
CH3C(O)-, CH3CH2C(0)-, CH3CH2CH2C(0)-, (CH3)2CHC(O)-, CH3(CH2)3C(0)-,
(CH3)2CHCH2C(0)-, CH3CH2CH(CH3)C(O)-, (CH3)3CC(O)-, CH3(CH2)4C(O)-,
CH3(CH2)5C(O)-, and the like. It is selected from the scope of the indicated carbon
atom number.
[0041] In the specification, the indication of "Ca-Cbhaloalkylcarbonyl" means
haloalkyl-C(O)- groups wherein the haloalkyl has carbon atom number of a to b, and
includes for example FCH2C(0)-, CICH2C(O)-, F2CHC(O)-, CI2CHC(O)-, CF3C(O)-,
CICF2C(O)-, BrCF2C(0)-, CCI3C(0)-, CF3CF2C(O)-, CICH2CH2CH2C(O)-,
CF3CF2CF2C(O)-, CICH2C(CH3)2C(O)-, and the like. It is selected from the scope of
the indicated carbon atom number.
[0042] In the specification, the indication of "Ca-Cbcycloalkylcarbonyl" means
cycloalkyl-C(O)- groups wherein the cycloalkyl has carbon atom number of a to b,
and includes for example cyclopropyl-C(O)-, l-methylcyclopropyl-C(O)-, 2-
methycyclopropyl-C(O)-, 2,2-dimethycyclopropyl-C(O)-, 2,2,3,3-
tetramethycyclopropyl-C(O)-, cyclobutyl-C(O)-, cyclopentyl-C(O)-, cyclohexyl-C(O)-,
and the like. It is selected from the scope of the indicated carbon atom number.
[0043] In the specification, the indication of "Ca-Cbhalocycloalkylcarbonyl" means
halocycloalkyl-C(O)- groups wherein the halocycloalkyl has carbon atom number of a
to b, and includes for example 2,2-dichlorocyclopropyl-C(0)-, 2,2-
dibromocyclopropyl-C(O)-, 2,2-difluoro-1-methylcyclopropyl-C(O)-, 2,2-dichloro-1-
methylcyclopropyl-C(O)-, 2,2-dibromo-1-methylcyclopropyl-C(O)-, 2,2-dichloro-3,3-
dimethylcyclopropyl-C(O)-, and the like. It is selected from the scope of the
indicated carbon atom number.
[0044] In the specification, the indication of "Ca-Cbalkoxycarbonyl" means alkyl-OC(
O)- groups wherein the alkyl has carbon atom number of a to b, and includes for
example CH3OC(O)-, CH3CH2OC(O)-, CH3CH2CH2OC(O)-, (CH3)2CHOC(O)-,
CH3(CH2)3OC(0)-, (CH3)2CHCH2OC(0)-, (CH3)3COC(O)-, and the like. It is selected
from the scope of the indicated carbon atom number.
[0045] In the specification, the indication of "Ca-Cbhaloalkoxycarbonyl" means
haloalkyl-O-C(O)- groups wherein the haloalkyl has carbon atom number of a to b,
and includes for example CICH2CH2OC(O)-, CF3CH2OC(O)-, and the like. It is
selected from the scope of the indicated carbon atom number. [0046] In the
specification, the indication of "Ca-Cbalkylthiocarbonyl" means alkyl-S-C(O)- groups
wherein the alkyl has carbon atom number of a to b, and includes for example
CH3SC(O)-, CH3CH2SC(O)-, CH3CH2CH2SC(O)-, (CH3)2CHSC(O)-, CH3(CH2)3SC(0)-,
(CH3)2CHCH2SC(O)-, (CH3)3CSC(0)-, and the like. It is selected from the scope of the
indicated carbon atom number.
[0047] In the specification, the indication of "Ca-Cbalkoxythiocarbonyl" means
alkyl-O-C(S)- groups wherein the alkyl has carbon atom number of a to b, and
includes for example CH3OC(S)-, CH3CH2OC(S)-, and the like. It is selected from the
scope of the indicated carbon atom number.
[0048] In the specification, the indication of "Ca-Cbalkyldithiocarbonyl" means
alkyl-S-C(S)- groups wherein the alkyl has carbon atom number of a to b, and
includes for example CH3SC(S)-, CH3CH2SC(S)-, and the like. It is selected from the
scope of the indicated carbon atom number.
[0049] In the specification, the indication of "Ca-Cbalkylaminocarbonyl" means
carbamoyl groups, which either hydrogen atom is substituted with the abovementioned
alkyl group having carbon atom number of a to b, and includes for
example CH3NHC(0)-, CH3CH2NHC(O)-, CH3CH2CH2NHC(O)-, (CH3)2CHNHC(O)-,
CH3(CH2)3NHC(0)-, (CH3)2CHCH2NHC(0)-, CH3CH2CH(CH3)NHC(O)-, (CH3)3CNHC(0)-,
and the like. It is selected from the scope of the indicated carbon atom number.
[0050] In the specification, the indication of "Ca-Cbcycloalkylminocarbonyl" means
carbamoyl groups, which either hydrogen atom is substituted with the abovementioned
cycloalkyl group having carbon atom number of a to b, and includes for
example cyclopropyl-NHC(O)-, cyclobutyl-NHC(O)-, cyclopentyl-NHC(O)-,
cyclohexyl-NHC(O)-, and the like. It is selected from the scope of the indicated
carbon atom number.
[0051] In the specification, the indication of "di(Ca-Cbalkyl)aminocarbonyl" means
carbamoyl groups, which both hydrogen atoms are substituted with the abovementioned
alkyl group having carbon atom number of a to b that may be identical
with or different from each other, and includes for example (CH3)2NC(0)-,
CH3CH2N(CH3)C(0)-, (CH3CH2)2NC(0)-, (CH3CH2CH2)2NC(O)-,
(CH3CH2CH2CH2)2NC(O)-, and the like. It is selected from the scope of the indicated
carbon atom number.
[0052] In the specification, the indication of "Ca-Cbalkylaminothiocarbonyl" means
thiocarbamoyl groups, which either hydrogen atom is substituted with the abovementioned
alkyl group having carbon atom number of a to b, and includes for
example CH3NHC(S)-, CH3CH2NHC(S)-, CH3CH2CH2NHC(S)-, (CH3)2CHNHC(S)-,
CH3(CH2)3NHC(S)-, (CH3)2CHCH2NHC(S)-, CH3CH2CH(CH3)NHC(S)-, (CH3)3CNHC(S)-,
and the like. It is selected from the scope of the indicated carbon atom number.
[0053] In the specification, the indication of "di(Ca-Cbalkyl)aminothiocarbonyl"
means thiocarbamoyl groups, which both hydrogen atoms are substituted with the
above-mentioned alkyl group having carbon atom number of a to b that may be
identical with or different from each other, and includes for example (CH3)2NC(S)-,
CH3CH2N(CH3)C(S)-, (CH3CH2)2NC(S)-, (CH3CH2CH2)2NC(S)-, (CH3CH2CH2CH2)2NC(S)-,
and the like. It is selected from the scope of the indicated carbon atom number.
[0054] In the specification, the indication of "Ca-Cbalkylaminosulfonyl" means
sulfamoyl groups, which either hydrogen atom is substituted with the abovementioned
alkyl group having carbon atom number of a to b, and includes for
example CH3NHSO2-, CH3CH2NHSO2-, CH3CH2CH2NHSO2-, (CH3)2CHNHSO2-,
CH3(CH2)3NHSO2-, (CH3)2CHCH2NHS02-, CH3CH2CH(CH3)NHSO2-, (CH3)3CNHSO2, and
the like. It is selected from the scope of the indicated carbon atom number. [0055]
In the specification, the indication of "di(Ca-Cbalkyl)aminosulfonyl" means sulfamoyl
groups, which both hydrogen atoms are substituted with the above-mentioned alkyl
group having carbon atom number of a to b that may be identical with or different
from each other, and includes for example (CH3)2NSO2-, CH3CH2N(CH3)SO2-,
(CH3CH2)2NSO2-, (CH3CH2CH2)2NSO2-, (CH3CH2CH2CH2)2NSO2-, and the like. It is
selected from the scope of the indicated carbon atom number. [0056] In the
specification, the indication of "di(Ca-Cbalkyl)phosphoryl" means
phosphoryl groups, which both hydrogen atoms are substituted with the abovementioned
alkyl group having carbon atom number of a to b that may be identical
with or different from each other, and includes for example (CH3O)2P(O)-,
(CH3CH2O)2P(0)-, and the like. It is selected from the scope of the indicated carbon
atom number.
[0057] In the specification, the indication of "di(Ca-Cbalkyl)thiophosphoryl" means
thiophosphoryl groups, which both hydrogen atoms are substituted with the abovementioned
alkyl group having carbon atom number of a to b that may be identical
with or different from each other, and includes for example (CH3O)2P(S)-,
(CH3CH2O)2P(S)-, and the like. It is selected from the scope of the indicated carbon
atom number.
[0058] In the specification, the indication of "tri(Ca-Cbalkyl)silyl" means silyl
groups substituted with the above-mentioned alkyl group having carbon atom
number of a to b that may be identical with or different from each other, and includes
for example trimethylsilyl, triethylsilyl, tri(n-propyl)silyl, ethyldimethylsilyl, npropyldimethylsilyl,
n-butyldimethylsilyl, i-butyldimethylsilyl, t-butyldimethylsilyl, and
the like. It is selected from the scope of the indicated carbon atom number. [0059]
In the specification, the indication of "Ca-Cbalkylcarbonyloxy" means alkylcarbonyl-Ogroups
wherein the alkyl has carbon atom number of a to b, and includes for
example CH3C(O)-O-, CH3CH2C(0)-0-, CH3CH2CH2C(O)-O-, (CH3)2CHC(O)-O-,
CH3(CH2)3C(O)-O-, (CH3)2CHCH2C(O)-0-, CH3CH2CH(CH3)C(O)-O-, (CH3)3CC(O)-O-,
and the like. It is selected from the scope of the indicated carbon atom number.
[0060] In the specification, the indication of "Ca-Cbalkylsulfonyloxy" means
alkylsulfonyl-0- groups wherein the alkyl has carbon atom number of a to b, and
includes for example CH3S02-0-, CH3CH2S02-O-, CH3CH2CH2SO2-O-, (CH3)2CHSO2-O-,
and the like. It is selected from the scope of the indicated carbon atom number.
[0061] In the specification, the indication of "Ca-Cbhaloalkylsulfonyloxy" means
haloalkylsulfonyl-O- groups wherein the haloalkyl has carbon atom number of a to b,
and includes for example difluoromethanesulfonyl-O-, trifluoromethanesulfonyl-0-,
chlorodifluoromethanesulfonyl-0-, bromodifluoromethanesulfonyl-O-, and the like. It
is selected from the scope of the indicated carbon atom number. [0062] In the
specification, the indication of "Ca-Cbcycloalkyl Cd-Cealkyl", "Ca-Cbhalocycloalkyl Cd-
Cealkyl", "Ca-Cbalkoxy Cd-Cealkyl", "Ca-Cbhaloalkoxy Cd-Cealkyl",
"benzyloxy Cd-Cealkyl", "Ca-Cbalkylthio Cd-Cealkyl", "Ca-Cbhaloalkylthio Cd-Cealkyl",
"phenylthio Cd-Cealkyl", "phenylthio Cd-Cealkyl substituted with (Z)p1", "Ca-Cbalkylsulfinyl
Cd-Cealkyl", "Ca-Cbhaloalkylsulfinyl Cd-Cealkyl", "Ca-Cbalkylsulfonyl Cd-Cealkyl", "Ca-
Cbhaloalkylsulfonyl Cd-Cealkyl", "Ca-Cbalkylcarbonyl Cd-Cealkyl", "Ca-Cbhaloalkylcarbonyl
Cd-Cealkyl", "Ca-Cbalkoxycarbonyl Cd-Cealkyl", "Ca-Cbhaloalkoxycarbonyl Cd-Cealkyl", "Ca-
Cbalkylaminocarbonyl Cd-Cealkyl", "di(Ca-Cbalkyl) aminocarbonyl Cd-Cealkyl", "tri(Ca-
Cbalkyl) silyl Cd-Cealkyl", "phenyl Cd-Cealkyl", "phenyl Cd-Cealkyl substituted with (Z)p1",
"Cd-Cealkyl substituted with any one of D-1 to D-60" or "Cd-Cealkyl substituted with any
one of E-1 to E-49" means straight-chain or branched-chain hydrocarbon groups
having carbon atom number of d to e, which a hydrogen atom (hydrogen atoms)
bonded to carbon atom is (are) arbitrarily substituted with the Ca-Cbcycloalkyl, Ca-
Cbhalocycloalkyl, Ca-Cbalkoxy, Ca-Cbhaloalkoxy, benzyloxy, Ca-Cbalkylthio, Ca-
Cbhaloalkylthio, phenylthio, phenylthio substituted with (Z)p1, Ca-Cbalkylsulfinyl, Ca-
Cbhaloalkylsulfinyl, Ca-Cbalkylsulfonyl, Ca-Cbhaloalkylsulfonyl, Ca-Cbalkylcarbonyl, Ca-
Cbhaloalkylcarbonyl, Ca-Cbalkoxycarbonyl, Ga-Cbhaloalkoxycarbonyl, Ca-
Cbalkylaminocarbonyl, di(Ca-Cbalkyl) aminocarbonyl, tri(Ca-Cbalkyl) silyl, phenyl, phenyl
substituted with (Z)p1) D-1 to D-60 or E-1 to E-49 that has the meaning mentioned
above, respectively. It is selected from the scope of the indicated carbon atom
number.
[0063] In the specification, the indication of "Ca-Cbalkyl arbitrarily substituted with
R4", "Ca-Cbalkyl arbitrarily substituted with R16", "Ca-Cbalkyl arbitrarily substituted with
R24" or "Ca-Cbalkyl arbitrarily substituted with R32" means straight-chain or branchedchain
hydrocarbon groups having carbon atom number of d to e, which a hydrogen
atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with R4,
R16, R24 or R32. It is selected from the scope of the indicated carbon atom number. In
this case, when two or more substituents R4, R16, R24 or R32are present on the Ca-Cbalkyl,
respective R4, R16, R24 or R32 may be identical with or different from each other.
[0064] In the specification, the indication of "Ca-Cbhaloalkoxy Cd-Cehaloalkyl"
means the haloalkyl having carbon atom number of d to e, which a hydrogen atom
(hydrogen atoms) or a halogen atom (halogen atoms) bonded to carbon atom is
(are) arbitrarily substituted with the Ca-Cbhaloalkoxy, and includes for example 2,2,2-
trifluoro-1 -(2,2,2-trifluoroethoxy)-1 -(trifluoromethyl)ethyl, 3(1,2-dichloro-1,2,2-
trifluoroethoxy)-1,1,2,2,3,3-hexafluoropropyl, and the like. It is selected from the
scope of the indicated carbon atom number.
[0065] In the specification, the indication of "Ca-Cbalkenyl Cd-Cecycloalkyl" or "Ca-
Cbhaloalkenyl Cd-Cecycloalkyl" means the cycloalkyl having carbon atom number of d
to e, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are)
arbitrarily substituted with Ca-Cbalkenyl or Ca-Cbhaloalkenyl, and includes for example
2-vinylcyclopropyl, 3,3-dimethyl-2-(2-methyl-1-propenyl)cyclopropyl, 2-(2,2-
dichloethenyl)-3,3-dimethylcyclopropyl, 2-(2-chloro-3,3,3-trifluoro-1-propenyl)-3,3-
dimethylcyclopropyl, 2-allylcyclopentyl, and the like. It is selected from the scope of
the indicated carbon atom number.
[0066] In the specification, the indication of "Ca-Cbcycloalkyl arbitrarily substituted
with R4", "Ca-Cbcycloalkyl arbitrarily substituted with R16", "Ca-Cbcycloalkyl arbitrarily
substituted with R24" or "Ca-Cbcycloalkyl arbitrarily substituted with R32" means the
cycloalkyl groups having carbon atom number of a to b, which a hydrogen atom
(hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted with R4, R16,
R24 or R32. The substitution for R4, R16, R24 or R32 may be in the ring structure moiety,
the side chain moiety or both of them. In this case, when two or more substituents
R4, R16, R24 or R32are present on the Ca-Cbcycloalkyl, respective R4, R16, R24 or R32 may be
identical with or different from each other. [0067] In the specification, the indication
of "phenyl Ca-Cbalkenyl" or "phenyl Ca-Cbalkenyl substituted with (Z)p1" means the
alkenyl having carbon atom number of a to b, which a hydrogen atom (hydrogen
atoms) bonded to carbon atom is (are) arbitrarily substituted phenyl or phenyl
substituted with (Z)P1. It is selected from the scope of the indicated carbon atom
number.
[0068] In the specification, the indication of "Ca-Cbalkenyl arbitrarily substituted
with R4", "Ca-Cbalkenyl arbitrarily substituted with R16", "Ca-Cbalkenyl arbitrarily
substituted with R24" or "Ca-Cbalkenyl arbitrarily substituted with R32" means the alkenyl
groups having carbon atom number of a to b, which a hydrogen atom (hydrogen
atoms) bonded to carbon atom is (are) arbitrarily substituted with R4, R16, R24 or R32. It
is selected from the scope of the indicated carbon atom number. In this case, when
two or more substituents R4, R16, R24 or R32are present on the Ca-Cbalkenyl, respective
R4, R16, R24 or R32may be identical with or different from each other.
[0069] In the specification, the indication of "phenyl Ca-Cbalkynyl" or "phenyl Ca-
Cbalkynyl substituted with (Z)p1" means the alkynyl having carbon atom number of a to
b, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are)
arbitrarily substituted phenyl or phenyl substituted with (Z)p1. It is selected from the
ope of the indicated carbon atom number.
[0070] In the specification, the indication of "Ca-Cbalkynyl arbitrarily substituted
with R4", "Ca-Cbalkynyl arbitrarily substituted with R16", "Ca-Cbalkynyl arbitrarily
substituted with R4" or "Ca-Cbalkynyl arbitrarily substituted with R32" means the alkynyl
groups having carbon atom number of a to b, which a hydrogen atom (hydrogen
atoms) bonded to carbon atom is (are) arbitrarily substituted with R4, R16, R24 or R32. It
is selected from the scope of the indicated carbon atom number. In this case, when
two or more substituents R4, R16, R24 or R32 are present on the Ca-Cbalkenyl, respective
R4, R16, R24 or R32may be identical with or different from each other.
[0071] In the specification, the indication of "phenyl Ca-Cbalkoxy" or "phenyl Ca-
Cbalkoxy substituted with (Z)p1" means the Ca-Cbalkoxy, which a hydrogen atom
(hydrogen atoms) bonded to carbon atom is (are) arbitrarily substituted phenyl or
phenyl substituted with (Z)p1. The concrete examples of Ca-Cbalkoxy are for example
-CH2O-, -CH(CH3)O-, -C(CH3)2O-, -CH2CH2O-, -CH(CH3)CH2O-, -C(CH3)2CH20-, and
the like. It is selected from the scope of the indicated carbon atom number.
[0072] In the specification, the indication of "phenyl Ca-Cbalkylcarbonyl" or "phenyl
Ca-Cbalkylcarbonyl substituted with (Z)P1" means the Ca-Cbalkylcarbonyl, which a
hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily
substituted phenyl or phenyl substituted with (Z)p1. The concrete examples of Ca-
Cbalkylcarbonyl are for example -CH2C(O)-, -CH(CH3)C(O)-, -C(CH3)2C(O)-, -
CH2CH2C(O)-, -CH(CH3)CH2C(0)-, -C(CH3)2CH2C(0)-, -CH2CH(CH3)C(O)-, -
CH2C(CH3)2C(O)-, -CH2CH2CH2C(O)-? and the like. It is selected from the scope of the
indicated carbon atom number.
[0073] In the specification, the indication of "phenyl Ca-Cbalkoxycarbonyl" or
"phenyl Ca-Cbalkoxycarbonyl substituted with (Z)p1" means the Ca-Cbalkoxycarbonyl,
which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are) arbitrarily
substituted phenyl or phenyl substituted with (Z)p1. The concrete examples of Ca-
Cbalkoxycarbonyl are for example -CH20-C(0)-, -CH(CH3)O-C(O)-, -C(CH3)2O-C(O)-, -
CH2CH2O-C(0)-, -CH(CH3)CH2O-C(O)-, -C(CH3)2CH2O-C(0)-, and the like. It is
selected from the scope of the indicated carbon atom number. [0074] In the
specification, the indication of "phenyl Ca-Cbalkylaminocarbonyl" or "phenyl Ca-
Cbalkylaminocarbonyl substituted with (Z)p1" means the Ca-Cbalkylaminocarbonyl,
which a hydrogen atom (hydrogen atoms) bonded to
carbon atom is (are) arbitrarily substituted phenyl or phenyl substituted with (Z)p1.
The concrete examples of Ca-Cbalkylaminocarbonyl are for example -CH2NH-C(O)-,
-CH(CH3)NH-C(0)-, -C(CH3)2NH-C(O)-, -CH2CH2NH-C(O)-, -CH(CH3)CH2NH-C(O)-,
C(CH3)2CH2NH-C(O)-, and the like. It is selected from the scope of the indicated
carbon atom number.
[0075] In the specification, concrete examples of the indication of "R1 and R2
together may form 3- to 8-membered ring together with the nitrogen atom bonding
them by forming C2 to C7 alkylene chain, in this case, the alkylene chain may contain
one oxygen atom, sulfur atom or nitrogen atom",
"R10 together with R9 may form 3- to 7-membered ring with the nitrogen atom bonding
them by forming C2-C6alkylene chain, in this case, the alkylene chain may contain
one oxygen atom, sulfur atom or nitrogen atom",
"R18 together wiing C4-C7alkyth R17 may form 5- to 8-membered ring with the nitrogen
atom
bonding them by formlene chain, in this case, the alkylene chain may
contain one oxygen atom or sulfur atom",
"R26 together with R25 may form 3- to 6-membered ring with the nitrogen atom
bonding them by forming C2-C5alkylene chain, in this case, the alkylene chain may
contain one oxygen atom or sulfur atom",
"R29 together with R28 may form 3- to 6-membered ring with the nitrogen atom
bonding them by forming C2-C5alkylene chain, in this case, the alkylene chain may
contain one oxygen atom, sulfur atom or nitrogen atom",
"R34 together with R33 may form 3- to 6-membered ring with the nitrogen atom
bonding them by forming C2-C5alkylene chain, in this case, the alkylene chain may
contain one oxygen atom or sulfur atom",
are for example aziridine, azetidine, pyrrolidine, oxazolidine, thiazoridine,
imidazolidine, piperidine, morpholine, thiomorpholine, piperazine, homopiperidine,
heptamethyleneimine, and the like. It is selected from the scope of the indicated
carbon atom number.
[0076] In the specification, concrete examples of the indication of "R7 together
with R6 may form 3- to 7-membered ring with the nitrogen atom bonding them by
forming C2-C6alkylene chain, in this case, the alkylene chain may contain one
oxygen atom, sulfur atom or nitrogen atom" are for example aziridine, azetidine,
azetidin-2-one, pyrrolidine, pyrrrolidin-2-one, oxazolidine, oxazolidin-2-one,
thiazoridine, thiazoridin-2-one, imidazolidine, imidazolidin-2-one, piperidine,
piperidin-2-one, morpholine, tetrahydro-1,3-oxadin-2-one, thiomorpholine,
tetrahydro-1,3-thiazd the like. It is selected from the scope of the indicated
carbon atom number.in-2-one, piperazine, tetrahydropyrimidin-2-one,
homopiperidine,
homopiperidin-2-one, an
[0077] In the specification, concrete examples of the indication of "R11 together
with R9 may form 5- to 7-membered ring with the nitrogen atom bonding them by
forming C2-C4alkylene chain, in this case, the alkylene chain may contain one
oxygen atom, sulfur atom or nitrogen atom" are for example isoxazoline, oxazoline,
thiazoline, imidazoline, 1,4,2-dioxazoline, 1,4,2-oxathiazoline, 1,2,4-oxadiazoline,
dihydro-1,2-oxadine, dihydro-1,3-oxadine, dihydro-1,3-thiazine,
3,4,5,6-tetrahydropyrimidine, dihydro-1,4,2-dioxadine, dihydro-1,4,2-oxathiazine,
dihydro-4H-1,2,4-oxadiazine, tetrahydro-1,2-oxazepine, and the like. It is selected
from the scope of the indicated carbon atom number.
[0078] In the specification, concrete examples of the indication of "R31 together
with R30 may form 5- to 7-membered ring with the nitrogen atom bonding them by
forming C2-C4alkylene chain, in this case, the alkylene chain may contain one
oxygen atom, sulfur atom or nitrogen atom" are for example oxazoline, thiazoline,
imidazoline, dihydro-1,3-oxazine, dihydro-1,3-thiazine, 3,4,5,6-tetrahydropyrimidine,
dihydro-1,4,2-dioxadine, and the like. It is selected from the scope of the indicated
carbon atom number.
[0079] In the compounds included in the present invention, the combination of
the atoms of A1, A2 and A3 includes for example the following groups.
That is, A-l: A1, A2 and A3 are carbon atoms.
A-ll: A1 is nitrogen atom, A2 and A3 are carbon atoms.
A-lll: A2 is nitrogen atom, A1 and A3 are carbon atoms.
A-IV: A1 and A3 are nitrogen atom, A2 is carbon atom.
A-V: A2 and A3 are nitrogen atom, A1 is carbon atom.
[0080] In the compounds included in the present invention, the substituent G
includes for example aromatic 6-membered rings shown in any one of G-1 to G-10
and aromatic 5-membered rings shown in any one of G-11 to G-25. Among them,
aromatic 6-membered rings shown in G-1, G-3 and G-4 and aromatic 5-membered
rings shown in any one of G-13, G-14, G-17, G-18, G-20, G-21 and G-22 are
preferable, and aromatic 6-membered ring shown in G-1 is particularly preferable.
[0081] In the compounds included in the present invention, the substituent W
includes for example oxygen atom or sulfur atom.
[0082] In the compounds included in the present invention, the substituent X
cludes for example the following groups. In each case mentioned below, when m
is an integer of 2 or more, Xs may be identical with or different from each other.
That is, X-l: halogen atom and C1-C6haloalkyl.
X-ll: halogen atom, C1-C6alkyl, C1-C6haloalkylC1-C6alkoxy, C1-C6alkylsulfonyloxy,
C1-C6alkylthio, C1-C6alkylsulfinyl and C1-C6alkylsulfonyl.
X-lll: halogen atom, C1-C6haloalkyl, C1-C6haloalkoxy, C1-C3haloalkoxy C1-
C3haloalkoxy, C1-C6haloalkylsulfonyloxy C1-C6haloalklylthio,C1-C6haloalkylsulfinyl
and C1-C6haloalkylsulfonyl.
X-IV: halogen atom, C1-C6haloalkyl, cyano, nitro, -SF5 and -Si(R13)(R14)R12 wherein
R12 is C1-C6alkyl, phenyl or phenyl substituted with (Z)p1, R13 and R14 independently of
each other are C1-C6alkyl.
X-V: halogen atom and C1-C6alkyl arbitrarily substituted with R4 wherein R4 is
halegen atom, cyano, -OH, C1-C6alkoxy, C1-C6haloalkoxy,C1-C6alkylthio, C1-
C6haloalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-
C6haloalkylsulfonyl or tri(C1-C6alkyl)silyl.
X-VI: halogen atom, C1-C6haloalkyl, C3-C8cycloalkyl, C3-C8halocycloalkyl, C2-
C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, E-10, E-12, E-18, E-32,
E-35 andE-43.
X-VII: halogen atom, CrC6haloalkyl, -OR5, -OSO2R5 and -S(O)rR5 wherein R5 is Cr
C6alkyl, CrC6haloalkyl, C1-C3haloalkoxy C1-C3haloalkyl, C3-C8cycloalkyl, C3-
C8halocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, E-4
to E-9, E-23 to E-27 or E-28, r is an integer of 0 to 2.
X-VIII: halogen atom, C1-C6haloalkyl, -C(O)OR9, -C(O)SR9, -C(S)OR9, -C(S)SR9, -
C(S)NHR10, -C(S)N(R10)R9, -CH=NOR11 and -C(R9)=NOR11 wherein R9 is C1-C6alkyl,
C1-C6haloalkyl, C3-C8cycloalkyl or C3-C8halocycloalkyl, R10 is hydrogen atom or C,-
C6alkyl, or R10 together with R9 may form 5- or 6-membered ring with the nitrogen
atom bonding them by forming C4-C5alkylene chain, in this case, the alkylene chain
may contain one oxygen atom or sulfur atom, R11 is C1-C6alkyl or C1-C6haloalkyl, or
R11 together with R9may form 5- or 6-membered ring with the atom bonding them by
forming C2-C3alkylene chain, in this case, the alkylene chain may be arbitrarily
substituted with Chalky!.
X-IX: m is 2, two adjacent Xs form 5- or 6-membered ring with the carbon atom
bonding them by forming -CF2OCF2-, -OCF2O-, -CF2OCF20- or -OCF2CF2O-.
[0083] In the compounds included in the present invention, m indicating the
number of substituent X is an integer of 0 to 5. Among them, m is preferably 1, 2
and 3.
[0084] In the compounds included in the present invention, the substituent Y
includes for example the following groups. In each case mentioned below, when n
is an integer of 2 or more, Ys may be identical with or different from each other.
That is, Y-l: halogen atom, C1-C6alkyl and C1-C6haloalkyl.
Y-ll: halogen atom, C1-C6alkyl, cyano, nitro, -C(0)NH2 and -C(S)NH2.
Y-lll: halogen atom, C1-C6alkyl and C1-C6alkyl arbitrarily substututed with C1-C6alkyl
and R4wherein R4 is halogen atom, cyano, -OH, C1-C6alkoxy, C1-C6haloalkoxy, C1-
C6alkylthio, C1-C6haloalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-
C6alkylsulfonyl, C1-C6haloalkylsulfonyl or tri(C1-C6alkyl)silyl.
Y-IV: halogen atom, C1-C6alkyl, -OR5, -OS02R5 and -S(O)rR5 wherein R5 is C1-
C6alkyl,C1-C6haloalkyl, C1-C3haloalkoxy C1-C3haloalkyl, C3-C8cycloalkyl, C3-
C8halocycloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, E-4
to E-9, E-23 to E-27 or E-28, r is an integer of 0 to 2.
Y-V: halogen atom, C1-C6alkyl, -NHR7, -N(R7)R6 wherein R6 is C1-C6alkyl, C1-
C6haloalkyl, -S(O)2R9, -CHO, -C(0)R9, -C(O)OR9, -C(0)SR9, -C(S)OR9 or -C(S)SR9,
R7 is hydrogen atom, C1-C6alkyl or C1-C6haloalkyl, R9 is C1-C6alkyl, C1-C6haloalkyl,
C3-C8cycloalkyl or C3-C8halocycloalkyl and -N=C(R9)OR8 wherein R8 is C1-C6alkyl, R9
is C1-C6alkyl or C1-C6haloalkyl.
Y-VI: halogen atom, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkylthio, C1-
C6alkylamino
and di(C1-C6alkyl)amino.
[0085] In the compounds included in the present invention, n indicating the
number of substituent Y is an integer of 0 to 4. Among them, n is preferably 0 and
1.
[0086] In the compounds included in the present invention, the substituent R1
includes for example the following groups.
That is, R1-l: C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R16 (wherein R16 is
halogen atom, C3-C6cycloalkyl, C3-C6halocycloalkyl, phenyl, phenyl substituted with
(Z)p1, D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 to E-12, E-18, E-19, E-32, E-35,
E-43, M-2, M-3, M-5, M-8, M-9 or M-10), C3-C8cycloalkyl and C3-C8halocycloalkyl.
R1-ll: C1-C6alkyl arbitrarily substituted with -OR25 wherein R25is C1-C6alkyl,
C1-C6haloalkyl, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6alkylaminocarbonyl,
di(C1-C6alkyl)aminocarbonyl or C1-C6alkylsulfonyl.
R1-lll: C1-C6alkyl arbitrarily substituted with -N(R26)R25 wherein R25is C1-C6alkyl,
C1-C6haloalkyl, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl,C1-C6alkylaminocarbonyl,
di(C1-C6alkyl)aminocarbonyl or C1-C6alkylsulfonyl, R26 is hydrogen or C1-C6alkyl. R1-
IV: C1-C6alkyl arbitrarily substituted with -S(O)rR27 wherein R27is C1-C6alkyl, C1-
C6haloalkyl or tri(C1-C4alkyl)silyl C1-C4alkyl, r is an integer of 0 to 2. R1-V: C1-C6alkyl
arbitrarily substituted with R16 wherein R16 is cyano, -C(O)R28, -C(O)OR28, -C(O)NHR29, -
C(O)N(R29)R28, -C(0)N(R29)OR28, -C(S)NHR29, -C(S)N(R29)R28, -S02NHR29, -SO2N(R29)R28, -
C(R31)=NOH, -C(R31)=NOR30, -C(=NR31)OR30 or -C(=NR31)SR30, R28 is C1-C6alkyl, C1-
C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl,C1-C6alkoxy C1-C4alkyl, C1-C6alkylthio C1-
C4alkyl, cyano C1-C6alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1,
C3-C6cycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, phenyl or phenyl
substituted with (Z)p1, R29 is hydrogen atom, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl,
R30 is C1-C6alkyl or C3-C6cycloalkyl C1-C4alkyl, R31is hydrogen atom or C1-C6alkyl, or
R31 together with R30 may for 5- or 6-membered ring with the atom bonding them by
forming C2-C3alkylene chain.
R1-VI: C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, phenyl substituted
with (Z)p1, D-8, D-10, D-11, D-13, D-15, D-17, D-18, D-21 to D-23, D-26, D-27, D-29 to
D-37, D-39, D-40, D-42, D-45, D-47, D-48, D-50, D-51, D-53, D-54, D-56, D-58, E-5,
E-7 and E-9.
R1-VII: -N(R20)R19 wherein R19 is CrC6haloalkyl, C3-C6cycloalkyl, -C(O)R28, -C(O)OR28, -
C(O)NHR29, -C(O)N(R29)R28, -C(S)NHR29, -C(S)N(R29)R28, phenyl, phenyl substituted with
(Z)p1, D-3, D-4, D-21, D-47, D-50, D-51, D-53 or D-54, R20 is hydrogen atom, C1-
C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4aIkylthio C1-C4aIkyl, cyano C1-C6alkyl, C3-
C6alkenyl, C3-C6alkynyl, -CHO, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl or C1-
C6alkylsulfonyl, R28 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, (C1-
C6alkoxy C1-C4alkyl, C1-C6alkylthio C1-C4alkyl, cyano C1-C6alkyl, phenyl C1-C4aIkyl,
phenyl C1-C4alkyl substituted with (Z)p1, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl,
C3-C6alkynyl, phenyl or phenyl substituted with (Z)p1, R29 is hydrogen atom, C1-C6alkyl,
C3-C6alkenyl or C3-C6alkynyl. R1-VIII: C1-C6alkyl, C1-C6haloalkyl, C1-C6alkyl arbitrarily
substituted with R16 (wherein R16 is cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-
C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio,C1-C6haloalkylthio, C1-C6alkylsulfinyl, C1-
C6haloalkylsulfinyl,C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, (C1-C6alkylcarbonyl, -
C(O)OR28, -C(O)NHR29, -C(0)N(R29)R28, -C(S)NH2> -C(R31)=NOH, -C(R31)=NOR30,
phenyl, phenyl substituted with (Z)p1, D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 to E-7,
E-10, E-11 or E-32, R28 is (C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C3-
C6cycloalkyl, C3-
C8alkenyl or C3-C8alkynyl, R29 is hydrogen atom or C1-C6alkyl, R30 is C1-C6alkyl, R31is
hydrogen or C1-C6alkyl), C3-C6cycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, -
N(R20)R19 (wherein R19 isC1-C6haloalkyl, -C(O)R28, -C(O)OR28, phenyl, phenyl substituted
with (Z)p1, D-3, D-4, D-21, D-47, D-50, D-51, D-53 or D-54, R20 is hydrogen atom or C1-
C6alkyl, R28 is C1-C6alkyl,C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C3-C6cycloalkyl,
C3-C8alkenyl or C3-C8alkynyl), phenyl substituted with (Z)p1, D-8, D-10, D-13, D-15, D-
18, D-21, D-34, D-35, D-50 and D-51. R1-IX: C1-C6haloalkyl, C1-C6alkyl arbitrarily
substituted with R16 (wherein R16 is cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-
C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, CrC6haloalkylthio, C1-C6alkylsulfinyl, C1-
C6haloalkylsulfinyl, C1-C6alkylsulfonyl,C1-C6haloalkylsulfonyl, C1-C6alkylcarbonyl, -
C(0)OR28, -C(O)NHR29, -C(O)N(R29)R28, -C(S)NH2, -C(R31)=NOH, -C(R31)=NOR30,
phenyl substituted with (Z)p1, D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 to E-7, E-10,
E-11 or E-32, R28 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C3-
C6cycloalkyl, C3-C8alkenyl or C3-C8alkynyl, R29 is hydrogen atom or C1-C6alkyl, R30 is C1-
C6alkyl, R31is hydrogen or CrC6alkyl), C3-C6cycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-
C6alkynyl, -N(R20)R19 (wherein R19 is C1-C6haloalkyl, -C(O)R28, -C(O)OR28, phenyl, phenyl
substituted with (Z)P1, D-3, D-4, D-21, D-47, D-50, D-51, D-53 or D-54, R20 is hydrogen
atom or C,-C6alkyl, R28 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl CrC4alkyl, C3-
C6cycloalkyl, C3-C8alkenyl or C3-C8alkynyl), phenyl substituted with (Z)p1, D-8, D-10, D-
13, D-15, D-18, D-21, D-34, D-35, D-50 and D-51.
R1-X: C1-C8haloalkyl, C1-C6alkyl arbitrarily substituted with R16 (wherein R16 is C3-
C6cycloalkyl, C1-C6alkoxy, C1-C6alkylthio, C1-C6alkylsulfinyl,C1-C6alkylsulfonyl, -
C(O)NH2, -C(O)NHR28, -C(S)NH2, -C(R31)=NOH, -C(R31)=NOR30, D-1 to D-4, D-8 to D-38,
D-47 to D-54, E-4 to E-7, E-10, E-11 or E-32, R28 is C1-C6alkyl, C1-C6haloalkyl, C3-
C6cycloalkyl, C3-C8alkenyl or C3-C8alkynyl, R30 is C1-C6alkyl, R31 is hydrogen or C1-
C6alkyl), C3-C6cycloalkyl, C3-C8alkenyl, C3-C8haloalkenyl, C3-C8alkynyl, -N(R20)R19 (wherein
R19 is CrC6haloalkyl, -C(O)R28, -C(O)OR28, phenyl, D-3, D-4, D-21, D-47, D-50, D-51,
D-53 or D-54, R20 is hydrogen atom or C1-C6alkyR28 is C1-C6alkyl, C1-C6haloalkyl, C3-
C6cycloalkyl C1-C4alkyl, C3-C6cycloalkyl, C3-C8alkenyl or C3-C8alkynyl), D-8, D-10, D-
13, D-15, D-18, D-21, D-34, D-35, D-50 and D-51. R1-XI: C1-C6alkyl and phenyl C1-
C6alkyl.
R1-XII: C1-C6alkyl, C1-C8alkyl arbitrarily substituted with R16 (wherein R16 is halogen
atom, C3-C6cycloalkyl, C3-C6halocycloalkyl, phenyl, phenyl substituted with (Z)p1, D-1 to
D-4, D-8 to D-42, D-47 to D-55, E-4 to E-12, E-14, E-16 to E-19, E-21 to E-23, E-
26 to E-35, E-40 to E-45, E-48, M-2, M-3, M-5, M-8 to M-10, M-14, M-15 or M-16),
C3-C8cycloalkyl and C3-C8halocycloalkyl.
R1-XIII: C1-C8alkyl arbitrarily substituted with -OR25 wherein R25 is hydrogen atom, C1-
C6alkyl, C1-C6haloalkyl, -C(O)R33, -C(O)OR33, -C(O)NHR34, -C(O)N(R34)R33, -C(S)NHR34, -
C(S)N(R34)R33, -S(0)2R33, -S(O)2N(R34)R33, di(C1-C6alkyl)thiophosphoryl, phenyl or phenyl
substituted with (Z)p1, R33 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C3-
C6halocycloalkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-
C6alkenyl, C3-C6alkynyl, phenyl or phenyl substituted with (Z)p1, R34is hydrogen atom or
C1-C6alkyl.
R1-XIV : C1-C8alkyl arbitrarily substituted with -N(R26)R25 wherein R25 is C1-C6alkyl, C1-
C6haloalkyl, -C(O)R33, -C(O)OR33, -C(O)SR33, -C(O)NHR34, -C(O)N(R34)R33, -C(S)R33, -
C(S)OR33, -C(S)SR33, -C(S)NHR34, -C(S)N(R34)R33, -S(O)2R33 or -S(O)2N(R34)R33, R26 is
hydrogen atom or C1-C6alkyl, or R26 together with R25may form 4- to 6-membered ring
with the nitrogen atom bonding them by forming C3-C5alkylene chain, in this case, the
alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may
be substituted with C1-C6alkyl, oxo or thioxo, R33 is C1-C6alkyl, C1-C6haloalkyl, C3-
C6cycloalkyl, C3-C6halocycloalkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with
(Z)p1, C3-C6alkenyl, C3-C6alkynyl, phenyl or phenyl substituted with (Z)p1, R34 is
hydrogen atom or C1-C6alkyl. R1-XV: C1-C8alkyl arbitrarily substituted with -S(O)rR27
wherein R27 is C1-C6alkyl, C1-C6haloalkyl, tri( C1-C4alkyl)silyl C1-C4alkyl, C1-C6alkylthio,
-C(O)NHR34, -C(O)N(R34)R33, -C(S)NHR34, -C(S)N(R34)R33, phenyl, phenyl substituted with
(Z)p1, D-47 or D-50, R33 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C3-
C6halocycloalkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted with (Z)p1, C3-
C6alkenyl, C3-C6alkynyl, phenyl or phenyl substituted with (Z)p1, R34is hydrogen atom or
(C1-C6alkyl, r is an integer of 0 to 2.
R1-XVI : C1-C8alkyl arbitrarily substituted with R16 wherein R16 is cyano, -SO2NHR29, -
SO2N(R29)R28, -CHO, -C(0)R28, -C(O)OR28, -C(O)NHR29, -C(O)N(R29)R28, -C(S)NHR29, -
C(S)N(R29)R28, -C(R31)=NOH, -C(R31)=NOR30, -C(=NR31)OR30, -C(=NR31)SR30, -
C(=NR31)N(R30)R29, -C(=NOR31)NHR29 or -C(=NOR31)N(R30)R29, R28 is C1-C6alkyl, C1-C6alkyl
arbitrarily substituted with R32, C3-C6cycloalkyl, C3-C6halocycloalkyl, C3-C6alkenyl, C3-
C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkenyl, phenyl or phenyl substituted with (Z)p1,
R29 is hydrogen atom,C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl, or R29 together with R28
may form 3- to 6-membered ring with the nitrogen atom bonding them by forming C2-
C5alkylene chain, in this
case, the alkylene chain may contain one oxygen atom or sulfur atom, R30 is C1-
C6alkyl, C3-C6cycloalkyl C1-C4alkyl, phenyl C1-C4alkyl, phenyl C1-C4alkyl substituted
with (Z)p1, C3-C8alkenyl or C3-C8alkynyl, R31 is hydrogen atom or C1-C6alkyl, or R31
together with R30 may form 5- or 6-membered ring with the atom bonding them by
forming C2-C3alkylene chain, in this case, the alkylene chain may be arbitrarily
substituted with calkyl, R32 is halogen atom, cyano, C3-C6cycloalkyl, C3-
C6halocycloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-
C4alkoxycarbonyl, -C(O)NH2, C1-C4alkylaminocarbonyl, di(C1-C4alkyl)aminocarbonyl,
phenyl or phenyl substituted with (Z)p1. R1-XVII: C3-C8alkenyl, C3-C8haloalkenyl, C3-
C8alkynyl, C3-C8haloalkynyl, phenyl substituted with (Z)p1, D-8 to D-13, D-15 to D-18,
D-21 to D-23, D-26, D-27, D-29 to D-37, D-39, D-40, D-42, D-45 to D-58, E-5, E-7,
E-9, E-24, E-25, E-27, E-28, E-30, E-31 and E-34.
R1-XVIII: -N(R20)R19 wherein R19 isC1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl Cr
C6alkyl, phenyl C1-C6alkyl, phenyl C1-C6alkyl substituted with (Z)p1, C3-C6cycloalkyl,
C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, -C(O)R28, -C(O)OR28, -C(O)NHR29, -
C(0)N(R29)R28, -C(S)NHR29, -C(S)N(R29)R28, (C1-C6alkylsulfonyl, Cr C6haloalkylsulfonyl,
phenylsulfonyl, phenylsulfonyl substituted with (Z)p1, phenyl, phenyl substituted with
(Z)p1, D-1 to D-4, D-18, D-21, D-25, D-30 to D-35, D-47 to D-55 or D-56, R20 is
hydrogen atom, Chalky!, C1-C4alkoxy C1-C4alkyl, C1-C4aIkylthio C1-C4alkyl, cyano
C1-C6alkyl, C3-C6alkenyl, C3-C6alkynyl, -CHO, C1-C6alkylcarbonyl, C1-
C6haloalkylcarbonyl, C1-C6alkoxycarbonyl, C1-C6haloalkoxycarbonyl or C1-
C6alkylsufonyl, R28 is alkyl, C1-C6alkyl arbitrarily substituted with R32, C3-C6cycloalkyl,
C3-C6halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl,
phChenyl or phenyl substituted with (Z)p1, R29 is hydrogen atom, C1-C6alkyl, C3-
C6alkenyl or C3-C6alkynyl, R29 together with R28 may form 3- to 6-membered ring with the
nitrogen atom bonding them by forming C2-C5alkylene chain, in this case, the alkylene
chain may contain one oxygen atom or sulfur atom, R32 is hydrogen atom, cyano, C3-
C6cycloalkyl, C3-C6halocycloalkyl, C1-C4alkoxy, Cr C4haloalkoxy, C1-C4alkylthio, C1-
C4haloalkylthio, C1-C4alkoxycarbonyl, -C(O)NH2, C1-C4alkylaminocarbonyl, di(C1-
C4alkyl)aminocarbonyl, phenyl or phenyl substituted with (Z)P1.
[0087] In the compounds included in the present invention, the substituent R2
includes for example the following groups. That is, R2-l: hydrogen atom.
R2-ll: C1-C6alkyl, C1-C6haloalkyl and C3-C6cycloalkyl.
R2-lll: C1-C4alkoxy C1-C4alkyl1 C1-C4alkylthio C1-C4alkyl and cyano C1-C6alkyl.
R2-IV: C3-C6alkenyl and C3-C6alkynyl.
R2-V: -OH, C1-C6alkoxy,C1-C6alkylcarbonyloxy, C1-C6alkoxycarbonyloxy and C1-
C6alkylsulfonyloxy.
R2-VI: C1-C6haloalkylthio, phenylthio, phenylthio substituted with (Z)p1 and
-SN(R18)R17 wherein R17 is C1-C6alkyl, C1-C6alkoxycarbonyl C1-C4alkyl or
C1-C6alkoxycarbony, R18 is C1-C6alkyl or benzyl.
R2-VII: -NHR20 (wherein R20 is hydrogen atom, C1-C6alkyl, -CHO, C1-C6alkylcarbonyl,
C1-C6alkoxycarbonyl orC1-C6alkylsulfonyl), -N=CHR19b and -N=C(R19b)R19a wherein
R19a is CrC6alkyl, R19b is hydrogen atom or C1-C6alkyl.
R2-VIII: -C(O)R9, -C(O)OR9, -C(O)SR9, -C(S)OR9, -C(S)SR9 (wherein R9 is C1-C6alkyl,
C1-C6haloalkyl, C3-C6cycloalkyl C1-C4alkyl, C1-C6alkoxy C1-C4alkyl, C1-C6alkylthio C1-
C4alkyl, cyano C1-C6alkyl, phenyl C1-C4alkyl, C3-C8cycloalkyl, C3-C8halocycloalkyl,
C3-C6alkenyl or C3-C6alkynyl) and C1-C6alkylsulfonyl.
R2-IX: 3- to 7-membered ring that R2 forms together with R1 is aziridine, azetidine,
pyrrolidine, oxazolidine, thiazoridine, piperidine, morpholine, thiomorpholine and
homopiperidine.
R2-X: hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl,
cyano C1-C6alkyl, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6alkynyl, -OH,
C1-C6alkylcarbonyloxy,C1-C6alkylsulfonyloxy, -NH2l -C(O)R9, -C(O)OR9, -C(O)SR9,
-C(S)OR9 and -C(S)SR9 wherein R9 isC1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl
C1-C4alkyl, C1-C6alkoxy C1-C4alkyl, C1-C6alkylthio C1-C4alkyl, cyano C1-C6alkyl,
C3-C8cycloalkyl, C3-C6alkenyl or C3-C6alkynyl.
R2-XI: hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, cyano C1-C6alkyl, C3-
C6alkynyl, -C(O)R9 and -C(O)OR9 wherein R9 is CrCealkyl, C1-C6alkoxy C1-C4alkyl,
C1-C6alkylthio C1-C4alkyl, C3-C8cycloalkyl, C3-C6alkenyl or C3-C6alkynyl.
[0088] In the compounds included in the present invention, the substituent R3
includes for example the following groups.
That is, R3-l: C1-C6haloalkyl and C3-C8halocycloalkyl.
R3-ll: C1-C6alkyl, C3-C8cycloalkyl, E-4 to E-7, E-23 to E-27 and E-28.
R3-lll: C1-C4alkoxy C1-C4haloalkyl, C1-C4haloalkoxy C1-C4haloalkyl,C1-C4alkylthio
C1-
C4haloalkyl, C1-C4alkylsulfinyl C1-C4haloalkyl, C1-C4alkylsulfonyl C1-C4haloalkyl, C1-
C4haloalkylthio C1-C4haloalkyl, C1-C4haloalkylsulfinyl C1-C4haloalkyl, C1-
C4haloalkylsulfonyl C1-C4haloalkyl and cyano C1-C6haloalkyl.
R3-IV: C3-C6cycloalkyl C1-C4alkyl, C3-C6halocycloalkyl C1-C4alkyl, C1-C4alkoxy C1-
C4alkyl, (C1-C4haloalkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C1-C4alkylsulfinyl C1-
C4alkyl,C1-C4alkylsulfonyl C1-C4alkyl,C1-C4haloalkylthio C1-C4alkyl, C1-
C4haloalkylsulfinyl C1-C4alkyl, C1-C4haloalkylsulfonyl C1-C4alkyl and cyano C1-C6alkyl.
R3-V: C1-C6haloalkyl, C1-C4alkoxy C1-C4haloalkyl, C1-C4haloalkoxy C1-C4haloalkyl, C1-
C4alkylthio C1-C4haloalkyl, C1-C4haloalkylthio C1-C4haloalkyl, cyano C1-C6haloalkyl
and C3-C8halocycloalkyl. R3-VI: C1-C6haloalkyl.
R3-VII: C1-C6alkyl arbitrarily substituted with two or more arbitrary halogen atoms.
[0089] Each group showing the scope of each substituent in the compounds
included in the present invention can be arbitrarily combined one another, and all
combination thereof falls within the scope of the present invention. Examples of the
combination of the scope of X, Y and R1 include for example the combination showin
in Table 1. In the meantime, the combination of Table 1 is for illustrative purposes,
and the present invention is not limited thereto.
(Table Removed) [0090] The compounds of the present invention can beproduced for example
according to the methods mentioned below. Production Method A
(Figure Removed) [0091] The compound of formula (1-1) wherein A1, A2, A3, G, X, Y, R1, R2, R3, m
and n are as defined above that is the compound of formula (1) wherein W is oxygen
atom can be obtained by reacting the compound of formula (5) wherein A1, A2, A3, G,
X, Y, R3, m and n are as defined above with the compound of formula (6) wherein R1
and R2 are as defined above by use of a condensation agent, optionally by using a
solvent inactive for the reaction, optionally in the presence of a base. [0092] The
reaction substrates can be used in an amount of 1 to 100 equivalents of the
compound of formula (6) based on 1 equivalent of the compound of formula
(5).
[0093] The condensation agent is not specifically limited if it is a compound used
for ordinary amide synthesis, but it is for example Mukaiyama agent (2-chloro-Nmethylpyridinium
iodide), DCC (1,3-dicyclohexyl carbodiimide), WSC (1-ethyl-3-(3-
dimethylaminopropyl)-carbodiimide hydrochloride), CDI (carbonyl diimidazole),
dimethylpropynyl sulfonium bromide, propagyl triphenyl phosphonium bromide,
DEPC (diethyl phosphorocyanidate) or the like, and can be used in an amount of 1 to
4 equivalents based on the compound of formula (5).
[0094] In case where a solvent is used, th, but it includes for example aromatic
hydrocarbons such as benzene solvent is not specifically limited if it dose not inhibit
the progress of the reactione, toluene, xylene or the like, aliphatic hydrocarbons
such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or
the like, aromatic halogenated hydrocarbons such as chlorobenzene,
dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro
methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane,
trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-
dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl
acetate, ethyl propionate or the like, amides such as N,N-dimethylformamide, N.Ndimethylacetamide,
N-methyl-2-pyrolidone or the like, amines such as triethyl
amine, tributyl amine, N,N-dimethyl aniline or the like, pyridines such as pyridine,
picoline or the like, acetonitrile and dimethyl sulfoxide, and the like. These solvents
may be used alone or in a mixture of two or more. [0095] The addition of a base
is not necessarily required. However, when the base is used, alkali metal
hydroxides such as sodium hydroxide, potassium hydroxide or the like, alkali metal
carbonates such as sodium carbonate, potassium carbonate or the like, alkali metal
bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate
or the like, organic bases such as triethyamine, tributylamine, N,N-dimethylaniline,
pyridine, 4-(dimethylamino)pyridine, imidazole, 1,8-diazabicyclo[5.4.0]-7-undecene,
and the like can be used in an amount of 1 to 4 equivalents based on the compound
of formula (5).
[0096] The reaction temperature may be an arbitrary temperature ranging from -
60°C to the reflux temperature of a reaction mixture, and the reaction time may be
an arbitrary time ranging from 5 minutes to 100 hours although it varies depending
on the concentration of the reaction substrates or the reaction temperature. [0097]
Generally, it is preferable to carry out the reaction by using 1 to 20 equivalents of the
compound of formula (6) and 1 to 4 equivalent of the condensation agent such as
WSC (1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride), CDI (carbonyl
diimidazole) or the like based on 1 equivalent of the compound of formula (5),
optionally in the presence of 1 to 4 equivalents of a base such as potassium
carbonate, triethylamine, pyridine, 4-(dimethylamino)pyridine or the like, without
solvent or in a solvent such as dichloromethane, chloroform, diethyl ether,
tetrahydrofurane, 1,4-dioxane or the like, at a temperature ranging from 0°C to the
reflux temperature of these solvents for 10 minutes to 24 hours. [0098] In
addition, the compound of formula (1-1) according to the present invention can be
also synthesized by reacting the compound of formula (7) wherein A1, A2, A3, G, X,
Y, R3, m and n are as defined above, J1 is chlorine atom, bromine atom,
CrC4alkylcarbonyloxy (for example pivaloyloxy), C1-C4alkoxycarbonyloxy (for example
isobutyloxycarbonyloxy) or azolyl (for example imidazol-1-yl) that can be
synthesized according to a known method disclosed in documents from the
compound of formula (5), for example a method by reacting with a chlorinating agent
such as thionyl chloride, phosphorus pentachloride or oxalyl chloride, a method by
reacting with a organic acid halide such as pivaloyl chloride or isobutyl chlorformate,
etc. optionally in the presence of a base, or a method by reacting with carbonyl
diimidazole or sulfonyl diimidazole, etc., with the compound of formula (6), optionally
by using a solvent inactive for the reaction, optionally in the presence of a base.
[0099] The reaction substrates can be used in an amount of 1 to 50 equivalents
of the compound of formula (6) based on 1 equivalent of the compound of formula
(7).
[0100] In case where a solvent is used, the solvent is not specifically limited if it
dose not inhibit the progress of the reaction, but it includes for example aromatic
hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons
such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or
the like, aromatic halogenated hydrocarbons such as chlorobenzene,
dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro
methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane,
trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-
dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl
acetate, ethyl propionate or the like, amides such as N,N-dimethylformamide, N,Ndimethylacetamide,
N-methyl-2-pyrolidone or the like, amines such as triethyl amine,
tributyl amine, N,N-dimethyl aniline or the like, pyridines such as pyridine, picoline or
the like, acetonitrile and water, and the like. These solvents may be used alone or in
a mixture of two or more. [0101] The addition of a base is not necessarily
required. However, when the base is used, alkali metal hydroxides such as sodium
hydroxide, potassium hydroxide or the like, alkali metal carbonates such as sodium
carbonate, potassium carbonate or the like, alkali metal bicarbonates such as sodium
hydrogen carbonate,
potassium hydrogen carbonate or the like, organic bases such as triethyamine,
tributylamine, N,N-dimethylaniline, pyridine, 4-(dimethylamino)pyridine, imidazole,
1,8-diazabicyclo[5.4.0]-7-undecene, and the like can be used in an amount of 1 to 4
equivalents based on the compound of formula (7).
[0102] The reaction temperature may be an arbitrary temperature ranging from -
60°C to the reflux temperature of a reaction mixture, and the reaction time may be
an arbitrary time ranging from 5 minutes to 100 hours although it varies depending
on the concentration of the reaction substrates or the reaction temperature. [0103]
Generally, it is preferable to carry out the reaction by using 1 to 10 equivalents of
the compound of formula (6) based on 1 equivalent of the compound of formula (7),
optionally in the presence of 1 to 2 equivalents of a base such as potassium
carbonate, triethylamine, pyridine, 4-(dimethylamino)pyridine or the like, without
solvent or in a solvent such as dichloromethane, chloroform, diethyl ether,
tetrahydrofurane, 1,4-dioxane, ethyl acetate, acetonitrile or the like, at a temperature
ranging from 0°C to the reflux temperature of these solvents for 10 minutes to 24
hours.
Production Method B

(Formula Removed) [0104] Hydroxamic chloride of formula (9) wherein A1, A2, A3, W, Y, R1, R2 and n
are as defined above, J means halogen atom such as chlorine atom and bromine
atom can be obtained by halogenating the compound of formula (8) wherein A1, A2,
A3, W, Y, R1, R2 and n are as defined above using a halogenating reagent optionally
(Figure Removed
)by using a solvent inactive for the reaction, optionally in the presence of a base.
[0105] Halogenating agents include for example N-halosuccinimides such as Nchlorosuccinimide,
N-bromosuccinimide or the likike, hypohalogenous acid esters
such as hypochlorous acid-t-butyl ester or the like, simple substance halogens such
as chlorine gas or the like, and it can be used in an amount of 1 to 10 equivalents
based on the compound of formula (8).e, hypohalogenous acid alkali metal salts
such as sodium hypochlorite or the l
[0106] In case where a solvent is used, the solvent is not specifically limited if it
dose not inhibit the progress of the reaction, but it includes for example aromatic
hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons
such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or
the like, aromatic halogenated hydrocarbons such as chlorobenzene,
dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro
methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane,
trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-
dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl
acetate, ethyl propionate or the like, amides such as N,N-dimethylformamide, N,Ndimethylacetamide,
N-methyl-2-pyrolidone or the like, alcohols such as methanol,
ethanol, ethylene glycol or the like, carboxylic acids such as acetic acid, propionic
acid or the like, acetonitrile and water, and the like. These solvents may be used
alone or in a mixture of two or more. [0107] The reaction temperature may be an
arbitrary temperature ranging from -60°C to the reflux temperature of a reaction
mixture, and the reaction time may be an arbitrary time ranging from 5 minutes to 24
hours although it varies depending on the concentration of the reaction substrates or
th A1, A2, e reaction temperature. [0108] The compounds of formula (1) whereinA3,
G, W, X, Y, R1, R2, R3, m and n are as defined above according to the present
invention can be obtained by reacting the compound of formula (9) with the
compound of formula (10) wherein G, X, R3 and m are as defined above in the
presence of a base optionally by use of a solvent inactive for the reaction.
[0109] The reaction substrates can be used in an amount of 1 to 5 equivalents of
the compound of formula (10) based on 1 equivalent of the compound of formula (9).
[0110] The used base includes for example alkali metal hydroxides such as
sodium hydroxide, potassium hydroxide or the like, alkali metal carbonates such as
sodium carbonate, potassium carbonate or the like, alkali metal bicarbonates such
as sodium hydrogen carbonate, potassium hydrogen carbonate or the like, organic
bases such as triethyamine, tributylamine, N,N-dimethylaniline, pyridine, 4-
(dimethylamino)pyridine, imidazole, 1,8-diazabicyclo[5.4.0]-7-undecene, and the like
can be used in an amount of 1 to 5 equivalents based on the compound of formula
(9).
[0111] In case where a solvent is used, the solvent is not specifically limited if it
dose not inhibit the progress of the reaction, but it includes for example aromatic
hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons
such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or
the like, aromatic halogenated hydrocarbons such as chlorobenzene,
dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro
methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane,
trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-
dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl
acetate, ethyl propionate or the like, amides such as N,N-dimethylformamide, N.Ndimethylacetamide,
N-methyl-2-pyrolidone or the like, and acetonitrile, and the like.
These solvents may be used alone or in a mixture of two or more.
[0112] The reaction temperature may be an arbitrary temperature ranging from -
60°C to the reflux temperature of a reaction mixture, and the reaction time may be
an arbitrary time ranging from 5 minutes to 100 hours although it varies depending
on the concentration of the reaction substrates or the reaction temperature. [0113]
Generally, the compound of formula (9) can be obtained for example by carrying
out the reaction by using 1 to 2 equivalents of a halogenating agent such as Nchlorosuccinimide,
sodium hypochlorite aqueous solution, hypochlorous acid-tbutyl
ester, chlorine gas or the like based on 1 equivalent of the compound of formula
(8) in a solven, 1,4-dioxane, N,N-dimt such as dichloromethane, chloroform,
1,2-dimethoxyethane, tetrahydrofuraneethylformamide or the like, at a temperature
ranging from 0°C to the reflux temperature of these solvents for 10 minutes to 2
hours. Then, preferably without the isolation of the compound of formula (9), 1 to 2
equivalents of the compound of formula (10) and 1 to 2 equivalents of a base such
as sodium carbonate, sodium hydrogen carbonate, triethyl amine or the like are
added, and the reaction is carried out at a temperature ranging from 0°C to the reflux
temperature of these solvents for 10 minutes to 24 hours. Production Method C
(1-2)
[0114]
The compound of formula (1-1) wherein A1, A2, A3, G, X, Y, R1, R3, m and n are as
defined above and R2 has the same meaning defined above excluding hydrogen
atom according to the present invention that is the compound of formula (1) wherein
W is oxygen atom can be obtained by reacting the compound of formula (1-2)
wherein A1, A2, A3, G, X, Y, R1, R3, m and n are as defined above that is the compound
of formula (1) wherein W is oxygen atom and R2is hydrogen atom with the
compound of formula (11) wherein R2 has the same meaning defined above
excluding hydrogen atom, J3 is a good leaving group such as chlorine atom, bromine
atom, iodine atom, C1-C4alkylcarbonyloxy (for example pivaloyloxy), C1-
C4alkylsulfonate (for example methane sulfonyloxy), C1-C4haloalkylsulfonate (for
example trifluoromethane sulfonyloxy), arylsulfonate (for example benzene
sulfonyloxy, p-toluene sulfonyloxy) or azolyl (for example imidazol-1-yl), optionally in
the presence of a base, optionally by using a solvent inactive for the reaction.
[0115] The reaction substrates can be used in an amount of 1 to 50 equivalents
of the compound of formula (11) based on 1 equivalent of the compound of formula
(1-2).
[0116] In case where a solvent is used, the solvent is not specifically limited if it
dose not inhibit the progress of the reaction, but it includes for example aromatic
hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons
such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or
the like, aromatic halogenated hydrocarbons such as chlorobenzene,
dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro
methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane,
trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-
dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl
acetate, ethyl propionate or the like, amides such as N,N-dimethylformamide, N,Ndimethylacetamide,
N-methyl-2-pyrolidone or the like, amines such as triethyl amine,
tributyl amine, N,N-dimethyl aniline or the like, pyridines such as pyridine, picoline or
the like, alcoholes such as methanol, ethanol,
,3 O-
(1-1)
ethylene glycol or the like, acetonitrile, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-
imidazolidinone and water, and the like. These solvents may be used alone or in a
mixture of two or more.
[0117] When the base is used, alkali metal hydride such as sodium hydride,
potassium hydride or the like, alkali metal hydroxides such as sodium hydroxide,
potassium hydroxide or the like, alkali metal alkoxides such as sodium ethoxide,
potassium t-butoxide or the like, alkali metal amides such as lithium
diisopropylamide, lithium hexamethyl disilazane, sodium amide or the like, organic
metal compounds such as t-butyl lithium or the like, alkali metal carbonates such as
sodium carbonate, potassium carbonate, sodium hydrogen carbonate or the like,
organic bases such as triethyamine, tributylamine, N,N-dimethylaniline, pyridine, 4-
(dimethylamino)pyridine, imidazole, 1,8-diazabicyclo[5.4.0]-7-undecene, and the
like can be used in an amount of 1 to 4 equivalents based on the compound of
formula (1-2).
[0118] The reaction temperature may be an arbitrary temperature ranging from -
60°C to the reflux temperature of a reaction mixture, and the reaction time may be
an arbitrary time ranging from 5 minutes to 100 hours although it varies depending
on the concentration of the reaction substrates or the reaction temperature. [0119]
Generally, it is preferable to carry out the reaction by using 1 to 10 equivalents
of the compound of formula (11) based on 1 equivalent of the compound of formula
(1-2), in a polar solvent such as tetrahydrofurane, 1,4-dioxane, acetonitrile,
N,N-dimethylformamide or the like, optionally in the presence of 1 to 3 equivalents
of a base such as sodium hydride, potassium t-butoxide, potassium hydroxide,
potassium carbonate, triethylamine, pyridine or the like, based on 1 equivalent
of the compound of formula (1-2), at a temperature ranging from 0 to 90°C for 10
minutes to 24 hours. Production Method D
(Figure Removed) [0120] The compound of formula (1-3) wherein A1, A2, A3, G, X, Y, R1, R2, R3, m
(Figure Removed)and n are as defined above according to the present invention that is the compound
(1-3)
of formula (1) wherein W is sulfur atom can be obtained by reacting the compound of
formula (1-1) wherein A1, A2, A3, G, X, Y, R1, R2, R3, m and n are as defined above
according to the present invention that is the compound of formula (1) wherein W is
oxygen atom with a sulfurizing agent such as diphosphorus pentasulfide,
diphosphorus pentasulfide-HMDO (hexamethyldisiloxane), Lawesson's Reagent
(2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide), optionally by
using a solvent inactive for the reaction, optionally in the presence of a base. [0121]
The reaction substrates can be used in an amount of 1 to 50 equivalents of the
sulfurizing agent based on 1 equivalent of the compound of formula (1-1). [0122]
In case where a solvent is used, the solvent is not specifically limited if it dose not
inhibit the progress of the reaction, but it includes for example aromatic
hydrocarbons such as benzene, toluene, xylene or the like, aliphatic hydrocarbons
such as hexane, heptane or the like, alicyclic hydrocarbons such as cyclohexane or
the like, aromatic halogenated hydrocarbons such as chlorobenzene,
dichlorobenzene or the like, aliphatic halogenated hydrocarbons such as dichloro
methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane,
trichloroethylene, tetrachloroethylene or the like, ethers such as diethyl ether, 1,2-
dimethoxyethane, tetrahydrofuran, 1,4-dioxane or the like, amines such as triethyl
amine, tributyl amine, N,N-dimethyl aniline or the like, pyridines such as pyridine,
picoline or the like, and HMPA (hexamethylphosphoric triamide), and the like.
These solvents may be used alone or in a mixture of two or more.
[0123] The addition of a base is not necessarily required. However, when the
base is used, alkali metal carbonates such as sodium carbonate, potassium
carbonate, sodium hydrogen carbonate or the like, organic bases such as
triethyamine, tributylamine, N,N-dimethylaniline, pyridine, 4-(dimethylamino)pyridine,
imidazole, 1,8-diazabicyclo[5.4.0]-7-undecene, and the like can be used in an
amount of 1 to 10 equivalents based on the compound of formula (1-1). [0124]
The reaction temperature may be an arbitrary temperature ranging from 0°C to the
reflux temperature of a reaction mixture, and the reaction time may be an arbitrary
time ranging from 5 minutes to 100 hours although it varies depending on the
concentration of the reaction substrates or the reaction temperature. [0125]
Generally, it is preferable to carry out the reaction by using 1 to 10 equivalents of a
sulfurizing agent such as diphosphorus pentasulfide, diphosphorus pentasulfide-
HMDO, Lawesson's Reagent or the like, based on 1 equivalent of the
compound of formula (1-1), optionally in the presence of 1 to 4 equivalents of a base
such as sodium hydrogen carbonate, triethyamine, pyridine or the like, in a solvent
such as benzene, toluene, chlorobenzene, dichloromethane, chloroform, 1,2-
dimethoxyethane, tetrahydrofurane, 1,4-dioxane, HMPA or the like, at a temperature
ranging from room temperature to the reflux temperature of the reaction mixture for
10 minutes to 50 hours, or in a solvent amount of pyridine at a temperature of 80°C
to the reflux temperature of the reaction mixture for 1 to 3 hours. [0126] In
Production Method A to Production Method D, the aimed compound of the present
invention can be obtained by subjecting the reaction mixture after the completion of
the reaction to ordinary post-treatment such as a direct concentration, or a
concentration after dissolving in an organic solvent and washing with water or a
concentration after placing in ice water and extracting with an organic solvent. In
addition, when a purification is required, it can be separated and purified by an
arbitrary purification process such as recrystallization, column chromatograph, thin
layer chromatograph, liquid chromatograph collection or the like. [0127] The
compound of formula (5) used in Production Method A can be synthesized as
follows, for example. Reaction Scheme 1
00. 41 CO/Pd
H20
or 1)
BuLi
2)C02
CO/Pd Rb-OH
[0128] That is, the
compound of formula (5) wherein A1, A2, A3, G, X, Y, R3, m and n are as defined
above can be obtained by reacting the compound of formula (12) wherein A1, A2,
A3, G, X, Y, R3, m and n are as defined above, J4 is bromine
73
OH
(12)
(X)
atom, iodine atom, halosulfonyloxy (for example fluorosulfonyloxy), C1-
C4haloalkylsulfonyloxy (for example trifluoromethane sulfonyloxy) or arylsulfonyloxy
(for example benzenesulfonyloxy) according to a known method disclosed in
documents, for example by CO insertion reaction by use of a transition metal catalyst
such as palladium or the like stated in J. Org. Chem., 1999, vol. 64, p. 6921 or the
like, or by a process by lithiation and then reaction with carbonic acid gas stated in
Chem. Rev., 1990, vol. 90, p. 879.
[0129] In addition, the compound of formula (5) can be obtained by subjecting
the compound of formula (12) to a reaction according to a reaction condition for CO
insertion reaction by use of a transition metal catalyst such as palladium or the like
stated in J. Org. Chem., 1974, vol. 39, p. 3318 or the like to convert the compound of
formula (13) wherein A1, A2, A3, G, X, Y, R3, m and n are as defined above, Rb is C1-
C6alkyl such as methyl, ethyl or the like, and then hydrolizing according to an
ordinary ester hydrolysis disclosed in documents, for example a reaction condition
stated in Angew. Chem., 1951, vol. 63, p. 329, J. Am. Chem. Soc., 1929, vol. 51, p.
1865 or the like.
[0130] Some of the compounds of formula (6) used in Production Method A are
known compounds, and a part thereof is commercially available. Also, the
compounds other than the above-mentioned compounds can be synthesized
according to methods stated in for example Justus Liebigs Ann. Chem., 1979, p.
920, US 5,990,323, WO 96/11200 or the like, and general synthetic methods for
primary or secondary alkyl amines disclosed in documents. [0131] The
compounds of formula (8) used in Production Method B can be synthesized as
follows, for example. Reaction Scheme 2
o m.
R'
(14) (8)
[0132] That is, the compound of formula (8) wherein A1, A2, A3, W, Y, R1, R2 and n
are as defined above can be easily synthesized by reacting the compound of formula
(14) wherein A1, A2, A3, W, Y, R1, R2 and n are as defined above with hydroxyamine or
the salt thereof according to known methods disclosed in documents, for example
the method stated in J. Med. Chem., 2001, vol. 44, p. 2308 or the like. [0133]
The compounds of formula (10) used in Production Method B can be
synthesized as follows, for example. Reaction Scheme 3
(X)m
(17)
[0134] That is, the compound of formula (10) wherein G, X, R3 and m
are as defined above can be obtained by reacting the known compound of formula
(15) wherein G, X and m are as defined above, J5 is bromine atom, iodine atom, C1-
C4haloalkylsulfonyloxy (for example trifluoromethanesulfonyloxy), -B(OH)2, 4,4,5,5-
tetramethyl-1,3,2-dioxaborolan-2-yl, -Si(OEt)3, -ZnCI, -ZnBr or -Znl, etc. with the
compound of formula (16) wherein R3 is as defined above, J6 is halogen atom such
as bromine atom, iodine atom or the like, or -B(OH)2 according to an ordinary
crosscoupling reaction by use of a transition metal catalyst such as palladium or the
like disclosed in documents, for example a reaction condtioin stated in J. Org.
Chem., 1991, vol. 56, p. 7336, Tetrahedron Lett., 2001, vol. 42, p. 4083, or the like.
[0135] Some of the compounds of formula (16) used in the above-mentioned
process are known compounds, and a part thereof is commercially available. Also,
the compounds other than the above-mentioned compounds can be synthesized
according to methods disclosed in documents, for example a method stated in J.
Am. Chem. Soc., 1971, vol. 93, p. 1925, Tetrahedron Lett., 1990, vol. 31, p. 1919
and 2001, vol. 42, p. 4083 or the like.
[0136] In addition, the compounds of formula (10) can be obtained by reacting
the compound of formula (17) wherein G, X, R3 and m are as defined above
according to a reaction of converting carbonyl to olefine disclosed in documents, for
example areaction condition stated in J. Org. Chem., 1986, vol. 51, p. 5252 and
(15)
(10)
1994, vol. 59, p. 2898, Synthesis, 1991, p. 29, Tetrahedron Lett., 1985, vol. 26, p.
5579 or the like.
[0137] Some of the compounds of formula (11) used in Production method C are
known compounds, and a part thereof is commercially available. Also, the
compounds other than the above-mentioned compounds can be easily synthesized
according to methods disclosed in documents, for example a method stated in
Chem. Lett., 1976, p. 373, J. Am. Chem. Soc., 1964, vol. 86, p. 4383, J. Org. Chem.,
1976, vol. 41, p. 4028 and 1978, vol. 43, p. 3244, Org. Synth., 1988, Corrective vol.
6, p. 101, Tetrahedron Lett., 1972, p. 4339, GB 2,161,802, EP 0,051,273or the like.
[0138] The compounds of formula (12) can be synthesized as follows, for
example. Reaction Scheme 4
(Y)n
A1 halogenation
(12)
[0139] That is, the compounds of formula (12) wherein A1, A2, A3, G, X, Y, R3, m, n
and J4 are as defined above can be obtained by halogenating the compound of
formula (18) wherein A1, A2, A3, Y, n and J4 are as defined above under a condition
similar to that of Production Method B to obtain the compound of formula (19)
wherein A1, A2, A3, Y, n, J3 and J4 are as defied above, and then reacting it with the
compound of formula (10) wherein G, X, R3 and m are as defined above. [0140]
The compound of formula (18) can be easily synthesized by use of the
corresponding known substituted aromatic aldehyde similarly to the process
described in Reaction Scheme 2. [0141] The compound of formula (14) can be
synthesized for example
acccording to Reaction Scheme 5 or Reaction Scheme 6.
Reaction Scheme 5
[0142] The compounds of formula (14) wherein A1, A2, A3, W, Y, R1, R2 and n are as
defined above can be obtained by subjecting the compound of formula (20) wherein
A1, A2, A3, W, Y, R1, R2, n and J4 are as defined above to CO insertion reaction
according to known methods disclosed in documents, for example the reaction by
use of a transition metal catalyst such as palladium or the like in the presence of
hydride source such as formic acid or the like stated in Bull. Chem. Soc. Jpn., 1994,
vol. 67, p. 2329, J. Am. Chem. Soc., 1986, vol. 108, p. 452, or the like. Reaction
Scheme 6
[0143] The compounds of formula (14-1) wherein A1, A2, A3, Y, R1, R2 and n are as
defined above that are the compounds of formula (14) wherein W is oxygen atom
can be synthesized by reacting the known compound of formula (21) wherein A1, A2,
A3, Y and n are as defined above with the compound of formula (6) wherein R1 and
R2 are as defined above by use of the method similar to Production Method A. [0144]
The compounds of formula (17) can be synthesized as follows, for
example. Reaction
Scheme 7
(26)
[0145] That is, the compounds
of formula (17) wherein X, R3 and
m are as defined above, G
is benzene ring can be obtained by
reacting the known compound of
formula (23) wherein X and m are as defined above, G is benzene ring with the
known compound of formula (24) wherein R3 is as defined above, J7 is a leaving
group such as halogen atom, trifluoromethanesulfonyloxy, 2-pyridyloxy or the like, or
the known compound of formula (25) wherein R3 is as defined above according to a
genaral acylating reaction of aromatic ring disclosed in documents, for example a
method stated in Chem. Lett., 1990, p. 783, J. Org. Chem., 1991, vol. 56, p. 1963 or
the like.
[0146] In addition, the compound of formula (17) wherein G, X, R3 and m are as
defined above can be obtained according to general methods disclosed in
documents for example by a method stated in J. Am. Chem. Soc., 1955, vol. 77, p.
3657, Tetrahedron Lett., 1980, vol. 21, p. 2129 and 1991, vol. 32, p. 2003, US
5,514,816 in which the compound of formula (26) wherein G, X and m are as defined
above, J8 is bromine atom or iodine atom is lithiated and the resulting compound is
reacted with the known compound of formula (27) wherein R3 is as defined above, J9 is
halogen atom, hydroxy, metal salt (for example, -OLi, -ONa), C1-C4alkoxy (for
example, methoxy, ethoxy), di(C1-C4alkyl)amino (for example, diethylamino), C1-
C4alkoxy C1-C4alkyl amino(for example O,N-dimethylhydroxyamino) or cyclic amino
(for example, piperidin-1-yl, morpholin-4-yl, 4-methylpiperadin-1-yl), or the known
compound of formula (25), or by a method stated in Heterocycles, 1987, vol.
221, Synth. Commun., 1985, vol. 15, p. 1291 and 1990, vol. 20, p. 1469, DE
19727042, or the like in which a Grignard reagent is formed and then it is reacted
with the compound of formula (27) or the compound of formula (25).
[0147] The compounds of formula (20) can be synthesized according to for
example Reaction Scheme 8 or Reaction Scheme 9.
Reaction Scheme 8
[0148] The
compounds of
formula (20-1) wherein A1, A2, A3, Y, R1, R2, n and J4 are as defined above that are
the compounds of formula (20) wherein W is oxygen atom can be obtained by
reacting the known compound of formula (28) wherein A1, A2, A3, Y, n and J4 are as
defined above with the compound of formula (6) wherein R1 and R2 are as defined
above by use of the method similar to Production Method A. Reaction Scheme 9
[0149] The compounds of formula (20-2) wherein A1, A2, A3, Y, R1, R2, n and J5 are
as defined above that are the compounds of formula (20) wherein W is sulfur atom
can be obtained by reacting the compound of formula (20-1) wherein A1, A2, A3, Y, R1,
R2, n and J4 are as defined above that are the compounds of formula (20) wherein W
is oxygen atom with a sulfurizing agent such as diphosphorus
pentasulfide, diphosphorus pentasulfide-HMDO (hexamethyldisiloxane), Lawesson's
Reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide) under
a condition similar to that of Production Method D.
[0150] In each reaction, after the completion of the reaction, each production
intermediate that is a starting compound in Production Method A to Produciton
Method C can be obtained by carrying out normal post-treatments. [0151] In
addition, each production intermediate produced by the above-mentioned methods
can be used for the following reaction step as such without isolation or purification.
[0152] The active compounds included in the present invention concretely
include for example the compounds shown in Tables 2 and 3. The compounds that
can be used as novel production intermediates for producing the active compounds
included in the present invention concretely include for example the compounds
shown in Tables 4 to 6. In the interim, the compounds shown in Tables 2 to 6 are
for purposes of illustration and the present invention is not limited thereto. [0153]
In the meantime, in Tables, the indication "Et" means ethyl, hereinafter similarly
thereto, "n-Pr" and "Pr-n" mean normal propyl, "i-Pr" and "Pr-i" mean isopropyl, "c-Pr"
and "Pr-c" mean cyclopropyl, "n-Bu" and "Bu-n" mean normal butyl, "s-Bu" and "Bu-s"
mean secondary butyl, "i-Bu" and "Bu-i" mean isobutyl, "t-Bu" and "Bu-t" mean
tertiary butyl, "c-Bu" and "Bu-c" mean cyclobutyl, "n-Pen" and "Pen-n" mean normal
pentyl, "c-Pen" and "Pen-c" mean cyclopentyl, "n-Hex" and "Hex-n" mean normal
hexyl, "c-Hex" and "Hex-c" mean cyclohexyl,phthyl, "2- "Hept" means heptyl, "Oct"
means octyl, "Ph" means phenyl, "1-Naph" means 1-naNaph" means 2-naphthyl, and
in Tables, aromatic heterocyclic rings of D-1a to D-59a are the following structures,
respectively
In the table, the number showing the substitution position of substituents (X)mand
(Y)n corresponds to the position number indicated in the following structural
formulae. The indication "-" means no-substitution.
In addition, substituent G in the formulae [2]-1 to [2]-4 is the structure shown by the
following G-1 to G-22, respectively.
[0154] The compounds of the present invention can effectively control in a low
concentration so-called agricultural insects injuring agricultural and horticultural
crops and trees, so-called domestic animal pests parasitizing domestic animals and
260
domestic fowls, so-called hygienic pests having an adverse affect on human being's
environment such as houses, insects as so-called stored grain insects injuring grains
and the like stored in storehouses, and any pests of acarids, crustaceans, mollusks
and nematodes generating in the similar scenes.
[0155] The insects, acarids, crustaceans, mollusks and nematodos that the
compounds of the present invention can control concretely include for example the
followings:
Lepidoptera insects, such as Adoxophyes honmai, Adoxophyes orana faciata,
Archips breviplicanus, Archips fuscocupreanus, Grapholita molesta, Homona
magnanima, Leguminivora glycinivorella, Matsumuraeses phaseoli, Pandemis
heparana, Bucculatrix pyrivorella, Lyonetia clerkella, Lyonetia prunifoliella malinella,
Caloptilia theivora, Phyllonorycter ringoniella, Phyllocnistis citrella, Acrolepiopsis
sapporensis, Acrolepiopsis suzukiella, Plutella xylostella, Stathmopoda masinissa,
Helcystogramma triannulella, Pectinophora gossypiella, Carposina sasakii, Cydla
pomonella, Chilo suppressalis, Cnaphalocrocis medinalis, Conogethes punctiferalis,
Diaphania indica, Etiella zinckenella, Glyphodes pyloalis, Hellula undalis, Ostrinia
furnacalis, Ostrinia scapulalis, Ostrinia nubilalis, Parapediasia teterrella, Parnara
guttata, Pieris brassicae, Pieris rapae crucivora, Ascotis selenaria, Pseudoplusia
includens, Euproctis pseudoconspersa, Lymantria dispar, Orgyia thyellina,
Hyphantria cunea, Lemyra imparilis, Adris tyrannus, Aedia leucomelas, Agrotis
ipsilon, Agrotis segetum, Autographa nigrisigna, Ctenoplusia agnata, Helicoverpa
armigera, Helicoverpa assulta, Helicoverpa zea, Heliothis virescens, Mamestra
brassicae, Mythimna separata, Naranga aenescens, Spodoptera eridania,
Spodoptera exigua, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura,
Spodoptera depravata, Trichoplusia ni, Endopiza viteana, Manduca
quinquemaculata, Manduca sexta, or the like;
Thysanoptera insects, such as Frankliniella intonsa, Frankliniella occidentalis,
Heliothrips haemorrhoidalis, Scirtothrips dorsalis, Thrips palmi, Thrips tabaci,
Ponticulothrips diospyrosi, or the like;
Hemiptera insects, such as Dolycoris baccarum, Eurydema rugosum, Eysarcoris
aeneus, Eysarcoris lewisi, Eysarcoris ventralis, Glaucias subpunctatus,
Halyomorpha halys, Nezara antennata, Nezara viridula, Piezodorus hybneri, Plautia
crossota, Scotinophora lurida, Cletus punctiger, Leptocorisa chinensis, Riptortus
clavatus, Rhopalus msculatus, Cavelerius saccharivorus, Togo hemipterus,
Dysdercus cingulatus, Stephanitis pyrioides, Halticus insularis, Lygus lineolaris,
Stenodema sibiricum, Stenotus rubrovittatus, Trigonotylus caelestialium, Arboridia
apicalis, Balclutha saltuella, Epiacanthus stramineus, Empoasca fabae, Empoasca
nipponica, Empoasca onukii, Empoasca sakaii, Macrosteles striifrons, Nephotettix
cinctinceps, Psuedatomoscelis seriatus, Laodelphax striatella, Nilaparvata lugens,
Sogatella furcifera, Diaphorina citri, Psylla pyrisuga, Aleurocanthus spiniferus,
Bemisia argentifolii, Bemisia tabaci, Dialeurodes citri, Trialeurodes vaporariorum,
Viteus vitifolii, Aphis gossypii, Aphis spiraecoia, Myzus persicae, Toxoptera aurantii,
Drosicha corpulenta, Icerya purchasi, Phenacoccus solani, Pianococcus citri,
Planococcus kuraunhiae, Pseudococcus comstocki, Ceroplastes ceriferus,
Ceroplastes rubens, Aonidiella aurantii, Comstockaspis perniciosa, Fiorinia theae,
Pseudaonidia paeoniae, Pseudaulacaspis pentagona, Pseudaulacaspis prunicola,
Unaspis euonymi, Unaspis yanonensis, Cimex lectularius, or the like;
Coleoptera insects, such as Anomala cuprea, Anomala rufocuprea, Gametis
jucunda, Heptophylla picea, Popillia japonica, Lepinotarsa decemiineata, Melanotus
fortnumi, Melanotus tamsuyensis, Lasioderma serricorne, Epuraea domina,
Epilachna varivestis, Epilachna vigintioctopunctata, Tenebrio molitor, Tribolium
castaneum, Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris,
Xylotrechus pyrrhoderus, Callosobruchus chinensis, Aulacophora femoralis,
Chaetocnema concinna, Diabrotica undecimpunctata, Diabrotica virgifera, Diabrotica
barberi, Oulema oryzae, Phyllotreta striolata, Psylliodes angusticollis, Rhynchites
heros, Cylas formicarius, Anthonomus grandis, Echinocnemus squameus, Euscepes
postfasciatus, Hypera postica, Lissohoptrus oryzophilus, Otiorhynchus sulcatus,
Sitophilus granarius, Sitophilus zeamais, Sphenophorus venatus vestitus, Paederus
fuscipes, or the like;
Diptera insects, such as Asphondylia yushimai, Sitodiplosis mosellana, Bactrocera
cucurbitae, Bactrocera dorsalis, Ceratitis capitata, Hydrellia griseola, Drosophila
suzukii, Agromyza oryzae, Chromatomyia horticola, Liriomyza bryoniae, Liriomyza
chinensis, Liriomyza sativae, Liriomyza trifolii, Delia platura, Pegomya cunicularia,
Rhagoletis pomonella, Mayetiola destructor, Musca domestica, Stomoxys calcitrans,
Melophagus ovinus, Hypoderma bovis, Hypoderma lineatum, Oestrus ovis, Glossina
palpalis, Glossina morsitans, Prosimulium yezoensis, Tabanus trigonus,
Telmatoscopus albipunctatus, Leptoconops nipponensis, Culex pipiens pallens,
Aedes aegypti, Aedes albopicutus, Anopheles hyracanus sinesis, or the like;
Hymenoptera insects, such as Apethymus kuri, Athalia rosae, Arge pagana,
Neodiprion sertifer, Dryocosmus kuriphilus, Eciton burchelli, Eciton schmitti,
Camponotus japonicus, Vespa mandarina, Myrmecia spp., Solenopsis spp.,
Monomorium pharaonis, or the like;
Orthoptera insects, such as Teleogryllus emma, Gryllotalpa orientalis, Locusta
migratoria, Oxya yezoensis, Schistocerca gregaria, or the like;
Collembola insects, such as Onychiurus folsomi, Onychiurus sibiricus, Bourletiella
hortensis, or the like;
Dictyoptera insect, such as Periplaneta fuliginosa, Periplaneta japonica, Blattella
germanica, or the like;
Isoptera insects, such as Coptotermes formosanus, Reticulitermes speratus,
Odontotermes formosanus, or the like;
Siphonaptera insects, such as Ctenocephalidae felis, Ctenocephalides canis,
Echidnophaga gallinacea, Pulex irritans, Xenopsylla cheopis, or the like;
Mallophaga insects, such as Menacanthus stramineus, Bovicola bovis, or the like;
Anoplura insects, such as Haematopinus eurysternus, Haematopinus suis,
Linognathus vituli, Solenopotes capillatus, or the like;
Tarsonemid mites, such as Phytonemus pallidus, Polyphagotarsonemus latus,
Tarsonemus bilobatus, or the like;
Eupodid mites, such as Penthaleus erythrocephalus, Penthaleus major, or the like;
Spider mites, such as Oligonychus shinkajii, Panonychus citri, Panonychus mori,
Panonychus ulmi, Tetranychus kanzawai, Tetranychus urticae, or the like;
Eriophyid mites, such as Acaphylla theavagrans, Aceria tulipae, Aculops lycopersici,
Aculops pelekassi, Aculus schlechtendali, Eriophyes chibaensis, Phyllocoptruta
oleivora, or the like;
Acarid mites, such as Rhizoglyphus robini, Tyrophagus putrescentiae, Tyrophagus
similis, or the like;
Bee brood mites, such as Varroa jacobsoni, or thelike;
Ixodides, such as Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis
longicornis, Haemophysalis flava, Haemophysalis campanulata, Ixodes ovatus,
Ixodes persulcatus, Amblyomma spp., Dermacentor spp., or the like;
Cheyletidae, such as Cheyletiella yasguri, Cheyletiella blakei, or the like;
Demodicidae, such as Demodex canis, Demodex cati, or the like;
Psoroptidae, such as Psoroptes ovis, or the like;
Scarcoptidae, such as Sarcoptes scabiei, Notoedres cati, Knemidocoptes spp., or
the like;
Crustacea, such as Armadillidium vulgare, or the like;
Gastropoda, such as Pomacea canaliculata, Achatina fulica, Meghimatium
bilineatum, Umax Valentiana, Acusta despecta sieboldiana, Euhadra peliomphala,
or the like;
Nematodes, such as Prathylenchus coffeae, Prathylenchus penetrans,
Prathylenchus vulnus, Globodera rostochiensis, Heterodera glycines, Meloidogyne
hapla, Meloidogyne incognita, Aphelenchoides besseyi, Bursaphelenchus
xylophilus, or the like. But the present invention is not limited thereto.
[0156] The endo-parasites of domestic animals, domestic fowls, pets and the like
that the compounds of the present invention can control concretely include for
example the followings:
Nematodes, such as Haemonchus, Trichostrongylus, Ostertagia, Nematodirus,
Cooperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia, Trichuris,
Storongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia,
Oxyuris, Ancylostoma, Uncinaria, Toxascaris, Parascaris, or the like;
Filariidae in nematodes, such as Wuchereria, Brugia, Onchoceca, Dirofilaria, Loa, or
the like;
Dracunculidae in nematodes, such as Deacunculus, or the like;
Cestoda, such as Dipylidium caninum, Taenia taeniaeformis, Taenia solium, Taenia
saginata, Hymenolepis diminuta, Moniezia benedeni, Diphyllobothrium latum,
Diphyllobothrium erinacei, Echinococcus granulosus, Echinococcus multilocularis, or
the like;
Trematoda, such as Fasciola hepatica.F.gigantica, Paragonimus westermanii,
Fasciolopsic bruski, Eurytrema pancreaticum.E.coelomaticum, Clonorchis sinensis,
Schistosoma japonicum, Schistosoma haematobium, Schistosoma mansoni, or the
like;
Eimeria spp., such as Eimeria tenella, Eimeria acervulina, Eimeria brunetti, Eimeria
maxima, Eimeria necatrix, Eimeria bovis, Eimeria ovinoidalis, or the like;
Trypanosomsa cruzi, Leishmania spp., Plasmodium spp., Babesis spp.,
Trichomonadidae spp., Histomanas spp., Giardia spp., Toxoplasma spp.,
Entamoeba histolytica, Theileria spp., or the like. But the present invention is not
limited thereto.
[0157] Further, the compounds of the present invention are effective for pests
acquiring high resistance against existing insecticides such as organic phosphorus
compounds, carbamate compounds or pyrethroid compounds, etc.
[0158] That is, the compounds of the present invention can effectively control
pests that belong to insects such as Collembola, Dictyoptera, Orthoptera, Isoptera,
Thysanoptera, Hemiptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, Isoptera
and Anoplura, Acarina, Gastropoda and Nematoda, in a low concentration. On the
other hand, the compounds of the present invention have an extremely useful
charactristic that they have little adverse affect on mammals, fishes, crustaceans and
useful insects (beneficial insect such as honeybee, bumblebee or the like, or,
natural enemies such as Aphytis lingnanensis, Aphidius colemani, Orius strigicollis,
Amblyseius californicus, or the like).
[0159] When the compounds of the present invention are used, they can be
generally mixed with a suitable solid carrier or liquid carrier, optionally along with
surfactant, penetrating agent, spreading agent, thickner, anti-freezing agent, binder,
anti-caking agent, disintegrating agent, anti-foaming agent, preservative, stabilizer,
and the like, and can be formulated into any desired forms for practical use, such as
soluble concentrates, emulsifiable concentrates, wettable powders, water soluble
powders, water dispersible granules, water soluble granules, suspension
concentrates, concentrated emulsions, suspoemulsions, microemulsions, dustable
powders, granules, tablets and emulsifiable gels. From the viewpoint of an
elimination or reduction of labor and an improvement of safety, the formulations in
any desired forms described above may be included into a water-soluble bag made
of water-soluble capsule or water-soluble film.
[0160] The solid carrier includes, for example, natural minerals such as quartz,
calcite, sepiolite, dolomaite, chalk, kaolinite, pyrofilite, celicite, halocite,
methahalocite, kibushi clay, gairome clay, pottery stone, zeaklite, allophane, white
sand, mica, talc, bentonite, activeted earth, acid china clay, pumice, attapulgite,
zeolite and diatomaceous earth, etc., calcined products of natural minerals such as
calcined clay, perlite, white sand balloon (loam balloon), vermiculite, attapulgus clay
and calcined diatomaceous earth, etc., inorganic salts such as magnesium
carbonate, calcium carbonate, sodium carbonate, sodium hydrogen carbonate,
ammonium sulfate, sodium sulfate, magnesium sulfate, diammonium hydrogen
phosphate, ammonium dihydrogen phosphate and potassium chloride, etc.,
saccharides such as glucose, fructose, sucrose and lactose, etc., polysaccharides
such as starch, powder cellulose and dextrin, etc., organic materials such as urea,
urea derivatives, benzoic acid and a salt of benzoic acid, etc., plants such as wood
powder, cork powder, corn head stem, walnut shell and tobacco stem, etc., fly ash,
white carbon (e.g., hydrated synthetic silica, anhydrous synthetic silica and hydrated
synthetic silicate, etc.) and feritilizers, etc.
[0161] As the liquid carrier, there may be mentioned, for example, aromatic
hydrocarbons such as xyiene, alkyl(C9 or C10, etc.)benzene, phenylxylylethane and
alkyl(C, or C3l etc.Jnaphthalene, etc., aliphatic hydrocarbons such as machine oil,
normal paraffin, isoparaffin and naphthene, etc., a mixture of aromatic hydrocarbons
and aliphatic hydrocarbons such as kerosene, etc., alcohols such as ethanol,
isopropanol, cyclohexanol, phenoxyethanol and benzylalcohol, etc., polyvalent
alcohols such as ethylene glycol, propyleneglycol, diethylene glycol, hexylene glycol,
polyethylene glycol and polypropyleneglycol, etc., ethers such as propyl cellosolve,
butyl cellosolve, phenyl cellosolve, propyleneglycol monomethyl ether,
propyleneglycol monoethyl ether, propyleneglycol monopropyl ether, propyleneglycol
monobutyl ether and propyleneglycol monophenyl ether, etc., ketones such as
acetophenone, cyclohexanone and y-butyrolactone, etc., esters such as aliphatic
acid methyl ester, dialkyl succinate, dialkyl glutamate, dialkyl adipate and dialkyl
phthalate, etc., acid amides such as N-alkyKC^ C8 or C12, etc.)pyrrolidone, etc., oil
and fats such as soybean oil, linseed oil, rapeseed oil, coconut oil, cottonseed oil and
caster oil, etc., dimethylsulfoxide and water.
[0162] These solid and liquid carriers may be used alone or in combination of two
or more kinds in combination.
[0163] As the surfactant, there may be mentioned, for example, nonionic
surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl (mono- or
di-)phenyl ether, polyoxyethylene (mono-, di- or tri-)styrylphenyl ether,
polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid
(mono- or di-)ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester,
caster oil-ethylene oxide adducts, acetylene glycol, acetylene alcohol, ethylene
oxide adducts of acetylene glycol, ethylene oxide adducts of acetylene alcohol and
alkyl glycoside, etc., anionic surfactants such as alkyl sulfate, alkylbenzenesulfonate,
lignine sulfonate, alkylsulfosuccinate, naphthalene sulfonate, alkylnaphthalene
sulfonate, formalin condensate salt of naphthalene sulfonic acid, formalin
condensate salt of alkylnaphthalene sulfonic acid, polyoxyethylene alkyl ether sulfate
or phosphate, polyoxyethylene (mono- or di-)alkylphenyl ether sulfate or phosphate,
polyoxyethylene (mono-, di- or tri-)styrylphenyl ether sulfate or phosphate,
polycarboxylate (e.g., polyacryaltes, polymaleates and copolymer materials of
maleic acid and olefin, etc.) and polystyrenesulfonate, etc., cationic surfactants such
as alkylamine salt and alkyl quaternary ammonium salt, etc., amphoteric surfactants
such as amino acid type and betaine type, etc., silicone type surfactants and fluorine
type surfactants.
[0164] A content of these surfactants is not specifically limited, and it is desirably
in the range of 0.05 to 20 parts by weight in general based on 100 parts by weight of
the preparation according to the present invention. Also, these surfactants may be
used alone or in combination of two or more kinds in combination.
[0165] A dose of the compound of the present invention to be applied may vary
depending on the place to be applied, time to be applied, method to be applied,
crops to cultivate, etc., and in general, it is suitable in an amount of about 0.005 to 50
kg or so per a hectare (ha) as an amount of the effective ingredient.
[0166] On the other hand, when the compound of the present invention is used
for controlling ecto- or endo-parasites of mammals and birds as domestic animals
and pets, the effective amount of the compound of the present invention together
with additives for formulations can be administered through oral administration,
parenteral administration such as injection (intramuscular, subcutaneous,
intravenous, intraperitoneal) or the like; transdermal administration such as dipping,
spray, bathing, washing, pouring-on and spotting-on, and dusting, or the like ;
transnasal administration. The compound of the present invention can be also
administered through a formed product by use of a strip, a plate, a band, a collar, an
ear mark, a limb band, a labe apparatus, or the like. In administration, the
compound of the present invention can be formed in an arbitrary dosage form that is
suited for the administration route.
[0167] The arbitrary dosage form includes solid preparations such as a dustable
powder, a granule, wettable powder, a pellete, a tablet, a bolus, a capsule, a formed
product containing an active compound; liquid formulations such as an injectable
liquid formulation, an oral liquid formulation, a liquid formulation used on skin or in
body cavity; solution preparations such as a pour-on agent, a spot-on agent, a
flowable agent, an emulsifiable concentrate; semi-solid preparations such as an
ointment, gel or the like.
The solid preparations can be mainly used through oral administration or
transdermal administratin by diluting with water or the like, or by environmental
treatment. The solid preparations can be prepared by mixing the active
compound with suitable excipients and optionally auxiliary substances and
converting to a desired form. The suitable excipients include for example
inorganic substances such as carbonates, hydrogen carbonates, phosphates,
aluminum oxide, silica, clay or the like, organic substances such as sugar,
cellulose, milled cereal, starch or the like.
[0168] The injectable liquid formulation can be administered intravenously,
intramuscularly and subcutaneously. The injectable liquid formulation can be
prepared by dissolving an acitve compound in a suitable solvent and optionally by
adding an additive such as a solubilizing agent, an acid, a base, a buffering salt, an
antioxidant, and a protective agent or the like. Suitable solvent is for example
water, ethanol, butanol, benzyl alcohol, glycerin, propylene glycol, poethylene glycol,
N-methylpyrrolidone, and a mixture thereof, a physiologically permissible vegetable
oil, a synthetic oil suitable for injection, or the like. The solubilizing agent includes
polyvinyl pyrrolidone, polyoxyethylated castor oil and polyoxyethylated sorbitan
ester, or the like. The protective agent includes benzyl alcohol, trichlorobutanol, phydroxybenzoic
acid ester and n-butanol or the like.
[0169] The oral liquid formulation can be administered directly or after dilution.
It can be prepared similarly to the injectable liquid formulation.
[0170] The flowable agent and the emulsifiable concentrate can be administered
directly or after dilution through transdermal administration or environmental
treatment.
[0171] The liquid formulation used on skin can be administered by pouring on,
spreading, rubbing, atomizing, spraying, or dipping (dipping, bathing or washing).
These liquid can be prepared similarly to the injectable liquid formulation.
[0172] The pour-on agent and the spot-on agent are poured or atomized on the
limited spot on the skin, thereby the active compound can be penetrated into the skin
and act in the whole body. The pour-on agent and the spot-on agent can be
prepared by dissolving, suspending or emulsifying an active ingredient in a suitable
skin-fitted solvent or solvent mixture. If required, an auxiliary substance such as a
surfactant, a colorant, an absorption promoting agent, an antioxidant, a light
stabilizer and an adhesive, etc. may be added.
[0173] Suitable solvent includes water, alkanol, glycol, polyethylene glycol,
polypropylene glycol, glycerin, benzyl alcohol, phenylethanol, phenoxyethanol, ethyl
acetate, butyl acetate, benzyl benzoate, dipropylene glycol monomethyl ether,
diethylene glycol monobutyl ether, acetone, methyl ethyl ketone, aromatic and/or
aliphatic hydrocarbon, vegetable or synthetic oil, DMF, liquid paraffin, light-duty liquid
paraffin, silicone, dimethylacetamide, N-methylpyrrolidone or 2,2-dimethyl-4-oxymethylene-
1,3-dioxolane. The absorption promoting agent includes DMSO,
isopropyl myristate, dipropylene glycol pelargonate, silicone oil, aliphatic ester,
triglyceride and fatty alcohol. The antioxidant includes sulfite, metabisulfite,
ascorbic acid, butylhydroxytoluene, butylhydroxyanisole and tocopherol.
[0174] The emusifiable concentrate can be administrated orally, subcutaneously
or injectably. The emusifiable concentrate can be prepared by dissolving an active
ingredient in a hydrophobic phase or a hydrophilic phase, and then homogenating
the resulting solution with a suitable emulsifying agent optionally with further an
auxiliary substance such as a colorant, an absortion promoting agent, a protective
agent, an antioxidant, a light screen and a thickening agent.
[0175] The hydrophobic phase (oil) includes paraffin oil, silicone oil, sesameseed
oil, oil of almonds, castor oil, synthetic triglyceride, ethyl stearate, di-n-butyryl
adipate, hexyl laurate, dipropylene glycol pelargonate, ester of branched short chain
length aliphatic acid with saturated aliphatic acid of chain length C16 to C18,
isopropyl myristate, isopropyl palmitate, capryl/caprylic acid ester of saturated fatty
alcohol of chain length C12 to C18, isopropyl stearate, oleyl oleate, decyl oleate,
ethyl oleate, ethyl lactate, wax-like fatty acid ester, dibutyl phthalate, diisopropyl
adipate, isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol.
[0176] The hydrophilic phase includes water, propylene glycol, glycerin, sorbitol.
[0177] The emulsifying agent includes non-ionic surfactants such as
polyoxyethylated castor oil, polyoxyethylated sorbitan mono-olefinate, sorbitan
monostearate, glycerin monostearate, polyoxyethyl stearate, alkylphenol polyglycol
ether; amphoteric surfactants such as di-sodium N-lauryl p-iminodipropionate,
lecithin or the like; anionic surfactants such as sodium lauryl sulfate, fatty alcohol
sulfric acid ether, monoethanol amine salt of mono/dialkylpolyglycol orthophosphate
or the like; cationic surfactants such as cetyl chloride trimethylammonium or the like.
[0178] The other auxiliary substance includes carbocymethylcellulose,
methylcellulose, polyacrylate, arginate, gelatin, gum arabic, polyvinyl pyrrolidone,
polyvinyl aocohol, methylvinyl ether, copolymer of maleic anhydride, polyethylene
glycol, wax, colloidal silica.
[0179] The semi-solid preparation can be administered by coating or spreading
on the skin, or by introducing in body cavity. The gel can be prepared by adding a
thickener in an amount enough to provide a clear substance having a viscosity of
ointment in a solution prepared for the injectable liquid formulation as mentioned
above.
[0180] Next, formulation examples of the preparation in case where the
compound of the present invention is used are shown below. Provided that
formulation examples of the present invention are not limited only thereto. In the
interim, in the following Formulation Examples, "part(s)" mean part(s) by weight.
(Wettable powder)
Compound of the present invention 0.1 to 80 parts
Solid carrier 5 to 98.9 parts
Surfactant 1 to 10 parts
Others 0 to 5 parts
As other components, there may be mentioned, for example, a non-caking agent, a
decomposition preventing agent, and the like.
(Emulsifiable concentrate)
Compound of the present invention 0.1 to 30 parts
Liquid carrier 45 to 95 parts
Surfactant 4.9 to 15 parts
Others 0 to 10 parts
As other components, there may be mentioned, for example, a spreading agent, a
decomposition preventing agent, and the like.
(Suspension concentrate)
Compound of the present invention 0.1 to 70 parts
Liquid carrier 15 to 98.89 parts
Surfactant 1 to 12 parts
Others 0.01 to 30 parts
As other components, there may be mentioned, for example, an antifreezing agent, a
thicknening agent, and the like.
(Water dispersible granule)
Compound of the present invention 0.1 to 90 parts
Solid carrier 0 to 98.9 parts
Surfactant 1 to 20 parts
Others 0 to 10 parts
As other components, there may be mentioned, for example, a binder, a
decomposition preventing agent, and the like.
(Soluble concentrate)
Compound of the present invention 0.01 to 70 parts
Liquid carrier 20 to 99.99 parts
Others 0 to 10 parts
As other components, there may be mentioned, for example, an antifreezing agent, a
spreading agent, and the like.
(Granule)
Compound of the present invention 0.01 to 80 parts
Solid carrier 10 to 99.99 parts
Others 0 to 10 parts
As other components, there may be mentioned, for example, a binder, a
decomposition preventing agent, and the like.
(Dustable powder)
Compound of the present invention 0.01 to 30 parts
Solid carrier 65 to 99.99 parts
Others 0 to 5 parts
As other components, there may be mentioned, for example, a drift preventing
agent, a decomposition preventing agent, and the like.
[0181] Next, formulation examples using the compound of the present invention
as an effective ingredient are described in more detail, but the present invention is
not limited thereto. In the interim, in the following Formulation Examples, "part(s)"
mean part(s) by weight.
(Formulation Example 1) Wettable powder
Compound of the present invention No. 5-075 20 parts
Pyrophylite 74 parts
Solpol 5039 4 parts
(A mixture of a nonionic surfactant and an anionic surfactant: available from TOHO
Chemical Industry Co., LTD, Tradename)
CARPREX #80D 2 parts
(Synthetic hydrated silicic acid: available from Shionogi & Co., Ltd., Tradename)
The above materials are uniformly mixed and pulverized to make wettable powder.
(Formulation Example 2) Emulsion
Compound of the present invention No. 5-075 5 parts
Xylene 75 parts
N-methylpyrrolidone 15 parts
Solpol 2680 5 parts
(A mixture of a nonionic surfactant and an anionic surfactant: available from TOHO
Chemical Industry Co., LTD, Tradename)
The above materials are uniformly mixed to make emulsifiable concentrate.
(Formulation Example 3) Suspension concentrate
Compound of the present invention No. 5-075 25 parts
AgrisolS-710 10 parts
(a nonionic surfactant: available from KAO CORPORATION, Tradename)
LunoxlOOOC 0.5 part
(an anionic surfactant: available from TOHO Chemical Industry Co., LTD,
Tradename)
Xanthan gum 0.2 part
Water 64.3 parts
The above materials are uniformly mixed, and then, wet pulverized to make
suspension concentrate.
(Formulation Example 4) Water dispersible granule
Compound of the present invention No. 5-075 75 parts
HITENOLNE-15 5 parts
(an anionic surfactant: available from DAI-ICHI KOGYO SEIYAKU CO., LTD.,
Tradename)
VANILLEXN 10 parts
(an anionic surfactant: available from Nippon Paper Chemicals Co., Ltd.,
Tradename)
CARPREX#80D 10 parts
(Synthetic hydrated silicic acid: available from Shionogi & Co., Ltd., Tradename)
The above materials are uniformly mixed and pulverized, and then, a small amount
of water is added to the mixture and the resulting mixture is mixed under stirring,
granulated by an extrusion granulator, and dried to make water dispersible granule.
(Formulation Example 5) Granule
Compound of the present invention No. 5-075 5 parts
Bentonite 50 parts
Talc 45 parts
The above materials are uniformly mixed and pulverized, and then, a small amount
of water is added to the mixture and the resulting mixture is mixed under stirring,
granulated by an extrusion granulator, and dried to make granule.
(Formulation Example 6) Dustable powder
Compound of the present invention No. 5-075 3 parts
CARPREX #80D 0.5 parts
(Synthetic hydrated silicic acid: available from Shionogi & Co., Ltd., Tradename)
Kaolinite 95 parts
Diisopropyl phosphate 1.5 parts
The above materials are uniformly mixed and pulverized to make dustable powder.
When the formulation is used, it is sprayed by diluting with water in 1- to 1000-fold
concentration, or directly without dilution.
(Formulation Example 7) Wettable powder preparation
Compound of the present invention No. 5-086 25 parts
Sodium diisobutylnaphthalenesulfonate 1 part
Calcium n-dodecylbenzenesulfonate 10 parts
Alkylaryl polyglycol ether 12 parts
Sodium salt of naphthalenesulfonic acid formalin condensate 3 parts
Emulsion type silicone 1 part
Silicon dioxide 3 parts
Kaoline 45 parts
(Formulation Example 8) Water-soluble concentrate preparation
Compound of the present invention No. 5-086 20 parts
Polyoxyethylene lauryl ether 3 parts
Sodium dioctylsulfosuccinate 3.5 parts
Dimethylsulfoxide 37 parts
2-Propanol 36.5 parts
(Formulation Example 9) Liquid formulation for atomization
Compound of the present invention No. 5-086 2 parts
Dimethylsulfoxide 10 parts
2-Propanol 35 parts
Acetone 53 parts
(Formulation Example 10) Liquid formulation for transdermal administration
Compound of the present invention No. 5-086 5 parts
Hexylene glycol 50 parts
Isopropanol 45 parts
(Formulation Example 11) Liquid formulation for transdermal administration
Compound of the present invention No. 5-086 5 parts
Propylene glycol monomethy! ether 50 parts
Dipropylene glycol 45 parts
(Formulation Example 12) Liquid formulation for transdermal administration
(pouring-on)
Compound of the present invention No. 5-086 2 parts
Light-duty liquid paraffin 98 parts
(Formulation Example 13) Liquid formulation for transdermal administration
(pouring-on)
Compound of the present invention No. 5-086 2 parts
Light-duty liquid paraffin 58 parts
Olive oil 30 parts
ODO-H 9 parts
Shinetsu silicone 1 part
[0182] Also, when the compound of the present invention is used as an
agricultural chemicals, it may be mixed with other kinds of herbicides, various kinds
of insecticides, acaricides, nematocides, fungicides, vegetable growth regulators,
synergists, fertilizers, soil improvers, etc., and applied, at the time of preparing the
formulation or at the time of spreading, if necessary.
[0183] In particular, by mixing with the other agricultural chemicals or plant
hormones and applying the mixture, it can be expected that a cost is reduced due to
reduction in a dose to be applied, enlargement in insecticidal spectrum or higher
prevention and extinction effect of noxious organisms due to synergistic effect by
mixing agricultural chemicals. At this time, it is possible to use the compound with a
plural number of the conventionally known agricultural chemicals in combination
simultaneously. As the kinds of the agricultural chemicals to be used in admixture
with the compound of the present invention, there may be mentioned, for example,
the compounds described in Farm Chemicals Handbook, 1999 ed. and the like.
Specific examples of the general names can be enumerated below, but the invention
is not necessarily limited only thereto.
Fungicides: acibenzolar-S-methyl, acylaminobenzamide, amobam, ampropyfos,
anilazine, azaconazole, azoxystrobin, benalaxyl, benodanil, benomyl, benthiazole,
benzamacril, binapacryl, biphenyl, bitertanol, bethoxazine, bordeaux mixture,
blasticidin-S, bromoconazole, bupirimate, buthiobate, calcium polysulfide, captafol,
captan, copper oxychloride, carpropamid, carbendazim, carboxin, CGA-279202 (test
name), chinomethionat, chlobenthiazone, chlorfenazol, chloroneb, chlorothalonil,
chlozolinate, cufraneb, cymoxanil, cyproconazol, cyprodinil, cyprofuram, dazomet,
debacarb, dichlorophen, diclobutrazol, diclhlofluanid, diclomedine, dicloran,
diethofencarb, diclocymet, difenoconazole, diflumetorim, dimethirimol,
dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione,
ditalimfos, dithianon, dodemorph, dodine, drazoxolon, edifenphos, epoxiconazole,
etaconazole, ethirimol, etridiazole, famoxadone, fenarimol, febuconazole,
fenamidone, fendazosulam, fenfuram, fenhexamid, fenpiclonil, fenpropidin,
fenpropimorph, fentin, ferbam, ferimzone, fluazinam, fludioxonil, fluoroimide,
fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetylaluminium,
fuberidazole, furalaxyl, furametpyr, guazatine, hexachlorobenzene,
hexaconazole, hymexazol, imazalil, imibenconazole, iminoctadine, ipconazole,
iprobenfos, iprodione, isoprothiolane, iprovalicarb, kasugamycin, kresoxim-methyl,
mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metconazole,
methasulfocarb, metiram, metominostrobin, myclobutanil, MTF-753 (test name),
nabam, nickel bis(dimethyldithiocarbamate), nitrothal-isopropyl, nuarimol, NNF-9425
(test name), octhilinone, ofurace, oxadixyl, oxycarboxin, oxpoconazole fumarate,
pefurzoate, penconazole, pencycuron, phthalide, piperalin, polyoxins, potassium
hydrogen carbonate, probenazole, prochloraz, procymidone, propamocarb
hydrochloride, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil,
pyroquilon, quinomethionate, quinoxyfen, quintozene, RH 7281 (test name), sodium
hydrogen carbonate, sodium hypochlorite, sulfur, spiroxamine, tebuconazole,
tecnazene, tetraconazole, thiabendazole, thiadiazin/milneb, thifluzamide,
thiophanate-methyl, thiram, tolclofos-methyl, tolylfluanid, triadimefon, toriadimenol,
triazoxide, tricyclazole, tridemorph, triflumizole, triforine, triticonazole, validamycin,
vinclozolin, zinc sulfate, zineb, ziram, and shiitake mushroom hyphae extract, etc.;
Bactericides: streptomycin, tecloftalam, oxyterracycline, and oxolinic acid, etc.;
Nematocides: aldoxycarb, cadusafos, fosthiazate, fosthietan, oxamyl, and
fenamiphos, etc.;
Acaricides: acequinocyl, amitraz, bifenazate, bromopropylate, chinomethionat,
chlorobezilate, clofentezine, cyhexatine, dicofol, dienochlor, etoxazole, fenazaquin,
fenbutatin oxide, fenpropathrin, fenproximate, halfenprox, hexythiazox, milbemectin,
propargite, pyridaben, pyrimidifen, and tebufenpyrad, etc.;
Insecticides: abamectin, acephate, acetamipirid, aldicarb, allethrin, azinphos-methyl,
bendiocarb, benfuracarb, bensultap, bifenthrin, buprofezin, butocarboxim, carbaryl,
carbofuran, carbosulfan, cartap, chlorfenapyr, chlorpyrifos, chlorfenvinphos,
chlorfluazuron, clothianidin, chromafenozide, chlorpyrifos-methyl, cycloprothrin,
cyfluthrin, beta-cyfluthrin, cypermethrin, cyromazine, cyhalothrin, lambdacyhalothrin,
deltamethrin, diafenthiuron, diazinon, diacloden, diflubenzuron,
dimethylvinphos, diofenolan, disulfoton, dimethoate, emamectin-benzoate, EPN,
esfenvalerate, ethiofencarb, ethiprole, etofenprox, etrimfos, fenitrothion, fenobucarb,
fenoxycarb, fenpropathrin, fenvalerate, fipronil, fluacrypyrim, flucythrinate,
flufenoxuron, flufenprox, tau-fluvalinate, fonophos, formetanate, formothion,
furathiocarb, halofenozide, hexaflumuron, hydramethylnon, imidacloprid, isofenphos,
indoxacarb, isoprocarb, isoxathion, lufenuron, malathion, metaldehyde,
methamidophos, methidathion, methacrifos, metalcarb, methomyl, methoprene,
methoxychlor, methoxyfenozide, monocrotophos, muscalure, nidinotefuran,
nitenpyram, omethoate, oxydemeton-methyl, oxamyl, parathion, parathion-methyl,
permethrin, phenthoate, phoxim, phorate, phosalone, phosmet, phosphamidon,
pirimicarb, pirimiphos-methyl, profenofos, protrifenbute, pymetrozine, pyraclofos,
pyriproxyfen, rotenone, sulprofos, silafluofen, spinosad, sulfotep, tebfenozide,
teflubenzuron, tefluthorin, terbufos, tetrachlorvinphos, thiacloprid, thiocyclam,
thiodicarb, thiamethoxam, thiofanox, thiometon, tolfenpyrad, tralomethrin, trichlorfon,
triazuron, triflumuron, and vamidothion, etc.
Examples
[0184] Hereinafter, the present invention will be explained in more detail by
specifically referring to Synthetic Examples and Test Examples of the compound of
the present invention as working examples to which the present invention is not
limited.
(Synthetic Examples)
Synthetic Example 1
Production of the compound of the present invention by use of L-COS (parallel
liquid-phase synthesis system of MORITEX Corporation)
[0185] In 15 bials of L-COS in which stirrers were placed, 1.5 mmol of each npropylamine,
i-propylamine, s-butylamine, t-butylamine, n-pentylamine, 2,2-
dimethylpropylamine, n-hexylamine, cyclohexylamine, benzylamine, 4-
trifluoromethylbenzylamine, 1-phenylethylamine, 2-phenylethylamine, 2-(4-
phenoxyphenyl)ethylamine, 3-phenylpropylamine and trans-2-
phenylcyclopropylamine was weighed, each bial was covered and placed in a
reaction vessel of L-COS. With stirring at room temperature, in each bial, 5 ml of a
solution of 4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]
benzoic acid in N.N-dimethylformamide-chlroform (1:3) (0.2 mmol/ml), 1 ml of a
solution of 4-(dimethylamino) pyridine in chloroform (0.25 mmol/ml), and then 1.5 ml
of a solution of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride in
chloroform (1.0 mmol/ml) were added in that order, and continued to stir at the same
temperature for 16 hours. After the completion of the reaction, 3 ml of cold water
was added in each bials, and the organic phases were collected, and subjected to
purification with medium-pressure preparative liquid chromatography (Yamazen
Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted
with ethyl acetate-hexane (1:3 to 1:1 gradient), and the aimed product was obtained
as white to yellow solid. In addition, the product was confirmed with LC-MS (Waters
LC-MS system, detector: ZMD, analysis condition: 254nm, 80%CH3CN-20%H2O-
0.1%HCOOH, ionization: positive electrospray).
4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-npropylbenzoic
acid amide; 0.26 g, [M++H]=444.94.
4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-ipropylbenzoic
acid amide; 0.23 g, [M*+H]=444.94.
N-s-butyl-4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]
benzoic acid amide; 0.20 g, [M*+H]=458.93.
N-t-butyl-4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]
benzoic acid amide; 0.21 g, [M++H]=458.92.
4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-npentylbenzoic
acid amide; 0.31 g, [M++H]=473.02.
4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2-
dimethylpropyl) benzoic acid amide; 0.27 g, [M++H]=472.94.
4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N>nhexylbenzoic
acid amide; 0.26 g, [M++H]=486.96.
N-cyclohexyl-4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]
benzoic acid amide; 0.26 g, [M++H]=484.93.
N-benzyl-4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]
benzoic acid amide; 0.34 g, [lvT+H]=492.86.
4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(4-
trifluoromethylbenzyl) benzoic acid amide; 0.34 g, [M++H]=560.97.
4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(1-
phenylethyl) benzoic acid amide; 0.26 g, [lvT+H]=506.88.
4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2-
phenylethyl) benzoic acid amide; 0.37 g, [M++H]=507.01.
4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-[2-(4-
phenoxyphenyl)ethyl] benzoic acid amide; 0.36 g, [M++H]=598.95.
4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(3-
phenylpropyl) benzoic acid amide; 0.31 g, [M++H]=520.97.
4-[5-(3,4-d ichloropheny l)-5-trifluoromethyl-4,5-d ihyd roisoxazol-3-yl]-N-(trans-2-
phenylcyclopropyl) benzoic acid amide; 0.21 g, [M++H]=518.88.
Synthetic Example 2
Production of the compound of the present invention by use of L-COS (parallel
liquid-phase synthesis system of MORITEX Corporation)
[0186] Ten (10) bials of L-COS in which stirrers were placed were assigned a
number of 1 to 10, respectively. 1.0 mmol of 3-chloro-4-fluorophenyl boric acid was
weighed in the bials of Nos. 1 and 6,1.0 mmol of 3,5-bis(trifluoromethyl)phenyl boric
acid was weighed in the bials of Nos. 2 and 7,1.0 mmol of 3-trifluoromethylphenyl
boric acid was weighed in the bials of Nos. 3 and 8,1.0 mmol of 3-
trifluoromethoxyphenyl boric acid was weighed in the bials of Nos. 4 and 9, and 1.0
mmol of 2-naphthyl boric acid was weighed in the bials of Nos. 5 and 10, Then,
0.05 mmol of dichlorobis(triphenylphosphine) palladium (II) was added in each bial,
the bial was filled with nitrogen and covered, and placed in a reaction vessel of LCOS.
With stirring at room temperature, in each bial, 3 ml of a solution of 2-bromo-
3,3,3-trifluoropropene in 1,2-dimethoxyethane (0.5 mmol/ml), 1.5 ml of water, and
then 1 ml of a solution of triethylamine in 1,2-dimethoxyethane (6.0 mmol/ml) were
added in that order, and stirred at 75°C for 3.5 hours. Then, the bials were cooled
to 0°C, 1.5 ml of a solution of N-benzyl-4-(chlrohydroxyiminomethyl) benzoic acid
amide in 1,2-dimethoxyethane (0.7 mmol/ml) was added in the bials of Nos. 1 to 5,
and 1.5 ml of a solution of 4-chlorohydroxyiminomethyl-N-(2,2,2-trifluoroethyl)
benzoic acid amide in 1,2-dimethoxyethan (0.7 mmol/ml) was added in the bials of
Nos. 6 to 10, and the bials were continued to stir at room temperature for 16 hours.
After the completion of the reaction, the organic phase was collected, aqueous
phase was extracted with 5 ml of chloroform, the chloroform was added to the
organic phase, and the solvent was distilled off under reduced pressure. The
residue was subjected to purification with medium-pressure preparative liquid
chromatography (Yamazen Corporation, medium pressure preparative system;
YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:3 to 1:1 gradient), and
the aimed product was obtained as white to yellow solid. In addition, the product
was confirmed with LC-MS (Waters LC-MS system, detector: ZMD, analysis
condition: 254nm, 80%CH3CN-20%H2O-0.1%HCOOH, ionization: positive
electrospray).
N-benzyl-4-[5-(3-chloro-4-fluorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]
benzoic acid amide; 0.28 g, [M++H]=476.80.
N-benzyl-4-[5-[3,5-bis(trifluoromethyl)phenyl]-5-trifluoromethyl-4,5-dihydroisoxazol-
3-yl] benzoic acid amide; 0.25 g, [M++H]=560.76.
N-benzyl-4-[5-(3-trifluoromethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]
benzoic acid amide; 0.26 g, [M++H]=492.82.
N-benzyl-4-[5-(3-trifluoromethoxyphenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]
benzoic acid amide; 0.25 g, [M++H]=508.80.
N-benzyl-4-[5-(2-naphthyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl] benzoic acid
amide; 0.09 g, [M++H]=474.86.
4-[5-(3-chloro-4-fluorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-
trifluoroethyl) benzoic acid amide; 0.29 g, [M++H]=468.76.
4-[5-[3,5-bis(trifluoromethyl)phenyl]-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-
(2,2,2-trifluoroethyl) benzoic acid amide; 0.29 g, [M++H]=552.72.
4-[5-(3-trifluoromethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-
trifluoroethyl) benzoic acid amide; 0.18 g, [M++H]=484.78.
4-[5-(3-trifluoromethoxyphenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-
trifluoroethyl) benzoic acid amide; 0.27 g, [M++H]=500.76.
4-[5-(2-naphthyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)
benzoic acid amide; 0.14 g, [M*+H]=466.83.
Synthetic Example 3
4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-
(2,2,2-trifluoroethyl) benzoic acid amide (Compound of the present invention No.
3-060)
Step 1: Production of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene
[0187] In a solution of 25.0 g of 3,5-dichlorophenyl boric acid in 200 ml of
tetrahydrofuran and 100 ml of water, 27.5 g of 2-bromo-3,3,3-trifluoropropene, 38.0 g
of potassium carbonate and 1.84 g of dichlorobis(triphenylphosphine) palladium (II)
were added, and stirred under reflux with heat for 3 hours. After the completion of
the reaction and cooling to room temperature, 500 ml of ice water was added, and
extracted with ethyl acetate (500 ml x 1). The organic phase was washed with
water, dried over anhydrous sodium sulfate, the solvent was distilled off under
reduced pressure. The residue was purified with silica gel column chromatography
that was eluated with hexane, and 25.7 g of the aimed product was obtained as
colorless oily substance.
1H NMR (CDCI3, Me4Si, 300MHz) 57.41 (t, J=2.0Hz, 1H), 7.3-7.35 (m, 2H), 6.05 (q,
J=3.2Hz, 1H), 5.82 (q, J=3.2Hz, 1H).
Step 2: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-
dihydroisoxazol-3-yl] benzoic acid methyl ester
[0188] In a solution of 2.70 g of 4-(hydroxyiminomethyl)methyl) benzoic acid
methyl ester in 15 ml of N,N-dimethylformamide, 2.04 g of N-chlorosuccinic acid
imide was added, and stirred at 40°C for 40 minutes. Then, the reaction mixture
was cooled to 0°C, 3.40 g of 3,5-dichloro-1-(1-trifluoromethylethenyl) benzene and
1.72 g of triethylamine were added, continued to stir at room temperature for 18
hours. After the completion of the reaction, the reaction mixture was poured into
100 mi of ice water, extracted with ethyl acetate (50 ml x 2), the organic phase was
washed with water, dehydrated with saturated sodium chloride aqueous solution and
dried over anhydrous sodium sulfate, and then the solvent was distilled off under
reduced pressure. The residual solid was subjected to purification with mediumpressure
preparative liquid chromatography (Yamazen Corporation, medium
pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetatehexane
(1:1 to 1:3 gradient), and 4.05 g of the aimed product was obtained as white
crystal.
Melting point 94.0 to 96.0°C
1H NMR (CDCI3, Me4Si, 300MHz) 6 8.10 (d, J=8.4Hz, 2H), 7.74 (d, J=8.4Hz, 2H),
7.43 (s, 2H), 7.26 (s, 1H), 4.12 (d, J=17.3Hz, 1H), 3.94 (s, 3H), 3.74 (d, J=17.3Hz,
1H).
Step 3: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-
dihydroisoxazol-3-yl] benzoic acid
[0189] In a solution of 3.99 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-
dihydroisoxazol-3-yl] benzoic acid methyl ester in 50 ml of methanol, a solution of
2.00 g of potassium hydroxide in 25 ml of water was added, stirred at room
temperature for 3 days and then at 40°C for 5 hours. After the completion of the
reaction, the reaction mixture was cooled with ice, and poured in 200 ml of water,
and adjusted to pH 1-2 with concentrated hydrochloric acid, and then extracted with
ethyl acetate (50 ml x 2), the organic phase was washed with water, dehydrated with
saturated sodium chloride aqueous solution and dried over anhydrous sodium
sulfate, and then the solvent was distilled off under reduced pressure to obtain 3.87 g
of the aimed product as pale yellow crystal.
Melting point 237.0 to 240.0°C
'H NMR (CDCI3-DMSO-d6, Me4Si, 300MHz) 6 8.09 (d, J=8.4Hz, 2H), 7.76 (d,
J=8.4Hz, 2H), 7.54 (s, 2H), 7.44 (s, 1H), 4.18 (d, J=17.7Hz, 1H), 3.86 (d, J=17.7Hz,
1H).
Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-
dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl) benzoic acid amide
[0190] In a suspension of 1.00 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl] benzoic acid in 10 ml of benzene, 0.44 g of thionyl chloride
and a catalytic amount (2 to 3 drops) of N,N-dimethylformamide were added, and
stirred under reflux with heat for 2.5 hous. After the completion of the reaction, the
solvent was distilled off under reduced pressure to obtain 1.81 g of crude 4-[5-(3,5-
dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl] benzoic acid chloride as
pale yellow oily substance.
In a solution of 0.29 g of 2,2,2-trifluoroethylamine and 0.37 g of triethylamine in 20 ml
of chloroform, 1.81 g of the crude 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-
dihydroisoxazol-3-yl] benzoic acid chloride dissolved in 10 ml of chloroform was
added dropwise with cooling with ice and with stirring. After the completion of
addition dropwise, the mixture was continued to stir at room temperature further for
30 minutes. After the completion of the reaction, the reaction mixture was poured in
100 ml of water, and extracted with chloroform (20 ml x 3), the organic phase was
washed with water, dehydrated with saturated sodium chloride aqueous solution and
dried over anhydrous sodium sulfate, and passed through a glass filter packed with
silica gel, and then the solvent was distilled off under reduced pressure. The
residual solid was washed with hexane to obtain 1.05 g of the aimed product as
white crystal.
Melting point 94.0 to 96.0°C
1H NMR (CDCI3, Me4Si, 300MHz) d 7.86 (d, J=8.4Hz, 2H), 7.76 (d, J=8.4Hz, 2H),
7.51 (s, 2H), 7.44 (s, 1H), 6.47 (t, J=6.3Hz, 1H), 4.14 (qd, J=18.5, 6.3Hz, 2H), 4.11
(d, J=17.4Hz, 1H), 3.73 (d, J=17.4Hz, 1H).
Synthetic Example 4
N-Benzyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-
2-fluoro benzoic acid amide (Compound of the present invention No. 5-039)
Step 1: Production of 3-(4-bromomethyl-3-fluorophenyl)-5-(3,5-dichlorophenyl)-
5-trifluoromethyl-4,5-dihydroisoxazole
[0191] In a solution of 1.50 g of 5-(3,5-dichlorophenyl)-3-(3-fluoro-4-
methylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole synthesized from 3-fluoro-4-
methylphenylaldoxime and 3,5-dichloro-1-(1-trifluoromethylethenyl) benzene
similarly to Step 2 of Synthetic Example 3 in 50 ml of 1,2-dichloroethane, 0.68 g of
N-bromosuccinic acid imide and a catalytic amount of azobisisobutyronitrile were
added, and stirred under nitrogen atmosphere and under reflux with heat for 1 hour.
After the completion of the reaction, the reaction mixture was left and cooled to room
temperature, poured in 50 ml of water, extracted with chloroform (50 ml x 1). The
organic phase was dehydrated with saturated sodium chloride aqueous solution and
dried over anhydrous sodium sulfate, and then the solvent was distilled off under
reduced pressure to obtain crude aimed product as pale yellow oily substance. The
resulting product was used as such without purification for the next step.
1H NMR (CDCI3 Me4Si, 400MHz) 5 7.45-7.6 (m, 6H), 4.51 (s, 2H), 4.05 (d,
J=17.2Hz, 1H), 3.67 (d, J=17.2Hz, 1H).
Step 2: Production of 3-(4-acetoxymethyl-3-fluorophenyl)-5-(3,5-dichlorophenyl)-
5-trifluoromethyl-4,5-dihydroisoxazole
[0192] In a solution of crude 3-(4-bromomethyl-3-fluorophenyl)-5-(3,5-
dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 30 ml of acetic acid, 1.50 g
of potassium acetate was added, and stirred under reflux with heat for 1.5 hour.
After the completion of the reaction, the reaction mixture was left and cooled to room
temperature, and neutralized by pouring in 100 ml of saturated sodium hydrogen
carbonate aqueous solution. The organic phase was collected, dehydrated with
saturated sodium chloride aqueous solution and dried over anhydrous sodium
sulfate, and then the solvent was distilled off under reduced pressure to obtain 1.50 g
of crude aimed product as pale yellow oily substance. The resulting product was
used as such without purification for the next step.
1H NMR (CDCI3, Me4Si, 400MHz) 6 7.2-7.55 (m, 6H), 5.20 (s, 2H), 4.05 (d,
J=17.2Hz, 1H), 3.67 (d, J=17.2Hz, 1H), 2.14 (s, 3H).
Step 3: Production of 5-(3,5-dichlorophenyl)-3-(3-fluoro-4-hydroxymethylphenyl)-
5-trifluoromethyl-4,5-dihydroisoxazole
[0193] In a solution of 1.50 g of crude 3-(4-acetoxymethyl-3-fluorophenyl)-5-(3,5-
dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 10 ml of ethanol, 2.00 g of
sodium hydroxide dissolved in 20 ml of water was added, and stirred under reflux
with heat for 4.5 hours. After the completion of the reaction, the reaction mixture
was cooled with ice, and adjusted to pH 2-3 by carefully adding concentrated
hydrochloric acid, and extracted with ethyl acetate (50 ml x 1). The organic phase
was dehydrated with saturated sodium chloride aqueous solution and dried over
anhydrous sodium sulfate, and then the solvent was distilled off under reduced
pressure. The residue was purified with silica gel column chromatography that was
eluated with ethyl acetate-hexane (1:2) to obtain 0.95 g of the aimed product as pale
yellow resinous substance.
1H NMR (CDCI3) Me4Si, 400MHz) 6 7.5-7.6 (m, 3H), 7.4-7.45 (m, 3H), 4.81 (s, 2H),
4.06 (d, J=17.2Hz, 1H), 3.68 (d, J=17.2Hz, 1H), 1.87 (bs, 1H).
Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-fluoro benzoic acid
[0194] In a solution of 0.95 g of 5-(3,5-dichlorophenyl)-3-(3-fluoro-4-
hydroxymethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 25 ml of acetone,
Johnes' Reagent prepared from 1.50 g of chromic acid, 1.2 ml of concentrated
sulfuric acid and 7 ml of water was added dropwise under cooling with ice and with
stirring, after the completion of the addition dropwise, continued to stir at room
temperature for further 1.5 hour. After the completion of the reaction, the reaction
mixture was poured in 50 ml of water and extracted with diethyl ether (50 ml x 1).
The organic phase was dehydrated with saturated sodium chloride aqueous solution
and dried over anhydrous sodium sulfate, and then the solvent was distilled off under
reduced pressure. The residual solid was washed with hexane to obtain 0.67 g of
the aimed product as beige crystal.
Melting point 172.0 to 174.0°C
1H NMR (CDCI3, Me4Si, 300MHz) 8 8.05-8.15 (m, 1H), 7.45-7.55 (m, 5H), 4.08 (d,
J=17.3Hz, 1H), 3.71 (d, J=17.3Hz, 1H).
Step 5: Production of N-benzyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-fluoro benzoic acid amide
[0195] In a solution of 0.15 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-
dihydroisoxazol-3-yl]-2-fluoro benzoic acid in 10 ml of dichloromethane, 0.3 ml of
oxalyl chloride and 2 drops of N.N-dimethylformamide were added at room
temperature, and stirred at the same temperature for 10 minutes. After the
completion of the reaction, the solvent was distilled off under reduced pressure, the
remaining white solid was dissolved in 10 ml of chloroform, and 0.3 ml of
benzylamine and then 0.3 ml of triethylamine were added under cooling with ice,
after the completion of the addition, continued to stir at room temperature for further
20 minutes. After the completion of the reaction, 40 ml of water was poured in the
reaction mixture, and extracted with ethyl acetate (50 ml x 1). The organic phase
was dehydrated with saturated sodium chloride aqueous solution and dried over
anhydrous sodium sulfate, and then the solvent was distilled off under reduced
pressure. The residue was purified with silica gel column chromatography that was
eluated with ethyl acetate-hexane (1:2) to obtain 0.14 g of the aimed product as
white crystal.
Melting point 172.0 to 176.0°C
1H NMR (CDCI3 Me4Si, 400MHz) 5 8.20 (t, J=8.0Hz, 1H), 7.25-7.55 (m, 10H), 7.05
(t, J=5.6Hz, 1H), 4.68 (d, J=5.6Hz, 2H), 4.07 (d, J=17.6Hz, 1H), 3.70 (d, J=17.6Hz,
1H).
Synthetic Example 5
4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-nitro-N-
(2-pyridylmethyl) benzoic acid amide (Compound of the present invention No. 5-339)
Step 1: Production of 4-bromo-3-nitrobenzaldoxime
[0196] In a solution of 5.0 g of 4-bromo-3-nitrobenzaldehyde in 50 ml of
methanol, 3.6 ml of 50% hydroxyamine aqueous solution was added with stirring at
room temperature, and continued to stir at the same temperature for 18 hours.
After the completion of the reaction, 60 ml of water was added in the reaction
mixture, and precipitated solid was filtered off, washed with water and then dried to
obtain 5.0 g of the aimed product as yellow crystal.
1H NMR (CDCI3-DMSO-d6, Me4Si, 400MHz) 6 11.18 (s, 1H), 8.09 (s, 1H), 8.07 (d,
J=2.0Hz, 1H), 7.73 (d, J=8.4Hz, 1H), 7.62 (dd, J=8.4, 2.0Hz, 1H).
Step 2: Production of 3-(4-bromo-3-nitrophenyl)-5-(3,5-dichlorophenyl)-5-
trifluoromethyl-4,5-dihydroisoxazole
[0197] In a solution of 1.27 g of 4-bromo-3-nitrobenzaldoxime in 16 ml of N,Ndimethylformamide,
0.74 g of N-chlorosuccinic acid imide was added, and stirred at
35°C for 90 minutes. Then, the reaction mixture was cooled with ice, 1.20 g of 3,5-
dichloro-1-(1-trifluoromethylethenyl) benzene synthesized in Step 1 of Synthetic
Example 3 and 0.60 g of triethylamine were added, continued to stir at room
temperature for 18 hours. After the completion of the reaction, the reaction mixture
was poured in 50 ml of ice water, extracted with ethyl acetate (50 ml x 2), the organic
phase was dehydrated with saturated sodium chloride aqueous solution and dried
over anhydrous sodium sulfate, and then the solvent was distilled off under reduced
pressure. The residual solid was subjected to purification with medium-pressure
preparative liquid chromatography (Yamazen Corporation, medium pressure
preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:2 to
1:4 gradient), and 1.10 g of the aimed product was obtained as yellow crystal.
Melting point 179.0 to 181.0°C
1H NMR (CDCI3, Me4Si, 400MHz) 8 8.06 (d, J=2.0Hz, 1H), 7.84 (d, J=8.4Hz, 1H),
7.78 (dd, J=8.4, 2.0Hz, 1H), 7.45-7.55 (m, 2H), 7.45 (t, J=1.8Hz, 1H), 4.09 (d,
J=17.2Hz, 1H), 3.72 (d, J=17.4Hz, 1H).
Step 3: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-nitrobenzoic acid ethyl ester
[0198] In a solution of 2.0 g of 3-(4-bromo-3-nitrophenyl)-5-(3,5-dichlorophenyl)-
5-trifluoromethyl-4,5-dihydroisoxazole in 30 ml of ethanol in an autoclave, 0.40 g of
sodium acetate, 88.0 mg of 1,1'-bis(diphenylphosphino) ferrocene and 18.0 mg of
palladium (II) acetate were added, and stirred under 0.9 MPa carbon monoxide
atmosphere at 100°C for 3 hours. After the completion of the reaction, the reaction
mixture was left and cooled to room temperature, and the solvent was distilled off
under reduced pressure, and the residue was dissolved in 100 ml of ethyl acetate,
washed with water, dried over anhydrous sodium sulfate and the solvent was
distilled off under reduced pressure. The residual solid was subjected to
purification with medium-pressure preparative liquid chromatography (Yamazen
Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted
with ethyl acetate-hexane (1:2 to 1:4 gradient), and 0.66 g of the aimed product was
obtained as pale yellow crystal.
Melting point 160.0 to 162.0°C
1H NMR (CDCI3, Me4Si, 400MHz) 5 8.13 (d, J=1.6Hz, 1H), 7.99 (dd, J=8.1, 1.6Hz,
1H), 7.83 (d, J=8.1Hz, 1H), 7.45-7.55 (m, 2H), 7.45 (t, J=1.8Hz, 1H), 4.41 (q,
J=7.1Hz, 2H), 4.11 (d, J=17.2Hz, 1H), 3.74 (d, J=17.8Hz, 1H), 1.37 (t, J=7.1Hz, 3H).
Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-nitro-N-(2-pyridylmethyl) benzoic acid amide
[0199] In a solution of 0.36 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-
dihydroisoxazol-3-yl]-2-nitrobenzoic acid ethyl ester in 8 ml of ethanol, a solution of
0.40 g of potassium hydroxide in 2 ml of water was added, and stirred at room
temperature for 3 hours. After the completion of the reaction, the reaction mixture
was poured in 15 ml of water, adjusted to pH 4 with concentrated hydrochloric acid,
then extracted with ethyl acetate (20 ml x 2), the organic phase was washed with
water, and then dehydrated with saturated sodium chloride aqueous solution and
dried over over anhydrous sodium sulfate and the solvent was distilled off under
reduced pressure to obtain 0.40 g of crude 4-[5-(3,5-dichlorophenyl)-5-
trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-nitro benzoic acid as pale yellow oily
substance. The substance was dissolved in 10 ml of chloroform, and 0.24 g of 2-
picolylamine, 0.01 g of 4-(N,N-dimethylamino)pyridine and 0.35 g of 1-[3-
(diethylamino)propyl]-3-ethylcarbodiimide hydrochloride were added, and stirred at
room temperature for 18 hours. After the completion of the reaction, the solvent
was distilled off under reduced pressure. The residue was subjected to purification
with medium-pressure preparative liquid chromatography (Yamazen Corporation,
medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl
acetate-hexane (1:1 to 1:0 gradient), and 0.14 g of the aimed product was obtained
as colorless resinous substance.
1H NMR (CDCI3-DMSO-d6, Me4Si, 300MHz) 5 8.50 (d, J=4.8Hz, 1H), 8.25 (d,
J=1.7Hz, 1H), 8.03 (dd, J=8.1, 1.6Hz, 1H), 7.72 (td, J=7.7, 1.6Hz, 1H), 7.68 (d,
J=8.1Hz, 1H), 7.51 (d, J=1.5Hz, 2H), 7.45 (t, J=1.8Hz, 1H), 7.43 (bs, 1H), 7.36 (d,
J=7.9Hz, 1H), 7.23 (dd, J=6.8, 5.3Hz, 1H), 4.76 (d, J=4.8Hz, 2H), 4.13 (d, J=17.4Hz,
1H), 3.76 (d, J=17.4Hz, 1H).
Synthetic Example 6
4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxy-
N-(2,2,2-trifluoroethyl) benzoic acid amide (Compound of the present invention No.
5-317)
Step 1: Production of 4-hydroxyiminomethyl-2-methoxyphenyl trifluoromethane
sulfonate
[0200] In a solution of 3.0 g of 4-hydroxy-3-methoxybenzaldehyde and 2.4 g of
triethylamine in 50 ml of dichloromethane, 5.8 g of trifluoromethane sulfonic acid
anhydride was added dropwise under cooling with ice and with stirring, after the
completion of the addition dropwise, continued to stir at the same temperature for 30
minutes. After the completion of the reaction, the reaction mixture was washed with
50 ml of water and then with 30 ml of saturated sodium hydrogen carbonate aqueous
solution, and dehydrated with saturated sodium chloride aqueous solution and dried
over anhydrous magnesium sulfate, and then the solvent was distilled off under
reduced pressure. The residue was was dissolved in a mixture of 30 ml of ethanol
and 15 ml of water, 1.4 g of hydroxyamine hydrochloride and 1.7 g of sodium acetate
were added with stirring at room temperature, and continued to stir at the same
temperature for further 1 hour. After the completion of the reaction, the solvent was
ditilled off under reduced pressure, extracted with ethyl acetate (40 ml x 2), the
organic phase was washed with water (30 ml x 1), and then dehydrated with
saturated sodium chloride aqueous solution and dried over anhydrous magnesium
sulfate, and then the solvent was distilled off under reduced pressure to obtain 5.25 g
of the aimed product as brown oily substance.
Refractive index nD
20.2°c = 1.5082
1H NMR (CDCI3-DMSO-d6, Me4Si, 300MHz) 5 8.47 (bs, 1H), 8.11 (s, 1H), 7.32 (s,
1H), 7.24 (d, J=8.1Hz, 1H), 7.10 (d, J=8.1Hz, 1H), 3.94 (s, 3H).
Step 2: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-methoxyphenyltrifluoromethanesulfonate
[0201] In a solution of 2.0 g of 4-hydroxyiminomethyl-2-methoxyphenyl
trifluoromethane sulfonate in 30 ml of N.N-dimethylformamide, 0.9 g of Nchlorosuccinic
acid imide was added, and stirred at 40 to 50°C for 30 minutes.
Then, the reaction mixture was left and cooled to room temperature, 1.5 g of 3,5-
dichloro-1-(1-trifluoromethylethenyl) benzene synthesized in Step 1 of Synthetic
Example 3 and 0.7 g of triethylamine were added, and stirred at room temperature
for 90 minutes. After the completion of the reaction, the reaction mixture was
poured in 100 ml of ice water, extracted with ethyl acetate (50 ml x 2), the organic
phase was dehydrated with saturated sodium chloride aqueous solution and dried
over anhydrous magnesium sulfate, and then the solvent was distilled off under
reduced pressure. The residue was purified with silica gel column chromatography
that was eluated with ethyl acetate-hexane (1:7), and 1.4 g of the aimed product was
obtained as colorless resinous substance.
1H NMR (CDCI3,Me4Si, 300MHz) 8 7.50 (s, 2H), 7.44 (s, 1H), 7.25-7.3 (m, 2H), 7.11
(d, J=8.4Hz, 1H), 4.08 (d, J=17.1Hz, 1H), 3.97 (s, 3H), 3.69 (d, J=17.1Hz, 1H).
Step 3: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-methoxy benzoic acid ethyl ester
[0202] In a solution of 1.50 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-
dihydroisoxazol-3-yl]-2-methoxyphenyl trifluoromethane sulfonate in 25 ml of ethanol
in an autoclave, 0.27 g of sodium acetate, 31.0 mg of 1,1'-bis(diphenylphosphino)
ferrocene and 7.0 mg of palladium (II) acetate were added, and stirred under 0.96
Mpa carbon monoxide atmosphere at 100°C for 2 hours. After the completion of
the reaction, the reaction mixture was left and cooled to room temperature, and the
reaction mixture was poured in 100 ml of ice water, extracted with ethyl acetate (40
ml x 2). The organic phases together were dehydrated with saturated sodium
chloride aqueous solution and dried over anhydrous magnesium sulfate, and then
the solvent was distilled off under reduced pressure. The residue was purified with
silica gel column chromatography that was eluated with ethyl acetate-hexane (1:5),
and 1.20 g of the aimed product was obtained as white crystal.
Melting point 142.0-144.0°C
1H NMR (CDCI3, Me4Si, 300MHz) 6 7.82 (d, J=7.8Hz, 1H), 7.51 (s, 2H), 7.4-7.45 (m,
2H), 7.10 (d, J=7.8Hz, 1H), 4.37 (q, J=7.2Hz, 2H), 4.10 (d, J=17.4Hz, 1H), 3.95 (s,
3H), 3.71 (d, J=17.4Hz, 1H), 1.39 (t, J=7.2Hz, 3H).
Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-methoxy benzoic acid
[0203] In a solution of 1.07 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-
dihydroisoxazol-3-yl]-2-methoxy benzoic acid ethyl ester in 30 ml of ethanol, a
solution of 1.0 g of sodium hydroxide in 30 ml of water was added, stirred at 85°C for
1 hour. After the completion of the reaction, the solvent was distilled off under
reduced pressure. The residue was adjusted to pH 2 to 3 with concentrated
hydrochloric acid, and extracted with ethyl acetate (30 ml x 2). The organic phase
was dehydrated with saturated sodium chloride aqueous solution and dried over
anhydrous magnesium sulfate, and then the solvent was distilled off under reduced
pressure to obtain 1.0 g of the aimed product as pale yellow resinous substance.
1H NMR (CDCI3, Me4Si, 300MHz) 810.67 (bs, 1H), 8.24 (d, J=7.8Hz, 1H), 7.57 (s,
1H), 7.51 (s, 2H), 7.45 (s, 1H), 7.22 (d, J=7.8Hz, 1H), 4.05-4.15 (m, 4H), 3.74 (d,
J=17.4Hz, 1H).
Step 5: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-methoxy-N-(2,2,2-trifluoroethyl) benzoic acid amide
[0204] In a suspension of 0.25 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-methoxy benzoic acid in 15 ml of dichloromethane, 0.09
g of oxalyl chloride and 1 drop of N,N-dimethylformamide were added, and stirred at
room temperature for 1 hour. After the completion of the reaction, the solvent was
distilled off under reduced pressure, the residue was dissolved in 15 ml of
dichloromethane, and 0.09 g of triethylamine was added under cooling with ice, then
0.07 g of 2,2,2-trifluoroethylamine was added dropwise. After the completion of
addition dropwise, the mixture was continued to stir at the same temperature for
further 2 hours. Thereafter, the reaction mixture was diluted with 60 ml of
chloroform, washed with 50 ml of water, then dehydrated with saturated sodium
chloride aqueous solution and dried over anhydrous sodium sulfate, and then the
solvent was distilled off under reduced pressure. The residue was purified with
silica gel column chromatography that was eluated with ethyl acetate-hexane (1:2) to
obtain 0.25 g of the aimed product as colorless resinous substance.
1H NMR (CDCI3, Me4Si, 300MHz) 88.2-8.3 (m, 2H), 7.51 (s, 3H), 7.43 (s, 1H), 7.17
(d, J=7.8Hz, 1H), 4.05-4.2 (m, 3H), 4.05 (s, 3H), 3.74 (d, J=17.4Hz, 1H).
Synthetic Example 7
4-[5-(4-Fluoro-3-methylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-
(2,2,2-trifluoroethyl) benzole acid amide (Compound of the present invention No.
3-141)
Step 1: Production of 4-formyl-N-(2,2,2-trifluoroethyl) benzoic acid amide
[0205] In a suspension of 1.00 g of 4-formyl benzoic acid in 15 ml of benzene,
0.87 g of thionyl chloride and 2 drops of N,N-dimethylformamide were added, and
stirred under reflux with heat for 2 hours. After the completion of the reaction, the
reaction mixture was left and cooled to room temperature, and the solvent was
distilled off under reduced pressure to obtain 1.14 g of crude 4-formyl benzoic acid
chloride as white crystal. In a solution of 0.66 g of 2,2,2-trifluoroethylamine and
0.81 g of triethylamine in 6 ml of chlororform, the solution of 1.14 g of the crude 4-
formyl benzoic acid chloride in 6 ml of chloroform was added dropwise under cooling
with ice and with stirring, after the completion of the addition dropwise, continued to
stir at room temperature for further 18 hours. After the completion of the reaction,
the reaction mixture was added in 30 ml of water, extracted with chloroform (20 ml x
3). The organic phase was washed with water, dried over anhydrous sodium
sulfate, the solvent was distilled off under reduced pressure, the residual solid was
washed with hexane to obtain 1.32 g of the aimed product as white crystal.
Melting point 83.0 to 84.0°C
1H NMR (CDCI3, Me4Si, 400MHz) 510.09 (s, 1H), 7.96 (bs, 4H), 6.80 (bs, 1H), 4.05-
4.25 (m, 2H).
Step 2: Production of 4-hydroxyiminomethyl-N-(2,2,2-trifluoroethyl) benzoic acid
amide
[0206] In a solution of 4.11 g of 4-formyl-N-(2,2,2-trifluoroethyl) benzoic acid
amide in 30 ml of ethanol and 10 ml of water, 1.99 g of hydroxyamine hydochloride
and 2.51 g of anhydrous sodium acetate were added, stirred stirred at room
temperature for 3.5 hours. After the completion of the reaction, the reaction mixture
was poured in 100 ml of water, and then extracted with ethyl acetate (30 ml x 3), the
organic phase was washed with 50 ml of saturated sodium hydrogen carbonate
aqueous solution, then dehydrated with saturated sodium chloride aqueous solution
and dried over anhydrous sodium sulfate, and then the solvent was distilled off under
reduced pressure. The residual solid was washed with hexane to obtain 3.92 g of
the aimed product as white crystal.
Melting point 153.0 to 154.0°C
1H NMR (CDCI3, Me4Si, 400MHz) 510.89 (s, 1H), 8.08 (s, 1H), 8.03 (bs, 1H), 7.84 (d,
J=8.2Hz, 2H), 7.60 (d, J=8.2Hz, 2H), 3.95-4.1 (m, 2H).
Step 3: Production of 4-chlorohydroxyiminomethyl-(212,2-trifluoroethyl) benzoic acid
amide
[0207] In a solution of 3.80 g of 4-hydroxyiminomethyl-N-(2,2,2-trifluoroethyl)
benzoic acid amide in 50 ml of tetrahydrofyran, 20 ml of 3N hydrochloric acid was
added, 14 ml of 8% sodium hypochlorite aqueous solution was added dropwise with
stirring under ice cooling over 10 minutes, after the completion of addition dropwise,
continued to stir at the same temperature for further 15 minutes. After the
completion of the reaction, the reaction mixture was poured in 200 ml of water,
extracted with ethyl acetate (30 ml x 3), the organic phase was dehydrated with
saturated sodium chloride aqueous solution and dried over anhydrous sodium
sulfate, and the solvent was distilled off under reduced pressure. The resudual
solid was washed with hexane to obtain 4.15 g of the product as white crystal.
Melting point 158.0 to 160.0°C
1H NMR (CDCI3, Me4Si, 400MHz) 512.03 (s, 1H), 8.05 (t, J=6.0Hz, 1H), 7.93 (bs,
4H), 3.95-4.15 (m,2H).
Step 4: Production of 4-[5-(4-fluoro-3-methylphenyl)-5-trifluoromethyl-4,5-
dihydrooxazol-3-yl]-N-(2,2,2-trifluoroethyl) benzoic acid amide
[0208] In a solution of 0.21 g of 4-fluoro-3-methylphenyl boric acid and 0.23 g of
2-bromo-3,3,3-trifluoropropene in 6 ml of 1,2-dimethoxyethane and 2 ml of water,
0.24 g of sodium carbonate and 0.05 g of dichlorobis(triphenylphosphine) palladium
(II) were added, stirred at 75°C for 3 hours. Then, the reaction mixture was left and
cooled to room temperature, then a solution of 0.25 g of 4-
chlorohydroxyiminomethyl-N-(2,2,2-trifluoroethyl) benzoic acid amide in 4 ml of 1,2-
dimethoxyethane was added, continued to stir at the same temperature for further 18
hours. After the completion of the reaction, the reaction mixture was poured in 50
ml of water, extracted with ethyl acetate (10 ml x 3), the organic phase was
dehydrated with saturated sodium chloride aqueous solution and dried over
anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
The resudual solid was purified with silica gel column chromatography that was
eluated with chloroform to obtain 0.24 g of the product as white crystal.
Melting point 151.0 to 152.0°C
1H NMR (CDCI3, Me4Si, 400MHz) 87.86 (d, J=8.4Hz, 2H), 7.76 (d, J=8.4Hz, 2H),
7.35-7.5 (m, 2H), 7.0-7.15 (m, 1H), 6.39 (t, J=6.3Hz, 1H), 4.05-4.25 (m, 2H), 4.09 (d,
J=17.3Hz, 1H), 3.74 (d, J=17.3Hz, 1H), 2.32 (d, J=1.7Hz, 3H).
Synthetic Example 8
4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-
N-(2,2,2-trifluoroethyl) benzoic acid amide (Compound of the present invention No.
5-075)
Step 1: Production of 4-bromo-2-methyl-N-(2,2,2-trifluoroethyl) benzoic acid amide
[0209] In a solution of 5.00 g of 4-bromo-2-methyl benzoic acid and 3.45 g of
2,2,2-trifluoroethylamine in 30 ml of N,N-dimethylformamide, 5.79 g of 1-[3-
(diethylamino)propyl]-3-ethylcarbodiimide hydrochloride was added with stirring at
room temperature, and stirred at the same temperature for 1.5 hour. After the
completion of the reaction, 80 ml of water was added, and precipitated crystal was
filtered off, washed with water and dried to obtain 4.00 g of the aimed product as
white crystal.
Melting point 124.0 to 125.5°C
1H NMR (CDCI3, Me4Si, 400MHz) 87.40 (s, 1H), 7.36 (d, J=8.4Hz, 1H), 7.22 (d,
J=8.4Hz, 1H), 6.15 (bs, 1H), 4.0-4.15 (m, 2H), 2.39 (s, 3H).
Step 2: Production of 4-formyl-2-methyl-N-(2,2,2-trifluoroethyl) benzoic acid amide
[0210] In a solution of 1.00 g of 4-bromo-2-methyl-N-(2I2,2-trifluoroethyl) benzoic
acid amide in 15 ml of tetrahydrofuran under nitrogen atmosphere, 4.7 ml of n-butyl
lithium (1.58M hexane solution) was added dropwise at -70°C with stirring, and then
0.4 ml of N.N-dimethylformamide were added dropwise. After stirring at the same
temperature for 30 minutes, 10 ml of 1N hydrochloric acid and then 30 ml of water
were added, and extracted with ethyl acetate (30 ml x 2). The organic phase was
dehydrated with saturated sodiun chloride aqueous solution and dried over
anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure
to obtain 0.80 g of the aimed product as pale yellow crystal.
Melting point 99.0 to 104.0°C
1H NMR (CDCI3, Me4Si, 400MHz) 810.00 (s, 1H), 7.7-7.75 (m, 2H), 7.50 (d, J=7.5Hz,
1H), 6.27 (bs, 1H), 4.05-4.2 (m, 2H), 2.49 (s, 3H).
Step 3: Production of 4-hydroxyiminomethyl-2-methyl-N-(2,2,2-trifluoroethyl) benzoic
acid amide
[0211] In a solution of 0.8 g of 4-formyl-2-methyl-N-(2,2,2-trifluoroethyl) benzoic
acid amide in 10 ml of ethanol and 5 ml of water, 0.3 g of hydroxyamine
hydrochloride and 0.4 g of anhydrous sodium acetate were added with stirring at
room temperature, and stirred at the same temperature for 30 minutes. After the
completion of the reaction, the solvent was distilled off under reduced pressure, and
precipitated crystal was filtered off, washed with water and dried to obtain 0.5 g of
the aimed product as white crystal.
Melting point 190.5 to 194.0°C
1H NMR (CDCI3-DMSO-d6, Me4Si, 400MHz) 810.98 (s, 1H), 8.43 (bs, 1H), 8.07 (s,
1H), 7.35-7.55 (m, 3H), 3.95-4.1 (m, 2H), 2.43 (s, 3H).
Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxasol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl) benzoic acid amide
[0212] In a solution of 0.40 g of 4-hydroxyiminomethyl-2-methyl-N-(2,2,2-
trifluoroethyl) benzoic acid amide in 15 ml of N,N-dimethylformamide, 0.21 g of Nchlorosuccinc
acid imide was added, and stirred at 50°C for 30 minutes. Then, the
reaction mixture was left and cooled to room temperature, 0.34 g of 3,5-dichloro-1-
(1-trifluoromethylethenyl) benzene synthesized in Step 1 of Synthetic Example 3 and
0.16 g of triethylamine were added, and stirred at room temperature for 18 hours.
After the completion of the reaction, the reaction mixture was poured in 50 ml of ice
water, extracted with ethyl acetate (50 ml x 1), the organic phase was dehydrated
with saturated sodium chloride aqueous solution and dried over anhydrous sodium
sulfate, and then the solvent was distilled off under reduced pressure. The residue
was purified with silica gel column chromatography that was eluated with ethyl
acetate-hexane (1:2), and 0.45 g of the aimed product was obtained as white crystal.
Melting point 155.5 to 157.0°C
1H NMR (CDCI3, Me4Si, 400MHz) 57.4-7.55 (m, 6H), 6.13 (bs, 1H), 4.05-4.2 (m, 3H),
3.71 (d, J=17.4Hz, 1H), 2.45 (s, 3H).
Synthetic Example 9
4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-
(2-pyridylmethyl) benzoic acid amide (Compound of the present invention No. 5-234)
Step 1: Production of 4-bromo-2-methyl-N-(2-pyridylmethyl) benzoic acid amide
[0213] In a solution of 3.0 g of 4-bromo-2-methyl benzoic acid in 30 ml of
dichloromethane, 2.7 g of oxalyl chloride and 3 drops of N,N-dimethylformamide
were added under cooling with ice with stirring, and stirred at room temperature for 1
hour. After the completion of the reaction, the solvent was distilled off under
reduced pressure, the residue was dissolved in 30 ml of dichloromethane, 2.1 g of
triethylamine and 2.0 g of 2-picolylamine were added under cooling with ice with
stirring, and continued to stir at room temperature for 3 hours. After the completion
of the reaction, 50 ml of water was added in the reaction mixture, extracted with
chloroform (50 ml x 2), the organic phase was washed with water, dehydrated with
saturated sodium chloride aqueous solution and dried over anhydrous sodium
sulfate, and then the solvent was distilled off under reduced pressure. The residual
solid was washed with diisopropylether to obtain 3.7 g of the aimed product as yellow
crystal.
Melting point 86.0 to 87.5°C
1H NMR (CDCI3, Me4Si, 300MHz) 58.52 (d, J=4.8Hz, 1H), 7.69 (td, J=7.8,1.8Hz, 1H),
7.15-7.4 (m, 6H), 4.73 (d, J=4.8Hz, 2H), 2.45 (s, 3H).
Step 2: Production of 4-formyl-2-methyl-N-(2-pyridylmethyl) benzoic acid amide
[0214] In a solution of 2.0 g of 4-bromo-2-methyl-N-(2-pyridylmethyl) benzoic
acid amide in 20 ml of N,N-dimethylformamide in an autoclave, 0.67 g of sodium
formate and 0.10 g of dichlorobis(triphenylphosphine) palladium (II) were added, and
stirred under 1.05 MPa carbon monoxide atmosphere at 110°C for 3 hours. After
the completion of the reaction, the reaction mixture was left and cooled to room
temperature, and poured in 100 ml of water, and extracted with ethyl acetate (50 ml x
2). The organic phases together were dehydrated with saturated sodium chloride
aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent
was distilled off under reduced pressure. The residue was purified with silica gel
column chromatography that was eluated with ethyl acetate-hexane (9:1), and 0.50 g
of the aimed product was obtained as pale yellow crystal.
Melting point 79.5 to 83.0°C
1H NMR (CDCI3) Me4Si, 300MHz) 810.02 (s, 1H), 8.54 (d, J=5.1Hz, 1H), 7.6-7.8 (m,
4H), 7.15-7.4 (m, 3H), 4.77 (d, J=4.8Hz, 2H), 2.55 (s, 3H).
Step 3: Production of 4-hydroxyiminomethyl-2-methyl-N-(2-pyridylmethyl) benzoic
acid amide
[0215] In a solution of 0.50 g of 4-formyl-2-methyl-N-(2-pyridylmethyl) benzoic
acid amide in 10 ml of ethanol and 5 ml of water, 0.18 g of hydroxyamine
hydrochloride was added with stirring at room temperature, and stirred at the same
temperature for 12 hours. After the completion of the reaction, solid was filtered off,
ethanol was distilled off under reduced pressure, and 30 ml of saturated sodium
hydrogen carbonate aqueous solution was added in the remaining aqueous solution.
The precipitated crystal was filtered off, washed with water and dried to obtain 0.45 g
of the aimed product as pale yellow crystal.
Melting point 159.5 to 161.0°C
1H NMR (CDCI3-DMSO-d6, Me4Si, 300MHz) 611.89 (bs, 1H), 8.56 (d, J=4.2Hz, 1H),
8.03 (s, 1H), 7.90 (bs, 1H), 7.77 (t, J=7.8Hz, 1H), 7.47 (d, J=7.5Hz, 1H), 7.0-7.35 (m,
4H), 4.76 (d, J=6.0Hz, 2H), 2.36 (s, 3H).
Step 4: Production of 4-[5-(3,5-dichlorophenyl}-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2-pyridylmethyl) benzoic acid amide
[0216] In a solution of 0.45 g of 4-hydroxyiminomethyl-2-methyl-N-{2-
pyridylmethyl) benzoic acid amide in 10 ml of N.N-dimethylformamide, 0.25 g of Nchlorosuccinc
acid imide was added, and stirred at 70°C for 1 hour. Then, the
reaction mixture was left and cooled to room temperature, 0.41 g of 3,5-dichloro-1-
(1-trifluoromethylethenyl) benzene synthesized in Step 1 of Synthetic Example 3 and
0.25 g of potassium hydrogen carbonate were added, and stirred at room
temperature for 3 hours. After the completion of the reaction, the reaction mixture
was poured in 50 ml of ice water, extracted with ethyl acetate (60 ml x 1), the organic
phase was dehydrated with saturated sodium chloride aqueous solution and dried
over anhydrous magnesium sulfate, and then the solvent was distilled off under
reduced pressure. The residue was purified with silica gel column chromatography
that was eluated with ethyl acetate-hexane (3:1), and 0.30 g of the aimed product
was obtained as white crystal.
Melting point 131.0 to 135.5°C
1H NMR (CDCI3, Me4Si, 300MHz) 68.53 (d, J=5.0Hz, 1H), 7.65-7.75 (m, 1H), 7.2-
7.55 (m, 9H), 4.75 (d, J=4.9Hz, 2H), 4.09 (d, J=17.3Hz, 1H), 3.71 (d, J=17.3Hz, 1H),
2.50 (s, 3H).
Synthetic Example 10
4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-
(2-pyridylmethyl)-2-trifluoromethyl benzoic acid amide (Compound of the present
invention No. 5-315)
Step 1: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-iodo benzoic acid methyl ester
[0217] In a solution of 0.60 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-
dihydroisoxazol-3-yl]-2-iodo benzoic acid synthesized similarly to Steps 1 to 4 of
Synthetic Example 4 in 10 ml of methanol, 2 drops of concentrated sulfuric acid was
added, and stirred under reflux with heat for 20 hours. After the completion of the
reaction, the solvent was distilled off under reduced pressure, the residue was
neutralized with 10 ml of saturated sodium hydrogen carbonate aqueous solution,
then extracted with ethyl acetate (10 ml x 2). The organic phase was washed with
water, dehydrated with saturated sodium chloride aqueous solution and dried over
anhydrous sodium sulfate, and then the solvent was distilled off under reduced
pressure. The residue was purified with silica gel column chromatography that was
eluated with ethyl acetate-hexane (1:4), and 0.56 g of the aimed product was
obtained as colorless oily substance.
1H NMR (CDCI3, Me4Si, 400MHz) 68.22 (d, J=1.5Hz, 1H), 7.85 (d, J=8.2Hz, 1H),
7.75-7.8 (m, 1H), 7.5-7.55 (m, 2H), 7.4-7.45 (m, 1H), 4.07 (d, J=17.7Hz, 1H), 3.95 (s,
3H), 3.69 (d, J=17.2Hz, 1H).
Step 2: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-trifluoromethyl benzole acid methyl ester
[0218] In a solution of 0.51 g of of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-
dihydroisoxazol-3-yl]-2-iodo benzoic acid methyl ester in 5 ml of N,Ndimethylformamide,
0.18 g of copper (I) iodide, 0.06 g of potassium fluoride and 0.27
g of chlorodifluoro acetic acid methyl ester were added, and stirred at 120°C for 5
hours. After the completion of the reaction, the reaction mixture was left and cooled
to room temperature, 50 ml of water was added and extracted with ethyl acetate (50
ml x 2). The organic phase was washed with water, dehydrated with saturated
sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and
then the solvent was distilled off under reduced pressure. The residue was purified
with silica gel column chromatography that was eluated with ethyl acetate-hexane
(1:4), and 0.45 g of the aimed product was obtained as pale yellow oily substance.
1H NMR (CDCI3) Me4Si, 400MHz) 88.00 (d, J=1.1Hz, 1H), 7.85-7.95 (m, 2H), 7.5-
7.55 (m, 2H), 7.4-7.45 (m, 1H), 4.12 (d, J=7.1Hz, 1H), 3.96 (s, 3H), 3.94 (d, J=7.8Hz,
1H).
Step 3: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-trifluoromethyl benzoic acid
[0219] In a solution of 0.40 g of of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-trifluoromethyl benzoic acid methyl ester in 5 ml of
methanol, a solution of 0.10 g of sodium hydroxide in 2 ml of water was added, and
stirred at room temperature for 18 hours. After the completion of the reaction, 10ml
of water was added in the reaction mixture, washed with 5 ml of toluene, aqueous
phase was collected, adjusted to pH 1 to 2 with concentrated hydrochloric acid and
then extracted with ethyl acetate (20 ml x 2). The organic phase was washed with
water, dehydrated with saturated sodium chloride aqueous solution and dried over
anhydrous sodium sulfate, and then the solvent was distilled off under reduced
pressure to obtain 0.34 g of the aimed product as pale yellow resinous substance.
The resulting product was used as such without purification for the next step.
Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-N-(2-pyridylmethyl)-2-trifluoromethyl benzoic acid amide
[0220] In a solution of 0.15 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-
dihydroisoxazol-3-yl]-2-trifluoromethyl benzoic acid in 3 ml of dichloromethane, 0.06
g of oxalyl chloride and 1 drop of N,N-dimethylformamide were added under cooling
with ice with stirring, and stirred at room temperature for 2 hours. After the
completion of the reaction, the solvent was distilled off under reduced pressure, the
residue was dissolved in 3 ml of dichloromethane, and a solution of 0.05 g of 2-
picolylamine and 0.06 g of triethylamine in 1 ml of dichloromethane was added
dropwise, after the completion of the addition dropwise, continued to stir at room
temperature for 3 hours. After the completion of the reaction, 5 ml of water was
added in the reaction mixture, extracted with chloroform (5 ml x 2). The organic
phase was washed with water, dehydrated with saturated sodium chloride aqueous
solution and dried over anhydrous sodium sulfate, and then the solvent was distilled
off under reduced pressure. The residue was purified with silica gel column
chromatography that was eluated with ethyl acetate-hexane (1:3), and 0.05 g of the
aimed product was obtained as white crystal.
Melting point 69.0 to 70.0°C
1H NMR (CDCI3, Me4Si, 400MHz) 68.5-8.55 (m, 1H), 7.95 (bs, 1H), 7.91 (d, J=1.9Hz,
1H), 7.65-7.8 (m, 2H), 7.5-7.55 (m, 2H), 7.35-7.45 (m, 3H), 7.26 (t, J=4.9Hz, 1H),
4.77 (d, J=4.9Hz, 2H), 4.11 (d, J=17.4Hz, 1H), 3.73 (d, J=17.2Hz, 1H).
Synthetic Example 11
4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-phenyl-N-
(2-pyridylmethyl) benzoic acid amide (Compound of the present invention No. 5-344)
Step 1: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-phenyl benzoic acid methyl ester
[0221] In a solution of 0.70 g of 2-bromo-4-[5-(3,5-dichlorophenyl)-5-
trifluoromethyl-4,5-dihydroisoxazol-3-yl] benzoic acid methyl ester synthesized
similarly to Step 1 of Synthetic Example 10 in 20 ml of tetrahydrofuran and 10 ml of
water, 0.18 g of phenyl boric acid, 0.39 g of potassium carbonate and 0.05 g of
dichlorobis(triphenylphosphine) palladium (II) were added, and stirred under reflux
with heat for 1.5 hour. After the completion of the reaction, the solvent was distilled
off under reduced pressure, the residue was poured in 30 ml of water, then extracted
with ethyl acetate (50 ml x 1). The organic phase was washed with water,
dehydrated with saturated sodium chloride aqueous solution and dried over
anhydrous sodium sulfate, and then the solvent was distilled off under reduced
pressure. The residue was purified with silica gel column chromatography that was
eluated with ethyl acetate, and 0.78 g of the aimed product was obtained as brown
resinous substance.
1H NMR (CDCI3, Me4Si, 400MHz) 87.89 (d, J=8.4Hz, 1H), 7.74 (dd, J=8.0, 1.8Hz,
1H), 7.62 (d, J=1.4Hz, 1H), 7.51 (d, J=1.8Hz, 2H), 7.35-7.45 (m, 4H), 7.25-7.35 (m,
2H), 4.11 (d, J=16.8Hz, 1H), 3.73 (d, J=16.8Hz, 1H), 3.65 (s, 3H).
Step 2: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-phenyl benzoic acid
[0222] In a solution of 0.78 g of of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-phenyl benzoic acid methyl ester in 15 ml of ethanol, a
solution of 0.30 g of sodium hydroxide in 15 ml of water was added, and stirred at
60°C for 3 hours. After the completion of the reaction, ethanol was distilled off
under reduced pressure, adjusted to pH 1 to 2 with 12N hydrochloric acid, and then
extracted with ethyl acetate (50 ml x 1). The organic phase was washed with water,
dehydrated with saturated sodium chloride aqueous solution and dried over
anhydrous sodium sulfate, and then the solvent was distilled off under reduced
pressure to obtain 0.70 g of the aimed product as brown glass substance. The
resulting product was used as such without purification for the next step.
Step 3: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-phenyl-N-(2-pyridylmethyl) benzoic acid amide
[0223] In a solution of 0.3 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-
dihydroisoxazol-3-yl]-2-phenyl benzoic acid in 10 ml of chloroform, 0.3 ml of oxalyl
chloride and a catalytic amount (2 to 3 drops) of N,N-dimethylformamide were added
with stirring at room temperature, and stirred at the same temperature for 10
minutes. After the completion of the reaction, the solvent was distilled off under
reduced pressure, the residue was dissolved in 10 ml of chloroform, and under
cooling with ice with stirring 0.3 ml of 2-picolylamine and then 0.3 ml of triethylamine
were added, and continued to stir at room temperature for 20 minutes. After the
completion of the reaction, the reaction mixture was poured in 40 ml of water,
extracted with ethyl acetate (50 ml x 1). The organic phase was washed with water,
dehydrated with saturated sodium chloride aqueous solution and dried over
anhydrous sodium sulfate, and then the solvent was distilled off under reduced
pressure. The residue was purified with silica gel column chromatography that was
eluated with ethyl acetate-hexane (2:1), and 0.2 g of the aimed product was obtained
as white crystal.
Melting point 194.0 to 198.0°C
1H NMR (CDCI3, Me4Si, 400MHz) 68.3-8.35 (m, 1H), 7.25-7.8 (m, 12H), 7.1-7.15 (m,
1H), 7.40 (d, J=7.8Hz, 1H), 6.65-6.7 (m, 1H), 4.47 (d, J=5.0Hz, 2H), 4.12 (d,
J=17.0Hz, 1H), 3.74 (d, J=17.0Hz, 1H).
Synthetic Example 12
2-Amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-
N-(2,2,2-trifluoroethyl) benzoic acid amide (Compound of the present invention No.
5-329)
Step 1: Production of 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl] benzoic acid ethyl ester
[0224] In a solution of 0.60 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-nitro benzoic acid ethyl ester synthesized in Steps 1 to 3
of Shynthetic Example 5 in 6 ml of ethyl acetate, 2.0 ml of water, 0.6 ml of acetic acid
and 0.46 g of reduced iron were added, and stirred at 75°C for 2 hours. After the
completion of the reaction, the organic phase was collected, and the aqueous phase
was extracted with ethyl acetate (10 ml x 2). The organic phases together were
washed with water, dehydrated with saturated sodium chloride aqueous solution and
dried over anhydrous sodium sulfate, and then the solvent was distilled off under
reduced pressure to obtain 0.60 g of crude aimed product as brown oily substance.
The resulting product was used as such without purification for the next step.
Step 2: Production of 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl] benzoic acid
[0225] In a solution of 0.6 g of crude 2-amino-4-[5-(3,5-dichlorophenyl)-
5-trifluoromethyl-4,5-dihydroisoxazol-3-yl] benzoic acid ethyl ester in 7 ml of ethanol,
a solution of 0.5 g of potassium hydroxide in 2.0 ml of water was added, and stirred
at room temperature for 18 hours. After the completion of the reaction, 20 ml of ice
water was added in the reaction mixture, adjusted to pH 2 to 3 with concentrated
hydrochloric acid, and then extracted with ethyl acetate (20 ml x 2). The organic
phase was washed with water, dehydrated with saturated sodium chloride aqueous
solution and dried over anhydrous sodium sulfate, and then the solvent was distilled
off under reduced pressure to obtain 0.6 g of crude aimed product as yellow oily
substance. The resulting product was used as such without purification for the next
step.
Step 3: Production of 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl) benzoic acid amide
[0226] In a solution of 0.60 g of crude 2-amino-4-[5-(3,5-dichlorophenyl)-5-
trifluoromethyl-4,5-dihydroisoxazol-3-yl] benzoic acid in 6 ml of chloroform, 0.20 g of
2,2,2-trifluoroethylamine, 0.02 g of 4-(N,N-dimethylamino) pyridine and 0.33 g of 1-
[3-(diethylamino)propyl]-3-ethylcarbodiimide hydrochloride were added, and stirred
at room temperature for 20 hours. After the completion of the reaction, the reaction
mixture was subjected to purification with medium-pressure preparative liquid
chromatography (Yamazen Corporation, medium pressure preparative system;
YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:4), and 0.14 g of the
aimed product was obtained as pale yellow crystal.
Melting point 78.0 to 79.0°C
1H NMR (CDCI3) Me4Si, 400MHz) 67.50 (d, J=1.8Hz, 2H), 7.43 (t, J=1.8Hz, 1H), 7.39
(d, J=8.6Hz, 1H), 6.95-7.0 (m, 2H), 6.29 (t, J=7.0Hz, 1H), 5.68 (bs, 2H), 4.05-4.15
(m, 2H), 4.04 (d, J=17.2Hz, 1H), 3.67 (d, J=17.2Hz, 1H).
Synthetic Example 13
4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylthio-N-
(2-pyridylmethyl) benzoic acid amide (Compound of the present invention No. 5-323)
[0227] In a solution of 0.92 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-
dihydroisoxazol-3-yl]-2-fluoro-N-(2-pyridylmethyl) benzoic acid amide (Compound of
the present invention No. 5-041) synthesized similarly to Synthetic Example 4 in 12
ml of dimethylsulfoxide, 0.12 g of sodium methane thiolate was added with stirring at
room temperature, and stirred at 100°C for 90 minutes. After the completion of the
reaction, the reaction mixture was poured in 30 ml of water, and extracted with ethyl
acetate (20 ml x 3). The organic phase was washed with 30 ml of water,
dehydrated with saturated sodium chloride aqueous solution and dried over
anhydrous sodium sulfate, and then the solvent was distilled off under reduced
pressure. The residue was purified with silica gel column chromatography that was
eluated with chloroform, and 0.89 g of the aimed product was obtained as colorless
oily substance.
1H NMR (CDCI3, Me4Si, 300MHz) 88.51 (d, J=4.8Hz, 1H), 7.6-7.75 (m, 4H), 7.52 (bs,
2H), 7.42 (bs, 1H), 7.37 (bs, 1H), 7.34 (bs, 1H), 7.20 (dd, J=6.9, 1.8Hz, 1H), 4.74 (d,
J=4.8Hz, 2H), 4.10 (d, J=17.1Hz, 1H), 3.75 (d, J=17.1Hz, 1H), 2.47 (s, 3H).
Synthetic Example 14
4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylsulfinyl-
N-(2,2,2-trifluoroethyl) benzoic acid amide (Compound of the present invention No.
5-324)
[0228] In a solution of 0.38 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-
dihydroisoxazol-3-yl]-2-methylthio-N-(2,2,2-trifluoroethyl) benzoic acid amide
(Compound of the present invention No. 5-322) synthesized similarly to Synthetic
Example 13 in 6 ml of 1,2-dichloroethane, 0.10 g of N-chlorosuccinic acid imide was
added with stirring at room temperature, and stirred at the same temperature for 11
hours. After the completion of the reaction, the reaction mixture was poured in 30
ml of water, and extracted with ethyl acetate (20 ml x 3). The organic phase was
washed with 30 ml of saturated sodium hydrogen carbonate, dehydrated with
saturated sodium chloride aqueous solution and dried over anhydrous sodium
sulfate, and then the solvent was distilled off under reduced pressure. The residue
was purified with silica gel column chromatography that was eluated with ethyl
acetate-hexane (1:2), and 0.17 g of the aimed product was obtained as colorless oily
substance.
1H NMR (CDCI3) Me4Si, 300MHz) 88.16 (t, J=8.1Hz, 1H), 7.6-7.8 (m, 3H), 7.55 (d,
J=8.1Hz, 1H), 7.51 (d, J=8.1Hz, 1H), 7.15 and 7.11 (t, J=6.3Hz, 1H), 4.18 (qd,
J=18.5, 6.3Hz, 2H), 4.15 (d, J=17.7Hz, 1H), 3.80 (d, J=17.7Hz, 1H), 2.79 and 2.78
(s, 3H).
Synthetic Example 15
4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-
methylsulfonyl-N-(2,2,2-trifluoroethyl) benzoic acid amide (Compound of the present
invention No. 5-326)
[0229] In a solution of 0.25 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-
dihydroisoxazol-3-yl]-2-methylthio-N-(2,2,2-trifluoroethyl) benzoic acid amide
(Compound of the present invention No. 5-322) synthesized similarly to Synthetic
Example 13 in 6 ml of dichloromethane, 0.17 g of 3-chloroperbenzoic acid was
added with stirring at room temperature, and stirred at the same temperature for 3
days. After the completion of the reaction, the reaction mixture was poured in 30 ml
of sodium thiosulfate aqueous solution, and extracted with chloroform (10 ml x 3).
The organic phase was dehydrated with saturated sodium chloride aqueous solution
and dried over anhydrous sodium sulfate, and then the solvent was distilled off under
reduced pressure. The residue was purified with silica gel column chromatography
that was eluated with chloroform, and 0.20 g of the aimed product was obtained as
colorless oily substance.
1H NMR (CDCI3l Me4Si, 300MHz) 58.16 (t, J=8.4Hz, 1H), 8.05 (bs, 1H), 8.00 (s, 1H),
7.92 (s, 1H), 7.55 (d, J=8.4Hz, 1H), 7.52 (d, J=8.4Hz, 1H), 7.06 and 7.02 (t, J=6.4Hz,
1H), 4.17 (d, J=17.4Hz, 1H), 4.16 (qd, J=18.5, 6.3Hz, 2H), 3.79 (d, J=17.4Hz, 1H),
2.12(s, 3H).
Synthetic Example 16
2-Cyano-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2-
pyridylmethyl) benzoic acid amide (Compound of the present invention No. 5-341)
[0230] In a solution of 0.19 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-
dihydroisoxazol-3-yl]-2-iodo-N-(2-pyridylmethyl) benzoic acid amide (Compound of
the present invention No. 5-065) synthesized similarly to Synthetic Example 4 in 10
ml of dimethylacetamide, 36.0 mg of zinc cyanide, 4.8 mg of zinc, 11.0 mg of
tris(dibenzylideneacetone) dipalladium and 13.5 mg of 1,1'-
bis(diphenylphosphino)ferrocene were added, and stirred under nitrogen
atmosphere at 80 to 120°C for 5 hours. After the completion of the reaction, 30 ml
of ammonia water and 20 ml of water were added in the reaction mixture, and
extracted with ethyl acetate (50 ml x 1). The organic phase was washed with 30 ml
of water, dehydrated with saturated sodium chloride aqueous solution and dried over
anhydrous sodium sulfate, and then the solvent was distilled off under reduced
pressure. The residue was purified with silica gel column chromatography that was
eluated with ethylacetate-hexane (2:1), and 0.05 g of the aimed product was
obtained as brown resinous substance.
1H NMR (CDCI3, Me4Si, 400MHz) 88.5-8.6 (m, 1H), 8.12 (bs, 1H), 7.9-8.0 (m, 2H),
7.15-7.7 (m, 7H), 5.13 (bs, 2H), 4.14 (d, J=17.4Hz, 1H), 3.78 (d, J=17.4Hz, 1H).
Synthetic Example 17
2-Acetylamino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-
N-(2,2,2-trifluoroethyl) benzoic acid amide (Compound of the present invention No.
5-333)
[0231] In a solution of 0.05 g of 2-amino-4-[5-(3,5-dichlorophenyl)-5-
trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl) benzoic acid amide
(Compound of the present invention No. 5-329) synthesized in Synthetic Example 12
and 0.15 ml of triethylamine in 2 ml of chloroform, 0.10 ml of acetic anhydride was
added under cooling with ice with stirring, and stirred at room temperature for 20
hours. After the completion of the reaction, the reaction mixture was subjected to
purification with medium-pressure preparative liquid chromatography (Yamazen
Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted
with ethyl acetate-hexane (1:8 to 1:1 gradient), and 0.45 g of the aimed product was
obtained as pale yellow resinous substance.
1H NMR (CDCI3, Me4Si, 400MHz) 810.90 (bs, 1H), 8.77 (d, J=1.3Hz, 1H), 7.57 (dd,
J=8.4, 1.5Hz, 1H), 7.53 (d, J=8.4Hz, 1H), 7.50 (d, J=1.7Hz, 2H), 7.45 (t, J=1.8Hz,
1H), 6.82 (bs, 1H), 4.1-4.2 (m, 2H), 4.11 (d, J=17.0Hz, 1H), 3.73 (d, J=17.0Hz, 1H),
2.22 (s, 3H).
Synthetic Example 18
4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylamino-
N-(2,2,2-trifluoroethyl) benzoic acid amide (Compound of the present invention No.
5-331) and4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-
dimethylamino-N-(2,2,2-trifluoroethyl) benzoic acid amide (Compound of the present
invention No. 5-334)
[0232] In a solution of 0.25 g of 2-amino-4-[5-(3,5-dichlorophenyl)-5-
trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl) benzoic acid amide
(Compound of the present invention No. 5-329) synthesized in Synthetic Example 12
and 0.06 g of 36% formaldehyde aqueous solution in 7 ml of 1,2-dichloroethane,
1.00 g of sodium triacetoxy borohydride was added with stirring at room temperature
in three portions at 1 hour-interval, and continued to stir at the same temperature for
further 2 hours. After the completion of the reaction, the reaction mixture was
poured to 5 ml of ice water, the organic phase was collected, and the solvent was
distilled under reduced pressure. The resudue was subjected to purification with
medium-pressure preparative liquid chromatography (Yamazen Corporation,
medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl
acetate-hexane (0:1 to 1:3 gradient), and 0.13 g of 4-[5-(3,5-dichlorophenyl)-5-
trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylamino-N-(2,2,2-trifluoroethyl)
benzoic acid amide was obtained as pale yellow crystal, and 0.13 g of 4-[5-(3,5-
dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-dimethylamino-N-
(2,2,2-trifluoroethyl) benzoic acid amide was obtained as pale yellow resinous
substance.
4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylamino-
N-(2,2,2-trifluoroethyl) benzoic acid amide;
Melting point 156.0 to 158.0°C
1H NMR (CDCI3, Me4Si, 400MHz) 87.57 (bs, 1H), 7.52 (d, J=1.6Hz, 2H), 7.43 (t,
J=1.8Hz, 1H), 7.38 (d, J=8.2Hz, 1H), 6.92 (d, J=1.6Hz, 1H), 6.84 (dd, J=8.2, 1.6Hz,
1H), 6.31 (t, J=6.4Hz, 1H), 4.0-4.15 (m, 2H), 4.08 (d, J=17.2Hz, 1H), 3.70 (d,
J=17.2Hz, 1H), 2.91 (s, 3H).
4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-
dimethylamino-N-(2,2,2-trifluoroethyl) benzole acid amide;
1H NMR (CDCI3, Me4Si, 400MHz) 610.29 (t, J=6.2Hz, 1H), 8.22 (d, J=8.1Hz, 1H),
7.73 (d, J=1.7Hz, 1H), 7.52 (d, J=1.7Hz, 2H), 7.44 (t, J=1.8Hz, 1H), 7.33 (dd, J=8.1,
1.6Hz, 1H), 4.13 (qd, J=9.2, 6.2Hz, 2H), 4.10 (d, J=17.2Hz, 1H), 3.72 (d, J=17.2Hz,
1H),2.78(s,6H).
Synthetic Example 19
4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2-
methoxyiminoethyl)-2-methyl benzoic acid amide (Compound of the present
invention No. 5-113)
[0233] In a solution of 152 mg of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-
dihydroisoxazol-3-yl]-N-(2,2-dimethoxyethyl)-2-methyl benzoic acid amide
(Compound of the present invention No. 5-083) synthesized similarly to Synthetic
Example 5 in 14 ml of methaol-water (6:1) mixed solvent, 38 mg of methoxyamine
hydrochloride was added, and stirred under reflux with heat for 8 hours. After the
completion of the reaction, the reaction mixture was left and cooled to room
temperature, diluted by adding 80 ml of ethyl acetate, washed with water (30 ml x 2),
and dehydrated with saturated sodium chloride aqueous solution and dried over
anhydrous sodium sulfate, and then the solvent was distilled off under reduced
pressure. The residue was purified with silica gel column chromatography that was
eluated with ethylacetate-hexane (1:1), and 102 mg of the aimed product was
obtained as colorless resinous substance.
1H NMR (CDCI3, Me4Si, 300MHz) 87.45-7.55 (m, 6H), 7.45-7.55 and 6.83 (t,
J=4.5Hz, 1H), 7.4-7.45 (m, 1H), 6.28 and 6.16 (t, J=4.7Hz, 1H), 4.27 and 4.22 (t,
J=4.7Hz, 2H), 4.08 (d, J=17.1Hz, 1H), 3.92 and 3.85 (s, 3H), 3.70 (d, J=17.4Hz, 1H),
2.50 and 2.48 (s, 3H).
Synthetic Example 20
N-[4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-
methylbenzoyl] glycine (Compound of the present invention No. 5-127)
[0234] In a solution of 2.6 g of methyl N-[4-[5-(3,5-dichlorophenyl)-5-
trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoyl] glycine (Compound of the
present invention No. 5-128) synthesized similarly to Synthetic Example 5 in 10 ml of
methanol, a solution of 1.0 g of potassium hydroxide in 10 ml of water was added
with stirring at room temperature, and stirred at the same temperature for further 1
hour. After the completion of the reaction, 10 ml of 12N hydrochloric acid was
added and extracted with ethyl acetate (50 ml x 1), the organic phase was
dehydrated with saturated sodium chloride aqueous solution and dried over
anhydrous sodium sulfate, and then the solvent was distilled off under reduced
pressure to obtain 2.4 g of the aimed product as pale yellow resinous resinous
substance.
1H NMR (CDCI3, Me4Si, 300MHz) S7.4-7.55 (m, 6H), 6.35-6.85 (m, 2H), 4.23 (d,
J=5.7Hz, 2H), 4.08 (d, J=17.1Hz, 1H), 3.71 (d, J=17.1Hz, 1H), 2.44 (s, 3H).
Synthetic Example 21
4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-[N-
(2,2,2-trifluoroethyl) carbamoylmethyl] benzoic acid amide (Compound of the
present invention No. 5-151)
[0235] In a solution of 1.00 g of N-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-methylbenzoyl] glycine (Compound of the present
invention No. 5-127) synthesized in Synthetic Example 20 in 30 ml of
dichloromethane, 0.65 g of 1-[3-(diethylamino)propyl]-3-ethylcarbodiimide
hydrochloride was added, and stirred at room temperature for 15 minutes, then 0.40
g of 2,2,2-trifluoroethylamine and 0.40 g of 4-(N,N-dimethylamino)pyridine were
added and stirred at the same temperature for further 2 hours. After the completion
of the reaction, the solvent was distilled off under reduced pressure, the residue was
purified with silica gel column chromatography that was eluated with ethyl acetatehexane
(1:3), and then crystallized from hexane to obtain 0.48 g of the aimed
product as white crystal.
Melting point 173.5 to 175.5°C
1H NMR (CDCI3, Me4Si, 300MHz) 67.35-7.55 (m, 7H), 7.03 (t, J=5.1Hz, 1H), 4.21 (d,
J=5.1Hz, 2H), 4.09 (d, J=17.4Hz, 1H), 3.85-4.0 (m, 2H), 3.71 (d, J=17.4Hz, 1H), 2.43
(s, 3H).
Synthetic Example 22
4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N- (Nphenylcarbamoylmethyl)
benzoic acid amide (Compound of the present invention
No. 5-169)
[0236] In a solution of 0.40 g of N-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-methylbenzoyl] glycine (Compound of the present
invention No. 5-127) synthesized in Synthetic Example 20 and 0.08 g of pyridine in
10 ml of dichloromethane, 0.12 g of pivaloyl chloride was added, and stirred at room
temperature for 2 hours, then 0.50 g of aniline and 3 ml of triethylamine were added
and stirred at the same temperature for further 1 hour. After the completion of the
reaction, 20 ml of water was added in the reaction mixture and extracted with ethyl
acetate (50 ml x 1), the organic phase was dehydrated with saturated sodium
chloride aqueous solution and dried over anhydrous sodium sulfate, and then the
solvent was distilled off under reduced pressure. The residue was purified with
silica gel column chromatography that was eluated with ethyl acetate-hexane (2:1) to
obtain 0.12 g of the aimed product as white crystal.
Melting point 181.0 to 183.0°C
1H NMR (CDCI3, Me4Si, 300MHz) 88.54 (bs, 1H), 7.5-7.55 (m, 7H), 7.44 (t, J=2.0Hz,
1H), 7.31 (t, J=8.0Hz, 2H), 7.1-7.2 (m, 1H), 6.95 (bs, 1H), 4.34 (d, J=5.0Hz, 2H), 4.19
(d, J=17.2Hz, 1H), 3.70 (d, J=17.2Hz, 1H), 2.49 (s, 3H).
Synthetic Example 23
4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-Nmethyl-
N-(2-pyridylmethyl) benzoic acid amide (Compound of the present invention
No. 6-020)
[0237] In a solution of 0.35 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-
dihydroisoxazol-3-yl]-2-methyl-N-(2-pyridylmethyl) benzoic acid amide (Compound
of the present invention No. 5-234) synthesized similarly to Synthetic Example 5 in
20 ml of N,N-dimethylformamide, 0.04 g of 55% oily sodium hydride was added
under cooling with ice with stirring, and stirred at the same temperature for 30
minutes. Then, 0.12 g of methyl iodide was added and thereafter the temperature
was raised to room temperature, and continued to stir at the same temperature for
further 2 hours. After the completion of the reaction, the reaction mixture was
diluted with 80 ml of ethyl acetate, washed with water (50 ml x 2), dehydrated with
saturated sodium chloride aqueous solution and dried over anhydrous magnesium
sulfate, and then the solvent was distilled off under reduced pressure. The resudue
was purified with high performance liquid chromatography that was eluated with
acetonitrile-water (85:15) to obtain 0.25 g of the aimed product as colorless resinous
substance.
1H NMR (CDCI3, Me4Si, 300MHz) 68.5-8.6 (m, 1H), 7.6-7.75 (m, 1H), 7.05-7.55 (m,
8H), 4.43 and 4.89 (bs, 2H), 4.06 and 4.09 (d, J=17.4 and 17.1 Hz, 1H), 3.68 and
3.71 (d, J=17.4 and 17.1Hz, 1H), 2.85 and 3.13 (s, 3H), 2.35 and 2.38 (s, 3H).
Synthetic Example 24
7-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-d ihyd roisoxazol-3-yl]-1 -methyl-3-(2-
pyridylmethyl)-1,2,3,4-tetrahydroquinazolin-4-one (Compound of the present
invention No. 6-071)
[0238] In a solution of 0.06 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-
dihydroisoxazol-3-yl]-2-methylamino-N-(2-pyridylmethyl) benzoic acid amide
(Compound of the present invention No. 5-332) synthesized similarly to Synthetic
Example 18 in 5 ml of dichloromethane, 0.03 g of chloromethylether was added, and
stirred at the same temperature for 15 hours After the completion of the reaction,
the solvent was distilled off under reduced pressure, and the residue was purified
with silica gel column chromatography that was eluated with ethyl acetate-hexane
(3:1) to obtain 0.04 g of the aimed product as colorless oily substance.
1H NMR (CDCI3, Me4Si, 300MHz) 58.5-8.6 (m, 1H), 8.04 (d, J=7.8Hz, 1H), 7.6-7.75
(m, 1H), 7.4-7.55 (m, 4H), 7.15-7.3 (m, 1H), 7.10 (bs, 1H), 6.95-7.05 (m, 1H), 4.86 (s,
2H), 4.06 (s, 2H), 4.09 (d, J=17.4Hz, 1H), 3.70 (d, J=17.4Hz, 1H), 2.90 (s, 3H).
Synthetic Example 25
4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-
(2,2,2-trifluoroethyl) benzoic acid thioamide (Compound of the present invention No.
7-007)
[0239] A solution of 0.50 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-
dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl) benzoic acid amide
(Compound of the present invention No. 5-075) synthesized in Synthetic Example 8
and 0.41 g of Lawesson's Reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-
dithiadiphosphetan-2,4-disulfide) in 15 ml of toluene was stirred under reflux with
heat for 20 hours. After the completion of the reaction, the reaction mixture was left
and cooled to room temperature, and the reaction mixture was diluted with 60 ml of
ethyl acetate, washed with water (50 ml x 1), then dehydrated with saturated sodium
chloride aqueous solution and dried over anhydrous magnesium sulfate, and then
the solvent was distilled off under reduced pressure. The residue was purified with
silica gel column chromatography that was eluated with ethyl acetate-hexane (3:1) to
obtain 0.40 g of the aimed product as yellow resinous substance.
1H NMR (CDCI3, Me4Si, 300MHz) 67.2-7.5 (m, 7H), 4.55-4.7 (m, 2H), 4.06 (d,
J=17.1Hz, 1H), 3.68 (d, J=17.1Hz, 1H), 2.38 (s, 3H).
Synthetic Example 26
4-[5-(3-Bromodifluoromethoxyphenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-
methyl-N-(2,2,2-trifluoroethyl) benzoic acid amide (Compound of the present
invention No. 5-014)
Step 1: Production of 3-bromodifluoromethoxy-1-iodobenzene
[0240] In a suspension of 0.87 g of 55% oily sodium hydride in 20 ml of N,Ndimethylformamide,
a solution of 4.00 g of 3-iodophenol in 10 ml of N,Ndimethylformamide
was added dropwise with stirring under ice cooling , after the
completion of the addition dropwise, stirred at room temperature for 30 minutes.
The reaction mixture was added dropwise in a solution of 11.40 g of
dibromodifluoromethane in 20 ml of N,N-dimethylformamide under cooling with ice
with stirring, after the completion of the addition dropwise, continued to stir at room
temperature for 2 hours. After the completion of the reaction, 50 ml of water was
added in the reaction mixture, extracted with ethyl acetate (100 ml x 1), the organic
phase was washed with water, then dehydrated with saturated sodium chloride
aqueous solution and dried over anhydrous magnesium sulfate, and then the solvent
was distilled off under reduced pressure. The residue was purified with silica gel
column chromatography that was eluated with hexane to obtain 2.10 g of the aimed
product as colorless oily substance.
1H NMR (CDCI3, Me4Si, 300MHz) 87.65-7.7 (m, 1H), 7.55-7.65 (m, 1H), 7.2-7.3 (m,
1H), 7.15 (t, J=9.0Hz, 1H).
Step 2: Production of 3-bromodifluoromethoxy-1-(1-trifluoromethylethenyl) benzene
[0241] In 10 ml of a solution of 1-trifluoromethylethenyl zinc bromide prepared
according to the method described in documents in 1M tetrahydrofuran, 1.0 g of
3-bromodifluoromethoxy-1-iodobenzene and 0.05 g of
dichlorobis(triphenylphosphine) palladium (II) were added, and stirred under reflux
with heat for 2 hours. After the completion of the reaction, the reaction mixture was
poured in 20 ml of diluted hydrochloric acid, extracted with ethyl acetate (50 ml x 1).
The organic phase was dehydrated with saturated sodium chloride aqueous solution
and dried over anhydrous sodium sulfate, and then the solvent was distilled off under
reduced pressure. The residue was dissolved in hexane, and high polar impurities
were excluded by treating with silica gel to obtain 0.77 g of crude aimed product as
colorless oily substance. The resulting product was used as such without
purification for the next step.
Step 3: Production of 4-[5-(3-bromodifluoromethoxyphenyl)5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl) benzoic acid amide
[0242] In a solution of 0.3 g of 4-chlorohydroxyiminomethyl-2-methyl-N-(2,2,2-
trifluoroethyl) benzoic acid amide synthesized similarly to Steps 1 to 3 of Synthetic
Example 7 and 0.2 g of crude 3-bromodifluoromethoxy-1-(1-trifluoromethylethenyl)
benzene in 10 ml of 1,2-dimethoxyethane, 0.4 g of potassium hydrogen carbonate
was added, and stirred at room temperature for 18 hours. After the completion of
the reaction, the reaction mixture was poured in 20 ml of water, extracted with ethyl
acetate (50 ml x 1). The organic phase was dehydrated with saturated sodium
chloride aqueous solution and dried over anhydrous sodium sulfate, and then the
solvent was distilled off under reduced pressure. The residue was purified with
silica gel column chromatography that was eluated with ethyl acetate-hexane (1:1) to
obtain 0.29 g of the aimed product as colorless glass substance.
1H NMR (CDCI3, Me4Si, 400MHz) 87.5-7.6 (m, 5H), 7.41 (d, J=7.8Hz, 1H), 7.3-7.5
(m, 1H), 6.16 (t, J=6.6Hz, 1H), 4.05-4.15 (m, 3H), 3.74 (d, J=17.2Hz, 1H), 2.45 (s,
3H).
Synthetic Example 27
4-[5-Chlorodifluoromethyl-5-(3,5-dichlorophenyl)-4,5-dihydroisoxazol-3-yl]-2-
methyl-N-(2,2,2-trifluoroethyl) benzoic acid amide (Compound of the present
invention No. 5-355)
Step 1: Production of 2,3',5'-trichloro-2,2-difluoroacetophenone
[0243] In a solution of 5.0 g of 3,5-dichloro-1-iodobenzene in 50 ml of tbutylmethylether,
12.2 ml of n-butyl lithium (1.58M hexane solution) was added
dropwise at -78°C with stirring, after the completion of the addtion dropwise, stirred
at the same temperature for 30 minutes. 6.6 g of chlorodifluoroacetic acid methyl
ester was added dropwise at -78°C with stirring in the reaction mixture, after the
completion of the addition drropwise, continued to stir at 0°C for further 30 minutes.
After the completion of the reaction, the reaction mixture was poured in 100 ml of
saturated ammonium chloride aqueous solution, extracted with ethyl acetate (100 ml
x 1). The organic phase was dehydrated with saturated sodium chloride aqueous
solution and dried over anhydrous magnesium sulfate, and then the solvent was
distilled off under reduced pressure to obtain 4.6 g of crude aimed product as pale
yellow oily substance. The resulting product was used as such without purification
for the next step.
1H NMR (CDCI3, Me4Si, 300MHz) 57.97 (s, 2H), 7.68 (s, 1H).
Step 2: Production of 3,5-dichloro-1-[1-(chlorodifluorofluoromethyl)ethenyl] benzene
[0244] in a solution of 2.89 g of methyltriphenylphosphonium bromide in 15 ml of
tetrahydrofuran, 0.91 g of potassium t-butoxide was added, and stirred at room
temperature for 1 hour. Then, a solution of 2.00 g of 2,3',5'-trichloro-2I2-
difluoroacetophenone in 5 ml of tetrahydrofuran was added dropwise in the reaction
mixture under cooling with ice with stirring, after the completion of the addition
dropwise, continued to stir at room temperature for 1 hour. After the completion of
the reaction, the reaction mixture was poured in 50 ml of ice water, extracted with
ethyl acetate (50 ml x 1), the organic phase was dehydrated with saturated sodium
chloride aqueous solution and dried over anhydrous sodium sulfate, and then the
solvent was distilled off under reduced pressure. The residue was purified with
silica gel column chromatography that was eluated with hexane to obtain 1.50 g of
the aimed product as yellow oily substance.
1H NMR (CDCI3, Me4Si, 300MHz) 87.40 (s, 1H), 7.35 (s, 2H), 5.99 (s, 1H), 5.65 (s,
1H).
Step 3: Production of 4-[5-chlorodifluoromethyl-5-(3,5-dichlorophenyl)-
4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl) benzoic acid amide
[0245] In a solution of 0.25 g of 4-chlorohydroxyiminomethyl-2-rnethyl-N-(2,2,2-
trifluoroethyl) benzoic acid amide synthesized similarly to Steps 1 to 3 of Synthetic
Example 7 and 0.26 g of 3,5-dichloro-1-[1-(chlorodifluorofluoromethyl)ethenyl]
benzene in 3 ml of 1,2-dimethoxyethane, 0.43 g of potassium hydrogen carbonate
and a small amount of water were added, and stirred at room temperature for 15
hours. After the completion of the reaction, the reaction mixture was filtered and
thereby solid substance was excluded, and the filtrate was concentrated under
reduced pressure. The residue was purified with silica gel column chromatography
that was eluated with ethyl acetate-hexane (2:3) to obtain 0.28 g of the aimed
product as yellow oily substance.
1H NMR (CDCI3, Me4Si, 300MHz) 87.35-7.65 (m, 6H), 6.06 (t, J=6.1Hz, 1H), 4.0-4.25
(m, 3H), 3.72 (d, J=17.1Hz, 1H), 2.47 (s, 3H).
Synthetic Example 28
4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-
N-methoxycarbonyl-N-(2-pyridylmethyl) benzoic acid amide (Compound of the
present invention No. 6-043)
Step 1: Production of 5-(3,5-dichlorophenyl)-3-(3-methyl-4-nitrophenyl)-
5-trifluoromethyl-4,5-dihydroisoxazole
[0246] In a solution of 1.31 g of 3,5-dichloro-1-(1-trifluoromethylethenyl) benzene
synthesized in Step 1 of Synthetic Example 3 and 1.17 g of a-chloro-3-methyl-
4-nitrobenzaldoxime in 10 ml of tetrahydrofuran, 1.15 g of potassium hydrogen
carbonate and 1.50 g of water were added, and stirred at room temperature for 18
hours. After the completion of the reaction, tetrahydrofuran was removed from the
reaction mixture, 3 ml of water was added, and stirred under colloing with ice for
further 30 minutes. Precipitated crystal was filtered off, washed with 5 ml of water
and then 5 ml of diisopropyl ether to obtain 1.29 g of the aimed product as white
crystal.
Melting point 135.0 to 136.0°C
1H NMR (CDCI3) Me4Si, 300MHz) 68.03 (d, J=7.5Hz, 1H), 7.6-7.75 (m, 2H), 7.51 (bs,
2H), 7.44 (t, J=1.8Hz, 1H), 4.11 (d, J=17.4Hz, 1H), 3.73 (d, J=17.4Hz, 1H), 2.64 (s,
3H).
Step 2: Production of 3-(4-amino-3-methylphenyl)-5-(3,5-dichlorophenyl)-
5-trifluoromethyl-4,5-dihydroisoxazole
[0247] In a solution of 1.23 g of 5-(3,5-dichlorophenyl)-3-(3-methyl-
4-nitrophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 10 ml of ethyl acetate, 5.0 ml
of water, 5.0 ml of acetic acid and 0.66 g of reduced iron were added and stirred at
100°C for 2 hours. After the completion of the reaction, the reaction mixture was
filtered through Celite, 20 ml of water was added in the filtrate, extracted with ethyl
acetate (20 ml x 2). The organic phases together were washed with 10 ml of
saturated sodium hydrogen carbonate aqueous solution, and then with 10 ml of
water, thereafter dehydrated with saturated sodium chloride aqueous solution and
dried over anhydrous sodium sulfate, and then the solvent was distilled off under
reduced pressure to obtain 1.05 g of crude aimed product as red-brown oily
substance. The resulting product was used as such without purification for the next
step.
1H NMR (CDCI3) Me4Si, 300MHz) 87.52 (s, 2H), 7.35-7.5 (m, 2H), 7.31 (dd, J=8.0,
2.0HZ, 1H), 6.65 (d, J=8.4Hz, 1H), 4.05 (d, J=17.1Hz, 1H), 3.93 (bs, 2H), 3.64 (d,
J=17.1Hz, 1H), 2.17(8, 3H).
Step 3: Production of 3-(4-bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-
5-trifluoromethyl-4,5-dihydroisoxazole
[0248] in a solution of 0.50 g of 3-(4-amino-3-methylphenyl)-5-
(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 1.0 ml of 1,4-dioxane
and 2.0 ml of water, 1.0 ml of 47% hydrobromic acid was added, and stirred under
reflux with heat for 1 hour. Then, the reaction mixture was cooled with ice, and a
solution of 0.10 g of sodium nitrite in 1.0 ml of water was slowly added dropwise with
stirring at a temperature of 5°C or less, after the completion of the addition dropwise,
continued to stir at the same temperature for further 1 hour. The diazo mixture was
slowly added dropwise in a mixture of 1.0 ml of 47% hydrobromic acid and 0.28 g of
copper (I) bromide at 60°C with stirring, after the completion of the addition dropwise,
continued to stir at 60°C for further 2 hours. After the completion of the reaction, 10
ml of water was added in the reaction mixture, extracted with ethyl acetate (20 ml x
2), the organic phases together were washed with water, then dehydrated with
saturated sodium chloride aqueous solution and dried over anhydrous sodium
sulfate, and then the solvent was distilled off under reduced pressure. The residue
was purified with silica gel column chromatography that was eluated with ethyl
acetate-hexane (1:10) to obtain 0.43 g of the aimed product as pale yellow crystal.
Melting point 105.0 to 108.0°C
1H NMR (CDCI3, Me4Si, 300MHz) 57.59 (d, J=8.4Hz, 1H), 7.45-7.55 (m, 3H), 7.42 (t,
J=1.8Hz, 1H), 7.33 (dd, J=8.4, 2.1Hz, 1H), 4.07 (d, J=17.1Hz, 1H), 3.68 (d,
J=17.1Hz, 1H), 2.43 (s, 3H).
Step 4: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-methylbenzoic acid ethyl ester
[0249] In a solution of 15.0 g of 3-(4-bromo-3-methylphenyl)-5-(3,5-
dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 60 ml of ethanol in an
autoclave, 3.26 g of sodium acetate, 0.37 g of 1,1'-bis(diphenylphosphino) ferrocene
and 0.08 g of palladium (II) acetate were added, and stirred under 2.0 MPa carbon
monoxide atmosphere at 110°C for 3 hours. After the completion of the reaction,
the reaction mixture was left and cooled to room temperature, 200 ml of water was
added and extracted with ethyl acetate (200 ml x 2), the organic phase was washed
with water, dehydrated with saturated sodium chloride aqueous solution and dried
over anhydrous sodium sulfate and the solvent was distilled off under reduced
pressure. The residue was purified with silica gel column chromatography that was
eluted with ethyl acetate-hexane (1:8) to obtain 10.8 g of the aimed product as
colorless clear liquid.
Refractive index nD
214°c = 1.5474
1H NMR (CDCI3l Me4Si, 300MHz) 87.95 (d, J=8.4Hz, 1H), 7.45-7.65 (m, 4H), 7
.43 (t, J=1.8Hz, 1H), 4.37 (q, J=7.2Hz, 2H), 4.10 (d, J=17.4Hz, 1H), 3.71 (d,
J=17.1Hz, 1H), 2.62 (s, 3H), 1.40 (t, J=7.2Hz, 3H).
Step 5: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-methyl benzoic acid
[0250] In a solution of 10.79 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-methylbenzoic acid ethyl ester in 50 ml of ethanol and 10
ml of water, a solution of 2.0 g of sodium hydroxide in 10 ml of water was slowly
added with stirring at room temperature. Then, the reaction mixture was stirred at
80°C for 2 hours, after the completion of the reaction, ethanol was distilled off under
reduced pressure. The residue was adjusted to pH 1-2 with concentrated
hydrochloric acid with stirring at 50°C, then continued to stir at the same temperature
for 1 hour and then at 5°C for 1 hour. Presipitated crystal was filtered off, washed
with water and dried to obtain 9.36 g of the aimed product as white crystal.
Melting point 146.0 to 148.5°C
1H NMR (CDCI3, Me4Si, 300MHz) 88.12 (d, J=8.7Hz, 1H), 7.5-7.7 (m, 2H), 7.52 (d,
J=1.5Hz, 2H), 7.43 (d, J=1.5Hz, 1H), 4.11 (d, J=16.8Hz, 1H), 3.73 (d, J=17.4Hz, 1H),
2.69 (s, 3H).
Step 6: Production of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-methyl-N-methoxycarbonyl-N-(2-pyridylmethyl) benzoic
acid amide
[0251] In a solution of 1.00 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-
4,5-dihydroisoxazol-3-yl]-2-methyl benzoic acid in 30 ml of toluene, 0.43 g of thionyl
chloride and 3 drops of N,N-dimethylformamide were added, and stirred at 90°C for
1 hour. After the completion of the reaction, the solvent was distilled off under
reduced pressure, and the resudue was dissolved in 5 ml of tetrahydrofuran. In a
solution of 0.40 g of N-(2-pyridylmethyl) carbamic acid methyl ester in 5 ml of
tetrahydrofuran, 0.27 g of t-butoxy potassium was added at room temperature with
stirring, and stirred at the same temperature for 3 minutes. Then, the
above-mentioned solution of acid chloride in tetrahydrofuran was added dropwise in
the reaction mixture, after the completion of the addition dropwise, continued to stir
at the same temperature for further 1 hour. After the completion of the reaction, the
reaction mixture was diluted with 60 ml of ethyl acetate, washed with 50 ml of water,
then dehydrated with saturated sodium chloride aqueous solution and dried over
anhydrous sodium sulfate and the solvent was distilled off under reduced pressure.
The residue was purified with silica gel column chromatography that was eluted with
ethyl acetate-hexane (1:2 to 1:1) to obtain 0.75 g of the aimed product as yellow
resinous substance.
1H NMR (CDCI3, Me4Si, 300MHz) 68.56 (d, J=4.8Hz, 1H), 7.65-7.7 (m, 1H), 7.5-7.55
(m, 4H), 7.35-7.45 (m, 2H), 7.15-7.3 (m, 2H), 5.21 (s, 2H), 4.09 (d, J=17.4Hz, 1H),
3.70 (d, J=17.4Hz, 1H), 3.58 (s, 3H), 2.40 (s, 3H).
[0252] The compounds of the present invention can be produced according to
the above-mentioned production methods and working examples. The examples of
the compounds produced similarly to Synthetic Examples 1 to 28 are shown in
Tables 7 to 20 to which the present invention is not limited. In the meantime, in
Tables, the indication "Et" means ethyl, hereinafter similarly thereto, "n-Pr" and "Pr-n"
mean normal propyl, "i-Pri and "Pr-i" mean isopropyl, "c-Pr" and "Pr-c" mean
cyclopropyl, "n-Bu" and "Bu-n" mean normal butyl, "s-Bu" and "Bu-s" mean
secondary butyl, "i-Bu" and "Bu-i" mean isobutyl, "t-Bu" and "Bu-t" mean tertiary
butyl, "c-Bu" and "Bu-c" mean cyclobutyl, c-Pen" and "Pen-c" mean cyclopentyl, "n-
Hex" and "Hex-n" mean normal hexyl, "c-Hex" and "Hex-c" mean cyclohexyl, "Ph"
means phenyl, "TMS" means trimethylsilyl, and in Tables, aromatic heterocyclic rings
of D-1a to D-54b are the following structures, respectively
Among the compounds of the prsent invention, 1H NMR data of the compounds that
the measured value of molecular ion peak, melting point or refractive index is not
shown are shown in Table 21.
In the meantime, the indication of" (A)" in the table shows a condition in which
tetramethylsilane is used as standard substance in chloroform-d solvent and
measurement is carried out at 300MHz (CDCI3, Me4Si, 300MHz), hereinafter, the
indication "(B)" shows the measurement condition of (CDCI3, Me4Si, 400MHz), the
indication of "(C)" shows the measurement condition of (CDCI3-DMSO-d6, Me4Si,
300MHz), and the indication of "(D)" shows the measurement condition of (CDCI3-
DMSO-d6, Me4Si, 400MHz).
[0253] Next, usefulness of the compound of the present invention as a pesticide
is specifically explained in the following Test Examples to which the present invention
is not limited.
Test Example 1: Insecticidal test against cabbage moth
[0254] A 10% emulsifiable concentrate (depending on the compounds, 10%
wettable powder was applied for the test) of the compound of the present invention
was diluted with water containing a spreading agent to prepare a chemical solution
with a concentration of 500 ppm. To the chemical solution was dipped leaves of
cabbage for about 10 seconds, and after air-drying, they were placed in a laboratory
dish, then 5-cabbage moth (Plutella xylostella) in the stage of second instar larva per
the dish were released therein, and the dish was covered with a lid and contained at
a thermostat chamber at 25°C. A number of dead insect(s) after 6 days was
counted and a rate of dead insects was calculated by the following calculation
equation. Incidentally, the test was carried out with two districts.
Rate of dead insects (%) = (Number of dead insects/Number of released insects)
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No.1-005,1-006,1-015,1-016,1-
025,1-031,1-040,1-041,1-053,1-055-1-058,1-062~ 1-074,1-076,1-077,1-079~
1-096,1-098,1-101,1-102,1-104-1-110,1-113,1-114,1-116-1-140,1-145-1-
147,1-149-1-157,1-159-1-161,1-166-1-168,1-171,1-172,1-174,1-175,1-176
*,1-177*,1-178-1-184,1-185*, 1-187,1-188*. 1-189*, 1-190,1-194,1-196,1-
199,1-206*,1-207,1-209,1-212,1-214,1-215,1-225,1-226,2-001-2-005,2-011-
2-021,2-022*,2-024~2-027,2-028**,2-029**,2-030l2-031,2-032*,2-033,2-034*
*,2-035**,2-036-2-041,2-042**,2-043,2-044**,2-045**,2-046**,2-047*,2-048*
*,2-049**,2-050*,2-051*,2-052*,2-053,2-054** ,2-055**,3-002-3-004,3-
006,3-007,3-012,3-018,3-023,3-025-3-028,3-030-3-035,3-037,3-038,3-
040,3-043,3-044,3-046,3-047,3-050,3-055,3-058*,3-060,3-061*,3-062-3-
067,3-068*,3-069,3-070*,3-071*,3-073-3-075,3-077-3-081,3-084,3-085*,3-086
*,3-087-3-089,3-090* ,3-091*,3-092* ,3-093*,3-094-3-098,3-100*,3-102-
3-104,3-105*,3-106~3-108,3-109*,3-110*,3-111*,3-112*,3-113*,3-114,3-
115,3-116*,3-117,3-119~3-127,3-129,3-131,3-132*,3-133-3-136,3-138~
3-141,3-143,3-146,3-148,4-002,4-003*,4-004*,4-005,4-006*,4-008~4-010,5-001
* ,5-002* ,5-003 * ,5-004* ,5-005* ,5-006,5-007,5-008* ,5-009* ,5-010* ,5-011 * ,5-012
* ,5-013* ,5-014 * ,5-015* ,5-016,5-017,5-019,5-022* ,5-023* ,5-029* ,5-030-5-
035,5-036*,5-037*,5-038*,5-039*>5-040*,5-041*,5-042,5-043,5-044*,5-045
*,5-046*,5-047*,5-048*,5-049*,5-050*,5-051*,5-052*,5-053*,5-054-5-056,5-057
*,5-058*,5-059*,5-060*,5-061*,5-062*,5-063*,5-064*,5-065*,5-066,5-067*,5-068
*,5-069*,5-070*,5-071*,5-072*,5-073*,5-074*,5-075,5-075(+)*,5-075(-),5-076
*,5-077*,5-078*,5-079~5-082,5-083*,5-084,5-085*,5-086*I5-087*,5-088*,5-089
*,5-090**,5-091*,5-092*,5-093*,5-094*,5-095,5-097,5-098,5-099*,5-100*,5-101
*l5-102*,5-103*,5-104*,5-105*,5-106-5-108,5-109*,5-110,5-111*,5-112*,5-113
*,5-114*,5-115,5-116,5-117*,5-118*,5-119*,5-120**,5-121*,5-122*,5-123*,5-124
**,5-125,5-126*,5-127,5-128*,5-129,5-130*)5-131~5-133,5-134*,5-135-
5-137,5-138*,5-139*,5-140*,5-141*,5-142*,5-143,5-144*,5-145*,5-146,5-147
*,5-148*,5-149,5-150,5-151*,5-152-5-155,5-156*,5-158,5-159,5-160*,5-16r
*,5-162*,5-163,5-164,5-165*,5-166*,5-167,5-168**,5-169*,5-170~5-172,5-173*
*,5-174**)5-175,5-176*,5-177,5-178,5-179*,5-180*,5-181*,5-182*,5-183
*,5-184,5-185*,5-186*,5-187*,5-188*,5-189**,5-189(+)*,5-189(-),5-190(+)
*,5-190(-),5-191*,5-192*,5-193*,5-194*,5-195**,5-196**,5-197**,5-198-
5-200,5-201 *,5-202*,5-203**,5-204,5-205*,5-206*,5-207,5-208**,5-209,5-210
*,5-211*,5-212*,5-213*,5-214*,5-215*,5-216*,5-217**,5-218*,5-219*,5-219(+)
374
*,5-219(-)*,5-220*,5-221*,5-222*,5-223*,5-224*,5-225*,5-226*,5-227*,5-228
* ,5-229* ,5-230*,5-231*,5-232*,5-233*,5-234*.5-235**,5-236*,5-237,5-238
*,5-239*,5-240*,5-241*,5-242*,5-243**,5-244,5-245*,5-246*,5-247*,5-248,5-249
*,5-250,5-251*,5-252,5-253,5-254*,5-255,5-256*,5-257*.5-258**,5-259*,5-
260,5-261 *,5-262**,5-263**,5-264*,5-265*,5-266,5-267*,5-268*,5-270,5-
271,5-272*,5-273*,5-274*,5-275*,5-276*,5-277*,5-278*.5-279*.5-280,5-
281,5-282*,5-283*,5-284*,5-285*,5-286*,5-287,5-288*,5-289*,5-290,5-291
*, 5-292,5-293,5-294*, 5-295*, 5-296,5-298,5-299*, 5-300*. 5-301*. 5-302,5-303
*,5-304,5-305**,5-306*,5-307*,5-308**,5-309*,5-310**,5-311,5-312*,5-313
* ,5-314* ,5-315 * ,5-316,5-317* ,5-318* ,5-319* ,5-320* ,5-321,5-322,5-323* ,5-324-
5-326,5-328,5-329*,5-330*,5-331*,5-332*,5-333*,5-334*,5-335*,5-336*,5-
337,5-338*,5-339*,5-340,5-341,5-342*,5-343*,5-344*,5-345,5-346*,5-347,5-349
*,5-350-5-352,5-353*,5-354*,5-355*,5-356*,5-357*,5-358*,5-359**,5-360
*,5-361*,5-362*,5-363,5-366I5-372,5-374*)5-375*,5-376**,5-377**,5-378*,5-379
* * ,5-380* * ,5-381 * * ,5-383* ,5-384* ,5-385* *,5-386* *,5-387* ,5-389* ,5-390
*,5-391,5-392*,5-393*,5-395*,5-396**,5-397*l5-398*,5-399*,5-400*,5-401
*,5-402*,5-403~5-407,5-408*,5-409,5-410*,5-411*,5-412*)5-413*,5-414,5-415
*,5-416,5-417*,5-418*,5-419*,5-420*,5-421*,5-422*,5-423*,5-424*,5-425*,5-427
*,5-430*,5-431,5-432*,5-433*,5-434*,5-436,5-439*,5-440*,5-44r,5-442*,5-443
*,5-444*,5-445*,5-446*,5-447-5-449,5-452*,5-453*,5-454*,5-456,5-457,6-001
*,6-002,6-003*,6-004**,6-005,6-006**,6-007*,6-008*,6-009,6-010,6-011
*,6-012,6-013*,6-015**,6-016*,6-017*,6-018*,6-019*,6-020*,6-021*,6-022*
* ,6-023* ,6-024* * ,6-025,6-026* ,6-027* ,6-028* ,6-029* ,6-030,6-031 * ,6-032* ,6-033
*,6-034*,6-035*,6-036*,6-037*,6-038*,6-039*,6-040*,6-041*,6-042*,6-043
* ,6-044 * ,6-045 * ,6-046 * ,6-047 * ,6-048 * ,6-049 * ,6-050 * ,6-051 * ,6-052,6-053,6-054
*,6-055*,6-056*,6-057,6-058*,6-059*,6-060**,6-061,6-062* * ,6-063*,6-064*
* ,6-065* * ,6-066 * ,6-067* * ,6-071 * * ,6-074* ,6-075* ,6-076* ,6-078* ,6-079 * ,6-080
*,6-080(+)*,6-080(-)*,6-083*,6-084*,6-085~6-088,7-001,7-002*,7-003*,7-004
* ,7-005*.7-006*,7-007*,7-008*,7-009*,7-010*,8-002*,8-003*,8-004,9-
003,9-008,9-009,10-001,10-002*,10-003-10-005,11-006,11-018,11-024,11-025
*,11-026*,11-038,11-043,11-045,11-046,11-049*,11-050-11-052,11-054,11-058
-11-062,11-066,11-075,11-088,11-089,12-001,12-002.
In the interim, the indication of "*" shows that the insecticidal test was carried out by
use of a chemical solution of a concentration of 100ppm, and the indication "**"
shows that the insecticidal test was carried out by use of a chemical solution of a
concentration of 10ppm.
Test Example 2: Insecticidal test against common cutworm
[0255] A 10% emulsifiable concentrate (depending on the compounds, 10%
wettable powder was applied for the test) of the compound of the present invention
was diluted with water containing a spreading agent to prepare a chemical solution
with a concentration of 500 ppm. To the chemical solution was dipped leaves of
cabbage for about 10 seconds, and after air-drying, they were placed in a laboratory
dish, then 5-common cutworm (Spodoptera litura) in the stage of second instar larva
per the dish were released therein, and the dish was covered with a lid and
contained at a thermostat chamber at 25°C. A number of dead insect(s) after 6
days was counted and a rate of dead insects was calculated by the calculation
equation similar to that in Test Example 1. Incidentally, the test was carried out with
two districts.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No.1-005,1-015,1-016,1-057,1-
058,1-062,1-066l1-069,1-080,1-081,1-088,1-101,1-102,1-105~1-109,1-
118,1-122,1-123,1-125,1-127,1-129,1-130,1-132,1-153,1-156,1-157,1-166-
1-168,1-175,1-176,1-177*,1-182-1-184,1-185M-188*,1-189M-194,1-206
*,1-207,1-212,1-214,1-215,1-225,2-002,2-003,2-013)2-019-2-021,2-022*,2-024-
2-026,2-028,2-029,2-031,2-032,2-034-2-039,2-041,2-042,2-044-2-046,2-047
*,2-048,2-049,2-050*,2-051*,2-052*,2-054-2-056,3-006,3-018,3-026,3-030,3-032
~3-035,3-037,3-043,3-044,3-047,3-058,3-060~3-064,3-068*,3-069,3-070*,3-071
*, 3-072,3-078,3-079,3-081,3-083-3-086,3-089,3-090*, 3-091*, 3-093* ,3-
094,3-095,3-098,3-100*,3-102,3-103,3-105*,3-106,3-107,3-109,3-110*,3-111
*,3-112*,3-113*,3-114,3-115,3-116*,3-117,3-121,3-123-3-126,3-129,3-131,3-132
*,3-135)3-136,3-139,3-140,3-145,3-148,4-003*,4-004,4-006*,4-010,5-001*,5-002
*,5-003*,5-004*,5-005*,5-006,5-007,5-008*,5-009*,5-010,5-011,5-012*,5-013
* ,5-014* ,5-015* ,5-016,5-017,5-019,5-022* ,5-023* ,5-029* ,5-032,5-034,5-
035,5-036*,5-037*>5-038*,5-039*,5-040*,5-041*,5-042,5-045*,5-046*,5-047
*,5-048*,5-049*,5-050*,5-051*,5-052*,5-053*,5-054,5-057*,5-058*,5-059*,5-060
-5-064,5-065*,5-066-5-068,5-069*,5-070*,5-071*,5-072*,5-073-5-
075,5-075(+)*,5-076*,5-077*,5-078-5-081,5-083*,5-084,5-085,5-086*,5-087
*,5-088*,5-089*,5-090,5-091*,5-092*,5-093*,5-094*,5-099-5-101,5-102*,5-103
376
*,5-104*,5-105*)5-106,5-109,5-1ir,5-112,5-113*,5-114*,5-115,5-116,5-117
*,5-118,5-119*,5-120,5-12r,5-122~5-126,5-128*,5-130,5-132~5-134,5-
136,5-137,5-138*,5-139*,5-140-5-147,5-148*,5-149,5-151~5-156,5-159-
5-169,5-171~5-178,5-179*,5-180,5-181,5-182*,5-183*,5-184,5-185*,5-186
*,5-187*,5-188*,5-189,5-189(+),5-191*,5-192*,5-193~5-201,5-202*,5-
203,5-204,5-205*l5-206*,5-207-5-209,5-210*,5-211*,5-212*,5-213*,5-214
*, 5-215*, 5-216*, 5-217,5-218* ,5-219*, 5-219(+)*, 5-219(-),5-220*, 5-221,5-222
*,5-223*,5-224*,5-225,5-226*,5-227*,5-228,5-229,5-230*,5-231,5-232*,5-233
*,5-234*,5~235,5-236*,5-237*,5-239,5-240*,5-241*,5-242*,5-243~5-245,5-246
*,5-247*.5-249*,5-250,5-251,5-254*,5-256*,5-257-5-259,5-261*,5-262,5-
263,5-264*.5-265*.5-267,5-268*,5-269,5-271,5-272*,5-273*.5-274*,5-275-
5-277,5-278*,5-279*,5-280,5-282*,5-283*,5-284,5-285*,5-286*,5-288*,5-289
* ,5-291 * ,5-292,5-294 * ,5-295* ,5-296,5-298,5-299* ,5-300,5-301 *,5-302,5-
303,5-305,5-306*,5-307*,5-308-5-311,5-312*,5-313*,5-314*,5-315*,5-316,5-317
*, 5-318* ,5-319*, 5-320-5-322,5-323*, 5-329*, 5-330*, 5-331*. 5-332,5-333*, 5-334
*,5-335-5-337,5-338*,5-339*,5-341,5-342,5-343*.5-344*,5-345,5-346,5-349
*,5-351,5-353,5-354,5-355*,5-356-5-359,5-360*,5-361*,5-362*,5-363,5-374
*,5-375*,5-376I5-377,5-378*,5-379-5-386,5-387*,5-389*,5-390*,5-392*,5-393
*,5-395,5-396,5-397*,5-398*,5-399*,5-400*)5-401*,5-402*,5-405~5-407,5-408
*,5-409,5-410*,5-411*,5-412*,5-413*,5-415*,5-417*,5-418*,5-419*,5-420*,5-421
*,5-422*,5-423*,5-424*,5-425*,5-427*,5-430*,5-432*,5-433*,5-434*,5-439
*,5-440*,5-44r,5-442*,5-443*,5-444*,5-446*,5-447,5-452*,5-453*,5-454*,6-001
* ,6-002,6-003* ,6-004-6-006,6-007 * ,6-008* ,6-010,6-012,6-013,6-015,6-016,6-017
* ,6-018,6-019 * ,6-020 * ,6-021 * ,6-022-6-025,6-026 * ,6-027 * ,6-028-6-030,6-031
*,6-032*,6-033*,6-034*,6-035*,6-036~6-038,6-039*,6-040,6-041,6-042*,6-043
*,6-044,6-045,6-046*,6-047*,6-048*,6-049*.6-050* ,6-051*,6-053,6-054*,6-055
*,6-056,6-058-6-067,6-071,6-074*,6-075*,6-076*,6-078*,6-079*,6-080*,6-080(+)
* ,6-080(-) * ,6-083 * ,6-084* ,6-086,6-087,7-001,7-002* ,7-003* ,7-004* ,7-005* ,7-006
*,7-007*,7-008*,7-009*,7-010*,8-002*,8-003*,8-004,9-009,10-001~10-
005,11-024,11-025*,11-026*,11-038,11-049*,11-052,11-055,11-061,11-
062,11-066,11-070,12-001,12-002.
In the interim, the indication of "*" shows that the insecticidal test was carried out by
use of a chemical solution of a concentration of 100ppm.
Test Example 3: Insecticidal test against beet armyworm
[0256] A 10% emulsifiable concentrate (depending on the compounds, 10%
wettable powder was applied for the test) of the compound of the present invention
was diluted with water containing a spreading agent to prepare a chemical solution
with a concentration of 100 ppm. To the chemical solution was dipped leaves of
cabbage for about 10 seconds, and after air-drying, they were placed in a laboratory
dish, then 5-beet armyworm (Spodoptera exigua) in the stage of second instar larva
per the dish were released therein, and the dish was covered with a lid and
contained at a thermostat chamber at 25°C. A number of dead insect(s) after 6
days was counted and a rate of dead insects was calculated by the calculation
equation similar to that in Test Example 1. Incidentally, the test was carried out with
two districts.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No.1-015,1-016,1-057,1-058,1-062-
1-064,1-066,1-080,1-081,1-088,1-102,1-105,1-106,1-109,1-118,1-122,1-
123,1-125,1-127,1-151,1-153,1-155-1-157,1-166,1-175,1-189,1-207,1-
214,1-215,2-003,2-019,2-020,3-026,3-027,3-030,3-032,3-037,3-060,3-091,3-
093,3-095,3-109,3-110,3-112,3-125,5-001-5-005,5-008,5-009,5-029,5-
036,5-037,5-040,5-041,5-045,5-046,5-048,5-049,5-050,5-052,5-053,5-057-
5-059,5-061~5-065,5-067-5-069,5-071I5-073~5-075,5-075(+),5-076,5-083,5-086
-5-089,5-091,5-092,5-094,5-111,5-113,5-117-5-119,5-122,5-138-5-
142,5-147,5-148,5-151,5-160,5-165,5-174,5-182,5-183,5-185-5-188,5-
189(+),5-202,5-205,5-210-5-212,5-214~5-216,5-218,5-219,5-219(+),5-
220,5-223,5-226,5-227,5-230,5-232-5-234,5-236,5-239,5-241,5-247,5-
251,5-257,5-261,5-264,5-268,5-273-5-275,5-279,5-282,5-283,5-285,5-
286,5-288,5-291,5-294,5-295,5-301,5-306,5-307,5-309,5-310,5-312-5-
315,5-320,5-321,5-323,5-331 -5-334,5-339,5-341,5-355-5-357,5-360-5-
362,5-374,5-375,5-378,5-387,5-389,5-390,5-397,5-398,5-412,5-433,5-440,6-017-
6-021,6-026,6-027,6-031,6-033-6-041,6-043-6-045,6-048,6-049,6-058,6-
059,6-063-6-066,6-074-6-076,7-002,7-003,7-005-7-009,8-002,11-
024,11-025,11-026.
Test Example 4: Insecticidal test against oriental tea tortix
[0257] A 10% emulsifiable concentrate (depending on the compounds, 10%
wettable powder was applied for the test) of the compound of the present invention
was diluted with water containing a spreading agent to prepare a chemical solution
with a concentration of 100 ppm. To the chemical solution was dipped leaves of
cabbage for about 10 seconds, and after air-drying, they were placed in a laboratory
dish, then 5-oriental tea tortix (Homona magnanima) in the stage of second instar
larva per the dish were released therein, and the dish was covered with a lid and
contained at a thermostat chamber at 25°C. A number of dead insect(s) after 6
days was counted and a rate of dead insects was calculated by the calculation
equation similar to that in Test Example 1. Incidentally, the test was carried out with
two districts.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No. 1-015,1-016,1-057,1-058,1-062,1-0
80,1-105,1-107,1-0122,1-123,1-125,1-127,1-153,1-156,1-189,1-207,1-214,1-215,2-
003,2-034,2-035,2-051,2-052,3-037,3-060,3-095,3-110,3-112,3-125,3-129,4-003,5-
001,5-003-5-005,5-008,5-009,5-012,5-013,5-022,5-029,5-037,5-040,5-041,5-045
-5-050,5-052,5-053,5-057-5-059,5-061-5-065,5-069~5-071,5-073,5-075,5-075(
+),5-076,5-077,5-083,5-086~5-090,5-092~5-094,5-102,5-103,5-111,5-113,5-114,5
-117,5-119,5-121,5-122,5-138-5-142,5-147,5-148,5-151,5-156,5-160,5-161,5-165,
5-166,5-180,5-182,5-183,5-185,5-187,5-188,5-189(+),5-202,5-205,5-208,5-210-5-
212,5-214-5-216,5-218,5-219,5-219(+),5-220,5-221,5-223,5-226~5-228,5-230,5-
232-5-234,5-236,5-240-5-242,5-246,5-247,5-251,5-254,5-273-5-275,5-279,5-2
82,5-283,5-285,5-286,5-288,5-289,5-291,5-294,5-295,5-301,5-306,5-307,5-310,5-3
12,5-313,5-315,5-319,5-321,5-323,5-329,5-330,5-338,5-339,5-341,5-356,5-357,5-3
59,5-360,5-362,5-374,5-375,5-378,5-379,5-381,5-387-5-390,5-392,5-393,5-395-
5-399,5-401,5-412,5-418,5-419,5-430,5-433,5-434,5-441,6-001,6-003,6-017,6-018,
6-020,6-021,6-027,6-031,6-033-6-035,6-038-6-041,6-043,6-066,6-075,6-076,7-0
02-7-009,8-002,11-024,11-026.
Test Example 5: Insecticidal test against corn earworm
[0258] A 10% emulsifiable concentrate (depending on the compounds, 10%
wettable powder was applied for the test) of the compound of the present invention
was diluted with water containing a spreading agent to prepare a chemical solution
with a concentration of 100 ppm. To the chemical solution was dipped leaves of
cabbage for about 10 seconds, and after air-drying, they were placed in a laboratory
dish, then 1-corn earworm (Helicoverpa armigera) in the stage of second instar larva
per the dish were released therein, and the dish was covered with a lid and
contained at a thermostat chamber at 25°C. A number of dead insect(s) after 6
days was counted and a rate of dead insects was calculated by the calculation
equation similar to that in Test Example 1. Incidentally, the test was carried out with
twelve districts.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No.1-066,1-153,1-156,1-207,1-214,1-2
15,2-034,2-035,2-042,2-055,3-027,3-030,3-032,3-086,3-095,3-109,3-110,3-112,5-0
08,5-009,5-022,5-040,5-046,5-047,5-049,5-050,5-052,5-053,5-057-5-059,5-061-
5-063,5-065,5-068,5-070,5-071,5-075,5-075(+),5-076,5-077,5-083,5-086-5-089,5-
099-5-101,5-109,5-113,5-117,5-120-5-122,5-126,5-138,5-139,5-141,5-142,5-147
,5-148,5-151,5-156,5-160,5-165,5-169,5-177,5-180,5-185,5-189(+),5-193,5-208,5-2
10~5-212,5-214-5-219,5-219(+),5-223,5-227,5-228,5-230,5-231,5-233,5-234,5-2
36,5-241,5-245,5-246,5-249,5-251,5-254,5-261,5-264,5-269,5-273-5-275,5-279,5-
284,5-286,5-291,5-294,5-295,5-306,5-307,5-309,5-310,5-312-5-315,5-319,5-323,5
-331-5-336,5-338,5-339,5-341,5-353-5-355,5-357,5-359,5-360,5-374,5-375,5-37
8-5-381,5-383,5-384,5-387,5-389,5-390,5-393,5-395,5-397-5-400,5-408-5-413,
5-415,5-420-5-424,5-427,5-433,5-434,5-440,5-443,5-446,5-452-5-454,6-003,6-0
04,6-016-6-019,6-021,6-023,6-024,6-026,6-027,6-031,6-033-6-041,6-043-6-04
5,6-048,6-049,6-056,6-066,6-074-6-076,6-078,6-079,6-080,6-080(+),6-080(-),6-08
3,6-084,7-002-7-009,8-002,11-024.
Test Example 6: Insecticidal test against peach fruit moth
[0259] A 10% emulsifiable concentrate (depending on the compounds, 10%
wettable powder was applied for the test) of the compound of the present invention
was diluted with water containing a spreading agent to prepare a chemical solution
with a concentration of 100 ppm. To the chemical solution was dipped apple young
fruits on which peach fruit moth (Carpocina sasakii) laid eggs (20-egg/fruit) for about
10 seconds, and after air-drying, they were placed in a laboratory dish, and the dish
was covered with a lid and contained at a thermostat chamber at 25°C. A number
of dead insect(s) after 20 days was counted and a rate of dead insects was
calculated by the calculation equation similar to that in Test Example 1. Incidentally,
the test was carried out with two districts.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No.5-049,5-050,5-070,5-076,5-083,5-0
88,5-111,5-148,5-219,5-219(+),5-221,5-234,5-286,5-291,5-323,5-360,5-387,5-390,5
-398,6-027,6-039,7-008.
Test Example 7: Insecticidal test against Frankliniella occidentalis
[0260] A wet filter paper was laid in a styrol cup having an inner diameter of 7 cm,
a leaf of a common bean cut out so as to have the same diameter was laid theron,
and 10-Frankliniella occidentalis with first instar larva per leaf was inoculated thereon.
A 10% emulsifiable concentrate (depending on the compounds, 10% wettable
powder was applied for the test) of the compound of the present invention was
diluted with water containing a spreading agent to prepare a chemical solution with a
concentration of 500 ppm. The chemical solution was sprayed with a rotating spray
tower in an amount of 2.5 ml per styrol cup, and the styrol cups were covered with
lids and contained at a thermostat chamber at 25°C. A number of dead insect(s)
after 2 days was counted and a rate of dead insects was calculated by the
calculation equation similar to that in Test Example 1. Incidentally, the test was
carried out with two districts.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No. 1-175,1-177-1-179,1-182,2-020,2-
022,2-028*,2-029*,2-032,2-033,2-034*,2-035*,2-037*,2-038*,2-039*,2-040*,2-04
1*.2-042*,2-043*,2-044*,2-045*,2-046* ,2-047,2-048*.2-049*,2-050-2-052,3-068
,3-072*,3-080,3-084-3-086,3-090,3-093,3-105,3-107,3-109,3-110,3-112,3-114,3-1
22-3-125,3-132,3-135,3-136,4-004,4-006,5-001,5-003,5-009,5-013,5-022,5-023,5-
029,5-037-5-041,5-044~5-053,5-057-5-075,5-075(+),5-076-5-078,5-081-5-08
9,5-090* ,5-091 -5-094,5-099-5-105,5-109,5-111 -5-119,5-120* ,5-121 -5-123,5-
124*,5-126-5-128,5-129*,5-130,5-131*,5-134,5-137~5-142,5-143*,5-144,5-145,
5-146*,5-147,5-148,5-150,5-151)5-153*,5-154,5-156,5-158-5-160)5-161*,5-162,5
-164-5-166,5-167* ,5-168* ,5-169,5-171,5-172* ,5-178-5-188,5-189(+),5-190(+),5-
191 -5-194,5-201,5-202,5-205-5-207,5-208* ,5-210-5-216,5-217* ,5-218,5-219,5
-219(+),5-219(-),5-220~5-234,5-236-5-242,5-244-5-247,5-249,5-251 -5-254,5-2
55*,5-256,5-257,5-258*,5-259-5-261,5-264,5-265,5-269*,5-270,5-271* ,5-272-5-
283,5-284-5-289,5-291,5-292,5-294,5-295,5-297,5-299,5-300,5-301,5-302*,5-303
,5-306,5-307,5-309,5-310*,5-311~5-315,5-318,5-319,5-321-5-323,5-329-5-336)
5-338,5-339,5-341-5-346,5-348,5-349,5-353-5-358,5-360-5-362,5-374,5-375,5-
378,5-379*,5-380*,5-381*,5-383,5-384,5-385*,5-387~5-393,5-395,5-396*,5-397
-5-401,5-403-5-406,5-408-5-413,5-415,5-417-5-419,5-421,5-422,5-425,5-427,
5-430,5-432-5-434,5-439-5-443,5-445,5-446,5-449,5-452,5-453,6-001-6-003,6-
004 * ,6-005 * ,6-006 * ,6-007-6-013,6-015 * ,6-016-6-021,6-022 * ,6-023,6-024 * ,6-02
5*,6-026-6-050,6-054-6-056,6-058,6-059,6-063,6-066,6-070,6-071*,6-074-6-0
76,6-078~6-080,6-080(+),6-080(-),6-083-6-086,7-001,7-003~7-010,8-002,8-003,
10-002,10-005,11-024-11-026,11-043,11-045,11-054-11-056,11-059,11-070,11-
089,12-002.
In the interim, the indication of "*" shows that the insecticidal test was carried out by
use of a chemical solution of a concentration of 100ppm.
Test Example 8: Insecticidal test against Thrips palmi
[0261] A wet filter paper was laid in a styrol cup having an inner diameter of 7 cm,
a leaf of a common bean cut out so as to have the same diameter was laid theron,
and 10-Thrips palmi in the stage of adult per leaf was inoculated thereon. A 10%
emulsifiable concentrate (depending on the compounds, 10% wettable powder was
applied for the test) of the compound of the present invention was diluted with water
containing a spreading agent to prepare a chemical solution with a concentration of
100 ppm. The chemical solution was sprayed with a rotating spray tower in an
amount of 2.5 ml per styrol cup, and the styrol cups were covered with lids and
contained at a thermostat chamber at 25°C. A number of dead insect(s) after 2
days was counted and a rate of dead insects was calculated by the calculation
equation similar to that in Test Example 1. Incidentally, the test was carried out with
two districts.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No.1-179,1-196,2-022,2-024-2-026,2-
028,2-029,2-033,2-035,2-039,2-044-2-048,2-050-2-052,3-079,3-085,3-086,3-091
,3-110,3-112,3-124,3-131,3-148,4-003-4-005,4-010,5-001,5-003,5-006,5-008,5-01
2-5-015,5-022,5-023,5-029,5-036,5-037,5-040,5-045-5-053,5-057-5-063,5-065,
5-067,5-068,5-070~5-075,5-075(+),5-076~5-079,5-081~5-084,5-086~5-093,5-0
99,5-102-5-104,5-111-5-114,5-117-5-121,5-124,5-128-5-130,5-137-5-148,5-
151,5-153,5-156,5-160-5-162,5-165,5-166,5-179,5-180,5-182-5-186,5-188,5-189
(+),5-193,5-202,5-205,5-206,5-208~5-210,5-214-5-216,5-218,5-219,5-219(+),5-2
20,5-224-5-226,5-228-5-230,5-232-5-234,5-236,5-238,5-239,5-242,5-246,5-24
7,5-251,5-256-5-258,5-261,5-264,5-269,5-273-5-276,5-278,5-279,5-280,5-282,5-
283,5-285,5-286,5-288,5-289,5-291,5-294,5-295,5-299,5-303,5-306,5-309,5-310,5-
312-5-314,5-319,5-322,5-323,5-329,5-330,5-332,5-334,5-335,5-338,5-339,5-346,5
-349,5-353-5-362,5-374,5-375,5-378-5-381,5-383-5-385,5-387,5-389,5-390,5-3
95-5-401,5-408-5-413,5-415,5-418-5-424,5-427,5-430,5-432-5-434,5-439-5-
443,5-446,5-452-5-454,6-001,6-003-6-008,6-015,6-017-6-024,6-026-6-035,6-
037-6-041,6-043-6-045,6-047-6-049,6-054-6-056,6-058,6-059,6-063,6-066,6-
070,6-073~6-076,6-078-6-080,6-080(+),6-080(-),6-083,6-084,7-003,7-005~7-00
9,8-002,10-002,11-025,11-026,11-054,11-056,11-059,12-002.
Test Example 9: Insecticidal test against Eysarcoris lewisi
[0262] A 10% emulsifiable concentrate (depending on the compounds, 10%
wettable powder was applied for the test) of the compound of the present invention
was diluted with water containing a spreading agent to prepare a chemical solution
with a concentration of 500 ppm. To the chemical solution was dipped leave
sheaths of rice for about 10 seconds, and after air-drying, they were placed in a test
tube, then 5-Eysarcoris lewisi in the stage of first instar larva per the test tube were
released therein, and the test tube was covered with a sponge and contained at a
thermostat chamber at 25°C. A number of dead insect(s) after 2 days was counted
and a rate of dead insects was calculated by the calculation equation similar to that
in Test Example 1. Incidentally, the test was carried out with two districts.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No.1-015,1-050,1-051,1-175,1-209,2-0
29,2-034,2-035,2-042,2-044-2-052,2-054,2-055,3-047,3-068,3-070-3-072,3-086,
3-090,3-093,3-106,3-109-3-112,3-114,3-125,3-131,5-001,5-003,5-005,5-008,5-00
9,5-013-5-015,5-017,5-022,5-023,5-026,5-029,5-037-5-041,5-045-5-053,5-058
-5-065,5-067-5-069,5-071-5-075,5-075(+),5-076-5-078,5-081,5-083,5-084~5-
094,5-099-5-105,5-111-5-114,5-116-5-122,5-124,5-126,5-128,5-130,5-134,5-1
37-5-142,5-144,5-145,5-147,5-148,5-150,5-151,5-154,5-156,5-158-5-162,5-165,
5-166,5-168,5-169,5-171,5-173,5-174,5-179-5-189,5-189(+),5-191,5-195-5-197,
5-203,5-205,5-206,5-208-5-210,5-212-5-216,5-218,5-219,5-219(+),5-220-5-230
,5-232,5-233,5-235,5-236,5-238-5-247,5-249,5-251,5-254,5-256-5-262,5-264,5-2
65,5-273-5-279,5-283,5-285,5-286,5-288,5-289,5-291,5-294,5-295,5-299-5-301,
5-304-5-310,5-312-5-315,5-318-5-321,5-323,5-329,5-330,5-332,5-334,5-335,5-
338,5-339,5-341-5-344,5-346,5-348,5-353-5-360,5-362,5-374-5-387,5-389,5-3
90,5-392,5-393,5-395-5-401,5-403-5-405,5-408-5-413,5-415,5-417-5-419,5-4
21,5-422,5-427,5-431 -5-434,5-440,5-443,5-445,5-446,5-448,5-452,5-453,6-001,6-
006-6-013,6-015-6-024,6-026-6-029,6-031 -6-051,6-054-6-056,6-058-6-060
,6-062-6-067,6-070,6-071,6-074-6-076,6-078,6-079,6-080,6-080(+),6-080(-),6-08
3-6-086,7-002-7-010,11 -060.
Test Example 10: Insecticidal test against brown rice planthopper
[0263] A 10% emulsifiable concentrate (depending on the compounds, 10%
wettable powder was applied for the test) of the compound of the present invention
was diluted with water containing a spreading agent to prepare a chemical solution
with a concentration of 500 ppm. To the chemical solution was dipped leave
sheaths of rice for about 10 seconds, and after air-drying, they were placed in a test
tube, then 5-brown rice planthopper (Nilaparvata lugens) in the second instar larva
per the test tube were released therein, and the test tube was covered with a sponge
and contained at a thermostat chamber at 25°C. A number of dead insect(s) after 6
days was counted and a rate of dead insects was calculated by the calculation
equation similar to that in Test Example 1. Incidentally, the test was carried out with
two districts.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No.1-005-1-007,1-017,1-061,1-154,1-
175,1 -185,1 -188,1 -189,2-018,2-020,2-025-2-027,2-029,2-033,2-034,2-036,2-044,2
-046,2-051,2-052,2-054,3-013,3-068,3-070,3-072,3-075,3-109,3-112,3-125,5-001,5-
003,5-009,5-013,5-015,5-023,5-029,5-040,5-041,5-049,5-050,5-053,5-058,5-060,5-
061,5-063,5-065~5-068,5-070-5-074,5-075(+),5-076,5-077,5-080,5-081,5-083,5-
084,5-086-5-088,5-090-5-094,5-099,5-102,5-106,5-111,5-113,5-117-5-120,5-1
30,5-138-5-148,5-151-5-156,5-160,5-161,5-163,5-170,5-173,5-174,5-182,5-186,
5-189,5-189(+),5-195,5-197,5-203,5-205,5-208,5-210,5-212,5-214,5-216,5-219,5-2
19(+),5-220,5-226,5-230-5-232,5-234~5-236,5-239,5-240,5-242,5-243,5-245,5-2
46,5-251,5-254,5-257,5-258,5-261,5-262,5-264,5-265,5-273-5-275,5-279,5-280,5-
285,5-286,5-288,5-294,5-295,5-305-5-310,5-313,5-315,5-323,5-330,5-335,5-339,5
-341,5-344,5-353-5-360,5-374-5-377,5-379-5-388,5-390,5-392,5-393,5-396,5-3
98-5-401,5-405,5-410,5-412,5-413,5-419,5-421,5-422,5-427,5-432,5-433,5-440,5-
453,6-001,6-003,6-007,6-015-6-023,6-027-6-045,6-048-6-050,6-056,6-058-6-
065,6-076,6-078,6-079,6-080,6-080(+),6-080(-),6-083,6-086,7-001-7-004,7-006,7-
008,7-009,8-003,9-009,11-039,11-041,11-054.
Test Example 11: Insecticidal test against Bemisia argentifolii
[0264] A wet filter paper was laid in a styrol cup having an inner diameter of 7 cm,
a leaf of a tomato cut out on which Bemisia argentifolii laid eggs (10-egg/leaf) was
laid theron. A 10% emulsifiable concentrate (depending on the compounds, 10%
wettable powder was applied for the test) of the compound of the present invention
was diluted with water containing a spreading agent to prepare a chemical solution
with a concentration of 500 ppm. The chemical solution was sprayed with a rotating
spray tower in an amount of 2.5 ml per styrol cup, and the styrol cups were covered
with lids and contained at a thermostat chamber at 25°C. A number of dead
insect(s) after 6 days was counted and a rate of dead insects was calculated by the
calculation equation similar to that in Test Example 1. Incidentally, the test was
carried out with two districts.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No.1-011,1-182,2-024*,2-025*,2-026
* ,2-028 * ,2-029 * ,2-033,2-034 * ,2-035 * ,2-037 * ,2-044 * ,2-047,2-050,2-051,3-
068,3-079,3-090,3-112,3-125,4-003,4-006,5-001,5-003,5-005,5-007,5-009,5-
011,5-013-5-015,5-021 -5-023,5-029,5-035,5-037-5-041,5-045-5-053,5-057-
5-061,5-063,5-065,5-067-5-075,5-075(+),5-076-5-078,5-079* ,5-081,5-084-
5-089,5-090* ,5-091 -5-094,5-099-5-104,5-112-5-114,5-117,5-118,5-120
*,5-122,5-123,5-126,5-128,5-130,5-137~5-142,5-143*,5-144,5-145,5-146
*,5-148,5-151,5-153*,5-154,5-156,5-158~5-160,5-161*,5-162,5-164,5-165,5-167
* ,5-171,5-180,5-182-5-188,5-189(+),5-191,5-193,5-201,5-202,5-205-5-
207,5-208*,5-209-5-216,5-218,5-219,5-219(+),5-220~5-223,5-225-5-
234,5-236,5-238-5-242,5-245-5-247,5-249,5-254,5-258* ,5-261,5-264,5-273-
5-275,5-277-5-279,5-281,5-285-5-288,5-291,5-292,5-294,5-295,5-297,5-
299,5-301,5-306,5-309,5-310*,5-312-5-315,5-318,5-319,5-321,5-323,5-
330,5-332,5-335,5-339,5-341,5-344,5-345,5-353-5-358,5-359*,5-360,5-
362,5-374,5-375,5-378,5-379*,5-380*,5-381*,5-383,5-384,5-385*,5-387-5-
393,5-396* ,5-397-5-401,5-405,5-409,5-410,5-412,5-417,5-418,5-421,5-
422,5-427,5-430,5-433,5-434,5-440,5-446,5-453,6-001,6-003,6-009,6-011 -
385
6-013,6-016-6-018,6-020,6-021,6-022*,6-027,6-028,6-031-6-041,6-043,6-
044,6-048-6-050,6-056,6-074-6-076,6-078,6-079,6-083,7-001,7-003-7-
006,7-008-7-010,11-017,11 -024,11 -026,11 -028,11 -056.
In the interim, the indication of "*" shows that the insecticidal test was carried out by
use of a chemical solution of a concentration of 100ppm.
Test Example 12: Insecticidal test against green peach aphid
[0265] A wet cotton wool was laid in a laboratory dish having an inner diameter of
3 cm, a leaf of a cabbage cut out so as to have the same diameter was laid theron,
and 4-green peach aphid (Myzus persicae) in the stage of no-wing adult was left.
After 1 day, a 10% emulsifiable concentrate (depending on the compounds, 10%
wettable powder was applied for the test) of the compound of the present invention
was diluted with water containing a spreading agent to prepare a chemical solution
with a concentration of 500 ppm, and the chemical solution was sprayed with a
rotating spray tower (2.5 mg/cm2), and the laboratory dish was covered with lids and
contained at a thermostat chamber at 25°C. A number of dead insect(s) after 6
days was counted and a rate of dead insects was calculated by the calculation
equation similar to that in Test Example 1. Incidentally, the test was carried out with
two districts.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No. 1-006,1-063,1-067,1-069,1-153,1-
158,1-163,1-166,1-167,1-171,1-175,1-207,1-209,1-215,2-005,2-015,2-017,2-024*
,2-025*,2-026*,2-027,2-029*,2-034*,2-044*,2-046*,2-050,2-051,3-006,3-029,3-
064,3-068,3-089,3-110,3-114,3-125,3-131,3-139,3-143,4-003,5-001,5-003,5-005,5-
009,5-013,5-015,5-022,5-023,5-037-5-041,5-045-5-050,5-052,5-053,5-056,5-058
-5-061,5-063,5-065-5-068,5-070~5-075,5-075(+),5-076,5-077,5-079*, 5-081,5-
083-5-086,5-090 * ,5-091 -5-094,5-099,5-100,5-102,5-103,5-113,5-117,5-118,5-
128,5-130,5-134,5-138-5-142,5-143*,5-144,5-145,5-146*,5-147,5-148,5-151,5-
153*,5-154,5-156,5-158,5-160l5-161*,5-162,5-165,5-180-5-187,5-189(+),5-193,5-
202,5-205,5-209,5-210,5-212,5-214~5-216,5-219,5-219(+),5-220~5-223I5-226,5-
228,5-230,5-231,5-233,5-234,5-236,5-238,5-240,5-242,5-243*,5-245-5-247,5-
251,5-254,5-256,5-258*,5-259,5-261,5-264,5-272-5-275,5-277-5-280,5-282,5-
284-5-288,5-291,5-294,5-295,5-300,5-301,5-306,5-307,5-309,5-310*,5-313-5-
315,5-320,5-321,5-323,5-330,5-334,5-335,5-339,5-341,5-343,5-344,5-348,5-352,5-
353-5-358,5-359*,5-360,5-362,5-364,5-374,5-375,5-378,5-379*.5-380*.5-383,5-
384,5-385*,5-387,5-389,5-390,5-392,5-393,5-398,5-399,5-401,5-409,5-410,5-
415,5-418,5-421,5-422,5-427,5-433,5-434,5-440-5-442,5-446,5-453,6-001,6-
003,6-005*,6-007,6-009~6-012,6-015*,6-016~6-021,6-022*,6-027,6-028,6-030-
6-033,6-035-6-044,6-048-6-050,6-054,6-056-6-059,6-063,6-066,6-074-6-
076,6-078-6-080,6-083,6-084,6-086,7-003-7-007,7-009,9-004,10-002,11 -005,11 -
006,11-026,12-004.
In the interim, the indication of "*" shows that the insecticidal test was carried out by
use of a chemical solution of a concentration of 100ppm.
Test Example 13: Insecticidal test against Japanese mealybug
[0266] A wet filter paper was laid in a styrol cup having an inner diameter of 7 cm,
a leaf of a common bean cut out so as to have the same diameter was laid theron,
and 10-Japanese mealybug (Planococcus kraunhiae) in the first instar larva per leaf
was inoculated thereon. A 10% emulsifiable concentrate (depending on the
compounds, 10% wettable powder was applied for the test) of the compound of the
present invention was diluted with water containing a spreading agent to prepare a
chemical solution with a concentration of 500 ppm. The chemical solution was
sprayed with a rotating spray tower in an amount of 2.5 ml per styrol cup, and the
styrol cups were covered with lids and contained at a thermostat chamber at 25°C.
A number of dead insect(s) after 6 days was counted and a rate of dead insects was
calculated by the calculation equation similar to that in Test Example 1. Incidentally,
the test was carried out with two districts.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No.1-011,1-177,1-182,2-020,2-028*,2-029
*,2-033,2-034*,2-035*,2-037*,2-039*,2-040*,2-041*,2-042*,2-044*,2-045*,2-046
* ,2-047,2-048* ,2-049* ,2-050-2-052,2-055* ,3-065,3-069,3-085,3-086,3-091 -3-
093,3-104,3-109,3-125,4-003,4-004,4-006,5-001,5-003,5-005,5-007,5-009,5-013-
5-015,5-017,5-022,5-023,5-029,5-037,5-039-5-041,5-045-5-050,5-052,5-053,5-
057-5-061,5-063-5-065,5-067-5-075,5-075(+),5-076~5-078,5-081,5-083-5-
089,5-090*,5-091-5-094,5-098-5-105,5-109,5-111-5-114,5-116-5-118,5-
121,5-123,5-126,5-128,5-129*,5-130,5-131*,5-138~5-142,5-143*,5-144,5-145,5-
146*,5-147,5-148,5-151,5-153*,5-154,5-156,5-158~5-160,5-161*,5-162,5-164,5-
165,5-166,5-167*,5-168*,5-171,5-172*,5-179~5-188,5-189(+),5-190(+),5-192~5-
194,5-201,5-202,5-205)5-206,5-208*,5-210~5-212,5-214~5-216,5-219,5-
219(+),5-221,5-222l5-223,5-226-5-234l5-236-5-240,5-242l5-245~5-247,5-
249,5-251,5-253,5-254,5-255*,5-256)5-257,5-258*,5-259,5-261,5-264,5-269*,5-
271 *,5-272-5-288,5-291,5-292,5-295-5-297,5-299-5-301,5-302*,5-303,5-
306,5-307,5-309l5-310*,5-312-5-315,5-318,5-319,5-321,5-322,5-323,5-331,5-
332,5-334-5-336,5-338,5-339,5-344,5-345,5-348,5-349,5-353-5-358,5-360-5-
362,5-375,5-378,5-379*,5-380*,5-381*,5-383,5-384,5-385*,5-387,5-388,5-390,5-
392,5-393,5-395,5-396* ,5-397-5-399,5-401,5-406,5-407,5-410,5-412,5-417-5-
419,5-422,5-427,5-430-5-434,5-439-5-443,5-445,5-446,5-452,5-453,6-001-6-
003,6-005*,6-006*,6-007~6-013,6-015*,6-016~6-021,6-022*,6-023,6-024*,6-025
6-026-6-050I6-054~6-056,6-058,6-059,6-063,6-066,6-074~6-076,6-078-6-
080,6-080(+),6-083~6-085,7-003-7-010,8-003,9-003,10-002,11-024-11-026,11-
043,11-045,11-056,11-058,11-059,11-089,12-006.
In the interim, the indication of "*" shows that the insecticidal test was carried out by
use of a chemical solution of a concentration of 100ppm.
Test Example 14: Insecticidal test against cucurbit leaf beetle
[0267] A 10% emulsifiable concentrate (depending on the compounds, 10%
wettable powder was applied for the test) of the compound of the present invention
was diluted with water containing a spreading agent to prepare a chemical solution
with a concentration of 500 ppm. To the chemical solution was dipped leaves of
cucumber for about 10 seconds, and after air-drying, they were placed in a
laboratory dish, then 5-cucurbit leaf beetle (Aulacophora femoralis) in the stage of
second instar larva per the dish were released therein, and the dish was covered
with a lid and contained at a thermostat chamber at 25°C. A number of dead
insect(s) after 6 days was counted and a rate of dead insects was calculated by the
calculation equation similar to that in Test Example 1. Incidentally, the test was
carried out with two districts.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No. 1-005,1-015,1-016,1-040,1-042,1-055
-1-057,1-059,1-061-1-067,1-069-1-071,1-073,1-074,1-076,1-077,1-079-1-
081,1-083-1-085,1-087,1-088,1-090,1-092-1-095,1-098,1-099,1-102,1-104-1-
110,1-113,1-116,1-118,1-119,1-122-1-129,1-131,1-135,1-136,1-138,1-146,1-
147,1-151-1-153,1-155-1-157,1-159,1-166,1-167,1-171,1-172,1-174-1-177,1-
179-1-185,1-187-1-189,1-194,1-199,1-206,1-207,1-210,1-212,1-214,1-215,1-
220,1-225,2-001,2-004,2-006,2-011,2-013,2-019-2-022,2-025-2-029,2-031,2-
032,2-034-2-055,3-002,3-003,3-006,3-011,3-018,3-025-3-028,3-031 -3-035,3-
037,3-044,3-046,3-047,3-050,3-058,3-061-3-065,3-068-3-072,3-074,3-076,3-078
-3-081,3-084-3-087,3-089-3-095,3-097-3-116,3-118-3-125,3-127-3-132,3-
134-3-136,3-138-3-143,3-145-3-148,4-003-4-007,4-009-4-011,5-001-5-
015,5-017,5-021-5-023,5-028-5-042,5-044-5-075,5-075(+),5-075(-),5-076-5-
081,5-083-5-095,5-097,5-099-5-107,5-109-5-130,5-132-5-135,5-137-5-
156,5-158~5-189,5-189(+),5-190(+),5-191-5-219,5-219(+),5-219(-),5-220~5-
236,5-238-5-296,5-298-5-326,5-329-5-339,5-341-5-350,5-352-5-363,5-
365,5-369,5-371,5-374-5-403,5-405-5-413,5-415-5-419,5-421,5-422,5-425,5-
427,5-430-5-434,5-436,5-439-5-447,5-449,5-452,5-453,6-001 -6-013,6-015-6-
024,6-026-6-051,6-053-6-067,6-070,6-071,6-074-6-076,6-078-6-080,6-
080(+),6-080(-),6-083~6-086,7-001-7-010,8-001-8-004,9-003,9-009,10-002~
10-005,11-005,11-015,11-017,11-020,11-023-11-026,11-038,11-043,11-045,11-
046,11 -052-11 -054,11 -056-11 -060,11 -066,11 -067,11 -072,11 -076,12-006.
Test Example 15: Insecticidal test against serpentine leaf miner
[0268] A 10% emulsifiable concentrate (depending on the compounds, 10%
wettable powder was applied for the test) of the compound of the present invention
was diluted with water containing a spreading agent to prepare a chemical solution
with a concentration of 500 ppm. To the chemical solution was dipped leaves of
common bean on which serpentine leaf miner (Liriomyza trifolii) laid eggs (10
eggs/leaf) for about 10 seconds, and after air-drying, they were placed on a wet
filter paper laid in a styrol cup having an inner diameter of 7 cm, and the styrol cup
was covered with a lid and contained at a thermostat chamber at 25°C. A number
of dead insect(s) after 6 days was counted and a rate of dead insects was calculated
by the calculation equation similar to that in Test Example 1. Incidentally, the test
was carried out with two districts.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No.1-175,1-177,2-029*,2-034*,2-035*,2-
044*,2-045*,2-050,2-051,3-060,3-068,3-069,3-071,3-072*.3-085,3-086,3-093,3-
105,3-109,3-112,3-125,3-148,5-001,5-003,5-005,5-007,5-009,5-015,5-022,5-023,5-
036,5-037,5-040,5-041,5-045-5-053,5-058-5-061,5-063-5-065,5-067,5-068,5-
389
070~5-075,5-075(+),5-076,5-077,5-081,5-083,5-085-5-089,5-090*,5-091-5-
094,5-099-5-105,5-113,5-117~5-119,5-120*,5-121-5-123,5-124*,5-126,5-129*
,5-131 *)5-133*,5-138~5-142,5-144,5-145,5-147,5-148,5-150,5-151)5-154,5-156,5-
158,5-160,5-161 *,5-162,5-164~5-166,5-168*,5-169,5-171,5-172*, 5-178,5-180,5-
182-5-188)5-189(+),5-201,5-202,5-208*,5-209,5-210,5-212I5-214~5-216,5-217*
,5-219,5-219(+),5-221-5-223,5-226-5-234,5-236,5-238,5-239,5-241,5-245-5-
247,5-251,5-256,5-257,5-258*,5-259,5-261,5-264,5-265,5-270,5-274,5-275,5-
283,5-284,5-286,5-291,5-294,5-295,5-302*,5-303,5-306,5-309,5-310*,5-313-5-
315,5-319,5-323,5-335,5-336,5-338,5-339,5-341,5-344,5-345,5-353-5-358,5-
360,5-362,5-374)5-375,5-378,5-379*,5-380*l5-381*,5-383I5-384)5-385*,5-387,5-
388,5-390,5-392,5-393,5-395,5-396*,5-397-5-401,5-408-5-413,5-415,5-417-5-
419,5-421,5-422,5-425,5-427,5-430,5-432,5-433,5-439-5-441,5-443,5-445,5-
446,5-452,5-453,6-001,6-004*,6-005*,6-006*,6-007,6-008,6-011-6-013,6-015*,6-
016-6-021,6-022 * ,6-024 * ,6-025* ,6-027,6-031,6-033-6-041,6-043,6-044,6-048-
6-050,6-054-6-056,6-066,6-070,6-074-6-076,6-078,6-079,6-083,6-085,7-003,7-
005-7-009.
In the interim, the indication of "*" shows that the insecticidal test was carried out by
use of a chemical solution of a concentration of 100ppm.
Test Example 16: Insecticidal test against two-spotted spider mite
[0269] A wet filter paper was laid in a styrol cup having an inner diameter of 7 cm,
a leaf of a common bean cut out so as to have the same diameter was laid theron,
and 10 larvae of two-spotted spider mite (Tetranychus urticae) per leaf was
inoculated thereon. A 10% emulsifiable concentrate (depending on the compounds,
10% wettable powder was applied for the test) of the compound of the present
invention was diluted with water containing a spreading agent to prepare a chemical
solution with a concentration of 500 ppm. The chemical solution was sprayed with
a rotating spray tower in an amount of 2.5 ml per styrol cup, and the styrol cups were
covered with lids and contained at a thermostat chamber at 25°C. A number of
dead insect(s) after 6 days was counted and a rate of dead insects was calculated by
the calculation equation similar to that in Test Example 1. Incidentally, the test was
carried out with two districts.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No.1-177,1-182,2-027,2-028*,2-029*,2-
034*,2-035*,2-036,2-037*,2-039*,2-040*,2-041*,2-042*,2-044*,2-045*,2-046*,2-
047,2-048*,2-049*,2-050~2-052,3-068,3-084,3-086,3-109,3-110,3-112,3-114,3-
124,3-131,5-001,5-003,5-005,5-007-5-009,5-011,5-013,5-015,5-019,5-021,5-
022,5-023,5-028,5-029,5-035-5-037,5-040,5-041,5-045-5-053,5-057-5-075,5-
075(+),5-076~5-078,5-080-5-089,5-090*, 5-091 -5-094,5-098-5-105,5-109,5-
112-5-114,5-117-5-119,5-121~5-123,5-126,5-128,5-129*,5-130,5-132,5-134,5-
136~5-142,5-143*,5-144,5-145,5-146*,5-147,5-148,5-150~5-152,5-153*,5-154-
5-156,5-158-5-160,5-161 *,5-162~5-166,5-167*,5-168*,5-171,5-172*,5-177~5-
180,5-182-5-188,5-189*,5-189(+),5-190(+),5-191,5-192,5-196*,5-197*,5-199-5-
202,5-204-5-207,5-208*,5-209-5-212,5-214-5-216,5-218,5-219,5-219(+),5-
219(-),5-220~5-234,5-235*,5-236,5-238~5-242,5-243*,5-245-5-247,5-249,5-
251,5-254,5-255*,5-256,5-257,5-258*,5-259,5-261,5-264,5-265,5-269*.5-271*.5-
273-5-275,5-277-5-279,5-283-5-286,5-288,5-291,5-292,5-294,5-295,5-299-5-
301,5-306,5-307,5-312-5-316,5-321,5-323,5-325,5-330,5-336,5-338,5-339,5-
341,5-344,5-345,5-349,5-353-5-358,5-360,5-362,5-374,5-375,5-376*,5-377*,5-
378,5-379*,5-380*,5-38r,5-383,5-384,5-385*,5-386*,5-387-5-395,5-396*,5-397
-5-399,5-401,5-402,5-405,5-406,5-408-5-413,5-415,5-417-5-419,5-421,5-
422,5-425,5-427,5-430,5-432,5-433,5-440,5-441,5-443,5-445,5-452,5-453,6-001,6-
003,6-007,6-008,6-011~6-013,6-015*,6-016-6-021,6-023,6-027,6-030~6-044,6-
046-6-050,6-054-6-056,6-066,6-074-6-076,6-078,6-079,6-083-6-085,7-003-
7-010,8-003,10-002,11-026,12-002.
In the interim, the indication of "*" shows that the insecticidal test was carried out by
use of a chemical solution of a concentration of 100ppm.
Test Example 17: Insecticidal test against pink citrus rust mite
[0270] A wet filter paper was laid in a styrol cup having an inner diameter of 7 cm,
a leaf of a mandarin orange cut out so as to have the same diameter was laid theron,
and 10 larvae of pink citrus rust mite (Aculops pelekassi) per leaf was inoculated
thereon. A 10% emulsifiable concentrate (depending on the compounds, 10%
wettable powder was applied for the test) of the compound of the present invention
was diluted with water containing a spreading agent to prepare a chemical solution
with a concentration of 100 ppm. The chemical solution was sprayed with a rotating
spray tower in an amount of 2.5 ml per styrol cup, and the styrol cups were covered
with lids and contained at a thermostat chamber at 25°C. A number of dead
insect(s) after 6 days was counted and a rate of dead insects was calculated by the
calculation equation similar to that in Test Example 1. Incidentally, the test was
carried out with two districts.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No. 1-177,3-093,3-112,5-001 -5-003,5-
005,5-008,5-009,5-022,5-023,5-036,5-037,5-040,5-041,5-046,5-047,5-049,5-050,5-
053,5-057-5-059,5-061,5-063,5-065,5-066,5-069-5-071,5-074-5-077,5-081,5-
083,5-084,5-086,5-088,5-111 -5-113,5-121,5-137-5-140,5-148,5-151,5-174,5-
182,5-183,5-185,5-187,5-188,5-202,5-205,5-206,5-215,5-216,5-219-5-221,5-
225,5-226,5-233-5-235,5-241,5-247,5-274,5-285,5-291,5-294,5-295,5-301,5-
313,5-323,5-331,5-334,5-338,5-339,5-355,5-360,5-374,5-378,5-387-5-390,5-
393,5-397,5-398,6-003,6-017,6-020,6-021,6-027,6-031,6-033-6-035,6-043,6-
049,6-054,6-064,6-070,6-076,7-003,7-007-7-009,10-002.
Test Example 18: Insecticidal test against broad mite
[0271] A wet filter paper was laid in a styrol cup having an inner diameter of 7 cm,
a leaf of a common bean cut out so as to have the same diameter was laid theron,
and 10 adults of broad mite (Polyphagotarsonemus latus) per leaf was inoculated
thereon. A 10% emulsifiable concentrate (depending on the compounds, 10%
wettable powder was applied for the test) of the compound of the present invention
was diluted with water containing a spreading agent to prepare a chemical solution
with a concentration of 100 ppm. The chemical solution was sprayed with a rotating
spray tower in an amount of 2.5 ml per styrol cup, and the styrol cups were covered
with lids and contained at a thermostat chamber at 25°C. A number of dead
insect(s) after 2 days was counted and a rate of dead insects was calculated by the
calculation equation similar to that in Test Example 1. Incidentally, the test was
carried out with two districts.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No.3-093,5-009,5-036,5-037,5-040,5-
041,5-050,5-053,5-058,5-063,5-067,5-071,5-075-5-077,5-083,5-088,5-089,5-
113,5-121,5-140,5-147,5-148,5-151,5-174,5-179,5-185,5-188,5-214,5-215,5-219,5-
230,5-233-5-236,5-249,5-251,5-254,5-274,5-288,5-289,5-291,5-294,5-309,5-
332,5-339,5-355,5-360,5-374,5-375,5-387,5-398,6-017,6-026,6-031,6-033-6-
035,6-038,6-045,6-064,6-070,6-076,7-003,7-007-7-009.
Test Example 19: Insecticidal test against Ctenocephalides felis
[0272] After 400 jal of acetone solution in which 4 mg of the compound of the
present invention was dissolved in 40 ml of acetone (concentration 100 ppm) was
coated on the bottom face and side face of a laboratory dish having an inner
diameter of 5.3 cm, acetone was vaporized to prepare a thin film of the compound of
the present invention on the inner wall of the laboratory dish. As the surface area of
the inner wall is 40 cm2, the treated dosage is 1 jag/cm2. 10 adults of
Ctenocephalides felis (male and female are mixed) were left in the laboratory dish,
covered with lid and contained at a thermostat chamber at 25°C. A number of dead
insect(s) after 4 days was counted and a rate of dead insects was calculated by the
calculation equation similar to that in Test Example 1 . Incidentally, the test was
carried out with one district.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No.2-029*,2-052,5-002,5-003,5-005,5-
007,5-008,5-01 2,5-01 3,5-023,5-029,5-037,5-058,5-071*, 5-072,5-075*, 5-076*, 5-
077,5-086,5-088*,5-093*,5-100*,5-101*,5-111*,5-117,5-121,5-130*,5-138,5-
139,5-140*,5-142*,5-148*,5-160*,5-161*,5-165*,5-182*,5-184,5-187,5-188,5-
192,5-205,5-206,5-209,5-214*,5-218,5-219*,5-223,5-229,5-230,5-232,5-234*,5-
235*,5-236,5-238,5-240,5-241*,5-243*,5-245*, 5-247,5-264,5-274,5-287,5-291,5-
294,5-312,5-313,5-323,5-354*,5-356*,5-359*>5-360,5-362,5-378*,5-379*,5-383*
,5-384*,5-387*,5-389*,5-390,5-393,6-020,6-026,6-033,6-034*,6-035*,6-043*,6-
046~6-049,6-054,6-055,6-074,7-002*, 7-004,7-008,7-009.
In the interim, the indication of "*" shows that the insecticidal test was carried out
with a treated dosage of 0.1
Test Example 20: Insecticidal test against American dog tick
[0273] After 400 ^l of acetone solution in which 4 mg of the compound of the
present invention was dissolved in 40 ml of acetone (concentration 100 ppm) was
coated on the bottom face and side face of two laboratory dishes having an inner
diameter of 5.3 cm, acetone was vaporized to prepare a thin film of the compound of
the present invention on the inner wall of the laboratory dish. As the surface area of
the inner wall is 40 cm2, the treated dosage is 1 (ig/cm2. 10-American dog tick
(Dermacentor variabilis) (male and female are mixed) in the stage of protonymph
were left in the laboratory dishes, two laboratory dishes together were sealed with a
tape so that ticks do not escape, and contained at a thermostat chamber at 25°C. A
number of dead insect(s) after 4 days was counted and a rate of dead insects was
calculated by the calculation equation similar to that in Test Example 1 . Incidentally,
the test was carried out with one district.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
In the interim, the indication of \shows that the insecticidal test was carried out
with a treated dosage of 0.1
Test Example 21: Insecticidal test against German cockroach
[0274] A chemical solution having a concentration of 10 i^g/fil was prepared by
diluting the compound of the present invention with acetone. The chemical solution
was coated on the abdominal region of male adults of German cockroach (Blattella
germanica) in an amount of 1 jal per cockroach, and the treated cockroaches were
contained at a thermostat chamber at 25°C. A number of dead insect(s) after 2
days was counted and a rate of dead insects was calculated by the calculation
equation similar to that in Test Example 1 . Incidentally, the test was carried out with
five districts.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No. 5-075.
Test Example 22: Insecticidal test against Musca domestica
[0275] A chemical solution having a concentration of 1 ng/jil was prepared by
diluting the compound of the present invention with acetone. The chemical solution
was coated on the abdominal region of female adults of Musca domestica in an
amount of 1 jil per fly, and the treated flies were contained at a thermostat chamber
at 25°C. A number of dead insect(s) after 2 days was counted and a rate of dead
insects was calculated by the calculation equation similar to that in Test Example 1.
Incidentally, the test was carried out with ten districts.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No. 5-234.
Test Example 23: Insecticidal test against Eastern subterranean termite
[0276] A 10% emulsifiable concentrate (depending on the compounds, 10%
wettable powder was applied for the test) of the compound of the present invention
was diluted with water containing a spreading agent to prepare a chemical solution
with a concentration of 10 ppm. 0.5 ml of the chemical solution was added
dropwise in 10 g of sand and mixed. A filter paper and the sand treated with the
chemical solution were placed in a laboratory dish in which 1% agar was laid.
10-Eastern subterranean termite (Reticulitermes flavipes) per dish was left and
contained at a thermostat chamber at 25°C. A number of dead insect(s) after 2
days was counted and a rate of dead insects was calculated by the calculation
equation similar to that in Test Example 1.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No. 5-234.
Test Example 24: Insecticidal test against rust-red flour beetle
[0277] A chemical solution having a concentration of 0.1 mg/ml was prepared by
diluting the compound of the present invention with acetone. After 10 ml of the
chemical solution was added dropwise in 10 g of bran, 20 adults of rust-red flour
beetle (Tribolium castaneum) were left therein, and contained at a thermostat
chamber at 25°C. A number of dead insect(s) after 2 months was counted and a
rate of dead insects was calculated by the calculation equation similar to that in Test
Example 1. Incidentally, the test was carried out with two districts.
As a result, the following compounds showed an insecticidal rate of 80% or more
among the compounds tested.
The compounds of the present invention: No. 5-234.
Industrial Applicablity
[0278] The isoxazoline-substituted benzanilide compounds according to the
present invention are extremely useful compounds showing an excellent pesticidal
activity, particularly an insecticidal and acaricidal activity, and causing little adverse
effect against non-targeted beings such as mammals, fishes and useful insects.

We Claim:
1. An isoxazoline-substituted benzamide compound of formula (1) or a salt thereof:
(Formula Removed)
wherein A1 and A2 independently of one another are carbon atom or nitrogen
atom,
A3 is carbon atom,
G is benzene ring, nitrogen-containing 6-membered aromatic heterocyclic ring or
5-membered aromatic heterocyclic ring containing two or more hetero atoms
selected from sulfur atom and nitrogen atom,
W is oxygen atom or sulfur atom,
X is halogen atom, cyano, nitro, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4,
C3-C8cycloalkyl arbitrarily substituted with R4,
-OR5, -S(O)rR5, -CHO, -C(O)R9,
-C(O)OR9, -CH=NOR11, -C(R9)=NORi1, -Si(R13)(R14)R12 or phenyl, when m is 2 or 3,
each X may be identical with or different from each other,
further, when two Xs are adjacent, the adjacent two Xs may form 5-membered or
6-membered ring together with carbon atoms to which the two Xs are bonded by
forming -OCH2O-, or -CH=CHCH=CH-,,
Y is halogen atom, cyano, nitro, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4,
-OR5, -S(O)rR5, -NHR7, -N(R7)R6, phenyl or D-38, when n is 2, each Y may be
identical with or different from each other,
R1 and R2 independently of each other are hydrogen atom, C1-C12alkyl, C1-C12alkyl
arbitrarily substituted with R16, C3-C12cycloalkyl, C3-C12cycloalkyl arbitrarily
substituted with R16, C3-C12alkenyl, C3-C12alkenyl arbitrarily substituted with R16,
C3-C12alkynyl, -S(O)2R9, -OR19,
-NHR20, -N(R20)R19, -N=C(R19b)R19a, -C(O)R9, -C(O)OR9, -C(O)SR9,
-C(O)N(R10)R9, -C(S)N(R10)R9, -C(=NR11)OR9, -C(=NR11)SR9„ phenyl, phenyl

substituted with (Z)p1, D-8, D-13, D-15, D-17, D-21, D-25, D-35, D-39, D-42, D-47 to D-51, E-5, E-9 or E-17, or R1 and R2 together form =C(R2a)R1a, and further R1 and R2 together may form 5- to 7-membered ring together with the nitrogen atom bonding them by forming C4-C6 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with C1-C6alkyI, or formyl,
R1a and R2a together may form 5- or 6-membered ring together with the carbon atom bonding them by forming C4 or C5 alkylene chain or C4 or C5 alkenylene chain, in this case, the alkylene chain and the alkenyiene chain may contain one to three sulfur atoms or nitrogen atoms, and may be arbitrarily substituted with C1-C6alkyl, R3 is cyano, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4, C3-C8cycloalkyl, -C(O)OR9, -Si(R13)(R14)R12, phenyl, or D-47
D-1, D-3, D-6, D-8, D-10, D-11, D-13 to D-17, D-21 to D-31, D-34, D-35, D-38, D-39, D-42, D-47 to D-51, D-53 and D-54 are aromatic heterocyclic rings of the following formulae, respectively
(Formula Removed)
Z is halogen atom, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylsulfonyloxy, C1-C6alkylthio, C1-C6alkylsuifinyl, C1-C6alkylsulfonyl, di(C1-C6alkyl)amino, C1-C6alkoxycarbonyl, or -S(O)2NH2„ when p1, p2, p3 or p4 is an integer of 2 or more, each Z may be identical with or different from each other,
further, when two Zs are adjacent, the adjacent two Zs may form 5-membered or 6-membered ring together with carbon atoms to which the two Zs are bonded by forming -OCH2O- or -CH=CH-CH=CH-, in this case, hydrogen atoms bonded to each carbon atom forming the ring may be arbitrarily substituted with hafogen atom, E-4, E-5, E-9 to E-11, E-17, E-18, E-32, E-43 are saturated heterocyclic rings of the following formulae, repectively
(Formula Removed)
R4 is halogen atom, -OH, -OR5, -S(O)rR5 or -Si(R13}(R14)R12,
R5 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R24, phenyl or D-47,
R6 is C1-C6alkyl, C1-C6haloalkyl, -S(O)2R9, -CHO, -C(O)R9 or-C(O)OR9,
R7 is hydrogen atom, C1-C6alkyl, -CHO or C1-C6alky]carbonyl,
R9 is C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy C1-C4alkyl, C3-C8cycloalkyl,
C3-C6alkenyl, phenyl or D-47,
R10 is hydrogen atom,
R11 is hydrogen atom or C1-C6alkyl,, R11 together with R9 may form 5 -membered
ring with the atom bonding them by forming C2alkylene chain,
R12 is C1-C6a!kyl,
R13 and R14 independently of each other are d-Cealkyl,
R15 is hydrogen atom or C1-C6alkyl,
R16 is halogen atom, cyano, C3-C8cycloalkyl, C3-C8halocycloalkyl, -OR25,
-N(R26)R25, -S(O)rR27, -CHO, -C(O)R28, -C(O)OH,
-C(O)OR28, -C(O)NHR29, -C(O)N(R29)R28, -C(S)NHR29, -C(R31)=NOH,
-C(R31)=NOR30, -C(=NR31)OR30, -C(=NOR31)NHR29, -Si(R13)(R14)R12, phenyl,
phenyl substituted with (Z)p1, D-1, D-3, D-6, D-8, D-10, D-11, D-14to D-17, D-21 to
D-31, D-34, D-35, D-38, D-47 to D-51, D-53, E-4, E-5, E-10, E-11, E-18, E-32, E-43
or M-5,
M-5 is partially saturated heterocyclic ring of the following formula, respectively
(Formula Removed)
R19 is hydrogen atom, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R16, -CHO,
-C(O)R28, -C(O)OR28, -C(O)NHR29. -C(O)N(R29)R28, -C(S)NHR29, -C(S)N(R29)R28,
-S(O)2R28, phenyl, phenyl substituted with (Z)p1, D-21, D-47, D-50, D-51, D-53 or
D-54,
R19a is d-Csalkyl or D-47,
R19b is hydrogen atom or C1-C6alkyl,
R20 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C3-C6alkynyl,
-C(O)R9or-C(O)OR9,
R22 is C1-C6alkyl, when q2 or q3 is an integer of 2, each R22 may be identical with
or different from each other, further in case where two R22s are present on the same
carbon atom, the two R22s together may form oxo,
R23 is hydrogen atom or C1-C6alky1 substituted with R32, R24 is halogen atom, C1-C6haloalkoxy, phenyl or phenyl substituted with (Z)p1, R25 is hydrogen atom, C1-C8alkyl, C1-C8alkyl arbitrarily substituted with R32, -C(O)R33, -C(O)OR33, -C(O)NHR34, -S{O)2R33 or phenyl, R26 is hydrogen atom or C1-C6alkyl, or R26 together with R25 may form 6- to 6-membered ring with the nitrogen atom bonding them by forming C4-C5alkylene chain,
R27is C1-C6alkyl or C1-C8alkyl arbitrarily substituted with R32, R28 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R32, C3-C8cycloalkyl, C2-C8alkenyl, C2-Caalkenyl arbitrarily substituted with R32, C2-C8alkynyl, phenyl, phenyl substituted with (Z)p1, D-1 or D-47,
R29 is hydrogen atom, C1-C6alkyl, Ci-Cealkyl arbitrarily substituted with R32, C3-C6a(kenyl, C3-C6alkynyl, or phenyl, or R29 together with R28 may form 5- to 6-membered ring with the nitrogen atom bonding them by forming C4-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom,
R30 is C1-C8alkyl or C1-C8alkyl arbitrarily substituted with R32, R31 is hydrogen atom or C1-C6alkyl,, or R31 together with R30 may form 5-membered ring with the atom bonding them by forming C2alkylene chain, R32 is halogen atom, cyano, C3-C8cycloa!kyl, C3-C8halocycloalkyl, -OH, -OR33, -S(O)rR33,
-Si{R13)(R14)R12 phenyl, phenyl substituted with (Z)p1, D-1, D-3, D-22 or D-47, R33 is C1-C6alkyl or C1-C6haloalkyl, R34 is C1-C6alkyl or phenyl substituted with (Z)p1, m is an integer of 0 to 3, n is an integer of 0 to 2, p1 is an integer of 1 to 2, p2 is an integer of 0 to 2, p3 is an integer of 0 to 3, p4 is an integer of 0 to 2,
p5 is an integer of 0 or 1, q2 is an integer of 0 to 2, q 3 is an integer of 0 to 2, r is an integer of 0 to 2, and t is an integer of 0 or 1.
2. The isoxazoline-substituted benzamide compound or the salt thereof as claimed in claim 1, Wherein
G is an aromatic 6-membered ring shown in any one of G-l, G-3 and G-6 or an aromatic 5-membered ring shown in any one of G-l 8 and G-20
(Formula Removed)
X is halogen atom, cyano, nitro, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4,
C3-C8cycloa!kyl arbitrarily substituted with R4, -OR5, -S(O)rR5, -C(O)OR9,
-CH=NOR11,-C(R9)=NOR11,
-Si(R13)(R14)R12, phenyl, when m is an integer of 2 or 3, each X may be identical
with or different from each other,
further, when two Xs are adjacent, the adjacent two Xs may form 5-membered or 6-membered ring together with carbon atoms to which the two Xs are bonded by forming -OCH2O- or -CH=CHCH=CH-,
Y is halogen atom, cyano, nitro, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4, -OR5, -S(O)rR5, -NHR7, -N(R7)R6, phenyl or D-38, when n is an integer of 2, each Y may be identical with or different from each other, R1 is C1-C8alkyl, C1-C8alkyl arbitrarily substituted with R16, C3-C8cycloalkyl, C3-C8alkenyl, C3-C8haloalkenyl, C3-C8alkynyl, C1-C8alkoxy, -N(R20)R19, -N=C(R19b)R19a, -C(O)N(R10)R9, -C(S)N(R10)R9, phenyl, phenyl substituted with (Z)p1, D-8, D-13, D-15, D-17, D-21, D-35, D-39, D-42, D-47 to D-51, E-5 or E-9, R2is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C1-C4alkylsulfonyl C1-C4alkyl, cyano C1-C6alkyl, C1-C4alkoxycarbony C1-C4alkyl, C3-C6cycloalkyI, C3-C6alkenyl, C3-C6alkynyl, -S(O)2R9, -OH, -OR19, -NHR20, -N(R20)R19, -N=C(R19b)R19a, -C(O)R9, -C(O)OR9 or -C(O)SR9,
or R1 and R2 together form =C(R2a)R1a, and further R1 and R2 together may form 5-to 7-membered ring together with the nitrogen atom bonding them by forming C4 to C6 alkylene chain, in this case, the alkylene chain may contain one oxygen atom, sulfur atom or nitrogen atom, and may be arbitrarily substituted with C1-C6alkyl or formyl,
R1a and R2a together may form 5- or 6-membered ring together with the carbon
atom bonding them by forming C4 or C5 aikylene chain or C4 or C5 alkenylene chain,
in this case, the alkylene chain and the alkenylene chain may contain one to three
oxygen atoms, sulfur atoms or nitrogen atoms, and may be arbitrarily substituted
with CrCealkyl,
R3 is cyano, CrCealkyl, C1-C6alkyl arbitrarily substituted with R4, C3-C8cycloalkyl,
-C(O)OR9, -Si(R13)(R14)R12, phenyl or D-47
R4 is halogen atom, -OH, -OR5, -S(O)rR5, or -Si(R13)(R14)R12,
R5 is C1-C6alkyl, CrCehaloalkyl, C1-C3haloalkoxy C1-C3haloalkyl, phenyl, or D-47,
R5 is C1-C6alkyl, CrCehaloalkyl. -S(O)2R9, -CHO, -C(O)R9 or -C(O)OR9,
R7 is hydrogen atom or C1-C6alkyl,
R9 is C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy C1-C4alkyl, C3-C8cycloalkyl,
C3-C6alkenyl, or phenyl,
R10 is hydrogen atom,,
R11 is C1-C6alkyl, or R11 together with R9 may form 5-membered ring with the atom
bonding them by forming C2 alkylene chain, R12 is C1-C6alkyl,
R13 and R14 independently of each other are C1-C6alkyl, R15 is C1-C6alkyl,
R16 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, -OR25, -N(R26)R25, -S(O)rR27, -CHO, -C(O)R28, -C(O)OR28, -C(O)NHR29, -C(O)N(R29)R28, -C(S)NHR29, -C(R31)=NOH, -C(R31)=NOR30, -C(=NR31)OR30, -C(=NOR31)NHR29, -Si(R13)(R14)R12, phenyl, phenyl substituted with (Z)p1, D-1, D-3, D-6, D-8, D-10, D-11, D-14to D-17, D-21 to D-31, D-34, D-35, D-38, D-47 to D-51, D-53, E-4, E-5, E-10, E-11, E-18, E-32, E-43 or M-5,
R19 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R16, -CHO, -C(O)R28, -C(O)OR28, -C(O)NHR29, -C(O)N(R29)R28, -C(S)NHR29, -C(S)N(R29)R28, -S(O)2R28, phenyl, phenyl substituted with (Z)p1, D-21, D-47, D-50, D-51, D-53 or D-54 R19a is C1-C6alkyl, phenyl or D-47 R19b is hydrogen atom or C1-C6alkyl,
R20 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C3-C6alkynyl, -C(O)R9or-C(O)OR9,
R22 is C1-C6alkyl, when q2 or q3 is an integer of 2, each R22 may be identical with or different from each other, further in case where two R22s are present on the same carbon atom, the two R22s together may form oxo, R23 is hydrogen atom or C1-C6alkyl arbitrarily substituted with R32, R25 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, -C(O)R33, -C(O)OR33, -C(O)NHR34, -S(O)2R33 or phenyl,
R26 is hydrogen atom or C1-C6alkyl,, or R25 together with R25 may form 5- to 6-membered ring with the nitrogen atom bonding them by forming C4-C5alkylene chain,
R27 is C1-C6alk!yl, or phenyl C1-C4alkyl,
R28 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R32, C3-C6cyc!oalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, phenyl, phenyl substituted with (Z)p1, D-1 or D-47,
R29 is hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, C3-C6alkenyl or C3-C6alkynyl, or R29 together with R28 may form 5- to 6-membered ring with the nitrogen atom bonding them by forming C4-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom, R30 is C1-C6alkyl, C3-C6cycloalkyl C1-C4alkyl, tri(C1-C6alkyl)si!yl C1-C4alkyl or phenyl
C1-C4alkyl substituted with (Z)p1,,
R31 is hydrogen atom or C1-C6alkyl, or R31 together with R30 may form 5-membered
ring with the atom bonding them by forming C2alkylene chain,
R32 is halogen atom, cyano, C3-C8cycloalkyl, C3-C8halocycloalky!, -OR33, -S(O)rR33,
phenyl, phenyl substituted with (Z)p1, D-1, D-3, D-22 or D-47,
R33 is C1-C6alkylor C1-C6haloalkyl,
R34 is C1-C6alkyl.
3. The isoxazoline-substituted benzamide compound or the salt thereof as claimed in claim 2, wherein G is G-1,G-3,G-18 or G-20,
X is halogen atom, cyano, nrtro, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4, C3-C8halocycloalkyl, -OR5, -S(O)rR5, -C(O)OR9 or -Si(R13)(R14)R12, when m is 2 or 3, each X may be identical with or different from each other, Y is halogen atom, cyano, nitro, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4, -OR6, -S(O)rR5, -NHR7 or -N(R7)R6, when n is 2, each Y may be identical with or different from each other,
R1 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R16, C3-C8cycloalkyl, C3-C8alkenyl, C3-C8haloalkenyl, C3-C8alkynyl,
-N(R20)R19, -C(O)N(R10)R9, -C{S)N(R10)R9, phenyl substituted with (Z)p1, D-8, D-13, D-15 to D-17, D-21, D-35, D-39, D-42, D-47 to D-51, E-5 or E-9, R2 is hydrogen atom, C1-C6alkyl, C1-C6haloalkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkylthio C1-C4alkyl, cyano C1-C6alkyl, C3-C6cyc!oalkyl, C3-C6alkenyl, C3-C6alkynyl, -OH, C1-C6alkoxy, C1-C6alkylcarbonyloxy, C1-C6alkoxycarbonyloxy, C1-C6alkylsulfonyloxy, C1-C6alkylsulfonyl, -NHR20, -N=C(R19b)R19a, -C(O)R9, -C(O)OR9or-C(O)SR9,

or R2 together with R1 may form 5- to 7-membered ring with the nitrogen atom
bonding them by forming C4-C6alkylene chain, in this case, the alkylene chain may
contain one oxygen atom or sulfur atom,
R3 is C1-C6alkyl, C1-C6haloalkyl, C1-C4haloalkoxy C1-C4alkyl, C1-C4alkylthio
C1-C4haloalkyl or C3-C8cycloalkyl,
R4 is halogen atom, -OH, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio or
tri(C1-C6alkyl)silyl,
R5 is C1-C6alkyl, C1-C6haloalkyl or C1-C3haloalkoxy C1-C3haloalkyl,
R6 is C1-C6a!kyl, C1-C6haloalkyl, -S(O)2R9, -CHO, -C(O)R9 or -C(O)OR9,
R7 is hydrogen atom or C1-C6alkyI,
R9 is C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy C1-C4alkyl, C3-C8cycloalkyl or
C3-C6alkenyl,
R10 is hydrogen atom,
R11 is C1-C6alkyl, or R11 together with R9 may form 5-membered ring with the atom
bonding them by forming C2alkyiene chain,
R15 is C1-C6a!kyl,
R16 is halogen atom, cyano, C3-C6cycloalkyl, -OR25, -N(R26)R29, -S(O)rR27, -C(O)R26,
-C(O)OR28, -C(O)NHR29. -C(O)N(R29)R28, -C(S)NHR29, -C{R31)NOH,
-C(R31)=NOR30, -C(=NR31)OR30, phenyl, phenyl substituted with (Z)p1, D-1, D-3,
D-8, D-10, D-11, D-14 to D-17, D-21 to D-31, D-34, D-35, D-38, D-47 to D-51, D-53,
E-4, E-5, E-10, E-11, E-18, E-32, E-43 or M-5,
R19 is C1-C6alkyl, C1-C6haloalkyl, -C(O)R28, -C(O)OR28, -C(O)NHR29,
-C(O)N(R29)R28, -C(S)NHR29, -C{S)N(R29)R28, C1-C6aIkylsulfonyl, phenyl, phenyl
substituted with (Z)p1, D-21, D-47, D-50, D-51, D-53 or D-54,
R19a is C1-C6alkyl,
R18b is hydrogen atom or C1-C6alkyl,
R20 is hydrogen atom, C1-C6alkyI, C3-C6alkenyl, C3-C6alkynyl, C1-C6alkylcarbony! or
CrCsalkoxycarbonyl,
R22 is C1-C4a!kyl, or two R22 s present on the same carbon atom may together form
oxo,
R23 is hydrogen atom
R25 is hydrogen atom, C1-C6alkyl. C1-C6haloalkyl, -C(O)R33, -C(O)OR33,
-C(O)NHR34, -S(O)2R33 or phenyl,
R26 is hydrogen atom or C1-C6alkyl, or R26 together with R26 may form 5- to
6-membered ring with the nitrogen atom bonding them by forming C4-C5a!kylene
chain,
R27 is C1-C6alkyl,

R28 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R32, C3-C6cycloalkyl, C3-C6halocycloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, phenyl or phenyl
substituted with (Z)p1,
R29 is hydrogen atom, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl, or R29 together with R28 may form 5- to 6-membered ring with the nitrogen atom bonding them by forming C4-C5alkylene chain, in this case, the alkylene chain may contain one oxygen atom or sulfur atom,
R30 is C1-C6alkyl, C3-C6cycloalkyl C1-C4alkyl or phenyl C1-C4alkyl substituted with
(Z)P1,
R31 is hydrogen atom or C1-C6alkyl, or R31 together with R30 may form 5-membered
ring with the atom bonding them by forming C2alkylene chain,
R32 is halogen atom, cyano, C3-C6cycloalkyl, C3-C6halocycloalkyl, C1-C4alkoxy,
C1-C4alkylthio or phenyl,
R33 is C1-C6alkyl or C1-C6haloalkyl,
R34 is C1-C6alkyl,
m is an integer of 1 to 3,
n is an integer of 0 to 2,
q2 is an integer of 0 to 2, and
q3 is an integer of 0 to 2
4. The isoxazoline-substituted benzamide compound or the salt thereof as claimed in claim 3, wherein
A1 is carbon atom or nitrogen atom,
A2 and A3 are carbon atom,
G is G-1,
X is halogen atom, cyano, nitro, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4,
C3-C8halocycloalkyl, -OR5, -S(O)rR5 or tri(C1-C6alkyl)silyl, when m is 2 or 3, each X
may be identical with or different from each other,
Y is halogen atom, cyano, nitro, C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R4,
-OR5, -S(O)rR5, -NHR7 or -N(R7)R6, when n is 2, each Y may be identical with or
different from each other,
R1 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R16, C3-C8cycloalkyl,
C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl,
-N(R20)R19, -C(O)N(R10)R9, -C(S)N(R10)R9, phenyl substituted with (Z)p1, D-8, D-13,
D-15, D-17, D-21 „ D-35, D-39, D-42, D-47, D-48, D-50, D-51, E-5 or E-9,

R2 is hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, C1-C4alkytthio C1-C4alkyl, cyano C1-C6alkyl, C3-C6cycloalkyl, C3-C6alkenyl, C3-C6alkynyl, -OH, C1-C6alkylcarbonyloxy, C1-C6alkylsulfonyloxy, -NH2, -C(O)R9, -C(O)OR9 or -C(O)SR9,
R3 is C1-C6haloalkyl or C1-C4alkylthio C1-C4haloalkyl, R4 is halogen atom, -OH, C1-C6aikoxy, C1-C6haloalkoxy, C1-C6alkylthio, or
tri(C1-C6aIkyl)silyl,
R5 is C1-C6alkyl, C1-C6haloalkyl or C1-C3haloaIkoxy C1-C3haloalkyl,
R6 is C1-C6alkyl, C1-C6haloalkyl, -CHO, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl,
C1-C6alkoxycarbonyl, or C1-C6haloalkylsulfony),
R7 is hydrogen atom or C1-C6alkyl,
R9 is C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy C1-C4alkyl, C3-C8cycloalkyl or
C3-C6alkenyl,
R16 is halogen atom, cyano, C3-C6cycloalkyl, -OR25. -N(R26)R25, -S(O)rR27, -C(O)R28,
-C(O)OR28 -C(O)NHR29, -C(O)N(R29)R28, -C(S)NHR29, -C(R31)=NOH,
-C(R31)NOR30, -C(=NR31)OR30, phenyl, phenyl substituted with (Z)p1, D-1, D-3,
D-8, D-10, D-11, D-14 to D-17, D-21 to D-31, D-34, D-35, D-38, D-47 to D-51, D-53,
E-4, E-5, E-10, E-11, E-18, E-32, E-43 or M-5,
R19 is C1-C6haloalkyl, -C(O)R28, -C(O)OR28, -C(O)NHR29,
-C(O)N(R29)R28, -C(S)NHR29, -C(S)N(R29)R28, phenyl, phenyl substituted with (Z)p1,
D-21, D-47, D-50, D-51, D-53 or D-54,
R20 is hydrogen atom, C1-C6alkyl, C3-C6alkenyl, C3-C6alkynyl, C1-C6alkylcarbonyl or
C1 -C6alkoxycarbonyl,
R25 is C1-C6alkyl, C1-C6haloalkyl, C1-C6alkylcarbonyl, C1-C6alkoxycarbonyl,
C1-C6alkylaminocarbonyl or C1-C6alkylsulfonyl,
R26 is hydrogen atom or C1-C6alkyl,
R27 is C1-C6alkyl,,
R28 is C1-C6alkyl, C1-C6haloalkyl,, C1-C4-alkoxy C1-C4alkyl, C1-C4alkylthio
C1-C4alky, cyano C1-C6alkyl, phenyl C1-C4aIkyl, C3-C6cycloalkyl, C3-C6alkenyl,
C3-C6haloalkenyl, C3-C6alkynyl, phenyl or phenyl substituted with (Z)p1,
R29 is hydrogen atom, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl,
R30 is C1-C6alkyl or C3-C6cycloalkyl C1-C4alkyl,
R31 is hydrogen atom or C1-C6alkyl, or R31 together with R30 may form 5-membered
ring with the atom bonding them by forming C2alkylene chain.
5. The isoxazoline-substituted benzamide compound or the salt thereof as claimed in claim 4, wherein

X is halogen atom, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, C3-C8halocycloalkyl, OR5 or -S(O)rR5, when m is 2 or 3, each X may be identical with or different from each other, Y is halogen atom, cyano, nitro, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy,
C1-C4haloalkoxy, C1-C6alkylthio, C1-C6alkylsulfonyl, -NHR7 or -N(R7)R6,
R1 is C1-C6alkyl, C1-C6alkyl arbitrarily substituted with R16, C3-C6cycloalkyl,
C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, -N(R20)R19, D-8, D-13, D-15, D-21,
D-35, D-50 or D-51,
R2 is hydrogen atom, C1-C6alkyl, C1-C4alkoxy C1-C4alkyl, cyano C1-C6alkyl,
C3-C6alkynyl, -C(O)R9 or-C(O)OR9,
R3 is C1-C6haloalkyl,
R5 is C1-C6alkyl, C1-C6haloalkyl or C1-C3haloalkoxy C1-C3haloalkyl,
R6 is C1-C6alkyl, -CHO, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl,
C1-C6alkoxycarbonyl or C1-C6haloalkylsulfonyl,
R9 is C1-C6alkyl, C1-C6alkoxy C1-C4alkyl, C3-C8cycloalkyl or C3-C6alkenyl,
R16 is halogen atom, cyano, C3-C6cycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy,
C1-C6aikylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl,
C1-C6alkylcarbonyl,
-C(O)OR28, -C(O)NHR29, -C(O)N(R29)R28, -C(S)NH2. -C(R31)=NOH, -C(R31)=NOR30,
phenyl, phenyl substituted with (Z)p1, D-1, D-3, D-8, D-10, D-11, D-14 to D-17, D-21
to D-31, D-34, D-35, D-38, D-47 to D-51, D-53, E-4, E-5, E-10, E-11 or E-32
R19 is C1-C6haloalkyl, -C(O)R28, -C(O)OR28, phenyl, phenyl substituted with (Z)p1,
D-21, D-47, D-50, D-51, D-53 or D-54,
R20 is hydrogen atom or C1-C6alkyl,
R28 is C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C3-C6alkenyl or C3-C6alkynyl,
R29 is hydrogen atom or C1-C6alkyl,
R30 is C1-C6alkyl,
R31 is hydrogen atom or C1-C6alkyl, and
n is an integer of 0 or 1.
6. Isoxazoline-substituted benzamide compound and the salt thereof as claimed in any of claims 1 to 5 as and when used for the preparation of a pesticide, an agrochemical, an ento-and ecto- parasiticide, an insecticide or acaricide.