Specification
FORM 2
THE PATENTS ACT 1970
[39 OF 1970]
COMPLETE SPECIFICATION
[See Section 10]
"PESTICIDAL INDAZOLE OR BENZOTRIAZOLE DERIVATIVES'
SYNGENTA LIMITED, a British company, of Fernhurst, Haslemere, Surrey GU27 3JE, United Kingdom,
The following specification particularly describes the nature of the invention and the manner in which it is to be performed :-
The present invention relates to azine and azole derivatives, to processes for preparing them, to fungicidal, insecticidal, acaricidal, molluscicidal and nematicidal compositions comprising them, to methods of using them to combat fungal diseases (especially fungal diseases of plants) and to methods of using them to combat and control insect, acarine, mollusc and nematode pests.
Azole and azine derivatives are disclosed in W095/31448, W097/18198, WO98/02424 and WO98/05670.
The present invention provides a compound of formula (I):
wherein G is either
(0 (ii)
where M1 or M2 is bonded to A; n is 0 or 1; A is optionally substituted Cw alkylene, optionally substituted C2^ alkenylene, optionally substituted C^ alkyriylene, optionally substituted C,^ alkylenoxy, optionally substituted oxy(CM)alkylene, optionally substituted C,^ alkylenethio, optionally substituted thio(C,^)alkylene, optionally substituted C,^ allcylenarnino, optionally substituted ammo(C,_6)alkylene, optionally substituted [C^ alkyleneoxy(Cj^)alkylene], optionally substituted [Cw alkylenethio(C1^)alkylene], optionally substituted [C,^ atfsyIenesuffinyI(Cw)aifcyIene], optionally substituted fCw
*
alkylenesulfonyl(C1^5)alkylene] or optionally substituted [C,^ alkyleneamino(C,^)alkylene]; when G is (i), D is S, NR7, CR8=CR9, CR8=N, CR8=N(0), N=CR' or N(0)=CR9; when G is (ii), D is S or NR7; E is N, N-oxide or CR10; M1 is OC(=Y), N(RH)C(=Y), N=C(OR12), N=C(SR13) or N=C(NRUR") where O or N is the atom of attachment to the ring containing D and E; M2 is N-C(=Y) where N is the atom of attachment to the ring containing D and E; Y is O, S or NR16; J is N or CR17; R1 is hydrogen, halogen, optionally substituted C,^ alkyl, optionally substituted C^ alkenyl, optionally substituted C2^ alkynyl, optionally substituted C,^ alkoxy, optionally substituted C,^ alkylthio, optionally substituted C3.7 cycloalkyl, cyano, nitro or SF5; R2is optionally substituted C,.I0 alkyl, optionally substituted [C2^ alkenyl(Cw)alkyl], optionally substituted [C2J6 alkynyl(C,^)alkyl], optionally substituted C3.7 cycloalkyl, optionally substituted Cj.]0 alkylcarbonyl, optionally substituted C,.10 alkoxycarbonyl, formyl, optionally substituted C,.10 alkylaminocarbonyl, optionally substituted di(C,.,0)alkylaminocarbonyl, optionally substituted phenoxycarbonyl, optionally substituted C,^ alkylthio, optionally substituted C,^ alkylsulfinyl, optionally substituted C,^
If alkylsulfonyl, optionally substituted arylthio, optionally substituted arylsulfinyl, optionally substituted arylsulfonyl or R,8RI9NS; R3, R4 and R5 are, independently, hydrogen, halogen, optionally substituted C,^ alkyl, optionally substituted Cu alkoxy, optionally substituted C,^ alkylthio, optionally substituted C1H5 alkylsulfinyl, optionally substituted C,^ alkylsulfonyl, cyano, nitro, optionally substituted C,^ alkylcarbonyl, optionally substituted Cw
2(() alkoxycarbonyl or SF5; R6 is hydrogen, cyano, optionally substituted C,.20 alkyl, optionally substituted substituted C^ alkenyl(Cw)alkyl, optionally substituted C2.20 alkynyl(C,^)aIkyl, optionally substituted C^ cycloalkyl, optionally substituted Cs^ cycloalkenyl, formyl, optionally substituted C,.20 alkoxycarbonyl, optionally substituted C,.20 alkylcarbonyl, aminocarbonyl, optionally substituted C,.20 alkylaminocarbonyl, optionally substituted di-
2f (C^alkylarninocarbonyl, optionally substituted aryloxycarbonyl, optionally substituted arylcarbonyl, optionally substituted arylaminocarbonyl, optionally substituted N-alkyl-N-arylaminocarbonyl, optionally substituted diarylaminocarbonyl, optionally substituted heteroaryloxycarbonyl, optionally substituted heteroarylcarbonyl, optionally substituted heteroarylaminocarbonyl, optionally substituted alkylheteroarylaminocarbonyl, optionally
3 (J substituted dmeteroarylaminocarbonyl, optionally substituted phenyl, optionally substituted heteroaryl, optionally substituted heterocyclyl, optionally substituted C,.20 alkylsulfonyl or
optionally substituted arylsulfonyl; R7 is C,^ alkyl; R8 and R9 are, independently, hydrogen, halogen, cyano, nitro, optionally substituted CM alkyl, optionally substituted C^ alkenyl, optionally substituted C^ alkynyl or optionally substituted C,^ alkoxy; R10 is hydrogen, halogen, optionally substituted Cw alkyl, optionally substituted C2_6 alkenyl, optionally substituted C^ alkynyl, optionally substituted Cw alkoxy, optionally substituted C,^ alkylthio, optionally substituted C,^ alkylsulfinyl, optionally substituted Cw alkylsulfonyl, cyano, nitro, fonnyl, R20ON=<:(R21), optionally substituted CM alkylcarbonyl, optionally substituted C,^ alkoxycarbonyl or SF5; or R1 and R10 together with the atoms to which they are attached may be joined to form a five, six or seven-membered saturated or unsaturated If) ring carbocylic or heterocyclic ring which may contain one or two hetero atoms selected from O, N or S and which may be optionally substituted by CM alkyl, Cw haloalkyl or halogen; Rn is hydrogen, optionally substituted C,.10 alkyl, optionally substituted [C^ alkenyl(C, Jalkyl], optionally substituted [Cw alkynyl(CI^)alkyl], optionally substituted C3.7 cycloalkyl, optionally substituted C,.,0 alkylcarbonyl, optionally substituted C,.]0 1 (5 alkoxycarbonyl, fonnyl, optionally substituted C,.10 alkylaminocarbonyl, optionally
substituted di(CMO)alkylaminocarbOnyl, optionally substituted phenoxycarbonyl, optionally substituted Gw alkylthio, optionally substituted C,^ alkylsulfinyl, optionally substituted C^ alkylsulfonyl, optionally substituted arylthio, optionally substituted arylsulfinyl, optionally substituted arylsulfonyl or R^R^NS; R12 is optionally substituted C,.,0 alkyl, optionally 2p substituted [C^ alkenyl(Cw)alkyl], optionally substituted [C^ alkynyl(Cw)alkyI],
optionally substituted G^ cycloalkyl, optionally substituted C,.,0 alkylcarbonyl, optionally substituted C,.I0 alkoxycarbonyl, fonnyl, optionally substituted CM0 alkylaminocarbonyl, optionally substituted di(C,.,0)alkylammocarbonyl,, amino, optionally substituted C,^ alkylamino, optionally substituted di(C,^)alkylamino, optionally substituted 2)5 phenoxycarbonyl, tri(C,^)alkylsilyl, aryldi(CM)alkylsilyl, (CM)alkyldiarylsilyl or triarylsilyl; Ru is optionally substituted Cj-io alkyl, optionally substituted [C2^ alkenyl(C,^)alkyl], optionally substituted [C^ alkynyl(C1MS)alkyl], optionally substituted C3.7 cycloalkyl, optionally substituted C,.,0 alkylcarbonyl, optionally substituted C,.10 alkoxycarbonyl, optionally substituted CM0 alkylaminocarbonyl, optionally substituted di(CM0)alkyl-3|0 aminocarbonyl or optionally substituted phenoxycarbonyl); R14 and R15 are, independently optionally substituted C,.,0 alkyl, optionally substituted C,^ alkoxy, optionally substituted
[C2_6 alkenyl(Cw)alkyl], optionally substituted [C2_6 alkynyl(C,Jalkyl], optionally substituted C3.7 cycloalkyl, optionally substituted CM0 alkylcarbonyl, optionally substituted C,.)0 alkoxycarbonyl, formyl, optionally substituted Cwoalkylaniinocarbonyl, optionally substituted di(C,.i0)alkylaminocarbonyl, hydroxy, amino, optionally substituted C,^ alkylamino, optionally substituted di(CM)alkylamino, or optionally substituted phenoxycarbonyl; R16 is hydrogen, cyano, nitro, optionally substituted C,^ alkyl, optionally substituted C^ cycloalkyl, optionally substituted (C2^)alkenyl(Cw)alkyl, optionally substituted (CM)alkynyl(C, Jalkyl, optionally substituted phenyl, optionally substituted heteroaryl, optionally substituted Cw alkylcarbonyl, optionally substituted C,^ 1 p alkoxycarbonyl, optionally substituted C,^ alkylamino, optionally substituted di(C^alkyl¬amino, optionally substituted Cw alkylcarbonylamino, optionally substituted C,^ alkoxycarbonylamino, optionally substituted C,^ alkoxy, optionally substituted Cu alkyltbio, optionally substituted C,^ alkylsulfinyl, optionally substituted CM alkylsulfonyl, optionally substituted arylthio, optionally substituted arylsulfinyl, optionally substituted l|5 aiylsulfonyl or Ci#acyIoxy; R17 is hydrogen, halogen, nitro, cyano, optionally substituted C,^ alkyl, optionally substituted CM alkenyl, optionally substituted C2^ alkynyl, optionally substituted Cj., cycloalkyl, optionally substituted Cw alkoxycarbonyl, optionally substituted CM alkylcarbonyl, optionally substituted C^alkylaminocarbonyl, optionally substituted di(C,^)alkylaminocarbonyl, optionally substituted phenyl or optionally substituted 2)0 heteroaryl; R18 and R19 are, independently, optionally substituted CM alkyl or R18 and R19 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further hetero atoms selected from O, N or S and which may be optionally substituted by one or two Cw alkyl groups; R20 is hydrogen, optionally substituted phenyl, optionally substituted phenyl(CM)alkyl or optionally 2J5 substituted CU20 alkyl; R21 is hydrogen, optionally substituted phenyl or optionally
substituted Cw alkyl; and R22 and R23 are, independently, optionally substituted Cw alkyl or R22 and R23 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further hetero atoms selected from O, N or S and which may be optionally substituted by one or two Cw alkyl groups.
The compounds of formula (I) may exist in different geometric or optical isomers or tautomeric forms. This invention covers all such isomers and tautomers and mixtures thereof in all proportions.
When present, optional substituents on alkylene, alkenylene or alkynylene moieties include, subject to valency constraints, one or more of halogen, C^ alkyl, C^ haloalkyl, C,^ cyanoalkyl, C,^ alkoxy(C, J alkyl, Cw alkoxy, cyano, =0, =NR24 and =CR25R26, wherein R24 is CM alkyl, C1-6 haloalkyl, OR27 or R28R29N; where R25 and R26 are, independently, hydrogen, Cw alkyl, Cw alkoxy, Cw haloalkyl, cyano, C,^ alkoxycarbonyl, C,^ alkylcarbonyl or R30R31N; R27 is C,^ alkyl, CM haloalkyl or phenyl(C,.2)alkyl; R28 and R29 are, independently, hydrogen, CM alkyl, C3.7 cycloalkyl, CM alkenyl(CM)alkyl, C2^ alkynyl(CM)alkyl, C^ haloalkyl, Cw alkoxy(Cw)alkyl, Cw alkoxycarbonyl(C, Jalkyl, carboxy(Cw)alkyl or phenyl(C,.2)alkyl or R28 and R29 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further hetero atoms selected from 0, N or S and which may be optionally substituted by one or two-G$ alkyl groups; R30 and R31 are; independently, hydrogen^ GM alkyl; C^ cycloalkyl, CM a1kenyl(Cw)aJkyl, C2^ alkynyl(C,^)alkyl» Cj^ haloalkyl, C^alkoxy-(C,^)alkyl, CM alkoxycarbonyl(C1^)alkyl, carboxy(Cw)alkyl or phenyKC^alkyl; or R30 and R31 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further hetero atoms selected from O, N or S and which may be optionally substituted by one or two Cw alkyl groups.
Each alkyl moiety is a straight or branched chain and is, for example, methyl, ethyl, H-propyl, w-butyl, w-pentyl, w-hexyl, wo-propyl, w-butyl, sec-butyl, wo-butyl, tert-bxxtyl or weo-pentyl. When present, the optional substituents on alkyl include one or more of halogen, nitro, cyano, H02C, C,.,0 alkoxy (itself optionally substituted by C,.10 alkoxy), aryl-(CM)alkoxy, C,.]0 alkylthio, C,.10 alkylcarbonyl, ClA0 alkoxycarbonyl, Cw alkylamino-carbonyl, di(CM alkyl)aminocarbonyl, (Cw)alkylcarbonyloxy, optionally substituted phenyl, heteroaryl, aryloxy, arylcarbonyloxy, heteroaryloxy, heterocyclyl, heterocyclyloxy, C3.7 cycloalkyl (itself optionally substituted with (Cw)alkyl or halogen), €3.7 cycloalkyloxy, C5.7 cycloalkenyl, C,^ alkylsulfonyl, C,^ alkylsulfinyl, tri(CM)alkylsilyl, tri(C,^)alkylsilyl-(C, Jalkoxy, aryldi(CM)alkylsilyl, (CM)alkyldiarylsilyl, triaiylsilyl, =N-OR' and =N-NR'R"; where R' and R" are, independently, CM alkyl or C^ haloalkyl.
Alkenyl and alkynyl moieties can be in the form of straight or branched chains, and the alkenyl moieties, where appropriate, can be of either the (E)- or ©-configuration. Examples are vinyl, allyl and propargyl. When present, the optional substituents on alkenyl or alkynyl include one or more of halogen, aryl and C,., cycloalkyl.
In the context of this specification acyl is optionally substituted C,^ alkylcarbonyl (for example acetyl), optionally substituted C^ alkenylcarbonyl, optionally substituted C2^ alkynylcarbonyl, optionally substituted arylcarbonyl (for example benzoyl) or optionally substituted heteroarylcarbonyl.
Halogen is fluorine, chlorine, bromine or iodine.
Haloalkyl groups are alkyl groups which are optionally substituted with one or more
of the same or different halogen atoms and are, for example, CF3, CF2C1, CF3CH2 or CHr2CH2.
Aryl includes naphthyl, anthracyl, fluorenyl and indenyl but is preferably phenyl.
The term heteroaryl refers to an aromatic ring containing up to 10 atoms including 1|5 one or more heteroatoms (preferably one or two heteroatoms) selected from O, S and N.
Examples of such rings include pyridine, pyrimidine, furan, quinoline, quinazoline, pyrazole, thiophene, thiazole, oxazole and isoxazole.
The terms heterocycle and heterocyclyl refers to a non-aromatic ring containing up to 10 atoms including one or more (preferably one or two) heteroatoms selected from O, S 2p and N. Examples of such rings include 1,3-dioxolane, tetrahydrofuran and morpholine. It is preferred that heterocyclyl is optionally substituted by CM alkyl.
Cycloalkyl includes cyclopropyl, cyclopentyl and cyclohexyl. The optional substituents for cycloalkyl include halogen, cyano and Cj_3 alkyl.
Cycloalkenyl includes cyclopentenyl and cyclohexenyl. The optional substituents for 2|5 cycloalkenyl include C,.3 alkyl, halogen and cyano.
Carbocyclic rings include aryl, cycloalkyl and cycloalkenyl groups.
For substituted phenyl moieties, heterocyclyl and heteroaryl groups it is preferred that one or more substituents are independently selected from halogen, C^ alkyl, Cu haloalkyl, Cw alkoxy(CM)alkyl, C,^ alkoxy, C,^ haloalkoxy, CM alkylthio, Cw haloalkylthio, C,^ 3f) alkylsulfinyl, Cw haloalkylsulfinyl, C^ alkylsulfonyl, CM haloalkylsulfonyl, C^ alkenyl, C2^ haloalkenyl, C^ alkynyl, C3.7 cycloalkyl, nitro, cyano, C02H, C,^ alkylcarbonyl, C,^
,
alkoxycarbonyl, R32R33N or R34R35NC(0) wherein R32, R33, R34 and R35 are, independently, hydrogen or Cw alkyl.
It is to be understood that dialkylamino substituents include those where the dialkyl
groups together with the N atom to which they are attached form a five, six or seven-
membered heterocyclic ring which may contain one or two further hetero atoms selected
from O, N or S and which may be optionally substituted by one or two C,^ alkyl groups.
When heterocyclic rings are formed by joining two groups on an N atom, the resulting rings
are suitably pyrrolidine, piperidine, thiomorpholine and morpholine each of which may be
substituted by one or two (Ci^)alkyl groups.
11> In a further aspect, the present invention provides a compound of formula (IA):
(IA)
wherein A, G, J, R3, R4, R5 and R6 are as defined above for a compound of formula (I). More preferred compounds of formula (IA) are those wherein n is 0; A is C,^
l|> alkylene, Cw alkenylene, C,^ alkylenoxy, oxy(C,^)alkylene, Cw alkylenamino or C,^ alkylenethio, each of which is optionally substituted by Cui alkyl, C^haloalkyl, C,_3 cyanoalkyl, halogen, C,_3 alkoxy, Cw alkoxycarbonyl, cyano, =0, =NR36 or =CR37R38; when G is (i), D is S, NR7, CR8=CR9, CR8=N, CR8=N(0), N=CR9 or N(0)=CR9; when G is (ii), D is S or NR7; E is N or CR10; M1 is N(Rn)C(=Y) or N=C(SR13) where O or N is the atom of
2p attachment to the ring containing D and E; M2 is N-C(=Y) where N is the atom of attachment to the ring containing D and E; Y is O, S or NR16; J is N or CR17R' is hydrogen, halogen, C,^ alkyl, G^ alkenyl, C^ alkynyl, C,^ cyanoalkyl, Cw haloalkyl, C,^ alkoxy, C,^ haloalkoxy, Cw alkylthio, C,^ haloalkylthio, C^ cycloalkyl, C3.7 cycloalkyl(CM)alkyl, Cw alkoxy-(Cw)alkyl, cyano, nitro or SF5; R2 is C,.,0 alkyl, benzyloxymethyl, benzoyloxymethyl, C,. ^alkoxyCC! Jalkyl, Cw alkenyl(C^)alkyl, C^ alkynyl(C^)alkyl, C,.,0 alkylcarbonyl or Cwo alkoxycarbonyl; R3, R4 and R5 are, independently, selected from hydrogen, halogen, Cw
alkyl, Cw alkoxy, CM haioalkoxy, C,^ alkylthio, C^ haloalkylthio, C^ alkylsulfinyl, C,^ haloalkylsulfinyl, CM alkylsulfonyl, C,^ haloalkylsulfonyl, Cw haloalkyl, cyano, nitro, Cw alkylcarbonyl, C,^ alkoxycarbonyl or SF3; R6 is CM0 alkyl or Cj.jo haloalkyl (each one of which may be substituted with a Cw alkyloxime, CM haloalkyloxime, C,^ alkylhydrazone or C,^ haloalkylhydrazone group) or cyano, Cw cyanoalkyl, C^ alkenyl(Cw)alkyl, C2^ alkynylfQ.Jalkyl, C^ cycloalkyl, C3.7 halocycloalkyl, C3_7 cyanocycloalkyl, C,.3 aikyl(C3.7)cycloalkyl, C,.3alkyl(C3.7)halocycloalkyl, C5^ cycloalkenyl, C^ cycloalkyl(Cw)alkyl, C5^ cycloalkenyl(Cw)alkyl, C^ haloalkenyl (C^)alkyl, C,^ cyanoalkenyl(CM)alkyl, C,^ alkoxy(C,^)alkyl, C3^ alkenyloxy(C,Jalkyl, C^ alkynyloxy(Cw)alkyl, aryloxy(C,^)alkyl, formyl, C,^ carboxyalkyl, C,^ alkylcarbonyl-(C,^)alkyl, C2^s alkenylcarbonyl(C,Jalkyl, C2^ alkynylcarbonyl(C,^)alkyl, C,^ alkoxycarbonyl(Cw)alkyl, C3^ alkenyloxycarbonyl(Cu)alkyl, C3^ alkynyloxycarbonyl-(C, Jalkyl, aryloxycarbonyl(Ci^)alkyl, Cw alkylthio(C, Jalkyl, Cw alkylsulfinyl(Cw)alkyl, C,^ alkylsulfonyl(C,^)alkyl, aminocarbonyl(C,^)alkyl, aminocarbonyl(C2^)alkenyl, aminocarbonyl(C2^)alkynyl, Cw alkylaminocarbonyl(Cw)alkyl, di(Cw)alkyl-aminocarbonyl(CM)alkyl, Cwalkylarninocarbonyl(C2^)alkenyl(C,^)alkyl, di(CM)alkyl-aminocarbonyl(C2^)alkenyl(C,^)alkyl, alkylaminocarbonyl(C2^)alkynyl(Cu)alkyl, di-(C]^)alkylarninocarbonyl(C1^)alkynyl(C1^)alkyl, Cx4t alkoxycarbonyl, C,^ alkylcarbonyl, aminocarbonyl, CM alkylaminocarbonyl, di(C,^)alkylaminocarbonyl, phenyl (optionally substituted by halo, nitro, cyano, Cw alkyl* Cw haloalkyl, Cw alkoxy or Cw haioalkoxy), phenyl(CM)alkyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C,^ alkyl, C,_6 haloalkyl, C,^ alkoxy or CM haioalkoxy), phenyl(Cw)alkenyl(Cw)alkyl, (wherein the phenyl group is optionally substituted by halo, nitro, cyano, Cw alkyl, C,^ haloalkyl, Cw alkoxy, Cw alkylsulfonyl or C,^ haioalkoxy), heteroaryl (optionally substituted by halo, nitro, cyano, C,^ alkyl, C,^ haloalkyl, C^ alkoxy, C,^ alkylsulfonyl or Cj^s haioalkoxy), heterocyclyl (optionally substituted by halo, nitro, cyano, C,^ alkyl, C,^ haloalkyl, Cw alkoxy or Cw haioalkoxy), heteroaryl(CM)alkyl (where the heteroaryl may be substituted by halo, nitro, cyano, Cw alkyl, Cw haloalkyl, C,^ alkoxy or Cw haloalkoxy),or heterocyclyl(CM)alkyl (where the heterocyclyl may be substituted by halo, cyano, Cw alkyl, Cw haloalkyl, QX4> alkoxy or C^ haioalkoxy); R7 is CM alkyl; R8 and R9 independently are, hydrogen, halogen, CM alkyl, C^ haloalkyl C2 * alkenyl, C,* alkynyl, CM alkoxy or Cw
1-6
haloalkoxy; R1 is hydrogen, halogen, Cw alkyl, C^ alkenyl, Cw alkynyl, C,^ haloalkyl, C
alkoxy, Cw alkoxy (C,Jalkyl, C,^ haloalkoxy, C,^ alkylthio, C,^ haloalkylthio, C,^ alkylsulfinyl, CM haloalkylsulfinyl, C,^ alkylsulfonyl, CM haloalkylsulfonyl, Cw haloalkyl, cyano, nitro, formyl, R20ON=CH, C,^ alkylcarbonyl, C^ alkoxycarbonyl or SF5; or together R1 and R10 together with the atoms to which they are attached may be joined to form a five, six or seven-membered saturated or unsaturated ring carbocylic or heterocyclic ring which may contain one or two hetero atoms selected from O, N or S and which may be optionally substituted by Cw alkyl, Cw haloalkyl or halogen; R" is hydrogen, CM0 alkyl, benzyloxymethyl, benzoyloxymethyl, Cwalkoxy(Cj^)alkyl, C^ alkenyl(Cw)alkyl
1)0 (especially allyl), C^ alkynyl(C,^)alkyl (especially propargyl), C,.10 alkylcarbonyl or C,.10 alkoxycarbonyl (especially isobutoxycarbonyl); R13 is C,.10 alkyl, benzyloxymethyl, benzoyloxymethyl, Cwalkoxy(Cw)alkyl, C2^ alkenyl(Cw)alkyl (especially allyl), Q^ alkynyl(C,^)alkyl (especially propargyl), Cj.10 alkylcarbonyl or C,_,„ alkoxycarbonyl (especially wobutoxycarbonyl); R16 is cyano, nitro, C,^ alkyl, C,^ haloalkyl, C3.7 cycloalkyl,
15 G3.7 cycloalkyKC^alkyl, GH^C^alkenyl, CH^C^alkynyl, phenyl (optionally substituted by halo, nitro, cyano, Cw alkyl, C,^ haloalkyl, C,^ alkoxy or C,^ haloalkoxy) heteroaryl (optionally substituted by halo, nitro, cyano, CM alkyl, Cw haloalkyl, CI4i alkoxy or C,^ haloalkoxy), Cw alkylcarbonyl, C,^ alkoxycarbonyl, Cw alkylamino, di(Cw)alkylamino, C,^ alkylcarbonylamino, Cw alkoxycarbonylamino, C^ alkoxy, C,^ alkylthio, C,^ alkylsulfinyl,
2)0 C,^ alkylsulfonyl, Cw haloalkylthio, Cw haloalkylsulfinyl, Cw haloalkylsulfonyl, arylthio, arylsulfinyl, arylsulfonyl or (Cw)alkylC(0)0; R17 is hydrogen, halogen, nitro, cyano, C^ alkyl, C,^ haloalkyl, Cw cyanoalkyl, C^ alkenyl, C^^ alkynyl, C3.7 cycloalkyl, C2^ haloalkenyl, C3.7 cycloalkyl(C, Jalkyl, C1^alkox(C,^)alkyl, Cw alkoxycarbonyl, Cw alkylcarbonyl, CM alkylaminocarbonyl, di(CMalkylaminocarbonyl, phenyl (optionally
2J5 substituted by halo, nitro, cyano, Cw alkyl, Cw haloalkyl, C,^ alkoxy or C,^ haloalkoxy) or heteroaryl (optionally substituted by halo,nitro, cyano, Cw alkyl, C,^ haloalkyl, C,_6 alkoxy or C,^ haloalkoxy); R20 is Cw alkyl or phenyl(Ci_2)alkyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C,^ alkyl, Cw haloalkyl, Cw alkoxy or C,^ haloalkoxy); R36 is C^ alkyl, OR39 or NR40R41; R37 is hydrogen, Cw alkyl or C^ haloalkyl;
3|0 R38 is hydrogen, C^ alkyl, C,^ haloalkyl, C,^ alkoxy, cyano, Cw alkoxycarbonyl, Cw
alkylcarbonyl orNR42R43; R39 is CM alkyl or optionally substituted phenyl(C,.2)alkyl; R40 and
R41 independently are, hydrogen, Cui alkyl or phenyl (optionally substituted by halo, nitro, cyano, C,^ alkyl, C^ haloalkyl, C,^ alkoxy or Cw haloalkoxy); and R42 and R43 are, independently, hydrogen, C^ alkyl, Q_7 cycloalkyl, C3^ alkenyl, C3^ alkynyl, C2^ haloalkyl, C,^ alkoxy(C,^)alkyl, C,^ alkoxycarbonyl(CM)alkyl, carboxy(Cw)alkyl or phenyl(C,.2)alkyl; or R42 and R43 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further hetero atoms selected from O, N or S and which may be optionally substituted by one or two C,^ alkyl groups.
Preferably n is 0.
Preferably A is CM alkylene, -C(O)- or CM alkyleneoxy.
if) When G is (i), D is preferably S or CR8=CR9, where R8 and R9 are, independently,
hydrogen, halogen, C,^ alkyl, C,^ haloalkyl C2^ alkenyl, C,^ alkynyl, Cw alkoxy or C,^ haloalkoxy.
When G is (ii), D is preferably S.
Preferably E is N or CR10 where R10 is hydrogen, halogen, C,^ alkyl, CM haloalkyl, p Gw alkoxy, Gw haloalkoxy, G^ alkoxy (C^alkyl, CM alkylthio or SF5; or R1 and R10
together with the atoms to which they are attached form a benzene ring optionally substituted by Cw alkyl, C,^ haloalkyl or halogen.
Preferably G is (i).
Preferably M1 is N(Rn)G(=0) where R" is hydrogen, C1J6 alkyl, CM alkoxy-2|0 (Cw )alkyl, benzyloxymethyl or benzoyloxymethyl.
Preferably Y is 0.
Preferably J is N or CR<7 where R17 is hydrogen, C,^ alkyl, C,^ haloalkyl, cyano, halogen or nitro.
R1 is preferably hydrogen, halogen, C,^ alkyl, C^ alkenyl, Cw haloalkyl, Cu alkoxy, 2|5 C,^ haloalkoxy, Cw alkylthio, C^ haloalkylthio, C^ cycloalkyl, cyano, nitro or SF5.
R2 is preferably Cj.10 alkyl, C^ alkoxy(C,Jalkyl, ally! orpropargyl.
Preferably R3, R4and R5 are, independently, hydrogen, C,.3 alkyl or halogen.
R6 is preferably CMQ alkyl or C,.10 haloalkyl (each one of which may be substituted with a Cj^ alkyloxime, Cw haloalkyloxime, C,^ alkylhydrazone or C,^ haloalkylhydrazone 3p group) or C,^ cyanoalkyl, C2^ 3lkenyl(C^)alkyl, C^ alkynyl(Cw)alkyl, C^ cycloalkyl, C3.7
halocycloalkyl, C3.7 cyanocycloalkyl, C,.3 alkyl(C3_7)cycloalkyl, CJ.J alkyl(Cj.7)halocycloalkyl, C5-6 cycloalkenyl, C3.7 cycloalkyl(Cj^)alkyl, C^ cycloalkenyl(Cw)alkyl, C^ haloalkenyl-(ClJ6)alkyl, C,^cyanoalkenyl(CiJalkyl, Cw alkoxy(C^)aIkyl, C^ alkenyloxy(C, Jalkyl, C3^ alkynyloxy(Cw)alkyl, aryloxy(CM)alkyl, Cw carboxyalkyl, Cw alkylcarbonyl(C, Jalkyl, C2^ alkenylcarbonyl(C^)alkyl, C^ alkynylcarbonyl(C, Jalkyl, Cw alkoxycarbonyl(CM)alkyl, Cw alkenyloxycarbonyl(C, Jalkyl, C,^ alkynyloxycarbonyl(Cw)alkyl, aryloxycarbonyl-(C,Jalkyl, Cw alkylthio(CM)alkyl, Cw alkylsulfinyl(C,Jalkyl, CM alkylsulfonyl(C^)alkyl, aminocarbonyl(Cw)alkyl, aminocarbonyl(C2^)alkenyl, aminocarbonyl(C2^)alkynyl, C^ alkylaminocarbonyl(Cw)alkyl, di(Cw)alkylaminocarbonyl(Cw)alkyl, C^ alkyl-
1 p aminocarbonyl(Cw)alkenyl(Cw)alkyl, di(C, Jalkylaminocarbonyl(Cw)alkenyl(Cw)alkyl, alkylaminocarbonyl(C1^)alkynyl(Cl^)alkyl, di(CM)alkylanunocarbonyl(Cw)alkynyl-(Cw)alkyl, phenyl (optionally substituted by halo, nitro, cyano, Cw alkyl, CM haloalkyl, C,^ alkoxy or C,^ haloalkoxy), phenyl(CM)alkyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, Cw alkyl, C,_6 haloalkyl, C,^ alkoxy or Cw haloalkoxy),
l(5 phenyl(Cw)alkenyl(C1Jal]^l, (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C,^ alkyl, CM haloalkyl, C^ alkoxy, C,^ alkylsulfonyl or CM haloalkoxy), heteroaiyl (optionally substituted by halo, nitro, cyano, Cw alkyl, C,^ haloalkyl, CM alkoxy or C,^ haloalkoxy), heterocyclyl (wherein the heterocyclyl group is optionally substituted by halo, nitro, cyano, C,^ alkyl, Cw haloalkyl, C,^ alkoxy or C,^ haloalkoxy), heteroaryl-
2|0 (CM)alkyl (wherein the heteroaiyl group is optionally substituted by halo, nitro, cyano, Cw alkyl, Cw haloalkyl, Cw alkoxy, CM alkylsulfonyl or C,^ haloalkoxy)or heterocyclyl-(CM)alkyl (wherein the heterocyclyl group is optionally substituted by halo, nitro, cyano, C,^ alkyl, CM haloalkyl, Cw alkoxy or C,^ haloalkoxy).
Preferably the optionally substituted ring of formula
25
is optionally substituted isothiazolyl, optionally substituted pyridyl, optionally substituted pyrimidinyl, optionally substituted quinazolinyl and optionally substituted quinolinyl groups in which the optional substituents are chosen from halo, C,^ alkyl, C,^ haloalkyl, C,^ alkoxy, 3p C,^ alkoxy^j^alkyl or Cw haloalkoxy.
-WetH)753W
PCT/GBOO/01272
Preferably the optionally substituted ring of formula
15
20
More preferably A is CH2 or CH20, even more preferably CH2.
More preferably M1 is N(R")C(=0), where R11 is hydrogen, CM alkyl, CM alkoxy-(CM)alkyl, benzyloxymethyl or benzoyloxymethyl. It is especially preferred that R" is hydrogen, ethyl, ethoxymethyl, allyl or propargyl.
More preferably J is N or CR17, where R17 is hydrogen, methyl or halogen.
More preferably R2 is ethyl, ethoxymethyl, allyl or propargyl.
More preferably R3, R4 and R5 are independently, hydrogen, or halogen (especially fluorine); it is especially preferred that each of R3, R4 and R5 is hydrogen.
More preferably R6 is CM alkyl, C2_g haloalkyl, CM cyanoalkyl, C,.7 cycloalkyl, C,.3 alkyl (C3.7) cycloalkyl, Cw alkoxy (C,^) alkyl, heterocyclic (optionally substituted by halo, nitro, cyano, Cw alkyl, Cw haloalkyl, Cw alkoxy or Cw haloalkoxy), phenyl (optionally substituted by halogen, Cw alkyl, Cw haloalkyl, Cw alkoxy, nitro, cyano or C,^ alkylsulfonyl) or heteroaryl (optionally substituted by halogen, Cw alkyl, Cw haloalkyl, C,^ alkoxy, nitro, cyano or C,^ alkylsulfonyl).
Even more preferably R6 is CM alkyl, C^ haloalkyl, C,^alkoxy(C,^)alkyl, C3.7cycloalkyl or C3.7 cycloalkyl(C,^)alkyl.
Even more preferably the group
Most preferably the optionally substituted ring of formula
In a further aspect the present invention provides a compound of formula (IB):
10
15
(IB)
wherein R1 is hydrogen, halogen, Cw alkyl, Cw haloalkyl, CM alkoxy, Cw haloalkoxy, Cw alkylthio, C^ cycloalkyl or CM alkoxy(C,Jalkyl; R10 is hydrogen, halogen, CM alkyl, Cw haloalkyl, cyano, nitro, CHO, CH=NOR20, CM alkylcarbonyl, C,^ alkoxycarbonyl or Cw alkylS(0)q; or together R1 and R10 form a five or six membered saturated or unsaturated carbocyclic ring, optionally substituted by one or two Cw alkyl groups; R11 is hydrogen, Cw alkyl, CH2(CM haloalkyl), CM alkenyl, C^ alkynyl, Cw alkoxyCC, Jalkyl, CM alkylcarbonyl, Cw alkoxycarbonyl, formyl, optionally substituted phenoxycarbonyl, optionally substituted phenyl(CM)alkyl or S(0)pR44; R6 is hydrogen, C,_8 alkyl, CW haloalkyl,
CH cyanoalkyl, C^ alkenyl, C^ alkynyl, C3.7 cycloalkyl, C^ cycloalkyl(C, Jalkyl, C^ haloalkenyl, Cw alkoxy(Cw)alkyl, Cw carboxyalkyl, C^ alkylcarbonyl(C,^)alkyl, C,^ alkoxycarbonyl(ClH6)alkyl, CM alkylthio(C, Jalkyl, C1-6 alkylsulfinyl(C1^)alkyl, CM alkylsulfonyl(C,^)alkyl, aminocarbonyl(Ci^)alkyl, C,^ alkylaminocarbonyl(CI^)alkyl, di-(CI^)alkylaminocarbonyl(Cw)alkyl, optionally substituted phenyl, optionally substituted phenyl(Cw)alkyl or optionally substituted heteroaryl; R20 is hydrogen, C,^ alkyl, optionally substituted phenyl or optionally substituted phenyl(CM)alkyl; R44 is Cw alkyl, C^ haloalkyl or optionally substituted phenyl; Y is O or S; m is 0 or 1; and p and q are, independently, 0,1 or 2; provided that when R is C3.£ alkenyl, C3^ alkynyl or C3^ haloalkenyl, R* does not have lp an unsaturated carbon atom attached directly to N and provided that when Ru is Cw alkenyl or C3.j alkynyl, R" does not have an unsaturated carbon atom attached directly to N.
It is preferred that R1 is ethyl or, especially, methyl.
It is preferred that R10 is hydrogen, halogen (especially chloro) or cyano.
It is preferred that m is 0.
l|5 It is preferred that the compounds of the invention are of formula (la).
In one particular aspect the present invention provides a compound of formula (la) wherein R1 is CM alkyl (especially methyl or ethyl); R10 is hydrogen, halogen (especially chloro or bromo) or cyano; or R1 and R10 together form a cyclopentyl, cyclohexyl or phenyl ring; R" is hydrogen, CM alkyl (especially methyl or ethyl), phenyl(CM)alkyl (especially 2p benzyl), CM alkylcarbonyl (especially acetyl) or CM alkylsulfonyl (especially
methanesulfonyl); m is 0; Y is oxygen; and R6 is C,^ alkyl [optionally substituted with halogen, C,_, alkoxy, phenyl (itself optionally substituted with halogen), C02H, CONH2 (itself optionally substituted with CM alkyl), cyano, C3^ cycloalkyl or CO(CM alkoxy)], CM alkenyl, CM alkynyl, C3^ cycloalkyl, phenyl [optionally substituted with halogen, CM 2j> haloalkyl (especially CF3), nitro, C02H, or cyano] or heteroaryl (especially pyridyl or pyrimidinyl) [optionally substituted with CM alkyl or Ci^ haloalkyl].
In a further aspect the present invention provides a compound of formula (IC):
(IC)
wherein n is 0 or 1; A is optionally substituted C^ alkylene, optionally substituted C^ alkenylene, optionally substituted Cw alkynylene, optionally substituted C,^ alkylenoxy, optionally substituted oxy(C,^)alkylene, optionally substituted Cw alkylenethio, optionally substituted thio(Cw)alkylene, optionally substituted Cw alkylenamino, optionally substituted aminoCC^alkylene, optionally substituted [C,^ alkyleneoxy(C,^)alkylene], optionally substituted [Cw alkylenethio(Cw)alkylene], optionally substituted [Cw alkylenesulfinyl-(Cu)alkylene], optionally substituted [C,^ alkylenesulfonyl(C,^)alkylene] or optionally substituted [Cw alkyleneaminoCC, Jalkylene]; D is S, NR7, CR8=CR9, CR8=N, CR8=N(0), lp KNCR9 orNCO^GR9; R7 is Gu alkyl; EisN, N-oxide or CR10; M1 is OC(=Y), N(RU)C(=Y), N=C(OR12), N=C(SR13) or N=G(NR14R15) where O or N is the atom of attachment to the ring containing E and D; Y is O, S or NR16; J is N or CR17; Rl is hydrogen, halogen, optionally substituted CM alkyl, optionally substituted C2^ alkenyi, optionally substituted C2^ alkynyl, optionally substituted C,^ alkoxy, optionally substituted Clw6 alkylthio, optionally substituted
l|5 C^ cycloalkyl, cyano, nitro or SF5; R11 is hydrogen, optionally substituted C,.,,, alkyl, optionally substituted [C^ alkenyl(Cw)alkyl], optionally substituted [C2^ alkynyl -(Cw)alkyl], optionally substituted C3.7 cycloalkyl, optionally substituted Cj.,0 alkylcarbonyl, optionally substituted C,.10 alkoxycarbonyl, formyl, optionally substituted Cj.,0 alkylaminocarbonyl, optionally substituted di(C1.,0)alkylarninocarbonyl, optionally
2|0 substituted phenoxycarbonyl, optionally substituted C,^ alkylthio, optionally substituted Cw alkylsulfinyl, optionally substituted C,^ alkylsulfonyl, optionally substituted C,^ arylthio, optionally substituted C,^ arylsulfinyl, optionally substituted C,^ arylsulfonyl or R^R^NS; R12 is optionally substituted C,.10 alkyl, optionally substituted [C^ alkenyl(C1^)alkyl], optionally substituted [C^ alkynyl(Cw)alkyl], optionally substituted C3.7 cycloalkyl,
25 optionally substituted CM0 alkylcarbonyl, optionally substituted Cuw alkoxycarbonyl,
formyl, optionally substituted CMOaIkylaminocarbonyl, optionally substituted di(C,.10)alkyl-aminocarbonyl,, amino, optionally substituted Cu alkylamino, optionally substituted di-(C,^)alkylamino, optionally substituted phenoxycarbonyl, tri(CM)alkylsilyl, aryldi-(CM)alkylsilyl, (CM)alkyldiarylsilyl or triarylsilyl; R13 is optionally substituted CM0 alkyl, 5 optionally substituted [C2^ alkenyl(C,^)alkyl], optionally substituted [C2^ alkynyl-
(CM)alkyl], optionally substituted C3.7 cycloalkyl, optionally substituted C,.1C alkylcarbonyl, optionally substituted C,.10 alkoxycarbonyl, optionally substituted C,_10alkylarninocarbonyl, optionally substituted di(CI.,0)alkylaminocarbonyl or optionally substituted phenoxycarbonyl); RM and R15 are, independently optionally substituted CM0 alkyl, D optionally substituted CM alkoxy, optionally substituted [C2^ alkenyl(C,^)alkyl], optionally ( substituted [C2^ alkynyl(CM)alkyl], optionally substituted C^ cycloalkyl, optionally substituted CU10 alkylcarbonyl, optionally substituted C,.,0 alkoxycarbonyl, formyl, optionally substituted CMOalkylaminocarbonyl, optionally substituted di(CM0)alkyl-aminocarbonyl, hydroxy, amino, optionally substituted CM alkylamino, optionally 5 substituted di(C,^)alkylarnino, or optionally substituted phenoxycarbonyl; R3, RA and R5 are, independently, hydrogen, halogen, optionally substituted Gw alkyl, optionally substituted -C,^ alkoxy, optionally substituted C,^ alkyltbio, optionally substituted C,^ alkylsulfinyl, optionally substituted Cw alkylsulfonyl, cyano, nitro, optionally substituted CM alkylcarbonyl, optionally substituted Cw alkoxycarbonyl or SF5; R* is hydrogen, cyano, 3 optionally substituted C,.20 alkyl, optionally substituted Cj.20 alkenyl(Cw)alkyl, optionally substituted C2.20 alkynyl(Ci^)alkyl, optionally substituted C3.7 cycloalkyl, optionally substituted C5^ cycloalkenyl, formyl, optionally substituted C,.20 alkoxycarbonyl, optionally substituted C,.20 alkylcarbonyl, aminocarbonyl, optionally substituted C,.20alkylamino-carbonyl, optionally substituted d^C^alkylaminocarbonyl, optionally substituted 5 aryloxycarbonyl, optionally substituted arylcarbonyl, optionally substituted arylamino-carbonyl, optionally substituted N-alkyl-N-arylaminocarbonyl, optionally substituted diarylaminocarbonyl, optionally substituted heteroaryloxycarbonyl, optionally substituted heteroarylcarbonyl, optionally substituted heteroarylaminocarbonyl, optionally substituted alkylheteroarylaminocarbonyl, optionally substituted dmeteroarylaminocarbonyl, optionally I substituted phenyl, optionally substituted heteroaryl, optionally substituted heterocyclyl, optionally substituted C,.20 alkylsulfonyl, or optionally substituted arylsulfonyl; R8 and R9
are, independently, hydrogen, halogen, cyano, nitro, optionally substituted C,^ alkyl, optionally substituted C2^ alkenyl, optionally substituted C^ alkynyl or optionally substituted C^ alkoxy; R10 is hydrogen, halogen, optionally substituted Cw alkyl, optionally substituted C2^ alkenyl, optionally substituted C2^ alkynyl, optionally substituted Cw alkoxy, optionally substituted C,^ alkylthio, optionally substituted C^ alkylsulfinyl, optionally substituted C,^ alkylsulfonyl, cyano, nitro, formyl, R20ON=C(R21), optionally substituted C,^ alkylcarbonyl, optionally substituted Cw alkoxycarbonyl or SF5; or R1 and R10 together with the atoms to which they are attached may be joined to form a five, six or seven-membered saturated or unsaturated ring carbocylic or heterocyclic ring which may contain one or two lp hetero atoms selected from O, N or S and which may be optionally substituted by Cw alkyl, C^ haloalkyl or halogen; R16 is hydrogen, cyano, nitro, optionally substituted C w alkyl, optionally substituted C3.7 cycloalkyl, optionally substituted (C2^)alkenyl(C,^)alkyl, optionally substituted (C2^)alkynyl(Cw)alkyl, optionally substituted phenyl, optionally substituted heteroaryl, optionally substituted C^ alkylcarbonyl, optionally substituted C,^ 1|5 alkoxycarbonyl, optionally substituted Cw'alkylamino, optionally substituted di(C,^)alkyl-amino, optionally substituted CM alkylcarbonylamino, optionally substituted C,^ alkoxycarbonylamino, optionally substituted C,^ alkoxy, optionally substituted Cw alkylthio, optionally substituted CM alkylsulfinyl, optionally substituted Cw alkylsulfonyl, optionally substituted aryltbio, optionally substituted arylsulfinyl, optionally substituted
2)0 arylsulfonyl or CM acyloxy; R17 is hydrogen, halogen, nitro, cyano, optionally substituted -CM alkyl, optionally substituted C^ alkenyl, optionally substituted C2^ alkynyl, optionally substituted C^ cycloalkyl, optionally substituted C^ alkoxycarbonyl, optionally substituted C,^ alkylcarbonyl, optionally substituted CMalkylaminocarbonyl, optionally substituted di(C,^)alkylaniinocarbonyl, optionally substituted phenyl or optionally substituted
.2)5 heteroaryl; R22 and R23 are, independently, optionally substituted C,^ alkyl or R22 and R23 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further hetero atoms selected from O, N or S and which may be optionally substituted by one or two C,^ alkyl groups; R21 is hydrogen, optionally substituted phenyl or optionally substituted C,_6 alkyl; and R20 is hydrogen,
optionally substituted phenyl (Ci.2)alkyl or optionally substituted C,.20 alkyl.
The compounds of formula (IC) may exist in different geometric or optical isomers or tautomeric forms. This invention covers all such isomers and tautomers and mixtures thereof in all proportions.
In a further aspect, the present invention provides a compound of formula (ID):
5
wherein A, D, E, M1, Y, J, R1, R3, R4, R5 and R6 are as defined above for a compound of formula (IC). More preferred compounds of formula (ID) are those of formula (IE)
(IE)
1)
wherein D is S, NR7, CR8=CR9, CR8=N, CR8=N(0), N=CR9 or N(0)=CR9; E is N or CR10; R1 is hydrogen, halogen, C,^ alkyl, C2^ alkenyl, C^ alkynyl, CM cyanoalkyl, Cw haloalkyl, Cw alkoxy, Cw haloalkoxy, C,^ alkylthio, C,^ haloalkylthio, C3ws cycloalkyl, C3.7 cycloalkyl(CM)alkyl, Cw alkoxy(C, Jalkyl, cyano, nitro or SF5; A is Cw alkylene, Cw
115 alkenylene, C,^ alkylenoxy, oxy(C,^)alkylene, C,^ alkylenamino or C,^ alkylenethio, each of which is optionally substituted by C,.3 alkyl, Cui haloalkyl, C,.3 cyanoalkyl, halogen, Cj.3 alkoxy, C^ alkoxycarbonyl, cyano, =0, =NR36 or =CR37R38; M1 is N(R")C(=Y) or N=C(SR13) where O or N is the atom of attachment to the ring containing E and D; Y is O, S or NR16; J is N or CR17; Ru is hydrogen, Cj.,0 alkyl, benzyloxymethyl, benzoyloxymethyl,
2p C^alkoxy(C^)alkyl, Cw alkenyl(CM)alkyl (especially allyl), C2^ a!kynyl(C, Jalkyl
(especially propargyl), C,.10 alkylcarbonyl or C,.10 alkoxycarbonyl (especially wobutoxy-carbonyl); R13 is Cj.,0 alkyl, benzyloxymethyl, benzoyloxymethyl, C,^alkoxy(C, Jalkyl, C^ alkenyl(C^)alkyl (especially allyl), Cw alkynyl(CM)alkyl (especially propargyl), C,.)0 alkylcarbonyl or CM0 alkoxycarbonyl (especially wobutoxycarbonyl); R3, R4 and R5 are
25 independently selected from hydrogen, halogen, Cw alkyl, C,^ alkoxy, CM haloalkoxy, C,^
alkylthio, Cw haloalkylthio, C^ alkylsulfmyl, Cw haloalkylsulfinyl, C^ alkylsulfonyl, Cu haloalkylsulfonyl, CM haloalkyl, cyano, nitro, C,^ alkylcarbonyl, C^ alkoxycarbonyl or SF5; R6 is cyano, C,.g alkyl, C2^ haloalkyl, C^ cyanoalkyl, Cw alkenyl(Cw)alkyl, C^ alkynyl-(C,Jalkyl, C3_7 cycloalkyl, C3.7 halocycloalkyl, Cj.7 cyanocycloalkyl, C,.3 alkyl(C3.7)cyclo-alkyl, C,.3alkyl(C3.7)halocycloalkyl, C^ cycloalkenyl, C3.7 cycloalkyl(C,^)alkyl, CM cycloalkenyl(Cw)alkyl, C^ haloalkenyl(Cw)alkyl, Cwcyanoalkenyl(Cw)alkyl, Cw alkoxy(Cw)alkyl, C^ alkenyloxyCC, Jalkyl, Cw alkynyloxy(C^)alkyl, aryloxy(C, Jalkyl, formyl, C^ carboxyalkyl, Cw alkylcarbonyl(C,^)alkyl, C2^ alkenylcarbonyl(Cw)alkyl, C2^ alkynylcarbonyl(Gi^)alkyl, C,^ alkoxycarbonyl(C,^)alkyl, Cw alkenyloxycarbonyl-(Cw)alkyl, CM alkynyloxycarbonyl(Cw)alkyl, aryloxycarbonyl(Cw)alkyl, Cw alkylthio-(C,^)alkyl, Cw alkylsulfinyl(Cw)alkyl, Cw alkylsulfonyl(CM)alkyl, aminocarbonyl-(CM)alkyl, aminocarbonyl(C2^)alkenyl, aminocarbonyl(Cw)alkynyl, CM alkylamino-carbonyl(C,^)alkyl, di(Cw)alkylaminocarbonyl(C,^)alkyl, Cw alkylaminocarbonyl-(C^)akenyl(Cli6)alkyl, di(Cw)alkylaminocarbonyl(C2^)alkenyl(C,^)alkyl, alkylamino-carbbnyI(G2.i)alkynyl(Cw)al^
alkoxycarbonyl, C,^ alkylcarbonyl, arninocafbonylj GIi6alkylaminocarbonyl, di(G1^)alkyl-aminocarbonyl, phenyl (optionally substituted by halo, nitro, cyano, Cw alkyl, C,^ haloalkyl, Cj^s alkoxy or C,^ haloalkoxy), phenyl(CM)alkyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, CM alkyl, C,^ haloalkyl, Cw alkoxy or C,^ haloalkoxy), phenyl(C2j,)alkenyl(Gw)alkyl, (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C,^ alkyl, Cw haloalkyl, Cw alkoxy, Cw alkylsulfonyl or Cw haloalkoxy), heteroaryl (optionally substituted by halo, nitro, cyano, Cw alkyl, Cw haloalkyl, C,^ alkoxy, C|^ alkylsulfonyl or C1-6 haloalkoxy), heterocyclyl (optionally substituted by halo, nitro, cyano, C,^ alkyl, CM haloalkyl, CM alkoxy or C]^ haloalkoxy), heteroaryl(CM)alkyl (where the heteroaryl may be substituted by halo, nitro, cyano, C,^ alkyl, CM haloalkyl, C^ alkoxy or C,^ haloalkoxy),or.heterocyclyl(C,^)alkyl (where the heterocyclyl may be substituted by halo, cyano, Cw alkyl, C,^ haloalkyl, Cw alkoxy or C,^ haloalkoxy); R8 and R9 independently are, hydrogen, halogen, Cw alkyl, C,^ haloalkyl C^ alkenyl, Cw alkynyl, C,^ alkoxy or C,^ haloalkoxy; R10 is hydrogen, halogen, C,^ alkyl, C2^ alkenyl, CM alkynyl, C,^ haloalkyl, C,^ alkoxy, C,^ alkoxy (CM)alkyl, Cw haloalkoxy, Cw alkylthio, C,^ haloalkylthio, Cw alkylsulfinyl, C,^ haloalkylsulfinyl, Cw alkylsulfonyl, CM haloalkyl-
sulfonyl, Cw haloalkyl, cyano, nitro, formyl, CH=NOR20, CM alkylcarbonyl, Cw alkoxycarbonyl or SF5; or together R1 and R10 together with the atoms to which they are attached may be joined to form a five, six or seven-membered saturated or unsaturated ring carbocylic or heterocyclic ring which may contain one or two hetero atoms selected from O, N or S and which may be optionally substituted by CM alkyl, CM haloalkyl or halogen; R16 is cyano, nitro, CM alkyl, Cw haloalkyl, C3.7 cycloalkyl, C3.7 cycloalkyl(Cw)alkyl, CH2(C2 Jalkenyl, CH2(C2^)alkynyl, phenyl (optionally substituted by halo, nitro, cyano, C,^ alkyl, CM haloalkyl, Cw alkoxy or Cw haloalkoxy) heteroaryl (optionally substituted by halo, nitro, cyano, Cw alkyl, C,^ haloalkyl, Cw alkoxy or Cw haloalkoxy), Cw
10 alkylcarbonyl, Cw alkoxycarbonyl, C,^ alkylamino, di(Ci^)alkylamino, C,^
alkylcarbonylamino, Cw alkoxycarbonylamino, C,^ alkoxy, Cw alkylthio, Cw alkylsulfinyl, Cw alkylsulfonyl, CM haloalkylthio, C,^ haloalkylsulfinyl, Cw haloalkylsulfonyl, arylthio, arylsulfinyl, arylsulfonyl or OCO(C^)alkyl; R17 is hydrogen, halogen, nitro, cyano, Cug alkyl, C,^ haloalkyl, C,^ cyanoalkyl, C^ alkenyl, CM alkynyl, C^, cycloalkyl, C2_6
lfc haloalkenyl, Gj., cycloalkyKC, Jalkyl, CMalkox(Cw)alkyl, Cw alkoxycarbonyl, C,^ alkylcarbonyl, Gw alkylaminocarbonyl, di(C,^alkylaminocarbonyl, phenyl (optionally substituted by halo, nitro, cyano, C,^ alkyl, CM haloalkyl, Cw alkoxy or Cw haloalkoxy) or heteroaryl (optionally substituted by halo,nitro, cyano, C,^ alkyl, C,^ haloalkyl, C,^ alkoxy or Cw haloalkoxy); R36 is CM alkyl, OR39 or NR40R41; R37 is hydrogen, Cw alkyl or Cw
2D haloalkyl; R38 is hydrogen, Cw alkyl, C,^ haloalkyl, Cw alkoxy, cyano, CM alkoxycarbonyl, CM alkylcarbonyl or NR42R43; R22 and R23 independently are, hydrogen, Cw alkyl, CH2(CM haloalkyl), C,^ cyanoalkyl, Cu alkoxy(C, Jalkyl, Gw alkylthio(C, Jalkyl, Cw alkoxy-(Cw)alkoxy(Cw)alkyl, phenyl(CM)alkyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, Cw alkyl, C,^ haloalkyl, C,^ alkoxy or CM haloalkoxy), heteroaryl-
2|5 (CM)alkyl (wherein the heteroaryl group is optionally substituted by halo, nitro, cyano, C,^ alkyl, ClJb haloalkyl, C,^ alkoxy or C,^ haloalkoxy), heterocyclyl(CM)alkyl (wherein the heterocyclyl group is optionally substituted by halo, nitro, cyano, C^ alkyl, C,^ haloalkyl, CM alkoxy or C,^ haloalkoxy), or R22 and R23 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two
3|0 further hetero atoms selected from O, N or S and which may be optionally substituted by one or two C,^ alkyl groups; R39 is C,^ alkyl or optionally substituted phenyl(Cj.2)alkyl; R40 and
{
R41 independently are, hydrogen, C,_g alkyl or phenyl (optionally substituted by halo, nitro, cyano, Cw alkyl, Cw haloalkyl, Cw alkoxy or C]_6 haloalkoxy); R21 is hydrogen or C^ alkyl;
is C,^ alkyl or phenyl(Cj.2)alkyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C^ alkyl, CM haloalkyl, Cw alkoxy or C,^ haloalkoxy); and R42 and R43 independently, are, hydrogen, C,_8 alkyl, C3_7 cycloalkyl, C3^ alkenyl, C^ alkynyl, C^ haloalkyl, C,^ alkoxy (C^alkyl, CM alkoxycarbonyl(Cw)alkyl, carboxy(Cw)alkyl or phenyl(C,.2)alkyl; or R42 and R43 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further hetero atoms selected from O, N or S and which may be optionally substituted by one or two C,^ alkyl groups.
Preferably A is CM alkylene -C(O)- or CM alkyleneoxy. Preferably D is S or CR8=CR9, where R* and R' are, independently, hydrogen, halogen, CM alkyl, Cw haloalkyl C2^ alkenyl, CM alkynyl, Cw alkoxy or C,^ haloalkoxy. Preferably E is N or CR10 where R10 is hydrogen, halogen, Cw alkyl, Cw haloalkyl, 1(5 CM alkoxy, Gw haloalkoxy, CM alkoxy (C^)alkyl, CM alkylthio or SF3; or R1 and R10
together with Hie atoms to which they are attached form a benzene ring optionally substituted by CM alkyl, CM haloalkyl or halogen.
A preferred value of M1 is N(Rn)C(=0) where N is the atom of attachment to the ring containing E and D; and Rn is hydrogen, Ci4 alkyl, Cw alkpxy(C]j6 )alkyl, 2p benzyloxymethyl or benzoyloxymethyl. Preferably Y is O.
Preferably J is N or CR17 where R17 is hydrogen, Cw alkyl, Cw haloalkyl, cyano, halogen or nitro.
R1 is preferably hydrogen, halogen, Cw alkyl, Cw alkenyl, Cw haloalkyl, C,^ alkoxy, 2(5 Cw haloalkoxy, C,^ alkylthio, Cw haloalkylthio, G^ cycloalkyl, cyano, nitro or SF5. Preferably R3, R4and R5 are independently hydrogen, Cu alkyl or halogen. R6 is preferably CM alkyl, CM haloalkyl, Cw cyanoalkyl, C^ alkenyl(Cj^)alkyl, C^ alkynyl (Cw)alkyl, C3.7 cycloalkyl, C3.7 halocycloalkyl, C3.7 cyanocycloalkyl, C,.3alkyl-(C3_7)cycloalkyl, C^3 alkyl(C3.7)halocycloalkyl, CS4 cycloalkenyl, C3.7 cycloalkyl(C,^)alkyl, 3p Cj^s cycloalkenyl(Cw)alkyl, Cw haloalkenyl(CM)alkyl, C,^ cyanoalkenyl(Cw)alkyl, C,^ alkoxy(CM)alkyl, C^ alkenyloxy(C^)alkyl, C3^ alkynyloxy(Cw)alkyl, aryloxy(Cw)alkyl,
*
C^ carboxyalkyl, Cw alkylcarbonyl(C, Jalkyl, CM alkenylcarbonyl(C^)alkyl} C2^ alkynylcarbonyl(Cw)alkyl, Cw aikoxycarbonyl(Cw)alkyl, C^ alkenyloxycarbonyl(C^)-alkyl, C3^ alkynyloxycarbonyl(C, Jalkyl, aryloxycarbonyl(Cw)alkyl, Cw alkylthio(C,^> alkyl, C,^ alkylsulfinyl(C,^)alkyl, CM alkylsulfonyl(Cw)alkyl, aminocarbonyl(C,^)aIkyl, aminocarbonyl(C2.6)aIkenyl, aminocarbonyl(C2^)alkynyl, C,^ allcylarninocarbonyl(Ci_6)alkyl, di(Cw)alkylaminocarbonyl(Cw)alkyl, CM alkylaminocarbonyl(C,^)alkenyl(Cw)alkyl, di (Cw)alkylaminocarbonyl(Cw)alkenyl(Cu)alkyi, alkylanTinocarbonyl(Cw)alkynyl(C,^)alkyl, di(C, Jalkylaminocarbonyl(C,45)alkynyl(C1Jalkyl, phenyl (optionally substituted by halo, nitro, cyano, Cw alkyl, C,^ haloalkyl, C,^ alkoxy or C,^ haloalkoxy),j)henyl(Cw)alkyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C,^ alkyl, C,^ haloalkyl, C,^ alkoxy or Cw haloalkoxy), phenyl(C2j,)alkenyl(C, Jalkyl, (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C,^ alkyl, C,^ haloalkyl, C^ alkoxy, Cw alkylsulfonyl or CM haloalkoxy), heteroaryl (optionally substituted by halo, nitro, cyano, Cw alkyl, CM haloalkyl, C^ alkoxy or C^ haloalkoxy), heterocyclyl (wherein
1|5 the heterocyclyl group is optionally substituted by halo, nitro, cyano, C^ alkyl, C,^
haloalkyl, Gw alkoxy or Ci_6 haloalkoxy), heteroaryl(C]^)alkyl (wherein the heterbaryl group is optionally substituted by halo, nitro, cyano, C,^ alkyl, Cu haloalkyl, Cw alkoxy, C,^ alkylsulfonyl or C,^ haloalkoxy)or heterocyclyl(CM)alkyl (wherein the heterocyclyl group is optionally substituted by halo, nitro, cyano, C,^ alkyl, C,^ haloalkyl, Cw alkoxy or C,^
2p haloalkoxy).
More preferred optionally substituted rings of formula
2p include optionally substituted isothiazolyl, optionally substituted pyridyl, optionally substituted pyrimidinyl, optionally substituted quinazolinyl and optionally substituted quinolinyl groups in which the optional substituents are chosen from halo, C,^ alkyl, C,^ haloalkyl, Cw alkoxy, Cw alkoxy(Cw)alkyl or C^ haloalkoxy. Most preferred optionally substituted rings of formula
1)
15
More preferably A is CH2 or CH20, even more preferably CH2.
It is more preferred that M1 is NR1!C(=0), where R11 is hydrogen, CM alkyl, CM alkoxy (CM)alkyl, benzyloxymethyl or benzoyloxymethyl. It is especially preferred that Rn is hydrogen, ethyl, ethoxymethyl, allyl or propargyl
It is more preferred that R3, R4 and R5 are independently, hydrogen, or halogen (especially fluorine); it is especially preferred that each of R3, R4 and R5 is hydrogen.
More preferably J is N or CR17 where R17 is hydrogen, methyl, or halogen.
More preferably R6 is C,., alkyl, CM haloalkyl, C,_8 cyanoalkyl, C3.7 cycloalkyl, C,.3 alkyl (Cj.,) cycloalkyl, Cw alkoxy (C,^) alkyl, heterocyclic (optionally substituted by halo, nitro, cyano, C,^ alkyl, Cw haloalkyl, CM alkoxy or Cw haloalkoxy), phenyl (optionally substituted by halogen, Cw alkyl, C,^ haloalkyl, Cw alkoxy, nitro, cyano or Cw alkylsulfonyl) or heteroaryl (optionally substituted by halogen, Cw alkyl, Cw haloalkyl, C,^ alkoxy, nitro, cyano or C^ alkylsulfonyl).
Particularly preferred values of R^ are C,.g alkyl, G^ haloalkyl, iQ.6alkoxy(C,.6)alkyl, c ^cycloalkyl or C3.7 cycloalkyl(C,^)alkyl.
Particularly preferred values of the group:
23
The compounds in the following Tables illustrate compounds of the invention.
Table Al
Table Al provides 432 compounds of Formula Al wherein R1, D, E, R11, A and J are as defined in Table Al and R6 is methyl.
10
Compound
No. R1 D E R" A J
Al.l CH3 S C-Cl H CH2 N
A1.2 CH3 S C-Cl CH2CH3 CH2 N
A1.3 CH3 s C-Cl CHjC=CH2 CH2 N
A1.4 CH3 s C-Cl CH2C.CH CH2 N
A1.5 CH3 s C-Cl CH2OCH3 CH2 N
A1.6 CH3 s C-Ci CH2OCH2CH3 CH2 N
A1.7 CH3 s C-Br H CH2 N
A1.8 CH3 s C-Br CH2CH3 CH2 N
A1.9 CH3 s C-Br CH2C=CH2 CH2 N
ALIO CH3 s C-Br CH2C.CH CH2 N
Al.ll CH3 s C-Br CH2OCH3 CH2 N
A1.12 CH3 s C-Br CH2OCH2CH3 CH2 N
A1.13 CH2CH3 s C-Cl H CH2 N
A1.14 CH2CH3 s C-Cl CH2CH3 CH2 N
A1.15 CH2CH3 s C-Cl CH2C==CH2 CH2 N
A1.16 CH2CH3 s C-Cl CH2C.CH CH2 N
A1.17 CH2CH3 s C-Cl CH2OCH3 CH2 N
A1.18 CH2CH3 s C-Cl CH2OCH2CH3 CH2 N
M mo toto D-D s toto £9" IV
K JHD H DO s toto 191V
N JH3 totooto ■*so s to 09'IV
N JHD £HDOto ■*ao s to 65- IV
N 4HD HDDto *so s to 8£"IV
N dHD to=DzHD *ao s to LS'W
N dHD toto *so s to 95''IV
M JHD H -tao s to snv
N JHD totooto DO s to WIV
N JHD £HDOto DO s to env
N JHD HD'Dto DO s to znv
N dHO tooto D-D s to IS* IV
N iHD toto D-D s to OSIV
N JHD H D-D s to 6VIV
N (£HD)HD totooto JflO s toto 8KIV
N (to)HD tooto •ia-D s toto Z,fr'lV
N (£HD)HD HD'Dto ■ta-D s toto 9frIV
N (£HD)HD tooto ■*ao s toto stnv
N (to)HD toto ja-D s toto WW
K (to)HO H *ao s toto zvw
K (to)H3 totooto DO s toto zvxv
N (£HD)HD tooto D-D s toto itav
N (to)HD HDDto DO :■: S toto *■ 0fr"lV
N (to)HD *HDOto D-D s itoto 6£IV
M (toto toto D-D s toto 8fIV
M (to)HO H D-D s toto ^nv
N (£HD)HD totooto ■ta-D s to 9£TV
N (£HD)HD tooto *ao s to snv
N (to)HD HDDto ^ao s to t£'IV
N (£HD)HD tooto ^ao s to ££'IV
N (to)HD tozHD ^ao s to ZE'IV
N (to)HO H ja-D s to IHV
N (£HD)HD totooto D-D s to onv
M (to)HD tooto DO s to 6nv
M (£HD)HD HDDto D-D s to snv
N (to)HD tooto D-D s to LZ'IY
K (EHD)HD toto DO s to 9rtv
N (EHD)HD H D-D s to sriv
N ZHD totooto ■*ao s toto wriv
M ZHD tooto *ao s toto env
K to HDDto *ao s toto ZZ\Y
N to tooto ^ao s toto inv
K to toto *ao s toto onv
N to H ■*ao s toto 6l'IV
A 1.63 CH2CH3 S C-Cl CH2C=CH2 CHF N
A1.64 Cri2C—ri3 s C-Cl CH2C.CH CHF N
A1.65 Cri2Cri3 s C-Cl CH2OCH3 CHF N
Al.66 CH2CH3 s C-Cl CH2OCH2CH3 CHF N
A1.67 " CH2CH3 s C-Br H CHF N
A1.68 CH2CH3 s C-Br CH2CH3 CHF N
A1.69 CH2CH3 s C-Br CH2C=Gri2 CHF N
A1.70 CH2CH3 s C-Br CH2CCH CHF N
A1.71 CH2CH3 s C-Br CH2OCH3 CHF N
A1.72 CH2CH3 s C-Br CH2OCH2CH3 CHF N
A1.73 CH3 s C-Cl H CH20 N
A1.74 CH3 s C-Cl CH.2Cri3 CH20 N
A1.75 CH3 s C-Cl C.H2C=CH2 CH20 N
A1.76 CH3 s C-Cl CH2C.CH CH20 N
A1.77 CH3 s C-Cl CH2OCH3 CH20 N
A1.78 CH3 s C-Cl CH2OCH2CH3 CH20 N
A1.79 CH3 s C-Br H CH20 N
A1.80 CH3 s C-Br CH2CH3 CH20 N
A1.81 CH3 s C-Br CH20=Cri2 CH20 N
A1.82 CH3 s C-Br CH2CCH CH20 N
A1.83 CH3 s C-Br CH2OCH3 CH|0 N ■•/;
A1.84 CH3 s C-Br CH2OCH2CH3 CH20 N
A1.85 Cxi2Cri3 s C-Cl H CH20 N
A1.86 CH2CH3 s C-Cl CH2CH3 CH20 N
A1.87 CH2CH3 s C-Cl CH2C=CH2 CH2Q N
A1.88 C_ri2CH.3 s C-Cl CH2C.CH CH20 N
A1.89 CH2CH3 s C-Cl CH2OCH3 CH20 N
A1.90 CH2CH3 s C-Cl CH2OCH2CH3 CH20 N
A1.91 CH2CH3 s C-Br H CH20 N
A1.92 CH2CH3 s C-Br CH2Cri3 CH20 N
A 1.93 CH2CH3 s C-Br CH2C=CH2 CH20 N
A1.94 CH2CH3 s C-Br CH2C.CH CH20 N
A1.95 CH2CH3 s C-Br CH2OCH3 CH20 N
A1.96 CH2CH3 s C-Br CH2OCH2CH3 CH20 N
A1.97 CH3 CH=CH C-Cl H CH2 N
A1.98 CH3 CH=CH C-Cl CH2CH3 CH2 N
A1.99 CH3 CH=CH C-Cl CH2C=CH2 CH2 N
A1.100 CH3 CH=CH C-Cl CH2C.CH CH2 N
A1.101 CH3 CH=CH C-Cl CH2OCH3 CH2 N
A1.102 CH3 CH=CH C-Cl CH2OCH2CH3 CH2 N
A1.103 CH2CH3 CH=CH C-Cl H CH2 N
A1.104 CH2CH3 CH=CH C-Cl CH2CH3 CH2 N
A1.105 CH2CH3 CH=CH C-Cl CH2C^CH2 CH2 N
A1.106 CH2CH3 CH=CH C-Cl CH2C.CH CH2 N
A1.107 C.H2CH3 CH=CH C-Cl CH2OCH3 CH2 N
A1.108 CH2CH3 CH=CH C-Cl CH2OCH2CH3 CH2 N
A1.109 CH3 CH=CH C-Cl H CH(CH3) N
A1.110 CH3 CH=CH C-Cl CH2CH3 CH(CH3) N
Al.lll CH3 CH=CH C-Cl CH2C=CH2 CH(CH3) N
A1.112 CH3 CH=CH C-Cl CH2C.CH CH(CH3) N
A1.113 CH3 CH=CH C-Cl CH2OCH3 CH(CH3) N
A1.114 CH3 CH=CH C-Cl CH2OCH2CH3 CH(CHj) N
A1.115 CH2CH3 CH=CH C-Cl H CH(CH3) N
A1.116 (JH.2CH3 CH=CH C-Cl CH2Cri3 CH(CH3) N
A1.117 CH2CH3 CH=CH C-Cl CH2C=CH2 CH(CH3) N
A1.118 CH2CH3 CH=GH C-Cl CH2C.CH CH(CH3) N
A1.119 CH2CH3 CH=CH C-Cl CH2OCH3 ., CH(CH3) N
A1.120 CH2CH3 CH=CH C-Cl CH2OCH2CH3 CH(CH3) N
A1.121 CH3 CH=CH C-Cl H CHF N
A1.122 CH3 CH=CH C-Cl CH2CH3 CHF N
A1.123 CH3 CH=CH C-Cl CH2C=CH2 CHF N
A1.124 CH3 CH=CH C-Cl CH2C.CH CHF N
A1.125 CH3 CH=CH C-Cl CH2OCH3 CHF N
A1.126 CH3 CH=CH C-Cl CH2OCH2CH3 CHF N
A1.127 OH.2CH3: CH=CH C-Cl H .- CHF: N
A1.128 ; CH.2t-ri3 CH=CH ;:■> C-Cl CH2CH3 CHF N '
A1129 CH2CH3 CH=CH C-Cl CH2C=:Cri2 CHF N
A1.130 CH2CH3 GHNCH C-Cl CH2C.CH CHF N
A1.131 CH2CH3 CH=CH C-Cl CH2OCH3 CHF N
A1.132 CH2CH3 CH=CH C-Cl CH2OCH2CH3 CHF N
A1.133 CH3 CH=CH C-Cl H CH20 N
A1.134 CH3 CH=CH C-Cl CH2CH3 CH20 N
A1.135 CH3 CH=CH C-Cl CH2C=CH2 CH20 N
A1.136 CH3 CH=CH C-Cl CH2C.CH CH20 N
A1.137 CH3 CH=CH C-Cl CH2OCH3 CH20 N
A1.138 CH3 CH=CH C-Cl CH2OCH2CH3 CH20 N
A1.139 CH2CH3 CH=CH C-Cl H CH20 N
A1.140 Cri2CH3 CH=CH C-Cl CH2Cxi3 CH20 N
A1.141 CH2CH3 CH=CH C-Cl CH2C=CH2 CH20 N
A1.142 CH2CH3 CH=CH C-Cl CH2C.CH CH20 N
A1.143 CH2CH3 CH=CH C-Cl CH2OCH3 CH20 N
A1.144 CH2CH3 CH=CH C-Cl CH2OCH2CH3 CH20 N
A1.145 CH3 S C-Cl H CH2 C-H
Al.1.46 CH3 S C-Cl CH2Cri3 CH2 C-H
A1.147 CH3 s C-Cl CH2C=CH2 CH2 C-H
A1.148 CH3 s C-Cl CH2C.CH CH2 C-H
A1.149 CH3 s C-Cl CH2OCH3 CH2 C-H
A1.150 CH3 s C-Cl CH2OCH2CH3 CH2 C-H
A1.195 CH3 s C-Cl CH2C—CH2 CH(CH3) C-H
A1.196 CH3 s C-Cl CH2C.CH CH(CH3) C-H
A1.197 CH3 s C-Cl CH2OCH3 CH(CH3) C-H
A1.198 CH3 s C-Cl CH20CH2CH3 CH(CH3) C-H
A1.199 CH3 s C-Br H CH(CH3) C-H
AL200 CH3 s C-Br CH2CH3 CH(CH3) C-H
A1.201 CH3 s C-Br CH2C:=Cxi2 CH(CH3) C-H
A1.202 CH3 s C-Br CH2C.CH CH(CH3) C-H
AL203 CH3 s C-Br CH2OCH3 CH(CH3) C-H
A1.204 CH3 s C-Br CH2OCH2CH3 CH(CH3) C-H
A1.205 CH2CH3 s C-Cl H CH(CH3) C-H
A1.206 CIi2CH3 s C-Cl CH2CH3 CH(CH3) C-H
A1.207 CH2CH3 s C-Cl CH2C=Cri2 CH(CH3) C-H
A1.208 CH2CH3 s C-Cl CH2C.CH CH(CH3) C-H
A1.209 CH2CH3 s C-Cl CH2OCH3 CH(CH3) C-H
A1.210 CH2CH3 s C-Cl CH2OCH2CH3 CH(CH3) C-H
AL211 CH2CH3 s C-Br H CH(CH3) C-H
A1.212 CH2CH3 s C-Br CH2CH3 CH(CH3) C-H
A1.213 CH2CH3 s C-Br CH2C=CH2 CH(CH3) C-H
A1.214 CH2CH3 s C-Br CH2C.CH CH(CH3) C-H
A1.215 Ui20H3 i s C-Br CHiOCHj m^mo C-H
A1.216 CH2CH3 s C-Br CH2OCH2CH3 CHCCHj) C-H
A1.217 CH3 s C-Cl H CH(CH3) C-Cl
A1.218 CH3 s C-Cl CH2CH3 CH(CH3) C-Cl
A1.219 CH3 s C-Cl CH2C=CH2 CH(CH3) C-Cl
A1.220 CH3 s C-Cl CH2C.CH CH(CH3) C-Cl
A1.221 CH3 s C-Cl CH2OCH3 CH(CH3) C-Cl
A1.222 CH3 s C-Cl CH2OCH2CH3 CH(CH3) C-Cl
A1.223 CH3 s C-Br H CH(CH3) C-Cl
A1.224 CH3 s C-Br CH2CH3 CH(CH3) C-Cl
A1.225 CH3 s C-Br CH2C=CH2 CH(CH3) C-Cl
AL226 CH3 s C-Br CH2C.CH CH(CH3) C-Cl
A1.227 CH3 s C-Br CH2OCH3 CH(CH3) C-Cl
A1.228 CH3 s C-Br CH2OCH2CH3 CH(CH3) C-Cl
A1.229 CH2CH3 s C-Cl H CH(CH3) C-Cl
A1.230 CH2CH3 s C-Cl CH2CH3 CH(CH3) C-Cl
Ai.231 CH2CH3 s C-Cl CH2C=CH2 CH(CH3) C-Cl
A1.232 CH2CH3 s C-Cl CH2C.CH CH(CH3) C-Cl
A1.233 CH2CH3 s C-Cl CH2OCH3 CH(CH3) C-Cl
A1.234 CH2CH3 s C-Cl CH2OCH2CH3 CH(CH3) C-Cl
A1.235 CH2CH3 s C-Br H CH(CH3) C-Cl
A1.236 CH2CH3 s C-Br CH2CH3 CH(CH3) C-Cl
A1.237 CH2CH3 s C-Br Cxl2Cs=CH2 CH(CH3) C-Cl
A1.238 CH2CH3 0 C-Br CH2C.CH CH(CH3) C-Cl
A1.239 CH2CH3 S C-Br CH2OCH3 CH(CH3) C-Cl
A1.240 CH2CH3 s C-Br CH2OCH2CH3 CH(CH3) C-Cl
A1.241 CH3 s C-Cl H CHF C-H
A1.242 CH3 s C-Cl CH2CH3 CHF C-H
A1.243 CH3 s C-Cl CH2C=CH2 CHF C-H
A1.244 CH3 s C-Cl CH2C.CH CHF C-H
A1.245 CH3 s C-Cl CH2OCH3 CHF C-H
A1.246 CH3 s C-Cl CH2OCH2CH3 CHF C-H
A1.247 CH3 s C-Br H CHF C-H
A1.248 CH3 s C-Br CH2CH3 CHF C-H
A1.249 CH3 s C-Br CH2C=CH2 CHF C-H
A1.250 CH3 s C-Br CH2C,CH CHF C-H
A1.251 CH3 s C-Br CH2OCH3 CHF C-H
A1.252 CH3 s C-Br CH2OCH2CH3 CHF C-H
A1.253 CH2CH3 s C-Cl H CHF C-H
A1.254 CH2CH3 s C-Cl CH2CH3 CHF C-H
A1.255 CH2CH3 s C-Cl GH2C=CH2 CHF C-H
A1.256 CH2CH3 s C-Cl CH2C.CH CHF C-H
A1.257 CH2CH3 s C-Cl CH2OCH3 CHF C-H
A1.258 GJI2CH3 s C-Cl CH2OCH2CH3 CHF C-H
Al.259 V; GHjCIii S .:■■-,■{.■ C^Br iH,> ■ CHF C-H
A1.260 H CHjCH^ Sw C>Br CH2CH3 CHF C-H
Al.261 CHjCHj s C-Br CH2C=Cii2 CHF C-H
A1.262 CH2CH3 s C-Br CH2C.CH CHF C-H
A1.263 CH2CH3 s C-Br CH2OCH3 CHF C-H
A1.264 CH2CH3 s C-Br CH2OCH2CH3 CHF C-H
A1.265 CH3 s C-Cl H CHF C-Cl
A1.266 CH3 s C-Cl CH2CH3 CHF C-Cl
A1.267 CH3 s C-Cl Ori2C^^Cri2 CHF C-Cl
A1.268 CH3 s C-Cl CH2C.CH CHF C-Cl
A1.269 CH3 s C-Cl CH2OCH3 CHF C-Cl
AI.270 CH3 s C-Cl CH2OCH2CH3 CHF C-Cl
A1.271 CH3 s C-Br H CHF C-Cl
A1.272 CH3 s C-Br CH2CH3 CHF C-Cl
A1.273 CH3 s C-Br CH2C==CH2 CHF C-Cl
A1.274 CH3 s C-Br CH2C.CH CHF C-Cl
A1.275 CH3 s C-Br CH2OCH3 CHF C-Cl
A1.276 CH3 s C-Br CH2OCH2CH3 CHF C-Cl
A1.277 CH2CH3 s C-Cl H CHF C-Cl
A1.278 CH2CH3 s C-Cl CH2CH3 CHF C-Cl
A1.279 CH2CH3 s C-Cl CH2C==Crl2 CHF C-Cl
A1.280 CH2CH3 s C-Cl CH2C.CH CHF C-Cl
A1.281 CH2CH3 s C-Cl CH2OCH3 CHF C-Cl
A1.282 CH.2CH3 s C-Cl CH2OCH2CH3 CHF C-Cl
A1.283 CH2wi3 S C-Br H CHF C-Cl
A1.284 CH2CH3 s C-Br CH2CH3 CHF C-Cl
A1.285 CH2CH3 s C-Br CH2C=CH2 CHF C-Cl
A1.286 CH2CH3 s C-Br CH2C.CH CHF C-Cl
A1.287 CH2CH3 s C-Br CH2OCH3 CHF C-Cl
A1.288 CH2CH3 s C-Br CH2OCH2CH3 CHF C-Cl
A1.289 CH3 s C-Cl H CH20 C-H
A1.290 CH3 s C-Cl CH2CH3 CH20 C-H
A1.291 CH3 s C-Cl CH2C=CH2 CH20 C-H
A1.292 CH3 s C-Cl CH2C.CH CH20 C-H
A1.293 CH3 s C-Cl CH2OCH3 CH20 C-H
A1.294 CH3 s C-Cl CH2OCH2CH3 CH20 C-H
A1.295 CH3 s C-Br H CH20 C-H
A1.296 CH3 s C-Br CH2CH3 CH20 C-H
A1.297 CH3 s C-Br CH2C=CH2 CH20 C-H
A1.298 CH3 s C-Br CH2C.CH CH20 C-H
A1.299 CH3 s C-Br CH2OCH3 CH20 C-H
A1.300 CH3 s C-Br CH2OCH2CH3 CH20 C-H
A1.301 CH2CH3 s C-Cl H CH20 C-H
A1.302 CH2CH3 s C-Cl ; GH2CH3 CH20 C-H
A1.303; ■■; ,s j CH2CH3- s C-Gl GH2C=CHi n GHiQ ! C-H
AM04' CHjCH^ > S.:r -vy C-0 CH2C.CH CHiO ''■? C-H 1
A1.305 CH2CH3 s C-Cl CH2OCH3 CH20 C-H
A1.306 CH2GH3 s C-Cl CH2OCH2CH3 CH20 C-H
A1.307 CH2GH3 s C-Br H CH20 C-H
A1.308 CHJGHJ s C-Br CH2CH3 CH20 C-H
A1.309 CH2GH3 s C-Br C^O^C^ CH20 C-H
A1.310 CH2CH3 s C-Br CH2C.CH CH20 C-H
A1.311 CH2CH3 s C-Br CH2OCH3 CH20 C-H
A1.312 CH2CH3 s C-Br CH2OCH2CH3 CH20 C-H
A1.313 CH3 S C-Cl H CH20 C-H
A1.314 CH3 s C-Cl CH2CH3 CH20 C-H
A1.315 CH3 s C-Cl CH2C=CH2 CH20 C-H
A1.316 CH3 s C-Cl CH2C.CH CH20 C-H
A1.317 CH3 s C-Cl CH2OCH3 CH20 C-H
Al.31.8 CH3 s C-Cl CH2OCH2CH3 CH20 C-H
A1.319 CH3 s C-Br H CH20 C-H
A1.320 CH3 s C-Br CH2CH3 CH20 C-H
A1.321 CH3 s C-Br Cri2C:=Cri2 CH20 C-H
A1.322 CH3 s C-Br CH2C.CH CH20 C-H
A1.323 CH3 s C-Br CH2OCH3 CH20 C-H
A1.324 CH3 s C-Br CH2OCH2CH3 CH20 C-H
A1.325 CH2CH3 s C-Cl H CH20 C-Cl
A1.326 CH2CH3 s C-Cl CH2CH3 CH20 C-Cl
A1.327 CH2CH3 S C-Cl CH2C—CH2 CH20 C-Cl
A1.328 CH2CH3 S C-Cl CH2C.CH CH20 C-Cl
A1.329 CH2CH3 s C-Cl CH2OCH3 CH20 C-Cl
A1.330 CH2CH3 s C-Cl CH2OCH2CH3 CH20 C-Cl
A1.331 CH2CH3 s C-Br H CH20 C-Cl
AI.332 CH2CH3 s C-Br CH2CH3 CH20 C-Cl
A1.333 CH2CIi3 s C-Br CH2C=CH2 CH20 C-Cl
A1.334 CH2CH3 s C-Br CH2C.CH CH20 C-Cl
A1.335 CH2CH3 s C-Br CH2OCH3 CH20 C-Cl
A1.336 CH2CH3 s C-Br CH2OCH2CH3 CH20 C-Cl
A1.337 CH3 CH=CH C-Cl H CH2 C-H
A1.338 CH3 CH=CH C-Cl CH2CH3 CH2 C-H
A1.339 CH3 CH=CH C-Cl Cri2C'^Cri2 CH2 C-H
A1.340 CH3 CH=CH C-Cl CH2C.CH CH2 C-H
A1.341 CH3 CH=CH C-Cl CH2OCH3 CH2 C-H
A1.342 CH3 CH=CH C-Cl CH2OCH2CH3 CH2 C-H
A1.343 CH2CH3 CH=CH C-Cl H CH2 C-H
A1.344 CH2CH3 CH=CH C-Cl CH2CH3 CH2 C-H
A1.345 CH2CH3 CH=CH C-Cl CH2C=Cri2 CH2 C-H
A1.346 CH2CH3 CH=CH C-Cl CH2CCH CH2 C-H
A1.347 CH2CH3 CH=CH c-ei CH2QCH3 CH2 s C-H
A1.348 CH2€H3 CH=CH C-Cl GH2OCH2CH3 CH2 C-H
A1.349 CH3 CH=CH C-Cl H CH2 C-Cl
A1.350 CH3 CH=CH C-Cl CH2CH3 CH2 C-Cl
A1.351 CH3 CH=CH C-Cl CH2C=CH2 CH2 C-Cl
A1.352 CH3 CH=CH C-Cl CH2C.CH CH2 C-Cl
A1.353 CH3 CH=CH C-Cl CH2OCH3 CH2 C-Cl
A1.354 CH3 CH=CH C-Cl CH2OCH2CH3 CH2 C-Cl
A1.355 CH2CH3 CH=CH C-Cl H CH2 C-Cl
A1.356 CH2CH3 CH=CH C-Cl CH2CH3 CH2 C-Cl
A1.357 CH2CH3 CH=CH C-Cl CH2C=CH2 CH2 C-Cl
A1.358 CH2CH3 CH=CH C-Cl CH2C.CH CH2 C-Cl
A1.359 CH2CH3 CH=CH C-Cl CH2OCH3 CH2 C-Cl
A1.360 CH2Cri3 CH=CH C-Cl CH2OCH2CH3 CH2 C-Cl
A1.361 CH3 CH=CH C-Cl H CH(CH3) C-H
A1.362 CH3 CH=CH C-Cl Cri2Cri3 CH(CH3) C-H
A1.363 CH3 CH=CH C-Cl CH2C=CH2 CH(CH3) C-H
A1.364 CH3 CH=CH C-Cl CH2C.CH CH(CH3) C-H
A1.365 CH3 CH=CH C-Cl CH2OCH3 CH(CH3) C-H
A1.366 CH3 CH=CH C-Cl CH2OCH2CH3 CH(CH3) C-H
A1.367 CH2CH3 CH=CH C-Cl H CH(CH3) C-H
A1.368 CH2CH3 CH=CH C-Cl CH2CH3 CH(CH3) C-H
A1.369 CH2CH3 CH=CH C-Cl CH2C==Cri2 CH(CH3) C-H
A1.370 CH2CH3 CH=CH C-Cl CH2C.CH CH(CH3) C-H
A1.371 CH2CH3 CH=CH C-Cl CH2OCH3 CH(CH3) C-H
A1.372 CH2CH3 CH=CH C-Cl CH2OCH2CH3 CH(CH3) C-H
A1.373 CH3 CH=CH C-Cl H CH(CH3) C-Cl
A1.374 CH3 CH=CH C-Cl CH2CH3 CH(CH3) C-Cl
A1.375 CH3 CH=CH C-Cl CH2C=CH2 CH(CH3) C-Cl
A1.376 CH3 CH=CH C-Cl CHjC.CH CH(CH3) C-Cl
A1.377 CH3 CH=CH C-Cl CH2OCH3 CH(CH3) C-Cl
A1.378 CH3 CH=CH C-Cl CH2OCH2CH3 CH(CH3) C-Cl
A1.379 CH2CH3 CH=CH C-Cl H CH(CH3) C-Cl
A1.380 CH2CH3 CH=CH C-Cl CH2CH3 CH(CH3) C-Cl
A1.381 CH2CH3 CH=CH C-Cl CH2C=CH2 CH(CH3) C-Cl
A1.382 CH2CHj CH=CH C-Cl CH2C.CH CH(CH3) C-Cl
A1.383 L-HjC^rlj CH=CH C-Cl CH2OCH3 CH(CH3) C-Cl
A1.384 CH2CH3 CH=CH C-Cl CH2OCH2CH3 CH(CH3) C-Cl
A1.385 CH3 CH-CH C-Cl H CHF C-H
A1.386 CH3 CH=CH C-Cl CH2CH3 CHF C-H
A1.387 CH3 CH=CH C-Cl CH2C=CH2 CHF C-H
A1.388 CH3 CH=CH C-Cl CHjC-CH. CHF C-H
A1.389 CH3 GH=CH C-Cl CH2OCH3 CHF C-H
A1.390 CH3 CH=CH c-ei CH2OCH2CH3 CHF C-H
MA91 . CHjC^ii^ *€ai=GH ■;■; *e*cav>-: x&soc-:■•.■:.;.>. ,^:rd CHF C-H
A1.392 CH2CH3 CH*=CH C-Cl CH2GH3' CHF C^H
A1.393 CH2CH3 CH=CH C-Cl CH2C—CH2 CHF C-H
A1.394 CH2CH3 CH=CH C-Cl CH2C.CH CHF C-H
A1.395 GH2CHj CH=CH C-Cl CH2OCH3 CHF C-H
A1.396 CH2CH3 CH=CH C-Cl CH2OCH2CH3 CHF C-H
A1.397 CH3 CH=CH C-Cl H CHF C-Cl
A1.398 CH3 CH=CH C-Cl CH2CH3 CHF C-Cl
AL399 CH3 CH=CH C-Cl CH2C=CH2 CHF C-Cl
A1.400 CH3 CH=CH C-Cl CH2C.CH CHF C-Cl
A1.401 CH3 CH=CH C-Cl CH2OCH3 CHF C-Cl
A1.402 CH3 CH=CH C-Cl CH2OCH2CH3 CHF C-Cl
A1.403 CH2CH3 CH=CH C-Cl H CHF C-Cl
A1.404 CH2CH3 CH=CH C-Cl CH2CH3 CHF C-Cl
A1.405 CHJCHJ CH=CH C-Cl CH2C=CH2 CHF C-Cl
A1.406 CH2CH3 CH=CH C-Cl CH2C.CH CHF C-Cl
A1.407 CH2CH3 CH=CH C-Cl CH2OCH3 CHF C-Cl
A1.408 CH2CH3 CH=CH C-Cl CH2OCH2CH3 CHF C-Cl
A1.409 CH3 CH=CH C-Cl H CH20 C-H
A1.410 CH3 CH=CH C-Cl CH2CH3 CH20 C-H
A1.411 CH3 GH=CH C-Cl CH2C=CH2 CH20 C-H
A1.412 CH3 CH=CH C-Cl CH.2C-"Crl CH20 C-H
A1.413 CH3 CH=CH C-Cl CH2OCH3 CH20 C-H
A1.414 CH3 CH=CH C-Cl 1 CH2OCH2CH3 CH20 C-H
A1.415
CH2CH3 CH=CH C-Cl H CH20 C-H
A1.416 CH2CH3 CH=CH C-Cl CH2CH3 CH20 C-H
A1.417 CH2CH3 CH=CH C-Cl CH20:=Cri2 CH20 C-H
AL418 CH2CH3 CH=CH C-Cl CH2C.CH CH20 C-H
A1.419 CH2CH3 CH=CH C-Cl CH2OCH3 CH20 C-H
A1.420 CH2CH3 CH=CH C-Cl CH2OCH2CH3 CH20 C-H
A1.421 CH3 CH=CH C-Cl H CH20 C-Cl
A1.422 CH3 CH=CH C-Cl CH2Cri3 CH20 C-Cl
A1.423 CH3 CH=CH C-Cl GH2C=CH2 CH20 C-Cl
A1.424 CH3 CH=CH C-Cl CH2C.CH CH20 C-CI
A1.425 CH3 CH=CH C-Cl CH2OCH3 CH20 C-Cl
A1.426 CH3 CH=CH C-Cl CH2OCH2CH3 CH20 C-Cl
A1.427 CH2CH3 CH=CH C-Cl H CH20 C-Cl
A1.428 CH2CH3 CH=CH C-Cl CH2CH.3 CH20 C-Cl
A1.429 CH2CH3 CH=CH C-Cl \_H2C=CH2 CH20 C-Cl
A1.430 CH2CH3 CH=CH C-Cl CH2C.CH CH20 C-Cl
A1.431 CH2CH3 CH=CH C-Cl CH2OCH3 CH20 C-Cl
A1.432 CH2CH3 CH=CH C-Cl CH2OCH2CH3 CH20 C-Cl
Table A2
■Table A2 provides 432 compounds of Formula Al wherein RVDJ E, R11, A and J arc as defined in Table Al&ridR6 is^ ethyl.
Table A3
Table A3 provides 432 compounds of Formula Al wherein R1, D, E, Ru, A and J are as defined in Table Al and R6 is H-propyl.
Table A4
Table A4 provides 432 compounds of Formula Al wherein R1, D, E, Rn, A and J are as defined in Table Al and R6 is wo-propyl.
Table A5
Table A5 provides 432 compounds of Formula Al wherein R1, D, E, R", A and J are as defined in Table Al and R6 is /i-butyl.
Table A6
Table A6 provides 432 compounds of Formula Al wherein R1, D, E, R", A and J are as defined in Table Al and R6 is sec-butyl.
Table A7 Table A7 provides 432 compounds of Formula Al wherein R\ D, E, R", A and J are as defined in Table Al and R6 is iso-butyl.
Table A8
Table A8 provides 432 compounds of Formula Al wherein R1, D, E, R11, A and J are as defined in Table Al and R6 is tert-butyl.
Table A9
Table A9 provides 432 compounds of Formula Al wherein R\ D, E, R11, A and J are as defined in Table Al and R6 is w-pentyl.
Table A10
ljO Table A10 provides 432 compounds of Formula Al wherein R\ D, E, R", A and J
are as defined in Table Al and R6 is 1-methylbutyl.
Table All
Table Al 1 provides 432 compounds of Formula Al wherein R1, D, E, R11, A and J 1|5 are as defined in Table Al and R6 is 2-methylbutyl.
Table A12
Table A12 provides 432 compounds of Formula Al wherein R1, D, E, R", A and J are as defined in Table Al and R6 is 3-methylbutyl. 210
Table A13 Table A13 provides 432 compounds of Formula Al wherein R\ D, E, Rn, A and J are as defined in Table Al and R6 is heopentyl.
2|5 Table A14
Table A14 provides 432 compounds of Formula Al wherein R1, D, E, R11, A and J are as defined in Table Al and R6 is 2,2-dimethylbutyl.
Table A15
3|0 Table A15 provides 432 compounds of Formula Al wherein R\ D, E, R11, A and J
are as defined in Table Al and R6 is 2,2,2-trifluoroethyl.
Table A16
Table A16 provides 432 compounds of Formula Al wherein R1, D, E, R11, A and J 3f5 are as defined in Table Al and R6 is 2,2-difluoro-2-methoxyethyl.
Table A17
Table A17 provides 432 compounds of Formula Al wherein R\ D, E, R", A and J 4p are as defined in Table Al and R6 is 3,3,3-trifluoropropyl.
Table A18
Table A18 provides 432 compounds of Formula Al wherein R1, D, E, R11, A and J are as defined in Table Al and R6 is/>ara-fmorobenzyl.
45
Table A19
Table A19 provides 432 compounds of Formula Al wherein R1, D, E, R11, A and J are as defined in Table Al and R6 is 2,4-dichlorophenyl.
Table A20
Table A20 provides 432 compounds of Formula Al wherein R1, D, E, R11, A and J are as defined in Table Al and R6 is 2-chloro-4-trifluoromethylphenyl.
Table A21
ID Table A21 provides 432 compounds of Formula Al wherein R\ D, E, Ru, A and J
are as defined in Table Al and R6 is 4-trifluoromethylphenyl.
15
Table Bl
Table Bl provides 288 compounds of Formula Bl wherein R\ D, E, R11, A and J are as defined in Table Bl and R6 is methyl.
N
NUr
N-R"
(B1)
in
23
Table Bl
Compound No. R* D E R11 A J
Bl.l CH3 S C-Cl H CH2 C-H
B1.2 CH3 S C-Cl CH2CH3 CH2 C-H
B1.3 CH3 s C-Cl CH2C=CH2 CH2 C-H
B1.4 CH3 s C-Cl CH2C.CH CH2 C-H
B1.5 CH3 s C-Cl CH2OCH3 CH2 C-H
B1.6 CH3 s C-Cl CH2OCH2CH3 CH2 C-H
B1.7 CH3 s C-Br H CH2 C-H
B1.8 CH3 s C-Br CH2CH3 CH2 _^ C-H
B1.9 CH3 s C-Br CH2C=CH2 CH2 C-H
B1.10 CH3 s C-Br CH2C.CH CH2 C-H
BUI CH3 s C-Br CH2OCH3 CH2 C-H
B1.12 CH3 s C-Br CH2OCH2CH3 CH2 C-H
B1.13 CH2CH3 s C-Cl H CH2 C-H
B1.14 CH2CH3 s C-Cl CH2CH3 fCH2 C-H
Bl.15 CH2CH3 s C-Cl CH2C=CH2 CH2 C-H
B1.16 CH2CH3 s C-Cl CH2C.CH CH2 C-H
B1.17 CH2CH3 s C-Cl CH2OCH3 CH2 C-H
B1.18 CH2CH3 s C-Cl CH2OCH2CH3 CH2 C-H
B1.19 CH2CH3 s C-Br H CH2 C-H
B1.20 CH2CH3 s C-Br CH2CH3 CH2 C-H
27
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H-D JHD ZHD=DZHD ID-D s £HD:HD £9'18
HO JHD £HD:HD ID-D s £HDJHD 39'13
HO JHD H ID-D s £HDEHD 1913
HO JHD £HDzHDOzHD ■I9-D s £HD 09* i a
H-D JHD £HDO'HD ja-D s EHD 65' i a
HO JHD HDDZHD ■ia-D s £HD 8sia
H-D JHD zHD=DrHD m-o s £HD LS'IQ
H-D JHD £HDrHD •*a-D s £HD 9S*ia
H-D JHD H ja-D s £HD ssia
H-D JHD £HD'HDOrHD ID-D s £HD wia
H-D JHD £HDOzHD ID-D s £HD ££'ia
H-D JHD HD'D'HD D-D s £HD zsia
H-D JHD ZHD=DZHD ID-D s £HD ina
H-D JHD 'HD'HD ID-D s £HD osia
H-D JHD H ID-D s £HD 6^"ia
H-D (€HD)HD £HDzHDOzHD *a-D s £HDZHD 8ft a
H-D (eHD)HD 'HDOto •*a-D s £HDJHD LVW
H-D (£HD)HD HDDZHD ■ia-D s £HDJHD 9fr*ia
H-D (£HD)HD 3HD=DZHD ja-D s £HDCHD SVIQ
H-D (£HD)HD £HDJHD ja-D s £HDCHD trria
H-D (EHD)HD H ja-D s £HD:HD £VIQ
H-D (eHD)HD £HD*HDOJHD D-D! s £HDCHD zria
H-D (£HD)HD £HDO*HD ID-D s fli^ED iria
H-D (£HD)HD HDD'HD ID-D s £HDrHD on a
H-D (£HD)HD CHD=DCHD ID-D s £HDCHD 6£ia
H-D (£HD)HD £HDZHD D-D s £HD*HD sria
H-D (£HD)HD H ID-D s £HDCHD z,na
H-D (£HD)HD £HDEHDOzHD •ia-D s £HD 9rta
H-D (£HD)HD £HDOcHD •ta-D s £HD sna
H-D (£HD)HD HDD'HD •la-D s £HD n'iQ
H-D (£HD)HD JHD=DrHD *a-D s £HD ££'ta
H-D (£HD)HD £HDEHD *a-D s £HD zna
H-D (£HD)HD H •ia-D s £HD ina
H-D (£HD)HD £HDcHDOzHD ID-D s £HD or i a
H-D (£HD)HD £HDO'HD o-o s £HD 6Z'i a
H-D (£HD)HD HD'DZHD ID-D s £HD sna
H-D (£HD)HD EHD=D£HD ID-D s £HD zria
H-D (£HD)HD £HDZHD ID-D s £HD 9na
H-D (£HD)HD H ID-D s £HD sna
H-D EHD £HDcHDO:HD ia-D s £HDZHD *ria
H-D :HD cHDOzHD ^a-D s £HD'HD £na
H-D *HD HD'D'HD •ta-D s toto trie
H-D ZHD *HD=DZHD ja-D s £HDJHD ina
B1.65 CH2CH3 S C-Cl CH2OCH3 CHF C-H
B1.66 CH2CH3 s C-Cl CH2OCH2CH3 CHF C-H
B1.67 CH2CH.3 s C-Br H CHF C-H
B1.68 CH2CH3 s C-Br CH2CH3 CHF C-H
B1.69 CH2CH3 s C-Br CH2C=CH2 CHF C-H
B1.70 CH2CH3 s C-Br CH2C.CH CHF C-H
B1.71 CH2CH3 s C-Br CH2OCH3 CHF C-H
B1.72 CH2CH3 s C-Br CH2OCH2CH3 CHF C-H
B1.73 CH3 s C-Cl H CH20 C-H
B1.74 CH3 s C-Cl CH2CH3 CH20 C-H
B1.75 CH3 s C-Cl CH2C=CH2 CH20 C-H
B1..76 CH3 s C-Cl CH2C.CH CH20 C-H
B1.77 CH3 s C-Cl CH2OCH3 CH20 C-H
B1.78 CH3 s C-Cl CH2OCH2CH3 CH20 C-H
B1.79 CH3 s C-Br H CH20 C-H
B1.80 CH3 s C-Br CH2CH3 CH20 C-H
B1.81 CH3 s C-Br CH2C=CH2 CH20 C-H
B1.82 CH3 s C-Br CH2C.CH CH20 C-H
B1.83 CH3 s C-Br CH2OCH3 CH20 C-H
B.1.84 CH3 s C-Br CH2OCH2CH3 CH20 C-H
B1.85 GH2GH3 s C-Cl H ! CH20 C-H
B1.86 CH2CH3 S C-Cl CHjCHj CH20 C-H
B1.87 CH2CH3 s C-Cl CH2C=CH2 CH20 C-H
B1.88 CH2CH3 s C-Cl CH2C.CH CH20 C-H
B1.89 CH2CH3 s C-Cl CH2OCH3 CH20 C-H
B1.90 CH2CH3 s C-Cl CH2OCH2CH3 CH2Q C-H
B1.91 CH2CH3 s C-Br H CH20 C-H
B1.92 CH2CH3 S C-Br CH2CH3 CH20 C-H
B1.93 CH2CH3 s C-Br CH2C=CH2 CH20 C-H
B1.94 CH2CH3 s C-Br CH2C.CH CH20 C-H
B1.95 GH2CH3 s C-Br CH2OCH3 CH20 C-H
B1.96 CH2CH3 s C-Br CH2OCH2CH3 CH20 C-H
B1.97 CH3 s C-Cl H CH2 C-Cl
B1.98 CH3 s C-Cl CH2CH3 CH2 C-Cl
B1.99 CH3 s C-Cl CH2C=CH2 CH2 C-Cl
B1.100 CH3 s C-Cl CH2C.CH CH2 C-Cl
BL101 CH3 s C-Cl CH2OCH3 CH2 C-Cl
B1.102 CH3 s C-Cl CH2OCH2CH3 CH2 C-Cl
B1.103 CH3 s C-Br H CH2 C-Cl
B1.104 CH3 s C-Br CH2CH3 CH2 C-Cl
B1.105 CH3 s C-Br CH2C=CH2 CH2 C-Cl
B1.106 CH3 s C-Br CH2C.CH CH2 C-Cl
B1.107 CH3 s C-Br CH2OCH3 CH2 C-Cl
B1.108 CH3 S C-Br CH2OCH2CH3 CH2 C-Cl
B1.109 CH2CH3 S C-Cl H CH2 C-Cl
B1.110 CH2CH3 s C-Cl CH2CH3 CH2 C-Cl
Bl.lll CH2CH3 s C-Cl CH2vJ=CH2 CH2 C-Cl
B1.112 CH2CH3 s C-Cl CH2C.CH CH2 C-Cl
B1.113 CH2CH3 s C-Cl CH2OCH3 CH2 C-Cl
B1.114 CH2CH3 s C-Cl CH2OCH2CH3 CH2 C-Cl
B1.115 CH2CH3 s C-Br H CH2 C-Cl
B1.116 CH2CH3 s C-Br CH2CH3 CH2 C-Cl
B1.117 CH2CH3 s C-Br GH2C=CH2 CH2 C-Cl
B1.118 CH2CH3 s C-Br CH2C.CH CH2 C-Cl
B1.119 CH2CH3 s C-Br CH2OCH3 CH2 C-Cl
B1.120 CH2CH3 s C-Br CH2OCH2CH3 CH2 C-Cl
B1.121 CH3 s C-Cl H CH(CH3) C-Cl
B1.122 CH3 s C-Cl CH2CH3 CH(CH3) C-Cl
B1.123 CH3 s C-Cl CH2C=CH2 CH(CH3) C-Cl
B1.124 CH3 s C-Cl CH2C.CH CH(CH3) C-Cl
B1.125 CH3 s C-Cl CH2OCH3 CH(CH3) C-Cl
B1.126 CH3 s C-Cl CH2OCH2CH3 CH(CH3) C-Cl
B1.127 CH3 s C-Br H CH(CH3) C-Cl
B1.128 CH3 s C-Br CH2CH3 L CH(CH3) C-Cl
B1.129 CH3 > s C-Br CH2C=CH2 cwm C-Cl
B1.130 CH3 ':■ s C-Br CH2C.CH CH(Cm C-Cl
B1.131 CH3 s C-Br CH2OCH3 CH(CH3) C-Cl
B1.132 CH3 s C-Br CH2OCH2CH3 CH(CH3) C-Cl
B1.133 CH2CH3 s C-Cl H CH(CH3) C-Cl
B1.134 Crl2CH3 s C-Cl Orl2CH3 CH(CH3) C-Cl
B1.135 CH2CH3 s C-Cl CH2C=CH2 CH(CH3) C-Cl
B 1.136 CH2CH3 s C-Cl CH2C.CH CH(CH3) C-Cl
B1.137 CH2CH3 s C-Cl CH2OCH3 CH(CH3) C-Cl
B1.138 CH2CH3 s C-Cl CH2OCH2CH3 CH(CH3) C-Cl
B1.139 CH2CH3 s C-Br H CH(CH3) C-Cl
B1.140 CH2CH3 s C-Br OH2CH3 CH(CH3) C-Cl
B1.141 CH2CH3 s C-Br CH2C=CH2 CH(CH3) C-Cl
B 1.142 CH2CH3 s C-Br CH2C.CH CH(CH3) C-Cl
B1.143 CH2CH3 s C-Br CH2OCH3 CH(CH3) C-Cl
B1.144 CH2CH3 s C-Br CH2OCH2CH3 CH(CH3) C-Cl
B1.145 CH3 s C-Cl H CHF C-Cl
B1.146 CH3 s C-Cl CH2CH3 CHF C-Cl
B1.147 CH3 s C-Cl CH2C=CH2 CHF C-Cl
B1.148 CH3 s C-Cl CH2C.CH CHF C-Cl
B1.149 CH3 s C-Cl CH2OCH3 CHF C-Cl
B1.150 CH3 s C-Cl CH2OCH2CH3 CHF C-CI
B1.151 CH3 s C-Br H CHF C-Cl
B1.152 CH3 s C-Br CH2CH3 CHF C-Cl
1 HO ZHD HD'DCHD IDO HD=HD £HD 96rta
HO to to=DzHD IDO HD=HD to seria
HO to £HDZHD IDO HD=HO £HD fr6na
HO to H IDO HD=HD £HD £6na
IDO OzHD £HDcHDOto *HO S £HDZHD 36ria
IDO Oto eHDOto JSO S £HDCHD i6ria
IDO OzHD HDOzHD jao S £HDZHD 06na
IDO Oto to=DzHD JSO S £HD£HD 68113
IDO OzHD £HDZHD 'HO S £HDZHD 88113
IDO OzHD H jao S £HDZHD z,8iia
IDO Oto £HDtoOzHD IDO S £HDZHD 98iia
IDO OzHD £HDOto IDO S £HDZHD ssna
IDO OzHD HDDZHD IDO S £HDZHD wria
IDO OzHD zHD=Dto IDO S £HDZHD esrta
IDO OzHD £HDZHD IDO s £HDZHD z:sna
IDO OzHD H IDO s £HDZHD isria
IDO OzHD tozHDOzHD •ISO s £HD 08113
IDO OzHD £HDOzHD JflO s £HD 6LVIE
IDO oto HDDto ja-D s £HD SLVIQ
IDO OzHD ZHD=DZHD ■*ao s £HD una
IDO OzHD EHOcHD jao s £HD 9Z.II3
IDO OzHD H jao s £HD sz.na
IDO OzHD totooto IDO s £H0 tLvm
IDO OzHD £HDOto IDO s to eiria
IDO OzHD HD'D'HD IDO s to aria
IDO OzHD zHD=DzHO IDO s to una
IDO 0ZH0 £HDZHD IDO s to oz.na
IDO OzHD H IDO s to 69iia
IDO dHD £HOtoOzHD ■fao s toto 89iia
IDO dHD £HDOto jao s to'HD L9VIQ.
IDO dHD HDDZHD •tao s toto 99iia
IDO dHD ZHD=DCHD jao s £HDZHD £9na
IDO dHD £HDZHD jao s toto wria
IDO dHD H jao s toto e9ita
IDO dHD totooto IDO s toto 39ria
IDO dHD eHDOzHD IDO s toto i9iia
IDO dHD HDDto IDO s toto 09ria
IDO dHD ZHD=DZHD IDO s toto 6sna
IDO dHD £HDZHD IDO s toto ssna
IDO dHD H IDO s toto LSVW
IDO dHD £HDcHDO'HD jao s to 9sna
IDO dHD eHDOto jao s to ssna
IDO dHD HDDZHD *ao s to wna
IDO dHD zHD=Dto I -tao S to csna 1
B1.197 CH3 CH=CH C-Cl CH2OCH3 CH2 C-H
B1.198 CH3 CH=CH C-Cl CH20CH2CH3 CH2 C-H
B1.199 CH2CH3 CH=CH C-Cl H CH2 C-H
B 1.200 CH2CH3 CH=CH C-Cl CH2CH3 CH2 C-H
B1.201 CH2CH3 CH=CH C-Cl CH2C=CH2 CH2 C-H
B 1.202 CH2CH3 CH=CH C-Cl CH2C.CH CH2 C-H
B 1.203 CH2CH3 CH=CH C-Cl CH2OCH3 CH2 C-H
B 1.204 CH2CH3 CH=CH C-Cl CH2OCH2CH3 CH2 C-H
B 1.205 CH3 CH=CH C-Cl H CH2 C-Cl
B1.206 CH3 CH=CH C-Cl CH2CH3 CH2 C-Cl
B 1.207 CH3 CH=CH C-Cl CH2C=CH2 CH2 C-Cl
B 1.208 CH3 CH=CH C-Cl CH2C.CH CH2 C-Cl
B 1.209 CH3 CH=CH C-Cl CH2OCH3 CH2 C-Cl
B1.210 CH3 CH=CH C-Cl CH2OCH2CH3 CH2 C-Cl
B1.211 CH2CH3 CH=CH C-Cl H CH2 C-Cl
B1.212 CH2CH3 CH=CH C-Cl CH2CH3 CH2 C-Cl
B1.213 CH2CH3 CH=CH C-Cl CH2C=CH2 CH2 C-Cl
B1.214 CH2CH3 CH=CH C-Cl CH2C.CH CH2 C-Cl
B1.215 CH2CH3 CH=CH C-Cl CH2OCH3 CH2 C-Cl
BL216 CH2CH3 CH=CH C-Cl CH2OCH2CH3 CH2 C-Cl
B11217: :) CH3 . CH^CH) :&cr K?: ;■ >7:^;L:' iCH(CHi) C-H
B11218; CH3 1 CH=CH S&l CH2QH3/y.:,v CH(CM C-H
B1.2T9 CH3 CH=CH C-Cl CH2C=CH2 CH(CH3) C-H
B 1.220 CH3 CH=CH C-Cl CH2CCH CH(CH3) C-H
B1.221 CH3 CH=CH C-Cl CH2OCH3 CH(CH3) C-H
B 1.222 CH3 CH=CH C-Cl CH2OCH2CH3 CH(CH3) C-H
B 1.223 CH2CH3 CH=CH C-Cl H CH(CH3) C-H
B 1.224 CH2CH3 CH=CH C-Cl CH2CH3 CH(CH3) C-H
B 1.225 CH2CH3 CH=CH C-Cl CH2C=CH2 CH(CH3) C-H
B 1.226 CH2CI13 CH=CH C-Cl CH2C.CH CH(CH3) C-H
B 1.227 CH2CH3 CH=CH C-Cl CH2OCH3 CH(CH3) C-H
B 1.228 CH2CH3 CH=CH C-Cl CH2OCH2CH3 CH(CH3) C-H
B 1.229 CH3 CH=CH C-Cl H CH(CH3) C-Cl
B1.230 CH3 CH=CH C-Cl Cri2CH3 CH(CH3) C-Cl
B1.231 CH3 CH=CH C-Cl CH2C=CH2 CH(CH3) C-Cl
B 1.232 CH3 CH=CH C-Cl CH2C.CH CH(CH3) C-Cl
B 1.233 CH3 CH=CH C-Cl CH2OCH3 CH(CH3) C-Cl
B1.234 CH3 CH=CH C-Cl CH2OCH2CH3 CH(CH3) C-Cl
B 1.235 CH2CH3 CH=CH C-Cl H CH(CH3) C-Cl
B 1.236 Cxi2CH3 CH=CH C-Cl CH2CH3 CH(CH3) C-Cl
B 1.237 CH2CH3 CH=CH C-Cl OH2C=CH2 CH(CH3) C-Cl
B1.238 CH2CH3 CH=CH C-Cl CH2C.CH CH(CH3) C-Cl
B 1.239 CH2CH3 CH=CH C-Cl CH2OCH3 CH(CH3) C-Cl
| B 1.240 CH2CH3 CH=CH C-Cl CH2OCH2CH3 CH(CH3) C-Cl
B 1.241 CH3 CH=CH C-Cl H CHF C-H
B 1.242 CH3 CH=CH C-Cl CH2CH3 CHF C-H
B 1.243 CH3 CH=CH C-Cl Cti2C=C.H2 CHF C-H
B 1.244 CH3 CH=CH C-Cl CH2C.CH CHF C-H
B 1.245 CH3 CH=CH C-Cl CH2OCH3 CHF C-H
B 1.246 CH3 CH=CH C-Cl CH2OCH2CH3 CHF C-H
B 1.247 CH2CH3 CH=CH C-Cl H CHF C-H
B 1.248 CH2CH3 CH=CH C-Cl CH2CH3 CHF C-H
B 1.249 CH2CH3 CH=CH C-Cl CH2C=CH2 CHF C-H
B 1.250 CH2CH3 CH=CH C-Cl CH2C.CH CHF C-H
B1.251 CH2CH3 CH=CH C-Cl CH2OCH3 CHF C-H
B 1.252 CH2CH3 CH=CH C-Cl CH2OCH2CH3 CHF C-H
B 1.253 CH3 CH=CH C-Cl H CHF C-Cl
B 1.254 CH3 CH=CH C-Cl CH2CH3 CHF C-Cl
B 1.255 CH3 CH=CH C-Cl CH2C=CH2 CHF C-Cl
B 1.256 CH3 CH=CH C-Cl CH2C.CH CHF C-Cl
B .1.257 CH3 CH=CH C-Cl CH2OCH3 CHF C-Cl
B 1.258 CH3 CH=CH C-Cl CH2OCH2CH3 CHF C-Cl
B 1.259 CH2CH3 CH=CH C-CI H CHF C-Cl
B 1.260 CH2CH3 CH*CH C-Cl CH2CJI3 CHF C-Cl
BU261 mm* CH*CH C-Cl CH2C=CH2 CHF C-Cl
BH262 CHJCHJ CH=CH e-ci Gri2C.CH CHF C-Cl
B 1.263 CH2CH3 CH=CH C-Cl CH2OCH3 CHF C-Cl
B 1.264 CH2CH3 CH=CH C-Cl CH2OCH2CH3 CHF C-Cl
B 1.265 CH3 CH=CH C-Cl H CH20 C-H
B 1.266 CH3 CH=CH C-Cl CH2CH3 CH20 C-H
B 1.267 CH3 CH=CH C-Cl CH2C==CH2 CH20 C-H
B 1.268 CH3 CH=CH C-Cl CH2C.CH CH20 C-H
B 1.269 CH3 CH=CH C-Cl CH2OCH3 CH20 C-H
B 1.270 CH3 CH=CH C-Cl CH2OCH2CH3 CH20 C-H
B1.271 CH2CH3 CH-CH C-Cl H CH20 C-H
B 1.272 CH2CH3 CH=CH C-Cl CH2CH3 CH20 C-H
B 1.273 CJH.2CH3 CH=CH C-Cl CH2C—CH2 CH20 C-H
B 1.274 CH2CH3 CH=CH C-Cl CH2CCH CH20 C-H
B 1.275 CH2CH3 CH=CH C-Cl CH2OCH3 CH20 C-H
B 1.276 CH2CH3 CH=CH C-Cl CH2OCH2CH3 CH20 C-H
B 1.277 CH3 CH=CH C-Cl H CH20 C-Cl
B 1.278 CH3 CH=CH C-CI CH2CH3 CH20 C-Cl
B 1.279 CH3 CH=CH C-Cl CH2C=CH2 CH20 C-Cl
B 1.280 CH3 CH=CH C-Cl CH2C.CH CH20 C-Cl
B1.281 CH3 CH=CH C-Cl CH2OCH3 CH20 C-Cl
B 1.282 CH3 CH=CH C-Cl CH2OCH2CH3 CH20 C-Cl
B 1.283 CH2CH3 CH=CH C-Cl H CH20 C-Cl
B 1.284 CH2CH3 CH=CH C-Cl CH2CH3 CH20 C-Cl
B 1.285 Cr^CH^ CH=CH C-Cl CH2C=CH2 CH20 C-Cl
B 1.286 CHjCr^ CH=CH C-Cl CH2C.CH CH20 C-Cl
B 1.287 CHJCHJ CH=CH C-Cl CH2OCH3 CH20 C-Cl
B 1.288 CH2CH3 CH=CH C-Cl CH2OCH2CH3 CH20 C-Cl
Table B2
Table B2 provides 288 compounds of Formula Bl wherein R', D, E, R", A and J are x as defined in Table B1 and R6 is ethyl. i
Table B3 Table B3 provides 288 compounds of Formula Bl wherein R1, D, E, Rn, A and J are as defined in Table Bl and R6 is M-propyl.
1)
IS
Table B4
Table B4 provides 288 compounds of Formula Bl wherein R1, D, E, R", A and J are as defined in Table Bl and R6 is wo-propyl.
Table B5
Table B5 provides 288 compounds of Formula Bl wherein R1, D, E, R11, A and J are as defined in Table Bl and R6 is w-butyl.
TAbleB6
Table B6 providesi288 compounds of Formula Bl wherein R1, D, E, Ru, A and J are 2p as defined in Table B1 and R* is sec-butyl.
Table B7
Table B7 provides 288 compounds of Formula Bl wherein R\ D, E, Rn, A and J are as defined in Table Bl and R6 is z'so-butyl.
25
Table B8
Table B8 provides 288 compounds of Formula B1 wherein R1, D, E, R", A and J are as defined in Table B1 and R6 is tert-butyl.
»
Table B9
Table B9 provides 288 compounds of Formula Bl wherein R\ D, E, R11, A and J are as defined in Table B1 and R* is «-pentyl.
Table BIO
35
Table BIO provides 288 compounds of Formula Bl wherein R1, D, Es R", A and J are as defined in Table Bl and R6 is 1-methylbutyl.
Table Bll
Table Bll provides 288 compounds of Formula Bl wherein R1, D, E, R11, A and J 4D are as defined in Table B1 and R6 is 2-methylbutyl.
Table B12
Table B12 provides 288 compounds of Formula Bl wherein R], D, E, Rn, A and J are as defined in Table Bl and R6 is 3-methylbutyl.
Table B13
Table B13 provides 288 compounds of Formula Bl wherein R1, D, E, R", A and J are as defined in Table Bl and R6 is neopentyl.
Table B14
Table B14 provides 288 compounds of Formula Bl wherein R\ D, E, Ru, A and J are as defined in Table Bl and R6 is 2,2-dimethylbutyl.
Table B15
1
Table B15 provides 288 compounds of Formula Bl wherein Rl, D, E, Rn, A and J ) are as defined in Table B1 and R6 is 2,2,2-trifluoroethyl.
Table B16
Table B16 provides 288 compounds of Formula Bl wherein R', D, E, Rn, A and J are as defined in Table Bl and R6 is 2,2-difluoro-2-methoxyethyl. 2D
TalileB17
25
Table B17 provides 288 compounds of Formula Bl wherein R1, P, E, R", A and J are as defined in Table Bl and R6 is 3,3,3-trifluoropropyl.
Table B18
Table B18 provides 288 compounds of Formula Bl wherein R1, D, E, R", A and J are as defined in Table Bl and R* is^am-fluorobenzyl.
Table B19
Table B19 provides 288 compounds of Formula Bl wherein R1, D, E, R", A and J are as defined in Table Bl and R6 is 2,4-dichlorophenyl.
Table B20
3f Table B20 provides 288 compounds of Formula Bl wherein R\ D, E, RH, A and J
are as defined in Table Bl and R6 is 2-chloro-4-trifluoromethylphenyl.
Table CI
Table CI provides 144 compounds of Formula CI wherein X, R", A and J are as 40 defined in Table CI and R* is methyl.
Table CI
Compound
No X R" A J
Cl.l H H CH2 N
C1.2 H CH2CH3 CH2 N
CI.3 H CH2C=CH2 CH2 N
C1.4 H CH2C.CH CH2 N
C1.5 H CH2OCH3 CH2 N
C1.6 H CH2OCH2CH3 CH2 N
CI.7 H H CH(CH3) N
C1.8 H CH2CHj CH(CH3) N
C1.9 H CH2C=CH2 CH(CH3) N
C1.10 H CH2C.CH CH(CH3) N
Cl.ll H CH2OCH3 CH(CH3) N
C1.12 H CH2OCH2CH3 CH(CH3) N
C1.13 H H CHF N
CI.14 H CH2CH3 CHF N
CI.15 H CH2C=CH2 CHF N
ci:i6 ;H "" . CHjC.CH CHF " i W" '
cor iff CHaOCHjr 7: ;CHF -" 1 *N
cos H -'"■-' - CH2OGH2CH3 CHF !N-
C1.19 H H CH20 N
CI .20 H CH2CH3 CH20 N
CI.21 H CH2C=CH.2 CH20 N
C1.22 H CH2C.CH CH20 N
CI.23 H CH2OCH3 CH20 N
CI.24 H CH2OCH2CH3 CH20 N
CI.25 F H CH2 N
C1.26 F CH2CH3 CH2 N
CI.27 F CH2C=CH2 CH2 N
CI .28 F CH2CCH CH2 N
CI.29 F CH2OCH3 CH2 N
CI.30 F CH2OCH2CH3 CH2 N
C1.31 F H CH(CH3) N
CI.32 F CH2CH3 CH(CH3) N
CI.33 F CH2C=CH2 CH(CH3) N
CI.34 F CH2C.CH CH(CH3) N
CI.35 F CH2OCH3 CH(CH3) N
CI.36 F CH2OCH2CH3 CH(CH3) N
CI.37 F H CHF N
C1.38 F CH2CH3 CHF N
C1.39 F CH2C—CH2 CHF N
CI.40 F CHjC.CH CHF N 1
C1.41 F CH2OCH3 CHF N
CI.42 F CH2OCH2CH3 CHF N
CI.43 F H CH20 N
CI.44 F CH2CH3 CH20 N
CI.45 F CH2C=CH2 CH20 N
CI.46 F CH2C.CH CH20 N
CI.47 F CHjOCHj CH20 N
CI.48 F CH2OCH2CH3 CH20 N
CI.49 H H CH2 C-H
CI.50 H CH2CH3 CH2 C-H
C1.51 H Gri2C=CH.2 CH2 C-H
CI.52 H CH2C.CH CH2 C-H
CL53 H CH2OCH3 CH2 C-H
CI.54 H CH2OCH2CH3 CH2 C-H
CI.55 H H CH(CH3) C-H
CI.56 H CH2CH3 CH(CH3) C-H
C1.57 H CH2C=CH2 CH(CH3) C-H
CJ.58 H CH2C.CH CH(CH3) C-H
C1.59 H CH2OCH3 CH(CH3) C-H
CI. 60 H CH2OCH2CH3 CH(CH3) C-H
01.61 H H ;/ ;;.::::.:. CHF C-H
CI,62 H GrJ2CH3 CHF C-H
CI.63 H GH2C-=:CH2 CHF C-H
C1.64 H CH2C.CH CHF C-H
CI.65 H CH2OCH3 CHF C-H
CI.66 H CH2OCH2CH3 CHF C-H
CI.67 H H CH20 C-H
CI. 68 H CH2CH3 CH20 C-H
CI.69 H CH2C=CH2 CH20 C-H
CI.70 H CHjC.CH CH20 C-H
C1.71 H CH2OCH3 CH20 C-H
CI.72 H CH2OCH2CH3 CH20 C-H
CI.73 F H CH2 C-H
CI.74 F CH2CH3 CH2 C-H
CI.75 F CH2C=Cri2 CH2 C-H
C1.76 F CH2C.CH CH2 C-H
C1.77 F CH2OCH3 CH2 C-H
C1.78 F CH2OCH2CH3 CH2 C-H
CI.79 F H CH(CH3) C-H
C1.80 F CH2CH3 CH(CH3) C-H
C1.81 F CH2C=Cri2 CH(CH3) C-H
CI.82 F CH2C.CH CH(CH3) C-H
C1.83 F CH2OCH3 CH(CH3) C-H
C1.84 F CH2OCH2CH3 CH(CH3) C-H
C1.85 F H CHF C-H
C1.86 F CH2CH3 CHF C-H
CI.87 F CJi2C=CH2 CHF C-H
C1.88 F CH2C.CH CHF C-H
C1.89 F CH2OCH3 CHF C-H
CI.90 F CH2OCH2CH3 CHF C-H
C1.91 F H CH20 C-H
CI.92 F CH2CH3 CH20 C-H
CI.93 F CH2C=CH2 CH20 C-H
CI.94 F CH2C.CH CH20 C-H
CI.95 F CH2OCH3 CH20 C-H
C1.96 F CH2OCH2CH, CH20 C-H
CI.97 H H CH2 C-Cl
CI.98 H CH2CH3 CH2 C-Cl
CI.99 H CH2C=CH2 CH2 C-Cl
CI.100 H CH2C.CH CH2 C-Cl
Cl.lOl H CH2OCH3 CH2 C-Cl
CI.102 H CH2OCH2CH3 CH2 C-Cl
CI.103 H H CH(CH3) C-Cl
CI.104 H CH2CH3 CH(CH3) C-Cl
C1.105 H CH2C=CH2 CH(CH3) C-Cl
C1.106 H CH2G.CIi CH(CH3) C-Cl
C1.107 H CH2OCH3 CH(CH3) C-Cl
CI.108 H CH2OCH2CH3 CH(CH3) C-Cl
C1.109 H H CHF C-Cl
CI.110 H CH2CH3 CHF C-Cl
CI.Ill H CH2C=CH2 CHF C-Cl
CI.112 H CH2C.CH CHF C-Cl
C1.113 H CH2OCH3 CHF C-Cl
CI.114 H CH2OCH2CH3 CHF C-Cl
CI.115 H H CH20 C-Cl
CI.116 H CH2CH3 CH20 C-Cl
CI.117 H CH2C—CH2 CH20 C-Cl
CI.118 H CH2C.CH CH20 C-Cl
C1.119 H CH2OCH3 CH20 C-Cl
C1.120 H CH2OCH2CH3 CH20 C-Cl
CI.121 F H CH2 C-Cl
C1.122 F CH2CH3 CH2 C-Cl
C1.123 F CH2D=CH2 CH2 C-Cl
C1.124 F CH2C.CH CH2 C-Cl
CI.125 F CH2OCH3 CH2 C-Cl
C1.126 F CH2OCH2CH3 CH2 C-Cl
C1.127 F H CH(CH3) C-Cl
CI.128 F CH2CH3 CH(CH3) C-Cl
CI.129
F CH2C—CH2 CH(CH3) C-CI
CI.130 F CH2C.CH CH(CH3) C-Cl
CI.131 F CH2OCH3 CH(CH3) C-Cl
CI.132 F CH2OCH2CH3 CH(CH3) C-Cl
C1.133 F H CHF C-Cl
C1.134 F CH2CH3 CHF C-Cl
CI.135 F CH2C=CH2 CHF C-Cl
CI.136 F CH2C.CH CHF C-Cl
CI.137 F CH2OCH3 CHF C-Cl
C1.138 F CH2OCH2CH3 CHF C-Cl
CI.139 F H CH20 C-Cl
C1.140 F CH2CH.3 CH20 C-Cl
CI.141 F CH2C=CH2 CH20 C-Cl
CI.142 F CHjC.CH CH20 C-Cl
CI.143 F CH2OCH3 CH20 C-Cl
CI.144 F CH2OCH2CH3 CH20 C-Cl
Table C2
Table C2 provides 144 compounds of Formula CI wherein X, Rn, A and J are as defined in Table CI and R* is ethyl.
>"" Table C3
Table C3 provides 144 compounds of Formula CI wherein X, R11, A and J are as defined in Table CI and R6 is w-propyl.
Table C4
Table C4 provides 144 compounds of Formula CI wherein X, R", A and J are as defined in Table CI and R6 is wo-propyl.
Table C5
Table C5 provides 144 compounds of Formula CI wherein X, Rn, A and J are as defined in Table CI and R6 is w-butyl.
Table C6
Table C6 provides 144 compounds of Formula CI wherein X, R11, A and J are as defined in Table CI and R6 is sec-butyl.
Table C7
Table C7 provides 144 compounds of Formula CI wherein X, Rn, A and J are as defined in Table CI and R6 is wo-butyl.
Table C8
Table C8 provides 144 compounds of Formula CI wherein X, R11, A and J are as defined in Table CI and R6 is tert-butyl.
Table C9
Table C9 provides 144 compounds of Formula CI wherein X, Rn, A and J are as defined in Table CI and R6 is w-pentyl.
Table CIO
Table CIO provides 144 compounds of Formula CI wherein X, Ru, A and J are as defined in Table CI and R6 is 1-methylbutyl.
it) Table Cll
Table Cll provides 144 compounds of Formula CI wherein X, Rn, A and J are as defined in Table CI and R6 is 2-methylbutyl.
Table C12
Table C12 provides 144 compounds of Formula CI wherein X, R", A and J are as defined in Table CI and R* is 3-methylbutyl.
Table C13
Table C13 provides 144 compounds of Formula CI wherein X, R11, A and J are as 2p defined in Table C1 and R6 is neopentyl.
TaMeC14 ■
Table C14 provides 144 compounds of Formula CI wherein X, R", A and J are as defined in Table CI and R6 is 2,2-dimethylbutyl. 2|5
Table C15 Table C15 provides 144 compounds of Formula CI wherein X, RM, A and J are as defined in Table CI and R6 is 2,2,2-trifluoroethyl.
3t) Table C16
Table C16 provides 144 compounds of Formula CI wherein X, R", A and J are as defined in Table CI and R6 is 2,2-difluoro-2-methoxyethyl.
Table C17
3£ Table C17 provides 144 compounds of Formula CI wherein X, Rn, A and J are as
defined in Table CI and R6 is 3,3,3-trifluoropropyl.
Table C18
Table C18 provides 144 compounds of Formula CI wherein X, R11, A and J are as 4|) defined in Table CI and R* is^ara-fluorobenzyl.
Table C19
T,able C19 provides 144 compounds of Formula CI wherein X, RM, A and J are as defined in Table CI and R6 is 2,4-dichlorophenyl.
Table C20
Table C20 provides 144 compounds of Formula CI wherein X, Rn, A and J are as defined in Table CI and R6 is 2-chloro-4-trifluoromethylphenyl.
Table Dl
Table Dl provides 96 compounds of Formula Dl wherein X, Rn, A and J are as defined in Table Dl and R6 is methyl.
(D1)
ID
Table Dl
Compound No X R" A J
Dl.l H H CH2 C-H
D1.2 H CH2CH3 CH2 C-H
D1.3 H CH2C=CH2 CH2 C-H
D1.4 H CH2C.CH CH2 C-H
DI.5 H CH2OCH3 CH2 C-H
D1.6 H CH2OCH2CH3 CH2 C-H
D1.7 H H CH(CH3) C-H
D1.8 H CH2CH3 CH(CH3) C-H
DL9 H CH.2C^CH2 CH(CH3) C-H
DUO H CH2CCH CH(CH3) C-H
Dl.ll H CH2OCH3 CH(CH3) C-H
D1.12 H CH2OCH2CH3 CH(CH3) C-H
D1.13 H H CHF C-H
D1.14 H CH2CH3 CHF C-H
D1.15 H CH2C=CH2 CHF C-H
D1.16 H CH2C-Crl CHF C-H
D1.28 F CH2C.CH CH2 C-H
D1.29 F CH2OCH3 CH2 C-H
D1.30 F CH2OCH2CH3 CH2 C-H
D1.31 F H CH(CH3) C-H
D1.32 F CH2CH3 CH(CH3) C-H
D133 F CH2OCH2 CH(CH3) C-H
D1.34 F CH2C.CH CH(CH3) C-H
D1.35 F CH2OCH3 CH(CH3) C-H
D1.36 F CH2OCH2CH3 CH(CH3) C-H
D1.37 F H CHF C-H
D1.38 F CH2CH3 CHF C-H
D1.39 F CH2C—CH2 CHF C-H
D1.40 F CH2C.CH CHF C-H
D1.41 F CH2OCH3 CHF C-H
D1.42 F CH2OCH2CH3 CHF C-H
D1.43 F H CH20 C-H
D1.44 F CH2CH3 CH20 C-H
D1.45 F CH2C=CH2 CH20 C-H
D1.46 F CH2C.CH CH20 C-H
D147 F CH2OCH3 CH20 C-H
D1.48 F CH2OCH2CH3 CH20 D-H
D1.49 H n .H:-- CH2 C-Cl
Dl.SO H CH2CH3 CH2 C-Cl
D1.51 H .'CH2C=GH2 CH2 C-Cl
D1.52 H CH2C.CH CH2 C-Cl
D1.53 H CH2OCH3 CH2 C-Cl
D1.54 H CH2OCH2CH3 CH2 C-Cl
D1.55 H H CH(CH3) C-Cl
D1.56 H CH2CH3 CH(CH3) C-Cl
D1.57 H CH2C=CH2 CH(CH3) C-Cl
D1.58 H CH2C.CH CH(CH3) C-Cl
D1.59 H CH2OCH3 CH(CH3) C-Cl
D1.60 H CH2OCH2CH3 CH(CH3) C-Cl
D1.61 H H CHF C-Cl
D1.62 H CH2CH3 CHF C-Cl
D1.63 H CH2CS=CH2 CHF C-Cl
D1.64 H CH2C.CH CHF C-Cl
D1.65 H CH2OCH3 CHF C-Cl
D1.66 H CH2OCH2CH3 CHF C-Cl
D1.67 H H CH20 C-Cl
D1.68 H CH2CH3 CH20 C-Cl
D1.69 H CH2C=CH2' CH20 C-Cl
D1.70 H CH2C.CH CH20 C-Cl
|D1.71 H CH2OCH3 1 CH20 C-Cl
D1.72 H CH2OCH2CH3 CH20 C-Cl
D1.73 F H CH2 C-Cl
D1.74 F CH2CH3 CH2 C-Cl
D1.75 F CH2Cs=Cri2 CH2 C-Cl
D1.76 F CH2C.CH CH2 C-Cl
D1.77 F CH2OCH3 CH2 C-Cl
D1.78 F CH2OCH2CH3 CH2 C-Cl
D1.79 F H CH(CH3) C-Cl
D1.80 F CH2CH3 CH(CH3) C-Cl
D1.81 F CH2C=CH2 CH(CH3) C-Cl
D1.82 F CH2C.CH CH(CH3) C-Cl
D1.83 F CH2OCH3 CH(CH3) c-ci
D1.84 F CH2OCH2CH3 CH(CH3) C-Cl
D1.85 F H CHF C-Cl
D1.86 F CH2CH3 CHF C-Cl
D1.87 F CH2C=CH2 CHF C-Cl
D1.88 F CH2C.CH CHF C-Cl
D1.89 F CH2OCH3 CHF C-Cl
D1.90 F CH2OCH2CH3 CHF C-Cl
D1.91 F H CH20 C-Cl
D1.92 F CH2CH3 , CH20 . C-Cl
D1.93 F CH2C=CH2 CH2G C-Cl
D1.94 F CH2C.CH CH20 C-Cl
D1.95 F CH2OCH3 CH20 C-Cl
DL96 F CH2OCH2CH3 CH20 C-Cl
Table D2
Table D2 provides 96 compounds of Formula Dl wherein X, Ru, A and J are as defined in Table Dl and R6 is ethyl.
Table D3
Table D3 provides 96 compounds of Formula Dl wherein X, Rn, A and J are as defined in Table Dl and R* is H-propyl.
10 Table D4
Table D4 provides 96 compounds of Formula Dl wherein X, R1', A and J are as defined in Table Dl and R6 is wo-propyl.
Table D5
1|5 Table D5 provides 96 compounds of Formula Dl wherein X, R11, A and J are as
defined in Table Dl and R6 is H-butyl.
20
Table D6
Table D6 provides 96 compounds of Formula Dl wherein X, R11, A and J are as defined in Table D1 and R6 is sec-butyl.
JWO^07*32ir7" -!PCT/GB00/8i272-
TableD7
Table D7 provides 96 compounds of Formula Dl wherein X, R", A and J are as defined in Table Dl and R6 is wo-butyl.
Table D8
Table D8 provides 96 compounds of Formula Dl wherein X, Rn, A and J are as defined in Table Dl and R6 is terf-butyl.
Table D9
l(3 Table D9 provides 96 compounds of Formula Dl wherein X, R11, A and J are as
defined in Table Dl and R6 is »-pentyl.
Table D10
Table D10 provides 96 compounds of Formula Dl wherein X, R", A and J are as 1(5 defined in Table D1 and R6 is 1 -methylbutyl.
Table Dll
Table Dll provides 96 compounds of Formula Dl wherein X, R11, A and J are as defined in Table Dl and R6 is 2-methylbutyl. 210
Table D12 Table D12 provides 96 compounds of Formula Dl wherein X, Rn, A and J are as defined in Table Dl and R* is 3-methylbutyl.
2|5 Table D13
Table D13 provides 96 compounds of Formula Dl wherein X, Ru, A and J are as defined in Table Dl and R6 is neopentyl.
Table D14
3J0 Table D14 provides 96 compounds of Formula Dl wherein X, Ru, A and J are as
defined in Table Dl and R6 is 2,2-dimethylbutyl.
Table D15
Table D15 provides 96 compounds of Formula Dl wherein X, Rn, A and J are as 3|5 defined in Table Dl and R6 is 2,2,2-trifluoroethyl.
Table D16
Table D16 provides 96 compounds of Formula Dl wherein X, R", A and J are as defined in Table Dl and R6 is 2,2-difluoro-2-methoxyethyl. 4(0
Table D17 Table D17 provides 96 compounds of Formula Dl wherein X, R", A and J are as defined in Table Dl and R6 is 3,3,3-trifluoropropyl.
4)5 Table D18
Table D18 provides 96 compounds of Formula Dl wherein X, Rn, A and J are as defined in Table Dl and R6 is/rara-fluorobenzyl.
Table D19
Table Dl 9 provides 96 compounds of Formula Dl wherein X, R11, A and J are as defined in Table Dl and R6 is 2,4-dichlorophenyl.
Table D20
Table D20 provides 96 compounds of Formula Dl wherein X, R11, A and J are as defined in Table Dl and R6 is 2-chloro-4-trifluoromethylphenyl.
it) Table El
Table El provides 432 compounds of Formula El wherein R1, D, E, R", A and J are as defined in Table Al and R6 is methyl.
15
Table E2
TableE2 provides 432 compounds of Formula El wherein RJ, D, E, R11, A and J are as defined in Table Al and R6 is ethyl. 210
Table E3 Table E3 provides 432 compounds of Formula El wherein R1, D, E, Ru, A and J are as defined in Table Al and R6 is w-propyl.
2|5 Table E4
Table E4 provides 432 compounds of Formula El wherein R\ D, E, Rn, A and J are as defined in Table Al and R6 is wo-propyl.
Table E5
3)0 Table E5 provides 432 compounds of Formula El wherein R1, D, E, Rn, A and J are
as defined in Table Al and R6 is «-butyl.
Table E6
Table E6 provides 432 compounds of Formula El wherein R1, D, E, R", A and J are 5 as defined in Table Al and R6 is sec-butyl.
Table E7
Table E7 provides 432 compounds of Formula El wherein R1, D, E, R11, A and J are as defined in Table Al and R6 is iso-butyl 40
Table E8 Table E8 provides 432 compounds of Formula El wherein R1, D, E, Rn, A and J are as defined in Table Al and R6 is te/7-butyl.
Table E9
Table E9 provides 432 compounds of Formula El wherein R1, D, E, R", A and J are as defined in Table Al and R6 is n-pentyl.
Table E10
Table E10 provides 432 compounds of Formula El wherein R1, D, E, R", A and J are as defined in Table Al and R6 is 1-methylbutyl.
Table Ell
l[) Table El 1 provides 432 compounds of Formula El wherein R1, D, E, Rn, A and J are
as defined in Table Al and R6 is 2-methylbutyl.
Table E12
Table E12 provides 432 compounds of Formula El wherein R1, D, E, Ru, A and J are 1 |5 as defined in Table Al and R6 is 3-methylbutyl.
Table E13
Table E13 provides 432 compounds of Formula El wherein R1, D, E, R", A and J are as defined in Table Al and R6 is neopentyl. 2|0
Table E14 Table E14 provides 432 compounds of Formula El wherein R1, D, E, R", A and J are as defined in Table Al and R6 is 2,2-dimethylbutyl.
2|5 Table E15
Table E15 provides 432 compounds of Formula El wherein R1, D, E, R", A and J are as defined in Table Al and R6 is 2,2,2-trifluoroethyl.
I Table E16
3(0 Table E16 provides 432 compounds of Formula El wherein R1, D, E, RM, A and J are
as defined in Table Al and R6 is 2,2-difluoro-2-methoxyethyl,
Table E17
Table El 7 provides 432 compounds of Formula El wherein R1, D, E, R", A and J are 3(5 as defined in Table Al and R6 is 3,3,3-tnfluoropropyl.
Table E18
Table El 8 provides 432 compounds of Formula El wherein R\ D, E, R", A and J are as defined in Table Al and R6 is/>ara-fluorobenzyl. 4|0
Table E19 Table E19 provides 432 compounds of Formula El wherein R1, D, E, R", A and J are as defined in Table Al and R6 is 2,4-dichlorophenyl.
4J5 Table E20
Table E20 provides 432 compounds of Formula El wherein R\ D, E, Ru, A and J are as defined in Table Al and R6 is 2-chloro-4-trifluoromethylphenyL
Table E21
Table E21 provides 432 compounds of Formula El wherein R1, D, E, R11, A and J are as defined in Table Al and R6 is 4-trifluoromethylphenyl.
Table E22 Table E22 provides 432 compounds of Formula El wherein R1, D, E, Rn, A and J are as defined in Table Al and R6 is COCH3.
Table Fl
1 f) Table F1 provides 432 compounds of Formula F1 wherein R!, D, E, R1', A and J are
as defined in Table Al and R6 is methyl.
N-D O f^V\,
(F1)
15
Table F2
Table F2 provides 432 compounds of Formula Fl wherein R1, D, E, R11, A and J are as defined in Table Al and R6 is ethyl.
2J0 Table F3
Table F3 provides 432 compounds of Formula Fl wherein R1, D, E, Rn, A and J are as defined in Table Al and R6 is w-propyl.
Table F4
2J5 Table F4 provides 432 compounds of Formula F1 wherein R1, D, E, R", A and J are
as defined in Table Al and R6 is wopropyl.
Table F5
Table F5 provides 432 compounds of Formula Fl wherein R\ D, E, R", A and J are 3p as defined in Table Al and R6 is n-buryi.
Table F6
Table F6 provides 432 compounds of Formula Fl wherein R1, D, E, Rn, A and J are as defined in Table Al and R6 is sec-butyl. 3|5
Table F7 Table F7 provides 432 compounds of Formula Fl wherein R\ D, E, R11, A and J are as defined in Table Al and R6 is wo-butyl.
4|D Table F8
Table F8 provides 432 compounds of Formula Fl wherein R1, D, E, R11, A and J are as defined in Table Al and R6 is tert-butyl.
Table F9
Table F9 provides 432 compounds of Formula Fl wherein R\ D, E, R", A and J are as defined in Table Al and R6 is n-pentyl.
Table F10
Table F10 provides 432 compounds of Formula Fl wherein R\ D, E, Ru, A and J are as defined in Table Al and R6 is l-methylbutyl.
Tableau
if) Table Fl 1 provides 432 compounds of Formula Fl wherein R\ D, E, Rn, A and J are
as defined in Table Al and R6 is 2-methylbutyl.
Table F12
Table F12 provides 432 compounds of Formula Fl wherein R1, D, E, Rn, A and J are l|5 as defined in Table Al and R6 is 3-methylbutyl.
Table F13
Table F13 provides 432 compounds of Formula Fl wherein R\ D, E, R11, A and J are as defined in Table Al and R6 is neopentyl. 2l0
Table F14 Table F14 provides 432 compounds of Fonnula Fl wherein Rl, D, E, Rn, A and J are as defined in Table Al and R6 is 2,2-dimethylbutyl.
2|5 Table F15
Table F15 provides 432 compounds of Formula Fl wherein R1, D, E, Rn, A and J are as defined in Table Al and R6 is 2,2,2-trifluoroethyl.
Table F16
3\) Table F16 provides 432 compounds of Fonnula Fl wherein R\ D, E, R", A and J are
as defined in Table Al and R* is 2,2-difluoro-2-methoxyethyl.
Table F17
Table F17 provides 432 compounds of Formula Fl wherein R1, D, E, Rn, A and J are 3 5 as defined in Table Al and R* is 3,3,3-trifluoropropyl.
Table F18
Table F18 provides 432 compounds of Formula Fl wherein R1, D, E, R", A and J are as defined in Table Al and R* is/rara-fluorobenzyl. 4t)
Table F19 Table F19 provides 432 compounds of Formula Fl wherein R1, D, E, R", A and J are as defined in Table Al and R* is 2,4-dichlorophenyl.
4^ Table F20
Table F20 provides 432 compounds of Formula Fl wherein R1, D, E, R", A and J are as defined in Table Al and R6 is 2-chloro-4-trifluoromethylphenyl.
Table F21
Table F21 provides 432 compounds of Formula Fl wherein R1, D, E, Rn, A and J are as defined in Table Al and R6 is 4-trifluoromethylphenyl.
Table F22 Table F22 provides 432 compounds of Formula Fl wherein R1, D, E, R", A and J are as defined in Table Al and R6 is COCH3.
Table Gl
if) Table Gl provides 144 compounds of Formula Gl wherein X, R11, A and J are as
defined in Table CI and R6 is methyl.
l|5 Table G2
Table G2 provides 144 compounds of Formula Gl wherein X, R11, A and J are as defined in Table CI and R* is ethyl.
Table G3
ip Table G3 provides 144 compounds of Formula Gl wherein X, R11, A and J are as
defined in Table CI and R6 is K-propyl.
Table G4
Table G4 provides 144 compounds of Formula Gl wherein X, R11, A and J are as 2(5 defined in Table CI and R6 is wo-propyl.
Table G5
Table G5 provides 144 compounds of Formula Gl wherein X, R", A and J are as defined in Table CI and R6 is w-butyL 3|D
Table G6 Table G6 provides 144 compounds of Formula Gl wherein X, Rn, A and J are as defined in Table CI and R6 is sec-butyl.
3|5 Table G7
Table Gl provides 144 compounds of Formula Gl wherein X, Ru, A and J are as defined in Table CI and R6 is wo-butyl.
Table G8
4|0 Table G8 provides 144 compounds of Formula Gl wherein X, Ru, A and J are as
defined in Table C1 and R6 is terf-butyl.
Table G9
Table G9 provides 144 compounds of Formula Gl wherein X, R", A and J are as defined in Table CI and R6 is «-pentyl.
Table G10
Table G10 provides 144 compounds of Fonnula Gl wherein X, R", A and J are as defined in Table CI and R6 is 1-methylbutyl.
Table Gil
1^) Table Gl 1 provides 144 compounds of Formula Gl wherein X, R11, A and J are as
defined in Table CI and R6 is 2-methylbutyl.
Table G12
Table G12 provides 144 compounds of Fonnula Gl wherein X, Rn, A and J are as 1 £ defined in Table C1 and R6 is 3-methylbutyl.
Table G13
Table G13 provides 144 compounds of Formula Gl wherein X, R", A and J are as defined in Table CI and R6 is neopentyl. 20
Table G14 Table G14 provides 144 compounds of Formula Gl wherein X, Rn, A and J are as defined in Table CI and R6 is 2^-dimethylbutyl.
2fc Table G15
Table G15 provides 144 compounds of Formula Gl wherein X, R", A and J are as defined in Table CI and R6 is 2,2,2-trifluoroethyl.
Table G16
3J) Table G16 provides 144 compounds of Formula Gl wherein X, R", A and J are as
defined in Table CI and R6 is 2,2-difluoro-2-methoxyethyl.
Table G17
Table G17 provides 144 compounds of Formula Gl wherein X, R", A and J are as 315 defined in Table C1 and R6 is 3,3,3-trifluoropropyl.
Table G18
Table G18 provides 144 compounds of Formula Gl wherein X, R", A and J are as defined in Table CI and R6 ispara-fluorobenzyl.
4b
Table G19
Table G19 provides 144 compounds of Formula Gl wherein X, R", A and J are as defined in Table CI and R6 is 2,4-dichlorophenyl.
4)5 Table G20
Table G20 provides 144 compounds of Formula Gl wherein X, R", A and J are as defined in Table CI and R6 is 2-chloro-4-trifluoromethylphenyl.
Table HI
Table HI provides 144 compounds of Formula HI wherein X, R11, A and J are as defined in Table CI and R6 is methyl.
Table H2
1)
Table H2 provides 144 compounds of Formula HI wherein X, R11, A and J are as defined in Table CI and R6 is ethyl.
Table H3
Table H3 provides 144 compounds of Formula HI wherein X, Rn, A and J are as defined in Table CI and R6 is w-propyl.
lp* Table H4
Table H4 provides 144 compounds of Formula HI wherein X, Rn, A and J are as defined in Table C1 and R6 is wo-propyl;
Table H5
2f) Table H5 provides 144 compounds of Formula HI wherein X, Rn, A and J are as
defined in Table CI and R6 is w-butyl.
Table H6
Table H6 provides 144 compounds of Formula HI wherein X, R", A and J are as 2|5 defined in Table CI and R6 is .sec-butyl.
Table H7
Table H7 provides 144 compounds of Formula HI wherein X, Rn, A and J are as defined in Table CI and R6 is wo-butyl. 30
Table H8 Table H8 provides 144 compounds of Formula HI wherein X, Rn, A and J are as defined in Table CI and R6 is /er/-butyl.
3p~ Table H9
Table H9 provides 144 compounds of Formula HI wherein X, R11, A and J are as defined in Table CI and R6 is «-pentyl.
Table H10
4J0 Table H10 provides 144 compounds of Formula HI wherein X, R11, A and J are as
defined in Table CI and R6 is 1-rnethylbutyl.
Table Hll
Table HI 1 provides 144 compounds of Formula HI wherein X, R", A and J are as defined in Table CI and R6 is 2-methylbutyl.
Table H12
Table H12 provides 144 compounds of Formula HI wherein X, Ru, A and J are as ■definedin Tabled and R6 is 3-methylbutyI.
Table H13
Table HI 3 provides 144 compounds of Formula HI wherein X, Rn, A and J are as defined in Table CI and R6 is neopentyl.
Table H14
Table H14 provides 144 compounds of Formula HI wherein X, R", A and J are as 1(5 defined m Table CI and RSs2>dimethylbutyl.
Table H15
Table HI 5 provides 144 compounds of FonnulaHl wherein X, R", A and J are as defined in Table CI and R6 is 2^,2-trifluoroethyl. 2|D
Table H16 Table H16 provides 144 compounds of Formula HI wherein X, R", A and J are as defined in Table CI andR* is 2^-difluoro-2-methoxyethyl.
2|5 TableH17
Table H17 provides 144 compounds of Formula HI wherein X, R", A and J are as defined in Table CI and R6 is 3,3,3-trifluoropropyl.
Table H18
3|0 Table H18 provides 144 compounds of Formula HI wherein X, R", A and J are as
defined in Table CI and R6 ispara-fluorobeDzyl.
Table H19
Table H19 provides 144 compounds of Formula HI wherein X, Rn, A and J are as 3(5 defined in Table CI and R6 is 2,4-dichlorophenyl.
Table H20
Table H20 provides 144 compounds of Formula HI wherein X, Rn, A and J are as defined in Table CI and R6 is 2-chloro-4»trifluoromethylphenyl. *0
Table II Table II provides 288 compounds of Formula II, wherein R1, D, E, R2, A and J are as defined in Table II and R6 is methyl.
Table II
1 Compouod
1 No. R1 ID IE R1 |A |J
11.1 CH3 S C-Cl H CH2 N
11.2 CH3 S C-Cl CH2CH3 CH2 N
11.3 CH3 S C-Cl CH2C—CH2 CH2 N
11.4 CH3 s C-Cl CH2C.CH CH2 N
11.5 CH3 s C-Cl CH2OCH3 CH2 N
11.6 CH3 s C-Cl CH2OCH2CH3 CH2 N
11.7 CH3 s C-Br H CH2 N
11.8 CH3 s C-Br C-.H.20xl3 CH2 N
11.9 CH3 s C-Br CHjC^CH^ CH2 N
11.10 CH3 s C-Br CH2C.CH CH2 N
11.11 CH3 s C-Br CH2OCH3 CH2 N
11.12 CH3 s C-Br CH2OCH2CH3 CH2 N
11.13 CH2CH3 ■r C-Cl n €H2 N
11.14 CH2CH3 s C-Cl Cxi2Crl3 CH2 N
11.15 OH2CH.3 s C-Cl CH2C=CH2 CH2 N
11.16 CH2CH3 s C-Cl CH2C.CH CH2 N
11.17 CH2CH3 s C-Cl CH2OCH3 CH2 N
11.18 CH2CH3 s C-Cl CH2OCH2CH3 CH2 N
11.19 CH2CH3 s C-Br H CH2 N
11.20 CH2CH3 s C-Br CH2CH3 CH2 N
11.21 CH2CH3 s C-Br CH2C=CH2 CH2 N
11.22 CH2CH3 s C-Br CH2CCH CH2 N
11.23 CH2CH3 s C-Br CH2OCH3 CH2 N
11.24 . CH2OH3 s C-Br CH2OCH2CH3 CH2 N
11.25 CH3 s C-Cl H CH(CH3) N
11.26 CH3 s C-Cl CH2CH3 CH(CH3) N
11.27 CH3 s C-Cl CH2C^CH.2 CH(CH3) N
11.28 CH3 s C-Cl CH2C.CH CH(CH3) N
11.29 CH3 s C-Cl CH2OCH3 CH(CH3) N
11.30 CH3 s C-Cl CH2OCH2CH3 CH(CH3) N
11.31 CH3 s C-Br H CH(CHJ N
11.32 CH3 s C-Br CH2CH3 CH(CH3) N
11.33 CH3 s C-Br CH2C=CH2 CH(CH3) N
11.34 CH3 s C-Br CH2C.CH CH(CH3) N
11.35 CH3 s C-Br CH2OCH3 CH(CH3) N
[11.36 CH3 s C-Br CH2OCH2CH3 CH(CH3) N
11.37 CH2CH3 S C-Cl H CH(CH3) N
11.38 CH2CH3 s C-Cl CH2CH3 CH(CH3) N
11.39 CH2CH3 s C-Cl Cr^C^Cr^ CH(CH3) N
11.40 CH2CH3 s C-Cl CHjC.CH CH(CH3) N
11.41 CH2CH3 s C-Cl CH2OCH3 CH(CH3) N
11.42 CH2CH3 s C-CI CH2OCH2CH3 CH(CH3) N
11.43 CH2CH3 s C-Br H CH(CH3) N
11.44 CH2CH3 s C-Br CH2CHj CH(CH3) N
11.45 CH2CH3 s C-Br Cri2C=:CH2 CH(CH3) N
11.46 CH2CH3 s C-Br CH2C.CH CH(CH3) N
11.47 CH2CH3 s C-Br CH2OCH3 CH(CH3) N
11.48 CH2CXI3 s C-Br CH2OCH2CH3 CH(CH3) N
11.49 CH3 s C-Cl H CHF N
11.50 CH3 s C-Cl CH2CH3 CHF N
11.51 CH3 s C-Cl Cxi2C=:C'H.2 CHF N
11.52 CH3 s C-Cl CH2C.CH CHF N
11.53 CH3 s C-Cl CH2OCH3 CHF N
11.54 CH3 s C-Cl CHJOCHJCHJ CHF N
11.55 CH3 s C-Br H CHF N
11.56 CH3 s C-Br CH2CH3 CHF N
11.57 {-!..:..'■■ CH3 r S ■■:■> ClBr ?CH2C=CH2 CHF N
11.58 CH3 ; > S .::\'-V car jCrljC.CH CHF N
11.59 CH3 s C-Br CH2OCH3 CHF N
IL60 CH3 s C-Br CH2OCH2CH3 CHF N
11.61 CH2CH3 s C-Cl H CHF N
11.62 CH2CH3 s C-Cl CIi2Crl3 CHF N
11.63 CH2CH3 s C-Cl CH2C=CH2 CHF N
11.64 CH2CH3 s C-Cl CH2C.CH CHF N
11.65 GH2CH3 s C-Cl CH2OCH3 CHF N
11.66 CH2CH3 s C-Cl CH2OCH2CH3 CHF N
11.67 CH2CH3 s C-Br H CHF N
11.68 CH2CH3 s C-Br Crl2Crl3 CHF N
11.69 CH2CH3 s C-Br CIi2C=CH2 CHF N
11.70 CH2CH3 s C-Br CHjC.CH CHF N
11.71 CH2CH3 s C-Br CH2OCH3 CHF N
11.72 CH2CH3 s C-Br CH20CH2CH3 CHF N
11.73 CH3 s C-Cl H CH20 N
11.74 CH3 s C-Cl CH2CH3 CH2Q N
11.75 CH3 s C-Cl CH2C=CH2 CH20 N
11.76 CH3 s C-Cl CH2C.CH CH20 N
11.77 CH3 s C-Cl CH2OCH3 CH20 N
11.78 CH3 s C-Cl CH2OCH2CH3 CH20 N
11.79 CH3 s C-Br H CH20 N
11.80 CH3 . S C-Br CH2CH3 CH2Q N
11.81 CH3 S C-Br CrijC—CH2 CH20 N
11.82 CH3 s C-Br CH2C.CH CH20 N
11.83 CH3 s C-Br CH2OCH3 CH20 N
11.84 CH3 s C-Br CH2OCH2CH3 CH20 N
11.85 CH2CH3 s C-Cl H CH20 N
11.86 CH2CH3 s C-Cl CH2CH3 CH20 N
11.87 CH2CH3 s C-Cl CH2C=CH2 CH20 N
11.88 CH2CH3 s C-Cl CH2C.CH CH20 N
11.89 CH2CH3 s C-Cl CH2OCH3 CH20 N
11.90 CH2CH3 s C-Cl CH2OCH2CH3 CH20 N
11.91 CH2CH3 s C-Br H CH20 N
11.92 CH2CH3 s C-Br CH2CH3 CH20 N
11.93 CH2CH3 s C-Br CH2C=CH2 CH20 N
11.94 CH2CH3 s C-Br CH2C.CH CH20 N
11.95 CH2CH3 s C-Br CH2OCH3 CH20 N
11.96 CHJCHJ s C-Br CH2OCH2CH3 CH20 N
11.97 CH3 s C-Cl H CH2 C-H
11.98 CH3 s C-Cl CH2CH3 CH2 C-H
11.99 CH3 s C-Cl CH2C=CH2 CH2 C-H
11,100 CH3 s C-Cl CH2C.CH CH2 C-H
I1J101 i CH3T>n S :-:.,- Q-€l '•CH^OC^ CH2 C-H
11402 CH3 i: s GO GH2OCH2CH3 CH2 C-H
11.103 CH3 s C-Br H CH2 C-H
11.104 CH3 s C-Br CH2CH3 CH2 C-H
11.105 CH3 s C-Br CH2C=CH2 CH2 C-H
11.106 CH3 s C-Br CH2C.CH CH2 C-H
11.107 CH3 s C-Br CH2OCH3 CH2 C-H
11.108 CH3 s C-Br CH2OCH2CH3 CH2 C-H
11.109 CH2CH3 s C-Cl H CH2 C-H
11.110 CH2CH3 s C-Cl CH2CH3 CH2 C-H
11.111 v^xi2CH3 s C-Cl CH2C==CH2 CH2 C-H
IL112 CH2CH3 s C-Cl CH2C.CH CH2 C-H
11.113 CH2CH3 s C-Cl CH2OCH3 CH2 C-H
11.114 CH2GH3 s C-Cl CH2OCH2CH3 CH2 C-H
11.115 CH2CH3 s C-Br H CH2 C-H
11.116 CH2CH3 s C-Br CH2CH3 CH2 C-H
11.117 CH2CH3 s C-Br CH2C=CH2 CH2 C-H
11.118 CH2CH3 s C-Br CH2C.CH CH2 C-H
11.119 CH2CH3 s C-Br CH2OCH3 CHa C-H
11.120 CH2CH3 s C-Br CH2OCH2CH3 CH2 C-H
11.121 CH3 s C-Cl H CH(CH3) C-H
11.122 CH3 s C-Cl CH2GH3 CH(CH3) C-H
11.123 CH3 s C-Cl CH2C=CH2 CH(CH3) C-H
11.124 CH3 s C-Cl CH2C.CH CH(CH3) C-H 1
11.125 CH3 S C-Cl CH2OCH3 CH(CH3) C-H
11.126 CH3 s C-Cl CH2OCH2CH3 CH(CH3) C-H
11.127 CH3 s C-Br H CH(CH3) C-H
11.128 CH3 s C-Br CH2CH3 CH(CH3) C-H
11.129 CH3 s C-Br CH2C=CH2 CH(CH3) C-H
11.130 CH3 s C-Br CH2C.CH CH(CH3) C-H
11.131 CH3 s C-Br CH2OCH3 CH(CH3) C-H
11.132 CH3 s C-Br CH2OCH2CH3 CH(CH3) C-H
11.133 CH2CH3 s C-Cl H CH(CH3) C-H
11.134 CH2CH3 s C-Cl CH2CH3 CH(CH3) C-H
11.135 CH2CH3 s C-Cl CH2C=CH2 CH(CH3) C-H
11.136 CH2CH3 s C-Cl CH2C.CH CH(CH3) C-H
11.137 Cr^CH^ s C-Cl CH2OCH3 CH(CH3) C-H
11.138 CH2CH3 , s C-Cl CH2OCH2CH3 CH(CH3) C-H
11.139 C-H2CH3 s C-Br H CH(CH3) C-H
11.140 CH2CH3 s C-Br CH2CH3 CH(CH3) C-H
11.141 CH2CH3 s C-Br CH2C=CH2 CH(CH3) C-H
11.142 CH2CH3 s C-Br CH2C.CH CH(CH3) C-H
11.143 CH2CH3 s C-Br CH2OCH3 CH(CH3) C-H
11.144 CI^CHj: ,s C-Br CH2OCH2CH3 CH(CH3) C-H
11.145 H■"> CH3 K s C-Cl H$V> ; CHF C-H
11.146 CH3 ; ;s ?;\ C-Cl GH2GH3 CHF C-H
11.147 CH3 s C-Cl GH2C=Cxi2 CHF C-H
11.148 CH3 s C-Ci CH2C.CH CHF C-H
11.149 CH3 s C-Cl CH2OCH3 CHF C-H
11.150 CH3 s C-Cl CH2OCH2CH3 CHF C-H
11.151 CH3 s C-Br H CHF C-H
11.152 CH3 s C-Br CH2CH3 CHF C-H
11.153 CH3 s C-Br CH2C==CH2 CHF C-H
11.154 CH3 s C-Br CH2C.CH CHF C-H
11.155 CH3 s C-Br CH2OCH3 CHF C-H
11.156 CH3 s C-Br CH2OCH2CH3 CHF C-H
11.157 CH2CH3 s C-Cl H CHF C-H
11.158 CH2Cxi3 s C-Cl GH2CH3 CHF C-H
11.159 CH2CH3 s C-Cl CH2C=CH2 CHF C-H
11.160 CH2CH3 s C-Cl CH2C.CH CHF C-H
11.161 CH2CH3 s C-Cl CH2OCH3 CHF C-H
11.162 CH2CH3 s C-Cl CH2OCH2CH3 CHF C-H
11.163 CH2CH3 s C-Br H CHF C-H
11.164 CH2CH3 s C-Br C/XijC-ri3 CHF C-H
11.165 CH2CH3 s C-Br CH2C=CH2 CHF C-H
11.166 CH2CH3 s C-Br CH2C.CH CHF C-H
11.167 CH2CH3 s C-Br CH2OCH3 CHF C-H
11.168 CH.2CH3 s C-Br 1 CH2OCH2CH3 CHF C-H
11.169 CH3 S C-Cl H CH20 C-H
11.170 CH3 S C-Cl CH2CH3 CH20 C-H
11.171 CH3 S C-Cl CH2C=CH2 CH20 C-H
11.172 CH3 S C-Cl CH2C.CH CH20 C-H
11.173 CH3 s C-Cl CH2OCH3 CH20 C-H
11.174 CH3 s C-Cl CH2OCH2CH3 CH20 C-H
11.175 CH3 s C-Br H CH20 C-H
11.176 CH3 s C-Br CH2CH3 CH20 C-H
11.177 CH3 s C-Br CH2C=CH2 CH20 C-H
11.178 CH3 s C-Br CH2C.CH CH20 C-H
11.179 CH3 s C-Br CH2OCH3 CH20 C-H
11.180 CH3 s C-Br CH2OCH2CH3 CH20 C-H
11.181 CH2CH3 s C-Cl H CH20 C-H
11.182 CH2CH3 s C-Cl CH2CH3 CH20 C-H
11.183 CH2CH3 s C-Cl CH2C=CH2 CH20 C-H
11.184 GH2CH3 s C-Cl CH2C.CH CH20 C-H
11.185 CH2CH3 s C-Cl CH2OCH3 CH20 C-H
11.186 CH2CH3 s C-Cl CH2OCH2CH3 CH20 C-H
11.187 Crl2CH.3 s C-Br H CH20 C-H
11.188 CH2CH3 s CBr GH2CH3 CH20 C-H
11.189 - CH2CI^ :s C-Br CH2C=Cri2 CHiO C-H
11.190 CH2CH3 s C-Br CHjC.CH CH20 C-H
11.191 CH2CH3 s C-Br CH2OCH3 CH20 C-H
11.192 CH2CH3 s C-Br CH2OCH2CH3 CH20 C-H
11.193 CH3 s C-Cl H CH2 C-Cl
11.194 CH3 s C-Cl CH2CH3 CH2 C-Cl
11.195 CH3 s C-Cl CH2C==Cri2 CH2 C-Cl
11.196 CH3 s C-Cl CH2C.CH CH2 C-Cl
11.197 CH3 s C-Cl CH2OCH3 CH2 C-Cl
11.198 CH3 s C-Cl CH2OCH2CH3 CH2 C-Cl
11.199 CH3 s C-Br H CH2 C-Cl
11.200 CH3 s C-Br CH2CH3 CH2 C-Cl
11.201 CH3 s C-Br CH2C=CH2 CH2 C-Cl
11.202 CH3 s C-Br CH2C.CH CH2 C-Cl
11.203 CH3 s C-Br CH2OCH3 CH2 C-Cl
11.204 CH3 s C-Br CH2OCH2CH3 CH2 C-Cl
11.205 CH2CH3 s C-Cl H CH2 C-Cl
11.206 CH2CH3 s C-Cl CH2CH3 CH2 C-Cl
11.207 CH2CH3 s C-Cl CH2C^CH2 CH2 C-Cl
11.208 CH2CH3 s C-Cl CH2C.CH CH2 C-Cl
11.209 CH2CH3 s C-Cl CH2OCH3 CH2 C-Cl
11.210 CH2CH3 s C-Cl CH2OCH2CH3 CH2 C-Cl
11.211 CH2CH3 s C-Br H CH2 C-Cl
11.212 CH2CH3 s C-Br C.Jri2Crl3 CH2 C-Cl
11.257 CH2CH3 S C-Cl CH2OCHj CHF C-Cl
11.258 CH2CH3 s C-Cl CH2OCH2CH3 CHF C-Cl
11.259 CH2CH3 s C-Br H CHF C-Cl
11.260 CH2CH3 s C-Br CH2CH3 CHF C-Cl
11.261 CH2CH3 s C-Br CH2C=:CH2 CHF C-Cl
11.262 CH2CH3 s C-Br CH2C.CH CHF C-Cl
11.263 CH2CH3 s C-Br CH2OCH3 CHF C-Cl
11.264 CH2CH3 s C-Br CH2OCH2CH3 CHF C-Cl
11.265 CH3 s C-Cl H CH20 C-Cl
11.266 CH3 s C-Cl CH2CH3 CH20 C-Cl
11.267 CH3 s C-Cl CH2C=CH2 CH20 C-Cl
11.268 CH3 s C-Cl CH2C.CH CH20 C-Cl
11.269 CH3 s C-Cl CH2OCH3 CH20 C-Cl
11.270 CH3 s C-Cl CH2OCH2CH3 CH20 C-Cl
11.271 CH3 s C-Br H CH20 C-Cl
11.272 CH3 s C-Br CH2CH3 CH20 C-Cl
11.273 CH3 s C-Br CH2C~CH2 CH20 C-Cl
11.274 CH3 s C-Br CH2C.CH CH20 C-Cl
11.275 CH3 s C-Br CH2OCH3 CH20 C-Cl
11.276 CH3 s C-Br CH2OCH2CH3 CH2p C-Cl
IIi277 £H£iM .s C-Cl ;a.v' 5.... ...■; CH20 C-Cl
11.278 GH2GH3 s C-Cl eH2CH3 CH20 C-Cl
11.279 GH2CH3 s C-Cl GH2C==CH2 CH20 C-Cl
11.280 CH2CH3 s C-Cl CH2C.CH CH20 C-Cl
11.281 CH2CH3 s C-CI CH2OCH3 CH20 C-Cl
11,282 CH2CH3 s C-Cl CH2OCH2CH3 CH20 C-Cl
11.283 CH2CH3 s C-Br H CH20 C-Cl
11.284 CH2CH3 s C-Br GH.2CH.3 CH20 C-Cl
11.285 CH2GH3 s C-Br CH2C=CH2 CH20 C-Cl
11.286 CH2CH3 s C-Br CH2C.CH CH20 C-Cl
11.287 CH2CH3 s C-Br CH2OCH3 CH20 C-Cl
11.288 G.H2CH3 s C-Br CH2OCH2CH3 CH20 C-Cl
Table 12
Table 12 provides 288 compounds of Formula II wherein X, R2, A and J are as defined in Table 11 and R6 is ethyl.
Table 13
Table 13 provides 288 compounds of Formula II wherein X, R2, A and J are as defined in Table II and R6 is w-propyl.
Table 14
Table 14 provides 288 compounds of Formula II wherein X, R2} A and J are as defined in Table 11 and R6 is wo-propyl.
V
Table 15
Table 15 provides 288 compounds of Formula II wherein X, R2, A and J are as defined in Table II and R6 is w-butyl.
i Table 16
Table 16 provides 288 compounds of Formula II wherein X, R2, A and J are as defined in Table II and R6 is sec-butyl.
Table 17
I (j) Table 17 provides 288 compounds of Formula 11 wherein X, R2, A and J are as
defined in Table II and R6 is wo-butyl.
Table 18
Table 18 provides 288 compounds of Formula II wherein X, R2, A and J are as
II defined in Table 11 and R6 is tert-butyl
Table 19
Table 19 provides 288 compounds of Formula II wherein X, R2, A and J are as defined in Table II and Rfi isw-pentyl. 2()
Table 110 Table 110 provides 288 compounds of Formula II wherein X, R\ A and J are as defined in Table II and R6 is 1-memylbutyl.
2fc Table 111
Table II1 provides 288 compounds of Formula II wherein X, R2, A and J are as defined in Table II and R6 is 2-methylbutyl.
Table 112
3f) Table 112 provides 288 compounds of Formula II wherein X, R2, A and J are as
defined in Table II and R6 is 3-methylbutyl.
Table 113
Table 113 provides 288 compounds of Formula II wherein X, R2, A and J are as 3 j> defined in Table II and R6 is neopentyl.
Table 114
Table 114 provides 288 compounds of Formula II wherein X, R2, A and J are as defined in Table II and R6 is 2,2-dimethylbutyl. 40
Table 115 Table 115 provides 288 compounds of Formula II wherein X, R\ A and J are as defined in Table 11 and R6 is 2,2,2-trifluoroethyl.
4fc Table 116
Table 116 provides 288 compounds of Formula II wherein X, R2, A and J are as defined in Table II and R6 is 2,2-difluoro-2-methoxyethyl.
Table 117
Table 117 provides 288 compounds of Formula II wherein X, R2, A and J are as defined in Table II and R6 is 3,3,3-trifluoropropyl.
Table 118
Table 118 provides 288 compounds of Formula II wherein X, R2, A and J are as defined in Table II and R6 ispara-fluorobenzyl.
lj) Table 119
Table 119 provides 288 compounds of Formula II wherein X, R2, A and J are as defined in Table II and R6 is 2,4-dichlorophenyl.
Table 120
Table 120 provides 288 compounds of Formula II wherein X, R2, A and J are as defined in Table II and R6 is 2-chloro-4-trifluoromethylphenyl.
Table Jl
Table Jl provides 288 compounds of Formula Jl, wherein R1, D, E, R2, A and J are as 2p defined in Table II and R6 is methyl.
Table J2
2(5 Table J2 provides 288 compounds of Formula Jl wherein R\ D, E, R\ A and J are as
defined in Table II and R6 is ethyl.
Table J3
Table J3 provides 288 compounds of Formula Jl wherein R1, D, E, R\ A and J are as ?|0 defined in Table II and R6 is «-propyl.
Table J4
Table J4 provides 288 compounds of Formula Jl wherein R1, D, E, R2, A and J are as defined in Table II and R* is wo-propyl.
Table J5
Table J5 provides 288 compounds of Formula Jl wherein R\ D, E, R2, A and J are as defined in Table II and R* is «-butyl.
3 Table J6
Table J6 provides 288 compounds of Formula Jl wherein R1, D, E, R2} A and J are as defined in Table Jl and R6 is .sec-butyl.
Table J7
Table J7 provides 288 compounds of Formula Jl wherein R1, D, E, R2, A and J are as defined in Table II and R6 is iso-butyl.
Table JS
Table J8 provides 288 compounds of Formula Jl wherein R1, D, E, R2, A and J are as defined in Table 11 and R6 is «r/-butyl.
Table J9
1 p Table J9 provides 288 compounds of Formula Jl wherein R1, D, E, R2, A and J are as
defined in Table 11 and R6 is n-pentyl.
Table J10
Table JIO provides 288 compounds of Formula Jl wherein R1, D, E, R\ A and J are 1(5 as defined in Table II and R6 is 1-methylbutyl.
Table Jll
Table Jl 1 provides 288 compounds of Formula Jl wherein R\ D, E, R2, A and J are as defined in Table 11 and R6 is 2-methylbutyl. 2J0
Table J12
Table J12 provides 288 compounds of Formula Jl wherein R1, D, E, R2, A and J are as defined in Table II and R6 is 3-methylbutyl.
2)5 Table J13
Table J13 provides 288 compounds of Formula Jl wherein R1, t>, E, R2, A and J are as defined in Table II and R* is neopentyl.
Table J14
3|0 Table J14 provides 288 compounds of Formula Jl wherein R1, D, E, R2, A and J are
as defined in Table II and R6 is 2,2-dimethylbutyl.
Table J15
Table J15 provides 288 compounds of Formula Jl wherein R\ D, E, R2, A and J are 3|5 as defined in Table 11 and R6 is 2,2,2-trifluoroethyl.
Table J16
Table J16 provides 288 compounds of Formula Jl wherein R1, D, E, R2, A and J are as defined in Table II and R* is 2,2-difluoro-2-methoxyethyl.
4|0
Table J17
Table J17 provides 288 compounds of Formula Jl wherein R\ D, E, R2, A and J are as defined in Table II and R* is 3,3>3-trifluoropropyl.
4^ Table J18
Table J18 provides 288 compounds of Formula Jl wherein R1, D, E, R2, A and J are as defined in Table II and R6 is/rara-fluorobenzyl.
Table J19
Table J19 provides 288 compounds of Formula Jl wherein R1, D, E, R2, A and J are as defined in Table II and R6 is 2,4-dichlorophenyl.
Table J20
Table J20 provides 288 compounds of Formula Jl wherein R1, D, E, R2, A and J are as defined in Table II and R6 is 2-chloro-4-trifluoromethylphenyl.
l|0 Table Kl
Table Kl provides 288 compounds of Fonnula Kl, wherein R1, D, E, R2, A and J are as defined in Table II and R6 is methyl.
R12
R15
Table K2
Table K2 provides 288 compounds of Formula Kl wherein R\ D, E, R2, A and J are as defined in Table II and R6 is ethyl,
2|0 TableK3
Table K3 provides 288 compounds of Formula Kl wherein R1, D, E, R2, A and J are as defined in Table 11 and R6 is w-propyl.
Table K4
2)5 Table K4 provides 288 compounds of Formula Kl wherein R1, D, E, R2, A and J are
as defined in Table II and R* is wo-propyl.
Table K5
Table K5 provides 288 compounds of Formula Kl wherein R\ D, E, R2, A and J are 3p as defined in Table II and R6 is «-butyl.
Table K6
Table K6 provides 288 compounds of Fonnula Kl wherein R1, D, E, R2, A and J are as defined in Table II and R6 is sec-butyl. 3|5
Table K7 Table K7 provides 288 compounds of Fonnula Kl wherein R1, D, E, R2, A and J are as defined in Table II and R6 is wo-butyl.
4) Table K8
Table K8 provides 288 compounds of Formula Kl wherein R1, D, E, R2, A and J are as defined in Table II and R6 is terf-butyl.
Table K9
Table K9 provides 288 compounds of Fonnula Kl wherein R1, D, E, R2, A and J are as defined in Table II and R6 is w-pentyl.
Table K10
Table K10 provides 288 compounds of Formula Kl wherein R\ D, E, R\ A and J are as defined in Table II and R* is 1-methylbutyl.
Table KU
1 JO Table Kl 1 provides 288 compounds of Fonnula Kl wherein R', D, E, R2, A and J are
as defined in Table II and R6 is 2-methylbutyl.
Table K12
Table K12 provides 288 compounds of Formula Kl wherein. R1, D, E, R\ A and J are 1|5 as defined in Table II and R6 is 3-methylbutyl.
Table K13
Table K13 provides 288 compounds of Formula Kl wherein R\ D, E, R2, A and J are as defined in Table II and R6 is neopentyl. 20
Table K14 Table K14 provides 288 compounds of Formula Kl wherein R1, D, E, R2, A and J are as defined in Table II and R6 is 2,2-dimethylbutyl.
2j5 TableKlS
Table K15 provides 288 compounds of Formula Kl wherein R1, D, E, R2, A and J are as defined in Table II and R6 is 2,2,2-trifluoroethyl.
Table K16
3|0 Table Kl 6 provides 288 compounds of Formula Kl wherein R1, D, E, R2, A and J are
as defined in Table II and R6 is 2,2-difluoro-2-methoxyethyI.
Table K17
Table K17 provides 288 compounds of Formula Kl wherein R\ D, E, R\ A and J are 3(5 as defined in Table II and R6 is 3,3,3-trifluoropropyl.
Table K18
Table K18 provides 288 compounds of Formula Kl wherein R1, D, E, R2, A and J are as defined in Table II and R6 is/?artf-fiuorobenzyl. 40
Table K19 Table K19 provides 288 compounds of Fonnula Kl wherein R', D, E, R2, A and J are as defined in Table II and R6 is 2,4-dichlorophenyl.
4|5 Table K20
Table K20 provides 288 compounds of Formula Kl wherein R1, D, E, R2, A and J are as defined in Table II and R6 is 2-chloro-4-trifiuoromethylphenyl.
Table LI
Table LI provides 192 compounds of Formula LI, wherein R1, D, E, R2, A and J are as defined in Table LI and R6 is methyl.
Table LI
Compound
No. R1 D E R2 A J
Ll.l CH3 S C-Cl H CH2 C-H
L1.2 CH3 S C-Cl CH2CH3 CH2 C-H
L1.3 CH3 s C-Cl CH2C=CH2 CH2 C-H
L1.4 CH3 s C-Cl CH2C.CH CH2 C-H
L1.5 CH3 s C-Cl CH2OCH3 CH2 C-H
L1.6 CH3 s C-Cl CH2OCH2CH3 CH2 C-H
L1.7 CH3 s C-Br H CH2 C-H
Lt:8 CH3 g, C-Br CH2CH3 CH2 C-H
L1.9 CH3 s C-Br CH2C=:CH2 CH2 C-H
LI.10 CH3 s C-Br CH2C.CH CH2 C-H
Ll.ll
CH3 s C-Br CH2OCH3 CH2 C-H
LI.12 CH3 s C-Br CH2OCH2CH3 CH2 C-H
LI.13 CH2CH3 s C-Cl H CH2 C-H
LI.14 CH2CH3 s C-Cl CH2CH3 CH2 C-H
LI.15 OH2CH3 s C-Cl CH2C=:CH2 CH2 C-H
LI.16 CH2CH3 s C-Cl CH2C.CH CH2 C-H
LI.17 CH2CH3 s C-Cl CH2OCH3 CH2 C-H
L1.18 CH2CH} s C-Cl CH2OCH2CH3 CH2 C-H
LI.19 CH2CH3 s C-Br H CH2 C-H
LI.20 CH2CH3 s C-Br CH2CH3 CH2 C-H
L1.21 CH2CH3 s C-Br CH2C=:CH2 CH2 C-H
LI.22 CH2CH3 s C-Br CH2C.CH CH2 C-H
LI.23 CH2CH3 s C-Br CH2OCH3 CH2 C-H
LI.24 CH2CH3 s C-Br CH2OCH2CH3 CH2 C-H
LI.25 CH3 s C-Cl H CH(CH3) C-H
LI.26 CH3 s C-Cl CH2CH3 CH(CH3) C-H
LI.27 CH3 s C-Cl CH2C=Cri2 CH(CH3) C-H
LI.28 CH3 s C-Cl CHjC.CH CH(CH3) C-H
LI.29 CH3 s C-Cl CH2OCH3 CH(CH3) C-H
L1.30 CH3 s C-Cl CH2OCH2CH3 CH(CH3) C-H
L1.31 CH3 s C-Br H CH(CH3) C-H
LI.32 CH3 S C-Br CH2CH3 CH(CH3) C-H
LI.33 CH3 S C-Br CH2C=CH2 CH(CH3) C-H
LI.34 CH3 S C-Br CH2C.CH CH(CH3) C-H
LI.35 CH3 S C-Br CH2OCH3 CH(CH3) C-H
LI.36 CH3 S C-Br CH2OCH2CH3 CH(CH3) C-H
LI.37 CHjCHg S C-Cl H CH(CH3) C-H
LI.38 CH2CH3 S C-Cl CH2CH3 CH(CH3) C-H
L1.39 Cri2Cri3 S C-Cl CH2C-^Cri2 CH(CH3) C-H
LI.40 CH2CH3 S C-Cl CH2C.CH CH(CH3) C-H
L1.41 CH2CH3 S C-Cl CH2OCH3 CH(CH3) C-H
LI.42 CH2CH3 S C-Cl CH2OCH2CH3 CH(CH3) C-H
LI.43 C.ri2CH3 S C-Br H CH(CH3) C-H
L1.44 CH2CH3 s C-Br CH2CH3 CH(CH3) C-H
LI.45 CH2CH3 s C-Br CH2C=:CJH.2 CH(CH3) C-H
LI.46 CH2CH3 s C-Br CH2C.CH CH(CH3) C-H
LI .47 CH2CH3 s C-Br CH2OCH3 CH(CH3) C-H
LI.48 CH2CH3 s C-Br CH2OCH2CH3 CH(CH3) C-H
LI.49 CH3 s C-Cl H CHF C-H
L1.50 CH3 s C-Cl CH2CH3 CHF C-H
LI.51 CH3 s C-Cl : Cri2C==Crl2 CHF C-H
LI.52; CH3 .;■ S V C-Cl CH2C.CH CHF C-H
L1.53 ; CH3 s C-Cl CH2pCH3 CHF C-H
L1.54 CH3 s C-Cl CH2OCH2CH3 CHF C-H
LI.55 CH3 s C-Br H CHF C-H
L1.56 CH3 s C-Br CH2CH3 CHF C-H
LI.57 CH3 s C-Br CH2C=CH2 CHF C-H
L1.58 CH3 s C-Br Cri2C.Cxi CHF C-H
LI.59 CH3 s C-Br CH2OCH3 CHF C-H
LI.60 CH3 s C-Br CH2OCH2CH3 CHF C-H
L1.61 CH2CH3 s C-Cl H CHF C-H
LI.62 CH2CH3 s C-Cl Cri2CH3 CHF C-H
LI.63 CH2CH3 s C-Cl CH2C=Cri2 CHF C-H
L1.64 OH2CH3 s C-Cl CH2C.CH CHF C-H
L1.65 CH2CH3 s C-Cl CH2OCH3 CHF C-H
LI.66 CH2CH3 s C-Cl CH2OCH2CH3 CHF C-H
LI.67 C_.xijCxi3 s C-Br H CHF C-H
LI.68 CH2CH3 s C-Br CH2CH3 CHF C-H
LI.69 CH2CH3 s C-Br Cri2C=CH2 CHF C-H
LI.70 CH2CH3 s C-Br CH2C.CH CHF C-H
L1.71 CH2CH3 s C-Br CH2OCH3 CHF C-H
LI.72 CrijCr^ s C-Br CH20CH2CH3 CHF C-H
LI.73 CH3 s C-Cl H CH20 C-H
L1.74 CH3 s C-Cl CIi2CH3 CH20 C-H
LI.75 CH3 s c-ci 1 CH2C=CH2 CH20 C-H
LI.76 CH3 S C-Cl CH2C.CH CH20 C-H
LI.77 CH3 s C-Cl CH2OCH3 CH20 C-H
L1.78 CH3 s C-Cl CH2OCH2CH3 CH20 C-H
LI .79 CH3 s C-Br H CH20 C-H
L1.80 CH3 s C-Br CH2CH3 CH20 C-H
L1.81 CH3 s C-Br CH2C=CH2 CH20 C-H
LI.82 CH3 s C-Br CH2C.CH CH20 C-H
LI.83 CH3 s C-Br CHjOCH^ CH20 C-H
L1.84 CH3 s C-Br CH2OCH2CH3 CH20 C-H
L1.85 CH2CH3 s C-Cl H CH20 C-H
L1.86 CH2CH3 s C-Cl CH2CH3 CH20 C-H
L1.87 CH2CH3 s C-Cl CH2C-CH2 CH20 C-H
L1.88 CHJGHJ s C-Cl CH2C.CH CH20 C-H
LI.89 CH2CH3 s C-Cl CH2OCH3 CH20 C-H
LI.90 CHJGHJ s C-Cl CH2OCH2CH3 CH20 C-H
L1.91 CH2CH3 S - C-Br H CH20 C-H
LI.92 CH2Cn3 s C-Br CHJCHJ CH20 C-H
LI .93 CHJCH3 s C-Br CH2C=ECH2 CH20 C-H
LI.94 CH2CH3 s C-Br CH2C.CH CH20 C-H
L1..95 CH2GH3 s C-Br CH2OCH3 CH20 C-H
Ll.96 CH^CsH^ s C-Br CH2OCH2CH3 CHjO C-H
Li.97 CH3 s C-Cl H CH2 C-Cl
LI.98 CH3 s C-Cl GH2CH3 CH2 C-Cl
LI.99 CH3 s C-Cl Cjl2CS!CH2 CH2 J C-Cl
L1.100 CH3 s C-Cl CH2C.CH CH2 C-Cl
L1.101 CH3 s C-Cl CH2OCH3 CH2 C-Cl
L1.102 CH3 s C-Cl CH2OCH2CH3 CH2 C-Cl
LI.103 CH3 s C-Br H CH2 C-Cl
LI.104 CH3 s C-Br CH2CH3 CH2 C-Cl
LI.105 CH3 s C-Br CH2C—CH2 CH2 C-Cl
LI. 106 CH3 s C-Br CH2C.CH CH2 C-Cl
LI.107 CH3 s C-Br CH2OCH3 CH2 C-Cl
LI.108 CH3 s C-Br CH2OCH2CH3 CH2 C-Cl
LI.109 CH2CH3 s C-Cl H CH2 C-Cl
L1.110 CH2CH3 s C-Cl CH2CH3 CH2 C-Cl
LI.Ill CH2CH3 s C-Cl C^C^CH;^ CH2 C-Cl
LI.112 CH2CH3 s C-Cl CH2C.CH CH2 C-Cl
LI.113 CH2CH3 s C-Cl CH2OCH3 CH2 C-Cl
LI.114 CH2CH3 s C-Cl CH2OCH2CH3 CH2 C-Cl
LI.115 CHjCH3 s C-Br H CH2 C-Cl
LI.116 CH2CH3 s C-Br CH2CH3 CH2 C-Cl
LI.117 CH2CH3 s C-Br CH2C:=CH2 CH2 C-Cl
L1.118 CH2CH3 s C-Bi CH2C.CH CH2 C-Cl
LI.119 CHjCH3 s C-Br CH2OCH3 CH2 C-Cl
LI.120 CH2CH3 S C-Br CH2OCH2CH3 CH2 C-Cl
L1.121 CH3 s C-Cl H CH(CH3) C-Cl
L1.122 CH3 s C-Cl CH2CH3 CH(CH3) C-Cl
L1.123 CH3 s C-Cl Cri2C=Cri2 CH(CH3) C-Cl
L1.124 CH3 s C-Cl CH2C.CH CH(CH3) C-Cl
LI.125 CH3 s C-Cl CH2OCH3 CH(CH3) C-Cl
L1.126 CH3 s C-Cl CH2OCH2CH3 CH(CH3) C-Cl
LI.127 CH3 s C-Br H CH(CH3) C-Cl
L1.128 CH3 s C-Br CHjCri3 CH(CH3) C-Cl
L1.129 CH3 s C-Br CH2C=CH2 CH(CH3) C-Cl
L1.130 CH3 s C-Br CH2C.CH CH(CH3) C-Cl
L1.131 CH3 s C-Br CH2OCH3 CH(CH3) C-Cl
L1.132 CH3 s C-Br CH2OCH2CH3 CH(CH3) C-Cl
LI.133 CH2CH3 s C-Cl H CH(CH3) C-Cl
L1.134 CH2CH3 s C-Cl CH2CH3 CH(CH3) C-Cl
L1.135 CH2CH3 s C-Cl CH2C=CH2 CH(CH3) C-Cl
L1.136 Cri2CH3 s C-Cl CH2C.CH CH(CH3) C-Cl
L1.137 CH2CH3 s C-Cl CH2OCH3 CH(CH3) C-Cl
LI.138 CH2CH3 s C-Cl CH2OCH2CH3 CH(CH3) C-Cl
L1.139 CH2CH3 s C-Br H CH(CH3) C-Cl
L1.140 CH^cfi3: s C-Br CH2CH3 CH(q«3) C-Cl
LL141 ;".■'."": CH2OH3; s C-fir CH2C=C--H2 CH(CH3) C-Cl
L1.142 CH2CH3 s C-Br CH2CCH CHCCHj) C-Cl
L1.143 CH2CH3 s C-Br CH2OCH3 CH(CH3) C-Cl
L1.144 CH2CH3 s C-Br CH2OCH2CH3 CH(CH3) C-Cl
LI. 145 CH3 s C-Cl H CHF C-Cl
LI.146 CH3 s C-Cl CH2CH3 CHF C-Cl
L1.147 CH3 s C-Cl CH2CS=CH2 CHF C-Cl
LI.148 CH3 s C-Cl OH.2C.Cr1
CHF C-Cl
L1.149 CH3 s C-Cl CH2OCH3 CHF C-Cl
L1.150 CH3 s C-Cl CH2OCH2CH3 CHF C-Cl
LI.151 CH3 s C-Br H CHF C-Cl
L1.152 CH3 s C-Br CH2CH3 CHF C-Cl
L1.153 CH3 s C-Br CH2C:=CH2 CHF C-Cl
LI.154 CH3 s C-Br C-ii2C.C-ri CHF C-Cl
L1.155 CH3 s C-Br CH2OCH3 CHF C-Cl
L1.156 CH3 s C-Br CH2OCH2CH3 CHF C-Cl
L1.157 CH2CH3 s C-Cl H CHF C-Cl
LI.158 CH2CH3 s C-Cl CH2CH3 CHF C-Cl
LI.159 CH2CH3 s C-Cl CH2C==CH2 CHF C-Cl
L1.160 CH2CH3 s C-Cl CH2C.CH CHF C-Cl
L1.161 CH2CH3 s C-Cl CH2OCH3 CHF C-Cl
LI.162 CH2CH3 s C-Cl CH2OCH2CH3 CHF C-Cl
LI.163 CHJCHJ s C-Br H CHF C-Cl
L1.164 CH2CH3 S C-Br CH.20rl3 CHF C-Cl
L1.165 01120113 s C-Br OH.2C:=Cri2 , CHF C-Cl
LI.166 01120113 s C-Br CH2C.CH CHF C-Cl
L1.167 OH2CH3 s C-Br CH2OCH3 CHF C-Cl
L1.168 CH2CH3 s C-Br CH2OCH2CH3 CHF C-Cl
L1.169 CH3 s C-Cl H CH20 C-Cl
LI.170 CH3 s C-Cl CH2CH3 CH20 C-Cl
L1.171 CH3 s C-Cl CH2C==CH2 CH20 C-Cl
LI.172 CH3 s C-Cl Cri2C.CH CH20 C-Cl
L1.173 CH3 s C-Cl CHjOCH3 CH20 C-Cl
L1.174 CH3 s C-Cl CH2OCH2CH3 CH20 C-Cl
L1.175 CH3 s C-Br H CH20 C-Cl
L1.176 CH3 s C-Br CH2CH3 CH20 C-Cl
L1.177 CH3 s C-Br CH20=OH.2 CH20 C-Cl
L1.178 CH3 s C-Br CHjC.CH CH20 C-Cl
L1.179 CH3 s C-Br CH2OCH3 CH20 C-Cl
L1.180 CH3 s C-Br CH2OCH2CH3 CH20 C-Cl
L1.181 OH2CH3 s C-Cl H CH20 C-Cl
L1.182 CH2CH3 s C-Cl CH2CH3 CH20 C-Cl
L1.183 C^CH^ s C-Cl CH2C=CH2 CH20 C-Cl
LL184 CH&H3 s C^Cl GH2C.CH CH20 C-Cl
LL185 CH2GH3 _ S C-Cl CH2OCH3 CHjO C-Cl
L1.186 CHJGIL; s C-Cl CH2OCH2CH3 CH20 C-CI
L1.187 0H2OH3 s C-Br H CH20 C-Cl
LI.188 Ori2Crl3 s C-Br CH2CH3 CH20 C-Cl
L1.189 CH2GH3 s C-Br CH2C—CH2 CH20 C-Cl
L1.190 CH2CH3 s C-Br CHjCCH CH20 C-Cl
L1.191 GH2CH3 s C-Br CH2OCH3 CH20 C-Cl
LI.192 CH2CH3 s C-Br CH20CH2CH3 CH20 C-Cl
Table L2
Table L2 provides 192 compounds of Formula LI wherein R1, D, E, R2, A and J are as defined in Table LI and R6 is ethyl.
Table L3
Table L3 provides 192 compounds of Formula LI wherein R1, D, E, R2, A and J are as defined in Table LI and R6 is w-propyl,
Table L4
Table L4 provides 192 compounds of Formula LI wherein R1, D, E, R2, A and J are as defined in Table LI and R6 is iso-propyl.
Table L5
Table L5 provides 192 compounds of Formula LI wherein R1, D, E, R2, A and J are as defined in Table LI and R6 is w-butyl.
Table L6
Table L6 provides 192 compounds of Formula LI wherein R1, D, E, R2, A and J are as defined in Table LI and R6 is sec-butyl.
Table L7
Table L7 provides 192 compounds of Formula LI wherein Rl, D, E, R2, A and J are as defined in Table LI and R6 is wo-butyl.
Table L8
lp Table L8 provides 192 compounds of Formula LI wherein R1, D, E, R2, A and J are
as defined in Table LI and R6 is tert-butyl
Table L9
Table L9 provides 192 compounds of Formula LI wherein R1, D, E, R2, A and J are ; l£ as defined in Table LI and R6 is w-pentyl.
Table L10
Table L10 provides 192 compounds of Formula LI wherein R1, D, E, R2, A and J are as defined in Table LI and R* is 1-methylbutyl. 2t)
Table Lll Table Lll provides 192 compounds of Formula LI wherein R1* D,E, R2, A and J are as defined in Table LI and R6 is 2-methylbutyl.
2(5 Table L12
Table L12 provides 192 compounds of Formula LI wherein R!, D, E, R2, A and J are as defined in Table LI and R6 is 3-methylbutyl.
Table L13
3p Table L13 provides 192 compounds of Formula LI wherein Rl, D, E, R2, A and J are
as defined in Table LI and R* is neopentyl.
Table L14
Table L14 provides 192 compounds of Formula LI wherein R1, D, E, R2, A and J are 3f as defined in Table L1 and R6 is 2,2-dimethylbutyl.
Table L15
Table L15 provides 192 compounds of Formula LI wherein R1, D, E, R2, A and J are as defined in Table LI and R6 is 2,2,2-trifluoroethyl. 40
Table L16 Table LI 6 provides 192 compounds of Formula LI wherein R1, D, E, R2, A and J are as defined in Table LI and R6 is 2,2-difluoro-2-methoxyethyl.
4£ Table L17
Table LI 7 provides 192 compounds of Formula LI wherein R1, D, E, R2, A and J are as defined in Table LI and R6 is 3,3,3-trifluoropropyl.
Table L18
Table LI 8 provides 192 compounds of Formula LI wherein R1, D, E, R\ A and J are as defined in Table LI and R6 is/7tfra-fluorobenzyl.
Table L19
Table L19 provides 192 compounds of Formula LI wherein R\ D, E, R2, A and J are as defined in Table LI and R6 is 2,4-dichlorophenyl.
Table L20
l{3 Table L20 provides 192 compounds of Formula LI wherein Rl, D, E, R2, A and J are
as defined in Table LI and R6 is 2-chloro-4-trifluoromethylphenyl.
The following abbreviations are used throughout this description:
m.p. = melting point ppm = parts per million
s = singlet br = broad
d = doublet dd = doublet of doublets
t = triplet q = quartet
m = multiplet
Table 1 shows selected NMR data, all with CDC13, as the solvent (unless otherwise l|5 stated; if a mixture of solvents is present, this is indicated as, for example (CDC13 / d$-DMSO)), (no attempt is made to list all characterising data in all cases) for compounds of Tables Al to L20.
TABLE 1
Compound No. lH NMR (CDC13 unless otherwise stated)
A3.1 1.0(t,3H); 2.15(m,2H); 2.35(s,3H); 4.0(s,2H); 4.7(t,2H); 7.35(dd,lH); 7.85(d,lH); 7.95(d,lH); 8.15(br,lH).
Al.l 2.35(s,3H); 4.0(s,2H); 4.5(s,3H); 7.35(dd,lH); 7.8(d,lH); 7.9(d,lH); 8.05(br,lH).
A18.1 (rf6-DMSO): 2.35(s,3H); 4.05(s,2H); 5.8(s,2H); 7.0(m,2H); 7.4(m,3H); 7.8(m,2H); 10.9(br,lH).
A15.1 2.4(s,3H); 4.0(s,2H); 5.3(q,2H); 7.4(dd,lH); 7.85(d,lH); 7.95(d,lH); 8.15(br,lH).
A9.1 0.9(t,3H); 1.35(m,4H); 2.15(m,2H); 2.4(s,3H); 4.05(s,2H); 4.7(t,2H); 7.35(dd,lH); 7.85(d,lH); 7.9(d,lH); 8.15(br,lH).
A20.1 2.4(s,3H); 4.05(s,2H); 7.45(dd,lH); 7.75(dd,lH); 7.95(m,3H); 8.05(m,lH); 8.2(br,lH).
A7.1 0.85(t,3H); 1.7(d,3H); 2.0-2.2(m,2H); 2.35(s,3H); 4.0(s,2H); 4.9(m,lH); 7.3(dd,lH); 7.85(d,lH); 7.9(d,lH); 8.15(br,lH).
A2.1 1.75(t,3H); 2.35(s,3H); 4.0(s,2H); 4.8(q,2H); 7.35(dd,lH); 7.8(br,lH); 7.9(d,lH); 8.1(br,lH).
A3.103 1.0(t,3H); 1.25(t,3H); 2.15(m,2H); 2.85(q,2H); 3.95(s,2H); 4.7(t,2H); 7.35(m,lH); 7.85(br,lH); 7.95(d,lH); 7.95(br,lH); 8.2(d,lH); 8.35(d,lH).
A13.1 1.05(s,9H); 2.4(s,3H); 4.05(s,2H); 4.55(s,2H); 7.35(dd,lH); 7.85(br,lH); 7.95(d,lH); 8.15(br,lH).
A3.2 0.95(t,3H); 1.2(t,3H); 2.13(m,2H); 2.5(s,3H); 3.65(br,2H), 3.8(br,2H); 4.65(t,2H); 7.15(br.d,lH); 7.5(br,lH); 7.78(dd,lH).
A3.6 0.95(t,3H); 1.2(t,3H); 2.1(naH); 2.5(s,3H); 3.6(q,2H), 3.7(br,2H); 4.7(t,2H); 5.1(br,2H); 7.15(br,lH); 7.55(br,lH); 7.8(d,lH).
A21.1 2.4(s,3H); 4.1(s,2H); 7.5(m,lH), 7.8-7.9(m,4H); 8.5(br.d,2H); 10.35(s,lH).
A16.1 2.39(s,3H); 3.61(s,3H); 4.03(s,2H); 5.19(t,2H); 7.40(dd,lH); 7.88(s,lH); 7.97(d,lH); 8.16(s,lH).
A10.1 1.0(d,6H); 2.03(q,2H); 2.37(s,3H); 2.37(m,lH); 4.0(s,2H); 4.77(dd,2H); 7.34(dd,lH); 7.83(s,lH); 7.92(d,lH); 8.16(s,lH).
A6.1 1.0(d,6H); 2.37(s,3H); 2.54(septet,lH); 4.03(s,2H); 4.56(cUH); 7.36(dd,IH); 7.84(s,lH); 7.94(d,lH).
13.2 0.95(t,3H); 1.4(t,3H); 2.12(m,2H); 2.5(s,3H); 3.9(q,2H); 4.2(s,2H); 4.65(t£H); 7.42(dd,lH); 7.8(br,lH); 7.81(br,lH).
13.6 0.95(t,3H); U5(t,3H); 2.1(m£H); 2.55(s,3H); 3.5(q,2H); 4.2(s,2H); 4.7(UH), 5.2(s,2H); 7.4(dd,lH); 7.8(m,2H).
El.l 2.35(s,3H); 4.1(s,2H); 4.3(s,3H); 7.55(m,2H); 8.0(d,lH); 8.3(br.s,lH).
E15.1 2.4(s,3H); 4.05(s,2H); 5.25(q,2H); 7.4(dd,lH); 7.6(d,lH); 8.15(d,lH); 8.3(br,lH).
F15.1 2.4(s,3H); 4.1(s,2H); 5.25(q,lH); 7.6(m,2H); 8.1(br.s,lH); 8.25(br,lH).
E22.1 2.40(s,3H); 3.03(s,3H); 4.10(s,2H); 7.52(dd,2H); 8.19(d,lH); 8.2(br,lH); 8.3(d,lH).
Fl.l 2.35(s,3H); 4.1(s,2H); 4.3(s,3H); 7.3(d,lH); 7.55(d,lH); 8.1(d,lH); 8.3(br.s,lH).
F22.1 2.40(s,3H); 3.03(s,3H); 4.09(s,2H); 7.66(dd,2H); 8.10(d,lH); 8.2(br,lH); 8.34(d,lH).
E6.145 0.94(d,6H); 2.36(m,lH); 2.36(s,3H); 3.98(s,2H); 4.22(H^J R'^R^J ° N £>^J'
(la) Ob) (Ic)
Those skilled in the art will recognise that analogous reactions involving sulfenylation, sulfonylation and acylation are possible when Y is O.
A compound of formula (la), where Rn is alkoxymethyl or acyloxymethyl, may also be prepared from a compound of formula (la), where Ru is hydrogen, by sequential reaction with formaldehyde and an alkylating or acylating agent.
Additional compounds of formula (la) may be prepared from a compound of formula (I), where Ru is hydrogen, by reaction with hydroxymethylbenzotriazole or benzotriazoles 1(0 and aldehydes according to the method of A.R.Katritzky et ah, J. Org. Chem., (1993), 58, 2086.
A compound of formula (Ic) where Y = S may be reacted with an alcohol, amine, O-alkylhydroxyl-amine or hydrazine, optionally in the presence of a mercuric salt (such as mercuric chloride), according to known procedures to give a compound of formula (Id) or 1(5 (Ie) respectively:
R3^< J
(id) (le)
where Re is H, optionally substituted alkyl, alkenyl or alkynyl, Rf is substituted alkyl, 2(0 alkenyl alkynyl, amino, substituted amino or alkoxy and Rg is optionally substituted alkyl, alkenyl or alkynyl.
A compound of formula (Id) where Re is hydrogen may be treated with an optionally substituted alkylating agent (such as an alkyl halide, chloromethylether, dialkyl sulfate or trialkyloxonium salt) optionally in the presence of a base to give a compound of formula (If).
25
Heteroaryl N-oxides can be produced by methods known to the skilled person.
It will be appreciated that compounds of fomula (la), (lb), (Ic), (Id), (Ie), (If), (IV), (V), (VI) and (VII) are all compounds of formula (I).
The compounds of formula (I) can be used to combat and control infestations of insect pests such as Lepidoptera, Diptera, Hemiptera, Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera, Hymenoptera and Isoptera and also other invertebrate pests, for ly example, acarine, nematode and mollusc pests. Insects, acarines, nematodes and molluscs are hereinafter collectively referred to as pests. The pests which may be combated and controlled by the use of the inventioncompounds include those pests associated with agriculture (which term includes the growing of crops for food and fibre products), horticulture and animal husbandry, companion animals, forestry and the storage of products 1 E> of vegetable origin (such as fruit, grain and timber); those pests associated with the damage of man-made structures and the transmission of diseases of man and animals; and also nuisance pests (such as flies).
Examples of pest species which may be controlled by the compounds of formula (I) include: Myzuspersicae (aphid), Aphis gossypii (aphid), Aphis fabae (aphid), Lygus spp.
2D (capsids), Dysdercus spp. (capsids), Nilaparvata lugens (planthopper), Nephotettixc incticeps (leafhopper), Nezara spp. (stinkbugs), Euschistus spp. (stinkbugs), Leptocorisa spp. (stinkbugs), FranMiniella occidentalis (thrip), Thrips spp. (thrips), Leptinotarsa decemlineata (Colorado potato beetle), Anthonomus grandis (boll weevil), Aonidiella spp. (scale insects), Trialeurodes spp. (white flies), Bemisia tabaci (white fly), Ostrinia mibilalis
2fc (European com borer), Spodoptera littoralis (cotton leafworm), Heliothis virescens (tobacco budworm), Helicoverpa armigera (cotton bollworm), Helicoverpa zea (cotton bollworm), Sylepta derogata (cotton leaf roller), Pieris brassicae (white butterfly), Plutella xylostella (diamond back moth), Agrotis spp. (cutworms), Chilo suppressalis (rice stem borer), Locusta
migratoria (locust), Chortiocetes termini/era (locust), Diabrotica spp. (rootworms), Panonychus ulmi (European red mite), Panonychus citri (citrus red mite), Tetranychus urticae (two-spotted spider mite), Tetranychus cinnabarinus (carmine spider mite), Phyllocoptruta oleivora (citrus rust mite), Polyphagotarsonemus lotus (broad mite), Brevipalpus spp. (flat mites), Boophilus microplus (cattle tick), Dermacentor variabilis (American dog tick), Ctenocephalides felis (cat flea), Liriomyza spp. (leafminer), Musca domestica (housefly), Aedes aegypti (mosquito), Anopheles spp. (mosquitoes), Culex spp. (mosquitoes), Lucillia spp. (blowflies), Blattella germanica (cockroach), Periplaneta americana (cockroach), Blatta orientalis (cockroach), termites of the Mastotermitidae (for example Mastotermes spp.), the Kalotermitidae (for example Neotermes spp.), the Rhinotermitidae (for example Coptotermesformosanus, Reticulitermes flavipes, R. speratu, R. virginicus, R. hesperus, and R. santonensis) and the Termitidae (for example Globitermes sulphureus), Solenopsis geminata (fire ant), Monomorium pharaonis (pharaoh's ant), Damalinia spp. and Linognathus spp. (biting and sucking lice), Meloidogyne spp. (root knot nematodes); Globodera spp. andfieterodera spp. (cyst nematodes), Pratylenchus spp. (lesion nematodes), Rhodopholus spp: (banana burrowing nematodes), Tylenchulus spp.(citrus nematodes), Haemonchus contortus (barber pole worm), Caenorhabditis elegans (vinegar eelworm), Trichostrongylus spp. (gastro intestinal nematodes) and Deroceras reticulatum (slug).
The compounds of formula (I) are also active fungicides and may be used to control one or more of the following pathogens: Pyricularia oryzae (Magnaporthe grisea) on rice and wheat and other Pyricularia spp. on other hosts; Puccinia recondita, Puccinia striiformis and other rusts on wheat, Puccinia hordei, Puccinia striiformis and other rusts on barley, and rusts on other hosts (for example turf, rye, coffee, pears, apples, peanuts, sugar beet, vegetables and ornamental plants); Erysiphe cichoracearum on cucurbits (for example melon); Erysiphe graminis (powdery mildew) on barley, wheat, rye and turf and other powdery mildews on various hosts, such as Sphaerotheca macularis on hops, Sphaerotheca fiisca (Sphaerotheca fuligined) on cucurbits (for example cucumber), Leveillula taurica on tomatoes, aubergine and green pepper, Podosphaera leucotricha on apples and Uncinula necator on vines; Cochliobolus spp., Helminthosporium spp., Drechslera spp. (Pyrenophora spp.), Rhynchosporium spp., Mycosphaerella graminicola (Septoria tritici) and
Phaeosphaeria nodorum (Stagonospora nodorum or Septoria nodorum), Pseudocercosporella herpotrichoides and Gaeumannomyces graminis on cereals (for example wheat, barley, rye), turf and other hosts; Cercospora arachidicola and Cercosporidium personatum on peanuts and other Cercospora spp. on other hosts, for example sugar beet, bananas, soya beans and rice; Botrytis cinerea (grey mould) on tomatoes, strawberries, vegetables, vines and other hosts and other Botrytis spp. on other hosts; Alternaria spp. on vegetables (for example carrots), oil-seed rape, apples, tomatoes, potatoes, cereals (for example wheat) and other hosts; Venturia spp. (including Venturia inaequalis (scab)) on apples, pears, stone fruit, tree nuts and other hosts; Cladosporium spp. on a range
lp of hosts including cereals (for example wheat) and tomatoes; Monilinia spp. on stone fruit, tree nuts and other hosts; Didymella spp. on tomatoes, turf, wheat, cucurbits and other hosts; Phoma spp. on oil-seed rape, turf, rice, potatoes, wheat and other hosts; Aspergillus spp. and Aureobasidium spp. on wheat, lumber and other hosts; Ascochyta spp. on peas, wheat, barley and other hosts; Stemphylium spp. (Pleospora spp.) on apples,-pears, onions and other hosts;
l|5 summer diseases (for example bitter rot {Glomerellacingulatd), black rot or frogeye leaf spot {Botryosphaeriaobiusa)i Brooks fruit spot (Mycosphaerellapomi), Cedar apple rust {Gymnosporangiumjuniperi-virginianae), sooty blotch (Gloeodes pomigena), fiyspeck {Schizothyrium pomi) and white rot (Botryosphaeria dothidea)) on apples and pears; Plasmopara viticola on vines; other downy mildews, such as Bremia lactucae on lettuce,
2)0 Peronospora spp. on soybeans, tobacco, onions and other hosts, Pseudoperonospora humuli on hops and Pseudoperonospora cubensis on cucurbits; Pythium spp. (including Pythium ultimum) on turf and other hosts; Phytophthora infestans on potatoes and tomatoes and other Phytophthora spp. on vegetables, strawberries, avocado, pepper, ornamentals, tobacco, cocoa and other hosts; Thanatephorus cucumeris on rice and turf and other Rhizoctonia spp.
2}5 on various hosts such as wheat and barley, peanuts, vegetables, cotton and turf; Sclerotinia spp. on turf, peanuts, potatoes, oil-seed rape and other hosts; Sclerotium spp. on turf, peanuts and other hosts; Gibberellafujikuroi on rice; Colletotrichum spp. on a range of hosts including turf, coffee and vegetables; Laetisariafuciformis on turf; Mycosphaerella spp. on bananas, peanuts, citrus, pecans, papaya and other hosts; Diaporthe spp. on citrus, soybean,
3)0 melon, pears, lupin and other hosts; Elsinoe spp. on citrus, vines, olives, pecans, roses and other hosts; Verticillium spp. on a range of hosts including hops, potatoes and tomatoes;
Pyrenopeziza spp. on oil-seed rape and other hosts; Oncobasidium theobromae on cocoa
causing vascular streak dieback; Fusarium spp., Typhula spp., Microdochium nivale,
Ustilago spp., Urocystis spp., Tilletia spp. and Claviceps purpurea on a variety of hosts but
particularly wheat, barley, turf and maize; Ramularia spp. on sugar beet, barley and other
hosts; post-harvest diseases particularly of fruit (for example Penicillium digitatum,
Penicillium italicum and Trichoderma viride on oranges, Colletotrichum musae and
Gloeosporium musarum on bananas and Botrytis cinerea on grapes); other pathogens on
vines, notably Eutypa lata, Guignardia bidwellii, Phettinus igniarus, Phomopsis viticola,
Pseudopeziza tracheiphila and Stereum hirsutum; other pathogens on trees (for example
Lophodermium seditiosum) or lumber, notably Cephaloascusfragrans, Ceratocystis spp.,
Ophiostoma piceae, Penicillium spp., Trichoderma pseudokoningii, Trichoderma viride,
Trichoderma harzianum, Aspergillus niger, Leptographium lindbergi and Aureobasidium
pullulans; and fungal vectors of viral diseases (for example Polymyxa graminis on cereals as
the vector of barley yellow mosaic virus (B YMV) and Polymyxa betae on sugar beet as the
vector of rhizomania)i i L ■>'■■'-'■
A compound of formula (I) may move acropetally, basipetally or locally in plant tissue to be active against one or more fungi. Moreover, a compound of formula (I) may be volatile enough to be active in the vapour phase against one or more fungi on the plant. The invention therefore provides a method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), or a composition containing a compound of formula (I), to a pest, a locus of pest, or to a plant susceptible to attack by a pest, and a method of combating and controlling fungi which comprises applying a fungicidally effective amount of a compound of formula (I), or a composition containing a compound of formula (I), to a plant, to a seed of a plant, to the locus of the plant or seed, to soil or to any other growm medium (for example a nutrient solution). The compounds of formula (I) are preferably used against insects, acarines, nematodes or fungi.
The term "plant" as used herein includes seedlings, bushes and trees. Furthermore, the fungicidal method of the invention includes protectant, curative, systemic, eradicant and antisporulant treatments.
As fungicides, the compounds of formula (I) are preferably used for agricultural, horticultural and turfgrass purposes in the form of a composition.
In order to apply a compound of formula (I) as an insecticide, acaricide, nematicide or molluscicide to a pest, a locus of pest, or to a plant susceptible to attack by a pest, or, as a 5 fungicide to a plant, to a seed of a plant, to the locus of the plant or seed, to soil or to any other growth medium, a compound of formula (I) is usually formulated into a composition which includes, in addition to the compound of formula (I), a suitable inert diluent or carrier and, optionally, a surface active agent (SFA). SFAs are chemicals which are able to modify the properties of an interface (for example, liquid/solid, liquid/air or liquid/liquid interfaces)
13 by lowering the inteifacial tension and thereby leading to changes in other properties (for example dispersion, emulsification and wetting). It is preferred that all compositions (both solid and liquid formulations) comprise, by weight, 0.0001 to 95%, more preferably 1 to 85%, for example 5 to 60%, of a compound of formula (I). The composition is generally used for the control of pests or fungi such that a compound of formula (I) is applied at a rate
15 of from 0.1 g to 10kg per hectare, preferably from 1 g to 6kg per hectare, more preferably from lg to lkg per hectare.
When used in a seed dressing, a compound of formula (I) is used at a rate of 0.0001 g to lOg (for example O.OOlg or 0.05g), preferably 0.005g to lOg, more preferably 0.005g to 4g, per kilogram of seed.
23 In another aspect the present invention provides an insecticidal, acaricidal,
nematicidal, molruscicidal or fungicidal composition comprising an insecticidally, acaricidally, nematicidally, molluscicidally or fungicidally effective amount of a compound of formula (I) and a suitable carrier or diluent therefor. The composition is preferably an insecticidal, acaricidal, nematicidal or fungicidal composition.
25 In a still further aspect the invention provides a method of combating and controlling
pests or fungi at a locus which comprises treating the pests or fungi or the locus of the pests or fungi with an insecticidally, acaricidally, nematicidally, molluscicidally or fungicidally effective amount of a composition comprising a compound of formula (I). The compounds of formula (I) are preferably used against insects, acarines, nematodes or fungi.
3) The compositions can be chosen from a number of formulation types, including
dustable powders (DP), soluble powders (SP), water soluble granules (SG), water dispersible
granules (WG), wettable powders (WP), granules (GR) (slow or fast release), soluble concentrates (SL), oil miscible liquids (OL), ultra low volume liquids (UL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsions (both oil in water (EW) and water in oil (EO)), micro-emulsions (ME), suspension concentrates (SC), aerosols, fogging/smoke formulations, capsule suspensions (CS) and seed treatment formulations. The formulation type chosen in any instance will depend upon the particular purpose envisaged and the physical, chemical and biological properties of the compound of formula
Dustable powders (DP) may be prepared by mixing a compound of formula (I) with lp one or more solid diluents (for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulphur, lime, flours, talc and other organic and inorganic solid carriers) and mechanically grinding the mixture to a fine powder. Soluble powders (SP) may be prepared by mixing a compound of formula (I) with one or
1|5 more water-soluble inorganic salts {such as sodium bicarbonate; sodium carbonate or
magnesium sulphate) or one or more Water-soluble organic solids (such as a polysaccharide) and, optionally, one or more wetting agents, one or more dispersing agents or a mixture of said agents to improve water dispersibility/solubility. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water soluble granules (SG).
2)0 Wettable powders (WP) may be prepared by mixing a compound of formula (I) with
one or more solid diluents or carriers, one or more wetting agents and, preferably, one or more dispersing agents and, optionally, one or more suspending agents to facilitate the dispersion in liquids. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water dispersible granules (WG).
2|5 Granules (GR) may be formed either by granulating a mixture of a compound of
formula (I) and one or more powdered solid diluents or carriers, or from pre-formed blank granules by absorbing a compound of formula (I) (or a solution thereof, in a suitable agent) in a porous granular material (such as pumice, attapulgite clays, fuller's earth, kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing a compound of formula (I) (or a
3p solution thereof, in a suitable agent) on to a hard core material (such as sands, silicates, mineral carbonates, sulphates or phosphates) and drying if necessary. Agents which are
commonly used to aid absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters) and sticking agents (such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils). One or more other additives may also be included in granules (for example an emulsifying agent, wetting agent or dispersing agent).
Dispersible Concentrates (DC) may be prepared by dissolving a compound of
formula (I) in water or an organic solvent, such as a ketone, alcohol or glycol ether. These
solutions may contain a surface active agent (for example to improve water dilution or
prevent crystallisation in a spray tank).
lp Emulsifiable concentrates (EC) or oil-in-water emulsions (EW) may be prepared by
dissolving a compound of formula (I) in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of said agents). Suitable organic solvents for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; 1(5 SOLVESSO is a Registered Trade Mark), ketones (such as cyclohexanone or
methylcyclohexanone) and alcohols (such as benzyl alcohol, furfuryl alcohol or butanol), N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone), dimethyl amides of fatty acids (such as Cg* fatty alcohols and phosphoric acid (predominately mono-esters) or phosphorus pentoxide (predominately di-esters), for example the reaction between lauryl alcohol and tetraphosphoric acid; additionally these products may be ethoxylated), sulphosuccinamates, paraffin or define sulphonates, taurates and lignosulphonates.
Suitable SFAs of the amphoteric type include betaines, propionates and glycinates.
3p Suitable SFAs of the non-ionic type include condensation products of alkylene
oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with
fatty alcohols (such as oieyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenol, nonylphenol or octylcresol); partial esters derived from long chain fatty acids or hexitol anhydrides; condensation products of said partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide); alkanolamides; simple esters (for example fatty acid polyethylene glycol esters); amine oxides (for example lauryl dimethyl amine oxide); and lecithins.
Suitable suspending agents include hydrophilic colloids (such as polysaccharides,
polyvinylpyrrolidone or sodium carboxymethylcellulose) and swelling clays (such as
bentonite or attapulgite).
1 p A compound of formula (I) may be applied by any of the known means of applying
pesticidal or fungicidal compounds. For example, it may be applied, formulated or unformulated, to the pests or to a locus of the pests (such as a habitat of the pests, or a growing plant liable to infestation by the pests) or to any part of the plant, including the foliage, stems, branches or roots, to the seed before it is planted or to other media in which 1(5 plants are growing or are to be planted (such as soil surrounding the roots, the soil generally, paddy water or hydroponic culture systems), directly or it may be sprayed on, dusted on, applied by dipping, applied as a cream or paste formulation, applied as a vapour or applied through distribution or incorporation of a composition (such as a granular composition or a composition packed in a water-soluble bag) in soil or an aqueous environment.
2p A compound of formula (I) may also be injected into plants or sprayed onto
vegetation using electrodynamic spraying techniques or other low volume methods, or applied by land or aerial irrigation systems.
Compositions for use as aqueous preparations (aqueous solutions or dispersions) are generally supplied in the form of a concentrate containing a high proportion of the active
2(5 ingredient, the concentrate being added to water before use. These concentrates, which may include DCs, SCs, ECs, EWs, MEs SGs, SPs, WPs, WGs and CSs, are often required to withstand storage for prolonged periods and, after such storage, to be capable of addition to water to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment. Such aqueous preparations may
3p contain varying amounts of a compound of formula (I) (for example 0.0001 to 10%, by weight) depending upon the purpose for which they are to be used.
A compound of formula (I) may be used in mixtures with fertilisers (for example nitrogen-, potassium- or phosphonis-containing fertilisers). Suitable formulation types include granules of fertiliser. The mixtures suitably contain up to 25% by weight of the compound of formula (I).
The invention therefore also provides a fertiliser composition comprising a fertiliser and a compound of formula (I).
The compositions of this invention may contain other compounds having biological activity, for example micronutrients or compounds having similar or complementary fungicidal activity or which possess plant growth regulating, herbicidal, insecticidal, lp nematicidal or acaricidal activity.
By including another fungicide, the resulting composition may have a broader
spectrum of activity or a greater level of intrinsic activity than the compound of formula (I)
alone. Further the other fungicide may have a synergistic effect on the fungicidal activity of
the compound of formula (I).
1)5 The compound of formula (I) may be the sole active ingredient of the composition or
it may be admixed with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide or plant growth regulator where appropriate. An additional active ingredient may: provide a composition having a broader spectrum of activity or increased persistence at a locus; synergise the activity or complement the activity (for 2j0 example by increasing the speed of effect or overcoming repellency) of the compound of formula (I); or help to overcome or prevent the development of resistance to individual components. The particular additional active ingredient will depend upon the intended utility of the composition. Examples of suitable pesticides include the following:
a) Pyrethroids, such as peimethrin, cypermethrin, fenvalerate, esfenvalerate, deltamethrin,
2)5 cyhalothrin (in particular lambda-cyhalothrin), bifenthrin, fenpropathrin, cyfluthrin,
tefluthrin, fish safe pyrethroids (for example ethofenprox), natural pyrethrin, tetramethrin, s-bioallethrin, fenfluthrin, prallethrin or 5-berizyl-3-furylmethyl-(E)-(lR,3S)-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate;
b) Organophosphates, such as, profenofos, sulprofos, acephate, methyl parathion,
30 azinphos-methyl, demeton-s-methyl, heptenophos, thiometon, fenamiphos, monocrotophos, profenofos, triazophos, methamidophos, dimethoate, phosphamidon, malathion, chlorpyrifos,
phosalone, terbufos, fensulfothion, fonofos, phorate, phoxim, pirirniphos-methyl, pirimiphos-ethyl, fenitrothion, fosthiazate or diazinon;
c) Carbamates (including aryl carbamates), such as pirimicarb, triazamate, cloethocarb,
carbofuran, furathiocarb, ethiofencarb, aldicarb, tbiofurox, carbosulfan, bendiocarb,
5 fenobucarb, propoxur, methomyl or oxamyl;
d) Benzoyl ureas, such as diflubenzuron, triflumuron, hexaflurnuron, flufenoxuron or chlorfluazuron;
e) Organic tin compounds, such as cyhexatin, fenbutatin oxide or azocyclotin;
f) Pyrazoles, such as tebufenpyrad and fenpyroximate;
10 g) Macrolides, such as avennectins or milbemycins, for example abamectin, emamectin
benzoate, ivermectin, milbemycin, spinosad or azadirachtin;
h) Hormones or pheromones;
i) Organochlorine compounds such as endosulfan, benzene hexachloride, DDT, chlordane or
dieldrin; ]5 j) Amidmes, such as cWordmiefonn or amitraz*
k) Fumigant agents, such as chloropicrin, dichloropropane, methyl bromide or metam;
1) Chloronicotinyl compounds such as imidacloprid, thiacloprid, acetamiprid, nitenpyram or
thiamethoxam;
m) Diacylhydrazines, such as tebufenozide, chromafenozide or methoxyfenozide; \ 0 n) Diphenyl ethers, such as diofenolan or pyriproxifen;
o) Indoxacarb;
p) Chlorfenapyr; or
q) Pymetrozine.
In addition to the major chemical classes of pesticide listed above, other pesticides i 5 having particular targets may be employed in the composition, if appropriate for the intended
utility of the composition. For instance, selective insecticides for particular crops, for
example stemborer specific insecticides (such as cartap) or hopper specific insecticides (such
as buprofezin) for use in rice may be employed. Alternatively insecticides or acaricides
specific for particular insect species/stages may also be included in the compositions (for 10 example acaricidal ovo-larvicides, such as clofentezine, flubenzirnine, hexythiazox or
tetradifon; acaricidal motilicides, such as dicofol or propargite; acaricides, such as
bromopropylate or chlorobenzilate; or growth regulators, such as hydramethylnon, cyromazine, methoprene, chlorfluazuron or diflubenzuron).
Examples of fungicidal compounds which may be included in the composition of the mvenh^nare(J^-iV-memyl-2-[2-(2,5Hiimethylphenoxymethyl)phenyl]-2-niethoxy-iminoacetamide (SSF-129), 4-bromo-2-cyano-JV^-dimethyl-6-trifluoromethyl-benzin^dazole-l-sulphonarnide,a-[iV-(3-chloro-2,6-xylyl)-2-methoxy-acetarnido]-y-butyrolactone, 4-chloro-2-cyano-Ay^-d^emyl-5-/vtolylimidazole-l -sulfonamide (IKF-916, cyamidazosulfamid), 3-5-dichloro-AH3-cMoro-l-ethyl-l-methyl-2-oxopropyl)-4-methylben2amide (RH-7281, zoxamide), N-allyl-4,5,-dimethyl-2-
lp trimethylsilylthiophene-3-carboxamide (MON65500), ^-(l-cyano-l^-dimethylpropyl)^-(2,4-dicmorophenoxy)propionamide(AC382042),7^-(2-methoxy-5-pyridyl)-cyclopropane carboxamide, acibenzolar (CGA245704), alanycarb, aldimorph, anilazine, azaconazole, azoxystrobin, benalaxyl, benomyl, biloxazol, bitertanol, blasticidin S, bromuconazole, bupirimate, captafol, captan, carbendazim, carbendazim chlorhydrate, carboxin, carpropamid,
1|5 carvone, CGA41396, CGA41397, chinomethionate, chlorothalonil,chlorozolinate,
clozylacon, copper containing compounds such as copper oxychloride, copper oxyquinolate, copper sulphate, copper tallate and Bordeaux mixture, cymoxanil, cyproconazole, cyprodinil, debacarb, di-2-pyridyl disulphide l,l'-dioxide, dichlofluanid, diclomezine, dicloran, diethofencarb, difenoconazole, difenzoquat, diflumetorim, 0,0-di-wo-propyl-iS'-benzyl
2)0 thiophosphate, dimefluazole, dimetconazole, dimethomorph, dimethirimol, diniconazole, dinocap, dithianon, dodecyl dimethyl ammonium chloride, dodemorph, dodine, doguadine, edifenphos, epoxiconazole, ethirimol, ethyl(Z)-JV-benzyl-JV([methyl(methyl-tbioemylideneammooxycarbonyl)animo3tbio)-p-alaninate, etridiazole, famoxadone, fenamidone (RPA407213), fenarimol, fenbuconazole, fenfuram, fenhexamid (KBR2738),
2j5 fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, fluoroimide, fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fuberidazole, furalaxyl, furametpyr, guazatine, hexaconazole, hydroxyisoxazole, hymexazole, imazalil, imibenconazole, iminoctadine, iminoctadine triacetate, ipconazole, iprobenfos, iprodione, iprovalicarb (SZX0722), isopropanyl butyl
3p carbamate, isoprothiolane, kasugamycin, kresoxim-methyl, L Yl 86054, LY211795,
LY248908, mancozeb, maneb, mefenoxam, mepanipyrim, mepronil, metalaxyl, metconazole,
metiram, metiram-zinc, metominostrobin, myclobutanil, neoasozin, nickel dimethyldithio-carbamate, nitrothal-wopropyl, nuarimol, ofurace, organomercury compounds, oxadixyl, oxasulfuron, oxolinic acid, oxpoconazole, oxycarboxin, pefurazoate, penconazole, pencycuron, phenazin oxide, phosetyl-Al, phosphorus acids, phthalide, picoxystrobin (ZA1963), polyoxin D, polyram, probenazole, prochloraz, procymidone, propamocarb, prop-iconazole, propineb, propionic acid, pyrazophos, pyrifenox, pvrimethanil, pyroquilon, pyr-oxyfur, pyrrolnitrin, quaternary ammonium compounds, quinomethionate, quinoxyfen, quintozene, sipconazole (F-155), sodium pentachlorophenate, spiroxamine, streptomycin, sulphur, tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole, thifluzamid, 2-(thiocyanomemylthio)benzothiazole, thiophanate-methyl, thiram, timibenconazole, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazbutil, triazoxide, tricyclazole, tridemorph, trifloxystrobin (CGA279202), triforine, triflumizole, triticonazole, validamycin A, vapam, vinclozolin, zineb and ziram.
The compounds of formula (I) may be mixed with soil, peat or other rooting media for the protection of plants against seed-borne, soil-bome or foliar fungal diseases.
Examples of suitable synergists for use in the compositions include piperonyl butoxide, sesamex, safroxan and dodecyl imidazole.
Suitable herbicides and plant-growth regulators for inclusion in the compositions will depend upon the intended target and the effect required.
An example of a rice selective herbicide which may be included is propanil. An example of a plant growth regulator for use in cotton is PTX™.
Some mixtures may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional formulation type. In these circumstances other formulation types may be prepared. For example, where one active ingredient is a water insoluble solid and the other a water insoluble liquid, it may nevertheless be possible to disperse each active ingredient in the same continuous aqueous phase by dispersing the solid active ingredient as a suspension (using a preparation analogous to that of an SC) but dispersing the liquid active ingredient as an emulsion (using a preparation analogous to that of an EW). The resultant composition is a suspoemulsion (SE) formulation.
The invention is illustrated by the following Examples.
EXAMPLE 1
This Example illustrates the preparation of N-(4-chloro-3-methylisothiazol-5-yl)-(2-
propylbenzotriazol-5-yl)acetamide (Compound No.A3.1).
Step 1 - Preparation of methyl 4-aminophenvlacetate.
5 4-Aminophenylacetic acid (1 OOg) was suspended in methanol (1000ml) and gaseous
hydrogen chloride was passed through until the mixture was saturated. The mixture was heated at 50°C for 2hours and was then allowed to cool to room temperature. The solvent was evaporated in vacuo and the residue was taken up in aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic extract was washed with brine, dried 10 over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo to afford methyl 4-aminophenylacetate as a pale brown liquid.
*H NMR (CDC13) 5 ppm: 3.5(s,2H); 3.7(s,3H); 6.65(m,2H); 7.05(m,2H). Step 2 - Preparation of methyl 4-acetamido-3-nitrophenvlacetate.
Methyl 4-aminophenylacetate (1 lOg, 0.667mol) was added dropwise to acetic ] 5 anhydride «500nu% mamtaining the temperature of the reaction mixture below 30°C by
external cooling. Once the addition was complete the mixture was cooled to below 10°C and concentrated nitric acid (85 ml) was added dropwise. Once the addition of the acid was complete, the mixture was allowed to warm to room temperature and poured onto a mixture of ice and water. The precipitated solid was collected by filtration and dried to give methyl 10 4-acetamido-3-nitrophenylacetate (120g) as a pale yellow solid.
'HNMR (CDCI3) 5 ppm: 2.3(s,3H); 3.65(s,2H); 3.7(s,3H); 7.55(dd,lH); 8.1(d,lH); 8.7(d,lH); 10.3(b,lH). Step 3 - Preparation of methyl 4-acetamido-3-aminophenvlacetate.
Methyl 4-acetamido-3-nitrophenylacetate (40g, 0.159mol)) was dissolved in 15 methanol (400ml) and hydrogenated at 5bar over a 5% palladium on carbon catalyst. The catalyst was removed by filtration and the filtrate evaporated in vacuo to give methyl 4-acetamidoO-aminophenylacetate. Step 4 - Preparation of methyl (benzotriazol-5-vDacetate.
Methyl 4-acetamido-3-aminophenylacetate (77g, 0.373mol) was taken up in a ; 0 mixture of acetic acid (210ml) and water (210ml) and cooled to below 5°C. A solution of sodium nitrite (38.63g, 0.559mol) in water (200ml) was added dropwise, and once the
addition was complete the mixture was stirred for 4hours, warming slowly to room temperature. The mixture was diluted with ethyl acetate and the insoluble material removed by filtration. The filtrate was washed with brine, dried over anhydrous magnesium sulfate, filtered and the solvent evaporated in vacuo, to give a viscous residue (51g) which was then dissolved in a solution of methanol (400ml) previously saturated with hydrogen chloride and the mixture stirred for 2hours. The solvent was removed in vacuo, the residue taken up in water, neutralised with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo to afford methyl 5-benzotriazoleacetate (35g) as a reddish liquid which crystallised on standing.
'HNMR (CDCI3) 5 ppm: 3.7(s,3H); 3.8(s, 2H); 7.35(d,lH); 7.8(b,2H); 13.6(b,lH). Step 5 - Preparation of methyl (2-propvlbenzotriazol-5-vl)acetate.
A solution of methyl 5-benzotriazoleacetate (lOg, 0.0523mol) in N,N-dimethylformamide was added dropwise to a chilled (ice-bath) suspension of sodium hydride (60% dispersion in oil, 2.3g, 0.0575rnol) in N,N-dimethylfonnamide. When the addition was complete, the ice-bath was removed and the mixture stirred for lhour. N-Pfopyl iodide (9.78g, 0.0575mol) was added dropwise, and once the addition was complete the mixture was stirred at room temperature for 3hours. The reaction mixture was poured onto ice/water, and extracted with ethyl acetate. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo. The residue was further purified by column chromatography to afford methyl (2-propylbenzotriazol-5-yl)acetate((4.8g).
lH NMR (CDC13) 8 ppm: 0.9(t,3H); 2.1(m,2H); 3.7(s,3H); 3.8(s,2H); 4.65(t,2H); 7.3(dd,lH); 7.7(d,lH); 7.8(d,lH). Step 6 - Preparation of (2-propvlbenzotriazol-5-vDacetic acid.
The acetate prepared in Step 5 above (4.8g, 0.0206mol) was dissolved in methanol (60ml) and potassium hydroxide flakes (1.27g, 0.0226mol) added. The mixture was refluxed for 2hours, men cooled and the solvent evaporated in vacuo. The residual solid was dissolved in water and extracted with diethyl ether. The aqueous solution was acidified to pH 1 by addition of dilute aqueous hydrochloric acid and extracted with ethyl acetate. The ethyl acetate extract was washed with brine, dried over anhydrous magnesium sulfate,
filtered and the filtrate evaporated in vacuo to afford (2-propylbenzotriazol-5-yl)acetic acid (3.6g) as a colourless solid. Step 7
The acid prepared in Step 6 (0.438g, 0.002mol) was dissolved in dichloromethane (5ml) and one drop of N,N-dimethyl formamide was added. Oxalyl chloride (0.307g, 0.0022mol) was added dropwise, and the mixture stirred at room temperature for 2hours. The solvent was removed in vacuo, the residue taken up in xylene and added to a mixture of 5-amino-4-chloro-3-methylisothiazole (0.446g, 0.003mol) in xylene and heated at reflux for 2hours. The mixture was cooled to room temperature and the solvent evaporated in vacuo. The
1(0 residue was taken up in ethyl acetate, washed sequentially with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo. The residue was further purified by flash column chromatography, eluting with 2:1 hexane : ethyl acetate, to give the title compound (0.34g) as a sandy-coloured solid.
}5 EXAMPLE 2
This Example illustrates the preparation of N-(4-chloro-3-methylisothiazol-5-yl)-N-(ethoxymethyl)-(2-propylbenzotriazol-5-yl)acetamide (Compound No. A3.6) and N-[2-emoxymemyl-4-chloro-3-memylisothiazolin-5-ylidene]-(2-propylbenzo-triazol-5-yl)acetamide(Compound No. 13.6).
2)0 Lithium bis(trimethylsilyl)amide (1.0 M solution in tetrahydrofuran, 3.3ml,
0.0033mol) was added dropwise to a solution of N-(4-chloro-3-methylisothiazol-5-yl)-(2-propylbenzotriazol-5-yl)acetamide (Compound No.A3.1) (0.699g, 0.002mol) in tetrahydrofuran (10ml) and once the addition was complete the mixture was stirred at room temperature for 30minutes. Chloromethyiethyl ether (0.620g, 0.0066mol) was added and the
2(5 mixture was stirred at room temperature for 2hours. The mixture was poured into water, neutralised, and extracted with ethyl acetate. The organic extract was dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was further purified by flash column chromatography, eluting initially with 2:1 hexane : ethyl acetate and then with ethyl acetate to give N-(4-chloro-3-methylisothiazol-5-yl)-N-(ethoxymethyl>
3p (2-propylbenzotriazol-5-yl)acetamide (0.135g) as an orange gum and N-[2-ethoxymethyl-4-
chloro-3-methylisothiazolin-5-ylidene]-(2-propylbenzotriazol-5-yl) acetamide (0.128g) as a colourless solid, m.p. 108-109 °C.
EXAMPLE 3 This Example illustrates the preparation of N-(4-chloro-3-methylisothiazol-5-yl)-[2-(2-methylpropyl)indazol-5-yl]acetamide (Compound No.A6.145). Step 1 - Preparation of 4-bromo-2-methvlacetanilide.
Acetic anhydride (15.2ml, 0.16mol) was added dropwise to a stirred mixture of 4-bromo-2-methylaniline (lO.Og, 0.054mol) and sodium acetate (2.52g, 0.056mol) in toluene (] 50ml). Once the addition was complete the mixture was warmed to S5°C and stirred for
l|0 40minutes. The mixture was cooled to room temperature, diluted with ethyl acetate and washed with water. The organic solution was evaporated in vacuo, a further quantity of toluene was added and then the solvent was evaporated to give 4-bromo-2-methylacetanilide (12.3g), as a colourless solid. Step 2 - Preparation of 5-bromoindazole.
1|5 ; te/^Butyl nitrite (8 <34gi 0.08 lmol) was added dropwise, over 30mirmtes, to a
suspension of 4-bromo^2-methylacetanilide (12.3g) in toluene (300ml) at 65°G and the mixture was stirred at 65°C for 45minutes and then at 90°C for 3hours. The mixture was cooled to room temperature and the solvent was removed in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 2:1 diethyl ether.hexane to give
2(0 5-bromoindazole (4.12g), as a sand-coloured solid.
'HNMR^DClj) S: 7.27(m,lH); 7.40-7.54(m,2H); 7.94(m,lH); 8.06(br,lH)ppm. Step 3 - Preparation of 5-bromo-l -(2-methvlpropvninda7.nle and 5-bromo-2-(2-methvlpropvDindazole.
Sodium hydride (80% suspension in oil, 0.7g, 0.023mol) was suspended in
2|5 iV^-dimethylformamide (DMF) (10ml) and then a solution of 5-bromoindazole (4.1 g, 0.021mol) in DMF (40ml) was added dropwise over 30minutes. Once the addition was complete the mixture was stirred at ambient temperature for 75minutes and then a solution of l-bromo-2-methylpropane (3.7g, 0.027mol) in DMF (25ml) was added over lOminutes. The mixture was stirred for 5hours and was then allowed to stand at ambient temperature
3p overnight. The mixture was poured into water, extracted with diethyl ether and then the organic extract was washed further with water, dried over anhydrous magnesium sulfate,
filtered and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 1:1 diethyl ether:hexane to give 5-bromo-l-(2-methylpropyl)indazole (2.67g) and 5-bromo-2-(2-methylpropyl)indazole (1.49g), each as an orange oil.
5-Bromo-l-(2-methylpropyl)indazole:
]H NMR (CDCI3) S: 0.92(d,6H); 2.32(m,lH); 4.16(d,2H); 7.28(m,lH); 7.44(m,lH); 7.86(m,lH); 7.92(s,lH)ppm.
5-Bromo-2-(2-methylpropyl)indazole:
'H NMR(CDC13) 5: 0.94(d,6H); 2.38(m,lH); 4.18(d,2H); 7.32(m,lH); 7.58(m,lH); 10 7.82(m,2H)ppm.
Step 4 - Preparation of ethyl f2-C2-methvlpropyl)indazol-5-vl1acetate.
5-Bromo-2-(2-methylpropyl)indazole (1.41 g, 0.0056mol) and palladium acetate (0.063g, 0.00028mol) were stirred in toluene (10ml) under an atmosphere of nitrogen. Ethyl trimethylsilylacetate (2.35ml, 0.0115moI), potassium ter/-butoxide (0,66g, 0.059mol) and a 1 f> 10% w/v solution of tri-fe/Y-butylphosphine in toluene (0.97ml, 0.00048mol) were added sequentially and then the mixture was heated to 90°C for 105minutes. The mixture was cooled to room temperature, diluted with diethyl ether and filtered through diatomaceous earth and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 2:1 diethyl ether: hexane to give ethyl[2-(2-2|0 methylpropyl)indazol-5-yl]acetate (1.85g),as a yellow oil.
'H NMR (CDC13) 5: 0.96(d,6H); 1.27(t,3H); 2.39(m,lH); 3.68(s,2H); 4.12-
4.22(m,4H); 7.22(m,lH); 7.54(m,lH); 7.68(m,lH); 7.84(s,lH) ppm.
Step 5 - Preparation of N-(4-chloro-3-methvlisothiazol-S-vlVf2-(2-methvloropyl'>indazol-5-
yllacetamide.
2j5 Sodium methoxide (0.42g, 0.0078mol) was added to a solution of 5-amino-4-chloro-
3-methylisothiazole (0.46g, 0.003 lmol) in tetrahydrofuran (THF) (15ml) and the mixture was stirred at ambient temperature for 15minutes. A solution of ethyl[2-(2-methylpropyl)indazol-5-yljacetate (0.80g, 0.003 lmol) in THF was added dropwise and, once the addition was complete, the mixture was stirred at ambient temperature for 3hours. The :|0 mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution and then the organic extract was dried over anhydrous magnesium sulfate, filtered
and the filtrate was evaporated in vacuo. The residue was triturated with diethyl ether to give N-(4-chlorc-3-methylisotMa2»l-5-yl)-[2-(2-methylpropyl)indazol-5-yl]acetamide(0.78g)as a pale-brown solid (m.p. 133-135°C).
EXAMPLE 4 This Example illustrates the preparation of H-(4-chloro-3-methylisothiazol-5-yl)-N-(emoxymethyl)-[2-(2-methylpropyl)indazol-5-yl]acetamide (Compound No.A6.150) and N-[2-ethoxymemyl-4-chloro-3-memylisotluazolin-5-yUdene]-[2<2-memylpropyl)indazol-5-yl) acetamide (Compound No.I6.102).
N-(4
Documents
Application Documents
| # |
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Date |
| 1 |
in-pct-2001-1332-mum-canceeled page(17-4-2006).pdf |
2018-08-08 |
| 1 |
in-pct-2001-1332-mum-form-pct-ipea-409(30-10-2001).pdf |
2001-10-30 |
| 2 |
in-pct-2001-1332-mum-form 5(30-10-2001).pdf |
2001-10-30 |
| 2 |
in-pct-2001-1332-mum-claim(granted)-(17-4-2006).pdf |
2018-08-08 |
| 3 |
in-pct-2001-1332-mum-form 3(30-10-2001).pdf |
2001-10-30 |
| 4 |
in-pct-2001-1332-mum-form 1(30-10-2001).pdf |
2001-10-30 |
| 4 |
in-pct-2001-1332-mum-correspondence(6-9-2006).pdf |
2018-08-08 |
| 5 |
in-pct-2001-1332-mum-form 18(10-11-2005).pdf |
2005-11-10 |
| 5 |
in-pct-2001-1332-mum-correspondence(ipo)-(1-12-2006).pdf |
2018-08-08 |
| 6 |
in-pct-2001-1332-mum-power of authority(6-9-2006).pdf |
2018-08-08 |
| 7 |
in-pct-2001-1332-mum-power of authority(17-4-2006).pdf |
2018-08-08 |
| 7 |
in-pct-2001-1332-mum-form 2(granted)-(17-4-2006).pdf |
2018-08-08 |
| 8 |
in-pct-2001-1332-mum-petition under rule 137(17-4-2006).pdf |
2018-08-08 |
| 8 |
in-pct-2001-1332-mum-form 3(17-4-2006).pdf |
2018-08-08 |
| 9 |
in-pct-2001-1332-mum-petition under rule 137(17-4-2006).pdf |
2018-08-08 |
| 9 |
in-pct-2001-1332-mum-form 3(17-4-2006).pdf |
2018-08-08 |
| 10 |
in-pct-2001-1332-mum-form 2(granted)-(17-4-2006).pdf |
2018-08-08 |
| 10 |
in-pct-2001-1332-mum-power of authority(17-4-2006).pdf |
2018-08-08 |
| 11 |
in-pct-2001-1332-mum-power of authority(6-9-2006).pdf |
2018-08-08 |
| 12 |
in-pct-2001-1332-mum-form 18(10-11-2005).pdf |
2005-11-10 |
| 12 |
in-pct-2001-1332-mum-correspondence(ipo)-(1-12-2006).pdf |
2018-08-08 |
| 13 |
in-pct-2001-1332-mum-form 1(30-10-2001).pdf |
2001-10-30 |
| 13 |
in-pct-2001-1332-mum-correspondence(6-9-2006).pdf |
2018-08-08 |
| 14 |
in-pct-2001-1332-mum-form 3(30-10-2001).pdf |
2001-10-30 |
| 15 |
in-pct-2001-1332-mum-form 5(30-10-2001).pdf |
2001-10-30 |
| 15 |
in-pct-2001-1332-mum-claim(granted)-(17-4-2006).pdf |
2018-08-08 |
| 16 |
in-pct-2001-1332-mum-form-pct-ipea-409(30-10-2001).pdf |
2001-10-30 |
| 16 |
in-pct-2001-1332-mum-canceeled page(17-4-2006).pdf |
2018-08-08 |
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