Claims
- 1. A compound having the formula: ##STR14## wherein: R.sub.2 is H, halogen, hydroxy, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, CN, NO.sub.2, --S(O).sub.n R.sub.8, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, hydroxycarbonyl, aminosulfonyl, alkylaminosulfonyl, or dialkylaminosulfonyl;
- R.sub.3 is CN;
- R.sub.4 is --S(O).sub.n R.sub.8 ;
- R.sub.5 is hydrogen, halogen, --NR.sub.9 R.sub.10, --N.dbd.CR.sub.11 R.sub.19, --S(O).sub.n R.sub.8, formyl, alkylcarbonyl, haloalkylcarbonyl, cyano, alkyl, haloalkyl, hydrazino, alkoxycarbonyl, alkylthiocarbonyl, 1H-pyrrol-1-yl or 1H-pyrazol-1-yl;
- R.sub.8 is alkyl, haloalkyl, alkenyl, or alkynyl, or R.sub.8 is a cycloalkyl ring having 3 to 5 carbon atoms;
- R.sub.11 is H or alkyl;
- R.sub.19 is hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, amino, monoalkylamino, or dialkylamino; or R.sub.19 is phenyl, thienyl, pyridyl or furyl, each of which is unsubstituted or substituted with one or more substituents selected from the group consisting of alkyl, haloalkyl, halogen, NO.sub.2, CN, alkoxy, haloalkoxy, OII, alkylcarbonyl and alkylcarbonyloxy;
- R.sub.9 and R.sub.10, independently of each other, are H, alkyl, haloalkyl, alkylcarbonyl, haloalkylcarbonyl, R.sub.8 S(O).sub.n, formyl, alkenyl, alkynyl, alkoxycarbonyl, alkylthiocarbonyl, or aroyl; or R.sub.9 and R.sub.10 are joined so as to together form a divalent radical having 4 to 6 atoms in the chain, said divalent radical being alkylene, alkyleneoxyalkylene or alkyleneaminoalkylene, the alkyl portions of R.sub.9 and R.sub.10 being optionally substituted by R.sub.7 ;
- R.sub.7 is cyano, nitro, alkoxy, haloalkoxy, R.sub.8 S(O).sub.n, --C(O)alkyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, --CO.sub.2 H, halogen, hydroxy, aminosulfonyl, alkylaminosulfonyl or dialkylaminosulfonyl;
- Z is N or C--R.sub.16 ;
- n is zero, one or two;
- R.sub.12, R.sub.13, R.sub.15 and R.sub.16 independently of one another, are hydrogen, halogen, alkyl, haloalkyl, cyanoalkyl, cyano, nitro, amino, hydrazino, alkoxy, haloalkoxy, alkylsulfenyl, alkylsulfinyl, alkylsulfonyl, haloalkylsulfenyl, haloalkylsulfinyl, haloalkylsulfonyl, formyl, alkylcarbonyl or alkoxycarbonyl; and
- R.sub.22, R.sub.23, R.sub.24, R.sub.25, and R.sub.26, independently of one another, are hydrogen, halogen, allyl, haloalkyl, cyanoalkyl, cyano, nitro, amino, hydrazino, alkoxy, haloalkoxy, haloalkylcarbonyl, formyl, alkylcarbonyl, thioamide, amide, alkoxycarbonyl, SF.sub.5, or R.sub.8 S(O).sub.n ; or R.sub.22 and R.sub.23 or R.sub.23 and R.sub.24 or R.sub.25 and R.sub.26 together form divinylidene (CH.dbd.CH CH.dbd.CH--), methylenedioxy (--O--CH.sub.2 --O--) or difluoromethylenedioxy (--O--CF.sub.2 --O--) so as to form a cyclic ring vicinal to the phenyl ring;
- or a pesticidally acceptable salt thereof.
- 2. A compound according to claim 1, having formula (Ia).
- 3. A compound according to claim 1, wherein R.sub.9 and R.sub.10 are joined together to form with the adjacent nitrogen atom a morpholine, pyrrolidine, piperidine or piperazine ring, optionally substituted by R.sub.7.
- 4. A compound according to claim 1, wherein R.sub.24 is halogen, haloalkyl or haloalkoxy.
- 5. A compound according to claim 1, wherein R.sub.5 is --NR.sub.9 R.sub.10.
- 6. A compound according to claim 5, wherein R.sub.5 is --NH.sub.2.
- 7. A compound according to claim 1, wherein R.sub.8 is lower alkyl or haloalkyl.
- 8. A compound according to claim 1, having at least one feature selected from the group consisting of:
- R.sub.5 is hydrogen, halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.-- haloalkyl, or --NR.sub.9 R.sub.10 ;
- R.sub.8 is methyl, ethyl, --CF.sub.3, --CFCl.sub.2, or --CF.sub.2 Cl;
- R.sub.12 and R.sub.16, independently of each other, are F, Cl, Br or H;
- R.sub.13 and R.sub.15 are H;
- R.sub.24 is --CF.sub.3, OCF.sub.3, --CHF.sub.2, --S(O).sub.n CF.sub.3, --CFCl.sub.2, --CF.sub.2 Cl, --OCF.sub.2 Cl, -OCFCl.sub.2, Cl, Br or F; and
- Z is CCl, CF, CBr or N.
- 9. A compound according to claim 1, wherein the S(O).sub.n R.sub.8 substituent of formula (Ia) or (Ib) is: methylthio, methylthio, methylsulfinyl, methylsulfonyl, ethylsulfinyl, ethylsulfonyl, ethylthio, cyclopropylsulfinyl, cyclopropylthio, cyclopropylsulfonyl, isopropylsulfinyl, isopropylsulfonyl, isopropylthio, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, dichlorofluoromethylthio, dichlorofluoromethylsulfinyl, dichlorofluoromethylsulfonyl, chlorodifluoromethylthio, chlorodifluoromethylsulfonyl or chlorodifluoromethylsulfinyl.
- 10. A compound according to claim 8, wherein the S(O).sub.n R.sub.8 substituent of formula (Ia) or (Ib) is: trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, dichlorofluoromethylthio, dichlorofluoromethylsulfinyl, dichlorofluoromethylsulfonyl, chlorodifluoromethylthio, chlorodifluoromethylsulfonyl or chlorodifluoromethylsulfinyl.
- 11. The compound of formula (Ia) according to claim 2, which is 4-dichlorofluoromethylsulfenyl 1-[2-fluoro-4-(4-trifluoromethylphenyl)phenyl]imidazole.
- 12. A pesticidal composition comprising:
- (a) a pesticidally effective amount of a compound having the formula: ##STR15## wherein: R.sub.2 is H, halogen, hydroxy, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, CN, NO.sub.2, --S(O).sub.n R.sub.8, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, hydroxycarbonyl, aminosulfonyl, alkylaminosulfonyl, or dialkylaminosulfonyl;
- R.sub.3 is CN;
- R.sub.4 is S(O).sub.n R.sub.8 ;
- R.sub.5 is hydrogen, halogen, --NR.sub.9 R.sub.10, --N.dbd.CR.sub.11 R.sub.19, --S(O).sub.n R.sub.8, formyl, alkylcarbonyl, haloalkylcarbonyl, cyano, alkyl, haloalkyl, hydrazino, alkoxycarbonyl, alkylthiocarbonyl, 1H-pyrrol-1-yl or 1H-pyrazol-1-yl:
- R.sub.8 is alkyl, haloalkyl, alkenyl, or alkynyl, or R.sub.8 is a cycloalkyl ring having 3 to 5 carbon atoms;
- R.sub.11 is H or alkyl;
- R.sub.19 is hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, amino, monoalkylamino, or dialkylamino; or R.sub.19 is phenyl, thienyl, pyridyl or furyl, each of which is unsubstituted or substituted with one or more substituents selected from the group consisting of alkyl, haloalkyl, halogen, NO.sub.2, CN, alkoxy, haloalkoxy, OH, alkylcarbonyl and alkylcarbonyloxy;
- R.sub.9 and R.sub.10, independently of each other, are H, alkyl, haloalkyl, alkylcarbonyl, haloalkylcarbonyl R.sub.8 S(O).sub.n, formyl, alkenyl, alkynyl, alkoxycarbonyl, alkylthiocarbonyl, or aroyl; or R.sub.9 and R.sub.10 are joined so as to together form a divalent radical baying 4 to 6 atoms in the chain, said divalent radical being alkylene, alkyleneoxyalkylene or alkyleneaminoalkylene the alkyl portions of R.sub.9 and R.sub.10 being optionally substituted by R.sub.7 ;
- R.sub.7 is cyano, nitro, alkoxy, haloalkoxy, R.sub.8 S(O).sub.n, --C(O)alkyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, --CO.sub.2 H, halogen, hydroxy, aminosulfonyl, alkylaminosulfonyl or dialkylaminosulfonyl;
- Z is N or C--R.sub.16,;
- n is zero, one or two;
- R.sub.12, R.sub.13, R.sub.15 and R.sub.16, independently of one another, are hydrogen, halogen, alkyl, haloalkyl, cyanoalkyl, cyano, nitro, amino, hydrazino, alkoxy, haloalkoxy, alkylsulfenyl, alkylsulfinyl, alkylsulfonyl, haloalkylsulfenyl, haloalkylsulfinyl, haloalkylsulfonyl, formyl, alkylcarbonyl or alkoxycarbonyl; and
- R.sub.22, R.sub.23, R.sub.24, R.sub.25, and R.sub.26, independently of one another, are hydrogen, halogen, alkyl, haloalkyl, cyanoalkyl, cyano, nitro, amino, hydrazino, alkoxy, haloalkoxy, haloalkylcarbonyl, formyl, alkylcarbonyl, thioamide, amide, alkoxycarbonyl, SF.sub.5, or R.sub.8 S(O).sub.n ; or R.sub.22 and R.sub.23 or R.sub.23 and R.sub.24 or R.sub.25 and R.sub.26 together form divinylidene (CH.dbd.CH--CH.dbd.CH--), methylenedioxy (--O--CH.sub.2 --O--) or difluoromethylenedioxy (--O--CF.sub.2 --O--) so as to form a cyclic ring vicinal to the phenyl ring;
- or a pesticidally acceptable salt thereof; and
- (b) a pesticidally acceptable carrier thereof.
- 13. A composition according to claim 12, wherein the compound has formula (Ia).
- 14. A composition according to claim 12, comprising from 0.001 to 95% of compound of formula (Ia) or (Ib).
- 15. A composition according to claim 13, comprising from 0.001 to 95% of compound of formula (Ia).
- 16. A method for controlling pests at a locus comprising applying to said locus a pesticidally effective amount of a compound having the formula: ##STR16## wherein: R.sub.2 is H, halogen, hydroxy, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, CN, NO.sub.2, --S(O).sub.n R.sub.8, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, hydroxycarbonyl, aminosulfonyl, alkylaminosulfonyl, or dialkylaminosulfonyl;
- R.sub.3 is CN;
- R.sub.4 is --S(O).sub.n R.sub.8 ;
- R.sub.5 is hydrogen, halogen, --NR.sub.9 R.sub.10, --N.dbd.CR.sub.11 R.sub.19, --S(O).sub.n R.sub.8, formyl, alkylcarbonyl, haloalkylcarbonyl, cyano, alkyl, haloalkyl, hydrazino, alkoxycarbonyl, alkylthiocarbonyl, 1H-pyrrol-1-yl or 1H-pyrazol-1-yl;
- R.sub.8 is alkyl, haloalkyl, alkenyl, or alkynyl, or R.sub.8 is a cycloalkyl ring having 3 to 5 carbon atoms;
- R .sub.11 is H or alkyl;
- R.sub.19 is hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, amino, monoalkylamino, or dialkylamino; or R.sub.19 is phenyl, thienyl, pyridyl or furyl, each of which is unsubstituted or substituted with one or more substituents selected from the group consisting of alkyl, haloalkyl, halogen, NO.sub.2, CN, alkoxy, haloalkoxy, OH, alkylcarbonyl and alkylcarbonyloxy;
- R.sub.9 and R.sub.10, independently of each other are H, alkyl, haloalkyl, alkylcarbonyl, haloalkylcarbonyl, R.sub.8 S(O).sub.n, formyl, alkenyl, alkynyl, alkoxycarbonyl alkylthiocarbonyl, or aroyl; or R.sub.9 and R.sub.10 are joined so as to together form a divalent radical having 4 to 6 atoms in the chain, said divalent radical being alkylene, alkyleneoxyalkylene or alkyleneaminoalkylene, the alkyl portions of R.sub.9 and R.sub.10 being optionally substituted by R.sub.7 ;
- R.sub.7 is cyano, nitro, alkoxy, haloalkoxy, R.sub.8 S(O).sub.n, --C(O)alkyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, --CO.sub.2 H, halogen, hydroxy, aminosulfonyl, alkylaminosulfonyl or dialkylaminosulfonyl;
- Z is N or C--R.sub.16 ;
- n is zero, one or two;
- R.sub.12, R.sub.13, R.sub.15 and R.sub.16, independently of one another, are hydrogen, halogen, alkyl, haloalkyl, cyanoalkyl, cyano, nitro, amino, hydrazino, alkoxy, haloalkoxy, alkylsulfenyl, alkylsulfinyl, alkylsulfonyl, haloalkylsulfenyl, haloalkylsulfinyl, haloalkylsulfonyl, formyl, alkylcarbonyl or alkoxycarbonyl; and
- R.sub.22, R.sub.23, R.sub.24, R.sub.25, and R.sub.26, independently of one another, are hydrogen, halogen, alkyl, haloalkyl, cyanoalkyl, cyano, nitro, amino, hydrazino, alkoxy, haloalkoxy, haloalkylcarbonyl, formyl, alkylcarbonyl, thioamide, amide, alkoxycarbonyl, SF.sub.5, or R.sub.8 S(O).sub.n ; or R.sub.22 and R.sub.23 or R.sub.23 and R.sub.24 or R.sub.25 and R.sub.26 together form divinylidene (CH.dbd.CH--CH.dbd.CH--), methylenedioxy (--O--CH.sub.2 --O--) or difluoromethylenedioxy (--O--CF.sub.2 --O--) so as to form a cyclic ring vicinal to the phenyl ring;
- or a pesticidally acceptable salt thereof.
- 17. A method according to claim 16, wherein the compound has formula (Ia).
- 18. A method according to claim 16, wherein said pests are insects and wherein said pesticidally effective amount is an insecticidally effective amount.
- 19. A method according to claim 17, wherein said pests are insects and wherein said pesticidally effective amount as an insecticidally effective amount.
- 20. A method according to claim 16, comprising applying to said locus from about 0.01 to about 2 kg/ha of compound of formula (Ia) or (Ib).
- 21. A method according to claim 17, comprising applying to said locus from about 0.01 to about 2 kg/ha of compound of formula (Ia).
- 22. A method according to claim 20, comprising applying to said locus from about 0.1 to about 1 kg/ha of compound of formula (Ia) or (Ib).
- 23. A method according to claim 21, comprising applying to said locus from about 0.1 to about 1 kg/ha of compound of formula (Ia).
- 24. A method for controlling pests at a locus comprising applying to said locus a pesticidally effective amount of a composition as claimed in claim 12.
- 25. A method for controlling pests at a locus comprising applying to said locus a pesticidally effective amount of a composition as claimed in claim 13.
- 26. A method according to claim 24, wherein said pests are insects and wherein said pesticidally effective amount is an insecticidally effective amount.
- 27. A method according to claim 25, wherein said pests arc insects and wherein said pesticidally effective amount is an insecticidally effective.
- 28. A process for preparing a compound of formula (Ia) or (Ib) according to claim 1, which comprises:
- (a) reacting a compound of the formula; ##STR17## wherein R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.12, R.sub.13, R.sub.15 and Z are as defined in claim 1, with a boric acid or ester in the presence of a coupling catalyst to form a compound of the formula: ##STR18## wherein R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.12, R.sub.13, R.sub.15 and Z are as defined in claim 1 and R.sub.30 is hydrogen, alkyl, or divalent lower alkylene such that B(OR.sub.30).sub.2 forms a cyclic borate ester; followed by reacting the resultant compound of formula (IIIa) or (IIIb) with a compound of the formula: ##STR19## wherein R.sub.22, R.sub.3, R.sub.24, R.sub.25 and R.sub.26 are as defined in claim 1 and R.sub.20 is bromine, iodine or O--SO.sub.2 CF.sub.3 ;
- (b) reacting a compound of formula (IIa) or (IIb) above with a compound of formula (IV): ##STR20## wherein R.sub.22, R.sub.23, R.sub.24, R.sub.25, and R.sub.26 are as defined in claim 1 and R.sub.30 is as defined above;
- (c) reacting a compound of formula (IIa) or (IIb) above with a hexaalkylstannane to form a compound of the formula: ##STR21## wherein R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.12, R.sub.13, R.sub.15 and Z art as defined in claim 1; followed by reacting the resultant compound of formula (Va) or (Vb) with a compound of formula (IV) above in the presence of a coupling catalyst; or
- (d) reacting a compound of formula (IIa) or (IIb) above with a compound of formula (VI) above in the presence of a coupling catalyst.
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a divisional of U.S. patent application Ser. No. 08/963,631, filed Nov. 4, 1997, now U.S. Pat. No. 5,922,884, which claims the priority of U.S. Provisional Patent Application Ser. No. 60/030,128, filed Nov. 4, 1996. Both prior applications are incorporated by reference herein in their entireties and relied upon.
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Divisions (1)
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Number |
Date |
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Parent |
963631 |
Nov 1997 |
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