Claims
- 1. A compound having the formula ##STR13## wherein: .dbd.X is NR.sup.3, .dbd.O or an electron pair;
- R.sup.1 is C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, or C.sub.4 -C.sub.8 (cycloalkyl)alkyl, each of which is optionally substituted by one or more halogen;
- R.sup.2 and R.sup.3 are independantly selected from H; C.sub.1 C.sub.6 alkyl; C.sub.1 -C.sub.6 haloalkyl; COR.sup.4 ; S(O).sub.p R.sup.4 ; CN; NO.sub.2 ; COOR.sup.4 ; CONR.sup.4 R.sup.5 ; C(O)SR.sup.4 ; C(S)OR.sup.4 ; SO.sub.2 NR.sup.4 R.sup.5 ; P(O).sub.q (R.sup.4)(R.sup.5); P(O).sub.q (OR.sup.4)(R.sup.5); P(O).sub.q (OR.sup.4)(OR.sup.5); C--(NR.sup.4)NR.sup.5 R.sup.6 ; CH.dbd.NR.sup.4 ; C.dbd.(NR.sup.4)(OR.sup.5); C(S)N(R.sup.4)(R.sup.5); C(O)C(O)R.sup.4 ; C(O)C(O)OR.sup.4 ; C(O)C(O)NR.sup.4 R.sup.5 ; and CONR.sup.4 SO.sub.2 R.sup.5 :
- m is 1 or 2;
- p is 0, 1 or 2;
- q is 0 or 1;
- R.sup.4, R.sup.5 and R.sup.6 are independently selected from H; NO.sub.2 ; CN; CIIO; R.sup.14 ; phenyl optionally substituted by one or more R.sup.14, halogen, CN, NO.sub.2, OR.sup.14, SR.sup.14, COR.sup.14, COOR.sup.14, or OR.sup.14 ; halogen; COR.sup.14 ; COOR.sup.14 ; CHO; and OH;
- Q is Q-1 as designated below: ##STR14## R.sup.7 is CN, NO.sub.2, H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, halogen, CHO, COR.sup.20 ;
- R.sup.8 is H, halogen, CN, S(O).sub.p R.sup.14, OR.sup.4, NR.sup.16 R.sup.17, N(R.sup.16)CON(R.sup.17)(R.sup.18), N.sub.3 or NH(C.sub.1 -C.sub.5 alkyl) substituted by one or more OH, OR.sup.14, S(O).sub.p R.sup.14, CN, NO.sub.2, COOR.sup.14 or CON(R.sup.16)(R.sup.17);
- Ar is phenyl, optionally bearing one or more substituents selected from the group consisting of halogen, R.sup.15, OR.sup.15, SF.sub.5 and S(O).sub.p R.sup.15 ; or Ar is 2-pyrldyl, optionally bearing one or more substituents selected from the group consisting of halogen, R.sup.15, OR.sup.15, SF.sub.5 and S(O).sub.p R.sup.14 ;
- R.sup.14 and R.sup.19 are independently selected from C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, and C.sub.4 -C.sub.8 (cycloalkyl)alkyl, each of which is optionally substituted by one or more halogen;
- R.sup.15 is C.sub.1 -C.sub.6 alkyl, optionally substituted by one or more halogen;
- R.sup.16, R.sup.17 and R.sup.18 are independently selected from H, NO.sub.2, CN, CHO, R.sup.19, COR.sup.19, and COOR.sup.19 ;
- R.sup.20 is C.sub.1 -C.sub.6 alkyl, optionally substituted by one or more halogen; and
- Z is an anionic counter ion.
- 2. A compound according to claim 1, having formula (I).
- 3. A compound according to claim 2, wherein .dbd.X is .dbd.NH, --O or an electron pair.
- 4. A compound according to claim 3, wherein .dbd.X is .dbd.O or an electron pair.
- 5. A compound according to claim 1, wherein R.sup.1 is C.sub.1 -C.sub.6 alkyl, optionally substituted by one or more halogen.
- 6. A compound according to claim 5, wherein R.sup.1 is methyl or ethyl.
- 7. A compound according to claim 1, wherein R.sup.2 is H.
- 8. A compound according to claim 1, wherein R.sup.2 is COOR.sup.4.
- 9. A compound according to claim 8, wherein R.sup.4 is C.sub.1 -C.sub.6 alkyl.
- 10. A compound according to claim 1, wherein R.sup.2 is S(O).sub.p R.sup.4.
- 11. A compound according to claim 10 wherein p is two and R.sup.4 is C.sub.1 -C.sub.6 alkyl or phenyl optionally substituted by one or more R.sup.14.
- 12. A compound according to claim 1 wherein R.sup.2 is CN.
- 13. A compound according to claim 1, wherein R.sup.2 is CONR.sup.4 R.sup.5.
- 14. A compound according to claim 13, wherein R.sup.4 is H or C.sub.1 -C.sub.6 alkyl and R.sup.5 is C.sub.1 -C.sub.6 alkyl, or wherein R.sup.4 is H and R.sup.5 is COR.sup.14 wherein R.sup.14 is C.sub.1 -C.sub.6 alkyl, optionally substituted by one or more halogen.
- 15. A compound according to claim 1, wherein R.sup.2 is COR.sup.4.
- 16. A compound according to claim 15, wherein R.sup.4 is H or C.sub.1 -C.sub.6 alkyl.
- 17. A compound according to claim 1, wherein R.sup.2 is P(O).sub.q (OR.sup.4)(OR.sup.5) or P(O).sub.q (R.sup.4)(R.sup.5).
- 18. A compound according to claim 17, wherein q is one and R.sup.4 and R.sup.5 are each C.sub.1 -C.sub.6 alkyl.
- 19. A compound according to claim 1 wherein R.sup.7 is CN, H or C.sub.1 -C.sub.4 alkyl.
- 20. A compound according to claim 19, wherein R.sup.7 is CN.
- 21. A compound according to claim 1, wherein R.sup.8 is N(R.sup.16)(R.sup.17).
- 22. A compound according to claim 21, wherein R.sup.8 is NH.sub.2.
- 23. A compound according to claim 22, wherein R.sup.7 is CN.
- 24. A compound according to claim 1, wherein Ar is phenyl, substituted in the 2 and 6 positions by halogen and in the 4-position by halogenated C.sub.1 -C.sub.6 alkyl or SF.sub.5 or OR.sup.15.
- 25. A compound according to claim 24, wherein Ar is 2,6-dichloro 4 trifluoromethylphenyl.
- 26. A compound according to claim 1, wherein Ar is 2-pyridyl substituted in the 3 position by halogen and in the 5-position by halogenated C.sub.1 -C.sub.6 alkyl or SF.sub.5 or OR.sup.15.
- 27. A compound according to claim 26, wherein Ar is 3-chloro-5-trifluoromethylpyrid-2-yl.
- 28. A compound according to claim 1, wherein Z is Cl.sup.-, Br.sup.-, I.sup.-, P.sup.-, OSO.sub.2 R.sup.1, ClO.sub.4.sup.-, OCOR.sup.4-, BF.sub.4.sup.-, SbF.sub.6.sup.-, SO.sub.3.sup.- HSO.sub.4.sup.-, a phosphate anion or a hydrogenophosphate anion.
- 29. The compound according to claim 1, having the formula: ##STR15## wherein: (a) R.sup.1 is ethyl and R.sup.2 is COO(tert-butyl);
- (b) R.sup.1 is ethyl and R.sup.2 is COCH.sub.3 ;
- (c) R.sup.1 is ethyl and R.sup.2 is COOCH.sub.3 ;
- (d) R.sup.1 is ethyl and R.sup.2 is SO.sub.2 CH.sub.3 ;
- (e) R.sup.1 is ethyl and R.sup.2 is CONHCH.sub.3 ;
- (f) R.sup.1 is ethyl and R.sup.2 is CN;
- (g) R.sup.1 is ethyl and R.sup.2 is CHO;
- (h) R.sup.1 is methyl and R.sup.2 is COCH.sub.3 ;
- (i) R.sup.1 is ethyl and R.sup.2 is PO(OC.sub.2 H.sub.5).sub.2 ;
- (j) R.sup.1 is ethyl and R.sup.2 is CON(CH.sub.3).sub.2 ;
- (k) R.sup.1 is ethyl and R.sup.2 is PO(CH.sub.3).sub.2 ;
- (l) R.sup.1 is ethyl and R.sup.2 is CONHCOCCl.sub.3 ;
- (m) R.sup.1 is ethyl and R.sup.2 is CONHCOCH.sub.2 Cl; or
- (n) R.sup.1 is methyl and R.sup.2 is ##STR16##30.
- 30. The compound according to claim 1, having the formula: wherein:
- (a) R.sup.1 is ethyl, X is O and R.sup.2 is COO(tert-butyl);
- (b) R.sup.1 is ethyl, X is O and R.sup.2 is COOCH.sub.3 ; or
- (c) R.sup.1 is ethyl, X is O and R.sup.2 is H.
- 31. The compound according to claim 1, which is;
- 2,4,6-trimethylbenzenesulfonic acid, compound with S-4-[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]pyrazolyl-S-ethylsulfilimine;
- 2,4,6-trimethlylbenzenesulfonic acid, compound with S-4-[5- amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]pyrazolyl-S-methylsulfimine;
- 2,4,6-trimethylbenzenesulfonic acid, compound with S-4-[5amino-1-(2,6-dichloro-4-trifluoromethyl)phenyl]pyrazolyl-S-methylsulfilimine;
- 2. 4,6-trimethylbenzenesulfonic acid, compound with S4-[5amino-1-(2,6-dichloro-4-trifluoromethyl)phenyl-3-methyl]pyrazolyl-S-methylsulfilimine;
- 2,4,6-trimethylbenzenesulfonic acid, compound with S4-[5-amino-1-(2,6dichloro-4-trifluoromethyl)phenyl-3-ethyl]pyrazolyl-S-ethylsulfilimine; {[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]4-(1H-pyrazolyl)}-S-ethyl-N-(tert-butoxycarbonyl)sulfilimine;
- S-{[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-ethyl-N-acetylsulfilimine:
- S-{[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-ethyl-N-(methoxycarbonyl)sulfilimine;
- S-{[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-ethyl-N-(methylsulfonyl)sulfilimine;
- S-{[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-ethyl-N-(methoxycarbonyl)sulfilimine;
- S-{[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-ethyl-N-(cyanol)sulfilimine;
- S-{[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-ethyl-N-(formyl)sulfilimine;
- S-{[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-methyl-N-acetylsulfilimine;
- S {[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]4-(1H-pyrazolyl)}ethyl-N-(diethylphosphoryl)sulfilimine;
- S-{[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-ethyl-N-(dimethylcarbonyl)sulfilimine;
- S-{[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-ethyl-N-(dimethylcarbonyl)sulfilimine;
- S-{[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-ethyl-N-(trichloroacetylamino)carbonyl)sulfilimine;
- S-{[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-ethyl-N-(chloroacetylamino)carbonyl)sulfilimine;
- S-{[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-ethyl-N-(methylthiocarbonyl)sulfilimine;
- S-{[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-ethyl-N-(ethoxycarbonylmethyl)aminocarbonyl)sulfilimine;
- S-{[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-methyl-N-methylthiocarbonyl)sulfilimine;
- S-{[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-methyl-N-ethoxycarbonylaminocarbonyl)sulfilimine;
- S-{[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-methyl-N-(formyl)sulfilimine;
- S-{[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-methyl-N-(cyano)sulfilimine;
- S-{[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-methyl-N-(1,2 dioxopropy)sulfilimine;
- S-{[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-methyl-N-(tert-buloxycarbony)sulfilimine;
- S-{[5-amino-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-methyl-N-(formyl)sulfilimine;
- S-{[5-amino-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-methyl-N-(acetyl)sulfilimine;
- S-{[5-amino-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-methyl-N-(cyano)sulfilimine;
- S-{[5-amino-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-methyl-N-(formyl)sulfilimine;
- S-{[5-amino-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-methyl-N-(cyano)sulfilimine;
- S-{[5-amino-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-methyl-N-(formyl)sulfilimine;
- S-{[5-amino-1-(2,6-dichloro-4-trifluoromethyl)phenyl]-4-(1H-pyrazolyl)}-S-methyl-N-(cyano)sulfilimine;
- N-(tert-butoxycarbonyl)S-4-[5amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenylpyrazolyl]-S-ethylsulfoximine;
- N-acetyl S-4-[5-amino-3-cyano-1-(2,6-dichloro-4trifluoromethyl)phenylpyrazolyl]-S-ethylsulfoximine;
- S-4-[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenylpyrazolyl]-S-ethylsulfoximine;
- S-[5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)phenyl-4-(1H-pyrazolyl)]-S-methyl-N-[(4-methylphenyl)sulfonyl]sulfilimine; or
- S-4-[5-amino-3-cyano-1-(2-(3-chloro-5-trifluoromethyl) pyridyl)pyrazolyl]-S-ethylsulfoxide.
- 32. A pesticidal composition comprising a pesticidally effective amount of a compound of formula (I) or (II) as claimed in claim 1 and an agriculturally acceptable inert carrier therefor.
- 33. A composition according to claim 32, wherein the pesticidally effective amount is an arthropodicidally effective amount.
- 34. A composition according to claim 33, wherein the arthropodicidally effective amount is an insecticidally effective amount.
- 35. A composition according to claim 32, wherein the pesticidally effective amount is a nematocidally effective amount.
- 36. A composition according to claim 32, further comprising an agriculturally acceptable surfactant.
- 37. A method for controlling pests at a locus, said method comprising applying to said locus a pesticidally effective amount of a compound of formula (I) or (II) as claimed in claim 1.
- 38. A method according to claim 37 for controlling arthropods at a locus, said method comprising applying said locus an arthropodicidally effective amount of a compound of formula (I) or (II).
- 39. A method according to claim 38 for controlling insects at a locus, said method comprising applying to said locus an insecticidally effective amount of a compound of formula (I) or (II).
- 40. A method according to claim 37 for controlling nematodes at a locus, said method comprising applying to said locus a nematocidally effective amount of a compound of formula (I) or (II).
Parent Case Info
This application is the U.S. national stage of International Application No. PCT/EP96/02363, filed May 31, 1996 and designating the United States, which is a continuation-in-part of U.S. patent application Ser. No. 08/588,839, filed Jan. 19, 1996 and now abandoned, which is in turn a continuation of U.S. patent application Ser. No. 08/464,372, filed Jun. 5, 1995 and now abandoned.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/EP96/02363 |
5/31/1996 |
|
|
6/16/1998 |
6/16/1998 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO96/39389 |
12/12/1996 |
|
|
US Referenced Citations (11)
Number |
Name |
Date |
Kind |
4614533 |
Schallner et al. |
Sep 1986 |
|
4804675 |
Jensen-Korte et al. |
Feb 1989 |
|
4810720 |
Jensen-Korte et al. |
Mar 1989 |
|
4945165 |
Jensen-Korte et al. |
Jul 1990 |
|
5047550 |
D'Silva et al. |
Sep 1991 |
|
5079370 |
D'Silva et al. |
Jan 1992 |
|
5104994 |
Roberts et al. |
Apr 1992 |
|
5187185 |
Outcalt et al. |
Feb 1993 |
|
5223525 |
Wu et al. |
Jun 1993 |
|
5232940 |
Hatton et al. |
Aug 1993 |
|
5306694 |
Phillips et al. |
Apr 1994 |
|
Foreign Referenced Citations (7)
Number |
Date |
Country |
0201852 |
Nov 1986 |
EPX |
0352944 |
Jan 1990 |
EPX |
0403309 |
Dec 1990 |
EPX |
0418016 |
Mar 1991 |
EPX |
1603122 |
Nov 1981 |
GBX |
9306089 |
Apr 1993 |
WOX |
9421606 |
Sep 1994 |
WOX |
Non-Patent Literature Citations (1)
Entry |
Hatton et al, Chemical Abstracts, vol. 120 (1994), abstract No. 298625p. |
Continuations (1)
|
Number |
Date |
Country |
Parent |
464372 |
Jun 1995 |
|
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
588839 |
Jan 1996 |
|