Claims
- 1. All stereoisomeric forms and mixtures thereof of a compound of the formula ##STR28## wherein X is --O--, Y is --C.dbd.O, --C.dbd.S or --CH.sub.2 --, R.sub.1 is selected from the group consisting of hydrogen, halogen, saturated or unsaturated alkyl of 1 to 8 carbon atoms and saturated or unsaturated cycloalkyl of 3 to 8 carbon atoms, the latter two being unsubstituted or substituted with at least one halogen and carbocyclic aryl of 6 to 14 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen, --CF.sub.3, --NO.sub.2, --CN, halogen, alkoxy of 1 to 8 carbon atoms, aryl of 6 to 14 carbon atoms, an ester, saturated or unsaturated alkyl of 1 to 8 carbon atoms and saturated or unsaturated cycloalkyl of 3 to 8 carbon atoms, the latter two being unsubstituted or substituted with at least one halogen, R.sub.3 is selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms, --CN and --CN.tbd.CH and A is selected from the group consisting of ##STR29## wherein Z.sub.1 and Z.sub.2 are methyl or Z.sub.1 is hydrogen and Z.sub.2 is selected from the group consisting of ##STR30## Z.sub.3 is hydrogen or halogen, T.sub.1 and T.sub.2 are individually selected from the group consisting of hydrogen, halogen, --CF.sub.3, --CN, phenyl optionally substituted with a halogen and alkyl and alkoxy of 1 to 8 carbon atoms or taken together form ##STR31## or taken together with the cabon to which they are attached form a cycloalkyl of 3 to 6 carbon atoms, B is --O-- or --S--, a,b,c, and d are individually halogen, D is selected from the group consisting of hydrogen, halogen and alkoxy of 1 to 8 carbon atoms, G is --O-- or --S--, J is selected from the group consisting of optionally unsaturated alkyl and haloalkyl of 1 to 8 carbon atoms, optionally unsaturated cycloalky of 3 to 8 carbon atoms and carboxyclic aryl of 6 to 14 carbon atoms, all optionally substituted with at least one functional group, U is selected from the group consisting of halogen and alkyl and alkoxy of 1 to 8 carbon atoms optionally substituted with at least one halogen, m is 0,1 or 1 and if 2 the Us may be different, U' and V are individually selected from the group consisting of hydrogen, halogen and --CF.sub.3 and W is hydrogen or --CH.sub.3.
- 2. A compound of claim 1 wherein Y is ##STR32##
- 3. A compound of claim 1 wherein R.sub.3 is hydrogen.
- 4. A compound of claim 1 wherein R.sub.1 is alkenyl or alkynyl of 2 to 4 carbon atoms.
- 5. A compound of claim 1 wherein R.sub.1 is 2-propynyl.
- 6. A compound of claim 1 wherein R.sub.1 is 2-propenyl.
- 7. A compound of claim 1 wherein R.sub.2 is --CF.sub.3.
- 8. A compound of claim 1 wherein A is ##STR33## and Hal ia fluroine, chlorine, bromine or iodine.
- 9. A compound of claim 8 wherein Hal is bromine.
- 10. A compound of claim 1 wherein A is ##STR34## wherein Hal.sub.1 is a halogen, J.sub.1 is selected from the group consisting of alkyl of 1 to 8 carbon atoms and cycloalkyl of 3 to 8 carbon atoms, both optionally substituted with at least one halogen and the double bond has E geometry.
- 11. A compound of claim 10 wherein Hal.sub.1 is fluorine.
- 12. A compound of claim 1 wherein A is ##STR35## wherein J.sub.1 is selected from the group consisting of alkyl of 1 to 8 carbon atoms and cycloalkyl of 3 to 8 carbon atoms, both optionally substituted with at least one halogen and the double bond has Z geometry.
- 13. A compound of claim 12 wherein J.sub.1 is tert.-butyl.
- 14. A compound of claim 12 wherein J.sub.1 is ##STR36##
- 15. A compound of claim 1 wherein A is ##STR37##
- 16. A compound of claim 1 which is [2-oxo-3-(2-propynyl)-4-trifluoromethyl-2,3-dihydrooxazol-5yl]methyl[1R-{1.alpha.,3.alpha.,.DELTA.E}2,2-dimethyl-3-(3-oxo-3-(1,1-dimethylethoxy)-2-fluoropropenyl]-cyclopropane carboxylate.
- 17. An insecticidal composition comprising an claim 1 and an inert carrier.
- 18. A composition of claim 17 wherein Y is ##STR38##
- 19. A composition of claim 17 wherein R.sub.3 is hydrogen.
- 20. A composition of claim 17 wherein R.sub.1 is alkenyl or alkynyl of 2 to 4 carbon atoms.
- 21. A composition of claim 17 wherein R.sub.1 is 2-propynyl.
- 22. A compositionof claim 17 wherein R.sub.1 is 2-propenyl.
- 23. A composition of claim 17 wherein R.sub.2 is --CF.sub.3.
- 24. A composition of claim 17 wherein A is ##STR39## and Hal is fluorine, chlorine, bromine or iodine.
- 25. A composition of claim 17 wherein Hal is bromine.
- 26. A composition of claim 17 wherein A is ##STR40## wherein Hal.sub.1 is a halogen, J.sub.1 is selected from the group consisting of alkyl of 1 to 8 carbon atoms and cycloalkyl of 3 to 8 carbon atoms, both optionally substituted with at least one halogen and the double bond has E geometry.
- 27. A composition of claim 17 wherein Hal.sub.1 is fluorine.
- 28. A composition of claim 17 wherein A is ##STR41## wherein J.sub.1 is selected from the group consisting of alkyl of 1 to 8 carbon atoms and cycloalkyl of 3 to 8 carbon atoms, both optionally substituted with at least one halogen and the double bond has Z geometry.
- 29. A composition of claim 17 wherein J.sub.1 is tert-butyl.
- 30. A composition of claim 17 wherein J.sub.1 is ##STR42##
- 31. A composition of claim 17 wherein A is ##STR43##
- 32. An acaricidal composition comprising an acaricidally effective amount of at least one compound of claim 1 and an inert carrier.
- 33. A nematocidal composition comprising a nematocidally effective amount of at least one compound of claim 1 and an inert carrier.
- 34. A composition of claim 17 also containing at least one of the pyrethrinoid esters selected from the group consisting by esters of allethrolone, of 3,4,5,6-tetrahydrophthalimido-methyl alcohol, of 5-benzyl-3-furyl-methyl alcohol, of 3-phenoxy-benzyl alcohol and of .alpha.-cyanoj-3-phenoxy-benzyl alcohols with chrysanthemic acids, by the esters of 5-benzyl-3-furyl-methyl alcohol with 2,2-dimethy-3-(2-oxo-3,4,5,6-tetra-hydrothiophenylidene methyl)-cyclopropane-1-carboxylic acids, by the esters of 3-phenoxy-benzyl alcohol and of .alpha.-cyano-3-phenoxy-benzyl alcohols with 2,2-dimethy-3-(2,2-dibromovinyl)-cyclopropane-1-carboxylic acids, by esters of .alpha.-cyano-3-phenoxy-benzyl alcohol with 2,2-dimethyl-3-(2,2-dibromovinyl)-cyclopropane-1-carboxylic acids, by the esters of 3-phenoxy-benzyl alcohol with 2-parachlorophenyl-2-isopropyl acetic acids, by esters of allethrolones, of 3,4,5,6-tetrahydrophthalimido-methyl alcohol, of 5-benzyl-3-furylmethyl alcohol, of 3-phenoxy-benzyl alcohol and of .alpha.-cyano-3-phenoxy-benzyl alcohols with the 2,2-dimethyl-3-(1,2,2,2-tetrahaloethyl)-cyclopropane-1-carboxylic acids, in which "halo" represents a fluorine, chlorine or bromine atom, in all their possible stereoisomeric forms of the pyrethrinoid esters.
- 35. A composition of claim 17 wherein the active compound is [2-oxo-3-(2-propynyl)-4-trifluoromethyl-2,3-dihydrooxazol-5-yl]methyl[1R-{1.alpha., 3.alpha.,.DELTA.E}2,2-dimethyl-3-(3-oxo-1,1-dimethylethoxy)-2-fluoropropenyl]-cyclopropane carboxylate.
- 36. A composition of claim 17 also containing a pyrethrinoid synergist.
- 37. A method of combatting insecticides comprising contacting the insects with an insecticidally effective amount of at least one compound of claim 1.
- 38. A method of claim 37 wherein Y is ##STR44##
- 39. A method of claim 37 wherein R.sub.3 is hydrogen.
- 40. A method of claim 37 wherein R.sub.1 is alkenyl or alkynyl of 2 to 4 carbon atoms.
- 41. A method of claim 37 wherein R.sub.1 is 2-propynyl.
- 42. A method of claim 37 wherein R.sub.1 is 2-propenyl.
- 43. A method of claim 37 wherein R.sub.2 is --CF.sub.3.
- 44. A method of claim 37 wherein A is ##STR45## and Hal is fluorine, chlorine, bromine or iodine.
- 45. A method of claim 37 wherein Hal is bromine.
- 46. A method of claim 37 wherein A is ##STR46## wherein Hal.sub.1 is a halogen, J.sub.1 is selected from the group consisting of alkyl of 1 to 8 carbon atoms and cycloalkyl of 3 to 8 carbon atoms, both optionally substituted with at least one halogen and the double bond has E geometry.
- 47. A method of claim 37 wherein Hal.sub.1 is fluorine.
- 48. A method of claim 37 wherein A is ##STR47## wherein J.sub.1 is selected from the group consisting of alkyl of 1 to 8 carbon atoms and cycloalkyl of 3 to 8 carbon atoms, both optionally substituted with at least one halogen and the double bond has Z geometry.
- 49. A method of claim 37 wherein J.sub.1 is tert-butyl.
- 50. A method of claim 37 wherein J.sub.1 is ##STR48##
- 51. A method of claim 37 wherein A is ##STR49##
- 52. A method of combatting acariens comprising contacting acarien with an acaridically effective amount of at least one compound of claim 1.
- 53. A method of combatting nematodes comprising contacting nematodes with a nematocidally effective amount of at least one compound of claim 1.
- 54. The method of claim 37 wherein the active compound is [2-oxo-3-(2-propynyl)-4-trifluoromethyl-2,3-dihydrooxazol-5-yl]-methyl[1R-{1.alpha.,3.alpha.,.DELTA.E}2,2-dimethyl-ethoxy)-2-fluoropropenyl]-cyclopropane carboxylate.
Priority Claims (1)
Number |
Date |
Country |
Kind |
87 10202 |
Jul 1987 |
FRX |
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PRIOR APPLICATION
This application is a division of U.S. Pat. application Ser. No. 221,948 filed July 20, 1988, now U.S. Pat. No. 4,925,862.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
4083989 |
Kohn |
Apr 1978 |
|
Foreign Referenced Citations (1)
Number |
Date |
Country |
123719 |
Nov 1984 |
EPX |
Divisions (1)
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Number |
Date |
Country |
Parent |
221948 |
Jul 1988 |
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