Claims
- 1. A compound corresponding to the ##STR310## wherein R represents a nitrogen containing heterocyclic radical corresponding to one of the formulae ##STR311## each X independently represents chloro, fluoro, bromo, nitro, alkyl of 1 to 4 carbon atoms, amino, mono- or dialkylamino wherein each alkyl group independently contains from 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, cyano, trifluoromethyl, trichloromethyl, phenoxy or substituted phenoxy of the formula ##STR312## wherein each Z independently represents chloro, fluoro, bromo, nitro, cyano, alkoxy of 1 to 4 carbon atoms or alkylthio of 1 to 4 carbon atoms, with the proviso that when either n is 2 or 3, all X groups are sterically compatible with each other and all Z groups are sterically compatible with each other; Y represents oxygen or sulfur; each n can independently represent an integer of from 0 to 3, inclusive; R.sup.1 represents hydrogen, chloro, fluoro, bromo, alkyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, phenyl, phenylthio, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, thiocyanato, trifluoromethyl, trichloromethyl, amino, mono- or dialkylamino wherein each alkyl group independently contains from 1 to 4 carbon atoms; R.sup.2 represents methyl, ethyl, propyl or isobutyl and R.sup.3 represents methoxy, ethoxy, propoxy, ethyl, mono- or dialkylamino wherein each alkyl group independently contains from 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms or phenyl.
- 2. A compound as defined in claim 1 wherein the heterocyclic radical is ##STR313##
- 3. A compound as defined in claim 2 wherein R.sup.2 is methyl or ethyl and R.sup.3 is methoxy or ethoxy.
- 4. The compound as defined in claim 3 which is O,O-diethyl O-(1-(6-chloro-2-pyridinyl)-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 5. The compound as defined in claim 3 which is O,O-diethyl O-(1-(2-pyridinyl)-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 6. The compound as defined in claim 3 which is O,O-diethyl O-(1-(6-fluoro-2-pyridinyl)-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 7. The compound as defined in claim 3 which is O,O-diethyl O-(1-(2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 8. The compound as defined in claim 3 which is O,O-diethyl O-(1-(6-fluoro-2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 9. The compound as defined in claim 3 which is O,O-diethyl O-(1-(2-pyridinyl)-5-ethyl-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 10. The compound as defined in claim 3 which is O,O-diethyl O-(1-(6-phenoxy-2-pyridinyl)-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 11. The compound as defined in claim 3 which is O,O-diethyl O-(1-(6-phenoxy-2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 12. The compounds as defined in claim 3 which is O,O-dimethyl O-(1-(2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 13. The compound as defined in claim 3 which is O,O-diethyl O-(1-(2-pyridinyl)-5-(1-methylethyl)-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 14. The compound as defined in claim 3 which is O,O-dimethyl O-(1-(2-pyridinyl)-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 15. The compound as defined in claim 3 which is O,O-diethyl O-(1-(2-pyridinyl)-1H-1,2,4-triazol-3-yl)phosphate.
- 16. An insecticidal composition comprising an inert carrier in intimate admixture with insecticidally effective amount of an active compound corresponding to the formula ##STR314## wherein R represents a nitrogen containing heterocyclic radical corresponding to one of the formulae ##STR315## each X independently represents chloro, fluoro, bromo, nitro, alkyl of 1 to 4 carbon atoms, amino, mono- or dialkylamino wherein each alkyl group independently contains from 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, cyano, trifluoromethyl, trichloromethyl, phenoxy or substituted phenoxy of the formula ##STR316## wherein each Z independently represents chloro, fluoro, bromo, nitro, cyano, alkoxy of 1 to 4 carbon atoms or alkylthio of 1 to 4 carbon atoms, with the proviso that when either n is 2 or 3, all X groups are sterically compatible with each other and all Z groups are sterically compatible with each other; Y represents oxygen or sulfur; each n can independently represent an integer of from 0 to 3, inclusive; R.sup.1 represents hydrogen, chloro, fluoro, bromo, alkyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, phenyl, phenylthio, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, thiocyanato, trifluoromethyl, trichloromethyl, amino, mono- or dialkylamino wherein each alkyl group independently contains from 1 to 4 carbon atoms; R.sup.2 represents methyl, ethyl, propyl or isobutyl and R.sup. 3 represents methoxy, ethoxy, propoxy, ethyl, mono- or dialkylamino wherein each alkyl group independently contains from 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms or phenyl.
- 17. A composition as defined in claim 16 wherein the heterocyclic radical is ##STR317##
- 18. A composition as defined in claim 17 wherein R.sup.2 is methyl or ethyl and R.sup.3 is methoxy or ethoxy.
- 19. The composition as defined in claim 18 wherein the active compound is O,O-diethyl O-(1-(6-chloro-2-pyridinyl)-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 20. The composition as defined in claim 18 wherein the active compound is O,O-diethyl O-(1-(2-pyridinyl)-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 21. The composition as defined in claim 18 wherein the active compound is O,O-diethyl O-(1-(6-fluoro-2-pyridinyl)-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 22. The composition as defined in claim 18 wherein the active compound is O,O-diethyl O-(1-(2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 23. The composition as defined in claim 18 wherein the active compound is O,O-diethyl O-(1-(6-fluoro-2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 24. The composition as defined in claim 18 wherein the active compound is O,O-diethyl O-(1-(2-pyridinyl)-5-ethyl-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 25. The composition as defined in claim 18 wherein the active compound is O,O-diethyl O-(1-(6-phenoxy-2-pyridinyl)-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 26. The composition as defined in claim 18 wherein the active compound is O,O-diethyl O-(1-(6-phenoxy-2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 27. The composition as defined in claim 18 wherein the active compound is O,O-dimethyl O-(1-(2-pyridinyl-5-methyl-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 28. The composition as defined in claim 18 wherein the active compound is O,O-diethyl O-(1-(2-pyridinyl)-5-(1-methylethyl)-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 29. The composition as defined in claim 18 wherein the active compound is O,O-dimethyl O-(1-(2-pyridinyl)-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 30. The composition as defined in claim 18 wherein the active compound is O,O-diethyl O-(1-(2-pyridinyl)-1H-1,2,4-triazol-3-yl)phosphate.
- 31. A method for the kill and control of insects which comprises contacting said insects or their habitat with a composition containing as the active ingredient, an insecticidally effective amount of an active compound corresponding to the formula ##STR318## wherein R represents a nitrogen containing heterocyclic radical corresponding to one of the formulae ##STR319## each X independently represents chloro, fluoro, bromo, nitro, alkyl of 1 to 4 carbon atoms, amino, mono- or dialkylamino wherein each alkyl group independently contains from 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, cyano, trifluoromethyl, trichloromethyl, phenoxy or substituted phenoxy of the formula ##STR320## wherein each Z independently represents chloro, fluoro, bromo, nitro, cyano, alkoxy of 1 to 4 carbon atoms or alkylthio of 1 to 4 carbon atoms, with the proviso that when either n is 2 or 3, all X groups are sterically compatible with each other and all Z groups are sterically compatible with each other; Y represents oxygen
- or sulfur; each n can independently represent an integer of from 0 to 3, inclusive; R.sup.1 represents hydrogen, chloro, fluoro, bromo, alkyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, phenyl, phenylthio, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, thiocyanato, trifluoromethyl, trichloromethyl, amino, mono- or dialkylamino wherein each alkyl group independently contains from 1 to 4 carbon atoms; R.sup.2 represents methyl, ethyl, propyl or isobutyl and R.sup.3 represents methoxy, ethoxy, propoxy, ethyl, mono- or dialkylamino wherein each alkyl group independently contains from 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms or phenyl.
- 32. A method as defined in claim 31 wherein the heterocyclic radical is ##STR321##
- 33. A method as defined in claim 32 wherein R.sup.2 is methyl or ethyl and R.sup.3 is methoxy or ethoxy.
- 34. A method as defined in claim 33 wherein the active compound is O,O-diethyl O-(1-(6-chloro-2-pyridinyl)-1H-1,2,4-triazol-3-yl) phosphorothioate.
- 35. The method as defined in claim 33 wherein the active compound is 0.0-diethyl O-(1-(2-pyridinyl)-1H-1,2,4-triazol-3-yl) phosphorothioate.
- 36. The method as defined in claim 33 wherein the active compound is O,O-diethyl O-(1-(6-fluoro-2-pyridinyl)-1H-1,2,4-triazol-3-yl) phosphorothioate.
- 37. The method as defined in claim 33 wherein the active compound is O,O-diethyl O-(1-(2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl) phosphorothioate.
- 38. The method as defined in claim 33 wherein the active compound is O,O-diethyl O-(1-(6-fluoro-2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl) phosphorothioate.
- 39. The method as defined in claim 33 wherein the active compound is O,O-diethyl O-(1-(2-pyridinyl)-5-ethyl-1H-1,2,4-triazol-3-yl) phosphorothioate.
- 40. The method as defined in claim 33 wherein the active compound is O,O-diethyl O-(1-(6-phenoxy-2-pyridinyl)-1H-1,2,4-triazol-3-yl) phosphorothioate.
- 41. The method as defined in claim 33 wherein the active compound is O,O-diethyl O-(1-(6-phenoxy-2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl) phosphorothioate.
- 42. The method as defined in claim 33 wherein the active compound is O,O-dimethyl 0-(1-(2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl) phosphorothioate.
- 43. The method as defined in claim 33 wherein the active compound is O,O-diethyl O-(1-(2-pyridinyl)-5-(1-methylethyl)-1H-1,2,4-triazol-3-yl) phosphorothioate.
- 44. The method as defined in claim 33 wherein the active compound is O,O-dimethyl 0-(1-(2-pyridinyl)-1H-1,2,4-triazol-3-yl) phosphorothioate.
- 45. The method as defined in claim 33 wherein the active compound is O,O-diethyl O-(1-(2-pyridinyl)-1H-1,2,4-triazol-3-yl) phosphate.
- 46. A compound as defined in claim 1 wherein the heterocyclic radical is ##STR322##
- 47. A compound as defined in claim 46 wherein R.sup.2 is methyl or ethyl and R.sup.3 is methoxy or ethoxy.
- 48. The compound as defined in claim 47 which is O,O-diethyl O-(1-(3-quinolinyl)-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 49. The compound as defined in claim 47 which is O,O-diethyl O-(1-(2-quinolinyl)-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 50. A composition as defined in claim 16 wherein the heterocyclic radical is ##STR323##
- 51. A composition as defined in claim 50 wherein R.sup.2 is methyl or ethyl and R.sup.3 is methoxy or ethoxy.
- 52. The composition as defined in claim 51 wherein the active compound is O,O-diethyl O-(1-(3-quinolinyl)-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 53. The composition as defined in claim 51 wherein the active compound is O,O-diethyl O-(1-(2-quinolinyl)-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 54. A method as defined in claim 31 wherein the heterocyclic radical is ##STR324##
- 55. A method as defined in claim 54 wherein R.sup.2 is methyl or ethyl and R.sup.3 is methoxy or ethoxy.
- 56. The method as defined in claim 55 wherein the active compound is O,O-diethyl O-(1-(3-quinolinyl)-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 57. The method as defined in claim 56 wherein the active compound is is O,O-diethyl O-(2-(2-quinolinyl)-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 58. The compound as defined in claim 3 which is O,O-dimethyl O-(1-(6-fluoro-2-pyridinyl)-5-methyl-1H:1,2,4-triazol-3-yl)phosphorothioate.
- 59. The compound as defined in claim 3 which is O,O-dimethyl O-(1-(6-trifluoromethyl-2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 60. The compound as defined in claim 3 which is O,O-diethyl O-(1-(6-(trifluoromethyl-2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 61. The composition as defined in claim 18 wherein the active compound is O,O-dimethyl O-(1-(6-fluoro-2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 62. The composition as defined in claim 19 wherein the active compound is O,O-dimethyl O-(1-(6-trifluoromethyl-2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 63. The composition as defined in claim 18 wherein the active compound is O,O-diethyl O-(1-(6-(trifluoromethyl-2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 64. The compound as defined in claim 33 wherein the active compound is O,O-dimethyl O-(1-(6-fluoro-2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 65. The compound as defined in claim 33 wherein the active compound is O,O-dimethyl O-(1-(6-trifluoromethyl-2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl)phosphorothioate.
- 66. The compound as defined in claim 33 wherein the active compound is O,O-diethyl O-(1-(6-(trifluoromethyl-2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl)phosphorothioate.
CROSS-REFERENCE TO RELATED APPLICATION
This is a continuation-in-part of Application Ser. No. 951,923, filed Oct. 13, 1978, now abandoned.
US Referenced Citations (11)
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
951923 |
Oct 1978 |
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