Claims
- 1. A herbicidal composition comprising an active thiolcarbamate herbicidal compound and an antidote therefor corresponding to the formula ##STR324## wherein R is haloalkyl having from 1 to 6 carbon atoms, inclusive; R.sub.1 and R.sub.2 can be the same or different and can be selected from the group consisting of alkyl having 1 to 20 carbon atoms, inclusive; haloalkyl-N-alkylamido having 3 to 20 carbon atoms, inclusive; haloalkylamido having 2 to 20 carbon atoms, inclusive; haloalkylamidoalkyl having 4 to 20 carbon atoms, inclusive; haloalkyl-N-alkylamidoalkyl having 3 to 20 carbon atoms, inclusive; and haloalkylamidoalkenyl having 4 to 20 carbon atoms, inclusive; substituted phenylalkyl wherein said substituents can be selected from halophenoxyalkylamidoalkyl having 9 to 20 carbon atoms, inclusive; .alpha.-haloalkylamidophenylalkyl having 9 to 20 carbon atoms, inclusive; .alpha.-haloalkylamidonitrophenylalkyl having 9 to 20 carbon atoms, inclusive; .alpha.-haloalkylamidohalophenylalkyl having 9 to 20 carbon atoms, inclusive; provided only one of R.sub.1 or R.sub.2 is alkyl and; said compound being antidotally active with said thiolcarbamate herbicide compound and wherein said compound is present in an amount varying between about 0.0001 to 30 parts by weight for each part by weight of the active herbicidal compound.
- 2. The composition as set forth in claim 1 wherein said active herbicidal compound is selected from EPTC, S-ethyl diisobutyl thiolcarbamate, S-propyl dipropyl thiolcarbamate, S-2,3,3-trichloroallyl-diisopropyl thiolcarbamate, S-ethyl cyclohexyl ethyl thiocarbamate, [2-chloro-2',6'-diethyl-N-(methoxymethyl) acetanilide,] S-ethyl hexahydro-1H-azepine-1-carbothioate, [2-chloro-N-isopropylacetanilide, N,N-diallyl-2-chloroacetamide,] S-4-chlorobenzyl diethyl thiolcarbamate, [2-chloro-4-ethylamino-6-isopropylamino-s-ethylamino-s-triazine-2-methylpropionitrile, 2-chloro-4-cyclopropylamino-6-isopropyl-amino-s-triazine, 2,4-D] and mixtures thereof.
- 3. A herbicidal composition comprising an active thiolcarbamate herbicidal compound and a nonphytotoxic antidotally effective amount of an antidote compound therefor corresponding to the formula ##STR325## wherein R is haloalkyl having from 1 to 6 carbon atoms, inclusive; R.sub.1 is selected from the group consisting of hydrogen, lower alkyl having from 1 to 20 carbon atoms, inclusive and haloalkylamidoalkyl having from 3 to 20 carbon atoms, inclusive, and R.sub.2 is substituted amido of the formula ##STR326## in which R.sub.3, R.sub.4 and R.sub.5 are the same or different each selected from the group consisting of hydrogen, alkyl having from 1 to 20 carbon atoms, inclusive, haloalkyl having from 1 to 20 carbon atoms, inclusive, alkenyl having from 2 to 12 carbon atoms, inclusive, halophenoxyalkyl having from 7 to 12 carbon atoms, inclusive, phenylalkyl having from 7 to 12 carbon atoms, inclusive and substituted phenylalkyl wherein said substituents are selected from the group consisting of nitro and halogen; provided that R.sub.3 is not hydrogen; said antidote being antidotally active with said thiolcarbamate herbicide compound and wherein said antidote is present in an amount ranging between about 0.0001 to 30 parts by weight for each part by weight of active herbicidal compound.
- 4. The composition as set forth in claim 3 wherein R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR327##
- 5. The composition as set forth in claim 3 wherein R is --CHCl.sub.2 ; R.sub.1 is --C.sub.2 H.sub.5 and R.sub.2 is ##STR328##
- 6. The composition as set forth in claim 3 wherein R is --CHCl.sub.2 ; R.sub.1 and R.sub.2 are ##STR329##
- 7. The composition as set forth in claim 3 wherein R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR330##
- 8. The composition as set forth in claim 3 wherein R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR331##
- 9. The composition as set forth in claim 3 wherein R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR332##
- 10. The composition as set forth in claim 3 wherein R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR333##
- 11. The composition as set forth in claim 3 wherein R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR334##
- 12. The composition as set forth in claim 3 wherein R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR335##
- 13. The composition as set forth in claim 3 wherein R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR336##
- 14. The composition as set forth in claim 3 wherein R is --CH.sub.2 Cl; R.sub.1 is H and R.sub.2 is ##STR337##
- 15. The composition as set forth in claim 3 wherein R is --CCl.sub.3 ; R.sub.1 is H and R.sub.2 is ##STR338##
- 16. The composition as set forth in claim 3 wherein R is --CH.sub.2 Cl; R.sub.1 is H and R.sub.2 is ##STR339##
- 17. The composition as set forth in claim 3 wherein R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR340##
- 18. A herbicidal composition comprising an active thiolcarbamate herbicidal compound and a nonphytotoxic antidotally effective amount of an antidote compound therefor corresponding to the formula ##STR341## wherein R is haloalkyl having from 1 to 6 carbon atoms, inclusive; R.sub.1 is selected from the group consisting of hydrogen, lower alkyl having from 1 to 20 carbon atoms, inclusive and haloalkylamidoalkyl having from 3 to 20 carbon atoms, inclusive, and R.sub.2 is substituted amido of the formula ##STR342## in which R.sub.3 is selected from the group consisting of alkylene having from 1 to 20 carbon atoms, inclusive and substituted alkylene having from 1 to 20 carbon atoms, inclusive wherein said substituents are selected from the group consisting of vinyl, halo, phenyl and substituted phenyl, said substituents are selected from the group consisting of nitro and halogen; R.sub.4 is selected from the group consisting of hydrogen, alkyl having from 1 to 20 carbon atoms, inclusive, haloalkyl having from 1 to 20 carbon atoms, inclusive and alkenyl having from 2 to 12 carbon atoms, inclusive, and R.sub.5 is selected from the group consisting of alkyl having from 1 to 20 carbon atoms, inclusive, haloalkyl having from 1 to 20 carbon atoms, inclusive and halophenoxyalkyl having from 7 to 12 carbon atoms, inclusive; said antidote being antidotally active with said thiolcarbamate herbicide compound and wherein said antidote is present in an amount ranging between about 0.0001 to 30 parts by weight for each part by weight of active herbicidal compound.
- 19. The method of increasing the resistance of crop seed to injury from an active thiolcarbamate herbicide compound, comprising applying to the surface of said seed a coating of an antidotally effective but substantially non-phytotoxic amount of an antidote compound corresponding to the formula ##STR343## wherein R is haloalkyl having from 1 to 6 carbon atoms, inclusive; R.sub.1 is selected from the group consisting of hydrogen, lower alkyl having from 1 to 20 carbon atoms, inclusive and haloalkylamidoalkyl having from 3 to 20 carbon atoms, inclusive, and R.sub.2 is substituted amido of the formula ##STR344## in which R.sub.3, R.sub.4 and R.sub.5 are the same or different each selected from the group consisting of hydrogen, alkyl having from 1 to 20 carbon atoms, inclusive, haloalkyl having from 1 to 20 carbon atoms, inclusive, alkenyl having from 2 to 12 carbon atoms, inclusive, halophenoxyalkyl having from 7 to 12 carbon atoms, inclusive, phenylalkyl having from 7 to 12 carbon atoms, inclusive and substituted phenylalkyl wherein said substituents are selected from nitro and halogen; provided that R.sub.3 is not hydrogen; said antidote being antidotally active with said thiolcarbamate herbicide.
- 20. Method of increasing the resistance of crop seed to injury from an active thiolcarbamate herbicide compound according to claim 19 wherein R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR345##
- 21. Method of increasing the resistance of crop seed to injury from an active thiolcarbamate herbicide compound according to claim 19 wherein R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR346##
- 22. Method of increasing the resistance of crop seed to injury from an active thiolcarbamate herbicide compound according to claim 19 wherein R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR347##
- 23. Method of increasing the resistance of crop seed to injury from an active thiolcarbamate herbicide compound according to claim 19 wherein R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR348##
- 24. Method of increasing the resistance of crop seed to injury from an active thiolcarbamate herbicide compound according to claim 19 wherein R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR349##
- 25. Method of increasing the resistance of crop seed to injury from an active thiolcarbamate herbicide compound according to claim 19 wherein R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR350##
- 26. Method of increasing the resistance of crop seed to injury from an active thiolcarbamate herbicide compound according to claim 19 wherein R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR351##
- 27. Method of increasing the resistance of crop seed to injury from an active thiolcarbamate herbicide compound according to claim 19 wherein R is --CH.sub.2 Cl; R.sub.1 is H and R.sub.2 is ##STR352##
- 28. Method of increasing the resistance of crop seed to injury from an active thiolcarbamate herbicide compound according to claim 19 wherein R is --CCl.sub.3 ; R.sub.1 is H and R.sub.2 is ##STR353##
- 29. Method of increasing the resistance of crop seed to injury from an active thiolcarbamate herbicide compound according to claim 19 wherein R is --CHCl.sub.2 ; R.sub.1 and R.sub.2 are ##STR354##
- 30. Method of increasing the resistance of crop seed to injury from an active thiolcarbamate herbicide compound according to claim 19 wherein R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR355##
- 31. Method of increasing the resistance of crop seed to injury from an active thiolcarbamate herbicide compound according to claim 19 wherein R is --CH.sub.2 Cl; R.sub.1 is H and R.sub.2 is ##STR356##
- 32. Method of increasing the resistance of crop seed to injury from an active thiolcarbamate herbicide compound according to claim 19 wherein R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR357##
- 33. Method of increasing the resistance of crop seed to injury from an active thiolcarbamate herbicide compound according to claim 19 wherein R is --CHCl.sub.2 ; R.sub.1 is --C.sub.2 H.sub.5 and R.sub.2 ##STR358##
- 34. The method of protecting a plant crop from injury due to an active thiolcarbamate herbicidal compound, comprising applying to the soil, in which an herbicidally effective amount of said active thiolcarbamate herbicidal compound is used, a non-phytotoxic antidotally effective amount of a compound corresponding to the formula ##STR359## wherein R is haloalkyl having from 1 to 6 carbon atoms, inclusive; R.sub.1 is selected from the group consisting of hydrogen, lower alkyl having from 1 to 20 carbon atoms, inclusive and haloalkylamidoalkyl having from 3 to 20 carbon atoms, inclusive, and R.sub.2 is substituted amido of the formula ##STR360## in which R.sub.3, R.sub.4 and R.sub.5 are the same or different each selected from the group consisting of hydrogen, alkyl having from 1 to 20 carbon atoms, inclusive, haloalkyl having from 1 to 20 carbon atoms, inclusive, alkenyl having from 2 to 12 carbon atoms, inclusive, halophenoxyalkyl having from 7 to 12 carbon atoms, inclusive, phenylalkyl having from 7 to 12 carbon atoms, inclusive and substituted phenylalkyl wherein said substituents are selected from the nitro and halogen; provided that R.sub.3 is not hydrogen.
- 35. The method of protecting crop plant from injury according to claim 34 in which R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR361##
- 36. The method of protecting crop plant from injury according to claim 34 in which R is --CHCl.sub.2 ; R.sub.1 is --C.sub.2 H.sub.5 and R.sub.2 is ##STR362##
- 37. The method of protecting crop plant from injury according to claim 34 in which R is --CHCl.sub.2 ; R.sub.1 and R.sub.2 are ##STR363##
- 38. The method of protecting crop plant from injury according to claim 34 in which R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR364##
- 39. The method of protecting crop plant from injury according to claim 34 in which R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR365##
- 40. The method of protecting crop plant from injury according to claim 34 in which R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR366##
- 41. The method of protecting crop plant from injury according to claim 34 in which R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR367##
- 42. The method of protecting crop plant from injury according to claim 34 in which R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR368##
- 43. The method of protecting plant crop from injury according to claim 34 in which R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR369##
- 44. The method of protecting crop plant from injury according to claim 34 in which R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR370##
- 45. The method of protecting crop plant from injury according to claim 34 in which R is --CH.sub.2 Cl; R.sub.1 is H and R.sub.2 is ##STR371##
- 46. The method of protecting crop plant from injury according to claim 34 in which R is --CCl.sub.3 ; R.sub.1 is H and R.sub.2 is ##STR372##
- 47. The method of protecting crop plant from injury according to claim 34 in which R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR373##
- 48. The method of protecting crop plant from injury according to claim 34 in which R is --CHCl.sub.2 ; R.sub.1 is H and R.sub.2 is ##STR374##
- 49. The method of increasing the resistance of crop seed to injury from an active thiolcarbamate herbicide compound, comprising applying to the surface of said seed a coating of an antidotally effective but substantially non-phytotoxic amount of an antidote compound corresponding to the formula ##STR375## wherein R is haloalkyl having from 1 to 6 carbon atoms, inclusive; R.sub.1 is selected from the group consisting of hydrogen, lower alkyl having from 1 to 20 carbon atoms, inclusive and haloalkylamidoalkyl having from 3 to 20 carbon atoms, inclusive, and R.sub.2 is substituted amido of the formula ##STR376## in which R.sub.3 is selected from the group consisting of alkylene having from 1 to 20 carbon atoms, inclusive and substituted alkylene having from 1 to 20 carbon atoms, inclusive wherein said substituents are selected from the group consisting of vinyl, halo, phenyl and substituted phenyl, said substituents are selected from the group consisting of nitro and halogen; R.sub.4 is selected from the group consisting of hydrogen, alkyl having from 1 to 20 carbon atoms, inclusive, haloalkyl having from 1 to 20 carbon atoms, inclusive and alkenyl having from 2 to 12 carbon atoms, inclusive, and R.sub.5 is selected from the group consisting of alkyl having from 1 to 20 carbon atoms, inclusive, haloalkyl having from 1 to 20 carbon atoms, inclusive and halophenoxyalkyl having from 7 to 12 carbon atoms, inclusive; said antidote compound antidotally active with said thiolcarbamate herbicide.
- 50. The method of protecting a plant crop from injury due to an active thiolcarbamate herbicidal compound, comprising applying to the soil, in which an herbicidally effective amount of said active thiolcarbamate herbicidal compound is used, a non-phytotoxic antidotally effective amount of a compound corresponding to the formula ##STR377## wherein R is haloalkyl having from 1 to 6 carbon atoms, inclusive; R.sub.1 is selected from the group consisting of hydrogen, lower alkyl having from 1 to 20 carbon atoms, inclusive and haloalkylamidoalkyl having from 3 to 20 carbon atoms, inclusive, and R.sub.2 is substituted amido of the formula ##STR378## in which R.sub.3 is selected from the group consisting of alkylene having from 1 to 20 carbon atoms, inclusive and substituted alkylene; R.sub.4 is selected from the group consisting of hydrogen, alkyl having from 1 to 20 carbon atoms, inclusive, wherein said substituents are selected from the group consisting of vinyl, halo, phenyl and substituted phenyl, said substituents are selected from the group consisting of nitro and halogen, haloalkyl having from 1 to 20 carbon atoms, inclusive and alkenyl having from 2 to 12 carbon atoms, inclusive, and R.sub.5 is selected from the group consisting of alkyl having from 1 to 20 carbon atoms, inclusive, haloalkyl having from 1 to 20 carbon atoms, inclusive and halophenoxyalkyl having from 7 to 12 carbon atoms, inclusive; said compound being antidotally active with said thiolcarbamate herbicide.
CROSS REFERENCE TO RELATED APPLICATION
This is a division of application Ser. No. 208,041 filed Dec. 9, 1971, now U.S. Pat. No. 4,137,070, which in turn is a continuation-in-part of Ser. No. 134,868, filed Apr. 16, 1971, now abandoned.
US Referenced Citations (7)
Non-Patent Literature Citations (4)
Entry |
McRae, "Herbicides" (1963), CA 61 p. 1190 (1964). |
Sterling Drug, "Bis (Haloalkanoyl) Diamines" (1962), CA 58 pp. 5520-5521 (1963). |
Hamm et al., "Herbicides" (1958), CA 54 pp. 20059-20060 (1960). |
Berberian, "In Vitro and in Vivo Amebicidal, etc." (1961), CA 56 p. 6604 (1962). |
Divisions (1)
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Number |
Date |
Country |
Parent |
208041 |
Dec 1971 |
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Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
134868 |
Apr 1971 |
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