Claims
- 1. A herbicidal composition comprising an active thiolcarbamate herbicide compound and an antidotally effective amount of an antidote compound having the formula ##STR345## wherein R is haloalkyl containing from 1 to about 6 carbon atoms, inclusive; and R.sub.1 and R.sub.2 are alkenyl containing from 2 to about 12 carbon atoms, inclusive; 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 herbicidal composition as set forth in claim 1 wherein said active thiocarbamate is selected from the group consisting of EPTC, S-ethyl diisobutyl thiocarbamate, S-propyl dipropyl thiocarbamate, S-2,3,3-trichloroallyl-diisopropyl thiocarbamate, S-ethyl cyclohexylethyl thiocarbamate or S-ethyl hexahydro-1H-azepine-1-carbothioate.
- 3. A herbicidal composition comprising an active S-alkyl thiolcarbamate pre-emergent herbicide and a corn crop protective agent comprising an effective but non-phytotoxic amount of N,N-dipropyl dichloroacetamide.
- 4. A herbicidal composition comprising an active S-alkyl thiolcarbamate pre-emergent herbicide and a corn crop protective agent comprising an effective but non-phytotoxic amount of N,N,-diisopropyl dichloroacetamide.
- 5. A herbicidal composition comprising an active thiolcarbamate herbicide compound and a non-phytotoxic antidotally effective amount of an amide of a haloalkanoic acid having from 2 to 7 carbon atoms, inclusive, said amide being antidotally active with said thiolcarbamate herbicide.
- 6. The herbicidal composition of claim 5 wherein said amide has the formula ##STR346## wherein R is C.sub.1 to C.sub.6 haloalkyl and R.sub.1 and R.sub.2 can be the same or different and can be selected from the group consisting of hydrogen;
- C.sub.1 -c.sub.20 haloalkyl;
- C.sub.2 -c.sub.12 alkenyl;
- C.sub.2 -c.sub.12 haloalkenyl;
- C.sub.2 -c.sub.12 alkynyl;
- C.sub.2 -c.sub.20 hydroxyalkyl;
- C.sub.2 -c.sub.20 cyanoalkyl;
- C.sub.2 -c.sub.20 cyanoalkenyl;
- C.sub.3 -c.sub.6 cycloalkyl;
- C.sub.4 -c.sub.8 alkylcycloalkyl;
- C.sub.2 -c.sub.20 alkoxyalkyl;
- C.sub.3 -c.sub.6 cycloalkenyl;
- phenyl;
- substituted phenyl wherein said substituents can be selected from alkyl C.sub.1 -C.sub.4, halogen, haloalkyl C.sub.1 -C.sub.4, alkoxy C.sub.1 -C.sub.4, haloalkylamido C.sub.1 -C.sub.4, phthalamido, hydroxy, alkylcarbamyloxy C.sub.2 -C.sub.6, alkenylcarbamyloxy C.sub.3 -C.sub.7, alkylamido C.sub.1 -C.sub.4, haloalkylamido C.sub.1 -C.sub.4, and alkylcarboalkenyl C.sub.4 -C.sub.10 ;
- phenylalkyl C.sub.7 -C.sub.10 ; and
- substituted phenylalkyl wherein said substituents can be selected from halogen, alkyl C.sub.1 -C.sub.2, dioxyalkylene C.sub.2 -C.sub.4, and halophenoxyalkylamidoalkyl C.sub.8 -C.sub.10 ;
- provided that when R`is hydrogen, R.sub.2 is other than hydrogen.
- 7. The method of controlling weed pests and protecting crop plants comprising adding to the habitat thereof an herbicidally effective amount of the composition as set forth in claim 1.
- 8. The method of claim 7 wherein the crop is corn and R is --CHCl.sub.2 ; R.sub.1 and R.sub.2 are each --CH--CH.dbd.CH.sub.2.
- 9. The method of claim 7 wherein the crop is wheat and R is --CHCl.sub.2 ; R.sub.1 and R.sub.2 are each --CH--CH.dbd.CH.sub.2.
- 10. The method of protecting a plant crop from injury due to an active herbicidal thiolcarbamate compound, comprising applying to the plant seed prior to planting a non-phytotoxic antidotally effective amount of a compound corresponding to the formula ##STR347## wherein R is haloalkyl containing from 1 to about 6 carbon atoms, inclusive; and R.sub.1 and R.sub.2 are alkenyl containing from 2 to about 12 carbon atoms, inclusive; said compound being antidotally active with said thiolcarbamate herbicide compound.
- 11. The method according to claim 10 wherein the antidote compound is N,N-diallyl.alpha.,.alpha.-dichloroacetamide.
- 12. The method of protecting corn from injury due to an active herbicidal thiolcarbamate compound, comprising applying to the soil a non-phytotoxic antidotally effective amount of a compound corresponding to the formula ##STR348## wherein R is haloalkyl containing from 1 to about 6 carbon atoms, inclusive; and R.sub.1 and R.sub.2 are alkenyl containing from 2 to about 12 carbon atoms, inclusive; said compound being antidotally active with said thiolcarbamate herbicide.
- 13. The method according to claim 12 wherein R is --CHCl.sub.2 and R.sub.1 and R.sub.2 are --CH.sub.2 --CH.dbd.CH.sub.2.
- 14. The method of controlling weed pests and protecting a plant crop from injury due to an active thiolcarbamate herbicide compound, comprising applying to the soil a herbicidally effective amount of said herbicide and a nonphytotoxic antidotally effective amount of an amide of a haloalkanoic acid having from 2 to 7 carbon atoms, inclusive, said amide being antidotally active with said thiolcarbamate herbicide.
- 15. The method of claim 14 wherein said amide has the formula ##STR349## wherein R is C.sub.1 to C.sub.6 haloalkyl and R.sub.1 and R.sub.2 can be the same or different and can be selected from the group consisting of
- hydrogen;
- C.sub.1 -c.sub.20 haloalkyl;
- C.sub.2 -c.sub.12 alkenyl;
- C.sub.2 -c.sub.12 haloalkenyl;
- C.sub.2 -c.sub.12 alkynyl;
- C.sub.1 -c.sub.20 hydroxyalkyl;
- C.sub.2 -c.sub.20 cyanoalkyl;
- C.sub.2 -c.sub.20 cyanoalkenyl;
- C.sub.3 -c.sub.6 cycloalkyl;
- C.sub.4 -c.sub.8 alkylcycloalkyl;
- C.sub.2 -c.sub.20 alkoxyalkyl;
- C.sub.3 -c.sub.6 cycloalkenyl;
- phenyl;
- substituted phenyl wherein said substituents can be selected from alkyl C.sub.1 -C.sub.4, halogen, haloalkyl C.sub.1 -C.sub.4, alkoxy C.sub.1 -C.sub.4, haloalkylamido C.sub.1 -C.sub.4, phthalamido, hydroxy, alkylcarbamyloxy C.sub.2 -C.sub.6, alkenylcarbamyloxy C.sub.3 -C.sub.7, alkylamido C.sub.1 -C.sub.4, haloalkylamido C.sub.1 -C.sub.4, and alkylcarboalkenyl C.sub.4 -C.sub.10 ;
- phenylalkyl C.sub.7 -C.sub.10 ; and
- substituted phenylalkyl wherein said substituents can be selected from halogen, alkyl C.sub.1 -C.sub.2, dioxyalkylene C.sub.2 -C.sub.4, and halophenoxyalkylamidoalkyl C.sub.8 -C.sub.10 ;
- provided that when R.sub.1 is hydrogen, R.sub.2 is other than hydrogen.
- 16. The method of increasing the resistance of crop plant 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 nonphytotoxic amount of an amide of a haloalkanoic acid having from 2 to 7 carbon atoms, inclusive, said amide being antidotally active with said thiolcarbamate herbicide in the presence of said seed.
- 17. The method of claim 16 wherein said amide has the formula ##STR350## wherein R is C.sub.1 to C.sub.6 haloalkyl and R.sub.1 and R.sub.2 can be the same or different and can be selected from the group consisting of
- hydrogen;
- C.sub.1 -c.sub.20 haloalkyl;
- C.sub.2 -c.sub.12 alkenyl;
- C.sub.2 -c.sub.12 haloalkenyl;
- C.sub.2 -c.sub.12 alkynyl;
- C.sub.1 -c.sub.20 hydroxyalkyl;
- C.sub.2 -c.sub.20 cyanoalkyl;
- C.sub.2 -c.sub.20 cyanoalkenyl;
- C.sub.3 -c.sub.6 cycloalkyl;
- C.sub.4 -c.sub.8 alkylcycloalkyl;
- C.sub.2 -c.sub.20 alkoxyalkyl;
- C.sub.3 -c.sub.6 cycloalkenyl;
- phenyl;
- substituted phenyl wherein said substituents can be selected from alkyl C.sub.1 -C.sub.4, halogen, haloalkyl C.sub.1 -C.sub.4, alkoxy C.sub.1 -C.sub.4, haloalkylamido C.sub.1 -C.sub.4, phthalamido, hydroxy, alkylcarbamyloxy C.sub.2 -C.sub.6, alkenylcarbamyloxy C.sub.3 -C.sub.7, alkylamido C.sub.1 -C.sub.4, haloalkylamido C.sub.1 -C.sub.4, and alkylcarboalkenyl C.sub.4 -C.sub.10 ;
- phenylalkyl C.sub.7 -C.sub.10 ; and
- substituted phenylalkyl wherein said substituents can be selected from halogen, alkyl C.sub.1 -C.sub.2, dioxyalkylene C.sub.2 -C.sub.4, and halophenoxyalkylamidoalkyl C.sub.8 -C.sub.10 ;
- provided that when R.sub.1 is hydrogen , R.sub.2 is other than hydrogen.
- 18. The method of protecting wheat from injury due to an active herbicidal thiolcarbamate compound, comprising applying to the soil a non-phytotoxic antidotally effective amount of a compound corresponding to the formula ##STR351## wherein R is haloalkyl containing from 1 to about 6 carbon atoms, inclusive; and R.sub.1 and R.sub.2 are alkenyl, containing from 2 to about 12 carbon atoms, inclusive, said compound being antidotally active with said thiolcarbamate herbicide.
- 19. The method for protecting corn from injury due to an active S-alkyl thiocarbamate pre-emergent herbicide comprising applying to the soil in the vicinity of the corn seed an effective but non-phytotoxic amount of N,N-diisopropyl dichloroacetamide.
- 20. The method for protecting corn seed in order to improve the resistance of the seed to ethyl N,N-dipropylthiolcarbamate, when applied preemergently, comprising applying to the surface of the corn seed a coating of an effective but substantially non-phytotoxic quantity of an amide of dichloroacetic acid.
- 21. The method for protecting corn from injury due to an active S-alkyl thiocarbamate pre-emergent herbicide comprising applying to the soil in the vicinity of the corn seed an effective but non-phytotoxic amount of N,N-dipropyl dichloroacetamide.
- 22. The method of protecting corn seed in order to improve the resistance of the seed to ethyl N,N-dipropylthiolcarbamate, when applied pre-emergently, comprising applying to the surface of the corn seed, prior to planting, a coating of an effective but substantially non-phytotoxic quantity of an amide of dichloroacetic acid.
- 23. The method of protecting corn seed in order to improve the resistance of the seed to ethyl N,N-dipropylthiolcarbamate, when applied pre-emergently, comprising applying to the surface of the corn seed, prior to planting, a coating of an effective but substantially non-phytotoxic quantity of N,N-diallyl dichloroacetamide.
- 24. The method for protecting corn from injury due to an active S-alkyl thiolcarbamate pre-emergent herbicide comprising applying to the soil in the vicinity of the corn seed an effective but non-phytotoxic amount of N,N-di-n-propyl dichloroacetamide.
- 25. The method of protecting a plant crop from injury due to an active herbicidal thiolcarbamate compound, comprising applying to the surface of the plant seed prior to planting an effective but substantially non-phytotoxic antidotally quantity of an amide of dichloroacetic acid, said amide being antidotally active with said thiolcarbamate herbicide compound.
CROSS REFERENCE TO RELATED APPLICATION
This application is a continuation-in-part of copending application, Ser. No. 134,868, filed Apr. 16, 1971 now abandoned.
US Referenced Citations (8)
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
134868 |
Apr 1971 |
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