Claims
- 1. A composition for use in protecting crops against the herbicidal action of a haloacetanilide comprising an effective amount of a compound of the formula: ##STR57## wherein n is 0, 1 or 2,
- m is 0 or 1,
- Ar is unsubstituted phenyl, phenyl substituted with from one to three substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and halo, or naphthyl, and
- R.sub.8 is alkyl of 1 to 4 carbon atoms, benzyl or phenyl, in a quantity sufficient to provide a protective action against said haloacetanilide, in combination with an inert liquid or solid carrier for the compound.
- 2. A composition according to claim 1 wherein n is 2 when m is 1 and Ar is phenyl substituted with one or two substituents selected from the group consisting of methyl, methoxy, chloro or bromo.
- 3. A composition according to claim 2 wherein R.sub.8 is n-butyl or phenyl.
- 4. A composition according to claim 4 in which the compound is .alpha.-(2,4-dichlorophenyl)-.alpha.-[(O-triphenyl-tin)-oximino]-acetonitrile.
- 5. A composition according to claims 4 which the compound is .alpha.-(4-methoxyphenyl)-.alpha.-[(O-triphenyl-tin)-oximio]-acetonitrile.
- 6. In the method of combating weed growth in a crop through the application of a herbicidal haloacetanilide, the improvement which comprises applying to said crop, the seed or seedling from which said crop is grown, or to the habitat of the crop's growth a compound of the formula: ##STR58## wherein n is 0, 1 or 2,
- m is 0 or 1,
- X is hydrogen, cyano, alkyl of 1 to 4 carbon atoms or carboalkoxy in which alkoxy contains 1 to 4 carbon atoms,
- Ar is unsubstituted phenyl, phenyl substituted with from one to three substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and halo, or naphthyl, and
- R.sub.8 is alkyl of 1 to 4 carbon atoms, benzyl or phenyl, in a quantity sufficient to protect the crop from the herbicidal effects of said haloacetanilide.
- 7. The improvement according to claim 6 wherein in said compound X is cyano or methyl, n is 2 when m is 1, and Ar is phenyl substituted with one or two substituents selected from the group consisting of methyl, methoxy, chloro and bromo.
- 8. The improvement according to claim 7 wherein R.sub.8 is n-butyl or phenyl.
- 9. The improvement according to claim 8 wherein m is 0 and X is cyano.
- 10. The improvement according to claim 6 in which the compound is .alpha.-(4-methoxyphenyl)-.alpha.-[(O-triphenyl-tin-oximino]acetonitrile, .alpha.-(2,4-dichlorophenyl)-.alpha.-[(O-triphenyl-tin)-oximino]-acetonitrile, .alpha.-phenylsulfonyl-.alpha.-[(O-tri-n-butyl-tin)-oximino]-acetonitrile, .alpha.-(4-methylphenylsulfonyl)-[(O-triphenyl-tin)-oximino]-acetonitrile, .alpha.-(3,4-dimethylphenyl)-.alpha.-[(O-tri-n-butyl-tin)-oximino]-acetonitrile, .alpha.-(4-bromophenyl)-.alpha.-[(O-triphenyl-tin)-oximino]-acetonitrile, .alpha.-phenyl-.alpha.-[(O-triphenyl-tin)-oximino]-acetonitrile, .alpha.-(4-methylphenyl-sulfonyl)-.alpha.-[(O-tri-n-butyl-tin)-oximino]-acetonitrile or .alpha.-(2,4-dichlorophenyl)-.alpha.-[(O-tri-n-butyl-tin)-oximino]-acetonitrile.
- 11. The improvement according to claim 10 wherein said compound is .alpha.-(4-methoxyphenyl)-.alpha.-[(O-triphenyl-tin)-oximino]-acetonitrile
- 12. The improvement according to claim 10 wherein said compound is .alpha.-(2,4-dichlorophenyl)-.alpha.-[(O-triphenyl-tin)-oximino]acetonitrile.
- 13. The improvement according to claim 12 in which the haloacetanilide is N-(1-methyl-2-methoxyethyl)-N-chloroacetyl-2-ethyl-6-methylaniline.
- 14. The improvement according to claim 10 wherein said haloacetanilide is N-(1-methyl-2-methoxyethyl)-N-chloroacetyl-2-ethyl-6-methylaniline or N-n-propoxyethyl-N-chloroacetyl-2,6-diethylaniline and said compound is applied, prior to the application of the haloacetanilide, to the seeds from which said crop is grown.
- 15. The improvement according to claim 10 wherein said haloacetanilide is N-(1-methyl-2-methoxyethyl)-N-chloroacetyl-2-ethyl-6-methylaniline or N-n-propoxyethyl-N-chloroacetyl-2,6-diethylaniline and said compound is applied, prior to the application of the haloacetanilide, to the soil in which said crop is grown.
- 16. The improvement according to claim 10 wherein said haloacetanilide is N-(1-methyl-2-methoxyethyl)-N-chloroacetyl-2-ethyl-6-methylaniline or N-n-propoxyethyl-N-chloroacetyl-2,6-diethylaniline, said crop is rice and said compound is applied to the roots of rice seedlings.
- 17. A method of selectively controlling weed growth in a crop which comprises applying an effective amount of a haloacetanilide herbicide to a crop grown from seed which has been treated with a quantity of a compound of the formula ##STR59## wherein n is 0, 1 or 2,
- m is 0 or 1,
- X is hydrogen, cyano, alkyl of 1 to 4 carbon atoms or or carboalkoxy in which alkoxy contains 1 to 4 carbon atoms,
- Ar is unsubstituted phenyl, phenyl substituted with from one to three substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and halo, or naphthyl, and
- R.sub.8 is alkyl of 1 to 4 carbon atoms, benzyl or phenyl, sufficient to protect the crop from the herbicidal effects of said haloacetanilide.
- 18. The method according to claim 17 wherein, in said compound, X is cyano or methyl, n is 2 when m is 1, and Ar is phenyl substituted with one or two substituents selected from the group consisting of methyl, methoxy, chloro and bromo.
- 19. The method according to claim 17 in which the compound is .alpha.-(4-methoxyphenyl)-.alpha.-[(O-triphenyl-tin-oximino]-acetonitrile, .alpha.-(2,4-dichlorophenyl)-.alpha.-[(O-triphenyl-tin)-oximino]-acetonitrile, .alpha.-phenylsulfonyl-.alpha.-[(O-tri-n-butyl-tin)-oximino]-acetonitrile, .alpha.-(4-methylphenylsulfonyl)-[(O-triphenyl-tin)-oximino]-acetonitrile, .alpha.-(3,4-dimethylphenyl)-.alpha.-[(O-tri-n-butyl-tin)-oximino]-acetonitrile, .alpha.-(4-bromophenyl)-.alpha.-[(O-triphenyl-tin)-oximino]-acetonitrile, .alpha.-phenyl-.alpha.-[(O-triphenyl-tin)-oximino]-acetonitrile, .alpha.-(4-methylphenyl-sulfonyl)-.alpha.-[(O-tri-n-butyl-tin)-oximino]-acetonitrile or .alpha.-(2,4-dichlorophenyl)-.alpha.-[(O-tri-n-butyl-tin)-oximino]-aceto-nitrile.
- 20. The method according to claim 19 wherein said compound is .alpha.-(4-methoxyphenyl)-.alpha.-[(O-triphenyl-tin)-oximino]-acetonitrile.
- 21. The method according to claim 19 wherein said compound is .alpha.-(2,4-dichlorophenyl)-.alpha.-[(O-triphenyl-tin)-oximino]acetonitrile.
Priority Claims (1)
Number |
Date |
Country |
Kind |
9200/78 |
Aug 1978 |
CHX |
|
Parent Case Info
This is a divisional of application Ser. No. 271,310 filed on June 8, 1981, now abandoned, which is a division of application Ser. No. 068,262, filed on Aug. 20, 1979, now U.S. Pat. No. 4,294,772.
US Referenced Citations (8)
Divisions (2)
|
Number |
Date |
Country |
Parent |
271310 |
Jun 1981 |
|
Parent |
068262 |
Aug 1979 |
|