Claims
- 1. Compounds having the formula ##STR10## wherein X is chlorine, bromine or iodine;
- Y is O, S or --NH--;
- R is a C.sub.5-7 1-cycloalken-1-yl radical which may be substituted with C.sub.1-6 alkyl;
- R.sub.1 and R.sub.2 are hydrogen or C.sub.1-6 alkyl and
- R.sub.3 is C.sub.1-6 alkyl, haloalkyl or alkoxyalkyl or alkenyl, haloalkenyl or alkynyl having up to 4 carbon atoms, cyclopropylmethyl, acetyl when Y is --NH-- or pivaloyl or 2-cyanopropyl when Y is O.
- 2. Compounds according to claim 1 wherein R is a 1-cyclohexen-1yl radical.
- 3. Compounds according to claim 2 wherein said 1-cyclohexen-1-yl radical is substituted with a C.sub.1-6 alkyl group on at least one of the ortho carbon atoms relative to the amide nitrogen atom.
- 4. Compounds according to claim 3 wherein X is chlorine, Y is S, R.sub.1, R.sub.2 and R.sub.3 are C.sub.1-6 alkyl groups.
- 5. Compunds according to claim 3, wherein X is chlorine, Y is NH, R.sub.1 and R.sub.2 are hydrogen and R.sub.3 is acetyl.
- 6. Compounds according to claim 3 wherein X is chlorine, Y is 0 and R.sub.1 and R.sub.2 are hydrogen.
- 7. Compounds according to claim 6 wherein R.sub.3 is C.sub.1-6 alkyl or haloalkyl.
- 8. Compounds according to claim 6 wherein R.sub.3 is alkenyl or haloalkenyl having up to 4 carbon atoms.
- 9. Compounds according to claim 6 wherein R.sub.3 is propargyl alkynyl.
- 10. Compounds according to claim 6 wherein R.sub.3 is C.sub.1-6 alkoxyalkyl.
- 11. Compounds according to claim 6 wherein R.sub.3 is cyclopropylmethyl.
- 12. Compound according to claim 7 which is N-(methoxymethyl)-N-(2,6-dimethyl-1-cyclohexen-1-yl)-2-chloroacetamide.
- 13. Compound according to claim 7 which is N-(ethoxymethyl)-N-(2,6-dimethyl-1-cyclohexen-1-yl)-2-chloroacetamide.
- 14. Compound according to claim 7 which is N-(ethoxymethyl)-N-(2-methyl-6-ethyl-1-cyclohexen-1-yl)-2-chloroacetamide.
- 15. Compound according to claim 7 which is N-(ethoxymethyl)-N-(2-ethyl-6-methyl-1-cyclohexen-yl)-2-chloroacetamide.
- 16. Compound according to claim 7 which is N-(isobutoxymethyl)-N-(2,6-dimethyl-1-cyclohexen-1-yl)-2-chloroacetamide.
- 17. Compound according to claim 7 which is N-(butoxymethyl)-N-(2,6-dimethyl-1-cyclohexen-1-yl)-2-chloroacetamide.
- 18. Compounds according to claim 1 wherein R is a 1-cyclopenten-1-yl radical, R.sub.1 and R.sub.2 are hydrogen, R.sub.3 is C.sub.1-6 alkyl and Y is O.
- 19. Compounds according to claim 18 wherein said 1-cyclopenten-1-yl radical is substituted with C.sub.1-6 alkyl group on at least one of the carbon atoms ortho to the amide nitrogen.
- 20. Compound according to claim 19 which is N-(ethoxymethyl)-N-(2,5-dimethyl-1-cyclopenten-1-yl)-2-chloroacetamide.
- 21. Compound according to claim 19 which is N-(n-propoxymethyl)-N-(2,5-dimethyl-1-cyclopenten-1-yl)-2-chloroacetamide.
- 22. Herbicidal compositions comprising a herbicidally-effective amount of a compound having the formula ##STR11## wherein X is chlorine, bromine or iodine;
- Y is O, S or --NH--;
- R is a C.sub.5-7 1-cycloalken-1-yl radical which may be substituted with C.sub.1-6 alkyl;
- R.sub.1 and R.sub.2 are hydrogen or C.sub.1-6 alkyl and
- R.sub.3 is C.sub.1-6 alkyl, haloalkyl or alkoxyalkyl or alkenyl, haloalkenyl or alkynyl having up to 4 carbon atoms, cyclopropylmethyl, acetyl when Y is --NH-- or pivaloyl or 2-cyanopropyl when Y is O.
- 23. Compositions according to claim 22 wherein R is a 1-cyclohexen-1-yl radical.
- 24. Compositions according to claim 23 wherein said 1-cyclohexen-1-yl radical is substituted with a C.sub.1-6 alkyl group on at least one of the ortho carbon atoms relative to the amide nitrogen atom.
- 25. Composition according to claim 24 wherein said compound is N-(methoxymethyl)-N-(2,6-dimethyl-1-cyclohexen-1-yl)-2-chloroacetamide.
- 26. Composition according to claim 24 wherein said compound is N-(ethoxymethyl)-N-(2,6-dimethyl-1-cyclohexen-1-yl)-2-chloroacetamide.
- 27. Composition according to claim 24 wherein said composition is a mixture of N-(ethoxymethyl)-N-(2-methyl-6-ethyl-1-cyclohexen-1-yl)-2-chloroacetamide and N-(ethoxymethyl)-N-(2-ethyl-6-methyl-1-cyclohexen-1-yl)-2-chloroacetamide.
- 28. Composition according to claim 24 wherein said compound is N-(isobutoxymethyl)-N-(2,6-dimethyl-1-cyclohexen-1-yl)-2-chloroacetamide.
- 29. Composition according to claim 24 wherein said compound is N-(butoxymethyl)-N-(2,6-dimethyl-1-cyclohexen-1-yl)-2-chloroacetamide.
- 30. Compositions according to claim 22 wherein R is a 1-cyclopenten-1-yl radical, R.sub.1 and R.sub.2 are hydrogen, R.sub.3 is a C.sub.1-6 alkyl and Y is O.
- 31. Compositions according to claim 30 wherein said 1-cyclopenten-1-yl radical is substituted with a C.sub.1-6 alkyl group on at least one carbon atom ortho to the amide nitrogen atom.
- 32. Composition according to claim 31 wherein said compound is N-(ethoxymethyl)-N-(2,5-dimethyl-1-cyclopenten-1-yl)-2-chloroacetamide.
- 33. Composition according to claim 31 wherein said compound is N-(n-propoxymethyl)-N-(2,5-dimethyl-1-cyclopenten-1-yl)-2-chloroacetamide.
- 34. Method for controlling undesirable plants associated with monocotyledonous and dicotyledonous crop plants which comprises applying to the locus of said plants a herbicidally-effective amount of a compound having the formula ##STR12## wherein X is chlorine, bromine or iodine;
- Y is O, S or --NH--;
- R is C.sub.5-7 1-cycloalken-1-yl radical which may be substituted with C.sub.1-6 alkyl;
- R.sub.1 and R.sub.2 are hydrogen or C.sub.1-6 alkyl and
- R.sub.3 is C.sub.1-6 alkyl, haloalkyl or alkoxyalkyl or alkenyl, haloalkenyl or alkynyl having up to 4 carbon atoms, cyclopropylmethyl, acetyl when Y is --NH-- or pivaloyl or 2-cyanopropyl when Y is O.
- 35. Method according to claim 34 wherein R is a 1-cyclohexen-1-yl radical.
- 36. Method according to claim 35 wherein said 1-cyclohexen-1-yl radical is substituted with a C.sub.1-6 alkyl group
- 37. Method according to claim 36 wherein said compound is N-(methoxymethyl)-N-(2,6-dimethyl-1-cyclohexen-1-yl)-2-chloroacetamide.
- 38. Method according to claim 36 wherein said compound is (ethoxymethyl)-N-(2,6-dimethyl-1-cyclohexen-1-yl)-2-chloroacetamide.
- 39. Method according to claim 36 wherein said composition is a mixture of N-(ethoxymethyl)-N-(2-methyl-6-ethyl-1-cyclohexen-1-yl)-2-chloroacetamide and N-(ethoxymethyl)-N-(2-ethyl-6-methyl-1-cyclohexen-1-yl)-2-chloroacetamide.
- 40. Method according to claim 36 wherein said compound is N-(propoxymethyl)-N-(2,6-dimethyl-1-cyclohexen-1-yl)-2-chloroacetamide.
- 41. Method according to claim 36 wherein said compound is N-(butoxymetyl)-N-(2,6-dimethyl-1-cyclohexen-1-yl)-2-chloroacetamide.
- 42. Method according to claim 34 wherein R is a 1-cyclopenten-1-yl radical, R.sub.1 and R.sub.2 are hydrogen, R.sub.3 is a C.sub.1-6 alkyl and Y is O.
- 43. Method according to claim 42 wherein said 1-cyclopenten-1-yl radical is substituted with a C.sub.1-6 alkyl radical in at least one ortho position relative to the amide nitrogen atom.
- 44. Method accordig to claim 43 wherein said compound is N-(ethoxymethyl)-N-(2,6-dimethyl-1-cyclopenten-1-yl)-2-chloroacetamide.
- 45. Method according to claim 43 wherein said compound is N-(n-propoxymethyl)-N-(2,6-dimethyl-1-cyclopenten-1-yl)-2-chloroacetamide.
Parent Case Info
This application is a continuation-in-part of Ser. No. 897,472, filed Apr. 18, 1978, now abandoned.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
3574746 |
Chupp |
Apr 1971 |
|
4025554 |
Tournayre et al. |
May 1977 |
|
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
897472 |
Apr 1978 |
|