Herbicidal substituted 2-(1-(oxyamino)-alkylidene)-cyclohexane-1,3-diones

Abstract

Substituted 2-[1-(oxyamino)alkylidene]-cyclohexane-1,3-diones have herbicidal activity against grassy weeds.

What is claimed is: 
     
       1. A compound of the formula ##STR45## wherein R is alkyl of 1 to 6 carbon atoms or phenyl; R 1  is haloalkenyl of 2 to 6 carbon atoms and 1 to 3 halogen atoms, p-halobenzyl or p-trifluoromethylbenzyl;   R 2  and R 3  are independently hydrogen, alkyl of 1 to 3 carbon atoms, alkylthio of 1 to 6 carbon atoms, or alkylthioalkyl of 2 to 8 carbon atoms;   R 4  is hydrogen, or carbalkoxy of 2 to 4 carbon atoms;   R 5  is hydrogen, a cation, or ##STR46## wherein R 6  is alkyl of 1 to 6 carbon atoms, phenyl or naphthyl.   
     
     
       2. The compound of claim 1 wherein R 4  and R 5  are each hydrogen. 
     
     
       3. The compound of claim 2 wherein R is alkyl of 1 to 6 carbon atoms. 
     
     
       4. The compound of claim 3 wherein R 1  is said haloalkenyl. 
     
     
       5. The compound according to claim 4 wherein R 2  and R 3  are alkyl of 1 to 3 carbon atoms. 
     
     
       6. The compound according to claim 5 wherein R is propyl, R 2  and R 3  are methyl and R 1  is 3-trans-chloroallyl. 
     
     
       7. The compound according to claim 5 wherein R is ethyl, R 2  and R 3  are methyl and R 1  is 3-trans-chloroallyl. 
     
     
       8. The compound of claim 1 wherein R 1  is p-halobenzyl or p-trifluoromethylbenzyl. 
     
     
       9. The compound of claim 8 wherein R 2  and R 3  are independently alkyl of 1 to 3 carbon atoms. 
     
     
       10. The compound of claim 9 wherein R is ethyl or propyl, R 2  and R 3  are each methyl, R 4  is hydrogen and R 1  is p-chlorobenzyl. 
     
     
       11. The compound of claim 9 wherein R is ethyl or propyl, R 2  and R 3  are each methyl, R 4  is hydrogen and R 1  is p-trifluoromethylbenzyl. 
     
     
       12. The compound of claim 1 wherein R is alkyl and one of R 2  or R 3  is hydrogen and the other is alkylthioalkyl. 
     
     
       13. The compound of claim 12 wherein R 4  is hydrogen. 
     
     
       14. The compound of claim 13 wherein R 1  is haloalkenyl or p-halobenzyl and R is ethyl or propyl. 
     
     
       15. The compound of claim 14 wherein R 5  is hydrogen and R is propyl. 
     
     
       16. The compound of claim 1 wherein R is ethyl or propyl and one of R 2  or R 3  is hydrogen and the other is 2-ethylthiopropyl. 
     
     
       17. The compound of claim 16 wherein R is propyl, R 4  is hydrogen and R 1  is haloalkenyl or p-halobenzyl. 
     
     
       18. The compound of claim 17 wherein R 1  is 3-transchloroallyl or 4-chlorobenzyl. 
     
     
       19. The compound of claim 18 wherein R 1  is 3-transchloroallyl and R 5  is hydrogen. 
     
     
       20. The compound of claim 18 wherein R 1  is 4-chlorobenzyl and R 5  is hydrogen. 
     
     
       21. A herbicidal composition comprising a biologically inert carrier and a herbicidally effective amount of a compound of the formula defined in claim 1. 
     
     
       22. A method of killing vegetation which comprises applying to said vegetation or its growth environment a herbicidally effective amount of a compound of the formula defined in claim 1. 
     
     
       23. A method of killing crabgrass, watergrass or wild oats which comprises applying thereto or its growth environment a herbicidally effective amount of a compound of the formula defined in claim 1. 
     
     
       24. A method of killing watergrass which comprises applying thereto or its growth environment a herbicidally effective amount of a compound of the formula defined in claim 1. .Iadd. 
     
     
       25.  The compound of claim 3 wherein R 1  is 3-transchloroallyl or p-chlorobenzyl. .Iaddend. .Iadd.26. The compound of claim 25 wherein R 1  is 3-transchloroallyl. .Iaddend. .Iadd.27. The compound of claim 26 wherein R is alkyl having 1 to 3 carbon atoms. .Iaddend. .Iadd.28. The compound of claim 27 wherein one of R 2  or R 3  is hydrogen and the other is alkylthioalkyl. .Iaddend. .Iadd.29. The compound of claim 28 wherein R is ethyl or propyl. .Iaddend. .Iadd.30. The compound of claim 25 wherein R 1  is p-chlorobenzyl, R is alkyl having 1 to 3 carbon atoms and one of R 2  or R 3  is hydrogen and the other is alkylthioalkyl. .Iaddend. .Iadd.31. The compound of claim 30 wherein R is ethyl or propyl. .Iaddend. .Iadd.32. The compound of claim 16 wherein R is ethyl, R 4  is hydrogen and R 1  is haloalkenyl or p-halobenzyl. .Iaddend. .Iadd.33. The compound of claim 32 wherein R 1  is 3-transchloroallyl or 4-chlorobenzyl. .Iaddend. .Iadd.34. The compound of claim 33 wherein R 1  is 3-transchloroallyl and R 5  is hydrogen. .Iaddend. .Iadd.35. The compound of claim 33 wherein R 1  is 4-chlorobenzyl and R 5  is 
     
     
        hydrogen. .Iadd.36.  A compound having the formula ##STR47## wherein R is methyl, ethyl or propyl; R 1  is 3-transchloroallyl or 4-chlorobenzyl; R 2  and R 3  are each methyl or one of R 2  or R 3  is hydrogen and the other is 2-ethylthiopropyl; R 4  is 
     
     
        hydrogen and R 5  is hydrogen. .Iaddend. .Iadd.37.  The compound of claim 36 wherein one of R 2  or R 3  is hydrogen and the other is 2-ethylthiopropyl. .Iaddend. .Iadd.38. The compound of claim 37 wherein R 1  is 3-transchloroallyl. .Iaddend. .Iadd.39. The compound of claim 38 wherein R is ethyl or propyl. .Iaddend. .Iadd.40. The compound of claim 38 wherein R is methyl. .Iaddend. .Iadd.41. The compound of claim 37 wherein R 1  is 4-chlorobenzyl. .Iaddend. .Iadd.42. The compound of claim 41 wherein R is ethyl or propyl. .Iaddend. .Iadd.43. The compound of claim 41 wherein R is methyl. .Iaddend. .Iadd.44. A herbicidal composition comprising a carrier and a herbicidally effective amount of the compound 
     
     
        of claim 34. .Iaddend. .Iadd.45.  A method for killing grassy weeds which comprises applying a herbicidally effective amount of the compound of claim 34 to said grasses or their growth medium. .Iaddend. .Iadd.46. A herbicidal composition comprising a carrier and a herbicidally effective amount of the compound of claim 19. .Iaddend. .Iadd.47. A method for killing grassy weeds which comprises applying a herbicidally effective amount of the compound of claim 19 to said grasses or their growth medium. .Iaddend.