Substituted phenoxybenzoic acids and derivatives thereof

Abstract

Metal salts and amine salts of 2-nitro-5-(halophenoxy)benzoic acids comprise a class of compounds that are highly effective pre- and post-emergence herbicides.

What is claimed is: 
     
       1. The method for controlling plant growth that comprises applying an herbicidal amount of an herbicidal compound having the formula: ##STR2## wherein X is halogen, n is 1 to 5, and M is alkali metal (Li, Na, K), .[.alkaline earth metal, a transition metal, ammonium, alkylammonium (C 1  -C 30 ), alkanolammonium (C 1  -C 3 ), alkyl (C 1  -C 30 ) dialkanol (C 2  -C 3 ) ammonium, dioxyalkylene (C 2  -C 3 ) alkyl (C 1  -C 30 )ammonium, dialkylammonium (C 1  -C 30 ), trialkylammonium (C 1  -C 30 ), alkoxyalkylammonium (C 2  -C 6 ) dialkoxyalkylammonium (C 3  -C 6 ), aminoalkylammonium (C 1  -C 30 ), dialkylaminoalkylammonium (C 3  -C 8 ), alkenylammonium (C 2  -C 22 ), alkyl (C 1  -C 30  aminoalkyl (C 2  -C 6 ) ammonium, alkenyl (C 2  -C 30 ) aminoalkyl (C 2  -C 6 ) ammonium, alkynyl (C 3  -C 12 ) ammonium dialkenylammonium (C 4  -C 12 ), cycloalkylammonium (C 3  -C 6 ), alkyl (C 1  -C 30 ) ammonium alkyl (C 2  -C 6 ) ammonium, benzylammonium, anilinium, substituted anilinium, guanidinium or heterocyclicammonium (C.sub. 4 -C 6 )..]. .Iadd.alkylammonium (C 1  -C 4 ), or alkanolammonium (C 1  -C 3 ). .Iaddend. .[. 
     
     
       2.  The method of claim 1, wherein said compound is butylammonium 2-nitro-5-(2',4'-dichlorophenoxy)benzoate..]. .[.3. The method of claim 1, wherein said compound is methoxypropylammonium 2-nitro-5-(2',4'-dichlorophenoxy) benzoate..]. .[.4. The method of claim 1, wherein said compound is cyclohexylammonium 2-nitro-5-(2',4'-dichlorophenoxy) benzoate..]. .[.5. The method of claim 1, wherein said compound is 2,2-dimethoxyethylammonium 2-nitro-5-(2',4'-dichlorophenoxy)benzoate..]. .[.6. The method of claim 1, wherein said compound is allylammonium 2-nitro-5-(2',4'-dichlorophenoxy)benzoate..]. .[.7. The method of claim 1, wherein said compound is arachidyl (90%) behenyl (10%) aminopropylammonium 2-nitro-5-(2',4'-dichlorophenoxy)benzoate..]. .[.8. The method of claim 1, wherein said compound is potassium 
     
     
        2-nitro-5-(2',4'-dichlorophenoxy)benzoate..]. 9. The method of claim 1, wherein said compund is ethanolammonium 
     
     
        2-nitro-5-(2',4',6'-trichlorophenoxy)benzoate. 10. The method of claim 1, wherein said compound is sodium 
     
     
        2-nitro-5-(2',4',6'-trichlorophenoxy)benzoate. 11. An herbicidal composition comprising a carrier for an herbicide and an herbicidal amount of an herbicidal compound having the formula: ##STR3## wherein X is halogen, n is 1 to 5, and M is alkali metal (Li, Na, K), .[.alkaline earth metal, a transition metal, ammonium, alkylammonium (C 1  4 -C 30 ), alkanolammonium (C 1  -C 3 ), alkyl (C 1  -C 30 ), dialkanol (C 2  -C 3 ) ammonium, dioxyalkylene (C 2  -C 3 ) alkyl (C 1  -C 30 )ammonium, dialkylammonium (C 1  -C 30 ), trialkylammonium (C 1  -C 30 ), alkoxyalkylammonium (C 2  -C 6 ) dialkoxyalkylammonium (C 3  -C 6 ), aminoalkylammonium (C 1  -C 30 ), dialkylaminoalkylammonium (C 3  -C 8 ), alkenylammonium (C 2  -C 22 ), alkyl (C 1  -C 30 ) aminoalkyl (C 2  -C 6 ) ammonium, alkenyl (C 2  -C 30 ) aminoalkyl (C 2  -C 6 ) ammonium, alkynyl (C 3  -C 12 )ammonium, dialkenylammonium (C 4  -C 12 ), cycloalkylammonium (C 3  -C 6 ), alkyl (C 1  -C 30 ) ammonium alkyl (C 2  -C 6 ) ammonium, benzylammonium, anilinium, substituted anilinium, guanidinium or heterocyclicammonium (C 4  -C 6 )..]. .Iadd.alkylammonium (C 1  -C 4 ), or alkanolammonium (C 1   
     
     
        -C 3 ). .Iaddend. .[.12.  The composition of claim 11, wherein said compound is butylammonium 2-nitro-5-(2',4'-dichlorophenoxy)benzoate..]. .[.13. The composition of claim 11, wherein said compound is methoxypropylammonium 2-nitro-5-(2',4'-dichlorophenoxy)benzoate..]. .[.14. The composition of claim 11, wherein said compound is cyclohexylammonium 2-nitro-5-(2',4'-dichlorophenoxy)benzoate.]. .[.15. The composition of claim 11, wherein said compound is 2,2-dimethoxyethylammonium 2-nitro-5-(2',4'-dichlorophenoxy)benzoate..]. .[.16. The composition of claim 11, wherein said compound is allylammonium 2-nitro-5-(2',4'-dichlorophenoxy)benzoate..]. .[.17. The composition of claim 11, wherein said compound is arachidyl (90% ) behenyl (10%) aminopropylammonium 2-nitro-5-(2',4'-dichlorophenoxy benzoate..]. .[.18. The composition of claim 11, wherein said compound is potassium 
     
     
        2-nitro-5-(2',4'-dichlorophenoxy)benzoate..]. 19. The composition of claim 11, wherein said compound is ethanolammonium 
     
     
        2-nitro-5-(2',4',6'-trichlorophenoxy)benzoate. 20. The composition of claim 11, wherein said compound is sodium 2-nitro-5-(2',4',6'-trichlorophenoxy)benzoate.