Patent GB-1038184-A (GB)
Title: New n-monoalkoxy amides of substituted phenoxy alkanoic acids, herbicidal compositions and process for preparing said amides
IPC: C07C51/60
Filed: 1963-11-07
Abstract: The invention relates to compounds of the general formula <FORM:1038184/C2/1> wherein A is hydrogen, chlorine, or unsubstituted lower alkyl group; E is hydrogen or chlorine; D is a halogen atom, provided that when A is chlorine or alkyl groups, D is chlorine, and when E is chlorine, A and D are both chlorine; X is hydrogen or alkyl group; Y is an alkyl group; and Z is an unsubstituted alkylene group containing from one to four carbon atoms.  Compounds claimed per se are N - methoxy 2 - methyl - 4 - chlorophenoxy-acetamide. N - methoxy - N - methyl 2-methyl - 4 - chlorophenoxyacetamide. N-methoxy 2,4 - dichlorophenoxyacetamide. N - methoxy - N - methyl 2,4 - dichlorophenoxyacetamide. N - methoxy 2,4,5 - trichlorophenoxyacetamide. N - methoxy - N - methyl 2,4,5 - trichlorophenoxyacetamide.  N - methoxy 4 - chloroacetamide.  N - methoxy 4-bromoacetamide. N - methoxy - N - methyl 4-chloroacetamide. N - methoxy - N - methyl 4-bromoacetamide. a  - (N - methoxy - N - methyl 2 - methyl 4 - chlorophenoxy) propionamide. N - ethoxy 2 - methyl - 4 - chlorophenoxyacetamide. N - ethoxy - N - methyl 2 - methyl - 4-chlorophenoxyacetamide. N - ethoxy 2,4 - di-chlorophenoxyacetamide. N - ethoxy - N-methyl 2,4 - dichlorophenoxyacetamide.  N-ethoxy 2,4,5 - trichlorophenoxyacetamide.  N-ethoxy - N - methyl 2,4,5 - trichlorophenoxyacetamide. N - ethoxy - N - methyl 4 - chlorophenoxyacetamide. The compounds may be prepared by reacting a compound of the formula <FORM:1038184/C2/2> where R is a halogen atom with an amine of the formula <FORM:1038184/C2/3> where X is hydrogen or alkyl group and Y is an alkyl group.  In an example N-methoxy-N-methyl - 2 - methyl 4 - chlorophenoxy acetamide is prepared by refluxing N-methoxy-N-methyl amine hydrochloride with 2-methyl-4-chlorophenoxy acetyl chloride.  Many other examples are given.ALSO:Herbicidal compositions comprises active ingredient the compounds of the general formula <FORM:1038184/A5-A6/1> wherein A is hydrogen, chlorine, or unsubstituted lower alkyl groups; E is hydrogen or chlorine; D is a halogen atom, provided that when A is chlorine or an alkyl group, D is chlorine, and when E is chlorine, A and D are both chlorine; X is hydrogen or an alkyl group; Y is an alkyl group; and Z is an unsubstituted alkylene group containing from one to four carbon atoms, together with an inert solid or liquid carrier.  Emulsifying agents, other pesticides, spreaders, adhesives, stickers, fertilizers, activators, synergists may also be incorporated.  Specified active ingredients are N-methoxy 2-methyl-4-chlorophenoxyacetamide. N-methoxy-N-methyl 2-methyl-4-chlorophenoxyacetamide.  N-methoxy 2, 4-dichlorophenoxyacetamide.  N-methoxy-N-methyl 2, 4-dichlorophenoxyacetamide.  N-methoxy 2, 4, 5-trichlorophenoxyacetamide.  N-methoxy-N-methyl 2, 4, 5-trichlorophenoxyacetamide.  N-methoxy 4-chloroacetamide. N-methoxy 4-bromoacetamide.  N-methoxy-N-methyl 4-chloroacetamide. N-methoxy-N-methyl 4-bromoacetamide.  a -(N-methoxy-N-methyl 2-methyl 4-chlorophenoxy) propionamide.  N-ethoxy 2-methyl-4-chlorophenoxyacetamide.  N-ethoxy-N-methyl 2-methyl-4-chlorophenoxyacetamide.  N-ethoxy 2, 4-dichlorophenoxyacetamide.  N-ethoxy-N-methyl 2, 4-dichlorophenoxyacetamide.  N-ethoxy 2, 4, 5-trichlorophenoxyacetamide.  N-ethoxy-N-methyl 2, 4, 5-trichlorophenoxyacetamide.  N-ethoxy-N-methyl 4-chlorophenoxyacetamide.  Many carriers are specified.