Patent GB-1021014-A (GB)
Title: Novel herbicidal compounds and compositions
Inventor: YATES JOHN
IPC: C07C57/60
Filed: 1963-07-19
Abstract: The invention relates to compounds of the general formula <FORM:1021014/C2/1> wherein Y represents a chlorine or bromine atom and R represents an alkyl or alkenyl group of 1-10 carbon atoms, n is 1-5, and Z is a CN group, a CONHR1 or CONR1R2 group wherein R1 and R2 is an alkyl group of 1-10 C atoms, or a COOR3 group wherein R3 represents a hydrogen atom, an alkali metal, an ammonium or a substituted ammonium group, or an alkyl group of 1-10 carbon atoms; excluding the compounds 2 - (2 - chlorophenyl) - propionitrile, 2 - (4 - chlorophenylpropionic acid), 2 - (2,4-dichlorophenyl) -propionic acid, and 2 - (3,4-dichlorophenyl)-propionic acid.  Illustrative of many compounds claimed per se are 2-(4-bromophenyl) - N,N - dimethylpropionamide, 2 - (2,4 - dichlorophenyl) - N,N - dimethylbutyramide, 2 - (2,3,6 - trichlorophenyl) - N,N-dimethylpropionamide, 2 - (4 - chlorophenyl) propionitrile, 2 - (2,4 - dichlorophenyl) pentanonitrile, 2 - (2,4 - dichlorophenyl) - 4 - pentenonitrile, 2 - (2,3 - dichlorophenyl) propionic acid, 2 - (2,4 - dichlorophenyl) pentanoic acid, 2 - (2,4 - dichlorophenyl) - 4 - pentenoic acid. The amides are prepared by reacting an acid chloride of the general formula <FORM:1021014/C2/2> where Y R and n are as indicated above with an amine of the general formula HNR1R2 or HNR1H wherein R1 and R2 are as indicated above, under anhydrous or substantially anhydrous conditions. The nitriles are prepared by reacting in an inert solvent a halogen substituted phenyl acetonitrile having the general formula <FORM:1021014/C2/3> wherein Y and n are as indicated above, with an alkyl halide or an alkenyl halide having the formula RX, wherein R is as indicated above and X is a halogen atom, in the presence of a basic alkylation catalyst e.g. sodium amide or sodium hydride.  The acids are prepared by hydrolysing a nitrile having the general formula <FORM:1021014/C2/4> wherein R Y and n are as indicated above. Many examples are given.ALSO:Herbicidal compositions comprise active ingredient one or more compounds having the formula <FORM:1021014/A5-A6/1> wherein Y represents a chlorine or bromine atom and R represents an alkyl or alkenyl group of 1-10 carbon atoms, n is 1-5, and Z represents a CN group, a CONHR1 or CONR1R2 group where R1 and R2 represent an alkyl group of 1-10 carbon atoms, or a COOR3 group wherein R3 represents a hydrogen atom, an alkali metal, an ammonium or a substituted ammonium group, or an alkyl group of 1-10 carbon atoms; together with a carrier and/or surface active agent.  Many solid and liquid carriers are specified.  The composition may contain other ingredients e.g. conditioning agents such as sodium polyphosphate, cellulose ethers or ethylene diamine tetra acetic acid other herbicides pesticides or stickers wetting and emulsifying agents. Many active ingredients are specified among them 2-(4-Bromophenyl)-N, N-dimethylpropionamide, 2-(2, 4-Dichlorophenyl)-N, N-dimethylbutyramide, 2-(2, 3, 6-Trichlorophenyl)-N, N-dimethylpropionamide, 2-(4-Chlorophenyl) propionitrile, 2-(2, 4-Dichlorophenyl) pentanonitrile, 2-(2, 4-Dichlorophenyl)-4-pentenonitrile, 2-(2, 3-Dichlorophenyl) propionic acid, 2-(2, 4-Dichlorophenyl) pentanoic acid, 2-(2, 4-Dichlorophenyl)-4-pentenoic acid.