Patent GB-979132-A (GB)
Title: Imines
Inventor: LAWS GEORGE FREDERICK
Filed: 1960-02-13
Abstract: The invention comprises imines of the general formula <FORM:0979132/C1/1> wherein R1 and R2 are hydrogen or chlorine and R3 is a hydrocarbon radical i.e. an alkyl, aryl or aralkyl radical substituted or unsubstituted, and salts and functional derivatives thereof. Specified radicals are R1 chlorine, R2 hydrogen, R3 methyl, ethyl, isopropyl, normal butyl, stearyl, benzyl, phenyl, metachlorophenyl, 2:3:6-trichlorobenzyl, beta-hydroxyethyl and carboethoxymethyl. The compounds are produced by reacting together an amine of the formula NH2R3 with an aldehyde of the formula <FORM:0979132/C1/2> wherein R1 and R2 are hydrogen or chlorine and R3 is a hydrocarbon radical substituted or unsubstituted. The compounds are used as active ingredients in herbicidal compositions. Specified compounds are N-(normal-butyl)-2:3:6-trichlorobenzaldimine, N - (stearyl) - 2:3:6 - trichlorobenzaldimine, N-(phenyl)2:3:6-trichlorobenzaldimine and N-(meta-chlorophenyl) - 2:3:6-trichlorobenzaldimine, N-(2:3:6-trichloro-benzyl) -2:3:6-trichlorobenzaldimine N-ethyl-2:3:6-trichlorobenzaldimine, N-isopropyl-2:3:6-trichlorobenzaldimine, N - methyl - 2:3:6-trichlorobenzaldimine, N-(beta-hydroxyethyl)-2:3:6-trichlorobenzaldimine, N-(carboethoxymethyl)-2:3:6-trichlorobenzaldimine, respectively produced by reacting 2:3:6-trichlorobenzaldehyde with N-butylamine, stearylamine, aniline, m-chloroaniline, 2:3:6-trichlorobenzylamine, ethyl amine, isopropyl amine, methyl amine, ethanol amine, glycine ethyl ester.ALSO:Herbicidal compositions compise as active ingredient an imine of the general formula <FORM:0979132/A5-A6/1> wherein R1 and R2 are hydrogen or chlorine and R3 is a hydrocarbon radical, i.e. an alkyl aryl or aralkyl radical substituted or unsubstituted, and salts and functional derivatives thereof.  The active ingredients may be: (a) dissolved in a water-immiscible solvent, such as for example a high boiling aromatic hydrocarbon containing dissolved emulsifying agents so as to act as a self-emulsifiable oil in addition to water, (b) dissolved in an organic solvent, such for example methyl cellosolve or propanol, and the resulting solution used as such or dispersed in water with or without a wetting agent, (c) admixed with a wetting agent or a non-solvent diluent to be used as such or to form a product which is dispersible in water, (d) mixed with a wetting agent, with or without the incorporation of powdered or divided solid materials, so that a wettable product is obtained which is capable of use as such or as a suspension or dispersion in water, (e) incorporated with solid inert media comprising powdered or divided solid materials, for example clays, sands, talc, mica, fertilizers and the like, such products either comprising dust or larger particle size materials, (f) used in the form of aqueous solutions of the water-soluble salts, e.g. halide and nitrate with or without wetting or dispersing agents, organic solvents, stichers and the like.  There may also be included in the composition other herbicides, e.g. 2 - methyl - 4 - chlorophenoxyacetic acid, 2 : 4 - dichlorophenoxyacetic acid, para-chlorphenyl dimethyl urea. Specified active ingredients are N-(normal-butyl)-2 : 3 : 6-trichlorobenzaldimine, N-(stearyl) - 2 : 3 : 6 - trichlorobenzaldimine, N - (phenyl) - 2 : 3 : 6 - trichlorobenzaldimine and N - (meta - chlorophenyl)-2 : 3 : 6 - trichlorobenzaldimine, N - (2 : 3 : 6-trichlorobenzyl) - 2 : 3 : 6 - trichlorobenzaldimine, N - ethyl - 2 : 3 : 6 - trichlorobenzaldimine, N - isopropyl - 2 : 3 : 6 - trichlorobenzaldimine, N - methyl - 2 : 3 : 6 - trichlorobenzaldimine, N - (beta - hydroxyethyl) - 2 : 3 : 6-trichlorobenzladimine, N - (carboethoxymethyl)-2 : 3 : 6-trichlorobenzaldimine.