Haloaryloxyalkyl esters of -a, -a, -ß-trichloropropionic acid

摘要

The invention comprises an a ,a ,b -trichloropropionate of a (haloaryl)-oxy alkanol, the alkylene chain of said alkanol containing from 2 to 4 carbon atoms inclusive. Such esters are prepared by the reaction of a ,a ,b -trichloropropionic acid with a (haloaryl)-oxyalkanol, the alkylene chain of said alkanol containing from 2 to 4 carbon atoms, preferably in the presence of an acid catalyst such as sulphuric acid, a phenol-sulphonic acid or a cation exchange resin in the acid form and conveniently in a waterimmiscible solvent such as ethylene dichloride or toluene. Water may be removed azeotropically during the reaction and the solvent separated and recycled. The catalyst may be added during the reaction. Examples relate to the production of 2-(2,4,5-trichlorophenoxy)-ethyl-; 2-(2,4,5-trichlorophenoxy) - 1 - propyl-; 1 - (2,4,5 - trichlorophenoxy) - 2 - propyl-; 2-(3,4 - dichlorophenoxy) - ethyl -; 2 - (3,4 - dichlorophenoxy) - 1 - propyl -; 1 - (3,4 - dichlorophenoxy) - 2 - propyl -; 2 - (2,4 - dibromophenoxy)-ethyl- and 2-(4-chloro-2-methylphenoxy)-ethyl a ,a ,b - trichloropropionates. Other products stated to be prepared similarly are 2-(2,4-dichlorophenoxy) - ethyl -; 1 - (2,4 - dichlorophenoxy) - 2 - propyl -; 3 - (4 - chlorophenoxy) - 1 - propyl -; 2 - (4 - bromophenoxy) - ethyl -; 1 - (4 - bromophenoxy) - 2 - propyl -; 1 - (pentachlorophenoxy) - 2 - propyl -; 2 - (2 - bromo - 4 - chlorophenoxy) - ethyl - and 3 - (2,4 - dichlorophenoxy) - 1 - butyl a ,a ,b - trichloropropionates. The products are employed in herbicidal, insecticidal and bactericidal compositions (see Group VI). Haloaryloxyalkanols employed as starting materials are prepared by reacting an alkali metal salt of an appropriate phenol with a monohaloaliphatic alcohol such as ethylene chlorohydrin, propylene chlorohydrin, 2-chloro-1-propanol, 3 - bromo - 1 - propanol, 3 - chloro - 1 - propanol, 3 - chloro - 2 - butanol and 3 - chloro-1-butanol.ALSO:Herbicidal, insecticidal and bactericidal compositions comprise as active ingredient an a ,a ,b -trichloropropionate of a (haloaryl) oxyalkanol, the alkylene chain of which contains from 2 to 4 carbon atoms (see Group IV (b). The active ingredients may be dispersed in finely-divided solids, in water or in oil-in-water emulsions with or without wetting, dispersing or emulsifying agents. Active ingredients specified include 2 - (2,4,5 - trichlorophenoxy) - ethyl -, 1 - (3,4-dichlorophenoxy) - 2 - propyl -, 2 - (2,4 - dibromo - phenoxy) - ethyl - and 2 - (4 - chloro - 2 - methyl phenoxy) - ethyl a ,a ,b - trichloropropionates.