Patent GB-771865-A (GB)
Title: Sulphite diesters and insecticides and herbicides containing í¡ í¡
IPC: C07C381/04
Filed: 1955-08-22
Abstract: The invention comprises sulphite diesters of the formula <FORM:0771865/IV(b)/1> in which R is an alkyl group of from 1 to 15 carbon atoms, n is 1 or 2, m is 2 or 3 and discrete carbon atoms of CmH2m are connected to the adjacent oxygen atoms, and R1 is an aryl or haloaryl radical of the benzene or naphthalene series. They are prepared by reacting the appropriate alcohols ROOCCnH2nOH and HOCmH2mOR1 with thionyl chloride in either order but preferably in the order given above, the second stage being advantageously carried out in the presence of a proton acceptor such as benzene, xylene or solvent naphtha.  The preparation of carbethoxymethyl chlorosulphinate from thionyl chloride and ethyl glycolate and of 1 - (carbobutoxy) ethyl chlorosulphinate from thionyl chloride and butyl lactate is described, and then the conversion of the first of these two intermediates into carbethoxymethyl 2-phenoxyethyl sulphite by reaction with 2-phenoxyethanol in the presence of pyridine and solvent naphtha with ice-water cooling.  The following sulphites are also referred to: carbethoxymethyl 2 - (p - tert - butylphenoxy) ethyl, carbethoxymethyl 2 - phenylisopropyl, carbethoxymethyl 2 - (p - tert - butylphenoxy) - iso - propyl, carbethoxymethyl 2 - (2 - naphthoxy) - isopropyl, 1 - (carbobutoxy) ethyl 2 - (p - tert - butylphenoxy) isopropyl, carbomethoxymethyl 2 - (2,4 - dichlorophenoxy) ethyl, carbethoxymethyl 2 - (2,4 - dichlorophenoxy) ethyl, 2-carbododecoxyethyl 2 - (2,4 - dichlorophenoxy) ethyl, carbethoxymethyl 2-(4-chlorophenoxy) ethyl, carbethoxymethyl 2-(2,4,5-trichlorophenoxy) ethyl, 1 - (carbobutoxy) ethyl 2-(4-chlorophenoxy) ethyl, 1 - (carbobutoxy) ethyl 2 - (2,4 - dichlorophenoxy) ethyl and carbeth - oxymethyl 2 - (2,4 - dichlorophenoxy) isopropyl sulphites.  A further list of compounds according to the invention, which includes bromo and fluoro substituted benzene derivatives, is also given.ALSO:A plant growth regulant comprises a compound of the formula: <FORM:0771865/I/1> in which R is an alkyl group having 1 to 15 carbon atoms, n is 1 or 2, m is 2 or 3 and discrete carbon atoms of CmH2m are connected to the adjacent oxygen atoms, and R1 is a haloaryl radical of the benzene or naphthalene series, together with powdered solid carriers such as mineral silicates e.g. mica, talc, pyrophillite and clays or together with surface-active dispersing agents, or with both a carrier and a dispersing agent.ALSO:An insecticide, and, when the active constituent contains halogen atoms, a herbicide, comprises a compound of the formula <FORM:0771865/VI/1> in which R is an alkyl group having 1 to 15 carbon atoms, n is 1 or 2, m is 2 or 3 and discrete carbon atoms of CmH2m are connected to the adjacent oxygen atoms, and R1 is an aryl or halo aryl radical of the benzene or naphthalene series, together with powdered solid carriers such as mineral silicates e.g. mica, talc, pyrophillite and clays or together with surface-active dispersing agents, or with both a carrier and a dispersing agent.  Examples describe the use of (1) aqueous emulsions prepared by dissolving in a sulphite of the invention the reaction product of castor oil and ethylene oxide and then adding water, and (2) mixtures of the sulphites of the invention with the condensation product of ethylene oxide and an alylated phenol dispersed in water.