GB979399A - Bis-(polychlorovinyl) sulphides - Google Patents

Abstract

The invention comprises bis-(polychlorovinyl) sulphides of the general formula <FORM:0979399/C1/1> wherein at least 4 X's are chlorine atoms and the remainder are hydrogen atoms or dichloromethyl or trichloromethyl radicals. The compounds are prepared by the reaction of sulphur dichloride or the appropriate polychloroalkyl-or polychlorovinyl-sulphenyl chlorides with polychloroolefines, which contain at least two chlorine atoms and at least one hydrogen at the double bond, in the presence of a Friedel-Crafts catalyst to give the bis (polychloroalkyl)- or polychloroalkyl-polychlorovinyl-sulphides which are subsequently dehydrohalogenated. The addition of sulphur dichloride to the chlorinated olefines is preferably carried out using AlCl3, e.g. 0.05 moles based on SCl2, as the catalyst; the preferred reactant ratio is 2 moles olefine to 1 mole SCl2 and suitable temperatures lie in the range 0-40 DEG C. The reaction using sulphenyl chlorides may be effected under similar conditions using 1 mole appropriate sulphenyl chloride per mole chloroolefine; this latter reaction permits the preparation of asymmetrical compounds of the above formula, e.g., 1, 2, 2, 2-tetrachloro-11, 21, 21-trichloro-ethyl sulphide, 1,2,2,21, 21, 21-hexachlorodiethyl sulphide. Suitable polychloroolefine starting materials are, e.g. 1,1- or 1,2-dichloroethylene, trichloroethylene, 1,2,3,3- or 1,1,3,3-tetrachloropropyl-1-ene or 1, 2, 3, 3, 3-pentachloropropylene. Hydrogen chloride is eliminated from the bis (polychloroalkyl)- or polychloroalkyl-polychlorovinyl-sulphides with the aid of known reagents, e.g., metal oxides, hydroxides or alcoholates or salts of weak acids, e.g., carbonates or acetates, or ammonia or amines. Dehydrohalogenation may be carried out at room temperatures or above. The compounds of the invention are used as nematocides (see Division A5). Examples describe the preparation of bis (1, 2-dichlorovinyl) sulphide and bis-(1, 2, 2-trichlorovinyl) sulphide. Specification 954,440 is referred to.ALSO:Nematocidal compositions comprise bis-(polychlorovinyl) sulphides of the general formula <FORM:0979399/A5-A6/1> wherein at least 4 X's are chlorine and the remainder are hydrogen atoms or dichloromethyl or trichloromethyl radicals, and a solid or liquid diluent or carrier.