Patent GB-955946-A (GB)
Title: N-polyhaloethylthio compounds and their use as fungicidal compositions
IPC: C07D233/72
Filed: 1962-01-15
Abstract: The invention relates to compounds containing the grouping: <FORM:0955946/C2/1> where Y is chlorine or bromine, X is hydrogen, chlorine or bromine, at least two X's being chlorine or bromine, and the nitrogen atom is linked to at least one amide group, which may be a carboxyamide, thioamide, sulfonamide or sulphinamide group. When the nitrogen atom is linked to only one amide group, the other valency may be satisfied by hydrogen, as in butyramide, benzamide, nicotinamide, methane-sulphonamide, butanesulphonamide, benzene-sulphonamide, naphthalene-sulphonamide, or diethylaminosulphonamide, or by an alkyl, aryl, alicyclic or heterocyclic group such as a methyl, ethyl, pentyl, phenyl, tolyl, chlorophenyl, naphthyl, furyl, thionyl or pyridyl group.  When the nitrogen atom is linked to two amide groups, the products may be either of the formulae: <FORM:0955946/C2/2> where Y and X are as above, Z is -CO-, -CS-, -SO- or -SO2-, R and R1 may be aliphatic, alicyclic, aromatic or heterocyclic radicals and R11 may be an aliphatic radical; derivatives of hydantoin and of oxazolidine-2, 4-dione are mentioned in this connection. The products may be prepared by reacting an appropriate polyhalo-ethyl sulphonyl chloride or bromide with the corresponding amide or imide or its metal salt. In the examples, (1) succinimide is treated with sodium hydroxide in aqueous solution and a solution of 1,1,2,2-tetrachloroethyl sulphenyl chloride in hexane is added, yielding N-(1,1,2,2-tetrachloroethylthio) succinimide; the corresponding 1,2,2- and 1,1,2-trichloro compounds, the 1,2,2,2-tetrachloro compound and the pentachloro compound are similarly obtainable, as also are N-(1,1,2,2-tetrachloroethylthio) diglycolimide, N-(1, 1, 2, 2-tetrachloroethylthio) glutarimide, N-(1, 1, 2, 2-tetrachloroethylthio) maleimide and N-(1,1,2,2-tetrachloroethylthio) 2,3-dibromosuccinimide; (2) 5,5-dimethylhydantoin is treated in sodium hydroxide solution with 1, 2, 2, 2-tetrachloroethyl sulphenyl chloride to yield 3-(1, 2, 2, 2-tetrachloroethylthio)-5, 5-dimethylhydantoin; the corresponding 1, 1, 2, 2-tetrachloro, 2-chloro-1, 2, 2-tribromo, 2-bromo-1, 2, 2-trichloro and pentachloro compounds are similarly obtainable, as also are 3-(1, 2, 2-tri-chloroethylthio) hydantoin and the corresponding 1, 1, 2, 2-tetrachloro and 2-bromo-1, 1, 2-trichloro compounds and 3-(1, 1, 2, 2-tetrachloroethylthio) -5- (1-ethylamyl) hydantoin, 3-(1, 1, 2, 2-tetrachloroethylthio)-5, 5-(21, 21, 41-trimethylpentamethylene) hydantoin and methyl 2,4-dioxo -N- (1, 1, 2, 2-tetrachloroethylthio)-thiazolidyl-5 acetate; (3) N-(4-chlorophenyl) ethane sulphonamide is treated in sodium hydroxide solution with 1, 1, 2, 2-tetrachloroethyl sulphonyl chloride to yield N-(4-chlorophenyl)-N-(1, 1, 2, 2-tetrachloroethylthio)ethane sulphonamide; N-methyl -N- (1, 2, 2-trichlorovinylthio) -4- chlorobenzene sulphonamide, N-phenyl -N- (1, 2, 2-trichlorovinylthio)-dimethylamino-sulphonamide, N-ethyl -N- (1, 2, 2, 2-tetrachloroethylthio)benzene sulphonamide, N-methyl -N- (1, 2, 2, 2-tetrachloroethylthio) -4-chlorobenzene sulphonamide, N-phenyl -N-(1, 2, 2, 2-tetrachloroethylthio)-dimethylamino-sulphonamide, N-methyl -N- (1, 1, 2, 2-tetrachloroethylthio) -4- chlorobenzene sulphonamide, N-(2-bromo-1, 2, 2-trichloroethylthio) -N- methyl -4- chlorobenzene sulphonamide, N-(1, 2-dibromo-1, 2-dichloroethylthio) -N-methyl -4- chlorobenzene sulphonamide, N-methyl -N- pentachloroethylthio -4- chlorobenzene sulphonamide and N-allyl -N- (1, 1, 2, 2-tetrachloroethylthio)benzene sulphonamide are similarly obtainable. The products are useful as fungicides. Specification 930,224 is referred to.ALSO:As fungicides, use is made of compounds containing the grouping <FORM:0955946/A5-A6/1> where Y is chlorine or bromine, X is hydrogen' chlorine or bromine, at least two X's being chlorine or bromine, and the nitrogen atom is linked to at least one amide group, which may be a carboxyamide, thioamide, sulfonamide or sulphinamide group (see Division C2).  When the nitrogen atom is linked to only one amide group, the other valency may be satisfied by hydrogen, as in butyramide, benzamide, nicotinamide, methanesulphonamide, butanesulphonamide, benzenesulphonamide, naphthalenesulphonamide, or diethylaminosulphonamide, or by an alkyl, aryl, alicyclic or heterocyclic group such as a methyl, ethyl, pentyl, phenyl, tolyl, chlorophenyl, naphthyl, furyl, thienyl or pyridyl group.  When the nitrogen atom is linked to two amide groups, the products may be of either of the formul  <FORM:0955946/A5-A6/2> where Y and X are as above, Z is -CO-, -CS-, -SO- or -SO2-, R and R1 may be aliphatic, alicyclic, aromatic or heterocyclic radicals and R11 may be an aliphatic radical; derivatives of hydantoin and of oxazolidine-2,4-dione are mentioned in this connection.  The compounds may be used in association with solid carriers or liquid media and applied to plants or seeds or sprayed upon the soil. Experimental results of the use of some of the products are given. Additives for fungicidal compositions include known toxicants, solvents, emulsifying agents and dispersing agents.  Specified forms are dusts and wettable powders.  Specification 930,224 is referred to.