GB972008A - Halogenated methylthiohydantoins - Google Patents

Abstract

The invention comprises compounds of formula <FORM:0972008/C1/1> where R1 is H, or an alkyl, carboxylic acyl or nitro radical, and R2 and R3 are H, or substituted or unsubstituted alkyl, cycloalkyl, aralkyl, aryl, or heterocyclic radicals, or R2 and R3 together form a substituted or unsubstituted polymethylene bridge. Indicated substituents of R2 and R3 are alkyl, alkoxy, or alkoxycarbonyl radicals or halogen atoms. The compounds are made by reacting hydantoins of formula <FORM:0972008/C1/2> where R1, R2 and R3 have the same meaning as above, with fluorodichloromethane sulphenic acid chloride, preferably in an aqueous medium or an inert organic solvent such as benzene, dioxan, or chloroform, in the presence of an acid-binding agent. The compounds may also be prepared by reacting the corresponding 3-trichloromethylthiohydantoins with commercial anhydrous hydrofluoric acid. This reaction is generally carried out at atmospheric pressure at 0-20 DEG C. with excess hydrogen fluoride present as solvent. Organic solvents, e.g. nitrobenzene, diethylether, dioxan, and tetrahydrofuran may also be used. Examples are given in which R2 and R3 are H1 -CH3, and carboethoxy groups, and in which R2 is H, and R3 is a phenyl or hexyl group, and where R2 is carboethoxy and R3 is a methyl group. Examples also show compounds in which R2 and R3 together form a polymethylene bridge, e.g. where R2 and R3 together are hexyl or pentyl, the hexyl radical is also shown substituted by methyl groups. The compounds are useful as pesticides, especially fungicides (see Division A5).ALSO:New pesticidal, especially fungicidal, compositions, containing compounds of formula <FORM:0972008/A5-A6/1> where R1 is H, or an alkyl, carboxylic acyl, or nitro group, and R2 and R3 are H, or substituted or unsubstituted alkyl, cycloalkyl, aralkyl, aryl or heterocyclic residues, or together form a substituted or unsubstituted polymethylene bridge. The compounds are used in suitable solid or liquid extenders or diluents, as dusts, or aqueous suspensions, solutions or emulsions. Combination with other fungicides and/or insecticides is possible. The compositions may contain adhesives and non-ionic emulsifiers.