N-sulfenylated 2-amino-4-chloro-thiazole sulfon amides, their use, process for their production, and the 2,4-dichloro-thiazole sulfochloride and 2-amino-4-chloro-thiazole sulfon amide derivatives

摘要

The fungicidally active N-sulfenylated 2-amino-4-chlorothiazole-sulfonamides of the formula IMAGE in which R¹ and R² independently of one another are hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl or an aromatic or non-aromatic heterocyclic radical and R³ and R 4 independently of one another represent hydrogen, alkyl, cycloalkyl, aryl or aralkyl or for the dichloro-halomethyl-sulfenyl radical -S-CCl2X, in which X represents fluorine, chlorine or bromine, and furthermore one of the pairs of substituents R¹ and R³ or R² and R 4 together with the N atom which they substitute can mean morpholino or thiomorpholino, where at least one of the radicals R³ and R 4 represents the radical -S-CCl2X, can be prepared in that in a first stage 2,4-dichlorothiazole is reacted with chlorosulfonic acid to give 2,4-dichlorothiazole sulfonic acid chloride, in a second stage the 2,4-dichlorothiazole sulfonic acid chloride with primary amines or with a primary and a secondary amine to 2-amino-4-chloro-thiazole-sulfonamides and in a third step the sulfonamides mentioned with dichloro-halomethylsulfenyl chlorides to give the substances of formula (I).