N-SULFENYLATED 2-AMINO-4-CHLORINE-THIAZOLE-SULFONAMIDES, THEIR USE, METHOD FOR THE PRODUCTION THEREOF AND THE INTERMEDIATES PRODUCED THEREOF 2,4-DICHLOR-THIAZOLE-SULPHONE ACID CHLORIDE SOURLORIDE

摘要

The fungicidally active N-sulphenylated 2-amino-4-chloro-thiazole-sulphonamides of the formula IMAGE (I) wherein R1 and R2 independently of one another denote hydrogen, alkyl, alkenyl, alkinyl, cycloalkyl, aryl, aralkyl or an aromatic or a non-aromatic heterocyclic radical and R3 and R4 independently of one another stand for hydrogen, alkyl, cycloalkyl, aryl or aralkyl or for the dichlorohalogenomethyl-sulphenyl radical -S-CCl2X, in which X denotes fluorine, chlorine or bromine, and where furthermore one of the pairs of substituents R1 and R3 or R2 and R4 together with the nitrogen atom which they substitute can denote morpholino or thiomorpholino, with at least one of the radicals R3 and R4 standing for the radical -S-CCl2X, can be prepared in a process in which, in a first step, 2,4-dichloro-thiazole is reacted with chlorosulphonic acid to give 2,4-dichloro-thiazole-sulphonyl chloride, in which, in a second step, the 2,4-dichloro-thiazole-sulphonyl chloride is reacted with primary amines or with a primary and a secondary amine to give 2-amino-4-chloro-thiazole-sulphonamides, and in which, in a third step, the sulphonamides mentioned are reacted with dichlorohalogenomethylsulphenyl chlorides to give the substances of the formula (I).