N-sulphenylated 2-amino-4-chloro-thiazole-sulphonamides, their use, process for their preparation, and the intermediates 2,4-dichlorothiazole-sulphonyl chloride and 2-amino-4-chloro-thiazole-sulphonamides

US4906650A · kind A · utility

Assignee

• BAYER HEALTHCARE LLC · DE

Inventors

• Gunther Beck · Leverkusen, DE
• Bernd Baasner · Bensberg, DE
• Michael Schwamborn · Cologne, DE
• Wilhelm Brandes · Leichlingen, DE

Key dates

• Filing date: Feb 8, 1989
• Grant date: Mar 6, 1990
• Expiry date: Feb 8, 2009

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D277/52
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The fungicidally active N-sulphenylated 2-amino-4-chloro-thiazole-sulphonamides of the formula ##STR1## wherein R.sup.1 and R.sup.2 independently of one another denote hydrogen, alkyl, alkenyl, alkinyl, cycloalkyl, aryl, aralkyl or an aromatic or a non-aromatic heterocyclic radical and PA0 R.sup.3 and R.sup.4 independently of one another stand for hydrogen, alkyl, cycloalkyl, aryl or aralkyl or for the dichlorohalogenomethyl-sulphenyl radical --S--CCl.sub.2 X, in which X denotes fluorine, chlorine or bromine, and where furthermore one of the pairs of substituents R.sup.1 and R.sup.3 or R.sup.2 and PA0 R.sup.4 together with the nitrogen atom which they substitute can denote morpholino or thiomorpholino, with at least one of the radicals R.sup.3 and R.sup.4 standing for the radical --S--CCl.sub.2 X, 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, th…