benzothiadiazoles biologically active, their processes of preparation, products containing these compounds as active ingredients, and their application in agriculture and horticulture

摘要

1303711 Benzothiadiazoles PHILIPS GLOEILAMPENFABRIEKEN NV 16 Feb 1970 [19 Feb 1969] 7314/70 Heading C2C [Also in Divisions A5 and Cl] Compounds of formula wherein X is the group -OCHR 1 COOR, in which R 1 is hydrogen or C 1-3 alkyl and R is hydrogen or C 1-10 alkyl, Y is chlorine or bromine, n is 0, 1, 2 or 3 and Z is hydrogen or C 1-3 -alkyl, are prepared by (a) etherification, (b) halogenation or (c) ester hydrolysis. The products have herbicidal, pesticidal and plant growth regulant activity (see Division A5). 6 - Hydroxy - benzothiadiazole starting materials are prepared by hydrolysis of their methyl ethers. 6 - Methoxy - benzothiadiazoles are prepared by (a) replacement of a chlorine atom by reaction with sodium methoxide, (b) chlorination or (c) reduction of an o-dinitro-benzene or an onitro-aniline to the corresponding diamine, followed by cyclization with thionyl chloride. 2 - Chloro - 4 - methoxy - 6 - nitro - aniline is prepared by reaction of 2-chloro-6-nitro-phenyl azide with sulphuric acid to give 2-chloro-4- hydroxy - 6 - nitro - aniline, followed by methylation. 2,3,5 - Trichloro - 6 - nitro - aniline is prepared by nitration of 2,3,5-trichloro-acetanilide. 2,4 - Dichloro - 5,6 - dinitro - anisole is prepared by nitration of 2,4-dichloro-anisole.