Metabolism of 3‐chloro‐4‐methoxyaniline and some N‐acyl derivatives in soil

Abstract

3‐Chloro‐4‐methoxyaniline at concentrations of 10ppm or more in soil is converted to a mixture of 3,3′dichloro‐4,4′‐dimethoxyazobenzene, 3‐chlorobenzoquinone‐4‐(3‐chloro‐4‐methoxy)anil and its reduction product 2,3′‐dichloro‐4‐hydroxy‐4‐'methoxydiphenylamine, probably by a free radical mechanism.The herbicide metoxuron, N'‐(3‐chloro‐4‐methoxyphenyl)‐N,N‐dimethylurea and its demethylated metabolites probably break down to the amine too slowly in soil for coupling products to be detected. 3‐Chloro‐4‐methoxyacetanilide at 25 ppm rapidly gives rise to amine coupling products in soil slurries and ethyl N‐(3‐chloro‐4‐methoxyphenyl)carbamate does so after two months in the slurries.