The metabolism of chlorotoluron in the rat

Metabolism of N-[3-chloro-4-(.beta.-D-glucosylmethyl)phenyl]urea, a metabolite of chlorotoluron, in rats and Japanese quail

“…It was partly hydrolyzed to the aglycon. The aglycon was further metabolized to the corresponding carboxyphenyl derivative, the aglycon acid, a route that had been previously shown by Muecke et al (1976). Both the aglycon and the aglycon acid probably formed glucuronide conjugates which were further converted into polysaccharides.…”

“…Since very little information is available on the fate of glucoside conjugates, their bioavailability, and toxicological significance in animals, we have investigated the fate of N-[3-chloro-4-(d-D-glucosylmethyl) toluron glucoside), a glucoside of a chlorotoluron metabolite, JV-[3-chloro-4-(hydroxymethyl)phenyl]urea, in rat and Japanese quail. The metabolic fate of chlorotoluron has been reported previously (Muecke et al, 1976;Hinderer and Menzer, 1976a,b). The amino group of the 4-nitro-o-toluidine was then replaced by a chlorine according to the method of Albert and Linnell (1936) using the Grignard reaction.…”

Metabolism in human embryonic lung cell cultures of three phenylurea herbicides: chlorotoluron, fluometuron, and metobromuron

“…It seemed that only oxidative dealkylation of carbamoyl group substituents was involved in the metabolism of these three phenylurea molecules. Chlorotoluron has also been shown to be resistant to metabolic attack in rat hepatic microsomal systems (Hinderer and Menzer, 1976a), although it is readily degraded in rats in vivo (Mucke et al, 1976).…”

“…Only a few studies have been reported on the metabolism of these compounds. Mucke et al (1976) administered [ 14C] chlorotoluron to rats and found that chlorotoluron was demethylated to TV-(3chloro-4-methylphenyl)-TV'-methylurea and TV-(3-chloro-4-methylphenyl)urea. It was then further oxidized to form benzylic alcohol derivatives and benzoic acid derivatives.…”

Use of ion cluster analysis in a metabolic study of pencycuron, a phenylurea fungicide, in rabbits

“…Tateishi et al (1978) demonstrated that the S-methyl group was formed through three reactions: mercapturic acid conjugation, S-C cleavage, and methylation by S-methyltransferase of liver microsome. Although Muecke et al (1976) confirmed the methylthiolation of chlorotoluron in the rat, the mechanisms of those pathways are not understood at present. As indicated in this report, estimating the structure of an unknown metabolite can be facilitated by the use of ion cluster analysis, even if the metabolite was not completely separated and its amount was very small.…”