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During the course of our previous studies, l, 2) Mucoy javanicus was found to metabolize 2, 3and 2, 4-dichloro-l-nitrobenzenes (DCNB) into the corresponding benzenamines, 3or 4chloro-2-methylthio-l-nitrobenzene and 3or 4-chloro-2-methylthiobenzenamine. On the basis of the metabolite structure, two reactions, namely, reduction of the nitro group and/or substitution of the ortho chlorine atom by a methylthio group were responsible for the formation of these metabolites. However, no information was obtained about a metabolic pathway or a source of the sulfur atom in methylthio-containing metabolites. Lamoureux and Rusness" have recently reported on the pentachloronitrobenzene (PCNB) metabolism in onions, proposing a mechanism of pentachloro-methylthiobenzene (PCMTB) formation. Their investigation shows that S(pentachlorophenyl)cysteine, which is suggested to be an intermediate derived from S-(pentachlorophenyl)glutathione, is metabolized to pentachlorobenzenethiol, followed by methylation to PCMTB. Their results suggest the formation of methylthio-containing metabolites from DCNB by M. javanicus via the similar pathway to that yielding PCMTB from PCNB in onions. This paper is to present some lines of evidence for the presence of a metabolic pathway in the fungus to afford methylthio-containing metabolites (5, 6) from 2, 4-DCNB (1) via its glutathione conjugate [S-(5-chloro-2-nitrophenyl)glutathione, 2]. For example, first, glutathione S-transferase (GST) activity was detected in the cell-free extract of M. javanicus, and glutathione conjugate 2 derived from 2, 4DCNB (1) was successfully isolated from the enzymatic reaction mixture. Second, further metabolism of 2, a cysteine conjugate [S-(5chloro-2-nitrophenyl)cysteine, 3], or 5-chloro-2nitrobenzenethiol (4) resulted in the formation *Microbial Metabolism of Chlorinated Nitro-

nippon nōyaku gakkaishi

A Glutathione Conjugate of 2, 4-Dichloro-1-nitrobenzene: Its Detection as a Metabolic Intermediate and Further Metabolism in &lt;i&gt;Mucor javanicus&lt;/i&gt;