Pentachloronitrobenzene transformation

Initially formed polar metabolites such as phenols and amines may be conjugated to water-soluble terminal metabolites that are excreted into the medium and function as an effective mechanism of detoxification. For example, pentachlorophenol and pentachlorothiophenol produced from pentachloronitrobenzene conjugated represented the major metabolites. Although the naphthalene dihydrodiol was the major metabolite produced from naphthalene, the further transformation... 

Tetrahymena thermophila transforms pentachloronitrobenzene to the corresponding aniline and pentachlorothioanisole (Figure 2.24) (Murphy et al. 1982). 

Tas DO, SG Pavlostathis (2005) Microbial reductive transformation of pentachloronitrobenzene under metha-nogenic conditions. Environ Sci Technol 39 8264-8272. 

Pentachloronitrobenzene (PCNB) is another example of a nitroaromatic agrochemical that is known to undergo facile reduction in anaerobic systems. PCNB has been identified as a pollutant in river water and groundwater (Fushiwaki et al., 1990). Reduction of PCNB results in the formation of pentachloroaniline, which is fairly resistant to further transformation pathways (Wang and Broadbent, 1973 Kuhn and Suflita, 1989a) (Equation 3.23). 

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