Identification of the biochemical degradation pathway of triazophos and its intermediate in Diaphorobacter sp. TPD-1 |
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Authors: | Yang Chengli Li Rong Song Yao Chen Kai Li Shunpeng Jiang Jiandong |
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Institution: | (1) Department of Microbiology, Key Laboratory for Microbiological Engineering of Agricultural Environment of Ministry of Agriculture, College of Life Sciences, Nanjing Agricultural University, Nanjing, 210095, People’s Republic of China;(2) Department of Bioengineering, School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094, People’s Republic of China; |
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Abstract: | Triazophos is one of the most widely used organophosphorus insecticides usually detectable in the environment. A bacterial
strain, Diaphorobacter sp. TPD-1, capable of using triazophos and its intermediate, 1-phenyl-3-hydroxy-1,2,4-triazole (PHT), as its sole carbon
sources for growth was isolated from a triazophos-contaminated soil in China. This strain could completely degrade 50 mg l−1 triazophos and PHT to non-detectable level in 24 and 56 h, respectively. During PHT degradation, three metabolites were detected
and identified based on tandem mass spectrometry (MS/MS) analysis. Using this information, a biochemical degradation pathway
of triazophos by Diaphorobacter sp. TPD-1 was proposed. The first step involved in the degradation of triazophos is the hydrolysis of the P–O ester bond
of triazophos to form PHT and o,o-diethyl phosphorothioic acid, then the triazol ring of PHT is subsequently cleaved to form (E)-1-formyl-2-phenyldiazene.
Subsequently, (E)-1-formyl-2-phenyldiazene is transformed to 2-phenylhydrazinecarboxylic acid by adding one molecular of H2O. Finally, the carboxyl group of 2-phenylhydrazinecarboxylic acid is decarboxylated to form phenylhydrazine. |
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