Skip to main content
Log in

Identification of the Biochemical Degradation Pathway of Triazophos and its Intermediate in Diaphorobacter sp. TPD-1

  • Published:
Current Microbiology Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Alexis JH, Li C, Ian CS (2001) Thermal stability of organophosphorus pesticide triazophos and its relevance in the assessment of risk to the consumer of triazophos residues in food. J Agric Food Chem 49:103–106

    Article  Google Scholar 

  2. Andersona BS, Hunta JW (2003) Integrated assessment of the impacts of agricultural drain water in the Salinas River (California, USA). Environ Pollut 124:523–532

    Article  Google Scholar 

  3. Aungpradit T, Sutthivaiyakit P, Martens D et al (2007) Photocatalytic degradation of triazophos in aqueous titanium dioxide suspension: identification of intermediates and degradation pathways. J Hazard Mater 146:204–213

    Article  PubMed  CAS  Google Scholar 

  4. Cai TM, Qian LH, Cai S et al. (2010) Biodegradation of Benazolin-ethyl by strain Methyloversatilis sp. cd-1 isolated from activated sludge. Curr Microbiol. doi:10.1007/s00284-010-9746-7

  5. Cheng S, Xiao J, Xiao H et al (2007) Technical note phytoremediation of triazophos by Canna indica Linn. in a hydroponic system. Int J Phytoremediation 9:453–463

    Article  PubMed  CAS  Google Scholar 

  6. Dai QH, Zhang RF, Jiang JD et al (2007) Cloning of triazophos hydrolase gene and the determination of the hydrolysate. China Environ Sci 27:777–780

    CAS  Google Scholar 

  7. Guo XQ, Li R, Lin D et al (2009) Isolation and characterization of a triazophos-degrading strain GS-1 and its degrading characteristics. Microbiology (China) 36:1143–1149

    CAS  Google Scholar 

  8. Holt JG, Krieg NR, Sneath PHA et al (1994) Bergey’s manual of determinative bacteriology, 9th edn. The Williams and Wilkins Company, Baltimore

    Google Scholar 

  9. Li XH, He J, Li SP (2007) Isolation of a chlorpyrifos-degrading bacterium, Sphingomonas sp strain Dsp-2, and cloning of the mpd gene. Res Microbiol 158:143–149

    Article  PubMed  CAS  Google Scholar 

  10. Li W, Qiu SP, Wu YJ (2008) Triazophos residues and dissipation rates in wheat crops and soil. Ecotoxicol Environ Saf 69:312–316

    Article  PubMed  CAS  Google Scholar 

  11. Li RX, Yang CP, Chen H et al (2009) Removal of triazophos pesticide from wastewater with Fenton reagent. J Hazard Mater 67:1028–1032

    Article  Google Scholar 

  12. Lin KD, Yuan DX (2005) Degradation kinetics and products of triazophos in intertidal sediment. J Environ Sci (China) 17:933–936

    CAS  Google Scholar 

  13. Lin KD, Yuan DX, Chen M et al (2004) Kinetics and products of photo-Fenton degradation of triazophos. J Agric Food Chem 52:7614–7620

    Article  PubMed  CAS  Google Scholar 

  14. Lin KD, Yuan DX, Deng YZ et al (2004) Hydrolytic products and kinetics of triazophos in buffered and alkaline solutions with different values of pH. J Agric Food Chem 52:5404–5411

    Article  CAS  Google Scholar 

  15. Rovedatti MG (2001) Monitoring of organochlorine and organophosphorus pesticides in the water of the Reconquista River. Water Res 35:3457–3461

    Article  PubMed  CAS  Google Scholar 

  16. Sawaya WN, Fawzia A, Awadhi A (2000) Dietary intake of organophosphate pesticides in Kuwait (analytical, nutritional and clinical methods section). Food Chem 69:331–338

    Article  CAS  Google Scholar 

  17. Singh BK, Walker A (2006) Microbial degradation of organophosphorus compounds. FEMS Microbiol Rev 30:428–471

    Article  PubMed  CAS  Google Scholar 

  18. Velazquez A, Xamena N, Creus A, Marcos R (1990) Mutagenic evaluation of the organophosphorus insecticides methyl parathion and triazophos in Drosophila melanogaster. J Toxicol Environ Health 31:313–325

    Article  PubMed  CAS  Google Scholar 

  19. Wang LH, Zhang L, Chen HL et al (2005) Isolation of a triazophos-degrading strain Klebsiella sp E6 effectively utilizing triazophos as sole nitrogen source. FEMS Microbiol Lett 253:259–265

    Article  PubMed  CAS  Google Scholar 

  20. Wang XD, Liu XJ, Yang S et al (2007) Removal and toxicological response of triazophos by Chlamydomonas reinhardtii. Bull Environ Contam Toxicol 78:67–71

    Article  PubMed  CAS  Google Scholar 

  21. Wilson KH, Blitchington RB, Greene RC (1990) Amplification of bacterial-16s ribosomal DNA with polymerase chain-reaction. J Clin Microbiol 28:1942–1946

    PubMed  CAS  Google Scholar 

  22. Xiao HP, Cheng SP, Wu ZB (2010) Microbial community variation in phytoremediation of triazophos by Canna indica Linn. in a hydroponic system. J Environ Sci (China) 8:1225–1231

    Google Scholar 

Download references

Acknowledgments

This work was supported by grants from the Major Projects on Control and Rectification of Water Body Pollution (2009ZX07103-002), the Chinese National Natural Science Foundation (31070100), and the Key Technology R&D Program of Jiangsu Province (BE2008669).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jiandong Jiang.

Additional information

Chenli Yang and Rong Li contributed equally to this article.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yang, C., Li, R., Song, Y. et al. Identification of the Biochemical Degradation Pathway of Triazophos and its Intermediate in Diaphorobacter sp. TPD-1. Curr Microbiol 62, 1294–1301 (2011). https://doi.org/10.1007/s00284-010-9859-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00284-010-9859-z

Keywords

Navigation