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Microbial hydroxylation of imidacloprid for the synthesis of highly insecticidal olefin imidacloprid

  • Yi-jun Dai
  • Sheng YuanEmail author
  • Feng Ge
  • Ting Chen
  • Shang-cheng Xu
  • Jue-ping Ni
Applied Microbial and Cell Physiology

Abstract

Microorganisms that bring about the aerobic transformation of imidacloprid (IMI) were isolated and screened, and the microbial regio- and stereoselective hydroxylation of IMI was studied. Some bacteria and fungi transformed IMI to 5-hydroxyl IMI. Bacterium Stenotrophomonas maltophilia CGMCC 1.1788 resting cells transformed IMI into R-5-hydroxyl IMI at the highest conversion rate. The enzyme catalyzed the stereoselective hydroxylation at position C12 of IMI in the imidazolidine ring. Under acidic conditions, 5-hydroxyl IMI was converted into olefin IMI in high molar conversion yield. The olefin IMI exhibited about 19 and 2.2 times more insecticidal efficacy than IMI against horsebean aphid imago and nymph, respectively, and about 1.4 times more active than IMI against brown planthopper imago. The transformation rate of IMI by resting cells of S. maltophilia CGMCC 1.1788 was promoted significantly by some carbohydrates and organic acids. The reaction medium with 5% sucrose resulted in 8.3 times greater biotransformation yield as compared with that without sucrose.

Keywords

Imidacloprid Transformation Activity Acetamiprid Brown Planthopper Biotransformation Product 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Notes

Acknowledgements

We are thankful for support from the 10th Five Years Project for the National Key Technologies R&D Program (2004BA308A22-12) and the Jiangsu Academic Natural Science Foundation (04KJB180071). We especially thank Dr. Ji-Hua Liu of China Pharmaceutical University for conducting M.S. studies and Dr. Jia-Hong Zhou for conducting NMR studies. We sincerely acknowledge Dr. Bing-Xiang Wang for analytical assistance.

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Copyright information

© Springer-Verlag 2005

Authors and Affiliations

  • Yi-jun Dai
    • 1
  • Sheng Yuan
    • 1
    Email author
  • Feng Ge
    • 1
  • Ting Chen
    • 1
  • Shang-cheng Xu
    • 2
  • Jue-ping Ni
    • 2
  1. 1.Jiangsu Key Lab for Bioresource Technology, Key Lab for Microbial Technology in College of Life ScienceNanjing Normal UniversityNanjingPR China
  2. 2.Jiangsu Pesticide Research InstituteNanjingPR China

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