NDLI: Hydroxylation of thiacloprid by bacterium Stenotrophomonas maltophilia CGMCC1.1788

Content Provider	Springer Nature Link
Author	Zhao, Yin Juan Dai, Yi Jun Yu, Ci Gang Luo, Jun Xu, Wen Ping Ni, Jue Ping Yuan, Sheng
Copyright Year	2009
Abstract	Chloropyridinyl neonicotinoid insecticides play a major role in crop protection and flea control on cats and dogs. Imidacloprid, thiacloprid and acetamiprid have in common the 6-chloro-3-pyridinylmethyl group but differ in the nitroguanidine or cyanoamidine substituent on an acyclic or cyclic moiety. Our previous study found that Stenotrophomonas maltophilia CGMCC 1.1788 could hydroxylate imidacloprid to 5-hydroxy imidacloprid, and 5-hydroxy imidacloprid was easily converted to 10–19 times higher insecticidal olefin imidacloprid against aphid or whitefly. Acetamiprid could be transformed by S. maltophilia to form N-demethylation product(IM 2-1). In this paper, we examined S. maltophilia CGMCC 1.1788’s ability of transformation of thiacloprid. S. maltophilia CGMCC 1.1788 can hydroxylate thiacloprid to 4-hydroxy thiacloprid characterized by HPLC-MS/MS and NMR analysis, however 4-hydroxy thiacloprid could not be converted to olefin thiacloprid under acid conditions like imidacloprid, whereas oxidized and decyonated simultaneously to form 4-ketone thiacloprid imine in alkaline solution. Bioassays indicated that 4-hydroxy thiacloprid had 156 times lower insecticidal activity than thiacloprid, and the ketone-imine derivative almost had no toxicity towards aphid. Though both imidacloprid and thiacloprid are hydroxylated by S. maltophilia CGMCC 1.1788 at the same carbon atom position, however the structural difference between in imidacloprid and thiacloprid, originate the entire discrepancy in bioefficacy of metabolite and its further degrading pathway. These results explain that why thiacloprid is classified as not relevant grade for soil and seed applications, whereas imidacloprid is recommended and acetamiprid is limited.
Starting Page	761
Ending Page	768
Page Count	8
File Format	PDF
ISSN	09239820
Journal	Biodegradation
Volume Number	20
Issue Number	6
e-ISSN	15729729
Language	English
Publisher	Springer Netherlands
Publisher Date	2009-05-07
Publisher Place	Dordrecht
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Hydroxylation Imidacloprid Thiacloprid Acetamiprid Stenotrophomonas maltophilia Waste Management/Waste Technology Waste Water Technology / Water Pollution Control / Water Management / Aquatic Pollution Terrestrial Pollution Geochemistry Soil Science & Conservation Microbiology
Content Type	Text
Resource Type	Article
Subject	Environmental Chemistry Pollution Environmental Engineering Bioengineering Microbiology

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