Hydroxylation of thiacloprid by bacterium Stenotrophomonas maltophilia CGMCC1.1788
| Autor: | Jueping Ni, Cigang Yu, Jun Luo, Sheng Yuan, Yin-Juan Zhao, Wenping Xu, Yi-Jun Dai |
|---|---|
| Rok vydání: | 2009 |
| Předmět: |
Magnetic Resonance Spectroscopy
Time Factors Environmental Engineering Piperonyl Butoxide Pyridines Stereochemistry Stenotrophomonas maltophilia Thiazines Bioengineering Whitefly Hydroxylation Microbiology Acetamiprid Neonicotinoids chemistry.chemical_compound Imidacloprid Animals Environmental Chemistry Biotransformation Chromatography High Pressure Liquid biology Imidazoles Neonicotinoid Nitro Compounds biology.organism_classification Thiacloprid Pollution Solutions Nitroguanidine chemistry Aphids Biological Assay |
| Zdroj: | Biodegradation. 20:761-768 |
| ISSN: | 1572-9729 0923-9820 |
| DOI: | 10.1007/s10532-009-9264-0 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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