Hydroxylation of thiacloprid by bacterium Stenotrophomonas maltophilia CGMCC1.1788.
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.
Zhao
Yin-Juan
YJ
Jiangsu Engineering and Technology Research Center for Industrialization of Microbial Resources, Jiangsu Key Laboratory for Biodiversity and Biotechnology, College of Life Science, Nanjing Normal University, 210046, Nanjing, People's Republic of China.
Dai
Yi-Jun
YJ
Yu
Ci-Gang
CG
Luo
Jun
J
Xu
Wen-Ping
WP
Ni
Jue-Ping
JP
Yuan
Sheng
S
D000818:Animals; D001042:Aphids / Q000187:drug effects; D001681:Biological Assay; D001711:Biotransformation / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D006900:Hydroxylation / Q000187:drug effects; D007093:Imidazoles / Q000737:chemistry / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D000073943:Neonicotinoids; D009574:Nitro Compounds / Q000737:chemistry / Q000378:metabolism; D010882:Piperonyl Butoxide / Q000494:pharmacology; D011725:Pyridines / Q000737:chemistry / Q000378:metabolism*; D012996:Solutions; D020615:Stenotrophomonas maltophilia / Q000166:cytology / Q000187:drug effects / Q000378:metabolism*; D013843:Thiazines / Q000737:chemistry / Q000378:metabolism*; D013997:Time Factors
D007093:Imidazoles; D000073943:Neonicotinoids; D009574:Nitro Compounds; D011725:Pyridines; D012996:Solutions; D013843:Thiazines; C082359:imidacloprid; C464485:acetamiprid; C417209:thiacloprid; D010882:Piperonyl Butoxide