Hydroxylation of thiacloprid by bacterium Stenotrophomonas maltophilia CGMCC1.1788

Biodegradation

Volumn 20, Issue 6, 2009, Pages 761-768

  Zhao, Yin Juan ^a   Dai, Yi Jun ^a   Yu, Ci Gang ^a   Luo, Jun ^a   Xu, Wen Ping ^a   Ni, Jue Ping ^b   Yuan, Sheng ^a  

^a NANJING NORMAL UNIVERSITY   (China)

^b Jiangsu Pesticide Research Institute   (China)

Author keywords

Acetamiprid; Hydroxylation; Imidacloprid; Stenotrophomonas maltophilia; Thiacloprid

Indexed keywords

ACETAMIPRID; ACID CONDITIONS; ALKALINE SOLUTIONS; CARBON ATOMS; CROP PROTECTION; DEMETHYLATION; HPLC-MS/MS; IMIDACLOPRID; IMIDACLOPRIDS; IMINE DERIVATIVES; INSECTICIDAL ACTIVITY; NEONICOTINOID INSECTICIDES; NMR ANALYSIS; STENOTROPHOMONAS MALTOPHILIA; STRUCTURAL DIFFERENCES; THIACLOPRID;

HYDROXYLATION; KETONES; NITROGEN COMPOUNDS; OLEFINS;

INSECTICIDES;

ACETAMIPRID; IMIDACLOPRID; IMIDAZOLE DERIVATIVE; NITRO DERIVATIVE; PIPERONYL BUTOXIDE; PYRIDINE DERIVATIVE; THIACLOPRID; THIAZINE DERIVATIVE;

APHID; BACTERIUM; BIOASSAY; FLEA; INSECTICIDE; LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; TOXICITY; TRANSFORMATION; WHITEFLY;

ANIMAL; APHID; ARTICLE; BIOASSAY; BIOTRANSFORMATION; CHEMISTRY; CYTOLOGY; DRUG EFFECT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROXYLATION; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUTION AND SOLUBILITY; STENOTROPHOMONAS MALTOPHILIA; TIME;

ANIMALS; APHIDS; BIOLOGICAL ASSAY; BIOTRANSFORMATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HYDROXYLATION; IMIDAZOLES; MAGNETIC RESONANCE SPECTROSCOPY; NITRO COMPOUNDS; PIPERONYL BUTOXIDE; PYRIDINES; SOLUTIONS; STENOTROPHOMONAS MALTOPHILIA; THIAZINES; TIME FACTORS;

ALEYRODIDAE; APHIDIDAE; BACTERIA (MICROORGANISMS); CANIS FAMILIARIS; SIPHONAPTERA (FLEAS); STENOTROPHOMONAS MALTOPHILIA;

EID: 70350273383     PISSN: 09239820     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10532-009-9264-0     Document Type: Article

References (17)

1. Chen T, Dai YJ, Ding JF, Yuan S (2008) N-demethylation of neonicotinoid insecticide acetamiprid by bacterium Stenotrophomonas maltophilia CGMCC1.1788. Biodegradation 19:651-658. doi:10.1007/s10532-007-9170-2.
2. Dai YJ, Yuan S, Ge F, Chen T, Xu SC, Ni JP (2006) Microbial hydroxylation of imidacloprid for the synthesis of highly insecticidal olefin imidacloprid. Appl Microbiol Biotechnol 71:927-934. doi:10.1007/s00253-005-0223-3.
3. Dai YJ, Chen T, Ge F, Huan Y, Yuan S, Zhu FF (2007) Enhanced hydroxylation of imidacloprid by Stenotrophomonas maltophilia upon addition of sucrose. Appl Microbiol Biotechnol 74:995-1000. doi:10.1007/s00253-006-0762-2.
4. Elbert A, Erdelen C, Hattori Y, Kuhnhold J, Nauen R, Schmidt HW (2000) Thiacloprid: a novel neonicotinoid insecticide for foliar application. Proc British Crop Prot Conf-Pests and Diseases, BCPC, Farnham, Surrey, Surrey, UK, pp 21-26.
5. Elbert A, Haas M, Springer B, Thielert W, Nauen R (2008) Applied aspects of neonicotinoid uses in crop protection. Pest Manag Sci 64:1099-1105. doi:10.1002/ps.1616.
6. Horowitz A, Mendelson Z, Weintraub P, Ishaaya I (1998) Comparative toxicity of foliar and systemic applications of acetamiprid and imidacloprid against the cotton whitefly, Bemisia tabaci (Hemiptera: Aleyrodidae). Bull Entomol Res 88(4):437-442.
7. Jouben N, Heckel DG, Haas M, Schuphan I, Schmidt B (2008) Metabolism of imidacloprid and DDT by P450 CYP6G1 expressed in cell cultures of Nicotiana tabacum suggests detoxification of these insecticides in Cyp6g1-overexpressing strains of Drosophila melanogaster, leading to resistance. Pest Manag Sci 64:65-73. doi:10.1002/ps.1472.
8. Klein O (2001) Behavior of thiacloprid (YRC 2894) in plants and animals. Pflanzenschutz-Nachichten Bayer 54:209-240. Available on http://www.agro.bayer.com.
9. Krohn J (2001) Behavior of thiacloprid in the environment. Pflanzenschutz-Nachrichten Bayer 54(2):281-289. Available on http://www.agro.bayer.com.
10. Krohn J, Hellpointner E (2002) Environmental fate of imidacloprid. Pflanzenschutz-Nachr Bayer 55:3-26. Available on http://www.agro.bayer.com.
11. Matsuzaki F, Wariishi H (2004) Functional diversity of cytochrome P450 s of the white-rot fungus Phanerochaete chrysosporium. Biochem Biophys Res Commun 324:387-393. doi:10.1016/j.bbrc.2004.09.062.
12. Nauen R, Rechmann U, Armborst S, Stupp HP, Elbert A (1999) Whitefly-active metabolites of imidacloprid: biological efficacy and translocation in cotton plants. Pestic Sci 55:265-271. doi:10.1002/(SICI)1096-9063(199903)55:3<265::AID-PS891>3.0.CO;2-C.
13. Nauen R, Ebbinghaus-Kintscher U, Salgado VL, Kaussmannb M (2003) Thiamethoxam is a neonicotinoid precursor converted to clothianidin in insects and plants. Pestic Biochem Physiol 76:55-59. doi:10.1016/S0048-3575(03)00065-8.
14. Rouchaud J, Gustin F, Wauters A (1994) Soil biodegradation and leaf transfer of insecticide imidacloprid applied in seed dressing in sugar beet crops. Bull Environ Contam Toxicol 53:344-350. doi:10.1007/BF00197224.
15. Sato A, Watanabe T, Watanabe Y, Harazono K, Fukatsu T (2002) Screening for basidiomycetous fungi capable of degrading 2, 7-dichlorodibenzo-p-dioxin. FEMS Microbiol Lett 213:213-217. doi:10.1111/j.1574-6968.2002.tb11308.x.
16. Schulz-Jander D, Casida J (2002) Imidacloprid insecticide metabolism:human cytochrome P450 isozymes differ in selectivity for imidazolidine oxidation versus nitroimine reduction. Toxicol Lett 132:65-70. doi:10.1016/S0378-4274(02)00068-1.
17. Tomizawa M, Lee DL, Casida JE (2000) Neonicotinoid insecticides: molecular features conferring selectivity for insect versus mammalian nicotinic receptors. J Agric Food Chem 48:6016-6024. doi:10.1021/jf000873c.