Cycloxaprid insecticide: Nicotinic acetylcholine receptor binding site and metabolism

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 33, 2013, Pages 7883-7888

  Shao, Xusheng ^a,b   Swenson, Tami L ^a   Casida, John E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

cycloxaprid; honeybee; house fly; metabolism; mouse; neonicotinoid; nicotinic acetylcholine receptor

Indexed keywords

CYCLOXAPRID; HONEYBEE; HOUSE-FLIES; MOUSE; NEONICOTINOIDS; NICOTINIC ACETYLCHOLINE RECEPTORS;

ASSAYS; HOUSES; INSECTICIDES; METABOLISM; PHYSIOLOGY;

MAMMALS;

CYCLOXAPRID; FUSED HETEROCYCLIC RINGS; IMIDACLOPRID; IMIDAZOLE DERIVATIVE; INSECT PROTEIN; INSECTICIDE; NICOTINIC RECEPTOR; NICOTINIC RECEPTOR BLOCKING AGENT; NITRO DERIVATIVE; PYRIDINE DERIVATIVE;

ANIMAL; ARTICLE; BEE; BINDING SITE; CHEMISTRY; HOUSE FLY; KINETICS; MALE; METABOLISM; MOUSE;

ANIMALS; BEES; BINDING SITES; HETEROCYCLIC COMPOUNDS, 3-RING; HOUSEFLIES; IMIDAZOLES; INSECT PROTEINS; INSECTICIDES; KINETICS; MALE; MICE; NICOTINIC ANTAGONISTS; NITRO COMPOUNDS; PYRIDINES; RECEPTORS, NICOTINIC;

EID: 84883168098     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf4030695     Document Type: Article

References (19)

1. Qian, X.; Li, Z.; Shao, X.; Xu, X.; Xu, Z.; Song, G. Divalent and oxabridged neonicotinoid compounds and their preparation methods thereof. U.S. Patent 2012/0245126 A1, 2012.
2. Shao, X.; Liu, Z.; Xu, X.; Li, Z.; Qian, X. Overall status of neonicotinoid insecticides in China: Production, application and innovation J. Pestic. Sci. 2013, 38, 1-9
3. Shao, X.; Ye, Z.; Bao, H.; Liu, Z.; Xu, X.; Li, Z.; Qian, X. Advanced research on cis-neonicotinoids Chimia 2011, 65, 957-960
4. Shao, X.; Lee, P. W.; Liu, Z.; Xu, X.; Li, Z.; Qian, X. cis-Configuration: A new tactic/ rationale for neonicotinoid molecular design J. Agric. Food Chem. 2011, 59, 2943-2949
5. Cui, L.; Sun, L.; Yang, D.; Yan, X.; Yuan, H. Effects of cycloxaprid, a novel cis-nitromethylene neonicotinoid insecticide, on the feeding behavior of Sitobion avenae Pest Manage. Sci. 2012, 68, 1484-1491
6. Shao, X.; Fu, H.; Xu, X.; Xu, X.; Liu, Z.; Li, Z.; Qian, X. Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid: Design, synthesis, crystal structure, and insecticidal activities J. Agric. Food Chem. 2010, 58, 2696-2702
7. Kagabu, S.; Moriya, K.; Shibuya, K.; Hattori, Y.; Tsuboi, S.; Shiokawa, K. 1-(6-Halonicotinyl)-2-nitromethylene-imidazolidines as potential new insecticides Biosci., Biotechnol., Biochem. 1992, 56, 362-363
8. 125I]neonicotinoid photoaffinity probe for the Drosophila nicotinic acetylcholine receptor Bioconjugate Chem. 1997, 8, 7-14
9. Kagabu, S. Proneonicotinoid J. Pestic. Sci. 2011, 36, 205-211
10. Kagabu, S.; Ogawa, M.; Makimura, M.; Nishimura, K. Insecticidal and neuroblocking activities in the American cockroach (Periplaneta americana L.) of Mannich bases of nitromethylene imidazolidine neonicotinoids J. Pestic. Sci. 2005, 30, 44-46
11. Tomizawa, M.; Lee, D. L.; Casida, J. E. Neonicotinoid insecticides: Molecular features conferring selectivity for insect versus mammalian nicotinic receptors J. Agric. Food Chem. 2000, 48, 6016-6024
12. Tomizawa, M.; Casida, J. E. Selective toxicity of neonicotinoids attributable to specificity of insect and mammalian nicotinic receptors Annu. Rev. Entomol. 2003, 48, 339-364
13. Chao, S. L.; Casida, J. E. Interaction of imidacloprid metabolites and analogs with the nicotinic acetylcholine receptor of mouse brain in relation to toxicity Pestic. Biochem. Physiol. 1997, 58, 77-88
14. Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal. Biochem. 1976, 72, 248-254
15. Ford, K. A.; Casida, J. E. Chloropyridinyl neonicotinoid insecticides: Diverse molecular substituents contribute to facile metabolism in mice Chem. Res. Toxicol. 2006, 19, 944-951
16. Ford, K. A.; Casida, J. E. Unique and common metabolites of thiamethoxam, clothianidin, and dinotefuran in mice Chem. Res. Toxicol. 2006, 19, 1549-1556
17. Casida, J. E. Neonicotinoid metabolism: Compounds, substituents, pathways, enzymes, organisms, and relevance J. Agric. Food Chem. 2011, 59, 2923-2931
18. Yamamoto, I.; Casida, J. E., Eds. Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor; Springer: New York, 1999; 300 pp.
19. Kleier, D.; Holden, I.; Casida, J. E.; Ruzo, L. O. Novel photoreactions of an insecticidal nitromethylene heterocycle J. Agric. Food Chem. 1985, 33, 998-1000