The DOI matches its Crossref record; 37 of the 37 references it cites were found in a registry or an index.
Neonicotinoid Metabolism: Compounds, Substituents, Pathways, Enzymes, Organisms, and Relevance
Abstract
Neonicotinoids are one of the three principal insecticide chemotypes. The seven major commercial neonicotinoids are readily biodegraded by metabolic attack at their N-heterocyclylmethyl moiety, heterocyclic or acyclic spacer, and N-nitroimine, nitromethylene, or N-cyanoimine tip. Phase I metabolism is largely dependent on microsomal CYP450 isozymes with situ selectivity in hydroxylation, desaturation, dealkylation, sulfoxidation, and nitro reduction. Cytosolic aldehyde oxidase is a nitroreductase for some neonicotinoids. Phase II metabolism involves methylation, acetylation, and formation of glucuronide, glucoside, amino acid, and sulfate- and glutathione-derived conjugates. Some neonicotinoids act as proinsecticides with metabolism to more potent nicotinic agonists. Pest resistance is more commonly due to synergist-reversible CYP450 detoxification than to nAChR mutants or variants. Metabolites in some cases contribute to mammalian hepatotoxicity and carcinogenesis and in others to enhanced plant vigor and stress shields. These relationships explain much of neonicotinoid comparative toxicology and provide the basis for continued and improved safety and effectiveness of this chemotype.
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Cites
Overview of the Status and Global Strategy for Neonicotinoids
Jeschke, P., Nauen, R., Schindler, M., & Elbert, A. (2011) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf101303g · Cited by 1,867
NEONICOTINOID INSECTICIDE TOXICOLOGY: Mechanisms of Selective Action
Tomizawa, M., & Casida, J. E. (2005) · Annual Review of Pharmacology and Toxicology · doi:10.1146/annurev.pharmtox.45.120403.095930 · Cited by 1,741
Self-citationTomizawa, M., & Casida, J. E. (2003) · Annual Review of Entomology · doi:10.1146/annurev.ento.48.091801.112731 · Cited by 899
Self-citationNeonicotinoids—from zero to hero in insecticide chemistry
Jeschke, P., & Nauen, R. (2008) · Pest Management Science · doi:10.1002/ps.1631 · Cited by 870
Thiamethoxam is a neonicotinoid precursor converted to clothianidin in insects and plants
Nauen, R., Ebbinghaus-Kintscher, U., Salgado, V. L., & Kaussmann, M. (2003) · Pesticide Biochemistry and Physiology · doi:10.1016/s0048-3575(03)00065-8 · Cited by 490
Colorado Potato Beetle Resistance to Insecticides
Alyokhin, A., Baker, M., Mota-Sanchez, D., Dively, G., & Grafius, E. (2008) · American Journal of Potato Research · doi:10.1007/s12230-008-9052-0 · Cited by 478
Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor
(1999) · Springer eBooks · doi:10.1007/978-4-431-67933-2 · Cited by 348
Nauen, R., Ebbinghaus‐Kintscher, U., & Schmuck, R. (2001) · Pest Management Science · doi:10.1002/ps.331 · Cited by 287
Daborn, P., Boundy, S., Yen, J., Pittendrigh, B., & ffrench-Constant, R. (2001) · Molecular Genetics and Genomics · doi:10.1007/s004380100531 · Cited by 278
Tomizawa, M., Lee, D. L., & Casida, J. E. (2000) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf000873c · Cited by 247
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Cited by
Hladik, M. L., Kolpin, D. W., & Kuivila, K. M. (2014) · Environmental Pollution · doi:10.1016/j.envpol.2014.06.033 · Cited by 407
Metadata
- Authors
- Casida, J. E.
- Venue
- Journal of Agricultural and Food Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-08-23
- Volume
- 59
- Issue
- 7
- Pages
- 2923-2931
- ISSN
- 0021-8561 (ISSN-L)
- 1520-5118
- OpenAlex
- W2048043678
- Cited by
- 375
- References
- 37
- FWCI
- 13.46
- Type
- journal article
- Language
- en
- Open access
- closed
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