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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Citations
Cites
Overview of the Status and Global Strategy for Neonicotinoids
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NEONICOTINOID INSECTICIDE TOXICOLOGY: Mechanisms of Selective Action
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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
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Self-citationMetabolism of imidacloprid in Apis mellifera
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Structure and diversity of insect nicotinic acetylcholine receptors
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Self-citationThiamethoxam Induced Mouse Liver Tumors and Their Relevance to Humans
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Self-citationNitroso-Imidacloprid Irreversibly Inhibits Rabbit Aldehyde Oxidase
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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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