Neonicotinoid Metabolism: Compounds, Substituents, Pathways, Enzymes, Organisms, and Relevance
Top Cited Papers
- 23 August 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Agricultural and Food Chemistry
- Vol. 59 (7), 2923-2931
- https://doi.org/10.1021/jf102438c
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.This publication has 61 references indexed in Scilit:
- Discovery of Imidacloprid and Further Developments from Strategic Molecular DesignsJournal of Agricultural and Food Chemistry, 2010
- Overview of the Status and Global Strategy for NeonicotinoidsJournal of Agricultural and Food Chemistry, 2010
- Molecular Recognition of Neonicotinoid Insecticides: The Determinants of Life or DeathAccounts of Chemical Research, 2008
- Neonicotinoids—from zero to hero in insecticide chemistryPest Management Science, 2008
- NEONICOTINOID INSECTICIDE TOXICOLOGY: Mechanisms of Selective ActionAnnual Review of Pharmacology and Toxicology, 2005
- Neonicotinoid InsecticidesPublished by Elsevier BV ,2005
- Absorption, Tissue Distribution, Excretion, and Metabolism of Clothianidin in RatsJournal of Agricultural and Food Chemistry, 2003
- SELECTIVE TOXICITY OF NEONICOTINOIDS ATTRIBUTABLE TO SPECIFICITY OF INSECT AND MAMMALIAN NICOTINIC RECEPTORSAnnual Review of Entomology, 2003
- Nicotinoid Insecticides and the Nicotinic Acetylcholine ReceptorPublished by Springer Science and Business Media LLC ,1999
- Discovery of Chloronicotinyl InsecticidesPublished by Springer Science and Business Media LLC ,1999