Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 56, Issue 21, Pages 10168-10175Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jf8020909
Keywords
Clothiandin; comparative metabolism; imidacloprid; LC-MSD; neonicotinoid insecticide; neonicotinoid pharmacokinetics; plant metabolism; thiamethoxam
Funding
- Rita Nichiporuk of the Mass Spectrometry Facility
- Department of Chemistry at Berkeley
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The metabolism of seven commercial neonicotinoid insecticides was compared in spinach seedlings (Spinacia oleracea) using HPLC-DAD and LC-MSD to analyze the large number and great variety of metabolites. The parent neonicotinoid levels in the foliage following hydroponic treatment varied from differences in uptake and persistence. The metabolic reactions included nitro reduction, cyano hydrolysis, demethylation, sulfoxidation, imidazolidine and thiazolidine hydroxylation and olefin formation, oxadiazine hydroxylation and ring opening, and chloropyridinyl dechlorination. The identified phase I plant metabolites were generally the same as those in mammals, but the phase I I metabolites differed in the conjugating moieties. Novel plant metabolites were various neonicotinoid-derived O- and N-glucosides and -gentiobiosides and nine amino acid conjugates of chloropyridinylcarboxylic acid. Metabolites known to be active on nicotinic acetylcholine receptors included the desnitro- and descyanoguanidines and olefin derivatives. The findings highlight both metabolites common to several neonicotinoids and those that are compound specific.
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