Comparative metabolism and pharmacokinetics of seven neonicotinoid insecticides in spinach

J Agric Food Chem. 2008 Nov 12;56(21):10168-75. doi: 10.1021/jf8020909. Epub 2008 Oct 16.

Abstract

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 II 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.

Publication types

  • Comparative Study
  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Guanidines / metabolism*
  • Guanidines / pharmacokinetics*
  • Insecticides / metabolism*
  • Insecticides / pharmacokinetics*
  • Nitro Compounds / metabolism*
  • Nitro Compounds / pharmacokinetics*
  • Pyridines / metabolism*
  • Pyridines / pharmacokinetics*
  • Spinacia oleracea / drug effects
  • Spinacia oleracea / metabolism*
  • Thiazoles / metabolism*
  • Thiazoles / pharmacokinetics*

Substances

  • Guanidines
  • Insecticides
  • Nitro Compounds
  • Pyridines
  • Thiazoles