Metabolism of [(14)c]chlorantraniliprole in the lactating goat

J Agric Food Chem. 2011 Feb 23;59(4):1316-23. doi: 10.1021/jf103558n. Epub 2011 Jan 11.

Abstract

Metabolism of [(14)C]chlorantraniliprole {3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)carbonyl]phenyl]-1- (3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide} was investigated in a lactating goat following seven consecutive daily single oral doses. Each dose was equivalent to 10.4 mg/kg of feed. There was no significant transfer of residues of either chlorantraniliprole or its metabolites into fat, meat, or milk. Chlorantraniliprole and its metabolites accounted for 93.57% of the administered dose and were eliminated primarily in the excreta. Residues in meat, milk, liver, and kidney together accounted for ca. 1.5% of the administered radioactivity. A total of 19 metabolites including 3 glucuronide conjugates and intact chlorantraniliprole were identified in the feces, urine, or tissues by comparison of their HPLC retention times, mass spectral fragments (LC-MS/MS), or multiple reaction monitoring (MRM) transitions to authentic synthesized standards. The major metabolic pathways of [(14)C]chlorantraniliprole in the goat were N-demethylation, methylphenyl hydroxylation, and further oxidation to the carboxylic acid; loss of water from the N-hydroxymethyl group to yield various cyclic metabolites; and hydrolysis of N-methyl amides to form benzoic acid derivatives. Minor metabolic reactions involved cleavage of the amide bridge between the phenyl and heterocyclic rings of chlorantraniliprole.

MeSH terms

  • Animals
  • Carbon Radioisotopes
  • Diet
  • Feces / chemistry
  • Female
  • Goats / metabolism*
  • Insecticides / administration & dosage
  • Insecticides / metabolism
  • Insecticides / pharmacokinetics*
  • Kidney / chemistry
  • Lactation / metabolism*
  • Liver / chemistry
  • Mass Spectrometry
  • Meat / analysis
  • Milk / chemistry
  • Pesticide Residues / analysis
  • ortho-Aminobenzoates / administration & dosage
  • ortho-Aminobenzoates / metabolism
  • ortho-Aminobenzoates / pharmacokinetics*

Substances

  • Carbon Radioisotopes
  • Insecticides
  • Pesticide Residues
  • ortho-Aminobenzoates
  • chlorantranilipole