title: Metabolism of [(14)c]chlorantraniliprole in the lactating goat.
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.
authors.affiliation: DuPont Crop Protection, Stine-Haskell Research Center, Newark, Delaware 19714-0030, United States. venkat.gaddamidi@usa.dupont.com
authors.forename: Venkat
authors.initials: V
authors.lastname: Gaddamidi
authors.forename: Martin T
authors.initials: MT
authors.lastname: Scott
authors.forename: R Scott
authors.initials: RS
authors.lastname: Swain
authors.forename: David
authors.initials: D
authors.lastname: Macpherson
authors.forename: Chris
authors.initials: C
authors.lastname: Lowrie
mesh_terms: D000818:Animals; D002250:Carbon Radioisotopes; D004032:Diet; D005243:Feces / Q000737:chemistry; D005260:Female; D006041:Goats / Q000378:metabolism*; D007306:Insecticides / Q000008:administration & dosage / Q000378:metabolism / Q000493:pharmacokinetics*; D007668:Kidney / Q000737:chemistry; D007774:Lactation / Q000378:metabolism*; D008099:Liver / Q000737:chemistry; D013058:Mass Spectrometry; D008460:Meat / Q000032:analysis; D008892:Milk / Q000737:chemistry; D010573:Pesticide Residues / Q000032:analysis; D062367:ortho-Aminobenzoates / Q000008:administration & dosage / Q000378:metabolism / Q000493:pharmacokinetics*
chemical_list: D002250:Carbon Radioisotopes; D007306:Insecticides; D010573:Pesticide Residues; D062367:ortho-Aminobenzoates; C517733:chlorantranilipole