Rat intestinal metabolism of crufomate (4-tert-butyl-2-chlorophenyl methyl methylphosphoramidate)

Everted sacs of rat small intestine metabolized crufomate (4-tert-butyl-2-chlorophenyl methyl methylphosphoramidate) under in vitro conditions to form six 14C-labeled metabolites in quantities sufficient for isolation and identification. These metabolites were 4-tert-butyl-2-chlorophenyl methyl phosphoramidate (25%), 2-chloro-4(2-hydroxy-1,1-dimethylethyl)phenyl methyl methylphosphoramidate (19%), 2-[3-chloro-4-[[(methoxy) (methyl-amino)phosphoinyl]oxy]phenyl]-2-methylpropionic acid (2%), 4-tert-butyl-2-chlorophenol (0.8%) and its glucuronide (6%), and the aromatic glucuronide of 2-chloro-4(2-hydroxy-1,1-dimethylethyl)phenol (1%). These intestinal metabolites may represent precursory stages in the overall metabolism of crufomate.