Characterization of bound phenthoate residues in citrus

The metabolism and fate of phenyl ring-labeled 14C-phenthoate (0,0-dimethyl S-[alpha-(carboethoxy)benzyl] phosphorodithioate) was examined in the Valencia orange fruit with emphasis on the characterization of bound phenthoate residues in the fruit peel. The products recovered from the citrus fruit wash were unchanged phenthoate, phenthoate oxon, demethyl phenthoate, phenthoate acid, ethyl mandelate, and mandelic acid. The same products, with the exception of phenthoate oxon, were found in the acetone extract of the fruit peel. Enzymatic hydrolysis of the bound residue in the peel with beta-glucosidase, followed by acidic and basic hydrolysis gave ethyl mandelate as the major product, followed by mandelic acid, demethyl phenthoate and phenthoate acid. Phenthoate was metabolized and conjugated in citrus fruits into detoxication products.