Diphenamid Metabolism in Pepper and an Ozone Effect. II. Herbicide Metabolite Characterization

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Abstract
Metabolites of diphenamid (N,N-dimethyl-2,2-diphenyl-acetamide) were purified from extracts of pepper plants (Capsicum frutescens L. ‘Early Calwonder’) treated via nutrient solution with the herbicide or several of its analogs. The major metabolites were characterized. Diphenamid was metabolized partially via a previously unreported pathway to N,N-dimethyl-2-phenyl-2-[(hydroxyphenyl)-β-0-D-glucosyl] acetamide and its monomethyl analog, and to N-hydroxymethyl glycosides previously reported in other species. Ozone fumigation stimulated the production of both types of glycoside-conjugates. Leaves of plants that had been treated with 30 μM diphenamid and fumigated with ozone for 146 to 149 h contained 304 and 560 nmoles per gram of fresh weight of the hydroxyphenyl and N-hydroxymethyl conjugates, respectively.