Metabolism of the herbicide 2-(α-naphthoxy)-N,N-diethyl propionamide (R-7465) by tomato plants (Lycopersicon esculentum Mill. ‘Mechanical Harvester’) was investigated. Ring-labeled R-7465-14C was taken up rapidly by the roots and distributed throughout the leaves within 8 hr. R-7465 was converted primarily into water soluble metabolites. The principal metabolite was identified as a hexose conjugate of 2-(α-naphthoxy-4-hydroxy)-N,N-diethyl propionamide. This metabolite represented 47% of the soluble radioactivity in the plant. A different hexose conjugate of 2-(α-naphthoxy-4-hydroxy)-N,N-diethyl propionamide together with a hexose conjugate of 2-(α-naphthoxy-4-hydroxy)-N-ethyl propionamide accounted for another 22% of the radioactivity. Nonmetabolized R-7465 was found to represent only 5% of the total soluble radioactivity. Other identified metabolites included 2-(α-napthoxy)-N-ethyl propionamide, 2-(α-naphthoxy-5-hydroxy)-N,N-diethyl propionamide, and 1,4-naphthoquinone. None of these metabolites individually represented more than 3% of the soluble radioactivity in the plants. Ring hydroxylation and N-dealkylation appeared to be the initial steps in detoxification of R-7465 followed by conjugation with sugars.
Generation of blue chrysanthemums by anthocyanin B-ring hydroxylation and glucosylation and its coloration mechanism
