Add time:07/21/2019         Source:sciencedirect.com

The plant metabolism of the phenylurea herbicide isoproturon (IPU) was studied in aseptic cell suspension cultures of soybean and wheat. After incubation with the14C-labeled herbicide (1 ppm) over 48 h, total metabolic rates were 45–54%. The predominant metabolites in soybean were identified as monodesmethyl-IPU, 2-hydroxy-IPU, and 2-hydroxy-monodesmethyl-IPU. The major metabolic pathway identified for wheat was the conversion of IPU to 2-hydroxy-IPU as the primary metabolite and then to 2-hydroxy-monodesmethyl-IPU. 2-Hydroxy-IPU and an olefinic metabolite (isopropenyl-IPU) are described here for the first time. Metabolite identification was based on high-performance liquid chromatography retention times as well as time-of-flight/secondary-ion mass spectrometry and1H nuclear magnetic resonance spectroscopy. Wheat microsomes catalyzed the NADPH-dependent conversion of isoproturon to monodesmethyl and 2-hydroxy-monodesmethyl metabolites. 2-Hydroxy-IPU was only a minor enzymatic product so there was a remarkable difference between the primary cellular and enzymatic metabolites.14C Incorporation into the wheat-insoluble residue fraction increased from 3% (48 h) to 14% (7 days). A sequential solubilization procedure indicated that binding occurred mainly to the operationally defined hemicellulose (65%) and lignin (10%) fractions. Simulated stomach conditions (pH 1, 37° C, 24 h) released only about 5% of total bound radioactivity. The similarity of IPU metabolism in microbial, plant, and animal systems is discussed, with 2-hydroxy-monodesmethyl-IPU being a common metabolite.

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