Acifluorfen metabolism in soybean: Diphenylether bond cleavage and the formation of homoglutathione, cysteine, and glucose conjugates |
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| Authors: | D S Frear H R Swanson E R Mansager |
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| Abstract: | Metabolism of the substituted diphenylether herbicide, acifluorfen sodium 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate], was studied in excised leaf tissues of soybean Glycine max (L.) Merr. ‘Evans’]. Studies with chlorophenyl-14C]- and nitrophenyl-14C]acifluorfen showed that the diphenylether bond was rapidly cleaved. From 85 to 95% of the absorbed 14C]acifluorfen was metabolized in less than 24 hr. Major polar metabolites were isolated and purified by solvent partitioning, adsorption, thin layer, and high-performance liquid chromatography. The major chlorophenyl-14C]-labeled metabolite was identified as a malonyl-β-
-glucoside (I) of 2-chloro-4-trifluoromethylphenol. Major nitrophenyl-14C]-labeled metabolites were identified as a homoglutathione conjugate S-(3-carboxy-4-nitrophenyl) γ-glutamyl-cysteinyl-β-alanine] (II), and a cysteine conjugate S-(3-carboxy-4-nitrophenyl)cysteine] (III). |
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