Synthesis and Herbicidal Activity of New 2-(1-Carbamoyl-1, 2, 4-triazol-3-ylsulfonyl) alkanoates

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A series of new 2-(1-N, N-dialkylcarbamoyl-1, 2, 4-triazol-3-ylsulfonyl) alkanoates were synthesized and examined for herbicidal activity against weeds. The herbicidal efficacy varied with the substituents at the α-position of the alkoxycarbonyl group and on the nitrogen atom of the carbamoyl moiety. Among the compounds synthesized, 1-N, N-dialkylcarbamoyl-1, 2, 4-triazole derivatives having a branched alkyl group at the α-position of the alkoxycarbonyl group exhibited the most potent herbicidal activity. The chirality of the α-position had no effect on the activity. On the basis of biological evaluations, isopropyl 2-(1-N, N-diethylcarbamoyl-1, 2, 4-triazol-3-ylsulfonyl)-4-methylpentanoate was selected as a promising herbicidal candidate for transplanted rice. Studies on structure-activity relationships using the hydrophobicity parameter logk′ revealed that hydrophobicity markedly influenced the herbicidal activity.
日本農薬学会の論文