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Synthesis and Herbicidal Activity of New 2-(1-Carbamoyl-1,2,4-triazol-3-ylsulfonyl)alkanoates
Tomoyuki YANO, Tomoko YOSHII, Takuya UEDA, Masahiro HORI and Kenji HIRAI
J. Pestic. Sci.
27, 97-105 (2002)
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 alpha-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 alpha-position of the alkoxycarbonyl group exhibited the most potent herbicidal activity. The chirality of the alpha-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 log k' revealed that hydrophobicity markedly influenced the herbicidal activity.
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