Synthesis and Herbicidal Activity of <i>N</i>-(2-Pyridyloxiran-2-ylmethyl)benzenesulfonamide Derivatives

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  • HOSOKAWA Akemi
    Agricultural Chemicals Laboratory, Yokohama Research Center, Mitsubishi Chemical Co., Ltd.
  • KATSURADA Manabu
    Agricultural Chemicals Laboratory, Yokohama Research Center, Mitsubishi Chemical Co., Ltd.
  • MIKAMI Emiko
    Agricultural Chemicals Laboratory, Yokohama Research Center, Mitsubishi Chemical Co., Ltd.
  • IKEDA Osamu
    Agricultural Chemicals Laboratory, Yokohama Research Center, Mitsubishi Chemical Co., Ltd.
  • MINAMI Noriko
    Agricultural Chemicals Laboratory, Yokohama Research Center, Mitsubishi Chemical Co., Ltd.
  • JIKIHARA Tetsuo
    Agricultural Chemicals Laboratory, Yokohama Research Center, Mitsubishi Chemical Co., Ltd.

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Other Title
  • <i>N</i>-(2-ピリジルオキシラン-2-イルメチル)ベンゼンスルホンアミド誘導体の合成および除草活性
  • Synthesis and Herbicidal Activity of N-(2-Phyridyloxiran-2-ylmethyl)benzenesulfonamide Derivatives
  • Synehesis and Herbicidal Activity of Novel Oxirane Derivatives (Part 2)

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Abstract

In the course of studies on sulfonamides with aryl substitutedoxirane moiety, we found that compounds having a pyridyl group on 2-position of the oxiran-2-ylmethyl moiety possessed herbicidal activity. As a result of elaborate study, 4-chloro-N-[2-(6-chloropyridin-2-yl)oxiran-2-ylmethyl]-3, N-dimethylbenzenesulfonamide and N-[2-(6-chloropyridin-2-yl) oxiran-2-ylmethyl]-N-methyl-5, 6, 7, 8-tetrahydronaphthalene-2-sulfonamide were discovered as potential rice herbicides. The former compound showed complete control of Echinochloa oryzicola (barnyardgrass) up to 2 leaf stage and broad herbicidal spectrum. The latter compound showed remarkable selectivity between rice and Echinochloa oryzicola.

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