Discovery and Development of New Rice Herbicide, Indanofan.

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  • Jikihara Tetsuo
    Agrochemicals Laboratory, Specialty Chemicals Research Center, Mitsubishi Chemical Corporation
  • Hosokawa Akemi
    三菱化学株式会社機能化学品研究センターAPI研究所

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  • 除草剤インダノファンの創製
  • ジョソウザイ インダノファン ノ ソウセイ

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Abstract

Indanofan ((RS) -2-[[2-(3-chlorophenyl) oxiranyl] methyl] -3-eth ylindan-1, 3-dione), a novel class of grass herbicide, was discovered by Mitsubishi Chemical Corporation during the study of oxiran containing herbicidally active compounds. It was introduced into the market in 1999, and is now widely used as the active ingredient for One-shot rice herbicides in Japan. It controls Echinochloa oryzicola of 0 to 2.5 leaf-stage at 100 to 150g a.i./ha for enough periods even at low temperature.<BR>Indanofan is characterized by its unique chemical structure due to indan-1, 3-dione and 2-phenyl substituted oxirane moieties bridged via methylene carbon atom. This paper describes firstly the drug design process for indanofan, lead generation and lead optimization, and secondly the synthesis and manufacturing process of indanofan and its key intermediates, 2-ethylindan-1, 3-dione and 1-chloro-3- (1-chloromethylvinyl) benzene including the oxidation process using high concentration peracetic acid.

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