Synthesis and Antifungal Activity of 5-Methoxy-2-nitrophenylphosphoramidothioates

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  • KOHSAKA Hideo
    Pesticides Research Laboratory, Takarazuka Research Center, Sumitomo Chemical Co., Ltd.
  • OGURI Yukio
    Pesticides Research Laboratory, Takarazuka Research Center, Sumitomo Chemical Co., Ltd.
  • SASAKI Mitsuru
    Pesticides Research Laboratory, Takarazuka Research Center, Sumitomo Chemical Co., Ltd.
  • MUKAI Kunio
    Pesticides Research Laboratory, Takarazuka Research Center, Sumitomo Chemical Co., Ltd.

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Other Title
  • 5-メトキシ-2-ニトロフェニルチオノリン酸アミド類の合成と抗菌活性
  • 5-メトキシー2-ニトロフェニルチオノリン酸アミド類の合成と抗菌活性〔英文〕
  • 5 メトキシ 2 ニトロフェニルチオノリンサン アミドルイ ノ ゴウセイ ト

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Abstract

Thirty-three 5-methoxy-2-nitrophenylphosphoramidothioates and phosphonamidothioates were synthesized and tested for their antifungal activity against downy mildew on cucumber in greenhouse pot tests. Among the compounds O-ethyl O-(5-methoxy-2-nitrophenyl) phosphoramidothioates having either an isopropylamino group, a 1-cyano-2-propylamino group, a 1-methoxy-2-butylamino group, or a s-butylamino group showed the highest activity. A 1-methoxy-2-propylamino group, a 3-methoxypropylamino group and a 1, 1-dioxotetrahydrothiophen-3-ylamino group effectively reduced the phytotoxicity without affecting the antifungal activity. Among N-isopropylphosphoramidothioates and phosphonamidothioates, O-methyl or O-ethyl phosphoramidothioates showed the highest activity. Chloromethylphosphonamidothioate was also effective, but phenylphosphonamidothioate was not effective. O-Ethyl O-(5-methoxy-2-nitrophenyl) N-s-butylphosphoramidate was hardly effective.

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