定量的構造活性相関の応用による殺菌剤の分子設計

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概要

• 論文の詳細を見る

• The design of new cyclic N-phenylimide fungicides was performed by using a QSAR technique, the Hansch-Fujita method. Furthermore, a computer program called PREHAC, which aids in the impartial selection of substituents for the synthesis of highly bioactive compounds among congeners based on the Hansch-Fujita method, was developed and used effectively for the above-mentioned fungicide design. 3, 5-Dihalo substituents on the benzene ring moiety enhance greatly the antifungal activity of cyclic N-phenylimides against Sclerotinia sclerotorum, Botrytis cinerea, etc. The relationships between the chemical structure and antifungal activity against B. cinerea of a number of N-phenylsuccinimides and related N-phenyl-1, 2-dimethylcyclopropanedicarboximides having various benzene ring substituents were analyzed for the purpose of the clarification of the physicochemical meaning of 3, 5-dihalo substituents and the search for substitutes for them. The high antifungtal actibvity of the cyclic N-(3.5-dihalopheny) imides was rationalized by the hydrophobicity and electron-withdrawing properties of halogen atoms. In addition, the steric bulk of one of the two halogen atoms was revealed to be unfavorable to this activity. It was concluded that 3, 5-dihalo sub-stitutions were most desirable for high activity of this series of compounds. The antifungal activity of N-(3.5-dichlorophenyl)succinimides and 3-(3, 5-dichlorophenyl)-2, 4-oxazolidine-diones, having various substituents on the imido rings, against B. cinerea was related only with the hydrophobicity of the imido ring moieties including the substituents. The 1-iso-valeroyl derivative of 3-(3, 5-dichiorophenyl)-2, 4-imidazolidinedione (isovaledione) was designed as a new fungicide against Alternaria diseases. The activity of 1-acy1-3-(3, 5-di-chlorophenyl)-2, 4-imidazolidinediones against A. kikuchiana was related parabolically with both the hydrophobicity and steric bulkiness of the acyl moiety substituents. The higher the electron-donating power of the substituents and the smaller their minimum width in the direction perpendicular to the bond axis, the greater was the activity.

• 日本農薬学会の論文
• 1985-08-20

著者

• 高山 千代蔵

  Agricultural Chemicals Research Laboratory Sumitomo Chemical Co. Ltd.

• 高山 千代蔵

  住友化学工業株式会社宝塚総合研究所農薬研究所

• 高山 千代蔵

  住友化学工業 (株) 宝塚綜合研究所

関連論文

• 有機リン剤の脂質二重膜への分配
• イエバエに対する含複素環ピレスロイドの殺虫活性およびその構造活性相関
• 非テルペン型幼若ホルモン様活性物質のコンホメーション解析および安定コンホメーションにおける立体類似性
• 殺虫剤α-シアノベンジルシクロプロパンカルボン酸エステル類の構造活性相関
• N-(3, 5-Dichlorophenyl)cyclopropanedicarboximides の抗菌活性に及ぼすシクロプロパン環上メチル基の効果
• 抗菌活性を有する 1-アシル-3-(3, 5-ジクロロフェニル)-2, 4-イミダゾリジンジオン類の定量的構造活性相関
• 除草活性を有する N-(1-methyl-1-phenylethyl) phenylacetamides の定量的構造活性相関
• N-Benzylbutanamide 類のハマスゲに対する除草活性の定量的構造活性相関
• O, O-Dialkyl O-aryl phosphorothioates および関連化合物の合成と抗菌活性
• 除草活性を有する N-benzyl-2-bromo-3, 3-dimethylbutanamides の定量的構造活性相関
• 除草活性を有する N-(1-methyl-1-phenylethyl)-acylamides の定量的構造活性相関
• 殺菌活性を有する N-(3, 4-diethoxyphenyl)-carbamate 類の定量的構造活性相関
• 1-Acyl-3-(3, 5-dichlorophenyl)-2, 4-imidazolidinediones の抗菌活性に及ぼすアシル部分の置換基の立体効果
• 殺菌活性を有する N-benzylacylamides の定量的構造活性相関
• 農薬の定量的構造活性相関と活性間の相関解析 (コンピュ-タと有機化学特集号)
• 定量的構造活性相関の応用による殺菌剤の分子設計
• N-Benzylbutanamides の除草活性におけるアシル部分およびアミン部分の置換基の立体効果
• コンピュ-タ-ケミストリ-とデ-タベ-ス (計算"器"化学--フラスコにかえて計算機を)
• 農薬の定量的構造活性相関と活性間の相関解析
• 新しい含フッ素農薬の展望
• N-フェニルイミド系殺菌剤の構造活性相関とドラッグデザイン (構造活性相関とドラッグデザイン)
• 生理活性物質研究とコンピュ-タ

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