N-ベンジルブタンアミド系除草剤の開発に関する研究

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概要

• 論文の詳細を見る

• The N-benzylbutanamides like N-(1-methyl-1-phenylethyl)-2-bromo-3, 3-dimethylbutanamide (bromobutide, S-47) with bulky substituents in the acid and amine moieties are new herbicides that are extremely effective against annual and also perennial weeds. These herbicides were designed according to previous quantitative structure-activity studies. Systematic modification of the amide at both the acid and amine moieties gave herbicides with bulky substituents that might inhibit degradation mechanisms. The effect of the substituents was analyzed by using Hansch-Fujita method. The herbicidal activity of N-(1-methyl-1-phenylethyl) acylamides against bulrush was related parabolically with both the hydrophobicity and minimum width of the substituents at the acid moiety. The greater the maximum width, the higher the activity. When tested against purple nutsedge, the greater the steric bulk of the substituents, the higher the activity and the haloalkyl substituent was detrimental to the activity. The activity of N-(α-substituted benzyl)-2-bromo-3, 3-dimethylbutanamides against bulrush was related parabolically with the maximum distance from the nitrogen atom to the edge of the α-substituents. The length of the benzene ring substituents was responsible for the variation in activity of the substituted phenyl derivatives. The N-[1-methyl-1-(p-methyl-phenyl) ethyl] group was favorable to the activity against purple nutsedge. The crystal structure of bromobutide was examined by X-ray analysis and the R-configuration at the acid moiety was essential to high activity. Bromobutide showed a broad herbicidal spectrum by controlling various weeds such as barnyardgrass, monochoria, bulrush, slender spikerush, spikerush, sedges and arrowhead with safety to the rice plant under paddy conditions and purple nutsedge, yellow nutsedge and barnyardgrass under upland conditions. N-(1-Methyl-1-phenylethyl)-2-ethyl-3, 3-dimethylbutanamide exhibited strong herbicidal activity under upland conditions against purple nutsedge. These compounds showed extensive movement in soil and gave good residual activities.

• 日本農薬学会の論文
• 1984-08-20

著者

• 桐野 修

  Pesticides Research Laboratory Takarazuka Research Center Sumitomo Chemical Co. Ltd.

• 桐野 修

  住友化学工業 (株) 宝塚総合研究所

関連論文

• 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
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• 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
• N-Benzylbutanamide およびその光学活性体の結晶構造と除草活性
• 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
• N-アリルアミノアセトニトリルの Fusarium oxysporum による病害防除機作 : アミノニトリルのフザリウム病防除活性(第 4 報)
• 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
• 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
• 農薬の定量的構造活性相関と活性間の相関解析
• ジクロロビニルシクロプロパンカルボン酸置換ベンジルエステル類の感受性および kdr-抵抗性ネッタイイエカ, Culex quinquefasciatus, に対する殺虫活性
• N-ベンジルブタンアミド系除草剤の開発に関する研究
• 農薬開発における定量的構造活性相関の応用 (薬物の構造活性相関-2-ドラッグデザインと作用機作研究の実際)

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