Structure-Activity Relationships in Fungicidal 1-(2-Benyl-3, 3-dimethylbutanoyl)imidazoles and Related Compounds

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1-(2-Benzyl-3, 3-dimethylbutanoyl)imidazoles and related compounds were prepared and tested for their fungicidal activity against powdery mildew on barley (Erysiphe graminis) and gray mold on cucumber (Botrytis cinerea) by pot tests. The benzyl group at the 2-position of 1-(3, 3-dimethylbutanoyl)imidazoles was necessary for high activity against both fungi. Substitution at the 2- or 3-position of the benzene ring of 1-(2-benzyl-3, 3-dimethylbutanoyl)imidazoles was unfavorable to the activity. The activity of ten 1-(2-benzyl-3, 3-dimethylbutanoyl)imidazoles with various substituents at the 4-position of the benzene ring against both fungi was shown by a regression analysis to be correlated with the electronic property of the 4-substituents, in which the stronger the electron-withdrawing power, the higher the activity. The activity of 1-acyltriazoles was lower than that of 1-acylimidazoles, especially against B. cinerea. The (+)-isomer of 1-[2-(4-substituted benzyl)-3, 3-dimethylbutanoyl]imidazoles was superior to the (-)-isomer in controlling both fungi.
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