Structure-Activity Relationships of the Azole Fungicide Metconazole and Its Related Azolylmethylcycloalkanols

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  • アゾール系殺菌剤メトコナゾールとその関連アゾリルメチルシクロアルカノール誘導体の構造活性相関

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Abstract

Metconazole, (1RS, 5RS; 1RS, 5SR)-5-(4-chlorobenzyl)-2, 2-dimethyl-1-(1H-1, 2, 4-triazol-1-ylmethyl)cyclopentanol, is a novel triazole fungicide containing a cyclopentane ring. The related compounds, cyclopentanol, cyclohexanol and cycloheptanol derivatives having none or gem-dimethyl groups at the 2-position on the cycloalkane ring were synthesized, and their fungicidal activities were compared. The gem-dimethyl groups at the 2-position on the cyclohexane and cycloheptane rings were important for fungicidal activity as well as the case of the cyclopentanols. The cis-isomers of the cyclopentanols and the cycloheptanols showed higher fungicidal activities than the trans-isomers of them. On the contrary, the trans-isomers of the cyclohexanols were more active than the cis-isomers of them, but less active than the cis-isomers of the cyclopentanols and the cycloheptanols. Among the cis-cycloalkanols, the cyclopentanols and the cycloheptanols showed higher activities than the cyclohexanols. The conformational analysis of these cycloalkanols indicated that the relative three-dimensional orientation of the two important aromatic rings, triazole and benzene, of the cycloalkanols affected their fungicidal activities.

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