Metconazole, (1
RS, 5
RS; 1
RS, 5
SR)-5-(4-chlorobenzyl)-2, 2-dimethyl-1-(1
H-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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