Abstract
Enantiomers of a seed treatment fungicide, ipconazole, (1RS, 2SR, 5RS; 1RS, 2SR, 5SR)-2-(4-Chlorobenzyl)-5-isopropyl-1-(1H-1, 2, 4-triazol-1-ylmethyl)cyclopentanol, and its related compounds which have no or differing alkyl groups at the fifth position on the cyclopentane ring in place of the isopropyl group were prepared, and their fungicidal and plant growth inhibitory activities were examined. Of the eighteen enantiomers tested, high fungicidal activity was observed for nine enantiomers with identical absolute configuration types. Two fungicidal enantiomers substituted with no alkyl group or a methyl group (I-B and II-B, respectively) retarded the growth of wheat and cucumber. The other enantiomers did not affect the growth of wheat or cucumber except non-fungicidal enantiomers substituted with an ethyl group, which caused growth inhibition of wheat seedlings. The morphology of plants treated with I-B or II-B was similar to that of plants treated with uniconazole, a known gibberellin biosynthesis inhibitor.
