STRUCTURE-ACTIVITY-RELATIONSHIPS OF ENANTIOMERS OF THE AZOLE FUNGICIDE IPCONAZOLE AND ITS RELATED-COMPOUNDS - FUNGICIDAL AND PLANT-GROWTH INHIBITORY ACTIVITIES

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