1997
DOI: 10.1584/jpestics.22.119
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Synthesis of Stereoisomers of Ipconazole and Their Fungicidal and Plant Growth Inhibitory Activities

Abstract: Two racemic diastereomers 5a and 5b, both of which are active ingredient of a seed treatment fungicide on rice, Ipconazole, (1RS, 2SR, 5RS; 1RS, 2SR, 5SR)-2-(4-chloropenzyl)-5-isopropyl-l-(1H-1, 2, 4-triazol-l-ylmethyl)cyclopentanol, and two other racemic diastereomers (1RS, 2RS, 5RS)-5c and (1RS, 2RS, 5SR)-5d were synthesized, and fungicidal activity and plant growth inhibitory activity were examined. Enantiomers of 5a and 5b were prepared, and their fungicidal activities were also examined. Racemic diastereo… Show more

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Cited by 8 publications
(2 citation statements)
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“…Wettable powders, waterdispersible granules, emulsifiable concentrates. Ipconazole can be prepared by reaction of methyl 3-isopropyl-2-oxocyclopentanecarboxylate with 4-chlorobenzyl chloride affording 2-(4-chlorobenzyl)-5-isopropylcyclopentane, which is treated with trimethylsulfoxonium iodide to yield 4-(4-chlorobenzyl)-7-isopropyl-1-oxaspiro [2,4]heptane, which is treated with 1,2,4-triazole in the presence of sodium hydride [128].…”
Section: Triazolesmentioning
confidence: 99%
“…Wettable powders, waterdispersible granules, emulsifiable concentrates. Ipconazole can be prepared by reaction of methyl 3-isopropyl-2-oxocyclopentanecarboxylate with 4-chlorobenzyl chloride affording 2-(4-chlorobenzyl)-5-isopropylcyclopentane, which is treated with trimethylsulfoxonium iodide to yield 4-(4-chlorobenzyl)-7-isopropyl-1-oxaspiro [2,4]heptane, which is treated with 1,2,4-triazole in the presence of sodium hydride [128].…”
Section: Triazolesmentioning
confidence: 99%
“…1) contain three asymmetric carbons, and as a consequence, there are four possible racemic diastereomers and eight enantiomers. 13) There are cis and trans isomers with respect to the hydroxy group and the benzyl group, and each isomer has further cis and trans isomers with respect to the hydroxy group and the alkyl substituent on the cyclopentane ring. Furthermore, each racemic diastereomer consists of two enantiomers.…”
Section: Introductionmentioning
confidence: 99%