Synthesis and Bleaching Activity of 3-Propargylthio-4-(substituted phenyl)-4<i>H</i>-1, 2, 4-triazoles

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  • TAKEHARA Koji
    Laboratory of Pesticide Chemistry, Department of Agricultural Chemistry, Kyushu University
  • YAMADA Naotaka
    Laboratory of Pesticide Chemistry, Department of Agricultural Chemistry, Kyushu University
  • HAKIRA Hidetoshi
    Laboratory of Pesticide Chemistry, Department of Agricultural Chemistry, Kyushu University
  • KUWANO Eiichi
    Laboratory of Pesticide Chemistry, Department of Agricultural Chemistry, Kyushu University
  • TANIGUCHI Eiji
    Laboratory of Pesticide Chemistry, Department of Agricultural Chemistry, Kyushu University

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Other Title
  • 3-プロパルギルチオ-4-置換フェニル-4<i>H</i>-1,2,4-トリアゾール類の合成とその白化活性
  • 3-プロパルギルチオー4-置換フェニルー4H-1,2,4-トリアゾール類の合成とその白化活性〔英文〕
  • 3 プロパルギルチオ 4 チカン フェニル 4H 1 2 4 トリアゾールルイ

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Abstract

A number of 3-alkylthio-4-aryl-4H-1, 2, 4-triazoles were synthesized and evaluated for their bleaching activity by using a lettuce seedling test. In a series of 4-phenyl-4H-1, 2, 4-triazoles, 3-propylthio and 3-propargylthio analogs caused complete bleaching symptoms at 50ppm, while the activity fell off with increasing or decreasing size of the alkylthio group at the 3-position of the triazole ring. The introduction of a chloro, trifluoromethyl, methyl or ethoxy substituent at the meta- or para-position on the benzene ring increased the activity in comparison with that of the phenyl analog. 4-(3-Chlorophenyl and 4-chlorophenyl)-3-propargylthio-4H-1, 2, 4-triazole (16 and 17) markedly reduced β-carotene content as well as chlorophyll in plants. Inhibition of β-carotene formation was accompanied by an accumulation of large amounts of phytoene, suggesting that these 1, 2, 4-triazoles inhibit the desaturation of phytoene.

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