Systematic Syntheses and Structure-Activity Relationships of Substituted and Nonsubstituted Isochroman-3-ones as Plant Growth Regulators

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  • WATANABE Katsuji
    Laboratory of Pesticide Chemistry, Faculty of Agriculture, Kyushu University Department of Agro-Environmental management, Kyushu National Agricultural Experiment Station, Nishigoshi
  • TANIGUCHI Eiji
    Laboratory of Pesticide Chemistry, Faculty of Agriculture, Kyushu University

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Other Title
  • 植物成長調節剤としてのイソクロマン-3-オン類の系統的な合成と構造活性相関について
  • 植物成長調節剤としてのイソクロマンー3-オン類の系統的な合成と構造活性相関について〔英文〕
  • ショクブツ セイチョウ チョウセツザイ トシテノ イソクロマン 3 オンルイ

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In order to obtain lead compounds for new plant growth regulators, systematic syntheses of isochroman-3-ones and their plant growth regulating activity were investigated. 1-Substituted isochroman-3-ones were synthesized by the reduction and cyclization of 2-acylphenylacetic acids which were obtained by dichromate oxidation of 3-substituted indenes. 1-Substituted-6, 7-dimethoxyisochroman-3-ones were synthesized in a similar manner from the corresponding 2-acylphenylacetic acids which were obtained by the Freidel-Crafts acylation of 3, 4-dimethoxyphenylacetic acid with acyl halides. The isochroman-3-ones without substituent on the 1-position were obtained by regio selective chloromethylation or hydroxymethylation of phenylacetic acids. The isochroman-3-ones without substituent on the lactone ring had no activity on hypocotyl and radicule elongations of lettuce seedlings at 10ppm. The 1-phenyl, benzyl and stryl substituted compounds promoted the radicule elongation while inhibited the hypocotyl elongation of lettuce seedlings at 10ppm. We concluded that the inhibition might be attributed to auxin transport inhibition and the elongation might be attributed to antiauxin activity.

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