Effect of further substitutions at 5-, 6-, 7-, or 8-position of 3-[3-(4-methoxyphenyl)-1-hydroxyprop-2-yl]coumarin on phytotoxicity.

IF 1.5 4区 农林科学 Q2 ENTOMOLOGY Journal of Pesticide Science Pub Date : 2023-08-20 DOI:10.1584/jpestics.D23-016
Satoshi Yamauchi, Hazna Sartiva, Hisashi Nishiwaki
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Abstract

Derivatives of the coumarin ring in (R)-3-[3-(4-methoxyphenyl)-1-hydroxyprop-2-yl]coumarin 2, which is a lignan structure, were synthesized to clarify their structure-phytotoxicity relationships. The growth-inhibitory activity of the 8-OCH3 derivative 8 (IC50=228 µM) was more potent against the roots of lettuce seedlings than the compound without substituents 2. As for the roots of Italian ryegrass seedlings, the presence of the methoxy group at the 7- or 8-position was extremely effective for inhibiting growth (7-OCH3 7: IC50=121 µM, 8-OCH3 8: 56.7 µM). Methyl derivatives at the 5- or 8-position showed activity levels similar to those of the compound without substituents 2 (5-CH3 13: IC50=214 µM, 8-CH3 16: IC50=225 µM). The activities of OH- and F-derivatives were not observed or were lower.

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3-[3-(4-甲氧基苯基)-1-羟基-2-基]香豆素在5-、6-、7-或8-位的进一步取代对植物毒性的影响。
合成了木脂素结构的(R)-3-[3-(4-甲氧基苯基)-1-羟基-2-基]香豆素2中香豆素环的衍生物,以阐明它们的结构-植物毒性关系。8-OCH3衍生物8的生长抑制活性(IC50=228 µM)比没有取代基的化合物2对莴苣幼苗的根更有效。对于意大利黑麦草幼苗的根,在7-或8-位存在甲氧基对抑制生长非常有效(7-OCH37:IC50=121 µM,8-OCH3 8:56.7 µM)。5-或8-位的甲基衍生物显示出与没有取代基2的化合物相似的活性水平(5-CH3 13:IC50=214 µM,8-CH3 16:IC50=225 µM)。OH-和F-衍生物的活性没有观察到或较低。
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来源期刊
Journal of Pesticide Science
Journal of Pesticide Science 农林科学-昆虫学
CiteScore
4.30
自引率
4.20%
发文量
28
审稿时长
18-36 weeks
期刊介绍: The Journal of Pesticide Science publishes the results of original research regarding the chemistry and biochemistry of pesticides including bio-based materials. It also covers their metabolism, toxicology, environmental fate and formulation.
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