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。

IF 1.5 4区 农林科学 Q2 ENTOMOLOGY
Satoshi Yamauchi, Hazna Sartiva, Hisashi Nishiwaki
{"title":"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。","authors":"Satoshi Yamauchi,&nbsp;Hazna Sartiva,&nbsp;Hisashi Nishiwaki","doi":"10.1584/jpestics.D23-016","DOIUrl":null,"url":null,"abstract":"<p><p>Derivatives of the coumarin ring in (<i>R</i>)-3-[3-(4-methoxyphenyl)-1-hydroxyprop-2-yl]coumarin <b>2</b>, which is a lignan structure, were synthesized to clarify their structure-phytotoxicity relationships. The growth-inhibitory activity of the 8-OCH<sub>3</sub> derivative <b>8</b> (IC<sub>50</sub>=228 µM) was more potent against the roots of lettuce seedlings than the compound without substituents <b>2</b>. 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-OCH<sub>3</sub> <b>7</b>: IC<sub>50</sub>=121 µM, 8-OCH<sub>3</sub> <b>8</b>: 56.7 µM). Methyl derivatives at the 5- or 8-position showed activity levels similar to those of the compound without substituents <b>2</b> (5-CH<sub>3</sub> <b>13</b>: IC<sub>50</sub>=214 µM, 8-CH<sub>3</sub> <b>16</b>: IC<sub>50</sub>=225 µM). The activities of OH- and F-derivatives were not observed or were lower.</p>","PeriodicalId":16712,"journal":{"name":"Journal of Pesticide Science","volume":"48 3","pages":"93-98"},"PeriodicalIF":1.5000,"publicationDate":"2023-08-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://ftp.ncbi.nlm.nih.gov/pub/pmc/oa_pdf/f2/8e/jps-48-3-D23-016.PMC10513945.pdf","citationCount":"0","resultStr":"{\"title\":\"Effect of further substitutions at 5-, 6-, 7-, or 8-position of 3-[3-(4-methoxyphenyl)-1-hydroxyprop-2-yl]coumarin on phytotoxicity.\",\"authors\":\"Satoshi Yamauchi,&nbsp;Hazna Sartiva,&nbsp;Hisashi Nishiwaki\",\"doi\":\"10.1584/jpestics.D23-016\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>Derivatives of the coumarin ring in (<i>R</i>)-3-[3-(4-methoxyphenyl)-1-hydroxyprop-2-yl]coumarin <b>2</b>, which is a lignan structure, were synthesized to clarify their structure-phytotoxicity relationships. The growth-inhibitory activity of the 8-OCH<sub>3</sub> derivative <b>8</b> (IC<sub>50</sub>=228 µM) was more potent against the roots of lettuce seedlings than the compound without substituents <b>2</b>. 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-OCH<sub>3</sub> <b>7</b>: IC<sub>50</sub>=121 µM, 8-OCH<sub>3</sub> <b>8</b>: 56.7 µM). Methyl derivatives at the 5- or 8-position showed activity levels similar to those of the compound without substituents <b>2</b> (5-CH<sub>3</sub> <b>13</b>: IC<sub>50</sub>=214 µM, 8-CH<sub>3</sub> <b>16</b>: IC<sub>50</sub>=225 µM). The activities of OH- and F-derivatives were not observed or were lower.</p>\",\"PeriodicalId\":16712,\"journal\":{\"name\":\"Journal of Pesticide Science\",\"volume\":\"48 3\",\"pages\":\"93-98\"},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2023-08-20\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://ftp.ncbi.nlm.nih.gov/pub/pmc/oa_pdf/f2/8e/jps-48-3-D23-016.PMC10513945.pdf\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Pesticide Science\",\"FirstCategoryId\":\"97\",\"ListUrlMain\":\"https://doi.org/10.1584/jpestics.D23-016\",\"RegionNum\":4,\"RegionCategory\":\"农林科学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"ENTOMOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Pesticide Science","FirstCategoryId":"97","ListUrlMain":"https://doi.org/10.1584/jpestics.D23-016","RegionNum":4,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"ENTOMOLOGY","Score":null,"Total":0}
引用次数: 0

摘要

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。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

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

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

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

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

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.

求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
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.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信