{"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, Hazna Sartiva, 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":null,"pages":null},"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, Hazna Sartiva, 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\":null,\"pages\":null},\"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}
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-OCH37: IC50=121 µM, 8-OCH38: 56.7 µM). Methyl derivatives at the 5- or 8-position showed activity levels similar to those of the compound without substituents 2 (5-CH313: IC50=214 µM, 8-CH316: IC50=225 µM). The activities of OH- and F-derivatives were not observed or were lower.
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.
![Effect of further substitutions at 5-, 6-, 7-, or 8-position of 3-[3-(4-methoxyphenyl)-1-hydroxyprop-2-yl]coumarin on phytotoxicity.](https://img.booksci.cn/booksciimg/2023-8/2023120378230905339628757792806.jpg)
![Effect of further substitutions at 5-, 6-, 7-, or 8-position of 3-[3-(4-methoxyphenyl)-1-hydroxyprop-2-yl]coumarin on phytotoxicity.](https://img.booksci.cn/booksciimg/2023-8/2023120378258179902835269780496.jpg)
![Effect of further substitutions at 5-, 6-, 7-, or 8-position of 3-[3-(4-methoxyphenyl)-1-hydroxyprop-2-yl]coumarin on phytotoxicity.](https://img.booksci.cn/booksciimg/2023-8/202312037827606866443091716403.jpg)
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