Synthesis and herbicidal activity of optically active cinmethylin, its enantiomer, and C3-substituted cinmethylin analogs.

IF 1.5 4区 农林科学 Q2 ENTOMOLOGY Journal of Pesticide Science Pub Date : 2023-02-20 DOI:10.1584/jpestics.D22-051
Narihito Ogawa, Shoya Toyoshima, Shinya Sekikawa, Masahiro Ishijima, Kyosuke Katagiri, Chihiro Uematsu, Tatsuya Hirano, Akihito Ootaka, Jun Suzuki
{"title":"Synthesis and herbicidal activity of optically active cinmethylin, its enantiomer, and C3-substituted cinmethylin analogs.","authors":"Narihito Ogawa,&nbsp;Shoya Toyoshima,&nbsp;Shinya Sekikawa,&nbsp;Masahiro Ishijima,&nbsp;Kyosuke Katagiri,&nbsp;Chihiro Uematsu,&nbsp;Tatsuya Hirano,&nbsp;Akihito Ootaka,&nbsp;Jun Suzuki","doi":"10.1584/jpestics.D22-051","DOIUrl":null,"url":null,"abstract":"<p><p>We investigated the synthesis and herbicidal activity of optically active cinmethylin, its enantiomer, and C3-substituted cinmethylin analogs. Optically active cinmethylin could be obtained in seven steps with the Sharpless asymmetric dihydroxylation of α-terpinene. The synthesized cinmethylin and its enantiomer showed similar herbicidal activity, which was independent of the stereochemistry. Next, we synthesized cinmethylin analogs with various substituents at the C3 position. We found that analogs with methylene, oxime, ketone, or methyl groups at the C3 position show excellent herbicidal activity.</p>","PeriodicalId":16712,"journal":{"name":"Journal of Pesticide Science","volume":"48 1","pages":"11-16"},"PeriodicalIF":1.5000,"publicationDate":"2023-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://ftp.ncbi.nlm.nih.gov/pub/pmc/oa_pdf/5b/d0/jps-48-1-D22-051.PMC9978247.pdf","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Pesticide Science","FirstCategoryId":"97","ListUrlMain":"https://doi.org/10.1584/jpestics.D22-051","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

Abstract

We investigated the synthesis and herbicidal activity of optically active cinmethylin, its enantiomer, and C3-substituted cinmethylin analogs. Optically active cinmethylin could be obtained in seven steps with the Sharpless asymmetric dihydroxylation of α-terpinene. The synthesized cinmethylin and its enantiomer showed similar herbicidal activity, which was independent of the stereochemistry. Next, we synthesized cinmethylin analogs with various substituents at the C3 position. We found that analogs with methylene, oxime, ketone, or methyl groups at the C3 position show excellent herbicidal activity.

Abstract Image

Abstract Image

Abstract Image

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
旋光性辛甲基林及其对映体和c3取代辛甲基林类似物的合成及其除草活性。
研究了旋光性辛甲基林及其对映体和c3取代辛甲基林类似物的合成及其除草活性。α-萜烯经Sharpless不对称二羟基化反应,经7步反应制得光学活性的五甲基林。合成的五甲基林及其对映体具有相似的除草活性,且与立体化学无关。接下来,我们合成了具有不同C3取代基的辛甲基林类似物。我们发现在C3位置上含有亚甲基、肟、酮或甲基的类似物具有良好的除草活性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 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.
期刊最新文献
Effect of pyriofenone on the infection processes and cytological features of Blumeria graminis on wheat leaves Synthesis and biological evaluation of burnettiene A derivatives enabling discovery of novel fungicide candidates. Enhanced disease resistance against Botrytis cinerea by strigolactone-mediated immune priming in Arabidopsis thaliana A reliable quantification of organophosphorus pesticides in brown rice samples for proficiency testing using Japanese official analytical method, QuEChERS, and modified QuEChERS combined with isotope dilution mass spectrometry Bacterial Pesticides: Mechanism of Action, Possibility of Food Contamination, and Residue Analysis Using MS
×
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
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 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 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1