Synthesis and herbicidal activities of 2‐((3‐pyridinyl‐2‐oxo‐2,3‐dihydrobenzo[d]thiazol‐6‐yl)oxy)propionates

Author:

Chen Yu1,Li Zhanbin1,Huang Yuqian1,Li Wenqi1,Wei Shaopeng12ORCID,Ji Zhiqin12ORCID

Affiliation:

1. College of Plant Protection Northwest A&F University Yangling China

2. Shaanxi Province Key Laboratory Research & Development on Botanical Pesticides Northwest A&F University Yangling China

Abstract

AbstractBACKGROUNDThe discovery of lead compounds is fundamental to herbicide innovation, yet the limited availability of valuable lead compounds has impeded their progress in recent years. The study presents a novel molecular scaffold that exhibits remarkably potent herbicidal activity.RESULTSThrough a scaffold‐hopping strategy, a highly potent lead compound for herbicides, namely 3‐(2‐pyridinyl)‐benzothiazol‐2‐one, was unexpectedly discovered during attempts to structurally modify haloxyfop, a commercial aryl‐oxy‐phenoxy‐propionate herbicide. To investigate the structure–activity relationship (SAR) of the newly discovered herbicidal chemicals, a series of 2‐(2‐oxo‐3‐(pyridin‐2‐yl)‐2,3‐dihydrobenzo[d]thiazol‐6‐yloxy)propanoic acid derivatives, I‐01 ~ I‐27, were designed and synthesized. SAR analysis revealed that trifluoromethyl at the 5‐position of pyridine is crucial for herbicidal activity, whereas additional fluorine or Cl atom at the 3‐position of pyridine significantly enhances activity. Carboxylic ester derivatives exhibit superior herbicidal activity compared with amide derivatives. Moreover, the activity of carboxylic ester derivatives decreases with C chain extension, but the introduction of O atoms in the side chain benefits activity enhancement. Pot experiments conducted in a glasshouse demonstrated that I‐01 and I‐09 exhibited potent postemergence herbicidal activity against broadleaf weeds, and completely inhibited growth of Amaranthus retroflex, Abutilon theophrasti and Portulaca oleracea at a dosage of 75 g ha−1.CONCLUSIONDespite the initial goal of scaffold‐hopping not being achieved, we have successfully identified a novel molecular scaffold exhibiting exceptional herbicidal activity, thereby presenting innovative prospects for herbicide development. © 2024 Society of Chemical Industry.

Funder

National Natural Science Foundation of China

Publisher

Wiley

Cited by 1 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

同舟云学术

1.学者识别学者识别

2.学术分析学术分析

3.人才评估人才评估

"同舟云学术"是以全球学者为主线,采集、加工和组织学术论文而形成的新型学术文献查询和分析系统,可以对全球学者进行文献检索和人才价值评估。用户可以通过关注某些学科领域的顶尖人物而持续追踪该领域的学科进展和研究前沿。经过近期的数据扩容,当前同舟云学术共收录了国内外主流学术期刊6万余种,收集的期刊论文及会议论文总量共计约1.5亿篇,并以每天添加12000余篇中外论文的速度递增。我们也可以为用户提供个性化、定制化的学者数据。欢迎来电咨询!咨询电话:010-8811{复制后删除}0370

www.globalauthorid.com

TOP

Copyright © 2019-2024 北京同舟云网络信息技术有限公司
京公网安备11010802033243号  京ICP备18003416号-3