A Potential Fungicide against Pseudoperonospora Cubensis: Design, Synthesis and 3D-QSAR of New Pyrazole-5-Carboxamide Derivatives.

IF 1.7 4区化学 Q3 CHEMISTRY, ORGANIC Current organic synthesis Pub Date : 2023-03-27 DOI:10.2174/1570179420666230327145745

Lizeng Wang, Shixiang Pan, Zhaokai Yang, Aiying Guan, Xufeng Sun, Jinbo Zhang, Zhinian Li, Changling Liu, Xinling Yang

{"title":"A Potential Fungicide against Pseudoperonospora Cubensis: Design, Synthesis and 3D-QSAR of New Pyrazole-5-Carboxamide Derivatives.","authors":"Lizeng Wang, Shixiang Pan, Zhaokai Yang, Aiying Guan, Xufeng Sun, Jinbo Zhang, Zhinian Li, Changling Liu, Xinling Yang","doi":"10.2174/1570179420666230327145745","DOIUrl":null,"url":null,"abstract":"Background: Downy mildew is one of the major fungi causing signiﬁcant economic losses to crops. The resistance of this fungus to current fungicides is increasing and new fungicides with a unique mode of action are needed.Objective: To find a novel pyrazole amide derivative as a potential fungicide.Methods: A series of pyrazole-5-carboxamide derivatives containing a diaryl ether were designed and synthesized by the Intermediate derivatization method (IDM). Their fungicidal activities against Pseudoperonospora cubensis (P. cubensis, cucumber downy mildew) were evaluated in the greenhouse.Results: Bioassays indicated that several compounds exhibited excellent fungicidal activity against P. cubensis in vivo. In particular, T24 (EC50 = 0.88 mg L-1) had the highest activity compared with Dimethomorph and Fluazinam and other analogues. The relationship between the activity and the structure of these derivatives was analyzed, and an accurate and reliable three-dimensional quantitative structure-activity relationship (3D-QSAR) model was established to determine that electrostatic and steric fields had important effects on the improvement of fungicidal activity.Conclusion: The novel pyrazole-5-carboxamide derivative T24 can be considered a potential fungicide for P. cubensis control.","PeriodicalId":11101,"journal":{"name":"Current organic synthesis","volume":null,"pages":null},"PeriodicalIF":1.7000,"publicationDate":"2023-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Current organic synthesis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.2174/1570179420666230327145745","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

Abstract

Background: Downy mildew is one of the major fungi causing signiﬁcant economic losses to crops. The resistance of this fungus to current fungicides is increasing and new fungicides with a unique mode of action are needed.

Objective: To find a novel pyrazole amide derivative as a potential fungicide.

Methods: A series of pyrazole-5-carboxamide derivatives containing a diaryl ether were designed and synthesized by the Intermediate derivatization method (IDM). Their fungicidal activities against Pseudoperonospora cubensis (P. cubensis, cucumber downy mildew) were evaluated in the greenhouse.

Results: Bioassays indicated that several compounds exhibited excellent fungicidal activity against P. cubensis in vivo. In particular, T24 (EC₅₀ = 0.88 mg L^-1) had the highest activity compared with Dimethomorph and Fluazinam and other analogues. The relationship between the activity and the structure of these derivatives was analyzed, and an accurate and reliable three-dimensional quantitative structure-activity relationship (3D-QSAR) model was established to determine that electrostatic and steric fields had important effects on the improvement of fungicidal activity.

Conclusion: The novel pyrazole-5-carboxamide derivative T24 can be considered a potential fungicide for P. cubensis control.

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

一种潜在的防霉剂:新型吡唑-5-羧酸酰胺衍生物的设计、合成和3D-QSAR。

背景:霜霉病是给农作物造成重大经济损失的主要真菌之一。该真菌对现有杀菌剂的抗性日益增强，需要具有独特作用模式的新型杀菌剂。目的:寻找一种新的吡唑酰胺衍生物作为潜在的杀菌剂。方法:采用中间衍生法(IDM)设计并合成了一系列含二芳基醚的吡唑-5-羧胺衍生物。在温室环境下，对其对黄瓜霜霉病的抑菌活性进行了评价。结果:生物测定表明，几种化合物在体内具有良好的杀霉活性。其中，T24 (EC50 = 0.88 mg L-1)的抑菌活性最高，高于噻虫啉和氟唑西南等类似物。分析了这些衍生物的活性与结构之间的关系，建立了准确可靠的三维定量构效关系(3D-QSAR)模型，确定了静电场和空间场对杀真菌活性的提高有重要作用。结论:新型吡唑-5-羧酸酰胺衍生物T24是一种很有潜力的杀真菌剂。

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

Current organic synthesis 化学-有机化学

CiteScore

3.40

自引率

5.60%

发文量

审稿时长

6-12 weeks

期刊介绍： Current Organic Synthesis publishes in-depth reviews, original research articles and letter/short communications on all areas of synthetic organic chemistry i.e. asymmetric synthesis, organometallic chemistry, novel synthetic approaches to complex organic molecules, carbohydrates, polymers, protein chemistry, DNA chemistry, supramolecular chemistry, molecular recognition and new synthetic methods in organic chemistry. The frontier reviews provide the current state of knowledge in these fields and are written by experts who are internationally known for their eminent research contributions. The journal is essential reading to all synthetic organic chemists. Current Organic Synthesis should prove to be of great interest to synthetic chemists in academia and industry who wish to keep abreast with recent developments in key fields of organic synthesis.