{"title":"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。","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":"<p><strong>Background: </strong>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.</p><p><strong>Objective: </strong>To find a novel pyrazole amide derivative as a potential fungicide.</p><p><strong>Methods: </strong>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.</p><p><strong>Results: </strong>Bioassays indicated that several compounds exhibited excellent fungicidal activity against P. cubensis in vivo. In particular, T24 (EC<sub>50</sub> = 0.88 mg L<sup>-1</sup>) 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.</p><p><strong>Conclusion: </strong>The novel pyrazole-5-carboxamide derivative T24 can be considered a potential fungicide for P. cubensis control.</p>","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":"{\"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\":\"<p><strong>Background: </strong>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.</p><p><strong>Objective: </strong>To find a novel pyrazole amide derivative as a potential fungicide.</p><p><strong>Methods: </strong>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.</p><p><strong>Results: </strong>Bioassays indicated that several compounds exhibited excellent fungicidal activity against P. cubensis in vivo. In particular, T24 (EC<sub>50</sub> = 0.88 mg L<sup>-1</sup>) 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.</p><p><strong>Conclusion: </strong>The novel pyrazole-5-carboxamide derivative T24 can be considered a potential fungicide for P. cubensis control.</p>\",\"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}","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}
A Potential Fungicide against Pseudoperonospora Cubensis: Design, Synthesis and 3D-QSAR of New Pyrazole-5-Carboxamide Derivatives.
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.
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.
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