文献类型：期刊文献

英文题名：Novel SDH Inhibitors as Antifungal Leads: From Azobenzene Derivatives to the 1,2,4-Oxadiazole Compounds

作者：Fu, Wen[1,2];Yuan, Qinglong[1];Zhang, Hangji[1];Li, Xiaoyan[3];Lu, Yiming[1];Yan, Wenming[4];Ye, Yonghao[5];Liu, Xili[6,7];Li, Zhong[1,9];Shao, Xusheng[1,8,9,10]

机构：[1]East China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China;[2]Guizhou Univ, Natl Key Lab Green Pesticide, Guiyang 550025, Guizhou, Peoples R China;[3]Yantai Inst China Agr Univ, Coll Humanities & Econ Management, Yantai 264670, Shandong, Peoples R China;[4]Shandong Yingxin Chem Co Ltd, Binzhou 256600, Shandong, Peoples R China;[5]Nanjing Agr Univ, Coll Plant Protect, State & Local Joint Engn Res Ctr Green Pesticide I, Nanjing 210095, Peoples R China;[6]Northwest A&F Univ, Coll Plant Protect, State Key Lab Crop Stress Resistance & High Effici, Yangling 712100, Shaanxi, Peoples R China;[7]China Agr Univ, Coll Plant Protect, Dept Plant Pathol, Beijing 100193, Peoples R China;[8]East China Univ Sci & Technol, Engn Res Ctr Pharmaceut Proc Chem, Sch Pharm, Minist Educ, Shanghai 200237, Peoples R China;[9]East China Univ Sci & Technol, State Key Lab Bioreactor Engn, Shanghai 200237, Peoples R China;[10]East China Univ Sci & Technol, Sch Pharm, Shanghai Frontier Sci Res Base Optogenet Tech Cell, Shanghai 200237, Peoples R China

年份：2024

卷号：72

期号：44

起止页码：24272

外文期刊名：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

收录：;EI(收录号：20244317269112);WOS:【SCI-EXPANDED(收录号:WOS:001340296000001)】；

基金：This work was financially supported by the National Natural Science Foundation of China (21877039, 32072441, 32472610, and 32402439), the National Key Research and Development Program of China (2018YFD0200100), the Innovation Program of Shanghai Municipal Education Commission (2017-01-07-00-02-E00037), Tobacco and Health funding program (2022539200340111), Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism (Shanghai Municipal Education Commission), and the project of National Key Laboratory of Green Pesticide/Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University (SKL-GPL-KF-202405).

语种：英文

外文关键词：SDH; azobenzene; 1,2,4-oxadiazole; antifungal lead; structural optimization

摘要：Azo-incorporating was reported to be an effective strategy for increasing SDH inhibitory activity but for poor in vivo control effects. Herein, the azo-incorporated compounds were structurally optimized to retain a preferential conformation by replacing the azo bond with their bioisosteres. Interestingly, the 1,2,4-oxadiazole compound D2 displayed a broad fungicidal spectrum as well as fluxapyroxad. More excitedly, compound D2 showed excellent antifungal activities against rice sheath blight disease both in vitro (EC50 = 0.001 mu g/mL) and in vivo (EC50 = 1.08 mu g/mL, EC95 = 4.67 mu g/mL). In addition, an extra pi-pi interaction was found between the 1,2,4-oxadiazole ring of compound D2 and the phenyl ring of residue D_Y586, which might interpret the enhanced potency of compound D2 against Rhizoctonia solani. Further structural optimizations of the 1,2,4-oxadiazole compounds gave several analogues that made a breakthrough in controlling rice blast disease. These 1,2,4-oxadiazole compounds, derived from azobenzene derivatives, could be antifungal leads especially against R. solani and Magnaporthe grisea, exemplifying an interesting mode of pesticide discovery and providing theoretical guidance for innovation of the SDHI fungicide.