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Discovery, Optimization, and Biological Evaluation of Novel Pyrazol-5-yl-phenoxybenzamide Derivatives as Potent Succinate Dehydrogenase Inhibitors

文献类型： 外文期刊

作者： Xu, Dan 1 ; Lin, Guo-Tai 1 ; Huang, Jia-Chuan 1 ; Sun, Jian 3 ; Wang, Wei 4 ; Liu, Xili 1 ; Xu, Gong 1 ;

作者机构： 1.Northwest A&F Univ, Coll Plant Protect, Key Lab Plant Protect Resources, Key Lab Integrated Pest Management Loess Plateau,M, Yangling 712100, Shaanxi, Peoples R China

2.Northwest A&F Univ, Coll Chem & Pharm, Shaanxi Key Lab Nat Prod & Chem Biol, Yangling 712100, Shaanxi, Peoples R China

3.Jilin Acad Agr Sci, Inst Agr Qual Stand & Testing Technol, Changchun 130033, Jilin, Peoples R China

4.Ningxia Univ, Sch Agr, Yinchuan 750021, Ningxia, Peoples R China

关键词： pyrazole; diphenyl ether; antifungal activity; structure-activity relationships; molecular docking

期刊名称：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY （ 影响因子：5.7； 五年影响因子：6.0 ）

ISSN： 0021-8561

年卷期： 2024 年 72 卷 31 期

页码：

收录情况： SCI

摘要： The diphenyl ether molecular pharmacophore has played a significant role in the development of fungicidal compounds. In this study, a variety of pyrazol-5-yl-phenoxybenzamide derivatives were synthesized and evaluated for their potential to act as succinate dehydrogenase inhibitors (SDHIs). The bioassay results indicate certain compounds to display a remarkable and broad-spectrum in their antifungal activities. Notably, compound 12x exhibited significant in vitro activities against Valsa mali, Gaeumannomyces graminis, and Botrytis cinerea, with EC50 values of 0.52, 1.46, and 3.42 mg/L, respectively. These values were lower or comparable to those of Fluxapyroxad (EC50 = 12.5, 1.93, and 8.33 mg/L, respectively). Additionally, compound 12x showed promising antifungal activities against Sclerotinia sclerotiorum (EC50 = 0.82 mg/L) and Rhizoctonia solani (EC50 = 1.86 mg/L), albeit lower than Fluxapyroxad (EC50 = 0.23 and 0.62 mg/L). Further in vivo experiments demonstrated compound 12x to possess effective protective antifungal activities against V. mali and S. sclerotiorum at a concentration of 100 mg/L, with inhibition rates of 66.7 and 89.3%, respectively. In comparison, Fluxapyroxad showed inhibition rates of 29.2 and 96.4% against V. mali and S. sclerotiorum, respectively. Molecular docking analysis revealed that compound 12x interacts with SDH through hydrogen bonding, pi-cation, and pi-pi interactions, providing insights into the probable mechanism of action. Furthermore, compound 12x exhibited greater binding energy and SDH enzyme inhibitory activity than Fluxapyroxad (Delta Gcal = -46.8 kcal/mol, IC50 = 1.22 mg/L, compared to Delta Gcal = -41.1 kcal/mol, IC50 = 8.32 mg/L). Collectively, our results suggest that compound 12x could serve as a promising fungicidal lead compound for the development of more potent SDHIs for crop protection.

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