文献类型：期刊文献

英文题名：Design, Synthesis, and Biological Activity of Silicon-Containing Carboxamide Fungicides

作者：Quan, Xiaocao[1];Shen, Kunkun[1];Yang, Wu-Lin[1];Li, Zhong[1,2];Maienfisch, Peter[1,3]

机构：[1]East China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, State Key Lab Bioreactor Engn, Shanghai 200237, Peoples R China;[3]CreInSol Consulting & Biocontrols, CH-4118 Rodersdorf, Switzerland

年份：2024

卷号：72

期号：31

起止页码：17260

外文期刊名：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

收录：;EI(收录号：20243116780534);WOS:【SCI-EXPANDED(收录号:WOS:001279692400001)】；

基金：This research was financial supported by Innovation Program of Shanghai Municipal Education Commission (2017-01-07-00-02-E00037) and National Key Research Program of China (2017YFD0200505).

语种：英文

外文关键词：Boscalid; SDHI; silicon-containing compounds; carboxamide fungicides; bioisosteric replacement; structure activity relationship

摘要：Bioisosteric silicon replacement has proven to be a valuable strategy in the design of bioactive molecules for crop protection and drug development. Twenty-one novel carboxamides possessing a silicon-containing biphenyl moiety were synthesized and tested for their antifungal activity and succinate dehydrogenase (SDH) enzymatic inhibitory activity. Among these novel succinate dehydrogenase inhibitors (SDHIs), compounds 3a, 3e, 4l, and 4o possessing appropriate clog P and topological polar surface area values showed excellent inhibitory effects against Rhizoctonia solani, Sclerotinia sclerotiorum, Botrytis cinerea, and Fusarium graminearum at 10 mg/L in vitro, and the EC50 values of 4l and 4o were 0.52 and 0.16 mg/L against R. solani and 0.066 and 0.054 mg/L against S. sclerotiorum, respectively, which were superior to those of Boscalid. Moreover, compound 3a demonstrated superior SDH enzymatic inhibitory activity (IC50 = 8.70 mg/L), exhibiting 2.54-fold the potency of Boscalid (IC50 = 22.09 mg/L). Docking results and scanning electron microscope experiments revealed similar mode of action between compound 3a and Boscalid. The new silicon-containing carboxamide 3a is a promising SDHI candidate that deserves further investigation.