Design, Synthesis, and Antifungal Activities of Novel Aromatic Carboxamides Containing a Diphenylamine Scaffold

作者：Aigui Zhang, Ying Yue, Jian Hua Yang, Jiaxing Shi, Tao Ke, Hong Yan Jin, Taiping Hou · 发表于：Journal of Agricultural and Food Chemistry · 年份：2019 · DOI：10.1021/acs.jafc.9b00151 · 被引用次数：65 · 研究领域：Fungal Plant Pathogen Control、Plant Disease Resistance and Genetics、Plant-Microbe Interactions and Immunity

A series of novel N -(2-(phenylamino)-4-fluorophenyl)-pyrazole-4-carboxamides 1 – 15 and aromatic carboxamides with a diphenylamine scaffold 16 – 29 were designed, synthesized, and evaluated for their antifungal activities. In vitro experiments showed that compound 6 (EC 50 = 0.03 mg/L) was superior to bixafen (EC 50 = 0.04 mg/L) against Rhizoctoinia solani and compound 6 (IC 50 = 1.41 mg/L) was close to bixafen (IC 50 = 1.22 mg/L) against succinate dehydrogenase from R. solani . Additionally, in vivo pot experiments showed that compound 6 (EC 50 = 1.93 mg/L) was better than bixafen (EC 50 = 3.72 mg/L) and close to thifluzamide (EC 50 = 1.83 mg/L) against R. solani . In vivo field trials showed that compound 6 at 200 g ai ha –1 had 64.10% control efficacy against rice sheath blight after 21 days with two sprayings, close to thifluzamide (71.40%). Furthermore, molecular docking showed that compound 6 anchors in the binding site of SDH.