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

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journal contribution
posted on 12.04.2019 by Aigui Zhang, Ying Yue, Jian Yang, Jiaxing Shi, Ke Tao, Hong Jin, Taiping Hou
A series of novel N-(2-(phenylamino)-4-fluorophenyl)-pyrazole-4-carboxamides 115 and aromatic carboxamides with a diphenylamine scaffold 1629 were designed, synthesized, and evaluated for their antifungal activities. In vitro experiments showed that compound 6 (EC50 = 0.03 mg/L) was superior to bixafen (EC50 = 0.04 mg/L) against Rhizoctoinia solani and compound 6 (IC50 = 1.41 mg/L) was close to bixafen (IC50 = 1.22 mg/L) against succinate dehydrogenase from R. solani. Additionally, in vivo pot experiments showed that compound 6 (EC50 = 1.93 mg/L) was better than bixafen (EC50 = 3.72 mg/L) and close to thifluzamide (EC50 = 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.

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