Design, Synthesis, and Fungicidal Activities of Novel N -(Pyrazol-5-yl)benzamide Derivatives Containing a Diphenylamine Moiety

作者：Yidan Ma, Huan Zhou, Guo‐Tai Lin, Ke-Huan Wu, Gong Xu, Xili Liu, Dan Xu · 发表于：Journal of Agricultural and Food Chemistry · 年份：2024 · DOI：10.1021/acs.jafc.3c07567 · 被引用次数：21 · 研究领域：Fungal Plant Pathogen Control、Plant-Microbe Interactions and Immunity、Plant Disease Resistance and Genetics

To accelerate the development of novel fungicides, a variety of N -(pyrazol-5-yl)benzamide derivatives with a diphenylamine moiety were designed and synthesized using a pharmacophore recombination strategy based on the structure of pyrazol-5-yl-aminophenyl-benzamides. The bioassay results demonstrated that most of the target compounds had excellent in vitro antifungal activities against Sclerotinia sclerotiorum, Valsa mali, and Botrytis cinerea . In particular, compound 5IIIh exhibited remarkable activity against S. sclerotiorum (EC 50 = 0.37 mg/L), which was similar to that of fluxapyroxad (EC 50 = 0.27 mg/L). In addition, compound 5IIIc (EC 50 = 1.32 mg/L) was observed to be more effective against V. mali than fluxapyroxad (EC 50 = 12.8 mg/L) and comparable to trifloxystrobin (EC 50 = 1.62 mg/L). Furthermore, compound 5IIIh demonstrated remarkable in vivo protective antifungal properties against S. sclerotiorum, with an inhibition rate of 96.8% at 100 mg/L, which was close to that of fluxapyroxad (99.6%). Compounds 5IIIc (66.7%) and 5IIIh (62.9%) exhibited good in vivo antifungal effects against V. mali at 100 mg/L, which were superior to that of fluxapyroxad (11.1%) but lower than that of trifloxystrobin (88.9%). The succinate dehydrogenase (SDH) enzymatic inhibition assay was conducted to confirm the mechanism of action. Molecular docking analysis further revealed that compound 5IIIh has significant hydrogen-bonding, π–π, and p−π conjugation interactions with ARG 43, SER ...