Synthesis and fungicidal activity of novel benzimidazole derivatives bearing pyrimidine‐thioether moiety against Botrytis cinerea

Abstract

BACKGROUND: Botrytis cinerea is a serious plant fungus and strongly affects the yield and quality of crops. The main control strategy is the employment of fungicides. To research for efficient fungicide with novel structure, a series of novel benzimidazole derivatives bearing pyrimidine and thioether moieties were designed and synthesized.RESULTS: Some target compounds such as 4h, 4i, 4k, 4l, 4m, 4s, 4t and 4u exhibited notable fungicidal activities, with half maximal effective concentration (EC 50 ) values in the range 0.13-0.24 ∼g mL −1 , which means that their activities were comparable or higher than that of carbendazim (EC 50 = 0.21 ∼g mL −1 ). Among them, N-(4-fluorophenyl)-2-((4-(1H-benzimidazol-2-yl)-6-(4-methoxyphenyl) pyrimidin-2-yl)thio)acetamide (4m) displayed the best activity (EC 50 = 0.13 ∼g mL −1 ). Molecular electrostatic potential analysis of 4m elucidated that the NH moiety of benzimidazole ring was located in the positive potential region and may generate hydrogen bond with target amino acid residue. Molecular docking analysis revealed that there was one hydrogen bond and one π-π interaction between 4m and target protein.CONCLUSIONS: This study demonstrated that the benzimidazole derivatives bearing pyrimidine and thioether moieties can be further optimized as a lead compound for the control of B. cinerea. The combination of molecular electrostatic potential and molecular docking analyses may provide a valuable reference for studying the interaction between the ligand and target protein.

Design, synthesis, and fungicidal activity of novel N‐substituted piperazine‐containing phenylpyridines against cucumber downy mildew

“…The MEP is a critical factor in studying and predicting the interaction between molecules, which can help understand the electrostatic potential distribution of molecules and analyze the electrostatic interaction between receptors and target compounds. 42 On the electrostatic potential surface, the red region represents the strong negative potential, and the blue area represents the positive potential. From Fig.…”

Design, Synthesis and Antifungal Activities of Novel Quinazolinone Derivatives

“…药物分子的表面静电势是其重要的理化参数, 是分 析药物分子与受体蛋白相互作用的重要依据. 选取结构 相似, 但活性差异显著的 7a 和 7p 为研究对象, 采用 Gaussian 09 和 GaussView 6.0 软件 [24][25] , 基于密度泛函 理论, 使用 B3LYP/6-31G (d, p)基组对分子结构进行优 化, 然后对优化的结构进行分子表面静电势计算, 并绘 制静电势能图. 辅助材料(Supporting Information) 中间体 5a～5e 的 1 H NMR 谱图, 目标化合物 7a～7s 的 1 H NMR, 13 C NMR 和抑菌活性.…”

Novel Pyrimidine Derivatives Bearing a 1,3,4-Thiadiazole Skeleton: Design, Synthesis, and Antifungal Activity

“…Meanwhile, in the agricultural field, pyrimidine derivatives also have good biological activities such as antiviral ( Wu, et al, 2015 ; Zan et al, 2020 ), insecticidal ( Liu, et al, 2017 ; Wu, et al, 2019 ; Chen, et al, 2021 ; Liu, et al, 2021 ; Sun, et al, 2021 ), fungicidal ( Guan et al, 2017 ; Yan et al, 2020 ; Yang, et al, 2020 ), bactericidal ( Li et al, 2020 ), herbicidal ( Chen et al, 2019 ; Li et al, 2020 ), and anticancer ( Guo et al, 2020 ) properties. In the last few decades, some pyrimidine derivatives have been commercialized as pesticides for controlling plant diseases and insect pests.…”