Bai Zhiqiang, Dang Kunrong, Tang Jinrui, Yang Rongjing, Fan Liming, Li Qiu, Yang Yue, Ye Min, Su Fawu
State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, College of Plant Protection, Yunnan Agricultural University, Kunming 650201, China.
College of Science, Yunnan Agricultural University, Kunming 650201, China.
Molecules. 2025 Feb 26;30(5):1079. doi: 10.3390/molecules30051079.
To discover novel fungicides with good inhibitory effects on plant fungal diseases, twenty-five 3-indolyl-3-hydroxy oxindole derivatives (3a-3y) were synthesized. These newly derivatives were characterized by NMR and HRMS. Their antifungal activities against five plant pathogenic fungi were assessed in vitro. Most of the compounds exhibited moderate to excellent antifungal activities against the five pathogenic fungi. Notably, compounds , , , and displayed remarkable and broad-spectrum antifungal activities comparable to or superior to those of the fungicides carvacrol (CA) and phenazine-1-carboxylic acid (PCA). Among them, compound displayed the most excellent antifungal activity against Kühn (), with an EC of 3.44 mg/L, which was superior to CA (7.38 mg/L) and PCA (11.62 mg/L). Preliminary structure-activity relationship (SAR) results indicated that the introduction of I, Cl, or Br substituents at position 5 of the 3-hydroxy-2-oxindole and indole rings is crucial for compounds to exhibit good antifungal activity. The in vivo antifungal activity assay showed that compound 3u has good curative effects against . The current results suggest that these compounds are capable of serving as promising lead compounds.
为发现对植物真菌病害具有良好抑制作用的新型杀菌剂，合成了25种3-吲哚基-3-羟基氧化吲哚衍生物（3a - 3y）。这些新衍生物通过核磁共振（NMR）和高分辨质谱（HRMS）进行了表征。在体外评估了它们对五种植物病原真菌的抗真菌活性。大多数化合物对这五种病原真菌表现出中等至优异的抗真菌活性。值得注意的是，化合物 、 、 和 表现出显著的广谱抗真菌活性，与杀菌剂香芹酚（CA）和吩嗪-1-羧酸（PCA）相当或更优。其中，化合物 对 Kühn（ ）表现出最优异的抗真菌活性，其半数有效浓度（EC）为3.44 mg/L，优于CA（7.38 mg/L）和PCA（11.62 mg/L）。初步的构效关系（SAR）结果表明，在3-羟基-2-氧化吲哚和吲哚环的5位引入碘、氯或溴取代基对于化合物表现出良好的抗真菌活性至关重要。体内抗真菌活性测定表明化合物3u对 具有良好的防治效果。目前的结果表明这些化合物有望成为有前景的先导化合物。
