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Discovery of novel sulfonamide derivatives containing pinacolone moieties as fungicide candidates against Botrytis cinerea
Pest Management Science ( IF 3.8 ) Pub Date : 2025-01-03 , DOI: 10.1002/ps.8617
Wei Liu, Chaojie Liu, Ni An, Zhiqiu Qi, Huaiyu Bin, Xilun Wu, He Liu, Yuanhua Wu, Xinghai Li

BACKGROUNDBotrytis cinerea is one of the most serious plant diseases and severely threatens agricultural production. The rapidly intensifying resistance makes most commercial chemical fungicides lose control efficacy. Developing new fungicides with novel structures and modes of action is an effective measure to solve this problem.RESULTSIn this work, 29 novel sulfonamide compounds containing pinacolone scaffolds were designed and synthesized based on the active substructure splicing strategy. The biological activity assay on three kinds of Botrytis cinerea strains manifested that these compounds exhibit moderate to excellent antifungal activity. Compounds 3a‐1 and 3a‐11 displayed the highest in vitro antifungal activity similar to control agents carbendazim, procymidone, and boscalid. Compound 3c had the lowest EC50 value of 1.96 μg/mL against strain PJ‐02 compared to boscalid (6.90 μg/mL). Bioassay results on strawberry fruits and tomato pots indicated that compounds 3a‐1 and 3a‐11 also possess superb in vivo antifungal activity compared to control agents. The electronic conductivity measurement results showed that compound 3a‐1 can significantly increase the membrane permeability of Botrytis cinerea mycelium. Scanning electron microscopy observation revealed that compound 3a‐1 could cause the Botrytis cinerea mycelium to twist and break, and inhibit mycelium branching. Density functional theory calculation and molecular electrostatic potential distribution were also used to analyze the activity mechanism of target compounds.CONCLUSIONDue to their excellent antifungal activity against Botrytis cinerea, these novel sulfonamide derivatives containing pinacolone scaffolds could be considered qualified fungicide candidates. Preliminary exploration of the mechanism suggests that this kind of compound may possess a novel mode of action. © 2025 Society of Chemical Industry.

中文翻译:


发现含有频纳酮部分的新型磺胺衍生物作为针对灰葡萄孢菌的杀菌剂候选物



背景灰葡萄孢霉菌是最严重的植物病害之一,严重威胁农业生产。迅速增强的抗性使大多数商业化学杀菌剂失去了控制效果。开发具有新颖结构和作用方式的新型杀菌剂是解决这个问题的有效措施。结果本工作基于活性亚结构剪接策略设计合成了 29 种含有频哪酮支架的新型磺酰胺类化合物。对 3 种灰葡萄孢菌株的生物活性测定表明,这些化合物表现出中等至极好的抗真菌活性。化合物 3a-1 和 3a-11 显示出最高的体外抗真菌活性,类似于对照剂多菌灵、普罗咪酮和啶酰菌胺。与啶酰菌胺 (6.90 μg/mL) 相比,化合物 3c 对菌株 PJ-02 的 EC50 值最低,为 1.96 μg/mL。草莓果实和番茄盆的生物测定结果表明,与对照剂相比,化合物 3a-1 和 3a-11 也具有出色的体内抗真菌活性。电子电导率测量结果表明,化合物 3a-1 可以显著提高灰葡萄孢菌丝体的膜通透性。扫描电子显微镜观察显示,化合物 3a-1 可导致灰葡萄孢菌丝体扭曲和断裂,并抑制菌丝体分枝。密度泛函理论计算和分子静电势分布也用于分析目标化合物的活性机制。结论由于它们对灰葡萄孢菌具有出色的抗真菌活性,这些含有频纳酮支架的新型磺酰胺衍生物可被视为合格的杀菌剂候选者。 对机制的初步探索表明,这种化合物可能具有一种新的作用方式。© 2025 年化学工业学会。
更新日期:2025-01-03
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