Discovery of novel 1,5‐diaryl‐3‐trifluoropyrazoles as antifungal pesticides for crop protection,Pest Management Science

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Discovery of novel 1,5‐diaryl‐3‐trifluoropyrazoles as antifungal pesticides for crop protection
Pest Management Science ( IF 3.8 ) Pub Date : 2025-05-28 , DOI: 10.1002/ps.8909
Yihui Ma ₁ , Dangwei Yang ₁ , Guangyu Qin ₁ , Jun Yang ₁ , Xianglong Sun ₁ , Xiaoyu Gao ₁

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BACKGROUNDPlant diseases caused by phytopathogenic fungi continue to threaten global food security, driving the urgent need for discovery of antifungal agrochemicals with novel modes of action. The motif of 1,5‐diaryl‐3‐trifluoropyrazole was found to be associated with potential antifungal effect and HNNK‐5 was such an agrochemical being developed in our lab with moderate potency. This study took HNNK‐5 as the parent compound for lead optimization to discovery novel fungicides.RESULTTo further explore the antifungal potential of this class of compounds, a series of analogues of HNNK‐5 was designed and prepared. Among them, compound 7 was identified as the most potent member with much improved activity over the lead compound. Compound 7 almost completely inhibited the growth of all the tested fungal pathogens at 50 μg/mL with an EC50 range of 6.2–11.5 μg/mL, multiple‐fold less potent than the positive control azoxystrobin. Scanning electronic microscope (SEM) observation and fatty acid analysis showed that compound 7 treatment caused morphological changes and altered the amount of fatty acids of Fusarium oxysporum. Furthermore, compound 7 at higher application rates showed pronounced controlling effects against peanut root rot disease caused by Fusarium oxysporum in field study, similar to those of positive control azoxystrobin.CONCLUSIONThis study indicated that the characteristic structure of 1,5‐diaryl‐3‐trifluoropyrazole could be employed as a potential skeleton for antifungal pesticides development and provided compound 7 as a promising pesticide candidate for further development. © 2025 Society of Chemical Industry.

中文翻译：

发现新型 1,5-二芳基-3-三氟吡唑作为作物保护的抗真菌农药

背景由植物病原真菌引起的疾病继续威胁着全球粮食安全，推动了对发现具有新作用方式的抗真菌农用化学品的迫切需求。发现 1,5-二芳基-3-三氟吡唑的基序与潜在的抗真菌作用有关，而 HNNK-5 是我们实验室正在开发的一种具有中等效力的农用化学品。本研究以 HNNK-5 为母体化合物，进行先导优化，以发现新型杀菌剂。结果为了进一步探索这类化合物的抗真菌潜力，设计并制备了一系列 HNNK-5 类似物。其中，化合物 7 被确定为最有效的成员，其活性比先导化合物高得多。化合物 7 在 50 μg/mL 时几乎完全抑制了所有测试真菌病原体的生长，EC50 范围为 6.2–11.5 μg/mL，比阳性对照嘧菌酯低数倍。扫描电子显微镜（SEM）观察和脂肪酸分析表明，化合物 7 处理引起尖孢镰刀菌的形态变化并改变脂肪酸量。此外，在田间研究中，较高施用量的化合物 7 对尖孢镰刀菌引起的花生根腐病具有显著的控制效果，与阳性对照嘧菌酯相似。结论研究表明，1,5-二芳基-3-三氟吡唑的特征结构可以作为抗真菌农药开发的潜在骨架，并为化合物 7 提供了进一步开发的有前途的候选农药。© 2025 化工学会.

更新日期：2025-05-28

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