Liu Yingshuai, Sheng Guozhu, Liu Baohong, Yin Ruofei, Du Yaoyao, Li Bin
Plant Protection College, Shenyang Agricultural University, Shenyang, Liaoning, China.
Shandong Kangqiao Biotechnology Co., Ltd, Binzhou, Shandong, China.
PLoS One. 2025 Jul 2;20(7):e0327587. doi: 10.1371/journal.pone.0327587. eCollection 2025.
The acaricide propargite has been widely used for over 50 years without significant resistance issues. Addressing to the propargite defects of poor crop safety, thirty-six novel halogenated propargite analogues were designed, synthesized, and characterized using 1H NMR, 13C NMR spectroscopy, and HRMS. All target compounds were screened for activity against adult Tetranychus cinnabarinus (spider mites) and Myzus persicae (aphids). Two compounds exhibiting higher insecticidal activity were further evaluated for crop safety on cowpea seedlings. Structural modifications, such as replacing the tert-butyl group on the propargite benzene ring with chlorine or trifluoromethoxy, and substituting the propargyl group with fluorinated alkyl groups (e.g., 2-fluoroethyl or 3,3,3-trifluoropropyl), significantly enhanced both acaricidal and aphicidal activity. Compound 5.16 demonstrated superior acaricidal activity (LC50: 14.85 mg L-1) on Tetranychus cinnabarinus and excellent crop safety on cowpea seedlings. Additionally, Compound 5.32 exhibited both acaricidal (LC50: 14.32 mg L-1) and aphicidal activity, which is unusual in this chemical class. The compounds 5.16 and 5.32 could be used as promising leads for the discovery of novel acaricides or insecticides.
杀螨剂炔螨特已广泛使用50多年，未出现明显的抗性问题。针对炔螨特作物安全性差的缺陷，设计、合成了36种新型卤代炔螨特类似物，并采用1H NMR、13C NMR光谱和高分辨质谱对其进行了表征。对所有目标化合物进行了针对朱砂叶螨（红蜘蛛）成虫和桃蚜活性的筛选。对两种表现出较高杀虫活性的化合物进一步评估了其对豇豆幼苗的作物安全性。结构修饰，如用氯或三氟甲氧基取代炔螨特苯环上的叔丁基，并用氟化烷基（如2-氟乙基或3,3,3-三氟丙基）取代炔丙基，显著增强了杀螨和杀蚜活性。化合物5.16对朱砂叶螨表现出优异的杀螨活性（LC50：14.85mg L-1），对豇豆幼苗具有良好的作物安全性。此外，化合物5.32兼具杀螨活性（LC50：14.32mg L-1）和杀蚜活性，这在该化学类别中并不常见。化合物5.16和5.32有望作为发现新型杀螨剂或杀虫剂的先导化合物。
