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Discovery of HNPC-A188: a novel acaricide containing trifluoroethyl thioether and pyrimidin-4-amine
Medicinal Chemistry Research ( IF 2.6 ) Pub Date : 2024-05-20 , DOI: 10.1007/s00044-024-03231-1
Ting Xiao , Aiping Liu , Xingping Liu , Fujun Zhong , Guojun Li , Zhichang Huang , Zai Zhang , Yeguo Ren , Jiang-Sheng Li , Weidong Liu

Pyrimidifen is an excellent commercial acaricide, but it is not low toxic to mammals. Trifluoroethyl thioether derivatives exhibit excellent bioactivity, and flupentiofenox is the first commercially available trifluoroethyl thioether acaricide. To search for novel pesticides, we conducted research around pyrimidifen and flupentiofenox. By introducing trifluoroethyl thioether and F, Cl, CH3 substituents at different positions on the benzene ring, we successfully introduced trifluoroethyl thioether into the pyrimidine derivatives. Further optimization resulted in compound T7 (HNPC-A188)(5-chloro-6-(difluoromethyl)-N-(2-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenoxy)ethyl)pyrimidin-4-amine). HNPC-A188 exhibits excellent acaricidal activity with LC50 values of 0.19 mg/L against Tetranychus urticae, which can be compared with the commercial acaricide cyenopyrafen (LC50 = 0.13 mg/L).



中文翻译:


HNPC-A188的发现:一种含有三氟乙基硫醚和嘧啶-4-胺的新型杀螨剂



嘧啶芬是一种优良的商业杀螨剂,但对哺乳动物的毒性不低。三氟乙基硫醚衍生物表现出优异的生物活性,氟虫螨酯是第一个市售的三氟乙基硫醚杀螨剂。为了寻找新型农药,我们围绕嘧啶芬和氟虫螨酯进行了研究。通过在苯环上不同位置引入三氟乙基硫醚和F、Cl、CH 3 取代基,我们成功地将三氟乙基硫醚引入到嘧啶衍生物中。进一步优化得到化合物T7 (HNPC-A188)(5-氯-6-(二氟甲基)-N-(2-(2-氟-4-甲基-5-((2,2,2-三氟乙基)硫基))苯氧基)乙基)嘧啶-4-胺)。 HNPC-A188对二斑叶螨表现出优异的杀螨活性,LC 50 值为0.19 mg/L,可与市售杀螨剂氰吡芬(LC 50 = 0.13 mg/L)相媲美。 。

更新日期:2024-05-21
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