Abstract
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).
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Acknowledgements
We would like to thank the colleagues of National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry who have contributed to the discovery of HNPC-A188. And we also gratefully acknowledge support of this work by the National Natural Science Foundation of China (22177033) and Hunan Enterprise Science and Technology Innovation and Entrepreneurship Team Project (Haili New Materials Science and Technology Innovation and Entrepreneurship Team).
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Xiao, T., Liu, A., Liu, X. et al. Discovery of HNPC-A188: a novel acaricide containing trifluoroethyl thioether and pyrimidin-4-amine. Med Chem Res (2024). https://doi.org/10.1007/s00044-024-03231-1
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DOI: https://doi.org/10.1007/s00044-024-03231-1