ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Design, synthesis, and insecticidal/acaricidal evaluation of novel pyrimidinamine derivatives containing phenyloxazole moiety

Ning Zhang, Ming-Zhi Huang, Ai-Ping Liu, Min-Hua Liu, Li-Zhong Li, Chun-Ge Zhou, Ye-Guo Ren, Xiao-Ming Ou, Chu-Yun Long, Jiong Sun, Ming-Ming Dang, and Zhi-Li Lan

College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha, People’s Republic of China

E-mail: suxi789@126.com

Received: 21 January 2019  Accepted: 7 September 2019

Abstract:

A series of novel pyrimidinamine derivatives containing phenyloxazole moiety were designed and synthesized, and their structures were characterized by ¹H NMR, MS, and elemental analyses. The bioassay results displayed that some compounds exhibited remarkable insecticidal activities against Aphis fabae and Tetranychus cinnabarinus. Especially, 5-chloro-6-ethyl-2-methyl-N-((2-(p-tolyl)oxazol-4-yl)methyl)pyrimidin-4-amine (9o) showed potent activity against A. fabae, superior to that of the commercial insecticide, imidacloprid. In addition, 5-chloro-6-ethyl-2-methyl-N-((2-(4-(trifluoromethyl)phenyl)oxazol-4-yl)methyl)pyrimidin-4-amine (9r) showed potent activities against T. cinnabarinus, inferior to that of the commercial insecticide spirotetramat. The structure–activity relationship study for the target compounds was also discussed.

Keywords: Pyrimidinamines; Phenyloxazole moiety; Insecticidal/acaricidal activities; Structure–activity relationship study

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-019-00932-5

Chemical Papers 74 (3) 963–970 (2020)