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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)

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