Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (3): 787-793.DOI: 10.6023/cjoc201908024 Previous Articles     Next Articles


张燕, 尚俊峰, 李欢, 刘航, 宋海斌, 王宝雷, 李正名   

  1. 南开大学化学学院 元素有机化学国家重点实验室 天津 300071
  • 收稿日期:2019-08-16 修回日期:2019-10-09 发布日期:2019-11-07
  • 通讯作者: 王宝雷, 李正名;
  • 基金资助:

Synthesis and Biological Activities of Novel N-(2-(5-(3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-1,3,4-oxadiazol-2-yl)-4-chloro-6-methylphenyl) Amides

Zhang Yan, Shang Junfeng, Li Huan, Liu Hang, Song Haibin, Wang Baolei, Li Zhengming   

  1. State Key Laboratory of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071
  • Received:2019-08-16 Revised:2019-10-09 Published:2019-11-07
  • Supported by:
    Project supported by the Natural Science Foundation of Tianjin City (No. 17JCYBJC19900), the National Natural Science Foundation of China (No. 21772103) and the National Key Research and Development Program of China (Nos. 2017YFD0200505, 2018YFD0200100).

A series of novel aromatic amide compounds with N-pyridylpyrazole and 1,3,4-oxadiazole heterocyclic motifs were successfully synthesized with N-pyridylpyrazole carboxylic acid and 2-amino-3-methylbenzoic acid as the starting materials, via multi-step reactions of nucleophilic addition, cyclization, acylation, etc. The preliminary bioassay tests indicated that most of these compounds have apparent insecticidal activities, among which compounds N-(2-(5-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-1,3,4-oxadiazol-2-yl)-4-chloro-6-methylphenyl)acetamide (8a) and N-(2-(5-(3-bromo-1-(3-chloro-pyridin-2-yl)-1H-pyrazol-5-yl)-1,3,4-oxadiazol-2-yl)-4-chloro-6-methylphenyl)-3-chloro-2,2-dimethylpropanamide (8e) possessed a mortality rate of 70% towards Mythimna separata Walker at the concentration of 200 mg·L-1. Some of the compounds exhibited good fungicidal activities at 50 mg·L-1 against Sclerotinia sclerotiorum with the growth inhibitory rates of 54.5%~63.6%, which is more effective than the controls of triadimefon and chlorantraniliprole. Several compounds such as N-(2-(5-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-1,3,4-oxadiazol-2-yl)-4-chloro-6-methylphenyl)pivalamide (8f) and N-(2-(5-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-1,3,4-oxadiazol-2-yl)-4-chloro-6-methylphenyl)-4-fluoroben-zamide (8h) showed moderate fungicidal activity against Physalospora piricola. It is worth noting that compound 8e, which has favorable insecticidal and fungicidal activities towards Mythimna separata Walker and Sclerotinia sclerotiorum respectively, could be used as novel reference structure for new agrochemical innovations.

Key words: N-pyridylpyrazole derivatives, 1,3,4-oxadiazole, synthesis, insecticidal activity, fungicidal activity