Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (10): 2191-2198.DOI: 10.6023/cjoc201505026 Previous Articles     Next Articles



张大强, 徐高飞, 刘艳红, 王道全, 杨新玲, 袁德凯   

  1. 中国农业大学理学院应用化学系 北京 100193
  • 收稿日期:2015-05-15 修回日期:2015-06-05 发布日期:2015-06-16
  • 通讯作者: 袁德凯
  • 基金资助:

    国家自然科学基金(No. 20902107)资助项目.

Synthesis and Biological Study of Novel N-(1H-Pyrazol-4-yl)-1H-pyrazole-3(5)-carboxamides

Zhang Daqiang, Xu Gaofei, Liu Yanhong, Wang Daoquan, Yang Xinling, Yuan Dekai   

  1. Department of Applied Chemistry, Science College, China Agricultural University, Beijin 100193
  • Received:2015-05-15 Revised:2015-06-05 Published:2015-06-16
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 20902107).

In order to investigate the biological activity of novel pyrazole derivatives, a series of N-(substituted-1H-pyra-zol-4-yl)-1H-pyrazole-3(5)-carboxamides with bi-heterocyclic scaffold were designed and synthesized from ethyl 5-alkyl-1H-pyrazole-3-carboxylate via several steps. The structure of all 18 target compounds were confirmed by 1H NMR and HRMS. The single crystal of 10b was obtained in methanol, and the structural data was collected by X-ray diffraction. As the bioassay data showed, i) most of the target compounds showed good inhibition activity against tobacco mosaic virus (TMV), especially compounds 10b and 10l possessing higher activity compared to ningnanmycin or virazole at the same concentration; (ii) all compounds showed lethal activity against army worm (Mythimna separata) and the larva of mosquito (Culex pipiens pallens), 10d possessing 40% lethal activity against army worm at a concentration of 600×10-6 g/mL, and 10f, 10k possessing 70% activity against the lava of mosquito at a concentration of 5×10-6 g/mL; iii) all compounds showed poor fungicidal activity at a concentration of 50×10-6 g/mL, except for 10h possessing 64% inhibition rate to Phoma asparagi Sacc. and 10q possessing 50% inhibition rate to Rhizoctonia solani. The above results showed that the bi-pyrazole compounds reported here could be used as lead compounds as anti-plant virus or insecticidal agents for further study.

Key words: bi-heterocyclic scaffold, N-(1H-pyrazol-4-yl)-1H-pyrazole-3(5)-carboxamide, single crystal, anti-TMV activity, pesticidal activity, fungicidal activity