Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2813-2820.DOI: 10.6023/cjoc201903048 Previous Articles     Next Articles



陈英, 李普, 陈梅, 苏时军, 贺军, 张敏, 柳立伟, 薛伟*()   

  1. 贵州大学精细化工研究开发中心 绿色农药与农业生物工程国家重点实验室培育基地教育部绿色农药与生物工程重点实验室 贵阳 550025
  • 收稿日期:2019-03-23 修回日期:2019-04-18 发布日期:2019-06-12
  • 通讯作者: 薛伟
  • 基金资助:

Syntheses and Biological Activities of 1,4-Pentadien-3-oneDerivatives Containing Thioether Triazole Moiety

Chen Ying, Li Pu, Chen Mei, Su Shijun, He Jun, Zhang Min, Liu Liwei, Xue Wei*()   

  1. State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Bioengineering of Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025
  • Received:2019-03-23 Revised:2019-04-18 Published:2019-06-12
  • Contact: Xue Wei
  • Supported by:
    Project supported by the National Key Research and Development Program of China(2017YFD0200506);The National Natural Science Foundation of China(21867003)

A series of novel 1,4-pentadien-3-one derivatives containing thioether triazole units were synthesized by introducing triazoles bearing thiol groups into the structures of 1,4-pentadien-3-one. The structures of the newly synthesized compounds were assigned via 1H NMR, 13C NMR and HRMS. Bioassays indicated that some of the compounds showed potential antibacterial activities against X. citri, X. oryzae and R. solanacearum. Among them, compounds F4, F6 and F16 demonstrated appreciable inhibitory effect against Xanthomonas axonopodis pv. citri, with half-maximal effective concentration (EC50) values of 16.3, 9.9 and 15.9 μg/mL, which were better than commercial agent bismerthiazol (54.9 μg/mL). Compounds F1, F7 and F15 demonstrated appreciable inhibitory effects against Xanthomonas oryzae pv. Oryzae with EC50 values of 9.6, 19.2 and 21.3 μg/mL, which were better than commercial agent bismerthiazol (69.3 μg/mL). Compounds F3 and F6 also demonstrated appreciable inhibitory effects against Ralstonia solanacearum with EC50 values of 14.2 and 14.5 μg/mL, which were better than commercial agent bismerthiazol (82.6 μg/mL). The possible mechanism of the antibacterial activity of the target compound F6 against Xanthomonas axonopodis was investigated through scanning electron microscopy.

Key words: 1,4-pentadien-3-one, thioether triazole, biological activity, scanning electron microscope