Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 738-756.DOI: 10.6023/cjoc202007068 Previous Articles     Next Articles



石军1, 罗娜1, 丁慕晗1, 李传会1, 万苏然1, 李培甲1, 李君荭1, 鲍小平1,*()   

  1. 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 教育部绿色农药与农业生物工程重点实验室 贵阳 550025
  • 收稿日期:2020-07-29 修回日期:2020-08-11 发布日期:2020-09-16
  • 通讯作者: 鲍小平
  • 作者简介:
    * Corresponding author. E-mail:
  • 基金资助:
    贵州省自然科学基金(20201Z025); 贵州省教育厅科技拔尖人才支持计划(2018038); 贵州省高层次留学人才创新创业(201809)

Synthesis and Antimicrobial Activities of Novel 1,3,4-Oxa(Thia)- diazole Derivatives Containing 6-Fluoroquinazoline Moiety

Jun Shi1, Na Luo1, Muhan Ding1, Chuanhui Li1, Suran Wan1, Peijia Li1, Junhong Li1, Xiaoping Bao1,*()   

  1. 1 State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025
  • Received:2020-07-29 Revised:2020-08-11 Published:2020-09-16
  • Contact: Xiaoping Bao
  • Supported by:
    the Natural Science Foundation of Guizhou Province(20201Z025); the Young Top-Notch Talent Support Program of Guizhou Provincial Education Department(2018038); the Guizhou Provincial High-Level Overseas Talents Innovation and Entrepreneurship Program(201809)

To search efficient agricultural antimicrobial lead compounds, fifty 1,3,4-oxa(thia)diazole derivatives 6a~6y and 8a~8y containing 6-fluoroquinazoline moiety were designed, synthesized and evaluated for their antimicrobial activities, based on the method of the splicing of bioactive substructures. The structures of target compounds were fully characterized by 1H NMR, 13C NMR, and HRMS spectra, and two compounds 6i and 8x were further confirmed via single crystal X-ray diffraction analysis. The preliminary bioassays revealed that some compounds exhibited good antifungal activity in vitro. For example, compounds 6b, 6d, 6t, 6v and 6x were found to have the inhibition rates of 58%, 58%, 55%, 63% and 60% against Gibberella zeae at 50 μg/mL, respectively. Additionally, compounds 6v and 8v displayed the inhibition efficacies of 71% and 64% against Cytospora mandshurica at 50 μg/mL, respectively. Moreover, compound 6v demonstrated an inhibition rate of 72% against Colletotrichum gloeosporioides at 50 μg/mL. The above activities were all better than that of control agent Hymexazol (51%, 61%, and 70%, respectively). Finally, some compounds also showed certain inhibition potencies in vitro against tested bacteria at 100 μg/mL.

Key words: 1,3,4-oxadiazole, 1,3,4-thiadiazole, 6-fluoroquinazoline, synthesis, antimicrobial activity