有机化学 ›› 2020, Vol. 40 ›› Issue (2): 528-535.DOI: 10.6023/cjoc201907034 上一篇    下一篇

研究简报

芳基噻唑联哌啶酰胺类化合物的合成及生物活性

丁成荣, 潘亚运, 谭成侠   

  1. 浙江工业大学化学工程学院 杭州 310032
  • 收稿日期:2019-07-24 修回日期:2019-09-08 发布日期:2019-10-12
  • 通讯作者: 谭成侠 E-mail:tanchengxia@zjut.edu.cn
  • 基金资助:
    浙江省绿色农药2011协同创新中心开放基金资助项目.

Synthesis and Biological Activity of Aryl Thiazole Piperidine Amide Compounds

Ding Chengrong, Pan Yayun, Tan Chengxia   

  1. College of Chemical Engineering Science, Zhejiang University of Technology, Hangzhou 310032
  • Received:2019-07-24 Revised:2019-09-08 Published:2019-10-12
  • Supported by:
    Project supported by the Collaborative Innovation Center of Zhejiang Province Green Pesticide.

为了寻找具有生物活性的新型芳香基噻唑联哌啶酰胺类先导化合物,设计并合成了15个未见文献报道的芳基噻唑联哌啶酰胺类化合物,其结构经1H NMR、13C NMR和HRMS确证,生物活性测定结果显示,部分目标化合物表现出高效的抑菌和杀虫活性,如在200 μg/mL浓度下,5-(3-溴苯基)-4-甲基-2-(1-((4-硝基苯基)磺酰基)哌啶-4-基)噻唑(6b)对黄瓜霜霉病的抑菌活性为100%,优于嘧菌酯,5-(4-溴苯基)-2-(1-((4-氯苯基)磺酰基)哌啶-4-基)-4-甲基噻唑(6c)对水稻纹枯病的抑菌活性为58.86%,与嘧菌酯相当;在500 μg/mL浓度下,(4-(5-(3-溴苯基)-4-甲基噻唑-2-基)哌啶-1-基)(间甲基苯基)酮(6h)对粘虫的杀虫活性为100%.

关键词: 噻唑联哌啶, 芳香结构, 抑菌活性, 杀虫活性

In order to find a novel biologically active compound containing aromatic thiazole piperidine structure, 15 novel aryl thiazole piperidine amide derivatives were designed and synthesized. The structures of the target compounds were fully characterized by 1H NMR, 13C NMR and HRMS spectra. The bioactivity test showed that some target compounds had good fungicidal and insecticidal activity. For example, the inhibition rate of 5-(3-bromophenyl)-4-methyl-2-(1-((4-nitrophenyl)-sulfonyl)piperidin-4-yl)thiazole (6b) against Pseudoperonospora cubensis was 100% better than azoxystrobin, and the inhibition rate of 5-(4-bromophenyl)-2-(1-((4-chlorophenyl)sulfonyl)piperidin-4-yl)-4-methylthiazole (6c) against Rhizoctonia solani was 58.86% comparable to azoxystrobin at 200 μg/mL. The lethal rate of (4-(5-(3-bromophenyl)-4-methylthiazol-2-yl) piperidin-1-yl) (m-tolyl)methanone (6h) against Mythimna separata was 100% at 500 μg/mL.

Key words: piperidinylthiazole, aromatic structure, fungicidal activity, insecticidal activity