Synthesis and Biological Activity of Aryl Thiazole Piperidine Amide Compounds

doi:10.6023/cjoc201907034

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (2): 528-535.DOI: 10.6023/cjoc201907034 Previous Articles Next Articles

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

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

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.

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Abstract

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

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Ding Chengrong, Pan Yayun, Tan Chengxia. Synthesis and Biological Activity of Aryl Thiazole Piperidine Amide Compounds[J]. Chinese Journal of Organic Chemistry, 2020, 40(2): 528-535.

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芳基噻唑联哌啶酰胺类化合物的合成及生物活性

Synthesis and Biological Activity of Aryl Thiazole Piperidine Amide Compounds

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