摘要/Abstract

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


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