硫色酮甲酰胺衍生物的合成及其抑菌活性

doi:10.6023/cjoc202506027

有机化学

硫色酮甲酰胺衍生物的合成及其抑菌活性

周蒲^a, 苏子洋^a, 崔得运^b, 程绎南^*,a, 李毅^a, 周海峰^a, 孙炳剑^a, 李洪连^a

a.河南农业大学植保学院, 郑州, 邮编 450046;
b.河南省科学院高新技术研究中心, 郑州, 邮编 450002

收稿日期:2025-06-20 修回日期:2025-08-18

Synthesis of Thiochromone Formamide Derivatives and Antifungal Activities

Zhou Pu^a, Su Ziyang^a, Cui Deyun^b, Cheng Yi-nan^*,a, Li Yi^a, Zhou Haifeng^a, Sun Bingjian^a, Li Honglian^a

^aPlant Protection College of Henan Agricultural University, Zhengzhou 450046;
^bHigh & New Technology Research Center of Henan Academy of Sciences, Zhengzhou 450002

Received:2025-06-20 Revised:2025-08-18
Contact: ^*E-mail: chyn212@aliyun.com.
Supported by:
Key R&D Special Project of Henan Province (No 251111111600), Key Research Project Plan for Higher Education Institutions in Henan Province (NO. 25A210014), High-level Talent Research Start-up Project Funding of Henan Academy of Sciences (NO. 241802037).

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摘要/Abstract

设计了具有新型结构的2-取代硫色酮甲酰胺衍生物, 分别以2-氯苯乙酮和2-巯基苯甲酸为原料设计了两条相应化合物的合成路线, 合成了13个2-取代硫色酮甲酰胺衍生物, 其结构通过¹H NMR、¹³C NMR 和 HRMS 进行了表征, 利用平皿法研究了化合物对小麦全蚀病菌的抑制活性.构-效关系研究表明, 2-位取代基对化合物活性具有重要影响, 化合物6f对小麦全蚀病菌具有较好的抑制活性, 在50 mg/L浓度下可以达到100%的抑制率; 进一步研究结果表明化合物13e对小麦全蚀病菌的抑制效果突出, 在12.5 mg/L浓度下亦可以达到100%的抑制率, 其计算的EC₅₀值达到了0.07 mg/L的较低水平, 抑制活性超过了阳性对照硅噻菌胺(EC₅₀ 26.7 mg/L). 该研究将对活性化合物进一步结构设计与优化提供一定帮助, 为新农药的创制提供参考.

关键词: 硫色酮甲酰胺衍生物, 合成路线, 小麦全蚀病菌, 抑制活性

New thiochromone formamide derivatives substituted at position 2 were designed and two synthetic routes for these compounds were developed using 1-(2-chlorophenyl)ethanone and 2-mercaptobenzoic acid as materials respectively. Thirteen 2-substituted thiochromone formamides were synthesized. Their structures were characterized by ¹H NMR、¹³C NMR and HRMS. Their antifungal activities against Gaeumannomyces graminis var. tritici were evaluated in vitro by the plate method. The results of structure-activity relationship indicated that the group at position 2 of thiochromone formamide derivatives had an important influence on their antifungal activities against Gaeumannomyces graminis var. tritici. Compound 6f showed a good activity. Its inhibitory rate reached up to100% at 50 mg/L. Further results showed that the activity of compound 13e against Gaeumannomyces graminis var. tritici was excellent. Its inhibitory rate also reached up to100% at 12.5 mg/L with a lower value of EC₅₀ (0.07 mg/L) than positive control Silthiopham (EC₅₀ 26.7 mg/L). The results will provide some help for design of new active compounds and development of new fungicides.

Key words: thiochromone formamide derivatives, synthetic routes, Gaeumannomyces graminis var. tritici, inhibitory activities

引用此文

周蒲, 苏子洋, 崔得运, 程绎南, 李毅, 周海峰, 孙炳剑, 李洪连. 硫色酮甲酰胺衍生物的合成及其抑菌活性[J]. 有机化学, doi: 10.6023/cjoc202506027.

Zhou Pu, Su Ziyang, Cui Deyun, Cheng Yi-nan, Li Yi, Zhou Haifeng, Sun Bingjian, Li Honglian. Synthesis of Thiochromone Formamide Derivatives and Antifungal Activities[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202506027.

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