Synthesis of Thiophene Carboxamide Derivatives and Inhibitory Activity against Gaeumannomyces graminis var. tritici.

doi:10.6023/cjoc201401036

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (6): 1124-1131.DOI: 10.6023/cjoc201401036 Previous Articles Next Articles

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噻吩甲酰胺衍生物的合成及其对小麦全蚀病病原菌的抑制活性

谢桂英^a,b, 靳文波^a, 赵艳芹^a, 程绎南^a,b, 孙炳剑^a,b, 孙淑君^a,b, 汪梅子^a, 位丹丹^a, 李洪连^a,b

a. 河南农业大学植保学院郑州 450002;
b. 新型农药创制与应用河南省重点实验室郑州 450002

收稿日期:2014-01-22 修回日期:2014-02-21 发布日期:2014-03-12
通讯作者: 程绎南, 李洪连 E-mail:chyn212@aliyun.com;honglianli@sina.com
基金资助:
国家“十二五”粮食丰产科技工程（Nos. 2011BAD16B07，2012BAD04B07）及中国科学院现代农业示范和区域创新集群计划（No. CXJQ120111）资助项目.

Synthesis of Thiophene Carboxamide Derivatives and Inhibitory Activity against Gaeumannomyces graminis var. tritici.

Xie Guiying^a,b, Jin Wenbo^a, Zhao Yanqin^a, Cheng Yinan^a,b, Sun Bingjian^a,b, Sun Shujun^a,b, Wang Meizi^a, Wei Dandan^a, Li Honglian^a,b

a. College of Plant Protection, Henan Agricultural University, Zhengzhou 450002;
b. Henan Provincial Key Laboratory of the Discovery and Application of Novel Pesticide, Zhengzhou 450002

Received:2014-01-22 Revised:2014-02-21 Published:2014-03-12
Supported by:
Project supported by the National Food Production Technology Project of China during the Twelfth Five-Year Period (Nos. 2011BAD16B07, 2012BAD04B07) and the Modern Agriculture Demonstration and Regional Innovation Cluster Plan Project of the Chinese Academy of Sciences (No. CXJQ120111).

1. Synthesis of Thiophene Carboxamide Derivatives and Inhibitory Activity against Gaeumannomyces graminis var. tritici..PDF(8188KB)

Abstract

The procedures for synthesizing the substituted ester 2-hydrothiophene-3-carboxylate and its silanization were explored. The reaction conditions were optimized. And with the substituted thiophene as the framework, 20 new thiophene carboxamide derivatives were synthesized. The chemical structures of thiophene carboxamide derivatives were confirmed by ¹H NMR, ¹³C NMR, HRMS or elemental analysis techniques. The inhibitory activity against Gaeumannomyces graminis var. tritici was evaluated in vitro by the plate method. The preliminary structure-activity relationship indicated that the substituent bonded to the amide nitrogen atom and the steric hindrance of the substituent at 2nd position of the thiophene carboxamide had a significant influence on the activity. The compounds 7b～7d, 7l, 7m and 7o exhibited very high inhibitory activity. The results would be helpful for the design of lead compounds.

Key words: thiophene carboxamide derivative, synthesis, Gaeumannomyces graminis var. tritici., inhibitory activity

Cite this article

Xie Guiying, Jin Wenbo, Zhao Yanqin, Cheng Yinan, Sun Bingjian, Sun Shujun, Wang Meizi, Wei Dandan, Li Honglian. Synthesis of Thiophene Carboxamide Derivatives and Inhibitory Activity against Gaeumannomyces graminis var. tritici.[J]. Chin. J. Org. Chem., 2014, 34(6): 1124-1131.

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噻吩甲酰胺衍生物的合成及其对小麦全蚀病病原菌的抑制活性

Synthesis of Thiophene Carboxamide Derivatives and Inhibitory Activity against Gaeumannomyces graminis var. tritici.

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