Synthesis of 1,2,4-Triazole Benzamide Derivatives and Fungicidal Activity

doi:10.6023/cjoc202003040

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (8): 2575-2582.DOI: 10.6023/cjoc202003040 Previous Articles Next Articles

1,2,4-三唑取代的苯甲酰胺衍生物的合成及其抑菌活性

蒋振华^a, 程绎南^a,b, 申国富^a, 张蒙萌^a, 苏子洋^a, 孙连省^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:2020-03-16 修回日期:2020-04-17 发布日期:2020-05-20
通讯作者: 程绎南 E-mail:chyn212@aliyun.com
基金资助:
国家自然科学基金（No.U1704116）和国家重点研发计划（No.2017YFD0201700）资助项目.

Synthesis of 1,2,4-Triazole Benzamide Derivatives and Fungicidal Activity

Jiang Zhenhua^a, Cheng Yi'nan^a,b, Shen Guofu^a, Zhang Mengmeng^a, Su Ziyang^a, Sun Liansheng^a, Li Honglian^a,b

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

Received:2020-03-16 Revised:2020-04-17 Published:2020-05-20
Supported by:
Project supported by the National Natural Science Foundation of China (No. U1704116) and the National Key R&D Program of China (No. 2017YFD0201700).

1. cjoc202003040辅助材料.pdf(3367KB)

Abstract

The synthetic route of substituted 1,2,4-triazole benzamide derivatives was explored, which included several steps such as catalytic cross-coupling of 2,6-dichlorobenzonitrile with a triazole, amidation of nitrile, diazotization of amide and hydrolysis, and amidation of acid. Unreported 14 new 1,2,4-triazole benzamide derivatives were synthesized. Their chemical structures were characterized by ¹H NMR, ¹³C NMR and HRMS. Their antifungal activities against Gaeumannomyces graminis var. tritici and Fusarium pseudocerealum were evaluated in vitro by the plate method. The results indicated that antifungal activities of compound 2-chloro-N-phenyl-6-(1H-1,2,4-triazol-1-yl)benzamide (7i) against Gaeumannomyces graminis var. tritici reached up to 80% at the concentrations of 100 mg/L, and were comparable to the control level of silthiopham at the concentrations of 50 and 25 mg/L. However, these compounds didn't show obvious antifungal activities against Fusarium pseudocerealum.

Key words: 1,2,4-triazobenzamide derivatives, synthesis, Gaeumannomyces graminis var. tritici, antifungal activity

Cite this article

Jiang Zhenhua, Cheng Yi'nan, Shen Guofu, Zhang Mengmeng, Su Ziyang, Sun Liansheng, Li Honglian. Synthesis of 1,2,4-Triazole Benzamide Derivatives and Fungicidal Activity[J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2575-2582.

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1,2,4-三唑取代的苯甲酰胺衍生物的合成及其抑菌活性

Synthesis of 1,2,4-Triazole Benzamide Derivatives and Fungicidal Activity

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