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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 8: 2575 - 2582

DOI: https://doi.org/10.6023/cjoc202003040

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

  • Jiang Zhenhua ,
  • Cheng Yi'nan ,
  • Shen Guofu ,
  • Zhang Mengmeng ,
  • Su Ziyang ,
  • Sun Liansheng ,
  • Li Honglian
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  • a Plant Protection College, Henan Agricultural University, Zhengzhou 450002;
    b Provincial Key Laboratory of the Discovery and Application of Novel Pesticide, Zhengzhou 450002

Received date: 2020-03-16

  Revised date: 2020-04-17

  Online published: 2020-05-19

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).

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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 . DOI: 10.6023/cjoc202003040

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