Design, Synthesis, and Assessment of Fungicidal Activity of Active Substructure 1,2,4-Triazole Containing Coumarin

文献类型： 外文期刊

第一作者： Lv, You

作者： Lv, You;Lv, You;Li, Kun;Yu, Zhenwu;Wu, Rongzhang;Chen, Angkun;Tian, Ruixi;Deng, Yuxuan;Tang, Liangfu;Fan, Zhijin;Li, Kun;Yu, Zhenwu;Wu, Rongzhang;Chen, Angkun;Tian, Ruixi;Deng, Yuxuan;Tang, Liangfu;Fan, Zhijin;Lei, Liu

作者机构：

关键词： Fusarium graminearum; coumarin; 1,2,4-triazole; 14-alpha demethylase; fungicidal activity

期刊名称：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY （ 影响因子：6.2； 五年影响因子：6.4 ）

ISSN： 0021-8561

年卷期： 2024 年 72 卷 49 期

页码：

收录情况： SCI

摘要： Fragment splicing and molecular docking are important techniques in the design of new agrochemicals. Based on our former discovery of 4-(3,4-dichloroisothiazole)-7-hydroxycumarins 1a and 1b as fungicidal leads, following fragment splicing and molecular docking, a series of bioactive substructure 1,2,4-triazole containing coumarins were designed and synthesized. In vitro fungicidal bioassay indicated that compound 7e was more active than 1b against Botrytis cinereal, Cercospora arachidicola, and Sclerotinia sclerotiorum, with a corresponding EC50 value of 4.02 vs 5.90, 6.03 vs 8.31, and 3.81 vs 5.37 mu g/mL, respectively. Compound 7e also showed an EC50 value of 4.15 mu g/mL against Fusarium graminearum. Moreover, compound 7e demonstrated a stronger inhibition than flutriafol against F. graminearum 14-alpha demethylase, with an IC50 value of 0.59 and 0.97 mu M, respectively. Calculation results based on density functional theory calculation (DFT), molecular dynamics (MD), and molecular mechanics/Poisson-Boltzmann surface area (MM/PBSA) studies gave a rational explanation between the activity of compound 7e and its structure. This study demonstrates that fragment splicing of 1,2,4-triazole and coumarin is a good technique for discovering a novel fungicide lead.

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