含1,2,4-三唑的N-苯基-乙酰胺类衍生物的合成及其杀菌活性

    Synthesis and fungicidal activity of N-phenylacetamide derivatives containing 1,2,4-triazole

    • 摘要: 为发现具有更好杀菌活性的化合物,以醚为桥将取代N-苯基-乙酰胺与1-(2,4-二氟苯基)-2-(1H-1,2,4-三唑-1-基)-乙醇进行拼接,设计并合成了一系列含1,2,4-三唑的N-苯基-乙酰胺类衍生物 (6a~6o),其结构均经核磁共振氢谱 (1H NMR)、碳谱 (13C NMR) 和高分辨质谱 (HRMS) 确证。菌丝生长速率法室内杀菌活性测定结果显示,化合物6j 对玉米小斑病菌 (Bipolaris maydis) 的EC50值为0.15 mg/L,室内毒力与对照药剂烯唑醇相当(0.12 mg/L)。化合物6a 对水稻纹枯病菌 (Rhizoctonia solani) 的EC50值为6.96 mg/L,室内毒力低于对照药剂烯唑醇(1.88 mg/L)。但盆栽结果显示,在200 和100 mg/L下,化合物6a 对水稻纹枯病的保护防效分别为76.65%和43.92%,高于对照药剂烯唑醇 (68.03%和42.02%);治疗防效分别为78.90%和45.05%,高于对照药剂烯唑醇 (75.56%和42.34%)。本研究合成的目标化合物具有一定的杀菌活性,丰富了三唑类杀菌剂的结构类型。

       

      Abstract: To discover compounds with better fungicidal activity, a series of N-phenylacetamide derivatives (6a-6o) containing 1,2,4-triazoles were designed and synthesized by combining substituted N-phenylacetamide with 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanol using an ether bridge. Their structures were confirmed by 1H NMR, 13C NMR, and HRMS analyses. The results of indoor fungicidal activity determination using the mycelial growth rate method showed that compound 6j had an EC50 value of 0.15 mg/L for Bipolaris maydis, with indoor toxicity comparable to that of the control agent diniconazole (0.12 mg/L). The EC50 value of compound 6a for Rhizoctonia solani was 6.96 mg/L, and its indoor toxicity is lower than that of the control agent diniconazole (1.88 mg/L). However, the potted results showed that at concentrations of 200 and 100 mg/L, the protective efficacy of compound 6a against rice sheath blight was 76.65% and 43.92%, respectively, which were higher than those of diniconazole (68.03% and 42.02%). The curative efficacy was 78.90% and 45.05%, respectively, which were higher than those of diniconazole (75.56% and 42.34%). The synthesized target compounds in this study have certain fungicidal activities, thereby enriching the structural types of triazole fungicides.

       

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