高亚强, 马俊豪, 游江, 周蒲, 张列雄, 徐志红. 含苯乙酮结构片段的吩嗪-1-羧酸酯类衍生物的合成及生物活性[J]. 农药学学报, 2021, 23(6): 1227-1234. DOI: 10.16801/j.issn.1008-7303.2021.0125
    引用本文: 高亚强, 马俊豪, 游江, 周蒲, 张列雄, 徐志红. 含苯乙酮结构片段的吩嗪-1-羧酸酯类衍生物的合成及生物活性[J]. 农药学学报, 2021, 23(6): 1227-1234. DOI: 10.16801/j.issn.1008-7303.2021.0125
    GAO Yaqiang, MA Junhao, YOU Jiang, ZHOU Pu, ZHANG Liexiong, XU Zhihong. Synthesis and bioactivities of phenazine-1-carboxylate derivatives containing acetophenone structural fragments[J]. Chinese Journal of Pesticide Science, 2021, 23(6): 1227-1234. DOI: 10.16801/j.issn.1008-7303.2021.0125
    Citation: GAO Yaqiang, MA Junhao, YOU Jiang, ZHOU Pu, ZHANG Liexiong, XU Zhihong. Synthesis and bioactivities of phenazine-1-carboxylate derivatives containing acetophenone structural fragments[J]. Chinese Journal of Pesticide Science, 2021, 23(6): 1227-1234. DOI: 10.16801/j.issn.1008-7303.2021.0125

    含苯乙酮结构片段的吩嗪-1-羧酸酯类衍生物的合成及生物活性

    Synthesis and bioactivities of phenazine-1-carboxylate derivatives containing acetophenone structural fragments

    • 摘要: 为了提高吩嗪-1-羧酸 (申嗪霉素) 的生物活性,以吩嗪-1-羧酸和不同取代的苯乙酮为原料,通过溴化反应和亲核取代反应,合成了22个未见文献报道的含苯乙酮结构片段的吩嗪-1-羧酸酯类化合物 3a3c6a6s ,其结构均得到核磁共振氢谱(1H NMR)、碳谱(13C NMR)和高分辨质谱确证。分别采用菌丝生长速率法和琼脂保湿浸叶法测定了目标化合物对6种植物病原菌的杀菌活性和对朱砂叶螨雌成螨的杀螨活性。杀菌活性测定结果表明:在0.2 mmol/L下大部分目标化合物对水稻纹枯病菌Rhizoctonia solani具有一定的抑制作用,其中 6b6e 的抑制率分别为56.05%和65.37%,低于对照药剂吩嗪-1-羧酸 (86.83%)。杀螨活性测定结果表明:药后24 h,大部分目标化合物对朱砂叶螨Tetranychus cinnabarinus雌成螨具有良好的杀螨活性,在1 mmol/L下化合物 6k6m 的校正死亡率分别为87.88%和90.82%,进一步测得其相应的LC50值分别为0.25 和0.19 mmol/L。本研究所合成的新化合物不仅具有一定的杀菌活性,还具有较好的杀螨活性,这为吩嗪-1-羧酸的进一步结构改造提供了新思路。

       

      Abstract: To improve the bioactivities of phenazine-1-carboxylic acid (shenqinmycin), 22 phenazine-1-carboxylate derivatives containing acetophenone structural fragments 3a - 3c and 6a - 6s , which have not been reported in literatures were synthesized by bromination reaction and nucleophilic substitution using phenazine-1-carboxylic acid and different substituted acetophenone as raw materials. And their structures were confirmed by 1H NMR, 13C NMR and high resolution mass spectrometry. The fungicidal activities of the target compounds against 6 plant pathogens and the acaricidal activities of adult mite of Tetranychus cinnatarinus were determined by mycelial growth rate method and agar moisturizing leaf soaking method, respectively. The results of fungicidal activity assay showed that most of the target compounds had certain inhibitory activities against Rhizoctonia solani. At the concentration of 0.2 mmol/L, the inhibition rates of compounds 6b and 6e against R. solani were 56.05% and 65.37%, respectively, which were lower than that of the control compound phenazine-1-carboxylic acid (86.83%). The results of acaricidal activity determination showed that: at 1 mmol/L, the corrected mortality rates of compounds 6k and 6m were 87.88% and 90.82%, respectively, and the LC50 values of compounds 6k and 6m against adult mite of T. cinnatarinus were 0.25 mmol/L and 0.19 mmol/L, respectively. The new compounds synthesized in this work not only had certain fungicidal activities, but also had better acaricidal activities. It provided a new idea for the further structural modification of phenazine-1-carboxylic acid.

       

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