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<p>To discover natural-derived fungicides, three series of 2-aryl-3,4-dihydroisoquinolinium salts (<b>6</b>–<b>8</b>) containing benzoate moieties were designed and synthesized based-on quaternary isoquinoline alkaloids. Their structures were confirmed by spectroscopic analysis. Antifungal activities against 10 phytopathogenic fungi were evaluated in vitro at 50 mg/L. Most of the title compounds exhibited moderate to excellent fungicidal activities, which were as active as the positive controls (chlorothalonil, carbendazim) and better than the reference model <b>9</b>. Furthermore, for <i>R. solani</i> and <i>R. cerealis</i> <b>8c</b> presented EC<sub>50</sub> values of 5.03 and 7.41 mg/L, respectively, equal to or <Emphasis FontCategory="NonProportional">superior</Emphasis> than chlorothalonil (4.63 mg/L, 15.0313 mg/L). The SARs studies indicated that introduce the benzoate moieties had significant effect on the antifungal activity, in which the presence of 3′-CO<sub>2</sub>Me (<b>7</b>) and 4′-CO<sub>2</sub>Me (<b>8</b>) derivatives were more active than 2′-CO<sub>2</sub>Me ones (<b>6</b>). Further mechanism studies on <i>R. solani</i> elucidated that compound <b>8c</b> could increase the permeability of the cell membrane, dramatically induce the accumulation of ROS. These results revealed that compound <b>8c</b> could represent as a potential lead for the development of antifungal agents.</p><p></p>

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Design, synthesis and antifungal study of novel 2-aryl-3,4-dihydroisoquinolin-2-ium salts containing benzoate moieties

  • 期刊论文

  • 发表日期：

    2025年1月22日

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  • Wei Chen,
  • Yanxi Jin,
  • Luyao Wang

摘要

To discover natural-derived fungicides, three series of 2-aryl-3,4-dihydroisoquinolinium salts (6–8) containing benzoate moieties were designed and synthesized based-on quaternary isoquinoline alkaloids. Their structures were confirmed by spectroscopic analysis. Antifungal activities against 10 phytopathogenic fungi were evaluated in vitro at 50 mg/L. Most of the title compounds exhibited moderate to excellent fungicidal activities, which were as active as the positive controls (chlorothalonil, carbendazim) and better than the reference model 9. Furthermore, for R. solani and R. cerealis 8c presented EC50 values of 5.03 and 7.41 mg/L, respectively, equal to or superior than chlorothalonil (4.63 mg/L, 15.0313 mg/L). The SARs studies indicated that introduce the benzoate moieties had significant effect on the antifungal activity, in which the presence of 3′-CO2Me (7) and 4′-CO2Me (8) derivatives were more active than 2′-CO2Me ones (6). Further mechanism studies on R. solani elucidated that compound 8c could increase the permeability of the cell membrane, dramatically induce the accumulation of ROS. These results revealed that compound 8c could represent as a potential lead for the development of antifungal agents.