Developing new pesticides with multi-function may be a suitable strategy to save time and cost and reduce the emergence of resistant strains of pests and pathogens. The organophosphorus derivatives have not been widely used in agriculture as fungicides. In this work, a series of six α-amino phosphonate derivatives were prepared and tested for their fungicidal and anti-phenol oxidase activities. The prepared compounds revealed a promising anti-fungal activity against Macrophomina phaseolina and Pythium aphanidermatum, especially M4, with MIC of 62 mg/L for M. phaseolina. M4 did not affect the fungus permeability rate of the cell membrane; however, it displayed a significant efficiency on mycelial soluble protein content. M4 and M3 with a hydroxyl group on the aniline moiety exhibited an observed anti-phenol oxidase activity. M4 inhibited the enzyme at 1 mg/mL. The DFT theoretical study revealed a significant correlation between the substituents of aniline moiety and the bioactivity of the studied compounds. The negative charge conspicuously influenced the anti-phenol oxidase activity. Our findings suggest the studied compounds as bases to design more effective α-amino phosphonate fungicides with additional anti-phenol oxidase activity.

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一些α-氨基膦酸酯衍生物的杀菌和抗酚氧化酶活性研究

开发新型多功能农药可能是节省时间和成本并减少害虫和病原体抗性菌株出现的合适策略。有机磷衍生物作为杀真菌剂尚未广泛用于农业。在这项工作中，制备了一系列六种 α-氨基膦酸酯衍生物并测试了它们的杀真菌和抗酚氧化酶活性。制备的化合物显示出有希望的抗真菌活性，对抗大叶腐霉和 Pythium aphanidermatum，尤其是 M4，对 M. phaseolina 的 MIC 为 62 mg/L。M4不影响细胞膜的真菌渗透率；然而，它对菌丝体可溶性蛋白质含量显示出显着的效率。在苯胺部分上具有羟基的 M4 和 M3 表现出观察到的抗酚氧化酶活性。M4 在 1 mg/mL 时抑制酶。DFT 理论研究揭示了苯胺部分的取代基与所研究化合物的生物活性之间存在显着相关性。负电荷显着影响抗酚氧化酶活性。我们的研究结果表明，所研究的化合物可作为设计更有效的具有额外抗酚氧化酶活性的 α-氨基膦酸盐杀菌剂的基础。