Instituto de Ciencias Químicas Aplicadas, Facultad de Ingeniería, Universidad Autónoma de Chile, El Llano Subercaseaux 2801, Santiago CP 8900000, Chile.
Departamento de Química, Universidad Técnica Federico Santa María, Avenida España 1680, Valparaíso CP 2340000, Chile.
Molecules. 2019 Nov 19;24(22):4196. doi: 10.3390/molecules24224196.
is a phytopathogen that causes extensive damage in different crops, and therefore, produces important economic losses all around the world. Chemical fungicides are a key factor for the control of this disease. However, ecological and environmental considerations, as well as the appearance of strains that are resistant to commercial fungicides, have prompted the quest for new antifungal agents which are of low ecological impact. In this work, a series of new 2-allylphenol derivatives was synthesized, and their structures were confirmed by FT-IR, NMR, and MS. Some of the synthesized compounds, more specifically nitro derivatives, exhibit strong growth inhibition of with EC as low as 10.0 µg/mL. This level of activity is similar to that exhibited by , a commonly-used commercial fungicide; therefore, these compounds might be of agricultural interest due to their potential use as fungicides against . The results indicate that this activity depends on the chemical structures of the 2-allylphenol derivatives, and that it is strongly enhanced in molecules where nitro and hydroxyl groups adopt a -para configuration. These effects are discussed in terms of the electronic distribution of the aromatic ring induced by substituent groups.
是一种植物病原菌,可对不同作物造成广泛的损害,从而在全球范围内造成重大经济损失。化学杀菌剂是控制这种疾病的关键因素。然而,生态和环境方面的考虑,以及对商业杀菌剂产生抗性的菌株的出现,促使人们寻求对生态影响较小的新型抗真菌剂。在这项工作中,合成了一系列新的 2-烯丙基酚衍生物,并通过 FT-IR、NMR 和 MS 确认了它们的结构。一些合成的化合物,特别是硝基衍生物,对 的生长抑制作用很强,EC 值低至 10.0 µg/mL。这种活性水平与常用的商业杀菌剂 相似;因此,由于它们可能作为杀菌剂用于防治 ,这些化合物可能具有农业应用价值。结果表明,这种活性取决于 2-烯丙基酚衍生物的化学结构,并且在硝基和羟基采用 -para 构型的分子中得到了强烈增强。这些效应是根据取代基基团诱导的芳环的电子分布来讨论的。