Medicinal Chemistry Laboratory, Pharmacy Department, Federal University of Sergipe, São Cristóvão, SE, Brazil.
Pest Manag Sci. 2012 Nov;68(11):1478-83. doi: 10.1002/ps.3331. Epub 2012 Jun 6.
Dengue fever is a severe public health problem for several countries. In order to find effective larvicides to aid control programs, the structure-activity relationships of eugenol derivatives against Aedes aegypti (Diptera: Culicidae) larvae were evaluated. Additionally, the composition and larvicidal activity of Syzygium aromaticum essential oil was assessed.
Four compounds representing 99.05% of S. aromaticum essential oil have been identified. The essential oil was active against Ae. aegypti larvae (LC(50) = 62.3 and 77.0 ppm, field-collected and Rockefeller larvae respectively). The larvicidal activity of eugenol, the major compound of the essential oil, was further evaluated (LC(50) = 93.3 and 71.9 ppm, field-collected and Rockefeller larvae respectively). The larvicidal activity and structure-activity relationships of synthetic derivatives of eugenol were also assessed. The larvicidal activity of the derivatives varied between 62.3 and 1614.9 ppm. Oxidation of eugenol allylic bond to a primary alcohol and removal of the phenolic proton resulted in decreased potency. However, oxidation of the same double bond in 1-benzoate-2-methoxy-4-(2-propen-1-yl)-phenol resulted in increased potency.
Structural characteristics were identified that may contribute to the understanding of the larvicidal activity of phenylpropanoids. The present approach may help future work in the search for larvicidal compounds.
登革热是多个国家严重的公共卫生问题。为了寻找有效的杀幼虫剂来辅助控制项目，评估了丁香酚衍生物对埃及伊蚊（双翅目：蚊科）幼虫的结构-活性关系。此外，评估了丁香属植物精油的组成和杀幼虫活性。
已鉴定出 4 种代表丁香属植物精油 99.05%的化合物。该精油对埃及伊蚊幼虫具有活性（LC 50 值分别为 62.3 和 77.0 ppm，分别为野外采集和洛克菲勒幼虫）。进一步评估了精油中主要化合物丁香酚的杀幼虫活性（LC 50 值分别为 93.3 和 71.9 ppm，分别为野外采集和洛克菲勒幼虫）。还评估了丁香酚合成衍生物的杀幼虫活性和结构-活性关系。衍生物的杀幼虫活性在 62.3 和 1614.9 ppm 之间变化。丁香酚烯丙基键的氧化和酚质子的去除导致活性降低。然而，在 1-苯甲酸-2-甲氧基-4-（2-丙烯-1-基）-苯酚中同一双键的氧化导致活性增加。
确定了可能有助于理解苯基丙烷类化合物杀幼虫活性的结构特征。本方法可能有助于未来寻找杀幼虫化合物的工作。
