College of Forestry, Jiangxi Agricultural University; National Forestry and Grassland Bureau Woody Spice (East China) Engineering Technology Research Center; National Forestry and Grassland Bureau/Jiangxi Provincial Camphor Engineering Technology Research Center; Collaborative Innovation Center of Jiangxi Typical Trees Cultivation and Utilization, Nanchang 330045, China.
Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing 210042, China.
Molecules. 2019 Aug 29;24(17):3144. doi: 10.3390/molecules24173144.
The development of new antifungal agents has always been a hot research topic in pesticide development. In this study, a series of derivatives of natural compound β-pinene were prepared, and the antifungal activities of these derivatives were evaluated. The purpose of this work is to develop some novel molecules as promising new fungicides.
Through a variety of chemical reactions, β-pinene was transformed into a series of β-pinene-based derivatives containing amide moieties and acylthiourea moieties. The antifungal activities of these derivatives against five plant pathogens including , , , sp. and were tested; preliminary structure-activity relationship was discussed.
Some derivatives exhibited moderate or significant antifungal activity due to the fusion of the amide moiety or the acylthiourea moiety with the pinane skeleton. The structure-activity relationship analysis showed that the fluorine atom and the strong electron withdrawing nitro group, or trifluoromethyl group on the benzene ring of the derivatives had a significant effect on the improvement of the antifungal activity against , , and sp. Meanwhile, the introduction of an ethyl group at the meta-position on the benzene ring of the derivatives could improve the antifungal activity against . Compounds , , , exhibited broad-spectrum antifungal activity against the tested strains. Compound had significant antifungal activity against (IC = 0.18 μmol/L). These derivatives were expected to be used as precursor molecules for novel pesticide development in further research.
新型抗真菌剂的开发一直是农药开发的热门研究课题。在本研究中，制备了一系列天然化合物β-蒎烯的衍生物，并评估了这些衍生物的抗真菌活性。这项工作的目的是开发一些新型分子作为有前途的新型杀菌剂。
通过多种化学反应，将β-蒎烯转化为一系列含有酰胺基和酰基硫脲基的β-蒎烯基衍生物。测试了这些衍生物对五种植物病原菌（包括 、 、 、 和 ）的抗真菌活性；初步探讨了结构-活性关系。
由于酰胺基或酰基硫脲基与蒎烷骨架的融合，一些衍生物表现出中等或显著的抗真菌活性。构效关系分析表明，苯环上取代基的氟原子和强吸电子硝基或三氟甲基对提高对 、 、 和 sp.的抗真菌活性有显著影响。同时，在苯环上取代基的间位引入乙基基团可以提高对 的抗真菌活性。化合物 、 、 、 对所测试的菌株表现出广谱抗真菌活性。化合物 对 （IC = 0.18 μmol/L）具有显著的抗真菌活性。这些衍生物有望在进一步的研究中作为新型农药开发的前体分子。
