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Antifungal Activity of β-Pinene-Based Hydronopyl Quaternary Ammonium Salts Against Phytopathogenic Fungi
Natural Product Communications ( IF 1.5 ) Pub Date : 2020-08-21 , DOI: 10.1177/1934578x20948365
Xue Zhen Feng 1 , Zhuanquan Xiao 2 , Li Zhang 1 , Shengliang Liao 1 , Shangxing Chen 1 , Hai Luo 1 , Lu He 1 , Guorong Fan 1 , Zongde Wang 1
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β-Pinene can be used as a cheap source to synthesize a large number of high value-added derivatives. In this study, a series of β-pinene derivatives was prepared, and the antifungal activities of the compounds were assessed against phytopathogenic fungi. Eight N-alkyl hydronopyl diethyl ammonium halide salts were synthesized by the reaction of hydronopyl diethyl ammonium halide with 8 halogenated alkanes. The structures of the synthesized products were characterized by Fourier-transform infrared spectroscopy and nuclear magnetic resonance spectroscopy and mass spectrometry. The antifungal activities of these derivatives were tested against 11 plant pathogens, and the preliminary structure-activity relationship is discussed. Some derivatives exhibited moderate to significant antifungal activity due to the fusion of the hydronopyl, a long-chain alkyl, bromine, and iodine anionic groups. In contrast to the structure-activity relationship of compounds 2a, 2b, and 2c, iodine ions in 2f, 2g, and 2f had a significant effect on enhancing the antifungal activity against Colletotrichum gloeosporioides, Sclerotinia sclerotiorum, Phytophthora capsici, Phomopsis, Sphaeropsis sapinea, Glomerella cingulata, and Fusicoccum aesculi. A higher molecular weight could increase the antifungal activity against Fusarium proliferatum, Alternaria kikuchiana, Sclerotinia sclerotiorum, P. capsici, Phomopsis, and S. sapinea. Compounds 2d and 2e exhibited broad-spectrum antifungal activity against the tested strains. These derivatives are expected to be used as precursor molecules for novel pesticide development in further research.



中文翻译:

β-P烯基羟丙基季铵盐类对植物病原真菌的抗真菌活性

β-P烯可用作合成大量高附加值衍生物的廉价来源。在这项研究中,制备了一系列的β-pine烯衍生物,并评估了该化合物对植物致病真菌的抗真菌活性。八N羟烷基二乙基卤化铵与8个卤代烷烃的反应合成了烷基-烷基羟乙基二卤化铵盐。用傅立叶变换红外光谱,核磁共振光谱和质谱对合成产物的结构进行了表征。测试了这些衍生物对11种植物病原体的抗真菌活性,并讨论了其初步的构效关系。由于羟丙基,长链烷基,溴和碘阴离子基团的融合,一些衍生物表现出中等至重要的抗真菌活性。与化合物2a2b2c的结构-活性关系相反,碘离子在2f中2克2F对增强抗抗真菌活性一个显著影响炭疽病,S clerotinia菌核病辣椒疫霉拟茎点霉枯梢炭疽病Fusicoccum aesculi。更高的分子量可以增加针对抗真菌活性镰刀菌梨黑斑病菌菌核病辣椒疫霉拟茎点霉,和S.梢。化合物2d2e显示出对测试菌株的广谱抗真菌活性。这些衍生物有望在进一步研究中用作新型农药开发的前体分子。

更新日期:2020-08-21
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