背景:天然产物丹皮酚是一种丰富且可持续的天然生物资源,及其衍生物具有各种独特的生物学功效。众所周知,席夫碱是一类具有广泛生物活性的有机化合物,包括抗真菌药,杀虫,抗病毒,和杀线虫。
结果:为了发现基于生物天然产品的农药,九种中间体(2-10),12磺酰基腙(11a-11c,12a-12c,13a-13c,和14a-14c)和20个亚苄基腙(18a-18r,19a,和20a)通过丹皮酚的结构修饰合成,其结构经质子核磁共振(1HNMR)表征,碳-13(13C)NMR,和高分辨率质谱(HRMS)。化合物14a的立体化学构型,18d,和18r通过单晶X射线衍射明确证实。此外,这些化合物作为抗卵菌的生物活性,抗真菌,和杀线虫剂对抗三种严重的农业害虫,辣椒疫霉,禾谷镰刀菌,和异型甘氨酸进行了评估。在所有测试的化合物中:(i)化合物7对辣椒疫霉表现出有希望的抗卵菌,具有15.81mgL-1的半最大有效浓度(EC50)值;(ii)化合物2、7、10和19a显示出对F.graminearum的有希望的抗真菌作用。EC50值分别为12.22、14.72、23.39和33.10mgL-1;(iii)十种化合物(12a-12c,14c,18g-18j,18m,和19a)显示出对H.甘氨酸的显着杀线虫活性,中位致死浓度(LC50)值均小于30.00mgL-1。特别是对于化合物18g,其LC50值最小,12.65mgL-1。
结论:研究结果表明,在丹皮酚的C5位引入硝基,或在C5和C3位置引入卤素,可以显着增强其对辣椒疫霉的生物活性,F.谷草,和H.甘氨酸。©2024化学工业学会。
BACKGROUND: The natural product paeonol is a rich and sustainable natural bioresource, and its derivatives have various unique biological efficacy. As is well known, Schiff bases are a class of organic compounds with a wide range of biological activities, including anti-fungal, insecticidal, anti-viral, and nematicidal.
RESULTS: To discover biorational natural product-based pesticides, nine intermediates (2-10), 12 sulfonylhydrazones (11a-11c, 12a-12c, 13a-13c, and 14a-14c) and 20 benzylidene hydrazones (18a-18r, 19a, and 20a) were synthesized by structural modification of paeonol, and their structures were characterized by proton nuclear magnetic resonance (1H NMR), carbon-13 (13C) NMR, and high-resolution mass spectrometry (HRMS). The stereochemical configurations of compounds 14a, 18d, and 18r were unambiguously confirmed by single-crystal X-ray diffraction. Furthermore, bioactivities of these compounds as anti-oomycete, anti-fungal, and nematicidal agents against three serious agricultural pests, Phytophthora capsici, Fusarium graminearum, and Heterodera glycines were evaluated. Among all tested compounds: (i) compound 7 exhibited promising anti-oomycete against Phytophthora capsici, with a half maximal effective concentration (EC50) value of 15.81 mg L-1; (ii) compounds 2, 7, 10, and 19a displayed promising anti-fungal against F. graminearum, with EC50 values of 12.22, 14.72, 23.39, and 33.10 mg L-1, respectively; (iii) ten compounds (12a-12c, 14c, 18g-18j, 18m, and 19a) showed significant nematicidal activity against H. glycines, with median lethal concentration (LC50) values all less than 30.00 mg L-1. Especially for compound 18g, its LC50 value is the smallest, at 12.65 mg L-1.
CONCLUSIONS: The research results indicate that introducing nitro groups at the C5 position of paeonol, or introducing halogens at both C5 and C3 positions, can significantly enhance its biological activity against Phytophthora capsici, F. graminearum, and H. glycines. © 2024 Society of Chemical Industry.