COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING
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2022
·Vol. 25
·期 6
·1031-1039
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IF 1.714
Chen Genqiang,Zhu Lina,Xia Yanfei,Yang Jinming,Zhang Song,Li Yuanhao,Guo Xiaolong,Sun Di,He Jiaxuan,Tian Yuee,Liu Shengming,Jiang Jia,Che Zhiping
Background: Developing the high-efficiency and low-risk small-molecule greennematocide is the key of effective control of the nematodes. Paeonol, is a naturally occurring phenolic compound, isolated from the root bark of Paeonia suffruticosa and the whole plant of Cynanchum paniculatum.
Due to its crucial phenolic ketone skeleton, modern biological science research has indicated that paeonol has a wide range of biological activities. Methods: The structural modification of paeonol into paeonol carbonyl hydrazone derivatives is a potential approach for the development
of novel nematodes, which showed more toxicity than paeonol. However, there are no reports on the nematicidal activity of paeonol carbonyl hydrazone derivatives to control Heterodera glycines. Results: We always endeavor to discover and develop biorational natural products-based pesticidal
agents, 4 significant intermediates and 21 novel 3/5(3,5)-(di)nitro/chloropaeonol carbonyl hydrazone derivatives were prepared, and their structures well characterized by 1H NMR, HRMS, MS, and mp. Due to the steric hindrance, the substituents on the C=N double bond of
all hydrazine compounds adopted E configuration. Results of nematicidal activity revealed that, among all compounds, especially 5-nitropaeonol (5) and 3,5-dinitropaeonol (7) displayed the most potent nematicidal activity H. glycines in vivo with LC50 values of 0.0323
and 0.0367 mg/mL, respectively. Conclusion: It suggested that for the 3/5(3,5)-(di)nitro/chloropaeonol carbonyl hydrazone derivatives, a nitro group introduced at C5 position of 1 was necessary for obtaining the potent compound as nematicidal agents. These preliminary results will pave
the way for further modification of paeonol in the development of potential new nematicides.
研究领域:
植物化学
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农药学
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药理学
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DOI
PubMed
高影响因子
PEST MANAGEMENT SCIENCE
·
2024
·
IF 3.8
Mei Hu,Xiaolong Guo,Yuee Tian,Yan Li,Yibo Liu,Xiaobo Huang,Genqiang Chen,Zhiping Che
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 ( 1 H NMR), carbon-13 ( 13 C) 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 (EC 50 ) value of 15.81 mg L −1 ; (ii) compounds 2, 7, 10, and 19a displayed promising anti-fungal against F. graminearum , with EC 50 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 (LC 50 ) values all less than 30.00 mg L −1 . Especially for compound 18g, its LC 50 value is the smallest, at 12.65 mg L −1 . CONCLUSION 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.
研究领域:
植物化学
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农药科学
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生物活性研究
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产品关联
DOI
PubMed
高影响因子
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