Design, Synthesis, and Antifungal Evaluation of 8‑Hydroxyquinoline Metal Complexes against Phytopathogenic Fungi

Phytopathogenic fungal infections have become a major threat to agricultural production, food security, and human health globally, and novel antifungal agents with simple chemical scaffolds and high efficiency are needed. In this study, we designed and synthesized 38 8-hydroxyquinoline metal complex...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2020-10, Vol.68 (40), p.11096-11104
Main Authors: Yin, Xiao-Dan, Ma, Kun-Yuan, Wang, Yu-Ling, Sun, Yu, Shang, Xiao-Fei, Zhao, Zhong-Min, Wang, Ren-Xuan, Chen, Yong-Jia, Zhu, Jia-Kai, Liu, Ying-Qian
Format: Article
Language:English
Subjects:
Agricultural and Environmental Chemistry
Ascomycota - drug effects
Ascomycota - growth & development
Botrytis - drug effects
Botrytis - growth & development
Brassica napus - microbiology
Drug Design
Fungicides, Industrial - chemical synthesis
Fungicides, Industrial - chemistry
Fungicides, Industrial - pharmacology
Fusarium - drug effects
Fusarium - growth & development
Molecular Structure
Oxyquinoline - chemistry
Oxyquinoline - pharmacology
Plant Diseases - microbiology
Structure-Activity Relationship
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Summary:Phytopathogenic fungal infections have become a major threat to agricultural production, food security, and human health globally, and novel antifungal agents with simple chemical scaffolds and high efficiency are needed. In this study, we designed and synthesized 38 8-hydroxyquinoline metal complexes and evaluated their antifungal activities. The results showed that most of the tested compounds possessed remarkable in vitro antifungal activity. Especially, compound 1e exhibited the highest antifungal potency among all target compounds, with EC50 values of 0.0940, 0.125, 2.95, and 5.96 μg/mL, respectively, against Sclerotinia sclerotiorum, Botrytis cinerea, Fusarium graminearum, and Magnaporthe oryzae. Preliminary mechanistic studies had shown that compound 1e might cause mycelial abnormalities of S. sclerotiorum, cell membrane permeability changes, leakage of cell contents, and inhibition of sclerotia formation and germination. Moreover, the results of in vivo antifungal activity of compound 1e against S. sclerotiorum showed that 1e possessed higher curative effects than that of the positive control azoxystrobin. Therefore, compound 1e is expected to be a novel leading structure for the development of new antifungal agents.
ISSN:0021-8561
1520-5118
DOI:10.1021/acs.jafc.0c01322