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Exploration of Fungicidal Activity and Mode of Action of Ferimzone Analogs. / Zhang, Yue; Li, Jing; Liu, Xiaoyu et al.
In: Journal of Agricultural and Food Chemistry, Vol. 71, No. 8, 01.03.2023, p. 3705-3718.

Research output: Contribution to journal › Article › peer-review

Harvard

Zhang, Y, Li, J, Liu, X, Gao, W, Song, S, Rong, Y, Tan, L, Glukhareva, TV, Bakulev, VA & Fan, Z 2023, 'Exploration of Fungicidal Activity and Mode of Action of Ferimzone Analogs', Journal of Agricultural and Food Chemistry, vol. 71, no. 8, pp. 3705-3718. https://doi.org/10.1021/acs.jafc.2c08504

APA

Zhang, Y., Li, J., Liu, X., Gao, W., Song, S., Rong, Y., Tan, L., Glukhareva, T. V., Bakulev, V. A., & Fan, Z. (2023). Exploration of Fungicidal Activity and Mode of Action of Ferimzone Analogs. Journal of Agricultural and Food Chemistry, 71(8), 3705-3718. https://doi.org/10.1021/acs.jafc.2c08504

Vancouver

Zhang Y, Li J, Liu X, Gao W, Song S, Rong Y et al. Exploration of Fungicidal Activity and Mode of Action of Ferimzone Analogs. Journal of Agricultural and Food Chemistry. 2023 Mar 1;71(8):3705-3718. doi: 10.1021/acs.jafc.2c08504

Author

Zhang, Yue ; Li, Jing ; Liu, Xiaoyu et al. / Exploration of Fungicidal Activity and Mode of Action of Ferimzone Analogs. In: Journal of Agricultural and Food Chemistry. 2023 ; Vol. 71, No. 8. pp. 3705-3718.

BibTeX

@article{28c87742b4a04a9e92d9b81de8e3a60f,
title = "Exploration of Fungicidal Activity and Mode of Action of Ferimzone Analogs",
abstract = "Lead discovery and molecular target identification are important for developing novel pesticides. Scaffold hopping, an effective approach of modern medicinal and agrochemical chemistry for a rational design of target molecules, is aiming to design novel molecules with similar structures and similar/better biological performance. Herein, 24 new ferimzone derivatives were designed and synthesized by a scaffold-hopping strategy. In vitro bioassays indicated that compound 5o showed similar potency to ferimzone against Cercospora arachidicola and 2-fold higher potency than ferimzone against Alternaria solani. Compounds 5q, 6a, and 6d displayed fungicidal activity with EC50 values ranging from 1.17 to 3.84 μg/mL against Rhizoctonia solani, and compounds 5q and 6a displayed 1.6-1.8-fold higher activity than ferimzone against Fusarium graminearum. The in vivo bioassays at 200 μg/mL indicated that compound 5q was more potent than ferimzone against Pyricularia oryzae (90% vs 70% efficacy, respectively). Density functional theory (DFT) calculations elucidated the structure-energy relationship. Although the mode of action of ferimzone is still unclear, studies suggested that compound 5q significantly inhibited the growth and reproduction of R. solani, and its energy metabolism pathways (e.g., starch, sucrose, lipids, and glutathione) were seriously downregulated after a 5q treatment. {\textcopyright} 2023 American Chemical Society.",
author = "Yue Zhang and Jing Li and Xiaoyu Liu and Wei Gao and Shuoshuo Song and Yaping Rong and Linyu Tan and Glukhareva, {Tatiana V.} and Bakulev, {Vasiliy A.} and Zhijin Fan",
note = "The authors appreciate Associate Professor Lai Chen at Hebei Agricultural University for his help in the homology modeling and docking by YASARA. This work was supported in part by the National Key Research & Development Program of China (nos. 2022YFD1700400 and 2022YFD1700402), the National Natural Science Foundation of China (nos. 32172443 and 31872007), and the Tianjin Development Program for Innovation and Entrepreneurship (no. 2019-11-06).",
year = "2023",
month = mar,
day = "1",
doi = "10.1021/acs.jafc.2c08504",
language = "English",
volume = "71",
pages = "3705--3718",
journal = "Journal of Agricultural and Food Chemistry",
issn = "0021-8561",
publisher = "American Chemical Society",
number = "8",

}

RIS

TY - JOUR

T1 - Exploration of Fungicidal Activity and Mode of Action of Ferimzone Analogs

AU - Zhang, Yue

AU - Li, Jing

AU - Liu, Xiaoyu

AU - Gao, Wei

AU - Song, Shuoshuo

AU - Rong, Yaping

AU - Tan, Linyu

AU - Glukhareva, Tatiana V.

AU - Bakulev, Vasiliy A.

AU - Fan, Zhijin

N1 - The authors appreciate Associate Professor Lai Chen at Hebei Agricultural University for his help in the homology modeling and docking by YASARA. This work was supported in part by the National Key Research & Development Program of China (nos. 2022YFD1700400 and 2022YFD1700402), the National Natural Science Foundation of China (nos. 32172443 and 31872007), and the Tianjin Development Program for Innovation and Entrepreneurship (no. 2019-11-06).

PY - 2023/3/1

Y1 - 2023/3/1

N2 - Lead discovery and molecular target identification are important for developing novel pesticides. Scaffold hopping, an effective approach of modern medicinal and agrochemical chemistry for a rational design of target molecules, is aiming to design novel molecules with similar structures and similar/better biological performance. Herein, 24 new ferimzone derivatives were designed and synthesized by a scaffold-hopping strategy. In vitro bioassays indicated that compound 5o showed similar potency to ferimzone against Cercospora arachidicola and 2-fold higher potency than ferimzone against Alternaria solani. Compounds 5q, 6a, and 6d displayed fungicidal activity with EC50 values ranging from 1.17 to 3.84 μg/mL against Rhizoctonia solani, and compounds 5q and 6a displayed 1.6-1.8-fold higher activity than ferimzone against Fusarium graminearum. The in vivo bioassays at 200 μg/mL indicated that compound 5q was more potent than ferimzone against Pyricularia oryzae (90% vs 70% efficacy, respectively). Density functional theory (DFT) calculations elucidated the structure-energy relationship. Although the mode of action of ferimzone is still unclear, studies suggested that compound 5q significantly inhibited the growth and reproduction of R. solani, and its energy metabolism pathways (e.g., starch, sucrose, lipids, and glutathione) were seriously downregulated after a 5q treatment. © 2023 American Chemical Society.

AB - Lead discovery and molecular target identification are important for developing novel pesticides. Scaffold hopping, an effective approach of modern medicinal and agrochemical chemistry for a rational design of target molecules, is aiming to design novel molecules with similar structures and similar/better biological performance. Herein, 24 new ferimzone derivatives were designed and synthesized by a scaffold-hopping strategy. In vitro bioassays indicated that compound 5o showed similar potency to ferimzone against Cercospora arachidicola and 2-fold higher potency than ferimzone against Alternaria solani. Compounds 5q, 6a, and 6d displayed fungicidal activity with EC50 values ranging from 1.17 to 3.84 μg/mL against Rhizoctonia solani, and compounds 5q and 6a displayed 1.6-1.8-fold higher activity than ferimzone against Fusarium graminearum. The in vivo bioassays at 200 μg/mL indicated that compound 5q was more potent than ferimzone against Pyricularia oryzae (90% vs 70% efficacy, respectively). Density functional theory (DFT) calculations elucidated the structure-energy relationship. Although the mode of action of ferimzone is still unclear, studies suggested that compound 5q significantly inhibited the growth and reproduction of R. solani, and its energy metabolism pathways (e.g., starch, sucrose, lipids, and glutathione) were seriously downregulated after a 5q treatment. © 2023 American Chemical Society.

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85148001840

U2 - 10.1021/acs.jafc.2c08504

DO - 10.1021/acs.jafc.2c08504

M3 - Article

VL - 71

SP - 3705

EP - 3718

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

SN - 0021-8561

IS - 8

ER -

ID: 36094676