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Herbicidal activity and molecular docking study of novel PPO inhibitors

Published online by Cambridge University Press:  28 August 2020

Li-Xia Zhao ,
Mao-Jun Jiang ,
Jia-Jun Hu ,
Yue-Li Zou ,
Shuang Gao ,
Ying Fu  and
Fei Ye
Li-Xia Zhao
Affiliation:
Associate Professor, Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin, China
Mao-Jun Jiang
Affiliation:
Master’s Degree Student, Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin, China
Jia-Jun Hu
Affiliation:
Master’s Degree Student, Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin, China
Yue-Li Zou
Affiliation:
Senior Experimentalist, Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin, China
Shuang Gao
Affiliation:
Associate Professor, Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin, China
Ying Fu*
Affiliation:
Professor, Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin, China
Fei Ye*
Affiliation:
Professor, Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin, China
*
Authors for correspondence: Ying Fu, Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin 150030, China. (Email: fuying@neau.edu.cn); and Fei Ye, Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin 150030, China. (Email: yefei@neau.edu.cn)
Authors for correspondence: Ying Fu, Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin 150030, China. (Email: fuying@neau.edu.cn); and Fei Ye, Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin 150030, China. (Email: yefei@neau.edu.cn)
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Abstract

Protoporphyrinogen oxidase (PPO) is an important target for discovering new herbicides that interfere with the synthesis of porphyrin. To discover new PPO inhibitors with improved biological activity, a series of new diphenyl ethers containing tetrahydrophthalimide were designed and synthesized. Among them, J6.1 (IC50 = 4.7 nM) and J6.3 (IC50 = 30.0 nM) show higher maize (Zea mays L.) PPO inhibitory activity than the commercial herbicides oxyfluorfen (IC50 = 117.9 nM) and flumioxazin (IC50 = 157.1 nM). The greenhouse herbicidal activity of J6.3 is comparable to that of oxyfluorfen, and it is greater than that of flumioxazin. Even at a dose of 300 g ai ha−1, cotton (Gossypium hirsutum L.) and peanut (Arachis hypogaea L.) show greater tolerance to J6.3, suggesting that J6.3 could be used for further development of new herbicide candidates in those fields. In addition, molecular docking has been used to further study the mechanism of action of J6.3. The results show that the introduction of a nitro group and tetrahydrophthalimide into the diphenyl ether structure is beneficial to biological activity.

Keywords

Biological activitydiphenyl ethertetrahydrophthalimide

Information

Type
Research Article
Information
Weed Science , Volume 68 , Issue 6 , November 2020 , pp. 565 - 574
Copyright
© The Author(s), 2020. Published by Cambridge University Press on behalf of the Weed Science Society of America

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Footnotes

Associate Editor: Dean Riechers, University of Illinois

*

These authors contributed equally to this work.

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