Novel Thiazole Phenoxypyridine Derivatives Protect Maize from Residual Pesticide Injury Caused by PPO-Inhibitor Fomesafen

Zhao, Li-Xia; Yin, Min-Lei; Wang, Qing-Rui; Zou, Yue-Li; Ren, Tao; Gao, Shuang; Fu, Ying; Ye, Fei

doi:10.3390/biom9100514

Open AccessArticle

Novel Thiazole Phenoxypyridine Derivatives Protect Maize from Residual Pesticide Injury Caused by PPO-Inhibitor Fomesafen

by

Li-Xia Zhao

,

Min-Lei Yin

,

Qing-Rui Wang

,

Yue-Li Zou

,

Tao Ren

,

Shuang Gao

,

Ying Fu

^*

and

Fei Ye

^*

Department of Applied Chemistry, College of Science, Northeast Agricultural University, Harbin 150030, China

^*

Authors to whom correspondence should be addressed.

Biomolecules 2019, 9(10), 514; https://doi.org/10.3390/biom9100514

Submission received: 28 August 2019 / Revised: 17 September 2019 / Accepted: 17 September 2019 / Published: 20 September 2019

Download

Browse Figures

Review Reports Versions Notes

Abstract

The herbicide fomesafen has the advantages of low toxicity and high selectivity, and the target of this compound is protoporphyrinogen IX oxidase (PPO, EC 1.3.3.4). However, this herbicide has a long residual period and can have phytotoxic effects on succeeding crops. To protect maize from fomesafen, a series of thiazole phenoxypyridines were designed based on structure–activity relationships, active substructure combinations, and bioisosterism. Bioassays showed that thiazole phenoxypyridines could improve maize tolerance under fomesafen toxicity stress to varying degrees at a dose of 10 mg·kg⁻¹. Compound 4i exhibited the best effects. After being treated by compound 4i, average recovery rates of growth index exceeded 72%, glutathione content markedly increased by 167% and glutathione S-transferase activity was almost 163% of fomesafen-treated group. More importantly, after being treated by compound 4i, the activity of PPO, the main target enzyme of fomesafen, recovered to 93% of the control level. The molecular docking result exhibited that the compound 4i could compete with fomesafen to bind with the herbicide target enzyme, which consequently attained the herbicide detoxification. The present work suggests that compound 4i could be developed as a potential safener to protect maize from fomesafen.

Keywords: PPO; thiazole phenoxypyridines; synthesis; safener activity; molecular docking

Graphical Abstract

Share and Cite

MDPI and ACS Style

Zhao, L.-X.; Yin, M.-L.; Wang, Q.-R.; Zou, Y.-L.; Ren, T.; Gao, S.; Fu, Y.; Ye, F. Novel Thiazole Phenoxypyridine Derivatives Protect Maize from Residual Pesticide Injury Caused by PPO-Inhibitor Fomesafen. Biomolecules 2019, 9, 514. https://doi.org/10.3390/biom9100514

AMA Style

Zhao L-X, Yin M-L, Wang Q-R, Zou Y-L, Ren T, Gao S, Fu Y, Ye F. Novel Thiazole Phenoxypyridine Derivatives Protect Maize from Residual Pesticide Injury Caused by PPO-Inhibitor Fomesafen. Biomolecules. 2019; 9(10):514. https://doi.org/10.3390/biom9100514

Chicago/Turabian Style

Zhao, Li-Xia, Min-Lei Yin, Qing-Rui Wang, Yue-Li Zou, Tao Ren, Shuang Gao, Ying Fu, and Fei Ye. 2019. "Novel Thiazole Phenoxypyridine Derivatives Protect Maize from Residual Pesticide Injury Caused by PPO-Inhibitor Fomesafen" Biomolecules 9, no. 10: 514. https://doi.org/10.3390/biom9100514

APA Style

Zhao, L.-X., Yin, M.-L., Wang, Q.-R., Zou, Y.-L., Ren, T., Gao, S., Fu, Y., & Ye, F. (2019). Novel Thiazole Phenoxypyridine Derivatives Protect Maize from Residual Pesticide Injury Caused by PPO-Inhibitor Fomesafen. Biomolecules, 9(10), 514. https://doi.org/10.3390/biom9100514

Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here.

Article Menu

Novel Thiazole Phenoxypyridine Derivatives Protect Maize from Residual Pesticide Injury Caused by PPO-Inhibitor Fomesafen

Abstract

Share and Cite

Article Metrics

Article Access Statistics

Further Information

Guidelines

MDPI Initiatives

Follow MDPI