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Cite the Following Article
Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors
Man-Man Wang, Hao Huang, Lei Shu, Jian-Min Liu, Jian-Qiu Zhang, Yi-Le Yan and Da-Yong Zhang
Beilstein J. Org. Chem. 2020, 16, 233–247.
https://doi.org/10.3762/bjoc.16.25
How to Cite
Wang, M.-M.; Huang, H.; Shu, L.; Liu, J.-M.; Zhang, J.-Q.; Yan, Y.-L.; Zhang, D.-Y. Beilstein J. Org. Chem. 2020, 16, 233–247. doi:10.3762/bjoc.16.25
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- Martins, F. A.; Daré, J. K.; Freitas, M. P. Computer-Assisted Proposition of Promising Aryloxyacetic Acid Derivatives as HPPD Inhibitors. Journal of agricultural and food chemistry 2022, 70, 8986–8993. doi:10.1021/acs.jafc.2c02954
- Shi, J.; Zhao, L.-X.; Wang, J.-Y.; Ye, T.; Wang, M.; Gao, S.; Ye, F.; Fu, Y. The novel 4-hydroxyphenylpyruvate dioxygenase inhibitors in vivo and in silico approach: 3D-QSAR analysis, molecular docking, bioassay and molecular dynamics. Arabian Journal of Chemistry 2022, 15, 103919. doi:10.1016/j.arabjc.2022.103919
- Zeng, H.; Zhang, W.; Wang, Z.; Geng, W.; Feng, G.; Gan, X. Novel Pyrazole Amides as Potential 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors. Journal of agricultural and food chemistry 2022, 70, 7400–7411. doi:10.1021/acs.jafc.2c02123
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- Mykhailiuk, P. K. Fluorinated Pyrazoles: From Synthesis to Applications. Chemical reviews 2020, 121, 1670–1715. doi:10.1021/acs.chemrev.0c01015
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