Design, Synthesis, and Bioevaluation of Substituted Phenyl Isoxazole Analogues as Herbicide Safeners

Herbicide safeners enhance herbicide detoxification in crops without affecting target weed sensitivity. To enhance crop tolerance to the toxicity-related stress caused by the herbicide acetochlor (ACT), a new class of substituted phenyl isoxazole derivatives was designed by an intermediate derivatiz...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2020-09, Vol.68 (39), p.10550-10559
Main Authors: Guo, Ke-Liang, Zhao, Li-Xia, Wang, Zi-Wei, Gao, Ying-Chao, Li, Juan-Juan, Gao, Shuang, Fu, Ying, Ye, Fei
Format: Article
Language:English
Subjects:
Agricultural and Environmental Chemistry
Drug Design
Herbicides - chemical synthesis
Herbicides - chemistry
Herbicides - pharmacology
Isoxazoles - chemistry
Isoxazoles - pharmacology
Oxazines - chemistry
Oxazines - pharmacology
Plant Weeds - drug effects
Plant Weeds - growth & development
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Summary:Herbicide safeners enhance herbicide detoxification in crops without affecting target weed sensitivity. To enhance crop tolerance to the toxicity-related stress caused by the herbicide acetochlor (ACT), a new class of substituted phenyl isoxazole derivatives was designed by an intermediate derivatization method as herbicide safeners. Microwave-assisted synthesis was used to prepare the phenyl isoxazole analogues, and all of the structures were confirmed via IR, 1H NMR, 13C NMR, and HRMS. Compound I-1 was further characterized by X-ray diffraction analysis. Bioassay results showed that most of the obtained compounds provided varying degrees of safening against ACT-induced injury by increasing the corn growth recovery, glutathione content, and glutathione S-transferase activity. In particular, compound I-20 showed excellent safener activity against ACT toxicity, comparable to that of the commercial safener benoxacor. Gaussian calculations have been performed and the results indicated that the nucleophilic ability of compound I-20 is higher than that of benoxacor, thus the activity is higher than that of benoxacor. These findings demonstrate that phenyl isoxazole derivatives possess great potential for protective management in cornfields.
ISSN:0021-8561
1520-5118
DOI:10.1021/acs.jafc.0c01867