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Isoxadifen-Ethyl Derivatives Protect Rice from Fenoxaprop-P-Ethyl–associated Injury during the Control of Weedy Rice

Published online by Cambridge University Press:  02 August 2017

Changchao Shen ,
Wenwei Tang ,
Dongqiang Zeng ,
Hongle Xu ,
Wangcang Su  and
Renhai Wu
Changchao Shen
Affiliation:
Graduate Student, Research Associate, Research Associate, and Associate Research Fellow, Institute of Plant Protection, Henan Academy of Agricultural Sciences, Zhengzhou, Henan 450002, China
Wenwei Tang
Affiliation:
Associate Professor and Professor, College of Agriculture, Guangxi University, Nanning, Guangxi 530005, China
Dongqiang Zeng
Affiliation:
Associate Professor and Professor, College of Agriculture, Guangxi University, Nanning, Guangxi 530005, China
Hongle Xu
Affiliation:
Graduate Student, Research Associate, Research Associate, and Associate Research Fellow, Institute of Plant Protection, Henan Academy of Agricultural Sciences, Zhengzhou, Henan 450002, China
Wangcang Su
Affiliation:
Graduate Student, Research Associate, Research Associate, and Associate Research Fellow, Institute of Plant Protection, Henan Academy of Agricultural Sciences, Zhengzhou, Henan 450002, China
Renhai Wu*
Affiliation:
Graduate Student, Research Associate, Research Associate, and Associate Research Fellow, Institute of Plant Protection, Henan Academy of Agricultural Sciences, Zhengzhou, Henan 450002, China
*
Corresponding author’s E-mail: renhai.wu@163.com
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Abstract

Fenoxaprop-P-ethyl, a phenoxy herbicide of the aryloxy–phenoxy–propionic acid group, had a strong control effect when applied POST to weedy rice in this study, with the effective concentrations of 294 μM and 218 μM of herbicide causing 50% inhibition (IC50) in plant height and fresh weight values, respectively. However, fenoxaprop-P-ethyl caused phytotoxicity in cultivated rice. Isoxadifen-ethyl, a widely used herbicide safener in rice, can decrease the phytotoxicity caused by fenoxaprop-P-ethyl. Owing to the extremely similar morphological features and physiological properties of weedy and cultivated rice, it is not practical to spray isoxadifen-ethyl directly on cultivated rice plants to safen them. Applying the safener directly to cultivated rice seeds may be a practical alternative method. To improve the biological activity of isoxadifen-ethyl seed treatments, novel compounds were designed by splicing other groups, including amines, amino acids, and 2- methoxy-5-nitrophenol sodium salt, to the parental structure of isoxadifen-ethyl. Through hydrolysis, acyl chlorination, acyl amination, and esterification, a series of isoxadifen-ethyl derivatives were synthesized and their structures were determined by mass spectrometry and 1H nuclear magnetic resonance spectroscopy. The biological activities of five of the isoxadifen-ethyl derivatives, which possessed recovery effects similar to isoxadifen-ethyl, were able to relieve herbicide phytotoxicity. In pot experiments, isoxadifen-ethyl showed almost no activity as a seed treatment, while three derivative compounds, when used independently as seed treatments, were able to prevent the damage caused by fenoxaprop-P-ethyl. The results will help to develop a new control method for weedy rice, thereby decreasing production costs and increasing farmers’ incomes.

Keywords

Fenoxaprop-P-ethylisoxadifen-ethylrice, Oryza sativa L.Isoxadifen-ethyl derivativesseed treatmentsynthesisweedy rice.
Type
Physiology/Chemistry/Biochemistry
Information
Weed Science , Volume 65 , Issue 5 , September 2017 , pp. 579 - 587
Copyright
© Weed Science Society of America, 2017 

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Footnotes

Associate Editor for this paper: Franck E. Dayan, Colorado State University

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