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Research on controllable degradation of sulfonylurea herbicides

In order to seek ecologically safer and environmentally benign sulfonylurea herbicides (SU), insight into the structure/bioassay/soil degradation tri-factor relationship was first established. With the introduction of various groups (alkyl, nitro, halogen, cyano etc. ) at the 5 th position of its be...

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Published in:RSC advances 2016-01, Vol.6 (27), p.2338-2347
Main Authors: Hua, Xue-Wen, Chen, Ming-Gui, Zhou, Shaa, Zhang, Dong-Kai, Liu, Ming, Zhou, Sha, Liu, Jing-Bo, Lei, Kang, Song, Hai-Bin, Li, Yong-Hong, Gu, Yu-Cheng, Li, Zheng-Ming
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container_issue 27
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container_title RSC advances
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creator Hua, Xue-Wen
Chen, Ming-Gui
Zhou, Shaa
Zhang, Dong-Kai
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Li, Yong-Hong
Gu, Yu-Cheng
Li, Zheng-Ming
description In order to seek ecologically safer and environmentally benign sulfonylurea herbicides (SU), insight into the structure/bioassay/soil degradation tri-factor relationship was first established. With the introduction of various groups (alkyl, nitro, halogen, cyano etc. ) at the 5 th position of its benzene ring, structural derivatives of chlorsulfuron were designed, synthesized, and evaluated for their herbicidal activity. The structures of the title compounds were confirmed by infrared spectroscopy, ultraviolet spectroscopy, 1 H and 13 C NMR, mass spectrometry, elemental analysis and X-ray diffraction. Bioassay results confirmed that most derivatives retained their superior herbicidal activities in comparison with chlorsulfuron. After investigating the soil degradation behavior of each molecule under set conditions, it was found that structures with electron-withdrawing substituents at the 5 th position of the benzene ring retained their long degradation half-lives, yet the introduction of electron-donating substituents accelerated the degradation rate. These results will provide a valuable clue to further explore the potential controllable degradation of SU and other herbicides, and to discover novel herbicides that are favorable for environmentally and ecologically sustainable development. Through studying structure, bioassay and soil degradation tri-factor relationship, potential controllable degradation of SU was firstly explored and summarized.
doi_str_mv 10.1039/c5ra25765d
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With the introduction of various groups (alkyl, nitro, halogen, cyano etc. ) at the 5 th position of its benzene ring, structural derivatives of chlorsulfuron were designed, synthesized, and evaluated for their herbicidal activity. The structures of the title compounds were confirmed by infrared spectroscopy, ultraviolet spectroscopy, 1 H and 13 C NMR, mass spectrometry, elemental analysis and X-ray diffraction. Bioassay results confirmed that most derivatives retained their superior herbicidal activities in comparison with chlorsulfuron. After investigating the soil degradation behavior of each molecule under set conditions, it was found that structures with electron-withdrawing substituents at the 5 th position of the benzene ring retained their long degradation half-lives, yet the introduction of electron-donating substituents accelerated the degradation rate. 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