- Controllable Soil Degradation Rate of 5-Substituted Sulfonylurea Herbicides as Novel AHAS Inhibitors
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Chlorsulfuron has been applied in wheat fields as a recognized herbicide worldwide, yet it was officially banned in China since 2014 for its soil persistence problem. On the basis of our previous research that 5-dimethylamino distinctively accelerated degradation rate in soils, a modified amino moiety (Ia-c) and monosubstituted amino group (Id-e) were introduced onto the fifth position of the benzene ring in sulfonylurea structures, as well as heterocyclic amino substituents (If-g) to seek a suitable soil degradation rate during such an in situ crop rotation system. Referring to the biological data and ScAHAS inhibition and ScAHAS docking results, they turned out to be AHAS inhibitors with high potent herbicidal activities. The various influence on soil degradation rate along with crop safety indicated that different substituents on the fifth position have exerted an apparent impact. Their united study of structure-activity-safety-degradation relationship has great potential to provide valuable information for further development of eco-friendly agrochemicals.
- Chen, An-Liang,Chen, Jie,Hua, Xue-Wen,Li, Yong-Hong,Li, Zheng-Ming,Liu, Bin,Meng, Fan-Fei,Wang, Bao-Lei,Zhou, Shaa
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p. 3017 - 3025
(2020/03/31)
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- Research on the controllable degradation of: N -methylamido and dialkylamino substituted at the 5thposition of the benzene ring in chlorsulfuron in acidic soil
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Owing to the lengthy residual problems associated with chlorsulfuron, metsulfuron-methyl, and ethametsulfuron, which prevents them from being used in the "annual multi-crop planting system", the application of these sulfonylurea herbicides (SU) has regrettably been terminated in China since 2014. In this field, we were the first to discover that the 5th position of the benzene ring in chlorsulfuron is a key point for influencing its degradation rate and the amino moiety at this position showed faster degradation rates and maintained their original potent bioactivity. In this study, we further elaborated on N-methylamido and dialkylamino substituents at the same position in chlorsulfuron to obtain 18 novel structures as M and N series. Their half-life degradation (DT50) values were faster, to varying degrees, than chlorsulfuron in acidic soil. It was found that most of the titled structures also retained their potent herbicidal activity and the crop safety of the M series towards corn greatly increased. Based on these data, a comprehensive graph describing the structure/degradation relationship was established first. Relating to the new molecules, their herbicidal activity (A), degradation rates (D), and crop safety (S) relationship were correlated and we used this approach to predict and explore the most preferable molecule, which coincided to the corresponding experimental data. The new concept of controllable degradation will provide us with more insight when searching for new ecological bioactive molecules in the future.
- Chen, Ming-Gui,Gu, Yu-Cheng,Li, Yong-Hong,Li, Zheng-Ming,Ma, Yi,Meng, Fan-Fei,Wu, Lei,Zhao, Yang-Yang,Zhou, Sha,Zhou, Shaa
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p. 17870 - 17880
(2020/09/01)
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- TGF-betaR1 inhibitor and application thereof
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The invention belongs to the field of medical chemistry, and particularly relates to a compound serving as a TGF-betaR1 inhibitor and application of the compound. Specifically, the invention providesa compound shown as a formula I or an isomer, a pharmaceutically acceptable salt, a solvate, a crystal or a prodrug thereof, a preparation method of the compounds, a pharmaceutical composition containing the compounds and application of the compounds or the composition to treatment and/or prevention of TGF-betaR1 related diseases, such as cancers, tissue hyperplasia diseases, fibrosis and inflammatory diseases. The compound provided by the invention shows significant inhibitory activity on TGF-betaR1 kinase, and is very expected to become a therapeutic agent for TGF-betaR1 related diseases.
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Paragraph 0922; 0924-0926
(2020/06/09)
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- Controllable Effect of Structural Modification of Sulfonylurea Herbicides on Soil Degradation
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The study of soil degradation behaviors of sulfonylurea herbicides in relation to their different structural attributes is utmost important for us to comprehend the development of new eco-friendly herbicides. It is postulated that the structural modification of the chemical structures could influence their degradation rates in soil. Nine devised structures were synthesized to study their herbicidal activity as well as their soil degradation behaviors respectively. The novel compounds I-3–I-7 were characterized by UV,1H NMR and13C NMR, MS and EA. Bioassays indicated that most of target compounds displayed superior herbicidal activities in comparison with Chlorsulfuron. Soil degradation results further confirmed our previous assumption that the introduction of electron-donating substituents at 5thposition of the benzene ring distinctly increased their degradation rates, among which dimethylamino and diethylamino groups can adjust the degradation rate to a more favorable status.
- Hua, Xuewen,Zhou, Shaa,Chen, Minggui,Wei, Wei,Liu, Ming,Lei, Kang,Zhou, Sha,Li, Yonghong,Wang, Baolei,Li, Zhengming
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p. 1135 - 1142
(2016/11/25)
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- Research on controllable degradation of sulfonylurea herbicides
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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 5th 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, 1H and 13C 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 5th 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.
- 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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p. 23038 - 23047
(2016/03/12)
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- Synthesis and evaluation of novel monosubstituted sulfonylurea derivatives as antituberculosis agents
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A series of novel monosubstituted sulfonylurea derivatives 10a-y were synthesized and characterized by 1H NMR, 13C NMR and HRMS. These compounds were evaluated against Mycobacterium tuberculosis H37Rv in vitro. The results showed compounds 10f, 10k and 10s exhibited moderate antituberculosis activities with MIC values in the range of 20-100 mg/L. Compounds 10b and 10o displayed good antituberculosis activities (MIC 10 mg/L), which were comparable with that of the sulfometuron methyl. Both of the two compounds showed little cytotoxicities, with an IC50 against THP-1 cells greater than 100 mg/L.
- Pan, Li,Jiang, Ying,Liu, Zhen,Liu, Xing-Hai,Liu, Zhuo,Wang, Gang,Li, Zheng-Ming,Wang, Di
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- COMPOSITIONS AND METHODS FOR INHIBITION OF THE JAK PATHWAY
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The invention encompasses compounds having formula (I-V) and the compositions and methods using these compounds in the treatment of conditions in which modulation of the JAK pathway or inhibition of JAK kinases, particularly JAK3, may be therapeutically useful.
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Page/Page column 194
(2008/06/13)
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- CATECHOLAMINE SURROGATES USEFUL AS BETA 3 AGONISTS
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Compounds of the formula STR1 and pharmaceutically acceptable salts thereof. These compounds are beta three adrenergic receptor agonists and are useful, therefore for example, in the treatment of diabetes, obesity and gastrointestinal diseases.
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