武磊, 李永红, 周莎, 李正名, 王忠文. 磺酰氨基氯磺隆的合成、除草活性、作物安全性及其土壤降解研究[J]. 农药学学报, 2022, 24(6): 1377-1384. DOI: 10.16801/j.issn.1008-7303.2022.0051
    引用本文: 武磊, 李永红, 周莎, 李正名, 王忠文. 磺酰氨基氯磺隆的合成、除草活性、作物安全性及其土壤降解研究[J]. 农药学学报, 2022, 24(6): 1377-1384. DOI: 10.16801/j.issn.1008-7303.2022.0051
    WU Lei, LI Yonghong, ZHOU Sha, LI Zhengming, WANG Zhongwen. Synthesis, herbicidal activity, crop safety and soil degradation of sulfonylamino-substituted chlorsulfuron[J]. Chinese Journal of Pesticide Science, 2022, 24(6): 1377-1384. DOI: 10.16801/j.issn.1008-7303.2022.0051
    Citation: WU Lei, LI Yonghong, ZHOU Sha, LI Zhengming, WANG Zhongwen. Synthesis, herbicidal activity, crop safety and soil degradation of sulfonylamino-substituted chlorsulfuron[J]. Chinese Journal of Pesticide Science, 2022, 24(6): 1377-1384. DOI: 10.16801/j.issn.1008-7303.2022.0051

    磺酰氨基氯磺隆的合成、除草活性、作物安全性及其土壤降解研究

    Synthesis, herbicidal activity, crop safety and soil degradation of sulfonylamino-substituted chlorsulfuron

    • 摘要: 基于活性亚结构拼接方法,在氯磺隆分子中苯环的5位引入不同磺酰氨基,设计合成了4个氯磺隆衍生物 ( H01 ~ H04 ),其结构经核磁共振氢谱(1H NMR)、碳谱(13C NMR)和高分辨质谱(HRMS)确证。初步的生物活性测试结果表明,目标化合物在有效成分150 g/hm2测试浓度下表现出较好的除草活性,其中:苗前处理时, H01H02H04 对油菜生长的抑制率均高于85%, H01 对反枝苋的抑制率为100%,优于对照药剂氯磺隆 (68.8%);苗后处理时, H04 对油菜和反枝苋的抑制率均与氯磺隆相当,对稗草的抑制率 (85.2%) 优于对照药剂氯磺隆 (68.8%)。安全性测试结果表明,目标化合物对小麦和玉米生长的抑制率均低于氯磺隆。苗前处理时, H01H04 对小麦安全, H01 ~ H04 对玉米的抑制率均低于氯磺隆;苗后处理时, H01 ~ H04 对玉米生长无抑制作用。降解试验结果表明, H01 ~ H04 在碱性土壤 (pH 8.39) 中的降解半衰期为44.43~53.32 d,比氯磺隆的半衰期 (157.53 d) 明显缩短。研究结果表明, H01H04 可作为潜在的小麦田和玉米田磺酰脲类除草剂候选药物。本文可为进一步设计具有高效除草活性、降解速率快以及作物安全性高的新型磺酰脲类除草剂提供参考。

       

      Abstract: Based on the splicing method of active substructures, four chlorsulfuron derivatives ( H01 - H04 ) were designed and synthesized by introducing different sulfonylamino groups on the 5-position of the benzene ring, which were confirmed with melting point, 1H NMR, 13C NMR and HRMS. The preliminary biological activity test results showed that the 5-sulfonylamino-substituted compounds exhibited good herbicidal activities. At concentration of 150 g a.i/hm2, the inhibition rates against Brassica napus of H01 , H02 and H04 were higher than 85% through pre-emergence treatment. In addition, the inhibition rates against Amaranthus retroflexus of H01 was 100%, which were better than chlorsulfuron (68.8%). For post-emergence treatment, the inhibition rates of H04 on B. napus and A. retroflexus were equivalent to that of chlorsulfuron. And the inhibition rates of H04 on Echinochloa crusgalli (85.2%) was better than that of chlorsulfuron (68.8%). The crop safety results indicated that the inhibition rates of these target compounds on the growth of wheat and corn were lower than that of chlrosulfuron. H01 and H04 showed safety to wheat growth through pre-emergence treatment. Additionally, the inhibition rates of H01 - H04 on corn were lower than chlorsulfuron. In the case of post-emergence treatment, H01 and H04 showed safety to corn. Alkaline soil (pH 8.39) degradation results indicated that the DT50 (half-life of degradation) values of H01 - H04 varied from 44.43 to 53.32 days, which was shorter than that of chlorsulfuron (157.53 days). Based on the results, H01 and H04 could be used as potential sulfonylurea herbicides on wheat and corn. This paper could provide a reference for the further design of new sulfonylurea herbicides with high herbicidal activity, rapid degradation rate and superior crop safety.

       

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