吴光燧, 段文贵, 林桂汕, 岑波, 赵莉, 雷福厚. N-（4-取代氨基磺酰基）苯基-酮基蒎酸酰胺的合成及生物活性[J]. 农药学学报, 2014, 16(1): 8-13. DOI: 10.3969/j.issn.1008-7303.2014.01.02
    引用本文: 吴光燧, 段文贵, 林桂汕, 岑波, 赵莉, 雷福厚. N-（4-取代氨基磺酰基）苯基-酮基蒎酸酰胺的合成及生物活性[J]. 农药学学报, 2014, 16(1): 8-13. DOI: 10.3969/j.issn.1008-7303.2014.01.02
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    WU Guangsui, DUAN Wengui, LIN Guishan, CEN Bo, ZHAO Li, LEI Fuhou. Synthesis and biological activity of N-(4-substituted amino-sulfonyl)-phenyl-ketopinamides[J]. Chinese Journal of Pesticide Science, 2014, 16(1): 8-13. DOI: 10.3969/j.issn.1008-7303.2014.01.02
    Citation: WU Guangsui, DUAN Wengui, LIN Guishan, CEN Bo, ZHAO Li, LEI Fuhou. Synthesis and biological activity of N-(4-substituted amino-sulfonyl)-phenyl-ketopinamides[J]. Chinese Journal of Pesticide Science, 2014, 16(1): 8-13. DOI: 10.3969/j.issn.1008-7303.2014.01.02
    shu

    N-（4-取代氨基磺酰基）苯基-酮基蒎酸酰胺的合成及生物活性

    Synthesis and biological activity of N-(4-substituted amino-sulfonyl)-phenyl-ketopinamides

      摘要
    • 摘要: 以D-（+）-樟脑磺酸为原料，经酰氯化和氧化反应制备得到酮基蒎酸（3），再经酰氯化得到酮基蒎酸酰氯（4）。4与对氨基苯磺酰胺类化合物发生N-酰化反应，得到8个未见文献报道的N-（4-取代氨基磺酰基）苯基-酮基蒎酸酰胺（5a~5h），其结构均经红外、质谱、核磁共振氢谱和碳谱确证。初步生物活性测试结果表明：目标化合物均有不同程度的杀菌和除草活性，其中5c（R=4-甲基嘧啶-2-基）在50 μg/mL下对番茄早疫病菌Alternaria solani的抑制率达90.4%，化合物5e（R=噻唑-2-基）在100 μg/mL下对油菜Brassica campestris胚根生长的抑制率达92.1%。

       

      Abstract: Ketopinic acid(3) was prepared by the acyl chlorination and oxidation of D-(+)-camphorsulfonic acid, followed by the acyl chlorination to obtain ketopinic acid chloride (4). Then, eight novel N-(4-substituted amino-sulfonyl)-phenyl-ketopinamides 5a-5h were synthesized by the reaction of 4 with various 4-amino benzenesulfonamides. Their structures were confirmed by FT-IR, ESI-MS, 1H NMR and 13C NMR. The preliminary bioassay showed that, all the target compounds exhibited different fungicidal activity and herbicidal activity, in which compound 5c (R=4-methyl-pyrimidin-2-yl) had the best inhibition rate of 90.4% against Alternaria solani at the concentration of 50 μg/mL, and compound 5e (R=thiazol-2-yl) had the best growth inhibition rate of 92.1% against rape root (Brassica campestris) at the concentration of 100 μg/mL.

       

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