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

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50μg/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100μg/mL下对油菜Brassica campestris胚根生长的抑制率达92.1%。

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

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.