张学良, 魏艳, 韦能春, 郝双红. 10种N-取代氨基香豆素的合成及生物活性[J]. 农药学学报, 2013, 15(1): 37-42.
    引用本文: 张学良, 魏艳, 韦能春, 郝双红. 10种N-取代氨基香豆素的合成及生物活性[J]. 农药学学报, 2013, 15(1): 37-42.
    ZHANG Xueliang, WEI Yan, WEI Nengchun, HAO Shuanghong. Synthesis and bioactivity of 10 N-substituted amino coumarins[J]. Chinese Journal of Pesticide Science, 2013, 15(1): 37-42.
    Citation: ZHANG Xueliang, WEI Yan, WEI Nengchun, HAO Shuanghong. Synthesis and bioactivity of 10 N-substituted amino coumarins[J]. Chinese Journal of Pesticide Science, 2013, 15(1): 37-42.

    10种N-取代氨基香豆素的合成及生物活性

    Synthesis and bioactivity of 10 N-substituted amino coumarins

    • 摘要: 基于结构拼接思想,设计合成了10个N-取代氨基香豆素类化合物,并测定了其抑菌及除草活性。6-硝基香豆素经Fe/NH4Cl还原得6-氨基香豆素,再与不同醛缩合得Schiff碱,最后经硼氢化钠还原制得10个N-取代氨基香豆素类化合物(4a~4J),其中9个未见文献报道,其结构均经红外光谱、核磁共振氢谱和质谱确认。抑菌活性测试结果表明,所有化合物对苹果腐烂病菌Valsa mali、葡萄白腐病菌Coniothyrium diplodiella、棉花枯萎病菌Fusarium oxysporium和柑橘炭疽病菌Citrusanthrax bacteria均有一定抑制作用,其中 4e 的抑菌活性最强,对苹果腐烂病菌和柑橘炭疽病菌的EC50值分别为7.53和12.93 mg/L,对其余2种植物病原菌的EC50值均小于25 mg/L;化合物 4f 次之,对苹果腐烂病菌和葡萄白腐病菌的EC50值均约为11 mg/L。除草活性测试结果表明,除 4f 外,所有目标化合物均有一定除草作用,其中 4c 的活性最强,100 mg/L下对反枝苋Amaranthus retroflexus种子根、茎生长的抑制率均为99%。

       

      Abstract: Under the guidance of substructure combination strategy,10 N-substituted amino coumarins were synthesized,their fungicidal and herbicidal activity was determined as well.6-amino coumarin was prepared from reducing of 6-nitro coumarin by Fe/NH4Cl and condensed with different aldehyde to give the intermediate Schiff base,which was then reduced by sodium borohydride to give N-substituted amino coumarins.Nine of the compounds were not reported in the literature.The structures of the synthesized compounds were confirmed by IR,1H NMR and ESI-MS.All the synthesized compounds showed certain inhibition against Valsa mali,Coniothyrium diplodiella,Fusarium oxysporium and Citrusanthrax bacteria. Compound 4e indicated the most fungicidal activity with EC50 value of 7.53 and 12.93 mg/L against V.mali and C.bacteria respectively,and 50 value of about 11 mg/L against V.mali and C.diplodiella.Furthermore,all the synthesized compounds except 4f have some herbicidal activity against the root and seedling development of Amaranthus retroflexus.The inhibitory rates of compound 4c against A.retroflexus were 99% at 100 mg/L.

       

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