紫苏醛基肟酯化合物的合成及性能
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TQ351

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国家自然科学基金项目(31460173);广西林产化学与工程重点实验室开放基金项目(GXFC15-01)


Synthesis and Properties of Perillaldehyde-based Oxime Ester Compounds
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the National Natural Science Foundation of China (31460173); the Open Fund of Guangxi Key Laboratory of Chemistry and Engineering of Forest Products (GXFC15-01)

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    摘要:

    以紫苏醛(Ⅰ)为原料,经缩合反应制得紫苏葶(Ⅱ),然后与系列酰氯进行酰化反应,以70% ~ 90%的收率得到21个紫苏醛基肟酯化合物Ⅲa ~ u,采用FTIR、NMR和ESI-MS对其进行了结构表征,并测试了目标化合物的除草和抑菌活性。结果表明:化合物Ⅲa ~ u的质量浓度为100 mg/L时,紫苏醛基甲基肟酯(Ⅲa)和紫苏醛基乙基肟酯(Ⅲb)对稗草幼苗株高生长的相对抑制率分别达到97.0%和91.0%,与阳性对照丙炔氟草胺的相对抑制率(97.5%)相当;紫苏醛基对氯苯基肟酯(Ⅲm)和紫苏醛基乙基肟酯(Ⅲb)对油菜胚根生长的相对抑制率分别为88.4%和79.6%,比丙炔氟草胺的相对抑制率(63.0%)更高。此外,在质量浓度为50 mg/L时,化合物Ⅲa ~ u对苹果轮纹病菌、黄瓜枯萎病菌、花生褐斑病菌、小麦赤霉病菌和番茄早疫病菌均有一定的抑菌活性,其中,Ⅲb对花生褐斑病菌和苹果轮纹病菌有较好的抑菌能力,相对抑菌率分别为85.0%和79.2%。

    Abstract:

    Perillartine (Ⅱ) was prepared by condensation reaction using perillaldehyde (Ⅰ) as starting material. Then, twenty-one perillaldehyde-based oxime esters (Ⅲa ~ u) were synthesized in 70% ~ 90% yields by O-acylation reaction of perillartine with a series of acyl chlorides. All the target compounds were characterized by FTIR, 1HNMR, 13CNMR, and ESI-MS. The herbicidal and antifungal activities were also evaluated in this study. The results showed that, at 100 mg/L, the target compounds perillaldehyde-based methyl oxime ester (Ⅲa) and perillaldehyde-based ethyl oxime ester (Ⅲb) had inhibition rates of 97.0% and 91.0% against seedling-growth of barnyard grass (Echinochloa crusgalli L.), respectively, displaying comparable herbicidal activity with the commercial herbicide flumioxazin with the inhibition rate of 97.5%. Perillaldehyde-based p-chlorophenyl oxime ester (Ⅲm) and perillaldehyde-based ethyl oxime ester (Ⅲb) had inhibition rates of 88.4% and 79.6% against the root of rape (Brassica campestris), exhibiting better herbicidal activity than the commercial herbicide flumioxazin with the inhibition rate of 63.0%. Besides, at 50 mg/L, the target compounds Ⅲa ~ u showed certain antifungal activities against Physalospora piricola, Fusarium oxysporum f. sp. Cucumerinum, Cercospora arachidicola, Fusarium graminearum and Alternaria solani, in which perillaldehyde-based ethyl oxime ester (Ⅲb) presented the best antifungal activity with the inhibition rates of 85.0% and 79.2% against C. arachidicola and P. piricola, respectively.

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林桂汕,马媛,段文贵,刘陆智,胡琼,雷福厚.紫苏醛基肟酯化合物的合成及性能[J].精细化工,2018,35(8):

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  • 收稿日期:2017-07-24
  • 最后修改日期:2017-11-05
  • 录用日期:2017-11-27
  • 在线发布日期: 2018-07-10
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