紫苏醛基肟酯化合物的合成及性能

Synthesis and Properties of Perillaldehyde-based Oxime Ester Compounds

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.