Page 184 - 201808

第 35 卷第 8 期 精 细 化 工 Vol.35, No.8
201 8 年 8 月 FINE CHEMICALS Aug. 2018

精细化工中间体
紫苏醛基肟酯化合物的合成及性能

1
1
1*
1
2
1
林桂汕 ，马 媛 ，段文贵 ，刘陆智 ，胡 琼 ，雷福厚
（1. 广西大学 化学化工学院，广西 南宁 530004；2. 广西林产化学与工程重点实验室，广西 南宁
530008）
摘要：以紫苏醛（Ⅰ）为原料，经缩合反应制得紫苏葶（Ⅱ），然后Ⅱ与系列酰氯进行酰化反应，以 70%~90%
1
13
的收率得到 21 个紫苏醛基肟酯化合物Ⅲa～u，采用 FTIR、 HNMR、 CNMR 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%。
关键词：紫苏醛；肟酯；除草活性；抑菌活性；精细化工中间体
中图分类号：TQ351 文献标识码：A 文章编号：1003-5214 (2018) 08-1432-09

Synthesis and Properties of Perillaldehyde-based Oxime Ester Compounds

1
1
2
1
1
1*
LIN Gui-shan , MA Yuan , DUAN Wen-gui , LIU Lu-zhi , HU Qiong , LEI Fu-hou
（1. School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, Guangxi, China; 2. Guangxi
Key Laboratory of Chemistry and Engineering of Forest Products, Nanning 530008, Guangxi, China）
Abstract: Perillartine (Ⅱ) was prepared by a condensation reaction using perillaldehyde (Ⅰ) as raw
material. Then, twenty-one perillaldehyde-based oxime esters (Ⅲa~u) were synthesized in 70%~90% yields
by O-acylation reactions of perillartine with a series of acyl chlorides. All target compounds were
13
1
characterized by FTIR, HNMR, CNMR, and ESI-MS. The herbicidal and antifungal activities of targeted
compounds were also evaluated. The results showed that at 100 mg/L, 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 (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 an inhibition rate of 63.0%. Besides, at 50 mg/L, compounds
Ⅲa~u showed certain antifungal activities against Physalospora piricola, Fusarium oxysporum f. sp.
Cucumerinum, Cercospora arachidicola, Fusarium graminearum and Alternaria solani, in which
compound Ⅲb presented the best antifungal activity against Cercospora arachidicola and Physalospora
piricola with inhibition rates of 85.0% and 79.2%, respectively.
Key words: perillaldehyde; oxime ester; herbicidal activity; antifungal activity; fine chemical intermediates
Foundation items: National Natural Science Foundation of China (31460173); Open Funding of Guangxi
Key Laboratory of Chemistry and Engineering of Forest Products (GXFC15-01)

收稿日期：2017-07-24; 定用日期：2017-11-28; DOI: 10.13550/j.jxhg.20170598
基金项目：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）
作者简介：林桂汕（1970—），男，副教授，硕士生导师。联系人：段文贵（1964—），男，教授，博士生导师，电话：0771-3239910，
E-mail：wgduan@gxu.edu.cn。