樟脑酸基酰腙类化合物的合成及其抑菌、除草活性研究

doi:10.3969/j.issn.0253-2417.2019.05.006

林产化学与工业 ›› 2019, Vol. 39 ›› Issue (5): 41-49.doi: 10.3969/j.issn.0253-2417.2019.05.006

樟脑酸基酰腙类化合物的合成及其抑菌、除草活性研究

郑万里, 马献力, 周小群, 李芳耀, 辛懋, 蒋彩娜

桂林医学院药学院, 广西桂林 541004

收稿日期:2019-03-26 出版日期:2019-10-25 发布日期:2019-11-01
通讯作者: 蒋彩娜,教授,硕士生导师,主要从事药物分析新技术研究;E-mail:jiangcaina@glmc.edu.cn E-mail:jiangcaina@glmc.edu.cn
作者简介:郑万里(1992-),男,安徽宿州人,硕士生,主要从事天然产物的改性及有机合成研究
基金资助:
桂林市科学研究与技术开发资助项目（20170108-10）；广西自然科学基金资助项目（2016GXNSFAA380323，2018GXNSFAA138165）

Synthesis, Antibacterial and Herbicidal Evaluation of Camphoric Acid-based Acylhydrazone Compounds

ZHENG Wanli, MA Xianli, ZHOU Xiaoqun, LI Fangyao, XIN Mao, JIANG Caina

Pharmacy School, Guilin Medical University, Guilin 541004, China

Received:2019-03-26 Online:2019-10-25 Published:2019-11-01

摘要/Abstract

摘要： 以樟脑酸为原料，先经过脱水反应制备樟脑酸酐，再与水合肼酰化制备N-氨基樟脑酰亚胺，然后分别与多氟取代苯甲醛、噻吩甲醛和呋喃甲醛缩合得到12个新型的樟脑酸基酰腙化合物4a~4l。利用傅里叶变换-红外光谱（FT-IR）、核磁共振（¹H NMR和¹³C NMR）以及电喷雾-质谱（ESI-MS）等对化合物进行结构表征。抑菌活性测试表明：质量浓度50 mg/L时，5-二氟苯基樟脑酸基酰腙（4i）、2-三氟甲基苯基樟脑酸基酰腙（4a）和2，3-二氟苯基樟脑酸基酰腙（4d）对苹果轮纹病菌的抑制率分别为90.6%、85.4%和82.2%。除草活性测试表明：质量浓度100 mg/L时，3-三氟甲基苯基樟脑酸基酰腙（4b）、3，4-二氟苯基樟脑酸基酰腙（4h）和3-噻吩基樟脑酸基酰腙（4k）对油菜胚根的生长抑制率分别为94.7%、95.6%和80.6%。其中化合物4i综合效果最好，50 mg/L时对苹果轮纹病菌的抑制率90.6%（活性级别为A级），100 mg/L时对油菜胚根的生长抑制率75.6%（活性级别为B级）。

关键词: 樟脑酸, 酰腙, 合成, 抑菌活性, 除草活性

Abstract: Camphoric anhydride (2) was prepared via dehydration reaction using camphoric acid (1) as starting material. N-aminocamphorimide (3) was prepared by the acylation of compound2 with hydrazine hydrate. And then, 12 novel camphoric acid-based acylhydrazone compounds4a-4l were synthesized by the condensation reaction between N-aminocamphorimide and polyfluoro-substituted benzaldehyde, thiophene-carbaldehyde or furaldehyde. The target compounds were characterized by means of Fourier transform infrared spectroscopy(FT-IR), nuclear magnetic resonance(¹H NMR and ¹³C NMR) and electrospray ionization-mass spectrometry(ESI-MS). The preliminary bioassay showed that 3, 5-difluorophenyl camphoric acid-based acylhydrazone (4i), 2-trifluoromethylphenyl camphoric acid-based acylhydrazone (4a) and 2, 3-difluorophenyl camphoric acid-based acylhydrazone (4d) exhibited excellent antifungal activities with the inhibition ratios of 90.6%, 85.4% and 82.2% against Botryosphaeria berengeriana at the mass concentration of 50 mg/L. Herbicidal evaluation results showed that most of the compounds had certain inhibitory effects on the growth of rape radicle at 100 mg/L. Among them, the growth inhibition rates of compounds 3-trifluoromethylphenyl camphoric acid-based acylhydrazone (4b), 3, 4-difluorophenyl camphoric acid-based acylhydrazone (4h) and 3-thienyl camphoric acid-based acylhydrazone (4k) on the radicle of rape(Brassica campestris) were 94.7%, 95.6% and 80.6%, respectively. Compound4i has the best overall effect, the inhibition ratio of 90.6% against B.dothidea at 50 mg/L (the activity level was A grade); the root growth inhibition rate of on root of rape (B. campestris) was 75.6% at 100 mg/L (the activity level was B grade).

Key words: camphoric acid, acylhydrazone, synthesis, antibacterial activity, herbicidal activity

中图分类号:

TQ351

郑万里, 马献力, 周小群, 李芳耀, 辛懋, 蒋彩娜. 樟脑酸基酰腙类化合物的合成及其抑菌、除草活性研究[J]. 林产化学与工业, 2019, 39(5): 41-49.

ZHENG Wanli, MA Xianli, ZHOU Xiaoqun, LI Fangyao, XIN Mao, JIANG Caina. Synthesis, Antibacterial and Herbicidal Evaluation of Camphoric Acid-based Acylhydrazone Compounds[J]. Chemistry and Industry of Forest Products, 2019, 39(5): 41-49.

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樟脑酸基酰腙类化合物的合成及其抑菌、除草活性研究

Synthesis, Antibacterial and Herbicidal Evaluation of Camphoric Acid-based Acylhydrazone Compounds

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