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林产化学与工业 ›› 2020, Vol. 40 ›› Issue (1): 77-83.doi: 10.3969/j.issn.0253-2417.2020.01.011

• 研究报告 • 上一篇    下一篇

莰烯醛肟及其烃基醚衍生物的合成与抑菌活性研究

冯雪贞1,肖转泉2,陈尚钘1,范国荣1,廖圣良1,王宗德1,*()   

  1. 1. 江西农业大学 林学院, 国家林业和草原局木本香料(华东)工程技术研究中心, 江西 南昌 330045
    2. 江西师范大学 化学化工学院, 江西 南昌 330027
  • 收稿日期:2019-07-07 出版日期:2020-02-28 发布日期:2020-03-06
  • 通讯作者: 王宗德 E-mail:zongdewang@163.com
  • 作者简介:冯雪贞(1996-),女,福建莆田人,硕士生,研究方向为植物资源化学利用
  • 基金资助:
    国家重点研发计划资助项目(2017YFD0600704);江西省杰出青年人才计划资助项目(20162BCB23030);国家自然科学基金资助项目(31660178)

Synthesis and Antibacterial Activity of ω-formylcamphene Oxime and Its Hydrocarbyl Ethers Derivatives

Xuezhen FENG1,Zhuanquan XIAO2,Shangxing CHEN1,Guorong FAN1,Shengliang LIAO1,Zongde WANG1,*()   

  1. 1. College of Forestry, Jiangxi Agriculture University, East China Woody Fragrance and Flavor Engineering and Technology Research Center of State Forestry and Steppe Administration, Nanchang 330045, China
    2. College of Chemistry, Jiangxi Normal University, Nanchang 330027, China
  • Received:2019-07-07 Online:2020-02-28 Published:2020-03-06
  • Contact: Zongde WANG E-mail:zongdewang@163.com
  • Supported by:
    国家重点研发计划资助项目(2017YFD0600704);江西省杰出青年人才计划资助项目(20162BCB23030);国家自然科学基金资助项目(31660178)

摘要:

由莰烯醛(1)与羟胺盐酸盐反应合成了莰烯醛肟(2),继而与卤代烃反应合成了5种莰烯醛肟烃基醚衍生物,分别为:莰烯醛肟乙基醚(3a)、莰烯醛肟正丙基醚(3b)、莰烯醛肟正丁基醚(3c)、莰烯醛肟正戊基醚(3d)和莰烯醛肟苄基醚(3e)。通过红外光谱、质谱和核磁共振等仪器分析手段对产物结构进行了确认。在此基础上,采用菌丝生长速率法,评价了莰烯醛肟及其烃基醚衍生物对12种植物病原真菌的生长抑制作用,结果表明:产物对12种植物病原真菌皆有一定抑制作用,其中莰烯醛肟的抑菌活性最优,并且对油茶炭疽病的抑制效果最好,EC50为39.25 mg/L,对水稻纹枯病菌、猕猴桃果实拟茎点霉、玉米赤霉病菌和毛竹枯梢病病原菌的EC50为40~50 mg/L;在质量浓度为500 mg/L时,莰烯醛肟对水稻纹枯病菌等9种植物病原真菌完全抑制,对松枯梢病菌和七叶树壳孢菌的抑制率达97%以上,当药液浓度降低时,莰烯醛肟对大部分病原菌的抑制率仍然超过百菌清500 mg/L时的抑制率。虽然莰烯醛肟烃基醚衍生物的抑菌活性较莰烯醛肟有所降低,但对毛竹枯梢病菌、梨链格孢菌和玉米赤霉病菌的抑制率皆高于(或等于)百菌清。

关键词: 莰烯醛, 莰烯醛肟, 相转移催化, 结构分析, 抑菌活性

Abstract:

ω-Formylcamphene oxime (2) was synthesized by the reaction of formylcamphene (1) with hydroxylamine hydrochloride.and then reacted with halohydrocarbon to synthesize five ω-formylcamphene oxime alkyl ether derivatives, such as ω-formylcamphene oxime ethyl ether (3a), ω-formylcamphene oxime propyl ether (3b), ω-formylcamphene oxime butyl ether (3c), ω-formylcamphene oxime n-pentyl ethers (3d), ω-formylcamphene oxime benzyl ethe (3e). Their structures were characterized by FI-IR, MS and NMR. The mycelium growth rate method was used to test the inhibitory effects of ω-formylcamphene oxime and its hydrocarbyl ethers on 12 kindsof plant pathogenic fungi. The results showed that the products had certain inhibitory effects on 12 kinds of plant pathogenic fungi, among which ω-formylcamphene oxime had the best activity and the best inhibitory against Colletotrichum gloeosporioides, EC50 was 39.25 mg/L. The EC50 values of Thanatephoruscu cumeris, Phomopsis sp., Fusarium avenaceum and Ceratosphaeria phyllostachydis sp. nov. were 40-50 mg/L. Under the concentration of 500 mg/L, ω-formylcamphene oxime completely inhibited 9 plant pathogenic fungi such as Thanatephorus cucumeris, and the inhibitory rates of ω-formylcamphene oxime against Sphaeropsi ssapinea and Fusicoccum aesuli were over 97%. When the medicament concentration of ω-formylcamphene oxime lowered, the inhibitory rates on most plant pathogenic fungi were still higher than that of chlorothalonil at 500 mg/L. Although the antibacteria activity of ω-formylcamphene oxime hydrocarbyl ethers was lower than that of ω-formylcamphene oxime, but the inhibitory rates of ω-formylcamphene oxime hydrocarbyl ethers against Ceratosphaeria phyllostachydis, Alternaria kikuchiana and Fusarium avenaceum were generally higher than that of chlorothalonil.

Key words: formylcamphene, ω-formylcamphene oxime, phase transfer catalysis, structural analysis, antibacterial activity

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