香茅醛缩醛类化合物的合成及其对小黄家蚁的驱避活性

›› 2014, Vol. 57 ›› Issue (8): 921-926.

香茅醛缩醛类化合物的合成及其对小黄家蚁的驱避活性

翁玉辉¹，肖转泉²，许锡招¹，陈金珠^3,*，范国荣¹，聂雪军¹，王宗德¹

(1. 江西农业大学林学院，国家林业局樟树工程技术研究中心，南昌 330045； 2. 江西师范大学化学化工学院，
南昌 330027； 3. 江西农业大学理学院，南昌 330045)

出版日期:2014-08-20 发布日期:2014-08-20

Synthesis of acetal derivatives of citronellal and their repellent activities against the pharaoh ant, Monomorium pharaonis (Hymenoptera: Formicidae)

WENG Yu-Hui¹, XIAO Zhuan-Quan², XU Xi-Zhao¹, CHEN Jin-Zhu^3,*, FAN Guo-Rong¹, NIE Xue-Jun¹, WANG Zong-De¹

(1. College of Forestry, Jiangxi Agricultural University, Camphor Engineering and Technology Research Center for State Forestry Administration, Nanchang 330045, China; 2. College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330027, China; 3. College of Science, Jiangxi Agricultural University, Nanchang 330045, China)

Online:2014-08-20 Published:2014-08-20

摘要/Abstract

摘要： 【目的】香茅醛类化合物具有较好的蚂蚁驱避活性，本研究旨在筛选具有良好驱避活性的新的萜类蚂蚁驱避剂。【方法】以香茅醛为原料合成了香茅醛二甲缩醛、香茅醛二乙缩醛、香茅醛二正丙缩醛、香茅醛二异丁缩醛、香茅醛乙二缩醛、香茅醛1,2-丙二缩醛和香茅醛1,3-丙二缩醛等化合物。所得产品经纯化后，用IR, MS, ¹H NMR及¹³C NMR进行结构表征，并在不同浓度下对小黄家蚁Monomorium pharaonis进行驱避活性测试。【结果】各化合物对小黄家蚁具有一定的驱避活性：在10 mg/mL的浓度下，除香茅醛二甲缩醛以外，其他化合物的驱避率均达到70%以上，其中香茅醛二乙缩醛、香茅醛乙二缩醛和香茅醛1,3-丙二缩醛对小黄家蚁的驱避率分别为87.47%，100%和97.53%。浓度为2.5 mg/mL时，其中5个化合物的驱避效果明显下降，但香茅醛乙二缩醛和香茅醛1,3-丙二缩醛仍然表现出很好的驱避活性，驱避率分别为85.33%和97.10%。方差分析也表明，香茅醛1,3-丙二缩醛在同一浓度下驱避效果最佳，其次是香茅醛乙二缩醛。【结论】结果说明，香茅醛二乙缩醛、香茅醛乙二缩醛和香茅醛1,3丙二缩醛可以用作小黄家蚁驱避剂，而香茅醛乙二缩醛和香茅醛1,3-丙二缩醛可以达到更好的驱避效果，使用浓度为2.5 mg/mL即可。本研究为良好萜类蚂蚁驱避剂的筛选提供了参考依据。

关键词: 香茅醛, 缩醛类化合物, 化学合成, 结构表征, 蚂蚁驱避剂, 驱避活性, 小黄家蚁

Abstract: 【Aim】 Citronellal has good repellent activity against ants. This study aims to seek novel ant terpenoid repellents. 【Methods】 A series of citronella acetals including citronellal dimethyl acetal, citronellal diethyl acetal, citronellal dipropyl acetal, citronellal diisobutyl acetal, citronellal glycol acetal, citronellal 1,2-propanediol acetal and citronellal 1,3-propanediol acetal were synthesized in this study using citronellal as the starting material. Their structures were characterized with IR, MS, ¹H NMR and ¹³C NMR after purification. The repellent activities of these compounds at different concentrations against the pharaoh ant, Monomorium pharaonis were tested. 【Results】 At the concentration of 10 mg/mL, all the compounds except citronellal dimethyl acetal had the repellent rate of more than 70%, and citronellal diethyl acetal, citronellal glycol acetal and citronellal 1,3-propanediol acetal had the repellent rates of 87.47%, 100% and 97.53%, respectively. When the concentrations of the compounds dropped to 2.5 mg/mL, the repellent activities of five compounds decreased significantly, while citronellal glycol acetal and citronellal 1,3-propanediol acetal still showed high repellent activities with the repellent rates of 85.33% and 97.10%, respectively. Variance analysis showed that citronellal 1,3-propanediol acetal had the strongest repellent effect, followed by citronellal glycol acetal. 【Conclusion】 The results suggest that citronellal diethyl acetal, citronellal glycol acetal and citronellal 1,3-propanediol acetal can be used for repelling M. pharaonis, and citronellal glycol acetal and citronellal 1,3-propanediol acetal can be better choices. This research provides a basic reference for screening good ant repellents.

Key words: Citronellal, acetal derivatives, chemical synthesis, structure characterization, ant repellent, repellent activity, Monomorium pharaonis

翁玉辉，肖转泉，许锡招，陈金珠，范国荣，聂雪军，王宗德. 香茅醛缩醛类化合物的合成及其对小黄家蚁的驱避活性[J]. , 2014, 57(8): 921-926.

[1]	陈新华, 万炜, 冯淑军, 许胜利, 杨建军, 段立清. 四种植物精油成分对枸杞棉蚜的生物活性[J]. 昆虫学报, 2019, 62(4): 453-460.
[2]	付磊磊, 李双阳, 何军, 马志卿, 张兴. 香芹酮和薄荷醇手性异构体对淡色库蚊熏蒸及驱避活性[J]. 昆虫学报, 2016, 59(7): 732-738.
[3]	许锡招, 宋杰, 王鹏, 范国荣, 陈金珠, 陈尚钘, 王宗德. 酰胺类蚊虫驱避化合物与引诱物氨分子缔合作用的计算[J]. , 2015, 58(6): 642-649.
[4]	李颗，李向辉，徐西林，袁哲明. 芳香羧酸衍生物驱避剂的非线性定量构效关系[J]. , 2014, 57(9): 1018-1024.
[5]	廖圣良，宋杰，范国荣，王鹏，王宗德，陈尚钘，姜志宽，陈金珠. 定量计算萜类蚊虫驱避化合物与羧酸缔合作用对其驱避活性的影响[J]. , 2014, 57(5): 547-556.
[6]	马卫宾，冯俊涛，马志卿，江志利，张兴. 冬青油与肉桂油对淡色库蚊的生物活性[J]. , 2013, 56(12): 1391-1396.
[7]	王宗德, 陈金珠, 宋湛谦, 姜志宽, 韩招久, 宋杰. 羟基香茅醛缩醛类化合物的合成及对蚊虫的驱避活性[J]. , 2010, 53(11): 1241-1247.
[8]	郝蕙玲, 邓晓军, 杜家纬. 猫薄荷精油有效成分的提取及其对白纹伊蚊、淡色库蚊的驱避活性[J]. , 2006, 49(3): 533-537.
[9]	万树青，徐汉虹，赵善欢，尚稚珍，蒋志胜，刘准. 多炔类化合物对亚洲玉米螟产卵驱避作用及玉米螟的触角电位反应[J]. , 2004, 47(3): 293-297.