基于Wolff-Kishner-黄鸣龙法合成红火蚁告警信息素及其触角电位反应

doi:10.3969/j.issn.1004-1524.2021.10.13

浙江农业学报 ›› 2021, Vol. 33 ›› Issue (10): 1897-1903.DOI: 10.3969/j.issn.1004-1524.2021.10.13

基于Wolff-Kishner-黄鸣龙法合成红火蚁告警信息素及其触角电位反应

王丽坤^a^,^b(), 黄俊^a^,^b, 章金明^b, 李晓维^a^,^b, 张治军^b, MUHAMMADHafeez^b, 吕要斌^a^,^b^,^*()

浙江省农业科学院 a.农产品质量安全危害因子与风险防控国家重点实验室(筹),浙江杭州 310021
浙江省农业科学院 b.植物保护与微生物研究所,浙江省植物有害生物防控重点实验室——省部共建国家重点实验室培育基地, 浙江杭州 310021

收稿日期:2020-08-25 出版日期:2021-10-25 发布日期:2021-11-02
通讯作者: 吕要斌
作者简介:*吕要斌,E-mail: luybcn@163.com
王丽坤(1989—),男,安徽安庆人,博士,助理研究员,研究方向为化学生态学和农药学。E-mail: wanglikun1314@sina.cn
基金资助:
浙江省“三农六方”科技协作项目(CTZB-F170623LWZ-SNY1-34)

Synthesis of red imported fire ant alarm pheromone based on Wolff-Kishner-Huangminlon reaction and its electroantennogram analysis

WANG Likun^a^,^b(), HUANG Jun^a^,^b, ZHANG Jinming^b, LI Xiaowei^a^,^b, ZHANG Zhijun^b, MUHAMMAD Hafeez^b, LYU Yaobin^a^,^b^,^*()

a. State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-Products (in Prepared), Hangzhou 310021, China
b. State Key Laboratory Breeding Base for Zhejiang Sustainable Pest and Disease Control, Institute of Plant Protection and Microbiology, Zhejiang Academy of Agricultural Sciences, Hangzhou 310021, China

Received:2020-08-25 Online:2021-10-25 Published:2021-11-02
Contact: LYU Yaobin

摘要/Abstract

摘要：

告警信息素是红火蚁(Solenopsis invicta Buren)中一类重要的信息素物质,具有引诱、趋避和聚集等多种活性,能够引起红火蚁强烈的行为反应。本研究通过Wolff-kishner-黄鸣龙还原法一步合成红火蚁告警信息素,并经气相色谱-质谱(GC-MS)和标准品对其结构进行鉴定和分析。结果表明,化合物纯度达到90.2%;该合成方法合理、简便和高效,反应条件可控,无安全隐患,适合工业化生产和应用。触角电位(EAG)实验表明,合成告警信息素能够引起红火蚁工蚁强烈的行为反应,并在100 μg剂量下EAG反应显著高于标准品(P<0.05)。

关键词: 红火蚁, Wolff-kishner-黄鸣龙还原法, 告警信息素, 合成

Abstract:

Alarm pheromone is an important pheromone in the red imported fire ant (Solenopsis invicta Buren). It can arouse a variety of behavioral response such as attracting, avoiding and recruitment. In the present study, the red imported fire ant was used as the research object. The alarm pheromone of the red imported fire ant was synthesized through the Wolff-kishner-Huangminlon reduction method by one step, and its structure was identified and analyzed by gas chromatography-mass spectrometry (GC-MS) and standard products. The results showed that the purity of the synthesized compound purity was 90.2%, the synthesis method was reasonable, simple and efficient, the reaction conditions were controllable, there was no hidden safety hazard, and it was suitable for industrial production and application. The electroantennogram (EAG) experiment showed that the synthetic alarm pheromone can cause strong behavioral responses of the red imported fire ant workers, and the EAG response was significantly higher than that of the standard product at a dose of 100 μg (P<0.05).

Key words: red imported fire ant, Wolff-Kishner-HuangMinlon reaction, alarm pheromone, synthesis

中图分类号:

S433
Q966

王丽坤, 黄俊, 章金明, 李晓维, 张治军, MUHAMMADHafeez, 吕要斌. 基于Wolff-Kishner-黄鸣龙法合成红火蚁告警信息素及其触角电位反应[J]. 浙江农业学报, 2021, 33(10): 1897-1903.

WANG Likun, HUANG Jun, ZHANG Jinming, LI Xiaowei, ZHANG Zhijun, MUHAMMAD Hafeez, LYU Yaobin. Synthesis of red imported fire ant alarm pheromone based on Wolff-Kishner-Huangminlon reaction and its electroantennogram analysis[J]. Acta Agriculturae Zhejiangensis, 2021, 33(10): 1897-1903.

图/表 5

图1 商品化标准品结构式[12,13,14]

Fig.1 Chemical structure of the commercial alarm pheromone[12,13,14]

图2 红火蚁告警信息素合成途径

Fig.2 Synthesis route of the alarm pheromone of the imported red fire ant

图3 标准品与合成化合物色谱图 1. 2-乙基-3,6-二甲基吡嗪;2. 2-乙基-3,5-二甲基吡嗪。

Fig.3 The TIC of the standard compound and synthetic chemical 1. 2-ethyl-3,6-dimethylpyrazine; 2. 2-ethyl-3,5-dimethylpyrazine.

图4 化合物2-乙基3,6-二甲基吡嗪质谱图

Fig.4 Mass spectrum of the synthetic compound of 2-ethyl-3,6-dimethylpyrazine

图5 红火蚁工蚁对测试样品的EAG反应 *表示合成化合物与标准品之间差异显著(P<0.05)。

Fig.5 EAG response of Solenopsis invicta workers to the tested odors * represented the significant difference between the synthetic compound and the standard(P<0.05).

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基于Wolff-Kishner-黄鸣龙法合成红火蚁告警信息素及其触角电位反应

Synthesis of red imported fire ant alarm pheromone based on Wolff-Kishner-Huangminlon reaction and its electroantennogram analysis

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