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

doi:10.3969/j.issn.1004-1524.2021.10.13

Acta Agriculturae Zhejiangensis ›› 2021, Vol. 33 ›› Issue (10): 1897-1903.DOI: 10.3969/j.issn.1004-1524.2021.10.13

• Plant Protection • Previous Articles Next Articles

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

Abstract

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

CLC Number:

S433
Q966

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.

Figures/Tables 5

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

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

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

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

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

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