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Chemical analysis of the female sex pheromone in Palpita nigropunctalis (Lepidoptera: Crambidae)

Author:
Yan, Qi, Fujino, Aguri, Naka, Hideshi, Dong, Shuang-Lin, Ando, Tetsu
Source:
Journal of Asia-Pacific entomology 2018 v.21 no.4 pp. 1283-1288
ISSN:
1226-8615
Subject:
Crambidae, Oleaceae, absorption, acetates, aldehydes, chemical analysis, chemical bonding, dimethyl disulfide, electroantennography, females, ions, males, moieties, pests, pheromone glands, sex pheromones, spectrometers, spectrophotometers
Abstract:
The lilac pyralid, Palpita nigropunctalis Bremer (Lepidoptera: Crambidae), is a common pest of Oleaceae plants. A crude extract of the female sex pheromone glands was examined by gas chromatography-electroantennogram detection (GC-EAD) and GC coupled to a mass spectrometer (GC/MS). The GC-EAD analysis revealed three EAG-active components (I–III) in a ratio of 1:0.2:0.01 (I: II: III). GC/MS analysis successfully recorded the mass spectra of I and II. For I, ions at m/z 238 (M+) and 220 ([M-18]+) indicated the structure of a monoenyl aldehyde with a 16-carbon chain. For II, M+ was not detected, but ions at m/z 222 ([M-60]+) and 61 ([AcOH+1]+) suggested that II was a monoenyl acetate with a 16-carbon chain. Further GC/MS analysis of the extract treated with dimethyl disulfide revealed that the double bonds in both I and II are located at the same position of 11th-carbon. In addition, the pheromone extract was examined by GC/Fourier transform-infrared spectrophotometer (GC/FT-IR). An IR spectrum of I showed characteristic absorption at 1716 and 966 cm−1, indicating a formyl group and E configuration of the double bond, respectively. In the case of II, absorption at 1745 and 968 cm−1 indicated an ester carbonyl and E configuration, respectively. Taken together and by comparison with authentic standards, I and II were confirmed as (E)-11-hexadecenal and (E)-11-hexadecenyl acetate, respectively; while III was speculated as (E)-11-hexadecen-1-ol. The synthetic I, II and III all coincided well with those of the natural components in chemical data, and elicited strong electroantennographic activity in male P. nigropunctalis.
Agid:
6258613