Identification of the Sex Pheromone Secreted by a Nettle Moth, Monema flavescens, Using Gas Chromatography/Fourier Transform Infrared Spectroscopy

• Published in: Journal of chemical ecology 2013-03, Vol.39 (3), p.350-357
• Main Authors: Shibasaki, Hiroshi, Yamamoto, Masanobu, Yan, Qi, Naka, Hideshi, Suzuki, Toshiro, Ando, Tetsu
• Format: Article
• Language: English
• Subjects: Agriculture; Animal and plant ecology; Animal, plant and microbial ecology; Animals; Behavior, Animal - drug effects; Biochemistry; Biological and medical sciences; Biological Microscopy; Biomedical and Life Sciences; Butterflies & moths; Chromatography, Gas; Ecology; Entomology; Female; Fourier transforms; Fruit trees; Fundamental and applied biological sciences. Psychology; Gas chromatography; General aspects; Infrared spectroscopy; Insecta; Invertebrates; Larvae; Life Sciences; Limacodidae; Male; Mass spectrometry; Moths - chemistry; Moths - drug effects; Moths - metabolism; Parasa; Prunus; Selenium Compounds - chemistry; Sex Attractants - analysis; Sex Attractants - chemical synthesis; Sex Attractants - pharmacology; Sex Attractants - secretion; Spectroscopy, Fourier Transform Infrared; Zinc Compounds - chemistry
• ISSN: 0098-0331; 1573-1561
• DOI: 10.1007/s10886-013-0253-8

The nettle moth Monema flavescens (Limacodidae) is a defoliator of fruit trees, such as Chinese plum and persimmon. The larvae of this species have spines containing a poison that causes serious irritation and inflammation in humans. Coupled gas chromatography-electroantennogram detection and gas chromatography/mass spectrometry analyses of a crude pheromone extract, combined with derivatization, indicated that female moths produced 8-decen-1-ol and 7,9-decadien-1-ol at a ratio of approximately 9:1. The E configuration of the double bonds was assigned for both components from infrared spectra, recorded on a gas chromatograph/Fourier transform-infrared spectrophotometer equipped with a zinc selenide disk cooled to −30 °C. The monoenyl and dienyl alcohols had absorptions characteristic of E geometry at 966 and 951 cm −1 , respectively. A band chromatogram at 951 cm −1 was useful for distinguishing geometric isomers, because terminal conjugated diene are difficult to resolve, even on high polarity columns. Furthermore, we identified the Z configuration of the same 7,9-dienyl alcohol secreted by another nettle moth, Parasa lepida lepida , through the absence of this absorption. In field trials, lures baited with a 9:1 mixture of ( E )-8-decen-1-ol and ( E )-7,9-decadien-1-ol attracted M. flavescens males. Furthermore, the field trials indicated that contamination with the ( Z )-diene reduced catches to the pheromone mixture more than did contamination with the ( Z )-monoene.