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Identification, Synthesis, and Field Evaluation of the Sex Pheromone of the Citrus Fruit Borer Ecdytolopha aurantiana

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Abstract

The sex pheromone of the citrus fruit borer Ecdytolopha aurantiana has been identified by gas chromatography coupled to an electroantennographic detector (GC-EAD). The electron impact mass spectral (EI-MS) fragmentation of the major EAD-active peak gave identifying features for a monounsaturated acetate. Further analyses by chemical ionization mass spectrometry (CI-MS), vapor-phase infrared spectroscopy (GC-IR), along with chemical derivatization (DMDS reaction), led to full characterization of the major component as (E)-8-dodecenyl acetate (E8–12 : Ac). The second constituent was identified as the related alcohol, (E)-8-dodecenol (E8–12 : OH). The two compounds were indistinguishable from the authentic synthetic standards in chemical and EAD analyses. Samples of the two compounds were obtained by a facile synthesis utilizing lithium chemistry. Field tests showed that captures in traps baited with a mixture of E8–12 : Ac and E8–12 : OH at 100 : 1 and 10 : 1 ratios were not significantly different from the catches in traps having two virgin females. Dosage tests showed better performance of traps baited with 1 mg than those with 0.1 mg of the pheromone blend, either in 100 : 1 or 10 : 1 ratio.

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Leal, W.S., Bento, J.M.S., Murata, Y. et al. Identification, Synthesis, and Field Evaluation of the Sex Pheromone of the Citrus Fruit Borer Ecdytolopha aurantiana. J Chem Ecol 27, 2041–2051 (2001). https://doi.org/10.1023/A:1012242904220

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  • DOI: https://doi.org/10.1023/A:1012242904220

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