title: Identification, synthesis, and field evaluation of the sex pheromone of the citrus fruit borer Ecdytolopha aurantiana.
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.
authors.affiliation: Department of Entomology, University of California, Davis 95616, USA. wsleal@ucdavis.edu
authors.forename: W S
authors.initials: WS
authors.lastname: Leal
authors.forename: J M
authors.initials: JM
authors.lastname: Bento
authors.forename: Y
authors.initials: Y
authors.lastname: Murata
authors.forename: M
authors.initials: M
authors.lastname: Ono
authors.forename: J R
authors.initials: JR
authors.lastname: Parra
authors.forename: E F
authors.initials: EF
authors.lastname: Vilela
mesh_terms: D000085:Acetates / Q000302:isolation & purification / Q000494:pharmacology*; D000438:Alcohols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D002849:Chromatography, Gas; D005229:Fatty Acids, Monounsaturated / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D008401:Gas Chromatography-Mass Spectrometry; D007814:Larva; D007915:Lepidoptera; D009068:Movement; D012724:Sex Attractants / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D012903:Smell
chemical_list: D000085:Acetates; D000438:Alcohols; D005229:Fatty Acids, Monounsaturated; D012724:Sex Attractants; C026162:8-dodecenyl acetate