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AssigneeNational Research Council of Canada
InventorsPeter Silk, Jon Sweeney, Krista Ryall, Barry Lyons
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The invention disclosed relates to the detection of the Emerald Ash Borer (EAB), Agrilus planipennis Fairmaire (Coleoptra: B-prestidae) and in particular to the use of contact sex phenomones therefor. Analyses of the elytral hydrocarbons from male and female emerald ash borer, that were freshly emerged vs. sexually mature (>10 days old) revealed a female-specific compound, 9-methyl-pentacosane (9-Me-C25), only present in sexually mature females. This material was synthesized by the Wittig reaction of 2-decanone with (n-hexadecyl)-triphenylphosphonium bromide followed by catalytic reduction to yield racemic 9-Me C25, which matched the natural compound by GC/MS (retention time and EI-mass spectrum). In field bioassays with freeze-killed sexually mature A. planipennis females, feral males spent significantly more time in contact and attempting copulation with unwashed females than with females that had been washed in n-hexane to remove the cuticular hydrocarbons. Hexane-washed females to which 9-Me-C25 had been reapplied elicited similar contact time and percentage of time attempting copulation as unwashed females, indicating that 9-methyl-pentacosane is a contact sex-pheromone component of A. planipennis. This is the first contact sex pheromone identified in the Buprestidae.
A composition for the attraction and detection of a sexually mature male Emerald Ash Borer (EAB) Agrilus planipennis Fairmaire (Coleoptra:
A method for the attraction and detection of a sexually mature male Emerald Ash Borer Agrilus planipennis (Coleoptra:
A process for making racemic 9-methyl pentacosane (9-MeC25), a racemic mixture of the 9R- and 9S-enantiomers, comprising (a) the base-catalyzed Wittig coupling of 2-decanone with (n-hexadecyl)triphenylphosphonium bromide to form an alkene, and (b) concomitant catalysed hydrogenation of the resultant alkene, using a noble metal catalyst e.g Pd/C.
A process for making pure (S)-9-methyl pentacosane (9-MeC25), comprising (a) alkylating (R)-citronellyl bromide with the Grignard reagent n-hexylmagnesium bromide in the presence of lithium tetrachlorocuprate as catalyst to form an alkene, (b) ozonloysis of the alkene followed by reductive workup with triphenylphosphine, (c) a Wittig reaction of the compound so formed with tridecyltriphenyl phosphonium bromide and n-butyllithium to form a mixture of cis and trans alkenes, and (d) hydrogenation thereof under a noble metal catalyst e.g. Pd/C, to form (S)-9-methylpentacosane (9-MeC25).
A process for making pure (R)-9-methylpentacosane(9-MeC25), comprising (a) alkylating (S)-citronellyl bromide with the Grignard reagent n-hexylmagnesium bromide in the presence of lithium tetrachlorocuprate as catalyst to form an alkene, (b) ozonloysis of the alkene followed by reductive workup with triphenylphosphine, (c) a Wittig reaction of the compound so formed with tridecyltriphenyl phosphonium bromide and n-butyllithium to form a mixture of cis and trans alkenes, and (d) hydrogenation thereof under a noble metal catalyst e.g. Pd/C, to form (R)-9-methylpentacosane (9-MeC25).
Dependencies are inferred from the claim text.