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Title: Identification and synthesis of hymenopteran pheromones
Author: Parker, Jane Elizabeth.
ISNI:       0000 0001 3470 432X
Awarding Body: University of Keele
Current Institution: Keele University
Date of Award: 2005
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GC-MS analysis of Camponotus floridanus revealed that queens and workers differ significantly in their cuticular hyrdrocarbons (CHC's) and surface compounds of their eggs. The CHC profiles comprised a complex mixture of straight and branched alkanes. Bioassays showed that the hydrocarbons on queens and queen eggs carry a signal that prevents workers from laying eggs and protects queen eggs from worker policing. GC-MS analysis also showed that the CHC's of C.jloridanus queens and workers and C. tortuganus workers differ between colonies. Synthesis of queen specific compounds was carried out in order to prepare a synthetic queen blend for use in bioassays. A synthetic route towards central-l ,5-dimethylalkanes was developed employing 3-methyl thiophene as a building block being sequentially acylated and reduced. A synthetic route towards 3-methyl carboxylic acids was also developed utilising the Homer-Wadsworth-Emmons reaction. The thiophene methodology was also used to prepare mono-methylalkanes and 3,X-dimethylalkanes. The metapleural glands of Acromyrmex echinator and its associated parasite Ainsinuator were analysed by GC-MS to compare the profiles of the two species. The 24 compounds identified included a range of carboxylic acids, lactones and ketoacids. The gland contents of the two species were found to be very similar. This was surprising as it was expected that the parasite would produce a lower number and amount of compounds due to the energy costs associated with their production. Attempts to further develop a synthetic route towards alkyl pyrazines was undertaken. Nitroalcohols were prepared from nitroalkanes and aldehdydes using alumina as a surface catalyst. Oxidation to nitroketones used pyridinium chlorochromate on silica and ultrasound. Attempts at the synthesis of tri and tetra substitued pyrazines were partially successful but not conclusive.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available