Dacus oleae

The Dacus fly (Dacus oleae, olive fly), a pest producing serious damage to olives and one related to other flies that attack a variety of fruits, is also highly susceptible to aldrin (6). 

Concerning the latter class of compounds a carbene insertion has been employed to prepare the major constituent of the sex attractant of the olive fly (Dacus oleae). 

Marko et al. used this approach during the total synthesis of one of the major components of the Dacus oleae sex pheromone mixture (Scheme 13.90) [59, 60], The desired spiro-ketal 246 was obtained in three steps and 51% overall yield starting from allylsilyl ether 106a. 

Cmjar R. M., Scalera G., Liscia A., Angioy A. M., Bigiani A., Pietra P. and Tomassini Barbarossa I. (1989) Morphology and EAG mapping of the antennal olfactory receptors in Dacus olea. Entomol. Exp. Appl. 51, 77-85. 

Our search for attractants is focused on the Tephritid family of fruit flies which Includes species that are of economic importance in Europe, Asia, Australia, and the Americas. It is estimated that the olive fly, Dacus oleae. causes ten percent fruit drop in European olives. Of the Infested fruit remaining on the trees, 25 percent of the flesh is destroyed (48). A conservative estimate of the annual cost of the recent Medfly infestation in California, not including capital outlays, is 59 million for chemical controls, 38 million for quarantine and fumigation, and 260 million in crop losses (49). It is estimated that 70% of the susceptible fruit in Egypt is infested by the Medfly (50) and a 50 million control program has been started there. 

Two important spiroketals, such as l,7-dioxaspiro[5.6]undecane (29a), the major component of the olive fruit fly (Dacus oleae) sex pheromone (Baker et ah, 1980 Fanelli et ah, 1983), and ( )-2-methyl-l,7-dioxaspiro[5.6]dodecane (29b), a component of pheromone of Andrena haemorrhoa (Bergstroem et al., 1981 Katsurada and Mori, 1984), have been prepared in a cascade process from polyfunctionalized nitroalkanes (26) (Ballini and Petrini, 1992). 

Baker, R., Francke, W., Herbert, R., Howse, P.E., Jones, O.T., and Reith, W. 1980. Identification and synthesis of the major sex pheromone of the olive fly (Dacus oleae). Journal of the Chemical Society, Chemical Communications, 2 52-3. 

Fanelli, R., Gariboldi, P., and Verotta, L. 1983. Studies on the sex pheromone of Dacus oleae. Analysis of the substances contained in the rectal glands. Experientia, 39(5) 502-5. 

C,H, 02, Mr 156.22, bp. 73 °C (4.0 kPa) (25,5R)-iso-mer [a] -100° (hexane) (2S,5S)-isomer [a] r%° (hexane). Aggregation pheromone of bark beetles of the genus Pityogenes. Males of P. chalcographm excrete this spiroacetal as a mixture of the (25,55)- and (25,5/()-isomers to attract males and females of the same species to colonize a host tree. Only the (25,5/ )-isomer has an attracting action which is dramatically increased by simultaneously excreted, extremely small amounts of methyl (2E,4Z)-2,4-decadienoate (C, H,g02, Mr 182.26). Isomers of C. are the pheromones conophthorin and olean, the sexual attractant of the olive fruit fly Dacus oleae. C. is currently the economically most important pheromone with a market value in 1995 of ca. 20 Mio. DM for its use against forest pests. 

C,H,602, Mr 156.22, bp. 77-78°C (1.73 kPa) liquid with a flower-like odor. O. is a chiral sex hormone secreted by female olive flies Dacus oleae. The natural product is racemic the (/f)-enantiomer, [alp -121.6°... 

Furthermore, 9 has an excellent efficacy in controlling Diptera spp. such as Rhagolethis cerasi, Dacus oleae and Ceratitis capitata in fruit crops like peaches and olives. 

Pheromones are important organic compounds in agriculture because they represent one means of baiting and trapping insects that may be harmful to crops. Olean, the sex pheromone for the olive fruit fly, Dacus oleae, can be synthesized from the hydroxyenol ether shown by treating it with a Brpnsted acid (H-A). 

Angioy, A. M., Liscia, A. and Pietra, P. (1978) The electrophysiological response of labellar and tarsal hairs of Dacus oleae (Gemel.) to salt and sugar stimulation. Boll, Soc, Ital, Biol, Sper, 54, 2115-21. 

Cirio, U. (1971) Reperti sul meccanismo stimolo-risposta nell ovideposizione del Dacus oleae Gmelin. Redia, 52, 577-600. 

Haniotakis, G. E. and Voyadjoglou, A. (1978) Oviposition regulation in Dacus oleae by various olive fruit characters. Ent. exp. appl., 24, 187-92. 

Vita, G. (1978) Individuazione del composto chimico che regola la deposizione delle uova del Dacus oleae. Rapporto Tecnico CNEN, RT/BIO 78) 17, 1-8. 

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