Oviposition-deterring pheromones

Klewer, N., Ruzicka, Z. and Schulz, S. (2007). (Z)-Pentacos-12-ene, an oviposition-deterring pheromone of Cheilomenes sexmaculata. J. Chem. Ecol., 33, 2167-2170. 

Treatment of bromide 454b with magnesium generates Grignard reagent 495 [114], which is readily alkylated with bromide 496. Acetonide 497 was subsequently converted to 498, the oviposition-deterring pheromone of Rhagoletis cerasi L. (Scheme 70). 

Oviposition deterring pheromone (host marking pheromones). 

The European cherry fruit fly, Rhagoletis cerasi, lays a single egg into half-ripe cherries. An oviposition-deterring pheromone, which prevents oviposition by a second female of the same species, was isolated from the feces of the insect. This compound was characterized as A [15(p-glucosyl)oxy-8-hydroxypalmitoyl]-taurine (76) (Fig. 2.30) (Hurter et al., 1987). 

Hurter, J., E. F. Boller, E. Stadler, B. Blattmann, H. R. Buser, N. U. Bosshard, L. Damm, M. W. Kozlowski, R. ScHONi, F. Raschdorf, R. Dahinden, E. Schlumpf, H. Fritz, W. J. Richter, and J. Schreiber, Oviposition-deterring pheromone in Rhagoletis cerasi L. Purification and determination of the chemical constitution, Experientia, 43, 157-164 (1987). 

Crnjar, R. M. and Prokopy, R. J. (1982) Morphology and electrophysiological mapping of oviposition-deterring pheromone receptors in Rhagoletis pomonella. J. Insect Physiol. 28, 393-400. 

Prokopy, R. J. (1981) Oviposition deterring pheromone system of apple maggot flies. In Management of Insect Pests With Semiochemicals (Mitchell, E. R., ed.) pp. 477-494. Plenum Press, New York. 

There are several other phytophagous insect groups in which the existence of oviposition-deterring pheromone deposited by adults or emanating from larvae has been demonstrated the agromyzid fly, Agromyza frontella (Quiring,... 

In none of the phytophagous insects releasing oviposition-deterring pheromone has the pheromone been fully chemically characterized. However, substantial progress toward this end has been made by Oshima et al. (1973) on Callosobruchus, by Mudd and Corbet (1973) on Ephestia, by Hurter et al. (1976) on R. cerasi, and by Dundulis, Tumlinson, and Prokopy (unpublished data) on R. pomonella. 

The residual properties of oviposition-deterring pheromones are of particular importance to the host discrimination process. In cases where deterrent components from occupied resources may be emitted until completion of larval development, such as pheromonal release by larvae of Ephestia, Plodia and Heliothis, host discrimination mediated by pheromone may remain at a high level. However, in cases where deterrent components have only moderate residual activity under dry conditions or are water-soluble, both of which characterize tephritid pheromones, host discrimination mediated by pheromone may break down well before the completion of larval development. Here, one might suspect selection would favor female detection of larvae, or their effects. This does in fact seem to be the case in R. complete (Cirio, 1972) and R. pomonella (Averill and Prokopy, unpublished data), but further research is needed to explore this aspect more fully. 

Roitberg, B. D. and Prokopy, R. J. (1983) Host deprivation influence on response of Rhagoletispomonella to its oviposition-deterring pheromone. PhysioL Ent, 8,69-72. 

Schoonhoven, L. M., Sparnaay, T., Van Wissen, W. and Meerman, J. (1981). Seven-week persistance of an oviposition-deterring pheromone. J. Chem. Ecol., 7, 583-8. 

Zimmerman, M. (1979) Oviposition behavior and the existence of an oviposition-deterring pheromone in Hylemya. Env. Ent., 8, 277-9. 

Boiler, E.F. J. Horter. 1985. Oviposition deterring pheromone in Rhagoletis cerasi behavioral laboratory test to measure pheromone activity. Entomol. Exp. Appl. 39 163-169. 

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