Carpophilus hemipterus

Figure 6.6 Structures of 2,3-dihydro-2,3,5-trimethyl-6-(1 -methyl-2 -oxobutyl)-4H-pyran-4-one (stegobinone), pheromone of Stegobium paniceum (L.) (Anobiidae) (Kuwahara et al., 1978) and (2E,4E,6E,8E)-3,5,7-trimethyl-2,4,6,8-decatetraene, pheromone component of Carpophilus hemipterus (L.) (Nitidulidae) (Bartelt et al., 1991). The carbon skeletons are identical, and likely derived through similar pathways (see text).

Bartelt R. J., Weisleder D., Dowd P. F. and Plattner R. D. (1992) Male-specific tetraene and triene hydrocarbons of Carpophilus hemipterus structure and pheromonal activity. J. Chem. Ecol. 18, 379 102. 

Petroski R. J. and Vaz R. (1995) Insect aggregation pheromone response synergized by host type volatiles. Molecular modeling evidence for close proximitiy binding of pheromone and coattractant in Carpophilus hemipterus (L.) (Coleoptera Nitidulidae). In Computer-Aided Molecular Design, eds C. H. Reynolds, M. K. Holloway and H. K. Cox, pp. 197-210. ACS Symposium Series 589, American Chemical Society, Washington, DC. 

Chapter 19 by Bartelt is devoted to the pheromonal role of short-chain hydrocarbons, especially short i n etli y l/etli y I - branched and unsaturated components in beetles. The most abundant components in Carpophilus hemipterus (Coleoptera, Nitidulidae) have been identified as (2/ ,4/ ,6/ ,8/ )-3,5,7-(rimc(hyl-2,4,6,8-decatetracnc and (2E,4E,6E,SE)-3,5,7-trimethyl-2,4,6,8-undecatetraene (Bartelt et al., 1990). Later studies showed that male C. hemipterus emit nine all-E tetraene hydrocarbons and one all-E triene hydrocarbon in addition to the two previously reported pheromonally active tetraenes (Bartelt et al., 1992). In their review of biologically active compounds in beetles, Francke and Dettner (2005) fisted only a few dozen of those pheromonal compounds, most of which were identified by Bartelt. 

Bartelt, R. J., Dowd, P. F., Vetter, R. S., Shorey, H. H. and Baker, T. C. (1992a). Responses of Carpophilus hemipterus (Coleoptera Nitidulidae) and other sap beetles to the pheromone of C. hemipterus and host-related coattractants in California field tests. Environ. Entomol., 21,1143-1153. 

Dowd, P.F. and Bartelt, R. J. (1991). Host-derived volatiles as attractants and pheromone synergists for driedfruit beetle, Carpophilus hemipterus. J. Chem. Ecol., 17, 285-308. 

Petroski, R. J. and Vaz, R. (1995). Insect aggregation pheromone response synergized by host-type volatiles molecular modeling evidence for close proximity binding of pheromone and coattractant in Carpophilus hemipterus (L.)... 

Several aggregation pheromones are metabolically altered fatty acids, or mixtures of these compounds. The most active attractants for the sawtoothed grain beetle, Orzyaephi-lus surinamensis, from oats were (2 )-nonenal and (2E,4E) nonadienal (Mikolajczak et al., 1984). The most abundant compound from a variety of food-related resources with pheromonal activity for males of the driedfruit beetle, Carpophilus hemipterus (Coleoptera Nitidulidae), was (2 ,4 ,6 , 8 )-3,5,7-trimethyl-2,4,6,8-decatetraene (Bartelt et al, 1990). 

Bartelt, R. j., P. F. Dowd, R. D. Plattner, and D. Weisleder, Aggregation pheromone of the driedfhiit beetle, Carpophilus hemipterus Wind-tunnel bioassay and identification of two novel tetraene hydrocarbons, J. Chem. Ecol., 16, 1015-1039 (1990). 

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