Nitidulidae

The male-produced volatiles eficiting responses from male and female antennae of the sap beetle, Colopterus truncatus Randall (Coleoptera Nitidulidae), were identified as (2A ,4A ,6A )-3,5-dimethyl-2,4,6-octa-triene, 2E, AE, 6T )-4,6-dimethyl-2,4,6-nonatriene and 2E, AE,6E,SE) 3,5,7-trimethyl-2,4,6,8-decatetraene. A fourth male-specific compound... 

Bartelt, R. J. and Weisleder, D. (1996). Polyketide origin of pheromones of Carpophilus davidsoni and C. mutilatus (Coleoptera Nitidulidae). Bioorganic and Medicinal Chemistry 4 429 138. 

Nardi J. B., Dowd P. F. and Bartelt R. J. (1996) Fine structure of cells specialized for secretion of aggregation pheromone in a nitidulid beetle Carpophilus freemani (Coleoptera Nitidulidae). Tissue Cell 28, 43-52. 

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).

Figure 6.7 Biosynthesis of (2 ,4 ,6 )-5-ethyl-3-methyl-2,4,6-nonatriene, pheromone component of Carpophilus freemani Dobson (Nitidulidae). The pathway is a modification of normal fatty acid biosynthesis, involving initiation with acetate elongation with first propionate (to provide the methyl branch), then butyrate (to provide the ethyl branch) and chain termination with a second butyrate. The final butyrate to add suffers a loss of C02, after adding in a unique head-to-head reaction. Intermediates of the pathway likely occur as activated (e.g. CoA) derivatives (Petroski et al., 1994 Bartelt and Weisleder, 1996).

Kohnle U., Densbom S., Kolsch P., Meyer H. and Francke W. (1992b) -7-Methyl-l,6-dioxaspiro[4.5] decane in the chemical communication of European Scolytidae and Nitidulidae (Coleoptera). J. Appl. Ent. 114, 187-192. 

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. 

Petroski R. J., Bartelt R. J. and Weisleder D. (1994) Biosynthesis of (2 ,4 ,6 )-5-ethyl-3-methyl-2,4,6-nonatriene the aggregation pheromone of Carpophilus freemani (Coleoptera Nitidulidae). Insect Biochem. Molec. Biol. 24, 69-78. 

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., Shorey, H.H. and Weisleder, D. (1990b). Aggregation pheromone of Carpophilus freemani (Coleoptera Nitidulidae) a blend of conjugated triene and tetraene hydrocarbons. Chemoecology, 1,105-113. 

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. 

Bartelt, R. J. and James, D. G. (1994). Aggregation pheromone of Australian sap beetle, Carpophilus davidsoni (Coleoptera Nitidulidae)../. Chem. Ecol., 20, 3207-3219. 

Carpophilus antiquus (Coleoptera Nitidulidae) and kairomonal use of C. lugubris pheromone by C. antiquus. J. Chem. Ecol., 19, 2203-2216. 

Blumberg, D., Goldenberg, S Bartelt, R. J. and Williams, R.N. (1993). Responses to synthetic aggregation pheromones, host-related volatiles, and their combinations by Carpophilus spp. (Coleoptera Nitidulidae) in laboratory and field tests. Environ. Entomol., 22, 837-842. 

Connell, W.A. (1956). Nitidulidae of Delaware. Bulletin Number 318 (Technical). 

Connell, W.A. (1991). Sap beetles (Nitidulidae, Coleoptera). In Insect and Mite Pests in Food, Vol. 1, ed. J. R. Gorham. Agricultural Handbook Number 65, United States Department of Agriculture and United States Department of Health and Human Services. Washington, DC United States Government Printing Office, pp. 151-174. 

Dorsey, C.K. and Leach, J.G. (1956). The bionomics of certain insects associated with oak wilt with particular reference to the Nitidulidae. J. Econ. Entomol., 49,... 

Dowd, P. F. (2000). Dusky sap beetles (Coleoptera Nitidulidae) and other kernel damaging insects in Bt and non-Bt sweet com in Illinois../. Econ. Entomol., 93, 1714-1720. 

Dowd, P.F. and Bartelt, R. J. (1993). Aggregation pheromone glands of Carpophilus freemani (Coleoptera Nitidulidae) and gland distribution among other sap beetles. Ann. Entomol. Soc. Am., 86, 464-469. 

Dowd, P.F., Bartelt, R. J. and Wicklow, D.T. (1992). Novel insect trap useful in capturing sap beetles (Coleoptera Nitidulidae) and other flying insects. J. Econ. Entomol., 85, 772-778. 

Dowd, P.F., Moore, D.E., Vega, F.E., McGuire, M.R., Bartelt, R.J., Nelson, T.C. and Miller, D.A. (1995). Occurrence of amermithid nematode parasite of Carpophilus lugubris (Coleoptera Nitidulidae) in central Illinois. Environ. Entomol., 24, 1245-1251. 

Comparison of trap designs for use with aggregation pheromone and synthetic co-attractant in a user-friendly attract and kill system to control Carpophilus spp. (Coleoptera Nitidulidae). Aust. J. Entomol., 46, 244-250. 

Coleoptera Nitidulidae) responses to aggregation pheromone plus decomposed fruit as co-attractant in stone fruit orchards in southern Australia. Gen. Appl. Entomol., 34, 33 42. 

James, D.G., Bartelt, R.J. and Moore, C.J. (1996b). Mass-trapping of Carpophilus spp. (Coleoptera Nitidulidae) in stone fruit orchards using synthetic aggregation pheromones and a coattractant development of a strategy for population suppression. J. Chem. Ecol., 22,1541-1556. 

James, D.G., Faulder, R. J. and Bartelt, R.J. (1995). Fauna and seasonal abundance of Carpophilus spp. (Coleoptera Nitidulidae) in four stone fruit growing regions of southeastern Australia as determined by pheromone-trapping. J. Aust. Entomol. Soc., 34, 327-333. 

---