Drugstore beetle

Dermestids. The two most common invaders are the carpet beetle and the drugstore beetle or cigaret beetle. The latter, although not exactly identical species, are comparable in their habitat and habits. They are all likely to fly into the plant. 

Attractive Compounds. Only little is known about the systems of chemical communication in anobiid beetles. Investigations have been mainly concerned with two economically important species, the cigarette beetle, Lasioderma serricorne, and the drugstore beetle, Stegobium paniceum. 

The pheromone produced by females of the drugstore beetle was the first to be identified in an anobiid beetle 2,3-dihydro-2,3,5-trimethyl-6-(r-methyl-2 -oxobutyl)-4ff-pyran-4-one (stegobinone) [256] which by independent synthesis [257] was shown to keep (2S,3R,1 R)-configuration 123. A second compound... 

The furniture beetle Anobium punctatum, a death-watch beetle, seems to use the same communication system as the drugstore beetle [263,264]. 

Kuwahara, Y., Fukami, H., Ishii, S., Matsumura, F. and Burkholder, W. E. (1975b). Studies on the isolation and bioassay of the sex pheromone of the drugstore beetle, Stegobium paniceum (Coleoptera Anobiidae). Journal of Chemical Ecology 1 413 122. 

Chemical studies on the Anobiidae sex pheromone of the drugstore beetle, Stegobium paniceum (L) (Coleoptera). Tetrahedron 34 1769-1774. 

Very recently (R, S )-4-methyl-5-hydroxy-3-heptanone has been identified as the major component of the aggregation pheromone of the rice weevil, sltophilus orvzae L., and the maize weevil, S. zeamals Motsch. (28). This compound is obviously very different in structure from the previously identified curculionid pheromones. In fact, it is very similar to the pheromone of two other stored-products pests, the drugstore beetle and the cigarette beetle, which are in the family Anobiidae (see later). Undoubtedly, we will find more diversity in structure as more curculionid pheromones are identified. 

Only two Anobiidae pheromones have been identified thus far. The drugstore beetle, Stegobium panlceum (L.), pheromone was identified as 2,3-dihydro-2,3,5-trimethyl-6-(l-methyl-2-oxo-butyl)-4H-pyran-4-one (XIV) (44) and the cigarette beetle, Lasloderma serrlcorne F., as 4,6-dimethyl-7-hydroxy-nonan-3-one (XV) (45). The similarity of these structures is worth noting. 

Strong protic acids will also cleave benzyl ethers. A highly stereoselective synthesis of the sex pheromone of the drugstore beetle Stegobium paniceum by Matteson and co-workers277 conveniently accomplished the debenzylation of the benzyl ether 151.1 with methanesulfonic add in chloroform [Scheme 4.151]. 

Slegohlmirte (2S,3S,5R)- Trimethyl-6-(l- methyl-2-oxo- propyl)-2,3- clihydrapyran-4- one Drugstore beetle (Slegobiiim paitic-eum) Fs Organoborane chemistry Titanium(IV) chloride -Sharpless asymmetric epoxidation [150] [160]"... 

Scientists at Fuji Flavor Co. synthesized stegobiene (74), which showed pheromone activity and could be used commercially to monitor the population of the drugstore beetle. 

Drugstore beetle (Stegobium paniceum) is a serious pest of a wide variety of commodities and stored products. In 1978 Y. Kuwahara et al. proposed the structure of stegobinone, the major and crystalline component of the female-produced sex pheromone of 5. paniceum, as 114 (Figure 4.69). Nothing was... 

Drugstore boetfo Sfe oi)/u/n paniceum) Western pine beetle [Oandroctonus brevicami ... 

The pheromone components of C. lugubris and C. hemipterus are undoubtedly related bios3mthetically. Although none of these compounds had been known prior to the nitidulid research, the 13-carbon pheromone component 1 of C. hemipterus has the same carbon skeleton as the pheromone of the drugstore beetle, Stegobium paniceum (14). A polyketide origin of this pheromone was proposed, in which the polyketide arose from the condensation of one acetate and four propionate units (L5). Polyketide biosyntheses have also been proposed for a number of related structures (16, 17). The... 

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