Cigarette beetle

Scheme 32 summarizes Matteson s synthesis of serricornin [(4S,6S,7S)-21], the female sex pheromone of the cigarette beetle (Lasioderma serricorne) via boronic esters [55]. Due to the highly stereoselective nature of boronic ester chemistry, this synthesis of 21 was quite efficient. 

Scheme 60 shows Oppolzer s synthesis of (2S,3R,rS,2 S)-serricorole (42), the female-produced sex pheromone components of the cigarette beetle (Lasio-... 

Howe, R.W. 1957. A laboratory study of the cigarette beetle, Lasioderma serricorne (F.) (Col., Anobiidae), with a critical review of the literature on its biology. Bull. Entomol. Res. 48, 9-56. 

Pierce, L.H. 1994. Using pheromones for location and suppression of phycitid moths and cigarette beetles in Hawaii A five year summary. In Proceedings of the 6th International Working Conference on Stored-Product Protection (E. Highley, EJ. Wright, HJ. Banks, and B.R. Champ, eds), Vol. 1, pp. 439—443. CAB, Wallingford, Australia. 

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. 

Additional compounds found in the pheromone gland of female cigarette beetles are (2S,3R,l R)-2,3-dihyro-2-ethyl-3,5-dimethyl-6-(r-methyl-2 -oxo-butyl)-4ff-pyran-4-one 121 (P-serricorone), its (rs)-epimer (a-serricorone), and its reduction product, serricorole, 122 which shows (l/S,2/S)-configuration [245-247]. These compounds showed only weak attractivity [245], however, they obviously act as oviposition deterrents [248,249]. 

Qualitative screening procedures were used to test toxins as sole carbon sources for growth of the cigarette beetle symbionts. 

Thus, the 1-naphthyl acetate activity from the cigarette beetle yeast does have properties, especially the solvent stability, that are likely to promote use for decontamination of lipophilic toxins. In addition, this activity (and in some cases additional molecular forms detected by gel electrophoresis) can be stimulated (based on higher activity relative to solvent controls) by malathion,... 

The cigarette beetle symbiont has many desirable properties for use in decontamination. As indicated earlier, it has a broad-spectrum... 

The sex pheromone of the female cigarette beetle Lasioderma serricome), commonly known as serricornin has been synthesized in seven steps from readily available racemic 1,4-diaoxa-8-thiaspirO [4.5]decane-6-... 

In an elegant asymmetric synthesis of natural serricornin (148) by Mori et al.164), an overall enantioselective alkylation of diethyl ketone via its SAMP-hydrazone (144) was again the key step. (148) is the sex pheromone of the female cigarette beetle,... 

Chuman, T., Kohno, M., Kato, K. and Noguchi, M. (1979). 4,6-Dimethyl-7-hydroxynonan-3-one, a sex pheromone of the cigarette beetle (Lasioderma serricorneF.). Tetrahedron Letters 20 2361-2364. 

Chuman T., Mockizuki K., Kato K., Ono M. and Okubo A. (1983) Serricorone and serricorole, new sex pheromone components of the cigarette beetle. Agric. Biol. Chem. 47, 1413-1415. 

Baker, J.E., Sukkestad, D.R., Nelson, D. R. and Fatland, C.L. (1979). Cuticular lipids of larvae and adults of the cigarette beetle, Lasioderma serricorne. Insect Biochem., 9, 603-611. 

Humans are not the only creatures with a sense of smell. We can find mates using our eyes alone (though smell does play a part) but insects cannot do this. They are small in a crowded world and they find others of their own species and the opposite sex by smell. Most insects produce volatile compounds that can be picked up by a potential mate in incredibly weak concentrations. Only 1.5 mg of serricornin, the sex pheromone of the cigarette beetle, could be isolated from 65000 female beetles—so there isn t much in each beetle. Nevertheless, the slightest whiff of it causes the males to gather and attempt frenzied copulation,... 

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. 

Methoprene, a juvenile hormone analog, is structurally similar to insect juvenile hormones (Figure 4.11) such as juvenile hormone III. It is used for control of mosquitoes (floodwater mosquitoes, 2-4 instars), cigarette beetles, horn flies, fungus gnats (on mushroom), fleas, etc. The oral LD50 for methoprene in rats is >34,600 mg/kg. 

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