Stegobium Research Articles

Phylogenetic position of yeastlike endosymbionts of anobiid beetles.

The Anobiid beetles Stegobium paniceum and Lasioderma serricorne possess the intracellular yeastlike symbionts Symbiotaphrina buchneri and Symbiotaphrina kochii, respectively, in the mycetome between the foregut and midgut. The nucleotide sequences of the small-subunit rRNA-encoding genes of the symbionts were determined for phylogenetic analysis. Five group I introns were found in the small-subunit rRNA-encoding genes of S. buchneri, but S. kochii lacked introns. The phylogenetic position of both symbionts was close to the class Discomycetes, which is a paraphyletic group. The two symbionts formed a monophyletic group distinct from the other major lineages. Both appear to have parted from other filamentous fungi during the early radiation of the euascomycetes and to have later become obligatory partners of the beetles.

Electrophoretic Karyotype of Intracellular Yeast-like Symbiotes in Rice Planthoppers and Anobiid Beetles

Chromosomal DNA molecules of intracellular yeast-like symbiotes (YLS) of three species of rice planthoppers and two species of anobiid beetles have been separated by pulsed-field gel electrophoresis. Probable chromosome numbers of Nilaparvata lugens, Sogatella furcifera, and Laodelphax striatellus, were 4, 4, and 5, respectively, and tentative genome sizes were 17.3, 17.6, and 20.1 Mbp, respectively, based upon migration of individual chromosome-sized DNA relative to the size standards of Schizosaccharomyces pombe, Hansenula wingei, and Saccharomyces cerevisiae chromosomes. Chromosome numbers of Lasioderma serricorne and Stegobium paniceum were 11 and 15, respectively, and total genome sizes were 20.9 and 15.1 Mbp, respectively. The chromosomes carrying ribosomal RNA genes were identified by Southern blot analysis. Chromosomal organization and the genome size of YLS were similar to those of nonsymbiotic yeasts and fungi.

High-precision asymmetric synthesis of stegobiol and stegobinone via boronic esters

Highly stereoselective boronic ester chemistry has been used to synthesize the drugstore beetle pheromones stegobiol and stegobinone. The convergent route utilizes a single intermediate, 2-(3-benzyloxy-1-chloro-2-methylpentyl)-4,5-dicyclohexyl-1,3,2-dioxaborolane, containing all of the stereogenic centers for both segments of the pheromones, 3-benzyloxy-2-methylpentanal and 5-(t-butyldimethylsiloxy)-4-methylhexan-4-one, requires only one chromatographic separation, and is the first synthesis to provide pure, crystalline samples

Evaluation of prallethrin aerosol to control stored product insect pests

Three aerosol formulations containing either 0.75, 1.00 or 1.50% prallethrin as the active ingredient were tested on seven common stored product insect pest species. Application at 0.2 g AI per 28.3 m3 killed all adult Cadra cautella (Walker) and Plodia interpunctella (Hübner), and at least 99% of the adult Oryzaephilus surinamensis (L.), Trogoderma variabile (Ballion) and Tribolium castaneum (Herbst). An application rate of 0.3 g AI per 28.3 m3 killed at least 90% of the adult Stegobium paniceum (L.). An application rate of 0.5 g AI per 28.3 m3 killed approx. 93% of adult Tribolium confusum (Duv.) and approx. 73% of Attagenus megatoma (F.) larvae. All insects still alive when final mortality assessments were made were knocked down. All T. confusum that survived a single application at 0.5 g were killed by a second application 1, 2 or 3 days later.

The effects of low oxygen atmospheres on museum pests

AbstractLaboratory cultures of a number of common museum pests including Tineola bisselliella (Hummel), Lasioderma serricorne (Fabricus), Stegobium paniceum (Linnaeus) and Anthrenus vorax (Linnaeus), were exposed to low oxygen atmospheres (0·4% oxygen, balance nitrogen) at 30°C for three weeks. Complete mortality was observed for all developmental stages. The possible application of low oxygen atmospheres as an alternative to conventional chemical fumigation techniques is discussed in terms of these experimental trials.

The Control of Insect Pests in Museum Collections: The Effects of Low Temperature on Stegobium paniceum (Linneaus), the Drugstore Beetle

The Control of Insect Pests in Museum Collections: The Effects of Low Temperature on Stegobium paniceum (Linneaus), the Drugstore Beetle

The Control of Insect Pests in Museum Collections: The Effects of Low Temperature on Stegobium Paniceum (Linneaus), the Drugstore Beetle

AbstractThe effect of time on mortality of various developmental stages of Stegobium paniceum (Linneaus) at −20°C was studied. Eggs, larvae, pupae and adult insects were collected and exposed to −20°C for 0–4 hours. Complete mortality was observed for all developmental stages after 1- hour exposure. The use of low temperatures as an alternative to conventional fumigation techniques for the treatment of insect-infested museum objects is discussed in terms of the results of these experimental trials.

Synthesis of 1′-Epi-stegobinone

1′-Epi-stegobinone [(2S,3R,1′S)-2,3-dihydro-2,3,5-trimethyl-6-(1′-methyl-2′-oxobutyl)-4H-pyran-4-one], an inhibitor of stegobinone, which is the sex pheromone of drugstore beetle (Stegobium paniceum L.), was synthesized by stereocontrol at C-2 and C-1′ starting from ethyl (R)-3-hydroxybutanoate and methyl (R)-3-hydroxypentanoate.

Synthesis of 1'-epi-stegobinone.

1′-Epi-stegobinone [(2S,3R,1′S)-2,3-dihydro-2,3,5-trimethyl-6-(1′-methyl-2′-oxobutyl)-4H-pyran-4-one], an inhibitor of stegobinone, which is the sex pheromone of drugstore beetle (Stegobium paniceum L.), was synthesized by stereocontrol at C-2 and C-1′ starting from ethyl (R)-3-hydroxybutanoate and methyl (R)-3-hydroxypentanoate.

Conformational Analyses of Stegobinone and 1'-Epi-stegobinone

Conformatial analyses of stegobinone,the sex pheromone of the drugstore beetle,and l'-epi-stegobinone were performed by the combination of detail NOE measurements and molecular mechanics calculations.

Inert atmosphere fumigation of museum objects

The use of inert atmospheres (low oxygen) as an alternative to conventional fumigation techniques was investigated. Mixed cultures of several common museum pests including Tineola bisselliella, Lasioderma serricorne, Stegobium paniceum, Anthrenus vorax and Lyctus brunneus were purged with nitrogen gas for one, two and three weeks under controlled environmental conditions. One hundred percent mortality was observed in all cases though further quantitative tests are required to establish statistically valid mortality rates.

Inhibition of male response of drugstore beetles to stegobinone by its isomer

Stegobinone, (2S, 3R, 1'R)-2,3,-dihy dro-2,3,5-trimethyl-6-(1'-methyl-2'-oxobutyl)-4H-pyran-4-one, the sex pheromone of drugstore beetles (Stegobium paniceum L.), elicited the pheromonal response from the males of the species in our bioassay system; however, the synthesized diastereomeric mixture of this compound was actually inactive to the males. Although the stegobinone isolated from the beetles of this species had significant activity, its enantiomeric [(±)-2S,3R,1'S-] and diatereomeric [(±)-2S,3S,1'RS-] isomers were inactive. Adding the (±)-2S,3R,1'S isomer to stegobinone significantly reduced the male response. Furthermore, the activity of Stegobinone vanished on keeping it at room temperature for two weeks. In such a stored stegobinone sample, the presence of 2S,3R,1'S isomer, the inhibitory component, was confirmed. This isomer might be produced by C-1' epimerization during storage.

Female sex pheromone of the common furniture beetleAnobium punctatum (Coleoptera: Anobiidae): Extraction, identification, and bioassays

Observations and reports on the common furniture beetleAnobium punctatum suggested that, on emergence, females use a sex pheromone to attract males. GLC analysis of ovipositor extracts showed the presence of a single component, which was found to be active by EAG and coupled GLC-EAG techniques, and to attract males in both walking and flying assays. The pheromone was identified by GC-MS as 2,3-dihydro-2,3,5-trimethyl-6-(1-methyl-2-oxobutyl)-4H-pyran-4-one (stegobinone), which is the sex pheromone of another anobiid, the drugstore beetle,Stegobium paniceum. MaleA. punctatum responded equally to ovipositor extracts of either species, at both the sensory (EAG) and behavioral levels, which poses the question as to how species specificity in mate attraction is achieved.

Survey of Stored-product and Other Economic Pests in Import Warehouses in Los Angeles1

Eighteen Los Angeles warehouses specializing in imported foods were surveyed for infestations of insects and other pests. A total of 42 species of insects, mites, birds, and rodents was found. Thirty-two were species of stored-product insects and mites found in 19 different types of food products from 11 of the warehouses. Other sites where insect pests were found included food-manufacturing machinery, packing rooms, static material, window sills, shelves, and rodent bait stations. Insects were also collected flying or crawling about. Stored-product insects most frequently found were Tribolium castaneum (Herbst), Lasioderma serricorne (F.), Oryzaephilus surinamensis (L.), Plodia interpunctella (Hübner), Trogoderma variabile Ballion, O. mercator (Fauvel), Stegobium paniceum (L.), Rhyzopertha dominica (F.),Cadra cautella (Walker), Blattella germanica (L.), Periplaneta Americana (L.), Ahasverus advena (Waltl), Sitophilus oryzae (L.), and S. zeamais Motschulsky. All are common pests in California. Two pests not known to occur in California, Lardoglyphus angelinae Olsen and Cryptolestes turcicus Grouvelle, were intercepted in sealed packages of food.

ChemInform Abstract: Pheromone Synthesis. Part 87. Synthesis of (2S,3R,1′R)‐Stegobinone. The Pheromone of the Drugstore Beetle, with Stereocontrol at C‐2 and C‐1′.

AbstractThe title compound (V) is prepared from the reaction of the acid (I) with the hydroxy ketone (II) as shown in the scheme.

シバンムシアリガタバチの防除に関する研究 : I. ジンサンシバンムシの殺虫剤感受性

シバンムシアリガタバチの防除に関する研究 : I. ジンサンシバンムシの殺虫剤感受性

Mating behaviour and the mechanism of male orientation in the anobiid bread beetle, Stegobium paniceum

ABSTRACT. An analysis of over 200 encounters between male and female Stegobium paniceum (L.) permitted identification of the main units of behaviour. Experiments showed that the orientation of the male with respect to the female consists of two components: pre‐mounting and post‐mounting. It is suggested that the female actively participates in directing the pre‐mounting component. In the post‐mounting component, however, the male appears to rely primarily on tactile cues which may be associated with the female dorsal setae.

Synthesis of ( 2s, 3r, 7rs)-stegobinone [2,3-dihydro-2,3,5-trimethyl-6-(1-methyl-2- oxobutyl)-4h-pyran-4-one] and its ( 2r, 3s, 7rs)-isomer : The pheromone of the drugstore beetle

Reaction of acetaldehyde with the trianion of 4,6-dimethylnonane-3,5,7-trione followed by acidification yielded a stereoisomeric mixture of stegobinone, the pheromone of Stegobium paniceum L. Acylation of the dianion derived from 4-methylheptane-3,5-dione with a mixed anhydride prepared from (2R, 3S)-3-hydroxy-2-methylbutanoic acid or its enantiomer led to (2S,3R,7RS)- or (2R, 3S, 7RS)-stegobinone. The natural pheromone possesses (2S,3R)-stereochemistry.

Post‐mating changes in the behaviour and activity of the female anobiid bread beetle, Stegobium paniceum

ABSTRACT. In an investigation of the effect of mating on the behaviour and activity of female Stegobium paniceum (L.) the following factors were examined: initiation of oviposition, amount of walking activity, refractory behaviour, and tendency to fly. 2–3 min in copula were sufficient to induce initiation of oviposition, increase the amount of walking activity and produce refractory behaviour. Mating was also shown to increase the occurrence of female flight behaviour. The number of females flying increased after oviposition had started and decreased when oviposition was complete. The greatest behavioural changes were found in females allowed to separate from males in their own time after a mean period in copula of 63 min. The significance of these changes and possible causative stimuli are discussed.

Rasterelektronenmikroskopische Untersuchungen an von Vorratsschädlingen angegriffenen Verpackungsfolien aus synthetischen Kunststoffen und abgewandelten Naturstoffen

Packaging foils made of cellulose actetate, cellophane, polyethylene, polypropylene, polystyrene, polyester, polyvinyl chloride, attacked byRhizopertha dominica F.,Stegobium paniceum L.,Tribolium castaneum Hbst. and larvae ofPlodia interpunctella Hbn. were examined with the scanning electron microscope (SEM).