Cockroaches pheromone components

Methylthiazolidine and 4-ethylguaiacol, male sex pheromone components of the cockroach Nauphoeta cinerea (Dictyoptera, Blaberidae) a reinvestigation. Journal of Chemical Ecology 18 2261-2276. 

Figure 10.1 Metabolic pathways for the biosynthesis of 3,11-dimethylnonacosan-2-one and related sex pheromone components of the female contact sex pheromone of the German cockroach, Blattella germanica.

Sirugue D., Bonnard O., Le Quere J. L., Farine J.-P. and Brossut R. (1992) 2-Methylthiazolidine and 4-ethylguaiacol, male sex pheromone components of the cockroach Nauphoeta cinerea (Dictyoptera, Blaberidae) a reinvestigation../. Chem. Ecol. 18, 2261-2276. 

For the preparation of the second component 421 of the cockroach pheromone Burgsthaler et al. 228) also used a Wittig reaction. Lithium acetylide is alkylated with the two halides 414 and 416 and the resulting alkynyl bromide 417 converted into the phosphonium salt. Olefination of the corresponding ylide with 9-bromo-2-nonanone 418 gives a (Z)/( )-mixture of olefin 419 which is converted into the pheromone 3,ll-dimethyl-29-hydroxynonacosan-2-one 421 by aeetoaeetate synthesis, hydrogenation, hydrolysis, and decarboxylation 228) (Scheme 73). 

Males of the scarab beede Amphimatton solstitialis are attracted to the pheromone (/ )-3-hydro.xy-2-butanone (A62), released by both males and females.368 Although the ( -enantiomer and 2,3-butanediol (A4) are also produced, they were not active in the field. 3-Hydroxy-2-butanone of unknown enantiomeric composition is the major sex pheromone component of male cockroach Leucophaea mademe2m The rhinoceros beetle Scapanes australis uses a 84 12 4 mixture of 2-butanol (A61) (R/S 67 33), 3-hydroxy-2-butanone (A62), and 2,3-butanediol (A4, RJl/S,S/meso 43 17 40), whereas the pheromone of another rhinoceros beetle Strategus aloeus is a 95.5 4.0 0.5 mixture of2-butanone (A63), 3-pentanone (A66), and 1-methylpropyl acetate (A64). As mixtures of all components of the natural secretion were used in this study, it is not clear whether all compounds really possess pheromonal activity.369... 

Figure 3 Structures of the sex pheromone components of the German cockroach Blattella germanica and related compounds.

Figure 4.54 Summary of the 7 978 synthesis of the pheromone components of the German cockroach...

Much of the communication between insects involves chemical messengers called pheromones A species of cockroach secretes a substance from its mandibular glands that alerts other cockroaches to its presence and causes them to congregate One of the principal components of this aggregation pheromone is the alkane shown in the bond line formula that follows Give the molecular formula of this substance and represent it by a condensed formula... 

In the Madera cockroach, Leucophaea maderae, male calling behavior involves the release of a sex pheromone from the abdominal sternal glands. The extracts of sternal glands attracted conspecific females over a distance and the compounds responsible were identified as hydroxy-3-butan-2-one, (27 , 37 )-butanediol, senecioic acid and ( )-2-octenoic acid. The same components are also present in the male tergal glands. 

In addition to mating-disruption pheromones, there are a number of naturally occurring, nonpheromonal attractants and repellents. Many are typically used as food additives or in cosmetics or perfumes, and are derived from diverse plant and animal sources. Capsaicin [44], the spicy component of chili peppers, is used in several bird, deer, and rodent repellents. Maple lactone [45], a common food additive and flavoring, is used in traps to attract cockroaches with its stale beer odor. Methyl... 

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