Aggregation arrestant pheromone of the German cockroach,Blattella germanica (L.) (Dictyoptera: Blattellidae): Isolation and structure elucidation of blattellastanoside-A and -B

The aggregation pheromone of the German cockroach,Blattella germanica, consists of attractant and arrestant, which can be detected by olfactometer and choice-chamber assay, respectively. Both were extracted from the frass-contaminated filter paper being used as a shelter. They were separated by solvent partition withn-butanol and water. The arrestant from then-butanol phase was purified by open column chromatography and then successive HPLC isolated two major arrestant components. Spectral evidence from SI-MS, HR-EI-MS, and NMR experiments with pulse techniques provided possible structures as 1-(6-chloro-4,5-epoxy-5-stigmast-3-yl)--d-glucopyranoside and 1-(6-chloro-5-hydroxy-5-stigmast-3-yl)--d-glu-copyranoside, denoted as blattellastanoside-A and blattellastanoside-B, respectively. They represented arrestant activity as median effective doses (ED₅₀) at 0.044 (A) and 3.2 (B) nmol on 1.0 cm² of Whatman No. 1 filter paper.     

2-Methylthiazolidine and 4-ethylguaiacol,male sex pheromone components of the cockroachNauphoeta cinerea (dictyoptera,blaberidae): A reinvestigation

InNauphoeta cinerea, male calling behavior is associated with sex pheromone release by the sternal glands. The male pheromone that attracts females from a distance is a mixture of 2-methylthiazolidine and 4-ethylguaiacol. It is active at very low concentrations, 0.05 and 0.01 ng, respectively. Two other compounds, 3-hydroxy-2-butanone and 2-methyl-2thiazoline, act at close range, keeping the female in the vicinity of the male. The function of the volatile pheromone and those of previously described contact pheromones are discussed in regard to their possible involvement in the establishment of male dominant-subordinate relationships.     

Male sex pheromone of cockroachEurycotis floridana (walker) (Blattidae,Polyzosteriinae): Role and composition of tergites 2 and 8 secretions

InEurycotis floridana, the male calling behavior is associated with the exposition of epidermal glands located under tergites 2, 7, and 8. 4-Hydroxy-5-methyl-3(2H)-furanone and 4-hydroxy-2,5-dimethyl-3(2H)-furanone were recently identified as the specific components of tergite 7 secretion. Methylene chloride extracts of tergite 7 and its major compound 4-hydroxy-5-methyl-3(2H)-furanone attract the conspecific females at a distance. Methylene chloride extracts of tergite 8 are also attractive at a distance to the females, whereas extracts of tergite 2 had no effect on males and females. Our GC investigations showed the absence of specific compounds in tergite 2 secretions. The GC-MS analyses revealed that the male secretion of the gland under tergite 8 is mainly a mixture of (2R*, 3R*)-butanediol, 1-dodecanol and benzyl 2-hydroxybenzoate. These compounds were tested at different concentrations on their own, or as a mixture. Only (2R*, 3R*)-butanediol and 1-dodecanol were attractive for the females. Their functions, as components of the male sex pheromone, in addition with the two derivatives of the furanone are discussed.     

Defensive secretion of Therea petiveriana: chemical identification and evidence of an alarm function

The volatile constituents of the supposed defensive secretions of the glandular pouches of the adults of both sexes of the cockroach Therea petiveriana have been shown to contain N-3-methylbutylacetamide (MBA) and N-3-methylbutylpropanamide (MBP), which represented 60% of the volatile fraction. The other 40% included acidic, aromatic, and aldehydic compounds. Behavioral experiments demonstrated that the secretion acts as an alarm pheromone for adults.     

Isolation and identification of 4,6,8-trimethyl-7,9-undecadien-5-ol,a female-specific compound,in tergal gland secretion ofCryptocercus punctulatus scudder (Dictyoptera: Cryptocercidae)

The secretion of the tergal glands ofCryptocercus punctulatus consists of a complex mixture of 27 compounds. Of this mixture, only one compound (compound B) is specific for females. By dissecting 200 tergal glands, 50 g of pure compound B was collected by preparative GC; it was identified as (Z, E-4,6,8-trimethyl-7,9-undecadien-5-oI. Its functions as well as its absolute configuration still have to be determined.     

A new component of the female sex pheromone ofBlattella germanica (L.) (Dictyoptera: Blattellidae) and interaction with other pheromone components

A fourth component, 3,11-dimethyi-2-heptacosanone, was identified as a cuticular contact sex pheromone of the female German cockroach,Blattella germanica. In behavioral assays, higher dosages of 3,11-dimethyl-2-heptacosanone were needed to elicit similar sexual responses in males to those elicited by the major pheromone component, 3,11-dimethyl-2-nonacosanone. A 1585 blend of the C₂₇ and C₂₉ methyl ketone homologs resulted in a dose-response curve intermediate between that of each of the components alone, indicating independence of activity of each component and lack of synergism. Moreover, the activity of 3,11-dimethyl-2-nonacosanone was not enhanced by female cuticular hydrocarbons. The relationship between sexual responses of males to females and to isolated female antennae, and the amount of cuticular pheromone on whole females was investigated. Cuticular sex pheromone found on females increased with the age of the female, as did the male response to whole females. However, a bimodal male response was elicited by isolated female antennae. Differences between behavioral and analytical assays of pheromone are discussed.     

The Male Abdominal Glands of <Emphasis Type="Italic">Leucophaea maderae</Emphasis>: Chemical Identification of the Volatile Secretion and Sex Pheromone Function

In Leucophaea maderae, male calling behavior involves the release of a sex pheromone from the abdominal sternal glands. An extract of sternal glands attracted conspecific females over a distance. The compounds present were identified as hydroxy-3-butan-2-one, (2R, 3R)-butanediol, senecioic acid, and (E)-2-octenoic acid. The same components are also present in male tergal glands. The identified compounds were tested on their own and in mixtures. Their biological function is discussed.     

Aggregation of larvae ofBlattella germanica (L.) by lactic acid present in excreta

Lactic acid has been identified in extracts of filter paper conditioned by the German cockroach,Blattella germanica (L.). One-to two-week old larvae aggregated on filter paper wetted with solutions of lactic acid.     

Seducin,male sex pheromone of the cockroachNauphoeta cinerea: Isolation,identification, and bioassay

The male sex pheromone of the cockroachNauphoeta cinerea was isolated from adult sternal glands and identified by gas chromatography-mass spectrometry. This pheromone, which attracts females from a distance, is a multicomponent blend. It is composed principally of three compounds: 3-hydroxy-2-butanone (acetoin), 2-methylthiazolidine, and 4-ethyl-2-meth-oxyphenol. A mixture of synthetic compounds in a ratio of 441 (2700 ng) elicits maximal response and short latency of response by receptive females, similar to that induced by male sternal gland extracts. Tested separately, each compound induces a positive response, but the moving times spent by females are generally longer than with the mixture or extracts. These three volatile compounds also are found in small amounts (about 1/40 of sternal glands) in tergal gland secretions licked by females. Acetoin also is found in the sternal and tergal glands of two closely related speciesLeucophaea maderae andHenschoutedenia flexivitta. The biological relationship of each compound and pheromone blend to behavioral response is discussed.     

Tergal glands of male and femaleCryptocercus punctulatus scudder (Dictyoptera: Cryptocercidae): Composition,sexual dimorphism,and geographic variation of secretion

Males and females ofCryptocercus punctulatus possess tergal glands, but they differ in position, size, morphology, and secretion chemistry. Compound A (linalyl acetate) is the most abundant of the 21 compounds found only in the secretion of these glands. Compound B, 4,6,8-trimethyl-7,9-undecadien-5-ol, is specific to the tergal secretion of females.C. punctulatus lives only in the United States; its distribution is disjunct. Compound A is found in samples from the eastern population but is absent in samples from the western population. The amount of compound B per gland in samples from the western population is at least twice as high as in the samples from the eastern populations.