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International audience; Males and females of Cryptocercus 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.

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 15∶85 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.

Males and females ofBlatta orientalis produce a volatile sex pheromone attractive at a distance. The male initiates courtship behavior by adopting a calling posture while emitting his sex pheromone. He exposes the anterior region of his tergites by stretching his abdomen horizontally. Morphological observations show the existence of male tergal glands on the anterior region of tergites 1 to 8. Behavioral assays of females utilizing methylene chloride extracts of various male body parts reveal that extracts of the anterior region of tergites are highly attractive and induce more positive responses that any other body part. Once near the male, the attracted female opens widely her genital atrium thus exposing her atrial glands. Behavioral assays reveal that these atrial glands are certainly the site of production of the female sex pheromone.

Two- to 12-day-old larvae ofBlattella germanica are repelled by certain volatile fatty acids present in the frass. Propionic, isovaleric, and valeric acids are strongly repellent, isobutyric acid is slightly repellent, and acetic and butyric acids are without effect. These results are discussed in relation to control of population density.

In the sequential courtship behavior of the German cockroach, Blattella germanica (Dictyoptera: Blattellidae), females feed on the tergal gland secretions from the male tergites. The phagostimulative components in the male secretions were composed of a complex mixture of oligosaccharides and phospholipids. Besides seven oligosaccharides previously identified, two new trisaccharides, O-α-D-glucopyranosyl-(1→6)-α-D-glucopyranosyl α-D-glucopyranoside and O-α-glucopyranosyl-(1→4)-O-α-glucopyranosyl- (1→1)-myo-inositol, were characterized as the sugar components of the secretions. The activity of the sugar components was compared in combination with the lipid fraction. Individual oligosaccharides exhibited the activity either alone or synergistically with the phospholipids. A complex mixture of these primary substances in the tergal gland secretions, thus, serves as a pheromonal phagostimulant in the precopulatory behavior, strongly eliciting feeding response in the female cockroach.

(3S,11S)-3,11-Dimethylnonacosan-2-one is a major component of the courtship stimulating, contact sex pheromone of the female German cockroach. Although the four synthetic stereoisomers of this compound have been tested in behavioral assays, their relative activity remains unresolved. Using isolated male antennae dosed with synthetic test compounds to assay male behavior, we found that at high doses all four stereoisomers elicited responses from 100% of the males. However, at physiologically relevant doses similar to those found on the female antenna, the (3S,11S)-isomer was the least effective of the four stereoisomers at eliciting courtship responses in males. This is the first example of a natural stereoisomer having less bioactivity than related stereoisomers that do not occur naturally. Another component of the sex pheromone blend, 3,11-dimethylheptacosan-2-one, was previously purified from the female's epicuticule and behaviorally assayed, but its activity was not confirmed through synthesis. We now confirm that synthetic (3S,11S)-3,11-dimethylheptacosan-2-one elicits behavioral responses, but less so than its C29 homolog.

Male cockroaches of the genus Blattella secrete courtshippheromones from abdominal tergal glands. Conspecific females mount courting males and feed on their tergal exudates. In the German cockroach, B. germanica, a complex mixture of oligosaccharides was previously identified as the major phagostimulants in the male tergal secretion. We compared the oligosaccharide compositions of three Blattella species from different habitats, B. germanica (house), B. lituricollis (field), and B.nipponica (forest), by gas chromatographic (GC) analysis of their trifluoroacetylated derivatives. The three possessed a series of maltooligosaccharides and oligoglucosyl trehaloses with α1→4 and α1→1 linkages in common. However, B. germanica was conspicuous for its accumulation of a oligoglucosyl trehalose with a α 1→6 linkage [O-α-D-glucopyranosyl-(1→6)-α-D-glucopyranosyl α-D-glucopyranoside] as the most prominent component of the secretion. Such diversification of the male pheromonal compositions within the genus might be reflected by biosynthetic systems in males and chemosensory properties in females suited for their natural habitat.

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.

Interactions between male Nauphoeta cinerea cockroaches are characterized by an elaborate ritual that leads to a stable dominant–subordinate hierarchy between two individuals. Chemical signals involving volatile sex pheromones and cuticular hydrocarbons play an important role in establishing and maintaining dominance status. The present study was performed to identify cuticular hydrocarbons in two- and three-times dominant or subordinate individuals obtained by forcing dyadic encounters. Two methods, i.e., solid-phase microextraction (SPME) and organic solvent extraction, were used to isolate cuticular hydrocarbons. A total of 23 peaks of cuticular hydrocarbons were identified. Analysis showed quantitative differences in hydrocarbon profiles of three-times dominant and subordinate individuals according to extraction method and dominance status. Dominant individuals were characterized by higher proportions of the monomethylalkanes 11- and 13-MeC36, 13- and 15-MeC38, and 11-, 13-, and 15-MeC35, while subordinate individuals had higher proportions of the following monomethylalkanes: 7-, 9-, and 11-MeC31, 5-MeC31, 3- and 8-MeC32, and 9-, 10- , 11-, and 12-MeC32. Discussion focuses on the reliability of hydrocarbons as indicators of dominance status and on their correlation with physiological processes.

Hydrocarbons (HC) are the most important waterproofing barrier on the cuticle of most terrestrial insects. Yet, the relationships among the type, amount, biophysical properties, and water retardation capacity of constituent HC are poorly understood. Melting temperatures and gas chromatographic profiles of HC of German cockroach tissues of various ages and stages were compared. The melting temperature (Tm) of oothecal HC was highest, Tm of epicuticular HC was substantially lower, and that of hemolymph HC was lowest. The epicuticular HC of older nymphs and adults had higher Tm than HC of the same sex and stage soon after the molt. The HC of females had higher Tm than did male HC. Principal components analysis suggested that normal and 3and 5-methylalkanes, which were more prevalent on the epicuticle, were associated with higher Tm, implicating these components of the HC blend in waterproofing roles. The cockroach ootheca is particularly well protected by an abundance of n-alkanes and its external HC exhibit the highest Tm of any HC blend. The methyl ketone sex pheromone components, which are derived from HC, appear to only slightly reduce the Tm of the epicuticular HC, probably because the methyl ketones represent only 1.12% of the mass of epicuticular HC. We suggest that the evolution of polar epicuticular chemical signals may be constrained by their tendency to increase water transpiration.

0098-0331 (Print) Comparative Study Journal Article; 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 behavior and reduced locomotory activity in the German cockroach is known to be caused by chemical compounds in the feces. The attractive and/or arrestant efficacy of three relevant substances was tested in first instars by a two-choice aggregation test and in adults with a locomotion compensator apparatus that allows quantification of taste-directed orientation and walking speed as a function of antennal stimulation. The three substances tested were a feces crude extract; a mixture of six carboxylic acids (mix G) out of a total of 29 that were identified in the feces extract and tested as single compounds and in various combinations; and a steroid glucoside denoted as blattellastanoside A, which has been suggested as an aggregation arrestant pheromone in Blattella germanica. With both of our test methods, feces extract and mix G proved to be very attractive, whereas the effects of blattellastanoside A were, if anything, very poor. Possible reasons for discrepancies are discussed.

We used bioassays to determine the sex pheromone production site in the female American cockroach (Periplaneta americana). Bioassayed extracts from various body parts aroused sexual responses from unmated males. However, the extract of hindgut (including both colon and rectum) induced strong responses. Colon extract stimulated the strongest sexual response. To compare the sex pheromone contents of atrial glands, pygidium, rectum, and colon, we recorded the EAG responses of male antennae to these extracts. Among the four tissues, colon extract caused the strongest EAG response. From gas chromatographic (GC) analysis, the quantities of periplanone-A (PA) and periplanone-B (PB) (the main sex pheromone components in female American cockroach) were 0.34 and 8.31 ng, respectively, in the colon of a virgin female. The ratio of PA to PB was ca. 1:24. The present results are different from those reported in a previous study, in which it was concluded that atrial glands are the sites of sex pheromone production in P. americana, and from GC analysis the quantity of PB was estimated to be 60 ng/female. There was no difference in sexual behaviors induced by colon and atrial glands of calling virgin females. It is unclear whether the colon is the sole sex pheromone source in the female American cockroach.

The biological activities of synthetic periplanone analogs, including four candidates of periplanone-A (P-A), were evaluated by behavioral and electroantennogram (EAG) assays. Among 16 periplanone analogs, six compounds evoked pheromonal activity from the male American cockroaches. The threshold dosages of these biological active analogs were 10-10(5) times lower than that of the known periplanone mimic, germacrene-D. The conformation required for eliciting the pheromonal activity is discussed in terms of the structure-activity relationship of these analogs. Hauptmann's P-A elicited the strongest pheromonal activity among four candidates of P-A in our bioassay, suggesting that Hauptmann's P-A is a natural P-A produced from female cockroaches.

Diploptera punctata, a Pacific islands cockroach, discharges a fine aerosol ofp-benzoquinones from a pair of tracheal glands in response to disturbance or CO2 anesthesia. In addition, the glands and their contents are shed at each molt. We measured the amount ofp-benzoquinones discharged in response to pinching and anesthesia and the filling of glands after discharge and molting. Roaches discharge highly variable amounts of quinones but appear to retain approximately 11% of their lifetime total benzoquinone content after repeated discharges. Roaches rapidly fill their glands after molting (18Μg quinone/day) but after discharging appear to refill at a much slower rate or not at all. This lack of refilling could result from an inability to produce quinones after a finite time period or in excess of a fixed quantity. The delayed accumulation ofp-benzoquinone with respect to the alkylated derivatives in newly molted adults suggests competition for aromatic amino acids between cuticular and defensive quinone synthesis.

Chemically mediated host location in the eulophid parasitoidAprostocetus hagenowii (Ratzeburg) was investigated. In Y-tube bioassays 77.6% of female parasitoids responded to aPeriplaneta americana (L.) ootheca; parasitoids did not respond to air with no volatile stimuli. Frass from adult cockroaches was as attractive as an ootheca. Bioassay of one ootheca equivalent of five lipid fractions (eluted with hexane and 1, 5, 10, and 30% ether in hexane) from silica gel column chromatography indicated that the active component was a hydrocarbon. Further separation and bioassay of oothecal hydrocarbons by AgNO3-impregnated silica gel column chromatography indicated that the biological activity was in one fraction. Gas chromatographic (GC) analysis of this fraction revealed a single peak; this peak was identified by researchers in 1963, 1969, and 1972 as (Z,Z)-6,9-heptacosadiene. Qualitative and quantitative GC analyses of total hydrocarbons from oothecae, frass, and adult females were essentially identical; 6,9-heptacosadiene was the dominant hydrocarbon from each source. The alkadiene was 37 times more abundant in frass than on the ootheca. The volatilization of the alkadiene from oothecae was demonstrated by aeration and trapping on Super Q adsorbent. The current study is the first evidence for biological activity of (Z,Z)-6,9-heptacosadiene, a major hydrocarbon component on adult female American cockroaches, on their oothecae, and in their frass.

The electroantennogram responses of synthetic (−)-periplanone-B (PB) and (−)-periplanone-A (PA) were evaluated by using the antennae of the unmated male American cockroachPeriplaneta americana L. The threshold concentrations of the pheromone activities for the two chemicals were similar. Neither a synergistic nor an inhibitory response was noted, and only an additive effect was detected when PA and PB were applied as a mixture.

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 4∶4∶1 (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.

The attractivity of virgin female odors of the American cockroach was examined in field experiments. Crude extracts of the female odor, the isolated sex pheromone fractions, periplanone-A and periplanone-B, and other compounds obtained during the isolation served as stimulants. An extract of male odors, obtained by identical collection methods, was used as a control. Males ofPeriplaneta americana were attracted by the crude extract and periplanone-B; males of the sympatric species,P. Australasiae, by periplanone-A. Experiments in which these components were presented subsequently and as mixtures indicate that, under certain conditions, periplanone-A may also function as an attracting substance forP. americana males and that periplanone-B and possibly some other components act as an inhibitor for males ofP. australasiae.

Many compounds related to (+)-bornyl acetate (a sex phero-mone mimic of the American cockroach) were synthesized and tested for sex pheromonal activity. All compounds except for esters of (+)- and (-)-borneol were inactive, whereas (+)-bornyl acetate (Ib) and propionate (Ic) showed the activity at 0.05 mg. Although (-)-bornyl propionate (IVc) is the enantiomer of Ic, it exhibited weak activity at 0.5 mg dose. On the basis of the behavioral assay results, important chemical factors in Ib for pheromonal activity were elucidated and are discussed in connection with another mimic, (+)-trans-verbenyl acetate. The M/ F ratio index in EAG was evaluated for both active and inactive compounds. The index demonstrated a good correlation with the behavioral activity.

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.

The structural relationships between the cuticular hydrocarbons and the contact sex pheromone of the female German cockroach,Blattella germanica, were investigated. Cuticular hexane extracts were separated into hydrocarbon and ketone fractions by TLC or silicic acid column chromatography. The ketone fraction (which contains the major contact sex pheromone component) was analyzed by GC-MS before and after reduction to ydrocarbon. In addition to 3,11-dimethyl-2-nonacosanone, 3,11-dimethyl-2-heptacosanone was also identified. Females have the 3,11- and 3,9-dimethyl C27 and C29 alkanes, but only the 3,11- isomer of the dimethylketones. Inddition to the hydrocarbon components previously reported, a number of new components were characterized. Although the ratios of cuticular hydrocarbons differ among nymphs, adult males, and adult females, they have qualitatively identical hydrocarbon profiles, suggesting that the production of the contact sex pheromone results from the sex-specific oxidation of 3,11-imethylalkanes to pheromone components by the female.

Bioassays were performed on malePeriplaneta americana L. using synthetic (−)-periplanone-B (P-B) and Hauptmann's (−)-periplanone-A (P-A), and their mixtures at various ratios to estimate the roles of both periplanones for the sexual communication of the species. Both P-A and P-B elicited qualitatively the same responses, such as antennal movement, rapid locomotion, wing raising, and homosexual behavior of male cockroaches, but the threshold of the pheromone activities for P-B was two orders of magnitude lower than that of P-A. Neither synergistic nor inhibitory but only a simple integrated effect on the responses was observed when mixtures of P-A and P-B were applied.

Female sex pheromones ofPeriplaneta americana, P. australasiae, andBlatta orientalis elicit locomotion and upwind orientation in conspecific males. Interspecific attraction between these species was observed in a wind tunnel assay for most species combinations, with the exception ofP. australasiae males not being attracted toP americana females. The role of twoP. americana sex pheromone components, periplanone-A (PA) and periplanone-B (PB) in male attraction was analyzed. PA induced locomotion in males of all three species, with highest threshold concentration inP. americana. PB was effective inP. americana andB. orientalis, but not inP. australasiae. Experiments with mixtures of both components confirmed an inhibitory influence of PB onP. australasiae males when it was added to PA in a ratio of 3∶1 or higher. SinceP. americana andP. australasiae have been found to be syntopous, and their daily mating periods overlap, the female sex pheromone ofP. americana is discussed as an isolating factor between both species.

The frass of the following omnivorous insects reared on natural and artificial diets was analyzed for volatile fatty acids:Blattella germanica, Acheta domesticus, Blaberus discoidalis. Acetic, propionic, isobutyric, butyric, isovaleric, and valeric acids were identified in all frass samples. The possible significance of volatile fatty acids in frass is discussed.