Qualitative and Quantitative Differences in Herbivore-Induced Plant Volatile Blends from Tomato Plants Infested by Either <Emphasis Type="Italic">Tuta absoluta</Emphasis> or <Emphasis Type="Italic">Bemisia tabaci</Emphasis>

Plants release a variety of volatile organic compounds that play multiple roles in the interactions with other plants and animals. Natural enemies of plant-feeding insects use these volatiles as cues to find their prey or host. Here, we report differences between the volatile blends of tomato plants infested with the whitefly Bemisia tabaci or the tomato borer Tuta absoluta. We compared the volatile emission of: (1) clean tomato plants; (2) tomato plants infested with T. absoluta larvae; and (3) tomato plants infested with B. tabaci adults, nymphs, and eggs. A total of 80 volatiles were recorded of which 10 occurred consistently only in the headspace of T. absoluta-infested plants. Many of the compounds detected in the headspace of the two herbivory treatments were emitted at different rates. Plants damaged by T. absoluta emitted at least 10 times higher levels of many compounds compared to plants damaged by B. tabaci and intact plants. The multivariate separation of T. absoluta-infested plants from those infested with B. tabaci was due largely to the chorismate-derived compounds as well as volatile metabolites of C₁₈-fatty acids and branched chain amino acids that had higher emission rates from T. absoluta-infested plants, whereas the cyclic sesquiterpenes α- and β-copaene, valencene, and aristolochene were emitted at significantly higher levels from B. tabaci-infested plants. Our findings imply that feeding by T. absoluta and B. tabaci induced emission of volatile blends that differ quantitatively and qualitatively, providing a chemical basis for the recently documented behavioral discrimination by two generalist predatory mirid species, natural enemies of T. absoluta and B. tabaci employed in biological control.     

Volatiles Emitted by Calling Males of Burying Beetles and <Emphasis Type="Italic">Ptomascopus morio</Emphasis> (Coleoptera: Silphidae: Nicrophorinae) Are Biogenetically Related

In burying beetles, Nicrophorus spp. (Coleoptera: Silphidae: Nicrophorinae) mate finding is mediated by male produced volatile compounds. To date, pheromone components of only two species have been identified. In an attempt to better understand the evolution of male pheromone signaling in burying beetles, we investigated the male released volatiles of ten Nicrophorus species and one closely related nicrophorine species, Ptomascopus mori. Volatiles emitted by calling males were collected in the laboratory by means of solid phase micro extraction and analyzed using gas chromatography coupled with mass spectrometry. Identified volatiles included short chain esters of 4-methylcarboxylic acids, terpenoids, and some other aliphatic compounds. The long-range volatile signals of the burying beetle species included in this study are blends of two to seven components. We found that methyl or ethyl esters of 4-methylheptanoic acid and 4-methyloctanoic acid are produced by eight of the ten investigated Nicrophorus species. These esters may play a key role in chemical communication. Their widespread occurrence suggests that these compounds did not evolve recently, but appeared relatively early in the phylogeny of the genus. Although Ptomascopus is considered the sister genus of Nicrophorus, P. morio males do not produce any of the Nicrophorus compounds, but release 3-methylalkan-2-ones, which are absent in Nicrophorus. A better understanding of the evolution of burying beetle pheromones, however, will only be possible once more species have been studied.     

Identification of Floral Volatiles and Pollinator Responses in Kiwifruit Cultivars, <Emphasis Type="Italic">Actinidia chinensis</Emphasis> var. <Emphasis Type="Italic">chinensis</Emphasis>

Volatiles emitted from unpollinated in situ flowers were collected from two male cultivars, ‘M33’, ‘M91’, and one female cultivar ‘Zesy002’ (Gold3) of kiwifruit (Actinidia chinensis var. chinensis). The samples were found to contain 48 compounds across the three cultivars with terpenes and straight chain alkenes dominating the headspace. Electrophysiological responses of honey bees (Apis mellifera) and bumble bees (Bombus terrestris) to the headspace of the kiwifruit flowers were recorded. Honey bees consistently responded to 11 floral volatiles from Gold3 pistillate flowers while bumble bees consistently responded to only five compounds from the pistillate flowers. Nonanal, 2-phenylethanol, 4-oxoisophorone and (3E,6E)-α-farnesene from pistillate flowers elicited responses from both bee species. Overall, honey bees were more sensitive to the straight chain hydrocarbons of the kiwifruit flowers than the bumble bees, which represented one of the main differences between the responses of the two bee species. The floral volatiles from staminate flowers of the male cultivars ‘M33’ and ‘M91’ varied greatly from those of the pistillate flowers of the female cultivar Gold3, with most of the bee active compounds significantly different from those in the Gold3 flower headspace. The total floral emissions of ‘M33’ flowers were significantly less than those of the Gold3 flowers, while the total floral emissions of the ‘M91’ flowers were significantly greater than those of the Gold3 flowers.     

Maxima of the Specific Heat at Constant Pressure of the <Emphasis Type="Italic">n</Emphasis>-Alkanes C<Subscript>7</Subscript>-C<Subscript>9</Subscript> in the Supercritical Region

Precision measurements of the specific heat at constant pressure, C _p , of high-purity samples of the normal alkanes C₇-C₉ in the supercritical region of state parameters are carried out using an adiabatic flow calorimeter equipped with a calorimetric flowmeter. Currently, this is the most accurate method. The coordinates of maxima of C _p on isobars are determined. A generalized equation for the line of the maxima of C _p in reduced coordinates π-τ and an equation for C _p along this line in corresponding states for the homologous series are obtained in terms of thermodynamic similarity theory using the most reliable published data. Existing experimental methods for determining the critical parameters of individual substances are analyzed.     

Volatile and Contact Chemical Cues Associated with Host and Mate Recognition Behavior of <Emphasis Type="Italic">Sphenophorus venatus</Emphasis> and <Emphasis Type="Italic">Sphenophorus parvulus</Emphasis> (Coleoptera: Dryophthoridae)

Beetles in the genus Sphenophorus Schönherr, or billbugs, potentially utilize both volatile and non-volatile behavior-modifying chemical signals. These insects are widely distributed across North America, often occurring in multi-species assemblages in grasses. However, details about their host- and mate-finding behavior are poorly understood. This study tested the hypothesis that volatile organic compounds from host-plants and conspecifics direct the dispersal behavior of hunting billbug S. venatus Say. Further, we characterized the cuticular hydrocarbon profiles of two widespread pest species, S. venatus and bluegrass billbug S. parvulus Gyllenhaal, to assess the potential role of contact pheromones in mate-recognition. In Y-tube olfactometer bioassays, S. venatus males were attracted to a combination of conspecifics and Cynodon dactylon host-plant material, as well as C. dactylon plant material alone. S. venatus females were attracted to a combination of male conspecifics and host-plants but were also attracted to male conspecifics alone. Field evaluation of a putative male-produced aggregation pheromone, 2-methyl-4-octanol, identified from two congeners, S. levis Vaurie and S. incurrens Gyllenhaal, did not support the hypothesis that S. venatus and S. parvulus were also attracted to this compound. Gas chromatography-mass spectrometry analysis of S. venatus and S. parvulus whole-body cuticular extracts indicated a series of hydrocarbons with qualitative and quantitative interspecific variation in addition to intraspecific quantitative variation between males and females. This study provides the first evidence that S. venatus orients toward host- and insect-derived volatile organic compounds and substantiates the presence of species-specific cuticular hydrocarbons that could serve as contact pheromones for sympatric Sphenophorus species.     

Impact of Chain Length on the Catalytic Performance in Hydroisomerization of <Emphasis Type="Italic">n</Emphasis>-Alkanes Over Commercial and Alkaline Treated *BEA Zeolites

The present paper highlights the influence of desilication of nanocrystal *BEA zeolites (CP811 and CP814E) by different alkaline treatments in presence of NaOH alone, NaOH?+?TPABr and NaOH?+?TBAOH, on the catalytic performance in the hydroisomerization reactions of n-alkanes (n-C₁₀, n-C₁₂ and n-C₁₄). The well-balanced catalyst was reached after impregnation of 1.5 wt% of Pt, where the activity and isomers selectivity was seen to be the maximum, knowing that the Pt content effect was studied on the CP811 zeolite catalyst. All the other catalysts were after impregnated by approximately 1.5 wt% of Pt. The improvement of the textural properties by means of desilication was not always accounting for the influence of the catalytic performance of the catalysts, but rather it may be the bifunctional characteristics in charge. The impact of chain length was investigated on the catalysts to study if the presence of the inter- and intracrystalline mesopores would account for better diffusion of larger molecules as, n-C₁₂ and n-C₁₄. It was found on the majority of the catalysts that the activity was high whether the chain length was, but the isomers selectivity was decreasing with chain length except on one catalyst that possesses high textural and bifunctional characteristics. Among the three n-alkanes studied, n-C₁₂ have marked the highest TOF values and lowest selectivity to isomers, a phenomenon attributed to the confinement effect that seems to increase the interaction of n-C₁₂ molecules with the acidic sites of the zeolites, apparently causing their strength to be higher. This effect was pronounced more with n-C₁₂ than the other two n-alkanes.

Graphical Abstract

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Crystal structure and thermal expansion of ammonium pentaborate NH<Subscript>4</Subscript>B<Subscript>5</Subscript>O<Subscript>8</Subscript>

Anhydrous ammonium pentaborate NH₄B₅O₈ has been synthesized by thermal dehydration of larderellite NH₄[B₅O₇(OH)₂] · H₂O at a temperature of 290°C for 7 h. The crystal structure has been determined from the X-ray powder diffraction data: a = 7.58667(5) Å, b = 12.00354(8) Å, c = 14.71199(8) Å, R _p = 6.23, R _wp = 7.98, R _B = 12.7, R _F = 8.95, and β-KB₅O₈ structure type. The double interpenetrating framework is formed by pentaborate groups, each consisting of a boron-oxygen tetrahedron and four triangles, in which all oxygen atoms are bridging. The thermal behavior of the NH₄B₅O₈ compound has been investigated using thermal X-ray diffraction. As for other pentaborates of this type, the thermal expansion of the NH₄B₅O₈ compound is anisotropic and reaches a maximum along the a axis. The thermal expansion coefficients are as follows: α _a = 39 × 10^?6, α _b = 6 × 10^?6, α _c = 20 × 10^?6, and α _V = 65 × 10^?6 °C^?1.     

Sexual Isolation and Cuticular Hydrocarbon Differences between <Emphasis Type="Italic">Drosophila santomea</Emphasis> and <Emphasis Type="Italic">Drosophila yakuba</Emphasis>

Drosophila santomea and Drosophila yakuba are two sister species inhabiting Saõ Tomé island. Previous studies showed that both species display strong reproductive isolation, although they can produce a few viable hybrids. Our study tried to understand the mechanism of this ethological isolation between two allopatric strains. A strong sexual isolation was confirmed, with a marked asymmetry. Comparisons of latency times to either courtship or copulation suggest that males do not discriminate females, whereas D. yakuba females, but not D. santomea females, accept their homospecifics more quickly. Cuticular hydrocarbon compositions of both species and sexes were also established with gas chromatography (GC) and GC/mass spectrometry analysis. All have (Z)-7-tricosene as their major compound. There are several quantitative differences between species for few minor compounds. The largest difference concerns n-heneicosane, which is more abundant in D. santomea than in D. yakuba flies (up to seven times more between males). A similar quantitative difference was also found in a pair of sympatric strains. Furthermore, D. yakuba males artificially perfumed with n-heneicosane were discriminated negatively by D. yakuba females, suggesting a role for this compound in the sexual isolation between these two species.     

A Comprehensive Study on the Synthesis and Micellization of Disymmetric Gemini Imidazolium Surfactants

Two groups of disymmetric Gemini imidazolium surfactants, [C₁₄C₄C _m im]Br₂ (m = 10, 12, 14) and [C _m C₄C _n im]Br₂ (m + n = 24, m = 12, 14, 16, 18) surfactants, were synthesized and their structures were confirmed by ¹H NMR and ESI–MS spectroscopy. Their adsorption at the air/water interface, thermodynamic parameters and aggregation behavior were explored by means of surface tension, electrical conductivity and steady-state fluorescence. A series of surface activity parameters, including cmc, γ _cmc, π _cmc, pC ₂₀, cmc/C ₂₀, Γ _max and A _min, were obtained from surface tension measurements. The results revealed that the overall hydrophobic chain length (N _c) for [C₁₄C₄C _m im]Br₂ and the disymmetry (m/n) for [C _m C₄C _n im]Br₂ had a significant effect on the surface activity. The cmc values decreased with an increase of N _c or m/n. The thermodynamic parameters of micellization (ΔG _m ^θ , ΔH _m ^θ , ΔS _m ^θ ) derived from the electrical conductivity indicated that the micellization process of [C₁₄C₄C _m im]Br₂ and [C _m C₄C _n im]Br₂ was entropy-driven at different temperatures, but the contribution of ΔH _m ^θ to ΔG _m ^θ was enhanced by increasing N _c or m/n. The micropolarity and micellar aggregation number (N _agg) were estimated by steady-state fluorescence measurements. The results showed that the surfactant with higher N _c or m/n can form larger micelles, due to a tighter micellar structure.     

Stability of polymer structures based on fullerene C<Subscript>60</Subscript> under their oxidation with oxygen

A comparative study of the oxidative destruction of the monomer face-centered cubic (FCC) lattice and various polymer [dimeric (D), orthorhombic (O), tetragonal (T), and rhombohedral (R)] phases of C₆₀ in an atmosphere of oxygen has been performed in the temperature range of 100–500°C with the use of a flow microunit connected to a gas chromatograph. From direct measurements of the content of CO₂ in the gaseous products of destruction, the temperature dependences of oxidation rates are measured for the materials under study. It has been established that, with respect to stability against oxidative destruction, different forms of C₆₀ may be arranged as follows: the monomer FCC phase of C₆₀ > D > O > T > R. The reasons behind this tendency are discussed.     

Conspecific and Heterogeneric Lacewings Respond to (<Emphasis Type="Italic">Z</Emphasis>)-4-Tridecene Identified from <Emphasis Type="Italic">Chrysopa formosa</Emphasis> (Neuroptera: Chrysopidae)

Green lacewings (Chrysopidae) are predators of soft-bodied pest insects and are among the most important biological control agents in crop protection. Chrysopa spp. are of special importance since, unlike most green lacewing species, adults are also predatory. The current study was undertaken in search of Chrysopa formosa compounds with semiochemical activity. Using coupled gas chromatography-electroantennography (GC-EAG), head and thorax extracts of C. formosa elicited EAG responses to a compound subsequently identified by coupled GC/mass spectrometry, microchemistry, chemical synthesis and GC peak enhancement as (Z)-4-tridecene. In field experiments, this compound decreased attraction of adult C. formosa to (1R,4aS,7S,7aR)-nepetalactol and that of Chrysoperla carnea species-complex to a ternary floral lure, with the inhibitory effect found to be dose-dependent. Our results suggest that (Z)-4-tridecene may serve as a general warning signal among multiple green lacewing species. Perspectives for potential practical applications are discussed.     

Purification,Surface Tensions,and Miscibility Gaps of Alkyldimethyl and Alkyldiethylphosphine Oxides

Alkyldimethyl (C _n DMPO) with chain lengths of n = 8 (octyl), 10 (decyl), 12 (dodecyl), and 14 (tetradecyl) as well as alkyldiethyl (C _n DEPO) phosphine oxides with chain lengths of n = 10, 12, and 14 were synthesized and purified to study how the adsorption properties and the location of the miscibility gap of these surfactants depend on the size of the head group and on the length of the alkyl chain. After surfactant purification, the surface tension isotherms were determined from which the cmc, the minimum surface tension σ_cmc, the maximum surface concentration Γ_max, and the minimum surface area A _min were obtained. As expected, for one homologous series, a decrease in the cmc and an increase in Γ_max was observed with increasing alkyl chain length. For two surfactants of the same alkyl chain length, the cmc values of the C _n DEPO surfactants are approximately two times lower than those of the C _n DMPO surfactants. However, the Γ_max values of C _n DEPO are lower than those of C _n DMPO as two ethyl chains are sterically more demanding than two methyl chains. In addition to the adsorption properties, the location of the miscibility gap as a function of the alkyl chain length and the head group size was studied. Its location depends on the total number of carbon atoms and not primarily on the length of the main alkyl chain. This observation reflects the decreasing water solubility which can be tuned by increasing the length of either the main alkyl chain or of the shorter head group chains.     

Unsaturated Cuticular Hydrocarbons Enhance Responses to Sex Pheromone in Spruce Budworm, <Emphasis Type="Italic">Choristoneura fumiferana</Emphasis>

The primary sex pheromone components of the female spruce budworm, Choristoneura fumiferana (Clem.) (Lepidoptera: Tortricidae), are (E)- and (Z)-11-tetradecenal, produced in 95:5 ratio. However, male flight responses to calling females in a wind tunnel were faster and maintained longer than responses to any synthetic aldehyde blend. Analyses of cuticular extracts from spruce budworm adults revealed series of n-alkanes and n-monoalkenes with predominantly odd numbers of carbon atoms from C₂₃- C₂₉ in both sexes. (Z,Z,Z)-3,6,9-tricosatriene and (Z,Z,Z)-3,6,9-pentacosatriene were identified only in cuticular extracts from females. Pheromonally naïve males showed wing fanning and circling responses to forewing scales from females but not to scales from males. Males also exhibited the same strong responses to scales excised from pharate females, indicating that the pheromone components are produced by females prior to emergence. (Z)-11-hexadecenal and (Z)-5-tricosene enhanced male responses to the primary sex pheromone aldehydes in wind tunnel bioassays, including higher proportions of in-flight and copulatory responses by males and increased time on the source. Addition of (Z,Z,Z)-3,6,9-tricosatriene to the 95/5 blend of (E)- and (Z)-11-tetradecenal released close-range copulatory responses including abdomen curling on treated septa. We propose that the sex pheromone blend of C. fumiferana is composed of the 95/5 blend of (E)- and (Z)-11-tetradecenal as primary components, with (Z)-11-hexadecenal, (Z)-5-tricosene and (Z,Z,Z)-3,6,9-tricosatriene fulfilling secondary roles in orientation and close-range courtship.     

Another new family of “extended” glucidoamphiphiles. Synthesis and surfactant properties for different sugar head groups and spacer arm lengths

Following a new four-step route, we prepared a family of “extended” glucidoamphiphiles from D-glucose, D-galactose, and xylitol in which the n-dodecyl chain is attached to the glucidic moiety by the linkage Z=O-Et-O-Et-O-(α-PP-O-) _n′ where-O-(α-PP-O-) _n is a poly-(α-propyloxy) commercial oligomeric mixture (with average length n=6, 10, and 14). This amphiphilic behavior study showed that (i) the glucose derivative exhibits water solubility and hydrophilic-lipophilic balance values that are close to those found for the glucose compound with Z=-O-(α-PP-O-) _n (without the Et-O-Et group), (ii) all these compounds are more strongly hydrophilic than the corresponding glucidic derivatives with Z=O, (iii) the increase of the poly-(α-propyloxy) chain length from ñ=6 to ñ=14 tends to reduce the hydrophilicity slightly.     

Volatiles of <Emphasis Type="Italic">Solena amplexicaulis</Emphasis> (Lam.) Gandhi Leaves Influencing Attraction of Two Generalist Insect Herbivores

Epilachna vigintioctopunctata Fabr. (Coleoptera: Coccinellidae) and Aulacophora foveicollis Lucas (Coleoptera: Chrysomelidae) are important pests of Solena amplexicaulis (Lam.) Gandhi (Cucurbitaceae), commonly known as creeping cucumber. The profiles of volatile organic compounds from undamaged plants, plants after 48 hr continuous feeding of adult females of either E. vigintioctopunctata or A. foveicollis, by adults of both species, and after mechanical damaging were identified and quantified by GC-MS and GC-FID analyses. Thirty two compounds were detected in volatiles of all treatments. In all plants, methyl jasmonate was the major compound. In Y-shaped glass tube olfactometer bioassays under laboratory conditions, both insect species showed a significant preference for complete volatile blends from insect damaged plants, compared to those of undamaged plants. Neither E. vigintioctopunctata nor A. foveicollis showed any preference for volatiles released by heterospecifically damaged plants vs. conspecifically damaged plants or plants attacked by both species. Epilachna vigintioctopunctata and A. foveicollis showed attraction to three different synthetic compounds, linalool oxide, nonanal, and E-2-nonenal in proportions present in volatiles of insect damaged plants. Both species were attracted by a synthetic blend of 1.64 μg linalool oxide?+?3.86 μg nonanal?+?2.23 μg E-2-nonenal, dissolved in 20 μl methylene chloride. This combination might be used as trapping tools in pest management strategies.     

Synthesis and crystal structure of the low-temperature modification of Li<Subscript>12</Subscript>Zn<Subscript>4</Subscript>(P<Subscript>2</Subscript>O<Subscript>7</Subscript>)<Subscript>5</Subscript>

The crystal structure of a low-temperature modification of the Li₁₂Zn₄(P₂O₇)₅ compound has been determined by full-profile analysis from the X-ray powder diffraction data. The compound crystallizes in the monoclinic crystal system (a = 5.130(1) Å, b = 13.454(1) Å, c = 8.205(1) Å, β = 90.36(1)°, space group P2₁/n, Z = 4) and has a framework structure in which the zinc and lithium atoms statistically occupy equivalent positions.     

Thermal behavior of layered perovskite-like compounds in the Bi<Subscript>4</Subscript>Ti<Subscript>3</Subscript>O<Subscript>12</Subscript>-BiFeO<Subscript>3</Subscript> system

The thermal properties of compounds of the general formula Bi _{m + 1} Fe _{m ? 3} Ti₃O_{3m + 3}, which are layered perovskite-like phases of the Aurivillius type, are investigated as a function of their composition. It is demonstrated that the temperature of decomposition of the Bi _{m + 1} Fe _{m ? 3} Ti₃O_{3m + 3} compounds decreases with an increase in the thickness of perovskite-like layers alternating in the structure and that the composition dependence of the temperature of the structural transition observed in these compounds exhibits a more complex behavior. The linear thermal expansion coefficients of all the compounds under investigation are found to be virtually independent of the composition.     

Dielectric study of side-chain liquid crystalline polyazomethine/fullerene C<Subscript>60</Subscript> nanocomposite

For side-chain liquid crystalline polyazomethine/fullerene C₆₀ nanocomposite (C₆₀ loading is 0.25 wt%), both real and imaginary components of the dielectric permittivity were investigated in wide regions of temperature and frequency. Analysis of frequency dependent permittivity allowed finding three relaxations (α, β ₁ and β ₂) in the nanocomposite. They were attributed to specific modes of molecular mobility. β-relaxations were described with the Arrhenius equation, whereas α-relaxation was described with the Vogel-Fulcher-Tammann equation. Anti-plasticization effect of the C₆₀ doping was shown to be manifested as an increase of the glass transition temperature of the nanocomposite as compared with that of the neat polymer.     

Sex Pheromone of the Cotton Mealybug, <Emphasis Type="Italic">Phenacoccus solenopsis</Emphasis>, with an Unusual Cyclobutane Structure

The cotton mealybug, Phenacoccus solenopsis, the distribution of which was formerly limited to Nearctic and Neotropical regions, recently invaded many countries in various regions including Asia, Africa, and the Pacific. More recently, P. solenopsis was newly recorded in Japan and is currently an emerging pest of agricultural crops. In this study, we determined the structure of a sex pheromone of P. solenopsis in order to develop an effective lure for monitoring this pest. From volatiles emitted by virgin adult females, we isolated a compound attractive to males. By means of coupled gas chromatography–mass spectrometry and nuclear magnetic resonance spectroscopy, we identified this as (2,2-dimethyl-3-isopropylidenecyclobutyl)methyl 3-methylbut-2-enoate. This compound was synthesized and shown to be attractive to male P. solenopsis. Analysis by gas chromatography using an enantioselective stationary phase and polarimetry analyses of the natural pheromone and synthetic enantiomers showed the natural compound to be the (R)-(?)-enantiomer. This compound is an ester of maconelliol, which has an unusual cyclobutane structure found in sex pheromones of other mealybug species, and senecioic acid, also found in the pheromones of other mealybug species. However, this is the first example of the ester of maconelliol and senecioic acid as a natural product.     

Multiple Roles of a Male-Specific Compound in the Sexual Behavior of the Dried Bean Beetle, <Emphasis Type="Italic">Acanthoscelides Obtectus</Emphasis>

Males of Acanthoscelides obtectus (Coleoptera: Chrysomelidae, Bruchinae) emit methyl (E,R)-2,4,5-tetradecatrienoate that attracts females for mating. This study identified further roles for this compound in the sexual behavior of A. obtectus. Earlier observations revealed that males touched females with their antennae while tandem-running with them and initiated mounting and copulation, whereas they showed no such behavior toward other males. A series of subsequent laboratory choice tests were set up to establish if certain cuticular compounds aid contact sex recognition in A. obtectus. Males chose virgin females over other males. The activity toward females could be eliminated by rinsing with hexane, but was regained by application of female extract onto previously rinsed females. Gas chromatographic (GC) comparison of hexane extracts revealed the presence of two male-specific compounds, methyl (E,R)-2,4,5-tetradecatrienoate and octadecanal, which were absent from the behaviorally active female samples. Of the two compounds, methyl (E,R)-2,4,5-tetradecatrienoate was found to be responsible for the inhibition of male sexual behavior, similar to that observed with crude male extracts applied to virgin females. Furthermore, males preferred virgin over mated females. GC analyses revealed the presence of methyl (E,R)-2,4,5-tetradecatrienoate in mated females in amounts sufficient to curtail mating attempts. It appears that methyl (E,R)-2,4,5-tetradecatrienoate, besides being a male-produced sex pheromone, acts as a male-recognition signal in A. obtectus. Males also transfer it onto females during mating, resulting in mated females being avoided by courting males.