Sex-pairing pheromones and reproductive isolation in three sympatric Cornitermes species (Isoptera, Termitidae, Syntermitinae)

The species-specificity of pairing has been studied in three sympatric Neotropical termites: Cornitermes bequaerti, Cornitermes cumulans and Cornitermes silvestrii (Termitidae, Syntermitinae). Bioassays showed that sex attraction was highly species-specific between C. bequaerti and C. cumulans but not between C. cumulans and C. silvestrii. The sex-pairing pheromone of the three species is secreted by the tergal glands of female alates. It consists of a common compound (3Z,6Z,8E)-dodeca-3,6,8-trien-1-ol. In C. bequaerti, this polyunsaturated alcohol is the only compound of the sex-pairing pheromone, whereas it is associated with the oxygenated sesquiterpene (E)-nerolidol in C. cumulans, and with (E)-nerolidol and (Z)-dodec-3-en-1-ol in C. silvestrii. (3Z,6Z,8E)-Dodeca-3,6,8-trien-1-ol is responsible for sexual attraction, whereas (E)-nerolidol, which is inactive in eliciting attraction of male alates, is responsible for the species-specificity of the attraction. This is the first time that a multicomponent sex-pairing pheromone has been identified in termites. The role of (Z)-dodec-3-en-1-ol present on the surface of the tergal glands of the female alates of C. silvestrii could not be definitively determined, but it is suggested that this compound could be involved in the species-specificity of sex attraction with other sympatric species of Cornitermes. Our study shows that the reproductive isolation in termites is due to a succession of factors, as the chronology of dispersal flights, the species-specificity of sex-pairing pheromones and the species-specific recognition.     

Sex-pairing pheromone of Ancistrotermes dimorphus (Isoptera: Macrotermitinae)

Ancistrotermes dimorphus is a common Macrotermitinae representative, facultative inquiline by its life-style, occurring in South-East China. Sex pheromone is used for couple formation and maintenance, and it is produced by and released from the female sternal gland and is highly attractive to males. Based on our combined behavioral, chemical and electrophysiological analyses, we identified (3Z,6Z)-dodeca-3,6-dien-1-ol as the female sex pheromone of A. dimorphus as it evoked the tandem behavior at short distance, and the active quantities ranged from 0.01 ng to 10 ng. Interestingly, GC–MS analyses of SPME extracts showed another compound specific to the female sternal gland, (3Z)-dodec-3-en-1-ol, which showed a clear GC-EAD response. However, this compound has no behavioral function in natural concentrations (0.1 ng), while higher amounts (1 ng) inhibit the attraction achieved by (3Z,6Z)-dodeca-3,6-dien-1-ol. The function of (3Z)-dodec-3-en-1-ol is not fully understood, but might be linked to recognition from sympatric species using the same major compound, enhancing the long-distance attraction, or informing about presence of other colonies using the compound as a trail-following pheromone. The sternal gland secretion of Ancistrotermes females contains additional candidate compounds, namely (3E,6Z)-dodeca-3,6-dien-1-ol and (6Z)-dodec-6-en-1-ol, which are not perceived by males’ antennae in biologically relevant amounts.     

Hickory shuckworm Cydia caryana: electroantennogram and flight tunnel studies of potential sex pheromone components

Electroantennogram (EAG) measurement of male Cydia caryana moth antennal olfactory response to monounsaturated 12 and 14 carbon alcohols and acetates indicated that the (E)-8-, (E)-10- conjugated double bond system of a dodecadien-1-ol acetate is a critical chemical structural component of the C. caryana sex pheromone. Additionally, EAG measurements implicated (E)-8-dodecen-1-ol acetate, (Z)-8-dodecen-1-ol acetate, (Z)-9-dodecen-1-ol acetate and (Z)-12-tetradecen-1-ol as potential minor pheromonal components. An EAG dosage-response study suggested that there were at least two heterologous populations of pheromone acceptors. Behavioral analysis of male moth response in a flight tunnel to compounds which evoked the stronger EAG responses suggested that (E,E)-8,10-dodecadien-1-ol acetate and (Z)-9-dodecen-1-ol acetate resemble or are C. caryana sex pheromonal components, while (Z)-8-dodecen-1-ol acetate and (E)-10-dodecen-1-ol acetate are either parapheromones or are minor pheromone components. Behavioral significance of (Z)-12-tetradecen-1-ol was difficult to interpret in the flight tunnel.

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Résumé Les réponses olfactives antennaires de Cydia caryana, mesurées par électroantennogrammes (EAG), aux alcools et acétates à carbones monounsaturés en positions 12 et 14, ont montré que le système conjugué de double liaison, (E)-8-, (E)-10- du dodecadien-1-ol acétate constitue un composé chimique strutural critique de la phéromone sexuelle de C. caryana.De plus, les acétates: (E)-8-dodecen-1-ol,(Z)-8-dodecen-1-ol,(Z)-9-dodecen-1-ol, et le (Z)-12-tetradecen-1-ol, se sont révélés en AEG comme des composés secondaires de la phéromone. L'étude par AEG de la relation dose-réponse a conduit à l'hypothèse de deux catégories de populations de récepteurs de phéromones. L'analyse comportementale des résponses des papillons mâles dans le tunnel de vol aux composés qui ont provoqués les plus forts AEG, on fait estimer que les acétates (E,E)-8,10-dodécadien-1-ol et (Z)-9-dodecen-1-ol ressemblent (ou sont) les constituants de la phéromone sexuelle de C. caryana; tandis que les (Z)-8-dodecen-1-ol et (E)-10-dodecen-1-ol sont, soit des paraphéromones, soit des constituants mineurs de la phéromone.La signification biologique du (Z)-12-tétradécen-1-ol a été difficile à interprêter avec les expériences en tunnel de vol.

     

Synthesis of (3E, 5Z)-3,5-Dodecadienylacetate,the Sex Pheromone of Phtheochroa cranaodes (Lepidoptera: Tortricidae)

(3E, 5Z)-3,5-Dodecadienyl acetate, the female sex pheromone of Phtheochroa cranaodes, was regio and stereo-selectively synthesized from 1-octyne and (E)-4-bromo-3-buten-1-ol by using Pd(PPh₃)₄, CuI and piperidine to afford the enyne (5). Further elaboration afforded the target pheromone. The synthetic pheromone was identified with the natural product by its MS and IR, data GLC retention time and biological activity.     

Reduction of the Acyl Group: The Critical Step in Bombykol Biosynthesis That Is Regulated in Vitro by the Neuropeptide Hormone in the Pheromone Gland of Bombyx mori

The sex pheromone of Bombyx mori, bombykol [(10E,12Z)-10,12-hexadecadien-1-ol], can be biosynthesized in four steps: construction of a hexadecanoic moiety from acetyl CoA, ?-11-desaturation, .?-10,12-desaturation, and reduction of the acyl group. This biosynthesis is regulated by a hormone named the pheromone biosynthesis activating neuropeptide (PBAN). To examine the steps that are accelerated by this neurohormone, pheromone glands excised from decapitated females were incubated in vitro with either ¹⁴C-Iabeled sodium acetate or one of three fatty acids [hexadecanoic acid, (Z)-11-hexadecenoic acid, or (10E,12Z)-10,12-hexadecadienoic acid]. After analyzing the radioactivity that was incorporated from each precursor into bombykol and the biosynthetic precursors, it was observed that the first three steps proceeded in glands both treated and untreated with synthetic PBAN of B. mori; however, the last step proceeded only in the treated glands. From this in vitro experiment, it can be concluded that the main regulatory role of PBAN is in the reduction of the acyl group in B. mori, as was shown by our previous in vivo experiment.     

Identification and field attraction of the female sex pheromone of a kiwifruit pest,Nokona feralis (Lepidoptera: Sesiidae)

Female sex pheromone of a clearwing moth Nokona feralis (Leech) (Lepidoptera: Sesiidae), a pest of kiwifruit, was identified to be a 7:3 mixture of (3E,13Z)-3,13-octadecadienyl acetate (E3,Z13-18:OAc) and (3E,13Z)-3,13-octadecadien-1-ol (E3,Z13-18:OH) by GC-EAD and GC/MS analyses. Males were attracted to wide-range mixtures of E3,Z13-18:OAc and E3,Z13-18:OH, and a 7:3 mixture of those two compounds strongly attracted the males in the field.     

Cynasibirolide A,One New Humulanolide Sesquiterpene from Cynanchum acutum subsp. sibiricum

Cynasibirolide A ( 1 ), one new humulanolide sesquiterpene, together with four known analogs, asteriscanolide ( 2 ), (1S,8S)-8-hydroxyhumula-2Z,6E,9E-trien-1,12-olide ( 3 ), (1S,7R)-8-oxohumula-2Z,9E-dien-1,12-olide ( 4 ), and (+)-6,7,9,10-tetrahydroasteriscunolide ( 5 ) were isolated from the roots and rhizomes of Cynanchum acutum subsp. sibiricum. Their structures and configurations were elucidated by spectroscopic methods, including 2D-NMR techniques, and the structure of 1 was confirmed by single-crystal X-ray diffraction. All compounds were evaluated for their anti-complementary activity in vitro, and compound 3 exhibited anti-complement effect with CH₅₀ value of 0.45 mM.     

An amide from salmea scandens

Costunolide and the isobutylamides of 2E,4E,8Z,10Z- and 2E,4E,8Z,10E-dodeca-2,4,8,10-tetraenoic acid were isolated from the roots of Salmea scandens.     

Morphology of the sternal and tergal glands producing the sexual pheromones and the aphrodisiacs among the cockroaches of the subfamily oxyhaloinae

Among cockroaches in the subfamily of Oxyhaloinae, the adult males produce two essential and successively active chemical signals: the sex pheromone attracting females from a distance secreted by the sternal glands, and the aphrodisiac required for mating which is secreted by the tergal glands. The adult males of the seven species studied, Nauphoeta cinerea, Henschoutedenia flexivitta, Leucophaea maderae, Jagrehnia madecassa, Gromphadorhina portentosa, G. laevigata, and G. chopardi, possess well-developed sternal and tergal glands whose number varies according to the species and methods of mating (three to six sternal glands and four to seven tergal glands). These glands are basically composed of type three glandular units (glandular cell + duct cell) and type 2 cells (modified oenocytes) which exhibit no significant external cuticular modification except for tergite 2 of L. maderae. The extreme variance in development of these glands can be linked to sexual behavior. The hypothesis put forward here is that of a regressive evolution of the tergal glands, related to a modification of the role played by the aphrodisiacs which they secrete.     

JBIR-66, a New Metabolite Isolated from Tunicate-Derived Saccharopolyspora sp. SS081219JE-28

In the course of our chemical screening program for new secondary metabolites, we isolated a new compound JBIR-66 (1) from the culture broth of the tunicate-derived actinomycete, Saccharopolyspora sp. SS081219JE-28. The structure of 1 was determined to be (3Z,6E,8E)-N-(4-acetamido-3-hydroxybutyl)-2-hydroxy-4,8-dimethylundeca-3,6,8-trienamide on the basis of extensive NMR and MS spectroscopic data.     

Syntheses,Characterizations, and Biological Activities of Tetradeca‐4,8‐dien‐1‐yl Acetates as Sex Attractants of Leaf‐Mining Moth of the Genus Phyllonorycter (Lepidoptera: Gracillariidae)

The four possible isomers of tetradeca‐4,8‐dien‐1‐yl acetate and corresponding alcohols were synthesized stereoselectively by synthetic routes employing Wittig coupling reaction for the preparation of (Z,E)‐ and (Z,Z)‐isomers, and alkylation of terminal alkynes for the preparation of (E,E)‐ and (E,Z)‐isomers as the key steps. Synthetic products were characterized by ¹³C‐ and ¹H‐NMR spectroscopy as well as mass‐spectrometric methods. All four isomers gave distinctive mass spectra where m/z 81 fragments clearly dominated. Elution order, followed by retention index presented in parenthesis, of tetradeca‐4,8‐dien‐1‐ols was determined as (Z,Z) (2082.1), (Z,E) (2082.8), (E,E) (2083.1), and (E,Z) (2083.2) from unpolar SPB‐1 column, and as (E,E) (2210.2), (Z,E) (2222.1), (E,Z) (2223.4), and (Z,Z) (2224.7) from polar DB‐WAX column. The isomers of tetradeca‐4,8‐dien‐1‐yl acetates eluted in the order of (Z,Z) (2176.1), (Z,E) (2178.4), (E,Z) (2185.9), and (E,E) (2186.4) from SPB‐1, and (Z,E) (2124.3), (E,E) (2157.7), (Z,Z) (2128.9), and (E,Z) (2135.9) from DB‐WAX columns. Field‐screening tests for attractiveness of tetradeca‐4,8‐dien‐1‐yl acetates revealed that (4Z,8E)‐tetradeca‐4,8‐dien‐1‐yl acetate significantly attracted Phyllonorycter coryli and Chrysoesthia drurella males. (4E,8E)‐Tetradeca‐4,8‐dien‐1‐yl acetate was the most efficient attractant for Ph. esperella and Ph. saportella males, and (4E,8Z)‐tetradeca‐4,8‐dien‐1‐yl acetate was attractive to Ph. cerasicolella males.     

(Z)-8-dodecenyl acetate: the major component of the female sex pheromone of Cryptophlebia batrachopa, a Tortricid pest of macadamia in Malawi

Ovipositor washings from virgin female Cryptophlebia batrachopa (Meyrick) (Lepidoptera: Tortricidae) were analysed by gas chromatography (GC) linked to electroantennography (EAG) and by high-resolution GC. The major EAG-active component in ovipositor washings was shown to be (Z)-8-dodecenyl acetate with less than 0.5% of the E isomer. GC analysis of ovipositor washings from C. leucotreta confirmed the presence of approximately equal amounts of (Z)- and (E)-8-dodecenyl acetates (Persoons et al., 1977). When pure (Z)-8-dodecenyl acetate and mixtures containing up to 50% of the E isomer were tested in the field in Malawi where both Cryptophlebia species occurred, C. batrachopa male moths were caught only in traps baited with 10% or less of the E isomer and highest catches were recorded for the pure Z isomer. By contrast C. leucotretra males were caught predominantly by traps baited with more than 10% E isomer and no catches were recorded for the pure Z isomer. (Z)-8-dodecenyl acetate containing 1% of the E isomer was found to attract male moths of Opogona spp.

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Résumé Les produits recueillis par lavages de l'ovipositeur de Cryptophlebia batrachopa Meyr. (Lep. Tortricidae) ont été analysés par chromatographie gazeuse (GC) associée à l'électroantennographie (EAG) et la GC à haute résolution. Le principal constituant actif en EAG provenant des lavages s'est révélé être le (Z)-8-dodécényl acétate avec moins de 0,5% de l'isomère E. L'analyse GC de ces produits de lavage de C. leucotreta ont confirmé la présence d'à peu près les mêmes quantités de (Z) et (E)-8-dodécényl acétates (Persoons et al., 1977). Quand des essais sur le terrain ont été effectués au Malawi, où existent les deux espèces de Cryptophlebia, avec du (Z)-8-dodécényl acétate et des mélanges comprenant jusqu'à 50% de l'isomère E, des mâles de C. batrachopa ont seuls été capturés dans des pièges contenant 10% ou moins de l'isomère E; les captures les plus élevées ont été obtenues avec l'isomère Z pur. A l'opposé, surtout des mâles de C. leucotreta ont été capturés dans des pièges garnis avec plus de 10% d'isomère E, et aucune capture n'a été obtenue avec l'isomère Z pur. Des mâles d'Opogona spp. ont été attirés par du (Z)-8-dodécényl acétate contenant 1% de l'isomère E.

     

Cockroach mating behaviors,sex pheromones,and abdominal glands (Dictyoptera: Blaberidae)

Two chemical signals are essential in all cockroach sexual behavioral sequences: the sex pheromone released by one partner, generally the female (for long distance attraction), and an aphrodisiac sex pheromone produced exclusively by male tergal glands (for female mounting and tergal contact or feeding behavior). Unlike the other cockroach groups, the males of the Oxyhaloinae species produce both chemical signals: the pheromone and the aphrodisiac. The occurrence of three patterns of mating behavior (A, B, and C), the production of male sex pheromones, and the existence in the male of developed sternal and tergal glands in seven related Oxyhaloinae species, make these cockroaches a useful model for studying the evolution of mating behavior patterns. The various types of mating behavior were not classified in the previous studies by Roth and Barth. In this report, they have been named type A (female in upper position), B (male in upper position), and C (male and female end to end). In type A mating, the male tergal glands, which are licked by the females, are well developed, whereas in types B and C, there is no licking of the male's tergal secretion by the females and the tergal glands are much less developed; the aphrodisiacs secreted by the tergal glands may no longer act in this case through contact chemoreception, but through an olfactory process involving volatile components. One common sex pheromone component seems to be acetoin. I suggest that the mating behavior tends from A toward B and C during the evolutionary process with a concomitant regression of the tergal glands and changes in the aphrodisiac emission levels. The mating behavioral sequences of cockroaches (Dictyoptera) and crickets (Orthoptera) show a striking degree of similarity and are probably examples of convergent evolution.     

Sex pheromone blend of Manduca sexta: Responses of central olfactory interneurons to antennal stimulation in male moths

Recently, chemical analysis of solvent rinses of the external surfaces of pheromone glands from female Manduca sexta revealed a blend of 12 aldehydes, including the previously identified sex pheromone component, (E,Z)-10,12-hexadecadienal (bombykal). Previous electrophysiological studies showed that olfactory (deutocerebral) interneurons in the antennal lobes of males exhibited a wide range of responsiveness to pheromonal stimulation of the ipsilateral antenna. These experiments were performed with crude extracts of pheromone glands as well as two synthetic compounds: the major pheromone component, bombykal, and (E,Z)-11,13-pentadecadienal, a mimic of a second component of the female's pheromone blend. Using intracellular methods, we have now reexamined similar olfactory interneurons, using each of the 12 chemically identified components as well as synthetic blends of various combinations of them. Eight of the 12 components isolated from female glands elicited some form of response in olfactory interneurons in males. In accordance with biochemical and behavioral data, the most potent are bombykal and two trienals, (E,E,E)- and (E,E,Z)-10,12,14-hexadecatrienal. We also conclude that the C₁₅ dienal is selective for one of the trienal receptors on the antenna, but is much less potent than the natural trienal stimulant.     

Ultrastructure of the glands producing sex pheromones of the male Nauphoeta cinerea (Insecta,Dictyoptera)

Summary The abdominal glands described here play a decisive role in the typical sexual behavior of Nauphoeta cinerea. Unlike other cockroaches, the males of this species produce two successive chemical signals: the sex pheromone itself, produced by the sternal glands, attracts the female from a distance, and the aphrodisiacs, secreted by the tergal glands, are licked by the female who is thus in a favorable position for mating. The well developed glandular apparatus is composed of 5 sternal glands (St3 to St7) and 7 tergal glands (T2 to T8). These glands appear as a thickening of the epithelium without significant modification of the external cuticle. The glandular epithelium is made up of several kinds of cells: ordinary epidermal cells (which only exist in the sternal glands), cells with microtubules, type 2 cells (oenocytes), and especially type 3 glandular units (composed of a secretory cell and a canal cell). The products secreted by the sternal glands are chiefly volatile products and fatty acids and those secreted by the tergal glands are primarily fatty acids and proteins. In this work, the relationship between the cytology of the glandular cells and the nature of the secreted products is discussed.     

Behavioral and electrophysiological responses of Helicoverpa assulta, H. armigera (Lepidoptera: Noctuidae), their F1 hybrids and backcross progenies to sex pheromone component blends

Two sibling species, Helicoverpa assulta and Helicoverpa armigera both use (Z)-9-hexadecenal and (Z)-11-hexadecenal as their sex pheromone components but in almost reversed ratios, 93:7 and 3:97, respectively. H. assulta and H. armigera males performed upwind flight in response to the H. assulta sex pheromone blend (93:7). H. armigera responded strongly to the H. armigera blend (3:97), whereas H. assulta males remained inactive upon exposure to this blend. Both species gave clear dose-dependent electrophysiological responses to (Z)-11-hexadecenal. However, (Z)-9-hexadecenal evoked strong dose-dependent electrophysiological responses in H. assulta males but not in H. armigera. The two male F₁ hybrids exhibited similar behavioral responses to two sex pheromone blends and electrophysiological responses to two pheromone components as H. armigera males. This indicated that H. armigera genes appear dominant in determining the behavioral response and electrophysiological responses. Behavioral and electrophysiological responses of backcrosses of male F₁ hybrids (H. armigera female × H. assulta male) with female H. assulta and H. armigera were close to that of H. assulta and H. armigera, respectively. However, backcrosses of female F₁ hybrids (H. assulta female × H. armigera male) with male H. assulta and H. armigera showed reduced behavioral responses but normal electrophysiological responses compared to males of the respective parental line.     

Use of pheromone chemistry to identify Grapholita lobarzewskii as an occasional pest of apple and plum

As shown by chemical analysis and field trapping, the sex pheromone of Grapholita lobarzewskii consists of a blend of (E)-8-dodecenyl acetate and (Z)-8-dodecenyl acetate. Maximum attractiveness was found at 80–95%. Dodecyl acetate and tetradecyl acetate, both present in the female gland, did not affect trap catch. G. lobarzewskii has recently gained importance as a pest of apple and plum, but has so far been referred to as Grapholita janthinana. The latter is attracted to the same two compounds, but in reversed portions (20% E).

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Zusammenfassung Chemische Analysen und Feldversuche zeigen, dass das Sexualpheromon des Kleinen Fruchtwicklers, G. lobarzewskii aus (E)-8-Dodecenylacetat (Z8-12:Ac) und (Z)-8-Dodecenylacetat (Z8-12:Ac) besteht. Die grösste Lockwirkung wurde mit einem Gemisch der beiden Substanzen bei einem E-Anteil von 80–95% erzielt. Dodecylacetat (12:Ac) und Tetradecylacetat (14:Ac) wurden ebenfalls in den weiblichen Pheromondrüsen nachgewiesen, hatten aber im Freiland keinen Einfluss auf die Lockwirkung. G. lobarzewskii tritt seit einiger Zeit in der Schweiz als Schädling von Apfel und Zwetschge auf und ist an ihrem charakteristischem Frassgang leicht erkennbar. Die Art wurde bisher irrtümlich als G. janthinana bezeichnet. G. janthinana lebt auf Rosaceen, und wird vom gleichen Substanzpaar angelockt, allerdings bei umgekehrtem Mischungsverhältnis (20% E).

     

A Convenient Synthesis of a Mixture of (Z,Z)-3,13-Octadecadienyl Acetate and Its (E,Z)-Isomer,the Attractant for the Cherrytree Borer

A 1:1 mixture of (Z, Z)-3,13-octadecadien-1-ol and its (E, Z)-isomer was synthesized by a Wittig reaction whose stereoselectivity was adjusted to give the products in the required ratio. The corresponding acetate mixture is useful as the attractant for Synanthedon hector.     

Responses of male winter moths (Operophtera brumata) to their sex attactant (3Z,6Z,9Z)-1,3,6,9 nonadecatetraene and to some structural analogues

Conclusion (3Z,6Z,9Z)-1,3,6,9-nonadecatetraene, the synthetic sex pheromone of the female of O. brumata is highly active in attracting males of this species in the field (Germany and Switzerland). No analogous compounds possessing attractivity to O. brumata males have been found up to now, nor did they show any inhibitory effects to the same species.Therefore (3Z,6Z,9Z)-1,3,6,9-nonadecatetraene (I) can be recommended as a good attractant in the prognosis or monitoring of this lepidopteran pest.     

Sex pheromones of Phyllonorycter acerifoliella and Ph. heegerella and communication peculiarities in three species of leafmining moths

Females of the leaf miner moth Phyllonorycter acerifoliella (Z.) [=Ph. sylvella (Hw.)] and Ph. heegerella (Z.) (Lepidoptera: Gracillariidae: Lithocolletinae) release their sex pheromone at the beginning of photophase. The periodicity of the `calling' behaviour of Ph. acerifoliella females was established. Three compounds from calling virgin Ph. heegerella females were collected by the Solid Phase Micro Extraction (SPME) technique and identified as (Z)-8-tetradecenyl acetate (Z8-14:OAc), tetradecyl acetate (14:OAc) and (Z)-8-tetradecenol (Z8-14:OH) in the ratio (88±3):(2±0.6):(10±5) by capillary gas chromatography and mass spectrometry. Field trapping experiments demonstrated that the first two compounds are important for the attraction of conspecific males. Z8-14:OAc was found to be attractive when tested separately, while 14:OAc acted as synergist. The attractivity of the three component blend was reduced by 10% admixture of either (E)-10-dodecenyl acetate (E10-12:OAc) or (Z)-10-tetradecenyl acetate (Z10-14:OAc).Field tests of Z10-, Z8- and E10-14:OAc, identified from Ph. acerifoliella females, demonstrated that the first two compounds were essential for the attraction of conspecific males; so both are sex pheromone components. The attractivity of the three component blend of Z10- Z8- and E10-14:OAc was reduced by 10% admixture of (E)-10-dodecenol (E10-12:OH). The following four semiochemical compounds, Z8-14:OAc, Z8-14:OH, E10-14:OAc and 14:OAc, identified from phyllonoryctid females, as well as two sex attraction antagonists for Ph. acerifoliella and Ph. heegerella males, E10-12:OAc and Z10-14:OAc, are new for the family Gracillariidae. The results of field trapping experiments revealed mechanisms ensuring the specificity of the chemocommunication systems in Ph. acerifoliella, Ph. heegerella and Ph. ulmifoliella (Hb.) moths.