Skip to main content
SpringerLink
Log in

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

  • Published:
Journal of Chemical Ecology Aims and scope Submit manuscript

Abstract

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • Bell, W.J., andGorton, R.E. 1978. Informational analysis of agonistic behaviour and dominance hierarchy formation in a cockroach,Nauphoeta cinerea.Behaviour 67:217–235.

    PubMed  Google Scholar 

  • Bell, W.J., Gorton, R.E., Tourtellot, M.K., andBreed, M.D. 1979. Comparison of male agonistic behavior in five species of cockroaches.Insect Soc. 26:252–263.

    Google Scholar 

  • Blum, M.S. 1981. Chemical Defense of Arthropods. Academic Press, New York, 562 pp.

    Google Scholar 

  • Breed, M.D., Smith, S.K., andGall, B.G. 1980. Systems of mate selection in a cockroach species with male dominance hierarchies.Anim. Behav. 28:130–134.

    Google Scholar 

  • Brossut, R., andSreng, L. 1985. L'univers chimique des Blattes.Bull. Soc. Entomol. Fr. 90:1266–1280.

    Google Scholar 

  • Brossut, R., Dubois, P., Rigaud, J., andSreng, L. 1975. Etude biochimique de la sécrétion des glandes tergales de Blattaria.Insect Biochem. 5:719–732.

    Google Scholar 

  • Charlton, R.E., andRoelofs, L.R. 1991. Biosynthesis of volatile, methyl-branched hydrocarbon sex pheromone from leucine by arctiid moths (Holomelina spp.).Arch. Insect Biochem Physiol. 18:81–97.

    Google Scholar 

  • Dettner, K., andSchwinger, G. 1980. Defensive substances from pygidial glands of water beetles.Biochem. Syst. Ecol. 8:89–95.

    Google Scholar 

  • Etievant, P.X., Mona, A., Pham-Delegue, M.H., andMasson, C.J. 1984. Isolation and identification of volatile constituents of sunflowers (Helianthus annuus L.).J. Agric. Food. Chem. 32:503–509.

    Google Scholar 

  • Ewing, L.S. 1972. Hierarchy and its relation to territory in the cockroachNauphoeta cinerea.Behavior 42:152–174.

    Google Scholar 

  • Ewing, L.S. 1973. Territoriality and the influence of females on the spacing of males in the cockroachNauphoeta cinerea.Behavior 45:182–303.

    Google Scholar 

  • Ewing, L.S., andEwing, A. 1973. Correlates of subordinate behavior in the cockroach,Nauphoeta cinerea.Anim. Behav. 21:571–578.

    Google Scholar 

  • Frattini, C., Bicchi, C., Baretti, C., andNano, G.M. 1976. Volatile aroma constituents of rhubarbs. Part 2.Riv. Ital. Essenze 58:132–135.

    Google Scholar 

  • Fukui, M., andTakahashi, S. 1983. Studies on the mating behavior of the cockroach,Nauphoeta cinerea (Olivier) (Dictyoptera: Blaberidae) III. Isolation and identification of intermale recognition pheromone.Appl. Entomol. Zool. 18:351–356.

    Google Scholar 

  • Gottschalk, G. 1986. Bacterial Metabolism, 2nd ed. Springer-Verlag, New York.

    Google Scholar 

  • Heller, S.R., andMilne, G.W.A. 1980. E.P.A./N.I.H. Mass Spectral Data Base. National Bureau of Standards (U.S.), U.S. Government Printing Office, Washington, D.C.

    Google Scholar 

  • Idstein, H., andSchreier, P. 1985a. Volatile constituents from papaya fruit (Carica papaya L., var. Solo).Lebensm.-Wiss. Technol. 18:164–169.

    Google Scholar 

  • Idstein, H., andSchreier, P. 1985b. Volatile constituents from guava (Psidium guajava L.).J. Agric. Food Chem. 33:138–143.

    Google Scholar 

  • Irvine, W.J., andSaxby, M.J. 1969. Constituents of certain tobacco types. III. Further volatile phenols of Latakia tobacco leaf.Agric. Biol. Chem. 34:2067–2070.

    Google Scholar 

  • Kamm, J.A., andButtery, R.G. 1984. Root volatile components of red clover: identification and bioassay with the clover root borer (Coleoptera: Scolytidae).Environ. Entomol. 13:1427–1430.

    Google Scholar 

  • Kamm, J.A., Buttery, R.G., andLing, L.C. 1984. Volatile components of red clover leaves, flowers, and seed pods: Possible insect attractants.J. Agric. Food Chem. 32:254–256.

    Google Scholar 

  • Kramer, S. 1964. Aggressive behavior in the courtship of cockroachNauphoeta cinerea.Am. Zool. 4:164.

    Google Scholar 

  • Longhurst, C., Baker, R., andHowse, P.E. 1980. A comparative analysis of mandibular gland secretions in ant tribeTetra morini.Insect Biochem. 10:107–112.

    Google Scholar 

  • MacFaddin, J.F. 1980. Biochemical Tests for Identification of Medical Bacteria, 2nd ed. Williams and Wilkins, Baltimore, pp. 308–320.

    Google Scholar 

  • MacGovern, T.P., andLadd, T.L., Jr. 1981. 2-Methoxyphenols, 1,2-dimethoxybenzenes, and 1,3-benzodioxoles as attractants for the northern corn rootworm (Coleoptera: Chrysomelidae).J. Econ. Entomol. 81:826–829.

    Google Scholar 

  • Menon, M. 1981. Morphological evidence for probable secreting site for the pheromone “Seducin” in males ofNauphoeta cinerea. I. Light microscope studies.J. Morphol. 168:229–237.

    Google Scholar 

  • Moore, A.J. 1988. Female preferences, male social status, and sexual selection inNauphoeta cinerea.Anim. Behav. 36:303–305.

    Google Scholar 

  • Moore, A.J. 1989. Sexual selection inNauphoeta cinerea: Inherited mating preferences?Behav. Genet. 19:717–724.

    PubMed  Google Scholar 

  • Moore, A.J. 1990a. The inheritance of social dominance, mating behaviour, and attractiveness to mates in maleNauphoeta cinerea.Anim. Behav. 39:388–397.

    Google Scholar 

  • Moore, A.J. 1990b. Sexual selection and genetics of pheromonally mediated social behavior inNauphoeta cinerea (Dictyoptera: Blaberidae).Entomol. Gener. 15:133–147.

    Google Scholar 

  • Nishida, R., Sato, R., Kuwabara, Y., Fukami, H., andIshii, S. 1976. Female sex pheromone of German cockroachBlattella germanica (L.) (Orthoptera: Blattellidae) responsible for male wing-raising. II. 29-hydroxy-3,11-dimethyl-2-nonacosanone.J. Chem. Ecol. 2:449–455.

    Google Scholar 

  • Perry, A.S. 1961. Metabolism of insecticides by various insect species.J. Agric. Food Chem. 00:266–272.

    Google Scholar 

  • Roth, L.M., andDateo, G.P. 1966. A sex pheromone produced by the male of the cockroachNauphoeta cinerea.J. Insect Physiol. 12:255–265.

    Google Scholar 

  • Roth, L.M., andWillis, E.R. 1952. A study of cockroach behavior.Am. Midl. Nat. 47:66–129.

    Google Scholar 

  • Schal, C., andBell, W.J. 1983. Determinants of dominant-subordinate interactions in males of the cockroachNauphoeta cinerea.Biol. Behav. 8:117–139.

    Google Scholar 

  • Schal, C., Burns, E.L., Jurenka, R.A., andBlomquist, G.J. 1990. A new component of the female sex pheromone ofBlattella germanica (L.) (Dictyoptera: Blattellidae) and interaction with other pheromone components.J. Chem. Ecol. 16:1997–2008.

    Google Scholar 

  • Sirugue, D. 1992. Comportement sexuel et hiérarchie chezLeucophaea maderae etNauphoeta cinerea (Dictyoptera, Blaberidae). Identification et rôle des phéromones sexuelles mâles. Thèse de Doctorat, Université de Bourgogne.

  • Sheehan, J.C., Beck, C.W., Henery-Logand, K.R., andRyan, J.J. 1956. The reaction of phthaloylglycyl chloride with 2-methyl-2-thiazoline.J. Am. Chem. Soc. 78:4478–4481.

    Google Scholar 

  • Smith, S., andBreed, M. 1982. Olfactory cues in discrimination among individuals in dominance hierarchies in the cockroach,Nauphoeta cinerea.Physiol. Entomol. 7:337–341.

    Google Scholar 

  • Sreng, L. 1979. Phéromones et comportement sexuel chezNauphoeta cinerea (Olivier) (Insecte, Dictyoptère).C.R. Acad. Sci. 289:687–690.

    Google Scholar 

  • Sreng, L. 1983. Comportement sexuel et communication chimique chez les blattes. Le cas deNauphoeta cinerea et des genres voisins. Thèse de Doctorat d'Etat, Université de Dijon.

  • Sreng, L. 1984. Morphology of the sternal and tergal glands producing the sexual pheromones and the aphrodisiacs among the cockroaches of the subfamily Osyhaloinae.J. Morphol. 182:279–294.

    Google Scholar 

  • Sreng, L. 1985. Ultrastructure of the glands producing sex pheromones of the maleNauphoeta cinerea (Insecta, Dictyoptera).Zoomorphology 105:133–142.

    Google Scholar 

  • Sreng, L. 1991. Seducin, male sex pheromone of the cockroachNauphoeta cinerea: Isolation, identification, and bioassay.J. Chem. Ecol. 16:2899–1912.

    Google Scholar 

  • Takahashi, S., andFukui, M. 1980. Studies on the mating behavior of the cockroachNauphoeta cinerea Olivier. 2. Wing raising stimulant in cuticular wax.Appl. Entomol. Zool. 15:159–166.

    Google Scholar 

  • Takahashi, S., andFukui, M. 1983. Studies on the mating behavior of the cockroachNauphoeta cinerea Olivier (Dictyoptera: Blaberidae). 4. Synthesis and biological activity of nauphoetin and related compounds.Appl. Entomol. Zool. 18:257–360.

    Google Scholar 

  • Welch, R.C., Johnston, J.C., andHunter-George, L.K. 1982. Volatile constituents of the muscadine grape (Vitis rotundifolia).J. Agric. Food Chem. 30:681–684.

    Google Scholar 

  • Wheeler, J.W. 1977. Properties of compounds used as chemical signals, pp. 61–70,in D. Müller-Scharze and M.M. Mozell, (eds.). Chemical Signals in Vertebrates. Plenum Press, New York.

    Google Scholar 

  • Yamanishi, T., Michiko, N., andNakatani, Y. 1970. Flavor of green tea. VIII. Flavor constituents in manufactured green tea.Agric. Biol. Chem. 34:599–608.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Zoologie UA CNRS 674, Université de Bourgogne, 6 Bd. Gabriel, 21000, Dijon, France

    Daniel Sirugue, Odile Bonnard, Jean-Pierre Farine & Rémy Brossut

  2. Laboratoire de Recherches sur les Arômes, INRA, 17 rue de Sully, 21000, Dijon, France

    Jean-Luc Le Quere

Authors
  1. Daniel Sirugue
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Odile Bonnard
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jean-Luc Le Quere
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jean-Pierre Farine
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Rémy Brossut
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sirugue, D., Bonnard, O., Le Quere, JL. et al. 2-Methylthiazolidine and 4-ethylguaiacol, male sex pheromone components of the cockroachNauphoeta cinerea (dictyoptera, blaberidae): A reinvestigation. J Chem Ecol 18, 2261–2276 (1992). https://doi.org/10.1007/BF00984949

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00984949

Key Words

Search

Navigation