Advertisement

Journal of Chemical Ecology

, Volume 8, Issue 5, pp 883–895 | Cite as

Structural significance of the alkyl substituent at the C-4 of (+)-trans-verbenyl acetate in sex pheromonal activity of the American cockroach

  • Hisao Takayanagi
  • Chikao Nishino
Article

Abstract

The significance of the alkyl group at the C-4 of (+)-trans-verbenyl acetate, which is the sex pheromone mimic of the American cockroach, was investigated. Seven alcohols possessing an ethyl, propyl, or dimethyl group at this position of the 6,6-dimethylbicyclo[3.1.1]heptane skeleton were synthesized and evaluated by behavioral assay. All of the alcohols were inactive, while three of four acetates of the 2α-alcohols induced sexual behavior in male cockroaches at the 0.02 or 0.5 mg dosage level, either of which is many orders of magnitude higher than the threshold level of the natural sex pheromones (10−8 mg). Among the acetates, the compounds with a methyl group or an α-oriented ethyl group at C-4 showed the highest activity. The results are discussed in terms of spatial requirements of the molecules for interactions with the receptor.

Key words

Sex pheromone mimics American cockroach Periplaneta americana [1R-(1α,2α,4α,5α)]-6 6-dimethyl-4-ethylbicyclo[3.1.1]heptan-2-yl acetate 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Adams, M.A., Nakanishi, K., Still, W.C., Arnold, E.V., Clardy, J., andPersoons, C.J. 1979. Sex pheromone of the American cockroach: Absolute configuration of periplanone-B.J. Am. Chem. Soc. 101:2495–2498.Google Scholar
  2. Kuriyama, K., Kondo, E., andTori, K. 1963. Conformation of ring A in some 2β-hydroxy and 2β-acetoxy-Δ4-3-ketosteroids.Tetrahedron Lett. 1963:1485–1491.Google Scholar
  3. Nishino, C., andTakayanagi, H. 1979a. Studies on the sex pheromone mimic of the American cockroach, (+)-trans-verbenyl acetate. Part I: Synthesis of verbenols and related alcohols and their PMR spectra with shift reagent.Agric. Biol. Chem. 43:1967–1974.Google Scholar
  4. Nishino, C., andTakayanagi, H. 1979b. Studies on the sex pheromone mimic of the American cockroach, (+)-trans-verbenyl acetate. Part III: Conformation of pinan-3-ol derivatives.Agric. Biol. Chem. 43:2399–2402.Google Scholar
  5. Nishino, C., andTakayanagi, H. 1979c. Studies on the sex pheromone mimic of the American cockroach, (+)-trans-verbenyl acetate. Part II: Conformational analysis of verbenols and related alcohols by PMR spectra with a chemical shift reagent.Agric. Biol. Chem. 43:2323–2329.Google Scholar
  6. Nishino, C., andTakayanagi, H. 1980. Studies on the sex pheromone mimic of the American cockroach, (+)-trans-verbenyl acetate. Part IV: Conformation of alcohols having apopinane skeleton.Agric. Biol. Chem. 44:1649–1652.Google Scholar
  7. Nishino, C., andTakayanagi, H. 1981. Studies on the sex pheromone mimic of the American cockroach, (+)-trans-verbenyl acetate. Part VI: Sex pheromonal activity of (+)-trans-verbenyl acetate and related compounds to the American cockroach,Periplaneta americana L.J. Chem. Ecol. 7:853–865.Google Scholar
  8. Nishino, C., Tobin, T.R., andBowers, W.S. 1977. Sex pheromone mimics of the American cockroach (Orthoptera: Blattidae) in monoterpenoids.Appl. Entomol. Zool. 12:287–290.Google Scholar
  9. Persoons, C.J. 1977. Structure elucidation of some insect pheromones: A contribution to the development of selective pest control agents. Thesis, Agricultural University, Wageningen, September 1977.Google Scholar
  10. Persoons, C.J., Verwiel, P.E.J., Talman, E., andRitter, F.J. 1979. Sex pheromone of the American cockroach,Periplaneta americana: Isolation and structure elucidation of periplanone-B.J. Chem. Ecol. 5:221–236.Google Scholar
  11. Roth, L.M., andWillis, E.R. 1952. A study of cockroach behavior.Am. Midl. Nat. 47:66–129.Google Scholar
  12. Takayanagi, H., andNishino, C. 1980. Studies on the sex pheromone mimic of the American cockroach, (+)-trans-verbenyl acetate. Part V: Synthesis of configurational isomers of verbenyl carboxylic acid and related compounds.Agric. Biol. Chem. 44:2877–2883.Google Scholar
  13. Talman, E., Verwiel, P.E.J., Ritter, F.J., andPersoons, C.J. 1978. Sex pheromones of the American cockroach,Periplaneta americana. Isr. J. Chem. 17:227–235.Google Scholar

Copyright information

© Plenum Publishing Corporation 1982

Authors and Affiliations

  • Hisao Takayanagi
    • 1
  • Chikao Nishino
    • 1
  1. 1.Mitsubishi-Kasei Institute of Life SciencesTokyoJapan

Personalised recommendations