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Sex Attractant Pheromone of the Red-Shouldered Stink Bug Thyanta pallidovirens: A Pheromone Blend with Multiple Redundant Components

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Abstract

The male-produced sex pheromone of the red-shouldered stink bug, Thyanta pallidovirens (Stål) (Hemiptera: Pentatomidae) consists of a blend of methyl (E2,Z4,Z6)-decatrienoate (E2,Z4,Z6–10:COOMe), and the sesquiterpenes (+)α-curcumene, (−)-zingiberene, and (−) -β-sesquiphellandrene. In laboratory bioassays, sexually mature males attracted sexually mature females but not males, and females did not attract either sex. Extracts of volatiles collected from sexually mature males contained compounds not present in extracts from females or sexually immature males, and male-produced extract was attractive to females. Biological activity was lost when the extract was fractionated, indicating that the pheromone consisted of at least two components having different chemical properties. Individually, pheromone components were not attractive to females, but E2,Z4,Z6–10:COOMe in combination with at least one of the three male-produced sesquiterpenes was attractive. The presence of more than one sesquiterpene in the blend did not increase attraction, indicating redundancy in the pheromone signal. Male extract was as attractive as a blend reconstructed from synthesized compounds, indicating all biologically active components had been identified. In bioassays conducted at dusk in a 1- × 1- × 1-m screen field cage, females were attracted to synthetic pheromone lures. In field trials, adult female T. pallidovirens were attracted to pheromone-baited traps in relatively low numbers. The profile of volatiles released by sexually mature males of a congeneric species, Thyanta accerra custator McAtee, was remarkably similar to that of male T. pallidovirens, with the exception that the former species produced (E)-2-decenal, a compound that was not found in T. pallidovirens extracts.

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REFERENCES

  • Adams, R. P. 1995. Identification of Essential Oil Components by Gas Chromatography/Mass Spectroscopy. Allured Pub. Corp., Carol Stream, Illinois.

    Google Scholar 

  • Aldrich, J. R. 1988. Chemical ecology of the Heteroptera. Annu. Rev. Entomol. 33:211–238.

    Google Scholar 

  • Aldrich, J. R. 1995. Chemical communication in the true bugs and parasitoid exploitation, pp. 318–363, in R. T. Cardé and W. J. Bell (eds.). Chemical Ecology of Insects II. Chapman & Hall, New York.

    Google Scholar 

  • Aldrich, J. R., Lusby, W. R., Marron, B. E., Nicolau, K. C., Hoffmann, M. P., and Wilson, L. T. 1989. Pheromone blends of green stink bugs and possible parasitoid selection. Naturwissenschaften 76:173–175.

    Google Scholar 

  • Aldrich, J. R., Hoffmann M. P., Kochansky, J. P., Lusby, W. R., Eger, J. E., and Payne, J. A. 1991. Identification and attractiveness of a major pheromone component for Nearctic Euschistus spp. stink bugs (Heteroptera: Pentatomidae). Environ. Entomol 20:477–483.

    Google Scholar 

  • Aldrich, J. R., Numata, H., Borges, M., Bin, F., Waite, G. K., and Lusby, W. R. 1993. Artifacts and pheromone blends from Nezara spp. and other stink bugs (Heteroptera: Pentatomidae). Z. Naturforsch. 48C:73–79.

    Google Scholar 

  • Aldrich, J. R., Rossi, M. C., and Bin, F. 1995. Behavioral correlates for minor volatile compounds from stink bugs (Heteroptera: Pentatomidae). J. Chem. Ecol. 21:1907–1920.

    Google Scholar 

  • ANONYMOUS. 1991. Integrated Pest Management for Apples and Pears. University of California Statewide IPM Project, DANR Pub. #3340.

  • Borges, M., Schmidt, F. G. V., Sujii, E. R., Medeiros, M. A., Mori, K., Zarbin, P. H. G., and Ferreira, J. T. B. 1998. Field responses of stink bugs to the natural and synthetic pheromone of the Neotropical brown stink bug, Euchistus heros (Heteroptera: Pentatomidae). Physiol. Entomol. 23:202–207.

    Google Scholar 

  • Buckingham, J. (ed.). 1994. Dictionary of Natural Products, 1st ed. Chapman & Hall, London.

    Google Scholar 

  • Chavan, S. P., Dhondge, V. D., Patil, S. S., Rao, Y. T. S., and Govande, C. A. 1997. Enantiospecific total synthesis of (C)-laevigatin. Tetrahedron Asymm. 8:2517–2518.

    Google Scholar 

  • Çokl, A., McBrien, H. M., and Millar, J. G. 2001. Comparison of substrate-borne vibrational signals of two stink bug species, Acrosternum hilare (Say) and Nezara viridula (L.) (Heteroptera: Pentatomidae). Ann. Entomol. Soc. Am. 94:471–479.

    Google Scholar 

  • Daane, K. M., Steffan, S.A., Yokota, G. Y., and Michaelides, T. J. 2000. Biological investigations of hemipteran pests to improve control and reduce the spread of the fungus Botryosphaeria dothidea. California Pistachio Industry Annual Report, CropYear 1999-2000; California Pistachio Commission, Fresno California, pp. 119–120.

    Google Scholar 

  • Federici, B. A. 1999. Broadscale use of pest-killing plants to be true test. Cal. Agric. 52:14–20.

    Google Scholar 

  • Gilby, A. R. and Waterhouse, D. F. 1965. The composition of the scent of the green vegetable bug Nezara viridula. Proc. R. Soc. London, Ser. B, Biol. Sci. 162:105–120.

    Google Scholar 

  • Greene, J. K., Turnipseed, S. G., Sullivan, M. J., and Herzog, G.A. 1999. Boll damage by southern green stink bug (Hemiptera: Pentatomidae) and tarnished plant bug (Hemiptera: Miridae) caged on transgenic Bacillus thuringiensis cotton. J. Econ. Entomol. 92:941–944.

    Google Scholar 

  • Hall, S. S., McEnroe, F. J., and Shue, H.-J. 1975. A convenient synthesis of the sesquiterpene (α)-α)-curcumene. VI. Application of alkylation-reduction to the total synthesis of terpenes. J. Org. Chem. 40:3306–3307.

    Google Scholar 

  • Harris, V. E. and Todd, J. W. 1980. Male-mediated aggregation of male, female and 5th-instar southern green stink bugs and concomitant attraction of a tachinid parasite, Trichopoda pennipes. Entomol. Exp. Appl. 27:117–126.

    Google Scholar 

  • Ho, H.-Y. and Millar, J. G. 2001a. Identification and synthesis of a male produced sex pheromone from the stink bug Chlorochroa sayi. J. Chem. Ecol. 27:1177–1201.

    Google Scholar 

  • Ho, H.-Y. and Millar, J. G. 2001b. Identification and synthesis of male-produced sex pheromone components of the stink bugs Chlorochroa ligata and Chlorochroa uhleri. J. Chem. Ecol. 27:2067–2095.

    Google Scholar 

  • Jackman, L. M. 1960. Hydrogenation-dehydrogenation reactions, pp. 329–364 in R. Raphael, E. C. Taylor, and H. Wynberg (eds.). Advances in Organic Chemistry. Methods and Results. Volume II. Interscience Publishers, New York.

    Google Scholar 

  • James, D. G., Heffer, R., and Amaike, M. 1996. Field attraction of Biprorulus bibax Breddin (Hemiptera: Pentatomidae) to synthetic aggregation pheromone and (E)-2-hexenal, a pentatomid defense chemical. J. Chem. Ecol. 22:1697–1708.

    Google Scholar 

  • Joulain, D. and KÖnig, W. A. 1998. The Atlas of Spectral Data of Sesquiterpene Hydrocarbons. E.B.-Verlag, Hamburg, Germany.

    Google Scholar 

  • KÖnig, W. A., Rieck, A., Hardt, I., Gehrcke, B., Kubeczka, K.-H., and Muhle, H. 1994. Enantiomeric composition of the chiral constituents of essential oils. Part 2: Sesquiterpene hydrocarbons. J. High Resolut. Chromatogr. 17:315–320.

    Google Scholar 

  • Leal, W. S., Kuwahara, S., Shi, X. W., Higuchi, H., Marino, C. E. B., Ono, M., and Meinwald, J. 1998. Male-released sex pheromone of the stink bug Piezodorus hybneri. J. Chem Ecol. 24:1817–1829.

    Google Scholar 

  • Lucchi, A. 1994. The scent gland system of Nezara viridula (L.) (Heteroptera Pentatomidae). III. Male ventral abdominal glands. Redia 77:1–10.

    Google Scholar 

  • Marques, F. A., McElfresh, J. S., and Millar, J. G. 2000. Female-produced sex pheromone of the predatory bug Geocoris punctipes. J. Chem. Ecol. 26:2843–2855.

    Google Scholar 

  • McBrien, H.M. and Millar, J.G. 1999. Phytophagous bugs, pp. 277–304 in J. Hardie and A. K. Minks (eds.). Pheromones of Non-Lepidopteran Insects Associated with Agricultural Plants. CABI Publishers, Wallingford, United Kingdom.

    Google Scholar 

  • McBrien, H. M., Millar, J. G., Gottlieb, L., Chen, X., and Rice, R. E. 2001. Male produced sex attractant pheromone of the green stink bug, Acrosternum hilare. J. Chem. Ecol. 27:1821–1839.

    Google Scholar 

  • McGhee, P. and Brunner, J. F. 1996. Biology and management of stink bugs in tree fruit. Paper 0423, Annual Meeting of the Entomological Society of America, Louisville, Kentucky, December 8-12, 1996.

  • McPherson, J. E. and McPherson, R. M. 2000. Stink Bugs of Economic Importance in America North of Mexico. CRC Press, Boca Raton, Florida.

    Google Scholar 

  • Miklas, N., Renou, M., Çokl, A., and Virant-Doberlet, M. 1999. Songs and pheromone interplay in sexual communication in Nezara viridula (Heteroptera: Pentatomidae). Poster #111, 16th Annual Meeting, International Society of Chemical Ecology; Marseille, November 13-17, 1999.

  • Millar, J. G. 1997. Methyl (2E,4Z,6Z)-deca-2,4,6-trienoate, a thermally unstable, sex-specific compound from the stink bug Thyanta pallidovirens. Tetrahedron Lett. 38:7971–7972.

    Google Scholar 

  • Millar, J. G. 1998. Rapid and simple isolation of zingiberene from essential oils. J. Nat. Prod. 61:1025–1026.

    Google Scholar 

  • Millar, J. G., Rice, R. E., Steffan, S. A., Daane, K. M., Cullen, E., and Zalom, F. G. 2001. Attraction of female digger wasps, Astata occidentalis Cresson (Hymenoptera: Sphecidae) to the sex pheromone of the stink bug Thyanta pallidovirens. Pan-Pac. Entomol. 77:244–248.

    Google Scholar 

  • Mitchell, W. C. and Mau, R. F. L 1971. Response of the female southern green stink bug and its parasite, Trichopoda pennipes, to male stink bug pheromones. J. Econ. Entomol. 64:856–859.

    Google Scholar 

  • Ota, D. and Çokl, A. 1991. Mate location in the southern green stink bug, Nezara viridula, mediated through substrate-borne signals on ivy. J. Insect Behav. 4:441–447.

    Google Scholar 

  • Pavis, C. and Malosse, C. 1986. A sex pheromone produced by mature males in the southern green stink bug, Nezara viridula (L.) (Heteroptera: Pentatomidae). C. R. Acad. Sci. III-Sci. Vie 303:273–276.

    Google Scholar 

  • Rice, R. E., Bentley, W. J., and Beede, R. H. 1988. Insect and mite pests of pistachios in California. University of California Division of Agricultural and Natural Resources, Pub #21452, Oakland, California.

  • Rider, D. A. and Chapin, J. B. 1992. Revision of the genus Thyanta Stål, 1862 (Heteroptera: Pentatomidae) II. North America, Central America, and theWest Indies. J. N.Y. Entomol. Soc. 100:42–98.

    Google Scholar 

  • Schaefer, C. W. and Panizzi, A. R. (eds.). 2000. Heteroptera of Economic Importance. CRC Press, Boca Raton, Florida.

    Google Scholar 

  • Schotzko, D. J. and O'keeffe, L. E. 1990. Effect of pea and lentil development on reproduction and longevity of Thyanta pallidovirens (Stal) (Hemiptera, Heteroptera, Pentatomidae. J. Econ. Entomol. 83:1333–1337.

    Google Scholar 

  • Steel, R. G. D., Torrie, J. H., and Dickey, D. A. 1997. Principles and Procedures of Statistics: A Biometrical Approach, 3rd ed. McGraw-Hill, New York.

    Google Scholar 

  • Sugie, H., Yoshida, M., Kawasaki, K., Noguchi, H., Moriya, S., Takagi, K., Fukuda, H., Fujiie, A., Yamanaka, M., Ohira, Y., Tsutsumi, T., Tsuda, K., Fukumoto, K., Yamashita, M., and Suzuki, H. 1996. Identification of the aggregation pheromone of the brown-winged green bug, Plautia stali Scott (Heteroptera: Pentatomidae). Appl. Entomol. Zool. 31:427–431.

    Google Scholar 

  • Sy, L.-K. and Brown, G. D. 1997. Total assignment of the 1H and 13C NMR chemical shifts of three bisabolane hydrocarbons by 2D-NMR spectroscopy. Magn. Reson. Chem. 35:424–425.

    Google Scholar 

  • Turnipseed, S. G. and Greene, J. K. 1996. Strategies for managing stink bugs in transgenic B. t. cotton. Proceedings, 1996 Beltwide Cotton Conference, National Cotton Council of America, Memphis, Tennessee, pp. 936–938. WANG, Q. and MILLAR, J. G. 1997. Reproductive behavior of Thyanta pallidovirens (Heteroptera: Miridae). Ann. Entomol. Soc. Am. 90:380-388.

  • Wilson, F. D., Flint, H. M., Deaton, W. R., Fischoff, D. A., Perlak, F. J., Armstrong, T. A., Fuchs, R. L., Berberich, S. A., Parks, N. J., and Stapp, B. R. 1992. Resistance of cotton lines containing a Bacillus thuringiensis toxin to pink bollworm (Lepidoptera: Gelechiidae) and other insects. J. Econ. Entomol. 85:1516–1521.

    Google Scholar 

  • Zar, J. H. 1984. Biostatistical Analysis, 2nd ed. Prentice-Hall, Englewood Cliffs, New Jersey.

    Google Scholar 

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McBrien, H.L., Millar, J.G., Rice, R.E. et al. Sex Attractant Pheromone of the Red-Shouldered Stink Bug Thyanta pallidovirens: A Pheromone Blend with Multiple Redundant Components. J Chem Ecol 28, 1797–1818 (2002). https://doi.org/10.1023/A:1020513218454

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