Male-produced pheromone of Spathius agrili, a parasitoid introduced for the biological control of the invasive emerald ash borer, Agrilus planipennis

Journal of Chemical Ecology

Volumn 38, Issue 4, 2012, Pages 389-399

  Cossé, Allard A ^a   Petroski, Richard J ^a   Zilkowski, Bruce W ^a   Vermillion, Karl ^a   Lelito, Jonathan P ^b   Cooperband, Miriam F ^b   Gould, Juli R ^b  

^a NATIONAL CENTER FOR AGRICULTURAL UTILIZATION RESEARCH   (United States)

^b UNITED STATES DEPARTMENT OF AGRICULTURE   (United States)

Author keywords

(4R,11E) tetradecen 4 olide; Biocontrol; Braconidae; Flight tunnel behavior; Hymenoptera; Invasive; Pheromone; Spathius agrili

Indexed keywords

PHEROMONE;

BAIT; BEETLE; BIOASSAY; BIOCONTROL AGENT; BIOLOGICAL CONTROL; DECIDUOUS TREE; DETECTION METHOD; INVASIVE SPECIES; PARASITOID; PEST SPECIES; PHEROMONE; TRAP (EQUIPMENT); WASP;

ANIMAL; ANIMAL BEHAVIOR; ARTICLE; BEETLE; BIOASSAY; BIOLOGICAL PEST CONTROL; DRUG EFFECT; FEMALE; HYMENOPTERA; INTRODUCED SPECIES; KINETICS; MALE; METABOLISM; METHODOLOGY; PARASITOLOGY; PHYSIOLOGY; SECRETION; SEXUAL DEVELOPMENT; SYNTHESIS;

ANIMALS; BEETLES; BEHAVIOR, ANIMAL; BIOLOGICAL ASSAY; FEMALE; HYMENOPTERA; INTRODUCED SPECIES; KINETICS; MALE; PEST CONTROL, BIOLOGICAL; PHEROMONES; SEX CHARACTERISTICS;

UNITED STATES;

AGRILUS PLANIPENNIS; BRACONIDAE; BUPRESTIDAE; COLEOPTERA; FRAXINUS; HYMENOPTERA; SPATHIUS AGRILI;

EID: 84859748876     PISSN: 00980331     EISSN: 15731561     Source Type: Journal    
DOI: 10.1007/s10886-012-0101-2     Document Type: Article

References (39)

1. Analytical Software. 1998. Statistix for Windows User's Manual. Analytical Software, Tallahassee, Florida.
2. Attygalle, A. B. 1998. Microchemical techniques, pp. 207-294, in J. G. Millar and K. F. Haynes (eds.), Methods in Chemical Ecology, Volume 1, Chemical Methods. Kluwer, Boston.
3. Ayasse, M., Paxton, R. J., and Tengö, J. 2001. Mating behavior and chemical communication in the order Hymenoptera. Annu Rev Entomol 46: 31-78.
4. Baker, K. V., Brown, J. M., Hughes, N., Skarnulis, A. J., and Sexton, A. 1991. Mechanical activation of magnesium turnings for the preparation of reactive Grignard reagents. J Org Chem 56: 698-703.
5. Bartelt, R. J., Schaner, A. M., and Jackson, L. L. 1989. Aggregation pheromone components in Drosophila mulleri. A chiral ester and an unsaturated ketone. J Chem Ecol 15: 399-411.
6. Bartelt, R. J., Dowd, P. F., Plattner, R. D., and Weisleder, D. 1990. Aggregation pheromone of driedfruit beetle. Carpophilus hemipterus: Wind-tunnel bioassay and identification of two novel tetraene hydrocarbons. J Chem Ecol 16: 1015-1039.
7. Bauer, L. S., Liu, Houping, Gao, Ruitong, Zhao, and Tonghai. 2006. Egg and larval parasitoids of emerald ash borer from China: potential for biocontrol in North America, pp. 48-49, in V. Mastro, R. Reardon, and G. Parra (comps). Proceedings of the 2005 emerald ash borer research and technology development meeting; 2005 September 26-27; Pittsburgh, PA. FHTET-2005-16. Morgantown, WV: U. S. Department of Agriculture, Forest Service, Forest Health Technology Enterprise Team.
8. Bauer, L. S., Liu, Houping, and Miller, D. 2009. Emerald ash borer biological control: rearing, releasing, establishment, and efficacy of parasitoids, pp. 7-8, in K. A. McManus, K. W. Gottschalk (eds.). Proceedings. 20th U. S. Department of Agriculture interagency research forum on invasive species 2009; 2009 January 13-16; Annapolis, MD. Gen. Tech. Rep. NRS-P-51. Newtown Square, PA: U. S. Department of Agriculture, Forest Service, Northern Research Station.
9. Bauer, L. S., Gould, J., Duan, J., and Ulyshen, M. 2011. Emerald ash borer biological control, pp. 70-73, in K. A. McManus, K. W. Gottschalk (eds.). Proceedings. 21st U. S. Department of Agriculture interagency research forum on invasive species 2010; 2010 January 12-15; Annapolis, MD. Gen. Tech. Rep. NRS-P-75. Newtown Square, PA: U. S. Department of Agriculture, Forest Service, Northern Research Station.
10. Bloch, R. and Brillet, C. 1991. Selective oxidation of primary-secondary diols to lactones catalyzed by tetrapropylammonium perruthenate. Synlett 1991: 829-830.
11. Collatz, J., Tolasch, T., Johannes, L., and Steidle, M. 2009. Mate finding in the parasitic wasp Cephalonomia tarsalis (Ashmead): more than one way to a female's heart. J Chem Ecol 35: 761-768.
12. Cooperband, M., Cossé, A., Hartness, A., and Mastro, V. C. 2011. Color preferences of Spathius agrili, a parasitoid of emerald ash borer. Poster presentation at: 2011 Emerald Ash Borer research and technology development meeting; 2011 October 12-13; Wooster, OH.
13. Cossé, A. A., Bartelt, R. J., James, D. G., and Petroski, R. J. 2001. Identification of a female-specific, antennally active volatile compound of the currant stem girdler. J Chem Ecol 27: 1841-1853.
14. Cossé, A. A., Petroski, R. J., Zilkowski, B. W., Lelito, J. P., and Gould, R. J. 2011. Pheromones of Spathius agrili and S. floridanus: Exotic and native parasitoids of the invasive emerald ash borer. Poster presented at: 27th Meeting of the International Society of Chemical Ecology, 24-28 July 2011; Vancouver, B. C., Canada.
15. El-Sayed, A. M., Gödde, J., and Arn, H. 1999. Sprayer for quantitative application of odor stimuli. Environ Entomol 28: 947-953.
16. El-sayed, A. M. 2011. The Pherobase: Database of Pheromones and Semiochemicals. (http://www. pherobase. com).
17. Emerald Ash Borer Info 2011. (http://emeraldashborer. info).
18. Haack, R. A., Jendek, E., Liu, H., Marchant, K. R., Petrice, T. R., Poland, T. M., and Ye, H. 2002. The emerald ash borer: A new exotic pest in North America. Newsletter Michigan Entomol Soc 47: 1-5.
19. Hijfte, L. V., Little, R. D., Petersen, J. L., and Moeller, K. D. 1987. Intramolecular 1, 3-diyl trapping reactions. Total synthesis of (±)-hypnophilan and (±)-coriolin. Formation of the trans-fused bicycle[3. 3. 0]octane ring system. J Org Chem 52: 4647-4661.
20. James, D. G., Petroski, R. J., Cossé, A. A., Zilkowski, B. W., and Bartelt, R. J. 2003. Bioactivity, synthesis, and chirality of the sex pheromone of currant stem girdler, Janus integer. J Chem Ecol 29: 2189-2199.
21. Keeling, C., Plettner, E., and Slessor, K. N. 2004. Hymenopteran Semiochemicals. Topics Curr Chem 239: 133-177.
22. Kuklev, D. V. and Smith, W. L. 2006. Chemical C2-elongation of polyunsaturated fatty acids. Chem Phys Lipids 144: 172-177.
23. Leal, W. S., Kuwahara, S., Ono, M., and Kubota, S. 1996. (R, Z)-7, 15-hexadecadien-4-olide, sex pheromone of the yellowish elongate chafer, Heptophylla picea. Bioorg Med Chem 4: 315-321.
24. 16 alcohols, acetates and aldehydes commonly found in lepidopteran pheromone blends. J Braz Chem Soc 11: 592-599.
25. Miyashita, M., Yoshikoshi, A., and Grieco, P. A. 1977. Pyridinium-p-toluenesulfonate. A mild and efficient catalyst for the tetrahydro-pyranylation of alcohols. J Org Chem 42: 3772-3774.
26. Paddon-Jones, G. C., Moore, C. J., Breckneil, D. J., König, W. A., and Kitching, W. 1997. Synthesis and absolute stereochemistry of Hagen's-gland lactones in some parasitic wasps (Hymenoptera: Braconidae). Tett Lett 38: 3479-3482.
27. Petroski, R. J. 2003a. Preparation of monotetrahydropyranylated short-chain symmetrical diols. Syn Commun 33: 3251-3259.
28. Petroski, R. J. 2003b. Oxidation of monotetrahydropyranylated short-chain symmetrical diols. Syn Commun 33: 3243-3250.
29. Quimio, G. M. and Walter, G. H. 2000. Swarming, Delayed Sexual Maturation of Males, and Mating Behavior of Fopius arisanus (Sonan) (Hymenoptera: Braconidae). J Insect Behav 13: 797-813.
30. Ray, A. M., Swift, I. P., McElfresh, J. S., Alten, R. L., and Millar, J. G. 2011. (R)-Desmolactone, female-produced sex pheromone component of Desmocerus californicus, a longhorned beetle in the subfamily Lepturinae. Presentation presented at: 27th Meeting of the International Society of Chemical Ecology, 24-28 July 2011; Vancouver, B. C., Canada.
31. Ruther, J., Stahl, L. M., Steiner, S., Garbe, L. A., and Tolasch, T. 2007. A male sex pheromone in a parasitic wasp and control of the behavioral response by the female's mating status. J Exp Biol 210: 2163-2169.
32. Schaner, A. M. and Jackson, L. L. 1992. (Z)-10-heptadecen-2-one and other 2-ketones in the aggregation pheromone blend of Drosophila martensis, D. buzzatii, and D. serido. J Chem Ecol 18: 53-64.
33. Trost, B. M., Ball, Z. T., and Jo{double acute}ge 2002. A chemoselective reduction of alkynes to (E)-alkenes. J Am Chem Soc 124: 7922-7923.
34. WILEY 2005. Wiley. Spectral Library, [CD-ROM], 7th ed. Wiley, New York.
35. Williams, H. J., Wong, M., Wharton, R. A., and Vinson, S. B. 1988. Hagen's gland morphology and chemical content analysis for three species of parasitic wasps (Hymenoptera: Braconidae). J Chem Ecol 14: 1727-1736.
36. Willy, W. E., McKean, D. R., and Garcia, B. A. 1976. Conversion of alkyl chlorides to bromides, selective reactions of mixed bromochloroalkanes, and halogen exchange. Bull Chem Soc Jpn 49(7): 1989-1995.
37. Yang, Z. Q., Strazanac, J. S., Marsh, P. M., van Achterberg, C., and Choi, W. Y. 2005. First recorded parasitoid from China of Agrilus planipennis: A new species of Spathius (Hymenoptera: Braconidae: Doryctinae). Ann Entomol Soc Am 98: 636-642.
38. Yang, Z. Q., Wang, X. Y., Gould, J. R., Reardon, R. C., Zhang, Y. N., Liu, G. J., and Liu, E. S. 2010. Biology and behavior of Spathius agrili, a parasitoid of the emerald ash borer, Agrilus planipennis, in China. J Ins Sci 10: 1-13.
39. Zilkowski, B. W., Bartelt, R. J., Cossé, A. A., and Petroski, R. J. 2006. Male-Produced Aggregation Pheromone Compounds from the Eggplant Flea Beetle (Epitrix fuscula): Identification, Synthesis, and Field Biossays. J Chem Ecol 32: 2543-2558.