Electroantennogram responses of six Bactrocera and Zeugodacus species to raspberry ketone analogues
Matthew S. Siderhurst A D , Soo J. Park B , Ian M. Jamie B and Stefano G. De Faveri C
+ Author Affiliations
- Author Affiliations
A Department of Chemistry, Eastern Mennonite University, 1200 Park Road, Harrisonburg, VA 22802, USA.
B Department of Molecular Sciences, Macquarie University, North Ryde, NSW 2109, Australia.
C Department of Agriculture and Fisheries, 28 Peters Street, Mareeba, Qld 4880, Australia.
D Corresponding author. Email: matthew.siderhurst@emu.edu
Environmental Chemistry 14(6) 378-384 https://doi.org/10.1071/EN17091
Submitted: 4 May 2017 Accepted: 6 July 2017 Published: 23 November 2017
Environmental context. Queensland fruit fly is a major pest of fruits and vegetables in eastern Australia, sometimes causing complete loss of unprotected crops. Odours that attract fruit flies can help control these pests and this study investigated how six fruit fly species smell these chemicals. The strength of fly responses to tested odours gives insight into the way flies smell and provides information for making better attractants, potentially reducing insecticide use.
Abstract. The Queensland fruit fly (Bactrocera tryoni, Q-fly) is a major horticultural pest in eastern Australia. The deployment of male lures comprises an important component of several detection and control strategies for this pest. A novel fluorinated analogue of raspberry ketone (RK), raspberry ketone trifluoroacetate (RKTA), has been developed with the aim of further improving Q-fly control. RKTA elicited strong electroantennogram (EAG) responses from Q-flies whereas cuelure (CL) and melolure (ML) responses were not significantly greater than a negative control. Further experimentation showed that RKTA also elicited EAG response from five other fruit fly species, included flies known to be strongly attracted to CL (B. neohumeralis, B. kraussi and B. frauenfeldi), weakly attracted to CL (B. jarvisi), or non-responsive to CL (Zeugodacus cucumis), whereas seven other compounds, RK, CL, ML, raspberry ketone difluoroacetate, raspberry ketone monofluoroacetate, anisyl acetone and trimethylsilyl raspberry ketone, elicited only weak responses comparable with a negative control. However, fly EAG responses to RKTA are likely due at least in part to trifluoroethanoic acid, which is a hydrolysis product of RKTA and elicited strong EAG responses from all six species when tested alone. Furthermore, whereas ethanoic acid, methanoic acid and trifluoroethanoic acid all elicited strong EAG responses in Q-flies, the only corresponding RK ester to elicit an EAG response was RKTA, suggesting that RKTA hydrolyses quickly, whereas CL and ML do not. This is in contrast to the idea that CL readily hydrolyses on contact with atmospheric moisture, an assertion that has been made in the literature repeatedly.
Additional keywords: Bactrocera tryoni, cuelure, fruit fly, melolure, lures, tephritidae.
References
[1] R. A. I. Drew, The tropical fruit flies (Diptera: Tephritidae: Dacinae) of the Australasian and Oceanian regions. Mem. Queensl. Mus. 1989, 26, 1.[2] R. W. Sutherst, T. Yonow, The geographical distribution of the Queensland fruit fly, Bactrocera (Dacus) tryoni, in relation to climate. Aust. J. Agric. Res. 1998, 49, 935.
| The geographical distribution of the Queensland fruit fly, Bactrocera (Dacus) tryoni, in relation to climate.Crossref | GoogleScholarGoogle Scholar |
[3] A. R. Clarke, L. S. Powell, C. W. Weldon, P. W. Taylor, The ecology of Bactrocera tryoni (Diptera: Tephritidae): what do we know to assist pest management? Ann. Appl. Biol. 2011, 158, 26.
| The ecology of Bactrocera tryoni (Diptera: Tephritidae): what do we know to assist pest management?Crossref | GoogleScholarGoogle Scholar |
[4] R. Osborne, A. Meats, M. Frommer, J. A. Sved, R. A. I. Drew, M. K. Robson, Australian distribution of 17 species of fruit flies (Diptera: Tephritidae) caught in cue lure in February 1994. Ann. Appl. Biol. 1997, 36, 45.
[5] B. C. Dominiak, D. Daniels, Review of the past and present distribution of Mediterranean fruit fly (Ceratitis capitata Weidemann) and Queensland fruit fly (Bactrocera tryoni Froggatt) in Australia. Aust. J. Entomol. 2012, 51, 104.
| Review of the past and present distribution of Mediterranean fruit fly (Ceratitis capitata Weidemann) and Queensland fruit fly (Bactrocera tryoni Froggatt) in Australia.Crossref | GoogleScholarGoogle Scholar |
[6] R. W. Sutherst, B. S. Collyer, T. Yonow, The vulnerability of Australian horticulture to the Queensland fruit fly, Bactrocera (Dacus) tryoni, under climate change. Aust. J. Agric. Res. 2000, 51, 467.
| The vulnerability of Australian horticulture to the Queensland fruit fly, Bactrocera (Dacus) tryoni, under climate change.Crossref | GoogleScholarGoogle Scholar |
[7] M. Beroza, B. H. Alexander, L. F. Steiner, W. C. Mitchell, D. H. Miyashita, New synthetic lures for the male melon fly. Science 1960, 131, 1044.
| New synthetic lures for the male melon fly.Crossref | GoogleScholarGoogle Scholar | 1:STN:280:DC%2BC3cvhtlWktg%3D%3D&md5=f2c04cfcb8a0c64ad746b4bb33588642CAS |
[8] L. Bauer, A. J. Birch, A. J. Ryan, Studies in relation to biosynthesis. VI. Rheosmin. Aust. J. Chem. 1955, 8, 534.
| Studies in relation to biosynthesis. VI. Rheosmin.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG28Xlt1Gksw%3D%3D&md5=21af80f97180ac765a19c0c9c375db79CAS |
[9] B. H. Alexander, M. Beroza, T. A. Oda, L. F. Steiner, D. H. Miyashita, W. C. Mitchell, The development of male melon fly attractants. J. Agric. Food Chem. 1962, 10, 270.
| The development of male melon fly attractants.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF2cXks1Cqs7c%3D&md5=70d9cfe9847bcb73e1ff0b13f9e7b155CAS |
[10] S. J. Park, R. Morelli, B. L. Hanssen, J. F. Jamie, I. M. Jamie, M. S. Siderhurst, P. W. Taylor, Raspberry ketone analogs: vapour pressure measurements and attractiveness to Queensland fruit fly, Bactrocera tryoni (Froggatt) (Diptera: Tephritidae). PLoS One 2016, 11, e0155827.
| Raspberry ketone analogs: vapour pressure measurements and attractiveness to Queensland fruit fly, Bactrocera tryoni (Froggatt) (Diptera: Tephritidae).Crossref | GoogleScholarGoogle Scholar |
[11] R. L. Metcalf, E. R. Metcalf, Fruit flies of the family Tephritidae, in Plant Kairomones in Insect Ecology and Control (Eds R. L. Metcalf, E. R. Metcalf) 1992, pp. 109–52 (Chapman Hall: New York, NY).
[12] V. Casaña-Giner, J. E. Oliver, E. Jang, L. Carvalho, Syntheses and behavioral evaluations of fluorinated and silylated analogs of raspberry ketone as attractants for the melon fly, Bactrocera cucurbitae (Coquillett). J. Entomol. Sci. 2003, 38, 111.
[13] V. Casaña-Giner, J. E. Oliver, E. B. Jang, L. Carvalho, A. Khrimian, A. B. DeMilo, G. T. Mcquate, Raspberry ketone formate as an attractant for the melon fly (Diptera: Tephritidae). J. Entomol. Sci. 2003, 38, 120.
[14] R. L. Metcalf, E. R. Metcalf, W. C. Mitchell, Benzyl acetate as attractants for male oriental fruit fly, Dacus dorsalis, and the male melon fly, Dacus cucurbitae. Proc. Natl. Acad. Sci. USA 1986, 83, 1549.
| Benzyl acetate as attractants for male oriental fruit fly, Dacus dorsalis, and the male melon fly, Dacus cucurbitae.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL28XktVaiu78%3D&md5=e608df902dc9ce99eff73c62e61cbb50CAS |
[15] R. L. Metcalf, W. C. Mitchell, E. R. Metcalf, Olfactory receptors in the melon fly Dacus cucurbitae and the oriental fruit fly Dacus dorsalis. Proc. Natl. Acad. Sci. USA 1983, 80, 3143.
| Olfactory receptors in the melon fly Dacus cucurbitae and the oriental fruit fly Dacus dorsalis.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3sXktlKhu7Y%3D&md5=8b812280b363b4d534b47eeaeb70ed47CAS |
[16] R. L. Metcalf, Chemical ecology of Dacinae fruit flies (Diptera: Tephritidae). Ann. Entomol. Soc. Am. 1990, 83, 1017.
| Chemical ecology of Dacinae fruit flies (Diptera: Tephritidae).Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXktVGgs78%3D&md5=c36260648438cfc3d2a199834ef881a9CAS |
[17] K. Rameash, J. Thomas, M. Chellapan, M. P. Mathew, Studies on dispensers of melolure in the attraction of melon fly, Bactrocera cucurbitae. Indian J. Plant Prot. 2009, 37, 55.
[18] R. I. Vargas, J. C. Piñero, E. B. Jang, R. F. L. Mau, J. D. Stark, L. Gomez, L. Stoltman, A. Mafra-Neto, Response of melon fly (Diptera: Tephritidae) to weathered SPLAT-Spinosad-Cue-Lure. J. Econ. Entomol. 2010, 103, 1594.
| Response of melon fly (Diptera: Tephritidae) to weathered SPLAT-Spinosad-Cue-Lure.Crossref | GoogleScholarGoogle Scholar |
[19] E. B. Jang, V. Casana-Giner, J. E. Oliver, Field captures of wild melon fly (Diptera: Tephritidae) with an improved male attractant, raspberry ketone formate. J. Econ. Entomol. 2007, 100, 1124.
| Field captures of wild melon fly (Diptera: Tephritidae) with an improved male attractant, raspberry ketone formate.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtVWktLzM&md5=10a023bebf725c1f30e092449a888e3bCAS |
[20] T. Shelly, J. Renshaw, R. Dunivin, T. Morris, T. Giles, E. Andress, A. Diaz, M. War, J. Nishimoto, R. Kurashima, Release–recapture of Bactrocera fruit flies (Diptera:Tephritidae): comparing the efficacy of liquid and solid formulations of male lures in Florida, California and Hawaii. Fla. Entomol. 2013, 96, 305.
| Release–recapture of Bactrocera fruit flies (Diptera:Tephritidae): comparing the efficacy of liquid and solid formulations of male lures in Florida, California and Hawaii.Crossref | GoogleScholarGoogle Scholar |
[21] B. C. Dominiak, A. J. Campbell, E. B. Jang, A. Ramsey, B. G. Fanson, Field evaluation of melolure, a formate analogue of cuelure, in Sydney, New South Wales, Australia. J. Econ. Entomol. 2013, 108, 1176.
| Field evaluation of melolure, a formate analogue of cuelure, in Sydney, New South Wales, Australia.Crossref | GoogleScholarGoogle Scholar |
[22] M. S. Siderhurst, S. J. Park, C. N. Buller, I. M. Jamie, N. C. Manoukis, E. B. Jang, P. W. Taylor, Raspberry ketone trifluoroacetate, a new attractant for the Queensland fruit fly, Bactrocera tryoni (Froggatt). J. Chem. Ecol. 2016, 42, 156.
| Raspberry ketone trifluoroacetate, a new attractant for the Queensland fruit fly, Bactrocera tryoni (Froggatt).Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC28XksFCmt78%3D&md5=a9135be6e739eb254cfb1f5d2ae42ae0CAS |
[23] M. S. Siderhurst, E. B. Jang, Female-biased attraction of oriental fruit fly, Bactrocera dorsalis (Hendel), to a blend of host fruit volatiles from Terminalia catappa L. J. Chem. Ecol. 2006, 32, 2513.
| Female-biased attraction of oriental fruit fly, Bactrocera dorsalis (Hendel), to a blend of host fruit volatiles from Terminalia catappa L.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xht1Wgu7fP&md5=3841eccb9d0fad7f049198ff7f11d119CAS |
[24] A. Zhang, C. Linn, S. Wright, R. Prokopy, W. Reissig, W. Roelofs, Identification of a new blend of apple volatiles attractive to the apple maggot, Rhagoletis pomonella. J. Chem. Ecol. 1999, 25, 1221.
| Identification of a new blend of apple volatiles attractive to the apple maggot, Rhagoletis pomonella.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXktlersLg%3D&md5=fdc5cfe5363cf4a3473a144f311e225eCAS |
[25] L. Cruz-López, E. A. Malo, J. C. Rojas, Sex pheromone of Anastrepha striata. J. Chem. Ecol. 2015, 41, 458.
| Sex pheromone of Anastrepha striata.Crossref | GoogleScholarGoogle Scholar |
[26] J. Alagarmalai, D. Nestel, D. Dragushich, E. Nemny-Lavy, L. Anshelevich, A. Zada, V. Soroker, Identification of host attractants for the Ethiopian fruit fly, Dacus ciliatus Loew. J. Chem. Ecol. 2009, 35, 542.
| Identification of host attractants for the Ethiopian fruit fly, Dacus ciliatus Loew.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXmtlWlsbc%3D&md5=e1283d151f790c00d5953624d39d719fCAS |
[27] M. S. Siderhurst, E. B. Jang, Cucumber volatile blend attractive to female melon fly, Bactrocera cucurbitae (Coquillett). J. Chem. Ecol. 2010, 36, 699.
| Cucumber volatile blend attractive to female melon fly, Bactrocera cucurbitae (Coquillett).Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXotlChu7s%3D&md5=21397300103ce90ec02dbc5e086182f1CAS |
[28] P. E. Kendra, W. S. Montgomery, N. D. Epsky, R. R. Heath, Electroantennogram and behavioral responses of Anastrepha suspensa (Diptera: Tephritidae) to putrescine and ammonium bicarbonate lures. Environ. Entomol. 2009, 38, 1259.
| Electroantennogram and behavioral responses of Anastrepha suspensa (Diptera: Tephritidae) to putrescine and ammonium bicarbonate lures.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtVKrt7jP&md5=501773b0136feafe19f0ecada5ca16b7CAS |
[29] E. B. Jang, D. M. Light, J. C. Dickens, T. P. McGovern, J. T. Nagata, Electroantennogram responses of Mediterranean fruit fly, Ceratitis capitata (Diptera: Tephritidae) to trimedlure and its trans isomers. J. Chem. Ecol. 1989, 15, 2219.
| Electroantennogram responses of Mediterranean fruit fly, Ceratitis capitata (Diptera: Tephritidae) to trimedlure and its trans isomers.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXlsVyrsb4%3D&md5=bc5ac32e967d54e142a985ed7403860bCAS |
[30] C. D. Hull, B. W. Cribb, Olfaction in the Queensland fruit fly, Bactrocera tryoni. I: Identification of olfactory receptor neuron types responding to environmental odors. J. Chem. Ecol. 2001, 27, 871.
| Olfaction in the Queensland fruit fly, Bactrocera tryoni. I: Identification of olfactory receptor neuron types responding to environmental odors.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXlt1GgsL8%3D&md5=0169122d6aa093c1fbf2ce378f8b0b17CAS |
[31] C. D. Hull, B. W. Cribb, Olfaction in the Queensland fruit fly, Bactrocera tryoni. II: Response spectra and temporal encoding characteristics of the carbon dioxide receptors. J. Chem. Ecol. 2001, 27, 889.
| Olfaction in the Queensland fruit fly, Bactrocera tryoni. II: Response spectra and temporal encoding characteristics of the carbon dioxide receptors.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXlt1GgsLw%3D&md5=044b8ed364190eb15a374d67cdb0714cCAS |
[32] D. Pérez-Staples, C. W. Weldon, C. Smallridge, P. W. Taylor, Pre-lease feeding on yeast hydrolysate enhances sexual competitiveness of sterile male Queensland fruit flies in field cages. Entomol. Exp. Appl. 2009, 131, 159.
| Pre-lease feeding on yeast hydrolysate enhances sexual competitiveness of sterile male Queensland fruit flies in field cages.Crossref | GoogleScholarGoogle Scholar |
[33] C. W. Weldon, J. Prenter, P. W. Taylor, Activity patterns of Queensland fruit flies (Bactrocera tryoni) are affected by both mass-rearing and sterilization. Physiol. Entomol. 2010, 35, 148.
| Activity patterns of Queensland fruit flies (Bactrocera tryoni) are affected by both mass-rearing and sterilization.Crossref | GoogleScholarGoogle Scholar |
[34] B. Fanson, S. Sundaralingam, L. Jiang, B. Dominiak, G. D’arcy, A review of 16 years of quality control parameters at a mass‐rearing facility producing Queensland fruit fly, Bactrocera tryoni.. Entomol. Exp. Appl. 2014, 151, 152.
| A review of 16 years of quality control parameters at a mass‐rearing facility producing Queensland fruit fly, Bactrocera tryoni..Crossref | GoogleScholarGoogle Scholar |
[35] N. W. Heather, R. J. Corcoran, Dacus tryoni, in Handbook of Insect Rearing (Eds P. Singh, R. F. Moore) 1985, pp. 41–8 (Elsevier: Amsterdam).
[36] B. Neises, W. Steglich, Simple method for the esterification of carboxylic acids. Angew. Chem. Int. Ed. Engl. 1978, 17, 522.
| Simple method for the esterification of carboxylic acids.Crossref | GoogleScholarGoogle Scholar |
[37] T. Poisson, V. Dalla, C. Papamicaël, G. Dupas, F. Marsais, V. Levacher, DMAP-organocatalyzed O-silyl-O-(or C-)-benzoyl interconversions by means of benzoyl fluoride. Synlett 2007, 3, 0381.
| DMAP-organocatalyzed O-silyl-O-(or C-)-benzoyl interconversions by means of benzoyl fluoride.Crossref | GoogleScholarGoogle Scholar |
[38] JMP Statistical Discovery Software, version 10.0.0, SAS Institute 2012 (SAS Institute Inc.: Cary, NC).
[39] K. Lee, J. Lin, C. Wu, Electroantennogram of the oriental fruit fly, Bactrocera dorsalis (Hendel) (Diptera: Trypetidae) to some short-chain organic acids. Chin. J. Entomol 1998, 18, 1.
[40] B. Dominiak, C. Clifford, S. Nielsen, Queensland fruit fly (Bactrocera tryoni Froggatt) attraction to and chemical analysis of male annihilation blocks using three concentrations of cuelure at Dubbo, New South Wales, Australia. Plant Prot. Q. 2009, 24, 157.
[41] R. Drew, The responses of fruit fly species (Diptera: Tephritidae) in the South Pacific area to male attractants. Aust. J. Entomol. 1974, 13, 267.
| The responses of fruit fly species (Diptera: Tephritidae) in the South Pacific area to male attractants.Crossref | GoogleScholarGoogle Scholar |
[42] R. L. Metcalf, Chemical ecology of Dacinae fruit flies (Diptera: Tephritidae). Ann. Entomol. Soc. Am. 1990, 83, 1017.
| Chemical ecology of Dacinae fruit flies (Diptera: Tephritidae).Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXktVGgs78%3D&md5=c36260648438cfc3d2a199834ef881a9CAS |
[43] S. J. Park, M. S. Siderhurst, I. Jamie, P. W. Taylor, Hydrolysis of Queensland fruit fly, Bactrocera tryoni (Froggatt), attractants: kinetics and implications for biological activity. Aust. J. Chem. 2016, 69, 1162.
| Hydrolysis of Queensland fruit fly, Bactrocera tryoni (Froggatt), attractants: kinetics and implications for biological activity.Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC28Xhs1aqt7rK&md5=3768d0323175cc774a484328a7b07f53CAS |
