Abstract
Aromia bungii is a serious pest of stone fruit trees including cherries, plums, peaches and apricots. It is native to eastern Asia but has recently been introduced into and has established in Japan, Germany and Italy and has been intercepted in cargo entering the USA and Great Britain. We synthesized the naturally produced enantiomer of the major pheromone component, (E)-2-cis-6,7-epoxynonenal, and in field tests, comparing its attractiveness to that of the racemate. We also tested different ratios of a minor pheromone component, (2E,6Z)-nona-2,6-dienal, on attraction to the major component. Lastly, we conducted a dose–response assay to determine the optimal loading rates. Addition of the minor component at a ratio of 0.31 mg minor to 25 mg major component is more than double the trap captures of males but not females. Using this ratio, we found no difference in trap captures with 10 mg, 32 mg or 100 mg of the major component, but the 10 mg load attracted significantly more females than the 3.2 mg load, and only the 32 mg load attracted significantly more males than the 3.2 mg load. The natural enantiomer was significantly more attractive to females than the racemate. However, the multi-step, low-yielding synthesis likely will prohibit the insect-produced enantiomer from being used for operational trapping. The addition of the minor component to the racemate significantly increased trap catches, and the dose–response assay did not indicate significant differences in loads above 10 mg of the racemic major component when formulated with ~ 1.2% of the minor component.
Similar content being viewed by others
References
Anonymous (2013) The first longicorn beetle in Japan confirmed in Aichi, damaging cherry and Japanese apricot trees (June 21, 2013). Jpn Agric News. http://english.agrinews.co.jp/?p=482. Accessed 26 Mar 2017
Anonymous (2015) Aromia bungii (Coleoptera: Cerambycidae). Redneck longhorned beetle. Eur Med Plant Prot Org Bull OEPP/EPPO Bull 45(1):4–8. https://gd.eppo.int/download/doc/297_ds_AROMBU_en.pdf. Accessed 9 July 2018
Burmeister EG, Hendrich L, Balke M (2012) Der Asiatische Moschusbock Aromia bungii (Faldermann, 1835)—Erstfund für Deutschland. Nachr bl Bayer Entomol 61:29–31
CABI (2018) Datasheet, Aromia bungii (red necked longicorn). https://www.cabi.org/isc/datasheet/118984#EF51C788-F9D6-4F79-B667-F7DD03B02F65. Accessed 28 Sept 2018
Chong JM (1989) Enantioselective synthesis of sitophilate, the granary weevil aggregation pheromone. Tetrahedron 45:623–628
European and Mediterranean Plant Protection Organization, EPPO (2014) Pest risk analysis for Aromia bungii. EPPO, Paris. https://www.eppo.int/QUARANTINE/Pest_Risk_Analysis/PRAdocs_insects/15_21043_PRA_record_Aromia_bungii.pdf. Accessed 9 Mar 2017
Fukaya M, Kiriyama S, Yasui H (2017) Mate-location flight of the red-necked longicorn beetle, Aromia bungii (Coleoptera: Cerambycidae): an invasive pest lethal to Rosaceae trees. Appl Entomol Zool 52:559–565
Gao Y, Klunder JM, Hanson RM, Masamune H, Ko SY, Sharpless KB (1987) Catalytic asymmetric epoxidation and kinetic resolution: modified procedures including in situ derivatization. J Am Chem Soc 109:5765–5780
Garonna AP, Nugnes F, Espinosa B et al (2013) Aromia bungii, a new Asian worm found in Campania. Inf Agrar 69:60–62
Hanks LM, Millar JG (2016) Sex and aggregation pheromones of cerambycid beetles: basic science and practical applications. J Chem Ecol 42:631–654
Iwabuchi K, Takahashi J, Nakagawa Y, Sakai T (1986) Behavioral responses of female grape borer Xylotrechus pyrrhoderus Bates (Coleoptera: Cerambycidae) to synthetic male sex pheromone components. Appl Entomol Zool 21:21–27
Lacey ES, Ginzel MD, Millar JG, Hanks LM (2004) Male-produced aggregation pheromone of the cerambycid beetle Neoclytus acuminatus acuminatus. J Chem Ecol 30:1493–1507
Ma W, Sun L, Yu L, Wang J, Chen J (2007) Study on the Occurrence and Life History in Aromia bungii (Faldermann). Acta Agric Bor Sin 22:247–249
Meier LR, Zou Y, Millar JG, Mongold-Diers JA, Hanks LM (2016) Synergism between enantiomers creates species-specific pheromone blends and minimizes cross-attraction for two species of cerambycid beetles. J Chem Ecol 42:1181–1192
Millar JG, Hanks LM (2017) Chemical ecology of cerambycids. In: Wang Q (ed) Cerambycidae of the world: biology and pest management. CRC Press/Taylor and Francis, Boca Raton, pp 161–196
Mori K (2018) Pheromone synthesis. Part 263: synthesis of the racemate and the enantiomers of (E)-cis-6,7-epoxy-2-nonenal, the male-produced pheromone of the red-necked longhorn beetle, Aromia bungii. Tetrahedron 74:1444–1448
Ray AM, Millar JG, Moreira JA, McElfresh JS, Mitchell RF, Barbour JD, Hanks LM (2015) North American species of cerambycid beetles in the genus Neoclytus share a common hydroxyhexanone-hexanediol pheromone structural motif. J Econ Entomol 108:1860–1868
Tanuwidjaja J, Ng S-S, Jamison TF (2009) Total synthesis of ent-dioxepandehydrothyrsiferol via a bromonium-initiated epoxide-opening cascade. J Am Chem Soc 131:12084–12085
Taylor RJ, Campbell L, McAllister GD (2008) (±)-trans-3,3′-(1,2-Cyclopropanediyl)bis-2-(E)-propenoic acid, diethyl ester: tandem oxidation procedure (TOP) using MnO2 oxidation-stabilized phosphorane trapping. Org Synth 85:15–26
Underwood BS, Tanuwidjaja J, Ng S-S, Jamison TF (2013) Total syntheses of the squalene-derived halogenated polyethers ent-dioxepandehydrothyrsiferol and armatol A via bromonium-and Lewis acid-initiated epoxide-opening cascades. Tetrahedron 69:5205–5220
Wang Q (2017) Cerambycid pests in agricultural and horticultural crops. In: Wang Q (ed) Cerambycidae of the world: biology and pest management. CRC Press, Boca Raton
Wang JT, Sun L, Liu T, Zhang L (2007) Research on the occurrence character and control measure of Aromia bungii. J Hebei Ag Sci 11(2):41–43
Wei J, Liu X, Niu Y, Wang J (2013) Identification of volatiles released from the living adult Aromia bungii Faldermann. For Pest Dis 32:8–10 (in Chinese)
Xu T, Yasui H, Teale SA, Fujiwara-Tsujii N, Wickham JD, Fukaya M, Hansen L, Kiriyama S, Hao D, Nakano A, Zhang L, Watanabe T, Tokoru M, Millar JG (2017) Identification of a male-produced sex-aggregation pheromone for a highly invasive cerambycid beetle, Aromia bungii. Sci Rep 7:7330
Yasui H, Fujiwara-Tsujii N, Yasuda T, Fukaya M, Kiriyama S, Nakano A, Watanabe T, Mori K (2018) Electroantennographic responses and field attraction of an emerging invader, the red-necked longicorn beetle Aromia bungii (Coleoptera: Cerambycidae), to the chiral and racemic forms of its male-produced aggregation-sex pheromone. Appl Entomol Zool 1:6. https://doi.org/10.1007/s13355-018-0600-x
Yu G, Gao B (2005) Bionomics of Aromia bungii. For Pest Dis 24:15–16
Acknowledgements
We thank Shuo Tian and Yingyi Cheng of Nanjing Forestry University for assistance with the field experiments, and two anonymous reviewers for their helpful suggestions.
Funding
This study was funded by grants from the United States Department of Agriculture, Animal and Plant Health Inspection Service-Plant Protection and Quarantine program (USDA-APHIS-PPQ) Grants 17-8130-1422-CA and 18-8130-1422-CA) to JGM and SAT.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest.
Ethical approval
The laboratory research was conducted at the University of California, Riverside. All methods met the ethical requirements of the respective universities and followed guidelines of the Committee of Publication Ethics.
Research involving human participants and/or animals
This article does not involve any studies with human participants or vertebrate animals.
Additional information
Communicated by P.G. Becher.
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Zou, Y., Hansen, L., Xu, T. et al. Optimizing pheromone-based lures for the invasive red-necked longhorn beetle, Aromia bungii. J Pest Sci 92, 1217–1225 (2019). https://doi.org/10.1007/s10340-019-01108-6
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10340-019-01108-6