Synthesis and field testing of esters of (2R)-butan-2-ol and (2S)-butan-2-ol and monounsaturated fatty acids as sex attractants for the males of Procridinae species (Lepidoptera: Zygaenidae)
DOI:
https://doi.org/10.57065/shilap.474Parole chiave:
Lepidoptera, Zygaenidae, Procridinae, Adscita geryon, Jordanita notata, EFETOV-S-5, EFETOV-S-S-5, sex attractant, CrimeaAbstract
In the family Zygaenidae (Lepidoptera) with more than 1000 species a complete chemical analysis of the structure of female sex pheromones has been carried out for only three species of the subfamily Procridinae while sex attractants have been found for males of more than 60 species of two subfamilies: Procridinae and Zygaeninae. The synthesis of new sex attractants was performed from (Z)-dodec-5-enoic acid and R- and S-enantiomers of butan-2-ol at the Crimean Federal University in 2021. The biological activity of received esters was tested during fieldwork in the Crimean Peninsula. It has been proved that (2R)-butan-2-yl (Z)-dodec-5-enoate (named EFETOV-S-5) and (2S)-butan-2-yl (Z)-dodec-5-enoate (named EFETOV-S-S-5) are sex attractants for the males of Jordanita (Tremewania) notata (Zeller, 1847), while (2S)-butan-2-yl (Z)-dodec-5-enoate (EFETOV-S-S-5) is a sex attractant for Adscita (Adscita) geryon (Hübner, 1813). In addition, (2R)-butan-2-yl (Z)-hexadec-9-enoate and (2S)-butan-2-yl (Z)-hexadec-9-enoate were synthesised in 2022. However, these esters did not attract any of the Zygaenidae species which are common in the Crimea.
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Can, F., Efetov, K. A., Burman, J., Kaya, K., Kucherenko, E. E., Ularlı, B., & Tarmann, G. M. (2019). A study of the Zygaenidae (Lepidoptera) fauna of Central Anatolia, Turkey. Turkish Journal of Entomology (Türkiye Entomoloji Dergisi), 43(2), 189-199. https://doi.org/10.16970/entoted.512580 DOI: https://doi.org/10.16970/entoted.512580
Can Cengiz, F., Efetov, K. A., Kaya, K., Kucherenko, E. E., Okyar, Z., & Tarmann, G. M. (2018). Zygaenidae (Lepidoptera) of Thrace Region of Turkey. Nota lepidopterologica, 41(1), 23-36. https://doi.org/10.3897/nl.41.21065 DOI: https://doi.org/10.3897/nl.41.21065
Drouet, E., Toshova, T. B., & Efetov, K. A. (2021). Results of the use of synthetic sex attractant lures for Zygaenidae in south-eastern France (Lepidoptera: Zygaenidae). SHILAP Revista de lepidopterología, 49(193), 183-191. DOI: https://doi.org/10.57065/shilap.334
Efetov, K. A. (1996a). The description of the female of Adscita (Zygaenoprocris) rjabovi (Alberti, 1938) (Lepidoptera: Zygaenidae, Procridinae). Entomologist’s Gazette, 47(1), 31-35.
Efetov, K. A. (1996b). The description of the female of Illiberis (Alterasvenia) yuennanensis Alberti, 1951(Lepidoptera: Zygaenidae, Procridinae). Entomologist’s Gazette, 47(2), 111-113.
Efetov, K. A. (1998). A revision of the genus Goe Hampson, [1893] (Lepidoptera: Zygaenidae, Procridinae), with descriptions of two new species. Entomologist’s Gazette, 49(1), 49-62.
Efetov, K. A. (1999). Inouela gen. n. from Japan and Taiwan (Lepidoptera: Zygaenidae, Chalcosiinae). Entomologist’s Gazette, 50(2), 91-95.
Efetov, K. A. (2001). On the systematic position of Zygaenoprocris Hampson, 1900 (Lepidoptera: Zygaenidae, Procridinae) and the erection of two new subgenera. Entomologist’s Gazette, 52(1), 41-48.
Efetov, K. A. (2005). The Zygaenidae (Lepidoptera) of the Crimea and other regions of Eurasia. CSMU Press.
Efetov, K. A. (2006). Nine new species of the genus Chrysartona Swinhoe, 1892 (Lepidoptera: Zygaenidae, Procridinae). Entomologist’s Gazette, 57(1), 23-50.
Efetov, K. A. (2010). Illiberis (Hedina) louisi sp. nov. (Lepidoptera: Zygaenidae, Procridinae) from China. Entomologist’s Gazette, 61(4), 235-241.
Efetov, K. A., Can, F., Toshova, T. B., & Subchev, M. (2010). New sex attractant for Jordanita anatolica (Naufock) (Lepidoptera: Zygaenidae: Procridinae). Acta zoologica bulgarica, 62(3), 315-319.
Efetov, K. A., & Hayashi, E. (2008). On the chaetotaxy of the first instar larva of Artona martini Efetov, 1997 (Lepidoptera: Zygaenidae, Procridinae, Artonini). Entomologist’s Gazette, 59(2), 101-104.
Efetov, K. A., Hofmann, A., & Tarmann, G. M. (2014a). Application of two molecular approaches (use of sex attractants and DNA barcoding) allowed to rediscover Zygaenoprocris eberti (Alberti, 1968) (Lepidoptera, Zygaenidae, Procridinae), hitherto known only from the female holotype. Nota lepidopterologica, 37(2), 151-160. https://doi.org/10.3897/nl.37.7871 DOI: https://doi.org/10.3897/nl.37.7871
Efetov, K. A., Hofmann, A., Tarmann, G. M., & Tremewan, W. G. (2014b). Taxonomic comments on the treatment of the Zygaenidae (Lepidoptera) in volume 3 of Moths of Europe, Zygaenids, Pyralids 1 and Brachodids (2012). Nota lepidopterologica, 37(2), 123-133. https://doi.org/10.3897/nl.37.7940 DOI: https://doi.org/10.3897/nl.37.7940
Efetov, K. A., Kirsanova, A. V., Lazareva, Z. S., Parshkova, E. V., Tarmann, G. M., Rougerie, R., & Hebert, P. D. N. (2019a). DNA barcoding of Zygaenidae (Lepidoptera): results and perspectives. Nota lepidopterologica, 42(2), 137-150. https://doi.org/10.3897/nl.42.33190 DOI: https://doi.org/10.3897/nl.42.33190
Efetov, K. A., & Knyazev, S. A. (2014). New records of Jordanita (Roccia) volgensis (Möschler, 1862) (Lepidoptera: Zygaenidae, Procridinae) from Siberia (Russia) and Ukraine. Entomologist’s Gazette, 65(3), 175-178.
Efetov, K. A., Knyazev, S. A., & Kucherenko, E. E. (2022). The first record of Jordanita (Solaniterna) subsolana (Staudinger, 1862) from Kazakhstan (Lepidoptera: Zygaenidae, Procridinae). SHILAP Revista de lepidopterología, 50(198), 233-239. https://doi.org/10.57065/shilap.127 DOI: https://doi.org/10.57065/shilap.127
Efetov, K. A., Koshio, C., & Kucherenko, E. E. (2018). A new synthetic sex attractant for males of Illiberis (Primilliberis) pruni Dyar, 1905 (Lepidoptera: Zygaenidae, Procridinae). SHILAP Revista de lepidopterología, 46(182), 263-270.
Efetov, K. A., & Kucherenko, E. E. (2020). Structural analysis of sex pheromones and attractants in Zygaenidae (Insecta, Lepidoptera): biochemical and evolutionary aspects. Journal of Evolutionary Biochemistry and Physiology, 56(5), 381-395. https://doi.org/10.1134/S0022093020050014 DOI: https://doi.org/10.1134/S0022093020050014
Efetov, K. A., & Kucherenko, E. E. (2021). Enantiomers of 2-butyl dodec-2-enoate as sex attractants. Russian Journal of Bioorganic Chemistry, 47(5), 1043-1050. https://doi.org/10.1134/S1068162021050241 DOI: https://doi.org/10.1134/S1068162021050241
Efetov, K. A., Kucherenko, E. E., Parshkova, E. V., & Tarmann, G. M. (2016). 2-butyl 2-dodecenoate, a new sex attractant for Jordanita (Tremewania) notata (Zeller, 1847) and some other Procridinae species (Lepidoptera: Zygaenidae). SHILAP Revista de lepidopterología, 44(175), 519-527.
Efetov, K. A., Kucherenko, E. E., & Tarmann, G. M. (2019b). New synthetic sex attractants for the males of two endemic Iberian Procridinae species (Lepidoptera: Zygaenidae). SHILAP Revista de lepidopterología, 47(186), 307-315.
Efetov, K. A., Kucherenko, E. E., & Tarmann, G. M. (2020). An application of the synthetic sex attractants from the series “EFETOV-2” for studying Procridinae in Italy (Lepidoptera: Zygaenidae). SHILAP Revista de lepidopterología, 48(192), 733-749. DOI: https://doi.org/10.57065/shilap.351
Efetov, K. A., Parshkova, E. V., Baevsky, M. Y., & Poddubov, A. I. (2014c). Sec-butyl ester of dodecenoate: synthesis and attractive properties. Ukrainian Biochemical Journal, 86(6), 175-182. https://doi.org/10.15407/ubj86.06.175 DOI: https://doi.org/10.15407/ubj86.06.175
Efetov, K. A., Parshkova, E. V., & Koshio, C. (2004). The karyotype of Illiberis (Primilliberis) rotundata Jordan, [1907] (Lepidoptera: Zygaenidae, Procridinae). Entomologist’s Gazette, 55(3), 167-170.
Efetov, K. A., Parshkova, E. V., Tarasova, L. G., & Tarmann, G. M. (2015a). The karyotypes of Procridinae (Lepidoptera: Zygaenidae), with the first record of the karyotype of Pollanisus commoni Tarmann, 2004, a representative of the tribe Artonini. Entomologist’s Gazette, 66(2), 121-125.
Efetov, K. A., & Savchuk, V. V. (2009). The first record of Jordanita (Roccia) volgensis (Möschler, 1862) (Lepidoptera: Zygaenidae, Procridinae) from the Crimea. Entomologist’s Gazette, 60(3), 155-158.
Efetov, K. A., Subchev, M. A., Toshova, T. B., & Kiselev, V. M. (2011). Attraction of Zygaenoprocris taftana (Alberti, 1939) and Jordanita horni (Alberti, 1937) (Lepidoptera: Zygaenidae, Procridinae) by synthetic sex pheromones in Armenia. Entomologist’s Gazette, 62(2), 113-121.
Efetov, K. A., & Tarmann, G. M. (1999). On the systematic position of Procris fusca Leech, [1889] (Lepidoptera: Zygaenidae, Procridinae). Entomologist’s Gazette, 50(3), 163-168.
Efetov, K. A., & Tarmann, G. M. (2013a). Illiberis (Alterasvenia) cernyi sp. nov. (Lepidoptera: Zygaenidae, Procridinae) from northern Thailand. Entomologist’s Gazette, 64(1), 33-39.
Efetov, K. A., & Tarmann, G. M. (2013b). Chrysartona (Chrystarmanna) mineti sp. nov. (Lepidoptera: Zygaenidae, Procridinae) from northern Vietnam. Entomologist’s Gazette, 64(3), 197-206.
Efetov, K. A., & Tarmann, G. M. (2014a). Illiberis (Alterasvenia) banmauka sp. nov. (Lepidoptera: Zygaenidae, Procridinae) from China and Myanmar. Entomologist’s Gazette, 65(1), 62-70.
Efetov, K. A., & Tarmann, G. M. (2014b). A new European species, Adscita dujardini sp. nov. (Lepidoptera: Zygaenidae, Procridinae) confirmed by DNA analysis. Entomologist’s Gazette, 65(3), 179-200.
Efetov, K. A., & Tarmann, G. M. (2016a). Pseudophacusa multidentata Efetov & Tarmann, a new genus and species of Procridini from Myanmar, China, and Laos (Lepidoptera: Zygaenidae, Procridinae). SHILAP Revista de lepidopterología, 44(173), 81-89.
Efetov, K. A., & Tarmann, G. M. (2016b). A new Illiberis species: I. (Alterasvenia) kislovskyi (Lepidoptera: Zygaenidae, Procridinae) from Myanmar. Entomologist’s Gazette, 67(2), 137-142.
Efetov, K. A., & Tarmann, G. M. (2017a). The hypothetical ground plan of the Zygaenidae, with a review of the possible autapomorphies of the Procridinae and the description of the Inouelinae subfam. nov. Journal of the Lepidopterists’ Society, 71(1), 20-49. https://doi.org/10.18473/lepi.v71i1.a5 DOI: https://doi.org/10.18473/lepi.v71i1.a5
Efetov, K. A., & Tarmann, G. M. (2017b). Thibetana keili Efetov & Tarmann, a new species of the genus Thibetana Efetov & Tarmann, 1995, from Tibet (Lepidoptera: Zygaenidae, Procridinae, Artonini). SHILAP Revista de lepidopterología, 45(180): 581-587.
Efetov, K. A., Tarmann, G. M., Hayashi, E., & Parshkova, E. V. (2006). New data on the chaetotaxy of the first instar larvae of Procridini and Artonini (Lepidoptera: Zygaenidae, Procridinae). Entomologist’s Gazette, 57(4), 229-233.
Efetov, K. A., Tarmann, G. M., & Parshkova, E. V. (2019c). “Ino Budensis var. Mollis” Grum-Grshimailo, 1893 (Lepidoptera: Zygaenidae) from Eastern Asia recognized as a valid species on the base of morphological and molecular analysis. Zootaxa, 4619(3), 518-526. http://dx.doi.org/10.11646/zootaxa.4619.3.5 DOI: https://doi.org/10.11646/zootaxa.4619.3.5
Efetov, K. A., Tarmann, G. M., Toshova, T. B., & Subchev, M. A. (2015b). Enantiomers of 2-butyl 7Z-dodecenoate are sex attractants for males of Adscita mannii (Lederer, 1853), A. geryon (Hübner, 1813), and Jordanita notata (Zeller, 1847) (Lepidoptera: Zygaenidae, Procridinae) in Italy. Nota lepidopterologica, 38(2), 161-169. https://doi.org/10.3897/nl.38.6312 DOI: https://doi.org/10.3897/nl.38.6312
El-Sayed, A. M. (2022). The Pherobase: database of pheromones and semiochemicals. http://www.pherobase.com
Knyazev, S. A., Efetov, K. A., & Ponomaryov, K. B. (2015). Zygaenidae (Lepidoptera) from Omsk Region. Zoologicheskiy Zhurnal, 94(11), 1297-1302.
Landolt, P. J., Heath, R. R., & Tarmann G. (1991). Zygaenidae trapped with enantiomers of 2-butyl (Z)-7-tetradecenoate. The Journal of the Lepidopterists’ Society, 45(1), 63-65.
Nahirnic-Beshkova, A., Beshkov, S., Kucherenko, E. E., & Efetov, K. A. (2021). Theresimima ampellophaga (Bayle-Barelle, 1808) rediscovered in the Republic of North Macedonia by using sex attractant traps (Lepidoptera: Zygaenidae). SHILAP Revista de lepidopterología, 49(193), 161-170. DOI: https://doi.org/10.57065/shilap.332
Priesner, E., Naumann, C., & Stertenbrink, J. (1984). Specificity of synthetic sex-attractants in Zygaena moths. Zeitschrift für Naturforschung, 39(7-8), 841-844. DOI: https://doi.org/10.1515/znc-1984-7-826
Razov, J., Efetov, K. A., Franin, K., Toshova, T. B., & Subchev, M. A. (2017). The application of sex pheromone traps for recording the Procridinae fauna (Lepidoptera: Zygaenidae) in Croatia. Entomologist’s Gazette, 68(1), 49-53.
Subchev, M. (2014). Sex pheromone communication in the family Zygaenidae (Insecta: Lepidoptera): a review. Acta zoologica bulgarica, 66(2), 147-157.
Subchev, M. A., Efetov, K. A., Toshova, T. B., & Koshio, C. (2016). Sex pheromones as isolating mechanisms in two closely related Illiberis species - I. (Primilliberis) rotundata Jordan, 1907, and I. (P.) pruni Dyar, 1905 (Lepidoptera: Zygaenidae, Procridinae). Entomologist’s Gazette, 67(1), 51-57.
Subchev, M., Efetov, K. A., Toshova, T., Parshkova, E. V., Tóth, M., & Francke, W. (2010). New sex attractants for species of the zygaenid subfamily Procridinae (Lepidoptera: Zygaenidae). Entomologia Generalis (Stuttgart),32(4), 243-250. DOI: https://doi.org/10.1127/entom.gen/32/2010/243
Subchev, M. A., Koshio, C., Toshova, T. B., & Efetov, K. A. (2012). Illiberis (Primilliberis) rotundata Jordan (Lepidoptera: Zygaenidae: Procridinae) male sex attractant: Optimization and use for seasonal monitoring. Entomological Science, 15, 137-139. DOI: https://doi.org/10.1111/j.1479-8298.2011.00485.x
Subchev, M., Koshio, C., Toshova T., Efetov, K. A., & Francke, W. (2013). (2R)-butyl (7Z)-dodecenoate, a main sex pheromone component of Illiberis (Primilliberis) pruni Dyar (Lepidoptera: Zygaenidae: Procridinae)?. Acta zoologica bulgarica, 65(3), 391-396.
Vrenozi, B., Toshova, T. B., Efetov, K. A., Kucherenko, E. E., Rredhi, A., & Tarmann, G. M. (2019). The first well-documented record of the vine bud moth Theresimima ampellophaga (Bayle-Barelle, 1808) in Albania established by field screening of sex pheromone and sex attractant traps (Lepidoptera: Zygaenidae, Procridinae). SHILAP Revista de lepidopterología, 47(187), 567-576.
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