Introduction

In recent years, there has been an increasing amount of literature on various approaches to the study of pheromone systems in Lepidoptera. Much of the current research on these attractant molecules pays particular attention to their chemical structure, isomerism and biosynthesis ( El-Sayed, 2022). In the family Zygaenidae (Lepidoptera) which includes five subfamilies ( Efetov, 1999, Efetov et al. 2014b; Efetov & Tarmann, 2017a) with more than 1000 species ( Efetov, 1996a, 1996b, 1998, 1999, 2001, 2006, 2010; Efetov & Hayashi, 2008; Efetov et al. 2004, 2006, 2015a, 2019a, 2019c; Efetov & Knyazev, 2014; Efetov & Savchuk, 2009; Efetov & Tarmann, 1999, 2013a, 2013b, 2014a, 2014b, 2016a, 2016b, 2017a, 2017b; Knyazev et al. 2015) a complete chemical analysis of the structure of female sex pheromones has been carried out for only three species (all are pests) of the subfamily Procridinae ( Efetov & Kucherenko, 2020; Subchev, 2014). There is a little more information on sex attractants (chemicals that are not naturally produced by the same species but found to be attractive in field or laboratory experiments) for Zygaenidae species. Sex attractants have been found for males of more than 60 species of two subfamilies Procridinae and Zygaeninae ( Drouet et al. 2021; Efetov et al. 2010, 2011, 2014a, 2015b; Landolt et al. 1991; Priesner et al. 1984; Razov et al. 2017; Subchev, 2014; Subchev et al. 2010, 2012, 2013, 2016).

Previously, we had already synthesised (2 R)-butan-2-yl dodec-2-enoate (named EFETOV-S-2, another name is (2 R)-butyl 2-dodecenoate) and (2 S)-butan-2-yl dodec-2-enoate (named EFETOV-S-S-2, another name is (2 S)-butyl 2-dodecenoate). In different countries of the world field experiments with these esters (alone or in racemic mixture) have confirmed their attractive properties for almost 30 Zygaenidae species ( Can et al. 2019; Can Cengiz et al. 2018; Efetov et al. 2014c, 2016, 2018, 2019b, 2020, 2022; Efetov & Kucherenko, 2021; Nahirnić-Beshkova et al. 2021; Vrenozi et al. 2019).

The aims of the present work were: 1) to synthesise esters of (2 R)-butan-2-ol or (2 S)-butan-2-ol and (Z)-dodec-5-enoic acid as well as (Z)-hexadec-9-enoic acid; 2) to test obtained esters as sex attractants for Zygaenidae species in the Crimean Peninsula.

Materials and methods

S ynthesis of the target esters

Commercial chemicals (2 S)-butan-2-ol, (2 R)-butan-2-ol, (Z)-dodec-5-enoic acid were purchased from Sigma-Aldrich, USA and (Z)-hexadec-9-enoic acid from Toronto Research Chemicals, Canada. All chemicals were of 99% purity. Synthesis of (2 S)-butan-2-yl (Z)-dodec-5-enoate and (2 R)-butan-2-yl ( Z)-dodec-5-enoate was performed in two stages: (1) synthesis of acyl chloride; (2) alcoholysis of acyl chloride.

1. 1. Synthesis of (Z)-dodec-5-enoyl chloride. 5 g (0.025 mol) of (Z)-dodec-5-enoic acid was placed in a 50 ml round-bottom flask equipped with a water-cooled reflux condenser. 10 ml of anhydrous benzene, 0.5 ml of N,N-dimethylformamide and 2.2 ml (0.03 mol) of thionyl dichloride were added. The reaction mass was heated to boiling and maintained at boiling point for one hour. At the end of the reaction, the solvent (benzene) and excess of thionyl dichloride were removed under vacuum on a rotary evaporator. Acyl chloride was used at the stage of synthesis of the corresponding ester.
2. 2. Synthesis of (2 S)-butan-2-yl (Z)-dodec-5-enoate. 10 ml of anhydrous benzene, 3 ml (0.3 mol) of (2 S)-butan-2-ol and 3 ml (0.03 mol) of pre-dried pyridine were added to a 50 ml round-bottom flask equipped with a water-cooled reflux condenser containing the previously synthesized ( Z)-dodec-5-enoyl chloride and 0.5 ml of N,N-dimethylformamide. The reaction mass was heated to boiling and maintained at boiling point for one hour. After completion of the reaction, the pyridine hydrochloride was removed by filtration on a Schott filter under vacuum. The precipitate was washed with 20 ml of anhydrous benzene. The filtrate was washed on a separating funnel with two portions of 20 ml of 5% hydrochloric acid solution, separating the excess of pyridine. Then the filtrate was washed with two portions of 20 ml of 10% sodium hydroxide solution, with the aim of removing unreacted acid and alcohol. The benzene layer was separated. After removing the benzene on a rotary evaporator, 4.5 g of (2 S)-butan-2-yl (Z)-dodec-5-enoate were obtained (85% purity according to high-performance liquid chromatography). Synthesis of (2 R)-butan-2-yl (Z)-dodec-5-enoate (75% purity according to HPLC) was performed from (2 R)-butan-2-ol by a similar procedure. As a result, two esters, viz. (2 S)-butan-2-yl (Z)-dodec-5-enoate and (2 R)-butan-2-yl (Z)-dodec-5-enoate, were obtained and called EFETOV-S-S-5 and EFETOV-S-5, respectively ( Figures 1-2). EFETOV-S-S-5 was obtained two times and these samples were conventionally marked EFETOV-S-S-5(60) and EFETOV-S-S-5(85).

(2 S)-butan-2-yl (Z)-hexadec-9-enoate and (2 R)-butan-2-yl (Z)-hexadec-9-enoate were synthesised as described above but at the first stage ( Z)-hexadec-9-enoyl chloride was obtained by treating ( Z)-hexadec-9-enoic acid with thionyl dichloride.

P reparation of lures

Synthetic attractant candidate compounds were used without solvents in a dose of 50 μl for preparation each lure. Different types of esters were loaded on rubber dispensers which were fixed on cardboard rectangles after the attractant adsorption. All baits were marked as ‘EFETOV-S-5’ for (2 R)-butan-2-yl (Z)-dodec-5-enoate, ‘EFETOV-S-S-5’ for (2 S)-butan-2-yl (Z)-dodec-5-enoate, ‘EFETOV-S-9-16’ for (2 R)-butan-2-yl (Z)-hexadec-9-enoate, and ‘EFETOV-S-S-9-16’ for (2 S)-butan-2-yl (Z)-hexadec-9-enoate.

As a positive control, we used rubber caps impregnated with 50 μl of the sex attractant EFETOV-2 (the racemic mixture of (2 R)-butan-2-yl dodec-2-enoate and (2 S)-butan-2-yl dodec-2-enoate), which had been synthesised earlier according to the procedure published by Efetov et al. (2014c). The efficacy of baits with EFETOV-2 has been proven for seven species of Zygaenidae of the Crimean fauna ( Efetov & Kucherenko, 2021). Empty rubber caps without any synthetic compounds were used as a negative control.

The lures with labelled cardboard holders were fixed in transparent plastic Delta traps containing removable sticky layers ( Figure 3).

F ield experiments

Attempts to observe the attraction of males of Zygaenidae species to synthetic esters were conducted in 2021 (with EFETOV-S-5 and EFETOV-S-S-5) and 2022 (with EFETOV-S-9-16 and EFETOV-S-S-9-16) at four localities of the Crimean Peninsula in biotopes corresponding to the preferred habitats of the target species ( Efetov, 2005). The experimental and control traps were hung on bushes or trees at a height of 1.0-1.5 m above the ground. The distance between different types of traps was at least 10 meters. The traps were inspected on average once a week. Sometimes we just put the baits on rocks on the ground (the distance between the baits was not less than several meters). In this case, we collected attracted moths by catching them with a net near the rubber caps. All specimens (captured and glued moths) were determined by examination of the genitalia by K. A. Efetov.

The list of the studied localities of the Crimean Peninsula and the time of observations are presented below ( Figure 4).

Locality 1: vic. Belogorsk, Mt. Sary-Kaya, 230-239 m, grassy slope near steep calcareous edge of the mountain ( Figure 5). Periods of observation: 15-V-2021 -15-VII-2021, one trap with EFETOV-S-5, one trap with EFETOV-S-S-5(60), one trap with EFETOV-S-S-5(85), and one control trap (without attractant); 06-V-2022 - 02-VII-2022, one trap with EFETOV-S-9-16, one trap with EFETOV-S-S-9-16, and one control trap (without attractant).

Locality 2: vic. Simferopol, Bitak, 320 m, grassy slope near steep calcareous edge of the mountain. Periods of observation: 16-V-2021 - 08-VII-2021, one trap with EFETOV-S-5, one trap with EFETOV-S-S-5(85), and one control trap (without attractant); 06-V-2022 - 01-VII-2022, one trap with EFETOV-S-9-16, one trap with EFETOV-S-S-9-16, and one control trap (without attractant).

Locality 3: Mt. Chatyr-Dag, 514 m, grassy slope near deciduous forest ( Figure 6). Periods of observation: 16-V-2021 - 08-VII-2021, one trap with EFETOV-S-5, one trap with EFETOV-S-S-5(60), one trap with EFETOV-S-S-5(85), and one control trap (without attractant); 23-V-2022 - 29-VII-2022, one trap with EFETOV-S-9-16, one trap with EFETOV-S-S-9-16, and one control trap (without attractant).

Locality 4: vic. Luchistoye, NE of Alushta, 376 m, abandoned vineyard near the lake. Periods of observation: 16-V-2021 - 24-IX-2021, one trap with EFETOV-S-5, one trap with EFETOV-S-S-5(60), one trap with EFETOV-S-S-5(85), one trap with EFETOV-2, and one control trap (without attractant); 23-V-2022 - 04-VIII-2022, one trap with EFETOV-S-9-16, one trap with EFETOV-S-S-9-16, one trap with EFETOV-2, and one control trap (without attractant).

Results and discussion

During our field screening tests the attraction of two Procridinae species to the baits with new synthetic compounds EFETOV-S-5 and EFETOV-S-S-5 was recorded, viz. Adscita ( Adscita) geryon (Hübner, 1813) and Jordanita (Tremewania) notata (Zeller, 1847) ( Figure 3). No specimens were attracted by the lures EFETOV-S-9-16 and EFETOV-S-S-9-16. In addition, the males of Theresimima ampellophaga (Bayle-Barelle, 1809) were found in sticky traps with the baits EFETOV-2, which were used as a positive control in our experiments in 2021-2022. Traps without attractant (the negative control) were empty in all studied localities. The list of attracted specimens, type of lures, and the time of observation are provided below.

A. geryon (Hübner, 1813)

Locality 1, trap with EFETOV-S-S-5(60), 1 ♂, 20-V-2021; 1 ♂, 04-VI-2021; trap with EFETOV-S-S-5(85), 2 ♂♂, 20-V-2021; 1 ♂, 04-VI-2021; locality 2, trap with EFETOV-S-S-5(85), 1 ♂, 22-V-2021; locality 3, trap with EFETOV-S-S-5(60), 2 ♂♂, 29-VI-2021; trap with EFETOV-S-S-5(85), 1 ♂, 31-V-2021; 1 ♂, 22-VI-2021; near rubber cap with EFETOV-S-S-5(85), 1 ♂, 07-VI-2021.

J. notata (Zeller, 1847)

Locality 1, trap with EFETOV-S-5, 12 ♂♂, 20-V-2021; 9 ♂♂, 27-V-2021; 3 ♂♂, 04-VI-2021; 1 ♂, 12-VI-2021; trap with EFETOV-S-S-5(60), 2 ♂♂, 20-V-2021; 6 ♂♂, 27-V-2021; 8 ♂♂, 04-VI-2021; near trap with EFETOV-S-S-5(60), 1 ♂, 27-V-2021; trap with EFETOV-S-S-5(85), 13 ♂♂, 20-V-2021; 3 ♂♂, 27-V-2021; near trap with EFETOV-S-S-5(85), 4 ♂♂, 27-V-2021.

Th. ampellophaga (Bayle-Barelle, 1809)

Locality 4, trap with EFETOV-2, 17 ♂♂, 15-VII-2021; 7 ♂♂, 24-VII-2021; 2 ♂♂, 29-VII-2021; 7 ♂♂, 14-VII-2022; 8 ♂♂, 22-VII-2022; 3 ♂♂, 29-VII-2022.

In total, 25 males of J. notata were attracted to the baits EFETOV-S-5 and 37 males came to lures with EFETOV-S-S-5 (17 males to EFETOV-S-S-5(60) and 20 males to EFETOV-S-S-5(85)), whereas all 11 males of A. geryon were attracted only to EFETOV-S-S-5 (4 males to EFETOV-S-S-5(60) and 7 males to EFETOV-S-S-5(85)). No specimens of J. notata and A. geryon were found in sticky traps with EFETOV-S-9-16 and EFETOV-S-S-9-16. However, at the same time some males of both species were caught by a net near the rubber caps with attractant EFETOV-2 when we put them on the rocks on the ground during inspection of the traps. Previously, attractiveness of EFETOV-2 has been proved for both of these species ( Efetov et al. 2016). Thus, only esters of butan-2-ol and (Z)-dodec-5-enoic acid, but not of (Z)-hexadec-9-enoic acid, can be considered new sex attractants for males of J. notata and A. geryon.

It should be noted that 44 males of Th. ampellophaga were found in sticky traps with sex attractant EFETOV-2, that was used as a positive control in 2021-2022 in locality 4. However, the males of this species were absent in traps with newly synthesized esters. Besides this, some other Zygaenidae species (observed in the biotopes on the wing) did not respond to the tested baits. These species were Rhagades (Rhagades) pruni ([Denis & Schiffermüller], 1775), Jordanita (Roccia) budensis (Speyer & Speyer, 1858), J. (Jordanita) graeca (Jordan, 1907), J. (J.) chloros (Hübner, 1813), J. (J.) globulariae (Hübner, 1793), J. (Solaniterna) subsolana (Staudinger, 1862) (all Procridinae) and Zygaena (Mesembrynus) purpuralis (Brünnich, 1763), Z. (Agrumenia) viciae ([Denis & Schiffermüller], 1775), Z. (Lictoria) loti ([Denis & Schiffermüller], 1775), Z. (Z.) filipendulae (Linnaeus, 1758) (all Zygaeninae).

Previously, Efetov et al. (2015b, 2016, 2020), Efetov & Kucherenko (2021), Razov et al. (2017), Subchev et al. (2010) have shown that the R- and S-enantiomers of 2-butan-2-yl dodec-2-enoate and 2-butan-2-yl dodec-7-enoate are sex attractants for males of A. geryon, J. notata and some other species. These esters differ from each other and from the esters (2 R)-butan-2-yl dodec-5-enoate and (2 S)-butan-2-yl dodec-5-enoate by the position of the double bond in the acid radical, but this change affects the attractive properties of the esters in relation to males of the same species.

In our fieldwork, A. geryon were attracted to the S-enantiomer of 2-butan-2-yl dodec-5-enoate. This is in good agreement with the data which have been obtained earlier in Bulgaria, Crimea, Hungary and Italy ( Efetov et al. 2015b; Subchev et al. 2010), where males of this species were mainly attracted to the S-enantiomer of 2-butan-2-yl dodec-7-enoate alone or in a mixture with the corresponding R-enantiomer. In the case of (2 R)-butan-2-yl dodec-7-enoate and (2 S)-butan-2-yl dodec-7-enoate, the presence of the R-enantiomer does not influence the attractiveness of the S-enantiomer. The males of A. geryon were not found in sticky traps with the racemic mixture of 2-butan-2-yl dodec-2-enoate and its enantiomers alone. The males only flew up at a close distance of about 20-50 cm to the rubber caps with EFETOV-2 and then flew away. The main catches of this species in field trials with the enantiomers of 2-butan-2-yl dodec-5-enoate and 2-butan-2-yl dodec-7-enoate were recorded in sticky traps.

The main catches of J. notata were recorded in traps baited with (2 R)-butan-2-yl dodec-2-enoate, (2 R)-butan-2-yl dodec-5-enoate, (2 R)-butan-2-yl dodec-7-enoate or in traps with lures containing these compounds in mixtures with other substances ( Efetov et al. 2015b, 2016, 2020; Efetov & Kucherenko, 2021; Razov et al. 2017; Subchev et al. 2010). The presence of the corresponding S-enantiomers does not inhibit the attractiveness of the R-enantiomers for J. notata. It is clear that the stereoisomerism of the ester molecules is more important for their recognition by the olfactory receptors of males of this species than the position of the double bond in acid radicals.

In the Crimea in many localities two species, viz. A. geryon and A. albanica (Naufock, 1926), are sympatric and syntopic. When we performed experiments with R- and S-enantiomers of 2-butan-2-yl dodec-7-enoate and 2-butan-2-yl tetradec-9-enoate not only the males of A. geryon were attracted mainly to left isomers, but two males of A. albanica were attracted to mixtures containing (2 S)-butan-2-yl dodec-7-enoate (one male was in a trap with S- and R-enantiomers of 2-butan-2-yl dodec-7-enoate in 2006 and one male was in a trap with S-enantiomers of 2-butan-2-yl dodec-7-enoate and 2-butan-2-yl tetradec-9-enoate in 2007) ( Subchev et al. 2010). It means that (2S)-butan-2-yl dodec-7-enoate is a sex attractant for A. albanica.

Conclusion

New sex attractants for two Procridinae species, viz. Adscita geryon and Jordanita notata, were found. A. geryon males reacted to lures with (2 S)-butan-2-yl (Z)-dodec-5-enoate (EFETOV-S-S-5), while J. notata males were attracted to the both enantiomers of 2-butan-2-yl (Z)-dodec-5-enoate (EFETOV-S-5 and EFETOV-S-S-5).

(2 R)-butan-2-yl (Z)-hexadec-9-enoate and (2 S)-butan-2-yl (Z)-hexadec-9-enoate did not attract Zygaenidae moths, at least those species inhabiting the Crimea.

Acknowledgments

We thank Dr A. Spalding (Great Britain) for editing the English typescript. Our study was financially supported by the Ministry of Science and Higher Education of RF, Priority-2030 program N 075-15-2021-1323.

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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

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://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

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.

Nahirnić-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. 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.

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.

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.

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.

Author notes

*Autor para la correspondencia / Corresponding author