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)

Abstract

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.

Sexual activity of males and distribution of Stygioides colchicus (Herrich-Schäffer, 1851) (Lepidoptera: Cossidae)

“…The authors, independently of each other, began using synthetic sex attractants around the end of the 80s of the last century. Using synthetic sex attractants, we identified specific details of the distribution of some species of Zygaenidae and Sesiidae (Efetov et al, 2011(Efetov et al, , 2015(Efetov et al, , 2018(Efetov et al, , 2022(Efetov et al, , 2023Subchev et al, 2016;Gorbunov, 2017Gorbunov, , 2018aGorbunov, , 2021Gorbunov, , 2022aRazov et al, 2017;Can Cengiz et al, 2018;Can et al, 2019;Vrenozi et al, 2019;Efetov, Gorbunov, 2021). In addition, with the help of synthetic sex attractants, we collected and described new species of Sesiidae (Gorbunov, 2018b;2020a-b, 2021, 2022a-b, 2023Gorbunov, Efetov, 2018), and also found a rare species of Zygaenidae, known for a long time only based on the holotype specimen (Efetov et al, 2014).…”

To the distribution of the genus Negotinthia O. Gorbunov, 2001 (Lepidoptera: Sesiidae) in the Crimea

“…1). It is well known that sex pheromones and sex attractants play an increasingly important role in faunal investigations of Lepidoptera, because they allow researchers to discover new species, detect populations of pest or rare species, monitor and control the seasonal flight of moths (Efetov et al 2010(Efetov et al , 2011(Efetov et al , 2015(Efetov et al , 2018(Efetov et al , 2019(Efetov et al , 2022(Efetov et al , 2023(Efetov et al , 2024Gorbunov 2015bGorbunov , 2016Gorbunov , 2017Gorbunov , 2018aGorbunov -c, 2019bGorbunov -c, 2020aGorbunov -b, 2012aGorbunov -b, 2022aGorbunov -d, 2023aEfetov & Gorbunov 2021).…”