Introduction

Currently, sex pheromones of insects are widely used for the detection and direct control of species (both protected and pest species) and for monitoring their numbers in various biotopes (MILLAR et al., 2010; OLEANDER et al., 2015; SUBCHEV, 2014; WITZGALL et al., 2010). Most probably, female sex pheromones are the main factor in the attraction and recognition of females by conspecific males in some groups of Lepidoptera that are represented by habitually very similar species, for example in the subfamily Procridinae of the family Zygaenidae (EFETOV, 1996, 1997a, 1997b, 1998, 2001a, 2001c, 2006, 2010; EFETOV et al., 2004; EFETOV & TARMANN, 2013a, 2013b, 2014a, 2014b; TOSHOVA et al., 2007; ZAGATTI & RENOU, 1984). The Procridinae are divided into two tribes: Artonini Tarmann, 1994, and Procridini Boisduval, 1828 (TARMANN, 1994; EFETOV et al., 2000, 2006; EFETOV & HAYASHI, 2008). The Procridinae are represented only by the Procridini in the western Palaearctis (EFETOV, 2005; EFETOV & TARMANN, 2012).

One Procridini species, Jordanita .Tremewania. notata (Zeller, 1847), is distributed from Spain and Portugal through central and southern Europe to Ukraine, Crimea, Northern Caucasus, Transcaucasia, Turkey, and north-western Iran (EFETOV & TARMANN, 1999; EFETOV, 2004, 2005). Not long ago it was shown that (2.)-butyl (7.)-dodecenoate, previously established as a female sex pheromone component of Illiberis .Primilliberis. rotundata Jordan, 1907 (SUBCHEV et al., 2009), is a sex attractant for the males of J. notata in the Crimea, Bulgaria (SUBCHEV et al., 2010) and Italy (EFETOV et al., 2012, 2015). In Eurasia the enantiomers of 2-butyl (7.)- dodecenoate and/or their mixtures are also sex attractants for males of some other Procridini species, viz. Rhagades .Rhagades. pruni ([Denis & Schiffermüller], 1775), Adscita .Adscita. geryon (Hübner, 1813), Adscita .Tarmannita. mannii (Lederer, 1853) (SUBCHEV et al., 2010; EFETOV et al., 2012), Zygaenoprocris.Molletia. taftana (Alberti, 1939) (EFETOV et al., 2011), .. (Zygaenoprocris. eberti (Alberti, 1968) (EFETOV et al., 2014a), .. (Praviela. anatolica (Naufock, 1929) (EFETOV et al., 2010), and J. .Rjabovia. horni (Alberti, 1937) (EFETOV et al., 2011). The mixtures of (2.)-butyl (7.)-dodecenoate and (2.)-butyl (9.)-tetradecenoate are sex attractants for males of I. .P.. rotundata (SUBCHEV et al., 2012) and .. (..) pruni Dyar, 1905 (SUBCHEV et al., 2013).

The aim of this work was to study the biological activity of another ester of sec-butanol and dodecenoate with a double bond in the second position in dodecenoate. This substance has been synthesized in our laboratory and its attractiveness for different species of the Procridinae was tested during field observations in the Crimea in 2013-2014.

Materials and methods

Sec-butanol (Sigma-Aldrich, Germany) and other reagents (Ukraine) were used for the synthesis of 2-butyl 2-dodecenoate (EFETOV et al., 2013, 2014b). The products of reactions were separated by vacuum distillation, the content of products was determined by a gas-liquid chromatography with a chromatograph “Tsvet-500”, thermal conductivity detector (katharometer). The column of 3 m, SP-2250 on Supelcoports, temperature of the column is 90-130º C, of the evaporator - 130-220º C, of the detector - 90-190º C. A chemical nature of the synthesized substance was confirmed using a method of nuclear magnetic resonance spectroscopy (EFETOV et al., 2014b).

For preparing baits, 2-butyl 2-dodecenoate was applied onto vial caps (200 microlitres per cap without solvent) composed of grey rubber. The baits were tested in home-made sticky Delta traps with removable sticky layers covered with Tanglefoot® insect glue and hung on bushes or trees at a height of 1.0-1.5 m above the ground. In all sites we also placed control traps with rubber caps but without the attractant (distance to the baited traps was not less than 10 metres).

Sometimes we merely placed the lure on stones on the ground. In this case we collected attracted specimens by netting them near the lure.

Field observations were made in six localities in the mountain region of the Crimean Peninsula (Fig. 1). A list of studied localities and periods of observation is provided below.

SITE I: vic. Dachnoye, N of Sudak, 110 m. Bushy mountain slope near decidous forest. Periods of observation: 16-VI-2013 - 18-VII-2013, one baited trap and one control trap; 3-V-2014 - 27-VII- 2014, one baited trap and one control trap.

SITE II: vic. Belogorsk, Mt. Sary-Kaya, 230-239 m. Grassy slope near steep calcareous edge of the mountain. Periods of observation: 30-V-2013 – 27-VII-2013, two baited traps and one control trap; 3-V-2014 - 27-VII-2014, one baited trap and one control trap.

SITE III: vic. Simferopol, Bitak, 320 m. Grassy slope near steep calcareous edge of the mountain. Periods of observation: 28-IV-2013 - 27-VII-2013, two baited traps and one control trap; 13-V-2014 - 31-VII-2014, one baited trap and one control trap.

SITE IV: Mt. Chatyr-Dag, 466-514 m. Clearings in decidous forest. Periods of observation: 5- VI-2013 - 4-VIII-2013, one baited trap and one control trap; 17-V-2014 - 31-VII-2014, three baited traps and two control traps.

SITE V: vic. Izobilnoye, N of Alushta, 180 m. Bushy slope between a vineyard and decidous forest. Periods of observation: 4-V-2014 - 7-VIII-2014, two baited traps and one control trap.

SITE VI: vic. Luchistoye, NE of Alushta, 376-388 m. Bushy mountain slope near the lake.

Periods of observation: 4-V-2014 - 7-VIII-2014, two baited traps and one control trap.

The nomenclature of the subfamily Procridinae follows the last revisions of the group (EFETOV, 2001b, 2001c; EFETOV & TARMANN, 2012).

All collected specimens have been determined by K. A. Efetov, based on examination of the genitalia.

Results and discussion

The total number of specimens attracted is shown in Table 1. Dates of inspection of the traps in different biotopes and type of attraction of specimens (glued in trap or netted near lures) are listed below. Procridinae males were absent in control traps (without attractant) in all localities.

Rhagades .Rhagades. pruni ([Denis & Schiffermüller], 1775)

vic. Luchistoye, NE of Alushta, 376 m, in trap with 2-butyl 2-dodecenoate: 1 1, 14-VI-2014; 1 1, 21-VI-2014.

Adscita .Adscita. geryon (Hübner, 1813)

vic. Simferopol, Bitak, 320 m, near lure with 2-butyl 2-dodecenoate: 4 11, 17-V-2014; 4 11, 27-V-2014.

Jordanita .Tremewania. notata (Zeller, 1847)

vic. Belogorsk, Mt. Sary-Kaya, 239 m, near lure with 2-butyl 2-dodecenoate: 1 1, 3-V-2014; in trap with 2-butyl 2-dodecenoate: 51 11, 18-V-2014; 17 11, 24-V-2014; 56 11, 1-VI-2014.

Jordanita .Jordanita. graeca (Jordan, 1907)

vic. Dachnoye, N of Sudak, 110 m, in trap with 2-butyl 2-dodecenoate: 1 1, 1-VI-2014. Vic. Belogorsk, Mt. Sary-Kaya, 230 m, near lure with 2-butyl 2-dodecenoate: 7 11, 30-V-2013; 26 11, 11-VI-2013, 2 11, 19-VI-2013; 10 11, 24-V-2014; in trap with 2-butyl 2-dodecenoate: 1 1, 11-VI2013. Vic. Simferopol, Bitak, 320 m, in trap with 2-butyl 2-dodecenoate: 1 1, 24-V-2013. Vic. Izobilnoye, N of Alushta, 180 m, in trap with 2-butyl 2-dodecenoate: 1 1, 25-V-2014. Vic. Luchistoye, NE of Alushta, 376 m, near lure with 2-butyl 2-dodecenoate: 2 11, 29-V-2014; in trap with 2-butyl 2-dodecenoate: 1 1, 25-V-2014; 388 m, near lure with 2-butyl 2-dodecenoate: 21 11, 25-V-2014; 21 11, 29-V-2014; 1 1, 31-V-2014.

Jordanita .Jordanita. globulariae (Hübner, 1793)

Mt. Chatyr-Dag, 466 m, in trap with 2-butyl 2-dodecenoate: 5 11, 23-VI-2013; 1 1, 31-V2014; 2 11, 14-VI-2014; 514 m, in trap with 2-butyl 2-dodecenoate: 1 1, 14-VI-2014; 1 1, 28-VI2014.

Jordanita .Solaniterna. subsolana (Staudinger, 1862)

vic. Izobilnoye, N of Alushta, 180 m, in trap with 2-butyl 2-dodecenoate: 1 1, 29-V-2014. Vic. Luchistoye, NE of Alushta, 376 m, in trap with 2-butyl 2-dodecenoate: 1 1, 25-V-2014; 1 1, 29-V- 2014.

An application of 2-butyl 2-dodecenoate demonstrated its high attractiveness for the males of J. notata. 125 male specimens were collected near Belogorsk from 3-V-2014 to 27-VII-2014, 124 of which were found in one sticky trap that was controlled once per week. The number of attracted males could have been higher, as the sticky layers during the maximum flight period every week were completely covered with specimens (Fig. 2).

Except for J. notata, males of Rh. pruni, A. geryon, J. graeca, J. globulariae, and J. subsolana were also attracted during our field observations. We found two different types of attraction.

1. J. notata and J. globulariae were found as glued specimens on sticky layers. Rh. pruni and

J. subsolana were also found in sticky traps but in small numbers (two and three specimens respectively).

2. The other two species, viz. J. graeca and A. geryon, came actively to the lures (rubber caps with 2-butyl 2-dodecenoate) that were placed in the biotope. Only five specimens (out of 95) of J. graeca were found in sticky traps. These differences in attraction are shown in Figs 3 and 4. Most probably the males (that came to the lure and did not adhere to the sticky layers) realized at a close distance that the 2-butyl 2-dodecenoate is not their natural pheromone.

Conclusion

It was shown that synthetic 2-butyl 2-dodecenoate attracts the males of Jordanita .Tremewania. notata and other Procridinae species: Rhagades .Rhagades. pruni, Adscita .Adscita. geryon, Jordanita .Jordanita. graeca, J. (..) globulariae, and .. (Solaniterna. subsolana. This substance can be used for identifying the presence of Procridinae species in different regions and for seasonal monitoring of these moths. While the attraction of J. graeca and .. globulariae by 2- butyl 2-dodecenoate we have already registered earlier (EFETOV et al., 2014b), the attractiveness of this substance for Rh. pruni, A. geryon, J. notata, and .. subsolana was found for the first time.

Agradecimientos

For help in preparing 2-butyl 2-dodecenoate we thank Dr M. Y. Baevsky and Mr A. I. Poddubov (both - Simferopol, Crimea).

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