Sex Pheromone of the Click Beetle Agriotes pilosellus (SCHöNHERR, 1718).

Agriotes pilosellus is a fairly common click beetle species distributed in open deciduous and mixed forests throughout a large area in Europe. To identify its sex pheromone, gland extracts of female beetles were analyzed using gas chromatography-mass spectrometry (GC-MS). The only volatile compounds present in the extracts were geranyl butanoate and (E)-8-hydroxygeranyl dibutanoate in a 1:3 ratio, identified by comparison with synthetic samples. Field experiments revealed a clear attraction of A. pilosellus - males towards traps baited with geranyl butanoate, which could be synergistically enhanced by the factor of almost ten by addition of (E)-8-hydroxygeranyl dibutanoate. The latter compound alone did not show any attractive effect. Both compounds correspond well to the structures known from other Agriotes species and may serve as an effective monitoring tool for entomofaunistic research.

Identification of the sex pheromone of Idolus picipennis (Bach, 1852) revealed the presence of a cryptic sibling species.

The click beetle Idolus picipennis represents the only species of its genus in Europe, where it is widely distributed but is rare and only occurs locally. In order to identify its sex pheromone we investigated gland extracts of females from populations in southern Germany. GC/MS analyses revealed two distinct types of gland compositions that correspond to slight but consistent morphological differences in the respective beetles. Extracts of one type contain four compounds, geranyl hexanoate (~ 40 %), (Z,E)-farnesyl hexanoate (~ 10 %), (E,E)-farnesyl hexanoate (~ 40 %), and (E,E)-farnesyl octanoate (~ 10 %), and this type belongs to the authentic I. picipennis (Bach 1852). Extracts of a second type contain neryl hexanoate (~10 %) and neryl octanoate (~ 90 %), and this type belongs to an Idolus species that apparently has been overlooked to date, presumably due to similarity with the authentic I. picipennis and insufficient material in collections. Synthetic blends of the identified compounds in their naturally-occurring ratios, as well as the main compounds alone, proved to be highly attractive to swarming males of the respective species in the field. A strong species-specific attraction also was observed in a locality where both species co-occur, thus confirming effective reproductive isolation. This study shows the potential of sex pheromones for monitoring rare and threatened insects as well as for detecting hitherto unknown cryptic species.

Sex Pheromone of Agriotes acuminatus (Stephens, 1830) (Coleoptera: Elateridae).

The click beetle species Agriotes acuminatus is distributed in open deciduous forests throughout a large area in Europe. In order to identify its sex pheromone, gland extracts of female beetles were investigated by using GC/MS. Neryl butanoate and 2,6-dimethyl-(Z,E)-2,6-octadien-1,8-diol dihexanoate, in a ratio of approximately 1:5, were the only volatile compounds present in the extracts. Structures of both esters were confirmed by synthesis. Field experiments revealed a strong attraction of A. acuminatus males towards neryl butanoate, which could be synergistically enhanced by addition of 2,6-dimethyl-(Z,E)-2,6-octadien-1,8-diol dihexanoate. The latter compound alone did not show any attractive effect. While all Agriotes spp. investigated to date use geranyl and/or (E,E)-farnesyl esters as sex pheromones, the nerol derivatives of A. acuminatus are the first (Z)-2-configurated pheromones within this genus.

Flower volatiles, crop varieties and bee responses.

Pollination contributes to an estimated one third of global food production, through both the improvement of the yield and the quality of crops. Volatile compounds emitted by crop flowers mediate plant-pollinator interactions, but differences between crop varieties are still little explored. We investigated whether the visitation of crop flowers is determined by variety-specific flower volatiles using strawberry varieties (Fragaria x ananassa Duchesne) and how this affects the pollination services of the wild bee Osmia bicornis L. Flower volatile compounds of three strawberry varieties were measured via headspace collection. Gas chromatography showed that the three strawberry varieties produced the same volatile compounds but with quantitative differences of the total amount of volatiles and between distinct compounds. Electroantennographic recordings showed that inexperienced females of Osmia bicornis had higher antennal responses to all volatile compounds than to controls of air and paraffin oil, however responses differed between compounds. The variety Sonata was found to emit a total higher level of volatiles and also higher levels of most of the compounds that evoked antennal responses compared with the other varieties Honeoye and Darselect. Sonata also received more flower visits from Osmia bicornis females under field conditions, compared with Honeoye. Our results suggest that differences in the emission of flower volatile compounds among strawberry varieties mediate their attractiveness to females of Osmia bicornis. Since quality and quantity of marketable fruits depend on optimal pollination, a better understanding of the role of flower volatiles in crop production is required and should be considered more closely in crop-variety breeding.

Sex pheromone of Elater ferrugineus L. (Coleoptera: Elateridae).

The rare European click beetle, Elater ferrugineus L., develops exclusively in old, hollow deciduous trees. As a result of massive habitat loss caused by modern forestry, it is threatened throughout its entire distribution range and regarded as an indicator species for undamaged natural forests. As E. ferrugineus lives cryptically and its populations are frequently overlooked, we investigated its sex pheromone to develop a reliable detection tool. Pheromone gland extracts of single female E. ferrugineus were examined by using gas chromatography-mass spectrometry (GC-MS). All samples contained 7-methyloctyl 5-methylhexanoate, 7-methyloctyl octanoate, 7-methyloctyl 7-methyloctanoate, and 7-methyloctyl (Z)-4-decenoate in a ratio of approximately 1:1:3:3. Structures of all four esters, which have not been reported as pheromone compounds before, were confirmed by synthesis. A blend of the components was tested in the field and proved to be attractive for E. ferrugineus males, which were found to swarm exclusively during the day. This blend provides a noninvasive and effective monitoring method for this cryptic species, promising future collection records of E. ferrugineus in regions where it exists below the limit of detection by conventional collecting methods.