(R)-acetoin-female sex pheromone of the summer chafer Amphimallon solstitiale (L.)

Extracts of Amphimallon solstitiale (L.), a well known, widely distributed and rather common European scarab beetle, were analyzed by GC-MS and GC-EAD. Acetoin -(R):(S) < 9:1 - as well as 2,3-butanediol -(2R,3R):(2S,3S) :meso = 1:1:9 - were present in extracts of both males and females. Although (2S,3S)-butanediol did not show any EAD activity, the other compounds elicited strong responses exclusively with male antennae. In contrast, several EAD active green leaf volatiles were detected equally well by male and female antennae. During preliminary field bioassays, (R)-acetoin was highly attractive to swarming males, whereas neither rac-acetoin nor the 2,3-butanediols showed activity. Therefore, (R)-acetoin is the female sex pheromone of A. solstitiale.     

Sex Pheromone of <Emphasis Type="BoldItalic">Agriotes acuminatus</Emphasis> (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.     

(S)-(+)-linalool,a mate attractant pheromone component in the bee Colletes cunicularius

Enantiomerically pure (S)-(+)-linalool was the main constituent in the extracts of the cephalic secretions of virgin females, mated females, freshly emerged males, and patrolling males of the solitary bee Colletes cunicularius. After copulation, the content of (S)-(+)-linalool emitted by the female was strongly reduced. Electrophysiological experiments revealed that both enantiomers of linalool elicited responses from the antennae of the males. Field tests using the pure enantiomers and the racemate of linalool showed that the number of male bees attracted was highest for (S)-(+)-linalool. The search flight activity in the mating flight area increased dramatically when patrolling males were presented with (S)-(+)-linalool vs (R)-(–)-linalool. Taken together, these data indicate a mate attractant pheromone function of (S)-(+)-linalool.     

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.

     

First Sex Pheromone of the Order Strepsiptera: (3R,5R,9R)-3,5,9-Trimethyldodecanal in Stylops melittae Kirby, 1802

The twisted-wing parasites (Strepsiptera) are an unusual and small order of insects with about 600 known species. As obligate endoparasitoids, they develop and spend most of their lives living in other insects. Adults show an extreme sexual dimorphism: The free-living males have large eyes, branched antennae, reduced forewings, and well developed hind wings, while the neotenic females of most species lack all external characters that normally define an insect, remain endoparasitic, and only extrude the cephalothorax from the host. Due to the males’ short life span of only a few hours, there must be an efficient means of mate finding. This is believed to be mediated by chemical cues released by virgin females. Here, we report the first identification and synthesis of a female-produced strepsipteran sex pheromone, (3R,5R,9R)-3,5,9-trimethyldodecanal, from Stylops melittae, a species parasitizing andrenid bees. We found this highly EAD-active compound to be present in cephalothoraxes of and released from unmated females, and synthetic samples proved to be extremely attractive when offered in the field during the swarming period of the males. The structural features of this new natural compound may further support the re-establishment of the Strepsiptera as the closest living relatives of the Coleoptera.     

Mate Finding in the Parasitic Wasp Cephalonomia tarsalis (Ashmead): More than one way to a Female’s Heart

The parasitic wasp, Cephalonomia tarsalis (Hymenoptera: Bethylidae), parasitizes larvae of the sawtoothed grain beetle, Oryzaephilus surinamensis (L.) (Coleoptera: Silvanidae), and is used for biological control of this worldwide pest of stored grain. To study the hypothesis that C. tarsalis not only mates at its natal patch but also uses olfactory cues to find mating partners elsewhere, we investigated semiochemical use by male C. tarsalis. Olfactometer experiments revealed that male C. tarsalis are arrested by odors emanating from the cocoons of conspecifics, from young unmated females, and from feces of the host. Dodecanal, which was identified from extracts of filter paper contaminated by young females, had an arresting effect on males but not on females and was, therefore, considered as a sex pheromone. These findings indicate that C. tarsalis is a species with partial local mate competition. Males mate with females: 1) at the emergence site following location of females by sex pheromones from their cocoons, and 2) after dispersal from the natal patch following location of females directly by dodecanal and indirectly by unidentified sexual kairomones from host feces.     

Sex Pheromone of <Emphasis Type="Italic">Elater ferrugineus</Emphasis> 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.     

Foreign-language Skills in Rove-Beetles? Evidence for Chemical Mimicry of Ant Alarm Pheromones in Myrmecophilous <Emphasis Type="Italic">Pella</Emphasis> Beetles (Coleoptera: Staphylinidae)

By using chemical analyses, as well as laboratory and field behavioral tests, we tested the hypothesis that rove beetles of the myrmecophilous genus Pella use alarm pheromone compounds to avert attacks by their host ant Lasius fuliginosus. The secretions of Pella funestus and P. humeralis contain quinones and different aliphatic compounds, mainly undecane and 6-methyl-5-hepten-2-one (sulcatone). The latter two chemicals are also found in L. fuliginosus pheromone glands. Behavioral tests confirmed that undecane serves as an “aggressive alarm”-inducing pheromone in L. fuliginosus, whereas sulcatone most likely is a “panic-alarm”-inducing pheromone. The main tergal-secretion compounds, various quinones and undecane, individually and in mixtures induced aggression in L. fuliginosus workers. When sulcatone was added to these compounds, the space around the odor source was avoided and a reduced number of aggressive acts observed, suggesting that sulcatone blocks the aggression-inducing effect of undecane and the quinones. These results support the hypothesis that Pella beetles mimic alarm pheromones of their hosts. This is a rare example of chemical mimicry in myrmecophilous insects in which chemicals other than cuticular hydrocarbons are used.     

Major Sex Pheromone Component of Female Herald Moth Scoliopteryx libatrix is the Novel Branched Alkene (6Z,13)-Methylheneicosene

The major component of the female-produced sex pheromone of Scoliopteryx libatrix has been characterized by chemical analysis, synthesis, electrophysiological studies and field tests as (6Z,13)-methylheneicosene, probably the 13S-isomer. This is the first example of a branched chain alkene as a sex pheromone in the Noctuidae and is markedly different from the pheromones of other members of the family. The systematic position of S. libatrix, belonging to a monotypic genus of a one-member subfamily within the Noctuidae, may reflect the unusual structure of the sex pheromone.     

Characteristic odor of Osmoderma eremita identified as a male-released pheromone

Osmoderma eremita (Scopoli) is an endangered scarab beetle living in hollow trees. It has mainly been known for its characteristic odor, typically described as a fruity, peachlike or plumlike aroma. The odor emanating from a single beetle can sometimes be perceived from a distance of several meters. In this paper, we show that the characteristic odor from O. eremita is caused by the compound (R)-(+)--decalactone, released in large quantities mainly or exclusively by male beetles. Antennae from male and female beetles responded in a similar way to (R)-(+)--decalactone in electroantennographic recordings. Field trapping experiments showed that (R)-(+)--decalactone is a pheromone attracting female beetles. Lactones similar to (R)-(+)--decalactone are frequently used as female-released sex pheromones by phytophagous scarabs. This is, however, the first evidence of a lactone used as a male-produced pheromone in scarab beetles. We propose that the strong signal from males is a sexually selected trait used to compete for females and matings. The signal could work within trees but also act as a guide to tree hollows, which are an essential resource for O. eremita. Males may, thus, attract females dispersing from their natal tree by advertising a suitable habitat. This signal could also be exploited by other males searching for tree hollows or for females, which would explain the catch of several males in our traps.