Holger Meyer

Semiochemicals from bark beetles: New results, remarks, and reflections

A brief survey is given about recent results in the identification of semiochemicals in bark beetles: Males ofIps sexdentatus (Boern.), stressed by the attack on resinous trees produce large amounts of 3(S)-1-methyl-5-(1-hydroxyl-1-methylethyl)-cyclohexa-1,3-diene. The compound appears to be derived from Δ3-carene and acts as a repellent. Males ofIps typographus (L.), stressed through the attack on unsuitable host material release 3-methyl-7-methylene-1,3(E), 8-nonatriene, which seems to act as a repellent. The odor bouquet of three species ofPityogenes is described. The occurrence of (+)-grandisol and other compounds related to weevil pheromones points to a close relation between Scolytidae and Curculionidae. Females ofDendroctonus simplex (Le Conte) use (−)-frontalin as the main pheromone. 6-Methyl-6-hepten-2-one, a minor component among the volatile compounds released by the females, is regarded as a possible precursor of frontalin. Similarly, (2R,5S)-2(1-hydroxyl-1-methylethyl)-5-methyltetrahydrofuran, pityol, a pheromone ofPityophthorus spp., is regarded to at least share a common biogenetic precursor with 6-methyl-5-hepten-2-ol, sulcatol. A new bicylic acetal, 2-ethyl-1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane, is described as an aggregation pheromone of the beech bark beetle,Taphrorychus bicolor (Herbst). Structural relationships between bark beetle pheromones and plant volatiles are discussed.

Pheromones in white pine cone beetle, Conophthorus coniperda (Schwarz) (Coleoptera: Scolytidae)

Female white pine cone beetles,Conophthorus coniperda, attacking second-year cones of eastern white pine,Pinus strobus L., produced a sex-specific pheromone that attracted conspecific males in laboratory bioassays and to field traps. Beetle response was enhanced by host monoterpenes. The female-produced compound was identified in volatiles collected on Porapak Q and in hindgut extracts as (+)-trans-pityol, (2R,5S)-(+)-2-(1-hydroxy-1-methylethyl)-5-methyltetrahydrofuran. Males and females produced and released the (E)-(-)-spiroacetal, (5S,7S)-(-)-7-methyl-1,6-dioxaspiro[4.5]decane, which was not an attractant for either sex, but acted as a repellent for males. Porapak Q-trapped volatiles from both sexes contained (+)-trans-pinocarveol and (-)-myrtenol. In addition, hindgut extracts of females containedtrans-verbenol, while males had pinocarvone and verbenone. Work in Georgia and Canada confirmed that the same isomers of pityol and spiroacetal are present in two distinct and widely separated populations ofC. coniperda.

The male pheromone of the old house borerHylotrupes bajulus (L.) (Coleoptera: Cerambycidae): Identification and female response

We report here the identification of the long-range, male-produced sex pheromone of the Old house borerHylotrupes bajulus. Chemical analysis of hexane extracts obtained by surface extraction from dissected prothoracic glands and from headspace samples of the two sexes, revealed male-specific compounds: (3R)-3-hydroxy-2-hexanone, 2-hydroxy-3-hexanone, the diastereomeric diols (2R, 3R)-2,3-hexanediol and (2S, 3R)-2,3-hexanediol, 2,3-hexanedione, as well as 1-butanol. In wind tunnel bioassays we tested the influence of these male-specific compounds from the prothoracal glands on the behaviour of unmated and mated females. Specific behavioural sequences of the tested females (activity, running behaviour, searching, cleaning, flying, extension of ovipositor) were recorded. Unmated females were attracted by male beetles, headspace extracts of males, synthetic blends of the major pheromone compounds as well as by the components (3R)-3-hydroxy-2-hexanone, and the diastereomeric diols. Hexane, female beetles and 2,3-hexanedione did not attract unmated females. The reactions of mated females to male beetles and headspace samples did not differ significantly from those of the controls. The results of the bioassays show that the two-stage premating behaviour is initiated by emission of a long-range sex pheromone from the male prothoracal glands, which functions as an activator, attractant, and possibly aphrodisiac for unmated females.

Volatile compounds in the larval frass ofDendroctonus valens andDendroctonus micans (Coleoptera: Scolytidae) in relation to oviposition by the predator,Rhizophagus grandis (Coleoptera: Rhizophagidae)

During a laboratory study evaluatingRhizophagus grandis (a specific native predator of the Eurasian bark beetle,Dendroctonus micans), as a potential biocontrol agent against the North American bark beetle,Dendroctonus valens, it was found that feeding larvae and laboratory-produced frass of the potential prey elicited very high oviposition responses in the predator. Comparative chemical analysis of this laboratory-produced larval frass revealed that one major volatile compound, (-)-fenchone, is associated with the larvae of bothDendroctonus species.D. micans also generated pinocamphone while oxygenated monoterpenes in the frass ofD. valens were camphor,cis-4-thujanol, fenchol, terpinen-4-ol, myrtenal, pinocarvone, borneol, verbenone, piperitone, campholenaldehyde,trans-myrtanol,cis-myrtanol,p-cymen-8-ol and 5-oxo-camphor. This range of prey-produced compounds with a possible biological effect onR. grandis was narrowed down subsequent to comparative analysis of field-collected larval frass. (-)-Fenchone, pinocamphone, camphor, terpinen-4-ol, borneol, fenchol, and verbenone were found to be common to both prey species. A mixture of these seven components was tested in a bioassay, where it elicited as much oviposition as did larval frass ofD. micans. The oviposition stimulants forR. grandis are thus clearly among the mixtures constituents.

The Secretion of the Ventral Glands in Nematus Sawfly Larvae

Abstract Nematine larvae possess ventral glands which contain compounds that protect the larvae from predation. More than 50 volatile compounds have been identified in secretions from the glands of 13 Nematus species. Monoterpenes constitute the major part of the secretion of five species in which long-chain aliphatic compounds (LCAC; C15–29) are also detected. In four other species, short-chain aliphatic compounds (SCAC; C6–8) and aromatic compounds are predominant, LCAC are also present, but monoterpenes are absent. In the four remaining species, the secretion is composed basically of LCAC. The diversity of chemotypes within the genus is discussed.