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The recognition of cerambycids as frequent and damaging invaders led to an increase in the interest in the chemical ecology of the group with the identification of pheromones and pheromone-like attractants for well over 100 species. Pheromone components of the Cerambycidae are often phylogenetically conserved, with a single compound serving as a pheromone component for several related species. In the subfamily Lamiinae, the compound 2-(undecyloxy)ethanol (monochamol) has been identified as an aggregation-sex pheromone for several species of the genus Monochamus. In other species, including Monochamus maculosus Haldeman, field trials have demonstrated that monochamol is a pheromone attractant, but at that point it was still unknown as to whether it was a pheromone for this species. Here we report the identification, and laboratory and field trials of a pheromone component produced by adult male M. maculosus. Chemical analyses of headspace volatile collections sampled from field collected beetles of both sexes revealed the presence of one male-specific compound that was identified as 2-(undecyloxy)ethanol. Electroantennography analyses showed that monochamol elicited responses from the antennae of female beetles. Traps baited with monochamol in the field captured M. maculosus adults of both sexes corroborating the identification of monochamol as the sex-aggregation pheromone of this species. The attractivity of monochamol to adult M. maculosus in our field trapping experiment was synergized by the addition of the host volatile α-pinene. [ABSTRACT FROM AUTHOR]

The longhorn beetle Graphisurus fasciatus (Degeer) ranges from southeastern Canada to Florida and west to Texas, and has frequently been caught during field trials testing attraction of other cerambycid species to their synthesized pheromones. Collections of headspace volatiles from live beetles revealed that males but not females produce a polyketide compound identified as (4R,6S,7E,9E)-4,6,8-trimethylundeca-7,9-dien-3-one ([4R,6S,7E,9E]-graphisurone). Field trials verified that beetles of both sexes were attracted to the synthesized compound, indicating that it is an aggregation-sex pheromone. This structure represents a new structural motif among cerambycid pheromones, and a new natural product. While this study was in progress, the same compound was isolated from males of the South American cerambycid Eutrypanus dorsalis (Germar), in the same subfamily (Lamiinae) and tribe (Acanthocinini) as G. fasciatus. Field trials in Brazil confirmed that (4R,6S,7E,9E)-graphisurone is also an aggregation-sex pheromone for E. dorsalis, and a possible pheromone for two additional sympatric lamiine species, Hylettus seniculus (Germar) (Acanthocinini) and Oreodera quinquetuberculata (Drapiez) (tribe Acrocinini). These results indicate that graphisurone may be shared among a number of related species, as has been found with many components of cerambycid pheromones. [ABSTRACT FROM AUTHOR]

A novel trisubstituted tetrahydropyran was isolated and identified from the sex-specific volatiles produced by males of the cerambycid beetle Macropophora accentifer (Olivier), a serious pest of citrus and other fruit crops in South America. The compound was the major component in the headspace volatiles, and it was synthesized in racemic form. However, in field trials, the racemate was only weakly attractive to beetles of both sexes, suggesting that attraction might be inhibited by the presence of the "unnatural" enantiomer in the racemate. Alternatively, the male-produced volatiles contained a number of minor and trace components, including a compound tentatively identified as a homolog of the major component, as well as a number of unsaturated 8-carbon alcohols and aldehydes. Further work is required to conclusively identify and synthesize these minor components, to determine whether one or more of them are crucial components of the active pheromone blend for this species. [ABSTRACT FROM AUTHOR]

We describe the identification and field testing of 3-methylthiopropan-1-ol (methionol) as a male-produced aggregation-sex pheromone for the cerambycid beetle Knulliana cincta cincta (Drury) (subfamily Cerambycinae, tribe Bothriospilini). The corresponding sulfoxide, 3-methylsulfinylpropan-1-ol, was also produced sex-specifically by males, but its function remains unclear because the measured release rates of this compound from five different types of release devices were very low to undetectable. Unexpectedly, adults of the cerambycine Elaphidion mucronatum (Say) (Elaphidiini), primarily females, also were attracted by methionol, despite males of this species producing an aggregation-sex pheromone of entirely different structure, (2E,6Z,9Z)-2,6,9-pentadecatrienal. [ABSTRACT FROM AUTHOR]

Cerambycid beetles of the subfamily Lamiinae use male-produced aggregation-sex pheromones that are attractive to both sexes. Terpenoid pheromones have been identified from species in the tribes Acanthoderini and Acanthocinini native to North and South America, comprised of (E)-6,10-dimethyl-5,9-undecadien-2-one (geranylacetone), the structurally related 6-methylhept-5-en-2-one (sulcatone), and/or specific enantiomers or nonracemic ratios of enantiomers of the related compounds (E)-6,10-dimethyl-5,9-undecadien-2-ol (fuscumol), its acetate ester, (E)-6,10-dimethyl-5,9-undecadien-2-yl acetate (fuscumol acetate), and 6-methylhept-5-en-2-ol (sulcatol). Here, we present new information about the chemical ecology of six acanthoderine and acanthocinine species native to the eastern USA. The pheromone of Astyleiopus variegatus (Haldeman) previously was identified as a blend of (S)-fuscumol and (S)-fuscumol acetate, and we report here that geranylacetone is a synergistic component. Males of Aegomorphus modestus (Gyllenhal), Lepturges angulatus (LeConte), and Lepturges confluens (Haldeman) were found to produce similar blends composed of the enantiomers of fuscumol acetate and geranylacetone, whereas males of Astylidius parvus (LeConte) and Sternidius alpha (Say) produced both enantiomers of fuscumol together with (R)-fuscumol acetate and geranylacetone. Field experiments with synthesized chemicals revealed that species with similar pheromone composition nevertheless differed in their responses to individual components, and to various blends of components, and in how attraction was influenced by chemicals that were pheromone components of other species. Sulcatone and/or sulcatol antagonized attraction of some species to pheromones of the geranylacetone class, suggesting that there is an adaptive advantage in an ability to detect these heterospecific compounds, such as in avoiding cross attraction to other cerambycid species, as yet unknown, that use pheromones composed of both chemical classes. [ABSTRACT FROM AUTHOR]

Males of several species in the large cerambycid beetle subfamily Lamiine, native to South and North America, are known to produce aggregation-sex pheromones composed of three related structures: the sesquiterpene catabolic product geranylacetone, its corresponding alcohol (known as fuscumol), and the acetate ester of the alcohol (fuscumol acetate). Here, we show that males of two lamiine species native to the eastern USA, Astylopsis macula (Say) and Leptostylus transversus (Gyllenhal) (both tribe Acanthocinini), produce pheromones composed of the structurally related (S)-6-methylhept-5-en-2-ol ([S]-sulcatol). Males of both species also produced 6-methylhept-5-en-2-one (sulcatone), and males of A. macula produced trace amounts of (R)-fuscumol acetate. Field experiments demonstrated that both species were attracted by (S)-sulcatol. Sulcatone was not attractive as a single component, nor did it influence attraction of A. macula to (S)-sulcatol, while its effect on L. transversus was unclear. Data from the field experiments, and a separate experiment using traps fitted with a timer mechanism that rotated trap jars, revealed that the two species overlap only slightly in both seasonal and daily flight period, thus minimizing interspecific attraction. Racemic fuscumol acetate and fuscumol antagonized attraction of both species to sulcatol. The identification of sulcatol as a cerambycid pheromone extends the known range of pheromone components in the subfamily Lamiinae. [ABSTRACT FROM AUTHOR]

We describe the identification, synthesis, and field bioassays of a novel aggregation-sex pheromone produced by males of Susuacanga octoguttata (Germar), a South American cerambycid beetle. Analyses of extracts of headspace volatiles produced by adult beetles revealed a sex-specific compound emitted by males which was identified as (Z)-7-hexadecene by microchemical and spectroscopic analyses. The synthesized pheromone was attractive to beetles of both sexes in field trials. This unsaturated hydrocarbon motif is unprecedented among cerambycid pheromones identified to date. During field bioassays, we serendipitously discovered that adults of S. octoguttata trapped in two Brazilian biomes differed considerably in elytral markings, although males from both populations produced (Z)-7-hexadecene as an aggregation-sex pheromone. [ABSTRACT FROM AUTHOR]

During field screening trials conducted in Brazil in 2015, adults of both sexes of the cerambycid beetles Cotyclytus curvatus (Germar) and Megacyllene acuta (Germar) (subfamily Cerambycinae, tribe Clytini) were significantly attracted to racemic 3-hydroxyhexan-2-one and racemic 2-methylbutan-1-ol, chemicals which previously have been identified as male-produced aggregation-sex pheromones of a number of cerambycid species endemic to other continents. Subsequent analyses of samples of beetle-produced volatiles revealed that males of C. curvatus sex-specifically produce only (R)-3-hydroxyhexan-2-one, whereas males of M. acuta produce the same compound along with lesser amounts of (2S,3S)-2,3-hexanediol and (S)-2-methylbutan-1-ol. Follow-up field trials showed that both sexes of both species were attracted to synthetic reconstructions of their respective pheromones, confirming that males produce aggregation-sex pheromones. The minor pheromone components of M. acuta, (S)-2-methylbutan-1-ol and (2S,3S)-2,3-hexanediol, synergized attraction of that species, but antagonized attraction of C. curvatus to (R)-3-hydroxyhexan-2-one. Beetles of other cerambycine species also were attracted in significant numbers, including Chrysoprasis linearis Bates, Cotyclytus dorsalis (Laporte & Gory), and Megacyllene falsa (Chevrolat). Our results provide further evidence that 3-hydroxyhexan-2-one is a major component of attractant pheromones of numerous cerambycine species world-wide. Our results also highlight our increasing understanding of the crucial role of minor pheromone components in imparting species specificity to cerambycid pheromone blends, as is known to occur in numerous species in other insect families. [ABSTRACT FROM AUTHOR]

An increasing body of evidence suggests that the volatile pheromones of cerambycid beetles are much more diverse in structure than previously hypothesized. Here, we describe the identification, synthesis, and field testing of (2 E,6 Z,9 Z)-2,6,9-pentadecatrienal as a male-produced aggregation-sex pheromone of the cerambycid Elaphidion mucronatum (Say) (subfamily Cerambycinae, tribe Elaphidiini). This novel structure is unlike any previously described cerambycid pheromone, and in field bioassays attracted only this species. Males produced about 9 μg of pheromone per 24 h period, and, in field trials, lures loaded with 10, 25, and 100 mg of synthetic pheromone attracted beetles of both sexes, whereas lures loaded with 1 mg of pheromone or less were not significantly attractive. Other typical cerambycine pheromones such as 3-hydroxy-2-hexanone, syn-2,3-hexanediol, and anti-2,3-hexanediol were not attractive to E. mucronatum, and when combined with (2 E,6 Z,9 Z)-2,6,9-pentadecatrienal, the former two compounds appeared to inhibit attraction. Unexpectedly, adults of the cerambycine Xylotrechus colonus (F.) were attracted in significant numbers to a blend of 3-hydroxyhexan-2-one and (2 E,6 Z,9 Z)-2,6,9-pentadecatrienal, even though there is no evidence that this species produces the latter compound. From timed pheromone trap catches, adults of E. mucronatum were determined to be active from dusk until shortly after midnight. [ABSTRACT FROM AUTHOR]

The compound 1-(1 H-pyrrol-2-yl)-1,2-propanedione ('pyrrole') is an important pheromone component of several Asian and South American species of longhorned beetles in the subfamily Cerambycinae. Here, we report the first confirmed identification of this compound as a pheromone component of a cerambycine species native to North America, the rare beetle Dryobius sexnotatus Linsley. Headspace volatiles from males contained ( R)-3-hydroxyhexan-2-one and pyrrole (ratio 1:0.13), neither of which were detected in samples from a female. A field bioassay confirmed that adults of both sexes were attracted only to the binary blend of racemic 3-hydroxyhexan-2-one plus pyrrole, and not by either compound alone. Adults of another cerambycine, Xylotrechus colonus (F.), were attracted by 3-hydroxyhexan-2-one, consistent with this compound being the primary component of the pheromone of this species; attraction was not influenced by the presence of pyrrole. This study attests to the effectiveness of pheromone-baited traps in capturing rarely encountered species of cerambycids. It also provides further evidence that pyrrole represents another conserved pheromone motif within the Cerambycinae, now having been found in representatives of five cerambycid tribes from three continents. [ABSTRACT FROM AUTHOR]

Research over the last decade has revealed extensive parsimony among pheromones within the large insect family Cerambycidae, with males of many species producing the same, or very similar aggregation pheromones. Among some species in the subfamily Cerambycinae, interspecific attraction is minimized by temporal segregation, and/or by minor pheromone components that synergize attraction of conspecifics or inhibit attraction of heterospecifics. Less is known about pheromone-based mechanisms of reproductive isolation among species in the largest subfamily, the Lamiinae. Here, we present evidence that the pheromone systems of two sympatric lamiine species consist of synergistic blends of enantiomers of ( E)-6,10-dimethyl-5,9-undecadien-2-ol (fuscumol) and the structurally related ( E)-6,10-dimethyl-5,9-undecadien-2-yl acetate (fuscumol acetate), as a mechanism by which species-specific blends of pheromone components can minimize interspecific attraction. Male Astylidius parvus (LeConte) were found to produce ( R) - and ( S)-fuscumol + ( R)-fuscumol acetate + geranylacetone, whereas males of Lepturges angulatus (LeConte) produced ( R)- and ( S)-fuscumol acetate + geranylacetone. Field experiments confirmed that adult beetles were attracted only by their species-specific blend of the enantiomers of fuscumol and fuscumol acetate, respectively, and not to the individual enantiomers. Because other lamiine species are known to produce single enantiomers or blends of enantiomers of fuscumol and/or fuscumol acetate, synergism between enantiomers, or inhibition by enantiomers, may be a widespread mechanism for forming species-specific pheromone blends in this subfamily. [ABSTRACT FROM AUTHOR]

We report the identification of a novel pheromone structure from males of the cerambycid beetle Tylonotus bimaculatus Haldeman (Cerambycinae: Hesperophanini), a species native to eastern North America. Volatiles collected from adult males contained (2 S,4 E)-2-hydroxyoct-4-en-3-one (71 %), (3 R,4 E)-3-hydroxyoct-4-en-2-one (15 %), ( E)-4-octen-2,3-dione (13 %), and 2,3-octanedione (1.5 %). Four independent field bioassays with synthetic compounds confirmed that adults of both sexes were attracted by the racemate of the major component, ( E)-2-hydroxyoct-4-en-3-one. No other cerambycid species were attracted in significant numbers. Attraction of both sexes is consistent with the male-produced pheromones of many other species in the subfamily Cerambycinae, but T. bimaculatus is unusual in having a pheromone chemistry that is so far unique among species in that subfamily. [ABSTRACT FROM AUTHOR]

Recent research has shown that volatile sex and aggregation-sex pheromones of many species of cerambycid beetles are highly conserved, with sympatric and synchronic species that are closely related (i.e., congeners), and even more distantly related (different subfamilies), using the same or similar pheromones. Here, we investigated mechanisms by which cross attraction is averted among seven cerambycid species that are native to eastern North America and active as adults in spring: Anelaphus pumilus (Newman), Cyrtophorus verrucosus (Olivier), Euderces pini (Olivier), Neoclytus caprea (Say), and the congeners Phymatodes aereus (Newman), P. amoenus (Say), and P. varius (F.). Males of these species produce ( R)-3-hydroxyhexan-2-one as their dominant or sole pheromone component. Our field bioassays support the hypothesis that cross attraction between species is averted or at least minimized by differences among species in seasonal phenology and circadian flight periods of adults, and/or by minor pheromone components that act as synergists for conspecifics and antagonists for heterospecifics. [ABSTRACT FROM AUTHOR]

Recent work suggests that closely related cerambycid species often share pheromone components, or even produce pheromone blends of identical composition. However, little is known of the pheromones of species in the subfamily Prioninae. During field bioassays in California, males of three species in the prionine genus Tragosoma were attracted to 2,3-hexanediols, common components of male-produced aggregation pheromones of beetles in the subfamily Cerambycinae. We report here that the female-produced sex pheromone of Tragosoma depsarium 'sp. nov. Laplante' is (2 R,3 R)-2,3-hexanediol, and provide evidence from field bioassays and electroantennography that the female-produced pheromone of both Tragosoma pilosicorne Casey and T. depsarium ' harrisi' LeConte may be (2 S,3 R)-2,3-hexanediol. Sexual dimorphism in the sculpting of the prothorax suggests that the pheromone glands are located in the prothorax of females. This is the second sex attractant pheromone structure identified from the subfamily Prioninae, and our results provide further evidence of pheromonal parsimony within the Cerambycidae, in this case extending across both subfamily and gender lines. [ABSTRACT FROM AUTHOR]