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1.
J Econ Entomol ; 2024 Apr 16.
Article En | MEDLINE | ID: mdl-38625049

3-Hydroxyhexan-2-one (3-C6-ketol) has emerged as the most conserved pheromone structure within the beetle family Cerambycidae. In this study, we report the sex-specific production of this compound by males of 12 species of South American cerambycid beetles. Males of Chrysoprasis chalybea Redtenbacher and Mallosoma zonatum (Sahlberg) (Tribe Dichophyiini), and Ambonus lippus (Germar), Eurysthea hirta (Kirby), Pantonyssus nigriceps Bates, Stizocera plicicollis (Germar), and Stizocera tristis (Guérin-Méneville) (Elaphidiini) produced 3R-C6-ketol as a single component, whereas males of Neoclytus pusillus (Laporte & Gory) (Clytini), Aglaoschema concolor (Gounelle), Orthostoma abdominale (Gyllenhal) (Compsocerini), Dorcacerus barbatus (Olivier), and Retrachydes thoracicus thoracicus (Olivier) (Trachyderini) produced 3R-C6-ketol, along with lesser amounts of other compounds. In field trials testing 8 known cerambycid pheromone compounds, C. chalybea, E. hirta, and R. t. thoracicus were attracted in significant numbers to traps baited with 3-C6-ketol. A second field experiment provided support for the strategy of using the attraction of cerambycid species to test lures as a method of providing leads to their likely pheromone components. Because both sexes are attracted to these aggregation-sex pheromones, live beetles can be obtained from baited traps to verify they produce the compound(s) to which they were attracted, that is, that the compounds are indeed pheromone components.

2.
J Econ Entomol ; 2024 Mar 31.
Article En | MEDLINE | ID: mdl-38555618

Male cerambycid beetles of the large subfamilies Cerambycinae and Lamiinae produce aggregation-sex pheromones that attract both sexes. The pheromones of many species are conserved among both closely related species (e.g., congeners) and more distantly related species (e.g., different subfamilies), including those endemic to different continents. This parsimony in pheromone structures suggests that multiple species may be attracted to traps baited with blends of pheromones, and such blends are finding use in delineating geographic ranges of native species and in surveillance programs for incursions of exotic species. Here, we present the results of a field experiment conducted at multiple sites in Iowa that tested the effects of deploying ethanol lures in tandem with a 6-component blend of common pheromone components for cerambycine and lamiine species and a 5-component blend that specifically targeted lamiines. Eight cerambycine species showed significant treatment effects, most of which were attracted to the 6-component blend, and ethanol increased attraction for half of these species. Two cerambycine species were attracted only by ethanol. Seven lamiine species were attracted by the lamiine-specific blend, alone or when combined with ethanol, and 3 of these species also were attracted to the 6-component blend. Taken together, these findings provide further evidence that carefully crafted blends of pheromones can be used to monitor the presence or abundance of multiple cerambycid species. Ethanol either increased the number of beetles attracted by pheromones or had no effect, so there is no apparent downside to deploying ethanol lures in combination with pheromones.

3.
J Chem Ecol ; 50(3-4): 122-128, 2024 Apr.
Article En | MEDLINE | ID: mdl-38388901

The scarab genus Osmoderma (Coleoptera: Scarabaeidae) includes several large species called hermit beetles that develop within dead and decaying hardwood trees. Males of at least three Palearctic species produce the aggregation-sex pheromone (R)-(+)-γ-decalactone, including the endangered O. eremita (Scopoli). However, hermit beetles have received less attention in the western hemisphere, resulting in a large gap in our knowledge of the chemical ecology of Nearctic species. Here, we identify (R)-( +)-γ-decalactone as the primary component of the aggregation-sex pheromone of the North American species Osmoderma eremicola (Knoch). Field trials at sites in Wisconsin and Illinois revealed that both sexes were attracted to lures containing (R)-(+)-γ-decalactone or the racemate, but only males of O. eremicola produced the pheromone in laboratory bioassays, alongside an occasional trace of the chain-length analog γ-dodecalactone. Females of the congener O. scabra (Palisot de Beauvois) were also significantly attracted by γ-decalactone, suggesting further conservation of the pheromone, as were females of the click beetle Elater abruptus Say (Coleoptera: Elateridae), suggesting that this compound may have widespread kairomonal activity. Further research is needed to explore the behavioral roles of both lactones in mediating behavioral and ecological interactions among these beetle species.


Coleoptera , Lactones , Sex Attractants , Animals , Coleoptera/physiology , Male , Female , Sex Attractants/chemistry , Sex Attractants/pharmacology , Sex Attractants/metabolism , Lactones/chemistry , Lactones/metabolism , Lactones/pharmacology , Pheromones/metabolism , Pheromones/chemistry , Pheromones/pharmacology
4.
Environ Entomol ; 53(1): 101-107, 2024 Feb 20.
Article En | MEDLINE | ID: mdl-38160262

As part of a long-term project on unraveling the use of pheromones in the large beetle family Cerambycidae, field trials were conducted with generic blends of known cerambycid pheromones at a desert site in southern California. In the first year of testing (2022), the species Eustromula valida (LeConte) (subfamily Cerambycinae, tribe Elaphidiini) and Aethecerinus latecinctus (Horn) (Cerambycinae, Trachyderini) were weakly attracted to one of the lure blends. In follow-up trials in 2023, only E. valida were caught, and collection of volatiles from both sexes of E. valida determined that males sex-specifically produced 3-methylthiopropan-1-ol (methionol), a compound that was not in the tested lure blends. Beetles of both sexes were strongly and specifically attracted to this compound in field bioassays, verifying that it is an aggregation-sex pheromone. No sympatric species were attracted to methionol while it was deployed in the field. Several recent studies have identified methionol as a pheromone component for other cerambycid species in both North and South America, suggesting it may represent another common pheromone component within the Cerambycidae.


Coleoptera , Sex Attractants , Sulfides , Female , Male , Animals , Sex Attractants/pharmacology , Pheromones/pharmacology , Propanols
5.
J Econ Entomol ; 116(6): 2035-2042, 2023 12 11.
Article En | MEDLINE | ID: mdl-37878589

Adult male cerambycid beetles of the subfamilies Cerambycinae and Lamiinae emit aggregation-sex pheromones that attract both sexes, and these chemicals can be utilized for quarantine surveillance for related exotic species which produce the same or similar pheromones. Here, we assess how attraction of 7 cerambycid species to pheromone-baited traps was influenced by the release rates of synthesized pheromones from polyethylene sachet emitters. Compounds tested included racemic 3-hydroxyhexan-2-one, the (R)-enantiomer of which is the sole or major pheromone component of numerous cerambycine species, and 2 compounds that are pheromone components of many lamiine species: (E)-6,10-dimethyl-5,9-undecadien-2-yl acetate (fuscumol acetate) and 6-methylhept-5-en-2-ol (sulcatol). We confirmed release rates of these compounds could be manipulated by varying the doses loaded into emitters. Various doses and concentrations, ranging from very dilute to the neat compounds, were then tested in field trials. Several species were most strongly attracted to the highest dose of a tested compound, one species to an intermediate dose, while another species was equally attracted regardless of dose. Our results demonstrate the importance of characterizing dose-response relationships for cerambycid species targeted by pheromone-based trapping.


Coleoptera , Sex Attractants , Female , Male , Animals , Coleoptera/physiology , Pheromones/pharmacology , Sex Attractants/pharmacology , Sexual Behavior, Animal , Acetates
6.
J Chem Ecol ; 49(7-8): 363-368, 2023 Aug.
Article En | MEDLINE | ID: mdl-37085723

The beetle family Disteniidae is currently considered to be closely related to the much larger family Cerambycidae, the longhorned beetles. The 300 + species of disteniids are mostly native to tropical and subtropical regions, with the only described North American species north of Mexico being Elytrimitatrix undata (F.). Here we describe the identification and field testing of (1R,4R)-quercivorol as a male-produced aggregation-sex pheromone component for E. undata. This is the first pheromone identified for any species within the family Disteniidae.


Coleoptera , Sex Attractants , Animals , Male , Sex Attractants/pharmacology , Pheromones , Monoterpenes
7.
J Chem Ecol ; 48(5-6): 569-582, 2022 Jun.
Article En | MEDLINE | ID: mdl-35501536

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.


Coleoptera , Sex Attractants , Spiders , Aldehydes , Animals , Female , Male , Pheromones , Sex Attractants/pharmacology
8.
J Chem Ecol ; 48(4): 347-358, 2022 Apr.
Article En | MEDLINE | ID: mdl-35366125

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.


Coleoptera , Sex Attractants , Animals , Female , Male , North America , Pheromones , Propanols , Sex Attractants/chemistry , Sulfides , Sulfur
9.
J Chem Ecol ; 48(7-8): 598-608, 2022 Aug.
Article En | MEDLINE | ID: mdl-35397045

Hexanoic acid, 1-octanol, 1,8-octanediol, octyl hexanoate, 1,8-octanediol monohexanoate, and 1,8-octanediol dihexanoate were identified in headspace volatiles collected from the crushed abdomen of a female click beetle of the species Parallelostethus attenuatus (Say) (Elaterinae, tribe Elaterini). In field trials carried out in Illinois, South Carolina, North Carolina, and Virginia, adult male beetles were strongly attracted to 1,8-octanediol dihexanoate alone. Blends of the dihexanoate with one or more of the other compounds proved to be less attractive than the dihexanoate alone, suggesting that the pheromone of this species may consist of a single compound. The symmetrical diester structure of the pheromone is a novel natural product and appears to be structurally unique among insect pheromones.


Coleoptera , Sex Attractants , Animals , Coleoptera/chemistry , Female , Male , North America , Pheromones/pharmacology , Sex Attractants/chemistry , Sex Attractants/pharmacology
10.
Insects ; 12(10)2021 Oct 02.
Article En | MEDLINE | ID: mdl-34680668

(1) Background: The principal aim of our work was to identify pheromone components for Plagionotus detritus (L.) (Coleoptera: Cerambycidae), which could be exploited for developing a pheromone-based monitoring system for the complementary purposes of plant protection in areas where it might become a pest, and natural conservation in areas where it is rare or endangered. (2) Methods: Collection and analysis of headspace volatiles were carried out with field-collected beetles. Bioactive volatile compounds identified [(R)-3-hydroxyhexan-2-one and (S)-2-hydroxyoctan-3-one] from extracts of males were purchased [(±)-3-hydroxyhexan-2-one], and synthesized [(S)-2-hydroxyoctan-3-one] and field-tested. Electroantennogram assays showed that antennae of the predatory beetle Clerus mutillarius F. (Coleoptera: Cleridae) also responded to the synthetic compounds. (3) Results: A two-component aggregation-sex pheromone consisting of (R)-3-hydroxyhexan-2-one and (S)-2-hydroxyoctan-3-one was identified for P. detritus. (±)-3-hydroxyhexan-2-one and (S)-2-hydroxyoctan-3-one attracted adults of P. detritus in field bioassays. Adults of the clerid C. mutillarius also were attracted to both compounds. The cerambycid Xylotrechus antilope Schönh was significantly attracted to traps baited with (S)-2-hydroxyoctan-3-one alone or the blend containing this compound. (4) Conclusions: Our data confirmed that 3-hydroxyhexan-2-one and 2-hydroxyoctan-3-one are male-produced pheromone components for P. detritus. These results show that both intraspecific and interspecific communication may play key roles in longhorn beetle life history and ecology, with closely and more distantly related species eavesdropping on each other's signals.

11.
J Chem Ecol ; 47(12): 941-949, 2021 Dec.
Article En | MEDLINE | ID: mdl-34532812

Here, we study the pheromone chemistry of two South American cerambycid beetle species, and their behavioral responses to candidate pheromone components. Adult males of Stizocera phtisica Gounelle (subfamily Cerambycinae: tribe Elaphidiini) produced a sex-specific blend of (R)-3-hydroxyhexan-2-one with lesser amounts of 3-methylthiopropan-1-ol. In field bioassays, traps baited with racemic 3-hydroxyhexan-2-one and 3-methylthiopropan-1-ol did not catch conspecific beetles, but did catch both sexes of a sympatric species, Chydarteres dimidiatus dimidiatus (F.) (Cerambycinae: Trachyderini). We found that males of this species also produce (R)-3-hydroxyhexan-2-one and 3-methylthiopropan-1-ol, and small amounts of 2-phenylethanol. Subsequent bioassays with these compounds showed that a blend of 3-hydroxyhexan-2-one and 3-methylthiopropan-1-ol constitutes the aggregation-sex pheromone of C. d. dimidiatus, with 2-phenylethanol not influencing the attraction of conspecifics. During the field bioassays, six other species in the Cerambycinae also were caught in significant numbers, including Aglaoschema ventrale (Germar) (tribe Compsocerini), congeners Chrysoprasis aurigena (Germar), Chrysoprasis linearis Bates, and an unidentified Chrysoprasis species (Dichophyiini), and Cotyclytus curvatus (Germar) and Itaclytus olivaceus (Laporte & Gory) (both Clytini), suggesting that one or more of the compounds tested are also pheromone components for these species.


Coleoptera/drug effects , Pheromones/pharmacology , Animals , Coleoptera/physiology , Hexanones/pharmacology , Male , South America , Species Specificity
12.
Environ Entomol ; 50(6): 1294-1298, 2021 12 17.
Article En | MEDLINE | ID: mdl-34401912

A number of recent studies have demonstrated the potential for using blends of pheromones of cerambycid beetles to attract several species simultaneously. Here, we tested the effects of adding the pheromones of two invasive species, Trichoferus campestris (Faldermann) and Aromia bungii (Faldermann), on the attraction of native species to a generic blend of synthesized pheromones, in season-long field trials at 12 sites in Pennsylvania. Of the four species attracted in significant numbers, Megacyllene caryae (Gahan), Phymatodes amoenus (Say), and P. testaceus (L.) (all subfamily Cerambycinae) were not significantly affected by the addition of the T. campestris pheromone trichoferone and the A. bungii pheromone (E)-2-cis-6,7-epoxynonenal to the generic blend. In contrast, trap catches of Sternidius alpha (Say) (subfamily Lamiinae) were completely shut down by addition of the pheromones of the two exotic species. In addition, there was no indication that any native species were attracted to trichoferone or (E)-2-cis-6,7-epoxynonenal, suggesting that these pheromones are probably not used by species native to eastern North America.


Coleoptera , Sex Attractants , Animals , Introduced Species , Pennsylvania , Pheromones/pharmacology , Seasons , Sex Attractants/pharmacology
13.
Insects ; 12(4)2021 Mar 24.
Article En | MEDLINE | ID: mdl-33805014

The Cerambycidae comprise a large and ecologically important family of wood-boring beetles. The purpose of this study was to examine the effectiveness of a generic lure as a potential monitoring tool. Working in a subtropical forest in southwest China, we set traps baited with generic lures at ground level (1 m) and canopy height (~18 m) across 22 randomly located forest plots (12 regenerating forest, 10 mature forest). Three stations were established per plot and each plot was trapped for 7 days in May-June 2013. In total, 4541 beetles of 71 species were caught, including 26 species with 10 or more individuals. We used Hierarchical Modeling of Species Communities (HMSC) to analyze the data and produced informative models for 18 species, showing that trap height, slope, elevation, and leaf-area index were important determinants of cerambycid distribution. Our results demonstrate the potential for using generic lures to detect and monitor cerambycid populations, both for regulatory purposes and for the study of cerambycid beetle ecology. Further research should focus on refining lure blends, and on repeated sampling to determine temporal and spatial dynamics of cerambycid communities.

14.
Environ Entomol ; 50(3): 599-604, 2021 06 18.
Article En | MEDLINE | ID: mdl-33724303

An increasing body of evidence indicates that cerambycid beetles native to different continents may share pheromone components, suggesting that these compounds arose as pheromone components early in the evolution of the family. Here, we describe the identification and field testing of the pheromone blends of two species in the subfamily Cerambycinae that share 2-nonanone as an important component of their male-produced aggregation-sex pheromones, the South American Stizocera consobrina Gounelle (tribe Elaphidiini) and the North American Heterachthes quadrimaculatus Haldeman (tribe Neoibidionini). Along with 2-nonanone, males of S. consobrina also produce 1-(1H-pyrrol-2-yl)-1,2-propanedione, whereas males of H. quadrimaculatus produce 10-methyldodecanol. Field bioassays conducted in Brazil (targeting S. consobrina) and Illinois (targeting H. quadrimaculatus) demonstrated that adults of both species were attracted only by the blends of both their pheromone components, and not to the individual components. The use of the pyrrole as a critical component for the former species is further evidence that this compound is a common pheromone structure among cerambycines in different biogeographical regions of the world.


Coleoptera , Sex Attractants , Animals , Brazil , Illinois , Ketones , Male , Pheromones
15.
J Econ Entomol ; 113(5): 2269-2275, 2020 10 16.
Article En | MEDLINE | ID: mdl-32696963

The wood-boring larvae of longhorned beetles (Coleoptera: Cerambycidae) can be important pests of woody plants, particularly as invasive species introduced by international commerce. Previous research has revealed that cerambycid species native to different parts of the world often share the same aggregation-sex pheromones and that pheromones of different species can be combined to create multi-species attractants that would be advantageous for surveillance monitoring for a number of species simultaneously. To explore the extent to which these chemicals can be combined into single lures, we developed four different blends of six to eight compounds and tested their effects as attractants for a community of longhorned beetle species in Iowa. The blends included known pheromones of species native to the study site, as well as pheromones identified from cerambycid species native to other parts of the world. The experiment confirmed that several cerambycid species were attracted by specific blends, in accordance with their known pheromone chemistry, and despite the presence of pheromone components of heterospecifics. This finding lends further support to developing multi-component blends that can effectively monitor for new incursions of multiple exotic species concurrently.


Coleoptera , Sex Attractants , Animals , Iowa , Larva , Pheromones/pharmacology , Sex Attractants/pharmacology
16.
Insects ; 11(4)2020 Apr 02.
Article En | MEDLINE | ID: mdl-32252447

We describe the identification, synthesis, and field-testing of aggregation-sex pheromones, or likely pheromone candidates, of seven species of South American cerambycid beetles in the subfamily Cerambycinae, of the tribes Eburiini and Neoibidionini. Analyses of extracts of volatiles released by adult males revealed that Eburodacrys dubitata White produce 11-methyltridecanal, whereas the males of Eburodacrys assimilis Gounelle, Eburodacrys flexuosa Gounelle, and Eburodacrys lenkoi Napp and Martins produce blends of this compound, along with its analog 10-methyldodecanal. In contrast, males of Compsibidion graphicum (Thomson) and Compsibidion sommeri (Thomson) produce blends of 10-methyldodecanal and its corresponding alcohol 10-methyldodecanol. The results from field bioassays with synthetic compounds showed that each species was specifically attracted to traps containing their reconstructed pheromone blend. However, E. assimilis was not trapped, possibly due to inhibition by non-natural enantiomers in the racemic test compounds. During the trials for the Compsibidion species, adults of another cerambycid species, Tetraopidion mucoriferum (Thomson), were captured in significant numbers in traps baited with 10-methyldodecanol, suggesting that this compound is a pheromone component for this species. This study demonstrates another case of conservation of pheromone structures within South American cerambycid species. It also highlights how blends of closely related structures, differing only in chain length or functional group, make the evolution of species-specific pheromone channels possible.

17.
J Chem Ecol ; 46(2): 232, 2020 02.
Article En | MEDLINE | ID: mdl-32016776

The original version of this article unfortunately contained a mistake. When filing the final publication details, we failed to include the following statement in our Acknowledgments paragraph: We thank the Almond Board of California for research funding.

18.
J Chem Ecol ; 46(1): 30-39, 2020 Jan.
Article En | MEDLINE | ID: mdl-31808075

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.


Coleoptera/chemistry , Pheromones/chemistry , Animals , Coleoptera/metabolism , Female , Gas Chromatography-Mass Spectrometry , Male , Pheromones/isolation & purification , Pheromones/pharmacology , Sexual Behavior, Animal/drug effects , Species Specificity , Stereoisomerism , Terpenes/chemistry , Terpenes/isolation & purification , Terpenes/pharmacology , Volatile Organic Compounds/chemistry , Volatile Organic Compounds/isolation & purification , Volatile Organic Compounds/pharmacology
19.
J Chem Ecol ; 46(1): 40-47, 2020 Jan.
Article En | MEDLINE | ID: mdl-31808076

Cuticular hydrocarbons (CHCs) are the main components of the epicuticular wax layer that in many insects functions as a barrier against desiccation. CHCs also play many other roles, including serving as sex pheromones, kairomones, primer pheromones, and colony-, caste-, species- and sex-recognition signals. In insects, CHC profiles can vary depending upon age, species, sex, and strain. Understanding factors associated with variation in hydrocarbon profiles is important for identifying potential vulnerabilities relating to pest ecology and life histories and for developing tools for pest monitoring and management strategies. In this study, we assessed potential sources of variation in CHC profiles in the navel orangeworm Amyelois transitella (Walker) (Lepidoptera: Pyralidae), an economically important pest of nut crops in California. Using coupled gas chromatography-mass spectrometry, we characterized and compared CHC profiles between adults of pyrethroid-resistant (R347) and susceptible (ALMOND) strains. We further compared CHC profiles from adults differing in age (1, 3, 5, and 7 d post-eclosion) and sex. Hydrocarbon profiles comprised 47 different CHCs in detectable quantities that ranged from C17 to C43 in chain length and included straight-chain alkanes and a variety of mono-, di-, and tri-methylalkanes. Adults from resistant populations had greater quantities of CHCs in total than those from susceptible strains, but relative quantities of individual components were similar. The six most abundant compounds were n-pentacosane, n-heptacosane, n-nonacosane, n-hentriacontane, 11,25 + 13,23 + 15,21-dimethylpentatriacontane, and 13,23 + 11,25 + 9,17-dimethylheptatriacontane. Post-eclosion, total CHCs increased with adult age, with males producing greater quantities than females at all ages. Our results show that CHC profiles vary depending on age, sex, and strain and suggest that CHC profiles may be useful as biomarkers to differentiate between insecticide- resistant and susceptible populations.


Hydrocarbons/chemistry , Moths/chemistry , Animals , Chromatography, High Pressure Liquid , Female , Hydrocarbons/analysis , Male , Mass Spectrometry , Moths/metabolism , Principal Component Analysis , Sex Characteristics , Time Factors
20.
J Chem Ecol ; 45(7): 537-548, 2019 Jul.
Article En | MEDLINE | ID: mdl-31254146

Longhorn beetles are ecologically important insects in forest ecosystems as decomposers of woody substrates, microhabitat engineers, and as components of forest food webs. These species can be greatly affected both positively and negatively by modern forestry management practices, and should be monitored accordingly. Through headspace sampling, coupled gas chromatography-electroantennography, gas chromatography-mass spectrometry, and field bioassays, we identified two compounds, 2-methyl-1-butanol and 3-hydroxy-2-hexanone, that constitute aggregation-sex pheromone attractants of three cerambycid species which breed primarily in different types of fresh, recently dead oak wood in Northern Europe: Pyrrhidium sanguineum (L.), Phymatodes alni ssp. alni (L.), and Phymatodes testaceus (L.) (Cerambycinae: Callidiini). Analyses of headspace volatiles collected from live insects indicated that the male-produced aggregation-sex pheromone of P. sanguineum is a 1-15:100 blend of (R)-2-methyl-1-butanol and (R)-3-hydroxy-2-hexanone, whereas the corresponding ratios for P. alni were 70-110:100. In field bioassays, adult P. sanguineum and P. alni were significantly attracted to multiple blends with varying ratios of the two compounds. When tested individually, the compounds were minimally attractive. In contrast, adult P. testaceus exhibited nonspecific attraction to both of the individual compounds and to different blends, despite the hydroxyketone not being part of its pheromone, which consists of (R)-2-methyl-1-butanol alone. Overall, our results suggest that a blend of 50:100 of racemic 2-methyl-1-butanol and 3-hydroxy-2-hexanone is appropriate for parallel, cost-efficient pheromone-based monitoring of all three species. In particular, these species could serve as useful indicators of how modern forestry practices affect a whole guild of saproxylic insects that require ephemeral deadwood substrates for successful breeding.


Coleoptera/physiology , Sex Attractants/chemistry , Animals , Europe , Female , Gas Chromatography-Mass Spectrometry , Hexanones/analysis , Hexanones/pharmacology , Male , Pentanols/analysis , Pentanols/pharmacology , Sex Attractants/pharmacology , Sexual Behavior, Animal/drug effects , Volatile Organic Compounds/chemistry , Volatile Organic Compounds/pharmacology
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