Search

The emerald ash borer, Agrilus planipennis Fairmaire (Coleoptera: Buprestidae), is a devastating insect pest in its introduced range. A trapping system that increases trap catches or detection rates in low-density populations would be beneficial for survey programs. Five trapping experiments were conducted to investigate factors influencing capture rates of male beetles on dark green traps baited with the A. planipennis pheromone, (3Z)-dodecen-12-olide ((3Z)-lactone), plus the green leaf volatile, (3Z)-hexenol. Low doses (0.001-1.0 mg) of (3Z)-lactone + (3Z)-hexenol did not consistently increase captures of male A. planipennis. In other experiments, mean captures of males were significantly higher on traps baited with a moderate dose (3.0 mg/septum) of (3Z)-lactone + (3Z)-hexenol, compared with lower doses (0.001, 0.1, and 1.0 mg) or (3Z)-hexenol alone. Next, we demonstrated that addition of (3Z)-lactone to traps baited with (3Z)-hexenol resulted in significantly greater increases in male captures when pairs of traps were placed on the same tree, than when traps were placed on adjacent trees. Moreover, significantly more A. planipennis were captured on pheromone-baited traps placed in the southern versus northern aspect of the crown. These results highlight the importance of experimental set-up for elucidating lure treatment effects and also suggests the (3Z)-lactone may be more active at close range. Our findings increase our understanding of the pheromone ecology of this species and lend support toward the use of dark green traps baited with 3.0 mg (3Z)-lactone + (3Z)-hexenol deployed in the south aspect of the canopy for detection programs for this insect., (© The Authors 2015. Published by Oxford University Press on behalf of Entomological Society of America. All rights reserved. For Permissions, please email: journals.permissions@oup.com.)

Analysis by gas chromatography/mass spectrometry (GC/MS) of volatiles from virgin female emerald ash borer, Agrilus planipennis Fairmaire confirmed the emission of (3Z)-lactone [(3Z)-dodecen-12-olide] but not its geometric isomer, (3E)-lactone [(3E)-dodecen-12-olide]. Gas chromatographic/electroantennographic (GC/EAD) analysis of synthetic (3Z)-lactone, which contained 10% (3E)-lactone, showed a strong response of male and female antennae to both isomers. EAG analysis with 0.01- to 100-μg dosages showed a positive dose response, with females giving significantly higher responses than males. In field experiments with sticky purple prism traps, neither lactone isomer affected catches when combined with ash foliar or cortical volatiles (green leaf volatiles or Phoebe oil, respectively). However, on green prism traps, the (3Z)-lactone significantly increased capture of male A. planipennis when traps were deployed in the canopy. Captures of males on traps with both (3E)-lactone and (3Z)-hexenol or with (3Z)-lactone and (3Z)-hexenol were increased by 45-100%, respectively, compared with traps baited with just (3Z)-hexenol. In olfactometer bioassays, males were significantly attracted to (3E)-lactone, but not the (3Z)-lactone or a 60:40 (3E):(3Z) blend. The combination of either (3E)- or (3Z)-lactone with Phoebe oil was not significantly attractive to males. Males were highly attracted to (3Z)-hexenol and the (3Z)-lactone + (3Z)-hexenol combination, providing support for the field trapping results. These data are the first to demonstrate increased attraction with a combination of a pheromone and a green leaf volatile in a Buprestid species.

Analyses of the elytral hydrocarbons from male and female emerald ash borer, Agrilus planipennis Fairmaire, that were freshly emerged vs. sexually mature (>10 days old) revealed a female-specific compound, 9-methyl-pentacosane (9-Me-C(25)), only present in sexually mature females. This material was synthesized by the Wittig reaction of 2-decanone with (n-hexadecyl)-triphenylphosphonium bromide followed by catalytic reduction to yield racemic 9-Me C(25), which matched the natural compound by gas chromatography/mass spectrometry (retention time and EI mass spectrum). In field bioassays with freeze-killed sexually mature A. planipennis females, feral males spent significantly more time in contact and attempting copulation with unwashed females than with females that had been washed in n-hexane to remove the cuticular lipids. Hexane-washed females to which 9-Me-C(25) had been reapplied elicited similar contact time and percentage of time attempting copulation as unwashed females, indicating that 9-methyl-pentacosane is a contact sex pheromone component of A. planipennis. This is the first contact sex pheromone identified in the Buprestidae.

The emerald ash borer (EAB), Agrilus planipennis Fairmaire (Coleoptera: Buprestidae), is a highly destructive primary pest of ash (Fraxinus sp., Oleaceae) trees outside of its native range. Ash is an important component of many ecosystems and its loss would be detrimental to both the economy and the environment. The present study aimed to improve our understanding of the effectiveness of green sticky prism traps baited with host kairomone and insect pheromone lures for A. planipennis and to collect data for modelling the range of attraction of the pheromone (3Z)‐dodecen‐12‐olide [(3Z)‐lactone]. Traps were deployed over a single flight season in urban locations of Ontario, Canada, with low densities of EAB. Traps were placed in pairs of trees separated by not more than 25 m. All traps contained the host kairomone, (3Z)‐hexenol, with the remaining half in each pairing additionally baited with (3Z)‐lactone pheromone. Both lure types were highly effective in capturing EAB, with >90% detection rates overall. However, traps baited with the lactone pheromone and host volatile lures doubled trap captures of EAB over distances of at least 25 m from the nearest traps baited with only host volatiles. Although the baseline detection rate of traps containing (3Z)‐hexenol alone is not significantly reduced compared with traps containing (3Z)‐lactone, the overall trap effectiveness is significantly increased when (3Z)‐lactone is present. The implications for the use of (3Z)‐lactone at 3 mg per septum dose in an early warning trapping system are discussed. Trap layout methods and risk‐based analysis models can now be further refined by including these data about the attractive range of lures and their behaviour in different plot environments. [ABSTRACT FROM AUTHOR]

Recent research has demonstrated that the emerald ash borer, Agrilus planipennis Fairmaire (Coleoptera: Buprestidae), uses visual and chemical cues when locating potential mates and host trees. Here, we present the first evidence of the production of possible acoustic cues generated by adult males and females. We demonstrate for the first time that simultaneous wing opening and head 'pumping' in both males and females produce specific and distinct sounds. Acoustic recordings demonstrate that these sounds consist of a phrase comprising a 'click' generated by wing opening, followed by two separate chirps corresponding to the outward and subsequent inward movement of the head. Mean primary and secondary chirp durations were 0.332 ± 0.038 and 0.414 ± 0.046 s for males and 0.414 ± 0.046 and 0.389 ± 0.032 s for females, respectively. Overall mean phrase durations were 0.905 ± 0.114 s in males and 1.133 ± 0.133 s in females. Mean maximum phrase frequencies were 8 706.1 ± 141.1 and 7 885.0 ± 499.2 Hz in males and females, respectively. There were no significant differences in sound parameters between males and females. To determine whether these events were related to mating pair formation, we observed the occurrence of these events in adults paired with either another male or female and lone adults, and observed the number of mating pairs in copula formed during or shortly after sound production by either of the mating party. The mean number of sound‐generating events per min was significantly greater in males paired with females (0.75 ± 0.15) and/or other males (0.55 ± 0.23) vs. unpaired males (0.14 ± 0.06). Conversely, the mean number of sound‐producing events for lone females (1.4 ± 0.2) was significantly greater than for females paired with either males (0.49 ± 0.18) or other females (0.38 ± 0.10). No mating pairs in copula were formed during any of our observations. Scanning electron microscopy images showed the presence of possible pars stridens and plectrum structures on the ventral surfaces of the gula and pronotum in both males and females. Furthermore, we observed that the proportion of males and females exhibiting these specific behaviors were significantly greater under both halogen and incandescent light than under darkness, signifying the importance of light source or type on the production of acoustic signals. Although we did not find evidence of these behaviors being related to the courtship sequence, our results indicate the presence of a previously undescribed sound‐generation behavior in A. planipennis that is significantly influenced by light conditions. A trap that utilizes attractive plant and pheromone volatiles to detect emerald ash borer (EAB) (Coleoptera: Buprestidae) adults is the principal method for monitoring EAB populations. This trap exploits visual and chemical cues used by EAB adults to locate host trees and one another. An additional, yet undescribed, sensory modality in EAB is the role of acoustic cues produced by adults. We describe for the first time the existence of quantifiable and detectable acoustic sounds generated by EAB adults. [ABSTRACT FROM AUTHOR]

Phasgonophora sulcata Westwood (Hymenoptera: Chalcididae) is a North American parasitoid now using Agrilus planipennis Fairmaire (Coleoptera: Buprestidae) as a novel host, and may prove useful in biocontrol. Unfortunately, information is lacking regarding mating and the presence of pheromones, which may be important when attempting to exploit this parasitoid within a management context. Herein we used olfactometer assays and behavioural observations to determine the courtship and mating sequences of P. sulcata. A significantly higher proportion of males oriented towards females over the control arm containing filtered air in an olfactometer regardless of the age classes of females or males examined. We also observed four pre-copulatory behaviours that were consistent in all mating pairs. Our results indicate that courtship may be mediated by male perception of female-produced pheromones. Understanding the courtship sequence may be useful in rearing laboratory populations, while the putative pheromones may be useful in detection and retention of P. sulcata populations. [ABSTRACT FROM PUBLISHER]

Monochamol (2-undecyloxy-1-ethanol) is a male-produced aggregation pheromone for several Monochamus Dejean (Coleoptera: Cerambycidae) species. We conducted trapping experiments in Canada, Poland, and China to test whether monochamol was attractive to additional Monochamus species and if attraction was synergised by plant volatiles and bark beetle (Coleoptera: Curculionidae) pheromones. We provide the first evidence of attraction for M. urussovii (Fischer) and M. saltuarius (Gebler) to monochamol or monochamol+kairomones. The highest numbers of M. urussovii were captured in traps baited with monochamol+plant volatiles (Manuka oil, ethanol and (95/5±) α−pinene). Captures of M. saltuarius were highest in traps baited with monochamol, with the addition of cubeb oil tending to reduce captures. The highest numbers of M. scutellatus (Say) were captured in traps baited with monochamol+kairomones. A similar pattern in trap captures was found for M. notatus (Drury), M. marmorator Kirby, M. carolinensis (Olivier), and M. mutator LeConte. Detection rates, that is, proportion of traps capturing at least one specimen, was highest for traps baited with monochamol plus kairomones, particularly for less-common species. These results support the emerging hypothesis that pheromone compounds can attract related cerambycid species with cumulative evidence for attraction to monochamol for 12 species of Monochamus worldwide. [ABSTRACT FROM PUBLISHER]

The emerald ash borer, Agrilus planipennis Fairmaire (Coleoptera: Buprestidae), is a serious invasive pest of North American ash ( Fraxinus spp.) that has caused devastating mortality since it was first identified in North America in 2002. In 2012, we conducted field trapping assays that tested the efficacy of purple prism and fluon-coated green multifunnel (Lindgren funnel) traps. Traps were baited with combinations of several lures that were previously shown to be attractive to A. planipennis: manuka oil-a sesquiterpene-rich oil, (3Z)-hexenol-a green leaf volatile, or (3Z)-dodecen-12-olide [= (3Z)-lactone], a sex pheromone. Eighty-nine blocks (trap lines) were tested throughout nine states along the outer edges of the currently known A. planipennis infestation in North America. Trap catch was highest on fluon-coated green multifunnel traps, and trap detections at sites with low A. planipennis population density ranged from 72 to 76% for all trap and lure types tested. (3Z)-hexenol and (3Z)-lactone baited traps functioned as well as (3Z)-hexenol and manuka oil-baited traps. Independent of the lure used, detection rates on green fluon-coated multifunnel traps were comparable with glued purple prism traps in areas with low A. planipennis population densities. [ABSTRACT FROM AUTHOR]

Emerald ash borer, Agrilus planipennis Fairmaire ( Coleoptera: Buprestidae), is a major pest of ash trees, Fraxinus spp. (Oleaceae), in North America. This study investigated the timing of reproductive development in female beetles and the influence of female reproductive maturity on attraction to host volatiles. Based on dissections of females of increasing age, females with access to males for mating, and thus presumed mated, developed mature eggs only after 18-24 days. In contrast, female beetles reared without access to males, and thus unmated, did not develop mature eggs at any age. Chemical analysis of cuticular hydrocarbons detected the contact sex pheromone, 9-methyl-pentacosane, in cohorts of females which were 8-9 days old and older, supporting previous research that this compound signals sexual maturity to males. Results from field-trapping bioassays demonstrated that stage of female reproductive maturity influenced their attraction to host volatiles: females caught on traps baited with foliar volatiles contained eggs and ovarioles that were significantly less developed than those on traps baited with bark sesquiterpenes. However, our results revealed that females with immature stages of ovarioles and undeveloped eggs, such as those observed in unmated females, were rarely ever caught on traps baited with either of the host volatile lures. Further research on host compounds attractive to immature females is critical for early detection and possible control of A. planipennis populations during the extended pre-oviposition period. [ABSTRACT FROM AUTHOR]

The invasive emerald ash borer, Agrilus planipennis Fairmaire ( Coleoptera: Buprestidae), is a major pest of ash trees, Fraxinus spp., in its introduced range in North America. Field studies were conducted to quantify the efficacy of traps baited with kairomone and pheromone lures for early detection of A. planipennis infestation. A trapping experiment demonstrated that green traps baited with the kairomone (3 Z)-hexenol detected at least one adult A. planipennis in 55.3% of plots with 'nil to low'-density infestations and in 100% of plots with 'moderate to high'-density A. planipennis infestations. Mean trap captures increased significantly with increasing infestation density. In terms of the optimal number of traps per plot, when one (3 Z)-hexenol-baited trap was placed per plot, the trap detected populations in 62% of the plots with 'low to moderate'-density infestations through branch sampling. Detectability was increased to 82% when two traps were placed per plot. Finally, addition of female-produced (3 Z)-lactone pheromone to traps significantly increased detection rates at both the trap and plot level, as compared with traps baited with the host volatile, (3 Z)-hexenol, alone (88 vs. 60%, respectively). Our results are the first to demonstrate the efficacy of baited green sticky traps for detecting low-density A. planipennis infestations, particularly when the (3 Z)-lactone pheromone is used. This combination is therefore recommended for development of early-detection protocols against A. planipennis. [ABSTRACT FROM AUTHOR]

Knowledge of buprestid chemical ecology is sparse but the appearance of the invasive pest Agrilus planipennis Fairmaire in North America has provided the impetus to study in detail the semiochemistry and ecology of this important buprestid. The macrocyclic lactone (3Z)-12-dodecenolide [(3Z)-lactone] is identified as a key antennally-active compound that is produced by females and attracts males. Though a weak trap attractant alone, when combined with the host kairomone (3Z)-hexenol and the important visual cue of a green canopy trap, significant increases in male trap capture occur, thus defining (3Z)-lactone as both a sex pheromone of A. planipennis as well as the first and only known buprestid pheromone. The non-natural stereoisomer (3E)-12-dodecenolide and the saturated analog, 12-dodecanolide also exhibit mimetic activities towards male A. planipennis, suggesting a notable plasticity in this pheromonal structural motif. Efficient synthetic routes to these compounds have been developed. A series of fluoro-12-dodecanolides has also been synthesized containing CF2 groups as a strategy to bias the conformational space accessed by these macrolides and to assess if the analogs may act as mimetics for 12-dodecanolide pheromones associated in A. planipennis. These compounds also afford a unique opportunity to study the binding affinities of lactone surrogates with A. planipennis chemosensory proteins and olfactory receptors. Some progress has also been made in identifying the genes involved in the reception, processing and degradation of volatiles in this invasive insect. It is now evident that the behavior and ecology of A. planipennis involves a complex pattern of sensory modalities, including visual, tactile, olfactory and potentially acoustic components. Earlier reviews focused on studies of attractive host volatiles in development of a trapping system for early detection and visual and contact phenomena in A. planipennis mate finding. This review will update the semiochemistry and chemical ecology of A. planipennis and discuss studies on chemistry and behavior that have identified female-produced pheromone components and host kairomones. [ABSTRACT FROM AUTHOR]

A series of five 12-dodecanolides have been synthesised containing CF 2 groups at C5, C6, C7, C8 and in one case, a double substitution at C5 & C8, as a strategy to bias the conformational space accessed by these macrocycles, and to assess if the analogues may act as mimetics of 13-membered macrolide pheromones associated with the emerald ash borer. Accordingly individual syntheses of 5,5-difluoro- 5 , 6,6-difluoro- 6 , 7,7-difluoro- 7 , 8,8-difluoro- 8 and 5,5,8,8-tetrafluoro- 9 , 12-dodecanolides are outlined, and X-ray structural data were obtained for three (5 , 8 and 9) of these compounds. The structures show clearly that the CF 2 groups occupy 'corner' locations in the macrocycle consistent with their ability to bias accessible conformations. The fluorine containing 12-dodecanolides all generated an electro-antennogram response in female beetles. Image 1 [ABSTRACT FROM AUTHOR]

Abstract: The identification of the sex pheromone of the elm spanworm Ennomos subsignaria (Hübner), as the chiral alkenyl epoxide (6Z)-cis-9,10-epoxy-nonadecene has been accomplished. Both enantiomers of (6Z)-cis-9,10-epoxy-nonadecene have been synthesized via two routes. The key steps in the first route were to prepare both threo-epoxy tosylates and then to perform an alkylative rearrangement of these intermediates to obtain the target molecules. An alternative enantioenriched synthesis that took advantage of the Sharpless dihydroxylation reaction was developed so that a common starting material could be used to access both enantiomers. A field study and GC/EAD testing indicated that Z6-cis-9S,10R-epoxy-nonadecene was the sex pheromone of the elm spanworm E. subsignaria (Hübner). [Copyright &y& Elsevier]