Investigating Photo-Degradation as a Potential Pheromone Production Pathway in Spotted Lanternfly, Lycorma delicatula.

Since its discovery in North America in 2014, the spotted lanternfly (SLF), Lycorma delicatula, has become an economic, ecological, and nuisance pest there. Developing early detection and monitoring tools is critical to their mitigation and control. Previous research found evidence that SLF may use pheromones to help locate each other for aggregation or mating. Pheromone production necessitates specific conditions by the insects, and these must be investigated and described. A chemical process called photo-degradation has been described as a final step in the production of pheromones in several diurnal insect species, in which cuticular hydrocarbons were broken down by sunlight into volatile pheromone components. In this study, photo-degradation was investigated as a possible pheromone production pathway for SLF. Extracts from SLF mixed-sex third and fourth nymphs and male or female adults were either exposed to simulated sunlight to produce a photo-degradative reaction (photo-degraded), or not exposed to light (crude), while volatiles were collected. Behavioral bioassays tested for attraction to volatiles from photo-degraded and crude samples and their residues. In third instars, only the volatile samples from photo-degraded mixed-sex extracts were attractive. Fourth instar males were attracted to both crude and photo-degraded residues, and volatiles of photo-degraded mixed-sex extracts. Fourth instar females were attracted to volatiles of crude and photo-degraded mixed-sex extracts, but not to residues. In adults, only males were attracted to body volatiles from crude and photo-degraded extracts of either sex. Examination of all volatile samples using gas chromatography coupled with mass spectrometry (GC-MS) revealed that most of the identified compounds in photo-degraded extracts were also present in crude extracts. However, the abundance of these compounds in photo-degraded samples were 10 to 250 times more than their abundance in the crude counterparts. Results from behavioral bioassays indicate that photo-degradation probably does not generate a long-range pheromone, but it may be involved in the production of a short-range sex-recognition pheromone in SLF. This study provides additional evidence of pheromonal activity in SLF.

Tracking invasions of a destructive defoliator, the gypsy moth (Erebidae: Lymantria dispar): Population structure, origin of intercepted specimens, and Asian introgression into North America.

Genetic data can help elucidate the dynamics of biological invasions, which are fueled by the constant expansion of international trade. The introduction of European gypsy moth (Lymantria dispar dispar) into North America is a classic example of human-aided invasion that has caused tremendous damage to North American temperate forests. Recently, the even more destructive Asian gypsy moth (mainly L. d. asiatica and L. d. japonica) has been intercepted in North America, mostly transported by cargo ships. To track invasion pathways, we developed a diagnostic panel of 60 DNA loci (55 nuclear and 5 mitochondrial) to characterize worldwide genetic differentiation within L. dispar and its sister species L. umbrosa. Hierarchical analyses supported strong differentiation and recovered five geographic groups that correspond to (1) North America, (2) Europe plus North Africa and Middle East, (3) the Urals, Central Asia, and Russian Siberia, (4) continental East Asia, and (5) the Japanese islands. Interestingly, L. umbrosa was grouped with L. d. japonica, and the introduced North American population exhibits remarkable distinctiveness from contemporary European counterparts. Each geographic group, except for North America, shows additional lower-level structures when analyzed individually, which provided the basis for inference of the origin of invasive specimens. Two assignment approaches consistently identified a coastal area of continental East Asia as the major source for Asian invasion during 2014-2015, with Japan being another source. By analyzing simulation and laboratory crosses, we further provided evidence for the occurrence of natural Asian-North American hybrids in the Pacific Northwest, raising concerns for introgression of Asian alleles that may accelerate range expansion of gypsy moth in North America. Our study demonstrates how genetic data contribute to bio-surveillance of invasive species with results that can inform regulatory management and reduce the frequency of trade-associated invasions.

Female-Produced Sex Pheromone of Tetrastichus planipennisi, a Parasitoid Introduced for Biological Control of the Invasive Emerald Ash Borer, Agrilus planipennis.

The Asian eulophid wasp Tetrastichus planipennisi is being released in North America as a biocontrol agent for the emerald ash borer (Agrilus planipennis), a very destructive invasive buprestid beetle that is devastating ash trees (Fraxinus spp.). We identified, synthesized, and tested a female-produced sex pheromone for the wasp. The key component eliciting behavioral responses from male wasps in flight tunnel bioassays was identified as (6S,10S)-(2E,4E,8E)-4,6,8,10-tetramethyltrideca-2,4,8-triene. Female specificity was demonstrated by gas chromatographic (GC) comparison of male and female volatile emissions and whole body extracts. The identification was aided by coupled gas chromatography/mass spectrometry analysis, microchemical reactions, NMR, GC analyses with a chiral stationary phase column, and matching GC retention times and mass spectra with those of synthetic standards. The tetramethyl-triene hydrocarbon was synthesized as a mixture of two enantiomeric pairs of diastereomers, and as the pure insect-produced stereoisomer. In flight-tunnel bioassays, males responded to both the natural pheromone and the chiral synthetic material by upwind flight and landing on the source. In contrast, the mixture of four stereoisomers was not attractive, indicating that one or more of the "unnatural" stereoisomers antagonized attraction. Field trials, using yellow pan traps baited with natural pheromone, captured significantly more male wasps than control traps over a four week trial. The identified pheromone could increase the efficiency and specificity of the current detection methods for Tetrastichus planipennisi and aid in the determination of parasitoid establishment at release sites.

Field Evaluation of a Binary Sex Pheromone for Sweetpotato Vine Borer (Lepidoptera: Crambidae) in Hawaii.

The sweetpotato vine borer, Omphisa anastomosalis (Guenée), is a primarily Asian pest of sweetpotato, Ipomoea batatas L. Damage by O. anastomosalis infestation can cause root yield losses of 30%-50%. A binary sex pheromone for O. anastomosalis, consisting of Type I [(10E,14E)-10,14-hexadecadienal (E10,E14-16:Ald)] and Type II [(3Z,6Z,9Z)-3,6,9-tricosatriene (Z3,Z6,Z9-23:H)] components, was identified in Vietnam from extracts of female pheromone glands. A structurally similar Type II compound [(3Z,6Z,9Z)-3,6,9-docosatriene (Z3,Z6,Z9-22:H)], not recovered from female pheromone glands, was also found to synergize the attractiveness of the Type I component. Additional field work has been needed to determine whether these synergistic enhancements of attractiveness also occur in other parts of the geographical distribution of this moth species. Herein, results of studies are reported which document that both Z3,Z6,Z9-23:H and Z3,Z6,Z9-22:H also synergistically enhance male response to E10,E14-16:Ald in Hawaii sweetpotato field populations. Trap catch tends to be enhanced with increase of dose and lower Type I:Type II ratios. Among the compound doses and ratios tested, trap catch increased with the addition of the Type II component by over 13 times relative to traps baited with the Type I component alone, which significantly enhanced sweetpotato vine borer detection. Using a 2.0 mg: 4.0 mg Type I: Type II loading, there was continued catch over 12 wk, during which time the Type I component weathered at a faster rate than the Type II component. This binary sex pheromone seems to have promise for both monitoring and suppression of field populations of O. anastomosalis throughout its geographical range.

Pheromones of three ambrosia beetles in the Euwallacea fornicatus species complex: ratios and preferences.

Three cryptic species in the Euwallacea fornicatus species complex were reared in laboratory colonies and investigated for the presence of pheromones. Collections of volatiles from combinations of diet, fungus, beetles, and galleries from polyphagous shot hole borer (Euwallacea sp. #1) revealed the presence of 2-heneicosanone and 2-tricosanone only in the presence of beetles, regardless of sex. Subsequent examination of volatiles from the other two species, tea shot hole borer (Euwallacea sp. #2) and Kuroshio shot hole borer (Euwallacea sp. #5), revealed these two ketones were present in all three species but in different ratios. In dual choice olfactometer behavioral bioassays, mature mated females were strongly attracted to a synthetic binary blend of ketones matching their own natural ratios. However, females in each species were repelled by ketone blends in ratios corresponding to the other two species. Males of each species responded similarly to females when presented with ratios matching their own or the other two species. The presence of these compounds in the three beetle species, in ratios unique to each species, and their strong species-specific attraction and repellency, suggests they are pheromones. The ecological function of these pheromones is discussed. In addition to the pheromones, the previously known attractant (1S,4R)-p-menth-2-en-1-ol (also known as quercivorol) was discovered in the presence of the fungal symbionts, but not in association with the beetles. Quercivorol was tested in a dual-choice olfactometer and was strongly attractive to all three species. This evidence suggests quercivorol functions as a kairomone for members of the E. fornicatus species complex, likely produced by the symbiotic fungi.

Quercivorol as a lure for the polyphagous and Kuroshio shot hole borers, Euwallacea spp. nr. fornicatus (Coleoptera: Scolytinae), vectors of Fusarium dieback.

The polyphagous shot hole borer and Kuroshio shot hole borer, two members of the Euwallacea fornicatus species complex (Coleoptera: Curculionidae: Scolytinae), are invasive ambrosia beetles that harbor distinct species of Fusarium fungal symbionts. Together with the damage caused by gallery construction, these two phytopathogenic Fusarium species are responsible for the emerging tree disease Fusarium dieback, which affects over 50 common tree species in Southern California. Host trees suffer branch dieback as the xylem is blocked by invading beetles and fungi, forcing the costly removal of dead and dying trees in urban areas. The beetles are also threatening natural riparian habitats, and avocado is susceptible to Fusarium dieback as well, resulting in damage to the avocado industries in California and Israel. Currently there are no adequate control mechanisms for shot hole borers. This paper summarizes efforts to find a suitable lure to monitor shot hole borer invasions and dispersal. Field trials were conducted in two counties in Southern California over a span of two years. We find that the chemical quercivorol is highly attractive to these beetles, and perform subsequent field experiments attempting to optimize this lure. We also explore other methods of increasing trap catch and effects of other potential attractants, as well as the deterrents verbenone and piperitone.

Polyols, not sugars, determine the structural diversity of anti-streptococcal liamocins produced by Aureobasidium pullulans strain NRRL 50380.

Liamocins are polyol lipids produced by the fungus Aureobasidium pullulans, and have selective antibacterial activity against Streptococcus species. Liamocins produced by A. pullulans strain NRRL 50380 on sucrose medium have a d-mannitol head group ester-linked to 3,5-dihydroxydecanoate acyl chains, three or four of which are joined together by 1,5-polyester bonds (liamocins Man-A1 and Man-B1), and similar 3'-O-acetylated analogs (Man-A2 and Man-B2). However, other types of liamocins are produced depending on the choice of strain and growth conditions. In the current study, growth on different polyols, but not sugars, resulted in considerable structural variation, including liamocins with d-galactitol (dulcitol), d-sorbitol (glucitol), d- and l-arabitol, d-xylitol, l-threitol and glycerol head groups. The head groups of liamocins produced on arabitol were shown to be entirely composed of d-arabitol. These liamocin variants were structurally characterized by NMR and MS, and tested for antibacterial activity. The new liamocin variants also had selective activity against Streptococcus. Liamocin structural variants are novel antibacterials against Streptococcus sp. that merit further investigation.

A Culture Method for Darkling Beetles, Blapstinus spp. (Coleoptera:Tenebrionidae).

Darkling beetles, Blapstinus spp., have become a serious pest of Cucurbitaceae crops, especially in California. A culture method was sought to provide large numbers (>500) of adult beetles of known age and sex that could be used for laboratory testing when needed. A method previously developed for Alphitobius diaperinus (Panzer) using a diet of ground chick feed, with apple slices as a moisture source, was modified for use with Blapstinus spp. and then compared with the same method substituting apple slices with zucchini as the moisture source. Rearing boxes set up with apple slices produced significantly more pupae and adults than boxes containing zucchini slices. However, using either zucchini or apples as a moisture source yielded over the target of 500 adults per rearing box. A previous method designed to sex A. diaperinus based on the presence (♀) or absence (♂) of second valvifers in the pupal stage also proved to be effective for sexing the Blapstinus spp.

Can Coffee Chemical Compounds and Insecticidal Plants Be Harnessed for Control of Major Coffee Pests?

Pests and pathogens threaten coffee production worldwide and are difficult to control using conventional methods, such as insecticides. We review the literature on the chemistry of coffee, concentrating on compounds most commonly reported from Coffea arabica and Coffea canephora. Differences in chemistry can distinguish coffee species and varieties, and plants grown under different biogeographic conditions exhibit different chemotypes. A number of chemical groups, such as alkaloids and caffeoylquinic acids, are known to be insecticidal, but most studies have investigated their effects on coffee quality and flavor. More research is required to bridge this gap in knowledge, so that coffee can be bred to be more resistant to pests. Furthermore, we report on some pesticidal plants that have been used for control of coffee pests. Locally sourced pesticidal plants have been underutilized and offer a sustainable alternative to conventional insecticides and could be used to augment breeding for resilience of coffee plants.

Discordant phylogenies suggest repeated host shifts in the Fusarium-Euwallacea ambrosia beetle mutualism.

The mutualism between xyleborine beetles in the genus Euwallacea (Coleoptera: Curculionidae: Scolytinae) and members of the Ambrosia Fusarium Clade (AFC) represents one of 11 known evolutionary origins of fungiculture by ambrosia beetles. Female Euwallacea beetles transport fusarial symbionts in paired mandibular mycangia from their natal gallery to woody hosts where they are cultivated in galleries as a source of food. Native to Asia, several exotic Euwallacea species were introduced into the United States and Israel within the past two decades and they now threaten urban landscapes, forests and avocado production. To assess species limits and to date the evolutionary diversification of the mutualists, we reconstructed the evolutionary histories of key representatives of the Fusarium and Euwallacea clades using maximum parsimony and maximum likelihood methods. Twelve species-level lineages, termed AF 1-12, were identified within the monophyletic AFC and seven among the Fusarium-farming Euwallacea. Bayesian diversification-time estimates placed the origin of the Euwallacea-Fusarium mutualism near the Oligocene-Miocene boundary ∼19-24 Mya. Most Euwallacea spp. appear to be associated with one species of Fusarium, but two species farmed two closely related fusaria. Euwallacea sp. #2 in Miami-Dade County, Florida cultivated Fusarium spp. AF-6 and AF-8 on avocado, and Euwallacea sp. #4 farmed Fusarium ambrosium AF-1 and Fusarium sp. AF-11 on Chinese tea in Sri Lanka. Cophylogenetic analyses indicated that the Euwallacea and Fusarium phylogenies were largely incongruent, apparently due to the beetles switching fusarial symbionts (i.e., host shifts) at least five times during the evolution of this mutualism. Three cospeciation events between Euwallacea and their AFC symbionts were detected, but randomization tests failed to reject the null hypothesis that the putative parallel cladogenesis is a stochastic pattern. Lastly, two collections of Euwallacea sp. #2 from Miami-Dade County, Florida shared an identical cytochrome oxidase subunit 1 (CO1) allele with Euwallacea validus, suggesting introgressive hybridization between these species and/or pseudogenous nature of this marker. Results of the present study highlight the importance of understanding the potential for and frequency of host-switching between Euwallacea and members of the AFC, and that these shifts may bring together more aggressive and virulent combinations of these invasive mutualists.

Attraction of Agrilus planipennis (Coleoptera: Buprestidae) to a volatile pheromone: effects of release rate, host volatile, and trap placement.

Attraction of emerald ash borer, Agrilus planipennis Fairmaire, to a volatile pheromone was demonstrated in three field experiments using baited green sticky traps. A dose-response curve was generated for male A. planipennis to increasing release rates of (3Z)-dodecen-12-olide ((3Z)-lactone) in combination with the green leaf volatile, (3Z)-hexenol. Only the lowest release rate (<2.50 µg/d) of (3Z)-lactone significantly increased captures of male A. planipennis, as compared with traps baited with (3Z)-hexenol alone. Effect of trap height, (3Z)-lactone, and (3Z)-hexenol and their interactions on the trap capture of A. planipennis was determined in a factorial experiment. Number of males per trap was significantly and positively affected by (3Z)-lactone, (3Z)-hexenol, and trap height whereas number of females per trap was affected by trap height only; none of the interactions were significant. As predicted, the greatest mean catch of males was in traps baited with (3Z)-lactone and (3Z)-hexenol placed high in the canopy. Electroantennogram tests on the bark volatile, 7-epi-sesquithujene, demonstrated the ability of male and female A. planipennis antennae to detect and respond to this compound, particularly the (+)-7-epi-sesquithujene isomer. Results from an olfactometer bioassay and field testing did not demonstrate attraction of either males or females to (+)-7-epi-sesquithujene. These data increase our understanding of the pheromone ecology of the invasive emerald ash borer, provide further confirmation of the behavioral activity of the female-produced lactone pheromone, and should increase the ability to detect A. planipennis infestations where they are present.

Influence of trap color and host volatiles on capture of the emerald ash borer (Coleoptera: Buprestidae).

Field trapping assays were conducted in 2009 and 2010 throughout western Michigan, to evaluate lures for adult emerald ash borer, A. planipennis Fairmaire (Coleoptera: Buprestidae). Several ash tree volatiles were tested on purple prism traps in 2009, and a dark green prism trap in 2010. In 2009, six bark oil distillate lure treatments were tested against manuka oil lures (used in 2008 by USDA APHIS PPQ emerald ash borer cooperative program). Purple traps baited with 80/20 (manuka/phoebe oil) significantly increased beetle catch compared with traps baited with manuka oil alone. In 2010 we monitored emerald ash borer attraction to dark green traps baited with six lure combinations of 80/20 (manuka/phoebe), manuka oil, and (3Z)-hexenol. Traps baited with manuka oil and (3Z)-hexenol caught significantly more male and total count insects than traps baited with manuka oil alone. Traps baited with manuka oil and (3Z)-hexenol did not catch more beetles when compared with traps baited with (3Z)-hexenol alone. When compared with unbaited green traps our results show that (3Z)-hexenol improved male catch significantly in only one of three field experiments using dark green traps. Dark green traps caught a high number of A. planipennis when unbaited while (3Z)-hexenol was seen to have a minimal (nonsignificant) trap catch effect at several different release rates. We hypothesize that the previously reported kairomonal attractancy of (3Z)-hexenol (for males) on light green traps is not as obvious here because of improved male attractancy to the darker green trap.

Male-produced pheromone of Spathius agrili, a parasitoid introduced for the biological control of the invasive emerald ash borer, Agrilus planipennis.

The braconid wasp, Spathius agrili, has been released in the U.S. as a biocontrol agent for the invasive emerald ash borer (Coleoptera: Buprestidae: Agrilus planipennis), a destructive pest of ash trees (Fraxinus spp.). We identified and synthesized seven male-specific volatile compounds. Three of these, dodecanal, (4R,11E)-tetradecen-4-olide, and (Z)-10-heptadecen-2-one, were the key behaviorally active components in flight tunnel bioassays. Male specificity was demonstrated by gas chromatographic comparison of male and female volatile emissions and whole body extracts. Identifications were aided by coupled gas chromatographic-mass spectrometric (GC-MS) analysis, microchemical reactions, NMR, chiral GC analysis, and GC and MS comparison with authentic standards. Both the racemic and chiral forms of the γ-lactone, as well as both E- and Z-isomers were synthesized. Flight tunnel behavioral tests showed positive male and female S. agrili responses to both natural pheromone and synthetic blends, with upwind flight and landing on the source. Large field-cage tests, using yellow sticky traps baited with pheromone, captured approximately 50% of the released male and female wasps in 24-h periods. The use of pheromone-baited traps in the field could simplify the current detection method for determining parasitoid establishment (i.e., laboriously felling and peeling ash trees for recovery of S. agrili from infested EAB larvae).

Two-carbon homologation of aldehydes and ketones to α,ß-unsaturated aldehydes.

Phosphonate reagents were developed for the two-carbon homologation of aldehydes or ketones to unbranched- or methyl-branched α,ß-unsaturated aldehydes. The phosphonate reagents, diethyl methylformyl-2-phosphonate dimethylhydrazone and diethyl ethylformyl-2-phosphonate dimethylhydrazone, contained a protected aldehyde group instead of the usual ester group. A homologation cycle entailed condensation of the reagent with the starting aldehyde, followed by removal of the dimethylhydrazone protective group with a biphasic mixture of 1 M HCl and petroleum ether. This robust two-step process worked with a variety of aldehydes and ketones. Overall isolated yields of unsaturated aldehyde products ranged from 71% to 86% after the condensation and deprotection steps.

Absolute configuration of 7-epi-sesquithujene.

7-epi-sesquithujene (1) is a bicyclic sesquiterpene isolated from phoebe oil, an essential oil of the Brazilian walnut tree, Phoebe porosa. It is also produced by stressed ash trees and has been shown to elicit strong electrophysiological responses on emerald ash borer, Agrilus planipennis, antennae. In the course of the development of a synthetic 7-epi-sesquithujene lure for field testing against the emerald ash borer, we found that the absolute configuration of this compound had not been determined. We isolated >95% pure 7-epi-sesquithujene from phoebe oil via successive fractionation and conventional and argentation (HPLC) chromatographies. The specific optical rotation of this compound matched that of a synthetic product of known configuration. We also synthesized two other stereoisomers of sesquithujene and developed a chiral GC method to separate all four. Based on the specific rotation, stereoselective syntheses, and chiral GC analyses, 7-epi-sesquithujene present in phoebe oil and white ash was found to have the 2S,6S,7R absolute configuration.

Male-specific sesquiterpenes from Phyllotreta flea beetles.

Flea beetles in several genera are known to possess male-specific sesquiterpenes, at least some of which serve as aggregation pheromones that attract both sexes. In continuing research on the chemical ecology of Phyllotreta flea beetles, six new male-specific sesquiterpenes were identified, one from P. striolata (hydroxyketone 9) and five from P. pusilla (aldehydes 10-12 and 14 and alcohol 13); both species are crop pests. The minute amounts from beetles provided mass spectra and chromatographic data but were insufficient for complete structure determination. However, it was discovered that the new compounds could all be produced by applying organic reactions to previously identified flea beetle sesquiterpenes, and the resulting, larger amounts of material permitted definitive structure analysis by NMR. Molecular modeling was used in conjunction with NMR to define relative configurations of several newly created stereogenic centers. The absolute configurations of natural 9-14 were established by chiral gas chromatography/mass spectrometry. In electrophysiological tests (GC-EAD) conducted with P. striolata, compound 9 was detected with high sensitivity by the beetle antennae, which is consistent with a pheromonal function. The research opens new possibilities for using behavioral chemicals to monitor or manage these pest species.

Evidence for a volatile pheromone in Agrilus planipennis Fairmaire (Coleoptera: Buprestidae) that increases attraction to a host foliar volatile.

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.

Methyl 6-methylsalicylate: a female-produced pheromone component of the parasitoid wasp Spalangia endius.

Sex-pheromone-related behavior and chemistry were studied in the wasp Spalangia endius Walker (Hymenoptera: Pteromalidae), a pupal parasitoid of the house fly, Musca domestica L. (Diptera: Muscidae). Males responded behaviorally to female extracts by arrestment, whereas females did not arrest to male extracts. In a comparison of male and female extracts by gas chromatography-mass spectrometry (GC-MS), two female-specific compounds were found. One was identified as methyl 6-methylsalicylate (gas chromatographic retention time and mass spectrum versus an authentic standard), but the chemical structure of the second compound is still unknown. Male antennae were sensitive to both compounds in electrophysiological tests (GC-EAD). Males responded behaviorally to methyl 6-methylsalicylate by arrestment, but did not arrest to the second compound. Methyl 6-methylsalicylate has been reported previously from some ant and beetle species, but never from the Pteromalidae. Chemical analysis of the extracts and the male behavioral results are consistent with the hypothesis that methyl 6-methylsalicylate functions as a female-emitted pheromone component at short range, but the exact role of both compounds in intersexual interactions in S. endius remains to be determined.

Male-produced aggregation pheromone of the lesser mealworm beetle, Alphitobius diaperinus.

The lesser mealworm beetle, Alphitobius diaperinus (Panzer), is a widespread serious pest in poultry production facilities and is difficult to control by conventional means. Although pheromone-based tools have become useful in the management of other beetle pests, no pheromone was known for A. diaperinus, and this study sought to develop basic pheromone information. Volatiles were collected in the laboratory from groups of male and female A. diaperinus maintained on poultry food (chick starter mash). Gas chromatographic-mass spectrometric analysis of volatiles collected from feeding males and females revealed five male-specific compounds that were identified as (R)-(+)-limonene, (E)-beta-ocimene, (S)-(+)-linalool, (R)-(+)-daucene, and 2-nonanone. Emission of these began 1-2 weeks after adult emergence and could continue for at least 1 year, ceasing and resuming in response to changes in food availability and quality and other factors. No female-specific compounds were discovered. A synthetic blend of the five male compounds was attractive to both sexes in poultry production facilities in Illinois and Arkansas, indicating that the blend functions as an aggregation pheromone, but it is not yet known whether all five compounds are required for activity. A new pitfall trap is described for field use.

Sex pheromone of the pine false webworm Acantholyda erythrocephala.

Females of the pine false webworm Acantholyda erythrocephala (L) produce the sex pheromone (Z)-6, 14-pentadecadienal, which attracts flying males in the field. By using gas chromatography coupled with electroantennographic detection (GC-EAD) and mass spectrometry (GC-MS), we detected (Z)-6,14-pentadecadienal in volatile collections and in whole body extracts of female A. erythrocephala. Females, but not males, also exhibited a 25-carbon cuticular hydrocarbon, (Z,Z)-1,9,15-pentacosatriene, which can oxidize to (Z)-6,14-pentadecadienal upon exposure to air and sunlight. (Z,Z)-1,9,15-Pentacosatriene and (Z)-6,14-pentadecadienal identifications were corroborated by comparison with synthetic standards. (Z)-6, 14-Pentadecadienal is the second pheromone identified for pamphilliid sawflies, and the first to elicit strong field attraction, and thus offer potential as a pheromone lure to aid in control of this forest pest.