Search

Brassicadiene, a novel tricyclic diterpene hydrocarbon, was identified by a combination of mass spectrometry, microchemical tests, and analysis of NMR spectra. The compound constitutes >90% of the volatile organic compounds produced by cauliflower seedlings, Brassica oleracea var. botrytis. The invasive stink bug Bagrada hilaris is strongly attracted to brassicadiene, providing a mechanism for this herbivore, which specializes on cruciferous plants, to locate its hosts in a nutrient-rich and vulnerable stage.

The compound 1-(1H-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.

Here, we describe a field experiment that tested for attraction of cerambycid beetles to odors from angiosperm hosts, and whether plant volatiles also serve to enhance attraction of beetles to their aggregation-sex pheromones. Traps were baited with a blend of synthesized chemicals that are common pheromone components of species in the subfamilies Cerambycinae and Lamiinae. The source of plant volatiles was chipped wood from trees of three angiosperm species, as well as from one nonhost, gymnosperm species. Bioassays were conducted in wooded areas of east-central Illinois. Traps were baited with the pheromone blend alone, the blend + wood chips from one tree species, wood chips alone, or a solvent control lure. Seven species of cerambycids were significantly attracted to the pheromone blend, with or without wood chips. In two cases, wood chips from angiosperms appeared to enhance attraction to pheromones, whereas they inhibited attraction in another three cases. Pine chips did not strongly influence attraction of any species. Overall, our results suggest that host plant volatiles from wood chips may improve trap catch with synthesized pheromones for some cerambycid species, but the effect is not general, necessitating case-by-case testing to determine how individual target species are affected.

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. Electronic supplementary material The online version of this article (10.1007/s10886-019-01082-4) contains supplementary material, which is available to authorized users.

This study identified chemicals found on the eggs of two stink bug species, one native to western North America, Euschistus conspersus, and an invasive species from Asia, Halyomorpha halys. The responses of two scelionid egg parasitoids, Trissolcus erugatus and Telenomus podisi, toward natural stink bug egg volatiles, and synthetic reconstructions of egg volatiles, were tested in bioassays. A compound, methyl (2E,4Z)-2,4-decadienoate, previously identified as the major component of the male-produced aggregation pheromone of E. conspersus, was the major volatile identified from extracts of E. conspersus eggs. In contrast, for H. halys, the sesquiterpenoids that compose the male-produced aggregation pheromone of this species were not detected on eggs, whereas the presence of hexadecanal, octadecanal, and eicosanal was detected. In laboratory olfactometer tests, both Tr. erugatus and Te. podisi females were attracted to extracts of E. conspersus eggs, and to synthetic methyl (2E,4Z)-2,4-decadienoate. However, female Tr. erugatus and Te. podisi wasps were repelled, both by extracts of H. halys eggs and by a blend of the aldehydes identified from H. halys eggs. A follow-up field study, using hexane-washed and intact E. conspersus as sentinel eggs, showed that the parasitoids Trissolcus erugatus and Gryon obesum emerged from these eggs. Sentinel hexane-washed eggs treated with 3 ng of methyl (2E,4Z)-2,4-decadienoate were parasitized more by these two species than were hexane-washed or unwashed eggs, whereas hexane-washed eggs treated with a comparable dose of the C16,18,20 aldehyde mixture were avoided by these parasitoids. In a further field experiment, Trissolcus basalis was the primary parasitoid found in sticky traps baited with methyl (2E,4Z)-2,4-decadienoate, indicating that this species was attracted to, but either did not oviposit or develop in the E. conspersus sentinel eggs in the previous experiment.

We report here the pheromone of Megacyllene antennata (White) (Coleoptera: Cerambycidae), a species native to southwestern North America whose larvae feed in woody tissues of mesquite (Prosopis species; Fabaceae). Adult males sex-specifically produced a blend of eight common natural products, including the monoterpene alcohol (S)-α-terpineol; the monoterpenes (S)-limonene and terpinolene; the aromatic alcohols (R)-1-phenylethanol and 2-phenylethanol; and (E)-2-hexenol, (E)-2-hexenal, and 1-hexanol. Individual males produced the components in varying amounts, but (S)-α-terpineol and (E)-2-hexenal were always present and together constituted the majority of the blend. A synthetic reconstruction of the complete blend attracted both males and females of M. antennata during field bioassays, as did all subsets of the blend that included (S)-α-terpineol and (E)-2-hexenol. Adults were most strongly attracted to blends of the latter two compounds when in ratios approaching parity. Neither of the compounds were present in the bouquet of volatiles emitted by host plants of the larvae.

The obscure mealybug, Pseudococcus viburni (Signoret) (Hemiptera: Pseudococcidae), is a cosmopolitan pest. In New Zealand, recently introduced management tools include the host-specific parasitoid Acerophagus maculipennis (Mercet) (Hymenoptera: Encyrtidae) established in 2001, and pheromone-baited monitoring traps available since 2005. Red delta traps baited with rubber septum lures impregnated with 4.0 μg of the mealybug synthetic sex pheromone, placed in apple orchards in Hawke's Bay and Nelson, trapped both male P. viburni and female A. maculipennis. Two generations of both species per year were discernible, but numbers were low in spring and parasitoids were not trapped during winter (June to September). Male P. viburni catches reached a plateau at a pheromone dose of ca. 1.0 μg per lure but numbers of A. maculipennis per trap increased up to 100 μg per lure, the maximum dose tested. A mathematical model showed that the lures had a half-life of about 7.4 days and were most attractive to P. viburni with a dose of 0.19 μg, and that the trap effectiveness decreased rapidly once the release rate dropped below the optimum. The model also predicted that the initial pheromone dose should be increased from 0.19 to 5.41 μg per lure as the desired period of deployment increased from 0 to 9 weeks. A dose of 4.0 μg had an initial relative effectiveness of about 55%, reached peak effectiveness after about 5 weeks, and fell to 55% relative effectiveness again after about 8.3 weeks. We conclude that an initial pheromone load of 4.0 μg is appropriate for practical monitoring of P. viburni during the New Zealand summer. Future applications of the sex pheromone for managing the pest and parasitoid are discussed.

The horticultural trade is an important pathway for the introduction and spread of invasive gastropods because potted plants are essentially portable microhabitats, which protect snails and slugs, especially buried eggs and juveniles, from desiccation and molluscicides. The identification of a drench or dip treatment would therefore be an important development in helping to manage this pathway. We assessed the potential of using eleven essential oils and one terpene against the eggs and juveniles of the quarantine snail pest, Cornu aspersum. Clove bud oil was most efficacious and based on Lethal Concentration 50 (LC50) values it was 22 times more toxic than the commercially available product Snail and Slug Away® which has cinnamon oil as its active ingredient. Importantly, at a concentration of 0.116 %, clove bud oil caused 100 % mortality of C. asperum eggs and juveniles in potted plants after 24 h and was not phytotoxic. Although more expensive than a widely used metaldehyde product (Slug-Fest All Weather Formula) clove bud oil causes rapid mortality, is pleasant smelling, is non-toxic to humans and is exempt from pesticide registration requirements and pesticide residue tolerance requirements under federal law in the United States. This exemption would decrease the time and costs associated with bringing a new molluscicide to market, which has clove bud oil as its active ingredient.

Many species of cerambycid beetles in the subfamily Cerambycinae are known to use male-produced pheromones composed of one or a few components such as 3-hydroxyalkan-2-ones and the related 2,3-alkanediols. Here, we show that this pheromone structure is characteristic of the cerambycine genus Neoclytus Thomson, based on laboratory and field studies of 10 species and subspecies. Males of seven taxa produced pheromones composed of ( R )-3-hydroxyhexan-2-one as a single component, and the synthetic pheromone attracted adults of both sexes in field bioassays, including the eastern North American taxa Neoclytus caprea (Say), Neoclytus mucronatus mucronatus (F.), and Neoclytus scutellaris (Olivier), and the western taxa Neoclytus conjunctus (LeConte), Neoclytus irroratus (LeConte), and Neoclytus modestus modestus Fall. Males of the eastern Neoclytus acuminatus acuminatus (F.) and the western Neoclytus tenuiscriptus Fall produced (2 S ,3 S )-2,3-hexanediol as their dominant or sole pheromone component. Preliminary data also revealed that males of the western Neoclytus balteatus LeConte produced a blend of ( R )-3-hydroxyhexan-2-one and (2 S ,3 S )-2,3-hexanediol but also (2 S ,3 S )-2,3-octanediol as a minor component. The fact that the hydroxyketone-hexanediol structural motif is consistent among these North American species provides further evidence of the high degree of conservation of pheromone structures among species in the subfamily Cerambycinae.

Male-specific volatile components, released by the dried bean beetle, Acanthoscelides obtectus, were identified as methyl (E,R)-2,4,5-tetradecatrienoate, methyl (2E,4Z,7Z)-2,4,7-decatrienoate, methyl (2E,4Z)-2,4-decadienoate, octadecanal and the sesquiterpenes (3Z,6E)- and (3E,6E)-α-farnesene. In olfactometer bioassays, pure methyl (E,R)-2,4,5-tetradecatrienoate was only weakly attractive to unmated females. However, a blend of the six identified compounds released in physiologically relevant ratios and doses proved to be as active as headspace odours collected from live males.

Environmental stresses, particularly water deficit, predispose eucalypt trees to attack by the eucalyptus longhorned borer, Phoracantha semipunctata F. (Coleoptera: Cerambycidae). Our experiments with potted eucalypts revealed that reduced tree water potential was associated with lower resistance to colonization by neonate P. semipunctata, but the linear relationship between water potential and colonization success was reversed at higher larval densities. There was no indication that the bark exudate “kino” served to defend trees from borer attack. Larvae were not able to colonize the cambium of eucalypt logs with high bark moisture, and survival was low under high moisture conditions in artificial hosts composed of pure cellulose. In trees and cut logs with moist bark, larvae failed to reach the cambium, feeding instead in poorer-quality tissues just beneath the bark surface. Our findings suggest that variation in resistance of eucalypts to attack by the borer is associated with moisture content of the bark.

The sex pheromone of the cloaked pug moth, Eupithecia abietaria Gotze, an important cone-feeding pest in spruce seed orchards in Europe, was investigated. Chemical and electrophysiological analyses of pheromone gland extracts of female moths and analogous analyses of synthetic hydrocarbons and epoxides of chain length C19 and C21 revealed (3Z,6Z,9Z)-3,6,9-nonadecatriene (3Z,6Z,9Z-19:H) and 3Z,6Z-cis-9,10-epoxynonadecadiene (3Z,6Z-cis-9,10-epoxy-19:H) as candidate pheromone components, which were found in a gland extract in a ratio of 95 : 5. In field trapping experiments, conspecific males were only attracted to a combination of 3Z,6Z,9Z-19:H and the (9S,10R)-enantiomer of 3Z,6Z-cis-9,10-epoxy-19:H. The (9R,10S)-enantiomer was not attractive, which is in agreement with studies on other Eupithecia species, for which males have only been attracted by the (9S,10R)-enantiomer of epoxides. Subsequent experiments showed that E. abietaria males were attracted to a wide range of ratios of the two active compounds and that trap catches increased with increasing dose of the binary blend. A two-component bait containing 300 μg 3Z,6Z,9Z-19:H and 33 μg of the (9S,10R)-enantiomer of 3Z,6Z-cis-9,10-epoxy-19:H was efficient for monitoring E. abietaria in spruce seed orchards in southern Sweden, where this species has probably been overlooked as an important pest in the past. With sex pheromones recently identified for two other moths that are major pests on spruce cones, the spruce seed moth, Cydia strobilella L., and the spruce coneworm, Dioryctria abietella Denis & Schiffermuller, pheromone-based monitoring can now be achieved for the whole guild of cone-feeding moths in European spruce seed orchards. (Less)

Bagrada hilaris Burmeister, is a stink bug native to Asia and Africa and invasive in the United States, Mexico, and more recently, South America. This species can cause serious damage to various vegetable crops in the genus Brassica, with seedlings being particularly susceptible to B. hilaris feeding activity. In this study, the role of volatile organic compounds (VOCs) emitted by seedlings of three Brassica species on the host preference of B. hilaris was evaluated. In dual choice arena and olfactometer bioassays, adult painted bugs preferred B. oleracea var. botrytis and B. napus over B. carinata. Volatiles from B. oleracea seedlings were collected and bioassayed with B. hilaris adults and late stage nymphs, using electroantennographic (EAG) and behavioral (olfactometer) techniques. When crude extracts of the VOCs from B. oleracea var. botrytis seedlings and liquid chromatography fractions thereof were bioassayed, B. hilaris adults and nymphs were attracted to the crude extract, and to a non-polar fraction containing hydrocarbons, whereas there were no responses to the more polar fractions. GC-MS analysis indicated that the main constituents of the non-polar fraction was an as yet unidentified diterpene hydrocarbon, with trace amounts of several other diterpene hydrocarbons. The major diterpene occurred in VOCs from both of the preferred host plants B. oleracea and B. napus, but not in VOCs of B. carinata. Our results suggest that this diterpene, alone or in combination with one or more of the minor compounds, is a key mediator in this insect-plant interaction, and could be a good candidate for use in lures for monitoring B. hilaris in the field.

The promethea moth Callosamia promethea is one of three species of silkmoths from the genus Callosamia that occur in North America. Cross attraction of males to heterospecific calling females has been observed in the field, and hybrid progeny have been produced by pairing heterospecifics in captivity. These observations suggest that all three species share or have considerable overlap in the sex attractant pheromones produced by females, so that other prezygotic isolating mechanisms, such as diel differences in reproductive activity, limit hybridization in the field. Coupled gas chromatography-electroantennogram detection and gas chromatography- mass-spectrometry analyses of extracts of volatiles collected from female promethea moths supported the identification of (4E,6E,11Z,13Z)-hexadeca-4,6,11,13-tetraenal [(4E,6E,11Z,13Z)-16:Ald] as the compound in extracts that elicited the largest responses from antennae of males. The identification was confirmed by non-selective synthesis of several isomers as analytical standards, and stereoselective synthesis of (4E,6E,11Z,13Z)-16:Ald for testing in field trials. Male moths were strongly attracted to synthetic (4E,6E,11Z,13Z)-16:Ald, suggesting that this compound is the major and possibly the only component of the sex pheromone of these large saturniid moths. Based on the cross-attraction of heterospecifics, it is likely that this is also a major pheromone component of the other two North American Callosamia species as well.

A variety of signals mediate reproductive behaviors of Tephritidae, and studies of such behaviors have focused predominantly on economically important tephritid pest species. Trupanea vicina (Wulp) (Diptera: Tephritidae: Tephritinae), an Asteraceae-feeding fruit fly, was not considered a pest until recently, when large populations developed on marigolds in California (USA) nurseries. Understanding courtship behavior and the signals that mediate mating behavior in T. vicina could produce leads for new methods of controlling this emerging pest species. Most of the sexual behaviors observed in T. vicina were expressed by males and reflected the general characteristics of known reproductive behaviors in the genus Trupanea. Analyses of headspace volatiles indicated the presence of almost exclusively one male-specific compound, 1-nonanol. Age-related changes were observed in the amount but not in the composition of the male-produced volatiles. Aerations of males showed no diel periodicity in 1-nonanol production, but an increase after mating. Solid-phase microextraction wipe samples from various body parts of male T. vicina showed that 1-nonanol was concentrated on the abdomens of males exhibiting pleural distension. Laboratory bioassays failed to detect any strong attraction of either sex to synthetic 1-nonanol. Although the functional role of 1-nonanol in T. vicina's biology is not yet clear, we suggest that it must have some role in the life history of this species, given the relatively large amounts in which it is produced, and the specialized structures used in its production and release. Analysis of cuticular hydrocarbons extracted from males and females showed pronounced sexual dimorphism in the cuticular lipid profiles, suggesting that these compounds may have a role as short-range and contact pheromones.

The grape mealybug, Pseudococcus maritimus (Ehrhorn), is the dominant mealybug in Washington's Concord grape vineyards (Vitis labrusca L.). It is a direct pest of fruit clusters and a vector of grapevine leafroll-associated viruses. Using traps baited with the sex pheromone of Ps. maritimus, we determined the optimal trap density for monitoring Ps. maritimus, with the goal of providing a more rapid monitoring method for Ps. maritimus than visual surveys. Varying densities of pheromone-baited traps (one, four, and eight traps per 12.14 ha) were deployed in Concord vineyards to monitor Ps. maritimus seasonal phenology in 2010 and 2011. In both years, flights of adult males were detected in early May and captures peaked twice per season in mid-June and mid-August, indicating two generations each year. Trap data were analyzed using Taylor's Power Law, Iwao's patchiness regression, and the K parameter of the negative binomial model to determine optimal sample size. The formula using the K parameter provided the lowest required sample size, showing that four to eight traps per 12.14 ha were needed to provide 30% sampling precision efficiency throughout the entire season. Fewer traps were needed during flight peaks when trap capture numbers were great. Only one pheromone-baited trap per 12.14 ha was sufficient to provide Ps. maritimus flight phenology data to make informed management decisions. Species-specific pheromone-baited traps deployed for Planococcus ficus (Signoret), Pseudococcus longispinus (Targioni Tozzetti), and Pseudococcus viburni (Signoret) did not detect any of these species in the vineyards sampled.

In this study, we evaluated the responses of Triatoma dimidiata Latreille (Hemiptera: Reduviidae) to volatiles emitted by conspecific females, males, mating pairs and metasternal gland (MG) extracts with a Y-tube olfactometer. The volatile compounds released by mating pairs and MGs of T. dimidiata were identified using solid-phase microextraction and coupled gas chromatography-mass spectrometry (GC-MS). Females were not attracted to volatiles emitted by males or MG extracts; however, they preferred clean air to their own volatiles or those from mating pairs. Males were attracted to volatiles emitted by males, females, mating pairs, pairs in which the male had the MG orifices occluded or MG extracts of both sexes. However, males were not attracted to volatiles emitted by pairs in which the female had the MG orifices occluded. The chemical analyses showed that 14 and 15 compounds were detected in the headspace of mating pairs and MG, respectively. Most of the compounds identified from MG except for isobutyric acid were also detected in the headspace of mating pairs. Both females and males were attracted to octanal and 6-methyl-5-hepten-2-one, and males were attracted to 3,5-dimethyl-2-hexanol. Males but not females were attracted to a seven-compound blend, formulated from compounds identified in attractive MG extracts.

Acutaspis albopicta (Cockerell) is one of seven exotic scale species detected on shipments of ‘Hass’ avocados entering California from Mexico. Here, we present the results of experiments to elucidate basic life history parameters of this species. The scale only reproduces sexually with unmated females producing no offspring. Unmated females survived up to 14 wk after settling on host fruits, whereas males survived for up to 62 h, with the majority dying within 46 h after emergence. Females laid a mean of 52.0 ± 2.8 eggs (range, 5–171 eggs). Lower humidity (50%) was detrimental to the survival of male scales compared with high humidity (75%), especially during the pupal stage. The optimal temperature for development of both sexes was 25°C. At this temperature, females developed from first instars to adults in ≈28 d, whereas males emerged from their pupal cases after ≈37 d. The adjusted lower developmental thresholds for females and males were 13.2 and 13.4°C, respectively. The upper developmental threshold for both females and males was ≈32°C. Total development from first instar to adult female was 329 degree days and to emerged male, 433 degree days.

In recent years, several attractant pheromones have been identified for cerambycid beetles, including 2-(undecyloxy)-ethanol (hereafter monochamol) for Monochamus galloprovincialis (Olivier), M. alternatus Hope, and M. scutellatus (Say). This study screened eight known cerambycid pheromones or their analogues (including monochamol) as potential attractants for M. carolinensis Olivier and M. titillator (F.), in the presence and absence of the host volatile α-pinene. Monochamol attracted M. carolinensis in the presence and absence of α-pinene, whereas M. titillator was only attracted to the combination of monochamol and α-pinene. (2R*,3R*)-2,3-Hexanediol also attracted both M. carolinensis and M. titillator, but only in the presence of α-pinene. Subsequent coupled gas chromatography—mass spectrometry and gas chromatography—electroantennogram detection analyses of extracts of volatiles collected from both sexes demonstrated that male M. carolinensis and M. titillator release monochamol, and that ant...

A pheromone-based system to locate and monitor Planococcus minor (Maskell), a pest of over 250 plants including citrus, grape, and cacao, was tested. The difficulty in distinguishing P. minor from the citrus mealybug, P. citri, makes finding and evaluating the impact of the pest challenging. Studies conducted in Puerto Rico determined that synthetic P. minor pheromone lures preaged 120 d in the field caught similar number of males as lures not aged (fresh). Molecular analysis of trapped mealybug males using mitochondrial cytochrome oxidase-1, the internal transcriber space two locus, and 28S-D2 gene showed the pheromone traps to be species specific. Traps baited with P. minor pheromone were used to monitor the pest in south Florida and to locate potential infestations. P. minor males were found at all locations studied in South Florida and were present in low numbers (1.03 ± 0.69 mean ± SE/trap/14 d). Over 14,000 terminals, fruit, and flowers were visually inspected over a 6 mo period of peak tra...

We report identification and field testing of 2-(undecyloxy)-ethanol (monochamol) as a sex-specific, aggregation pheromone component produced by males of Monochamus scutellatus scutellatus (Say) (Coleoptera: Cerambycidae), a longhorned beetle native to North America. A congener, Monochamus notatus (Drury), which uses the same hosts as M. s. scutellatus, also was attracted to this compound in field trials, suggesting it may be a pheromone component for this species as well. Panel traps were deployed along transects at each of five field sites in May 2010 to test attraction of native beetle species to a suite of cerambycid pheromone components, including monochamol, 3-hydroxyhexan-2-one, (2R*,3R*)- and (2R*, 3S*)-2,3-hexanediol, racemic (E/Z)-fuscumol, and (E/Z)-fuscumol acetate. In total, 209 adult M. s. scutellatus (136 females, 73 males) and 20 M. notatus (16 females, four males) were captured, of which 86 and 70%, respectively, were captured in traps baited with monochamol (means significantly different). Analysis of headspace volatiles from adult M. s. scutellatus by coupled gas chromatography-mass spectrometry and gas chromatography-electroantennogram detection confirmed that monochamol was produced only by males. Monochamol was not found in headspace extracts from adult M. notatus. This study provides further evidence that monochamol is a pheromone component common to several species in the genus Monochamus. The pheromone component should prove useful for monitoring native species for management purposes or conservation efforts, and for quarantine monitoring for exotic species.

During field trials of the two known cerambycid beetle pheromone components 3-hydroxyhexan-2-one and 1-(1 H -pyrrol-2-yl)-1,2-propanedione (henceforth “pyrrole”) in Guangxi and Anhui provinces in China, four species in the subfamily Cerambycinae were attracted to lures containing one of the two components, or the blend of the two. Thus, the invasive species Callidiellum villosulum (Fairmaire) (tribe Callidiini) and a second species, Xylotrechus buqueti (Castelnau & Gory) (tribe Clytini), were specifically attracted to the blend of 3-hydroxyhexan-2-one and the pyrrole. In contrast, Allotreus asiaticus (Schwarzer) (tribe Phoracanthini) and Semanotus bifasciatus Motschulsky (tribe Callidiini) were specifically attracted to the pyrrole as a single component. In most cases, both males and females were attracted, indicating that the compounds are likely to be aggregation-sex pheromones. The results indicate that the two compounds are conserved as pheromone components among species within at least three tribes within the subfamily Cerambycinae. For practical purposes, the attractants could find immediate use in surveillance programs aimed at detecting incursions of these species into new areas of the world, including the United States.

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.

We report the identification, synthesis, and first field bioassays of a pheromone component with a novel structure produced by adult males of Chlorida festiva (L.) and Chlorida costata Audinet-Serville, longhorn beetle species in the subfamily Cerambycinae. Headspace volatiles from males contained a sex-specific compound that was identified as (6E,8Z)-6,8-pentadecadienal. Traps baited with this compound captured adults of both species and sexes, consistent with the aggregation-sex pheromones produced by males of many species in this subfamily. This compound represents a new structural class of cerambycid pheromones, and it is the first pheromone identified from species in the tribe Bothriospilini.

We report the identification, synthesis, and field bioassay of a novel attractant pheromone produced by males of Eburodacrys vittata (Blanchard), a South American cerambycid beetle in the subfamily Cerambycinae. Headspace volatiles from males contained a sex-specific compound, identified as 10-methyldodecanal. In a field bioassay conducted in Brazil, significant numbers of males and females were caught in traps baited with synthesized racemic 10-methyldodecanal, consistent with the aggregation-sex pheromones produced by males of many cerambycine species. This compound represents a new structural class of cerambycid pheromones, and it is the first pheromone identified for a species in the tribe Eburiini.

We present data indicating that three species of cerambycid beetles (subfamily Cerambycinae) produce the common cerambycine pheromone component (R)-3-hydroxyhexan-2-one as well as an alkan-2-one component, a possible new motif for cerambycid pheromone components. GC/MS analyses of headspace volatiles produced by male beetles indicated that Cyrtophorus verrucosus (Olivier) produced (R)-3-hydroxyhexan-2-one but also nonan-2-one at ~18 % of the hydroxyketone component, whereas Orwellion gibbulum arizonense (Casey) and Parelaphidion aspersum (Haldeman) produced decan-2-one at ~40 and 7 % of the amount of the hydroxyketone, respectively. In field bioassays, adult C. verrucosus were attracted by (R)-3-hydroxyhexan-2-one alone, but attraction was significantly enhanced by nonan-2-one. This effect was lost if the quantity of nonan-2-one exceeded 100 % of the hydroxyketone, suggesting that beetles could discern ratios of the two chemicals and were most strongly attracted to those approximating the blend produced by males. We suggest that nonan-2-one plays a role in the species specificity of the pheromone signal of C. verrucosus, and that decan-2-one plays a similar role in the semiochemical communication of O. g. arizonense and P. aspersum.

Two species in the genus Monochamus Dejean (Coleoptera: Cerambycidae: Lamiinae) have recently been shown to have the same male-produced sex pheromone, 2-undecyloxy-1-ethanol (monochamol), suggesting that other congeners may share the same pheromone. We tested that hypothesis by conducting field bioassays of monochamol, in combination with bark-beetle pheromones and the host plant volatiles ethanol and α-pinene, in southern British Columbia, Canada. We captured 603 Monochamus clamator (LeConte), 63 Monochamus obtusus Casey, 245 Monochamus scutellatus (Say) (tribe Monochamini), and 42 Acanthocinus princeps (Walker) (tribe Acanthocinini). All three Monochamus species were significantly attracted to the combination of monochamol and host plant volatiles, whereas bark-beetle pheromones plus plant volatiles and plant volatiles alone were minimally attractive. Adding bark-beetle pheromones to the monochamol plus plant volatiles treatment synergised attraction of M. clamator, but not the other two Monochamus species. Acanthocinus princeps was most strongly attracted to the combination of bark-beetle pheromones and plant volatiles, and did not appear to be affected by the presence or absence of monochamol in baits. We conclude that monochamol is a likely pheromone component for the three Monochamus species, and that monochamol plus host plant volatiles is an effective attractant for these and perhaps other North American Monochamus species.

We evaluated attraction of cerambycid beetle species to blends of known cerambycid pheromones to determine whether such blends could be used as effective trap lures for detecting and monitoring multiple species simultaneously. Pheromone-baited traps captured 1,358 cerambycid beetles of which 1,101 (81.1%) belonged to three species in the subfamily Cerambycinae: Neoclytus acuminatus (F.), Neoclytus mucronatus (F.), and Xylotrechus colonus (F.). Beetles of these species were significantly attracted to synthetic blends that contained their pheromone components (isomers of 3-hydroxy-2-hexanone, 2,3-hexanediol, or both), despite the presence of pheromone components of different species, including other isomers of 2,3-hexanediol, (E/Z)-6,10-dimethyl-5,9-undecadien-2-yl acetate, and citral. In some cases, attraction was partially inhibited by the pheromone components of heterospecific species, whereas for N. acuminatus, attraction was completely inhibited when blends contained (2R*,3S*)-hexanediol, the racemic mixture of diastereomers of its pheromone, (2S,3S)-hexanediol. Among the remaining beetles captured were three species in the subfamily Lamiinae: Astyleiopus variegatus (Haldeman), Graphisurus fasciatus (Degeer), and Lepturges angulatus (LeConte). All three lamiine species were previously known to be attracted to (E/Z)-6,10-dimethyl-5,9-undecadien-2-yl acetate and were captured in significant numbers by blends containing that compound. Our results suggest that different types of cerambycid pheromones can be combined to create effective multispecies lures for use in surveillance programs that target exotic cerambycid species.

This study characterized several parameters associated with reproductive behaviors of a Californian population of the grape mealybug, Pseudococcus maritimus (Ehrhorn). Experiments with caged adults confirmed that females from this population could not reproduce parthenogenetically. Both sexes were capable of mating multiple times on the same day and on sequential days. Median times between copulations were short (

Host plant volatiles have been shown to strongly synergize the attraction of some longhorn beetle species (Coleoptera: Cerambycidae) to their pheromones. This synergism is well documented among species that infest conifers, but less so for angiosperm-infesting species. To explore the extent of this phenomenon in the Cerambycidae, we first tested the responses of a cerambycid community to a generic pheromone blend in the presence or absence of chipped material from host plants as a source of host volatiles. In the second phase, blends of oak and conifer volatiles were reconstructed, and tested at low, medium, and high release rates with the pheromone blend. For conifer-infesting species in the subfamilies Spondylidinae and Lamiinae, conifer volatiles released at the high rate synergized attraction of some species to the pheromone blend. When comparing high-release rate conifer blend with high-release rate α-pinene as a single component, species responses varied, with Asemum nitidum LeConte being most attracted to pheromones plus α-pinene, whereas Neospondylis upiformis (Mannerheim) were most attracted to pheromones plus conifer blend and ethanol. For oak-infesting species in the subfamily Cerambycinae, with the exception of Phymatodes grandis Casey, which were most attracted to pheromones plus ethanol, neither synthetic oak blend nor ethanol increased attraction to pheromones. The results indicate that the responses to combinations of pheromones with host plant volatiles varied from synergistic to antagonistic, depending on beetle species. Release rates of host plant volatiles also were important, with some high release rates being antagonistic for oak-infesting species, but acting synergistically for conifer-infesting species.

The beetle Monochamus alternatus Hope (Coleoptera: Cerambycidae) is an efficient vector of pine wood nematode, the causal pathogen of pine wilt disease, that has resulted in devastating losses of pines in much of Asia. We assessed the response of adult M. alternatus to 2-(undecyloxy)-ethanol, the male-produced pheromone of the congeneric M. galloprovincialis Dejean, in field experiments in Fujian Province, People's Republic of China. Both sexes of M. alternatus were attracted to lures consisting of 2-(undecyloxy)-ethanol combined with the host plant volatiles alpha-pinene and ethanol. A follow-up experiment showed that 2-(undecyloxy)-ethanol was synergized by both ethanol and alpha-pinene. Coupled gas-chromatography mass-spectrometry analyses of volatiles sampled from field-collected beetles of both sexes revealed that 2-(undecyloxy)-ethanol was a sex-specific pheromone component produced only by males. The combination of 2- (undecyloxy) -ethanol with ethanol and/or alpha-pinene will provide a valuable and badly needed tool for quarantine detection, monitoring, and management of M. alternatus.

In laboratory bioassays, male Pseudococcus viburni (Signoret) and Planococcus ficus Signoret were attracted to body sections of females that included the metathoracic legs. Extracts of the metathoracic legs of female P. ficus were much more attractive to males than extracts of the other legs, and males exhibited copulatory behavior towards these extracts. Scanning electron microscopy showed the presence of translucent pores on the coxae of mature but not immature females. Collectively, the data suggest that the female-produced sex pheromones of these species are released from the metathoracic legs, probably from the translucent pores.

(E)-6,10-dimethyl-5,9-undecadien-2-ol (fuscumol) is an important component of male-produced aggregation pheromones for several species of cerambycid beetles in the genus Tetropium (subfamily Aseminae ⁄ Spondylidinae). Here, we describe the experiments that tested the hypothesis that fuscumol and ⁄ or fuscumol acetate also are general attractants for species in the cerambycid subfamily Lamiinae. At field sites in northwestern Indiana and central Texas (USA), panel traps baited with fuscumol or its acetate captured 331 lamiine beetles, compared to 11 beetles captured in control traps. Three species were attracted to traps baited with fuscumol as a single component, whereas another four species were attracted to fuscumol acetate alone. Surprisingly, fuscumol acetate also attracted two species in the subfamily Cerambycinae: Xylotrechus colonus (Fabricius) (males of which produce a pheromone composed only of stereoisomers of 2,3-hexanediol and 3-hydroxyhexan-2-one), and Obrium maculatum (Olivier) (for which a pheromone has yet to be identified). In an independent field experiment in east-central Illinois (USA), traps baited with fuscumol and ⁄ or its acetate captured 136 beetles of eight lamiine species, all but one species of which were also captured in the other experiment. Blending fuscumol and its acetate did not inhibit responses of species to either of the individual compounds, but synergized their activity for one species. Our results support the hypothesis that fuscumol and fuscumol acetate are widespread pheromone components or attractants for a variety of cerambycid species, especially lamiines in the tribe Acanthocinini.

Experiments confirmed that female Pseudococcus longispinus (Targioni Tozzetti), Pseudococcus viburni (Signoret), and Planococcus ficus Signoret (Hemiptera: Pseudococcidae) must mate to produce viable offspring. Females of all three species were capable of mating multiple times on the same day and on sequential days (range, 1–8 times). Female reproductive output was not increased by multiple copulations. Male P. longispinus, P. viburni, and P. ficus also mated multiple times during their lifetimes (maximum of 9, 11, and 19 times, respectively). Male P. ficus had the highest mean number of copulations (9.6 ± 0.6), followed by P. longispinus and P. viburni. More than half of the P. ficus males survived their first day of copulations and remated the next day when presented with unmated females. P.viburni males also readily mated with unmated females on the day subsequent to their first copulations. Median times between copulations were short for males of all species (

The spruce coneworm, Dioryctria abietella Denis & Schiffermuller (Lepidoptera: Pyralidae), is a major pest in spruce seed orchards in Europe. Initial work on its pheromone ecology reported significant attraction of males to (9Z,11E)-tetradecadienyl acetate (9Z,11E-14:OAc), but this compound appeared to be a very weak attractant in field trials. In this study, we show that a second female-produced compound, the polyunsaturated long-chain hydrocarbon (3Z,6Z,9Z,12Z,15Z)-pentacosapentaene (C25 pentaene), is a strong synergist to 9Z,11E-14:OAc, and that both compounds are needed for significant attraction of males. In field-trapping experiments, the highest catches were obtained with high amounts of pentaene added to the acetate (acetate:pentaene ratio from 1 : 10 to 1 : 30) and the highest doses (1–3 mg per rubber septum dispenser) were the most attractive. Two potential behavioural synergists, (Z)-9-tetradecenyl acetate and (9Z,12E)-tetradecadienyl acetate, turned out to be behavioural antagonists and both reduced trap catch of D. abietella in a dose-dependent way when added individually to the binary blend. The recent discovery of the C25 pentaene as a pheromone component of D. abietella, as well as of three North American congeners, suggests that the use of a mixture of so-called type I and type II pheromone compounds is a widespread motif of sexual communication within the genus. The identification of a highly attractive sex pheromone will help in developing efficient strategies for monitoring and control of D. abietella populations in European spruce seed orchards. (Less)

We report the identification, synthesis, and field bioassays of a female-produced sex attractant pheromone component of the cerambycid beetle Ortholeptura valida (LeConte). Headspace volatiles from females contained a female-specific compound, (Z)-11-octadecen-1-yl acetate, which elicited a strong response from antennae of adult males in coupled gas chromatography-electroantennogram analyses. In field bioassays, significant numbers of males were collected by traps baited with this compound. The pheromone represents a new structural class of cerambycid pheromones, and is the first pheromone identified for a cerambycid species in the subfamily Lepturinae.

In field trials, adult Chlorochroa uhleri (Stal) (Heteroptera: Pentatomidae) of both sexes were caught in significant numbers in cylindrical screen traps baited with gray rubber septum lures loaded with the main component of the male-produced pheromone, methyl (E)-6-2,3-dihydrofarnesoate. Addition of the two possible minor components of the pheromone, methyl (E)-5-2,6,10-trimethyl-5,9-undecadienoate and methyl (2E,6E) -farnesoate, did not affect attraction. Combining the pheromone with different concentrations of volatiles mimicking the odors of a known host plant, alfalfa (Medicago sativa L.), had no significant effect on attraction of adult bugs, whereas combining the pheromone with the pheromones of two sympatric stink bug species, Chlorochroa sayi (Stal) and Euschistus conspersus Uhler, decreased trap captures, suggesting interference between the pheromones. Small numbers of Chlorochroa ligata (Say) adults also were attracted, but numbers caught were too low to allow statistical comparisons between lure blends. In field trials with C. sayi, all three of the male-specific pheromone compounds [methyl geranate, methyl citronellate, and methyl (E) -6-2,3-dihydrofarnesoate] were required for optimal attraction. As with C. uhleri, adults of both sexes were attracted to pheromone lures in approximately equal numbers. Because of the decreased volatility (=release rate) of methyl (E)-6-2,3-dihydrofarnesoate in comparison with the other two, lower molecular weight pheromone components, lures needed to be loaded with a disproportionately high amount of methyl (E)-6-2,3-dihydrofarnesoate to obtain the best trap catch. There was no indication that the pheromone components of C. uhleri or E. conspersus interfered with the attractiveness of the C. sayi pheromone in lures containing a blend of all three pheromones.

Little is known of the reproductive behavior of longhorned beetles (Coleoptera: Cerambycidae) in the subfamily Prioninae. Mallodon dasystomus (Say), the hardwood stump borer, is a widely distributed prionine that is native to the southern U.S. Here, we explored the chemically-mediated mating behavior of M. dasystomus, and tested the hypothesis that males recognize females by a contact pheromone. In mating bioassays, all males tested attempted to mate with females only after contacting females with their antennae. Moreover, all males attempted to mate with solvent-washed dead females treated with as little as 0.15 ± 0.03 female equivalents of conspecific cuticular extracts, confirming that compounds on the cuticle of females are essential for mate recognition. Cuticular hydrocarbon profiles of females contained 13 compounds that were not present in profiles of males. Among the female-specific compounds, two co-dominant methyl-branched alkanes, 2-methylhexacosane (2Me-C(26)) and 2-methyloctacosane (2Me-C(28)), accounted for 17% of the total hydrocarbons. Our strategy for identifying the contact pheromone was to synthesize and test the bioactivity of female specific compounds, starting with the most abundant. In bioassays, males displayed mating behavior in response to synthetic 2Me-C(26) and 2Me-C(28) when tested individually. Furthermore, when these compounds were tested in combination, they elicited the full progression of mating behaviors, suggesting that 2Me-C(26) and 2Me-C(28) make up the contact pheromone. These findings are further evidence of the critical role of contact pheromones in mating systems of longhorned beetles.

In 2006-2008, we tested (3Z,6Z,9Z,12Z,15Z)-pentacosapentaene (pentaene) with the pheromone components (Z)-11-hexadecenyl acetate (Z11-16:Ac) and (Z)-9-tetradecenyl acetate (Z9-14:Ac), as sex attractants for four sympatric species of coneworms, Dioryctria Zeller (Lepidoptera: Pyralidae) in slash (Pinus elliottii Engelm.) and loblolly pine (Pinus taeda L.) seed orchards in Georgia and Louisiana, respectively. The addition ofpentaene increased catches of male southern pine coneworm, Dioryctria amatella (Hulst), in wing traps baited with Z11-16:Ac, whereas catches of Dioryctria disclusa Heinrich in traps baited with Z9-14:Ac were unaffected by the addition of pentaene. The effect of pentaene on male Dioryctria merkeli Mutuura & Munroe was inconsistent. In 2006, pentaene seemed to inhibit attraction of D. merkeli to traps baited with Z9-14:Ac, whereas in a subsequent trial in 2008, moths were equally attracted to Z9-14:Ac with or without the pentaene. We caught too few Dioryctria clarioralis (Walker) in any experiment for meaningful analyses. Our field results with pentaene and the unresolved complexity of the taxonomy, ecology, and management of southern coneworms support the need for a comprehensive examination of the chemical ecology of Dioryctria spp.

We identified a four-component sex pheromone blend that is as attractive or more attractive to male navel orangeworm moths, Amyelois transitella (Walker) (Lepidoptera: Pyralidae), than either unmated females or hexane extracts of pheromone glands of females. The blend consisted of (11Z,13Z)-hexadecadienal; (11Z,13Z)-hexadecadien-1-ol; (11Z,13E)-hexadecadien-1-ol; and a hydrocarbon, (3Z,6Z,9Z,12Z,15Z)-tricosapentaene (C23 pentaene), in ratios of approximately 100:100:5:5. Other minor components of pheromone gland extracts included (11Z,13E)-hexadecadienal; (11E,13Z)-hexadecadienal; (11Z,13Z)-hexadecadien-1-yl acetate; (Z)-11-hexadecenal; hexadecanal; hexadecan-1-ol; and a second pentaene, (3Z,6Z,9Z,12Z,15Z)-pentacosapentaene (C25 pentaene). These minor components did not increase attraction of male navel orangeworm to the basic four-component blend. The use of another, cross-attracted pyralid moth, Pyralisfarinalis L., as a model species was crucial in implicating the C23 pentaene as an important component of the navel orangeworm pheromone blend. The four-component navel orangeworm pheromone blend was optimized using a combination of wind tunnel and field bioassays. Attractiveness of field deployed synthetic pheromone lures decreased rapidly despite incorporation of stabilizers and use of different release devices, suggesting that degradation products antagonize male navel orangeworm responses. Overall, the combination of type I lepidopteran pheromone components consisting of C16 aldehydes and alcohols with type II components consisting of long-chain polyunsaturated hydrocarbons has now been documented in several lepidopteran species and may indicate a paradigm shift in the range of compounds that constitute sex pheromone blends for individual lepidopteran species. This suggests that careful reexamination of pheromone gland contents for both type I and type II compounds may prove fruitful in species that have been studied but for which full attractant blends have eluded identification.

Feeding damage by larval coneworms (Lepidoptera: Pyralidae) on flowers and cones of pines can cause significant economic losses in pine seed orchards in the southern USA (Ebel et al. 1980, USDA Forest Service GTR SE-8, Asheville, NC). The south coastal coneworm, Dioryctria ebeli Mutuura & Monroe, is a common pest in seed orchards of slash pine (Pinus elliottii L.) in the coastal region of southeastern USA, particularly Florida (Ebel et al. 1980). With multiple generations per year, infestations of D. ebeli can be severe, especially in seed orchards infected by the southern pine cone rust, Cronartium strobilinum Hedgc. & Hahn (Merkel 1958, J. Forestry 56:651 ).

Males of the predaceous stink bug Podisus maculiventris (Say) (Heteroptera: Pentatomidae: Asopinae) emit low frequency tremulatory signals. Laser vibrometry was used to record and analyze naturally emitted signals, focusing on variation in signal velocity and frequency during transmission through plants (Phaseolus vulgaris L. and Plumbago auriculata Lam.) as a function of distance from the vibrational source. Signal velocity varied individually between 2 and 15 mm/s recorded on a plant close to the calling male and decreased by 0.3 to 1.5 dB/cm on bean and 0.3 to 0.9 dB/cm on plumbago. The dominant frequency of signals was variable at frequencies below 50 Hz. On bean frequencies centered around 10 Hz or 20 Hz were dominant for signals recorded at the source. Transmission through bean resulted in an increase in the 20 Hz peak relative to other frequencies in the signal. Variation of the dominant frequencies of signals transmitted through plumbago stems were more predictable, showing typical changes in amplitude relative to the distance from the source. The regular variation of the dominant frequency along the stem with linear increase of signal velocity at decreasing distance from the source may provide plant-dwelling insects with information about the distance to the calling individual.

We report the identification and field bioassays of a major component of the male-produced aggregation pheromone of Anelaphus inflaticollis Chemsak, an uncommon desert cerambycine beetle. Male A. inflaticollis produced a sex-specific blend of components that included (R)-3-hydroxyhexan-2-one, (S)-2-hydroxyhexan-3-one, 2,3-hexanedione, and (2R,3R)- and (2R,3S)-2,3-hexanediols. Field trials with baited bucket traps determined that the reconstructed synthetic pheromone blend and (R)-3-hydroxyhexan-2-one alone attracted adult A. inflaticollis of both sexes, with significantly more beetles being attracted to the blend. We conclude that (R)-3-hydroxyhexan-2-one is a major pheromone component of A. inflaticollis, and our results suggest that one or more of the minor components may further increase attraction of conspecifics. Scanning electron microscopy showed that male A. inflaticollis have pores on the prothorax that are consistent in structure with sex-specific pheromone gland pores in related species. Males also displayed stereotyped calling behavior similar to that observed in other cerambycine species. This study represents the first report of volatile pheromones for a cerambycine species in the tribe Elaphidiini.

Field trials of the sex pheromone of an important and potentially invasive pest of avocados, Persea americana Miller (Lauraceae), Stenoma catenifer Walsingham (Lepidoptera: Elachistidae), were carried out in commercial avocado orchards in Guatemala. The results indicated that the pheromone consists of a single component, (9Z)-9,13-tetradecadien-1-ynal; blends of this compound with a range of ratios of the corresponding alcohol and acetate, or with (6Z,9Z)-tricosadiene, which was present in pheromone gland extracts, were equally or less attractive to male moths than the single component. A range of doses from 10 microg to 1 mg were equally attractive, and lures remained attractive for periods of several weeks. Male moth flight activity peaked between 0230 and 0430 hours. Overall, trap catches were relatively low, similar to what was reported for the congeneric Stenoma cecropia Meyrick, suggesting that this species may use other signals in addition to pheromones during mate location. Nevertheless, the pheromone will be useful for detection of S. catenifer, particularly in areas where there is a risk of the moth invading and establishing due to increased commerce in fresh avocados, and for certifying export orchards as being free of S. catenifer.

Adults of both sexes of the cerambycid beetles Xylotrechus colonus (F.) and Sarosesthes fulminans (F.) were attracted to odors produced by male conspecifics in olfactometer bioassays. Analyses of headspace volatiles from adults revealed that male X. colonus produced a blend of (R)- and (S)-3-hydroxyhexan-2-one and (2 S,3 S)- and (2R,3R)-2,3-hexanediol, whereas male S. fulminans produced (R)-3-hydroxyhexan-2-one and (2 S,3R)-2,3-hexanediol. All of these compounds were absent in the headspace of females. Two field bioassays were conducted to confirm the biological activity of the synthesized pheromones: (1) enantiomerically enriched pheromone components were tested singly and in species-specific blends and (2) four-component mixture of racemic 3-hydroxyhexan-2-one plus racemic 2-hydroxyhexan-3-one and the four-component blend of the stereoisomers of 2,3-hexanediols were tested separately and as a combined eight-component blend. In these experiments, adult male and female X. colonus were captured in greatest numbers in traps baited with the reconstructed blend of components produced by males, although significant numbers were also captured in traps baited with (R)-3-hydroxyhexan-2-one alone or in blends with other compounds. Too few adult S. fulminans were captured for a statistical comparison among treatments, but all were caught in traps baited with lures containing (R)-3-hydroxyhexan-2-one. In addition to these two species, adults of two other species of cerambycid beetles, for which pheromones had previously been identified, were caught: Neoclytus a. acuminatus (F.) and its congener Neoclytus m. mucronatus (F.). Cross-attraction of beetles to pheromone blends of other species, and to individual pheromone components that are shared by two or more sympatric species, may facilitate location of larval hosts by species that compete for the same host species.

The fir coneworm, Dioryctria abietivorella (Groté), is a transcontinental pest of coniferous seed cones. Recently, the attractive pheromone components and lure blend for the fir coneworm in western Canada were identified as a 200 µg : 2000 µg ratio of (9Z,11E)-tetradecadienyl acetate (9Z,11E-14:Ac) and a polyunsaturated hydrocarbon, (3Z,6Z,9Z,12Z,15Z)-pentacosapentaene (C25 pentaene). A potential third component, (Z)-9-tetradecenyl acetate (9Z-14:Ac), which was detected in pheromone gland extracts, had no effect on males of the western population when added to the binary blend. In contrast, in eastern Canada (Quebec) we found that the 200 µg : 2000 µg binary blend was unattractive to male fir coneworms until 9Z-14:Ac was added. By means of several field experiments we established that a 67 µg : 200 µg : 2000 µg ratio of 9Z-14:Ac, 9Z,11E-14:Ac, and the C25 pentaene was attractive to fir coneworms in Quebec. Gas chromatography - mass spectrometry analysis of pheromone gland extracts of fir coneworm from Quebec confirmed the presence of the three components in extracts in an approximately 1 µg : 4 µg : 10 µg ratio of 9Z-14:Ac, 9Z,11E-14:Ac, and the C25 pentaene. Our results provide evidence that the eastern and western populations of D. abietivorella are distinct geographic pheromone races, with 9Z-14:Ac being required for attracting males of the eastern population but not males of the western population.

We report the identification, synthesis, and field bioassays of a volatile, male-produced aggregation pheromone of a long-horned beetle, the banded alder borer, Rosalia funebris Mots. Headspace collections from males contained a major male-specific compound, (Z)-3-decenyl (E)-2-hexenoate, and several minor components, identified as (Z)-3-decenol, (Z)-3-nonenyl (E)-2-hexenoate, and (Z)-3-decenyl (E)-3-hexenoate. The antennae of both males and females responded strongly to (Z)-3-decenyl (E)-2-hexenoate. We collected significant numbers of adult R. funebris in field bioassays using traps baited with this compound. This pheromone structure is unprecedented in the literature of cerambycid pheromones and distinct from the more common diol/hydroxyketone pheromone motif of many other species of the diverse subfamily Cerambycinae. This is the first pheromone identified for a species in the tribe Rosaliini.

Male Neoclytus acuminatus acuminatus (F.) (Coleoptera: Cerambycidae) attempt to mate with females only after touching them with their antennae, suggest- ing that mate recognition is mediated by contact pheromones in the cuticular wax layer of females. Consistent with that hypothesis, males exhibit similar responses to dead females in laboratory bioassays, but not to solvent-washed dead females with their cuticular hydrocarbons removed. The mating response of males is restored when solvent extracts are reapplied to carcasses of solvent-washed females, indicat- ing that the contact pheromone is present in solvent extracts. Solvent extracts of the female cuticle contain six methylalkanes that are not present in extracts of males, three of which (7Me-C 25 , 7Me-C 27 and 9Me-C 27 ) constitute almost 40% of the total hydrocarbons. The bioactivity of these three compounds is tested by applying syn- thetic standards to solvent-washed carcasses of females and presenting them to males. Standards are tested singly, pairwise and as the complete blend; freeze-killed females serve as controls. Males attempt to couple with solvent-washed female car- casses treated with 7Me-C 27 alone and in combination with 9Me-C 27 but only the complete blend elicits the same number of mounting and coupling attempts as does the control. These findings suggest that 7Me-C 27 (7-methylheptacosane) is the major component of the contact sex pheromone of N. a. acuminatus and that 7Me-C 25 and 9Me-C 27 act as synergists.

Odors from fresh chicken feces in water elicited upwind flight of host-seeking female Culex quinquefasciatus mosquitoes in a dual-choice olfactometer. Acidification of the slurry of chicken feces and water resulted in increased attraction, whereas alkaline slurries of chicken feces and water controls did not attract female mosquitoes. This is the first reported example of avian fecal odor eliciting upwind flight of female mosquitoes. Headspace odors from acidified slurries were sampled using solid phase micro-extraction (SPME) coated fibers. Eight volatile aldehydes [(E)-2-decenal, undecanal, dodecanal, tetradecanal, pentadecanal, hexadecanal, heptadecanal, and octadecanal] identified in the headspace of acidified chicken feces elicited electroantennogram responses from antennae of C. quinquefasciatus females. An improved electroantennogram technique in which four antennae were used in parallel for monitoring the GC effluent is described.