Male-Produced Aggregation Pheromone Compounds from the Eggplant Flea Beetle (Epitrix fuscula): Identification, Synthesis, and Field Biossays

Volatiles from the eggplant flea beetle, Epitrix fuscula Crotch (Coleoptera: Chrysomelidae), feeding on host foliage, were investigated. Six male-specific compounds were detected and were identified through the use of mass spectrometry, nuclear magnetic resonance (NMR) spectrometry, chiral and achiral gas chromatography, high-performance liquid chromatography, electrophysiology (gas chromatography-electroantennography, GC–EAD), and microchemical tests. The two most abundant of the six compounds were (2E,4E,6Z)-2,4,6-nonatrienal (1) and (2E,4E,6E)-2,4,6-nonatrienal (2). The other four compounds, present in minor amounts, were identified as himachalene sesquiterpenes; two of these, 3 and 4, were hydrocarbons and two, 5 and 6, were alcohols. All four sesquiterpenes were previously encountered from male flea beetles of Aphthona spp. and Phyllotreta cruciferae. Synthetic 1 and 2 matched the natural products by GC retention times, mass spectra, and NMR spectra. Sesquiterpenes 3–6 similarly matched synthetic standards and natural samples from the previously studied species in all ways, including chirality. Both natural and synthetic 1 and 2 gave positive GC–EAD responses, as did sesquiterpenes 3, 5, and 6. Field trials were conducted with a mixture of 1 and 2, and the baited traps were significantly more attractive than control traps to both male and female E. fuscula. The E. fuscula pheromone has potential for monitoring or controlling these pests in eggplants.Mention of trade names or commercial products in this article is solely for the purpose of providing specific information and does not imply recommendation or endorsement by the Department of Agriculture.     

Green Leaf Volatiles Interrupt Pheromone Response of Spruce Bark Beetle, Ips typographus

A synthetic mixture of nine green leaf volatiles (GLVs) including linalool was tested on antennae of Ips typographus (L.) with coupled gas chromatographic–electroantennographic detection (GC-EAD). Strong responses were found to 1-hexanol, (Z)-3-hexen-1-ol, and (E)-2-hexen-1-ol. Weak responses were recorded to (E)-3-hexen-1-ol, (Z)-2-hexen-1-ol and linalool, while hexanal, (E)-2-hexenal and (E)-3-hexenyl acetate elicited no EAD responses. In a laboratory walking bioassay, the attraction of I. typographus females to a synthetic pheromone source was significantly reduced when a mixture of the three most EAD-active GLV alcohols was added to the source. Further reduction in response was obtained when these three alcohols were combined with verbenone (Vn). In field trapping experiments, a blend of 1-hexanol, (Z)-3-hexen-1-ol, and (E)-2-hexen-1-ol reduced I. typographus trap catches by 85%, while ca. 70% reduction of trap catch was achieved by Vn or a blend of (E)-3-hexen-1-ol, (Z)-2-hexen-1-ol, and linalool. The strongest disruptive effect was found when Vn plus a blend of the three most EAD active GLV alcohols was added to the pheromone trap (95% catch reduction). Adding the blend of the three most EAD active alcohols to pheromone-baited traps significantly reduced the proportion of males captured. These three GLV alcohols were also disruptive in the laboratory and in the field when tested individually. Hexanal, (E)-2-hexenal, and (Z)-3-hexenyl acetate were inactive both in the lab and in the field. Our results suggest that these nonhost green leaf alcohols may explain part of the host selection behavior of conifer-attacking bark beetles and may offer a source of inhibitory signals for alternative management strategy for forest protection.     

Attraction of Piezodorus hybneri to the Aggregation Pheromone Components of Riptortus clavatus

The aggregation pheromone of Riptortus clavatus (Heteroptera: Alydidae) consists of (E)-2-hexenyl (Z)-3-hexenoate (E2HZ3H), (E)-2-hexenyl (E)-2-hexenoate (E2HE2H), and myristyl isobutyrate (MI). Experiments were conducted to examine the attraction of Piezodorus hybneri (Heteroptera: Pentatomidae) to the pheromone components of R. clavatus, individually and in combination, and to determine if P. hybneri produces these compounds. Electroantennogram (EAG) responses of P. hybneri to E2HE2H were significant in a dose dependent manner, while those to E2HZ3H were not significantly different from those to hexane and air. Field trapping tests using E2HZ3H, E2HE2H, and MI, individually or in combination, showed that only E2HE2H was attractive to P. hybneri. E2HE2H was not detected in whole-body extracts or volatile collections from either sex of P. hybneri adults. We propose that the response of P. hybneri adults to the R. clavatus aggregation pheromone may be related to finding suitable host plants.     

Male-Produced Aggregation Pheromone of the Cerambycid Beetle <Emphasis Type="Italic">Rosalia funebris</Emphasis>

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. Electronic supplementary material  The online version of this article (doi:) contains supplementary material, which is available to authorized users.     

Aggregation pheromone of square-necked grain beetle,Cathartus quadricollis (Guér.)

When feeding on rolled oats, male square-necked grain beetles,Cathartus quadricollis (Guér.), produced the aggregation pheromone (3R,6E)-7-methyl-6-nonen-3-yl acetate, for which the trival name quadrilure is proposed. The pheromone was highly attractive to both sexes in a two-choice, pitfall olfactometer modified to retain responding beetles by placing a food stimulus (an oat flake) in the glass vials containing the experimental and control stimuli. TheS enantiomer of the pheromone was inactive. Males also produced small amounts of (E)-7-methyl-6-nonen-3-one, (E)-7-methyl-6-nonen-3-ol, and (6E)-7-methyl-3-propyl-2,6-nonadienyl acetate, but these compounds were inactive in the laboratory bioassay. Segregated males and females both produced (R)-(–)-1-octen-3-ol, which by itself was repellent to both sexes but did not diminish beetle response to the aggregation pheromone.Coleoptera: Cucujidae.Research supported by the Natural Sciences and Engineering Research Council of Canada, Strategic Grant G1039 and Operating Grants A3881 and A3706.     

Isolation, Identification, Synthesis, and Field Evaluation of the Sex Pheromone of the Brazilian Population of Spodoptera frugiperda

Several studies have shown intraspecific geographical variation in the composition of sex pheromones. Pheromone lures from North America and Europe were not effective against the fall armyworm Spodoptera frugiperda (Smith, 1797) (Lepidoptera: Noctuidae) in Brazil, so we examined the composition of the sex pheromone produced by females from Brazilian populations. Virgin female gland extracts contained (Z)-7-dodecenyl acetate (Z7-12:Ac), (E)-7-dodecenyl acetate (E7-12:Ac), dodecyl acetate, (Z)-9-dodecenyl acetate, (Z)-9-tetradecenyl acetate (Z9-14:Ac), (Z)-10-tetradecenyl acetate, tetradecyl acetate/(Z)-11-tetradecenyl acetate (Z11-16:Ac), and (Z)-11-hexadecenyl acetate. The relative proportions of each acetate were 0.8:1.2:0.6:traces:82.8:0.3:1.5:12.9, respectively. This is the first time that E7-12:Ac has been reported from the pheromone gland of S. frugiperda. Only three compounds, Z9-14:Ac, Z7-12:Ac, and E7-12:Ac, elicited antennal responses, and there were no differences in catch between traps baited with either Z7-12:Ac + Z9-14:Ac or Z7-12:Ac + Z9-14:Ac + Z11-16:Ac blends. However, the Z7-12:Ac + Z9-14:Ac + E7-12:Ac blend was significantly better than Z7-12:Ac + Z9-14:Ac, indicating that E7-12:Ac is an active component in the sex pheromone of the Brazilian populations of S. frugiperda.     

Identification, Synthesis, and Field Evaluation of the Sex Pheromone of the Citrus Fruit Borer Ecdytolopha aurantiana

The sex pheromone of the citrus fruit borer Ecdytolopha aurantiana has been identified by gas chromatography coupled to an electroantennographic detector (GC-EAD). The electron impact mass spectral (EI-MS) fragmentation of the major EAD-active peak gave identifying features for a monounsaturated acetate. Further analyses by chemical ionization mass spectrometry (CI-MS), vapor-phase infrared spectroscopy (GC-IR), along with chemical derivatization (DMDS reaction), led to full characterization of the major component as (E)-8-dodecenyl acetate (E8–12 : Ac). The second constituent was identified as the related alcohol, (E)-8-dodecenol (E8–12 : OH). The two compounds were indistinguishable from the authentic synthetic standards in chemical and EAD analyses. Samples of the two compounds were obtained by a facile synthesis utilizing lithium chemistry. Field tests showed that captures in traps baited with a mixture of E8–12 : Ac and E8–12 : OH at 100 : 1 and 10 : 1 ratios were not significantly different from the catches in traps having two virgin females. Dosage tests showed better performance of traps baited with 1 mg than those with 0.1 mg of the pheromone blend, either in 100 : 1 or 10 : 1 ratio.     

Identification and Field Evaluation of Components of Female Sex Pheromone of Millet Stem Borer, Coniesta ignefusalis

Five active compounds were detected during analyses of ovipositor washings and effluvia from virgin female Coniesta ignefusalis moths by gas chromatography (GC) linked to electroantennographic (EAG) recording from a male moth. These were identified as (Z)-7-dodecen-1-ol (Z7–12:OH), (Z)-5-decen-1-ol (Z5–10:OH), (Z)-7-dodecenal (Z7–12:Ald), (Z)-7-dodecenyl acetate (Z7–12:Ac), and (Z)-9-tetradecen-1-ol (Z9–14:OH) by comparison of their GC retention times, mass spectra, and EAG activities with those of synthetic standards. Laboratory tests of dispensers for these compounds showed that release rates from polyethylene vials increased to relatively uniform values after three to four days, but release from septa was very rapid and nonuniform and decreased to low levels after two to three days. Trapping tests in Niger showed that the major component, Z7–12:OH, and two of the minor components, Z5–10:OH and Z7–12:Ald, were essential for attraction of male C. ignefusalis moths. The most attractive blend contained these three components in a 100:5:3.3 ratio in a polyethylene vial, which emitted the components in similar proportions to those produced by the female C. ignefusalis moth. Water traps baited with this blend containing 1 mg of Z7–12:OH caught more male C. ignefusalis moths than traps baited with newly emerged female moths. Addition of up to 10% of the corresponding E isomers of the pheromone components had no effect on catches, but addition of the other two minor components detected, Z7–12:Ac and/or Z9–14:OH, to the attractive blend at naturally occurring levels caused significant reductions in trap catch.     

Field Tests of Synthetic Sex Pheromone of the Apple Leafminer Moth, Phyllonorycter ringoniella

The apple leafminer moth, Phyllonorycter ringoniella, is becoming a more serious insect pest on apple trees with four to five generations a year in Korea. In order to devise a forecasting method for more accurate estimation of their numbers and development timing, the sex attractant was studied. Various ratios, from 10:0 to 0:10, of the two components, (Z)-10-tetradecenyl acetate (Z10–14:Ac) and (E,Z)-4,10-tetradecadienyl acetate (E4,Z10–14:Ac), identified from the sex pheromone gland (Jung and Boo, 1997), were tested for attractivity in terms of behavioral response (taxis, approach, and landing) against P. ringoniella males in a wind tunnel. The lure with Z10–14:Ac/E4,Z10–14:Ac in a ratio of 4:6 elicited the highest response in two (taxis and approach) measurement categories. For eliciting landing behavior, the two blends of 5:5 and 4:6 were best. The single component, Z10–14:Ac, elicited taxis behavior, but a combination of two chemicals was needed for eliciting all three behaviors. In the field, male attraction to various lure mixtures in Pherocon IC traps was usually greater than attraction to virgin females. The best field activity was in the lure baited with a 4:6 ratio of Z10–14:Ac and E4,Z10–14:Ac. Similar results were obtained from tests conducted in a net house. This optimum ratio for attracting P. ringoniella males in Korea is different from those reported in Japan (10:3) or China (7:3 to 6:4). The isomer E10–14:Ac neither improved nor depressed the number of catches when added at up to 10% of the total mixture to lures of the two components in the 4:6 ratio. The attractivity of the lures increased with higher amounts of the pheromones, up to 10 g in the wind-tunnel experiment and 5 mg in the apple orchard. The number of males captured was not significantly different among traps installed at 0.3, 1.5, or 2 m above the ground, or among wing, delta, or water traps. A rubber septum dispenser impregnated with 1 mg of the 4:6 mixture maintained its field attractivity for up to eight weeks.     

Sex Pheromone of Apple Blotch Leafminer, Phyllonorycter crataegella, and Its Effect on P. mespilella Pheromone Communication

(Z)-10,(Z)-12-Tetradecadienyl acetate (Z10,Z12–14:OAc) and (E)-10,(E)-12-tetradecadienyl acetate (E10,E12–14:OAc) are sex pheromone components of the apple blotch leafminer (ABLM), Phyllonorycter crataegella. Compounds extracted from female pheromone glands were identified by coupled gas chromatographic–electroantennographic detection (GC-EAD) analyses, retention index calculations of EAD-active compounds, and by comparative GC-EAD analyses of female ABLM-produced and authentic (synthetic) compounds. In field experiments in apple Malus domestica orchards in Connecticut, Z10,Z12–14:OAc alone attracted ABLM males. Addition of E10,E12–14:OAc to Z10,Z12–14:OAc at 0.1:10 or 1:10 ratios enhanced attractiveness of the lure. Geometrical isomers Z10,E12- or E10,Z12–14:OAc at equivalent ratios were behaviorally benign and slightly inhibitory, respectively. In field experiments in British Columbia, Z10,Z12–14:OAc plus E10,E12–14:OAc did not attract Phyllonorycter moths, supporting the contention that ABLM is not present in the fruit growing regions of British Columbia. Z10,Z12–14:OAc added to P. mespilella pheromone, (E)-4,(E)-10-dodecadienyl acetate, strongly inhibited response by P. mespilella males. Recognition of the ABLM pheromone blend by allopatric P. mespilella males suggests a phylogenetic relationship and previous sympatry of these two Phyllonorycter spp. If pheromonal attraction of ABLM males were reciprocally inhibited by P. mespilella pheromone, a generic Phyllonorycter pheromone blend could be tested for pheromone-based mating disruption of the apple leaf-mining Phyllonorycter guild in North America.     

Sex Pheromone of the Persimmon Fruit Moth, Stathmopoda masinissa: Identification and Laboratory Bioassay of (4E, 6Z)-4,6-Hexadecadien-1-ol Derivatives

Three electroantennogram (EAG)-active components were detected by gas chromatography coupled to an electroantennographic detector (GC–EAD) analysis of a hexane extract of the pheromone glands of the persimmon fruit moth, Stathmopoda masinissa. These compounds were identified as (4E,6Z)-4,6-hexadecadienal (E4,Z6-16:Ald) and the corresponding acetate (E4,Z6-16: OAc) and alcohol (E4,Z6-16:OH) by mass spectral, GC retention time (RT), and microchemical test data. The characteristic base peak of the aldehyde at m/z 84 provided a crucial piece of information suggesting the possibility of a 4,6-diene structure. The (4E,6Z)-isomer elicited the strongest EAG responses among the four geometrical isomers of each synthetic 4,6-hexadecadienyl compound. In a laboratory bioassay, only E4,Z6-16:OAc elicited male moth behavioral activity significantly different from the control; the activity of the acetate was not affected by addition of the aldehyde and alcohol. A preliminary field trial confirmed that E4,Z6-16:OAc as a single component attracted male moths. The possible roles of E4,Z6-16:Ald and E4,Z6-16:OH as components of lures for field use remain to be determined.     

(Z)-7-Tricosene and Monounsaturated Ketones as Sex Pheromone Components of the Australian Guava Moth Coscinoptycha improbana: Identification, Field Trapping, and Phenology

Pheromone gland extracts of the Australian guava moth Coscinoptycha improbana (Lepidoptera: Carposinidae), contained four compounds that elicited responses from male moth antennae in gas chromatography-electroantennogram detection (GC-EAD) analyses. These were identified by GC-mass spectrometry as (Z)-7-tricosene (Z7-23Hy), (Z)-7-octadecen-11-one (Z7-11-one-18Hy), (Z)-7-nonadecen-11-one (Z7-11-one-19Hy), and (Z)-7-tricosen-11-one (Z7-11-one-23Hy) at a ratio of 65:23.5:1.5:10, respectively. Z7-23Hy, Z7-11-one-18Hy, and Z7-11-one-23Hy have not previously been reported as lepidopteran sex pheromone components. Z7-11-one-18Hy was active as a single component, and was synergized by Z7-11-one-23Hy but not Z7-11-one-19Hy, although the latter compound was weakly attractive as a single component. Addition of Z7-23Hy further increased attraction. The amount of the major pheromone component, Z7-11-one-18Hy in female pheromone gland extracts was estimated to be 16.4 ng/female (N = 8). Phenological data gathered over a 12-mo period in 2002 and 2003 using the binary blend indicated that moths are active throughout the year. The pheromone has already been employed to monitor the spread of C. improbana in New Zealand and detect its presence in Queensland, Australia.     

Sex Pheromone of the Dogwood Borer, <Emphasis Type="Italic">Synanthedon scitula</Emphasis>

The sex pheromone of female dogwood borers (DWB) Synanthedon scitula (Harris) (Lepidoptera: Sesiidae) was determined to be an 88:6:6 ternary blend of (Z,Z)-3,13-octadecadienyl acetate (Z,Z-3,13-ODDA), (E,Z)-2,13-octadecadienyl acetate (E,Z-2,13-ODDA), and (Z,E)-3,13-octadecadienyl acetate (Z,E-3,13-ODDA) by gas chromatography–electroantennographic detection (GC–EAD) and gas chromatography–mass spectrometry (GC–MS). The major sex pheromone component, Z,Z-3,13-ODDA, was attractive as a single component. A blend of Z,Z-3,13-ODDA with 1–3% of E,Z-2,13-ODDA (binary blend) was more attractive than the single component. A third component, Z,E-3,13-ODDA, was sometimes observed in GC–EAD analyses, and enhanced attraction to the binary blend in some field bioassays. Lures containing 1 mg of binary and ternary blends attracted 18 and 28 times more male DWB moths, respectively, than caged virgin females in field trials. Attraction was strongly antagonized by addition of as little as 0.5% of E,Z-3,13-octadecadienyl acetate (E,Z-3,13-ODDA). In a period of 12 wk in 2004, more than 60,000 males were captured in sticky traps baited with synthetic pheromone blends in six apple orchards in Virginia, West Virginia, and North Carolina. Lure longevity trials showed that ∼76% of the pheromone remained in rubber septum lures after 12 wk in the field.     

Male-produced Aggregation Pheromone of Colopterus truncatus: Structure, Electrophysiological, and Behavioral Activity

A male-produced aggregation pheromone was demonstrated in Colopterus truncatus Randall (Coleoptera: Nitidulidae) by gas chromatographic comparisons of male and female volatile emissions. Male-specific compounds were identified with coupled gas chromatographic–mass spectrometric (GC-MS) analysis and GC and MS comparison of authentic standards. Physiological activity was evaluated by coupled gas chromatographic–electroantennographic (GC-EAG) recordings, and electroantennographic (EAG) assays of standards. The male-produced volatiles eliciting responses from male and female antennae (and relative abundance) were (2E,4E,6E)-3,5-dimethyl2,4,6-octatriene (1) (1.8), (2E,4E,6E)-4,6-dimethyl-2,4,6-nonatriene (2) (100), and (2E,4E,6E,8E)-3,5,7-trimethyl-2,4,6,8-decatetraene (3) (3.3). A fourth male-specific compound, (2E,4E,6E,8E)-4,6,8-trimethyl-2,4,6,8-undecatetraene (4) (0.6) was not EAG-active. EAG dose–response studies showed that the antennae were most sensitive to 2 followed by 3 and 1. Synthetic 2, binary blends of 1 and 3, and tertiary blends of 1, 2, and 3 were highly attractive in the field when synergized with fermenting whole-wheat bread dough. In the field, cross-attraction to the C. truncatus pheromone components was observed for Carpophilus lugubris Murray, C. antiquus Melsheimer, and C. brachypterus Say.     

Identification Of Sex Pheromone Components Of The Painted Apple Moth: A Tussock Moth With A Thermally Labile Pheromone Component

The sex pheromone of the painted apple moth, Teia anartoides (Lymantriidae) was investigated using GC-EAD and GC-MS analysis, derivatization, TLC analysis, and field cage and field trapping bioassays. The major sex pheromone components were identified as (6Z,9Z)-henicosa-6,9-dien-11-one and (6Z,9Z)-henicosa-6,9-diene. Other minor components of pheromone gland extracts included (6Z)-9R,10S-epoxyeicos-6-ene, (6Z)-9R,10S-epoxyhenicos-6-ene, (6Z,9Z)-henicosa-6,9-dien-11-ol, (6Z)-henicos-6-en-11-one, and (6Z, 8E)-henicosa-6,8-dien-11-one, but the roles of these minor components remain equivocal. In field cage and field experiments, a blend of all seven identified components [(6Z,9Z)-henicosa-6,9-dien-11-one (relative amount 100), (6Z,9Z)-henicosa-6,9-diene (100), (6Z)-9R,10S-epoxyeicos-6-ene (5), (6Z)-9R,10S-epoxyhenicos-6-ene (10), (6Z,9Z)-henicosa-6,9-dien-11-ol (5), (6Z)-henicos-6-en-11-one (1), and (6Z,8E)-henicosa-6,8-dien-11-one (25)] was as attractive to males as calling females, but tests with blends of the major component(s) with subsets of the minor components did not produce consistent results that unequivocally showed the various minor components to be critical components of the active blend. (6Z,9Z)-henicosa-6,9-dien-11-one is thermally labile and rearranges to (6Z,8E)-henicosa-6,8-dien-11-one and other products at ambient temperature, rendering the synthetic pheromone lure inactive after two days of field exposure.     

Identification of Sex Pheromone of Adzuki Bean Borer,Ostrinia scapulalis

By means of gas chromatography with electroantennographic detection (GC-EAD), gas chromatography–mass spectrometry (GC-MS), and a series of bioassays, (Z)-11-tetradecenyl acetate (Z11–14:OAc) and (E)-11-tetradecenyl acetate (E11–14:OAc) at a ratio of 100:3 were identified as the female sex pheromone of the adzuki bean borer,Ostrinia scapulalis. The average amounts ofZ11–14: OAc andE11–14:OAc in a single sex pheromone gland were 6.6 ± 2.4 ng and 0.2 ± 0.1 ng, respectively. In a wind-tunnel bioassay, the binary blend ofZ11- andE11–14:OAc elicited almost the same male behavioral responses as did virgin females and sex pheromone gland extract. In field trapping experiments, rubber septa impregnated with the binary blend (50 g/septum) attracted more males than virgin females. The sex pheromone ofO. scapulalis thus turned out to be similar to that of theZ-type European corn borer,O. nubilalis, in both components and their ratio.     

Heritable Variation in the Sex Pheromone of the Almond Moth, Cadra cautella

The sex pheromone of the female almond moth, Cadra cautella, constitutes a highly variable signal. Age and period of the L/D cycle had significant effects on the variation in titers of (Z,E)-9,12-tetradecadienyl acetate (Z9,E12-14:Ac) and (Z)-9-tetradecenyl acetate (Z9-14:Ac) and the ratio of Z9,E12-14:Ac to Z9-14:Ac. Across age classes, minimum and maximum mean titers (ng +/- SE) of Z9,E12-14:Ac and Z9-14:Ac ranged from 8.7 +/- 0.46 to 21 +/- 1.0 and from 2.0 +/- 0.14 to 2.9 +/- 0.15, respectively; the mean ratio of Z9,E12-14:Ac to Z9-14:Ac ranged from 5.2 +/- 0.21 to 11 +/- 0.40. The titers of Z9,E12-14:Ac and Z9-14:Ac and the ratio of Z9,E12-14:Ac to Z9-14:Ac were highest at the onset of the scotophase and lowest at the onset of the photophase. Similarly, the titer of Z9,E12-14:Ac and the ratio of Z9,E12-14:Ac to Z9-14:Ac were highest in females sampled 1 d postemergence and declined over all age classes. The titer of Z9-14:Ac increased from day 1 to day 2, and then declined to levels equivalent to day 1. Analysis of pupal and adult mass demonstrated a positive correlation (r = 0.874, P < 0.001); however, the titer of neither Z9,E12-14:Ac or Z9-14:Ac nor the ratio of Z9,E12-14:Ac to Z9-14:Ac were significantly correlated with pupal mass. Age-related variations in pheromone titer and ratios were heritable. The narrow-sense heritability of the observed variation in 1-d-old females, 1 hr into the scotophase is 1.2 +/- 0.32, 0.75 +/- 0.24, and 0.46 +/- 0.17 for the titer of Z9,E12-14:Ac and Z9-14:Ac and the ratio of Z9,E12-14:Ac to Z9-14:Ac, respectively. A significant additive genetic correlation was observed between that of Z9,E12-14:Ac and Z9-14:Ac, but not between that of either Z9,E12-14:Ac or Z9-14:Ac and the ratio of Z9,E12-14:Ac to Z9-14:Ac. The results of the genetic analyses suggest that the traits of titer of Z9,E12-14:Ac and Z9-14:Ac have a greater potential to respond to selection than the trait of ratio of Z9,E12-14:Ac to Z9-14:Ac.     

Characterization of Pheromone Blend for Grapevine Moth, Lobesia botrana by Using Flight Track Recording

The behavioral responses of Lobesia botrana males to calling females, pheromone gland extracts, and synthetic sex pheromones were recorded in a wind tunnel. Gland extracts and synthetic pheromones were released from a pheromone evaporator. The numbers of males reaching the source and their flight tracks in response to calling females and pheromone gland extracts were compared to those of synthetic blends. Upwind flights to natural sex pheromone were straighter and faster than to a three-component blend of (E)-7,(Z)-9-dodecadienyl acetate (E7,Z9–12:Ac), (E)-7,(Z)-9-dodecadien-1-ol (E7,Z9–12:OH), and (Z)-9-docecenyl acetate (Z9–12:Ac) (100:20:5). The optimum ratio of E7,Z9–12:OH and Z9–12:Ac to E7,Z9–12:Ac was found to be 5% and 1%, respectively. An additional seven compounds identified in the sex pheromone gland were investigated for their biological activity. Two unsaturated acetates, i.e., (E)-9-dodecenyl acetate (E9–12:Ac) and 11-dodecenyl acetate (11–12:Ac), increased the number of males reaching the source as well as straightness, linear velocity, and decreased the track angle of upwind flight. Optimum response was obtained by releasing 10 pg/min E7,Z9–12:Ac in a mixture with 0.5 pg/min E7,Z9–12:OH, 0.1 pg/min Z9–12:Ac, 0.1 pg/min E9– 12:Ac and 1 pg/min 11-12–Ac. The saturated acetates previously identified in the female glands were biologically inactive.     

Isolation, Identification and Field Tests of the Sex Pheromone of the Carambola Fruit Borer, Eucosma notanthes

Two components, (Z)-8-dodecenyl acetate (Z8-12:Ac) and (Z)-8-dodecenol (Z8-12:OH), were isolated from sex pheromone glands of the carambola fruit borer, Eucosma notanthes, and were identified by GC, and GC-MS, chemical derivatization, and comparison of retention times. The ratio of the alcohol to acetate in the sex pheromone extracts was 2.7. However, synthetic mixtures (1 mg) in ratios ranging from 0.5 to 1.5 were more effective than other blends in trapping male moths in field tests.     

Aggregation pheromones of the flat grain beetle,Cryptolestes pusillus (Coleoptera: Cucujidae)

Aggregation pheromones were isolated fromCryptolestes pusillus (Schönherr), a coleopteran pest of stored products. Porapak Q-captured beetle and frass volatiles were fractionated by preparative gas-liquid chromatography. The fractions were bioassayed with an arena olfactometer and/or with a two-choice, pitfall olfactometer. Three biologically active, male-produced compounds eliciting aggregation behavior from adultC. pusillus were isolated and identified by spectroscopic methods as (Z)-3-dodecenolide (I), (Z)-5-tetradecen-13-olide (II), and (Z,Z)-3,6-dodecadienolide (III). Compound I was the major volatile produced and was active alone. Compound II was not active alone, but synergized the response to I. Compound III was active alone at higher concentrations, but did not significantly increase the response when added to the most active mixture of I and II, and so it is probably not part of the aggregation pheromone. Pheromone production increased dramatically when the insects were aerated on a food source.Research supported in part by the Natural Sciences and Engineering Research Council of Canada, Operating Grants A3881 and A3785, Strategic Grant 60958, and a Graduate Scholarship to J. G. Millar.