Identification of a novel moth sex pheromone inEriocrania cicatricella (Zett.) (Lepidoptera: Eriocraniidae) and its phylogenetic implications

Extracts from different body parts of adult femaleEriocrania cicatricella (Zett.) were tested for electrophysiological activity on conspecific male antennae. Extracts from the Vth abdominal segment, containing a pair of exocrine glands, elicited the largest electroantennographic response when compared to extracts of other body parts. Female extracts were analyzed by gas chromatography with simultaneous flame ionization and electroantennographic detection (EAD). The EAD active peaks were identified as (Z)-4-hepten-2-one, (2R)-heptane-2-ol, and (2R)-(Z)-4-hepten-2-ol by coinjection on a gas chromatography and by comparison of mass spectra with those of synthetic standards. In field tests, a blend of these three pheromone components was highly attractive to conspecific males, and a subtractive assay confirmed that the unsaturated alcohol is the major pheromone component, whereas no definite behavioral activity could be assigned to the ketone or the saturated alcohol. A bait containing the two alcohols withS-configuration was attractive to maleE. sparrmannella (Bosc), whereas no males ofE. cicatricella were found in these traps. The sex pheromone compounds inE. cicatricella are chemically similar to pheromones reported in Trichoptera and they are produced in homologous glands.     

(E)- and (Z)-6-nonen-2-one: Biosynthetic precursors ofEndo- andexo-brevicomin in two bark beetles (Coleoptera: Scolytidae)

The ability of (E)- and (Z)-6-nonen-2-one to serve as precursors of the common scolytid pheromonesEndo- andexo-brevicomin was examined in vivo. When mountain pine beetles (MPB),Dendroctonus ponderosae Hopkins, or western balsam bark beetles (WBBB),Dryocoetes confusus Swaine, were exposed to [6,7-D₂](E)-6-nonen-2-one, theEndo-brevicomin produced was enriched with two deuterium atoms per molecule (as determined by GC-MS), indicating that (E)-6-nonen-2-one served as a precursor of this pheromone. Similarly, when the beetles were exposed to [4,4-D₂](Z)-6-nonen-2-one, theexo-brevicomin produced was enriched with two deuterium atoms per molecule. Evidence in support of biological relevance of the latter observation include: (1) (Z)-6-nonen-2-one was found in the volatiles of male MPBs and WBBBs, indicating that this is a natural metabolite; (2) theexo-brevicomin produced by MPB was shown to be of natural (+) chirality by complexation chromatography; and (3) female WBBBs and MPBs (which are not known to produceexo-brevicomin) produced significantly lessexo-brevicomin when exposed to the precursor than did the males.     

Pheromonal secretions from glands on the 5th abdominal sternite of hydropsychid and rhyacophilid caddisflies (Trichoptera)

Extracts of different body parts of adult Trichoptera were tested for electrophysiological activity. Extracts of the IVth and Vth abdominal sternites of femaleHydropsyche angustipennis, Rhyacophila nubila, andR. fasciata, containing a paired exocrine gland, elicited significant electroan-tennographic responses when tested on conspecific male antennae. The paired gland occurs also in males of all the species, and inH. angustipennis, extracts from males were more active than female extracts when tested on male antennae. Female and male extracts from all species were analyzed by gas chromatography with simultaneous flame ionization and electroantennographic detection (EAD). EAD-active peaks in female extracts, stimulating male antennae, were identified inH. angustipennis as nonan-2-one; and inR. nubila andR. fasciata as heptan-2-one, heptan-2-ol, nonan-2-one, and nonan-2-ol. EAD-active components from maleH. angustipennis stimulating male antennae were octan-2-one, nonan-2-one (major peak), (Z)-6-nonen-2-one, decan-2-one, and a methylbranched decan-2-one. Female extracts and synthetic mixtures of compounds identified from femaleH. angustipennis andR. fasciata were tested for attractivity in the field. High catches with control traps obscured the results, but a synthetic mixture of the four identified compounds was significantly attractive and not different from female extracts for attracting maleR. fasciata. InH. angustipennis, a synthetic six-component male blend, in which nonan-2-one was the major component, attracted significant numbers of male and femaleH. angustipennis. Extracts of maleR. nubila andR. fasciata contained acetophenone and hexanoic and octanoic acids but did not have any electrophysiological or behavioral activity on either male or female antennae of conspecifics. The occurrence of a female sex pheromone inRhyacophila and an aggregation pheromone inHydropsyche corresponds to earlier described differences in mating behaviors in the Rhyacophilidae and Hydropsychidae.     

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.     

(6Z,9Z-3R,4S)-Epoxy-heptadecadiene: major sex pheromone component of the larch looper,Semiothisa sexmaculata (Packard) (Lepidoptera: Geometridae)

Gas chromatographic-electroantennographic analysis (GC-EAD) of female larch looper,Semiothisa sexmaculata (Packard), gland extracts revealed two EAD-active compounds. Retention index calculations, GC-mass spectroscopy in selected ion monitoring mode, and GC-EAD analysis of authentic standards identified the compounds as (3Z,6Z,9Z)-heptadecatriene (3Z,6Z,9Z-17H) and (6Z,9Z)-cis-3,4-epoxy-heptadecadiene (6Z,9Z-cis-3,4-epoxy-17H). Chirality determination of the monoepoxydiene in gland extracts was impeded by small quantities, but field experiments indicated that maleS. sexmaculata were most strongly attracted to enantiomerically enriched 6Z,9Z-3R,4S-epoxy-17H (69% ee), while maleS. neptaria (Guenée) responded well to various blends of theR,S- and S,R-epoxide enantiomers. Binary combinations of theR,S-epoxide enantiomer with 3Z,6Z,9Z-17H significantly inhibited response by maleS. sexmaculata, but strongly enhanced attraction of sympatric maleS. marmorata Ferguson. Enantiomerically enriched 6Z,9Z-3R,4S-epoxy-17H can be used as a trap bait to monitor populations of the larch-defoliatingS. sexmaculata. Whether 6Z,9Z-3R,4S-epoxy-17H serves as single component sex pheromone inS. sexmaculata or small amounts of 6Z,9Z-3S,4R-epoxy-17H synergize or suppress optimal attraction, will be tested as chirally pure monoepoxydienes become available.     

A sex attractant for the scarab beetle Anomala solida Er

(R,Z)-5-(-)-(Oct-1-enyl)oxacyclopentan-2-one (R-buibuilactone) attracted male Anomala solida Er. (Coleoptera: Scarabaeidae, Rutelinae), a vineyard and orchard pest in Southeastern Europe. The presence of the corresponding (S) enantiomer or of 2-(E)-nonen-1-ol (a frequently found pheromone component in other Anomala spp.) in the bait did not influence catches. Traps baited with (R,Z)-5-(-)-(oct-1-enyl)oxacyclopentan-2-one were successfully used for monitoring the flight of A. solida, and may have practical applications for detection, monitoring, and mass trapping of the pest.     

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.     

(3Z,6Z,9Z)-Nonadecatriene and enantiomers of (3Z,9Z)-cis-6,7-Epoxy-nonadecadiene as sex attractants for two geometrid and one noctuid moth species

Sex attractants for the geometrid mothsEufidonia convergaria andCaripeta angustiorata, and the noctuid mothRivula propinqualis have been elucidated during field screening of a series of (3Z,6Z,9Z)-triene hydrocarbons (C_17–22), and the racemic and enantiomerically enriched monoepoxydienes derived from those hydrocarbons. Biologically active compounds were identified by a combination of field testing of synthetic standards, electroantennography, and coupled gas chromatography-electroantennogram detection.E. convergaria males were optimally attracted by a 11 blend of (3Z,9Z)-(6S,7R)-epoxy-nonadecadiene (3Z,9Z-6S,7R-epoxy-19H); other abbreviations follow the same system) with (3Z,6Z,9Z)-nonadecatriene (3Z,6Z,9Z-19H). The 6R,7S enantiomer of the epoxide had no apparent biological activity, either as an attractant or as a behavioral antagonist. Male moths also were attracted to blends of the C₁₈ and C₂₀ homologs of the triene and the epoxide. 3Z,6Z,9Z-19H and 3Z,6Z-cis-6,7-epoxy-19H were identified inE. convergaria female pheromone gland extracts. Males of the geometrid moth speciesC. angustiorata were attracted by a 11 blend of 3Z,6Z,9Z-19H and enantiomerically enriched 3Z,9Z-6R,7S-epoxy-19H. Males of the noctuid mothR. propinqualis were attracted by an approximately 101 blend of 3Z,6Z,9Z-19H and enantiomerically enriched 3Z,9Z-6S, 7R-epoxy-19H. The components were synergistic, with neither being attractive alone. The blend ratio was quite specific, as the attractiveness of blends decreased sharply on either side of the optimum ratio.Issued as NRC No. 30266.     

Species discrimination in five species of winter-flying geometrids (Lepidoptera) based on chirality of semiochemicals and flight season

Enantiomer separation of (6Z,9Z)-cis-3,4-epoxynonadecadiene and (3Z,9Z)-cis-6,7-epoxynonadecadiene could be achieved using chiral high-resolution gas chromatography and a cyclodextrin-bond column. (3Z,9Z)-(6R,7S)-Epoxynonadecadiene was identified from ovipositor extracts ofColotois pen-Naria, while inErannis defoliaria the 6S,7R-enantiomer was found. In field trapping tests pure synthetic enantiomers caught only conspecific males of these species. (3Z,6Z,9Z)-Nonadecatriene was found in both species, while the presence of (3Z,6Z,9Z)-heneicosatriene was indicated inC. Pennaria only. A 10103 blend of (3Z,9Z)-(6R,7S)-epoxynonadecadiene, (3Z,6Z,9Z)-heneicosatriene, and (3Z,6Z,9Z)-nonadecatriene was found to be optimal for catchingC. Pennaria, whileE. Defoliaria males were optimally caught by a 11 mixture of (3Z,9Z)-(6S,7R)-epoxynonadecadiene and (3Z,6Z,9Z)-nona-decatriene. (6Z,9Z)-(3S,4R)-Epoxynonadecadiene was identified from ovipositor extracts ofAgriopis (Erannis) aurantiaria. In field tests the pure enantiomer proved to be a highly specific sex attractant for both the late autumn/early winter flyingA. Aurantiaria and the late winter/early spring flyingA. Leucophearia. Males ofAgriopis marginaria, which fly in late winter/early spring, were attracted to (3Z,9Z)-(6S,7R)-epoxynonadecadiene. The addition of (3Z,6Z,9Z)-nonadecatriene to theS,R-enantiomer increased captures. Optimal catches were recorded with a 103 epoxide-hydrocarbon blend. Enantiomer specificity in all species was confirmed in EAG measurements.     

Biological activity of (3R,5S,6R)- and (3S,5R,6S)-3,5-dimethyl-6-(methylethyl)-3,4,5,6-tetrahydropyran-2-one,a pheromone ofMacrocentrus grandii (Goidanich) (Hymenoptera: Braconidae)

In a previous study we reported identification of (3R*,5S*,6R*)-3,5-dimethyl-6-(methylethyl)-3,4,5,6-tetrahydropyran-2-one as a component of the pheromone ofMacrocentrus grandii Goidanich. The lactone was present in male and female wasps, and laboratory and field bioassays demonstrated that both sources of the lactone elicit flight initiation, upwind anemotaxis, and casting in male wasps. In the present study, the synthetic (3R,5S,6R)- and (3S,5R,6S)-lactone enantiomers (RSR andSRS, respectively) were bioassayed for biological activity. In wind tunnel studies theSRS enantiomer elicited flight initiation, upwind anemotaxis, and casting by male wasps comparable to lactone derived from male and female wasps. Flight response to theRSR enantiomer averaged 14 percent of theSRS enantiomer. No specific ratio of the stereoisomers was found more attractive than theSRS enantiomer alone. Field studies demonstrated theSRS enantiomer was active alone in attracting male wasps. When paired with (Z)-4-tridecenal (a previously identified female-derived sex pheromone), theSRS enantiomer yielded a synergistic response comparable to (Z)-4-tridecenal plus female-derived lactone.     

(2S,12Z)-2-Acetoxy-12-heptadecene: Major Sex Pheromone Component of Pistachio Twig Borer, Kermania pistaciella

The sex pheromone of the pistachio twig borer, Kermania pistaciella (Lepidoptera: Oinophilidae), one of the most important insect pests of pistachio, Pistacia vera, in Turkey and Iran, was identified. In gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometric analyses of pheromone gland extracts of female K. pistaciella from Turkey, (2S,12Z)-2-acetoxy-12-heptadecene was identified as the major candidate pheromone component. In field experiments in Turkey, lures containing synthetic (2S,12Z)-2-acetoxy-12-heptadecene attracted large numbers of male moths. Its attractiveness was significantly reduced by the presence of the R-enantiomer or of either enantiomer of the corresponding alcohol. (2S,12Z)-2-Acetoxy-12-heptadecene is the first pheromone component identified in the Oinophilidae and the first secondary acetate pheromone component identified in the Lepidoptera. An erratum to this article can be found at     

Study of female sex pheromone of leopard moth,Zeuzera pyrina L. Isolation and identification of three components

Three compounds have been identified in the abdominal tip extracts from the female leopard moth,Zeuzera pyrina L. Gas-liquid chromatography and mass spectroscopy data showed that (E, Z)-2, 13-octadecadien-1-ol acetate was the main component and that (Z)-13-octadecen-1-ol acetate and octadecan-1-ol acetate were secondary components. The electroanten-nographic responses of maleZ. pyrina to nanogram amounts of all four 2, 13-octadecadien-1-ol acetate isomers indicated that theE, Z isomer had the maximum activity. A strong EAG response was also recorded for (Z)-7-do-decen-1-ol acetate, which was not detected in the female extracts.     

Pheromone chirality of african palm weevil,Rhynchophorus phoenicis (F.) and palmetto weevil,Rhynchophorus cruentatus (F.) (Coleoptera: Curculionidae)

There are four stereoisomers of both 3-methyl-octan-4-ol, the aggregation pheromone of the African palm weevil,Rhynchophorus phoenicis (F.) and 5-methyl-octan-4-ol, the aggregation pheromone of the palmetto weevil,Rhynchophorus cruentatus (F.). Synthetic stereoisomers of 3-methyl-octan-4-ol and 5-methyl-octan-4-ol were baseline-separated on a Cyclodex-B fused silica column. Use of this column in gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometric (GC-MS) analyses revealed that only one stereoisomer, (3S,4S)-3-methyl-octan-4-ol and (4S,5S)-5-methyl-octan-4-ol, is produced by maleR. phoenicis and maleR. cruentatus, respectively, and elicits good antennal responses by conspecific male and female weevils. In field trapping experiments, withR. phoenicis in Côte d'Ivoire andR. cruentatus in Florida, (3S,4S)-3-methyl-octan-4-ol and (4S,5S)-5-methyl-octan-4-ol strongly enhanced attraction of fresh palm tissue, whereas other stereoisomers were behaviorally benign. Stereoisomeric 3-methyl-octan-4-ol and 5-methyl-octan-4-ol may be utilized to monitor and/or manage populations of these two palm weevils.     

(Z,Z)-6,9-heneicosadien-11-one,labile sex pheromone of the whitemarked tussock moth,Orgyia leucostigma

The whitemarked tussock moth (WMTM), Orgyia leucostigma (J. E. Smith), is a major pest of coniferous and deciduous trees in eastern Canada. Chemical identification of its sex pheromone depended primarily on GC-EAD and HPLC analysis, with confirmation of behavioral activity by wind tunnel and field tests. We identified (Z,Z)-6,9-heneicosadien-11-one (Z,Z-6,9-ket) at 4–5 ng/female as the only essential sex pheromone component. Also detected in female extracts were (Z)-6-heneicosen-11-one (Z6-ket) at 2.5 ng/female, (Z,E)-6,8-heneicosadien-11-one (Z,E-6,8-ket) at about 0.5 ng/female, and a trace amount of (Z,E)-6,9-heneicosadien-11-one. Traps containing as little as 1 g of Z,Z-6,9-ket attracted males at low population levels, indicating it is a potent sex attractant. Traps baited with Z6-ket attracted few males, and in wind-tunnel bioassays it was at least 100-fold less attractive to males than Z,Z-6,9-ket. No improvement in trap catch occurred with the addition of Z6-ket in various binary mixtures with Z,Z-6,9-ket, including the female ratio, and a ternary mixture of Z,Z-6,9-ket, Z6-ket, and Z,E-6,8-ket in the 9:5:1 ratio detected in females was no better than Z,Z-6,9-ket alone. We attribute the presence of Z,E-6,8-ket and Z,E-6,9-ket in female extracts to the spontaneous and rapid stereospecific isomerization of Z,Z-6,9-ket at room temperature. Male flight began at sunset but peaked during the second half of the night.     

Identification of the white peach scale sex pheromone

Micro techniques were used to obtain spectroscopic and degradative information from less than 5g of the sex attractant of female white peach scale,Pseudaulascaspis pentagons (Targioni-Tozzetti) isolated from airborne collections. The pheromone was identified as (Z)-3,9-dimethyl-6-isopropenyl-3,9-decadien-1-ol propionate. Both enantiomers of theZ isomer and also the enantiomers of theE isomer were prepared from (R)-or (S)-limonene. Bioassays of material with minimum enantiomeric purity of 95% showed that at extreme dilution only theR,Z isomer attracted male white peach scale; however activity of theS,Z enantiomer could not be completely excluded.Mention of a commercial or proprietary product in this paper does not constitute an endorsement of that product by the USDA.     

Chirality of israeli pine bast scale,Matsucoccus josephi (homoptera: Matsucoccidae) sex pheromone

The absolute configuration of the sex pheromone of the Israeli pine bast scale,Matsucoccus josephi, was determined as (2E,5R,6E,8E)-5,7-dimethyl-2,6,8-decatrien-4-one, designated here asR-E with 10% (2E,5S,6E,8E)-5,7-dimethyl-2,6,8-decatrien-4-one, designated asS-E. The chirality of the quantitatively minorZ isomer was (2E,5R,6Z,8E)-5,7-dimethyl-2,6,8-decatrien-4-one (R-Z). Chiral assignments were made by comparative gas chromatographic (GC) analysis of naturalM. josephi pheromone with stereoselectively synthesized stereoisomers on a chiral Cyclodex-B column, which separated the enantiomers with baseline resolution. In gas chromatographic-electroantennographic detection (GC-EAD) analysis of the racemicZ andE isomers, the latter elicited the stronger antennal response by maleM. josephi. In GC-EAD of all four stereoisomers, employing the chiral column,R-E was the most active stereoisomer. In field testsR-E attracted 10 times more males ofM. josephi than didS-E. The racemicE/Z pheromone mixture, containing all four stereoisomers in approximately equal amounts, attracted as many maleM. josephi as did an equivalent amount ofR-E, indicating that the other stereoisomers are not inhibitory. The same keto-diene moiety with the same chiral center and configuration in all three known Matsucoccidae sex pheromones implies a common biosynthetic pathway and phylogenetic relationship.Contribution from the Agricultural Research Organization, the Volcani Center, No. 1496-E, 1994 series.Part of the work was performed during a sabbatical leave of E.D. at Simon Fraser University.     

Identification of a sex pheromone component of the geometrid moth <Emphasis Type="Italic">Milionia basalis pryeri</Emphasis>

A single component in extracts of virgin female Milionia basalis pryeri moths elicited responses from male moth antennae. This compound (ca. 7 ng/female) was identified as (Z,Z)-(3S,4R)-3,4-epoxynonadeca-6,9-diene by GC-MS and NMR analyses, microchemical reactions, and comparative chiral HPLC. In a field test, synthetic (Z,Z)-(3S,4R)-3,4-epoxynonadeca-6,9-diene attracted male moths.The opposite enantiomer, the racemic mixture, and virgin female moths held in small cages attracted no more moths than the solvent controls.     

Moth Scale-Derived Kairomones Used by Egg–Larval Parasitoid Ascogaster quadridentata to Locate Eggs of Its Host, Cydia pomonella

We determined that location of host (Cydia pomonella) eggs by Ascogaster quadridentata is mediated by kairomones, investigated potential sources of the kairomones and identified a blend of kairomones from the source that was attractive to A. quadridentata. In Y-tube olfactometer bioassays, female A. quadridentata were attracted to Porapak Q-collected volatiles from female C. pomonella scales and eggs, but not to C. pomonella sex pheromone. Scales of C. pomonella were also attractive to male A. quadridentata. Coupled gas chromatographic–electroantennographic detection analysis of scale volatile extracts revealed numerous compounds that elicited responses from male or female A. quadridentata antennae, including heptanal, octanal, nonanal, decanal, undecan-2-one, dodecanal, pentadecan-2-one, (Z)-6-pentadecen-2-one, (Z)-9-hexadecenal, (Z)-6-heptadecen-2-one, and 3,7,11-trimethyl-2E,6E,10-dodecatrien-1-ol acetate. A synthetic blend of these compounds at quantities and ratios equivalent to Porapak Q scale volatile extract was attractive to female A. quadridentata in a Y-tube olfactometer bioassay.     

(<Emphasis Type="Italic">Z,Z</Emphasis>)-6,9-Heneicosadien-11-One: Major Sex Pheromone Component Of Painted Apple Moth, <Emphasis Type="Italic">Teia anartoides</Emphasis>

(Z, Z)-6,9-Heneicosadien-11-one (Z6Z9-11-one-21Hy) was identified as the major sex pheromone component of the painted apple moth (PAM), Teia anartoides (Lepidoptera: Lymantriidae), on the basis of (1) comparative gas chromatographic-electroantennographic detection (GC-EAD) analyses, GC-mass spectrometry (MS), high-performance liquid chromatography (HPLC)-MS, and HPLC-UV/visible spectroscopy of pheromone gland extracts and authentic standards; (2) GC-EAD analyses of effluvia of calling females; and (3) wind tunnel and field trapping experiments with a synthetic standard. In field experiments in Australia, synthetic Z6Z9-11-one-21Hy as a single component attracted male moths. Wind tunnel experiments suggested that a 4-component blend consisting of Z6Z9-11-one-21Hy, (6Z,9R,10S)-cis-9,10-epoxy-heneicosene (Z6-9R10S-epo-21Hy), (E, E)-7,9-heneicosadien-6,11-dione (E7E9-6,11-dione-21Hy), and 6-hydroxy-(E, E)-7,9-heneicosadien-11-one (E7E9-6-ol-11-one-21Hy) (all present in pheromone gland extracts) might induce more males to orient toward, approach, and contact the source than did Z6Z9-11-one-21Hy as a single component. Additional experiments are needed to determine conclusively whether or not Z6-9R10S-epo-21Hy, E7E9-6,11-dione-21Hy, and E7E9-6-ol-11-one-21Hy might be minor sex pheromone components of PAM. Moreover, attractiveness of synthetic pheromone and virgin PAM females needs to be compared to determine whether synthetic pheromone could replace PAM females as trap baits in the program to monitor eradication of exotic PAM in New Zealand.     

Novel type of sex pheromone structure identified fromStigmella malella (Stainton) (Lepidoptera: Nepticulidae)

Short-chain unsaturated chiral methyl carbinols are identified as a new class of lepidopteran pheromone components. The natural female-produced pheromone of the banded apple pigmyStigmella malella (=Nepticula malella) (Stainton) (Lepidoptera: Nepticulidae) was identified to be a mixture of (S)-(E)-6,8-nonadien-2-ol and (S)-(Z)-6,8-nonadien-2-ol. For monitoring traps, a 10:3E:Z blend at 100–1000 µg is recommended. It is suggested that pheromones with similar structures may be specific to Nepticulidae and other related microlepidopteran families.