(3R*,5S*,6R*)-3,5-dimethyl-6-(methylethyl)-3,4,5,6-tetrahydropyran-2-one,a third sex pheromone component forMacrocentrus grandii (goidanich) (Hymenoptera: Braconidae) and evidence for its utility at eclosion

The compound (3R^*,5S^*,6R^*)-3,5-dimethyl-6-(methylethyl)-3, 4,5,6-tetrahydropyran-2-one was identified as a sex pheromone component ofM. grandii. Laboratory and field bioassays demonstrated that it elicits flight initiation, upwind anemotaxis, and casting in male wasps. The compound acts synergistically with (Z)-4-tridecenal, a previously identified sex pheromone component of femaleM. grandii, to increase male response to the aldehyde component. The source of the lactone was determined to be the mandibular glands of male and female wasps. At eclosion a majority of male-female and female-only cocoon masses released the lactone and attracted male wasps. Male-only cocoon masses were not attractive at eclosion and the lactone component was either not released or released at below-threshold concentration. Mating was observed to occur following eclosion in laboratory and field studies.     

(Z)-4-Tridecenal,a pheromonally active air oxidation product from a series of (Z,Z)-9,13 dienes inMacrocentrus grandii Goidanich (Hymenoptera: Braconidae)

(Z)-4-Tridecenal was identified as a sex pheromone component ofMacrocentrus grandii, a larval parasitoid of the European corn borer. The aldehyde was found to be a common air oxidation product from a series of (Z,Z)-9,13-dienes of 27–33, 35, 37, 39, and 41 carbon atoms in female wasps. Synthetic (Z)-4-tridecenal and (Z,Z)-9,13-heptacosdiene each elicited flight initiation, upwind anemotaxis, casting, landing on the source, walking, wing fanning, and copulatory attempts by male wasps in a wind-tunnel. Field studies demonstrated that both compounds are synergized by a more polar component. Synthetic (E)-4-tridecenal was not attractive.     

Absolute configuration of sex pheromone for tea tussock moth,Euproctis pseudoconspersa (strand)via synthesis of (R)- and (S)-10, 14-dimethyl-1-pentadecyl isobutyrates

(R)- and (S)-10,14-dimethyl-1-pentadecyl isobutyrates were synthesized from (S)- and (R)-citronellols, respectively. TheR enantiomer was as active as the natural pheromone but theS enantiomer was less active in the electrophysiological analyses, which provided conclusive proof that the absolute configuration of the natural pheromone isR.     

(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.     

(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     

Pheromone specificity inEriocrania semipurpurella (Stephens) andE. sangii (Wood) (Lepidoptera: Eriocraniidae) based on chirality of semiochemicals

The fifth abdominal segment of femaleEriocrania semipurpurella (Stephens) andE. sangii (Wood) contains a pair of exocrine glands. Hexane extracts of this segment were prepared from both species and analyzed by gas chromatography with simultaneous flame ionization and electroantennographic detection (EAD). For both species, the EAD active peaks were identified as nonan-2-one, (Z)-6-nonen-2-one, and (Z)-6-nonen-2-ol by means of mass spectrometry and comparison of retention indices with those of synthetic standards. Enantiomeric separation of chiral alcohols from the female extracts was achieved by gas chromatographic analysis on a cyclodextrin column. InE. semipurpurella, a mixture of (2S,6Z)-nonen-2-ol and (2R,6Z)-nonen-2-ol (2: I) was found, whereas inE. sangii (2S,6Z)-nonen-2-ol was the predominant enantiomer and only traces of theR enantiomer were indicated by the antennal response. In field tests, a blend of the three compounds was not attractive to conspecific males. A subtractive assay showed that the alcohol in various enantiomeric mixtures was the only attractive compound, whereas addition of (Z)-6-nonen-2-one to the alcohol completely inhibited the attraction of both species. A trapping experiment including a wide range of ratios between theR andS enantiomers showed that baits containing 95–100% of theS enantiomer were attractive to maleE. sangii, whereas males ofE. semipurpurella were attracted to all tested ratios of the enantiomers. However, the response profiles of maleE. semipurpurella differed between populations from southern Sweden, south Finland, and the Kola Peninsula in Russia. In south Sweden males were maximally attracted to a racemic mixture of the alcohols. At the Kola PeninsulaE. semipurpurella was attracted to baits containing 95–100% of theR enantiomer. In south Finland all tested ratios between 0 and 100%R enantiomer trappedE. semipurpurella, but the trap catches appeared to be bimodally distributed with peaks around 15 and 70%R enantiomer. The trapping results suggest the existence of pheromone races or sibling species among the specimens identified asE. semipurpurella.Dedicated to Prof. H. J. Bestmann on the occasion of his 70th birthday.     

Identification,synthesis, and bioactivity of a male-produced aggregation pheromone in assassin bug,Pristhesancus Plagipennis (Hemiptera: Reduviidae)

Pristhesancus plagipennis, a large Australian assassin bug, possesses three pairs of dorsal abdominal glands (DAGs). In the male, the anterior and posterior glands are hypertrophied and secrete an attractant pheromone. Gas chromatography-mass spectrometry (GC-MS) analyses of male DAG extracts and airborne volatiles emitted from calling males showed the pheromone signature to be dominated by a novel component. Subsequent chemical manipulations, GC-MS, and chiral-column analyses established its identity as (Z)-3-hexenyl (R)-2-hydroxy-3-methylbutyrate. Minor components included 3-methylbutanol, 2-phenylethanol, (Z)-3-hexenol, decanal, (E)-2-hexenoic acid, and three minor hexenyl esters. Bioactivity studies using laboratory olfactometers and outdoor flight cages demonstrated attraction by femaleP. plagipennis to calling males, heptane extracts of male posterior DAGs and a synthetic formulation of the (Z)R enantiomer of the major ester, alone or in combination with other components of male anterior and posterior DAGs. Males were also attracted to the major ester. The racemate andS enantiomer of the ester were not attractive. Contamination of the (Z)R enantiomer with 30–60% of theE isomer also made the compound nonattractive. This is the first report of an aggregation pheromone in the Reduviidae. The prospects for pheromonal manipulation ofP. plagipennis populations to enhance the value of this predator in horticultural ecosystems, are discussed.     

(Z,Z)-4,7-tridecadien-(S)-2-yl acetate: sex pheromone of Douglas-fir cone gall midge,Contarinia oregonensis

Our objectives were to identify and field test the sex pheromone of female Douglas-fir cone gall midge, Contarinia oregonensis (Diptera: Cecidomyiidae). Coupled gas chromatographic–electroantennographic detection (GC-EAD) analyses of pheromone extract revealed a single compound (A) that elicited responses from male antennae. Hydrogenation of pheromone extract, followed by renewed GC-EAD analysis, revealed a new EAD-active compound with chromatographic characteristics identical to those of tridecan-2-yl acetate on five fused silica columns (DB-5, DB-210, DB-23, SP-1000, and Cyclodex-B). Syntheses, chromatography, and retention index calculations of all possible tridecen-2-yl acetates suggested that the candidate pheromone A was a tridecadien-2-yl acetate with nonconjugated double bonds. Synthetic candidate pheromone component (Z,Z)-4,7-tridecadien-2-yl acetate (Z4Z7) cochromatographed with A on all analytical columns and elicited comparable antennal activity. In GC-EAD analyses that separated the enantiomers (Z,Z)-4,7-tridecadien-(S)-2-yl acetate (2S-Z4Z7) and (Z,Z)-4,7-tridecadien-(R)-2-yl acetate (2R-Z4Z7) with baseline resolution, only 2S-Z4Z7 as a component in a racemic standard or in pheromone extract elicited antennal responses. In Douglas-fir seed orchards, sticky traps baited with 2S-Z4Z7 captured male C. oregonensis, whereas 2R-Z4Z7 was behaviorally benign. Comparable catches of males in traps baited with racemic Z4Z7 (50 g) or virgin female C. oregonensis suggested that synthetic pheromone baits could be developed for monitoring C. oregonensis populations in commercial Douglas-fir seed orchards.     

Absolute configuration of mosquito oviposition attractant pheromone, 6-acetoxy-5-hexadecanolide

6-Acetoxy-5-hexadecanolide (Ia) in the oviposition attractant pheromone released from egg apical droplets of the mosquitoCulex pipiens fatigans Wied. is shown to be the (–)-(5R,6S)- enantiomer. Identification was by chromatography of the 6-trifluoroacetoxy derivatives of the natural pheromone and of the synthetic (–)-(5R,6S)- (Ib) and (+)-(5S,6R)- (IIb) enantiomers on a capillary column having a chiral stationary phase comprising a derivative of (1S,3S)-chrysanthemic acid. The synthetic (–)-(5R,6S)- enantiomer (Ia) attracted oviposition of four fold more mosquito egg rafts than the control (P < 0.01) whereas for the (5S,6R)- enantiomer (IIa) there was no statistically significant oviposition attraction.     

Enantiomers of (Z,Z)-6,9-Heneicosadien-11-OL: Sex Pheromone Components of Orgyia detrita

(6Z,9Z,11S)-6,9-Heneicosadien-11-ol (Z6Z9-11S-ol-C21) and (6Z,9Z,11R)-6,9-heneicosadien-11-ol (Z6Z9-11R-ol-C21) were identified as major sex pheromone components of female tussock moths, Orgyia detritaGuérin-Méneville (Lepidoptera: Lymantriidae), on the basis of (1) analyses of pheromone gland extracts of female O. detrita by coupled gas chromatographic-electroantennographic detection (GC-EAD) and GC mass spectrometry, and (2) field trapping experiments with synthetic standards. Z6Z9-11S-ol-C21 and Z6Z9-11R-ol-C21 in combination, but not singly, attracted significant numbers of male moths. Racemic Z6Z9-11-ol-C21 was more attractive than the 1:3.5 (R:S) blend ratio found in pheromone gland extracts from female moths. Lower and higher homologues of Z6Z9-11-ol-C21 were also detected in GC-EAD recordings of pheromone extracts, and the racemic compounds enhanced attractiveness of Z6Z9-11-ol-C21 in field experiments. Because of trace amounts of these homologues in extracts, their enantiomeric composition could not be determined. This is the first report of secondary alcohols as pheromone components in the ditrysian (advanced) Lepidoptera.     

Enzymes in organic synthesis. 27. Lipase-Catalyzed Synthesis of (5R,6S)-6-Acetoxyalkan-5-olides – homologues of the mosquito oviposition attractant pheromone

Sixteen homologous (5R*,6S*)-6-hydroxyalkan-5-olides rac- 5 and their acetoxy derivatives rac- 6 were synthesized from the corresponding methyl (Z)-alk-5-enoates 3 by osmium(VIII) oxide catalyzed cis-hydroxylation to the dihydroxy esters rac- 4 and hydrolysis of these esters followed by lactonization. Pancreatin-catalyzed lactonization of the dihydroxy esters rac- 4 afforded enantiomerically enriched hydroxy lactones ent- 5 , five of which were obtained enantiomerically pure by recrystallization. Acetylation of the 6-hydroxyalkan-5-olides rac- 5 by vinyl acetate catalyzed by the lipase SP 526 provided enantiomerically enriched 6-acetoxyalkan-5-olides 6 with an enantiomeric excess of more than 90% in nine cases. These compounds are known as mosquito oviposition attractant pheromone ( 6h ) or its homologues.     

Structure-activity studies on aggregation pheromone components ofPityogenes chalcographus (Coleoptera: Scolytidae)

Syntheses of all four Stereoisomers (2S,5S; 2S,5R;2R,5R; and2R,5S) of chalcogran, a major component of the aggregation pheromone ofPityogenes chalcographus, and of all four isomers (2Z,4Z; 2Z,4E; 2E,4E; and 2E,4Z) of methyl 2,4-decadienoate (MD), the second major pheromone component, are briefly described. Attraction responses of walking beetles of both sexes were tested to mixtures of the synergistic pheromone components or analogs. These bioassays showed that theE,Z isomer of MD is the most active when tested with chalcogran. When tested with (E,Z)-MD, (2S,5R)-chalcogran was the most active stereoisomer, while 2R,5R and 2R,5S isomers had intermediate activities, and the 2S,5S isomer was inactive. There was no evidence that the relatively less active Stereoisomers of chalcogran inhibited or promoted attraction to (2S,5R)-chalcogran with (E,Z)-MD. Male beetles only produce the activeE,Z isomer of MD (inactive alone) and their hindguts contain the most active (2S,5R)- and least active (2S,5S)-chalcogran. A mixture of all MD isomers with racemic chalcogran was not significantly different in attractivity compared to (E,Z)-MD with racemic chalcogran, indicating no synergistic or inhibitory effects of the inactive isomers of MD.     

Multicomponent sex pheromone inMacrocentrus grandii Goidanich (Hymenoptera: Braconidae)

A multicomponent sex pheromone inMacrocentms grandii Goidanich (Hymenoptera: Braconidae) was demonstrated using wind-tunnel and field bioassays. In wind-tunnel bioassays, three Florisii fractions from female wasps (hexane, 5%, and 50% ether in hexane) and one from male wasps (50% ether in hexane) were attractive to males. The hexane and 5% ether in hexane fractions each elicited similar male behavioral responses. These included upwind anemotaxis, casting, landing on the source, wing fanning, and mating attempts between males. The 50% ether in hexane fraction, whether male- or female-derived, initiated a strong flight response by males but few landings on the source. In addition, the 50% ether in hexane fraction was found to synergize strongly the hexane fraction. All females tested in the wind tunnel gave no responses to male- or female-derived extracts. Field tests generally supported the wind-tunnel results, although no field attraction was observed for the 5% ether in hexane fraction.     

(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.     

(Z)-11-Hexadecenal and (3Z,6Z,9Z)-tricosatriene: sex pheromone components of the red banded mango caterpillar Deanolis sublimbalis

The sex pheromone of the red banded mango caterpillar, Deanolis sublimbalis (Lepidoptera: Crambidae), a serious pest of the mango Mangifera indica (Anacardiaceae) in India and Southeast Asia and a recent invader into northern Australia, has been identified. Three candidate compounds were identified from pheromone gland extracts of female moths, using gas chromatography (GC), GC-electroantennographic detection and GC-mass spectrometric analyses, in conjunction with dimethyldisulfide derivatization. Field bioassays established that both (Z)-11-hexadecenal (Z11-16:Ald) and (3Z,6Z,9Z)-tricosatriene (3Z,6Z,9Z-23:Hy) were required for attraction of male D. sublimbalis moths, and 1,000 μg of a 1:1 mix of Z11-16:Ald and 3Z,6Z,9Z-23:Hy was more attractive to male moths than caged virgin females. However, the binary blend was only attractive when the isomeric purity of the monounsaturated aldehyde was >99%, suggesting that the (E)-isomer was inhibitory. Although (Z)-11-hexadecen-1-ol (Z11-16:OH) was tentatively identified in gland extracts, the addition of this compound to the binary blend did not increase the numbers of moths captured. The pheromone can now be used in integrated pest management strategies. Electronic Supplementary Material Supplementary material is available for this article at and is accessible for authorized users.     

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.     

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.     

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.     

Sex-specific activity of (R)-(−)- and (S)- (+)-1,7-dioxaspiro[5.5]undecane,the major pheromone ofDacus oleae

1,7-Dioxaspiro[5.5]undecane (olean), the major component of the female sex attractant pheromone blend of the olive fruit flyDacus oleae (Gmelin) was shown to be released as a racemate. The response of males and females to pure (R)-(–) and (S)-(+)-enantiomers was tested under laboratory and field conditions. Males in laboratory and field tests responded only to (R)-(–)-olean, which functions as a sex attractant. Females responded only to (S)-(+)-olean in laboratory tests but not in the field. There are indications that the latter enantiomer fuctions as a short-range arrestant throughout the day and as an aphrodisiac in the process of mating.Diptera: Tephritidae.     

(<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.