Parthenogenesis,calling behavior,and insect-released volatiles of leafminer moth Phyllonorycter emberizaepenella

We proved that the leafminer moth Phyllonorycter emberizaepenella (Lepidoptera: Gracillariidae) reproduces by parthenogenesis of the thelytoky type. Despite a complete absence of males, parthenogenetically reproducing females diurnally demonstrated the calling posture normally used for releasing signaling compounds. Two compounds, which we collected from a calling female, were identified as potential sex pheromone components: (8E,10E)-8,10-tetradecadienyl acetate and (8E,10E)-8,10-tetradecadienol, the latter occurring only in trace amounts. In field experiments, no males were attracted to traps baited with either the potential sex pheromone or with virgin females. Both the pattern of behavior and the chemical characteristics of the pheromone of Ph. emberizaepenella species were similar to those known for Lepidoptera with the usual amphimictic mode of reproduction. Theoretical speculations that in thelytoky, where there is no need to find a sexual partner, the individuals would obtain certain advantages due to reduction in their sexual behavior, were, thus, not confirmed for Ph. emberizaepenella.     

Sex pheromone of tomato fruit borer, Neoleucinodes elegantalis

Five candidate pheromone components were identified by analyzing pheromone gland extracts by gas chromatography (GC), coupled GC-electroantennographic detection (EAD), and coupled GC-mass spectrometry (MS): (E)-11-hexadecenol(E11–16 : OH), (Z)-11-hexadecenol (Z11–16 : OH),(E)-11-hexadecenal, (E)-11-hexadecenyl acetate, and (Z)-3,(Z)-6,(Z)-9-tricosatriene (Z3,Z6,Z9–23 : Hy). In electroantennogram (EAG) recordings, synthetic E11–16 : OH elicited stronger antennal responses at low doses than other candidate pheromone components. Field tests demonstrated that synthetic E11–16 : OH as a trap bait was effective in attracting males, whereas addition of Z11–16 : OH inhibited the males' response. Z3,Z6,Z9–23 : Hy strongly enhanced attractiveness of E11–16 : OH, but was not attractive by itself. A pheromone blend with synergistic behavioral activity of an alcohol (E11–16 : OH) and hydrocarbon (Z3,Z6,Z9–23 : Hy) component is most unusual in the Lepidoptera. The synthetic two-component pheromone is approximately 60 times more attractive than the female-produced blend and might facilitate the control of this pest.     

Sex pheromone of the chokecherry leafroller moth,Sparganothis directana

(E)-9,11-Dodecadienyl acetate and (Z)-9,11-dodecadienyl acetate in conjunction with (E)-11-tetradecenyl acetate and (Z)-11-tetradecenyl acetate were found to comprise the sex pheromone ofSparganothis directana, based on chemical analysis, electroantennogram tests, and field trapping. (E)-9-Dodecenyl acetate and (Z)-9-dodecenyl acetate were also found in gland extracts but did not influence trap catches. The relative amounts of these compounds in the gland were 3521928 106, in the order named. Only (E)-9,1 1-dodecadienyl acetate, (E)-11-tetradecenyl acetate, and (Z)-11-tetradecenyl acetate were required for attraction of males to traps, dispensed in the relative amounts 501238, respectively.Lepidoptera: Tortricidae.Supported by National Science Foundation grant PCM 78-13241.     

Sex Attractant Pheromone of Saturniid Moth Coloradia velda

The female-produced sex attractant pheromone of Coloradia velda has been identified by a combination of analytical methods and field tests as a blend of (10E,12Z)-hexadecadien-1-yl acetate (10E,12Z–16:Ac), (10E,12E)-hexadecadien-1-yl acetate (10E,12E–16:Ac), and (10E,12Z)-hexadecadien-1-ol (10E,12Z–16:OH) in a 10:1:0.33 ratio, respectively. The corresponding aldehyde (10E,12Z–16:Ald) was also found in extracts of female pheromone glands, but in blends with 10E,12Z–16:Ac and 10E,12E–16:Ac at low doses did not significantly increase the attractiveness of baits to male moths.     

Sex pheromone of European corn borer.

Sex gland extracts ofOstrinia nubilalis females collected in the wild or laboratory-reared from Switzerland, Italy, and Hungary were analyzed. Individuals collected in the north of Switzerland contained (Z)- and (E)-11-tetradecenyl acetate at the approximate ratio of 973 (Z type), in accordance with field responses of males and previous findings. On the other hand, females from a laboratory culture derived from field collections made in the same area and reared for four to five generations contained theZ andE isomers at ratios of ca. 397 and 3565, respectively. In the south, one of the eight wild females analyzed was of theZ type and the rest intermediate, whereas males were predominantly trapped with blends of the two isomers containing 60 to 97E. In a laboratory culture reared for one to two generations from corn borers collected in Hungary, three of nine females were of the intermediate type and the restZ. Small amounts of (Z)-11-hexadecenyl acetate were detected in female glands of theE strain; however, no effect of this compound could be observed in the field.     

Sex pheromone components of the oblique-banded leafroller,Choristoneura rosaceana in the Okanagan Valley of British Columbia

(Z)-11-Tetradecen-1-yl acetate, (E)-11-tetradecen-1-yl acetate, and (Z)-11-tetradecen-1-ol were previously reported as the sex pheromone in New York strains of the oblique-banded leafroller,Choristoneura rosaceana (Harris), and (E)-11-tetradecen-1-ol was tentatively identified in female tip extracts. For Okanagan Valley strains ofC. rosaceana, an additional component, (Z)-11-tetradecenal, was identified from female tip extracts by split-less capillary gas-liquid chromatography and mass spectroscopy and was strongly stimulatory in electroantennogram studies. In field tests, 3 mg of 96.521.5 (Z)-11-tetradecen-1-yl acetate, (E)-11-tetradecen-1-yl acetate, and (Z)-11-tetradecen-1-ol (containing approx. 1%E isomer) was not as attractive as female-baited traps, and significant numbers of European leafrollerArchips rosanus L. were attracted. The above blend with 1% (Z)-11-tetradecenal added was significantly more attractive than traps baited with femaleC. rosaceana, butA. rosanus males were still attracted. Increased percentages of (Z)-11-tetradecenal up to 4% caused increased catches ofC. rosaceana and decreased catches ofA. rosanus. Low amounts of (E)-11-tetradecen-1-ol and (E)-11-tetradecenal male also contribute to increased specificity of the synthetic pheromone blend toC. rosaceana.Lepidoptera: Tortricidae.Contribution No. 638, Agriculture Canada, Research Station, Summerland, British Columbia, Canada.     

Sex pheromone of hickory shuckwormCydia caryana Development of an effective field Lure

Extracts of the sex pheromone glands of femaleCydia caryana were evaluated by electroantennography and gas chromatography-mass spectrometry. These studies suggested the following compounds were potential sex pheromone components: (Z)-8- and/or (E)-9-dodecenyl acetate (50 pg/female), dodecyl acetate (40 pg/female), and (E, E)-8,10-dodecadienyl acetate (25 pg/female). In field tests only the diene produced trap catch, and when the other components were added to the diene, trap catch was not increased. When the diene was formulated in red natural rubber septa, only transient and low catches were obtained, but when gray halobutyl isoprene elastomeric septa were used, high and consistent catches were obtained for eight weeks. Catches depended on the ratio of (E, E)-8,10 to (E, Z)-8,10 isomers. High catches were obtained for anEE toEZ ratio of 100 0.6, and insignificant catches were obtained when the ratio was 100 3. Equivalent catches were obtained for dosages of 50, 100, and 200 g/septum.     

Sex pheromone of the woodbine leafroller moth,Sparganothis sp.

The sex pheromone of the woodbine leafroller,Sparganothis sp., includes (E)-11-tetradecen-1-ol, (Z)-11-tetradecen-1-ol, and (E)-11-tetradecen-1-yl acetate, based on chemical analysis of gland extracts, electroantennogram tests, and field trapping. Highest trap catches were obtained when these compounds were dispensed in the relative proportions observed in the female gland. (Z)-11-Tetradecen-1-yl acetate also was found in gland extracts, but significantly reduced trap catches. The saturated compounds tetradecan-1-ol and tetradecan-1-yl acetate were found in gland extracts as well, but were not tested. The amounts of these compounds per female gland were 127, 93, 17, 20, 25, and 3 ng, in the order named.Lepidoptera: Tortricidae.Supported by National Science Foundation Grant PCM 78-13241.     

Sex pheromone components of the buck moth Hemileuca maia

The sex attractant pheromone blend of Hemileuca maia (Lepidoptera: Saturniidae) from the vicinity of Baton Rouge, Louisiana, has been identified. The major component of the blend is (E10,Z12)-hexadeca-10,12-dienal (E10,Z12–16:Ald), in combination with the minor components (E10,Z12)-hexadeca-10,12-dien-1-ol (E10,Z12–16:OH), and (E10,Z12)-hexadeca-10,12-dien-1-yl acetate (E10,Z12–16:Ac). Ratios of the compounds in extracts of female pheromone glands varied around a mean of 100:7.4:6.3. None of the three components were attractive to male moths when tested as single components. Several other compounds were tentatively identified from female pheromone gland extracts, including E10,E12–16:Ald, E10,E12–16:OH, and E10,E12–16:Ac, but addition of these components, either alone or in combination, at biologically relevant rates, did not significantly increase the attractiveness of lures. The saturated analogs, hexadecanal, hexadecanol, and hexadecyl acetate, also were identified in gland extracts, but had no apparent effect as pheromone components.     

Sex pheromone of fall armyworm

Two components of the fall armyworm,Spodoptera frugiperda (J.E. Smith), sex pheromone, (Z)-9-dodecen-1-ol acetate (DDA) and (Z)-9-tetradecen-1-ol (TDA), were tested alone and in combination to determine their effects on male sexual response and inhibition of mating in the laboratory. The threshold response for FAW males was lower for TDA than for DDA, and males responded to TDA over a wider range of dosages. Although TDA is not attractive to FAW males in the field, this compound was highly effective in reducing mating under laboratory conditions.cooperating with the Insect Attractants, Behavior, and Basic Biology Research Laboratory, Gainesville, Florida 32604.     

Sex pheromone components of the blueberry leaftier mothCroesia curvalana kearfott (Lepidoptera: Tortricidae)

The GC-MS and GC-EAD analyses of sex-gland components and sex-gland-released volatiles have identified (E)- and (Z)-11-tetradecenal (9010) and (E)- and (Z)-11-tetradecenyl acetate (8515) as components of the sex pheromone chemical communication system ofCroesia curvalana (Kearfott). The aldehyde-to-acetate ratio of 91 was found in the gland-released components. This blend at a 0.1–1 g/day release rate from PVC lures was shown to be as effective as virgin females in the trapping of maleC. curvalana.     

Identification, Synthesis, and Field Testing of the Sex Pheromone of the Citrus Leafminer, Phyllocnistis citrella

The citrus leafminer is an important vector of citrus canker in many of the major citrus production areas of the world. (7Z,11Z)-Hexadecadienal was reported as a sex attractant for this insect in the 1980s, based on trap catches during pheromone screening trials in Japan. However, attempts to reproduce this work in other areas of the world have not been successful. We report here that (7Z,11Z)-hexadecadienal is only one component of the pheromone, with the other critical component being the analogous trienal, (7Z,11Z,13E)-hexadecatrienal. Both compounds were identified in the effluvia from live female moths by coupled gas chromatography (GC)-electroantennography using nonpolar and polar GC columns, and the identifications were confirmed by comparisons of mass spectra with those of authentic standards. Stereoisomers of the two compounds, and a number of analogs, were synthesized to confirm the identifications. In field trials, neither compound alone was attractive to male moths, but blends of the two were highly attractive, with thousands of insects being caught per trial. Addition of the isomeric (7Z,11Z,13Z)-hexadecatrienal inhibited attraction to the two-component blend. Electronic Supplementary Material Supplementary material is available for this article at and accessible for authorized users. This paper and the preceding paper (Leal et al.) were submitted within a few days of each other. The editors and the authors agreed that they should be published in tandem.     

A Male Sex Pheromone in a Scorpionfly

It has been postulated that males of a number of scorpionfly species produce sex pheromones. This is based on the observation that females often respond only to conspecific males when they evert their genital pouch, the proposed site of pheromone release. In this study, we prove that in Panorpa germanica (Mecoptera, Panorpidae), the eversion of a male’s genital pouch is associated with the release of a volatile sex pheromone. In dual choice situations, females showed a high preference for ‘calling’ (males with everted genital pouch) over noncalling individuals. Volatiles emitted by males and females were collected and identified by coupled gas chromatography–mass spectrometry. Two aldehydes [(2E,6Z)-nona-2,6-dienal and (E)-non-2-enal] were characteristic of calling males but not of noncalling or immature males or females. Bioassays with synthetic compounds confirmed that the identified substances are attractive to females. To the best of our knowledge, this is the first identification of a sex pheromone in scorpionflies.     

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 components of the obliquebanded leafroller moth,Choristoneura rosaceana

Previously, (Z)-11-tetradecen-1-yl acetate was reported as the sex pheromone of the obliquebanded leafroller,Choristoneura rosaceana (Harris). A mixture of 92% (Z)-11-tetradecen-1-yl acetate and 8% (E)-tetradecen-1-yl acetate has been reported as an attractant for this insect. (E)-11-tetradecen-1-yl acetate and (Z)-11-tetradecen-1-ol have now been isolated and identified from female tip extracts and shown to be behaviorally active; in addition, there is some evidence for the presence of (E)-11-tetradecen-1-ol in these extracts. TheZE ratio for both the acetates and the alcohols in these tip extracts was about 982; the proportion of alcohols was rather variable, but the acetates always predominated. Maximum trap catches fn the field during the course of this study were obtained with 5 mg of 955 (Z)(E)-11-tetradecen-1-yl acetates containing 0.5–10% (Z)-11-tetradecen-1-ol (approx. 1%Eisomer) in polyethylene caps. No evidence was found for the presence of (Z)-11-tetradecenal in female tip extracts, and this compound was found to be ineffective in increasing trap catches.Lepidoptera: Tortricidae: Tortricinae.This research was supported in part by the Rockefeller Foundation, and by NSF Grant No. GB-38020.     

Sensory and behavioral effects of gossyplure alcohol on sex pheromone response of male pink bollworm moths,Pectinophora gossypiella

(Z,Z)- and (Z,E)-7,11-hexadecadienol, reported to be pheromone precursors, interfere with the normal sequence of behavioral response of malePectinophora gossypiella to sex pheromone. The magnitude of the interference can be diminished with higher release rates of the sex pheromone. (Z,Z)-7,11-Hexadecadienol is more effective than itsZ,E isomer in eliciting the reduction in the behavioral response. Electroantennographic evidence suggests that each alcohol may be interfering more with receptor sites for the conformationally similar pheromone acetate than with receptor sites for the other pheromone isomer. Defining behavioral and physiological effects of pheromone analogs such as the alcohols of gossyplure may help to determine their potential for behavioral manipulations.     

Sex Pheromone of the Saturniid Moth, <Emphasis Type="Italic">Hemileuca burnsi</Emphasis>, from the Western Mojave Desert of California

The sex pheromone blend of Hemileuca burnsi (Lepidoptera: Saturniidae) from the western Mojave Desert was determined to be a combination of (10E,12Z)-hexadecadien-1-yl acetate (E10,Z12-16:Ac), (10E,12Z)-hexadecadien-1-ol (E10,Z12-16:OH), (10E,12E)-hexadecadien-1-yl acetate (E10,E12-16:Ac), and hexadecyl acetate (16:Ac). (10E,12Z)-Hexadecadienal (E10,Z12-16:Ald) was tentatively identified in pheromone gland extracts based on electroantennographic responses and, when added to the above blend, it enhanced trap captures at low doses. The mean ratio of the compounds in extracts of pheromone glands was 100:23:232:14:0.4 (E10,Z12-16:Ac: E10,E12-16:Ac: 16:Ac: E10,Z12-16:OH: E10,Z12-16:Ald). Field trials indicated that although E10,Z12-16:Ac and E10,Z12-16:OH were essential for attraction, the two-component blend was not attractive by itself. Addition of the three other compounds was necessary for maximum attraction, rendering this the most complicated pheromone blend described for a Hemileuca species to date. Similarities between the sex pheromone of H. burnsi and that of the allopatric Hemileuca electra electra and differences between the blends of H. burnsi and that of the sympatric H. electra mojavensis support a case for reproductive character displacement in the pheromone communication channel of H. electra.     

Sex pheromone evidence for two distinct taxa withinGraphania mutans (Walker)

The sex pheromones of two populations ofGraphania mutans (Walker) were analyzed. Females from an Auckland population produced (Z)-9-tetradecenol (Z9-14OH), (Z)-9-tetradecenyl acetate (Z9-14OAc), (Z)-7-tetradecenol (Z7-14OH) and (Z)-7-tetradecenyl acetate (Z7-14OAc), while females from a Lincoln population produced these four compounds and a large amount of (Z)-9-tetradecenal (Z9-14Ald). Significant differences, paralleling the difference between females, were observed when the responses of males of both populations to the above and other related compounds were tested by electroantennogram, field-trapping, and wind-tunnel bioassays. The most distinct difference was observed in the wind tunnel. Males from both taxa flew upwind and touched pheromone sources containing sex pheromone extract of females of their own taxon, but either did not initiate upwind flight or arrested upwind flight shortly after taking flight in response to extract from females of the other taxon. The difference between the pheromone systems of the two populations is probably due to the presence and importance of Z9-14Ald in the pheromone blend of the Lincoln population. Thus the addition of a relatively large amount of Z9-14Aid to a four-component pheromone blend (i.e., Z9-14OH, Z9-14OAc, Z7-14OH, andZ7-14OAc) attractive to Auckland males completely suppressed trap catches of male G.Mutans in Auckland but large numbers of males were caught at both Lincoln and Nelson in traps baited with this five-component blend. In wind-tunnel studies, the addition of even small (1% of amount of Z9-14OH) amounts ofZ9-14Ald to the four-component blend resulted in a significantly greater proportion of Auckland males arresting upwind flight than to the four-com ponent blend. It is suggested that these two populations of G. nations represent distinct sibling species within the described concept.LepidopteraNoctuidaeHadeninae.     

Sex attractants for Geometrid and Noctuid moths

Male moths belonging to 17 species of Geometridae and nine species of Noctuidae were captured in traps baited with synthetic chemicals as part of a field screening program. The compounds tested were the C₁₈-C₂₂ homologs of: (1) (3Z,6Z,9Z)-triene hydrocarbons; (2) mixtures containing equal quantities of (3Z,6Z)-cis-9,10-expoxydienes, (3Z,92Z)-cis-6,7-epoxydienes, and (6Z,9Z)-cis-3,4-epoxydienes; (3) (3Z,6Z)-9S,10R-epoxydienes; (4) (3Z,6Z)-9R,10S-epoxydienes; and (5) (3Z,6Z,9Z,11E)-nonadecatetraene. Field captures and electroantennographic assays revealed a high degree of specificity in the responses of many species to the synthetic chemicals. In several species the ability of males to discriminate between the 9S,10R and 9R,10S enantiomers of the monoepoxydiene isomers was clearly shown. Synergists and inhibitors were discovered for several of the reported attractants, some of which were not previously known to have semiochemical activity. The geometrid moths captured includedEpirrhoe sperryi (Herbulot),Mesoleuca ruficillata (Guenée),Triphosa haesitata (Guenée),Metanema inatomaria (Guenée),Prochoerodes transversata (Drury),Cabera erythemaria (Guenée),Synaxis jubararia (Hulst),Dysstroma brunneata ethela (Hulst),Eulithes testata (Linnaeus),Sicya macularia (Harris),Xanthorhoe iduata (Guenée),X. abrasaria aquilonaria (Herrich-Schäffer),X. munitata (Hübner),Itame loricaria (Eversmann),Eupithecia annulata (Hulst),E. rovocastaliata (Packard) andE. satyrata dodata (Taylor). The noctuid moths captured includedBleptina caradrinalis (Guenée),Idia américalis (Guenée),I. aemula (Hübner),Rivula propinqualis (Guenée),Lomanaltes eductalis (Walker),Spargaloma sexpunctata (Grote),Caenurgina distincta (Neumuller),Euclidia cuspidea (Hübner), andZale duplicata (Bethune). Six of the nine noctuid species captured belong to three subfamilies for which sex attractants had not been reported previously. Details for the stereospecific synthesis of (3Z,6Z)-cis-9,10-epoxydienes are also reported.Issued as NRCC No. 24314.     

Sex pheromone of femaleMyelois cribrella Hübner (Lepidoptera: Pyralidae)

Females ofMyelois cribrella contain about 20 ng/gland of the primary sex pheromone components (Z)-9-tetradecenyl acetate, (9Z,12E)-9,12-tetradecadienyl acetate, and (Z)-11-hexadecenyl acetate in proportions of 4115, respectively. These physiologically active components are accompanied by a number of related compounds such as (Z)-9-tetradecen-1-ol, hexadecyl acetate, (9Z,12E)-9,12-tetradecadien-1-ol, (Z)-11-hexadecen-1-ol, octadecyl acetate, octadecan-1-ol, and eicosyl and docosyl acetates. Octadecyl acetate, the most abundant component, represents about 42 ng/female moth; however, no physiological activity could be attributed to it. In field tests, a trap baited with a 1-mg mixture of (Z)-9-tetradecenyl acetate, (9Z,12E)-9,12-tetradecadienyl acetate, and (Z)-11-hexadecenyl acetate in a ratio of 121 caught more male moths than three live female moths.Pheromones, 58. Pheromones, 57: Bestmann et al. (1987).