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.     

Identification of unique pheromone components for soybean looper mothPseudoplusia includens

Analysis of sex pheromone glands from individual female soybean looper moths showed that in addition to the previously identified main component (Z)-7-dodecenyl acetate, the compounds dodecyl acetate, 11-dodecenyl acetate, (Z)-7-dodecenyl propionate, and (Z)-7-dodecenyl butanoate were also produced. Two of the components, 12OAc and 11–12OAc, were not detected in a single analysis of female effluvium. Flight-tunnel tests showed that the five-component and three-component blends were equal to each other and to a female extract (> 80% source contacts) and that the mixtures were superior toZ7–12OAc alone. Field tests indicated that the five-component blend was significantly more attractive thanZ7–12OAc alone at a dosage of 1 mg, but that the blend was only slightly better at 3 mg.     

Pheromone variation among eastern European and a western Asian population of the turnip mothAgrotis segetum

The female sex pheromone composition and the male electro-physiological response with respect to the three main sex pheromone components, (Z)-5-decenyl acetate, (Z)-7-dodecenyl acetate, and (Z)-9-tetradecenyl acetate, were investigated in populations ofAgrotis segetum from Armenia and Bulgaria. The percentage composition of the female-produced pheromone was 15247 and 14257 for the respective populations. Corresponding male receptor frequencies were 9901 and 6922. EAG response profiles of the male antennae were similar for the two populations. The populations from Armenia and Bulgaria differed from the earlier investigated French and Swedish populations, which have larger amounts of (Z)-5-decenyl acetate in gland extracts and have a majority of (Z)-5-decenyl acetate-sensitive receptors. Investigation of receptor frequencies on antennae of male Hungarian moths showed that individuals could be classified as either Swedish or Armenian/Bulgarian type. Males of the Swedish type were preferentially attracted to the three-component pheromone blend, whereas blends of (Z)-7-dodecenyl and (Z)-9-tetradecenyl acetate, and (Z)-7-dodecenol [pure or in mixture with (Z)-5-decenol] attracted the Armenian/Bulgarian type. The nature of pheromone variation among European and Asian populations of the turnip moth and possible mechanisms maintaining the variation are discussed.Schiff. (Lepidoptera: Noctuidae).     

A four-component pheromone blend for optimum attraction of redbacked cutworm males,Euxoa ochrogaster (Guenée)

Four acetates,Z-5-decenyl acetate,Z-5-,Z-7-, andZ-9-dodecenyl acetates, in microgram ratios of 120021 or 120062 were excellent, specific sex pheromone blends for capturing male redbacked cutworm moths in cone traps. Blends in ratios of 120021 and 220021 at 1000 g/ rubber septum dispenser remained highly effective for 6 weeks under field conditions. The essential minor components,Z-5-decenyl,Z-7-, andZ-9-dodecenyl acetates, became inhibitory at concentrations of about 10% in the blends, and this may be an important general phenomenon in lepidopteran pheromones. Blends involving a parapheromone,Z-5-undecenyl acetate, withZ-5-,Z-7-, andZ-9-dodecenyl acetate, in microgram ratios of 820021 or 2020062 were also excellent specific attractants for this species. TheZ-8-dodecenyl acetate had no obvious effect on the attraction of the redbacked cutworm males.     

Individual variation in sex pheromone of smaller tea tortrix moth,Adoxophyes sp. (Lepidoptera: Tortricidae)

Female smaller tea tortrix mothsAdoxophyes sp. (Lepidoptera: Tortricidae), which initiated calling at 1, 2, or 3 days old, respectively, were analyzed individually for (Z)-11-tetradecenyl acetate (Z11-14:OAc) and (Z)-9-tetradecenyl acetate (Z9–14: OAc) in the pheromone gland via GLC. Among different age groups, broad and similar distributions were found for pheromone quantity (¯X=58.6±52.9 ng/female; range 1.3–219.8 ng/female). The ratio of the two pheromone components averaged 6535 but ranged from 8416 to 4060. The significance of the pheromone blend variation to the attraction of males was tested in a field experiment. The ratio of males trapped by the most attractive blend versus the least attractive one was 2.2.     

Sex pheromone ofAdoxophyes orana: Additional components and variability in ratio of (Z)-9- and (Z)-11-tetradecenyl acetate

Twelve products related to the sex pheromone main components (Z)-9- and (Z)-11-tetradecenyl acetate (Z9–14Ac andZ11–14Ac, respectively), were identified in female pheromone gland extracts of the laboratory-reared summerfruit tortrix moth,Adoxophyes orana F.v R. These are the geometric isomers and the alcohols of the main components, (Z)-9-dodecenyl acetate, (Z)-11-hexadecenyl acetate, and saturated acetates of 12–22 carbons. The ratio ofZ9–14Ac toZ11–14Ac in individuals varied from 3.51 to 111 with an average of 6.2; their total added up to 462 ng/female with an average of 182 ng for 2- to 7-day-old individuals. No qualitative or quantitative differences were observed between laboratory and field insects.Z9–14Ac,Z11–14Ac and the corresponding alcohols were also found in female effluvia. Addition of either of the two alcohols to a blend of the two acetates augmented trap catch in the field. The same was true for (Z)-9,(E)-12-tetradecadienyl acetate which was not detected in gland extracts.     

Sex pheromone ofGrapholita funebrana occurrence ofZ-8- andZ-10-Tetradecenyl acetate as secondary components

Z-8-Dodecenyl acetate (Z8–12Ac),E-8-dodecenyl acetate (E8–12Ac),Z-8-tetradecenyl acetate (Z8–14Ac),Z-10-tetradecenyl acetate (Z10–14Ac), andZ-8-dodecen-1-ol (Z8–12OH) were identified in the proportions 10013052 in female sex gland extracts ofGrapholita funebrana, accompanied by saturated acetates from 12 to 20 carbons with tetradecyl acetate predominating.Z10–14Ac has not previously been described as a lepidopteran sex pheromone component. Best attraction of males is obtained withZ8–12Ac in the presence of a higher proportion ofE8–12Ac than in the female. Inclusion of the 14-carbon acetates did not augmentG. funebrana catches but inhibitedG. molesta. On the other hand, addition ofZ8–12OH at the level optimal forG. molesta reduced attraction ofG. funebrana.     

Calling behavior and pheromone titer in the smaller tea tortrix moth,Adoxophyes sp. (Lepidoptera: Tortricidae)

The calling behavior and pheromone titer in the female smaller tea tortrix moth,Adoxophyes sp., were investigated under a 1410-hr light-dark photoperiod. Quantitative gas chromatographic analysis of ovipositor extract for (Z)-11-tetradecenyl acetate (Z11–14Ac) and (Z)-9-tetradecenyl acetate (Z9–14Ac), the major pheromone components of this species, obtained on the third day postemergence, indicated that extractable amounts of sex pheromone were present throughout the period of observation. Maximal pheromone titer and calling activity was reached at 8 and 10 hr after onset of scotophase, respectively. The ratio ofZ11–14Ac toZ9–14Ac through the 24-hr period varied significantly. The significance of the sex pheromone component ratio variation on the attraction of males was tested in a field experiment. The ratio of males trapped by the most attractive blend versus the least attractive one was 2.16.     

Comparing the effectiveness of sexual communication disruption in the oriental fruit moth (Grapholitha molesta) using different combinations and dosages of its pheromone blend

The relative efficacy of disruptant blends comprised of different combinations of the Oriental fruit moth's pheromone components was determined in field tests. Disruption was evaluated by comparing male moth catch at synthetic and female-baited traps in disruptant and non-treatment areas. Three atmospheric dosages of a 8-dodecenyl acetate (93.5%Z6.5%E) blend, representing two successive 10-fold decreases in concentration (2.5 × 10^–2 g/hectare/day to 2.5 × 10^–4 g/hectare/day) were tested alone and in combination with an additional percentage of (Z)-8-dodecen-1-ol. Male moth orientation to traps was eliminated in plots exposed to the two highest binary acetate dosages. However, significantly more males were captured in synthetic-baited traps in the lowest acetate-alone treatment, indicating a diminution of disruption efficiency. In contrast, inclusion of (Z)-8-dodecen-1-ol in the disruptant blend effected essentially complete disruption of orientation at all concentrations tested. Mating success ofG. molesta pairs confined in small cages apparently was not affected by the presence of relatively high concentrations of the binary acetate and the acetate-alcohol blends. This suggests that habituation and/or adaptation of male response, at least for comparatively close-range behaviors, did not occur.Lepidoptera: Tortricidae.Published as Journal Article No. 9569 of the Michigan Agricultural Experiment Station.     

Sex pheromone of aPlanotortrix excessana sibling species and reinvestigation of related species

The sex pheromone of aPlanotortrix excessana sibling species was investigated. Females were found to produce eight potential pheromone components: dodecyl acetate, tetradecyl acetate (14OAc). (Z)-5-tetradecenyl acetate (Z5-14OAc), (Z)-7-tetradecenyl acetate (Z7-14OAc), (Z)-9-tetradecenyl acetate, hexadecyl acetate, (Z)-7-hexadecenyl acetate, and (Z)-9-hexadecenyl acetate. When these compounds were bioassayed using field-trapping and wind-tunnel techniques, only 14OAc,Z5-14OAc, andZ7-14OAc were found to be behaviorally active. The sex pheromone glands of females of other species including,Planotortrix MBS,Planotortrix M,P. notophaea, Ctenopseustis servana, and aC. obliquana sibling species, were also found to containZ5-14OAc orZ7-14OAc, singly or in combination. In the case ofPlanotortrix M, the addition ofZ7-14OAc to the previously identified sex pheromone blend ofZ5-14OAc and 14OAc was found to increase trap captures of male moths of this species. Thus in these New Zealand species (and in some Australian species),Z5-14OAc andZ7-14OAc appear to be utilized in combination in pheromonal communication just as (Z)-11-tetradecenyl acetate and (E)-11-tetradecenyl acetate are used by many species of Holarctic Tortricidae in the tribe Archipini.Lepidoptera: Tortricidae: Tortricinae.     

Sex pheromone components of corn stalk borerSesamia nonagriodes (Lef.) isolation,identification, and field tests

Z-11-Hexadecenyl acetate (Z11–16OAc), dodecyl acetate (12OAc),Z-11-hexadecenal (Z11–16Aid), andZ-11-hexadecenol (Z11– 16OH), were found in pheromone gland extracts of femaleSesamia nonagriodes (Lef.) [Lepidoptera: Noctuidae]. These four components were also present in airborne volatiles collected from calling virgin females in a 651889 ratio. Hexadecyl acetate (16OAc) was also detected but found to be inactive. The identification was based on multicolumn GC analysis, mass spectrometry, and field activity.Z11–16OAc is the major sex pheromone component; the addition of the secondary components individually decreased male captures. The blend of the four synthetic components in 691588 ratio was highly attractive to males; 200 g per trap was the most effective concentration in field tests.Lepidoptera: Noctuidae     

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.     

Identification and field testing of additional components of female sex pheromone of African armyworm,Spodoptera exempta (Lepidoptera: Noctuidae)

Ovipositor washings from virgin femaleSpodoptera exempta (Walker) (Lepidoptera: Noctuidae) were analyzed by high-resolution gas chromatography (GC) linked to a male electroantennogram (EAG). GC retention times of the two major EAG responses observed were consistent with their assignment as (Z)-9-tetradecenyl acetate and (Z,E)-9,12-tetradecadienyl acetate, as previously identified. However, three other EAG responses were also noted that had GC retention times consistent with (Z)-9-tetradecenal, (Z)-9-tetradecen-1-o 1, and (Z)-11-hexadecenyl acetate. The components were present in the ratio of 10051.53.54, respectively. Further analysis of the ovipositor washings by GC linked to a mass spectrometer (GC-MS) confirmed these findings and indicated the presence of a sixth component consistent with (Z)-11-tetradecenyl acetate present at 2 % of the major component. In field tests carried out in Kenya, (Z)-11-hexadecenyl acetate was the only newly identified component to enhance the catch of the original two-component mixture when presented in their natural ratio. The addition of (Z)-9-tetradecen-1-ol reduced catch, while (Z)-9-tetradecenal and (Z)-11-tetradecenyl acetate had no apparent effect.     

Comparison of electroantennograms from female and male cabbage looper moths (Trichoplusia ni) of different ages and for various pheromone concentrations

The electroantennogram (EAG) responses of both male and femaleTrichoplusia ni to two components of the female-released sex pheromone were determined over a range of concentrations of chemical and age of insect. The EAG was at a peak at a dose of 100 g for both dodecyl acetate and (Z)-7-dodecenyl acetate (Z7–12OAc) for both sexes. The EAG responses varied with age of the insect. Responsiveness to both components was at a maximum at three days postemergence for males followed by a fairly rapid senescence, and for females it peaked at three days followed by a rapid senescence forZ7–12OAc but not for dodcecyl acetate.     

Intraspecific variation of two components in sex pheromone gland ofPlanotortrix excessana sibling species

Two components, (Z)-5- and (Z)-7-tetradecenyl acetates, in the sex pheromone gland of aPlanotortrix excessana sibling species, were found to vary continuously from a ratio of 397 to 7129 in individual female moths reared from wild larvae collected around New Zealand. Two laboratory colonies were established from populations representing extremes of these ratios. Although both the ratios and the total quantities of the components in individual female moths from both colonies were significantly different from each other, there was a small number of females that overlapped in both ratio and quantity. The variation was confirmed as intraspecific in a field cage experiment with male moths from both populations mating with tethered female moths from both populations.Lepidoptera: Tortricidae: Tortricinae.     

Aggregation pheromone characterization and comparison inDrosophila ananassae andDrosophila bipectinata

(Z)-11-Octadecenyl acetate (Z11–18Ac) and (Z)-11-eicosenyl acetate (Z11–20Ac) were identified as the aggregation pheromones ofDrosophila ananassae, andZ11–20Ac was identified as the aggregation pheromone ofDrosophila bipectinata. Z11–18Ac andZ11–20Ac were not attractive alone; however, in combination with fermenting food odors, the acetates attracted flies of both sexes in a wind-tunnel olfactometer. The pheromones were present in the ejaculatory bulb of sexually mature male flies and transferred to the female during mating. MaleD. bipectinata released little if anyZ11–20Ac to the food; however, recently mated females releasedZ11–20Ac to the surrounding surfaces in just a few hours after mating.D. ananassae males, on the other hand, appeared to release moreZ11–18Ac andZ11–20Ac to the surroundings than mated females. AlthoughD. bipectinata males had noZ11–18Ac, flies were as attracted toZ11–18Ac as to an equal quantity ofZ11–20Ac.D. ananassae were attracted toZ11–18Ac but not toZ11–16Ac orZ11–20Ac. However,Z11–20Ac in combination withZ11–18Ac was significantly more attractive thanZ11–18Ac alone.     

9,11-Dodecadienyl alcohols,acetates, or aldehydes as synthetic chemical sex attractants for four Lepidoptera:Cosmopterix gemmiferella (Clemens),Dichrorampha simulana (Clemens),Tortricidia testacea (Packard), and anAncylis sp.

Four lepidoptera were lured to field traps containing various combinations of 9,11-dodecadienes with alcohol, acetate, or aldehyde functional groups. All species required two chemical components for best attraction.Cosmopterix gemmiferella was most responsive to a combination of (9Z)-9,11-dodecadienyl acetate and (9E)-9,11-dodecadienyl acetate in 21 ratio;Dichrorampha simulana to (9E)-9,11-dodecadienyl acetate and (9E)-9,11-dodecadien-1-ol in 101 ratio;Tortricidia testacea to (9Z)-9,11-dodecadienal and (9E)-9,11-dodecadienal in 101 ratio; andAncylis sp. to (9Z)-9,11-dodecadienyl acetate and (9Z)-9,11-dodecadien-1-ol in 101 ratio.     

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.     

Oriental fruit moth pheromone component emission rates measured after collection by glass-surface adsorption

We collected and quantified both synthetic and natural Oriental fruit moth [Grapholitha molesta (Busck)] sex pheromone components in 250-ml round-bottom flasks by hexane rinsing of compounds adsorbed on the glass walls. This simple procedure collected 100% of the pheromone evaporated inside the flask and was useful for quantifying both nanogram and microgram amounts of emitted pheromone. Emission rates of (Z)-8-dodecenyl acetate from 1000, 100, and 10 g-loaded rubber septa were 219, 12, and 1.2 ng/hr, respectively.G. molesta females emitted this component at 3.2 ng/hr, close to the emission rate from a 10 g-loaded septum, which evokes long-range and close-range behaviors in the male. The corresponding alcohol, (Z)-8-dodecenyl alcohol, was emitted from rubber septa ca. 3 times faster than the acetate.Lepidoptera: Tortricidae.Paper of the Michigan State Agricultural Experiment Station.     

Optimized conditions for sex attractant trapping of male redbacked cutworm moths,Euxoa ochrogaster (Guenée)

Mixtures of (Z)-5- and (Z)-7-dodecenyl acetates in ratios >1001 are powerful, specific sex attractants for redbacked cutworm male moths. Bioactive lures were produced by admixture of these pure compounds or through syntheses involving catalytic bond shifting. Best field trapping was obtained with 2001 (Z)-5(Z)-7 ratio, at lure doses (on rubber) of 0.1–2.0 mg, using cone swivel traps with 10- to 13-mm orifices, or Pherocon® 1-CP sticky traps, at a height of 50–90 cm. The pheromone traps were more efficient than large blacklight traps and captured the various morphological forms of the moth in similar ratios.Lepidoptera: NoctuidaeIssued as NRCC No. 18206.