Identification of sex attractant pheromone components of the tussock moth,Euproctis taiwana (Shiraki) (Lepidoptera: Lymantriidae)

Two compounds were isolated and identified from abdominal tips of the female tussock moth,Euproctis taiwana (Shiraki), by a combination of gas chromatography-electroantennographic detection, coupled gas chromatography-mass spectrometric analysis, microreaction, and synthesis. These compounds were (Z)-16-methyl-9-heptadecenyl isobutyrate (74.8%) and 16-methylheptadecyl isobutyrate (25.2%). Their total amount was determined to be ca. 29.8 ng/female. Field bioassays showed that (Z)-16-methyl-9-heptadecenyl isobutyrate is a sex attractant for the male moths. These chemical compounds had not previously been found as the sex pheromone components in the genusEuproctis.     

Components of the sex pheromone of the female spotted stalk borer,Chilo partellus (Swinhoe) (Lepidoptera: Pyralidae): Identification and preliminary field trials

FemaleChilo partellus (Swinhoe) abdominal tip extracts were examined by gas-liquid chromatography (GLC) combined with simultaneous electroantennographic (EAG) recording from the male moth. Two olfactory stimulants were detected and identified as (Z)-11-hexadecenal (I) and (Z)-11-hexadecen-1-ol (II) by their GLC behavior, microchemical reactions, and comparison with synthetic materials. Both compounds were detected in volatiles emitted by the calling female moth. Synthetic (Z)-9-tetradecenyl formate, a structural analog of aldehyde (I), also elicited a significant EAG response from the male moth. Field trials carried out in India using synthetic (I) and (II) as bait in water traps showed that compound (I) was highly attractive to maleC. partellus; compound (II) was not attractive, and its addition to (I) significantly reduced trap catches.     

Sex pheromone of the pea moth,Cydia nigricana (F.) (Lepidoptera: Olethreutidae)

The sex pheromone of the pea moth,Cydia nigricana (F.), was identified as (E,E)-8,10-dodecadien-1-ylacetate (E,E8,10–12Ac) (approximately 0.1 ng/abdominal tip), in vacuum distillates of virgin female abdominal tips and volatiles emitted by calling females, from its chemical properties and capillary gas chromatography and mass spectrometry data. SyntheticE,E8,10–12Ac and the natural pheromone elicited similar quantitative electrophysiological and behavioral responses from male moths. Other related compounds which also attract male moths in the field,viz., (E)-10-dodecen-1-yl acetate, (E,E)-8,10-dodecadien-1-ol, and (E,E)-8,10-dodecadienal, were not detected in the pheromone andE,E8,10–12Ac was not found in male moths.     

Identification of a four-component sex pheromone of the female oriental fruit moth,Grapholitha molesta (Lepidoptera: Tortricidae)

The female-emitted pheromone ofGrapholitha molesta (Busck), the Oriental fruit moth, was collected by holding females in glass flasks during calling. Flask washes were found to contain four pheromone components: (Z)-8-dodecenyl acetate and (E)-8-dodecenyl acetate in a 1007 ratio, and (Z)-8-dodecen-1-ol and dodecanol in a 10020 ratio. The ratio of (Z)-8-acetate to (Z)-8-dodecen-1-ol was approx. 10030. Approximately 0.1–0.2 ng of pheromone was recovered per female per hour of calling.Published as Journal Article No. 8598 of the Michigan State University Agricultural Experiment Station.     

Codling moth,Cydia pomonella, (Lepidoptera: Tortricidae): Is its sex pheromone multicomponent?

When the nine identified components in the effluvium of calling female codling moths were compared to pure synthetic (E,E)-8,10-dodecadien-1-ol in flight-tunnel tests, equal responses were obtained over a concentration range of 300-fold. When synthetic (E,E)-8,10-dodecadien-1-ol was compared to extract of female sex pheromone glands by a male wing-flutter bioassay, or in flight-tunnel tests, equal responses were obtained over a concentration range of 1000-fold. The sum total of these and previous studies indicate that the codling moth sex pheromone consists of only one component.     

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.     

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.     

Identification and bioassay of sex pheromone components of carob moth,Ectomyelois ceratoniae (Zeller)

Three sex pheromone components of the carob moth were isolated and identified from the extract of female pheromone glands, using a variety of techniques including coupled gas chromatographic-electroantennographic recordings, coupled gas chromatographic-mass spectrometric analysis, microozonolysis, electroantennographic assays of monounsaturated standards, wind-tunnel bioassays, and field trials. The major component was identified as (Z,E)-9,11,13-tetradecatrienal, a novel lepidopterous pheromone component structure. Two minor components, either one of which improves the upwind flight response of males when blended with the major component, were identified as (Z,E)-9,11-tetradecadienal, and (Z)-9-tetra-decenal.     

Novel sex pheromone components from the fall cankerworm moth,Alsophila pometaria

A sex pheromone extract from fall cankerworm moths,Alsophila pometaria, attracted conspecific males in field tests. Four EAG-active components were isolated from the extract and identified by GC-MS, highfield PMR spectroscopy, and microchemical techniques asn-nonadecane (I), (Z,Z,Z)-3,6,9-nonadecatriene (II), (Z,Z,Z,E)-3,6,9,11-nonadecatetraene (III), and (Z,Z,Z,Z)-3,6,9,11-nonadecatetrane (IV). Studies of the behavioral responses of male moths in a flight tunnel to the isolated components showed II, III, and IV were the major components of the sex pheromone. No sex pheromone behavioral responses were observed for I.Lepidoptera: Geometridae.issued as NRCC No. 22964.     

Nantucket pine tip moth,Rhyacionia frustrana: Identification of two sex pheromone components

Two compounds identified as components of the sex pheromone system ofRhyacionia frustrana are (E)-9-dodecen-1-yl acetate (I) and (E)-9,11-dodecadien-1-yl acetate (II), which were found in female gland extracts in the ratio of 964, respectively. The identifications were based on chemical and instrumental analyses, electroantennogram studies, and field trapping tests. The optimum ratio for trapping maleR. frustrana is the range of 955 to 97.52.5 (III), when dispensed from rubber septa at a loading of ca. 1000/g/lure. In addition to these two compounds, evidence was obtained for the presence of dodecan-1-ol and (E)-9-dodecen-1-ol in female tip extracts and in female effluvium, and for dodecan-1-yl acetate in female tip extracts.Lepidoptera: Tortricidae: Olethreutinae.Supported in part by the Rockefeller Foundation and by National Science Foundation grants GB-38020 and PCM 78-13241.     

Isolation and identification of sex pheromone ofSymmetrischema tangolias (Gyen) (Lepidoptera: Gelechiidae)

The sex pheromone of the South American potato tuber mothSymmetrischema tangolias (syn.:Symmetrischema plaesiosema) was identified as a 2:1 mixture of (E,Z)-3,7-tetradecadien-1-ol acetate and (E)-3-tetradecen-1-ol acetate by means of dual-column GC, EAG, GC-EAD, GC-MS, NMR, and wind-tunnel bioassays. (Z)-5-Tetradecen-1-ol acetate and (Z)-7-tetradecen-1-ol acetate were also identified in the pheromone gland extract. MaleS. tangolias were able to detect these acetates (EAG), but their addition to the two-component sex pheromone did not improve attractiveness. Field trials in Cajamarca and Cusco, Peru, showed that traps baited with the synthetic sex pheromone were able to catch large numbers of maleS. tangolias.     

Codling moth (Cydia pomonella): Disruptants of sex pheromonal communication

In a small section of an apple orchard, six traps were placed each in control and test areas and baited with live virgin female codling moths. Gray elastomer septa were used to dispense communication disruptants around the traps. Dyed male codling moths were released in control and test areas, and the numbers of males captured in control and test traps were compared. In 1991, linear regression curves of percent communication disruption versus logarithm of dose were obtained for three compositions: (E,E)-8,10-dodecadien-1-ol, codlemone (1); codlemone + dodecan-1-ol + tetradecan-1-ol (2); and an equilibrium mixture of the four isomers of 8,10-dodecadien-1-ol (30, (61%EE, 14%ZE, 20%EZ, and 5%ZZ). All three regressions gaver ² values greater than 0.90. At the 95% confidence limits, slopes and intercepts of compositions 1 and 2 were equivalent, and different from that of composition 3, which produced the greatest percentages of disruption at all doses. In 1992, five treatments were compared at a single dose: 1, 3, none (4), (Z,E)-8,10-dodecadien-1-ol (5), (E,Z)-8,10-dodecadien-1-ol (6). Compositions 5 and 6 gave the greatest and similar percentages of disruption and were different from codlemone (1) and 4 (95% confidence), but not from composition 3. Communication disruption produced by composition 3 was greater than (codlemone), which was greater than 4.     

Sex pheromone of the european sunflower moth,Homoeosoma nebulellum (Den. & Schiff.) (Lepidoptera: Pyralidae)

Four components, (Z)-9-tetradecenal (8.6%), (Z,E)-9,12-tetradecadienal (4.8%), (Z)-11-hexadecenal (49.5%), and (Z)-13-octadecenal (37.1%), were identified in extracts of female pheromone glands of the European sunflower moth,Homoeosoma nebulellum (Lepidoptera: Pyralidae) using GC and GC-MS analyses. EAG and single-cell recordings of male antennal receptors gave strong evidence for (Z,E)-9,12-tetradecadienal as the antennal key compound of sex pheromone detection in this species. This result was confirmed by field trapping; removal of (Z,E)-9,12-tetradecadienal from quaternary blends completely suppressed the male catches. The synthetic blends with this compound as a major component caught five times less males than the blends reproducing the ratio found in the female extracts [5% of (Z,E)-9,12-tetradecadienal only]. The occurrence of a minor component perceived as the most biologically relevant compound is discussed.     

Anemotactic response threshold of the Indian meal moth,Plodia interpunctella (Hübner) (Lepidoptera: Pyralidae), to its sex pheromone

The effect of different concentrations of the sex pheromone (Z,E)-9,12-tetradecadien-1-ol acetate on the upwind anemotactic behavior of the malePlodia interpunctella (Hübner) was measured at 23 ± 1 ° C and 34 ± 1 ° C. The stimulus-response regression lines were analyzed by a new procedure that accounts both for control responses in the absence of pheromone and also for peak responses below 100% in the presence of concentrations considerably above the normal physiological levels. From the regression line for each temperature, the upwind anemotactic thresholds were calculated to be 1.34 × 10⁶ molecules/cm³ at 23 ° C and 1.65 × 10⁴ molecules/cm³ at 34 ° C, similar to other thresholds reported in the literature. Since departures from the two lines occurred at the highest concentrations tested, near 10⁸ molecules/cm³, the upwind anemotactic behavior may change qualitatively above an altered-behavior threshold that is about two orders of magnitude higher than the upwind anemotactic threshold. The lower response at 23 ° C suggests that cool temperatures inhibit flight in response to pheromonal stimulation.Mention of a commercial or proprietary product in this paper does not constitute an endorsement of that product by the USDA.     

(Z,E)-3,5-Tetradecadien-1-ol acetate sex attractant for the carpenterworm moth,prionoxystus robiniae (peck) (Lepidoptera: Cossidae)

Electroantennogram analyses of female gland extract and of male antennal responses to synthetic standards suggested that (Z,E)-3,5-tetradecadien-1-ol acetate is a pheromone component for the carpenterworm moth,Prionoxystus robiniae (Peck). The four 3,5-geometrical isomers were synthesized and bioassayed in the laboratory and the field in 1972, 1973, and 1974. TheZ,E isomer was found to be active in the laboratory and a good attractant in the field. The synthesis of theZ,E isomer also produced considerable quantities of theE,E isomer, which is difficult to remove completely. TheE,E isomer does not inhibit the response of males to theZ,E isomer when it is present in amounts up to 20% of theZ,E isomer. The addition of a keeper, a volatility modifier, or an antioxidant prolonged the activity of the attractant for as much as 43 days. (Z,E)-3,5-Tetradecadien-1-ol acetate may be a natural pheromone, but it has not been chemically defined from female extract. There is EAG evidence that a second pheromonal component may be present. The attractant nevertheless provides a tool for population survey, behavioral studies, evaluation of economic impact, and possibly control.     

Variability in pheromone composition and periodicity of pheromone titer in potato tuberworm moth,Phthorimaea operculella (Lepidoptera: Gelechiidae)

The ratios and quantities of the pheromone components, (E,Z)-4,7-tridecadien-1-yl acetate (diene) and (E,Z,Z)-4,7.10-tridecatrien-1-yl acetate (triene), in the glands of individual female potato tuberworm moths (Phthorimaea operculella) originating from the United States (California) and Japan (Nagoya) were analyzed by gas chromatography. Quantities of glandextracted pheromone components of Nagoya females fluctuated in a periodic fashion during the photoperiod. Maximal titers coincided with the onset of scotophase (and calling), then gradually declined to minimal levels soon after lights-on. The average daily pheromone quantities decreased significantly as females aged. Both populations exhibited considerable variation in the ratio of the two components. The proportions of triene in the blend ranged from 27% to 88% (triene –X = 56 ± 13% SD; CV = 23%) for California females and from 16% to 71% (42 ± 13%; CV = 31%) for Nagoya females. Nagoya females also stored significantly higher amounts of pheromone in their glands (8.6 ± 3.9 ng) than did California females (2.7 ± 1.4). The differences between the populations, while substantial, would probably not be sufficient to impart a barrier to panmixis, given the wide range of component ratios favored by the males.     

Role of pheromone components in evoking behavioral responses from male potato tuberworm moth,Phthorimaea operculella (Zeller) (Lepidoptera: Gelechiidae)

Responses of the male potato tuberworm moth,Phthorimaea operculella (Zeller), to two sex pheromone components and female crude extract were studied. Both in a wind tunnel and the field, males were better able to locate a source consisting of a 11 mixture of (E,Z)-4,7-tridecadien-1-yl acetate and (E,Z,Z)-4,7,10-tridecatrien-1-yl acetate than a source consisting of the triene alone. The addition of the diene increased the time spent in the vicinity of the pheromone source, time spent on the source itself, and also increased the average number of visits to the source per individual when compared to the triene alone. The triene elicited high levels of locomotor activity and may play a major role in eliciting earlier (long-range) steps in the behavioral sequence of sexually activated moths. The diene appeared to influence later (short-range) behavior. The behavioral responses of males to a 11 mixture of the diene and triene were similar to those elicited by female crude extract.From a thesis submitted by M. Toth to the Australian National University in fulfillment of the requirements for the degree of Master of Science.These studies were supported by an Australian Department of Education award under the AEAP award scheme.     

Sugar beet crown borer,Hulstia undulatella (Clemens) 1: Identification and field tests of female sex pheromone gland components

Electroantennogram profiles of saturated and monounsaturated 12-, 14-, and 16-carbon acetates, and 12- and 14-carbon alcohols implicated (Z)-9-tetradecen-1-ol acetate (Z9-14: Ac) as a component of the female sex pheromone ofHulstia undulatella (Clemens). Gas chromatography-mass spectrometric analysis of extract of the female sex pheromone glands showed the presence of Z9-14:Ac (8.5 ng/female), (Z)-9-tetradecen-1-ol (Z9-14:OH), and (Z)-11-hexadecen-1-ol acetate (Z11-16:Ac) in a ratio of 100421, respectively. In tests in sugar beet fields, Z9-14:Ac alone produced some trap catch. Addition of Z9-14: OH did not increase catch while addition of Z11-16:Ac eliminated catch, but addition of both Z9-14:OH and Z11-16: Ac increased catch sevenfold. A combination of Z9-14: OH and Z11-16: Ac without Z9-14: Ac did not produce trap catch. A lure of 200 g Z9-14:Ac+16 g Z9-14:OH+42 g Z11-16:Ac is suggested for use in monitoring traps.Lepidoptera: Pyralidae: Phycitinae.     

Identification of sex pheromones of two sibling species in dingy cutworm complex,Feltia jaculifera (GN.) (Lepidoptera: Noctuidae)

The sex pheromone components of the two sibling species of the dingy cutworm that occur on the prairies of western Canada were identified in abdomen-tip extracts from calling female moths. Three monounsaturated acetates, (Z)-7-dodecenyl acetate, (Z)-9-tetradecenyl acetate, and (Z)-11-hexadecenyl acetate, are common to both species in ratios of 100133 for species A and 0.30.5100 for species B. The most effective synthetic blends for the attraction of male moths in the field consisted of these three components in ratios of 1010 at 8.8g/lure for species A and 112000 at 500g/lure for species B. The addition of Z5-12Ac to either blend reduced the catches and the addition of Z7-12OH orZ11-16OH to the three-component blend reduced the catches of species B males. The species are morphologically indistinguishable, but the identity of the males attracted to the synthetic blends could be confirmed by their antennal responses to a test blend of the three components using a GC-EAD system. Both synthetic attractant blends are competitive with females and will be useful for studying the distribution, biology, and relative abundances of the two species.Contribution no. 3879005 of the Lethbridge Research Station.     

Apple ermine moth,Yponomeuta malinellus Zeller Two components of female sex pheromone gland highly effective in field trapping tests

When electroantennographic responses of maleYponomeuta malinellus Zeller to model compounds were determined at dosages of 0.3–30 ng, the strongest responses were obtained from (Z)-9-dodecen-1-ol acetate (Z9–12Ac). Also, strong responses were obtained from (Z)-11-tetradecenal (Z11–14A1) and (Z)-11-tetradecen-1-ol (Zl1–14OH). At a dosage of 0.3 ng,Z11–14A1 produced a stronger response thanZ11–14OH, while at a dosage of 30 ng,Z11–14OH andZ11–14A1 produced equal responses. Gas chromatographic and mass spectral analysis of extracts of female sex pheromone glands showed the presence ofZ9–12Ac, tetradecan-1-ol (14OH), (E)-11-tetradecen-1-ol (E11–14OH),Z11–14OH, hexadecan-1-ol, and hexadecan-1-ol acetate in a ratio of 0.62003710014035. In field tests,Z9–12Ac andZ11–14OH together were required for trap catch, and addition ofZ11–14A1,E11–14OH, 14OH, or (Z)-11-tetradecen-1-ol acetate did not increase catch. Ratios in rubber septa of 0.599.5 to 1.598.5 (Z9–12 Ac/Z11–14OH) captured the most males and captures were statistically equivalent for dosages of 10–1000 g/rubber septum. Traps baited with the synthetic lure produced better catches than those baited with females.Lepidoptera: Yponomeutidae.