Role of female-produced sex pheromone in behavioral reproductive isolation betweenTrichoplusia ni (Hübner) andPseudoplusia includens (Walker) (Lepidoptera: Noctuidae,plusiinae)

In laboratory flight tunnel bioassays, response rates of male cabbage looper,Trichoplusia ni (Hübner), to female soybean looper,Pseudoplusia includens (Walker), were similar to response rates of maleT. ni to conspecific females for plume tracking and source contact. Male soybean loopers, however, exhibited a greatly reduced response to female cabbage loopers compared to conspecific females. Similar differences were observed in male responses to extracts of female abdominal tips. Studies of flight tunnel responses of male soybean loopers to the different chemicals known to be components of the female cabbage looper sex pheromone indicated that the reduction in response was due to inhibitory effects of (Z)-5-dodecen-1-ol acetate and (Z)-9-tetradecen-1-ol acetate, when added singly to (Z)-7-dodecen-1-ol acetate (major component of both species) at release rates and at ratios close to those observed in female cabbage loopers.     

Sex pheromone of fall armyworm,Spodoptera frugiperda (J.E. Smith)

Analyses of extracts of pheromone glands and of volatiles from calling female fall armyworm moths,Spodoptera frugiperda (J.E. Smith), revealed the presence of the following compounds: dodecan-1-ol acetate, (Z)-7-dodecen-1-ol acetate, 11-dodecen-1-ol acetate, (Z)-9-tetradecenal, (Z)-9-tetradecen-1-ol acetate, (Z)-11-hexadecenal, and (Z)-11-hexadecen-1-ol acetate. The volatiles emitted by calling females differed from the gland extract in that the two aldehydes were absent. Field tests were conducted with sticky traps baited with rubber septa formulated to release blends with the same component ratios as those emitted by calling females. These tests demonstrated that both (Z)-7-dodecen-1-ol acetate and (Z)-9-tetradecen-1-ol acetate are required for optimum activity and that this blend is a significantly better lure than either virgin females or 25 mg of (Z)-9-dodecen-1-ol acetate in a polyethylene vial, the previously used standard. Addition of the other three acetates found in the volatiles did not significantly increase the effectiveness of the two-component blend as a bait for Pherocon 1C or International Pheromones moth traps.Mention of a commercial or proprietary product does not constitute an endorsement by the USDA.     

Effects of host plant,Gossypium hirsutum L., on sexual attraction of cabbage looper moths,Trichoplusia ni (Hübner) (Lepidoptera: Noctuidae)

Unmated female or male cabbage looper moths,Trichoplusia ni (Hübner), were attracted more often in a flight tunnel to a cage with moths of the opposite sex and a bouquet of cotton foliage. Increased sexual attractiveness of females with plants may be a result of stimulation of pheromone release in response to plant odor, since more males were attracted when odor of cotton foliage was passed over females than when odor of females was passed over cotton foliage before venting into the flight tunnel. Increased sexual attractiveness of males with plants is due in part to host odor enhancement of female attraction to male pheromone, since more females were attracted to synthetic male pheromone (a blend of enantiomers of linalool and isomers of cresol) and a cotton leaf extract than were attracted to male pheromone alone. A short synthesis procedure was developed for (S)-(+)-linalool, the major component of the male sex pheromone, isolated from hair pencils, used in these tests.     

Identification of volatile sex pheromone components released by the southern armyworm,Spodoptera eridania (Cramer)

Analysis of sex pheromone gland extracts and volatile pheromone components collected from the calling female southern armyworm,Spodoptera eridania (Cramer), by high-resolution capillary gas chromatography and mass spectroscopy indicated that a number of 14-carbon mono- and diunsaturated acetates and a monounsaturated 16-carbon acetate were produced. Gland extracts also indicated the presence of (Z)-9-tetradecen-1-ol. However, this compound was not found in collections of volatiles. Field trapping studies indicated that the volatile blend composed of (Z)-9-tetradecen-1-ol acetate (60%), (Z)-9-(E)-12-tetradecadien-1-ol acetate (17%), (Z)-9-(Z)-12-tetradecadien-1-ol acetate (15%), (Z)-9-(E)-11-tetradecadien-1-ol acetate (5%), and (Z)-11-hexadecen-1-ol acetate (3 %) was an effective trap bait for males of this species. The addition of (Z)-9-tetradecen-1-ol to the acetate blends tested resulted in the capture of beet armyworm,S. exigua (Hubner), males which provides further evidence that the alcohol is a pheromone component of this species.     

Female Sex Pheromone of a Carpenter Moth, Cossus insularis (Lepidoptera: Cossidae)

This study describes the identification of a sex pheromone component of a cossid moth, Cossus insularis. Coupled gas chromatographic–electroantennographic detection (GC–EAD) analysis of solid-phase microextraction (SPME) collections of volatiles released by live female moths showed that two compounds elicited EAG responses from the antennae of male moths. These compounds were identified as (E)-3-tetradecenyl acetate (E3-14:Ac) and (Z)-3-tetradecenyl acetate (Z3-14:Ac) by mass spectral analysis and retention index comparisons with synthetic standards. The ratio of E3-14:Ac and Z3-14:Ac was 95:5 in the effluvia of a female. In field bioassays, sticky traps baited with blends of E3-14:Ac and Z3-14:Ac showed that E3-14:Ac is an essential component of the pheromone. However, the role of Z3-14:Ac is unclear, because E3-14:Ac as a single component was as attractive to male moths as blends of E3-14:Ac and Z3-14:Ac, including the 95:5 blend released by live female moths.     

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.     

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.     

Sex attractant of the alfalfa looperAutographa californica and the celery looperAnagrapha falcifera (Lepidoptera: Noctuidae)

In field tests, traps baited with a combination of (Z)-7-dodecen-1-ol acetate (previously proposed to be the sex pheromone ofA. californica) and (Z)-7-dodecen-1-ol formate caught about 100 times as many males as (Z)-7-dodecen-1-ol acetate did alone. Highest catches of males were obtained with traps baited with 0.5 mg of (Z)-7-dodecen-1-ol acetate and 0.1 mg of (Z)-7-dodecen-1-ol formate impregnated on red rubber sleeve stoppers. The celery looper,Anagrapha falcifera, was also caught in traps baited with a combination of these two chemicals.     

(Z)-9-tetradecen-1-ol acetate

(Z)-9-Tetradecen-1-ol acetate [(Z)-9-TDA], identified originally as the sex pheromone of the fall armyworm,Spodoptera frugiperda (J.E. Smith), acted as a secondary sex pheromone when it was tested in sticky traps in field tests. Low-level synergism was obtained when 2 and 10% quantities of (Z)-9-TDA were added to 100 g of (Z)-9-dodecen-1-ol acetate, which is now considered the primary sex pheromone.Lepidoptera: Noctuidae.In cooperation with the University of Georgia College of Agriculture Experiment Stations, Coastal Plain Station, Tifton, Georgia 31794.Mention of a proprietary product does not constitute endorsement by the USDA.     

(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     

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 and Field Evaluation of Components of Female Sex Pheromone of Millet Stem Borer, Coniesta ignefusalis

Five active compounds were detected during analyses of ovipositor washings and effluvia from virgin female Coniesta ignefusalis moths by gas chromatography (GC) linked to electroantennographic (EAG) recording from a male moth. These were identified as (Z)-7-dodecen-1-ol (Z7–12:OH), (Z)-5-decen-1-ol (Z5–10:OH), (Z)-7-dodecenal (Z7–12:Ald), (Z)-7-dodecenyl acetate (Z7–12:Ac), and (Z)-9-tetradecen-1-ol (Z9–14:OH) by comparison of their GC retention times, mass spectra, and EAG activities with those of synthetic standards. Laboratory tests of dispensers for these compounds showed that release rates from polyethylene vials increased to relatively uniform values after three to four days, but release from septa was very rapid and nonuniform and decreased to low levels after two to three days. Trapping tests in Niger showed that the major component, Z7–12:OH, and two of the minor components, Z5–10:OH and Z7–12:Ald, were essential for attraction of male C. ignefusalis moths. The most attractive blend contained these three components in a 100:5:3.3 ratio in a polyethylene vial, which emitted the components in similar proportions to those produced by the female C. ignefusalis moth. Water traps baited with this blend containing 1 mg of Z7–12:OH caught more male C. ignefusalis moths than traps baited with newly emerged female moths. Addition of up to 10% of the corresponding E isomers of the pheromone components had no effect on catches, but addition of the other two minor components detected, Z7–12:Ac and/or Z9–14:OH, to the attractive blend at naturally occurring levels caused significant reductions in trap catch.     

Female sex pheromone of the Yunnan pine caterpillar moth Dendrolimus houi: first (E,Z)-isomers in pheromone components of Dendrolimus spp

The Yunnan pine caterpillar Dendrolimus houi Lajonquière is a serious defoliator of coniferous forests in southwestern China. Gas chromatography–electroantennography (GC–EAG) analyses of extracts of female sex pheromone glands of D. houi moths revealed the presence of three compounds eliciting antennal responses. These were identified as (5E,7Z)-5,7-dodecadien-1-ol (E5,Z7-12:OH), (5E,7Z)-5,7-dodecadien-1-yl acetate (E5,Z7-12:OAc), and (5E,7Z)-5,7-dodecadienal (E5,Z7-12:Ald) by comparison of their GC retention indices, mass spectra, and EAG activities with those of synthetic standards. Average amounts of E5,Z7-12:OH, E5,Z7-12:OAc, and E5,Z7-12:Ald per calling virgin D. houi female were 14.7 ± 12.9 ng (± SD), 5.8 ± 5.4 ng, and 0.8 ± 1.4 ng, respectively, in a ratio of 100:39.7:5.6. These three components were also collected from the headspace of calling virgin female moths by solid-phase microextraction (SPME). In addition, trace quantities of (Z)-5-dodecen-1-ol (Z5-12:OH), (5Z,7E)-5,7-dodecadien-1-ol (Z5,E7-12:OH), (5E,7E)-5,7-dodecadien-1-ol (E5,E7-12:OH), (5Z,7E)-5,7-dodecadien-1-yl acetate (Z5,E7-12:OAc), (5Z,7Z)-5,7-dodecadien-1-yl acetate (Z5,Z7-12:OAc), and (5E,7E)-5,7-dodecadien-1-yl acetate (E5,E7-12:OAc) were tentatively identified in female pheromone gland extracts by selected ion monitoring GC-MS. Field trapping experiments showed that E5,Z7-12:OH, E5,Z7-12:OAc, and E5,Z7-12:Ald were essential for attraction of male D. houi moths. Traps baited with a 20:1:1 blend (alcohol/acetate/aldehyde) loaded on gray rubber septa were as effective as traps baited with virgin female moths. The optimum ratio of acetate to aldehyde was 1:1, and this ratio was more critical than the ratio of either compound to the alcohol. This represents the first example of (E,Z)-isomers in pheromone blends of Dendrolimus species.     

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.     

Identification of sex pheromone produced by female sweetpotato weevil,Cylas formicarius elegantulus (Summers)

A sex pheromone of the sweetpotato weevil,Cylas formicarius elegantulus (Summers), was obtained from collections of volatiles from virgin females, and pheromone was isolated by means of liquid and gas chromatography. The purification procedure was monitored by quantitative laboratory and field bioassays and the compound was identified as (Z)-3-dodecen-1-ol (E)-2-butenoate by means of spectroscopic and microchemical methods. Synthesis, followed by laboratory and field bioassays, showed that the biological activity of the synthetic material was qualitatively and quantitatively indistinguishable from that of the purified natural product.Mention of a commercial or proprietary product does not constitute an endorsement by the USDA.     

Effect of release rate and ratio of (Z)-11-hexadecen-1-ol from synthetic pheromone blends on trap capture ofHeliothis subflexa (Lepidoptera: Noctuidae)

Response of maleHeliothis subflexa to pheromone-baited traps containing blends of tetradecanal, (Z)-9-tetradecanal, hexadecanal, (Z)-7-hexadecenal, (Z)-9-hexadecenal, (Z)-11-hexadecenal, hexadecan-1-ol acetate, (Z)-7-hexadecen-1-ol acetate, (Z)-9-hexadecen-1-ol acetate, (Z)-11-hexadecen-1-ol acetate, (Z)-9-hexadecen-1-ol, and (Z)-11-hexadecen-1-ol was evaluated. Analysis of trap capture data indicated that (Z)-11-hexadecen-1-ol was a critical component of the pheromone blend. It was determined from emission rate data and measurements of the ratio of pheromone components emitted from rubber septa tested that a significant increase in trap capture of maleH. subflexa occurred when the blends investigated released the alcohol in a narrow range relative to the total amount of pheromone emitted. The optimum range of release ratio of the alcohol for the capture of males in sticky traps was determined to be 0.9–3.5% of the pheromone blend. This release ratio range was reduced to 0.9–1.6% when bucket traps were used.     

Evolution of behavioral responses to sex pheromone in mutant laboratory colonies ofTrichoplusia ni

Male cabbage looper moths,Trichoplusia ni, from two colonies in which all females express an abnormal sex pheromone production phenotype were evaluated in a laboratory wind tunnel for upwind flight responses to the normal and abnormal sex pheromones. The abnormal sex pheromone blend consisted of 20 times as much (Z)-9-tetradecenyl acetate and 30-fold less (Z)-5-dodecenyl acetate compared to the normal pheromone blend. Initially, these males exhibited poor behavioral responses to the abnormal sex pheromone and maximum responses to the normal pheromone blend, indicating that there was no linkage between signal production and response. After 49 generations of laboratory rearing, males from the mutant colonies maintained good responses to the normal pheromone and increased their behavioral response to the abnormal sex pheromone to the same levels as for the normal pheromone. Over the same period, normal males maintained their preference for the normal pheromone. These results indicated that evolution had occurred in mutant colonies in favor of greater male responsiveness to the abnormal sex pheromone, resulting in the broadening of the response spectrum to pheromone blend ratios. This evolution presumably resulted from a mating advantage to those males that did not discriminate against mutant-type females in the mutant colonies.     

(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.     

Sex Pheromone of the Common Sheep Moth, Hemileuca eglanterina, from the San Gabriel Mountains of California

The sex pheromone of Hemileuca eglanterina from the San Gabriel Mountains, California, was determined to be a combination of E10,Z12-hexadeca-10,12-dien-1-yl acetate, E10,Z12-hexadeca-10,12-dien-1-ol, and E10,Z12-hexadeca-10,12-dienal. Ratios of the compounds in extracts of female pheromone glands varied around a mean of 100 : 48 : 1.1 of the acetate, alcohol, and aldehyde, respectively. Field trials with synthetic compounds indicated that the optimum ratio of alcohol to aldehyde was 10 : 1 and that this ratio was more critical than the ratio of either compound to the acetate. A synthetic blend of 100 : 10 : 1 acetatendash;alcoholndash;aldehyde was effective at attracting male moths in the field. Additional compounds found in both extract and aeration samples failed to significantly increase trap catches of male moths, although some of these minor components elicited responses from male moth antennae in coupled gas chromatography–electroantennography studies.     

Sexual Maturation and Temporal Variation of Neural Responses in Adult Colorado Potato Beetles to Volatiles Emitted by Potato Plants

Neural responses of the Colorado potato beetle (CPB), Leptinotarsa decemlineata to volatiles emitted by potato plants, Solanum tuberosum L were investigated. Amplitudes of electroantennograms to measured amounts of a standard odorant, (Z)-3-hexenyl acetate, increased from day of emergence through at least six to eight days of adulthood. Among 20 potato volatiles examined, several constitutive compounds, e.g., the green leaf volatiles (Z)-3-hexen-1-ol, (E)-2-hexen-1-ol, and (Z)-3-hexenyl butyrate, and systemic volatiles released primarily in response to insect feeding, e.g., (±)-linalool, nonanal, methyl salicylate, and indole, were the most effective stimuli. A statistic called linear age-skew (linear orthogonal polynomial) was used to examine differences in responses to potato volatiles between young and mature CPB. Based on plots of linear age-skew and overall neural responsiveness, 10 volatiles could be identified for which responses increased at a rate similar to or greater than the standard. The results are discussed with regard to the relationship of the CPB to its host plant and developmental studies of insect sensory responses to chemical signals.