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 components of the fruit-tree leaf roller,Archips argyrospilus (Walker) (Lepidoptera: Tortricidae), in British Columbia

In field experiments in the Okanagan Valley, British Columbia, the pheromone blend of (11Z)-tetradecen-1-ol acetate (Z11-14:OAc), (11E)-tetradecen-1-ol acetate (E 11-14:OAc), (9Z)-tetradecen-1-ol acetate (Z9-14:OAc) and dodecan-1-ol acetate (12: OAc) at a 1006421 ratio (western FTLR blend) attracted significantly more male fruit-tree leaf roller (FTLR),Archips argyrospilus (Walker), than did the previously reported four-component blend and modifications thereof. Addition of (11Z)-tetradecen-1-ol (Z11-14:OH) to the western FTLR blend in a ratio of 4% relative toZ11-14: OAc further significantly enhanced attraction. Compounds were identified and their ratio determined by coupled gas chromatographic-electroantennographic (GC-EAD) and coupled GC-mass spectrometric analyses of female FTLR pheromone gland extracts and by retention index calculations of candidate pheromone components. Determination and use of geographically specific pheromonal blends may be required for optimal, semiochemical-based biorational control of FTLR and other lepidopteran orchard pests.     

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.     

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 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.     

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.     

Sex pheromone of the avocado pest,Amorbia cuneana (Walsingham) (Lepidoptera: Tortricidae)

The major volatile components in the extract of the female sex pheromone gland ofAmorbia cuneana consisted of (E,E)- and (E,Z)-10,12-tetradecadien-1-ol acetates. The identification was based on electroantennogram bioassay of gas Chromatographic effluent from sex pheromone gland extract, relative retention times on polar and nonpolar gas chromatographic columns, chemical degradation (ozonolysis, saponification), mass spectrometry, chemical synthetic methods, and field tests. Based on mass spectrometry and retention times by capillary gas chromatography, traces of (E)-10-tetradecen-1-ol acetate and 1-tetradecanol acetate were also present in the extract. Traps baited with a combination of synthetic (E,E)- and (E,Z)-10,12-tetradecadien-1-ol acetates caught more males than did traps baited with females.This paper reports the results of research only. Mention of a commercial product in this paper does not constitute a recommendation by the U.S. Department of Agriculture.     

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.     

Sex pheromone of female african white rice stem borer,Maliarpha separatella (Lepidoptera: Pyralidae) from Sierra Leone: Identification and field testing

Analysis of ovipositor washings of femaleMaliarpha separatella from Sierra Leone by high-resolution gas chromatography (GC) linked to a male electroantennograph (EAG) indicated the presence of three electrophysiologically active compounds. The GC retention times of these compounds were consistent with those of (Z)-9-tetradecen-1-ol, (Z,E)-9,12-tetradecadien-1-ol, and (E,E)-10,12-tetradecadien-1-ol. Analysis by El and CI mass spectrometry of ovipositor washings confirmed these identifications and also indicated the presence of the saturated analog, tetradecan-1-ol. There was no evidence, from these analyses, of the corresponding aldehydes or acetates. The EAG-active compounds were present in the ovipositor washings in a ratio of approximately 23.51, with the major component constituting approximately 0.4 ng per ovipositor. GC-MS analysis of entrained female effluvia confirmed that the EAG-active compounds were released by virgin females. Field testing of the EAG-active compounds indicated that (Z,E)-9,12-tetradecadien-1-ol and (E,E)10,12-tetradecadien-1-ol were attractive to male moths in ratios of between 9:1 and 39:1, while (Z)-9-tetradecen-1-ol was found to reduce trap catch when added to blends of the other two compounds.     

Sex pheromone components of the variegated leafroller moth,Platynota flavedana

Female tip extracts of the variegated leafroller moth,Platynota flavedana (Clemens), were analyzed and found to contain a mixture of (E)-11-tetradecen-1-ol and (Z)-11-tetradecen-1-ol (91), as well as a mixture of (E)-11-tetradecenyl acetate and (Z)-11-tetradecenyl acetate (2-31). Small amounts of tetradecen-1-ol and tetradecyl acetate probably are also present. In the field, a mixture of the two alcohols (8416,EZ ratio) attracted significantly more male moths of this species than any other mixture tested. The data indicate that the acetates are probably not used as pheromone components.Lepidoptera:Tortricidae:Tortricinae.This research was supported in part by the Rockefeller Foundation and by NSF Grant No. GB-38020.     

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.     

(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.     

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).     

Sex Pheromones and Reproductive Isolation of Three Species in Genus <Emphasis Type="Italic">Adoxophyes</Emphasis>

We tested differences in female pheromone production and male response in three species of the genus Adoxophyes in Korea. Females of all three species produced mixtures of (Z)-9-tetradecenyl acetate (Z9–14:OAc) and (Z)-11-tetradecenyl acetate (Z11–14:OAc) as major components but in quite different ratios. The ratio of Z9–14:OAc and Z11–14:OAc in pheromone gland extracts was estimated to be ca. 100:200 for Adoxophyes honmai, 100:25 for Adoxophyes orana, and 100:4,000 for Adoxophyes sp. Field tests showed that males of each species were preferentially attracted to the two-component blends of Z9–14:OAc and Z11–14:OAc mimicking the blends found in pheromone gland extracts of conspecific females. The effects of minor components identified in gland extracts on trap catches varied with species. Addition of 10-methyldodecyl acetate (10me-12:OAc) or (E)-11-tetradecenyl acetate (E11–14:OAc) to the binary blend of Z9–14:OAc and Z11–14:OAc significantly increased captures of A. honmai males, whereas E11–14:OAc exhibited a strongly antagonistic effect on catches of Adoxophyes sp. males. Moreover, (Z)-9-tetradecen-1-ol (Z9–14:OH) or (Z)-11-tetradecen-1-ol (Z11–14:OH) added to the binary blends increased attraction of male A. orana but not A. honmai and Adoxophyes sp. males, suggesting that these minor components, in addition to the relative ratios of the two major components, play an important role in reproductive isolation between Adoxophyes species in the southern and midwestern Korea where these species occur sympatrically.     

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.     

Characterization of Pheromone Blend for Grapevine Moth, Lobesia botrana by Using Flight Track Recording

The behavioral responses of Lobesia botrana males to calling females, pheromone gland extracts, and synthetic sex pheromones were recorded in a wind tunnel. Gland extracts and synthetic pheromones were released from a pheromone evaporator. The numbers of males reaching the source and their flight tracks in response to calling females and pheromone gland extracts were compared to those of synthetic blends. Upwind flights to natural sex pheromone were straighter and faster than to a three-component blend of (E)-7,(Z)-9-dodecadienyl acetate (E7,Z9–12:Ac), (E)-7,(Z)-9-dodecadien-1-ol (E7,Z9–12:OH), and (Z)-9-docecenyl acetate (Z9–12:Ac) (100:20:5). The optimum ratio of E7,Z9–12:OH and Z9–12:Ac to E7,Z9–12:Ac was found to be 5% and 1%, respectively. An additional seven compounds identified in the sex pheromone gland were investigated for their biological activity. Two unsaturated acetates, i.e., (E)-9-dodecenyl acetate (E9–12:Ac) and 11-dodecenyl acetate (11–12:Ac), increased the number of males reaching the source as well as straightness, linear velocity, and decreased the track angle of upwind flight. Optimum response was obtained by releasing 10 pg/min E7,Z9–12:Ac in a mixture with 0.5 pg/min E7,Z9–12:OH, 0.1 pg/min Z9–12:Ac, 0.1 pg/min E9– 12:Ac and 1 pg/min 11-12–Ac. The saturated acetates previously identified in the female glands were biologically inactive.     

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.     

Sex pheromone ofPandemis heparana (Den. and Schiff.) (Lepidoptera:Tortricidae)

90% (Z)-11-tetradecen-1-yl acetate, 5% (Z)-9-tetradecen-1-yl acetate, 5% (Z)-11-tetradecen-1-ol, dodecyl acetate (<1%), and tetradecyl acetate (<1%) were identified from gland extracts ofPandemis heparana females by gas chromatography and gas chromatography-mass spectrometry analysis (including mass fragmentography studies), chemical characterization, total synthesis, laboratory and field bioassays. In the field, a mixture of (Z)-11-tetradecen-l-yl acetate and (Z)-9-tetradecen-l-yl acetate (955) was found to be essential for attractiveness ofP. heparana males.     

Isolation, Identification, Synthesis, and Field Evaluation of the Sex Pheromone of the Brazilian Population of Spodoptera frugiperda

Several studies have shown intraspecific geographical variation in the composition of sex pheromones. Pheromone lures from North America and Europe were not effective against the fall armyworm Spodoptera frugiperda (Smith, 1797) (Lepidoptera: Noctuidae) in Brazil, so we examined the composition of the sex pheromone produced by females from Brazilian populations. Virgin female gland extracts contained (Z)-7-dodecenyl acetate (Z7-12:Ac), (E)-7-dodecenyl acetate (E7-12:Ac), dodecyl acetate, (Z)-9-dodecenyl acetate, (Z)-9-tetradecenyl acetate (Z9-14:Ac), (Z)-10-tetradecenyl acetate, tetradecyl acetate/(Z)-11-tetradecenyl acetate (Z11-16:Ac), and (Z)-11-hexadecenyl acetate. The relative proportions of each acetate were 0.8:1.2:0.6:traces:82.8:0.3:1.5:12.9, respectively. This is the first time that E7-12:Ac has been reported from the pheromone gland of S. frugiperda. Only three compounds, Z9-14:Ac, Z7-12:Ac, and E7-12:Ac, elicited antennal responses, and there were no differences in catch between traps baited with either Z7-12:Ac + Z9-14:Ac or Z7-12:Ac + Z9-14:Ac + Z11-16:Ac blends. However, the Z7-12:Ac + Z9-14:Ac + E7-12:Ac blend was significantly better than Z7-12:Ac + Z9-14:Ac, indicating that E7-12:Ac is an active component in the sex pheromone of the Brazilian populations of S. frugiperda.     

Green Leaf Volatiles Interrupt Pheromone Response of Spruce Bark Beetle, Ips typographus

A synthetic mixture of nine green leaf volatiles (GLVs) including linalool was tested on antennae of Ips typographus (L.) with coupled gas chromatographic–electroantennographic detection (GC-EAD). Strong responses were found to 1-hexanol, (Z)-3-hexen-1-ol, and (E)-2-hexen-1-ol. Weak responses were recorded to (E)-3-hexen-1-ol, (Z)-2-hexen-1-ol and linalool, while hexanal, (E)-2-hexenal and (E)-3-hexenyl acetate elicited no EAD responses. In a laboratory walking bioassay, the attraction of I. typographus females to a synthetic pheromone source was significantly reduced when a mixture of the three most EAD-active GLV alcohols was added to the source. Further reduction in response was obtained when these three alcohols were combined with verbenone (Vn). In field trapping experiments, a blend of 1-hexanol, (Z)-3-hexen-1-ol, and (E)-2-hexen-1-ol reduced I. typographus trap catches by 85%, while ca. 70% reduction of trap catch was achieved by Vn or a blend of (E)-3-hexen-1-ol, (Z)-2-hexen-1-ol, and linalool. The strongest disruptive effect was found when Vn plus a blend of the three most EAD active GLV alcohols was added to the pheromone trap (95% catch reduction). Adding the blend of the three most EAD active alcohols to pheromone-baited traps significantly reduced the proportion of males captured. These three GLV alcohols were also disruptive in the laboratory and in the field when tested individually. Hexanal, (E)-2-hexenal, and (Z)-3-hexenyl acetate were inactive both in the lab and in the field. Our results suggest that these nonhost green leaf alcohols may explain part of the host selection behavior of conifer-attacking bark beetles and may offer a source of inhibitory signals for alternative management strategy for forest protection.