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1.
(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.  相似文献   

2.
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.  相似文献   

3.
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.  相似文献   

4.
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.  相似文献   

5.
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.  相似文献   

6.
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.  相似文献   

7.
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.  相似文献   

8.
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.  相似文献   

9.
The grass webworm Herpetogramma licarsisalis (Lepidoptera: Crambidae), which has recently established in pasture in Northland, New Zealand, is an important pest of many tropical and subtropical grasses. Two pheromone components, (Z)-11-hexadecen-1-yl acetate (Z11–16:Ac) and (11Z,13E)-hexadecadien-1-yl acetate (Z11,E13–16:Ac), were identified in pheromone gland extracts of female moths by gas chromatography (GC), GC-electroantennographic detection, and GC-mass spectrometry in conjunction with microchemical tests (dimethyldisulfide and 4-methyl-1,2,4-triazoline-3,5-dione derivatizations). Z11,E13–16:Ac and its geometric isomer (11E,13Z)-hexadecadien-1-yl acetate (E11,Z13–16:Ac) were synthesized via stereoselective Wittig reactions, and the identity of the diene present in the pheromone glands was confirmed to be Z11,E13–16:Ac. Field bioassays at Indooroopilly in Brisbane, Australia, established that Z11,E13–16:Ac was necessary and sufficient for attraction of male grass webworm moths and that the corresponding alcohol, (11Z,13E)-hexadecadien-1-ol (Z11,E13–16:OH), had a strong inhibitory effect on trap catches at the ratios tested. When mixed with Z11,E13–16:Ac in various ratios, Z11–16:Ac had no effect on the attractiveness of lures. Electronic supplementary material The online version of this article (doi:) contains supplementary material, which is available to authorized users.  相似文献   

10.
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.  相似文献   

11.
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).  相似文献   

12.
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.  相似文献   

13.
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.  相似文献   

14.
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.  相似文献   

15.
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.  相似文献   

16.
Field attraction ofCydia nigricana males to synthetic female sex pheromone (E,E)-8,10-dodecadien-1-yl acetate, formulated on red rubber septa, declined continuously during two weeks. This was due to isomerization of (E,E)-8,10-dodecadien-1-yl acetate: eight days after application of purifiedE,E isomer, the proportion ofE,Z;Z,E; andZ,Z isomers in rubber septa aged in the laboratory was 4%; a 5% addition of any one of these isomers to fresh lures of (E,E)-8,10-dodecadien-1-yl acetate significantly reduced male attraction. Stereospecific syntheses of (E,Z)-, (Z,E)-, and (Z,Z)-8,10-dodecadien-1-yl acetate are described. The pheromone gland ofCydia nigricana contains 0.8 ng/female of (E,E)-8,10-dodecadien-1-yl acetate, accompanied by three monounsaturated acetates, (E)-9-dodecen-1-yl acetate, (Z)-5-tetradecen-1-yl acetate, and (Z)-7-tetradecen-1-yl acetate (0.1 ng/female each). These compounds did not augment male trap catch when added to (E,E)-8,10-dodecadien-1-yl acetate.  相似文献   

17.
(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.  相似文献   

18.
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.  相似文献   

19.
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.  相似文献   

20.
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.  相似文献   

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