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1.
A chemical analysis of the crude sex pheromone gland extracts of virgin calling Paranthrene tabaniformis females, obtained from the European part of Kazakhstan, revealed the presence of five compounds: (3E,13Z)-octadeca-3,13-dien-1-ol (E3,Z13-18:OH), (3Z,13Z)-octadeca-3,13-dien-1-ol (Z3,Z13-18:OH), (2E,13Z)-octadeca-2,13-dien-1-ol (E2,Z13-18:OH), (13Z)-octadec-13-en-1-ol (Z13-18:OH), and octadecan-1-ol (18:OH) at the ratios 64.0:32.4: 1.4:0.9:1.3, which are structurally related to sex pheromone components of clearwing moths. Our previous field tests showed synergistic effects of Z3,Z13-18:OH and E2,Z13-18:OH to attract P. tabaniformis males, when these compounds were tested in binary mixtures with the known sex pheromone E3,Z13-18:OH. The three dienic alcohols should all be considered as sex pheromone components of the P. tabaniformis species, while the role of Z13-18:OH and 18:OH remained unclear.  相似文献   

2.
Female sex pheromone of a clearwing moth Nokona feralis (Leech) (Lepidoptera: Sesiidae), a pest of kiwifruit, was identified to be a 7:3 mixture of (3E,13Z)-3,13-octadecadienyl acetate (E3,Z13-18:OAc) and (3E,13Z)-3,13-octadecadien-1-ol (E3,Z13-18:OH) by GC-EAD and GC/MS analyses. Males were attracted to wide-range mixtures of E3,Z13-18:OAc and E3,Z13-18:OH, and a 7:3 mixture of those two compounds strongly attracted the males in the field.  相似文献   

3.
The Japanese persimmon treeborer, Synanthedon tenuis (Butler) (Lepidoptera: Sesiidae), is a harmful pest of persimmon trees (Diospyros spp.). Because males of this species are known to be attracted by (3Z,13Z)-3,13-octadecadienyl acetate (Z3,Z13-18:OAc), a mating disruptant composed of a 1:1 mixture of Z3,Z13-18:OAc and the (3E,13Z)-isomer, the original target of which is an allied pest, S. hector (Butler), has been diverted to control S. tenuis. However, the sex pheromone secreted by S. tenuis females has not been characterized. Analyses of pheromone gland extracts using gas chromatography (GC) equipped with an electroantennographic detector (GC-EAD) and GC combined with mass spectrometry (GC–MS) detected only Z3,Z13-18:OAc, and no other known sesiid pheromone components were found. In a persimmon orchard, S. tenuis males were selectively attracted by a lure baited with Z3,Z13-18:OAc among four geometrical isomers of 3,13-octadecadienyl acetate, indicating that males strictly discriminated among the configurations of the two double bonds. Lures baited with single Z3,Z13-18:OAc attracted only S. tenuis. Further field experiments revealed that the attractiveness of Z3,Z13-18:OAc is significantly inhibited by the addition of the (3E,13Z) isomer or the parent alcohol.  相似文献   

4.
Sex attractants for 3 Sesiidae and 3 Tineidae moth species in West-Kazakhstan and Lithuania were discovered by field screening tests of (3Z,13Z)-, (3E,13Z)- and (2E,13Z)-octadecadien-1-ols and their acetates as well as of some binary mixtures of these compounds. Total amount of chemicals was 0.3 mg/dispenser. Males of Synanthedon serica were attracted by a 5:5 mixture of 3E,13Z-18:OAc and 2E,13Z-18:OAc, Chamaesphecia bibioniformis by a 9:1 mixture of 3Z,13Z-18:OAc and 3E,13Z-18:OAc, Paranthrene tabaniformis by a 1:9 mixture of 3Z,13Z-18:OH and 3E,13Z-18:OH, Tinea nonimella by a 1:9 mixture of 3E,13Z-18:OH and 2E,13Z-18:OH, Monopis monachella by a 1:9 mixture of 3Z,13Z-18:OH and 2E,13Z-18:OH, and Nemaxera betulinella by a 9:1 mixture of 2E,13Z-18:OAc and the corresponding alcohol. The periods of attraction to the traps were registered for males of S. serica and Ch. bibioniformis and were found to occur at 15-18 and 15-17 o'clock, local time, respectively.  相似文献   

5.
Several geometrical isomers of 3,13- and 2,13-octadecadien-1-ols and their acetates were synthesized starting from 1,8-octanediol or 1,9-nonanediol utilizing acetylene coupling reactions. In addition to commercially available compounds, all geometrical isomers of each dienyl compound were analyzed by NMR and GC-MS to accumulate chemical data for studies of sex pheromones secreted from clearwing moths classified into the family Sesiidae of Lepidoptera. Although acetoxy derivatives of the 3,13- and 2,13-dienes showed almost the same mass spectra, the alcohols were distinguished by comparing the relative intensities of [M-18](+) at m/z 248, indicating direct differentiation of the two positional isomers without derivatization. Furthermore, each geometrical isomer eluted from a high-polar GC column with a different retention time. Base on these data, a pheromone gland extract of a sesiid moth, Nokona pernix, was analyzed by GC-EAD and GC-MS, and two EAG-active components were identified, viz., the (3E,13Z)- and (3Z,13Z)-isomers of 3,13-octadecadien-1-ol in a ratio of 9:1. In the field, the synthetic compounds mixed in 9:1 ratio attracted N. pernix males well, while a single component scarcely attracted the males. The number of attracted males peaked in the middle of June, and a small second peak was observed in August.  相似文献   

6.
The sex pheromone blend of the butterbur borer, Ostrinia zaguliaevi (Lepidoptera: Pyralidae) was analyzed by means of gas chromatography-electroantennographic detection (GC-EAD), GC-mass spectrometry and a series of wind-tunnel bioassays. Four EAD-active compounds were detected in the female sex pheromone gland extract, and these were identified as tetradecyl acetate (14:OAc), (Z)-9-tetradecenyl acetate (Z9-14:OAc), (E)-11-tetradecenyl acetate (E11-14:OAc) and (Z)-11-tetradecenyl acetate (Z11-14:OAc). The average amounts ± s.d. of the four compounds in a single sex pheromone gland were 7.9±3.7 ng, 10.1±3.2 ng, 1.1±0.5 ng and 11.6±5.1 ng, respectively. In a wind-tunnel bioassay, the ternary blend of Z9-, E11- and Z11-14:OAc at a ratio found in the sex pheromone gland (45:5:50) elicited the same behavioral responses from the males as did virgin females and pheromone gland extract. Removal of any single compound from the ternary blend significantly diminished the pheromonal activity, whereas addition of 14:OAc to the ternary blend had no effect on the males' behavioral responses. Therefore, it was concluded that the sex pheromone blend of O. zaguliaevi is composed of Z9-14:OAc, E11-14:OAc and Z11-14:OAc at a ratio of 45:5:50.  相似文献   

7.
《Journal of Asia》2020,23(4):935-941
Hellula undalis is a harmful insect pest of green mustard in the Mekong Delta of Vietnam. In order to establish a tool for a sustainable pest control program, the sex pheromone of H. undalis inhabiting the Mekong Delta was examined. GC-EAD and GC–MS analyses of pheromone gland extracts from the virgin females elucidated three new components, (Z)-11-tetradecenyl acetate (Z11-14:OAc), (Z)-11-hexadecenal (Z11-16:Ald), and (11E,13E)-11,13-hexadecadien-1-ol, in addition to the known pheromone component (11E,13E)-11,13-hexadecadienal (E11,E13-16:Ald). Double bond positions of the two monoenyl components were determined by GC–MS analysis of the pheromone extract treated with dimethyl disulfide. On the other hand, GC–MS analysis of the female body extract detected the unsaturated hydrocarbon (3Z,6Z,9Z)-3,6,9-tricosatriene (Z3,Z6,Z9-23:H). Field examinations of their synthetic compounds indicated the significant role of E11,E13-16:Ald as a major component and a clear synergistic effect of the two monoenyl compounds as a minor component. Although the 3:3:7 mixture of Z11-14:OAc, E11-16:Ald, and E11,E13-16:Ald captured the largest number of males among the tested mixtures, the activity was still quite a bit lower than that of virgin females. However, the 3:3:7:1 mixture, which was prepared by adding a small amount of Z3,Z6,Z9-23:H to the 3:3:7 ternary lure, succeeded in attracting males more powerfully than the females did. This strong synergistic effect was not observed when the triene was added to unmixed E11,E13-16:Ald, indicating important roles of not only the triene but also the two monoenyl compounds as natural pheromone components.  相似文献   

8.
Several grams of labelled trans linoleic and linolenic acids with high chemical and isomeric purities (>97%) have been prepared for human metabolism studies. A total of 12.5 g of (9Z, 12E)-[1-(13)C]-octadeca-9,12-dienoic acid and 6.3 g of (9Z,12Z, 15E)-[1-(13)C]-octadeca-9,12,15-trienoic acid were obtained in, respectively, seven steps (7.8% overall yield) and 11 steps (7% overall yield) from 7-bromo-heptan-1-ol. The trans bromo precursors used for the labelling were synthesised by using copper-catalysed couplings. The trans fatty acids were then obtained via the nitrile derivatives. A total of 23.5 g of (9Z,12Z)-[1-(13)C]-octadeca-9, 12-dienoic acid and 10.4 g of (9Z,12Z,15Z)-[1-(13)C]-octadeca-9,12, 15-trienoic acid were prepared in five steps in, respectively, 32 and 18% overall yield. Large quantities of bromo and chloro precursors were synthesised from the commercially available acid according to Barton's procedure. In all cases, the main impurities (>0.5%) of each labelled fatty acid have been characterised.  相似文献   

9.
Dodecyl acetate (12:OAc) ( E )-10-dodecenyl acetate ( E 10-12:OAc) and ( E )-10-dodecenol ( E 10-12:OH) in the ratio 8 : 80 : 12 were collected by solid phase micro-extraction of the volatiles emitted by virgin signalling females of the spotted tentiform leafminer moth, Phyllonorycter blancardella . The same compounds in the ratio 8 : 79 : 13 were extracted from the sex pheromone glands of virgin signalling females of the same species. The chemical structures of the compounds were identified by gas chromatography and mass spectrometry. Trapping results obtained from field tests using synthetic components of the sex pheromone demonstrated that only one component, E 10–12:OAc, was essential for the attraction of conspecific males and should be considered as a sex pheromone.  相似文献   

10.
Olfactory receptor neuron (ORN) response was measured to assess why some males ("rare males") of the Asian corn borer (ACB), Ostrinia furnacalis, have a broad behavioral response to fly upwind to both the ACB and the European corn borer (ECB), Ostrinia nubilalis, pheromone blends. We performed single-sensillum electrophysiological recordings on ACB males that had been behaviorally assessed for upwind flight response to the ACB blend [60:40 (Z)-12-tetradecenyl acetate (Z12-14:OAc) to (E)-12-tetradecenyl acetate (E12-14:OAc)], as well as to ECB (Z-strain) and ECB (E-strain) blends [3:97 and 99:1 (Z)-11-tetradecenyl acetate (Z11-14:OAc) to (E)-11-tetradecenyl acetate (E11-14:OAc)]. Sensilla from all types of males had large- and small-spike-sized ORNs responding strongly to Z12- or E12-14:OAc, but weakly to Z11- and E11-14:OAc. In the majority of males ("normal males") that flew upwind only to the ACB blend, Z11-14:OAc elicited responses in an intermediate spike-sized ORN associated with behavioral antagonism that is mainly tuned to (Z)-9-tetradecenyl acetate (Z9-14:OAc). In the rare-type ACB males that flew to both the ACB and ECB pheromone blends, Z11-14:OAc did not stimulate this ORN. Increased responsiveness to ancestral pheromone components by ORNs associated with behavioral antagonism could be instrumental in reproductive character displacement, or in reinforcement and reproductive isolation during speciation by helping to increase assortative mating between males and females in derived populations that use novel sex pheromone blends.  相似文献   

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