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昆虫性信息素具有微量、高效、绿色等优点,利用性信息素防治害虫具有良好的应用前景。但随着对性信息素的研究不断深入,性信息素田间释放速率较快、易分解等问题日益凸显。为提高性信息素对银锭夜蛾的防治效果,以银锭夜蛾性信息素主要成分顺-7-十二碳烯乙酸酯(Z7-12:Ac)为母体结构,通过醇与酰氯或酸酐的反应,合成结构稳定且新颖的6种性信息素类似物,包括顺-7-十二碳烯-2,2-二氟代乙酸酯(Y1),顺-7-十二碳烯-2,2,2-三氟乙酸酯(Y2),顺-7-十二碳烯-2,2,3,3,3-五氟丙酸酯(Y3),顺-7-十二碳烯-2,2,2-三氟甲磺酸酯(Y4),顺-7-十二碳烯-2-溴丙酸酯(Y5),顺-7-十二碳烯-3-甲硫基丙酸酯(Y6),其结构经核磁共振(NMR)和高分辨质谱(HR-MS)表征。室内生物活性研究表明:所有的性信息素类似物在触角电生理试验(EAG)中均表现出一定的生物活性,其中Y1具有较好的剂量-效应关系,在浓度10 μg时EAG直接刺激响应值为2.07 mV。 相似文献
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松毛虫性信息素微量成分鉴定方法的研究 总被引:9,自引:0,他引:9
采用气相色谱-质谱分析确认了顺-5-,反-7-十二碳二烯乙酸酯是思茅松毛虫性信息素腺体的主要成分(次要成分由于含量极微且受杂质干扰,未能获得全扫描质谱图)。利用高分辨率毛细管气相色谱分析了思茅松毛虫性信息素腺体提取物的酯基转移和乙酰化反应的衍生物,进一步确认了顺-5-,反-7-十二碳二烯醇是思茅松毛虫性信息素腺体中的微量成分。探讨了功能团相互转换微量化学反应法鉴定松毛虫性信息素腺体中微量成分功能团和立体构型的优点。强调了性信息素微量成分鉴定工作在昆虫化学通讯系统研究中的重要性。 相似文献
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梨小食心虫性信息素顺-8-十二碳烯-1-醇乙酸酯及其反式异构体的合成 总被引:8,自引:0,他引:8
梨小食心虫(Grapholitha molesta Busck)是一种世界性的梨、桃、苹果等果树害虫.此虫在我国分布甚广.1969年Roelofs等鉴定其性信息素的结构为顺-8-十二碳烯-1-醇乙酸酯(1)[1],其后报道1与少量反-8-十二碳烯-1-醇乙酸酯(2)合用,则引诱活性可以增强[2]. 相似文献
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苹果蠹蛾性信息素的合成研究进展 总被引:2,自引:0,他引:2
综述了用Wittig反应构建烯烃、炔化物还原、烯烃硼氢化、山梨酸衍生物格氏偶联、油脂的氧化-还原等方法,合成苹果蠹蛾性信息素(8E,10E-十二碳二烯-l-醇)的研究进展。并介绍了其部分类似物的合成方法。参考文献21篇。 相似文献
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In this paper we present analytical studies of the sex pheromone components of the Egyptian armyworm Spodoptera littoralis (Lepidoptera, Noctuidae) by electroantennography (EAG) and coupled gas chromatography-electroantennographic detection (GC-EAD). EAG responses in three different preparations, using an insect's head, an excised antenna and a live insect, have been recorded. EAG depolarizations of live insects were significantly higher than those elicited by the insect's head or the excised antenna. The responses were dose-dependent. Live insects also allowed regular pheromone stimulations for 40 min with only 38% decrease of the EAG initial depolarization. The synthetic pheromone blend elicited the highest EAG activity (2.0+/-0.3 mV), followed by the major compound (Z,E)-9,11-tetradecadienyl acetate (I) (1.54+/-0.1mV), and the minor components (Z)-9-tetradecenyl acetate (II), (E)-11-tetradecenyl acetate (III), tetradecyl acetate (IV) and (Z)-11-tetradecenyl acetate (V) (1.21-1.32 mV range). (Z,E)-9,12-tetradecadienyl acetate (VI), although not present in the pheromone blend of our strain, also showed an EAG activity (1.32+/-0.09 mV) similar to that of the monoenic components. GC-EAD responses confirmed the composition of the sex pheromone blend, the major response being elicited by the main component I followed by the other minor compounds II-V. The new dienic compound found in the female pheromone gland, (E,E)-10,12-tetradecadienyl acetate (VII), was not electrophysiologically active. Regarding sensitivity, the minimum amount detectable to elicit an antennal response in our GC-EAD system was 15 pg of the major component. In our system, which was built with cheap and easily available materials, no cooling of the effluent at the outlet of the chromatographic column is required. 相似文献
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Novel monomeric and polymeric liquid crystalline compounds were synthesized as stationary phases for gas chromatography (GC) and supercritical fluid chromatography (SFC). Monomeric liquid crystalline compounds were used in packed column gas chromatography for the separation of isomeric aromatic compounds and insect sex pheromones. Liquid crystalline polymers possess long nematic ranges and a uniform coating was easily achieved in glass and fused silica capillaries, which could stand temperatures up to 250°C in GC and pressures of 200 MPa at 160°C in SFC. The columns provide excellent selectivity and resolution for fused ring aromatic compounds such as the isomers anthracene and phenanthrene or triphenylene and chrysene. 相似文献
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Two insect colonies of Elasmopalpus lignosellus were reared in our laboratory, the first being initiated from pupae obtained from a cornfield in the region of Sete Lagoas, Minas Gerais and the second from a cornfield in the region of Goiania, Goiás. From the two colonies, two extracts were prepared from the pheromone glands of virgin E. lignosellus females. The extract obtained from the first colony was designated as extract 1 while the extract obtained from the second colony was designated as extract 2. Extract 1 was analyzed by gas chromatography-mass spectrometry (GC-MS) with (Z)-9-hexadecenyl acetate [(Z)-9-HDA] and (Z)-11-hexadecenyl acetate [(Z)-11-HDA] being identified and confirmed by the formation of DMDS derivatives. In addition, a third acetate, which could be either (E)-8-hexadecenyl acetate [(E)-8-HDA] or (E)-9-hexadecenyl acetate [(E)-9-HDA] was detected by GC-MS. Extract 2 was analyzed by gas chromatography (GC) and gas chromatography-electroannetography (GC-EAD) revealing the presence of (Z)-11-HDA and (Z)-9-TDA. In addition, the same compounds elicited a response with the E. lignosellus male antenna obtained from the second insect colony. Electroantennography (EAG) screening with the male E. lignosellus antenna (obtained from the second insect colony) was conducted with the 23 possible tetradecenyl acetates (TDA) and 22 hexadecenyl acetates (HDA) as standards. Out of the 23 TDA isomers evaluated, only (Z)-9-TDA elicited a response and out of the 22 HDA [(Z) and (E) isomers gamma2 to delta13] evaluated only (Z)-11-HDA elicited a response. The acetate compositions of two extracts obtained from insects originating from the two states (Minas Gerais and Goiás) of Brazil were different from one another as well as from that obtained from insects in Tifton, GA, USA. The bioactivity data (GC-EAD) of the extract 2 differed from those reported for the Tifton, GA, USA population. These data suggest polymorphism in relation to the insect populations found in Brazil and in the USA. The possibility of the existence of an E. lignosellus sub-species cannot be ruled out. 相似文献
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A sensitive technique is described for the analysis of insect pheromones. Insect extracts are separated into fractions by column chromatography and are analyzed directly by quadrupole mass fragmentography on high-resolution glass capillary columns and by mass spectrometry. Applications are illustrated with two important pests. In the codling moth, trans-8, trans-10-dodecadien-1-ol was found to be present at a level of 3.5 ng per female, and in the European grapevine moth trans-7, cis-9-dodecadienyl acetate at a level of 1.6 ng. Both compounds appear to be present in high isomeric purity in the female insect and are absent in the corresponding males. 相似文献
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Two random reduction procedures (NH2NH2/H2O2 and NH2NH2/O2) were compared and conditions optimized for the reduction of two synthetic pheromone compounds (9Z,11E)-9,11-tetradecadienyl acetate and (9Z,12E)-9,12-tetradecadienyl acetate on a 300 microg scale at 60 degrees C. The relative amounts of the four products (completely reduced acetate, unreacted diene acetate and two monoene acetates), characterized by gas chromatography (GC) from the reaction mixture, depended on the reaction conditions. The reduction was straightforward without any detectable undesired side products. The reaction yields were reproducible with both the reducing reagents. The optimized reduction conditions thus established were utilized to reduce seven synthetic compounds (four diene and three triene acetates) on a micro scale (5 microg). In all cases, expected compounds were identified by GC-MS. After reduction, two methods were used to locate the position of double bonds in the partially reduced compounds. In the first method, the products from the above seven compounds were isolated by extraction with hexane and reacted with dimethyl disulfide to give the DMDS adducts. In the second method ("one-pot"), the reduced compounds were not isolated but instead, the solvents were evaporated and the DMDS derivatives formed. In both cases, determination of the position of the double bonds was possible by GC-MS analyses. The complete procedure (reduction and DMDS derivative formation) could be carried out on a 100 ng scale. Although neither of the partial reduction methods offered significant advantages over the other, partial reduction with NH2NH2/H2O2 was more convenient and hence should be the method of choice, together with DMDS derivative formation to locate double bonds in pheromones. In addition, a new procedure is described using ND2ND2/H2O2 and DMDS derivative formation capable of distinguishing between the double bond positions in (Z)-9-tetradecenyl acetate and (9Z,12E)-9,12-tetradecadienyl acetate (1:1 mixture). 相似文献
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Some insect sex pheromones 10-dodecen-1-ol acetates 5a(Z/E) and 12-tetradecen-1-ol acetates 5b(Z/E) have been synthesized from cis-13-docosenoic acid la and cis-15-tetracosenoic acid Ib via the isomerization of key intermediates 11-dodecen-1-ol acetate 4a and 13-tetradodecen-1-ol acetate 4b. 相似文献
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昆虫信息化合物相对蒸气压的气相色谱分析 总被引:1,自引:0,他引:1
报道了用012%胆固醇对氯肉桂酸酯(CPCC)和008%OV101液晶相毛细管柱气相色谱法测定化合物相对蒸汽压的方法及对60个昆虫信息化合物相对蒸汽压的测定结果。由此可直接利用公式计算昆虫信息素各组分的释放速率。使合成信息素最佳配比的选择方法大为简化。 相似文献
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Matthias Schott Christoph Wehrenfennig Tina Gasch Rolf-Alexander Düring Andreas Vilcinskas 《Analytical and bioanalytical chemistry》2013,405(23):7457-7467
Mating disruption is a sustainable method for the control of insect pests, involving the release of synthetic sex pheromones that disrupt the olfactory localization of females by males. However, the development and refinement of this strategy is hampered because current instruments lack the sensitivity to detect volatile organic chemicals in the field, and portable electroantennograms produce non-comparable relative units and distorted results in the presence of plant volatiles. To address the demand for more sensitive instruments that are suitable for the rapid in situ detection of airborne pheromones, we have developed a portable, automated needle trap device connected to a gas chromatograph, mass spectrometer, and electroantennographic detector (NTD-GC-MS/EAD) suitable for field applications. We tested the instrument by measuring the concentration of the sex pheromone (E,Z)-7,9-dodecadienyl acetate, which is used to disrupt the mating of the European grapevine moth Lobesia botrana (Lepidoptera: Tortricidae). Our data confirm that the instrument generates highly reproducible results and is highly sensitive, with a detection threshold of 3 ng/m3 (E,Z)-7,9-dodecadienyl acetate in outside air. 相似文献
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Anat Levi-Zada Daniela FeferLeonid Anshelevitch Anna LitovskyMarie Bengtsson Galina GindinVictoria Soroker 《Tetrahedron letters》2011,52(35):4550-4553
The identification of the sex pheromone of the lesser date moth, Batrachedra amydraula (Meyrick) was based on GC-MS analysis of volatiles released by virgin females using sequential SPME auto-sampling of headspace and by synthesis of the key component, (4Z,7Z)-4,7-decadien-1-yl acetate. Substantial capture of males in a date palm plantation using a bait consisting of the key component and 5Z-decen-1-yl acetate in a ratio of 1:2 indicated that these are the essential components of the sex pheromone. Addition of 4Z-decen-1-yl acetate and decan-1-yl acetate, which were also identified, did not affect trap-capture. The lesser date moth is the first member of the Batrachedridae whose sex pheromone has been identified. (4Z,7Z)-4,7-Decadien-1-yl acetate is a novel compound among moth sex pheromones. 相似文献