Isolation and structure of the sex-pheromone of the moth, Nudaurelia cytherea cytherea

The sex-pheromone of Nudaurelia cytherea cytherea has been isolated from the terminal segments of the female moth by solvent extraction, steam distillation, and column and gas-liquid chromatography. The structure was determined by infrared, nuclear magnetic resonance, and mass spectrometry as cis-dec-5-en-1-yl 3-methylbutanoate (isovalerate). The synthetic ester showed activity in field tests.     

The isolation and identification of the female sex pheromones of the red bollworm moth, Diparopsis castanea

The female sex pheromones of the red bollworm moth, Diparopsis castanea, were isolated by solvent extraction of the terminal abdominal segments of the female moth followed by purification of the solvent extract by liquid-solid and gas chromatography. The pheromones were identified by gas chromatographic analysis, micro-ozonolysis, infra-red and mass spectroscopy, and comparison with synthetic material. The major pheromone was 9,11-dodecadien-1-yl acetate (80 : 20 trans : cis). Minor components identified were trans 9-dodecen-1-yl acetate, 11-dodecen-1-yl acetate, and dodecan-1-yl acetate.     

Identification of the Sex Pheromone of the Tree Infesting Cossid Moth Coryphodema tristis (Lepidoptera: Cossidae)

The cossid moth (Coryphodema tristis) has a broad range of native tree hosts in South Africa. The moth recently moved into non-native Eucalyptus plantations in South Africa, on which it now causes significant damage. Here we investigate the chemicals involved in pheromone communication between the sexes of this moth in order to better understand its ecology, and with a view to potentially develop management tools for it. In particular, we characterize female gland extracts and headspace samples through coupled gas chromatography electro-antennographic detection (GC-EAD) and two dimensional gas chromatography mass spectrometry (GCxGC-MS). Tentative identities of the potential pheromone compounds were confirmed by comparing both retention time and mass spectra with authentic standards. Two electrophysiologically active pheromone compounds, tetradecyl acetate (14:OAc) and Z9-tetradecenyl acetate (Z9-14:OAc) were identified from pheromone gland extracts, and an additional compound (Z9-14:OH) from headspace samples. We further determined dose response curves for the identified compounds and six other structurally similar compounds that are common to the order Cossidae. Male antennae showed superior sensitivity toward Z9-14:OAc, Z7-tetradecenyl acetate (Z7-14:OAc), E9-tetradecenyl acetate (E9-14:OAc), Z9-tetradecenol (Z9-14:OH) and Z9-tetradecenal (Z9-14:Ald) when compared to female antennae. While we could show electrophysiological responses to single pheromone compounds, behavioral attraction of males was dependent on the synergistic effect of at least two of these compounds. Signal specificity is shown to be gained through pheromone blends. A field trial showed that a significant number of males were caught only in traps baited with a combination of Z9-14:OAc (circa 95% of the ratio) and Z9-14:OH. Addition of 14:OAc to this mixture also improved the number of males caught, although not significantly. This study represents a major step towards developing a useful attractant to be used in management tools for C. tristis and contributes to the understanding of chemical communication and biology of this group of insects.     

Sex Pheromone Composition and Male Trapping of the Peach Fruit Moth,Carposina sasakii (Matsumura) (Lepidoptera: Carposinidae) in Korea

Sex pheromone composition, mating behavior, and field trapping were analyzed for the peach fruit moth, Carposina sasakii(Matsumura) to develop a monitoring system with its sex pheromone. The upwind flying response of males to female was the most frequent at 4th to 5th hr after lights-off. The highest mating rate was seen at 5th hr after lights-off. The extract of female abdominal tip was analyzed with gas chromatography and proved to have two compounds, (Z)-7-eicosen-11-one and (Z)-7-nonadecen-11-one. In field-trapping, however, a lure containing (Z)-7-eicosen-11-one only showed the highest attractivity.     

Sex pheromone of the European pine shoot moth: chemical identification and field tests

The sex pheromone of the European pine shoot moth, Rhyacionia buoliana, has been isolated and, using chemical methods, its structure shown to be (E)-9-dodecenyl acetate. Field traps containing the synthetic pheromone were consistently more attractive than traps baited with unmated females.     

梨小食心虫成虫性比、日羽化节律及活动规律

梨小食心虫Grapholitha molesta(Busck)是我国重要的果树害虫,本文利用室内饲养观察、室外田间模拟、果园采集饲养等方法系统研究了梨小食心虫成虫的性比及日羽化节律;并利用性诱剂、糖醋液、黑光灯等诱集梨小食心虫成虫,研究了梨小食心虫成虫的活动规律。结果表明:1、田间采集调查表明,梨小食心虫成虫雌雄比例为1∶1.143,室内饲养雌雄比例为1∶1.708。2、梨小食心虫成虫羽化时间主要集中在4:00—10:00,其中以6:00—8:00羽化率最高;梨小食心虫在室外羽化时间比室内推迟2 h左右,室外梨小食心虫比室内普遍晚4 d羽化,这可能与室外温度和光照条件有关;雌虫羽化较雄虫早1² d;3、性诱剂和糖醋液诱集成虫高峰时间均为晚上20:00—22:00,说明梨小食心虫无论雄虫还是雌虫都在此期间活动;夜间各个时间段利用黑光灯都能诱到梨小食心虫成虫,说明梨小食心虫具有趋光性。结论:梨小食心虫雌雄比例为1∶1.12 d;3、性诱剂和糖醋液诱集成虫高峰时间均为晚上20:00—22:00,说明梨小食心虫无论雄虫还是雌虫都在此期间活动;夜间各个时间段利用黑光灯都能诱到梨小食心虫成虫,说明梨小食心虫具有趋光性。结论:梨小食心虫雌雄比例为1∶1.1¹.7,主要在早晨及上午羽化,雌虫较雄虫先羽化;在果园活动时间主要为晚上20:00—22:00。本结果可为梨小食心虫的田间性诱剂监测和诱捕、迷向防治提供指导。     

竹织叶野螟成虫求偶行为及其雌蛾性信息素分泌腺超微结构

【目的】蛾类昆虫性信息素的合成和释放与求偶行为的发生是一致的,其合成和释放的器官是性信息素腺体。为深入了解竹织叶野螟性信息素的分泌生理,开展了竹织叶野螟求偶行为及其性信息素腺体超微结构的研究。【方法】在光周期14L:10D、温度26±2℃、相对湿度80%±10％的室内条件下,观察研究了竹织叶野螟的求偶行为;依据求偶规律研究结果,选取最活跃日龄雌蛾,在暗期求偶高峰时间段,充分挤压其腹部末端,然后于第8节处横向切下,将切下的腹末标本处理后,借助显微镜和扫描电镜观察性信息素腺体的表面特征及超微结构。【结果】竹织叶野螟雌雄蛾求偶均具一定的程序性,且求偶行为只发生在暗期,暗期前5 h内雌蛾求偶率较低,6 h后求偶率明显升高,并在暗期7-8 h达到求偶高峰;求偶率与雌蛾日龄有密切关系,3日龄雌蛾求偶率最高,持续时间也最长。竹织叶野螟性信息素分泌腺位于腹部第8-9节节间膜上,是一完整的环状结构,显微镜下观察其分泌腺为一乳白色囊状体,扫描电镜下其腹面囊状体迂回褶皱多,大体分为3个褶皱区,除第1褶皱区外,其余褶皱区表面密布乳突、凹陷沟和刺状物,且刺状物顶端有孔;背面囊状体皱褶少,其表面形态与第2和第3褶皱区相似。【结论】研究结果有助于了解竹织叶野螟性信息素合成和释放的时辰节律,也为该虫性信息素的准确提取和鉴定、性信息素的生物合成及利用提供了科学依据。     

Moths behaving like butterflies. Evolutionary loss of long range attractant pheromones in castniid moths: a Paysandisia archon model

Background

In the course of evolution butterflies and moths developed two different reproductive behaviors. Whereas butterflies rely on visual stimuli for mate location, moths use the ‘female calling plus male seduction’ system, in which females release long-range sex pheromones to attract conspecific males. There are few exceptions from this pattern but in all cases known female moths possess sex pheromone glands which apparently have been lost in female butterflies. In the day-flying moth family Castniidae (“butterfly-moths”), which includes some important crop pests, no pheromones have been found so far.

Methodology/Principal Findings

Using a multidisciplinary approach we described the steps involved in the courtship of P. archon, showing that visual cues are the only ones used for mate location; showed that the morphology and fine structure of the antennae of this moth are strikingly similar to those of butterflies, with male sensilla apparently not suited to detect female-released long range pheromones; showed that its females lack pheromone-producing glands, and identified three compounds as putative male sex pheromone (MSP) components of P. archon, released from the proximal halves of male forewings and hindwings.

Conclusions/Significance

This study provides evidence for the first time in Lepidoptera that females of a moth do not produce any pheromone to attract males, and that mate location is achieved only visually by patrolling males, which may release a pheromone at short distance, putatively a mixture of Z,E-farnesal, E,E-farnesal, and (E,Z)-2,13-octadecadienol. The outlined behavior, long thought to be unique to butterflies, is likely to be widespread in Castniidae implying a novel, unparalleled butterfly-like reproductive behavior in moths. This will also have practical implications in applied entomology since it signifies that the monitoring/control of castniid pests should not be based on the use of female-produced pheromones, as it is usually done in many moths.     

RNA interference of pheromone biosynthesis-activating neuropeptide receptor suppresses mating behavior by inhibiting sex pheromone production in Plutella xylostella (L.)

Sex pheromone production is regulated by pheromone biosynthesis-activating neuropeptide (PBAN) in many lepidopteran species. We cloned a PBAN receptor (Plx-PBANr) gene from the female pheromone gland of the diamondback moth, Plutella xylostella (L.). Plx-PBANr encodes 338 amino acids and has conserved structural motifs implicating in promoting G protein coupling and tyrosine-based sorting signaling along with seven transmembrane domains, indicating a typical G protein-coupled receptor. The expression of Plx-PBANr was found only in the pheromone gland of female adults among examined tissues and developmental stages. Heterologous expression in human uterus cervical cancer cells revealed that Plx-PBANr induced significant calcium elevation when challenged with Plx-PBAN. Female P. xylostella injected with double-stranded RNA specific to Plx-PBANr showed suppression of the receptor gene expression and exhibited significant reduction in pheromone biosynthesis, which resulted in loss of male attractiveness. Taken together, the identified PBAN receptor is functional in PBAN signaling via calcium secondary messenger, which leads to activation of pheromone biosynthesis and male attraction.     

杨小舟蛾雌蛾性信息素活性成分的鉴定

【目的】鉴定杨小舟蛾Micromelalopha sieversi雌蛾性信息素活性成分的结构信息。【方法】采用正己烷浸提的方法提取杨小舟蛾性成熟处女雌蛾性腺中的活性成分;利用气相色谱-触角电位联用(GC-EAD)技术对其活性成分进行定位;性腺提取物与4-甲基-1,2,4-三唑啉-3,5-二酮(MTAD)进行微量化学反应,获得衍生物;利用气相色谱-质谱联用(GC-MS)技术分别对性腺提取物及MTAD衍生物进行质谱特征离子分析。【结果】GC-EAD结果显示,杨小舟蛾雄蛾触角对雌蛾性信息素腺体提取物中的一种成分有较好的反应;GC-MS分析结果表明,能引起雄蛾触角电生理反应的成分为十八碳的不饱和醛;MTAD衍生物的GC-MS结果显示,该活性成分的两个双键分别位于碳链的13和15位。【结论】本研究鉴定出杨小舟蛾雌蛾性信息素活性成分的平面结构为13,15-十八碳二烯醛,但双键的立体构型有待合成标准化合物进一步鉴定。本研究为杨小舟蛾性信息素备选化合物的筛选提供了方向,为信息素的结构确证奠定了基础。     

春尺蠖性信息素活性成分的提取和GC-MS鉴定

为了寻求高效无污染的防治害虫春尺蠖Apocheima cinerarius Erschoff的方法, 本实验对春尺蠖雌蛾性信息素进行了初步研究。本研究采取正己烷溶剂浸提法提取春尺蠖处女雌蛾性信息素腺体中的性信息素,运用气相色谱-触角电位联用仪(gas chromatography-electroantennographic detection, GC-EAD) 测定春尺蠖雄蛾触角对雌蛾性信息素腺体提取物中性信息素成分的活性反应, 并运用气相色谱-质谱联用仪(gas chromatograph-mass spectrum, GC-MS）鉴定信息素成分。GC-EAD结果显示雄蛾触角对雌蛾性信息素腺体提取物中的一种成分有较好的反应。GC-MS分析结果表明能引起雄蛾触角电生理反应的成分为含有十四个碳原子直链结构的不饱和乙酸酯, 但其双键位置有待合成标准化合物进一步分析鉴定。该研究结果为春尺蠖雌蛾性信息素备选化合物的筛选提供了方向, 为其结构的确定奠定了基础。     

1,3,5,7-Tetramethyldecyl Formate,Lardolure: Aggregation Pheromone of the Acarid Mite,Lardoglyphus konoi (Sasa et Asanuma) (Acarina: Acaridae)

From an acarid mite, Lardoglyphus konoi (Sasa et Asanuma) (Acarina: Acaridae), with its culture medium, an aggregation pheromone was isolated. The structure of the pheromone was determined as 1,3,5,7-tetramethyldecyl formate and identified by 11 steps of organic synthesis. The absolute configuration of C₁ was assigned as R. The compound has been assigned the trivial name lardolure. The synthesized diastereomeric mixture of racemates showed one-tenth of the activity of the natural pheromone against the test mite, Carpoglyphus lactis.     

Monoenyl hydrocarbons in female body wax of the yellow peach moth as synergists of aldehyde pheromone components

The non-polar components of female body wax and pheromone gland extracts of the yellow peach moth synergistically enhanced male behavioral responses from close to pheromone sources in wind tunnel tests when mixed with an aldehyde pheromone blend. When the non-polar fractions (NPFs) of female body wax were further separated by column chromatography, synergistic activities were found in the 3 and 50% ether in hexane fractions, and they additively increased male responses. The main components of the first fraction were (Z)-9-tricosene, (Z)-9-pentacosene, (Z)-9-heptacosene, (Z)-9-nonacosene and (Z)-9-hentriacontene. Only (Z)-9-heptacosene showed a significant synergistic effect in enhancing male responses, but the other components had no effect. A mixture of the five monoenyl hydrocarbons lost activity at lower doses than 5 ng. Natural ratios of these hydrocarbons in the female body wax and pheromone gland extracts were similar, but the amount of (Z)-9-heptacosene in the female body wax was significantly higher than in the pheromone gland extracts. We conclude that (Z)-9-heptacosene increases male responses to aldehyde pheromones, and unknown component(s) in the 50% ether in the hexane fraction are required for full synergistic enhancement by the NPFs of the female body wax and the pheromone gland extracts.     

Monitoring codling moth (Lepidoptera: Tortricidae) with a four‐component volatile blend compared to a sex pheromone‐based blend

Monitoring adult codling moth, Cydia pomonella (L.), is a crucial component in implementing effective integrated management programmes in apple, Malus domestica Borkhausen. Use of sex pheromone lures to track male populations has been the traditional approach, but their use in orchards treated with sex pheromone for mating disruption (MD) has been problematic. Development of kairomone and kairomone–pheromone combination lures has allowed the catch of female moths and has benefited several aspects of codling moth management through improved spray timings and action thresholds. Recently, a new four‐component volatile blend (4‐K) comprised of pear ester, (E,Z)‐2,4‐ethyl decadienoate (PE), (E)‐11 4,8‐dimethyl‐1,3,7‐nonatriene, all isomers of pyranoid linalool oxide and acetic acid (AA) has been characterized that has increased female moth catch threefold versus any previous blend. Field trapping studies were conducted to compare moth catches in traps baited with 4‐K versus the use of sex pheromone, (E,E)‐8,10‐dodecadien‐1‐ol (PH) in combination with PE and AA. Trials were conducted in orchards left either untreated, or treated with PH or PH + PE. Traps baited with 4‐K and 4‐K + PH lures caught significantly more females than traps baited with PH + PE + AA lures. Traps baited with 4‐K + PH lures caught significantly more total moths than traps baited with PH + PE + AA lures in all three orchards. Adding a PH lure to traps with the 4‐K lure did not affect female catch, but significantly increased male and total moth catches. These studies demonstrate that codling moth can be trapped effectively in apple under MD without the use of sex pheromone lures. The significant increase in female codling moth catch with the 4‐K lure suggests that efforts to improve spray timings and action threshold determinations as well as mass trapping might be enhanced with this new lure.     

Synthesis and biological activity of conformationally restricted gypsy moth pheromone mimics

The design and synthesis of a series of conformationally constrained mimics of gypsy moth sex pheromone, (+)-disparlure (7R,8S)-2-methyl-7,8-epoxyoctadecane, are described. The core structure of the mimics is derived from 5-(2′-hydroxyethyl)cyclopent-2-en-1-ol. Substituent optimization of the analogs was accomplished through the synthesis of mini-libraries and pure individual compounds, followed by electrophysiological experiments with male gypsy moth antennae. The electroantennogram results show that the analogs elicited weak to no antennal responses themselves. There was a clear structure–activity pattern for odorant activity, with ethyl substituents being best. Further, when puffed simultaneously with the pheromone, some of the compounds gave a significant enhancement of the antennal depolarization, indicating an additive or synergistic effect. A pure pheromone stimulus following a mixed compound/pheromone stimulus was generally not affected, with two exceptions: one compound enhanced and another inhibited a subsequent stimulus. The compounds also prolonged the stimulation of the antenna, which manifested itself in widened electroantennogram peaks. We tested the hypothesis that this prolonged stimulation may be due to the stabilization of a particular conformer of the pheromone-binding protein (PBP). Compounds that caused PBP2 to adopt a similar conformation than in the presence of pheromone also caused peak widening. This was not the case with PBP1.     

Stimulation of sex pheromone production by PBAN-like substance in the pine caterpillar moth, Dendrolimus punctatus (Lepidoptera: Lasiocampidae)

Sex pheromone production in the female pine caterpillar moth, Dendrolimus punctatus is controlled by a PBAN-like substance located in the head of female moth. Pheromone titer was significantly decreased by decapitation of female moth, and restored by injection of either Hez-PBAN or head extract prepared from male or female moth. Stimulation of pheromone production by head extract followed a dose-dependent pattern from 0.5 to at least 4 head equivalent. A gland in vitro assay was used to study the relationship between gland incubation time and pheromone production as well as calcium involvement in the stimulation of pheromone production by head extract. Maximum pheromone production was occurred at 60 min after pheromone gland was incubated with two equivalents of head extracts. In vitro experiments showed that the presence of calcium in the incubation medium was necessary for stimulation of pheromone production. The calcium ionophore, A 23187, alone stimulated pheromone production. The pheromone components (Z,E)-5,7-dodecadienol and its acetate and propionate were produced in these experiments but in addition to the aldehyde, (Z,E)-5,7-dodecadienal was also found. This indicates that females are capable of producing four oxygenated functional groups. The PBAN-like substance control of the pheromone biosynthetic pathway was investigated by monitoring the incorporation of the labeled precursor into both pheromone and pheromone intermediates.     

Pheromone release rate determines whether sexual communication of Oriental fruit moth is disrupted competitively vs. non‐competitively

Communicational disruption mechanisms for Oriental fruit moth, Grapholita molesta (Busck) (Lepidoptera: Tortricidae), were determined using a suite of mathematical tools and graphical operations that enable differentiation between competitive attraction and non‐competitive mechanisms of disruption. Research was conducted in 20 field cages, each covering 12 mature apple trees. Commercial monitoring lures releasing Oriental fruit moth pheromone at a rate of 0.04 μg h^?1 and distributed at densities of 0, 1, 2, 4, 8, and 17 per cage were used to evaluate the effect of low‐releasing dispensers on the disruption of sexual communication. Graphical analyses revealed that near‐female‐equivalent pheromone dispensers disrupted Oriental fruit moth competitively. Commercial mating disruption dispensers releasing Oriental fruit moth pheromone at 60 μg h^?1 and deployed at 0, 4, 6, 10, 15, 20, and 30 per cage were used to evaluate the effect of high‐releasing dispensers on the disruption of sexual communication. Oriental fruit moth disruption shifted to a non‐competitive mechanism for high‐releasing dispensers. This is the first time such a shift in disruption mechanism has been demonstrated against a background of otherwise identical experimental conditions. Near‐female‐equivalent pheromone dispensers were also used to quantify the additive effect of an attract‐and‐remove control strategy compared with competitive mating disruption. We report a five‐fold reduction in Oriental fruit moth captures under attract‐and‐remove compared to mating disruption using near‐female‐equivalent dispensers. Surprisingly, release of female Oriental fruit moths into these large‐cage disruption studies had no measurable impact on male trapping.