Moth Pheromone Research Articles

Synthesis of a tritium-labeled photoaffinity analog of the tussock moth pheromone: tritium NMR of vinyl tritons of (E)- and (Z)-alkene isomers

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis of a tritium-labeled photoaffinity analog of the tussock moth pheromone: tritium NMR of vinyl tritons of (E)- and (Z)-alkene isomersBachir Latli and Glenn D. PrestwichCite this: J. Org. Chem. 1988, 53, 19, 4603–4605Publication Date (Print):September 1, 1988Publication History Published online1 May 2002Published inissue 1 September 1988https://doi.org/10.1021/jo00254a043RIGHTS & PERMISSIONSArticle Views115Altmetric-Citations5LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (478 KB) Get e-Alerts Get e-Alerts

Multivariate analysis of the correlation between noctuidae subfamilies and the chemical structure of their sex pheromones or male attractants

Female-emitted pheromones and sex attractants of Noctuidae were investigated using a specific computer procedure to analyze data collected from the literature. Correspondence analysis was used to survey the structure-activity relationships of sex pheromones in seven subfamilies. Structural, stereochemical, and functional features of active molecules were related to taxonomy. This multidimensional analysis revealed that the prevalent chemical frame of noctuid moth pheromones was a monounsaturated acetate withZ stereochemistry and a double bond on the fifth carbon closest to the nonfunctional branch of the molecule. Possible phylogenetic relationships within Noctuidae and between Noctuidae and other families are discussed in light of the sex pheromone biochemistry. Female sex pheromones appeared to be an additional character to be considered in the classification of noctuid moths.

Biomechanics of the release of sex pheromone in moths: effects of body posture on local airflow

ABSTRACT. The calling posture of Spilosoma congrua Walker (Lepidoptera: Arctiidae) affects local airflow in ways that may impact on the release of chemical signals. Dried specimens of S. congrua imitating resting moths, calling moths, and moths with intermediate postures were placed in a wind tunnel. The wind speed was measured near the abdomenal tip where sex pheromone emission occurs. The calling posture, wings‐up, gave significantly greater mean wind speeds near the surface of the sex pheromone gland, effectively eliminating the dead air space that surrounds a non‐calling moth. The calling posture also decreased the relative intensity of turbulence near the pheromone gland surface.

Sex pheromone receptor proteins. Visualization using a radiolabeled photoaffinity analog.

A tritium-labeled photoaffinity analog of a moth pheromone was used to covalently modify pheromone-selective binding proteins in the antennal sensillum lymph and sensory dendritic membranes of the male silk moth, Antheraea polyphemus. This analog, (E,Z)-6,11-[3H]hexadecadienyl diazoacetate, allowed visualization of a 15-kilodalton soluble protein and a 69-kilodalton membrane protein in fluorescence autoradiograms of electrophoretically separated antennal proteins. Covalent modification of these proteins was specifically reduced when incubation and UV irradiation were conducted in the presence of excess unlabeled pheromone, (E,Z)-6,11-hexadecadienyl acetate. These experiments constitute the first direct evidence for a membrane protein of a chemosensory neuron interacting in a specific fashion with a biologically relevant odorant.

Distance orientation of biting flies to their hosts

In the first section of this review, the stimuli involved in orienting biting flies to their hosts from a distance are discussed under the following headings: (1) Appetitive search—driven by endogenous rhythms and hunger. (2) Activation—the switchover from search behaviour to active host-location brought about in the insect by host-originating stimuli including, depending on species, carbon dioxide, visual contact, and specific host odours. (3) Attraction—the process of active host-location through which the insect comes into the immediate vicinity of the host. This relies on host-originating stimuli including visual contact and olfactory stimuli such as carbon dioxide, volatiles such as acetone, and specific, usually very potent host-related odours. The second part of this review discusses the properties of the odour plumes biting flies rely on to locate the host. Possible methods of host-location using air-borne odour plumes are presented and the “positive anemotaxis” model based on moth pheromone work is stressed.

Intra-specific competition in the sex communication channel: a selective force in the evolution of moth pheromones?

A model for mate competition in moths sexually signalling with pheromones is presented. The model has four variables. N is the number of individuals of each sex per area unit. r is the length of the female odour plume as detected by a responding male. e is a parameter increasing with male ability to discriminate between concentrations. r-e becomes the competitive part of the female pheromone plume, i.e. the distance at which an upwind female is able to distract males from downwind plumes. Assuming a random distribution of males and females the number of matings in a generation can be calculated. Introducing a fourth parameter, B = surviving offspring of each sex from a mating, the population dynamics of the population can be described. Two special cases are analysed; (1) e = r, and (2) e = 0. In case (1) mating success increases with population density towards unity. In case (2) interference between the pheromone plumes of different females will lower the mating success at higher population densities. The stability of the communicating population decreases with increasing e and B. We conclude that there should be a strong selection pressure for male ability to discriminate between odour plumes under natural circumstances and for individually distinguishable pheromone plumes.

Evolution of Male Pheromones in Moths: Reproductive Isolation Through Sexual Selection?

Central to our understanding of the species concept is knowledge of the nature and evolution of reproductive isolating mechanisms. The once widely accepted model of Dobzhansky, which holds that isolation evolves through selection against hybrids of differentially adapted populations, is now largely rejected. This rejection is due to both theoretical difficulties and a paucity of examples of the predicted pattern of reproductive character displacement. From a survey of five families of Lepidoptera, entailing more than 800 species, evidence is given that male courtship pheromones have evolved within the context of sexual isolation as an adaptive response to mating mistakes between differentially adapted populations; however, distinct from the natural selection model of Dobzhansky, this report suggests the mechanism for change to be sexual selection.

Synthesis from D-xylose of the salt marsh caterpillar moth pheromone (3Z,6Z,9S,10R)-epoxyheneicosadiene and its (3Z,6E)-stereoisomer.

A ten-step synthesis of the title pheromone and its (3Z,6E)-stereoisomer from an acyclic derivative of D-xylose is described.

Evolution of the ermine moth pheromone tetradecyl acetate

The nine sympatric forms of small ermine moths of the genus Yponomeuta (Lepidoptere; Yponomeutidae) in the west palaearctic region show various degrees of differentiation1,2, including among other characteristics, differences in their sexual pheromones3. As is the case for many other moths4, the ermine moths so far analysed use delta 11-unsaturated acetates ((Z)-11-tetradecenyl, (E)-11-tetradecenyl and (Z)-11-hexadecenyl acetate) as primary pheromone components. Here for the first time in Lepidoptera we report that a saturated acetate, tetradecyl acetate, is the primary pheromone component5 of Y. rorellus (Hubner). Y. rorellus is almost monomorphic with respect to isoenzyme variation6 and has fewer chromosomes than its relatives7,8. We suggest that it has evolved through loss of unsaturated pheromone components in a ‘genetic revolution’ at a population bottleneck, and by the founders of the new species filling an empty communication niche, separated from that of the ancestral species.

Synthesis of (6z)-cis-9S,10R-epoxyheneicosene, a component of the ruby tiger moth pheromone

A 10-step synthesis of the titled pheromone and analogues from an acyclic derivative of D-Xylose is described.

The chemistry of .alpha.-silyl carbonyl compounds. 11. Reaction of .alpha.-silyl esters with grignard reagents: a synthesis of .beta.-keto silanes and ketones. Preparation of the douglas fir tussock moth pheromone

Preparation d'alcanones et alcenones a longue chaine dont l'heneicosene-6one-11 (pheromone)

Selenoesters in organic synthesis. 2. New synthesis of saturated and ?,?-unsaturated ketones and the synthesis of the Peach moth pheromone (Carposia niponensis)

1. Selenoesters react readily with a wide variety of organometallic reagents to give saturated ketones in high yields. 2. Treatment of alkenyl copper (I) derivatives with selenoesters (or chloroanhydrides) in the presence of hexamethylphosphoramide gives excellent yields of α,β-unsaturated ketones of varying structures. 3. The syntheses of the components of the Peach moth pheromoneCarposia niponensis, namely, Z-12-nonadecen-9-one and Z-13-eicosen-10-one, have been described.

EUROPEAN PINE SHOOT MOTH, RHYACIONIA BUOLIANA (LEPIDOPTERA: TORTRICIDAE): IDENTIFICATION OF ADDITIONAL PHEROMONE COMPONENTS RESULTING IN AN IMPROVED LURE

AbstractInvestigation of the European pine shoot moth pheromone has revealed three components in addition to the previously identified E-9-dodecenyl acetate (E9-12:Ac): E-9-dodecenol, dodecyl acetate, and dodecanol. Inclusion of E-9-dodecenol makes lures more attractive to the moth than unmated females or E9-12:Ac alone. Dodecyl acetate had no apparent effect when added to this more attractive mixture whereas dodecanol had an inhibitory effect. Dodecyl acetate appeared to mask the inhibitory effect of dodecanol when 0.3% or more of the former component is present in the lure. Relative proportions of components are critical in comparative testing or monitoring populations of the moth.

Stereochemical course of pheromone biosynthesis in the arctiid moth, Creatonotos transiens.

The biosynthetic conversion of a pyrrolizidine alkaloid (heliotrine, IV) to a male moth pheromone (hydroxydanaidal, III) is found to proceed with inversion of configuration at the remaining asymmetric center (C-7).

Analysis of moth pheromone acetates by selected ion monitoring using electron impact and chemical ionization mass spectrometry

Mass spectrometric determination of moth pheromone components by means of selected ion monitoring with electron impact and chemical ionization has been evaluated. For the analysis of acetates, chemical ionization with ammonia as reactant gas proved advantageous with respect to sensitivity and selectivity. A quantitative assay for determination of pheromone samples from individual turnip moth females (Agrotis segetum, Noctuidae), using internal standards, deuterated at the acyl group, was developed. The assay showed correct linearity in the investigated region (20–2000 pg). Signal to noise ratios for 100 pg of acetates using chemical ionization (ammonia as reactant gas) were in the range 10–50 depending on the degree of unsaturation. Conservative limits of detection (background signal + three times the standard deviation) and quantification (background signal + 10 times the standard deviation) were approximately 70 and 240 pg, respectively. A significant decrease in gland titre of (Z)‐5‐decenyl acetate and (Z)‐7‐dodecenyl acetate after mating was established. (Less)

Peach, Insecticide Tests, 1983

Abstract A 4-year-old block of Red Haven was used in the test. Nine trees arranged in a randomized block design were used for each treatment. Sprays were applied 4 and 17 May, to the foliage with 5-horsepower hydraulic sprayer set at 300 lb/in2 A tree gun with a No. 4 disc was used to apply 1 gal per tree. The spray was timed with the aid of oriental fruit moth (OFM) pheromone traps. All twig terminals per tree were inspected for wilting, due to OFM larval tunneling, on 4, 17, and 31 May. The OFM population was low.

ChemInform Abstract: A CONVENIENT METHOD FOR THE SYNTHESIS OF ACYCLIC KETONES. SYNTHESIS OF SEX PHEROMONE OF DOUGLAS FIR TUSSOCK MOTH

AbstractAusgehend von den Sulfonen (I) werden die Dithioverbindungen (V) dargestellt, deren milde Hydrolyse mit CUCI, ‐SiO, zu den acyclischen Ketonen (VI) führt.

Lemon odor helps identify male moth pheromone

Lemon odor helps identify male moth pheromone

A Convenient Method for the Synthesis of Acyclic Ketones. Synthesis of Sex Pheromone of Douglas Fir Tussock Moth

Abstract (α-Alkyl-α-methylthio)alkyl p-tolyl sulfones derived from the reaction of α-alkylated alkyl p-tolyl sulfones with dimethyl disulfide could be easily hydrolyzed by CuCl2–SiO2 to give the corresponding ketones in fairly good yields. This method was applied to the synthesis of Douglas Fir Tussock Moth Pheromone.

Continuous single sensillum recording as a detection method for moth pheromone components in the effluent of a gas chromatograph

ABSTRACT. Single sensillum recordings were made from male antennal pheromone receptors of Agrotis segetum (Schiff.) (Noctuidae) and Adoxophyes orana (F.v.R.) (Tortricidae). A gas chromatograph (GC) was used to prepare and to deliver the odour stimuli. Samples of female abdominal gland extracts were injected into the column of the GC and the responses of the receptor cells to the effluent were recorded continuously. The receptor cells responded with an increase of their action potential frequency during elution of the major pheromone components. The pheromone receptors of Agrotis showed a much higher sensitivity than those of Adoxophyes. In the extract of female glands from Agrotis, compounds were detected which have not been identified in previous studies of the sex pheromone of this species. It is suggested that the combination of GC techniques with direct single sensillum recording may serve as a valuable supplement to electro‐antennographic techniques.