Grigori Khaskin

• Simon Fraser University

Chemical communication is common in spiders but few pheromones have been identified. Female widow spiders in the genus Latrodectus spin webs that disseminate an attractive sex pheromone, and a contact pheromone on the silk elicits courtship behavior by males. The methyl ester of N-3-methylbutanoyl-O-(S)-2-methylbutanoyl-L-serine is a contact pherom...

This invention relates to compositions of one or more compounds that incorporate one or more allyl sulfide, allyl disulfide or allyl polysulfide moieties, or one or more allyl sulfide, allyl disulfide or allyl polysulfide moieties and one or more hydroxyl groups, used in effective amount in formulations, including emulsions, to repel blood-feeding...

Red-throated Caracaras Ibycter americanus (Falconidae) are specialist predators of social wasps in the Neotropics. It had been proposed that these caracaras possess chemical repellents that allow them to take the brood of wasp nests without being attacked by worker wasps. To determine how caracaras exploit nests of social wasps and whether chemical...

Synanthedon myopaeformis Borkhausen (Lepidoptera: Sesiidae) is a diurnal clearwing moth native to Eurasia that was recently introduced into British Columbia (BC) and Ontario, Canada, where it has become a serious pest in apple orchards. In BC, these moths commonly feed on nectar of inflorescences, particularly that of showy milkweed, Asclepias spec...

We identified and field-tested the sex pheromones of Dasineura oxycoccana (Johnson) (Diptera: Cecidomyiidae) midges collected from cranberry, Vaccinium macrocarpon Aiton, and from highbush blueberry, Vaccinium corymbosum L., commonly named cranberry tipworm (CTW) and blueberry gall midge (BGM), respectively. Coupled gas chromatographic-electroanten...

Close-range sexual communication of the egg parasitoid wasp Ooencyrtus kuvanae (Hymenoptera: Encyrtidae) takes place on host gypsy moth, Lymantria dispar (Lepidoptera: Lymantriidae), egg masses. We tested the hypothesis that mate recognition in O. kuvanae is mediated, in part, by low-volatility cuticular hydrocarbon (CHC) pheromone components. Gas...

Stale beer and peanut butter are effective baits for the German cockroach (GCRs), Blattella germanica (L.) (Dictyoptera: Blattellidae). In still-air arena olfactometer experiments it was previously shown that headspace volatile extracts of peanut butter and solvent extract of beer attract male GCRs. The objective of this study was to identify the s...

Garlic (Allium sativum) and its essential oil have long been used for their distinct flavour, therapeutic effects and as a topical and systemic insect repellent. We tested the hypothesis that the yellow fever mosquito, Aedes aegypti L. (Diptera: Culicidae), responds electrophysiologically and behaviourally to specific components of the steam-distil...

The volatile organic compounds emitted from ripening bananas that elicit an antennal response from the common fruit fly, Drosophila melanogaster, were analyzed by a combination of gas chromatographic-electroantennographic detection, mass spectrometry, and (1)H NMR spectroscopy. These analyses revealed that the headspace of ripening bananas contains...

Recently, (2S,12Z)-2-acetoxy-12-heptadecene was identified as the major sex pheromone component of the pistachio twig borer moth, Kermania pistaciella, one of the most serious insect pests of pistachio plantations in Iran and Turkey. In field studies, an attract-and-kill formulation containing (2S,12Z)-2-acetoxy-12-heptadecene demonstrated efficacy...

Adults and juveniles of the common bed bug, Cimex lectularius L. (Hemiptera: Cimicidae), return to and aggregate in harborages after foraging for hosts. We tested the hypothesis that the aggregation is mediated, in part, by an airborne aggregation pheromone. Volatiles from experimental C. lectularius harborages were captured on Porapak Q, fractiona...

In a field trapping experiment in an abandoned seed orchard of western red-cedar, Thuja plicata Donn × D. Don, in British Columbia, we show that attraction of male red-cedar cone midges, Mayetiola thujae (Hedlin), to the pheromone blend (2S,12S)-, (2S,13S)-, and (2S,14S)-diacetoxyheptadecane is reduced in the presence of a blend of all other stereo...

The Indian gypsy moth, Lymantria obfuscata (Lepidoptera: Lymantriidae), has been recognized as a distinct species since 1865 but closely resembles a diminutive form of gypsy moth, Lymantria dispar. We tested the hypothesis that the sex pheromones of L. obfuscata and L. dispar are similar. In laboratory mate acceptance studies, very few male L. disp...

The sex pheromone of the pistachio twig borer, Kermania pistaciella (Lepidoptera: Oinophilidae), one of the most important insect pests of pistachio, Pistacia vera, in Turkey and Iran, was identified. In gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometric analyses of pheromone gland extracts of female K. pistaciel...

The sex pheromone of the pistachio twig borer, Kermania pistaciella (Lepidoptera: Oinophilidae), one of the most important insect pests of pistachio, Pistacia vera, in Turkey and Iran, was identified. In gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometric analyses of pheromone gland extracts of female K. pistaciel...

The Paulownia bagworm, Clania variegata Snell. (Lepidoptera: Psychidae), is one of the most significant forest defoliators in China. In gas chromatographic (GC)-electroantennographic detection analyses of pheromone gland extracts of female C. variegata on three GC columns (DB-5, DB-23, DB-210), two compounds (A and B) elicited strong responses from...

Pheromonal communication of adult peach twig borers, Anarsia lineatella Zeller (Lepidoptera: Gelechiidae), was reinvestigated based on recent findings that virgin female-baited traps were more attractive to mate-seeking males than a two-component synthetic sex pheromone consisting of (E)-5-decen-1-yl acetate (1000 microg) and (E)-5-decen-1-ol (100...

We identified, synthesized, and field-tested the sex pheromone of female red cedar cone midge Mayetiola thujae (Hedlin) (Diptera: Cecidomyiidae), a pest insect in red cedar Thuja plicata seed orchards. Coupled gas chromatographic (GC)-electroantennographic detection analyses of pheromone extract revealed three components (A, B, C) that elicited res...

Our objective was to identify the sex pheromone of Lymantria bantaizana (Lepidoptera: Lymantriidae) whose larvae feed exclusively on walnut, Juglans spp., in China, and Japan. Coupled gas chromatographic-electroantennographic detection (GC-EAD) analyses of pheromone gland extracts revealed a single EAD-active component. Retention index calculations...

(Z,Z)-6,9-Heneicosadien-11-one (Z6Z9-11-one-21Hy) was identified as the major sex pheromone component of the painted apple moth (PAM), Teia anartoides (Lepidoptera: Lymantriidae), on the basis of (1) comparative gas chromatographic-electroantennographic detection (GC-EAD) analyses, GC-mass spectrometry (MS), high-performance liquid chromatography (...

Considering the vast Eurasian distribution of gypsy moth, Lymantria dispar (Lepidoptera: Lymantriidae), the many subspecies, and their presence in different lymantriid communities, we tested the hypothesis that L. dispar populations in eastern Asia employ one or more pheromone components in addition to the previously known single component pheromon...

In a recent study, evidence was presented that females of the aphidophagous midge Aphidoletes aphidimyza (Rondi) (Diptera: Cecidomyiidae) release a sex pheromone to attract mates. Our objectives were to identify and bioassay the pheromone. Coupled gas chromatographic-electroantennographic detection(GC-EAD) analyses of untreated and hydrogenated phe...

(6Z,9Z,11S)-6,9-Heneicosadien-11-ol (Z6Z9-11S-ol-C21) and (6Z,9Z,11R)-6,9-heneicosadien-11-ol (Z6Z9-11R-ol-C21) were identified as major sex pheromone components of female tussock moths, Orgyia detrita Guérin-Méneville (Lepidoptera: Lymantriidae), on the basis of (1) analyses of pheromone gland extracts of female O. detrita by coupled gas chromatog...

During peak calling activity by male oil palm bunch moths, Tirathaba mundella Walker (Lepidoptera: Pyralidae), their hairpencils, wings or entire body were extracted in hexane. Gas chromatographic-electroantennographic detection (GC-EAD) analyses of hair pencil extracts revealed four compounds that consistently elicited responses from female antenn...

Our objectives were to identify and field test the sex pheromone of female Douglas-fir cone gall midge, Contarinia oregonensis (Diptera: Ce-cidomyiidae). Coupled gas chromatographic-electroantennographic detection (GC-EAD) analyses of pheromone extract revealed a single compound (A) that elicited responses from male antennae. Hydrogenation of phero...

Pheromone extract of the female orange wheat blossom midge, Sitodiplosis mosellana (Géhin) (SM) (Diptera: Cecidomyiidae), was analyzed by coupled gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometry (MS), employing fused silica columns coated with DB-5, DB-210, DB-23 or SP-1000. These analyses revealed a single, EAD...

Pheromone extract of the female orange wheat blossom midge, Sitodiplosis mosellana (Géhin) (SM) (Diptera: Cecidomyiidae), was analyzed by coupled gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometry (MS), employing fused silica columns coated with DB-5, DB- 210, DB-23 or SP-1000. These analyses revealed a single, EA...

This study was undertaken to identify sex pheromone components of nettle caterpillars Darna trima and Darna bradleyi (Lepidoptera: Limacodidae) whose larvae defoliate oil palm, Elaeis guineensis, in southeast Asia. Coupled gas chromatographic–electroantennographic detection (GCEAD) analyses of pheromone gland extracts revealed two antennally active...

Gas chromatographic–electroantennographic detection (GC-EAD) analyses of pheromone gland extracts of female nettle caterpillars, Setora nitens, revealed four compounds that consistently elicited responses from male moth antennae. Retention indices on three fused silia columns (DB-5, DB-23, and DB-210) of two EAD-active compounds were almost identic...

cis-7,8-Epoxy-2-methyleicosane is a sex pheromone component of the Casuarina moth, Lymantria xylina Swinhoe. The compound was extracted from pheromone glands of female moths and was identified by coupled gas chromatographic–electroantennographic detection (GC-EAD) and GC–mass spectrometry. In field experiments in Taiwan, traps baited with either or...

We determined that location of host (Cydia pomonella) eggs by Ascogaster quadridentata is mediated by kairomones, investigated potential sources of the kairomones and identified a blend of kairomones from the source that was attractive to A. quadridentata. In Y-tube olfactometer bioassays, female A. quadridentata were attracted to Porapak Q-collect...

In 1996, the exotic white-spotted tussock moth (WSTM), Orgyia thyellina (Lepidoptera: Lymantriidae), was discovered in Auckland, New Zealand. Because establishment of WSTM would threaten New Zealand's orchard industry and international trade, eradication of WSTM with microbial insecticide was initiated. To monitor and complement eradication of WSTM...

Gas chromatographic–electroantennographic detection (GC-EAD) analyses of female nettle caterpillar, Setothosea asigna, pheromone gland extracts revealed seven antennally active compounds. Based on their retention indices on three fused silica columns (DB-5, DB-23, and DB-210), these compounds were hypothesized and, through comparative GC, GC-EAD an...

Three candidate sex pheromone components, (Z)6,(Z)9-, (Z)6,(E)8-, and (Z)6,(E)9-heneicosadien-11-one (Z6Z9, Z6E8, and Z6E9) were identified in pheromone gland extracts of female Douglas-fir tussock moths (DFTM), Orgyia pseudotsugata (McDunnough). Their occurrence in subnanogram quantities in extracts and structural conversion during analytical proc...

(E)-11,13-Tetradecadienal (E11,13-14:Ald) is the major sex pheromone component of the eastern blackheaded budworm (EBB),Acleris variana (Fern.). The compound was identified in female pheromone gland extracts by coupled gas chromatographic-electroantennographic detection (GC-EAD), coupled GC-mass spectrometry in selected ion monitoring mode, and ret...

3,13-Dimethylheptadecane (3,13-dime-17Hy) is the major sex pheromone component of the western false hemlock looper (WFHL),Nepytia freemani Munroe. It was identified in extracts of female pheromone glands by coupled gas chromatographic-electroantennographic detection (GC-EAD) and coupled GC-mass spectroscopy (GC-MS). Traps baited with 100μg of 3,13-...

Examination of the PMR spectra of eleven bicyclic thiolane 1,1-dioxide derivatives has enabled those features of the spectral parameters characteristic of the cis- and trans-orientation of the two condensed five-membered heterocycles to be established. The proton coupling constants show that the conformation of the 1,1-dioxothiolane ring in both ty...

The trans-3-chloro-4-thioureidosulfolanes, prepared in situ from the aminosulfolane (I) and the isothiocyanates (II), cyclize in the presence of amines to give the fused thiazolimines (III) or the imidazolethiones (IV) depending on the basicity of the amine used.

Reaction of trans-3-chloro-A-aminothiolane 1,1-dioxide hydrochloride with aryl isothiocyanates gives, according to the base involved, cis-perhydrothieno[3,4-d]imidazole-2-thione 5,5-dioxides or the hitherto undescribed cis-2-aryliminoperhydrothieno 3,4-d] thiazole 5,5-dioxides.

The aminohydroxysulfolane (I) reacts with the isothiocyanates (II) to give the corresponding thioureas which are cyclized in situ, producing the iminooxazoles (III).

Both cis- and trans-isomers of the perhydrothienooxazolethione dioxides (I) rearrange upon basic treatment, forming the cis-perhydrothienothiazolone dioxides (II).

Alkylation of trans-N-alkyl(or aryl)-N'-(3-hydroxy-1,1-dioxothiolan-4-yl) thioureas with ethyl p-toluenesulfonate, and the reaction of cyanogen bromide wiht an ethyl p-toluenesulfonate, and the reaction of cyanogen bromide with trans-3-hydroxy-4-aminothiolan-1,1-dioxides have given salts of trans-2-iminoperhydrothieno[3,4-d]-oxazole 5,5-dioxides. R...

The phenylaminothiolene dioxide (I) reacts with benzoyl isothiocyanate (II) to give the thiourea (III) which is cyclized upon treatment with alkali, forming the cis-perhydrothienoimidazolethione dioxide (IV).

cis-Perhydrothieno[3,4-d.]imidazol-2-one 5,5-dioxides were obtained in good yields by the reaction of N-(4-hydroxy-1,1-dioxothiolan-3-yl)-thioureas with methyl iodide and subsequent treatment of the mixture with aqueous triethylamine.

Die Aminothiolen-Sß-dioxide (I) reagieren mit Isothiocyanaten (II) oder mit Thiophosgen und Aminen (III) zu Perhydrothieno-imidazolthion-dioxiden (IV) mit cis- Ringverknüpfung.

It is shown that the cis and trans isomers of perhydrothieno[3,4-d]imidazole-2-thione 5,5-dioxides can be obtained in good yields from the accessible derivatives of thiolane and 2-thiolene 1,1-dioxides.

The reaction of monoalkyl(aryl)dithiocarbamic acid salts with 4-substituted 2-thiolene and 3,4-disubstituted thiolane 1,1-dioxides gave N-alkyl(aryl)thiolano-[3,4-d]thiazolidine-2-thione 5,5-dioxides, the structure of which was proved by x-ray diffraction studies. 1,1-Dioxothiol-3-en-3-yl esters were obtained with salts of dialkyl(heteryl)dithiocar...