Female-Produced Sex Pheromone of Tetrastichus planipennisi, a Parasitoid Introduced for Biological Control of the Invasive Emerald Ash Borer, Agrilus planipennis.

The Asian eulophid wasp Tetrastichus planipennisi is being released in North America as a biocontrol agent for the emerald ash borer (Agrilus planipennis), a very destructive invasive buprestid beetle that is devastating ash trees (Fraxinus spp.). We identified, synthesized, and tested a female-produced sex pheromone for the wasp.

Pheromones of three ambrosia beetles in the species complex: ratios and preferences.

Three cryptic species in the species complex were reared in laboratory colonies and investigated for the presence of pheromones. Collections of volatiles from combinations of diet, fungus, beetles, and galleries from polyphagous shot hole borer ( sp. #1) revealed the presence of 2-heneicosanone and 2-tricosanone only in the presence of beetles, regardless of sex.

Polyols, not sugars, determine the structural diversity of anti-streptococcal liamocins produced by Aureobasidium pullulans strain NRRL 50380.

Liamocins are polyol lipids produced by the fungus Aureobasidium pullulans, and have selective antibacterial activity against Streptococcus species. Liamocins produced by A. pullulans strain NRRL 50380 on sucrose medium have a d-mannitol head group ester-linked to 3,5-dihydroxydecanoate acyl chains, three or four of which are joined together by 1,5-polyester bonds (liamocins Man-A1 and Man-B1), and similar 3'-O-acetylated analogs (Man-A2 and Man-B2).

A Culture Method for Darkling Beetles, Blapstinus spp. (Coleoptera:Tenebrionidae).

Darkling beetles, Blapstinus spp., have become a serious pest of Cucurbitaceae crops, especially in California. A culture method was sought to provide large numbers (>500) of adult beetles of known age and sex that could be used for laboratory testing when needed.

Can Coffee Chemical Compounds and Insecticidal Plants Be Harnessed for Control of Major Coffee Pests?

Pests and pathogens threaten coffee production worldwide and are difficult to control using conventional methods, such as insecticides. We review the literature on the chemistry of coffee, concentrating on compounds most commonly reported from Coffea arabica and Coffea canephora. Differences in chemistry can distinguish coffee species and varieties, and plants grown under different biogeographic conditions exhibit different chemotypes.

Discordant phylogenies suggest repeated host shifts in the Fusarium-Euwallacea ambrosia beetle mutualism.

The mutualism between xyleborine beetles in the genus Euwallacea (Coleoptera: Curculionidae: Scolytinae) and members of the Ambrosia Fusarium Clade (AFC) represents one of 11 known evolutionary origins of fungiculture by ambrosia beetles. Female Euwallacea beetles transport fusarial symbionts in paired mandibular mycangia from their natal gallery to woody hosts where they are cultivated in galleries as a source of food. Native to Asia, several exotic Euwallacea species were introduced into the United States and Israel within the past two decades and they now threaten urban landscapes, forests and avocado production.

Attraction of Agrilus planipennis (Coleoptera: Buprestidae) to a volatile pheromone: effects of release rate, host volatile, and trap placement.

Attraction of emerald ash borer, Agrilus planipennis Fairmaire, to a volatile pheromone was demonstrated in three field experiments using baited green sticky traps. A dose-response curve was generated for male A. planipennis to increasing release rates of (3Z)-dodecen-12-olide ((3Z)-lactone) in combination with the green leaf volatile, (3Z)-hexenol.

Male-produced pheromone of Spathius agrili, a parasitoid introduced for the biological control of the invasive emerald ash borer, Agrilus planipennis.

The braconid wasp, Spathius agrili, has been released in the U.S. as a biocontrol agent for the invasive emerald ash borer (Coleoptera: Buprestidae: Agrilus planipennis), a destructive pest of ash trees (Fraxinus spp.

Two-carbon homologation of aldehydes and ketones to α,β-unsaturated aldehydes.

Phosphonate reagents were developed for the two-carbon homologation of aldehydes or ketones to unbranched- or methyl-branched α,β-unsaturated aldehydes. The phosphonate reagents, diethyl methylformyl-2-phosphonate dimethylhydrazone and diethyl ethylformyl-2-phosphonate dimethylhydrazone, contained a protected aldehyde group instead of the usual ester group. A homologation cycle entailed condensation of the reagent with the starting aldehyde, followed by removal of the dimethylhydrazone protective group with a biphasic mixture of 1 M HCl and petroleum ether.

Absolute configuration of 7-epi-sesquithujene.

7-epi-sesquithujene (1) is a bicyclic sesquiterpene isolated from phoebe oil, an essential oil of the Brazilian walnut tree, Phoebe porosa. It is also produced by stressed ash trees and has been shown to elicit strong electrophysiological responses on emerald ash borer, Agrilus planipennis, antennae. In the course of the development of a synthetic 7-epi-sesquithujene lure for field testing against the emerald ash borer, we found that the absolute configuration of this compound had not been determined.

Male-specific sesquiterpenes from Phyllotreta flea beetles.

Flea beetles in several genera are known to possess male-specific sesquiterpenes, at least some of which serve as aggregation pheromones that attract both sexes. In continuing research on the chemical ecology of Phyllotreta flea beetles, six new male-specific sesquiterpenes were identified, one from P. striolata (hydroxyketone 9) and five from P.

Methyl 6-methylsalicylate: a female-produced pheromone component of the parasitoid wasp Spalangia endius.

Sex-pheromone-related behavior and chemistry were studied in the wasp Spalangia endius Walker (Hymenoptera: Pteromalidae), a pupal parasitoid of the house fly, Musca domestica L. (Diptera: Muscidae). Males responded behaviorally to female extracts by arrestment, whereas females did not arrest to male extracts.

Sex pheromone of the pine false webworm Acantholyda erythrocephala.

Females of the pine false webworm Acantholyda erythrocephala (L) produce the sex pheromone (Z)-6, 14-pentadecadienal, which attracts flying males in the field. By using gas chromatography coupled with electroantennographic detection (GC-EAD) and mass spectrometry (GC-MS), we detected (Z)-6,14-pentadecadienal in volatile collections and in whole body extracts of female A. erythrocephala.

Male-produced aggregation pheromone of the lesser mealworm beetle, Alphitobius diaperinus.

The lesser mealworm beetle, Alphitobius diaperinus (Panzer), is a widespread serious pest in poultry production facilities and is difficult to control by conventional means. Although pheromone-based tools have become useful in the management of other beetle pests, no pheromone was known for A. diaperinus, and this study sought to develop basic pheromone information.

Antennally active macrolide from the emerald ash borer Agrilus planipennis emitted predominantly by females.

The macrocyclic lactone (3Z)-dodecen-12-olide was identified from the emissions of the emerald ash borer, Agrilus planipennis, feeding on ash foliage. The compound was detected from both sexes but was ca. 10 times more abundant from females.

Behaviorally active green leaf volatiles for monitoring the leaf beetle, Diorhabda elongata, a biocontrol agent of saltcedar, Tamarix spp.

Biological activity and chemistry of host plant volatiles were investigated for Diorhabda elongata, Brullé (Coleoptera: Chrysomelidae), a biological control agent for the invasive tree, saltcedar (Tamarix spp., Tamaricaceae). Gas chromatographic-electroantennographic detection (GC-EAD) analysis of volatiles collected from adult D.

Male-produced aggregation pheromone compounds from the eggplant flea beetle (Epitrix fuscula): identification, synthesis, and field biossays.

Volatiles from the eggplant flea beetle, Epitrix fuscula Crotch (Coleoptera: Chrysomelidae), feeding on host foliage, were investigated. Six male-specific compounds were detected and were identified through the use of mass spectrometry, nuclear magnetic resonance (NMR) spectrometry, chiral and achiral gas chromatography, high-performance liquid chromatography, electrophysiology (gas chromatography-electroantennography, GC-EAD), and microchemical tests. The two most abundant of the six compounds were (2E,4E,6Z)-2,4,6-nonatrienal (1) and (2E,4E,6E)-2,4,6-nonatrienal (2).

Dimethylfuran-lactone pheromone from males of Galerucella calmariensis and Galerucella pusilla.

Male Galerucella calmariensis and Galerucella pusilla (Coleoptera: Chrysomelidae) emit an aggregation pheromone while feeding on host foliage. Isolation of the compound from collected volatiles was guided by comparisons of gas chromatograms of extracts from males and females and by gas chromatography-electroantennographic detection. The compound was identified by a combination of spectrometric methods and microchemical tests as the novel dimethylfuran lactone, 12,13-dimethyl-5,14-dioxabicyclo[9.

Identification, synthesis, and field evaluation of the sex pheromone from the citrus leafminer, Phyllocnistis citrella.

Using male antenna as the sensing element, three electroantennographic detection (EAD)-active peaks were detected from pheromone gland extracts of the citrus leafminer, Phyllocnistis citrella. Based on gas chromatography (GC)-mass spectrometry and GC-infrared data, the semiochemicals were tentatively identified as a novel pheromone, (Z,Z,E)-7,11,13-hexadecatrienal, a previously identified attractant, (Z,Z)-7,11-hexadecadienal, and (Z)-7-hexadecenal in a ratio of 30:10:1, respectively. Identification was confirmed with synthetic compounds, which gave retention times identical to those of the natural products on three capillary columns with polar and nonpolar phases.

Pheromonal activity of compounds identified from male Phyllotreta cruciferae: field tests of racemic mixtures, pure enantiomers, and combinations with allyl isothiocyanate.

Four himachalene sesquiterpenes and (+)-gamma-cadinene, previously identified as possible pheromone components from males of a North American population of Phyllotreta cruciferae Goeze (Coleoptera, Chrysomelidae), were tested for attractiveness in field trapping experiments in Hungary. A mixture of the four synthetic racemic himachalene derivatives and (+)-gamma-cadinene from a botanical source was slightly attractive to beetles, but much more attractive when blended with the known host-plant-derived attractant allyl isothiocyanate. This result was consistent with a previous study in North America.

Responses of flea beetle Phyllotreta cruciferae to synthetic aggregation pheromone components and host plant volatiles in field trials.

Male-specific compounds, previously identified from Phyllotreta cruciferae and synthesized or isolated from natural sources, attracted both sexes of the beetle in field trials and therefore function as components of a male-produced aggregation pheromone. Six field experiments of 7 to 10 d duration each were conducted over 2 yr using modified boll weevil traps and two doses of pheromone. Treatments containing two doses of allyl isothiocyanate (AITC), a breakdown product of glucosinolates in Brassica napus L.

The aggregation pheromone of Diorhabda elongata, a biological control agent of saltcedar (Tamarix spp.): identification of two behaviorally active components.

The leaf beetle Diorhabda elongata Brullé (Coleoptera: Chrysomelidae) has been introduced as a biological control agent for saltcedars, Tamarix spp., an exotic, invasive weedy tree in the western United State. Gas chromatographic (GC) analysis of volatiles collected from feeding male or female beetles, or saltcedar foliage alone, showed two components produced almost exclusively by males.

Bioactivity, synthesis, and chirality of the sex pheromone of currant stem girdler, Janus integer.

It was previously reported that females of the currant stem girdler, Janus integer Norton (Hymenoptera: Cephidae), produce a compound, (Z)-9-octadecen-4-olide (1), that is sensitively detected by the antennae of males only. These characteristics suggested a pheromonal function, and this has now been confirmed with behavioral tests. Field tests conducted during two seasons in a commercial red currant field in Washington State showed that synthetic racemic 1 is attractive to male J.

Aggregation pheromone of the cereal leaf beetle: field evaluation and emission from males in the laboratory.

The previously identified, male-specific compound of the cereal leaf beetle (CLB, Chrysomelidae; Oulema melanopus), (E)-8-hydroxy-6-methyl-6-octen-3-one, was studied further with respect to field activity and emission rate from male beetles. In a 5-week field experiment in Oregon, the compound was shown to function as an aggregation pheromone in attracting male and female CLBs migrating from overwintering sites in spring. Traps baited with the synthetic compound (500 microg per rubber septum) caught 3.

Identification and electrophysiological activity of a novel hydroxy ketone emitted by male cereal leaf beetles.

Comparisons of collections of volatiles from male and female Oulema melanopus, feeding on host foliage (oats), revealed an electrophysiologically active male-specific compound, (E)-8-hydroxy-6-methyl-6-octen-3-one (7), which is a new natural product. The structure of 7 was elucidated by spectroscopic and microchemical studies and confirmed by chemical synthesis. Antennal electrophysiology showed the sensitive detection of 7 by both sexes, which is consistent with a male-produced aggregation pheromone.