Meyer Schwarz

Isolation, identification and synthesis of the sex pheromone of the citrus mealybug, Planococcus citri (risso)

Abstract The sex attractant pheromone of the citrus mealybug, Planococcus citri (Risso), has been Identified as (1 R - cis )-(+)-2,2-dimethyl-3-(1-methylethenyl)cyclobutanemethanol acetate (VI).

Sex pheromone of the Asian corn borer moth

Abstract By 1975, insect sex pheromones had been identified from 60 species (1) of moths (Lepidoptera), and nearly all of the 40 compounds involved had been found to be mono- or di-unsaturated C10 to C18 straight-chain aldehydes, alcohols, or acetates, and the sites of olefinic unsaturation were, with one exception (2), at odd-numbered positions in the carbon chain. Since that time, many more lepidopteran pheromone components have been identified, and mono-unsaturated compounds with unsaturation at even-numbered positions in the carbon chain remain extremely rare (3–6). However, in females of Ostrinia furnacalis (Guenee), called the Asian corn borer, we have discovered another mono-olefinic lepidopteran sex pheromone that has the site of unsaturation at ab even carbon position. Females of this corn-pest species produce a ca . 1:1 geometric mixture of ( Z )- and ( E )- 12-tetradecen-1-o1 acetate to attract and sexually stimulate males. On the other hand, the nearest taxonomic relative (7) of the Asian corn borer, the European corn borer, Ostrinia nubilalis (Hubner), uses a mixture of ( Z )- and ( E )-11-tetradecen-1-o1 acetate as its sex pheromone (8). Biochemical explanation of the paucity of monounsaturated moth sex pheromones with olefinic sites at even numbered carbon positions remains to be elucidated.

(E,Z)-2,13-octadecadien-1-ol acetate. A new pheromone structure for sesiid moths

Abstract (E,Z)-1,13-Octadecadien-1-ol acetate was identified from ovipositor extracts of the grape root borer and was shown to attract males of the species.

Identification of the pheromone of the Comstock mealybug

Abstract The Comstock mealybug, Pseudococcus comstocki (Kuwana) is a tiny insect that is a serious agricultural pest of citrus, pomegranates, and other fruit in California and elsewhere throughout the world. The fungus that forms on the insect secretions causes severe smutting and results in economic losses to fruit growers. The female insects emit a sex pheromone that attracts males, and traps containing live females have been used to detect infestations. This pheromone has now been isolated from volatiles trapped from an air stream passed over the insects. The identification as 2, 6-dimethyl-1, 5-heptadien-3-ol acetate was made on the basis of chromatographic and spectroscopic data of the natural material and its derivatives. This is the first pheromone identified from the mealybug family and its norterpene (9-carbon) skeleton is uncommon among insect pheromones. The compound was synthesized and shown to be highly attractive in field bioassay at concentrations as low as 0.2 μg per trap.

An unusual lepidopteran sex pheromone system in the bagworm moth.

The female sex pheromone of the bagworm moth is (R)-1-methylbutyl decanoate. The antipode is biologically inactive and it neither enhances nor detracts from the potency of the R enantiomer. Unlike other moths for which female pheromones have been identified, the female secretes the pheromone from glands on her thorax and it is disseminated from hair that is shed from her body.

Female sex pheromone of the melonworm,Diaphania hyalinata (Lepidoptera: Pyralidae), and analysis of male responses to pheromone in a flight tunnel

Ten C16 chain-length compounds were identified from heptane extracts of ovipositors of female melonworm,Diaphania hyalinata (L.). The major constituents of the extracts were (E)-11-hexadecenal and (E,E)-10,12-hexadecadienal [(E,E)-10,12–16:Ald] and the alcohols and acetates of these olefins were found in trace amounts (<2%). Extracts also contained traces of (E,Z)- and (Z,Z)-10,12-16:Ald, hexadecanal, and 1-hexadecanol. Analysis of the behavioral responses of males to synthetic mixtures of these compounds and responses to ovipositor extracts in a flight tunnel showed that a synthetic mixture of the 10 compounds elicited a behavioral repertoire from males that was indistinguishable from that elicited by ovipositor extract. Flight tunnel studies also indicated that six of the 10 compounds probably represent the essential components of the females sex pheromone.

Insect Juvenile Hormone: Activity of Selected Terpenoid Compounds

A nuimber of compounds with terpenoid skeletons attached to various functional groups were prepared and tested for their effects as a juvenile hormone in the yellow mealworm Tenebrio molitor. Several of these compounds showed high activity.

Isolation, identification, synthesis, and bioassay of the pheromone of the comstock mealybug and some analogs.

The sex pheromone of the Comstock mealybug,Pseudococcus comstocki (Kuwana) was isolated from volatiles trapped from air passing over virgin female insects. Combined gas chromatography, mass and infrared spectroscopy, and microreactions indicated that the structure was 2,6-dimethyl-1,5-heptadien-3-ol acetate. This was confirmed by synthesis; several analogs were also prepared. The natural and synthetic pheromone caused similar trap capture of male insects. Synthetic analogs were significantly less attractive in field tests and the addition of minor amounts of the corresponding alcohol to the pheromone appeared to enhance trap capture, but the results were not statistically conclusive.

European corn borer: Pheromonal catabolism and behavioral response to sex pheromone

When physiologically excessive amounts of the female sex pheromone of the European corn borer (ECB) or esters analogous to the pheromone were applied to the antennae of males, their behavioral responsiveness to pheromone in a flight tunnel was significantly impaired for 2 hr. Concurrent quantitative analyses of heptane extracts of the male antennae by gasliquid chromatography showed that the compounds applied to antennae were hydrolyzed and, at 2 and 4 hr posttreatment, little or none of the compound applied or hydrolysis product was detectable in the antennal extracts. After 4 hr of in vivo incubation, male responsiveness to pheromone was restored among moths treated with the analogs but not among moths treated with pheromone. Esterase activity on the antennae was moderately inhibited in vivo by a pheromone analog that is a so-called transition-state esterase inhibitor, 1,1, 1-trifluoro-14-heptadecen-2-one. However, the analog did not inhibit male behavior when it was coevaporated with pheromone in a flight-tunnel assay. Therefore, in the presence of pheromone, the analog did not compete well for esterase or the pheromone receptor. Treating the antennae of intact males with tetrahydrofuran obliterated sex pheromone response capability in males, but the treatment did not significantly attenuate esterase and other catabolic activity of the antennae. Indications are that degradation of esters on the ECB antennae involves substrate-nonspecific esterase activity and other metabolic processes that in turn remove hydrolysis products from the antennae. Maintenance of a males ability to respond to pheromone is linked to these processes.

Female sex pheromone of the pickleworm, Diaphania nitidalis (Lepidoptera: Pyralidae).

Heptane extracts of the ovipositors from pickleworm adults (Diaphania nitidalis) were found to contain (E)-11-hexadecenal along with proportionally smaller amounts of (Z)-11-hexadecenal, (E)- and (Z)-11-hexadecen-1-ol, hexadecanol, hexadecanal, and a trace amount of (E,Z)-10,12-hexadecadienal. Assays conducted in a flight tunnel and in the field showed that a synthetic mixture of the five unsaturated compounds elicited behavioral responses from pickleworm males that were indistinguishable from those elicited by extracts of the female or by mate-calling females. When any component was deleted from the set of five unsaturated compounds, the intensity and extent of male responses to the resulting mixtures were significantly attenuated. The female sex pheromone of the pickleworm resembles the pheromone of a congeneric species,D. hyalinata, but bioassays indicated that (E,E)-10,12-hexadecadienal, produced byD. hyalinata but not by the pickleworm, plays a role in pheromonal specificity.