Male-specific Compounds Research Articles

Male-produced aggregation pheromone of Colopterus truncatus: structure, electrophysiological, and behavioral activity

A male-produced aggregation pheromone was demonstrated in Colopterus truncatus Randall (Coleoptera: Nitidulidae) by gas chromatographic comparisons of male and female volatile emissions. Male-specific compounds were identified with coupled gas chromatographic–mass spectrometric (GC-MS) analysis and GC and MS comparison of authentic standards. Physiological activity was evaluated by coupled gas chromatographic–electroantennographic (GC-EAG) recordings, and electroantennographic (EAG) assays of standards. The male-produced volatiles eliciting responses from male and female antennae (and relative abundance) were (2E,4E,6E)-3,5-dimethyl2,4,6-octatriene (1) (1.8), (2E,4E,6E)-4,6-dimethyl-2,4,6-nonatriene (2) (100), and (2E,4E,6E,8E)-3,5,7-trimethyl-2,4,6,8-decatetraene (3) (3.3). A fourth male-specific compound, (2E,4E,6E,8E)-4,6,8-trimethyl-2,4,6,8-undecatetraene (4) (0.6) was not EAG-active. EAG dose–response studies showed that the antennae were most sensitive to 2 followed by 3 and 1. Synthetic 2, binary blends of 1 and 3, and tertiary blends of 1, 2, and 3 were highly attractive in the field when synergized with fermenting whole-wheat bread dough. In the field, cross-attraction to the C. truncatus pheromone components was observed for Carpophilus lugubris Murray, C. antiquus Melsheimer, and C. brachypterus Say.

Isopropyl (Z9) -hexadecenoate as a male attractant pheromone from the sternal gland of the rove beetle Aleochara curtala (Coleoptera: Staphylinidae)

In the rove beetle Aleochara curtula, a male specific sternal gland is described. Isopropyl (Z9)-hexadecenoate has been identified by GC/MS of surface and sternal gland extracts as a male specific compound. Its emission in the air was demonstrated by closed-loopstripping-analyses. In field experiments, conspecific males and females were attracted by the odor of carrion, caged males from laboratory cultures, and by the synthetic ester. Isopropyl (Z9)-hexadecenoate or live males, combined with fresh carrion attract more beetles than a fresh carcass alone. Isopropyl hexadecanoate as a minor compound was not attractive. The term “aggregation” pheromone and the ecological significance of attracting females to a fresh carcass allowing early copulation and egg-deposition are discussed.

Pheromone Sharing: Blends Based on the Same Compounds for Euschistus heros and Piezodorus guildinii

Pheromone compounds shared between two species of pentatomids from the soybean stink bug complex are reported. Two male-specific compounds (R t 27.47 and 29.62 min) were detected in the airborne extract of Piezodorus guildinii by gas chromatography and mass spectrometry analysis. The compounds were identified as methyl 2,6,10-trimethyldodecanoate and methyl 2,6,10-trimethyltridecanoate.

Cross-Attraction of Carpophilus humeralis to Pheromone Components of Other Carpophilus Species

The pineapple beetle, Carpophilus humeralis, is known from field tests to be more attracted to baits containing the pheromone blends of other Carpophilus species and food odors than to food odors alone, but a pheromone is not yet known for C. humeralis. Wind-tunnel bioassays were used to determine specifically which of the Carpophilus pheromone components were the most attractive for C. humeralis. Nine tetraene and triene components normally used in field studies, plus eight additional male-specific compounds from other Carpophilus species, and one additional analog, were used in these experiments. At the 10-ng level, 15 of 18 compounds tested with a food-related coattractant (propyl acetate) were more attractive for C. humeralis than the coattractant alone. With decreasing doses (1, 0.1, and 0.01 ng) the number of attractive compounds declined. Only one compound, (2E,4E,6E,8E)-3,5,7-trimethyl-2,4,6,8-decatetraene (1), had significant attraction for C. humeralis at 0.01 ng, close to the lower threshold level of pheromone attraction for other Carpophilus species. Responses to mixtures of compounds were explored. For example, 1 was synergistic with 4-ethyl-2-methoxyphenol (E), 2,5-diisopropylpyrazine (D), and 2-phenylethanol (P), which are known attractants for C. humeralis; a mixture of 1 plus E, D, and P was 20 times more attractive than 1 alone and five times more than E, D, plus P. The specificity of C. humeralis for certain tetraenes was similar to that exhibited by C. hemipterus, while the specificity for trienes was similar to that of C. freemani. The behavior of C. humeralis to these pheromone components suggests that it may have a pheromone like that of other Carpophilus species or that it could possibly use these compounds as host finding kairomones.

5-Methyl-2-phenyl-2-hexenal in the scent gland secretion of male cave crickets, Troglophilus cavicola and T. neglectus (Ensifera: Rhaphidophoridae)

5-Methyl-2-phenyl-2-hexenal, a distinctly smelling compound, was identified as a constituent of the male scent gland secretion of two species of cave crickets, Troglophilus cavicola and T. neglectus. It is the first proof of a male specific exocrine compound in grasshoppers. A pheromonal function of the component could not be established; its possible biological role is discussed.

Aggregation pheromone ofCarpophilus dimidiatus (F.) (Coleoptera: Nitidulidae) and responses toCarpophilus pheromones in South Carolina

The major component of the male-produced aggregation pheromone ofCarpophilus dimidiatus (F.) is (3E, 5E, 7E, 9E)-6,8-diethyl-4-methyl-3,5,7,9-dodecatetraene. It attracts beetles of both sexes in the field and is synergized by odors from fermenting bread dough; mean trap catches for the tetraene alone, tetraene plus dough, dough alone, and control were 24.5, 48.3, 0.02, and 0.00, respectively. In the laboratory, individual males produced 0.58 µg±0.35 µg (SD) of the tetraene per day, but males in groups of 10-50 produced <2% as much per beetle. A second male-specific compound, (3E, 5E, 7E, 9E)-5,7-diethyl-9-methyl-3,5,7,9-tridecatetraene, was also identified fromC. dimidiatus and is about 5% as abundant as the major pheromone component.Carpophilus flight activity was monitored for one year in South Carolina corn fields with the pheromones forC. dimidiatus, C. freemani Dobson,C. mutilatus Erichson,C. hemipterus (L.),C. lugubris Murray, andC. obsoletus Erichson, all in combination with bread dough. The first four of these species accounted for 18, 70, 5.7, and 0.03%, respectively, of the totalCarpophilus trapped, but noC. lugubris orC. obsoletus were captured. Captures ofC. freemani were as high as 11,400/trap/week. Species specificity for the first four pheromones was high, except that a synthetic impurity in theC. dimidiatus pheromone was somewhat attractive toC. freemani andC. mutilatus. Three other species captured.C. antiques Melsheimer,C. marginellus Motschulsky, andC. humeralis (F.), accounted for 0.005, 5.0, and 1.3% of the total catch, respectively.C. antiquus was attracted primarily to the pheromone ofC. dimidiatus, butC. marginellus andC. humeralis responded to most of the test pheromones. There were two major periods ofCarpophilus flight activity: February through June and September through November.

The male pheromone of the old house borerHylotrupes bajulus (L.) (Coleoptera: Cerambycidae): Identification and female response

We report here the identification of the long-range, male-produced sex pheromone of the Old house borerHylotrupes bajulus. Chemical analysis of hexane extracts obtained by surface extraction from dissected prothoracic glands and from headspace samples of the two sexes, revealed male-specific compounds: (3R)-3-hydroxy-2-hexanone, 2-hydroxy-3-hexanone, the diastereomeric diols (2R, 3R)-2,3-hexanediol and (2S, 3R)-2,3-hexanediol, 2,3-hexanedione, as well as 1-butanol.

Aggregation pheromone for the pepper weevil,Anthonomus eugenii cano (Coleoptera: Curculionidae): Identification and field activity

This study describes the identification of an aggregation pheromone for the pepper weevil,Anthonomus eugenii and field trials of a synthetic pheromone blend. Volatile collections and gas chromatography revealed the presence of six male-specific compounds. These compounds were identified using chromatographic and spectral techniques as: (Z)-2-(3,3-dimethylcyclohexylidene)ethanol, (E)-2-(3,3-dimethylcyclohexylidene)ethanol, (Z)-(3,3-dimethylcyclohexylidene)acetaldehyde, (E)-(3,3-dimethylcyclohexylidene)acetaldehyde, (E)-3,7-dimethyl-2,6-octadienoic acid (geranic acid), and (E)-3,7-dimethyl-2,6-octadien-1-ol (geraniol). The emission rates of these compounds from feeding males were determined to be about: 7.2, 4.8, 0.45, 0.30, 2.0, and 0.30µg/male/day, respectively. Sticky traps baited with a synthetic blend of these compounds captured more pepper weevils (both sexes) than did unbaited control traps or pheromone-baited boll weevil traps. Commercial and laboratory formulations of the synthetic pheromone were both attractive. However, the commercial formulation did not release geranic acid properly, and geranic acid is necessary for full activity. The pheromones of the pepper weevil and the boll weevil are compared. Improvements for increasing trap efficiency and possible uses for the pepper weevil pheromone are discussed. A convenient method for purifying geranic acid is also described.

Attractant pheromone for nearctic stink bug,Euschistus obscurus (Heteroptera: Pentatomidae): Insight into a neotropical relative

Volatiles fromEuschistus obscurus males were found to be attractive to conspecific females in bioassays. A new type of olfactometer assembled from commercially available glassware was used to bioassay aeration extracts of the Nearctic stink bug,E. obscurus. Fractionated extracts suggest that pheromonal activity is associated with late-eluting, male-specific compounds. Research onE. obscurus offered a means to indirectly study the pheromone of the Neotropical pest species,E. heros, without importing this soybean pest into the United States.

The Odor-Bouquet of Ips schmutzenhoferi Holzschuh (Col.: Scol.)

Abstract Ipsenol, Ipsdienol, and E-myrcenol are male specific compounds of Ips schmutzenhoferi. Overall 46 compounds could be identified from males and females. The diversity of oxygenated terpenes is particularly high in males.

A few chemical words exchanged by Drosophila during courtship and mating.

Experimental evidence and speculation relative to chemical messages exchanged byDrosophila during courtship and mating are reviewed. Only the speciesD. melanogaster andD. simulans are considered in detail. Emphasis is put on female aphrodisiacs, as they clearly participate in sex and species recognition. All the aphrodisiac molecules described are unsaturated long-chain hydrocarbons, and position 7 for a double bond seems important in both species. InD. melanogaster, only females are able to make 7,11-dienes, compounds which stimulate males of this species to court. InD. simulans, 7-tricosene plays a similar role but is produced by both sexes as well as maleD. melanogaster. In both species, polymorphism is shown for these molecules. Their biosynthesis is also considered and both preliminary biochemical and genetic data are introduced. Male-specific compounds which regulate male and female behaviors are also reviewed. For example,cis-vaccenyl acetate inhibits male courtship; one or two peptides control the female's receptivity and egg laying. Such compounds are transferred from males to females together with sperm.

Oxidation products of pinene in the bark beetle, Dendroctonus frontalis

Southern pine beetles were collected as they emerged from infested pine bolts and exposed in Petri dishes to α- and β-pinene for 20 hr. Changes in the volatile contents of the beetles' hindguts were detected by gas chromatography, and previously unidentified components were characterized by mass, i.r., and n.m.r. spectroscopy. A prominent compound in hindguts of both sexes before and after treatment was identified as myrtenol, and a less conspicuous, male-specific compound proved to be myrtenal. Upon exposure to α-pinene, males produced cis- and trans-verbenol, and 4-methyl-2-pentanol was found in both sexes. Compounds present after treatment with β-pinene vapour were identified as trans-pinocarveol in both sexes, and pinocarvone in the males.