Female-produced Sex Attractant Research Articles

(R)-Desmolactone is a sex pheromone or sex attractant for the endangered valley elderberry longhorn beetle Desmocerus californicus dimorphus and several congeners (Cerambycidae: Lepturinae).

We report here that (4R,9Z)-hexadec-9-en-4-olide [(R)-desmolactone] is a sex attractant or sex pheromone for multiple species and subspecies in the cerambycid genus Desmocerus. This compound was previously identified as a female-produced sex attractant pheromone of Desmocerus californicus californicus. Headspace volatiles from female Desmocerus aureipennis aureipennis contained (R)-desmolactone, and the antennae of adult males of two species responded strongly to synthetic (R)-desmolactone in coupled gas chromatography-electroantennogram analyses. In field bioassays in California, Oregon, and British Columbia, traps baited with synthetic (R)-desmolactone captured males of several Desmocerus species and subspecies. Only male beetles were captured, indicating that this compound acts as a sex-specific attractant, rather than as a signal for aggregation. In targeted field bioassays, males of the US federally threatened subspecies Desmocerus californicus dimorphus responded to the synthetic attractant in a dose dependent manner. Our results represent the first example of a “generic” sex pheromone used by multiple species in the subfamily Lepturinae, and demonstrate that pheromone-baited traps may be a sensitive and efficient method of monitoring the threatened species Desmocerus californicus dimorphus, commonly known as the valley elderberry longhorn beetle.

Female calling and male flight orientation and searching behaviors in Callisphyris apicicornis: evidence for a female-produced sex attractant pheromone

T. Curkovic, and C. Ferrera. 2012. Female calling and male flight orientation and searching behaviors in Callisphyris apicicornis: evidence for a female-produced sex attractant pheromone. Cien. Inv. Agr. 39(1): 147-158. Callisphyris apicicornis is a fruit pest of increasing concern in Chile. To aid in the identification of its sex pheromone for use in the management of this insect, “calling” (pheromone release) of females and “orientation and searching” behaviors of males to calling females were video recorded. Light intensity, wind speed, temperature, time of the day, and the frequency of individuals performing each step within both behavioral sequences were recorded as well. Drawings of the behavioral steps and ethograms (routes and returns) are also provided, including transition frequencies between behavioral steps. The calling behavior of females included diagnostic movements of the abdomen, legs, elytra, and wings, showing similarities to the descriptions of other cerambycid species in which females call. The orientation and searching behavior of males included zigzagging flights (characteristic steps observed in insects responding to airborne pheromone plumes) and landing on and searching for females in cages. Females called and males responded mainly between 9 AM and 1 PM. Both behaviors were performed in a non-random fashion and were stereotyped. Calling behavior was significantly affected by light (apparently triggering the behavior) but not by wind speed, ambient temperature, or female age. Males tended to respond most strongly to younger females, although these called significantly less frequently than older ones. These results strongly support the existence of a female-produced sex pheromone in C. apicicornis and provide the background information to aid in attempts of pheromone collection and identification. Male behavior characterization also provides a base-line to compare with tests to evaluate the activity of putative pheromones for this species. This study is one of the first reports of a cerambycid species in which the female calls and the male consequently responds to her and the first one on the characterization of the calling and oriented searching behaviors for a Necydalinae.

(R)-Desmolactone, A Female-produced Sex Pheromone Component of the Cerambycid Beetle Desmocerus californicus californicus (subfamily Lepturinae)

We report the identification, synthesis, and field bioassays of a female-produced sex attractant pheromone for the cerambycid beetle Desmocerus californicus californicus Horn. Headspace volatiles from females contained a sex-specific compound, (R)-desmolactone [(4R,9Z)-hexadec-9-en-4-olide], which elicited strong responses from the antennae of adult males in coupled gas chromatography-electroantennogram analyses. Short syntheses of both enantiomers were developed from commercial chiral synthons. In field bioassays, significant numbers of males were collected in traps baited with (R)-desmolactone, whereas the (S)-enantiomer attracted no males. The racemate was less attractive than the pure (R)-enantiomer, indicating some degree of antagonism by the unnatural enantiomer. This compound is the first example of a new structural class of cerambycid pheromones, and is the second pheromone identified for a species in the subfamily Lepturinae.

Cis-Vaccenyl Acetate, A Female-Produced Sex Pheromone Component of Ortholeptura valida, A Longhorned Beetle in the Subfamily Lepturinae

We report the identification, synthesis, and field bioassays of a female-produced sex attractant pheromone component of the cerambycid beetle Ortholeptura valida (LeConte). Headspace volatiles from females contained a female-specific compound, (Z)-11-octadecen-1-yl acetate, which elicited a strong response from antennae of adult males in coupled gas chromatography-electroantennogram analyses. In field bioassays, significant numbers of males were collected by traps baited with this compound. The pheromone represents a new structural class of cerambycid pheromones, and is the first pheromone identified for a cerambycid species in the subfamily Lepturinae.

Determination of the Relative and Absolute Configurations of the Female-produced Sex Pheromone of the Cerambycid Beetle Prionus californicus

We previously identified the basic structure of the female-produced sex attractant pheromone of the cerambycid beetle, Prionus californicus Motschulsky (Cerambycidae: Prioninae), as 3,5-dimethyldodecanoic acid. A synthesized mixture of the four stereoisomers of 3,5-dimethyldodecanoic acid was highly attractive to male beetles. Here, we describe stereoselective syntheses of three of the four possible stereoisomers, and the results of laboratory and field bioassays showing that male beetles are attracted specifically to (3R,5S)-3,5-dimethyldodecanoic acid, but not to its enantiomer, (3S,5R)-3,5-dimethyldodecanoic acid, indicating that the (3R,5S)-enantiomer is the active pheromone component. The diastereomeric (3R,5R)- and (3S,5S)-enantiomers were excluded from consideration because their gas chromatographic retention times were different from that of the insect-produced compound. The mixture of the four stereoisomers of 3,5-dimethyldodecanoic acid was as attractive to male P. californicus as the (3R,5S)-enantiomer, indicating that none of the other three stereoisomers inhibited responses to the active enantiomer. Beetles responded to as little as 10 ng and 10 μg of synthetic 3,5-dimethyldodecanoic acid in laboratory and field studies, respectively. Field studies indicated that capture rate did not increase with dosages of 3,5-dimethyldodecanoic acid greater than 100 μg. In field bioassays, males of a congeneric species, P. lecontei Lameere, were captured in southern California but not in Idaho.

Improved Synthesis of (3E,6Z,9Z)-1,3,6,9-Nonadecatetraene, Attraction Inhibitor of Bruce Spanworm, Operophtera bruceata, to Pheromone Traps for Monitoring Winter Moth, Operophtera brumata

The winter moth, Operophtera brumata (Lepidoptera: Geometridae), is an early-season defoliator that attacks a wide variety of hardwoods and, in some cases, conifers. The insect is native to Europe but has become established in at least three areas of North America including southeastern New England. The female-produced sex attractant pheromone of the winter moth was identified as (3Z,6Z,9Z)-1,3,6,9-nonadecatetraene (1), which also attracts a native congener, the Bruce spanworm, Operophtera bruceata . Dissection, or (for certainty) DNA molecular testing, is required to differentiate between males of the two species. Thus, a trapping method that is selective for winter moth would be desirable. A geometric isomer of the pheromone, (3E,6Z,9Z)-1,3,6,9-nonadecatetraene (2), can reportedly inhibit attraction of Bruce spanworm to traps without affecting winter moth catch, but use of the pheromone and inhibitor together has not been optimized, nor has the synthesis of the inhibitor. This paper presents two new syntheses of the inhibitor (3E,6Z,9Z)-1,3,6,9-nonadecatetraene based on the intermediate (3Z,6Z)-3,6-hexadecadien-1-ol (4), which has also been utilized in the synthesis of the pheromone. The syntheses combine traditional acetylenic chemistry and Wittig olefination reactions. In one approach, 2 was synthesized in 80% purity (20% being pheromone 1), and in the second, tetraene 2 of 96% purity (and free of 1) was produced in 25% overall yield from dienol 4. The last method benefitted from a refined TEMPO-mediated PhI(OAc)(2) oxidation of 4 and a two-carbon homologation of the corresponding aldehyde 7.

Identification of a Sex Attractant Pheromone for Male Winterform Pear Psylla, Cacopsylla pyricola

Pear psylla, Cacopsylla pyricola (Förster) (Hemiptera: Psyllidae), a major economic pest of pears, uses a female-produced sex attractant pheromone. We compared the chemical profiles obtained from cuticular extracts of diapausing and post-diapause winterform males and females to isolate and identify the pheromone. Post-diapause females produced significantly more of the cuticular hydrocarbon, 13-methylheptacosane, than post-diapause males and diapausing females. In olfactometer assays, conspecific males were attracted to synthetic racemic 13-methylheptacosane, whereas females were not, indicating that the behavioral response to this chemical is sex-specific. Furthermore, 13-methylheptacosane was as attractive to males as a cuticular extract of females, suggesting that this chemical was largely responsible for the female attractiveness. A field study showed that males but not females were attracted to 13-methylheptacosane, confirming the olfactometer results. This study provides evidence that 13-methylheptacosane is a sex attractant pheromone for C. pyricola winterform males. This is the first identification of a sex pheromone in the Psylloidea. Our results open the path to developing monitoring tools and possibly new strategies for integrated pest management of this insect.

Mating System of the European Hornet Vespa crabro: Male Seeking Strategies and Evidence for the Involvement of a Sex Pheromone

We describe details of the mate finding strategy of drones of the European hornet, Vespa crabro, and present evidence for the involvement of sex pheromones. Tests were carried out with free flying drones in natural habitats. Males patrolled the nest site itself, as well as nearby nonresource-based sites, without showing territorial behavior. Patrolling was restricted to sunny spots in the vegetation, and thus, the locations changed throughout the day. Drones were attracted to both caged gynes and to dead workers treated with gyne extracts, indicating the presence of a female-produced sex attractant. Treated workers also elicited copulation attempts by the attracted drones. Extracts from gynes, workers, and drones contained exclusively cuticular lipids, and the profile from gynes was much more diverse than that of workers and drones. The most striking differences observed related to the alkenes, monomethyl- and dimethylalkanes. The results provide a lead for potential attracting and copulation-releasing semiochemicals in V. crabro.

Methyl 2-(methylthio)benzoate: the unique sulfur-containing sex pheromone of Phyllophaga crinita.

The female-produced sex pheromone of Phyllophaga crinita (Burmeister) (Coleoptera: Scarabaeidae: Melolonthinae; the adult has no common name) is identified as methyl 2-(methylthio)benzoate. This is the first identification of a sulfur-containing, long-distance, female-produced sex attractant from any insect taxa. The root-feeding larvae of this species are serious pests in many crops in Texas and Mexico. In field tests, many P. crinita males were captured in traps baited with the authentic compound. Interestingly, a heteroatom analog, methyl 2-methoxybenzoate, also captured P. crinita males, but only at a dose 10,000 times higher than the lowest tested dose of the authentic pheromone.

Sex Attractant Pheromone of Saturniid Moth Coloradia velda

The female-produced sex attractant pheromone of Coloradia velda has been identified by a combination of analytical methods and field tests as a blend of (10E,12Z)-hexadecadien-1-yl acetate (10E,12Z–16:Ac), (10E,12E)-hexadecadien-1-yl acetate (10E,12E–16:Ac), and (10E,12Z)-hexadecadien-1-ol (10E,12Z–16:OH) in a 10:1:0.33 ratio, respectively. The corresponding aldehyde (10E,12Z–16:Ald) was also found in extracts of female pheromone glands, but in blends with 10E,12Z–16:Ac and 10E,12E–16:Ac at low doses did not significantly increase the attractiveness of baits to male moths.