Male-produced aggregation pheromone ofCarpophilus obsoletus (Coleoptera: Nitidulidae)

Males ofCarpophilus obsoletus Erichson produce an aggregation pheromone to which both sexes respond. The pheromone was identified by GC-MS as (2E,4E,6E,8E)-3,5,7-trimethyl-2,4,6,8-undecatetraene (1), which is also a minor constituent of the pheromone blends ofC. hemipterus (L.),C. freemani Dobson, andC. lugubris Murray. The pheromone was synergized in wind-tunnel bioassays by propyl acetate, a host-type coattractant. In a dose-response study, 50 pg of1, plus propyl acetate, was significantly more attractive than just propyl acetate. Pheromone emission from groups of 65 males, feeding on artificial diet, averaged 2.2 ng/male/day. Emissions from individual males were larger, averaging 72 ng/day and ranging as high as 388 ng/day. Synthetic1 was tested in a date garden in southern California (500 µg/rubber septum), using fermenting whole-wheat bread dough as the coattractant. The pheromone plus dough attracted significantly more beetles than dough alone (means were 4.2 and 0.0 beetles per week per trap). Captured beetles were 54% females. Field trap catches were highest during the months of July and August.All programs and services of the U.S. Department of Agriculture are offered on a nondiscriminatory basis without regard to race, color, national origin, religion, sex, age, marital status, or handicap. Mention of firm names or trade products does not imply endorsement by the U.S. Department of Agriculture over similar firms or products not mentioned.     

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.Names are necessary to report factually on available data; however, the USDA neither guarantees nor warrants the standard of the product, and the use of the names by USDA implies no approval of the product to the exclusion of others that may also be suitable.     

Male-produced aggregation pheromone ofCarpophilus mutilatus (Coleoptera: Nitidulidae)

Males ofCarpophilus mutilatus Erichson produce an aggregation pheromone to which both sexes respond. The pheromone includes two hydrocarbon components, (3E,5E,7E)-5-ethyl-7-methyl-3,5,7-undecatriene (1) and (3E,5E,7E)-6-ethyl-4-methyl-3,5,7-decatriene (2). These were emitted in a 101 ratio and in a total amount of ca. 5 ng per feeding male per day. All tested doses of1 and2, from 0.03 to 30 ng, were more attractive than controls in wind-tunnel tests, but there was no evidence of synergism between these trienes. Dramatic synergism between the pheromone and a food-type coattractant occurred in the field, however. In a date garden in southern California, traps with a combination of synthetic1 and fermenting whole-wheat bread dough attracted 22 times more beetles than dough by itself and 295 times more than1 by itself. Volatile collections from males also contained three oxygenated compounds that were absent from females. One of these was tetradecanal (ca. 5 ng per male per day), but the structures of the other two are presently undetermined (0.8 and 1.1 ng per male per day). No function for these was demonstrated. One compound originating in the artificial diet, 2-phenylethanol, was particularly attractive in the wind-tunnel bioassay, as was the chromatographic solvent, methanol.     

Aggregation pheromone of Australian SAP beetle,Carpophilus davidsoni (Coleoptera: Nitidulidae)

A male-produced aggregation pheromone was identified for the Australian sap beetle,Carpophilus davidsoni Dobson (Coleoptera: Nitidulidae), by bioassay-guided fractionation of volatiles collected from feeding beetles. The most abundant components were: (2E,4E,6E)-5-ethyl-3-methyl-2,4,6-nonatriene, (3E,5E,7E)-6-ethyl-4-methyl-3,5,7-decatriene, (2E,4E,6E,8E)-3,5,7-trimethyl-2,4,6,8-undecatetraene, and (2E,4E,6E,8E)-7-ethyl-3,5-dimethyl-2,4,6,8-undecatetraene. The relative abundance of these components in collections from individual males feeding on artificial diet was 100:7:9:31, respectively. Pheromone production began within several days after males were placed onto diet medium and continued for at least 20 weeks. Peak production was >3 µg total pheromone per male per day. Males in groups of 50–60 emitted less pheromone (the peak level was 0.09 µg per beetle per day), and the emissions from groups contained relatively little tetraene (proportions of the components listed above were 100:7:2:7, respectively). Three additional trienes and one additional tetraene were identified in minor amounts; the entire eight-component male-specific blend is qualitatively identical and quantitatively similar to that of the North American sibling species,C. freemani Dobson. A synthetic blend of the four major components on rubber septa, prepared to emit in the same proportions as from individual males, was highly attractive in the field when synergized with fermenting whole-wheat bread dough. Cross-attraction was observed in the field involving the pheromones ofC. davidsoni, C. hemipterus (L.), andC. mutilatus Erichson. Potential uses of the pheromones in pest management are discussed.Names are necessary to report factually on available data; however, the USDA neither guarantees nor warrants the standards of the products, and the use of the names by USDA implies no approval of the products to the exclusion of others that may also be suitable.     

Attraction ofCarpophilus Spp. (Coleoptera: Nitidulidae) to volatile compounds present in figs

Various volatile compounds present in ripening figs were attractive toCarpophilus hemipterus, C. mutilatus, C.freemani, andC. lugubris. Field tests demonstrated that traps baited with a mixture of acetaldehyde, ethyl alcohol, and ethyl acetate caught more adultC. hemipterus than those baited with (1) other mixtures involving various combinations of 19 compounds, (2) with 16 single compounds, or (3) with fig paste.This investigation was supported in part by a grant from the California Dried Fig Advisory Board.     

Identification of food volatiles attractive to dusky sap beetle,Carpophilus lugubris (Coleoptera: Nitidulidae)

The chemical mediation of host-finding was investigated for the dusky sap beetle,Carpophilus lugubris Murray. GC-MS analysis of the headspace volatiles above whole-wheat bread dough inoculated with baker's yeast, a substrate previously determined to be an effective attractant, revealed seven major components in the following order of decreasing concentration: ethanol, acetaldehyde, 2-methylpropanol, 3-methylbutanol, propanol, 2-methylbutanol, and ethyl acetate. Solutions of these seven compounds blended so as to mimic the odor of whole-wheat bread dough elicited upwind orientation from 1.8 m in a wind tunnel byC. lugubris at a level comparable to that elicited by the bread dough. A series of bioassays investigating the role of individual components from the synthetic blend determined that all seven compounds contributed to behavioral activity; however, the simplest blend evoking attraction comparable to bread dough included acetaldehyde, ethyl acetate, 2-methylpropanol, and 3-methylbutanol. Of these compounds, acetaldehyde was essential, ethyl acetate was interchangeable with ethanol or partially replaceable with propanol, and 2-methylpropanol and 3-methylbutanol were partially replaceable with a combination of the other alcohols. Headspace volatiles above aseptic or fungus-inoculated tomato, banana, sweet corn, and strawberry were also qualitatively and quantitatively analyzed. This study suggests thatC. lugubris locates its food sources by response to variable blends of common volatile constituents of plants and fungi.     

Attraction ofCarpophilus spp. (Coleoptera: Nitidulidae) to synthetic aggregation pheromones and host-related coattractants in Australian stone fruit orchards: Beetle phenology and pheromone dose studies

Synthetic aggregation pheromones ofCarpophilus hemipterus (L.) andCarpophilus mutilatus Erichson were field tested during a 10-month period in southern New South Wales stone fruit orchards to determineCarpophilus spp. phenology and the effect of two pheromone doses on attraction. Aggregation pheromones synergize the attraction of host volatiles toCarpophilus spp. Four major species,C. hemipterus, C. mutilatus, C. davidsoni Dobson andC. (Urophorus) humeralis (F.), were trapped, with greater numbers of each species inC. hemipterus pheromone/fermenting whole-wheat breaddough-baited traps, than in dough-only-traps. InC. mutilatus pheromone/ fermenting-dough-baited traps, onlyC. mutilatus andC. davidsoni responded in greater numbers than to dough-only traps. Beetles first appeared in traps in late September (early spring) when daily maximum temperatures averaged 17.5C. Trappings reached a peak during October and declined to very low levels in November–December (late spring-early summer). Numbers trapped of all species increased during February–March (late summer–early autumn), presumably due to the presence of abundant host resources (ripening and fallen fruit), and continued at high levels until May (late autumn). An 18-week study demonstrated significantly greater responses byCarpophilus spp. to 5000-g than to 500-g doses of C.hemipterus andC. mutilatus pheromones. Greatest responses to 5000g were recorded forC. hemipterus andC. mutilatus responding to their own pheromones (increased attraction over dough alone of 259x and 21.2x respectively). Implications of the study and the potential for using synthetic aggregation pheromones for managingCarpophilus spp. populations in Australian stone fruit are discussed.     

Male-specific tetraene and triene hydrocarbons ofCarpophilus hemipterus: Structure and pheromonal activity

Males ofCarpophilus hemipterus (L.), the dried-fruit beetle, (Coleoptera: Nitidulidae) were found to emit nine all-E tetraene and one all-E triene hydrocarbons in addition to two pheromonally active tetraenes that had been reported previously. The previously known compounds are (2E,4E,6E,8E)-3,5,7-trimethyl-2,4,6,8-decatetraene(1) and (2E,4E,6E,8E)-3, 5,7-trimethyl-2,4,6,8-undecatetraene(2). The new tetraenes were all related to structure1 by having one additional carbon at either one or two of the following four locations: at carbon 1 of the chain, at carbon 10 of the chain, at the 5-alkyl branch, or at the 7-alkyl branch. (Structure 2 also fits within this pattern.) The triene inC. hemipterus is (2E,4E,6E)-5-ethyl-3-methyl-2, 4,6-nonatriene. Also identified from volatile collections from the beetles were the 2Z and 4Z isomers of1. All structures were proven by synthesis, with NMR and mass spectral data for the compounds provided. Two of the newly discovered compounds, (2E,4E,6E,8E)-7-ethyl-3,5-dimethyl-2,4,6,8-decatetraene and (2E,4E,6E,8E)-7-ethyl-3,5-dimethyl-2,4,6,8-undecatetraene, were quite active in the wind-tunnel bioassay, but others, such as (2E,4E,6E,8E)-5-ethyl-3,7-dimethyl-2,4,6,8-decatetraene and (2E,4E,6E,8E)-4,6,8-trimethyl-2,4,6,8-undecatetraene were not. Structureactivity relationships are explored among the natural compounds and additional, synthetic analogs, which were never detected from the beetles. Some of these analogs, such as (2E,4E,6E,8E)-3,5-dimethyl-7-propyl-2,4,6,8-undecatetraene, were quite active in the bioassay. The biosynthesis of the beetle-derived compounds is discussed. A single biosynthetic scheme that lacks complete enzyme specificity at four specific steps could account for the entire series of compounds found in the beetles and their relative proportions. The definition of pheromone is discussed in relation to these hydrocarbons.     

Chemical characterization of fruit and fungal volatiles attractive to dried-fruit beetle,Carpophilus hemipterus (L.) (Coleoptera: Nitidulidae)

The chemical basis underlying orientation to fruit and fungal odors was investigated for the dried-fruit beetle,Carpophilus hemipterus (L.). In wind-tunnel bioassays of walking and flight response from 1.8 m, beetles were attracted to odors of the yeastSaccharomyces cerevisiae on agar, aseptic banana, or banana inoculated withS. cerevisiae, although both banana substrates elicited greater response than the yeast alone. When presented in a two-choice bioassay, the yeast-inoculated banana attracted approximately twice as many beetles as did the aseptic banana. GC-MS analysis of the headspace volatiles above these odor sources revealed a somewhat more complex and concentrated volatile profile for yeast-inoculated banana than for aseptic banana. The odor from yeast on agar had fewer components, and these were present at lower concentrations than the odors of either banana substrate. By blending mineral-oil or aqueous solutions of the 18 components of inoculated-banana odor in varying concentrations, it was possible to mimic closely the headspace profile of the natural odor. This synthetic odor also elicited beetle attraction in the wind tunnel at levels comparable to the inoculated banana. Through a series of bioassays in which individual components were subtracted from or added to a synthetic odor blend, it was determined that ethyl acetate, acetaldehyde, 2-pentanol, and 3-methylbutanol comprised the simplest blend of compounds evoking full behavioral response. However, 2-methylpropanol or butanol were apparently interchangeable with 3-methylbutanol in this blend, and comparable response could also be elicited by replacing acetaldehyde with a combination of both 2-pentanone and 3-hydroxy-2-butanone. Thus, our results suggest that this generalist insect herbivore locates its hosts by a long-range response to a variety of blends of common fruit volatiles, whose concentrations are enhanced by fungi.     

Aggregation pheromone of palmetto weevil,Rhynchophorus cruentatus (F.) (Coleoptera: Curculionidae)

5-Methyl-4-octanol is the major aggregation pheromone of the palmetto weevil,Rhynchophorus cruentatus (F.). The pheromone (cruentol) was identified by coupled gas chromatographic-electroantennographic (GC-EAD) analysis of male-produced volatiles, coupled GC-mass spectrometry (MS) in electron impact and chemical ionization mode, and coupled GC-high resolution MS. In laboratory and field assays, a diastereomeric mixture of synthetic cruentol greatly enhanced attraction of weevils to cabbage palmetto,Sabal palmetto (Walter), stem tissue, indicating that cruentol and host volatiles are synergistically attractive. An attractive lure in combination with efficient traps should facilitate development of semiochemical-based management forR. cruentatus.     

Identification of food volatiles attractive toGlischrochilus quadrisignatus andGlischrochilus fasciatus (Coleoptera: Nitidulidae)

Seven volatile compounds identified from the headspace of whole wheat bread dough were investigated for their role in attractingGlischrochilus quadrisignatus andG. fasciatus in the field. Traps baited with either whole wheat bread dough or a synthetic seven-component bread dough odor caught similar numbers of these beetles, suggesting that the seven-compound combination could simulate the behavioral effect of bread dough. A series of trials using traps baited with various combinations of these chemicals showed that five compounds were significantly active in attractingG. quadrisignatus andG. fasciatus, but not all were essential for maximum response. The simplest blend eliciting a level of response comparable to the seven-component combination included ethyl acetate, acetaldehyde, ethanol, and racemic 2-methylbutanol, of which ethyl acetate, ethanol, and acetaldehyde were essential and 2-methylbutanol was replaceable with 2-methylpropanol forG. quadrisignatus attraction. Ethyl acetate and ethanol were essential for comparable attraction ofG. fasciatus. The chemical mediation of food finding in G.quadrisignatus andG. fasciatus is discussed in the context of volatile blends characterized for other nitidulid species.     

Aggregation pheromone of the deodar weevll,Pissodes nemorensis (Coleoptera: Curculionidae): Isolation and activity of grandisol and grandisal

The bark weevilPissodes nemorensis, a pest of pines and exotic cedars in the southeastern United States, utilizes a male-produced aggregation pheromone. The presumed pheromone components, grandisol (cis-2-isopropenyl-1-methylcyclobutaneethanol) and its corresponding aldehyde, grandisal, were isolated from extracts of male volatiles and male hindguts. A field test in northern Florida showed that the combination of grandisol, grandisal, and slash pine (Pinus elliottii) bolts acted synergistically to attract large numbers of male and femaleP. nemorensis. These components deployed in various paired combinations were not as attractive as the tripartite mixture. There was no evidence that flying weevils were attracted to unbaited pine bolts. The aggregation pheromone forP. nemorensis appears to be similar to that of a parapatric sibling species,P. approximatus.     

Ipsenol: an aggregation pheromone forIps latidens (Leconte) (Coleoptera: Scolytidae)

Ipsenol was identified from the frass of male, but not female,Ips latidens from British Columbia, feeding in phloem tissue of lodgepole pine,Pinus contorta var.latifolia. The responses ofJ. latidens to sources of ips-enol andcis-verbenol were determined with multiple-funnel traps in stands of lodgepole pine in British Columbia. Ipsenol attracted both male and femaleI. latidens, verifying that it is a pheromone for this species. MaleI. latidens showed a slight preference for (S)-(–)-ipsenol.cis-Verbenol was not produced by beetles of either sex and, in contrast to an earlier report, both enantiomers inhibited attraction to ipsenol-baited traps. The predators,Enoclerus sphegeus andThanasimus undatulus (Cleridae), were attracted to traps baited withcis-verbenol and ipsenol.     

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.The mention of firm names or trade products does not imply endorsement or recommendation by the U.S. Department of Agriculture over other firms or similar products not mentioned. All programs and services of the U.S. Department of Agriculture are offered on a nondiscriminatory basis without regard to race, color, national origin, religion, sex, age, marital status or handicap.     

Sex pheromone biology and behavior of the cowpea weevilCallosobruchus maculatus (Coleoptera: Bruchidae)

Female cowpea weevils,Callosobruchus maculatus (F.), emitted a pheromone which excited males. Pheromone release began soon after emergence and continued for one week. Synchronization of pheromone release with calling behavior was demonstrated. Mating reduced pheromone release but not male response. Pheromone obtained by aeration collection was utilized for determining a quantitative dose-response relationship.Mention of a commercial product does not constitute an endorsement by the USDA.Visiting scholar on leave from Shanghai Institute of Entomology, PRC.     

Laboratory and field evidence for maleproduced aggregation pheromone inRhynchophorus cruentatus (F.) (Coleoptera: Curculionidae)

Laboratory and field assays were conducted to determine if palmetto weevil,Rhynchophorus cruentatus (F.), adults produce an aggregation pheromone. Attraction of females in a Y-tube olfactometer to conspecific males was greater than to clean air. Male and female attraction to conspecific male volatiles combined with host-palm,Sabal palmetto (Walter), volatiles was greater than to host-palm volatiles alone. Similarly, more weevils were caught in the field in traps baited with conspecific males plus host-palm tissue than in similar traps baited with only males, or palm tissue, or females, or females plus palm tissue. These results suggest thatR. cruentatus males produce an aggregation pheromone(s) that is highly attractive to conspecific adults of both sexes when combined with host-palm volatiles. This study is an important step towards understanding the chemical ecology ofR. cruentatus.     

Field trapping ofMigdolus fryanus westwood (Coleoptera: Cerambycidae) using natural sex pheromone

Migdolus fryanus is a sugarcane pest restricted to South America that is becoming more important due to the inefficacy of control methods against it. The larvae bore into the plant root system and the available insecticides can not give adequate protection. So, the search for alternate control strategies is mandatory. However, the literature on bioethological studies of the species is scarce. This work investigates the attraction of adult males in the field by females that is mediated by a sex pheromone that remains to be identified. Dissected female thoraces were more attractive than other body parts. A trap design for monitoring field populations of this species also is presented.     

Reproductive biology of the yellow-spotted longicorn beetle,Psacothea hilaris (pascoe) (Coleoptera: Cerambycidae). III. Identification of contact sex pheromone on female body surface

A major component of female contact sex pheromone of the yellow-spotted longicorn beetle,Psacothea hilaris (Pascoe), was isolated from the elytra and identified as (Z)-21-methyl-8-pentatriacontene. The synthetic compound released the typical mating behavior including holding, mounting, and abdominal bending in males, although its activity was considerably lower than the extract of female elytra when treated on a gelatin capsule as an artificial female model.To whom correspondence should be addressed. Midori Fukaya is a postdoctoral fellow of the Research Development Corporation of Japan.     

Sampling range of male sweetpotato weevils (Cylas formicarius elegantulus) (Summers) (Coleoptera: Curculionidae) to pheromone traps: Influence of pheromone dosage and lure age

Studies were conducted to determine the effects of sex pheromone dosage and lure age on movement of male sweetpotato weevils (SPW),Cylas formicarius elegantulus (Summers), using mark-release-recapture techniques. SPW trap counts from various downwind distances were compared for dosages ranging from 0.01 to 10.0 g and lure ages ranging from fresh (0 days old) to 64 days old. The percentages of male SPW recaptured decreased with an increase in release distance and decreased with a decrease in dosage at each corresponding distance. Most SPW were caught within the first 16-hr period. Slopes of percent recapture vs. release distance for the two higher dosages (10 g and 1.0 g) differed from those of the two lower dosages (0.1 and 0.01 g) but did not differ from each other. Intercepts were similar among the three higher dosages. Slopes did not differ among the five lure ages examined. Intercepts differed between fresh (0 days old) and 24-day-old septa at 16 hr and between fresh (0 days old) and 34-day-old septa at 40 hr. Previous exposure to pheromone (conditioning) did not increase percentages of SPW recaptured. Results indicate that male SPW are capable of traversing distances of at least 280 m in 16 hr. The pheromone tested in this study appears to be effective at dosages lower than any other coleopteran sex-pheromone system. Incorporation of this pheromone into a SPW management system may effectively reduce the use of insecticides.     

Evidence for a sex pheromone in the hide beetle,Dermestes maculatus (De Geer) (Coleoptera: Dermestidae)

Adults of the hide beetle,Dermestes maculatus (De Geer), were shown to have a female-produced sex pheromone which excited males. Male response was positively correlated with increasing age, but females produced a higher level of pheromone at 6–8 days of age than at younger or older ages. Extractable female pheromone and male response varied over the photophase with peak values that occurred during the latter hours. Quantitative bioassay indicated that the 50% male response level (RD₅₀) would be elicited by a pheromone exposure of 0.01 female equivalents (FE). Females extracted 24 hr after mating had a lower level of extractable pheromone than did virgin females of the same age.Mention of a proprietary product does not constitute an endorsement by the Minnesota Agricultural Experiment Station.