Chemistry of venom alkaloids in the antMegalomyrmex foreli (Myrmicinae) from Costa Rica

Chemical analysis of the venom of the myrmicine antMegalomyrmex foreli from Costa Rica revealed the presence of four major alkaloidal components. Two of these, 2-butyl-5-(E, 1-heptenyl)-5-pyrroline (3) and 2-butyl-5-(E, E, 1,3-heptadienyl)-5-pyrroline (4), constitute a new functional class of ant venom alkaloids, whose structures were assigned from their spectral and chemical behavior and unambiguous syntheses. The function of these compounds is suggested by field observations of the behavior ofM. foreli, its sting morphology, and the relative toxicity of 3 and 4 against termite workers.     

<Emphasis Type="Italic">E</Emphasis>-2-Ethylhexenal, <Emphasis Type="Italic">E</Emphasis>-2-Ethyl-2-Hexenol,Mellein, and 4-Hydroxymellein in <Emphasis Type="Italic">Camponotus</Emphasis> Species from Brunei

E-2-ethyl-2-hexen-1-ol (1), mellein (4), and 4-hydroxymellein (5) were identified as the major volatile compounds in the head and/or thorax of Camponotus quadrisectus. Neither 1 nor 5 have been previously detected in insects. Also identified were small amounts of m-cresol (2) and 6-methyl salicylic acid (3). E-2-ethylhexenal (6) and small amounts of 3 were identified in heads of Camponotus irritibilis from Kuala Belalong, Brunei. Compounds 2–4 occur in other Bornean camponotines with hypertrophied mandibular glands, and 4 is widespread in the tribe. The possibility of semiochemical parsimony (multiple functions) for these mandibular gland compounds is reviewed in the context of existing data on mandibular gland products of other camponotines, reported biological activities of the compounds, and secondary loss of metapleural glands in this ant group.     

Identification of the sex pheromone of threeMatsucoccus pine bast scales

Matsucoccus resinosae in the United States,M. matsumurae in China, andM. thunbergianae in Korea use (2E, 4E)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one (1) (matsuone) as the primary component of their sex attractant pheromones. The structure was postulated from mass and NMR spectra and confirmed by synthesis of analogs3, (2E,4E)-4,6,11,12-tetramethyl-2,4-tridecadien-7-one, and4, (2E,4Z)-4,6,11,12-tetramethyl-2,4-tridecadien-7-one. Both analogs were attractive to the males ofM. resinosae in laboratory bioassays and toM. matsumurae in laboratory and field tests, but the 4Z analog (4) was much less so than the 4E analog (3) and had inhibitory effects at high concentrations. Dodecanol, isolated from aeration and solvent extracts of femaleM. resinosae, evoked characteristic wing-raising by pedestrian males, but the role of this response was not determined.     

3-Hexyl-5-Methylindolizidine Isomers from Thief Ants, Solenopsis (Diplorhoptrum) Species

The venom alkaloids from the workers of nine collections of Solenopsis (Diplorhoptrum) from California contain either (5E,9E)-3-hexyl-5-methylindolizidine (1c) or (5Z,9E)-3-hexyl-5-methylindolizidine (1d) along with cis-2-methyl-6-nonylpiperidine. The structures of these compounds were determined from their mass spectra and by comparison of their GC-FTIR spectra with those of a synthetic mixture. In view of the facts that a third diastereomer of 3-hexyl-5-methylindolizidine had been reported in previous collections of Solenopsis (Diplorhoptrum) queens from Puerto Rico, and that indolizidines along with other ant venom alkaloids are sequestered by amphibians, the determination of species in this difficult group of ants is significant. In particular, the chemotaxonomic value of the stereochemistry of these venom alkaloids is discussed.     

Behavioral correlates for minor volatile compounds from stink bugs (Heteroptera: Pentatomidae)

Many terrestrial Heteroptera have small, but functional, dorsal abdominal glands as adults. The chemistry, and associated intra- and inter-specific behavior, for dorsal abdominal gland secretions from 10 species representing four genera of Pentatomidae was investigated. Eighteen volatile compounds were identified in species-specific blends from the dorsal abdominal gland secretions ofEuschistus, Acrosternum, andEurydema adults, including aliphatic, aromatic, and terpenoid constituents. Evidence from bioassays is presented that parasitic Tachinidae (Diptera) and Scelionidae (Hymenoptera) use these secretions as kairomones. A field experiment was performed to test the hypothesis that minor volatiles increase the specificity of the main pheromone component from NearcticEuschistus species, methyl (2E,4Z)-decadienoate. However, significantly fewer individuals ofE. tristigmus were captured in traps baited with the complete blend for this species than in traps baited with methyl (2E,4Z)-decadienoate alone. Thus, at the concentrations tested, these kinds of dorsal abdominal gland secretions may be epideictic, promoting spacing in the natural habitat.     

Outdoor attractancy of males ofMatsucoccus josephi (Homoptera: Matsucoccidae) andElatophilus hebraicus (Hemiptera: Anthocoridae) to synthetic female sex pheromone ofMatsucoccus josephi

The active component of the sex pheromone ofMatsucoccus josephi is (2E,6E,8E)-5,7-dimethyl-2,6,8-decatrien-4-one; the chemical is also a powerful kairomone of adult males and females of the bugElatophilus hebraicus the principal predator ofM. josephi. The presence of theZ isomer (2E,6Z,8E)-5,7-dimethyl-2,6,8-decatrien-4-one does not interfere with the attractancy of the activeE component forM. josephi males or the bug. Our results show a clear dose-response between trap catch ofM. josephi males andE. hebraicus. Conversely, increasing amounts of theZ isomer in the mixture did not affect the attraction of the scale insect males or the bug. The catch ofM. josephi males did not differ significantly among traps of different color, and was significantly higher with traps attached to the tree trunk than those suspended between trees. Comparison of the catch ofM. josephi among the three forests and between pine species suggests that the level of infestation ofPinus halepepsis andPinus brutia ssp.brutia is similar, despite the fact that the latter pine is resistant to the scale insect. Both sexes ofE. hebraicus were trapped in much lower numbers at the more infested sites. This may be related to interference with the activity ofE. hebraicus due to deterioration and drying of parts of the tree crowns and heavy colonization by generalist predators in injured trees.     

Chemistry of venom alkaloids in someSolenopsis (Diplorhoptrum) species from Puerto Rico

A number of 15-carbon alkaloids have been identified in venom extracts of four Puerto Rican species of ants in the genusSolenopsis (Diplorhoptrum). Workers of a species from El Verde produced thecis andtrans isomers of 2-methyl-6-nonylpiperidine with the latter isomer predominating. The same compounds were identified in queens of a species from Río Grande, but in this species no alkaloids were detected in worker extracts. Workers of aDiplorhoptrum species collected on Mona Island produced primarily atrans-2-methyl-6-(Z-4-nonenyl)piperidine,3, with smaller amounts of thecis isomer, whereas the major compound found in the queens of the same species on Mona Island was (5Z,9Z)-3-hexyl-5-methylindolizidine, identical with the alkaloid produced by queens of a species collected on Cabo Rojo. Surprisingly, workers of the Cabo Rojo species produced (5Z,9Z)- and (5E,9E)-3-butyl-5-propylindolizidine (4 and5, respectively) reported earlier as the 223AB indolizidines from skins of dendrobatid frogs. The possible significance of the qualitative and quantitative differences in the venom alkaloids synthesized by queens and workers is discussed as is the possibility that ants containing such alkaloids may serve as a dietary source for the skin alkaloids used by certain frogs in chemical defense.     

Semiochemicals from bark beetles: New results,remarks, and reflections

A brief survey is given about recent results in the identification of semiochemicals in bark beetles: Males ofIps sexdentatus (Boern.), stressed by the attack on resinous trees produce large amounts of 3(S)-1-methyl-5-(1-hydroxyl-1-methylethyl)-cyclohexa-1,3-diene. The compound appears to be derived from ³-carene and acts as a repellent. Males ofIps typographus (L.), stressed through the attack on unsuitable host material release 3-methyl-7-methylene-1,3(E), 8-nonatriene, which seems to act as a repellent. The odor bouquet of three species ofPityogenes is described. The occurrence of (+)-grandisol and other compounds related to weevil pheromones points to a close relation between Scolytidae and Curculionidae. Females ofDendroctonus simplex (Le Conte) use (–)-frontalin as the main pheromone. 6-Methyl-6-hepten-2-one, a minor component among the volatile compounds released by the females, is regarded as a possible precursor of frontalin. Similarly, (2R,5S)-2(1-hydroxyl-1-methylethyl)-5-methyltetrahydrofuran, pityol, a pheromone ofPityophthorus spp., is regarded to at least share a common biogenetic precursor with 6-methyl-5-hepten-2-ol, sulcatol. A new bicylic acetal, 2-ethyl-1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane, is described as an aggregation pheromone of the beech bark beetle,Taphrorychus bicolor (Herbst). Structural relationships between bark beetle pheromones and plant volatiles are discussed.     

Chirality of israeli pine bast scale,Matsucoccus josephi (homoptera: Matsucoccidae) sex pheromone

The absolute configuration of the sex pheromone of the Israeli pine bast scale,Matsucoccus josephi, was determined as (2E,5R,6E,8E)-5,7-dimethyl-2,6,8-decatrien-4-one, designated here asR-E with 10% (2E,5S,6E,8E)-5,7-dimethyl-2,6,8-decatrien-4-one, designated asS-E. The chirality of the quantitatively minorZ isomer was (2E,5R,6Z,8E)-5,7-dimethyl-2,6,8-decatrien-4-one (R-Z). Chiral assignments were made by comparative gas chromatographic (GC) analysis of naturalM. josephi pheromone with stereoselectively synthesized stereoisomers on a chiral Cyclodex-B column, which separated the enantiomers with baseline resolution. In gas chromatographic-electroantennographic detection (GC-EAD) analysis of the racemicZ andE isomers, the latter elicited the stronger antennal response by maleM. josephi. In GC-EAD of all four stereoisomers, employing the chiral column,R-E was the most active stereoisomer. In field testsR-E attracted 10 times more males ofM. josephi than didS-E. The racemicE/Z pheromone mixture, containing all four stereoisomers in approximately equal amounts, attracted as many maleM. josephi as did an equivalent amount ofR-E, indicating that the other stereoisomers are not inhibitory. The same keto-diene moiety with the same chiral center and configuration in all three known Matsucoccidae sex pheromones implies a common biosynthetic pathway and phylogenetic relationship.Contribution from the Agricultural Research Organization, the Volcani Center, No. 1496-E, 1994 series.Part of the work was performed during a sabbatical leave of E.D. at Simon Fraser University.     

Sex attractants for the white-barred groundling moth (Recurvaria leucatella clerck) and the lesser bud moth (R. nanella Hübner) (Lepidoptera: Gelechiidae)

In field tests synthetic (3E,5Z)-3,5-tetradecadienyl acetate was found to attract large numbers of males ofRecurvaria leucatella Clerck into sticky traps. The other geometrical isomers did not influence catches. Of the corresponding monoenic compounds, (3E)-3-tetradecenyl acetate was highly attractive to a close relative,Recurvaria nanella Hübner. The catches of the latter species were suppressed by higher amounts of (5Z)-5-tetradecenyl acetate added to the bait, and the addition of (3E)-3-tetradecenol or (3Z)-3-tetradecenyl acetate was without effect. The attractive compounds can be used in traps for monitoring the two pests.     

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). The other four compounds, present in minor amounts, were identified as himachalene sesquiterpenes; two of these, 3 and 4, were hydrocarbons and two, 5 and 6, were alcohols. All four sesquiterpenes were previously encountered from male flea beetles of Aphthona spp. and Phyllotreta cruciferae. Synthetic 1 and 2 matched the natural products by GC retention times, mass spectra, and NMR spectra. Sesquiterpenes 3–6 similarly matched synthetic standards and natural samples from the previously studied species in all ways, including chirality. Both natural and synthetic 1 and 2 gave positive GC–EAD responses, as did sesquiterpenes 3, 5, and 6. Field trials were conducted with a mixture of 1 and 2, and the baited traps were significantly more attractive than control traps to both male and female E. fuscula. The E. fuscula pheromone has potential for monitoring or controlling these pests in eggplants.Mention of trade names or commercial products in this article is solely for the purpose of providing specific information and does not imply recommendation or endorsement by the Department of Agriculture.     

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.     

Minor components in the sex pheromone of legume podborer: Maruca vitrata development of an attractive blend

The legume podborer, Maruca vitrata (syn. M. testulalis) (F.) (Lepidoptera: Pyralidae) is a pantropical pest of legume crops. Sex pheromone was collected by gland extraction or trapping of volatiles from virgin female moths originating in India, West Africa, or Taiwan. Analysis by GC-EAG and GC-MS confirmed previously published findings that (E,E)-10,12- hexadecadienal is the most abundant EAG-active component with 2–5% of (E,E)-10,12-hexadecadienol also present. At least one other EAG response was detected at retention times typical of monounsaturated hexadecenals or tetradecenyl acetates, but neither could be detected by GC-MS. Laboratory wind-tunnel bioassays and a field bioassay of blends of (E,E)-10,12-hexadecadienal with (E,E)-10,12-hexadecadienol and a range of monounsaturated hexadecenal and tetradecenyl acetate isomers indicated greatest attraction of males was to those including (E,E)-10,12-hexadecadienol and (E)-10-hexadecenal as minor components. In subsequent trapping experiments in cowpea fields in Benin, traps baited with a three-component blend of (E,E)-10,12-hexadecadienal and these two minor components in a 100:5:5 ratio caught significantly more males than traps baited with the major component alone, either two-component blend, or virgin female moths. Further blend optimization experiments did not produce a more attractive blend. No significant differences in catches were found between traps baited with polyethylene vials or rubber septa, or between lures containing 0.01 and 0.1 mg of synthetic pheromone. Significant numbers of female M. vitrata moths, up to 50% of total catches, were trapped with synthetic blends but not with virgin females. At present there is no clear explanation for this almost unprecedented finding, but the phenomenon may improve the predictive power of traps for population monitoring.     

Chemical communication in the dacetine antDaceton armigerum (Hymenoptera: Formicidae)

Contrary to previous assumptions,Daceton armigerum, the largest ant in the myrmicine tribe Dacetini, employs trail communication. We identified two anatomical sources of trail pheromones: Trails drawn with poison gland contents can last for more than seven days. Trails drawn with the newly discovered sternal glands (in the VIth and VIIth abdominal sternites) are effective but relatively short-lived. In addition, our bioassays revealed that the contents of the mandibular glands elicit alarm behavior, and secretions from the pygidial gland release attraction. When tested with artificial poison gland trails from seven other myrmicine species,Daceton did not exhibit trail following behavior. We confirmed, however, previous findings thatAtta respond toDaceton poison gland trails andSolenopsis followDaceton Dufour's gland trails.     

Aggregation pheromone ofCarpophilus antiquus (Coleoptera: Nitidulidae) and kairomonal use ofC. lugubris pheromone byC. antiquus

Males ofCarpophilus antiquus Melsheimer (Coleoptera: Nitidulidae) emit an aggregation pheromone that was found to be a novel hydrocarbon, (3E,5E,7E,9E)-6,8-diethyl-4-methyl-3,5,7,9-dodecatetraene. A synthetic scheme and spectra (mass and proton NMR) are given for the compound. Beetles produced the pheromone when feeding on a variety of media, including the brewer's yeast-based artificial diet, fermenting whole-wheat bread dough, corn, and prunes; live baker's yeast was generally added to the food media. Males held individually produced, on average, 25 × more pheromone per beetle than males held in groups of 10 or more. Pheromone was not produced until males were at least 5 days old but was still detected from the oldest beetles tested (47 days). In field tests, the pheromone was attractive to both sexes ofC. antiquus, and it was synergized by food volatiles: A combination of pheromone and fermenting whole wheat dough attracted 2.5× more beetles than pheromone alone, but dough by itself was not significantly more attractive than the control. Semiochemical interactions were studied amongC. antiquus and two other sympatric species for which pheromones are known,C. lugubris Murray andC. freemani Dobson.C. antiquus responded readily to the pheromone ofC. lugubris, but all other interspecific responses to the pheromones were weak. In a sample of naturally infested corn ears, the presence ofC. antiquus was strongly associated with the presence ofC. lugubris, as would be expected if the pheromone ofC. lugubris serves as a kairomone forC. antiquus.     

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.     

N-(2-methylpropyl)-(E,E)-2,4-decadienamide a mosquito larvicide fromAchillea millefolium L.

A methanol extract ofAchillea millefolium L. showed activity against 24-hr-old larvae ofAedes triseriatus. Bioassay- and TLC-monitored fractionation yielded a neutral fraction which was refined further by column chromatography to afford the antilarvalN-(2-methlpropyl)-(E,E)-2,4-decadienamide which was identified by spectral methods and through comparisons with a synthesized sample. Isolated and synthesized amides at 5 ppm resulted in 98 and 100% mortality of 24-hr-oldA. triseriatus larvae. TheN-(2-methylpropyl)-amides of decanoic and (E)-2-decenoic acids showed the same order of antilarval activity asN-(2-methylpropyl)-(E,E)-2,4-decadienamide, butN-(2-methylpropyl)sorbamide was inactive.     

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.     

Venom chemistry of ants in the genusMonomorium

A comparative analysis of the venomous alkaloids produced by ant species in the subgenusMonomorium of the genusMonomorium has been undertaken. All species produce mixtures of unsymmetricaltrans-2,5-dialkylpyrrolidines, but the proportions of the constituents may vary considerably between species. All alkaloids contain both C₆ and C₉ side chains which are present as C₉-saturated. C₆-monounsaturated, and both C₆-and C₉-monounsaturated dialkylpyrrolidines. The structure of 2-(1-hex-5-enyl)-5-(1-non-8-enyl)pyrrolidine, a previously undescribed alkaloid, was proved by unambiguous synthesis after the location of the double bonds was established by the methoxymercuration-demercuration followed by mass spectrometry. The possible chemotaxonomic significance of the mixtures of venomous alkaloids produced by these species ofMonomorium is discussed.     

Laboratory and field tests with the synthetic sex pheromone of threeMatsucoccus 1 pine bast scales

Matsunone, (2E,4E)-4.6,10,12-tetramethyl-2,4-tridecadien-7-one, is the primary sex pheromone ofMatsucoccus resinosae, M. thunbergianae, andM. matsumurae. The synthetic compound was tested in the laboratory and in field tests with all three species, and significantly more males responded to synthetic matsuone than to controls. The attraction of synthetic matsuone to males in field tests was not significantly different from that of virgin females at the same matsuone release rate. An analog of matsuone previously shown to be biologically active was also tested in the laboratory withM. resinosae andM. thunbergianae, and field tested withM. resinosae. The active analog required a dose approximately 100 times greater than matsuone to yield maximum laboratory bioassay response, and in field tests, attraction was not significantly different from controls at doses at which matsuone was significantly attractive.Homoptera: Coccoidea: Margarodidae.Deceased.