Rapid headspace analysis of commercial spearmint and peppermint teas using volatile 'fingerprints' and an electronic nose.

BACKGROUND: Spearmint and peppermint teas are widely consumed around the world for their flavor and therapeutic properties. Dynamic headspace sampling (HS) coupled to gas chromatography/mass spectrometry (GC-MS) with principal component analysis (PCA) of 'fingerprint' volatile profiles were used to investigate 27 spearmint and peppermint teas. Additionally, comparisons between mint teas were undertaken with an electronic nose (enose). RESULTS: Twenty compounds, all previously known in the literature, were identified using HS-GC-MS. PCA found distinct differences between the fingerprint volatile profiles of spearmint, peppermint and spearmint/peppermint combination teas. HS-GC-MS analysis performed with an achiral column allowed faster processing time and yielded tighter clustering of PCA tea groups than the analysis which used a chiral column. Two spearmint outliers were detected. One showed a high degree of variation in volatile composition and a second wholly overlapped with the peppermint PCA grouping. Enose analysis separated all treatments with no overlaps. CONCLUSION: Characterizing the volatile fingerprints of mint teas is critical to quality control for this valuable agricultural product. The results of this study show that fingerprint volatile profiles and enose analysis of mint teas are distinctive and could be used to rapidly identify unknown samples. With specific volatile profiles identified for each tea, samples could be tested in the laboratory, or potentially on a farm or along the supply chain, to confirm the provenance and authenticity of mint food or beverage commodities. © 2024 Society of Chemical Industry. This article has been contributed to by U.S. Government employees and their work is in the public domain in the USA.

Analysis of volatile profiles of green Hawai'ian coffee beans damaged by the coffee berry borer (Hypothenemus hampei).

BACKGROUND: The coffee berry borer (CBB), Hypothenemus hampei, is the most destructive insect pest of coffee globally, causing significant losses in yield and leading to 'off' flavors in damaged beans. Automated headspace sampling (AHS) and gas chromatography-mass spectrometry (GC-MS) were used to investigate changes in the volatile profiles of CBB-damaged green coffee beans. Green coffee from three coffee farms on the island of Hawai'i were sorted into three levels of CBB damage: non-damaged, slightly damaged (1-2 pinholes/bean), and heavily damaged (> 2 pinholes/bean). RESULTS: Distinct differences were found between green coffee bean samples based on the amounts of eight prominent volatiles. The amount of CBB damage was particularly correlated with the amount of both hexanal and 2-pentylfuran. Principal component analysis showed clustering of non-damaged green beans, which did not overlap with the slightly or heavily damaged clusters. Good separation was also found between a mixture of 50% slightly damaged and non-damaged coffee. However, 20% slightly damaged and non-damaged coffee clusters showed strong overlap. CONCLUSION: Understanding the effects of CBB damage on coffee flavor profiles is critical to quality control for this valuable agricultural product. The results of this study show that the volatile profiles of green coffee beans vary with CBB damage. With specific volatile profiles for CBB-damaged coffee identified, coffee samples can be tested in the lab, or potentially on the farm or in coffee mills, to identify high levels of CBB damage that may lead to off flavors and a reduction in product quality and value. © 2018 Society of Chemical Industry.

Volatile changes in Hawaiian noni fruit, Morinda citrifolia L., during ripening and fermentation.

BACKGROUND: Noni fruit (Morinda citrifolia L., Rubiaceae) has been used in traditional medicine throughout the tropics and subtropics and is now attracting interest in western medicine. Fermented noni juice is of particular interest for its promising antitumor activity. The present study collected and analyzed volatiles released at nine time intervals by noni fruit during ripening and fermentation using headspace autosampling coupled to gas chromatography-mass spectrometry. RESULTS: Twenty-three noni volatiles were identified and relatively quantified. In addition to volatiles previously identified in noni, four novel volatile 3-methyl-2/3-butenyl esters were identified via the synthesis of reference compounds. Principle component analysis (PCA) and canonical discriminant analysis (CDA) were used to facilitate multidimensional pattern recognition. PCA showed that ripening noni fruit cluster into three groups, pre-ripe, fully ripe (translucent) and fermented, based on released volatiles. CDA could 83.8% correctly classify noni samples when all ripeness stages were analyzed and 100% when samples were classified into the three PCA groupings. CONCLUSION: The results of the present study confirm the identities of 3-methyl-2/3-butenyl esters, both novel and previously identified, through the synthesis of reference compounds. These esters constitute a large percentage of the volatiles released by fully ripe and fermented noni and likely produced from the decomposition of noniosides, a group of unique glucosides present in the fruit. © 2017 Society of Chemical Industry.

Raspberry Ketone Trifluoroacetate, a New Attractant for the Queensland Fruit Fly, Bactrocera Tryoni (Froggatt).

Queensland fruit fly, Bactrocera tryoni (Q-fly), is a major pest of horticultural crops in eastern Australia. Lures that attract male Q-fly are important for detection of incursions and outbreaks, monitoring of populations, and control by mass trapping and male annihilation. Cuelure, an analog of naturally occurring raspberry ketone, is the standard Q-fly lure, but it has limited efficacy compared with lures that are available for some other fruit flies such as methyl eugenol for B. dorsalis. Melolure is a more recently developed raspberry ketone analog that has shown better attraction than cuelure in some field studies but not in others. A novel fluorinated analog of raspberry ketone, raspberry ketone trifluoroacetate (RKTA), has been developed as a potential improvement on cuelure and melolure. RKTA placed on laboratory cages containing 2-week-old Q-flies elicited strong behavioral responses from males. Quantification of Q-fly responses in these cages, using digital images to estimate numbers of flies aggregated near different lures, showed RKTA attracted and arrested significantly more flies than did cuelure or melolure. RKTA shows good potential as a new lure for improved surveillance and control of Q-fly.

Disruption of Darna pallivitta (Lepidoptera: Limacodidae) by Conventional and Mobile Pheromone Deployment.

Identification of the Darna pallivitta (Moore) pheromone component n-butyl (E)-7,9-decadienoate (E7,9-10:COOn-Bu) has made it possible to investigate communication disruption to control this lepidopteran pest. Conventional communication disruption trials showed marked decreases in the mean number of male moths captured in E7,9-10:COOnBu-treated fields compared with control fields. For traps baited with E7,9-10:COOnBu, percent disruptions were 94.4% and 92.1% for septa (1 g pheromone/ha, 1-wk trial duration) and spirals (6 g pheromone/ha, 8-wk trial duration) respectively. For traps baited with virgin female moths, percent disruption was 73.3% using septa disruptors (1 g pheromone/ha, 1-wk trial duration). Mobile communication disruption using Bactrocera cucurbitae (Coquillett) as carriers for E7,9-10:COOn-Bu was evaluated in the following three areas: fly survivorship, attraction of male moths to treated flies, and moth disruption in a small-scale field trial. Topical application of E7,9-10:COOnBu showed no significant decrease in survivorship at 50 and 80 µg/fly. However, decreased survivorship was observed at 100 µg/fly and linear regression showed E7,9-10:COOnBu dose was significantly correlated with B. cucurbitae survivorship. Traps containing honey-pheromone-fed flies attracted and caught D. pallivitta over a 1-wk period, demonstrating the attractiveness of the carrier. Releasing E7,9-10:COOnBu-fed B. cucurbitae (∼2 g pheromone/ha, 1-wk trial duration) resulted in significantly reduced trap catches in treatment fields compared with control fields on the first 2 d of the field trial. Percent disruptions were 84.7% (day 1) and 56.0% (day 2). These results suggest that both conventional communication disruption and mobile communication disruption have potential to control D. pallivitta.

Differential field responses of the little fire ant, Wasmannia auropunctata (Roger), to alarm pheromone enantiomers.

The little fire ant, Wasmannia auropunctata (Roger) (Hymenoptera: Formicidae), is an invasive ant with negative impacts on both biodiversity and agriculture throughout the tropics and subtropics. Field experiments were conducted in order to elucidate the relative attractiveness of the enantiomers of the alarm pheromones, 2,5-dimethyl-3-(2-methylbutyl)pyrazine and 3-methyl-2-(2-methylbutyl)pyrazine. The enantiomers tested were synthesized from commercially available (S)-2-methylbutan-1-ol or kinetically resolved (R)-2-methylbutan-1-ol, prepared using Pseudomonas cepacia lipase (PCL). Bioassays conducted in a macadamia orchard on the island of Hawaii demonstrated that W. auropunctata were preferentially attracted to the (S)-enantiomers of both alkyl pyrazines over the racemic mixtures in all experiments. To our knowledge, this is the first instance of differential attraction of ants to the enantiomers of chiral pyrazine pheromones despite many examples of these compounds in the literature. In addition, using a chiral column it was determined that (S)-2,5-dimethyl-3-(2-methylbutyl)pyrazine and (S)-3-methyl-2-(2-methylbutyl)pyrazine are the only enantiomers produced by W. auropunctata.

Wind effects on individual male and female Bactrocera jarvisi (Diptera: Tephritidae) tracked using harmonic radar.

Wind affects the movement of most volant insects. While the effects of wind on dispersal are relatively well understood at the population level, how wind influences the movement parameters of individual insects in the wild is less clear. Tephritid fruit flies, such as Bactrocera jarvisi, are major horticultural pests worldwide and while most tephritids are nondispersive when host plants are plentiful, records exist for potentially wind-assisted movements up to 200 km. In this study, harmonic radar (HR) was used to track the movements of both male and female lab-reared B. jarvisi in a papaya field. Overall flight directions were found to be correlated with wind direction, as were the subset of between-tree movements, while within-tree movements were not. Furthermore, the effect of wind direction on fly trajectories varied by step-distance but not strongly with wind speed. Mean path distance, step distance, flight direction, turning angle, and flight propensity did not vary by sex. Both male and female movements are well fit by 2-state hidden Markov models further supporting the observation that B. jarvisi move differently within (short steps with random direction) and between (longer more directional steps) trees. Data on flight directionality and step-distances determined in this study provide parameters for models that may help enhance current surveillance, control, and eradication methods, such as optimizing trap placements and pesticide applications, determining release sites for parasitoids, and setting quarantine boundaries after incursions.

Tracking and modeling the movement of Queensland fruit flies, Bactrocera tryoni, using harmonic radar in papaya fields.

Determining movement parameters for pest insects such as tephritid fruit flies is critical to developing models which can be used to increase the effectiveness of surveillance and control strategies. In this study, harmonic radar was used to track wild-caught male Queensland fruit flies (Qflies), Bactrocera tryoni, in papaya fields. Experiment 1 continuously tracked single flies which were prodded to induce movement. Qfly movements from this experiment showed greater mean squared displacement than predicted by both a simple random walk (RW) or a correlated random walk (CRW) model, suggesting that movement parameters derived from the entire data set do not adequately describe the movement of individual Qfly at all spatial scales or for all behavioral states. This conclusion is supported by both fractal and hidden Markov model (HMM) analysis. Lower fractal dimensions (straighter movement paths) were observed at larger spatial scales (> 2.5 m) suggesting that Qflies have qualitatively distinct movement at different scales. Further, a two-state HMM fit the observed movement data better than the CRW or RW models. Experiment 2 identified individual landing locations, twice a day, for groups of released Qflies, demonstrating that flies could be tracked over longer periods of time.

Radio Telemetry and Harmonic Radar Tracking of the Spotted Lanternfly, Lycorma delicatula (White) (Hemiptera: Fulgoridae).

Lycorma delicatula (White) (Hemiptera: Fulgoridae), spotted lanternfly (SLF), is an invasive pest that feeds and oviposits on numerous woody and herbaceous plants important to agricultural, forest, ornamental, and nursery industries. Describing and understanding SLF movements is key to implementing surveillance and control strategies for this pest and projecting population spread. We used radio telemetry (RT) and harmonic radar (HR) to track the movements of individual SLF at field sites in eastern Pennsylvania and northwestern New Jersey. SLF equipped with HR or RT tags were tracked in 2019 and 2020 from adult emergence until oviposition time, and their movements are described. Although the bulkier RT tags disproportionately affected the distance traveled by males, which are smaller than females, both males and females were more likely to be lost due to signal attenuation when affixed with the lighter-weight HR tags. Females were tracked moving longer distances than males, with maximum distances of 434 m by a single female and 57 m by a single male. A significant positive relationship was found between their height in trees and the distance of subsequent movement. Adult SLF were found in trees predominantly at heights between 6-9 m high. For the fraction of SLF found at eye level, males, but not females, significantly moved above eye level in the weeks prior to mating, likely resulting in the observed sex ratio shift that defines the Early-2 stage. During mating time, tracked SLF were significantly higher than 8 m and oriented to trees where tight aggregations of SLF were present. This orientation towards tight aggregations started when mating began and peaked in the following 2.5 weeks for males in Late-1 and the beginning of Late-2 (after oviposition began), whereas females started this orientation behavior a half-week after males, and this activity peaked for two weeks. Male and female SLF adults exhibited slight differences in host preference, and strong preferences for wild grape, black walnut, sweet birch, and tree-of-heaven were observed. The HR-tagged nymphs moved up to 27.6 m over a five-day period in a cornfield. Nitinol wire HR tags performed better than Wollaston process or tungsten wire tags. SLF movement parameters in the field are described.

Field trapping the little fire ant, Wasmannia auropunctata.

Two detection methods for the little fire ant, Wasmannia auropunctata (Roger) (Hymenoptera: Formicidae), both employing the pheromone attractant 2,5-dimethyl-3-(2-methylbutyl)pyrazine (2-MeBu-diMePy), were compared with peanut butter based detection, in order to evaluate differences in species specificity and detection reliability. Trapping was conducted using a transect through a macadamia orchard on the island of Hawaii. The transect consisted of a series of three-tree plots, each plot contained a peanut butter coated stick (the most common detection method used for W. auropunctata in Hawaii), a one-way trap treated with 2-MeBu-diMePy, and a piece of double-sided tape treated with 2-MeBu-diMePy. While there were no differences in the number of W. auropunctata counted with each detection method, and no differences in detection reliability (detecting the known presence of W. auropunctata in a plot), the pheromone-incorporating methods showed greater species specificity, retaining W. auropunctata almost exclusively. These results demonstrate the potential of pheromone-detection methods to selectively capture target ant species even when other ants are present and abundant. Combined data from all three detection methods and a previous visual survey along the transect showed a marked difference in the frequency of cohabitation among ant species. Of the 10 ant species collected, W. auropunctata was found as the sole ant species on a given tree at a significantly higher frequency than all other ant species except Pheidole fervens. 94% percent of the trees with W. auropunctata had only W. auropunctata, supporting previous observations that this species tends to displace other ant species. In addition, W. auropunctata microhabitat preferences were investigated using one-way traps containing 2-MeBu-diMePy, which were placed in three arboreal and three non-arboreal locations. While the number of ants captured did not differ by trap placement, when grouped, captures were significantly higher in arboreal than non-arboreal microhabitats.

Phenotypic disruption of cuticular hydrocarbon production in hybrids between sympatric species of Hawaiian picture-wing Drosophila.

Interspecies hybrids can express phenotypic traits far outside the range of parental species. The atypical traits of hybrids provide insight into differences in the factors that regulate the expression of these traits in the parental species. In some cases, the unusual phenotypic traits of hybrids can lead to phenotypic dysfunction with hybrids experiencing reduced survival or reproduction. Cuticular hydrocarbons (CHCs) in insects are important phenotypic traits that serve several functions, including desiccation resistance and pheromones for mating. We used gas chromatography mass spectrometry to investigate the differences in CHC production between two closely related sympatric Hawaiian picture-wing Drosophila species, Drosophila heteroneura and D. silvestris, and their F1 and backcross hybrid offspring. CHC profiles differed between males of the two species, with substantial sexual dimorphism in D. silvestris but limited sexual dimorphism in D. heteroneura. Surprisingly, F1 hybrids did not produce three CHCs, and the abundances of several other CHCs occurred outside the ranges present in the two parental species. Backcross hybrids produced all CHCs with greater variation than observed in F1 or parental species. Overall, these results suggest that the production of CHCs was disrupted in F1 and backcross hybrids, which may have important consequences for their survival or reproduction.

Harmonic radar tracking of individual melon flies, Zeugodacus cucurbitae, in Hawaii: Determining movement parameters in cage and field settings.

Tephritid fruit flies, such as the melon fly, Zeugodacus cucurbitae, are major horticultural pests worldwide and pose invasion risks due primarily to international trade. Determining movement parameters for fruit flies is critical to effective surveillance and control strategies, from setting quarantine boundaries after incursions to development of agent-based models for management. While mark-release-recapture, flight mills, and visual observations have been used to study tephritid movement, none of these techniques give a full picture of fruit fly movement in nature. Tracking tagged flies offers an alternative method which has the potential to observe individual fly movements in the field, mirroring studies conducted by ecologists on larger animals. In this study, harmonic radar (HR) tags were fabricated using superelastic nitinol wire which is light (tags weighed less than 1 mg), flexible, and does not tangle. Flight tests with wild melon flies showed no obvious adverse effects of HR tag attachment. Subsequent experiments successfully tracked HR tagged flies in large field cages, a papaya field, and open parkland. Unexpectedly, a majority of tagged flies showed strong flight directional biases with these biases varying between flies, similar to what has been observed in the migratory butterfly Pieris brassicae. In field cage experiments, 30 of the 36 flies observed (83%) showed directionally biased flights while similar biases were observed in roughly half the flies tracked in a papaya field. Turning angles from both cage and field experiments were non-random and indicate a strong bias toward continued "forward" movement. At least some of the observed direction bias can be explained by wind direction with a correlation observed between collective melon fly flight directions in field cage, papaya field, and open field experiments. However, individual mean flight directions coincided with the observed wind direction for only 9 out of the 25 flies in the cage experiment and half of the flies in the papaya field, suggesting wind is unlikely to be the only factor affecting flight direction. Individual flight distances (meters per flight) differed between the field cage, papaya field, and open field experiments with longer mean step-distances observed in the open field. Data on flight directionality and step-distances determined in this study might assist in the development of more effective control and better parametrize models of pest tephritid fruit fly movement.

Di- and tri-fluorinated analogs of methyl eugenol: attraction to and metabolism in the Oriental fruit fly, Bactrocera dorsalis (Hendel).

Oriental fruit fly, Bactrocera dorsalis (Hendel), males are attracted to the natural phenylpropanoid methyl eugenol (ME). They feed compulsively on ME and metabolize it to ring and side-chain hydroxylated compounds that have both pheromonal and allomonal properties. Previously, we demonstrated that mono-fluorination at the terminal carbon of the ME side-chain significantly reduced metabolic side-chain hydroxylation, while mono-fluorination of ME at position 4 of the aromatic ring blocked ring-hydroxylation but surprisingly enhanced side-chain hydroxylation. Here, we demonstrated that the introduction of fluorine atoms on both the ring and side-chain of ME blocks both positions that undergo enzymatic hydroxylation and, in particular, completely inhibits oxidative biotransformation of the allyl group. In laboratory experiments, B. dorsalis males initially were more attracted to both 1-fluoro-4,5-dimethoxy-2-(3,3-difluoro-2-propenyl)benzene (I) and 1-fluoro-4,5-dimethoxy-2-(3-fluoro-2-propenyl)benzene (II) than to ME. However, both I and II were taken up by flies at rates significantly less than that of ME. Flies fed with difluoroanalog II partially metabolized it to 5-fluoro-4-(3-fluoroprop-2-en-1-yl)-2-methoxyphenol (III), and flies fed with trifluoroanalog I produced 4-(3,3-difluoroprop-2-en-1-yl)-5-fluoro-2-methoxyphenol (V), but the rates of metabolism relative to rates of intakes were much lower compared to those of ME. Flies that consumed either the tri- or difluorinated analog showed higher post-feeding mortality than those that fed on methyl eugenol. In field trials, trifluoroanalog I was ∼90% less attractive to male B. dorsalis than ME, while difluoroanalog II was ∼50% less attractive. These results suggest that increasing fluorination can contribute to fly mortality, but the trade off with attractancy makes it unlikely that either a di or trifluorinated ME would be an improvement over ME for detection and/or eradication of this species.

Headspace GC-MS analysis of differences in intra- and interspecific Terpene profiles of Picea pungens Engelm. and P. abies (L.) Karst.

Conifer terpenes mediate a number of ecological roles such as deterring herbivory and allelopathic (plant-plant) communication. These terpenes also effect air quality and climate models and are used in chemotaxonomic studies. Herein we report on variation in both intra- and interspecific spruce terpenes using static headspace gas chromatography mass spectrometry (HS-GC-MS) and principal component analysis (PCA) of 'fingerprint' volatile profiles. Samples of blue spruce (Picea pungens), Norway spruce (P. abies), and cedar of Lebanon (Cedrus libani), an outgroup control, were analyzed by HS-GC-MS using both chiral and achiral GC columns. Headspace sampling parameters, temperature and heating time, were optimized to maximize detected terpenes. PCA of terpene 'fingerprint' profiles showed differences by species, by individual trees, but perhaps surprisingly not by environmental conditions. Analysis of blue and Norway spruce over several months show that volatile emissions remained remarkably constant unlike cedar of Lebanon, which showed a much greater variation in volatile profiles. Branches and buds from both spruces were found to release greater amounts of terpenes than samples of needles. The enantiomeric compositions of seven chiral monoterpenes were found to be largely similar between the three conifers with the exception of (-)-α-pinene, which was the dominant enantiomer released by Norway spruce and cedar of Lebanon, while (+)-α-pinene slightly predominated in blue spruce. While not the primary focus of this work, we believe this constitutes the first report on the enantiomeric composition of terpenes in cedar of Lebanon.

Ring-fluorinated analog of methyl eugenol: attractiveness to and metabolism in the oriental fruit fly, Bactrocera dorsalis (Hendel).

Oriental fruit fly, Bactrocera dorsalis (Hendel), males are highly attracted to the natural phenylpropanoid methyl eugenol (ME). They compulsively feed on ME and metabolize it to ring and side-chain hydroxylated compounds that have both pheromonal and allomonal functions. Side-chain metabolic activation of ME leading to (E)-coniferyl alcohol has long been recognized as a primary reason for hepatocarcinogenicity of this compound in rodents. Earlier, we demonstrated that introduction of a fluorine atom at the terminal carbon of the ME side chain significantly depressed metabolism and specifically reduced formation of coniferyl alcohol but had little effect on field attractiveness to B. dorsalis. In the current paper, we demonstrate that fluorination of ME at the 4 position of the aromatic ring blocks metabolic ring-hydroxylation but overall enhances side-chain metabolism by increasing production of fluorinated (E)-coniferyl alcohol. In laboratory experiments, oriental fruit fly males were attracted to and readily consumed 1,2-dimethoxy-4-fluoro-5-(2-propenyl)benzene (I) at rates similar to ME but metabolized it faster. Flies that consumed the fluorine analog were as healthy post feeding as ones fed on methyl eugenol. In field trials, the fluorine analog I was approximately 50% less attractive to male B. dorsalis than ME.

Raspberry Ketone Trifluoroacetate Trapping of Zeugodacus cucurbitae (Diptera: Tephritidae)in Hawaii.

Melon fly, Zeugodacus cucurbitae (Coquillett), is a serious pest of tropical horticulture, causing damage to cucurbits, other fruiting vegetables, and certain tree fruits. The deployment of male lures comprises an important component of several detection and control strategies for this pest, with the main male attractant currently in use being cuelure (CL). A novel fluorinated analog of CL, raspberry ketone trifluoroacetate (RKTA), has been developed for the control of Bactrocera tryoni, a related pest; here, we test this compound for attraction to Z. cucurbitae. In outdoor screen cage testing, observations showed both more flies on filter papers, and a higher percentage of flies feeding, on papers treated with RKTA than on those with CL or melolure (ML). Field trapping with both yellow sticky traps and bucket traps found that RKTA captured more flies during the first 6 h of trapping than CL, while trap captures in the subsequent 18 h did not differ between the two lures. When comparing combined 24 h trap captures, yellow sticky traps containing RKTA captured more flies than those with CL, while bucket trap captures did not vary by lure. Analysis of lures weathered on filter paper found that nearly all applied RKTA hydrolyzed to RK within 6 h. Fine-scale melon fly behaviors digitally recorded in the field showed median resting distances from the lure of responding flies were shorter for RKTA than for CL. This study demonstrates the inherent attractiveness of RKTA while also highlighting the instability of this compound due to hydrolysis.

Cucumber Lure Trapping of Zeugodacus cucurbitae (Diptera: Tephritidae) in Hawaii and Taiwan: Longevity and Nontargets Captures.

The melon fly, Zeugodacus cucurbitae (Coquillett), is a serious pest of tropical horticulture, causing damage to cucurbits, tree fruits, and fruiting vegetables. Melon flies are especially attractive to freshly sliced cucumber, and this has led to the identification of a nine-compound kairomone lure that can be used to trap both female and male flies. In this study, a seven-compound lure, containing (Z)-6-nonenal, (Z)-6-nonen-1-ol, 1-octen-3-ol, (E,Z)-2,6-nonadienal, (E)-2-nonenal, hexanal, and 1-hexanol, was formulated into PVC plugs (100 or 300 mg/plug) for field testing in wet traps. In Hawaii, 100 mg of the seven-compound cucumber lure, loaded in either plugs or glass capillaries, attracted more flies than traps containing Solulys protein over a 9-wk period. However, both cucumber lure formulations showed marked declines in the number of flies trapped after 3 wk. Similar results were obtained during a 6-wk field trial using 100 mg cucumber lure plugs in Taiwan. Increasing the cucumber lure loading rate to 300 mg/lure increased the effective trapping life of the attractant during a second 9-wk field trial conducted in Hawaii. The synthetic cucumber lure showed female-biased sex ratios in trap captures in the Taiwanese and second Hawaiian field trials. Protein lures captures were female-biased in all three field trials. Wet traps in Hawaii containing the cucumber lure were found to capture 25-30 nontarget insects/trap/week, less than half that captured with Solulys. Captured nontarget insects represented 37 families in 10 orders. The most common families caught were Ceratopogonidae (∼9 flies/trap) and Gryllidae (∼7 crickets/trap).

Raspberry Ketone Analogs: Vapour Pressure Measurements and Attractiveness to Queensland Fruit Fly, Bactrocera tryoni (Froggatt) (Diptera: Tephritidae).

The Queensland fruit fly, Bactrocera tryoni (Froggatt) (Q-fly), is a major horticultural pest in Eastern Australia. Effective monitoring, male annihilation technique (MAT) and mass trapping (MT) are all important for control and require strong lures to attract flies to traps or toxicants. Lure strength is thought to be related in part to volatility, but little vapour pressure data are available for most Q-fly lures. Raspberry ketone (4-(4-hydroxyphenyl)-2-butanone) and analogs that had esters (acetyl, difluoroacetyl, trifluoroacetyl, formyl, propionyl) and ethers (methyl ether, trimethylsilyl ether) in replacement of the phenolic group, and in one case also had modification of the 2-butanone side chain, were measured for their vapour pressures by differential scanning calorimetry (DSC), and their attractiveness to Q-fly was assessed in small cage environmentally controlled laboratory bioassays. Maximum response of one category of compounds, containing both 2-butanone side chain and ester group was found to be higher than that of the other group of compounds, of which either of 2-butanone or ester functionality was modified. However, linear relationship between vapour pressure and maximum response was not significant. The results of this study indicate that, while volatility may be a factor in lure effectiveness, molecular structure is the dominating factor for the series of molecules investigated.

Isolation and characterization of norharmane from Reticulitermes termites (Isoptera: Rhinotermitidae).

The fluorescent alkaloid norharmane has been isolated from Reticulitermes termites and characterized by 1H NMR, UV/Vis, mass spectrometry, and gas chromatography/mass spectrometry. Microcoil 1H NMR spectroscopy allowed spectra to be obtained from mass-limited material, facilitating the identification of norharmane, which is the major component in termite fluorescence under UV light. Norharmane was uniformly present at approximately 1 ng/mg in Reticulitermes tibialis Banks workers, soldiers, and alates; Reticulitermes flavipes (Kollar) workers; and Reticulitermes virginicus (Banks) workers. Some termites were observed to fluoresce with less intensity, but no differences in norharmane levels were detected. Mechanisms that may account for fluorescent differences are discussed as are the possible ecological implications of norharmane in termites.