General food semiochemicals attract omnivorous German cockroaches, Blattella germanica

Stale beer and peanut butter are effective baits for the German cockroach (GCRs), Blattella germanica (L.) (Dictyoptera: Blattellidae). In still-air arena olfactometer experiments it was previously shown that headspace volatile extracts of peanut butter and solvent extract of beer attract male GCRs. The objective of this study was to identify the semiochemicals that mediate attraction of GCRs to these sources. Coupled gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometric (MS) analyses of these attractive extracts, or fractions thereof, and of synthetic standards revealed many candidate semiochemicals. Elaborate olfactometer experiments determined that 1-hexanol from peanut butter, and ethanol and 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP) from beer, are the key semiochemicals of these food sources. 1-Hexanol is a well-known headspace volatile of decomposing lipids, ethanol conveys food fermentation, and DDMP with a caramel-type flavor has been found in several types of food. By responding to these rather general food-derived compounds, the omnivorous GCRs appear to exploit semiochemicals that indicate the presence of various food components, such as lipids and carbohydrates. Synthetic equivalents of these semiochemicals may be formulated as baits or be added to, and thus enhance the attractiveness of, natural food sources as trap or insecticidal baits.     

Sampling and monitoring of biogenic emissions by eucalyptus leaves using membrane extraction with sorbent interface (MESI)

Membrane extraction with sorbent interface (MESI) has been applied to monitor plant fragrance volatiles emitted into indoor air. The main components of the MESI system are a membrane module and a trap, which can be connected directly to a GC or GC-MS for simultaneous multicomponent extraction and monitoring. A polydimethylsiloxane (PDMS) membrane and two different traps, PDMS and Tenax, as well as a DC current supply for trap desorption have been applied in this research. After the membrane module is placed in contact with the plant, the MESI/GC-MS provides semicontinuous characterization of volatile compounds emitted. The MESI device has been applied to monitor the biogenic volatile organic compounds released during the first 8 h after a branch was cut from a Eucalyptus dunnii tree. The study demonstrates that the MESI system is a simple and useful tool for monitoring changes in emission processes as a function of time.     

八角尺蠖对八角叶及性信息素腺体浸提液的触角电位反应

触角电位（electroantennogram,EAG）技术是一个在昆虫性信息素和其它挥发性信息化学生物活性测定中的重要方法。本研究利用EAG技术,测定了八角尺蠖对丙酮、正己烷、乙醇和蒸馏水等4种不同溶剂所浸提的八角叶片及八角尺蠖性信息素腺体浸提液的电生理反应。结果表明,正己烷是八角尺蠖性信息素提取的最好溶剂,雄蛾对性信息素腺体浸提液的EAG反应比雌虫强烈,这在一定程度上反映了雄蛾可能更依赖于对雌蛾释放的性信息素的探测,而不是对寄主气味的探测;雄蛾对八角叶片的正己烷浸提液具有最强的EAG反应,而雌蛾则对八角叶片的丙酮浸提液的EAG反应最强,由此反映了雌雄个体在寻找寄主、繁殖后代等行为中的性别差异;雄蛾羽化后3h对八角叶片气味就有较强的EAG反应,在24h内EAG反应值随着羽化后时间的延长而增大,这反映了随着羽化后时间的延长,触角的机能随之趋于完善,因此对于外界的刺激更为敏感。本研究为利用八角尺蠖性信息素活性成分开展害虫的监测和无公害防治奠定基础。     

Emission of volatile chemicals from flowering dogwood (cornus Florida L.) flowers

Reproduction of flowering dogwood trees occurs via obligate out-crossing, and U.S. native bees have been suggested to be primary pollinators of this ecologically and economically important deciduous tree. Whether floral volatiles play a role in reproduction of the dogwood remains unclear. Objectives of this study were to identify principal volatile chemicals emitted from dogwood flowers and to assess a temporal volatile emission profile and volatile consistency across four cultivars. Inflorescences with intact bracts and 5 cm flower pedicel were removed from dogwood trees and subjected to headspace volatile collection. Six principal volatile compounds were detected from the flowers of the cultivar 'World's Fair' with 3-formylpyridine as the most abundant constituent. Subsequent headspace analyses performed using inflorescences without bracts or floral pedicels alone indicated that 3-formylpyridine, E-beta-ocimene, S-linalool, and ketoisophorone were mainly emitted from inflorescences. Experiments were also conducted to determine whether volatile emissions differed across time and between different cultivars of flowering dogwood. When volatile emission was analyzed for 48 h using 12 h light/dark cycles, the emission of several volatile compounds displayed diurnal patterns. Finally, whereas florets in inflorescences of four different dogwood cultivars emitted similar levels of the six principal floral volatile chemicals, 'Cherokee Brave' flowers alone yielded 4-methoxybenzaldehyde and germacrene-D. The implications of the findings of this study to dogwood breeding programs are discussed.     

Aroma content of fresh basil (Ocimum basilicum L.) leaves is affected by light reflected from colored mulches

Sweet basil (Ocimum basilicum L.) is an herb that is used to add a distinct aroma and flavor to food. Volatile compounds emitted from fully expanded fresh leaves grown in drip-irrigated plots that were covered with six colors of mulch were compared. The colors reflected a range of photosynthetic photon flux, far-red, red, and blue light from the soil surface to developing leaves. Our objective was to determine whether reflection from the different colors could influence concentrations of volatile compounds emitted from the fresh leaves. Volatile compounds were isolated by headspace sampling and quantified by gas chromatography. Twenty-six compounds were identified, of which the terpenoids linalool and 1,8-cineole comprised more than 50% of the total yield. Concentrations of volatile compounds from leaves that developed over green, blue, yellow, white, and red mulches followed the same patterns as they did for air-dried leaves of the same cultivar. However, the concentration of volatile compounds from fresh leaves was about 50-fold higher than those found in the previous study of air-dried leaves.     

Volatile composition of coffee berries at different stages of ripeness and their possible attraction to the coffee berry borer Hypothenemus hampei (Coleoptera: Curculionidae)

The analysis of volatile emissions of coffee berries in different physiological states of ripeness was performed using dynamic headspace and gas chromatography/mass spectrometry analysis for Coffea arabica, var. Colombia. The composition of the volatiles emitted by coffee berries is dominated by very high levels of alcohols, mainly ethanol, in all stages of ripeness in comparison with other compounds. Overripe coffee berries have high volatile emissions and show a composition dominated mainly by esters followed by alcohols, ketones, and aldehydes. The lowest level compounds were monoterpenes. 2-Methyl furan was detected in various ripening stages; this compound has not been previously reported as a coffee berry volatile. The presence of ethanol and other alcohols in the volatile composition might explain the effectiveness of using traps with mixed alcohols for detection and capture of coffee berry borers.     

Soil volatile analysis by proton transfer reaction-time of flight mass spectrometry (PTR-TOF-MS)

We analyzed the volatile organic compounds (VOCs) emitted from different soils by using the PTR-MS-TOF technique under laboratory conditions and compared them with soil chemical biochemical activities. The emitted VOCs were related to soil microbial biomass, soil respiration and some soil enzyme activities so as to evaluate if size and activity of soil microbial communities influenced the soil VOCs profiles. Our results showed that the emitted VOCs discriminated between soils with different properties and management, and differences in the VOCs emission profiles were likely related to the active metabolic pathways in the microbial communities of the three studied soil. Our results also showed that some soil enzyme activities such as β-glucosidase and arylsulfatase were possibly involved in the release of compounds fueling microbial metabolic pathways leading to the production of specific VOCs. It was concluded that the PTR-MS-TOF technique is suitable for analyze VOCs emission from soil and that studies comparing soil enzyme activities and soil volatile profiles can reveal the origin of VOCs and give further insights on microbial activity and soil functionality.     

Volatile organic compound (VOC) emissions from soil and litter samples

The production of nonmethane volatile organic compounds (VOCs) by soil microbes is likely to have an important influence on soil ecology and terrestrial biogeochemistry. However, soil VOC production has received relatively little attention, and we do not know how the emissions of microbially-produced VOCs vary across soil and litter types. We collected 40 root-free soil and litter samples from a diverse array of ecosystem types and conducted laboratory incubations in order to compare the types and quantities of VOCs emitted. VOC production rates were higher in litter samples than in soil samples, and the rates were correlated with microbial biomass and CO₂ production levels. On average, the litter samples produced more types of VOCs than the soil samples with litters emitting a number of VOCs (including terpenoids) that were not generally emitted from the soil samples. Across all of the samples, we identified 100 VOCs, and more than 70% of these compounds could not be positively identified by GC/MS analyses. Of those VOCs that could be identified, furfural and similar furan compounds were noteworthy in that they were emitted in large amounts from nearly every sample examined. Other identifiable VOCs produced across a range of soil and litter samples included propanoic and butanoic acids, which are known products of microbial fermentation. Together these results suggest a need for additional research examining the specific factors influencing VOC emissions from soil and the identification of specific VOCs emitted from soil and litter as many of these compounds are likely to have important effects on belowground ecology.     

Reduction of Carpophilus freemani dobson (Coleoptera: nitidulidae) aggregation pheromone response by synthetic analogues.

Analogues of (2E,4E,6E)-5-ethyl-3-methyl-2,4,6-nonatriene, the major component of the aggregation pheromone of Carpophilus freemani Dobson (Coleoptera: Nitidulidae), were synthesized and the potency of these compounds in suppressing the response of C. freemani to its pheromone in a wind tunnel bioassay was determined. The most potent compounds reduced behavioral response to pheromone 83-96% when the inhibitors were present in 10-fold excess. These compounds are (1Z, 3E,5E)-1-methoxy-3-ethyl-5-methyl-1,3,5-heptatriene, (1E,3E, 5E)-1-cyclopropyl-3-ethyl-5-methyl-1,3,5-heptatriene, and (1Z,3E, 5E)-1-cyclopropyl-3-ethyl-5-methyl-1,3,5-heptatriene. In the presence of fermenting bread dough (a pheromone synergist), the most potent inhibitory compound, (1Z,3E, 5E)-1-cyclopropyl-3-ethyl-5-methyl-1,3,5-heptatriene, was less effective in reducing mean landings (69% vs 99%) than when dough was absent. This inhibitory compound causes a reduction of response to pheromone but does not cause a reduction of response to fermenting food-type volatiles such as fermenting bread dough. Analogues of pheromones that strongly reduce response to pheromones by insects might be useful as biochemical probes to study the pharmacophoric (three-dimensional structure) requirements for pheromone perception.     

Flavor composition of cashew (Anacardium occidentale) and marmeleiro (Croton species) honeys

The aim of this work was to characterize the volatile fractions of two Brazilian honeys known as caju and marmeleiro. The volatile components were isolated by a column extraction technique using acetone as the extraction solvent. Totals of 59 and 36 volatile compounds were definitely or tentatively identified in the caju and marmeleiro honeys, respectively, using reference substances, mass spectral libraries, and the odor qualities of the compounds eluted from the GC column. Aroma extraction dilution analysis allowed the tentative identification of furfuryl mercaptan, benzyl alcohol, delta-octalactone, gamma-decalactone, eugenol, benzoic acid, isovaleric acid, phenylethyl alcohol, and 2-methoxyphenol as impact volatile compounds in the caju honey. In the marmeleiro honey, only isovaleric acid, gamma-decalactone, benzoic acid, and vanillin were considered to be potent odorants. This study showed that the medium- to high-boiling volatile compounds are important contributors to the characteristic aroma of these honeys.     

Evaluation of pheromone release from commercial mating disruption dispensers

Pome fruit growers and crop consultants have expressed concerns about the seasonal release performance of commercial codling moth mating disruption dispenser products. Because of these concerns, we developed a laboratory flow-through volatile collection system (VCS) for measuring the volatile release of the codling moth sex pheromone, codlemone, from commercially available hand-applied dispensers. Under controlled air-flow and temperature conditions, the released vapor was trapped onto a polyurethane foam adsorbent followed by solvent extraction, solvent reduction, and GC/MS determination. Method recovery and breakthrough validations were performed to demonstrate system reliability before determining codlemone release from commercial dispensers field-aged over 140 days. The volatile collection was carried out in a consistent manner among five dispenser types most commonly used by growers, so that direct comparison of performance could be made. The comparison showed differences in the amount of pheromone released and in the patterns of release throughout the season between dispenser types. The variation in release performance demonstrates the need for routine evaluation of commercially marketed mating disruption dispensers. We believe that the simple and cost-effective volatile collection system can assist pheromone dispenser manufacturers in determining seasonal dispenser performance before new products are introduced into the commercial market and in rapidly verifying dispenser release when field-aged dispenser efficacy is in question.     

A Pilot-Scale Evaluation of Greenroof Runoff Retention, Detention, and Quality

The aggregate potential health impact due to ambient volatile organic compounds on the population living in the area nearby the petrochemical industrial complex in Thailand was evaluated using measured air contaminants concentration. Airborne volatile organic compounds were collected using canisters and were analyzed by gas chromatography/mass spectrophotometer following the US.EPA TO 15 procedure. Composite samples taken over a 24-h period were collected monthly. Concentrations of volatile organic compounds (VOCs) were analyzed for a suite of 24 compounds covering both carcinogenic and non-carcinogenic substances. Results were determined and analyzed in order to evaluate their spatial variability and their potential health risk. Comparison of data from each monitoring site indicated that patterns of VOCs across sites were different from their major species and their concentrations which might be influenced by nearest potential emission sources. Carcinogenic VOCs such as benzene, 1,3butadiene, and 1,2 dichloroethane were found to be higher than their annual national standards. A potential cancer risk map was drawn based on benzene concentration in order to illustrate the zone of impact and the number in the population likely to be exposed. Results indicated that 82% of the total area, and 89.6% of the total population were within the impact area. It was suspected that high concentrations of benzene and 1,3 butadiene might be attributed by both the mobile source and the point source of emissions while 1,2 dichloroethane was suspected to be emitted from factories located upwind from the monitoring sites. Hazard quotients and hazard indexes were applied to determine chronic health effects with non-cancer endpoints. Calculated values of hazard indexes for each of the target organ systems were lower than 1, which indicated that the non-cancer chronic risk due to level of volatile organic compounds in the study area was less.     

Differences in the fragrances of pollen,leaves, and floral parts of garland (Chrysanthemum coronarium) and composition of the essential oils from flowerheads and leaves

Headspace analyses of pollen, whole flowerheads, ligulate and tubular florets, flower buds, involucral bracts, and leaves have been performed on the food plant Chrysanthemum coronarium L. (Asteraceae). The analyses permitted differences in the pattern of volatiles emitted by the different floral parts to be observed and the site and phenological stage of emission of these chemicals to be verified. Camphor and cis-chrysanthenyl acetate were emitted mainly by ligulate and tubular florets; the production of myrcene and (Z)-ocimene was higher in the flower buds, whereas beta-caryophyllene, (E,E)-alpha-farnesene, and (E)-beta-farnesene seemed attributable mainly to the involucral bracts. The leaves showed a quite different volatile profile, with (Z)-ocimene as the main constituent. Pollen showed a completely different composition of its volatiles, with perilla aldehyde, cis-chrysanthenyl acetate, and camphor among the principal compounds; many carbonylic compounds and linear hydrocarbons have been detected exclusively in pollen. Furthermore, the essential oils obtained from flowerheads and leaves have been studied. These samples showed mainly quantitative differences. Camphor (22.1%) and cis-chrysanthenyl acetate (19.9%) were the main constituents of the oil from flowers, whereas the oil from the leaves contained mainly (Z)-ocimene (45.4%) and myrcene (28.2%).     

Volatile compounds from Escherichia coli O157:H7 and their absorption by strawberry fruit

Volatile compounds emitted by cultures of two strains of the pathogenic bacterium Escherichia coliO157:H7 and a nonpathogenic strain of E. coli were trapped on Super-Q porous polymer and identified by GC-MS. The predominant compound produced by all three strains was indole with lesser amounts of other components including methyl ketones, 2-heptanone, 2-nonanone, 2-undecanone, and 2-tridecanone. The vapor-phase profiles of these strains were similar for most chemicals identified but differed with regard to ketones. Strawberry fruit was shown to be a suitable host for E. coli O157:H7 with the population of the bacterium either increasing or remaining stable after 3 days depending on inoculation level. Headspace analysis of the volatile compounds from inoculated fruit yielded no detectable quantity of indole. Strawberry fruit readily absorbed indole and other volatile compounds produced by the bacteria and in some cases metabolized the compounds to new volatile products. Thus, headspace "marker" compounds indicating possible bacterial contamination of fruit were largely removed from the vapor phase by the strawberries.     

Improved synthesis and deployment of (2S,3R)-2-(2Z,5Z-octadienyl)-3-nonyloxirane, a pheromone of the pink moth, Lymantria mathura

We report two new syntheses of (2S,3R)-2-(2Z,5Z-octadienyl)-3-nonyloxirane, the main sex pheromone component of the pink moth, Lymantria mathura. The key step in the first route was the construction of (Z,Z)-1-bromo-1,4-heptadiene (6), which was coupled in the final step with 2-iodomethyl-3-nonyloxirane 4 via a Grignard reaction. The second approach employed alkylation of 1,4-heptadiynyllithium with epoxy triflates 7 in ether/hexane and provided the pheromone in >/=37% overall yield from alcohol 2. The 4:1 ratio of pheromone enantiomers, reportedly the most attractive to pink moth males, can be directly crafted from appropriately selected Sharpless asymmetric epoxidation conditions.     

Nematicidal activity of volatile organic compounds emitted by Brassica juncea,Azadirachta indica,Canavalia ensiformis,Mucuna pruriens and Cajanus cajan against Meloidogyne incognita

Understanding the effect of plant volatile organic compounds (VOCs) on soil nematodes and water may explain plant damage in the field and how some nematode management strategies reduce soil nematode populations. M. incognita is a damaging plant pathogenic nematode that affects crops worldwide. The aims of this study were to evaluate the effect of the VOCs emitted by five common crops used for soil incorporation to control the second-stage juveniles (J₂) of Meloidogyne incognita. To investigate the “in vitro” role of water in the relationship between nematodes and plant VOCs. And to identify the volatile molecules by gas chromatography (GC/MS). The method used permitted the volatile molecules from macerated plant organs to only contact the J₂ nematodes by air. Plants organs from all plants macerated with and without water emitted VOCs that immobilized J₂ nematodes, with higher levels emitted when the plant organs were macerated without water. Only water exposed to VOCs from neem and mustard leaves were capable of immobilizing M. incognita J₂. The M. incognita J₂ exposed to neem and mustard VOCs and inoculated in tomato seedlings resulted in reduced gall formation and nematode reproduction, showing the nematicidal effect of the plant-emitted VOCs. GC/MS analysis revealed the presence of 58 and 32 molecules in the VOCs emitted from neem and mustard macerates, respectively. Alcohols were found in both the neem and mustard VOCs. Esters were found in the neem VOCs, and sulfur-containing compounds, mostly isothiocyanates, were found in mustard. Our results demonstrate that plant VOCs contain diversified molecules that affect M. incognita mobility, pathogenicity and reproduction. Nematode toxic VOCs may be retained in water, which prevents the VOCs from escaping into the air and causing the water to become toxic to nematodes. These data may explain part of the role of VOCs in the biofumigation process, through plant incorporation with the soil, and suggests that irrigation performed directly after incorporation may trap the VOCs in soil water and thereafter retain nematode toxicity longer than incorporation that is performed later.     

水稻二化螟性信息素和诱捕器组合的田间诱蛾效果比较

本研究比较了水稻二化螟性信息素的橡皮塞诱芯、毛细管诱芯与水盘、筒型诱捕器几种诱捕装置在田间实际的诱蛾效果,结果表明,传统的诱捕装置(即橡皮塞诱芯+水盘诱捕器)比新型筒型诱捕装置(即毛细管诱芯+筒型诱捕器)具有更好的诱捕效果,二者之间呈显著差异;在诱捕一代和二代二化螟成虫过程中,不同类型诱捕器诱蛾效果差异显著,而诱芯类型对诱捕效果没有显著差异。本文提出需要详细观察二化螟雄蛾的趋化性、进入诱捕器的行为,以改进诱捕器,提高诱捕效果。     

Role of ground trash volatiles in the selection of hibernation sites by boll weevils

Volatiles play a large role in governing the behavior of boll weevils (Anthonomus grandis Boheman). They are attracted to cotton plants, and the female is sexually attracted to the male. The attracting compounds in both instances are terpenoids. Primarily in the fall of the year, boll weevils seek hibernation sites in leaf trash, where they remain until the following spring or summer. In the present study, essential oils were prepared by steam distillation from several leaf samples known to be prevalent at hibernation sites, and the oils were analyzed by GLC-MS. On the basis of the resulting presumptive identifications by comparison with those of standards, a number of mixtures were formulated and were field tested, as were the essential oils. The field tests failed to support unambiguously the premise that boll weevils select hibernation sites on the basis of leaf odor alone. However, in the presence of the sex pheromone, beta-caryophyllene (P > T = 0.08), or a mixture of three sesquiterpene hydrocarbons (P > T = 0.10), or a mixture of alkyl alcohols (P > T = 0.15) increased captures. The response to formulations of the sex pheromone with beta-caryophyllene may be primarily sexual, based on its presence in female boll weevils.     

Significance of volatile compounds produced by spoilage bacteria in vacuum-packed cold-smoked salmon (Salmo salar) analyzed by GC-MS and multivariate regression

Changes were studied in the concentration of 38 volatile compounds during chilled storage at 5 degrees C of six lots of commercially produced vacuum-packed cold-smoked salmon and sterile cold-smoked salmon. The majority of volatile compounds produced during spoilage of cold-smoked salmon were alcohols, which were produced by microbial activity. Partial least-squares regression of volatile compounds and sensory results allowed for a multiple compound quality index to be developed. This index was based on volatile bacterial metabolites, 1-propanol and 2-butanone, and 2-furancarboxaldehyde produced by autolytic activity. Only a few of the volatile compounds produced during spoilage of cold-smoked salmon had an aroma value high enough to indicate contribution to the spoilage off-flavor of cold-smoked salmon. These were trimethylamine, 3-methylbutanal, 2-methyl-1-butanol, 3-methyl-1-butanol, 1-penten-3-ol, and 1-propanol. The potency and importance of these compounds was confirmed by gas chromatography-olfactometry. The present study provides valuable information on the bacterial reactions responsible for spoilage off-flavors of cold-smoked salmon, which can be used to develop biosensors for on-pack shelf-life determinations.     

Sex pheromone of browntail moth, Euproctis chrysorrhea (L.): synthesis and field deployment

The browntail moth, Euproctis chrysorrhea (L.), is native to Eurasia, where periodic outbreaks result in defoliation of forest, shade, and ornamental trees. In addition to the damage caused by defoliation, human contact with larval urticating hairs often results in severe dermatitis. Hence, tools for monitoring and controlling the moth populations are desirable. The female-produced sex pheromone of the browntail moth was identified previously, but the synthesis had not been published. This paper reports the synthesis of the pheromone of the browntail moth, (7Z,13Z,16Z,19Z)-docosatetraenyl isobutyrate, using in a key step a Wittig olefination of (6Z)-13-(tetrahydo-2H-pyran-2-yloxy)tridecenal. Field trapping studies were conducted with rubber septa and string formulations of the pheromone and included dose-response, pheromone purity, and dispenser-aging trials. It was found that traps baited with 250 microg of pheromone of 91-94% isomeric purity (main impurity presumably being the 13E isomer) on rubber septa are suitable for monitoring moth populations during the entire flight season.