松小蠹信息素马鞭烯醇和马鞭烯酮合成研究

以α-蒎烯为原料,控制反应温度及氧气流量,用松香酸钴催化,对α-蒎烯进行区域选择性氧化,得松小蠹信息素马鞭烯醇和马鞭烯酮,并用IR和MS谱验证了结构。对反应中的影响因素进行了研究和探讨,提出反应的优化条件,为马鞭烯醇和马鞭烯酮的扩大生产提供数据和依据。     

Olfactory Experience Modifies Semiochemical Responses in a Bark Beetle Predator

A typical feature of forest insect pests is their tendency to undergo large fluctuations in abundance, which can jeopardize the persistence of their predaceous natural enemies. One strategy that these predators may adopt to cope with these fluctuations would be to respond to sensory cues for multiple prey species. Another possible adaptation to temporal variation in the prey community could involve the learning of prey cues and switching behavior. We conducted three experiments to investigate the ability of the generalist bark beetle predator Thanasimus dubius (F.) (Coleoptera: Cleridae) to respond to different prey signals and to investigate the effect of olfactory experience. We first conducted a field choice test and a wind tunnel experiment to examine the kairomonal response of individual predators toward prey pheromone components (frontalin, ipsenol, ipsdienol, sulcatol) along with the pine monoterpene α-pinene, which is a volatile compound from the host of the prey. We also presented semiochemically naive predators with two prey pheromone components, frontalin and ipsenol, alone or associated with a reward. Our results showed that T. dubius populations are composed of generalists that can respond to a broad range of kairomonal signals. Naive T. dubius also were more attracted to ipsenol following its association with a reward. This work constitutes the first evidence that the behavior of a predatory insect involved in bark beetle population dynamics is influenced by previous olfactory experience, and provides a potential explanation for the pattern of prey switching observed in field studies.     

Volatiles from Potential Hosts of Rhopalicus tutela a Bark Beetle Parasitoid

Host location cues for parasitic wasps that attack bark beetle larvae concealed under the bark of spruce trees were analyzed by collecting odor samples from entrance holes into the bark beetle galleries, isolated larvae, and pupal chambers with or without bark beetle larvae. Odor samples were collected by dynamic headspace adsorptions on Porapak Q or static adsorptions by using solid-phase microextraction (SPME) with Carbowax–divinylbenzene as the adsorbing phase. Samples were analyzed by coupled gas chromatographic–electroantennographic detection (GC-EAD) and GC-mass spectrometry (GC-MS). The antennae of Rhopalicus tutela females responded primarily to oxygenated monoterpenes that are typical for damaged host trees. These compounds are attractive to bark beetle parasitoids in long-range host location, suggesting that they are used in both long- and short-range host location. No differences could be detected between samples collected from pupal chambers with or without mature larvae. Larvae outside pupal chambers emitted low quantities of the same compounds present in empty pupal chambers. The data support the hypothesis that volatiles used by host foraging parasitoids arise from the interaction between introduced microorganisms and the bark and/or vascular tissue of the host tree rather than from the bark beetle larvae.     

Attraction Modulated by Spacing of Pheromone Components and Anti-attractants in a Bark Beetle and a Moth

Orientation for insects in olfactory landscapes with high semiochemical diversity may be a challenging task. The partitioning of odor plumes into filaments that are interspersed with pockets of ‘clean air’ may help filament discrimination and upwind flight to attractive sources in the face of inhibitory signals. We studied the effect of distance between odor sources on trap catches of the beetle, Ips typographus, and the moth, Spodoptera littoralis. Insects were tested both to spatially separated pheromone components [cis-verbenol and 2-methyl-3-buten-2-ol for Ips; (Z,E)-9,11-tetradecadienyl acetate and (Z,E)-9,12-tetradecadienyl acetate for Spodoptera], and to separated pheromone and anti-attractant sources [non-host volatile (NHV) blend for Ips; (Z)-9-tetradecenyl acetate for Spodoptera]. Trap catch data were complemented with simulations of plume structure and plume overlap from two separated sources using a photo ionization detector and soap bubble generators. Trap catches of the beetle and the moth were both affected when odor sources in the respective traps were increasingly separated. However, this effect on trap catch occurred at smaller (roughly by an order of magnitude) odor source separation distances for the moth than for the beetle. This may reflect differences between the respective olfactory systems and central processing. For both species, the changes in trap catches in response to separation of pheromone components occurred at similar spacing distances as for separation of pheromone and anti-attractant sources. Overlap between two simulated plumes depended on distance between the two sources. In addition, the number of detected filaments and their concentration decreased with downwind distance. This implies that the response to separated odor sources in the two species might take place under different olfactory conditions. Deploying multiple sources of anti-attractant around a pheromone trap indicated long-distance (meter scale) effects of NHV on the beetle and a potential use for NHV in forest protection.     

Volatile Organic Compounds Emitted by Fungal Associates of Conifer Bark Beetles and their Potential in Bark Beetle Control

Conifer bark beetles attack and kill mature spruce and pine trees, especially during hot and dry conditions. These beetles are closely associated with ophiostomatoid fungi of the Ascomycetes, including the genera Ophiostoma, Grosmannia, and Endoconidiophora, which enhance beetle success by improving nutrition and modifying their substrate, but also have negative impacts on beetles by attracting predators and parasites. A survey of the literature and our own data revealed that ophiostomatoid fungi emit a variety of volatile organic compounds under laboratory conditions including fusel alcohols, terpenoids, aromatic compounds, and aliphatic alcohols. Many of these compounds already have been shown to elicit behavioral responses from bark beetles, functioning as attractants or repellents, often as synergists to compounds currently used in bark beetle control. Thus, these compounds could serve as valuable new agents for bark beetle management. However, bark beetle associations with fungi are very complex. Beetle behavior varies with the species of fungus, the stage of the beetle life cycle, the host tree quality, and probably with changes in the emission rate of fungal volatiles. Additional research on bark beetles and their symbiotic associates is necessary before the basic significance of ophiostomatoid fungal volatiles can be understood and their applied potential realized.     

Electrophysiological and Olfactometer Responses of Two Histerid Predators to Three Pine Bark Beetle Pheromones

We measured electrophysiological responses in the antennae of two predaceous hister beetles, Platysoma parallelum and Plegaderus transversus, exposed to racemic mixtures of primary aggregation pheromones of scolytid bark beetle prey, ipsenol, ipsdienol, and frontalin. No significant differences were found for either histerid species between male and female antennal responses to any of the three pheromones. Measurement of antennal threshold responses indicated that Pla. parallelum has increasing antennal sensitivity to ipsdienol, ipsenol, and frontalin. In contrast, Ple. transversus exhibited similar detection thresholds to all three pheromones. Pla. parallelum antennae exhibited different response amplitudes to the three pheromones at quantities above the detection threshold, while Ple. transversus had similar responses to each. Behavioral responses to the same three pheromones were evaluated for both histerid species using pedestrian olfactometer bioassays. Both species were attracted to frontalin and ipsenol, but not ipsdienol. Pla. parallelum was significantly more attracted to frontalin than ipsenol, while Ple. transversus showed no significant preference for either compound. Our results suggest that histerids that prey upon pine bark beetles may have different host or host habitat preferences, which could reduce interspecific competition.     

Green Leaf Volatiles Interrupt Pheromone Response of Spruce Bark Beetle, Ips typographus

A synthetic mixture of nine green leaf volatiles (GLVs) including linalool was tested on antennae of Ips typographus (L.) with coupled gas chromatographic–electroantennographic detection (GC-EAD). Strong responses were found to 1-hexanol, (Z)-3-hexen-1-ol, and (E)-2-hexen-1-ol. Weak responses were recorded to (E)-3-hexen-1-ol, (Z)-2-hexen-1-ol and linalool, while hexanal, (E)-2-hexenal and (E)-3-hexenyl acetate elicited no EAD responses. In a laboratory walking bioassay, the attraction of I. typographus females to a synthetic pheromone source was significantly reduced when a mixture of the three most EAD-active GLV alcohols was added to the source. Further reduction in response was obtained when these three alcohols were combined with verbenone (Vn). In field trapping experiments, a blend of 1-hexanol, (Z)-3-hexen-1-ol, and (E)-2-hexen-1-ol reduced I. typographus trap catches by 85%, while ca. 70% reduction of trap catch was achieved by Vn or a blend of (E)-3-hexen-1-ol, (Z)-2-hexen-1-ol, and linalool. The strongest disruptive effect was found when Vn plus a blend of the three most EAD active GLV alcohols was added to the pheromone trap (95% catch reduction). Adding the blend of the three most EAD active alcohols to pheromone-baited traps significantly reduced the proportion of males captured. These three GLV alcohols were also disruptive in the laboratory and in the field when tested individually. Hexanal, (E)-2-hexenal, and (Z)-3-hexenyl acetate were inactive both in the lab and in the field. Our results suggest that these nonhost green leaf alcohols may explain part of the host selection behavior of conifer-attacking bark beetles and may offer a source of inhibitory signals for alternative management strategy for forest protection.     

Influence of Some Fatty Acids on Oviposition by the Bruchid Beetle, Callosobruchus maculatus

The cowpea seed beetle, Callosobruchus maculatus, will lay its eggs on many potential hosts and inert surfaces. Oviposition on glass beads is stimulated by coating them with individual fatty acids. Nevertheless, female beetles reject mung seeds less frequently than beads treated with either an extract of mung seeds or, especially, an extract of mung seeds plus oleic acid. The addition of oleic acid to the extract resulted in a change in the sequence of oviposition behavior, notably an increase in a raised body position indicative of hosts of low acceptability. Fatty acids are present in the epicuticular waxes of legume seeds; wax extract of mung bean contains 32.4% fatty acid and 14 alkanes, whereas a wax extract of chickpea contains 5% fatty acid and 18 alkanes. Thus, chickpea may be a less acceptable host for oviposition than mung bean because of physical differences and/or because of chemical differences, including a reduced total level of fatty acid or the high proportion of oleic acid it is reported to contain. It is concluded that an appropriate mixture of fatty acids in the epicuticular waxes stimulates oviposition but that an elevated level of oleic acid in conjunction with others is deterrent.     

Spatial Displacement of Release Point can Enhance Activity of an Attractant Pheromone Synergist of a Bark Beetle

Flight responses of the southern pine beetle, Dendroctonus frontalis Zimmermann, to widely-spaced (>130 m) traps baited with pine volatiles (in turpentine) and the female-produced pheromone component frontalin were enhanced when a bait containing the male pheromone component (+)-endo-brevicomin was attached directly to the trap. However, displacing this bait 4–16 m horizontally from the trap significantly increased its synergistic effect. (+)-endo-Brevicomin enhanced catch to the same degree when the bait was positioned either on the trap or 32 m away. In another experiment, pairs of frontalin/turpentine-baited traps were established with 4 m spacing between traps and >100 m spacing between pairs. Attachment of either a racemic or (+)-endo-brevicomin bait to one trap of a pair caused a significant increase in catch by both traps, but catch in the trap lacking endo-brevicomin was increased more than in its endo-brevicomin-baited twin. In a third experiment, widely-spaced groups of three traps (in a line with 1 and 4 m spacing between the middle and outer traps) were baited uniformly with frontalin and turpentine, and the release rate of (+)-endo-brevicomin from the middle trap was varied across three orders of magnitude. Release rates sufficient to enhance total D. frontalis catch by the trio also caused relatively higher catches to occur in the outer traps than in the middle one. These experiments indicated that both male and female D. frontalis fly to and land preferentially at sources of frontalin and host odors when these are located some distance away from a source of endo-brevicomin. This behavior may have evolved in D. frontalis to allow host-seeking beetles to locate growing, multi-tree infestations while avoiding fully-colonized trees within these infestations. Our data demonstrate that trap spacing alone can qualitatively change the outcome of bait evaluation trials and may explain why many earlier experiments with endo-brevicomin failed to identify it as an aggregation pheromone synergist for D. frontalis. We believe that important aggregative functions of semiochemicals of other bark beetle species may have been similarly overlooked due to choice of experimental procedures.     

Analysis of Volatiles Induced by Oviposition of Elm Leaf Beetle Xanthogaleruca luteola on Ulmus minor

Egg deposition of the elm leaf beetle Xanthogaleruca luteola causes the emission of volatiles from its food plant, Ulmus minor. These volatiles are exploited by the egg parasitoid, Oomyzus gallerucae, to locate its host. In contrast to other tritrophic systems, the release of volatiles is not induced by feeding but by egg deposition. Previous investigations showed that the release is systemic and can be triggered by jasmonic acid. Comparison of headspace analysis revealed similarities in the blend of volatiles emitted following egg deposition and feeding. The mixture consists of more than 40 compounds; most of the substances are terpenoids. Leaves next to those carrying eggs emit fewer compounds. When treated with jasmonic acid, leaves emit a blend that consists almost exclusively of terpenoids. Dichloromethane extracts of leaves treated with jasmonic acid were also investigated. After separation of extracts of jasmonate induced elm leaves on silica, we obtained a fraction of terpenoid hydrocarbons that was attractive to the parasitoids. This indicates that jasmonic acid stimulates the production of terpenoid hydrocarbons that convey information of egg deposition to the parasitoid.     

Disruption by Conophthorin of the Kairomonal Response of Sawyer Beetles to Bark Beetle Pheromones

Antennally active nonhost angiosperm bark volatiles were tested for their ability to reduce the response of three common species of coniferophagous wood-boring Cerambycidae to attractant-baited multiple funnel traps in the southern interior of British Columbia. Of the nonhost volatiles tested, only conophthorin was behaviorally active, disrupting the attraction of sawyer beetles, Monochamus spp., to traps baited with the host volatiles -pinene and ethanol and the bark beetle pheromones ipsenol and ipsdienol. Conophthorin did not affect the attraction of sawyer beetles to the host kairomones -pinene and ethanol in the absence of bark beetle pheromones, nor did it have any behavioral effect on adults of Xylotrechus longitarsis, which were not attracted to bark beetle pheromones. These results indicate that conophthorin does not act as a general repellent for coniferophagous Cerambycidae, as it seems to do for many species of Scolytidae, but has the specific activity of disrupting the kairomonal response of sawyer beetles to bark beetle pheromones.     

Host-Plant Chemistry Influences Oviposition Choice of the Spicebush Swallowtail Butterfly

The spicebush swallowtail, Papilio troilus (L.), lays its eggs on plants in the family Lauraceae. Sassafras [Sassafras albidum (Nutt.) Nees], spicebush [Lindera benzoin (L.) Spreng.], redbay (Persea borbonia (L.)] and camphortree [Cinnamomum camphora (Nees) Eberm.] are four of its known host plants. In one-choice tests, free-flying spicebush swallowtail females laid eggs on chemical extracts of the leaves of each of these four hosts. In two-choice experiments, females always preferred to oviposit on an extract of sassafras compared to extracts of the other three hosts. It was shown for spicebush extract that this response was not due to oviposition experience. Previously we had identified one of the host plant chemicals acting as an oviposition stimulant in sassafras extract as 3-caffeoyl-muco-quinic acid (3-CmQA). Extracts of the other three hosts did not contain this compound. The addition of 3-CmQA alone to spicebush extract did not increase oviposition activity. It did, however, increase discrimination between hosts and nonhosts. When a fraction of sassafras extract containing 3-CmQA and other synergistic stimulants was added to spicebush extract, preference for sassafras extract was no longer recorded. These results show existing differences in oviposition chemistry among host plants of the spicebush swallowtail and how these differences can influence oviposition choice in bioassay experiments.     

Electrophysiological and Behavioral Responses of the Bark Beetle Dendroctonus rhizophagus to Volatiles from Host Pines and Conspecifics

The bark beetle Dendroctonus rhizophagus is endemic to northwestern Mexico where it kills immature pines?相似文献   

Oviposition Choice of Mexican Bean Beetle (Epilachna varivestis) Depends on Host Plants Cyanogenic Capacity

The choice of insect females as to where to lay their eggs strongly affects progeny survival and, thus, fitness. We conducted choice experiments with female Mexican bean beetles, which were offered lima bean plants differing in their cyanogenic capacity (HCNc), i.e., in the intensity of hydrogen cyanide release per time unit from damaged plant tissue. Females preferred to lay their eggs on plants with low HCNc. In contrast, the mere concentration of cyanide-containing precursors (the cyanogenic potential, HCNp) did not affect oviposition choices. Plant cyanogenesis occurs after tissue damage, which brings specific β-glucosidases in contact with their substrates, cyanogenic glycosides, from which they are separated by compartmentation in the intact plant tissue. Plants commonly store toxic compounds in an inactive form. Our results demonstrate that for cyanogenesis, which is widespread in plants, it is the toxic product itself rather than the precursor that affects oviposition choices of a specialized herbivore.     

Angiosperm Bark Volatiles Disrupt Response of Douglas-Fir Beetle, Dendroctonus pseudotsugae, to Attractant-Baited Traps

Antennally active, bark-derived, angiosperm volatiles were tested singly and in groups for their ability to disrupt the response of the Douglas-fir beetle (DFB), Dendroctonus pseudotsugae, to attractant-baited multiple-funnel traps. One compound, conophthorin, was active alone in reducing the response of beetles to the baited traps. Further experiments showed disruptive activity in two aliphatic green-leaf alcohols [1-hexanol and (Z)-3-hexen-1-ol], as well as guaiacol and benzyl alcohol, and three aliphatic aldehydes [nonanal, hexanal, and (E)-2-hexenal] but not in two aromatic aldehydes (benzaldehyde and salicylaldehyde). Every binary combination that included conophthorin or any two of the other groups, except aromatic aldehydes, significantly reduced the response of beetles to baited traps. Various ternary mixtures and the complete mixture of all the groups were generally the most effective treatments. These results provide evidence that DFBs recognize and avoid nonhosts while flying rather than landing on candidate hosts and testing them while in contact with the tree. Nonhost angiosperm bark volatiles may have practical utility on their own or in combination with the antiaggregation pheromone 3-methylcyclohex-3-en-1-one (MCH) to protect single trees, logs, or stands from attack by the DFB.     

Southern Pine Beetle, Dendroctonus frontalis, Antennal and Behavioral Responses to Nonhost Leaf and Bark Volatiles

A growing body of evidence suggests that bark beetles detect and avoid release points of volatile compounds associated with nonhost species, and thus such nonhost volatiles may have potential utility in the management of bark beetles. We used a coupled gas chromatograph-electroantennographic detector (GC-EAD) to assay the olfactory sensitivity of the southern pine beetle, Dendroctonus frontalis Zimmermann, to volatiles from leaves and bark of eight species of nonhost angiosperm trees that are common in the range of D. frontalis. Tree species sampled were red maple (Acer rubrum L.), mockernut hickory [Carya alba (L.) Nutt. ex Ell.], sweetgum (Liquidambar styraciflua L.), black tupelo (Nyssa sylvatica Marsh.), black cherry (Prunus serotina Ehrh.), southern red oak (Quercus falcata Michx.), blackjack oak [Quercus marilandica (L.) Muenchh.], and water oak (Quercus nigra L.). Beetle antennae responded to a total of 28 identifiable compounds in these samples. The relative olfactory responsiveness to 14 of these, as well as to nonanoic acid and four additional volatiles reported to be associated with nonhost angiosperms, was assessed in GC-EAD analyses of synthetic dilutions spanning six orders of magnitude. The largest response voltage amplitudes were obtained with trans-conophthorin, nonanoic acid, terpinen-4-ol, phenylethyl alcohol, and eucalyptol, whereas the lowest response thresholds were to nonanoic acid, nonanal, linalool, (E)-2-hexen-1-ol, and phenylethyl alcohol. Funnel traps baited with various combinations of eleven antennally-active angiosperm volatiles along with a standard attractant captured significantly fewer male and female D. frontalis than traps baited with the standard attractant alone. Our data suggest that a diversity of semiochemicals may be involved in host species discrimination by D. frontalis, and several may have utility in their management.     

Adaptation of Defensive Strategies by the Pea Aphid Mediates Predation Risk from the Predatory Lady Beetle

Within a species, individual animals adopt various defensive strategies to resist natural enemies, but the defensive strategies that are adopted in response to variations in predation risk are poorly understood. Here, we assessed consecutive foraging processes on cohorts of two biotypes (green and red) of the pea aphid, Acyrthosiphon pisum, by the predatory lady beetle Propylea japonica, to investigate the adaptive mechanism underlying the defensive strategy. We observed the behavioral responses of individuals (continue feeding or escape, i.e., walk away or drop off from initial feeding site), simultaneously quantified the amount of alarm pheromone, (E)-β-farnesene (EβF) released from cohorts using gas chromatography-mass spectrometry (GC-MS), and recorded the foraging times of predators in intervals. The results indicated that: (1) the anti-predator responses differed markedly between biotypes and among the stages of the consecutive foraging processes. (2) Few green cohorts tended to release EβF during the first foraging; those that did released only a low dose that did not increase the number of escapes. However, the amount of EβF rose rapidly following the second foraging process, which caused an intense escape response. In contrast, more red cohorts released greater amounts of EβF, which caused more individuals to escape from their innate feeding sites during the first foraging. During the second foraging, more red individuals tended to escape without releasing EβF in greater quantities. (3) The foraging time was effectively shortened in each biotype cohort that adopted diverse defensive strategies. This study of the defensive strategies of the pea aphid may contribute to understanding the intraspecific differences in aphid defense mechanisms.     

Responses of the Mediterranean Pine Shoot Beetle Tomicus destruens (Wollaston) to Pine Shoot and Bark Volatiles

The pine shoot beetle Tomicus destruens has two dispersal phases per generation. In the first, mature adults move toward trunks of dying pines to lay eggs; in the second, callow adults move toward the shoots of healthy pines for maturation feeding. However, there is no information on the chemical stimuli that govern host selection by T. destruens adults. The aims of this study were: (1) to identify the volatiles released by shoots and bark of stone pine that are behaviorally and electrophysiologically active on T. destruens; (2) to verify which blends and concentrations of such volatiles are differently active on males and females, as well as on callow and mature adults, during the two host search phases (breeding and feeding). A four-arm olfactometer was used to test the behavior of walking T. destruens adults toward various sources of volatiles including fresh shoots and bark, their collected volatiles, and two synthetic blends. For each odor, the behavior of both callow and mature males and females was recorded individually. Shoot and bark extracts were analyzed by coupled gas chromatography and mass spectrometry (GC-MS), and tested by gas chromatography coupled with electroantennography (GC-EAD) on T. destruens males and females. Two blends of two (alpha-pinene and beta-myrcene; blend A) and three (alpha-pinene, beta- myrcene, and alpha-terpinolene; blend B) synthetic compounds, chosen among those that induce EAD responses and known to be attractive for other bark beetle species, were tested in the olfactometer at five concentrations. Insect behavior was affected by the degree of sexual maturation but not by sex. Callow insects were attracted by shoots and their extracts, while mature individuals by bark and its extracts. Six extracted compounds were active on T. destruens antennae: limonene, (Z)-3-hexen-1-ol and beta-caryophyllene, alpha-pinene, beta-myrcene, and alpha-terpinolene. alpha-Terpinolene, released only by bark, was active only on mature insects, whereas (Z)-3-hexen-1-ol, released only by shoots, was active only on callows. Males and females showed similar EAD responses. Of the six extracted volatiles, two were attractive for callow adults (blend A) and three for matures (blend B). In both cases, responses were positively correlated with blend concentration, although a repellent effect was noted at the highest concentrations.     

Bacteria Associated with a Tree-Killing Insect Reduce Concentrations of Plant Defense Compounds

Bark beetles encounter a diverse array of constitutive and rapidly induced terpenes when attempting to colonize living conifers. Concentrations of these compounds at entry sites can rapidly reach levels toxic to beetles, their brood, and fungal symbionts. Large numbers of beetles can overwhelm tree defenses via pheromone-mediated mass attacks, but the mechanisms are poorly understood. We show that bacteria associated with mountain pine beetles can metabolize monoterpenes and diterpene acids. The abilities of different symbionts to reduce concentrations of different terpenes appear complementary. Serratia reduced concentrations of all monoterpenes applied to media by 55–75 %, except for α-pinene. Beetle-associated Rahnella reduced (?)- and (+)-α-pinene by 40 % and 45 %, respectively. Serratia and Brevundimonas reduced diterpene abietic acid levels by 100 % at low concentrations. However, high concentrations exhausted this ability, suggesting that opposing rates of bacterial metabolism and plant induction of terpenes are critical. The two major fungal symbionts of mountain pine beetle, Grosmannia clavigera and Ophiostoma montium were highly susceptible to abietic acid. Grosmannia clavigera did not reduce total monoterpene concentrations in lodgepole pine turpentine. We propose the ability of bark beetles to exert landscape-scale impacts may arise partly from micro-scale processes driven by bacterial symbionts.