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Odontothrips loti (Haliday) is a thrip pest of leguminous plants. The aggregation pheromone of this pest and its stereoisomers have been synthesized. The central of this strategy involved enantioselective cross‐coupling of racemic benzyl 2‐bromopropanoate with alkenyl Grignard, Evans' chiral auxiliaries and Yamaguchi esterification of chiral 2‐methylbutanoic acid with chiral lavandulol. [ABSTRACT FROM AUTHOR]

BACKGROUND: The chafer beetle, Holotrichia parallela, causes damage to numerous economically significant crops worldwide. Adult beetles exhibit aggregation behavior likely mediated by a male‐produced pheromone. Advancements in biological research technology have facilitated the identification of insect aggregation pheromones and promoted their applications as bait for trapping and monitoring pests. Currently, only a few active components of aggregation pheromones from Holotrichia species have been identified. However, the specific components of aggregation pheromones produced by H. parallela remain unknown. RESULT: In this study, we initially observed from Y‐tube olfactometer assays that both male and female H. parallela were significantly attracted to volatiles emitted by males, but not to those from females. We then collected hindgut crude extracts of male adults and carried out gas chromatography–mass spectrometry analysis to identify potential aggregation pheromone components. Pentadecyl acetate, cis‐13‐docosenol, and behenic acid were identified as male‐specific compounds in comparison to female extracts, serving as components of the aggregation pheromone in H. parallela. We further evaluated their attractiveness to H. parallea in both laboratory and field experiments. In laboratory settings, pentadecyl acetate, cis‐13‐docosenol, and behenic acid evoked significant responses to both males and females at specific concentrations, as evidenced by both electroantennography tests and behavioral bioassays. Under field conditions, traps baited with these three compounds captured significantly more H. parallela adults compared to control traps. CONCLUSION: In this study, we found that pentadecyl acetate, cis‐13‐docosenol, and behenic acid are specifically present in male H. parallela, serving as aggregation pheromones. Both laboratory and field‐trapping experiments suggest their potential as monitoring and controlling tools against H. parallela adults. © 2024 Society of Chemical Industry. [ABSTRACT FROM AUTHOR]

This study deals with the field application of lure traps for trapping of the adult red palm weevil (Rhynchophorus ferrugineus) at the date palm orchard of Sindh, Pakistan. The pheromone traps, were installed at the date palm orchard under the field conditions such as aggregation pheromone dosage, food material (molasses), ester (isoamyl acetate) and trap density. During the field trials, it was observed that the 3 mg/trap dose of aggregation pheromone along with the 500 g of molasses and 4 mg/trap of ester trapped maximum female adult insects. The 10 traps/ha was the optimized trap density. Moreover, the higher number of insects were trapped in March and the minimum catches were observed in the month of November, December, January and February. The total male and female adult weevils captured were (N=18 females 60% and N=12 males 40%) and the sex ratio was 2:3 male and female, respectively. [ABSTRACT FROM AUTHOR]

As a new vector insect of pine wood nematodes in China, the Monochamus saltuarius (Coleoptera: Cerambycidae) vectors pine wilt nematodes into healthy pine trees through feeding and oviposition, resulting in huge economic losses to forestry. A promising control strategy is to develop safe and efficient attractants. This study aims to screen for the key active volatiles of Pinus koraiensis (Pinales: Pinaceae), Pinus tabuliformis (Pinales: Pinaceae), and Picea asperata (Pinales: Pinaceae) that can attract M. saltuarius, and to study the synergistic attraction of the main attractant plant volatiles with ethanol and insect aggregation pheromones. The preference of M. saltuarius for three hosts is P. koraiensis > P. tabuliformis > Picea asperata. We detected 18 organic volatiles from three host plants. Through EAG assays and indoor Y-tube behavioral experiments, 3-carene, (-)-camphor, β-pinene, α-phellandrene, terpinolene, α-pinene, D-limonene, and myrcene were screened to have attractive effects on M. saltuarius. We found that 3-carene, β-pinene, and α-pinene are the most attractive kairomones in field experiments, which may play a crucial role in the host localization of M. saltuarius. Ethanol has a synergistic effect on the attractant activity of 3-carene and β-pinene, and the synergistic effect on β-pinene is the best. The mixture of ethanol, 2-undecyloxy-1-ethanol, and ipsdienol can significantly enhance the attraction effect of β-pinene on M. saltuarius. These new findings provide a theoretical basis for the development of attractants for adult M. saltuarius and contribute to the green control of M. saltuarius. [ABSTRACT FROM AUTHOR]

BACKGROUND: The stick tea thrips, Dendrothrips minowai Priesner, is one of the most important sucking pests that seriously infest tea plants (Camellia sinensis) in China. Given that D. minowai exhibit aggregation behaviors in tea plantations, this study evaluated the potential of aggregation pheromones for their control. RESULTS: H‐tube olfactometer assays showed that D. minowai larvae, adult females and adult males were significantly attracted to larvae rather than adult females and males under laboratory conditions. Subsequent gas chromatography–mass spectrometry analysis of volatiles from larvae, identified two larva‐specific components: dodecyl acetate and tetradecyl acetate. Electrophysiological and behavioral experiments confirmed the positive response of females and males to dodecyl acetate, tetradecyl acetate, and their blend (1:1.5). Deployment of these aggregation pheromones on sticky traps resulted in a 1.2‐ to 3.0‐fold increase in the capture of D. minowai adults compared with control traps. In addition, deployment of sticky traps baited with these aggregation pheromones within tea plantations resulted in a noteworthy reduction in the population of adult thrips per 100 leaves, 10 days following trap deployment. The reduction ranged from 29% to 59%, in comparison with the control. CONCLUSION: D. minowai larvae produce aggregation pheromones, dodecyl acetate and tetradecyl acetate, that can be useful for controlling tea thrips. © 2023 Society of Chemical Industry. [ABSTRACT FROM AUTHOR]

This work reports the first demonstration that a chemoresistive sensor can be used to detect the aggregation pheromone of flour beetles. To prepare the sensing element of such a sensor, a novel functionalization method was developed to amplify amine groups on the surface of carbon nanotubes (CNTs). Unlike traditional amine-amplification approaches in which amplification efficiency is significantly reduced by self-crosslinking, the current amine amplification process was self-crosslinking-free due to the use of a home-made compound in which amine groups were protected by Boc (tert-butyloxycarbonyl) protecting groups and could be deprotected as needed. The inkjet ink formulated from the functionalized CNTs, together with an amine-rich compound and a commercial silver nanoparticle-based inkjet ink, was used to fabricate (via inkjet-printing and drop-casting) lightweight, flexible, and miniature-sized chemiresistive sensors for 4,8-dimethyldecanal (DMD), a compound known to be the aggregation pheromone of several species of flour beetles. A home-built gas sensing system, including a commercial gas generator, a DMD permeation tube with its emission rate certified, a data-acquisition system, and some home-developed LabVIEW-based programs, was utilized to perform the DMD sensing trials. The sensors showed ultra-high sensitivity to synthetic aggregation pheromone DMD, as indicated by their prompt and significant responses to 100 ppb DMD vapor. A mechanism for the sensitive sensing of DMD is proposed. [ABSTRACT FROM AUTHOR]

The diel flight activity in Cathartus quadricollis (Guerin-Meneville) (Coleoptera: Silvanidae), a predator of two important pests in Hawaii, coffee berry borer, Hypothenemus hampei (Ferrari) and tropical nut borer, Hypothenemus obscurus (F.) (Coleoptera: Curculionidae: Scolytinae) was studied in a macadamia nut orchard using yellow sticky traps baited with pheromone and fungal volatile attractants. The study was conducted at different months throughout the year and at different times during the lunar cycle (new moon and full moon). Flight activity peaked in the late hours of the photophase into the early hours of the scotophase, between 1830 and 2000 h; flight activity also occurred but to a lesser extent in the early morning hours between 0700 and 1030 h. Numbers of captured C. quadricollis during periods of flight activity were negatively correlated with wind speed. The implications of these findings for the development of optimal pest management strategies including biological control are discussed. [ABSTRACT FROM AUTHOR]

The push–pull approach using semiochemicals in pest control requires both an attractant and a repellent. Many previous studies have arbitrarily tested one or more known insect repellents or plant essential oils (EOs) hoping to find repellents of an insect pest. We used a comprehensive approach that synergistically tests in the field numerous natural volatiles from commercial EOs to identify repellents of the red palm weevil Rhynchophorus ferrugineus (Coleoptera: Curculionidae), a worldwide pest of palms and date palms. Volatiles from 79 EOs in slow-release devices were divided into five groups and tested in traps with attractive pheromone compared to traps with pheromone alone. EO-treatment groups exhibiting repellency due to significant trap shutdown, were further subdivided into subgroups of four EOs each and tested further. Two groups of four EOs (cypress, desert wormwood, elemi, and Eucalyptus citriodora) and (niaouli, nutmeg, oregano, and orange sweet), or their corresponding mixtures of major volatiles, caused pheromone trap reductions of up to 92%. Further tests showed that seven of the eight EOs are similarly repellent as the corresponding subgroup. This systematic approach of successively testing sub-fractions of EOs in the field for trap shutdown should be useful to identify repellents of other insect pests of crops. [ABSTRACT FROM AUTHOR]

Death feigning is a behavior in which a prey is rendered motionless due to stimulation or threat by a predator. This anti-predator defense mechanism has been observed across a wide range of animal taxa and is considered adaptive. However, long durations of death feigning can decrease opportunities for feeding and reproduction, and therefore is a fitness cost as compared to environments without predators. Because death feigning is thought to be affected by the balance between survival and other fitness costs, selection pressure may drive individuals who are capable of plastic changes in the intensity of death feigning. Pheromones, which are important semiochemicals that affect foraging and reproductive success, may be one of the factors influencing the intensity of death-feigning behavior. In this study, we investigated the effect of an aggregation pheromone on the death-feigning behavior of the red flour beetle Tribolium castaneum. We found that beetles exposed to the pheromone showed a significantly shorter duration of death feigning than beetles that were not exposed to the pheromone. Therefore, our results suggest that an aggregation pheromone can plasticly alter the death-feigning behavior in T. castaneum. [ABSTRACT FROM AUTHOR]

The evolution of chemosensory receptors is key for the adaptation of animals to their environment. Recent knowledge acquired on the tri-dimensional structure of insect odorant receptors makes it possible to study the link between modifications in the receptor structure and evolution of response spectra in more depth. We investigated this question in palm weevils, several species of which are well-known invasive pests of ornamental or cultivated palm trees worldwide. These insects use aggregation pheromones to gather on their host plants for feeding and reproduction. An odorant receptor detecting the aggregation pheromone components was characterised in the Asian palm weevil Rhynchophorus ferrugineus. This study compared the response spectra of this receptor, RferOR1, and its ortholog in the American palm weevil R. palmarum, RpalOR1. Sequences of these two receptors exhibit more than 70 amino acid differences, but modelling of their 3D structures revealed that their putative binding pockets differ by only three amino acids, suggesting possible tuning conservation. Further functional characterization of RpalOR1 confirmed this hypothesis, as RpalOR1 and RferOR1 exhibited highly similar responses to coleopteran aggregation pheromones and chemically related molecules. Notably, we showed that R. ferrugineus pheromone compounds strongly activated RpalOR1, but we did not evidence any response to the R. palmarum pheromone compound rhynchophorol. Moreover, we discovered that several host plant volatiles also activated both pheromone receptors, although with lower sensitivity. This study not only reveals evolutionary conservation of odorant receptor tuning across the two palm weevil species, but also questions the specificity of pheromone detection usually observed in insects.

As a new vector insect of pine wood nematodes in China, the Monochamus saltuarius (Coleoptera: Cerambycidae) vectors pine wilt nematodes into healthy pine trees through feeding and oviposition, resulting in huge economic losses to forestry. A promising control strategy is to develop safe and efficient attractants. This study aims to screen for the key active volatiles of Pinus koraiensis (Pinales: Pinaceae), Pinus tabuliformis (Pinales: Pinaceae), and Picea asperata (Pinales: Pinaceae) that can attract M. saltuarius, and to study the synergistic attraction of the main attractant plant volatiles with ethanol and insect aggregation pheromones. The preference of M. saltuarius for three hosts is P. koraiensis > P. tabuliformis > Picea asperata. We detected 18 organic volatiles from three host plants. Through EAG assays and indoor Y-tube behavioral experiments, 3-carene, (-)-camphor, β-pinene, α-phellandrene, terpinolene, α-pinene, D-limonene, and myrcene were screened to have attractive effects on M. saltuarius. We found that 3-carene, β-pinene, and α-pinene are the most attractive kairomones in field experiments, which may play a crucial role in the host localization of M. saltuarius. Ethanol has a synergistic effect on the attractant activity of 3-carene and β-pinene, and the synergistic effect on β-pinene is the best. The mixture of ethanol, 2-undecyloxy-1-ethanol, and ipsdienol can significantly enhance the attraction effect of β-pinene on M. saltuarius. These new findings provide a theoretical basis for the development of attractants for adult M. saltuarius and contribute to the green control of M. saltuarius.

The brown‐winged green bug, Plautia stali Scott (Hemiptera: Pentatomidae), is a major pest in orchards in Japan and Korea. Large numbers of adults are attracted by aggregation pheromone [methyl (E,E,Z)‐2,4,6‐decatrienoate] and cause extensive damage to the fruit. To identify olfactory‐related genes in P. stali, we performed RNA sequencing (RNA‐seq) of adult antennae. Among the 27299 contigs, 16 putative odorant‐binding protein (OBP) genes were identified and designated as PstaOBP1–16, including 10 classic (i.e., containing six conserved cysteines) and six Plus‐C (i.e., containing more than six cysteines) OBP genes. Quantitative reverse‐transcription polymerase chain reaction (qRT‐PCR) revealed that four genes (PstaOBP1, 3, 6, and 7) were strongly expressed in the antennae. PstaOBP2 was detected throughout the insect body, with higher expression in the antennae, stylet, and tarsus. The remaining OBP genes were expressed in very small amounts. PstaOBP1, which showed the highest expression in adult antennae, was expressed in Escherichia coli (Migula) Castellani & Chalmers cells and the recombinant protein was subjected to a ligand‐binding competitive assay. PstaOBP1 bound to methyl (E,E,Z)‐2,4,6‐decatrienoate with high affinity. Of the other 26 compounds tested, hinokitiol and tropolone bound strongly to PstaOBP1. Hinokitiol is an odor component of hinoki cypress, a host tree of P. stali. Electrophysiological responses to methyl (E,E,Z)‐2,4,6‐decatrienoate and hinokitiol were detected using adult P. stali antennae. Combined, these results suggest that PstaOBP1 is involved in P. stali responses to pheromone and host plant volatiles. [ABSTRACT FROM AUTHOR]

Many wood-boring insects use aggregation pheromones during mass colonization of host trees. Bark beetles (Curculionidae: Scolytinae) are a model system, but much less is known about the role of semiochemicals during host selection by ambrosia beetles. As an ecological clade within the bark beetles, ambrosia beetles are obligately dependent on fungal mutualists for their sole source of nutrition. Mass colonization of trees growing in horticultural settings by exotic ambrosia beetles can occur, but aggregation cues have remained enigmatic. To elucidate this mechanism, we first characterized the fungal associates of the exotic, massaggregating ambrosia beetle Xylosandrus germanus in Southern Germany. Still-air olfactometer bioassays documented the attraction of X. germanus to its primary nutritional mutualist Ambrosiella grosmanniae and to a lesser extent another common fungal isolate (Acremonium sp.). During two-choice bioassays, X. germanus was preferentially attracted to branch sections (i.e., bolts) that were either pre-colonized by conspecifics or pre-inoculated with A. grosmanniae. Subsequent analyses identified microbial volatile organic compounds (MVOCs) that could potentially function as aggregation pheromones for X. germanus. To our knowledge, this is the first evidence for fungal volatiles as attractive cues during host selection by X. germanus. Adaptive benefits of responding to fungal cues associated with an infestation of conspecifics could be a function of locating a suitable substrate for cultivating fungal symbionts and/or increasing the likelihood of mating opportunities with the flightless males. However, this requires solutions for evolutionary conflict arising due to potential mixing of vertically transmitted and horizontally acquired symbiont strains, which are discussed. [ABSTRACT FROM AUTHOR]

Red palm weevil (RPW), Rhynchophorus ferrugineus (Coleoptera: Curculionidae), is rapidly infesting palm trees (Arecaceae) in several countries, threatening coconut, date, and oil cultivations. The male-produced aggregation pheromone in palm weevils has been reported to be secreted through the mouth to the rostrum, a snout-like projection key for pheromone emission and dispersion. The olfactory mechanisms that underlie peripheral odorant detection in RPW have been addressed at the antennal level. However, the rostrum remains unexplored. Through RNA-seq, 27 odorant-binding proteins (OBPs), 6 chemosensory proteins (CSPs), 4 sensory neuron membrane proteins (SNMPs), 21 gustatory receptors (GRs), 25 odorant receptors (ORs) (including one odorant receptor coreceptor, Orco) and 10 ionotropic receptors (IRs), were identified. We reported 27 novel rostrum-specific olfactory proteins (4 IRs, 11 GRs, 2 CSPs, 3 OBPs, and 7 ORs) in R. ferrugineus (Rfer). The OBPs (RferSOBPs) [Rfer with “S” indicating “snout” (rostrum)] were the most abundant transcripts compared with the rest of the olfactory proteins. We identified several rostrum OBPs, which predominately emerged through gene duplication, and were found expressed in both rostrum and antennae. Noticeably, we found R. ferrugineus pheromone-binding protein (RferOBP1768) paralog in the rostrum (RferOBP14) and mapped it in the same scaffold at a different position on the RPW genome as a recent duplicate. We found that an OR (RferSOR1) was the most abundant for both field-collected and lab-reared RPWs, in the rostrum and antennae. Likewise, up-regulated olfactory-related proteins were established in field conditions compared with those from laboratory-reared. We found a rostrum-specific, highly expressing RferSIR1 in IR93a-clade related to hygrosensation. The role of these olfactory proteins as targets for identifying more specific and powerful semiochemicals is discussed in the context of pest management.

Many wood-boring insects use aggregation pheromones during mass colonization of host trees. Bark beetles (Curculionidae: Scolytinae) are a model system, but much less is known about the role of semiochemicals during host selection by ambrosia beetles. As an ecological clade within the bark beetles, ambrosia beetles are obligately dependent on fungal mutualists for their sole source of nutrition. Mass colonization of trees growing in horticultural settings by exotic ambrosia beetles can occur, but aggregation cues have remained enigmatic. To elucidate this mechanism, we first characterized the fungal associates of the exotic, mass-aggregating ambrosia beetle Xylosandrus germanus in Southern Germany. Still-air olfactometer bioassays documented the attraction of X. germanus to its primary nutritional mutualist Ambrosiella grosmanniae and to a lesser extent another common fungal isolate (Acremonium sp.). During two-choice bioassays, X. germanus was preferentially attracted to branch sections (i.e., bolts) that were either pre-colonized by conspecifics or pre-inoculated with A. grosmanniae. Subsequent analyses identified microbial volatile organic compounds (MVOCs) that could potentially function as aggregation pheromones for X. germanus. To our knowledge, this is the first evidence for fungal volatiles as attractive cues during host selection by X. germanus. Adaptive benefits of responding to fungal cues associated with an infestation of conspecifics could be a function of locating a suitable substrate for cultivating fungal symbionts and/or increasing the likelihood of mating opportunities with the flightless males. However, this requires solutions for evolutionary conflict arising due to potential mixing of vertically transmitted and horizontally acquired symbiont strains, which are discussed.

Introduction: The striped ambrosia beetle Trypodendron lineatum (Coleoptera, Curculionidae, Scolytinae) is a major forest pest in the Holarctic region. It uses an aggregation pheromone and host and non-host volatiles to locate suitable host trees, primarily stressed or dying conifer trees. The beetles bore into the xylem and inoculate spores of their obligate fungal mutualist Phialophoropsis ferruginea inside their excavated egg galleries, with the fungus serving as the main food source for the developing larvae. Olfactory sensory neuron (OSN) responses to pheromones and host volatiles are poorly understood in T. lineatum and other ambrosia beetles, and nothing is known about potential responses to fungal volatiles. Methods: We screened responses of OSNs present in 170 antennal olfactory sensilla using single sensillum recordings (SSR) and 57 odor stimuli, including pheromones, host and non-host compounds, as well as volatiles produced by P. ferruginea and fungal symbionts of other scolytine beetles. Results and Discussion: Thirteen OSN classes were characterized based on their characteristic response profiles. An OSN class responding to the aggregation pheromone lineatin was clearly the most abundant on the antennae. In addition, four OSN classes responded specifically to volatile compounds originating from the obligate fungal mutualist and three responded to non-host plant volatiles. Our data also show that T. lineatum has OSN classes tuned to pheromones of other bark beetles. Several OSN classes showed similar response profiles to those previously described in the sympatric bark beetle Ips typographus, which may reflect their shared ancestry. [ABSTRACT FROM AUTHOR]

Simple Summary: The brown marmorated stink bug, Halyomorpha halys, is an invasive insect pest native to Asia that was accidently introduced into North America and Europe. The male-produced aggregation pheromone of H. halys has great application potential in population monitoring and control of this pest. In this study, we carried out a comprehensive bioinformatics analysis to identify the candidate genes involved in the biosynthesis of the male-specific sesquiterpene aggregation pheromone of H. halys. We identified a novel gene, designated as HhTPS1, which is related to the synthesis of the precursor molecule of the aggregation pheromone. Moreover, potential P450 reductase and transcription factors related to the aggregation pheromone biosynthesis pathway were detected. In addition, two olfactory-related genes, chemosensory protein 5 (HhCSP5) and olfactory receptor 85b (HhOr85b), were also identified, which are assumed to be involved in the olfactory recognition of this pheromone. Our results lay a solid foundation for further elucidating the biosynthesis of this aggregation pheromone and its behavioral regulation of H. halys. The aggregation pheromone of the brown marmorated stink bug, Halyomorpha halys (Stål), is produced by adult males, and plays an important role in the behavioral regulation of H. halys. However, information on the molecular mechanisms underlying this pheromone's biosynthesis is limited. In this study, HhTPS1, a key candidate synthase gene in the aggregation pheromone biosynthesis pathway of H. halys, was identified. Then, through weighted gene co-expression network analysis, the candidate P450 enzyme genes in the biosynthetic downstream of this pheromone and the related candidate transcription factor in this pathway were also identified. In addition, two olfactory-related genes, HhCSP5 and HhOr85b, involved in the recognition of the aggregation pheromone of H. halys, were detected. We further identified the key amino acid sites of HhTPS1 and HhCSP5 that interact with substrates by using molecular docking analysis. This study provides basic information for further investigations into the biosynthesis pathways and recognition mechanisms of aggregation pheromones in H. halys. It also provides key candidate genes for bioengineering bioactive aggregation pheromones necessary for the development of technologies for the monitoring and control of H. halys. [ABSTRACT FROM AUTHOR]

Introduction: The striped ambrosia beetle Trypodendron lineatum (Coleoptera, Curculionidae, Scolytinae) is a major forest pest in the Holarctic region. It uses an aggregation pheromone and host and non-host volatiles to locate suitable host trees, primarily stressed or dying conifer trees. The beetles bore into the xylem and inoculate spores of their obligate fungal mutualist Phialophoropsis ferruginea inside their excavated egg galleries, with the fungus serving as the main food source for the developing larvae. Olfactory sensory neuron (OSN) responses to pheromones and host volatiles are poorly understood in T. lineatum and other ambrosia beetles, and nothing is known about potential responses to fungal volatiles.Methods: We screened responses of OSNs present in 170 antennal olfactory sensilla using single sensillum recordings (SSR) and 57 odor stimuli, including pheromones, host and non-host compounds, as well as volatiles produced by P. ferruginea and fungal symbionts of other scolytine beetles.Results and Discussion: Thirteen OSN classes were characterized based on their characteristic response profiles. An OSN class responding to the aggregation pheromone lineatin was clearly the most abundant on the antennae. In addition, four OSN classes responded specifically to volatile compounds originating from the obligate fungal mutualist and three responded to non-host plant volatiles. Our data also show that T. lineatum has OSN classes tuned to pheromones of other bark beetles. Several OSN classes showed similar response profiles to those previously described in the sympatric bark beetle Ips typographus, which may reflect their shared ancestry.

Insects use a diverse array of specialized terpene metabolites as pheromones in intraspecific interactions. In contrast to plants and microbes, which employ enzymes called terpene synthases (TPSs) to synthesize terpene metabolites, limited information from few species is available about the enzymatic mechanisms underlying terpene pheromone biosynthesis in insects. Several stink bugs (Hemiptera: Pentatomidae), among them severe agricultural pests, release 15-carbon sesquiterpenes with a bisabolene skeleton as sex or aggregation pheromones. The harlequin bug, Murgantia histrionica, a specialist pest of crucifers, uses two stereoisomers of 10,11-epoxy-1-bisabolen-3-ol as a male-released aggregation pheromone called murgantiol. We show that MhTPS (MhIDS-1), an enzyme unrelated to plant and microbial TPSs but with similarity to trans-isoprenyl diphosphate synthases (IDS) of the core terpene biosynthetic pathway, catalyzes the formation of (1S,6S,7R)-1,10-bisaboladien-1-ol (sesquipiperitol) as a terpene intermediate in murgantiol biosynthesis. Sesquipiperitol, a so-far-unknown compound in animals, also occurs in plants, indicating convergent evolution in the biosynthesis of this sesquiterpene. RNAi-mediated knockdown of MhTPS mRNA confirmed the role of MhTPS in murgantiol biosynthesis. MhTPS expression is highly specific to tissues lining the cuticle of the abdominal sternites of mature males. Phylogenetic analysis suggests that MhTPS is derived from a trans-IDS progenitor and diverged from bona fide trans-IDS proteins including MhIDS-2, which functions as an (E,E)-farnesyl diphosphate (FPP) synthase. Structure-guided mutagenesis revealed several residues critical to MhTPS and MhFPPS activity. The emergence of an IDS-like protein with TPS activity in M. histrionica demonstrates that de novo terpene biosynthesis evolved in the Hemiptera in an adaptation for intraspecific communication.

Two closely related thrips species, Frankliniella occidentalis and Frankliniella intonsa, are important pests on agricultural and horticultural crops. They have several similarities, including occurrence patterns, host range, and aggregation pheromone compounds. However, there are very few reports about the chemosensory genes and olfactory mechanisms in these two species. To expand our knowledge of the thrips chemosensory system, we conducted antennal transcriptome analysis of two thrips species, and identified seven odorant-binding proteins (OBPs) and eight chemosensory proteins (CSPs) in F. occidentalis, as well as six OBPs and six CSPs in F. intonsa. OBPs and CSPs showed high sequence identity between the two thrips species. The RT-qPCR results showed that the orthologous genes FoccOBP1/3/4/5/6, FintOBP1/3/4/6, FoccCSP1/2/3, and FintCSP1/2 were highly expressed in male adults. Molecular docking results suggested that orthologous pairs FoccOBP4/FintOBP4, FoccOBP6/FintOBP6, and FoccCSP2/FintCSP2 might be involved in transporting the major aggregation pheromone compound neryl (S)-2-methylbutanoate, while orthologous pairs FoccOBP6/FintOBP6, FoccCSP2/FintCSP2, and FoccCSP3/FintCSP3 might be involved in transporting the minor aggregation pheromone compound (R)-lavandulyl acetate. These results will provide a fundamental basis for understanding the molecular mechanisms of pheromone reception in the two thrips species. [ABSTRACT FROM AUTHOR]

Sirex noctilio Fabricius (Hymenoptera Siricidae) is a major quarantine pest responsible for substantial economic losses in the pine industry. To achieve better pest control, (Z)-3-decen-ol was identified as the male pheromone and used as a field chemical trapping agent. However, the interactions between odorant-binding proteins (OBPs) and pheromones are poorly described. In this study, SnocOBP9 had a higher binding affinity with Z3D (Ki = 1.53 ± 0.09 μM) than other chemical ligands. Molecular dynamics simulation and binding mode analysis revealed that several nonpolar residues were the main drivers for hydrophobic interactions between SnocOBP9 and Z3D. Additionally, computational alanine scanning results indicated that five amino acids (MET54, PHE57, PHE71, PHE74, LEU116) in SnocOBP9 could potentially alter the binding affinity to Z3D. Finally, we used single-site-directed mutagenesis to substitute these five residues with alanine. These results imply that the five residues play crucial roles in the SnocOBP9-Z3D complex. Our research confirmed the function of SnocOBP9, uncovered the key residues involved in SnocOBP9-Z3D interactions, and provides an inspiration to improve the effects of pheromone agent traps. [ABSTRACT FROM AUTHOR]

Riptortus pedestris (Hemiptera: Alydidae) is a notable soybean pest, with diapause and non-diapause individuals showing different sensitivities to aggregation pheromones. This study aimed to investigate how R. pedestris detects aggregation pheromones through electroantennogram (EAG) and behavioral experiments, transcriptome sequencing and qRT-PCR, as well as competitive fluorescence-binding assay. Results indicated that diapausing females and males of R. pedestris exhibited a heightened EAG response and were more attracted to the aggregation pheromone components compared to their non-diapause counterparts. Transcriptome sequencing and qRT-PCR analyses revealed significantly higher expression of RpedOBP1 in the antennae of diapause females and males compared to non-diapausing R. pedestris. The competitive fluorescence-binding assay demonstrated that RpedOBP1 displayed the strongest binding affinity to E2HE2H, suggesting its crucial role in recognizing the aggregation pheromone. These findings have the potential to inform the development of integrated pest management strategies utilizing behavioral approaches for bean bug control. [Display omitted] • Diapause R. pedestris has a higher response to aggregation pheromone. • RNA-Seq and qRT-PCR revealed higher expression of RpedOBP1 in diapause R. pedestris. • RpedOBP1 had best binding affinities to main aggregation pheromone component, E2HE2H. [ABSTRACT FROM AUTHOR]

The red palm weevil (Rhynchophorus ferrugineus L) is an important pest for date palm plantation in all over the world. The present study deals with the optimization of different parameters for trapping of red palm weevil by utilizing pheromone traps. Different field trials have been performed at district Khairpur Mir's, Sindh-Pakistan. Therefore, different field trials have been performed at date palm orchards of district Khairpur Mir's, Sindh-Pakistan. During the field trials, various parameters such as aggregation pheromone (ferrugineol; 4-methyl-5-nonanol+ 4-methyl-5-nonanone), kairomone (Ethyl acetate, EA) dosages, effect of date fodder, trap density, the effect of trap color and seasonal changes have been optimized. From the results, it has been revealed that the traps baited with 300 g of date fodder, captured more adult red palm weevil as compared to the traps without date fodder. In addition, 3 mg/trap/day pheromone dose and 5 mg/trap/day EA captured the maximum number of adult red palm weevils and effective trap density was found to be 11 traps/ha, while further higher trap density has no significant difference. Moreover, the darker color traps catch a significant higher number of weevils as compared to white or light-colored bucket traps. [ABSTRACT FROM AUTHOR]

Flea beetles are common pests of vegetables, fruits, grains and other crops. The aggregation pheromone components of flea beetles, including fourteen sesquiterpenes and six unsaturated aldehydes, can be used for mass trapping and monitoring. It is a promising technology for control of flea beetles. The syntheses of the sesquiterpenes were described according to the strategies for the construction of chiral center, which consisted of chiral sources, enantioinduction and asymmetric catalytic reactions; whereas the preparations of unsaturated aldehydes were reviewed on basis of the approaches for constructing carbon-carbon double bonds, including aldol condensation, Wittig coupling, Wittig-Horner coupling and acetylenic ester isomerization. Moreover, the advantages and disadvantages of each method were discussed, as well as the prospects for the synthesis of aggregation pheromones of flea beetles. [ABSTRACT FROM AUTHOR]

Simple Summary: Bark beetle species of the genus Ips are among the major pests of Chinese conifer forests. Based on mitochondrial genome and SNP, we investigated the phylogenetic relationships and evolutionary trends of 19 populations of six Ips species that had serious outbreaks in recent years. Our results demonstrated the relationships between Ips evolution and host plants, pheromones, and altitudinal differences, and provided new insights into the mechanism of adaptive evolution of Ips bark beetles. Many bark beetles of the genus Ips are economically important insect pests that cause severe damage to conifer forests worldwide. In this study, sequencing the mitochondrial genome and restriction site-associated DNA of Ips bark beetles helps us understand their phylogenetic relationships, biogeographic history, and evolution of ecological traits (e.g., pheromones and host plants). Our results show that the same topology in phylogenetic trees constructed in different ways (ML/MP/BI) and with different data (mtDNA/SNP) helps us to clarify the phylogenetic relationships between Chinese Ips bark beetle populations and Euramerican species and their higher order clades; Ips bark beetles are polyphyletic. The structure of the mitochondrial genome of Ips bark beetles is similar and conserved to some extent, especially in the sibling species Ips typographus and Ips nitidus. Genetic differences among Ips species are mainly related to their geographic distribution and different hosts. The evolutionary pattern of aggregation pheromones of Ips species reflects their adaptations to the environment and differences among hosts in their evolutionary process. The evolution of Ips species is closely related to the uplift of the Qinghai-Tibet Plateau and host switching. Our study addresses the evolutionary trend and phylogenetic relationships of Ips bark beetles in China, and also provides a new perspective on the evolution of bark beetles and their relationships with host plants and pheromones. [ABSTRACT FROM AUTHOR]

The bean bug, Riptortus pedestris, is a polyphagous insect that feeds primarily on leguminous plants, especially soybean (Glycine max). Although the bean bug is an economically important pest of soybean, little is known about how the insect locates soybean fields. In this study, we examined the electroantennogram responses of R. pedestris to soybean volatiles and examined the behavioral responses of the adult bean bugs. R. pedestris adults were attracted more to their host-plant soybean, even when physical contact was absent, than to air or a non-host plant. Accordingly, we hypothesized that R. pedestris can recognize soybean through a plant's volatile organic compounds (VOCs). Five VOCs were identified from intact soybean plants at the vegetative stage: (Z)-3-hexen-1-ol, (Z)-3-hexenyl acetate, 4-ethylbenzaldehyde, α-farnesene, and methyl salicylate. Response spectra of the antennae to these volatiles clearly showed that both male and female R. pedestris can detect soybean volatiles. The adult bean bugs did not show behavioral orientation to any individual compounds but showed significant orientation to a particular blend of synthetic soybean volatiles when tested under laboratory conditions. In the field, this soybean volatile blend did not significantly attract the bean bugs, but it did interact synergistically with the aggregation pheromone to attract the bean bugs. These results highlight the role of host plant volatiles in the sensory ecology of R. pedestris and help explain colonization pattern of the bean bugs in soybean fields. [ABSTRACT FROM AUTHOR]

Alarm pheromones, which have been documented in many species of ants, are thought to elicit responses related to aggressive or defensive behaviour. The volatile odour 6‐methyl‐5‐hepten‐2‐one is described as an alarm pheromone in several species of ants, including the Australian meat ant, Iridomyrmex purpureus. The alarm pheromone is released by displaying workers that aggregate in the characteristic collective display grounds, located mid‐way between colonies or near contested food trees. Workers are typically more aggressive at the latter location, and the alarm pheromone may regulate the collective level of aggression. We investigated this possibility by exposing displaying workers to synthesised alarm pheromone 6‐methyl‐5‐hepten‐2‐one in a field experiment, and measuring their aggressive behaviour. We found no evidence that exposure to synthesised alarm pheromone caused changes in the aggressive level of workers. Subsequent field experiments revealed that the pheromone functions as an attractant, thereby increasing the density of displaying workers. More densely populated workers also display more aggressively, indicating that the interaction rate of displaying workers may determine the level of aggression in collective displays. This underlying mechanism can explain why displaying ants are more aggressive at the more densely populated food‐tree locations than those displaying at locations midway between two neighbouring colony nest sites. [ABSTRACT FROM AUTHOR]

The aggregation pheromone of the brown marmorated stink bug, Halyomorpha halys (Stål), is produced by adult males, and plays an important role in the behavioral regulation of H. halys. However, information on the molecular mechanisms underlying this pheromone’s biosynthesis is limited. In this study, HhTPS1, a key candidate synthase gene in the aggregation pheromone biosynthesis pathway of H. halys, was identified. Then, through weighted gene co-expression network analysis, the candidate P450 enzyme genes in the biosynthetic downstream of this pheromone and the related candidate transcription factor in this pathway were also identified. In addition, two olfactory-related genes, HhCSP5 and HhOr85b, involved in the recognition of the aggregation pheromone of H. halys, were detected. We further identified the key amino acid sites of HhTPS1 and HhCSP5 that interact with substrates by using molecular docking analysis. This study provides basic information for further investigations into the biosynthesis pathways and recognition mechanisms of aggregation pheromones in H. halys. It also provides key candidate genes for bioengineering bioactive aggregation pheromones necessary for the development of technologies for the monitoring and control of H. halys.

The work was initiated to study hygienic and toxicological indices of a synthetic analogue for the Sitophilus weevil aggregation pheromone. The toxicity testing of 5-hydroxy-4-methyl-3-heptanone demonstrated its extremely low toxicity for the warm-blood animals, as compared to the one of the typical pesticides. The average lethal dose of the product per orally administered to the white mice was established to be 4375.0 mg kg-1 LD16 and LD84 being 2225.0 mg kg-1 and 6550.0 mg kg-1, respectively. The average lethal dose for rabbits was 5900.0 mg kg-1 5-hydroxy-4-methyl-3-heptanone proved to have a mild skin and conjunctival irritant action, and equally mild functional cumulation. As to chronic toxicity, the acceptable daily dose of 4.3 mg/person/d was calculated and scientifically substantiated. The odor threshold was determined at the dose ranging from 0.35 to 0.7 mg l-1 with the practical limit ranging from 0.35 to 1.5 mg l-1, taste sensation threshold was found at the dose ranging from 1.0 to 3.0 mg l-1 with the practical limit ranging from 3.0 to 7.0 mg l-1

Red palm weevil (RPW) (Rhynchophorus ferrugineus Oliver Coleoptera: Curculionidae.) has gained a key pest status in Asia, Africa and Europe. Coconut (Cocos nucifera L.) plantations, date palms (Phoenix dactylifera) and oil palms (Elaeis guineensis) are the economically important crops attacked by this pest. Currently no effective methods are available to prevent and control this high-risk pest. In this scenario, pheromone trapping is the only option available for red palm weevil management in plantations. Use of pheromones traps is not only safe way to prevent the damage caused by the infestation by RPW and minimizes the use of pesticides. In this context, to evaluate the insect’s behavioural response to different blends of aggregation pheromone, a comparative dual path olfactometric experiment were conducted using laboratory reared Adult RPW. The experimental results demonstrated red palm weevil’s olfactory sensilla response to stimulate pheromone-responsive neurons (PRNs) by the different blends of aggregation pheromones. Experiments were carried out using different blend ratios of aggregation pheromones, results revealed that 7:1 ratio of 4-methyl-5-nonanol and 4-methyl-5-nonanone is the optimum blend ratio and demonstrated optimal influence on olfactory sensilla to efficiently stimulate PRNs of RPW for attraction. [ABSTRACT FROM AUTHOR]

Palm trees are of immense economic, sociocultural, touristic, and patrimonial significance all over the world, and date palm‐related knowledge, traditions, and practices are now included in UNESCOs list of the Intangible Cultural Heritage of Humanity. Of all the pests that infest these trees, the red palm weevil (RPW), Rhynchophorus ferrugineus (Olivier), is its primary enemy. The RPW is a category‐1 quarantine insect pest that causes enormous economic losses in palm tree cultivation worldwide. The RPW synchronizes mass gathering on the palm tree for feeding and mating, regulated by a male‐produced pheromone composed of two methyl‐branched compounds, (4RS, 5RS)‐4‐methylnonan‐5‐ol (ferrugineol) and 4(RS)‐methylnonan‐5‐one (ferrugineone). Despite the importance of odorant detection in long‐range orientation towards palm trees, palm colonization, and mating, the pheromone receptor has not been identified in this species. In this study, we report the identification and characterization of the first RPW pheromone receptor, RferOR1. Using gene silencing and functional expression in Drosophila olfactory receptor neurons, we demonstrate that RferOR1 is tuned to ferrugineol and ferrugineone and binds five other structurally related molecules. We reveal the lifetime expression of RferOR1, which correlates with adult mating success irrespective of age, a factor that could explain the wide distribution and spread of this pest. As palm weevils are challenging to control based on conventional methods, elucidation of the mechanisms of pheromone detection opens new routes for mating disruption and the early detection of this pest via the development of pheromone receptor‐based biosensors. [ABSTRACT FROM AUTHOR]

Melon weevil, Acytopeus curvirostris persicus Thompson (Col.: Curculionidae), is an important pest of cucurbits. Understanding the chemical ecology of this species could provide information for the development of nonchemical control measures. Field trapping experiments indicated adult insects respond to conspecific (a member of the same species) insects and host fruit. To determine attractiveness rate, two-way static experiments were carried out under laboratory conditions using conspecific insects, and to evaluate the role of the host plants melon (Cucumis melo L.), watermelon [Citrullus lanatus (Thunb)], cucumber (C. sativus L.), and colocynth [C. colocynthis (L.)]. Cucumber fruit had the most, and colocynth fruit, the least attraction. Adult insects were more attracted to a mated, or unmated, conspecific insect indicating existence of an aggregation pheromone. Results of the study provided the necessary background for the identification of host plant kairomone and aggregation pheromone of melon weevil. [ABSTRACT FROM AUTHOR]

Copyright of Brazilian Journal of Biology is the property of Instituto Internacional de Ecologia and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

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Many bark beetles of the genus Ips are economically important insect pests that cause severe damage to conifer forests worldwide. In this study, sequencing the mitochondrial genome and restriction site-associated DNA of Ips bark beetles helps us understand their phylogenetic relationships, biogeographic history, and evolution of ecological traits (e.g., pheromones and host plants). Our results show that the same topology in phylogenetic trees constructed in different ways (ML/MP/BI) and with different data (mtDNA/SNP) helps us to clarify the phylogenetic relationships between Chinese Ips bark beetle populations and Euramerican species and their higher order clades; Ips bark beetles are polyphyletic. The structure of the mitochondrial genome of Ips bark beetles is similar and conserved to some extent, especially in the sibling species Ips typographus and Ips nitidus. Genetic differences among Ips species are mainly related to their geographic distribution and different hosts. The evolutionary pattern of aggregation pheromones of Ips species reflects their adaptations to the environment and differences among hosts in their evolutionary process. The evolution of Ips species is closely related to the uplift of the Qinghai-Tibet Plateau and host switching. Our study addresses the evolutionary trend and phylogenetic relationships of Ips bark beetles in China, and also provides a new perspective on the evolution of bark beetles and their relationships with host plants and pheromones.

The symbiosis between the bark beetle (Ips subelongatus) and its fungal symbiont (Endoconidiophora fujiensis) poses a serious threat to larch forests. However, the signaling pathways between these symbiotic partners and their host/non-host trees are not fully understood. Inoculation of the host larch (Larix principis-rupprechtii) with two strains of E. fujiensis induced a rapid and long-term release of monoterpenes. Although the fungi had a level of tolerance to these compounds, many monoterpenes inhibited fungal growth in culture. Moreover, monoterpenes with stronger inhibitory effects on fungal growth exhibited weaker synergistic effects on the attraction of I. subelongatus to aggregation pheromone. Surprisingly, individual isomers of aggregation pheromone components promoted fungal symbiont growth in a culture medium. Non-host volatiles (NHVs) were tested and shown to completely inhibit the growth of fungal symbionts in culture but had no effects on beetle responses to aggregation pheromone, with the exception of (Z)-3-hexen-1-ol. These results reveal convergence and mutualism patterns in the evolution of I. subelongatus and E. fujiensis with respect to host tree volatiles but not in response to NHVs. Ultimately, we put forward a hypothesis that host plants are ecological and evolutionary determinants of bark beetle–fungus symbioses in terms of their complex signaling interactions. [ABSTRACT FROM AUTHOR]

We previously described a putative aggregation pheromone in adults of the sugar beet root maggot, Tetanops myopaeformis (von Röder) (Diptera: Ulidiidae), comprising nine compounds identified from males. Here, we conducted a series of experiments aimed at simplifying the blend of compounds necessary to achieve attraction as well as determining the dose that maximizes captures when formulated into an attractant lure. In all experiments, females showed stronger and more consistent evidence of attraction than males. White sticky traps baited with different blends of pheromone compounds that included the major component, (R)‐(−)‐2‐nonanol, showed significantly higher female captures relative to those baited with blends that excluded the major component. (R)‐(−)‐2‐nonanol alone was at least as effective as any blend that included this compound with other minor pheromone components. Lures using racemic 2‐nonanol were as effective as the (R) enantiomer for both females and males, with some evidence of weak attraction to the (S) enantiomer (which is not produced by males) observed as well. Maximum capture rates using racemic 2‐nonanol were estimated to occur with doses of ca. 795.5 and 621.6 mg for females and males, respectively. Addition of 2‐nonanol lures to standard orange sticky stake traps currently used to monitor flies increased captures of both sexes. The pheromone lure developed here could improve trapping efficiency of current monitoring programs for T. myopaeformis and may also be used to develop other management tools for this important pest of sugar beet. [ABSTRACT FROM AUTHOR]

Successful management of insect crop pests requires an understanding of the cues and spatial scales at which they function to affect rates of attack of preferred and non‐preferred host plants. A long‐standing conceptual framework in insect–plant ecology posits that there is hierarchical structure spanning host location, acceptance and attack that could be exploited for integrated pest management.We investigated how plant‐ and insect‐derived chemical cues affect successive decisions of host choice in aggregating insects, and tested predictions in the Cucurbita pepo–Acalymma vittatum system. Acalymma vittatum is an aggregating specialist beetle pest that strongly prefers zucchini (C. p. pepo) to summer squash (C. p. ovifera), two independent domesticates of C. pepo. We hypothesized that subspecies‐specific plant traits, especially volatile cues, interact with the male‐produced aggregation pheromone to amplify beetle preference for C. p. pepo.Differential beetle attack of C. pepo subspecies in the field is not determined by plant traits that affect host finding or differential aggregation due to pheromones: across two years, beetles had strong density‐dependent attraction to both subspecies when male beetles were feeding, and no interactions between plant volatiles and the male‐produced pheromone were detected. In the absence of male pheromone emission, beetles were equally unattracted to plants with or without beetle feeding.In contrast, plant traits that mediate insect acceptance appear to underlie differences in preference. At a local scale, beetles did not accept and emigrated from C. p. ovifera compared to C. p. pepo. Distinct volatile emissions were observed between subspecies, but further work is needed to identify if these volatiles promote emigration.Synthesis and applications. By dissecting pest preference during successive host choice decisions, we isolated a trait with implications for pest management. Beetles on cucurbits can be managed by employing cultivars with differential susceptibility (e.g. trap cropping), and the mechanistic knowledge presented here informs best practices and limitations for on‐farm applications. More broadly, pest management in diversified cropping systems can be enhanced through understanding how plant preference gradients affect herbivore movement and behaviour, and plant breeders can target traits to reduce herbivory in such systems. [ABSTRACT FROM AUTHOR]

The occurrence and damage of Riptortus pedestris has been on the rise in recent years, but the control efficacy by spraying insecticides is poor due to the quick moving of both adults and nymphs, which seriously threatens the revitalization and development of Chinese soybean industry. New control technologies for this pest are urgently needed to be researched and developed. The aggregation pheromone of R.pedestris is mainly produced and released by male adults, but is strongly attractive to female and male adults and nymphs. These semiochemicals could be used as a chemical lure and expected to be developed as green control techniques to suppress R.pedestris. The aggregation pheromone has been studied in Japan and South Korea for more than 20 years, but it lacks research in China. In this paper, the research progress on the identification and function, the influencing factors of synthesis and release, and the application in monitoring and control of R.pedestris aggregation pheromone are reviewed, and at meantime, the problems in the application are highlighted, and future directions are suggested. This paper provides an important reference for the research and the application in the pest control of R.pedestris aggregation pheromone in China. [ABSTRACT FROM AUTHOR]

An efficient synthesis of natural tribolure has been achieved through an asymmetric methylation as a key step. Natural tribolure is a mixture of four stereoisomers, so racemic 2-methylbutan-1-ol was used as starting material. After a C5+C4 strategy and then a mixed Evan's template inductive methylation, the key intermediate was obtained. Finally, the natural product tribolure (4:4:1:1 of stereoisomers, respectively) was obtained in 10 linear steps and in 34.2% overall yield. [ABSTRACT FROM AUTHOR]

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BACKGROUND: Insect pheromones and host volatiles are important for pest control due to their high efficiency and low potential for environmental pollution. The functions of myrtenol, myrtanol and myrtenal in pest–host interactions are unknown. This study aimed to determine the presence of myrtenol, myrtanol and myrtenal in newly emerged and emerged stages of Dendroctonus armandi, and in infected and healthy Pinus armandi, and to identify their roles in tree protection and pest management based on electroantennography (EAG), Y‐tube and toxicity experiments. RESULTS: Gas chromatographic and mass spectrometry (GC–MS) analyses, EAG, Y‐tube and toxicity assays revealed the following: (1) myrtenol was found in P. armandi phloem and did not exhibit significant toxicity towards D. armandi; (2) myrtanol was produced by infected P. armandi after D. armandi invasion and had significant toxicity towards D. armandi, especially females; and (3) myrtenal might represent an aggregation pheromone produced by female D. armandi to exert aggregation effects on other females, to help them overcome the resistance of P. armandi jointly and ensure a successful invasion, females remained in an aggregation state from leaving the host to mating in a new host. CONCLUSION: These findings suggest that myrtanol as a repellent has potential for the protection of P. armandi and that myrtenal could be used to trap and disorient D. armandi. © 2019 Society of Chemical Industry [ABSTRACT FROM AUTHOR]

Adults of both sexes of the cerambycid beetles Xylotrechus colonus (F.) and Sarosesthes fulminans (F.) were attracted to odors produced by male conspecifics in olfactometer bioassays. Analyses of headspace volatiles from adults revealed that male X. colonus produced a blend of (R)- and (S)-3-hydroxyhexan-2-one and (2 S,3 S)- and (2R,3R)-2,3-hexanediol, whereas male S. fulminans produced (R)-3-hydroxyhexan-2-one and (2 S,3R)-2,3-hexanediol. All of these compounds were absent in the headspace of females. Two field bioassays were conducted to confirm the biological activity of the synthesized pheromones: (1) enantiomerically enriched pheromone components were tested singly and in species-specific blends and (2) four-component mixture of racemic 3-hydroxyhexan-2-one plus racemic 2-hydroxyhexan-3-one and the four-component blend of the stereoisomers of 2,3-hexanediols were tested separately and as a combined eight-component blend. In these experiments, adult male and female X. colonus were captured in greatest numbers in traps baited with the reconstructed blend of components produced by males, although significant numbers were also captured in traps baited with (R)-3-hydroxyhexan-2-one alone or in blends with other compounds. Too few adult S. fulminans were captured for a statistical comparison among treatments, but all were caught in traps baited with lures containing (R)-3-hydroxyhexan-2-one. In addition to these two species, adults of two other species of cerambycid beetles, for which pheromones had previously been identified, were caught: Neoclytus a. acuminatus (F.) and its congener Neoclytus m. mucronatus (F.). Cross-attraction of beetles to pheromone blends of other species, and to individual pheromone components that are shared by two or more sympatric species, may facilitate location of larval hosts by species that compete for the same host species.