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The brown marmorated stink bug, Halyomorpha halys (Stål) (Hemiptera: Pentatomidae) is attracted to its male-produced aggregation pheromone, a ∼3.5:1 mixture of (3S,6S,7R,10S)- and (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol (SSRS and RSRS respectively), and also to the pheromone of its Asian sympatric species Plautia stali Scott (Hemiptera: Pentatomidae), methyl (2E,4E,6Z)-2,4,6-decatrienoate (MDT). A stereoisomeric mixture of (7R) 10,11-epoxy-1-bisabolen-3-ols (= mixed murgantiols) is used together in commercialized products with MDT because the latter is a synergist for H. halys attraction to mixed murgantiols. However, the optimal ratio for MDT combination with mixed murgantiols, and the sensitivity of bug captures to variation in ratio of the two pheromone components, have not been tested to date. Using black pyramid traps at two sites (in Maryland and West Virginia, United States), different ratios of mixed murgantiols to MDT were tested over two entire seasons. Also, captures using various ratios of the two active pheromone stereoisomers were undertaken in month-long trials with and without MDT. Results showed that H. halys adult and nymphal captures were relatively insensitive to the ratio of synthetic pheromone (mixed murgantiols) to MDT, as long as each was present in the trap. Captures of adults and nymphs were responsive to the lure loading of the SSRS isomer, but relatively insensitive to levels of the minor component, RSRS.The relative insensitivity of H. halys to these attractant ratios gives flexibility to development of more cost-efficient synthesis and trapping as well as other semiochemical-based management tactics.

Biochemical studies demonstrate that three steroids postulated to function as the sea lamprey migratory pheromone are released in sufficient quantities, and possess adequate stability and binding characteristics, to function as a multi-component pheromone in natural river waters. Mass spectrometric (MS) analyses of the holding water of recently fed larval lamprey demonstrated that each of these compounds is released at rates of 5-25 ng larva⁻¹ h⁻¹, adequate to produce picomolar (biologically relevant) concentrations in river waters. Petromyzonamine disulfate (PSDS) was released at about twice the rate of the other two components, petromyzonamine disulfate (PADS) and petromyzonol sulfate (PS). Unfed larvae also released all three steroids but only at about two-thirds the rate of fed larvae and in a different ratio. However, a behavioral test of fed and unfed larval holding waters suggested this change in pheromone ratio does not diminish pheromonal signal function in the winter when larvae are not feeding. A study of steroid degradation found that PADS and PSDS had half-lives of about 3 days, similar to values previously described for PS and sufficiently slow for the entire pheromone to persist in river mouths. Finally, both MS and electro-olfactogram recording found that contrary to previous suggestions, natural levels of natural organic matter found in streams do not bind to these steroids in ways that diminish their natural biological potency. In conclusion, it appears highly likely that a mixture of PADS, PSDS and PS is present at biologically relevant concentrations and ratios in many Great Lakes streams where it functions as a pheromonal attractant.

During the spring–summer seasons between 2019 and 2023, in the localities of Maquehue (La Araucanía Region) and Llifén (Los Ríos Region), we collected 262 virgin Proholopterus chilensis (1 female/2.3 males) specimens emerging from the live trunks of N. obliqua trees, an atypical sex ratio in Cerambycidae, suggesting high male competition for females. Virgin specimens of both sexes were individually placed in panel traps in the field, capturing only males (n = 184) over the field study seasons and only in traps baited with females. This fact preliminarily suggests the P. chilensis females emit possible “volatile or airborne” pheromones (eventually being a long-range sex pheromone), something unusual in Cerambycinae, the subfamily to which it currently belongs, although the taxonomic status of the species is under debate. In Llifén and Santiago (Metropolitan Region), behavioral observations were conducted, which allowed us to define the conditions necessary for male–female encounters that were replicated when carrying out volatile captures (Head Space Dynamic = HSD) and collections of compounds from terminalias excised from females. In field trials, virgin females less than ten days old were more attractive than older ones and attracted males during the night, i.e., between 23:00 and 5:00 AM, when the ambient temperature exceeded 11.6 °C. The aeration of females under the conditions described above and subsequent analysis of extracts by GC-MS allowed the identification of compounds absent in males and the control, including two oxygenated sesquiterpenes, a nitrogenous compound (C20), and a long-chain hydrocarbon (C26). From the terminalia extracts, hentriacontane, heptacosane, and heneicosyl, heptacosyl and docosyl acetates were identified by GC-MS, and their roles are unknown in the development of short-distance sexual behaviors, but they could serve to mark a trail leading the male towards the female in the final stage of approach for courtship/mating. Thus, we proposed the hypothesis that P. chilensis females emit both a long-range and a trail-pheromone, which, if confirmed, would be a rare case in this family. The specific identity of the compounds obtained by HSD, as well as the activities of these chemicals and those obtained from the terminalias, should be evaluated in future behavioral studies, as well as regarding their potential to attract males under field conditions. The current document is the first report on volatiles obtained from aerations and compounds extracted from female terminalia in P. chilensis.

The codling moth, Cydia pomonella, is an important fruit pest worldwide. As nocturnal animals, adults depend to a large extent on olfactory cues for detection of food and mates, and, for females, oviposition sites. In insects, odor detection is mediated by odorant receptors (ORs) and ionotropic receptors (IRs), which ensure the specificity of the olfactory sensory neuron responses. In this study, our aim was to identify chemosensory receptors in the codling moth as a means to uncover new targets for behavioral interference. Using next-generation sequencing techniques, we identified a total of 43 candidate ORs, one gustatory receptor and 15 IRs in the antennal transcriptome. Through Blast and sequence similarity analyses we annotated the insect obligatory co-receptor ORco, five genes clustering in a conserved clade containing sex pheromone receptors, one homolog of the Bombyx mori female-enriched receptor BmorOR30 (but no homologs of the other B. mori female-enriched receptors) and one gene clustering in the sugar receptor family. Among the candidate IRs, we identified homologs of the two highly conserved co-receptors IR8a and IR25a, and one homolog of an IR involved in phenylethyl amine detection in Drosophila. Our results open for functional characterization of the chemosensory receptors of C. pomonella, with potential for new or refined applications of semiochemicals for control of this pest insect.

The small black stem bug, Paratibraca (=  Glyphepom is) spinosa (Campos and Grazia 1998), is a rice pest in Brazil and is part of a complex of stink bugs that includes Oebalus poecilus (Dallas) and Tibraca limbativentris Stål. Together, these pentatomid species pose a serious threat to rice crops throughout South America. In this study, we identified the sex pheromone of P. spinosa . Our findings revealed that male P. spinosa produces four male-specific compounds identical to those produced by T. limbativentris males. These include (3 S ,6 S ,7 R )-1,10-bisaboladien-3-ol and (3 R ,6 S ,7 R )-1,10-bisaboladien-3-ol (zingiberenols), both sharing the same absolute configuration as the 1,10-bisaboladien-3-ol from T. limbativentris ; along with two minor male-specific components: the cis and trans isomers of 2,10-bisaboladien-1-ol (sesquipiperitol). Y-tube olfactometer bioassays demonstrated that P. spinosa females were attracted to the odours of live males, whereas males showed no attraction to either sex. Females were particularly drawn to male volatiles, especially the fraction containing the compounds 1,10-bisaboladien-3-ol and 2,10-bisaboladien-1-ol. When tested with synthetic compounds, females were attracted to a blend of the two isomers, (3 S ,6 S ,7 R )-1,10-bisaboladien-3-ol and (3 R ,6 S ,7 R )-1,10-bisaboladien-3-ol, in the same ratio as naturally produced by males. Given that the sex pheromone compounds identified in P. spinosa are identical to those of T. limbativentris , we conducted bioassays with live heterospecific insects. In olfactometer bioassays, the females of both species were attracted by the odours of heteroespecific males.

Chemical signals are important mediators of interactions within forest ecosystems. In insects, pheromone signals mediate intraspecific interactions such as mate location and acceptance. The evolution of pheromones in insects has been mostly studied from a theoretical perspective in the Lepidoptera. With this study, we aimed to broaden our understanding of pheromone communication in bark beetles. We first demonstrated that the enantiomeric ratios of ipsdienol produced by male I. avulsus, showed little variation. Subsequently, with field trapping trials we characterized the influence of the enantiomeric ratio of ipsdienol (pheromone component of I. avulsus) on I. avulsus captures and observed a great amount of variation in the receiver preference function. Most importantly, we demonstrated that responding individuals responded indiscriminately to all the enantiomeric ratios produced by the emitting individuals. These observations are consistent with the asymmetric tracking model which postulates that if the limiting sex is the emitting sex, responding individuals should not discriminate between emitted ratios. Consequently, responding individuals do not constrain the evolution of the signal. Our data suggest that, in I. avulsus, the composition of the aggregation pheromone signal might be more responsive to external selection forces, such as predation and metabolic constraints, as suggested by the asymmetric tracking model.

The almond moth Cadra cautella (Walker), a key pest of storage facilities, is difficult to manage using synthetic chemicals. Pheromone-based management methods remain a high priority due to advantages over conventional management practices, which typically use insecticides. Cadra cautella females release a blend of pheromone including (Z, E)-9,12-tetradecadienyl acetate (ZETA) and (Z)-9-tetradecadien-1-yl acetate (ZTA). The effect of these components on mating of C. cautella and how response varies with the population density and sex ratio remain unknown. In this study, the mating status of C. cautella was studied inside mating cages under different ratios of ZETA and ZTA diluted in hexane and at different population sizes either with equal or unequal sex ratio. The lowest percentage of mated females (highest mating disruption [MD] effects), corresponding to roughly 12.5%, was produced by a 5:1 and 3.3:1 ratio of ZETA:ZTA. Populations with equal sex ratio showed the lowest percentage of mated females, at 20% and 12.5% under lower and higher density, respectively. The next lowest percentage of mated females was produced when the sex ratio was set to 1: 2 and 2:1 male:female, with just 25% and 22.5% of moths mated, respectively. This study shows that mating status of C. cautella is influenced by ZETA:ZTA ratio, sex ratio, and population size. This current knowledge would have useful implications for mating disruption programs.

In forest protection, various types of trap systems are used against spruce bark beetles to treat the foci of infested areas. Traditionally, these include pheromone traps, treated trap trees, and recently also the application of Storanet insecticide nets used for the sanitation of infested wood (trees), which also serve as treated trap trees when pheromones are applied, and the Trinet P system, a variation to a treated trap tree – a tripod. On an aluminium tripod, there is a Storanet insecticide net baited with a pheromone dispenser similar to other types of trap systems. The sex ratio proves to be a significant aspect in the assessment of individual types of trap systems. It is more favourable to catch a larger number of female individuals given that they bear the future development of the population. With a higher number of captured male individuals, the number of females per one male in the insect gallery increases, and the population cannot be reduced sufficiently. The results show that all three types of measures can be characterised by a lower ratio of captured males (approximately 40%) and a higher representation of females (around 60%). Differences in individual types of trap systems are insignificant.

The pink bollworm, Pectinophora gossypiella, is a world-wide pest of cotton and in some parts of the cotton growing region is controlled by the mating disruption technique using synthetic sex pheromone. The sex pheromone consists of two compounds, (Z,Z)- and (Z,E)-7,11-hexadecadienyl acetates, in about a 50:50 ratio. However, recently, a population with sex pheromone compound ratios of about 62:38 were found in cotton fields that use mating disruption in Israel. To investigate how the change developed, we compared the pheromone gland transcriptomes between a reference laboratory population and a population obtained from an Israeli cotton field utilizing mating disruption. We analyzed four biological replicates from each population and found transcripts encoding 17 desaturases, 8 reductases, and 17 candidate acetyltransferases in both populations, which could be involved in sex pheromone biosynthesis. The expression abundance of some genes between the two populations was different. Some desaturases and candidate acetyltransferases were found to have mutated in one of the populations. The differentially expressed genes play potential roles in sex pheromone biosynthesis and could be involved in causing altered female sex pheromone ratios in the field population.

The tea tussock moth, Euproctis pseudoconspersa (Strand), is a serious pest, and its sex pheromone is (R)-10,14-dimethylpentadecyl isobutyrate. A new and concise asymmetric synthesis of the sex pheromone and its enantiomer was accomplished. The chiral methyl of the pheromone was introduced by Evans’s template, while the extension of the carbon chain was achieved through Li2CuCl4-catalyzed coupling of chiral tosylate with Grignard reagent.