Accelerated hermaphrodite maturation on male pheromones suggests a general principle of coordination between larval behavior and development.

Environment in general and social signals in particular could alter development. In Caenorhabditis elegans, male pheromones hasten development of hermaphrodite larvae. We show that this involves acceleration of growth and both somatic and germline development during the last larval stage (L4). Larvae exposed to male pheromones spend more time in L3 and less in the quiescent period between L3 and L4. This behavioral alteration improves provision in early L4, likely allowing for faster development. Larvae must be exposed to male pheromones in late L3 for behavioral and developmental effects to occur. Latter portions of other larval stages also contain periods of heightened sensitivity to environmental signals. Behavior during the early part of the larval stages is biased toward exploration, whereas later the emphasis shifts to food consumption. We argue that this organization allows assessment of the environment to identify the most suitable patch of resources, followed by acquisition of sufficient nutrition and salient information for the developmental events in the next larval stage. Evidence from other species indicates that such coordination of behavior and development may be a general feature of larval development.

Evolution of Acquired Perfumes and Endogenous Lipid Secretions in Orchid Bees.

Male orchid bees are unique in the animal kingdom for making perfumes that function as sex pheromone. Males collect volatile chemicals from the environment in the neotropical forests, including floral and non-floral sources, creating complex but species-specific blends. Male orchid bees exhibit several adaptations to facilitate perfume collection and storage. When collecting volatile compounds, males apply lipid substances that they secrete from cephalic labial glands onto the fragrant substrate. These lipids help dissolve and retain the volatiles, similar to the process of 'enfleurage' in the traditional perfume industry. We investigated how the chemical composition of acquired perfume and labial gland secretions varied across the phylogeny of orchid bees, including 65 species in five genera from Central and South America. Perfumes showed rapid evolution as revealed by low overall phylogenetic signal, in agreement with the idea that perfume compounds diverge rapidly and substantially among closely related species due to their role in species recognition. A possible exception were perfumes in the genus Eulaema, clustering closely in chemospace, partly mediated by high proportions of carvone and trans-carvone oxide. Labial gland secretions, in contrast, showed a strong phylogenetic signal at the genus level, with secretions of Eufriesea and Exaerete dominated by fatty acids and Eulaema dominated by saturated acetates of chain lengths 12 to 16 C-atoms. Secretions of the majority of Euglossa were heavily dominated by one unsaturated long chain diacetate, (9Z)-Eicosen-1,20-diyldiacetate. However, we also identified few highly divergent species of Euglossa in four subclades (11 species) that appear to have secondarily replaced the diacetate with other compounds. In comparison with environment-derived perfumes, the evolution of labial gland secretion is much slower, likely constrained by the underlying biochemical pathways, but perhaps influenced by perfume-solvent chemical interactions.

Fatty Acid Origin of Insect Pheromones.

Pheromones are utilized to a great extent in insects. Many of these pheromones are biosynthesized through a pathway involving fatty acids. This chapter will provide examples where the biosynthetic pathways of fatty acid-derived pheromones have been studied in detail. These include pheromones from Lepidoptera, Coleoptera, and Hymenoptera. Many species of Lepidoptera utilize fatty acids as precursors to pheromones with a functional group that include aldehydes, alcohols, and acetate esters. In addition, the biosynthesis of hydrocarbons will be briefly examined because many insects utilize hydrocarbons or modified hydrocarbons as pheromones.

Spotted Lanternflies Respond to Natural Pheromone Lures for Mate-Finding and Oviposition.

Using semiochemicals collected from spotted lanternflies Lycorma delicatula (Hemiptera: Fulgoridae) (SLF) and deployed in the field with circle traps, we demonstrated that SLF responded to SLF pheromones: in particular, this was the case for males while seeking mates and for females while ovipositing. The attractants consisted of SLF body extract emitted from diffuser lures and SLF honeydew on burlap ribbons, collected from heavily infested locations. Traps with attractants were deployed in field sites with very light SLF infestations to avoid competing signals of pre-existing aggregations. The number of SLF equivalents emitted by each diffuser per trapping period was used in a dose-response analysis. Three trees per block received either (1) a control hexane lure and a clean ribbon, (2) a lure containing SLF extract and a clean ribbon, or (3) a lure containing SLF extract and a honeydew-laden ribbon. Ten blocks were sampled three times per week for twelve weeks. We found a significant positive dose-response by males to SLF body extract only in the presence of SLF honeydew, indicating a synergistic effect between honeydew volatiles and body volatiles. This dose-response occurred for five weeks after mating started, after which males no longer responded. Subsequently, females had a significant positive dose-response to SLF extract only in the presence of honeydew when oviposition was their primary activity, continuing for two weeks, suggesting that females may use pheromones to aggregate for oviposition. The extract in the absence of honeydew did not result in a positive dose-response, nor did the hexane control. These findings suggest that SLF respond synergistically to the combination of pheromones present in both SLF honeydew and SLF bodies. Thus, combining key components from both sources may aid the development of semiochemical lures for SLF.

Interaction between females and males grapevine moth Lobesia botrana modifies further mating preference.

During reproduction, females may boost their fitness by being selective based on direct material benefits provided by the males, such as nuptial gifts. In Lepidoptera, male provides a spermatophore containing nutrients. However, virgin males produce a bigger spermatophore, containing spermatozoa and nutrients, allowing higher female fertility. Lepidoptera females that could detect the sexual status of males may thus prefer a male without previous mating experience (i.e. a virgin male). This mate selection could be achieved by the use of chemical indices, such as sexual pheromones and cuticular compounds, known to be possibly exchanged during reproduction, and which can be indicators of a previous mating experience and known to be possibly sources of information exchanged. In this study, we experimentally presented Lobesia botrana virgin males with females in order for them to be exposed to females' natural sexual pheromones or cuticular compounds. 12 or 48 h after the exposure of males to either females' sexual pheromones or cuticular compounds, these males were confronted to naïve females, which have a choice between them or a virgin non-exposed males. We highlighted that, despite producing a spermatophore of similar volume, all exposed virgin males were less likely to mate with females 12 h after exposure, while after 48 h of exposure this is only the case for virgin males exposed to sexual pheromones. L. botrana females may thus discriminate male sexual experience based on chemical cues (either from cues transferred directly from females to males, or from changes in the cuticular or pheromone males' profile) indicating past mating experiences. Mating duration was longer for males exposed to sexual pheromones after 12 h only, and for males exposed to cuticular compounds after 48 h only. Pheromones signal might be more persistent over time and seems to more easily gather information for males. The physiological reasoning behind this result still needs to be investigated.

The roles of TGFß and serotonin signaling in regulating proliferation of oocyte precursors and germline aging.

The decline of oocyte quality in aging but otherwise relatively healthy individuals compels a search for underlying mechanisms. Building upon a finding that exposure to male pheromone ascr#10 improves oocyte quality in C. elegans, we uncovered a regulatory cascade that promotes proliferation of oocyte precursors in adults and regulates oocyte quality. We found that the male pheromone promotes proliferation of oocyte precursors by upregulating LAG-2, a ligand of the Notch-like pathway in the germline stem cell niche. LAG-2 is upregulated by a TGFß-like ligand DAF-7 revealing similarity of regulatory mechanisms that promote germline proliferation in adults and larvae. A serotonin circuit that also regulates food search and consumption upregulates DAF-7 specifically in adults. The serotonin/DAF-7 signaling promotes germline expansion to compensate for oocyte expenditure which is increased by the male pheromone. Finally, we show that the earliest events in reproductive aging may be due to declining expression of LAG-2 and DAF-7. Our findings highlight neuronal signals that promote germline proliferation in response to the environment and argue that deteriorating oocyte quality may be due to reduced neuronal expression of key germline regulators.

Long-sperm precedence and other cryptic female choices in Drosophila melanogaster.

Females that mate multiply make postmating choices about which sperm fertilize their eggs (cryptic female choice); however, the male characteristics they use to make such choices remain unclear. In this study, we sought to understand female sperm use patterns by evaluating whether Drosophila melanogaster females adjust sperm use (second male paternity) in response to four main factors: male genotype, male courtship effort, male pheromone alteration, and male postmating reproductive morphology. Our experiment was replicated across four different D. melanogaster lines, in a full factorial design, including a pheromone manipulation in which second males were perfumed to resemble heterospecific (D. yakuba) males. We found that females prefer longer sperm-regardless of mating order-in almost all contexts; this observed pattern of 'long-sperm precedence' is consistent with female postcopulatory choice of high-fitness male traits. Nonetheless, we also found that this general preference can be plastically altered by females in response to effects including perfuming treatment; this differential female sperm use is between otherwise identical males, and therefore solely female-mediated. Furthermore, our finding that females exercise choice using diverse criteria suggests a possible mechanism for the maintenance of variation in sexually selected male traits.

Molecular Assessments of Antimicrobial Protein Enterocins and Quorum Sensing Genes and Their Role in Virulence of the Genus Enterococcus.

Enterococcus has emerged as an opportunistic pathogen because of its antibiotic resistance and virulence profile, which makes it a causative agent of several diseases like endocarditis, surgical site, and urinary tract infections. Currently, species of this genus are the 2nd most frequently isolated microorganisms from hospital-acquired infections. Significant association with hospitals and unhygienic conditions of the environments has made them resistant to a wide range of antibiotics. On the brighter side, enterococci have the ability to produce antimicrobial proteins (i.e., enterocins) that exhibit wide antagonistic activity, thus making them useful microbes in the food and pharmaceutical industries. Enterocins are also involved in niche control in gut microbiota which is regulated by the quorum sensing (QS) system. A bacterial communication system that is controlled by the fsr operon in enterococci consists of FsrABDC, ef1097, and GelE/SprE genes. Hence, the present study was conducted for molecular assessment of enterocins and quorum sensing genes, inter-environmental correlation, and species prevalence of enterococci isolated from different environmental niches of Karachi, Pakistan. Obtained results revealed the highest prevalence of E. faecium and E. faecalis in all environments. Bacterial antagonism and enterocin genes were observed significantly high in poultry environments. The inter-environmental correlation indicated a strong positive correlation of freshwater with sewage and soil environments. Similarly, the fsr regulatory system was mostly identified in poultry-related environments, and a significant correlation between QS system and biofilm formation was established. In conclusion, this study confirmed the high prevalence of E. faecium in all tested sources, high enterocin production in non-clinical environments, and more fsr regulatory genes in poultry-related environments.

Binding properties of chemosensory protein 4 in Riptortus pedestris to aggregation pheromones.

In insects, chemosensory proteins (CSPs) play an important role in the perception of the external environment and have been widely used for protein-binding characterization. Riptortus pedestris has received increased attention as a potential cause of soybean staygreen syndrome in recent years. In this study, we found that RpedCSP4 expression in the antennae of adult R. pedestris increased with age, with no significant difference in expression level observed between males and females, as determined through quantitative real-time polymerase chain reaction (qRT-PCR). Subsequently, we investigated the ability of RpedCSP4 to bind various ligands (five aggregated pheromone components and 13 soybean volatiles) using a prokaryotic expression system and fluorescence competitive binding assays. We found that RpedCSP4 binds to three aggregated pheromone components of R. pedestris, namely, ((E)-2-hexenyl (Z)-3-hexenoate (E2Z3), (E)-2-hexenyl (E)-2-hexenoate (E2E2), and (E)-2-hexenyl hexenoate (E2HH)), and that its binding capacities are most stable under acidic condition. Finally, the structure and protein-ligand interactions of RpedCSP4 were further analyzed via homology modeling, molecular docking, and targeted mutagenesis experiments. The L29A mutant exhibited a loss of binding ability to these three aggregated pheromone components. Our results show that the olfactory function of RpedCSP4 provides new insights into the binding mechanism of RpedCSPs to aggregation pheromones and contributes to discover new target candidates that will provide a theoretical basis for future population control of R. pedestris.

Can sympathetic induction be a convenient technique for breeding Amblypharyngodon mola (Hamilton, 1822)?

Mola carplet (Amblypharyngodon mola) is one of the most popular small fish species of the Indian subcontinent. There are limited studies on captive breeding of this species, which is important for aquaculture and the conservation prospects of this species. The conventional induced breeding method using an inducing agent (GnRHa and dopamine antagonist) is one of the most effective and prevalent methods of breeding fish. It is a laborious and time-consuming process, particularly in mass fish breeding and in lieu of that, a less time-consuming method - sympathetic induction of the broodstock, is used in some regions of India, particularly in big carp fish. However, this method has not been reported in commercial-scale breeding of small indigenous fish species. Therefore, an experiment was conducted to compare the spawning efficiency of Amblypharyngodon mola bred by sympathetic induction with the conventional complete induced breeding method. The spawning performance in terms of latency period, relative fecundity, fertilization rate, incubation period, and hatching rates of sympathetically induced Amblypharyngodon mola were compared to completely induced Amblypharyngodon mola brooders. Although the latency period (7.8 hrs), relative fecundity (39 nos./g), fertilization rates (81.61%) and spawning efficiency coefficient (0.681) were better in conventionally induced fish, but lower post-spawning mortality (1.29%) and better hatching rates (86.21%) were observed in sympathetically induced fish. The results indicate that quality offspring of Amblypharyngodon mola could be obtained in terms of survivability through sympathetic breeding. Sympathetic induction breeding could be a cost-effective, convenient, time-saving method of mass-scale breeding and aquaculture of Amblypharyngodon mola.

Chemical species recognition in an adaptive radiation of Hawaiian Tetragnatha spiders (Araneae: Tetragnathidae).

Studies of adaptive radiations have played a central role in our understanding of reproductive isolation. Yet the focus has been on human-biased visual and auditory signals, leaving gaps in our knowledge of other modalities. To date, studies on chemical signals in adaptive radiations have focused on systems with multimodal signalling, making it difficult to isolate the role chemicals play in reproductive isolation. In this study we examine the use of chemical signals in the species recognition and adaptive radiation of Hawaiian Tetragnatha spiders by focusing on entire communities of co-occurring species, and conducting behavioural assays in conjunction with chemical analysis of their silks using gas chromatography-mass spectrometry. Male spiders significantly preferred the silk extracts of conspecific mates over those of sympatric heterospecifics. The compounds found in the silk extracts, long chain alkyl methyl ethers, were remarkably species-specific in the combination and quantity. The differences in the profile were greatest between co-occurring species and between closely related sibling species. Lastly, there were significant differences in the chemical profile between two populations of a particular species. These findings provide key insights into the role chemical signals play in the attainment and maintenance of reproductive barriers between closely related co-occurring species.

C. elegans males optimize mate-preference decisions via sex-specific responses to multimodal sensory cues.

For sexually reproducing animals, selecting optimal mates is important for maximizing reproductive fitness. In the nematode C. elegans, populations reproduce largely by hermaphrodite self-fertilization, but the cross-fertilization of hermaphrodites by males also occurs. Males' ability to recognize hermaphrodites involves several sensory cues, but an integrated view of the ways males use these cues in their native context to assess characteristics of potential mates has been elusive. Here, we examine the mate-preference behavior of C. elegans males evoked by natively produced cues. We find that males use a combination of volatile sex pheromones (VSPs), ascaroside sex pheromones, surface-associated cues, and other signals to assess multiple features of potential mates. Specific aspects of mate preference are communicated by distinct signals: developmental stage and sex are signaled by ascaroside pheromones and surface cues, whereas the presence of a self-sperm-depleted hermaphrodite is likely signaled by VSPs. Furthermore, males prefer to interact with virgin over mated, and well-fed over food-deprived, hermaphrodites; these preferences are likely adaptive and are also mediated by ascarosides and other cues. Sex-typical mate-preference behavior depends on the sexual state of the nervous system, such that pan-neuronal genetic masculinization in hermaphrodites generates male-typical social behavior. We also identify an unexpected role for the sex-shared ASH sensory neurons in male attraction to ascaroside sex pheromones. Our findings lead to an integrated view in which the distinct physical properties of various mate-preference cues guide a flexible, stepwise behavioral program by which males assess multiple features of potential mates to optimize mate preference.

Homo- and hetero-oligomeric protein-protein associations explain autocrine and heterologous pheromone-cell interactions in Euplotes.

In Euplotes, protein pheromones regulate cell reproduction and mating by binding cells in autocrine or heterologous fashion, respectively. Pheromone binding sites (receptors) are identified with membrane-bound pheromone isoforms determined by the same genes specifying the soluble forms, establishing a structural equivalence in each cell type between the two twin proteins. Based on this equivalence, autocrine and heterologous pheromone/receptor interactions were investigated analyzing how native molecules of pheromones Er-1 and Er-13, distinctive of mating compatible E. raikovi cell types, associate into crystals. Er-1 and Er-13 crystals are equally formed by molecules that associate cooperatively into oligomeric chains rigorously taking a mutually opposite orientation, and each burying two interfaces. A minor interface is pheromone-specific, while a major one is common in Er-1 and Er-13 crystals. A close structural inspection of this interface suggests that it may be used by Er-1 and Er-13 to associate into heterodimers, yet inapt to further associate into higher complexes. Pheromone-molecule homo-oligomerization into chains accounts for clustering and internalization of autocrine pheromone/receptor complexes in growing cells, while the heterodimer unsuitability to oligomerize may explain why heterologous pheromone/receptor complexes fail clustering and internalization. Remaining on the cell surface, they are credited with a key role in cell-cell mating adhesion.

Complexity of Chemical Emissions Increases Concurrently with Sexual Maturity in Heliconius Butterflies.

Pheromone communication is widespread among animals. Since it is often involved in mate choice, pheromone production is often tightly controlled. Although male sex pheromones (MSPs) and anti-aphrodisiacs have been studied in some Heliconius butterfly species, little is known about the factors affecting their production and release in these long-lived butterflies. Here, we investigate the effect of post-eclosion age on chemical blends from pheromone-emitting tissues in Heliconius atthis and Heliconius charithonia, exhibiting respectively free-mating and pupal-mating strategies that are hypothesised to differently affect the timing of their pheromone emissions. We focus on two different tissues: the wing androconia, responsible for MSPs used in courtship, and the genital tip, the production site for anti-aphrodisiac pheromones that affect post-mating behaviour. Gas chromatography-mass spectrometric analysis of tissue extracts from virgin males and females of both species from day 0 to 8 post-eclosion demonstrates the following. Some ubiquitous fatty acid precursors are already detectable at day 0. The complexity of the chemical blends increases with age regardless of tissue or sex. No obvious difference in the time course of blend production was evident between the two species, but female tissues in H. charithonia were more affected by age than in H. atthis. We suggest that compounds unique to male androconia and genitals and whose amount increases with age are potential candidates for future investigation into their roles as pheromones. While this analysis revealed some of the complexity in Heliconius chemical ecology, the effects of other factors, such as the time of day, remain unknown.

Organotransition Metal Chemistry of Terpenes: Syntheses, Structures, Reactivity and Molecular Rearrangements.

The impact of organometallic chemistry on the terpene field only really blossomed in the 1960s and 1970s with the realisation that carbon-carbon bond formation under mild conditions could be achieved by using nickel or iron carbonyls as synthetic reagents. Concomitantly, the development of palladium derivatives capable of the controlled coupling of isoprene units attracted the attention of numerous highly talented researchers, including future Nobel laureates. We discuss briefly how early work on the syntheses of simple monoterpenes soon progressed to sesquiterpenes and diterpenes of increasing complexity, such as humulene, flexibilene, vitamin A, or pheromones of commercial value, in particular those used in perfumery (muscone, lavandulol), or grandisol and red scale pheromone as replacements for harmful pesticides. As the field progressed, there has been more emphasis on developing organometallic routes to enantiopure rather than racemic products, as well as gaining precise mechanistic data on the transformations, notably the course of metal-promoted molecular rearrangements that have long been a feature of terpene chemistry. We note the impact of the enormously enhanced analytical techniques, high-field NMR spectroscopy and X-ray crystallography, and their use to re-examine the originally proposed structures of terpenes and their organometallic derivatives. Finally, we highlight the very recent ground-breaking use of the crystalline sponge method to acquire structural data on low-melting or volatile terpenes. The literature cited herein covers the period 1959 to 2023.

Cutaneous application of SecurePig® FLASH, a Pig appeasing pheromone analogue, facilitates adaptation and manages social behavior during feeding in semi-extensive conditions.

BACKGROUND: Farm animals face several challenges throughout their lives, which can affect both their welfare and their productivity. Promoting adaptation in animals is one way of limiting these consequences. In various animal species, the use of maternal appeasing pheromones is efficient to reduce aggressiveness, improve adaptation and thus ensuring better welfare and productivity. This study sought to investigate the efficiency of a treatment with a Pig Appeasing Pheromone (PAP) on the behavior of pigs reared under semi-extensive conditions and exposed to a potential conflict- collective feeding. Animals (n = 14 divided in 2 groups of 7) were subjected to 3 different phases, (A) baseline - no pigs received the PAP, (B) SP - 2 out of the 7 pigs per group received the PAP and (C) AP- all pigs received the PAP. Behaviors related to feeding, aggression and locomotion were compared between the 3 phases of the study. RESULTS: Compared to the baseline period, we observed that the number of head knocks was reduced when some pigs (p < 0.001) and all pigs (p < 0.005) received the PAP. Similarly, we observed that the number of fleeing attempts was reduced when some pigs (p < 0.001) and all pigs (p < 0.001) were treated when compared to baseline. This number was lower in the AP phase than in the SP phase (p < 0.001). When all pigs were treated (AP), we also observed that they spent less time investigating the floor than during the two other phases (p < 0.001), but they seemed more likely to leave the feeder due to the presence or behavior of another pig of the group (SP vs. AP, p < 0.05). CONCLUSIONS: The PAP application improved adaptation in pigs by reducing aggressiveness and promoting conflict avoidance. Those results validate the efficiency of the pheromonal treatment under semi-extensive rearing conditions to help pigs to cope with a challenging situation. Using PAP in the pig industry seems interesting to limit unwanted consequences of farm practices on animal welfare and productivity, by promoting their adaptation.

Extreme olfactory sensitivity of silver and bighead carp to overlapping suites of 21-carbon steroids suggests that these species, and likely all other Cyprinoidei, employ them as pheromones.

Although well established that several fishes including goldfish in the suborder Cypinoidei within the family Cypriniformes use the maturation-inducing steroid 17,20ß-dihydroxy-pregn-4-ene-3-one (17,20ßP) and its metabolites as a priming pheromone which they detect with sensitivity and specificity, it is unclear whether and how other Cypriniformes might have evolved to do so. This study examined this question in the family Xenocyprididae. Using electro-olfactogram recording we tested the olfactory sensitivity of silver (Hypophthalmichthys molitrix) and bighead carp (H. nobilis) to a range of 213 steroids in 21 mixtures at 10-9M. While silver carp detected 6 of 21 mixtures, bighead carp detected 5 (p< 0.05). Silver carp were sensitive to 13 21-carbon steroids in these mixtures including 17,20ßP while bighead carp detected 9, including 8 detected by silver carp. This assortment of steroids overlapped that detected by goldfish (family Cyprinidae) but no non-Cyprinoid, suggesting common evolutionary origin and function with differences characteristic of species-specificity.

The vomeronasal system of the wolf (Canis lupus signatus): The singularities of a wild canid.

Wolves, akin to their fellow canids, extensively employ chemical signals for various aspects of communication, including territory maintenance, reproductive synchronisation and social hierarchy signalling. Pheromone-mediated chemical communication operates unconsciously among individuals, serving as an innate sensory modality that regulates both their physiology and behaviour. Despite its crucial role in the life of the wolf, there is a lacuna in comprehensive research on the neuroanatomical and physiological underpinnings of chemical communication within this species. This study investigates the vomeronasal system (VNS) of the Iberian wolf, simultaneously probing potential alterations brought about by dog domestication. Our findings demonstrate the presence of a fully functional VNS, vital for pheromone-mediated communication, in the Iberian wolf. While macroscopic similarities between the VNS of the wolf and the domestic dog are discernible, notable microscopic differences emerge. These distinctions include the presence of neuronal clusters associated with the sensory epithelium of the vomeronasal organ (VNO) and a heightened degree of differentiation of the accessory olfactory bulb (AOB). Immunohistochemical analyses reveal the expression of the two primary families of vomeronasal receptors (V1R and V2R) within the VNO. However, only the V1R family is expressed in the AOB. These findings not only yield profound insights into the VNS of the wolf but also hint at how domestication might have altered neural configurations that underpin species-specific behaviours. This understanding holds implications for the development of innovative strategies, such as the application of semiochemicals for wolf population management, aligning with contemporary conservation goals.

Discovery and properties of novel analogues of the aphid pheromones nepetalactone and nepetalactol.

BACKGROUND: Pheromones have unique advantages for pest control. Current aphid pheromone research focuses on alarm and sex pheromones. However, practical applications are limited so far, as (E)-ß-farnesene has only been investigated to a small extent as an alarm pheromone and only male aphids are targeted by sex pheromones. Previous literature reports electrophysiological responses and repellent behavior of asexual aphids to nepetalactone (1B), therefore our objective was to modify nepetalactone's structure to identify key fragments responsible for repellent effects, as guidance for subsequent modifications and further investigation. RESULTS: In this study, seven derivatives were designed and synthesized based on nepetalactol (1A) and nepetalactone (1B) as lead compounds. Free-choice tests, conducted using cowpea aphids (Aphis craccivora), revealed that the lactone moiety was crucial for the repellent activity, and the removal of the carbonyl group eliminated the repelling effect. Compound (±)1I, an analogue of nepetalactone (1B), demonstrated a significantly higher repellent value than nepetalactone (1B) at three different concentrations, and even at 0.1 mg/mL it maintained a considerable repellent effect (26.5%). Electrostatic potential and density functional theory calculations supported the importance of the carbonyl group for the repellent effects. CONCLUSION: The newly discovered para-pheromone (±)1I shows improved repellent effects and potential for development as a novel biological control agent. Based on our innovative findings, analogues with improved efficacy and properties can be designed and prepared. Our research contributes to understanding the effects of structural modifications on pheromone activity and properties, which is crucial for exploring novel pheromone-based products for crop protection. © 2024 Society of Chemical Industry.

Enhancing entomopathogenic nematode efficacy with Pheromones: A field study targeting the pecan weevil.

Consistent efficacy is required for entomopathogenic nematodes to gain wider adoption as biocontrol agents. Recently, we demonstrated that when exposed to nematode pheromone blends, entomopathogenic nematodes showed increased dispersal, infectivity, and efficacy under laboratory and greenhouse conditions. Prior to this study, the impact of entomopathogenic nematode-pheromone combinations on field efficacy had yet to be studied. Steinernema feltiae is a commercially available entomopathogenic nematode that has been shown to increase mortality in insect pests such as the pecan weevil Curculio caryae. In this study, the pecan weevil was used as a model system to evaluate changes in S. feltiae efficacy when treated with a partially purified ascaroside pheromone blend. Following exposure to the pheromone blend, the efficacy of S. feltiae significantly increased as measured with decreased C. caryae survival despite unfavorable environmental conditions. The results of this study highlight a potential new avenue for using entomopathogenic nematodes in field conditions. With increased efficacy, using entomopathogenic nematodes will reduce reliance on conventional management methods in pecan production, translating into more environmentally acceptable practices.