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Gas chromatography analysis of (a) natural (6S,10S)-(2E,4E,8E)-4,6,8,10-tetramethyltrideca-2,4,8-triene, (b) synthetic (6S,10S)-(2E,4E,8E)-4,6,8,10-tetramethyltrideca-2,4,8-triene, and (c) the mixture of four stereoisomers of (2E,4E,8E)-4,6,8,10-tetramethyltrideca-2,4,8-triene on a chiral stationary phase β-DEX 120 column (190 °C isothermal)
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The Asian eulophid wasp Tetrastichus planipennisi is being released in North America as a biocontrol agent for the emerald ash borer (Agrilus planipennis), a very destructive invasive buprestid beetle that is devastating ash trees (Fraxinus spp.). We identified, synthesized, and tested a female-produced sex pheromone for the wasp. The key component...
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Mechanical properties of small-diameter round timber from hardwood thinnings of common alder (
Alnus glutinosa
(L.) Gaertn.), European ash (
Fraxinus excelsior
L.), European birch (
Betula pendula
Roth. and
Betula pubescens
Ehrh.), and sycamore (
Acer pseudoplatanus
L.) can be evaluated by non-destructive testing on either standing tree...
Biogradska Gora National Park in Montenegro is part of the Dinaric Mountains mixed forest, which belongs to the montane region of the Dinaric Alps. This paper presents some of the main structural and ecological characteristics of the mixed broadleaved old-growth forest with beech [Fagus moesiaca (Domin, Maly) Czecz.], sycamore maple (Acer pseudopla...
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... Racemic 2-methylbutan-1-ol (MeBuOH), (S)-2-methylbutan-1-ol (S-MeBuOH), and racemic 2-methylpentan-1-ol (MePeOH) were purchased from Sigma-Aldrich (St. Louis, MO, USA). (R)-2-Methylbutan-1-ol (R-MeBuOH) was prepared by lipase-based kinetic resolution of racemic MeBuOH (Bello et al. 2015), and (S)-2-methylpentan-1-ol (S-MePeOH) was synthesized as described in Cossé et al. (2020). Racemic anti-2,3-octanediol (anti-C8-diol) was synthesized as described in Lacey et al. (2004), and (2S,3R)-2,3-octanediol as in Wickham et al. (2016). ...
During field screening trials in Brazil, adults of both sexes of the cerambycid beetle Achryson surinamum (L.) (Cerambycinae: Achrysonini) were significantly attracted to racemic anti-2,3-octanediol, previously identified as a sex and aggregation-sex pheromone of various cerambycid species across different continents. Analyses of beetle-produced volatiles revealed that males of A. surinamum sex-specifically produce (2S,3R)-2,3-octanediol, as well as lesser amounts of (S)-2-methylbutan-1-ol. In field trials, both sexes of beetles were attracted by reconstructions of the species’ pheromone blend with synthesized components, confirming males produce an aggregation-sex pheromone. During the trials, the cerambycine Sphaerion inerme White (Elaphidiini) was attracted to some of the test lures, providing leads to its attractant pheromone. Subsequent analysis of extracts of headspace volatiles from live adults of S. inerme revealed that males produce a blend of (R)-2-methylbutan-1-ol and (R)-2-methylpentan-1-ol. In field tests, blends of racemic 2-methylbutan-1-ol+2-methylpentan-1-ol attracted significant numbers of beetles of both sexes. This study provides further examples of how identification of attractant pheromones of cerambycid species can be expedited by leveraging prior knowledge of the pheromone chemistry of related species.
... Besides these short-chain aldehydes, some unsaturated long-chain aldehydes have been reported as sex pheromone components in parasitoid wasps. (61) and Tetrastichus planipennisi (Eulophidae) (62), respectively. In this study, using comprehensive electrophysiological analyses and behavioral tests, we discovered that 14:Ald and 2-Hep comprise the volatile sex pheromone of C. chlorideae. ...
Sex pheromones are pivotal for insect reproduction. However, the mechanism of sex pheromone communication remains enigmatic in hymenopteran parasitoids. Here we have identified the sex pheromone and elucidated the olfactory basis of sex pheromone communication in Campoletis chlorideae (Ichneumonidae), a solitary larval endoparasitoid of over 30 lepidopteran pests. Using coupled gas chromatography-electroantennogram detection, we identified two female-derived pheromone components, tetradecanal (14:Ald) and 2-heptadecanone (2-Hep) (1:4.6), eliciting strong antennal responses from males but weak responses from females. We observed that males but not females were attracted to both single components and the blend. The hexane-washed female cadavers failed to arouse males, and replenishing 14:Ald and 2-Hep could partially restore the sexual attraction of males. We further expressed six C. chlorideae male-biased odorant receptors in Drosophila T1 neurons and found that CchlOR18 and CchlOR47 were selectively tuned to 14:Ald and 2-Hep, respectively. To verify the biological significance of this data, we knocked down CchlOR18 and CchlOR47 individually or together in vivo and show that the attraction of C. chlorideae to their respective ligands was abolished. Moreover, the parasitoids defective in either of the receptors were less likely to court and copulate. Finally, we show that the sex pheromone and (Z)-jasmone, a potent female attractant, can synergistically affect behaviors of virgin males and virgin females and ultimately increase the parasitic efficiency of C. chlorideae. Our study provides new insights into the molecular mechanism of sex pheromone communication in C. chlorideae that may permit manipulation of parasitoid behavior for pest control.
Covering: 2013 to June 2022Pheromones are usually produced by insects in sub-microgram amounts, which prevents the elucidation of their structures by nuclear magnetic resonance (NMR). Instead, a synthetic reference material is needed to confirm the structure of the natural compounds. In addition, the provision of synthetic pheromones enables large-scale field trials for the development of environmentally friendly pest management tools. Because of these potential applications in pest control, insect pheromones are attractive targets for the development of synthetic procedures and the synthesis of these intraspecific chemical messengers has been at the core of numerous research efforts in the field of pheromone chemistry. The present review is a quick reference guide for the syntheses of insect pheromones published from 2013 to mid-2022, listing the synthesized compounds and highlighting current methodologies in organic synthesis, such as carbon-carbon coupling reactions, organo-transition metal chemistry including ring-closing olefin metathesis, asymmetric epoxidations and dihydroxylations, and enzymatic reactions.
