Discovery of the Aggregation Pheromone of the Brown Marmorated Stink Bug (<i>Halyomorpha halys</i>) through the Creation of Stereoisomeric Libraries of 1-Bisabolen-3-ols

Khrimian, Ashot; Zhang, Aijun; Weber, Donald C.; Ho, Hsiao-Yung; Aldrich, Jeffrey R.; Vermillion, Karl E.; Siegler, Maxime A.; Shirali, Shyam; Guzman, Filadelfo; Leskey, Tracy

doi:10.1021/np5003753

Cited by 156 publications

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“…We have shown that we can remove large quantities of individuals from the stink bug population in apple orchards throughout the season, especially during the late season when H. halys pressure is greatest (Nielsen and Hamilton 2009b;Nielsen et al 2011). In addition, attract-and-kill is most likely to succeed when both males and females are attracted by the pheromone source, which is the case for H. halys (Khrimian et al 2014).…”

Section: Discussionmentioning

confidence: 99%

“…: Hossain et al 2005). The two-component aggregation pheromone for H. halys has recently been identified as (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol and (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol in a 3.5:1 ratio (Khrimian et al 2014). In addition, the aggregation pheromone of the Oriental stink bug, Plautia stali Scott (Hemiptera: Pentatomidae), methyl (2E,4E,6Z)-2,4,6-decatrienoate (MDT) (Sugie et al 1996), serves as a strong synergist (Weber et al 2014a).…”

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Establishing the behavioral basis for an attract-and-kill strategy to manage the invasive Halyomorpha halys in apple orchards

et al. 2015

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Halyomorpha halys (Stål), the brown marmorated stink bug, is an invasive, polyphagous insect that causes serious economic injury in particular to specialty crops in the United States. Growers have been forced to respond by increasing the frequency of broad-spectrum insecticide (e.g., neonicotinoid, pyrethroid, and carbamate) applications. One strategy to reduce reliance on insecticides is known as ''attract-and-kill'' whereby the targeted insect is attracted to a spatially precise location to be eliminated by a killing agent such as an insecticide. This approach can substantially reduce the amount of insecticide used by sparing alternate row middle or whole block sprays. For apple orchards, we propose baiting select border row trees with the H. halys aggregation pheromone and synergist and subsequently treating these baited trees with effective insecticides to kill H. halys throughout the growing season. To evaluate the behavioral basis of this approach, we conducted orchard trials with black pyramid traps, harmonic radar, and trials using baited apple trees sprayed weekly to quantify H. halys arrestment area, retention time, adult and nymph annihilation, and fruit injury in and near these attract-and-kill sites. The arrestment area for H. halys was confined to a 2.5 m radius around the pheromone-and pheromone synergist-baited trap regardless of pheromone dose (84 or 840 mg), while the retention capacity of adults was significantly increased by pairing the aggregation pheromone and synergist with a fruiting host plant compared with non-host sites. Damage to fruit harvested from baited attract-and-kill trees was high, but minimal in surrounding unbaited neighboring apple trees. Our results suggest attract-and-kill may be an effective strategy for managing H. halys season-long.Keywords Integrated pest management Á Brown marmorated stink bug Á Behaviorally based management Á Harmonic radar Á Invasive species Á Pheromone Á Hemiptera Á Pentatomidae Key messages• Halyomorpha halys management relies on repeated insecticide applications to susceptible crops. • We evaluated the behavioral basis for a proposed attract-and-kill strategy in apple as a means to reduce insecticide inputs. • We found that attract-and-kill holds promise as H. halys activity was confined to a small arrestment area around a pheromone source, and the use of harmonic radar showed that retention time at these sites was greatest when a host plant (apple) was present. • High kill of H. halys was achieved in baited attract-andkill apple trees season-long with minimal damage on adjacent unbaited trees. Communicated by T. Haye.Electronic supplementary material The online version of this article (

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Establishing the behavioral basis for an attract-and-kill strategy to manage the invasive Halyomorpha halys in apple orchards

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“…Lastly, the brown marmorated stink bug, Halyomorpha halys, has been shown to share compound 3 as the main component of its aggregation pheromone, along with (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol (5), produced by the male bug in a 3.5:1 ratio. 9 The last two stink bug species are important agricultural pests for which the aggregation pheromones have successfully been used for detection and monitoring. 10,11 For syntheses of abovementioned bisabolenol stink bug pheromones, we earlier explored a rhodium-catalyzed asymmetric addition of trimethylaluminum to diastereomeric mixtures of cyclohex-2-enones.…”

Section: Introductionmentioning

confidence: 99%

“…10,11 For syntheses of abovementioned bisabolenol stink bug pheromones, we earlier explored a rhodium-catalyzed asymmetric addition of trimethylaluminum to diastereomeric mixtures of cyclohex-2-enones. 9 This conveniently provided two single stereoisomers from one reaction (Scheme 1) and thus allowed us to build a full library of stereoisomers of bisaboladienols and epoxybisabolenols. 8,9 Scheme 1.…”

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Expedient synthesis of bisabolenol stink bug pheromones via stereodefined cyclohex-2-enones

Shirali

Guzman

Weber

et al. 2017

Tetrahedron Letters

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Expedient synthesis of bisabolenol stink bug pheromones via stereodefined cyclohex-2-enones, Tetrahedron Letters (2017), doi: http://dx. ABSTRACTWe recently synthesized all stereoisomers of 1,10-bisaboladien-3-ol and 10,11-epoxy-1-bisabolen-3-ol, including three stink bug pheromones, via a rhodium-catalyzed asymmetric addition of trimethylaluminum to diastereomeric mixtures of cyclohex-2-enones. However, yields of trans isomers were low, and scaling reactions using expensive catalysts were cumbersome. Now we describe a new synthesis of bisabolenol stink bug pheromones via (S)-and (R)-4-((R)-6-methylhept-5-en-2-yl)cyclohex-2-enones prepared by enantioselective Michael additions of methyl vinyl ketone to (S)-and (R)-citronellals and lithium hydroxide monohydratecatalyzed stereoselective cyclizations of intermediate ketoaldehydes. Addition of methyllithiumto these enones provided cis-and trans-1,10-bisaboladien-3-ols, which were separated by chromatography on silica and further converted to 10,11-epoxy-1-bisabolen-3-ols. Thus, we developed more convenient syntheses of pheromones of the rice stink bug, the harlequin bug, and brown marmorated stink bug.

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Identification and characterization of capa and pyrokinin genes in the brown marmorated stink bug, Halyomorpha halys (Hemiptera): Gene structure, immunocytochemistry, and differential expression

Ahn

Choi

2018

Arch Insect Biochem Physiol

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CAPA and pyrokinin (PK) neuropeptides are produced from two different genes, capa and pyrokinin, respectively. In this study, we identified and characterized the capa and pyrokinin genes from the brown marmorated stink bug, Halyomorpha halys (Hemiptera). The capa gene encodes two CAPA-PVK (periviscerokinin) peptides (DAGLFPFPRVamide and EQLIPFPRVamide) and one CAPA-DH (diapause hormone; NGASGNGGLWFGPRLamide). The pyrokinin gene encodes three PK2 peptides (QLVSFRPRLamide, SPPFAPRLamide, and FYAPFSPRLamide). The whole-mounting immunocytochemistry revealed the neurons contained PRXamide-like peptides throughout the cerebral ganglia (CRG), gnathal ganglia (GNG), thoracic ganglia (TG), and abdominal ganglia (AG). A pair of neurosecretory cells in the CRG and three cell clusters in the GNG were found with the axonal projections extended through the lateral side. A pair of immunostained cells were found in the TG, while three pairs of cells were present in the fused AG. Different expression patterns of capa and pyrokinin genes were observed in the CRG-GNG, TG, and AG. The capa gene was highly expressed in the AG tissue, whereas the pyrokinin gene was strongly expressed in the CRG-GNG. Interestingly, different developmental stages showed similar expressions of both genes, with the highest from the first nymph, gradually decreasing to the female adult. Comparison of peptide sequences encoded from pyrokinin genes showed the PK1 peptide is lost in Heteroptera suborders including H. halys, but retained in other suborders. The missing PK1 from the pyrokinin gene might be compensated by CAPA-DH (=PK1-like) produced by the capa gene.

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Discovery of the Aggregation Pheromone of the Brown Marmorated Stink Bug (Halyomorpha halys) through the Creation of Stereoisomeric Libraries of 1-Bisabolen-3-ols

Cited by 156 publications

References 34 publications

Establishing the behavioral basis for an attract-and-kill strategy to manage the invasive Halyomorpha halys in apple orchards

Establishing the behavioral basis for an attract-and-kill strategy to manage the invasive Halyomorpha halys in apple orchards

Expedient synthesis of bisabolenol stink bug pheromones via stereodefined cyclohex-2-enones

Identification and characterization of capa and pyrokinin genes in the brown marmorated stink bug, Halyomorpha halys (Hemiptera): Gene structure, immunocytochemistry, and differential expression

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