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β-Thujone and Its Derivatives Modify the Probing Behavior of the Peach Potato Aphid

1
Department of Botany and Ecology, University of Zielona Góra, Szafrana 1, 65-516 Zielona Góra, Poland
2
Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland
3
Łukasiewicz Research Network–PORT Polish Center for Technology Development, Stabłowicka 147, 54-066 Wrocław, Poland
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(10), 1847; https://doi.org/10.3390/molecules24101847
Received: 7 March 2019 / Revised: 8 May 2019 / Accepted: 10 May 2019 / Published: 14 May 2019
(This article belongs to the Section Chemical Biology)
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Abstract

Thujone is a natural biologically active monoterpene ketone component of essential oils of numerous plants. The aim of the study was to evaluate the effect of β-thujone and β-thujone derivatives bisulfite adduct, lactone, oxime, and lactam application on behavior of Myzus persicae (Sulz.) (Hemiptera: Aphididae) during probing and settling. The choice and no-choice tests (aphid settling and Electrical Penetration Graph (EPG), respectively) revealed that stereochemistry of thujone was important for biological activity (β-thujone caused changes in aphid behavior while α-thujone did not) and that cyclopentane ring modifications and functional groups addition gave derivatives that possessed stronger and more durable deterrent effects. The most effective modification was the incorporation of a lactam moiety into the β-thujone molecule. Application of β-thujone lactam limited aphid settling for at least 24 h, caused restlessness in aphids and a delay or failure in reaching phloem phase by M. persicae. β-Thujone lactam can be considered a deterrent of medium potency with activity expressed at preingestive phase of aphid probing. Other compounds did not restrain aphid stylet penetration in non-phloem tissues but slightly limited sap ingestion (lactone, oxime), and restrained aphid settling for a period of less than 24 h (β-Thujone, bisulphite adduct, lactone). View Full-Text
Keywords: α-thujone; β-thujone; Beckmann rearrangement; Myzus persicae; antifeedants α-thujone; β-thujone; Beckmann rearrangement; Myzus persicae; antifeedants
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Wróblewska-Kurdyk, A.; Gniłka, R.; Dancewicz, K.; Grudniewska, A.; Wawrzeńczyk, C.; Gabryś, B. β-Thujone and Its Derivatives Modify the Probing Behavior of the Peach Potato Aphid. Molecules 2019, 24, 1847.

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