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

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 (Sulz.) (Hemiptera: Aphididae) du...

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Published in:Molecules (Basel, Switzerland) Switzerland), 2019-05, Vol.24 (10), p.1847
Main Authors: Wróblewska-Kurdyk, Anna, Gniłka, Radosław, Dancewicz, Katarzyna, Grudniewska, Aleksandra, Wawrzeńczyk, Czesław, Gabryś, Beata
Format: Article
Language:English
Subjects:
Amides
antifeedants
Aphididae
Beckmann rearrangement
Behavior
Biological activity
Bisulfite
Carbon
Chemicals
Cyclopentane
Essential oils
Functional groups
Herbivores
Ingestion
Insecticides
Insects
Myzus persicae
Nitrogen
Oils & fats
Phloem
Potatoes
Settling
Stereochemistry
Thujone
α-thujone
β-thujone
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Summary: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 (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 . 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).
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules24101847