Feeding Deterrent Activity of Terpenoid Lactones with the &lt;I&gt;p&lt;/I&gt;-Menthane System Against the Colorado Potato Beetle (Coleoptera: Chrysomelidae)

Szczepanik, M.; Dams, Iwona; Wawrzeńczyk, Czesław

doi:10.1603/0046-225x-34.6.1433

Cited by 34 publications

(32 citation statements)

References 64 publications

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“…They exhibited antifeedant activity towards storage insect pests, [16][17][18][19][20] aphids, 21,22 lesser mealworm 23,24 or colorado potato beetle. 2,25 Some of the obtained lactones also inhibited the growth of pathogenic fungi. 26 688 Andrzej Skrobiszewski et al In this paper, we report the synthesis of another series of lactones, namely, racemic β-aryl-γ -lactones derived from natural aromatic aldehydes.…”

Section: Introductionmentioning

confidence: 98%

Synthesis of β-aryl-γ-lactones and relationship: Structure – antifeedant and antifungal activity

et al. 2015

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Eighteen racemic β-aryl-γ -lactones derived from simple aromatic aldehydes have been obtained in the chemical synthesis. Iodolactones (5c and 6c) were synthesized from (E)-4-(benzo [d][1 ,3 ]-dioxol-5 -yl)-but-3-en-2-one (1). Reductive dehalogenation of iodolactones 5a-c and 6a-c afforded γ -ethyl-γ -lactones (7a-c, 8a-c) whereas the unsaturated lactones (9a-c, 10a-c) were obtained by dehydrohalogenation of iodolactones. All synthesized lactones were fully characterized by spectroscopic data (NMR, IR, HRMS) and subjected to the tests on the antifeedant activity towards Tribolium confusum, Trogoderma granarium and Sitophilus granaries as well to the tests on the antifungal activity towards four Fusarium species. The biological tests allowed to find some relationships between the structure and biological activity of the compounds studied. γ -Ethyl-γ -lactones 7a-c, 8a-c and unsaturated lactones 9a-c, 10a-c were usually stronger antifeedants than their parent iodolactones 5a-c and 6a-c. trans-Iodolactones 6a-c were more active than cis isomers 5a-c both in antifeedant and antifungal assays. The structure of aromatic substituent was the key factor in antifungal activity. The lactones with benzo [d][1,3]dioxole ring (5c, 6c, 7c, 8c, 9c) were the most active whereas those with unsubstituted benzene ring exhibited almost no activity.

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Section: Introductionmentioning

confidence: 98%

Synthesis of β-aryl-γ-lactones and relationship: Structure – antifeedant and antifungal activity

et al. 2015

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“…Aguerin B and chlorojanerin, isolated from Rhaponticum pulchrum , have been shown to be good feeding deterents against three stored‐product insect pests: Sitophilus granarius , Trogoderma granarium and Tribolium confusum . The synthetic lactones are also potent antifeedants . The chlorolactone obtained from β ‐cyclocitral is a good antifeedant against Tribolium confusum .…”

Section: Introductionmentioning

confidence: 99%

Lactones 46. Synthesis, antifeedant and antibacterial activity ofγ-lactones with ap-methoxyphenyl substituent

et al. 2015

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The results of biological tests showed that halogen atom removal significantly increased the antifeedant properties of γ-lactones with a p-methoxyphenyl substituent. Unsaturated lactones are most promising in the context of their possible industrial application as crop protection agents. Further structural modifications of lactones with aromatic rings are needed to find important structural factors increasing the antibacterial activity.

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“…In fi nding the alternative agents for pest control, one of the possibilities is the application of essential oils and plant extracts with repellent, antifeedant or masking effect against the insect pests (28). For this purpose, the plant extracts and essential oils were widely investigated for their biological activities (7,13,14,15,16,18,38).…”

Section: Introductionmentioning

confidence: 99%

Developmental and Feeding Alternations inLeptinotarsa DecemlineataSay. (Coleoptera: Hrysomelidae) Caused bySalvia OfficinalisL. (Lamiaceae) Essential Oil

Kostić¹,

Dražić²,

Popović³

et al. 2007

Biotechnology & Biotechnological Equipment

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Feeding Deterrent Activity of Terpenoid Lactones with the <I>p</I>-Menthane System Against the Colorado Potato Beetle (Coleoptera: Chrysomelidae)

Cited by 34 publications

References 64 publications

Synthesis of β-aryl-γ-lactones and relationship: Structure – antifeedant and antifungal activity

Synthesis of β-aryl-γ-lactones and relationship: Structure – antifeedant and antifungal activity

Lactones 46. Synthesis, antifeedant and antibacterial activity ofγ-lactones with ap-methoxyphenyl substituent

Developmental and Feeding Alternations inLeptinotarsa DecemlineataSay. (Coleoptera: Hrysomelidae) Caused bySalvia OfficinalisL. (Lamiaceae) Essential Oil

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