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2009 | 18 | 6 |

Tytuł artykułu

The effect of alpha-methylenelactone group on the feeding deterrent activity of natural and synthetic alkenes against colorado potato beetle, Leptinotarsa decemlineata Say

Warianty tytułu

Języki publikacji

EN

Abstrakty

EN
Studies on the feeding deterrent activity of some natural, cyclic terpenes (myrcene, (+)-3-carene, (+)-limonene, (±)-camphene), synthetic alkenes (2-methyl-1-pentene, 2,4,4-trimethyl-1-pentene, 1-methylcyclohexene, 1-tetradecene) and their derivatives α-methylenelactones in choice and no-choice tests against Colorado potato beetle with potato, Solanum tuberosum L. leaf discs as consuming food were carried out. Deterrent indexes determined in the tests show that the strongest antifeedant to larvae and adults of Leptinotarsa decemlineata was α-methylenelactone obtained from 2,4,4-trimethyl-1-pentene. The structure modification of (+)-3-carene and (±)-camphene via introduction of α-methylenelactone moiety increased their deterrent activity, especially against larvae. Other starting alkenes and α-methylenelactones obtained from them were weak deterrents to both developmental stages of L. decemlineata.

Słowa kluczowe

Wydawca

-

Rocznik

Tom

18

Numer

6

Opis fizyczny

p.1107-1112,fig.,ref.

Twórcy

  • Department of Invertebrate Zoology, Institute of General and Molecular Biology, Nicolaus Copernicus University, Gagarina 9, 87-100 Torun, Poland
autor
  • Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, 50-375 Wroclaw, Poland
  • Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, 50-375 Wroclaw, Poland

Bibliografia

  • 1. RAHARDJA U., WHALON M.E. Inheritance of resistance to Bacillus thuringiensis subsp.tenebrionis Cry IIIA deltaendotoxin in Colorado potato beetle (Coleoptera: Chrysomelidae). J. Econ.Entomol. 88, 21, 1995.
  • 2. ARPAIA S., CHIRIATTI K., GIORIO G. Predicting the adaptation of Colorado potato beetle (Coleoptera: Chrysomelidae) to transgenic eggplants expressing CryIII toxin: the role of gene dominance, migration, and fitness costs. J. Econ. Entomol. 91, 21, 1998.
  • 3. HERTELENDY L. Systems for control of Leptinotarsa decemlineata preventing development of resistance. Bulletin OEPP/EPPO Bulletin, 28, 459, 1998.
  • 4. LOSEVA O., IBRAHIM M., CANDAS M., KOLLER C.N., BAUER L.S., BULLA L.A. Changes in protease activity and Cry3a a toxin binding in the Colorado potato beetle: Implications for insect resistance to Bacillus thuringiensis toxins. Insect Biochem. Molec. 32, 567, 2002.
  • 5. WĘGOREK, P. History of the Colorado potato beetle (Leptinotarsa decemlineata Say) resistance to insecticides. ed. Institute of Plant Protection – National Research Institute Poznań, 2007. [In Polish].
  • 6. ISMAN M. Insect antifeedants. Pesticide Outlook-August, 13, 152, 2002.
  • 7. FRANCK B. Key building blocks of natural product biosynthesis and their significance in chemistry and medicine. Angew. Chem. Int. Ed. Engl. 18, 429, 1979.
  • 8. LAEKEMAN G.M., DE CLERCK F., VLIETINCK A.J., HERMAN A.G. Vernolepin: An antiplatelet compound of natural origin. N-S Arch. Pharmacol. 331, 108, 1985.
  • 9. RAMOS A., RIVERO R., VISOZO A., PILOTO J., GARCÍA A. Parthenin, a sesquiterpene lactone of Parthenium hysterophorus L. is a high toxicity clastogen. Mutat. Res. 514, 19, 2002.
  • 10. BOULANGER D., BROUILLETTE E., JASPAR F., MALOUIN F., MAINIL J., BUREAU F., LEKEUX P. Helenalin reduces Staphylococcus aureus infection in vitro and in vivo. Vet. Microbiol. 119, 330, 2007.
  • 11. NEERMAN M. F. Sesquiterpene lactones: a diverse class of compounds found in essential oils possessing antibacterial and antifungal properties. International Journal of Aromatherapy, 13, 114, 2003.
  • 12. SRIVASTAVA R. P., PROKSCH P., WRAY V. Toxicity and antifeedant acivity of sesquiterpene lactone from Encelia against Spodoptera littoralis. Phytochemistry, 29, 3445, 1990.
  • 13. KUPCHAN S. M., FESSLER D. C., EAKIN M. A., GIACOBBE T. J. Reactions of α-methylenelactone tumor inhibitors with model biological nucleophiles. Science, 168, 376, 1970.
  • 14. SZUMNY A., WAWRZEŃCZYK C. Lactones, Part 28: A new approach for the synthesis of α-methylene lactones from alkenes. Synlett. 10, 1523, 2006.
  • 15. NAWROT J., BŁOSZYK E., HARMATHA J., NOVOTNÝ L., DROŻDŻ B. Action of antifeedants of plant origin on beetles infesting stored products. Acta Entomol. Bohemos. 83, 327, 1986.
  • 16. LÓPEZ-OLGUÍN J., DE LA TORRE M., ORTEGO F., CASTANERA P., RODRÍGUEZ B. Structure activity relationships of natural and synthetic neo-clerodane diterpenes from Teucrium against Colorado potato beetle larvae. Phytochemistry, 50, 749, 1999.
  • 17. GOLS G. J. Z., VAN LOON J. J. A., MESSCHENDORP L. Antifeedant and toxic effects of drimanes on Colorado potato beetle larvae. Entomol. Exp. Appl. 79, 69, 1996.
  • 18. SZCZEPANIK M., GRABARCZYK M., SZUMNY A., WAWRZEŃCZYK C. Feeding deterrent activity of lactones with di- and trimethylcyclohexane system against lesser mealworm, Alphitobius diaperinus Panzer and Colorado potato beetle, Leptinotarsa decemlineata Say. J. Plant Protection Res. 43, 87, 2003.
  • 19. WAWRZEŃCZYK C., GRABARCZYK M., SZUMNY A., GABRYŚ B., DANCEWICZ K., NAWROT J., PRĄDZYŃSKA A., HALAREWICZ-PACAN A. Lactones19. [1]. Synthesis and antifeedant activity of lactones with methyl-, dimethyl- and trimethylcycloheksane system. Chemistry for Agriculture, (ed. Górecki, H., Dobrzański, Z., Kafarski, P.), 4, 117, 2003.
  • 20. DANCEWICZ K., KORDAN B., GABRYŚ B., SZUMNY A., WAWRZEŃCZYK C. Feeding deterrent activity of α-methylenelactones to pea aphid Acyrthosiphon pisum (Harris) and green peach aphid Myzus persicae (Sulzer). Pol. J. Natur. Sc. 20, 23, 2006.
  • 21. SZCZEPANIK M., SZUMNY A., GRUDNIEWSKA A., WAWRZEŃCZYK C. Feeding deterrent activity of α-methylenelactones against the lesser mealworm, Alphitobius diaperinus Panzer. Pestycydy/Pesticides, 4, 25, 2005.
  • 22. LOCHYŃSKI S. New biologically active terpenoids obtained from (+)-3-carene. Scientific Papers of the Institute of Organic Chemistry, Biochemistry and Biotechnology of the Wroclaw University of Technology No. 41, Monographs, No. 25, 2004 [In Polish].
  • 23. GONZÁLEZ–COLOMA A., VALENCIA F., MARTIN N., HOFFMANN J. J., HUTTER L., MARCO J. A., REINA M. Silphinene sesquiterpenes as model insect antifeedants. J. Chem. Ecol. 28, 117, 2002.
  • 24. SZCZEPANIK M., DAMS I., WAWRZEŃCZYK C. Feeding deterrent activity of terpenoid lactones with the pmenthane system against the Colorado potato beetle (Coleoptera:Chrysomelidae). Env. Entomol. 34, 1433, 2005.

Typ dokumentu

Bibliografia

Identyfikatory

Identyfikator YADDA

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