Feeding deterrent activity of terpenoid lactones with the p-menthane system against the Colorado potato beetle (Coleoptera: Chrysomelidae)

Environmental Entomology

Volumn 34, Issue 6, 2005, Pages 1433-1440

  Szczepanik, M ^a   Dams, I ^b   Wawrzenczyk C ^b  

^a NICOLAUS COPERNICUS UNIVERSITY   (Poland)

^b WROC AW UNIVERSITY OF ENVIRONMENTAL AND LIFE SCIENCES   (Poland)

Author keywords

Antifeedants; Isopulegol; Leptinotarsa decemlineata; Pulegone; Terpenoid lactones

Indexed keywords

ANTIFEEDANT; BEETLE; PEST CONTROL;

CHRYSOMELIDAE; COLEOPTERA; HEXAPODA; INSECTA; LEPTINOTARSA DECEMLINEATA;

EID: 29544439723     PISSN: 0046225X     EISSN: None     Source Type: Journal    
DOI: 10.1603/0046-225X-34.6.1433     Document Type: Article

References (68)

1. Appel, H. H., R.P.M. Bond, and K. H. Overton. 1963. Sesquiterpenoids - III. The constitution and stereochemistry of valdiviolide, fuegin, winterin and futronolide. Tetrahedron. 19: 635-641.
2. Asakawa, Y., G. D. Dawson, D. C. Griffiths, J.-Y. Lallemand, S. V. Ley, K. Mori, A. Mudd, M. Pezechk-Leclaire, J. A. Pickett, H. Watanabe, C. M. Woodcock, and Z. Zhong-Ning. 1988. Activity of drimane antifeedants and related compounds against aphids, and comparative biological effects and chemical activity of (-)-and (+)-polygodial. J. Chem. Ecol. 14: 1845-1855.
3. Avery, M. L., D. G. Decker, J. S. Humphrey, and C. C. Lankert. 1996. Mint plant derivatives as blackbird feeding deterrents. Crop Prot. 15: 461-464.
4. Bellés, X., F. Camps, J. Coll, and M.D. Pinlachs. 1985. Insect antifeedant activity of clerodane cliterpenoids against larvae of Spodoptera littoralis (Boisd.) (Lepidoptera). J. Chem. Ecol. 11: 1439-145.
5. Bentley, M. D., M. S. Rajah, M. J. Mendel, and A. R. Alford. 1990. Limonoid model insect antifeedants. J. Agric. Food Chem. 38: 1400-1403.
6. Bernays, E. A., and R. F. Chapman. 1977. Deterrent chemicals as a basic for oligophagy in Locusta migratoria (L.). Ecol. Entomol. 2: 1-18.
7. Bernays, E. A., and R. F. Chapman. 2000. Plant secondary compounds and grasshoppers: beyond plant defenses. J. Chem. Ecol. 26: 1773-1794.
8. Blaney, W. M., M.S.J. Simmonds, S. V. Ley, and R. B. Katz. 1987. An electrophysiological and behavioral study of insect antifeedant properties of natural and synthetic drimane-related compounds. Physiol. Entomol. 12: 281-289.
9. Blaney, W. M., M.S.J. Simmonds, S. V. Ley, J. C. Anderson, and P. L. Toolgood. 1990. Antifeedant effects of azadirachtin and structurally related compounds on lepidopterous larvae. Eutomol. Exp. Appl. 55: 149-160.
10. Casagrande, R. A. 1987. The Colorado potato beetle: 125 years of mismanagement. Bull. Entomol. Soc. Am. 33: 142-150.
11. Chapman, R. F. 1974. The chemical inhibition of feeding by phytophagous insects. Bull. Entomol. Res. 64: 339-363.
12. Coombs, J. J., D. S. Douches, W. Li, E. J. Grafus, and W. L. Pett. 2003. Field evaluation of natural, engineered and combined resistance mechanisms in potato for control of Colorado potato beetle. J. Am. Soc. Hort. Sci. 128: 219-224.
13. Dams, I., A. Bialońska, Z. Ciunik, and C. Wawrzeńezyk. 2004a. Lactones. 21. Synthesis and odoriferous properties of lactones with the p-menthane system. J. Agric. Food Chem. 52: 1630-1634.
14. Dams, I., A. Bialońska, Z. Ciunik, and C. Wawrzeńczyk. 2004b. Lactones. 22. Synthesis of terpenoid lactones with the p-menthane system. Eur. J. Org. Chem. 2662-2668.
15. Dams, I., A. Bialońska, Z. Ciunik, and C. Wawrzeńczyk. 2005a. Lactones. 23. Synthesis of cis-fused bicyclic hydroxy lactones with the p-Menthane System, Tetrahedron: Asymmetry 16: 2087-2097.
16. Dams, I., A. Bialońska, Z. Ciunik, and C. Wawrzeńczyk. 2005b. Lactones. 25. Synthesis of unsaturated δ-lactones with the p-menthane system. Eur. J. Org. Chem. (in press).
17. Daniewski, W. M., M. Gumułka, E. Pankowska, K. Ptaszyńska, E. Błoszyk, U. Jacobsson, and T. Norin. 1993. 3,8-Ethers of lactarane sesquiterpenes. Phytochemistry. 32: 1499-1502.
18. Daniewski, W. M., M. Gumułka, D. Przesmycka, K. Ptaszyńska, E. Błoszyk, and B. Drożdż. 1995. Sesquiterpenes of Lactarius origin, antifeedant - structure activity relationships. Phytochemistry. 38: 1161-1168.
19. Fontana, G., M. P. Paternostro, G. Savona, B. Rodriguez, and M. C. de la Torre. 1998. Neoclerodane diterpenoids from Teucrium massiliense. J. Nat. Prod. 61: 1242-1247.
20. Franzios, G., M. Mirotsou, E. Hatziapostolou, J. Kral, Z. G. Scouras, and P. Mavragani-Tsipodu. 1997. Insecticidal and genotoxic activities of mint essential oils. J. Agric. Food. Chem. 45: 2690-2694.
21. Gebbinck, E.A.K., C. T. Bouwman, M. Bourgois, B.J.M. Jansen, and Ae. de Groot. 1999. Synthesis and insect antifeedant activity of C-2 and C-5 substituted perhydrofurofurans and 3a-hydroxy-perhydrofurofurans (part I). Tetrahedron. 55: 11051-11076.
22. González-Coloma, A., F. Valencia, N. Martín, J. Hoffmann, L. Hutter, J. A. Marco, and M. Reina. 2002. Silphinene sesquiterpenes as model insect antifeedants. J. Chem. Ecol. 28: 117-129.
23. Gordon, W. P., A. J. Forte, R. J. McMurty, H. Gal, and S. D. Nelson. 1982. Hepatotoxicity and pulmonary toxicity of pennyroyal oil and its constituent terpenes in the mouse. Toxicol. Appl. Pharmacol. 65: 413-424.
24. Grunschober, F. 1979. Literature review of pulegone. Perfum Flavor. Int. 4: 15-17.
25. Gunderson, C. A., J. H. Samuelian, C. K. Evans, and L. B. Brattsten. 1985. Effects of the mint monoterpene pulegone on Spodoptera eridania (Lepidoptera: Noctuidae). Environ. Entomol. 14: 859-863.
26. Hare, J. D. 1990. Ecology and management of the Colorado potato beetle. Annu. Rev. Entomol. 35: 81-100.
27. Harris, C. R., and H. J. Svec. 1981. Colorado potato beetle resistance to carbofuran and several other insecticides in Quebec. J. Econ. Entomol. 74: 421-424.
28. Harmatha, J., and J. Nawrot. 1984. Comparison of the feeding deterrent activity of some sesquiterpene lactones and lignan lactone towards selected insect storage pests. Biochem. Syst. Ecol. 12: 95-98.
29. Harmatha, J., and J. Nawrot. 2002. Insect feeding deterrent activity of lignans and related phenylpropanoids with a methylenedioxyphenyl (piperonyl) structure moiety. Entomol. Exp. Appl. 104: 51-60.
30. Harwood, S. H., A. F. Moldenke, and R. E. Berry. 1990. Toxicity of peppermint monoterpenes to the variegated cutworm (Lepioptera: Noctuidae). J. Econ. Entomol. 83: 1761-1767.
31. Hough-Goldstein, J. A. 1990. Antifeedant effects of common herbs on the Colorado potato beetle (Coleoptera: Chrysomelidae). Environ. Entomol. 19: 234-238.
32. Hough-Goldstein, J. A., and C. B. Keil. 1991. Prospects for integrated control of the Colorado potato beetle (Coleoptera: Chrysomelidae) using Perillus bioculatus (Hemiptera: Pentatomidae) and various pesticides. J. Econ. Entomol. 84: 1645-1651.
33. Hsiao, T. H. 1976. Chemical and behavioral factor influencing food selection of Leptinotarsa beetle. Symp. Biol. Hung. 16: 95-99.
34. Inazuka, S. 1983. Monoterpenoids as repellents against the German cockroach. J. Pest. Sci. 8: 293-299.
35. Jermy, T., B. A. Butts, L. McDonought, D. L. Dreyer, and A. F. Rose. 1981. Antifeedants for the Colorado potato beetle. Antifeedant constituents of some plants from the sagebrush community. Insect Sci. Appl. 1: 237-242.
36. Johnston, R. L., and L. E. Sandovol. 1986. Susceptibility of Idaho populations of Colorado potato beetle to four classes of insecticides. Am. Potato J. 63: 81-85.
37. Kieslich, K. 1991. Biotransformations of industrial use. Acta Biotechnol. 11: 559-570.
38. Kubo, I., Y.-W. Lee, V. Balogh-Nair, K. Nakanishi, and A. Chapya. 1976. Structure of ajugarins. J.C.S. Chem. Commun. 949-950.
39. Labbé, C., F. Faini, C. Villgran, J. Coll, and D. S. Rycroft. 2005. Antifungal and insect antifeedant 2-phenylethanol esters from the liverwort Balantiopsis cancellata from Chile. J. Agric. Food Chem. 53: 247-249.
40. Lacey, L. A., D. R. Horton, R. L. Chauvin, and J. M. Stocker. 1999. Comparative efficacy of Beauveria bassiana, Bacillus thuringiensis, and aldicarb for control of Colorado poato beetle in an irrigated desert agroecosystem and their effects on biodiversity. Entomol. Exp. Appl. 93: 189-200.
41. Lawrencet, B. M. 2000. Essential oils: from agriculture to chemistry. Int. J. Aromather. 10: 82-98.
42. Lee, S., C. J. Peterson, and J. R. Coats. 2003. Fumigation toxicity of monoterpenoids to several stored product insects. J. Stor. Prod. Res. 39: 77-85.
43. Lewis, A. C., and H. F. van Emden. 1986. Assays for insect feeding, pp. 95-119. In J. R. Miller and T. A. Miller (eds.), Insect-plant interactions. Springer, New York.
44. Ley, S. V., and P. L. Toogood. 1990. Insect antifeedants. Chem. Br. 3: 31-35.
45. López-Olguín, J., M. de la Torre, F. Ortego, P. Castaňera, and B. Rodriguez. 1999. Structure activity relationships of natural and synthetic neo-clerodane diterpenes from Teucrium against Colorado potato beetle larvae. Phytochemistry. 50: 749-753.
46. Mason, J. R., and T. Primus. 1996. Response of European starlings to menthone derivatives: evidence for stereochemical differences in repellency. Crop Prot. 15: 723-726.
47. Menn, J. J. 1983. Present insecticides and approaches to discovery of environmentally acceptable chemicals for pest management, pp. 5-31. In D. L. Whitehead and W. S. Bowers (eds.), Natural products for innovative pest management. Pergamon, Oxford, UK.
48. Moorthy, B., P. Madyastha, and K. M. Madyastha. 1989. Hepatotoxicity of pulegone in rats: its effects on microsomal enzymes in vivo. Toxicology. 55: 327-337.
49. Munakata, K. 1975. Insect antifeeding substances in plant leaves. Pure Appl. Chem. 42: 57-66.
50. Murray, K. D., S. Hasegawa, and A. R. Alford. 1999. Antifeedant activity of citrus limonoids against Colorado potato beetle: comparison of aglycones and glucosides. Entomol. Exp. Appl. 92: 331-334.
51. Nawrot, J., B. Drożdż, and M. Holub. 1985. Feeding deterrent activity of some natural sesquiterpene lactones for selected storage pests. Herba Polonica. 31: 209-213.
52. Nawrot, J., E. Bloszyk, J. Harmatha, L. Novotný, and B. Drożdż. 1986. Action of antifeedants of plant origin on beetles infesting stored products. Acta Entomol. Bohemoslov. 83: 327-335.
53. Noronha, Ch., G. M. Duke, J. M. Chinn, and M. S. Goettel. 2001. Differential susceptibility to insecticides by Leptinotarsa decemlineata (Coleoptera) populations from western Canada. Phytoprotection. 82: 113-121.
54. Olsen, P., and I. Thorup. 1984. Neurotoxicity in rats dosed with peppermint oil and pulegone. Arch. Toxicol. Suppl. 7: 408-409.
55. Paruch, E., Z. Ciunik, J. Nawrot, and C. Wawrzeńczyk. 2000. Synthesis of terpenoid lactones - active insect antifeedants. J. Agric. Food. Chem. 48: 4973-4977.
56. Paruch, E., J. Nawrot, and C. Wawrzeńezyk. 2001. Feeding deterrent activity of some bi- and tricyclic terpenoid lactones. Pest Manag. Sci. 57: 776-780.
57. Paul, V. J., P. Ciminiello, and W. Fenical. 1988. Diterpenoid feeding deterrents from the pacific green alga Pseudochlorodesmis furcellata. Phytochemistry. 27: 1011-1014.
58. Radcliffe, E. B. 1982. Insect pests of potato. Annu. Rev. Entomol. 27: 173-204.
59. Rice, P. J., and J. R. Coats. 1994. Insecticidal properties of several monoterpenoids to the house fly (Diptera: Muscidae), red flour beetle (Coleoptera: Tenebrionidae) and southern maize rootworm (Coleoptera: Chrysomelidae). J. Econ. Entomol. 87: 1172-1179.
60. Rice, R. L., D. E. Lincolu, and J. H. Langenheim. 1978. Palatability of monoterpenoid compositional types of Satureja douglassi to a generalist molluscan herbivore, Ariolimax dolichophallus. Biochem. Syst. Ecol. 6: 45-53.
61. Schoonhoven, L. M. 1982. Biological aspects of antifeedants. Entomol. Exp. Appl. 31: 57-69.
62. Schrod, J., T., Basedow, and G. A. Langenbruch. 1996. Untersuchungen zur Bionomie und zur biologischen Bekämpfung des Kartoffelkäfers (Leptinotarsa decemlineata Say. Col., Chrysomelidae) an zwei Standorten in Südhessen (BRD). J. Appl. Entomol. 120: 019-626.
63. Streibl, M., J. Nawrot, and V. Herout. 1983. Feeding deterrent activity of enantiomeric isoalantones. Biochem. Syst. Ecol. 11: 381-382.
64. Tokoroyma, T. 2000. Synthesis of clerodane diterpenoids and related compounds. Stereoselective construction of the decalin skeleton with multiple contiguous stereogenic centers. Synthesis. 611-633.
65. Watanabe, K., Y. Shono, A. Kakimizu, A. Okada, N. Matsuo, A. Satoh, and H. Nishimura. 1993. New mosquito repellent from Eucalyptus camaldulensis. J. Agric. Food. Chem. 41: 2164-2166.
66. Wawrzeńezyk, C., E. Paruch, T. Olejniczak, A. Saletra, J. Nawrot, A. Pra̧dzyńska, A. Halarewicz-Pacan, and B. Gabryś. 1998. The effect of the compound configuration on the feeding deterrent activity of some terpenoid lactones. pp. 222-227. In D. Konopińska (ed.), Insects, chemical, physiological and environmental aspects. University of Wroclaw, Wroclaw, Poland.
67. Zabel, A., B. Manojlovic, S. Rajkovic, S. Stankovic, and M. Kostic. 2002. Effect of neem extract on Lymantria dispar L. (Lepidoptera: Lymantridae) and Leptinotarsa decemlineata Say. (Coleoptera: Chrysomelidae). J. Pest. Sci. 75: 19-25.
68. Zalkow, L. H., M. M. Gordon, and N. Lanir. 1979. Antifeedants from rayless goldenrod and oil of pennyroyal: toxic effect for the fall armyworm. J. Econ. Entomol. 72: 812-815.