Antifeedant and toxic effects of naturally occurring and synthetic quinones to the cabbage looper, Trichoplusia ni

Crop Protection

Volumn 31, Issue 1, 2012, Pages 8-14

  Akhtar, Yasmin ^a   Isman, Murray B ^a   Niehaus, Lourdes A ^a   Lee, Chi Hoon ^b,c   Lee, Hoi Seon ^b  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b Chonbuk National University   (South Korea)

^c Korea National Institute of Health   (South Korea)

Author keywords

Antifeedant effects; Cabbage looper; Neem; Quinones; Structure activity relationship; Toxicity

Indexed keywords

BIOASSAY; CATERPILLAR; EVERGREEN TREE; FEEDING BEHAVIOR; LEAFY VEGETABLE; ORGANIC COMPOUND; PEST CONTROL; TOXICITY;

AZADIRACHTA INDICA; BRASSICA OLERACEA VAR. CAPITATA; HEXAPODA; TRICHOPLUSIA NI;

EID: 80054092374     PISSN: 02612194     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cropro.2011.09.009     Document Type: Article

References (45)

1. Akhtar Y., Isman M.B., Lee C.H., Lee S.G., Lee H.S. Toxicity of quinones against two-spotted spider mite and three species of aphids in laboratory and greenhouse conditions. Ind. Crops Prod. 2011, 10.1016/j.indcrop.2011.07.033.
2. Akhtar Y., Isman M.B., Pudaru P.M., Nagabandi S., Nair R., Plettner E. Screening of dialkoxy benzenes and disubstituted cyclopentene derivatives against the cabbage looper, Trichoplusia ni, for the discovery of new feeding and oviposition deterrents. J. Agric. Food Chem. 2007, 55:10323-10330.
3. Akhtar Y., Yeoung Y.R., Isman M.B. Comparative bioactivity of selected extracts from Meliaceae and some commercial botanical insecticides against two noctuid caterpillars, Trichoplusia ni and Pseudaletia unipuncta. Phytochem. Rev. 2008, 7:77-88.
4. Akhtar Y., Yu Y., Isman M.B., Plettner E. Dialkoxybenzene and dialkoxyallylbenzene feeding and oviposition deterrents against the cabbage looper, Trichoplusia ni: potential insect behavior control agents. J. Agric. Food Chem. 2010, 58:4983-4991.
5. Banerjee S., Magdum S., kalena P.G., Banerji A. Insect growth regulatory activity of naturally occurring quinones and their derivatives in Dysdercus koenigii Fabr. (Hem., Pyrrhocoridae). J. Appl. Entomol. 2001, 125:25-30.
6. Burgueno-Tapia E., Castillo L., Gonzalez-Coloma A., Joseph-Nathen P. Antifeedant and phytotoxic activity of the sesquiterpene ρ-benzoquinone perezone and some of its derivatives. J. Chem. Ecol. 2008, 34:766-771.
7. Bernays E.A., Chapman R.F. Plant secondary compounds and grasshoppers: beyond plant defenses. J. Chem. Ecol. 2000, 26:1773-1794.
8. Cai Y.Z., Sun M., Xing J., Luo Q., Corke H. Structure-radical scavenging activity relationships of phenolic compounds from traditional Chinese medicinal plants. Life Sci. 2006, 78:2872-2888.
9. Carter F.L., Garlo A.M., Stanely J.B. Termiticidal components of wood extracts: 7-methyl-juglone from Diospyros virginiana. J. Agric. Food Chem. 1978, 26:869-873.
10. Davidson R.H., Lyon W.F. Insect Pests of Farm, Garden, and Orchard 1999, John Wiley & Sons Inc., USA.
11. Frazier J.L. The perception of plant allelochemicals that inhibit feeding. Molecular Aspects of Insect-Plant Associations 1986, 1-42. Plenum Press, New York. L.B. Brattsten, S. Ahmad (Eds.).
12. Ganapaty S., Thomas P.S., Fotso S., Laatsch H. Antitermitic quinones from Diospyros sylvatica. Phytochem. 2004, 65:1265-1271.
13. Günaydin K., Topçu G., Marana I.R. 1,5-Dihydroxyanthraquinones and an anthrone from roots of Rumex crispus. Nat. Prod. Lett. 2002, 16:65-70.
14. Isman M.B. Growth inhibitory and antifeedant effects of azadirachtin on six noctuids of regional economic importance. Pestic. Sci. 1993, 38:57-63.
15. Isman M.B. Insect antifeedants. Pestic. Outlook 2002, 13:129-176.
16. Isman M.B. Botanical insecticides, deterrents, and repellents in modern agriculture and an increasingly regulated world. Ann. Rev. Entomol. 2006, 51:45-66.
17. Jiang Z., Akhtar Y., Bradbury R., Zhang X., Isman M.B. Comparative toxicity of essential oils of Litsea pungens and Litsea cubeba and blends of their major constituents against the cabbage looper, Trichoplusia ni. J. Agric. Food Chem. 2009, 57:4833-4837.
18. Khambay B.P.S., Jewess P.J. The potential of natural naphthoquinones as the basis for a new class of pest control agents - an overview of research at IACR-Rothamsted. Crop Protect. 2000, 19:97-601.
19. Khambay B.P.S., Batty D., Jewess P.J., Bateman G.L., Hollomon D.W. Mode of action and pesticidal activity of the natural product dunnione and of some analogues. Pest Manag. Sc. 2003, 59:174-182.
20. Krishnakumari G.N., Bhuvaneswari, Swapna I.R. Antifeedant activity of quinones from Ventilago madaraspatana. Fitoterapia 2001, 72:672-675.
21. Kraiss H., Cullen E.M. Insect growth regulator effects of azadirachtin and neem oil on survivorship, development and fecundity of Aphis glycines (Homoptera: Aphididae) and its predator, Harmonia axyridis (Coleoptera: Coccinellidae). Pest Manag. Sci. 2008, 64:660-668.
22. Kubo I., Uchida M., Klocke J.A. Insect ecdysis inhibitor from the African medicinal plant, Plumbago capsensis (Plumbaginaceaea). Agric. Biol. Chem. 1983, 47:911-913.
23. Lee C.-H., Lee H.-S. Color alternation and acaricidal activity of juglone isolated from Caesalpinia sappan heartwoods against Dermatophagoides spp. J. Microbiol. Biotechnol. 2006, 16:1591-1596.
24. Lee C.-H., Lee H.-S. Acaricidal activity and function of mite indicator using plumbagin and its derivatives isolated from Diospyros kaki Thunb. roots (Ebenaceae). J. Microbiol. Biotechnol. 2008, 18:314-321.
25. Lee, C.H., 2009. Development of bio-functional materials using quinones and their derivatives derived from aromatic medicinal plants, Ph.D. Dissertation. Jeonju: Chonbuk National University.
26. Miller J.R., Cowles R.S. Stimulo-deterrent diversionary cropping: a concept and its possible application to onion maggot control. J. Chem. Ecol. 1990, 16:3197-3212.
27. Mota-Sanchez D., Bills P.S., Whalon M.E. Arthropod resistance to pesticides: status and overview. Pesticides in Agriculture and the Environment 2002, 241-272. Marcel Dekker Inc., New York. W.B. Wheeler (Ed.).
28. Mozaina K., Cantrell C.L., Mims A.B., Lax A.R., Tellez M.R. Activity of 1,4-Benzoquinones against formosan subterranean termites (Coptotermes formosanus). J. Agric. Food Chem. 2008, 56:4021-4026.
29. Papageorgiou V.P., Assimopoulou A.N., Couladouros E.A., Hepworth D., Nicolaou K.C. The chemistry and biology of alkannin, shikonin, and related naphthazarin natural products. Angew. Chem. Int. Ed. 1999, 38:270-300.
30. Park B.-S., Kim J.R., Lee S.-U., kim K.S., Takeoka G.R., Ahn Y.-J., Kim J.H. Selective growth-inhibiting effects of compounds identified in Tabebuia impetiginosa inner bark on human intestinal bacteria. J. Agric. Food Chem. 2005, 53:1152-1157.
31. Park B.S., Lee H.K., Lee S.E., Piao X.L., Takeoka G.R., Wong R.L., Ahn Y.J., Kim J.H. Antibacterial activity of Tabebuia impetiginosa Martius ex DC (Taheebo) against Helicobacter pylori. J. Ethnopharmacol. 2006, 105:255-262.
32. Pavunraj M., Muthu C., Ignacimuthu S., Janarthanan S., Duraipandiyan V., Raja N., Vimalraj S. Antifeedant activity of a novel 6-(4,7-hydroxy-heptyl) quinone from the leaves of the milkweed Pergularia daemia on the cotton bollworm Helicoverpa armigera (Hub.) and the tobacco armyworm Spodoptera litura (Fab.). Phytoparasitica 2011, 39:145-150. 10.1007/s12600-010-0141-5.
33. Seffrin R.D.C., Shikano I., Akhtar Y., Isman M.B. Effects of crude seed extracts of Annona atemoya and Annona squamosa L. against the cabbage looper, Trichoplusia ni in the laboratory and greenhouse. Crop Protect. 2010, 29:20-24.
34. Schultz T.W., Sinks G.D., Cronin M.T.D. Quinone-induced toxicity to Tetrahymena: structure-activity relationships. Aquatic Toxicol. 1997, 39:267-278.
35. Simmonds M.S.J., Manlove J.D., Blaney W.M., Khambay B.P.S. Effects of selected botanical insecticides on the behaviour and mortality of the glasshouse whitefly Trialeurodes vaporariorum and the parasitoid Encarsia formosa. Entomol. Exp. Appl. 2002, 102:39-47.
36. Analytical Software, Statistix 8 for Windows 95, 98, NT 2008, Statistix 8, Analytical Software, Tallahassee, Fl, USA.
37. Steinert J., Khalaf H., Rimpler M. High-performance liquid chromatographic separation of some naturally occurring naphthoquinones and anthraquinones. J. Chromatogr. A 1996, 723:206-209.
38. Tellez M., Osbrink W., Kobaisy M. Natural products as pesticidal agents for control of the Formosan termite (Coptotermes formosanus Shiraki). Sociobiology 2003, 41:153-167.
39. Tokunaga T., Takada N., Ueda M. Mechanism of antifeedant activity of plumbagin, a compound concerning the chemical defense in carnivorous plant. Tetrahedron Lett. 2004, 45:7115-7119.
40. Usher B.F., Bernays E.F., Berbehenn R.V. Antifeedant tests with larvae of Pseudaletia unipuncta: variability of behavioral response. Entomol. Exp. Appl. 1988, 48:203-212.
41. Wang P., Zhao J.Z., Rodrigo-Simon A., Kain W., Janmaat A.F., Shelton A.M., Ferré J., Myers J. Mechanism of resistance to Bacillus thuringiensis toxin Cry1Ac in a Greenhouse population of the cabbage looper, Trichoplusia ni. Appl. Environ. Microbiol. 2007, 73:1199-1207.
42. Wu J., Bauer C.E. RegB/RegA, a global redox-responding two-component system. Bacterial Signal Transduction: Network and Drug Targets 2007, 131-148. Landes Bioscience Eurekah, Georgetown, TX. R. Utsumi (Ed.).
43. Yang X., Summerhurst D.K., Koval S.F., Ficker C., Smith M.L., Bernards M.A. Isolation of an antimicrobial compound from Impatients balsamina L. using bioassay-guided fractionation. Phytother. Res. 2001, 15:676-680.
44. Yang Y.C., Lim M.Y., Lee H.S. Emodin isolated from Cassia obtusifolia (Leguminosae) seed shows larvicidal activity against three mosquito species. J. Agric. Food Chem. 2003, 51:7629-7631.
45. Zar J.H. Biostatistical Analysis 1984, Prentice-Hall, Englewood Cliffs, NJ, 130 pp. second ed.