Bioactivity and structure–activity relationship of natural methoxylated phenylpropenes and their derivatives against Aphis craccivora Koch (Hemiptera: Aphididae)

Springer Science and Business Media LLC - Tập 79 - Trang 209-214 - 2006
Dhananjay Kumar Tewary1, Anu Bhardwaj1, Anuj Sharma1, Arun Kumar Sinha1, Adarsh Shanker1
1Institute of Himalayan Bioresource Technology, Council of Scientific and Industrial Research, Palampur, India

Tóm tắt

In the light of recent increased interest in developing plant based secondary chemistry into products suitable for integrated pest management, the objective of the present study was to investigate the bioactivity in field simulated conditions and structure–activity relationship of some natural phenylpropenes and their related analogues (1–6) against Aphis craccivora. The activities of different compounds varied depending on the substitution of the functional groups and the side chain attached to the aromatic ring of the phenylpropene. Dimethyleugenol (5) showed maximum activity among all tested phenylpropenes with LC50 values 880 and 2,047 ppm against nymphs and adults respectively. Present study showed that phenylpropenes appear to be promising natural insecticides and may hold potential for identification of new lead structures against A. craccivora. The activity of the most active phenylpropene (5) was comparable with that of the chemical pesticide (dimethoate).

Tài liệu tham khảo

Abbott WS (1925) A method of computing the effectiveness of an insecticide. J Econ Entomol 18:265–267 Abdallah SA, Barakat AA, Badawy HMA, Soliman MMM (2004) Insecticidal activity of different wild plant extracts against the cowpea aphid, Aphis craccivora Koch. Paper presented at the first Arab conference of applied biological pest control, April 5–7, Cairo, Egypt Ahn YJ, Lee SB, Lee HS, Kim GH (1998) Insecticidal and acaricidal activity of carvacrol and β-thujaplicine derived from Thujopsis dolabrata var. Hondai sawdust. J Chem Ecol 24:81–90 Capasso R, Evindente A, Tremblay E, Sala A, Santoro C, Cristinzio G, Scognamiglio F (1994) Direct and mediated effects on Bactrocera oleae (Gmelin) [Diptera: Tephritidae] of natural phenols and some related synthetic compounds. Structure activity relationships. J Chem Ecol 20:1189–1199 De Paula JR, Viera IJC, Da Silva GF, Rodriguez FOE, Fernandes JB, Vieira PC, Pinheiro AL, Vilela EF (1997) Sesquiterpenes, triperpenoids, limonoids and flavonoids of Cedrela odorata graft and speculations on the induced resistance against Hypsipyla grandella. Phytochem 44:1449–1454 Dreyer DL, Jones KC (1981) Feeding deterrency of flavonoids and related phenolics towards Schizaphhis graminum and Myzus persicae; Aphid feeding deterrents in wheat. Phytochem 20:2489–2493 Flint ML (2000) How to manage pests. Pests in landscapes and gardens in UC IPM online state wide integrated pest management program. University of California, Agriculture and Natural resources Hamaraoui A, Regnault-Roger C (1997) Comparison of insecticidal activities of monoterpenes on two insect pests of cultures: Ceratitis capitata et Rhopalosiphum padi. Acta Gallica Botanica 144:413–417 Han Z, Li F (2004) Mutations in acetyl-cholinesterase associated with insecticide resistance in the cotton aphid, Aphis gossypii Glover. Insect Biochem Mol Biol 34:397–405 Harborne JB, Baxter H (1993) Phytochemical dictionary, a handbook of bioactive compounds from plants. Taylor and Francis Ltd., USA, pp 474 Harmatha J, Nawrot J (2002) Insect feeding deterrent activity of lignans and related phenylpropanoids with a methylenedioxyphenyl (piperonyl) structure moiety. Entomol Exp Appl 104:51–60 Henrick CA, (1995) Pyrethroids. In: Godfrey CRA (eds) Agrochemicals from Natural Products. Marcel Dekker, New York, pp 117 Holland JM, Winder L, Perry JN (2000) The impact of dimethoate on the spatial distribution of beneficial arthropods in winter wheat. Ann Appl Biol 136:93–105 Hollingsworth RG, Tabashnik BE Ullman DE, Johnson MW, Messing R (1994) Resistance of Aphis gossypii (Homoptera: Aphididae) to insecticides in Hawaii: Spatial patterns and relationship to insecticide use. J Econ Entomol 87:293–300 Hummelbrunner LA, Isman MB (2001) Acute, sublethal, antifeedant, and synergistic effects of monoterpenoid essential oil compounds on the tobacco cutworm, Spodoptera litura (Lep., Noctuidae). J Agric Food Chem 49:715–720 Isman MB, (2000) Plant essential oils for pest and disease management. Crop Protect 19:603–608 Isman MB, Wan AJ, Passreiter CM (2001) Insecticidal activity of essential oils to the tobacco cutworm, Spodoptera litura. Fitoterapia 72:65–68 Jansen JP (2000) A 3-year field study on the short-term effects of insecticides used to control cereal aphids on plant-dwelling predators in winter wheat. Pest Manage Sci 56:533–539 Khambay BPS, Jewess P (2000) 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 19:597–601 Kim DH, Ahn YJ (2001) Contact and fumigant activites of constitutents of Foenciculum vulgare fruit against three coleopteran stored product insects. Pest Manage Sci 57:301–306 Kim EH, Kim HK, Ahn YJ (2003) Acaricidal activity of clove bud oil compounds against Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari :pyroglyphidae). J Agric Food Chem 51:885–889 Lee SG, Kim SI, Ahn YJ, Kim JB, Lee BY (1997) Effectiveness of carvacrol derived from Thujopsis dolabrata var. hondai Sawdust against Thecodiplosis japonensis (Diptera: Cecidomyiidae). Pestic Sci 49:119–124 Obeng-Ofori D, Alder C, Reichmuth C (1997) Toxicity and repellency of 1,8-cineole, eugenol and camphor against stored product insects. Proceedings of the German society for general and applied entomology. Bayreuth, Germany 259–264 Obeng-ofori D, Reichmuth C (1997) Bioactivity of eugenol, a major component of Ocimum basilicum suave (Wild.) against four species of stored product Coleoptera. Int J Manage 43:89–94 Ofuya TI, Okuku IE (1994) Insecticidal effect of some plant extracts on the cowpea aphid Aphis craccivora Koch (Homoptera: Aphididae). Anzeir fuer Schaedlingskunde Pflanzenschutz Umweltschutz 67: 127–129. Department of Biology, Royal Holloway University London, Egham, UK Owen smith DN (1995) Condensed tannin in Erasgrostis chloromelas leaves deters feeding by a generalist grasshopper. Afri J Range Forage Sci 12:49–52 Palumbo J, Tickes B (2001) Cowpea aphids in Alfalfa in Yuma County farm notes. University of Arizona, Arizona Paneru RB, Le Patoure GNJ, Kennedy SH (1997) Toxicity of Acorus calamus rhizome powder from Eastern Nepal to Sitophilus granaries (L.) and Sitophilus oryzae (L.) (Coleoptera, Curculionidae). Crop Protect 16:759–763 Park BS, Lee SE, Choi WS, Jeong CY, Song C, Cho KY (2002) Crop Protect 21:249–251 Park C, Kim S, Ahn YJ (2003) Insecticidal activity of asarones identified in Acorus gramineus rhizome against three coleopteran stored product insects. J Stored Prod Res 39:333–342 Passreiter CM, Wilson J, Andersen R, Isman MB (2004) Metabolism of Thymol and trans-Anethole in Larvae of Spodoptera litura and Trichoplusia ni (Lepidoptera: Noctuidae). J Agric Food Chem 52:2540–2551 Regnault-Roger C, Ribodeau M, Hamraoui A, Bareau I, Blanchard P, Gil-Munoz M, Barberan FT (2004) Poloyphenolic compounds of mediterranean Lamiaceae and investigation of orientational effects on Acanthoscelides obtectus (Say). J Stored Prod Res 40:395–408 Saxena BP, Koul O, Tikku K, Atal CK (1977) A new insect chemosterilant isolated from Acorus calamus L. Nature 270:512–513 Schreiner I (2000) Cowpea aphids (Aphis craccivora Koch). Paper published in agricultural pests of the pacific, ADAP 2000–6 Shetlar DJ (2001) Aphids on trees and shrubs, HYG-2031–90. Ohio State University Extension Fact sheet. Department of Horticulture and Crop Science. Ohio State University, USA Sinha AK, Acharya R, Joshi BP (2002) A mild and convenient procedure for the conversion of toxic β-asarone into rare phenylpropanoids: 2, 4, 5-Trimethoxycinnamaldehyde and α-Asarone. J Nat Prod 65:764–765 Sinha AK, Joshi BP, Dogra R (2003) Microwave assisted rapid and economical process for the preparation of substituted phenylaldehydes from trans and cis-phenylpropenes: a commercial utilization of toxic cis-isomer. US Patent 6,544,390 Sinha AK (2003) Process for the preparation of 1–Propyl–2,4,5–trimethoxybenzene from toxic beta-asarone of Acorus calamus or from crude calamus oil containing beta-asarone. US Patent 6,528,041 Streloke M, Ascher KRS, Schmidt GH, Neumann WP (1989) Vapour pressure and volatility of β-asarone, the main ingredient of an indigigenous stored-product insecticide, Acorus calamus oil. Phytoparasitica 17:299–313 Suliman R, Saker I, Namora D (2003) Paper presented at The eighth Arab congress of plant protection, October 12–16, El-Beida city, Libya Tewary DK, Bhardwaj A, Shanker A (2005) Pesticidal activities in five medicinal plants collected from mid hills of western Himalayas. Ind Crops Prod 22(3):241–247 Welty C, Murphy J (1991) Wooly Apple Aphid. HYG-2,208–94 Ohio State University extension fact sheet, Department of Entomology, Ohio State University, USA