Bioefficacy of acyclic monoterpenes and their saturated derivatives against the West Nile vector Culex pipiens

Chemosphere

Volumn 96, Issue , 2014, Pages 74-80

  Michaelakis, Antonios ^a   Vidali, Veroniki P ^b   Papachristos, Dimitrios P ^a   Pitsinos, Emmanuel N ^b   Koliopoulos, George ^a   Couladouros, Elias A ^b,c   Polissiou, Moschos G ^c   Kimbaris, Athanasios C ^d  

^a BENAKI PHYTOPATHOLOGICAL INSTITUTE   (Greece)

^b INSTITUTE OF NANOSCIENCE AND NANOTECHNOLOGY   (Greece)

^c AGRICULTURAL UNIVERSITY OF ATHENS   (Greece)

^d DEMOCRITUS UNIVERSITY OF THRACE   (Greece)

Author keywords

Acyclic monoterpenes; Culex pipiens; Larvicide; Repellency; Structure activity relationships

Indexed keywords

ISOMERS; TOXICITY;

ACYCLIC MONOTERPENES; CULEX PIPIENS; LARVICIDE; REPELLENCY; STRUCTURE ACTIVITY RELATIONSHIPS;

MONOTERPENES;

ALCOHOL DERIVATIVE; BENZOYL PEROXIDE; BETA CITRAL; CARBONYL DERIVATIVE; CARBOXYL GROUP; CARBOXYLIC ACID; CITRAL; CITRONELLIC ACID; CITRONELLOL; CITRONELLYL ACETATE; DIETHYLTOLUAMIDE; DIHYDROCITRONELLAL; DIHYDROCITRONELLOL; DIHYDROCITRONELLYL ACETATE; DIHYDROLINALOOL; DIHYDROLINALYL ACETATE; ESTER; GERANIOL; GERANYL ACETATE; HYDROXYL GROUP; ICARIDIN; INSECT REPELLENT; LARVICIDAL AGENT; LINALOOL; LINALYL ACETATE; NEROL; NERYL ACETATE; TERPENE; TETRAHYDROLINALYL ACETATE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ACETATE; BIOASSAY; DISEASE VECTOR; FUNCTIONAL GROUP; MOSQUITO; OXIDATION; REPELLENT; SATURATION; TOXICITY;

ARTICLE; CHEMICAL BOND; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CULEX PIPIENS; HYDROGENATION; INSECTICIDAL ACTIVITY; LC 50; NONHUMAN; OXIDATION; REDUCTION; SYNTHESIS; TOXICITY TESTING;

CULEX PIPIENS;

ACYCLIC MONOTERPENES; CULEX PIPIENS; LARVICIDE; REPELLENCY; STRUCTURE-ACTIVITY RELATIONSHIPS;

ANIMALS; CULEX; INSECTICIDES; MONOTERPENES; MOSQUITO CONTROL; TOXICITY TESTS; WEST NILE FEVER;

EID: 84887606269     PISSN: 00456535     EISSN: 18791298     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2013.07.032     Document Type: Article

References (47)

1. Badolo A., Ilboudo-Sanogo E., Ouedraogo A.P., Costantini C. Evaluation of the sensitivity of Aedes aegypti and Anopheles gambiae complex mosquitoes to two insect repellents: DEET and KBR3023. Trop. Med. Int. Health 2004, 9:330-334.
2. Brared-Christensson J., Matura M., Gruvberger B., Bruze M., Karlberg A.T. Linalool - a significant contact sensitizer after air exposure. Contact Dermat. 2010, 62:32-41.
3. Bougioukou D.J., Walton A.Z., Stewart J.D. Towards preparative-scale, biocatalytic alkene reductions. Chem. Commun. 2010, 46:8558-8560.
4. Chantraine J.-M., Laurent D., Ballivian C., Saavedra G., Ibanez R., Vilaseca L.A. Insecticidal activity of essential oils on Aedes aegypti larvae. Phytother. Res. 1998, 12:350-354.
5. Cheng S.S., Liu J.Y., Huang C.G., Tsai K.H., Chen W.J., Chang S.T. Chemical composition and mosquito larvicidal activity of essential oils from Leaves of different Cinnamomum osmophloeum provenances. J. Agric. Food Chem. 2004, 52:4395-4400.
6. Cheng S.S., Liu J.Y., Huang C.G., Hsui Y.R., Chen W.J., Chang S.T. Insecticidal activities of leaf essential oils from Cinnamomum osmophloeum against three mosquito species. Bioresour. Technol. 2009, 100:457-464.
7. Koul O., Walia S., Dhaliwal G.S. Essential oils as green pesticides: potential and constraints. Biopestic. Int. 2008, 4:63-84.
8. Divkovic M., Peace C.K., Gerberick G.F., Basketter D.D. Hapten-protein binding: from theory to practical application in the in vitro prediction of skin sensitization. Contact Dermat. 2005, 53:189-200.
9. Environmental Protection Agency, 2008. Citronella Fact sheet. August 5 http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_021901.htm.
10. Giatropoulos A., Papachristos D.P., Kimbaris A., Koliopoulos G., Polissiou M.G., Emmanouel N., Michaelakis A. Evaluation of bioefficacy of three Citrus essential oils against the dengue vector Aedes albopictus (Diptera: Culicidae) in correlation to their components enantiomeric distribution. Parasitol. Res. 2012, 111:2253-2263.
11. Govere J.M., Durrheim D.V. Techniques for evaluating repellents. Insect Repellents: Principles, Method, User 2006, 281. Tayler and Francis-Publishing Inc., Boca Raton. M. Debboun, S.P. Frances, D. Strickman (Eds.).
12. Hagvall L., Backtrorp C., Norrby P.O., Karlberg A.T., Borje A. Experimental and theoretical investigations of the autoxidation of geranial: a dioxolane hydroxyperoxide identified as a skin sensitizer. Chem. Res. Toxicol. 2011, 24:1507-1515.
13. Hays W.J., Laws E.R. Handbook of Pesticide Entomology, vol. 1. General Principles 1991, Academic Press, New York.
14. Hubálek Z., Halouzka J. West Nile fever-a reemerging mosquito-borne viral disease in Europe. Emerg. Infect. Dis. 1999, 5:643-650.
15. Isman M.B., Miresmailli S., Machlial C. Commercial opportunities for pesticides based on plant essential oils in agriculture, industry and consumer products. Phytochem. Rev. 2011, 10:197-204.
16. Jha S.K., Cheon K.-S., Green M.M., Selinger J.V. Chiral optical properties of a helical polymer synthesized from nearly racemic chiral monomers highly diluted with achiral monomers. J. Am. Chem. Soc. 1999, 121:1665-1673.
17. Kaufman P.E., Mann R.S., Butler J.F. Evaluation of semiochemical toxicity to Aedes aegypti, Ae. albopictus and Anopheles quadrimaculatus (Diptera: Culicidae). Pest Manage. Sci. 2010, 66:497-504.
18. Klun J.A., Khrimian A., Margaryan A., Kramer M., Debboun M. Synthesis and repellent efficacy of a new chiral piperidine analog: comparison with DEET and Bayrepel activity in human-volunteer laboratory assays against Aedes aegypti and Anopheles stephensi. J. Med. Entomol. 2003, 40:293-299.
19. Kioulos I., Kampouraki A., Morou E., Skavdis G., Vontas J. Insecticide resistance status in the major WNV vector Culex pipiens from Greece. Pest Manage. Sci. 2013, 10.1002/ps.3595.
20. Koliopoulos G., Pitarokili D., Kioulos E., Michaelakis A., Tzakou O. Chemical composition and larvicidal evaluation of Mentha, Salvia and Melissa essential oils against the West Nile virus mosquito Culex pipiens. Parasitol. Res. 2010, 107:327-335.
21. Leal W.S., Uchida K. Application of GC-EAD to the determination of mosquito repellents derived from a plant Cymbopogon citratus. J. Asia Pac. Entom. 1998, 12:217-221.
22. Lopez O., Fernandez-Bolanos J.G., Gil M.V. New trends in pest control: the search for greener insecticides. Green Chem. 2005, 7:431-442.
23. Melliou E., Michaelakis A., Koliopoulos G., Skaltsounis A.L., Magiatis P. High quality bergamot oil from Greece: chemical analysis using enantiomeric GC-MS and larvicidal activity against the West Nile virus vector. Molecules 2009, 14:839-849.
24. Michaelakis A., Mihou A.P., Couladouros E.A., Zounos A.K., Koliopoulos G. Oviposition responses of Culex pipiens to a synthetic racemic Culex quinquefasciatus oviposition aggregation pheromone. J. Agric. Food Chem. 2005, 53:5225-5229.
25. Moore S.J., Lenglet A., Hill N. Plant-based insect repellents. Insect Repellents: Principles, Method, User 2007, 281. Tayler and Francis-Publishing Inc., Boca Raton. M. Debboun, S.P. Frances, D. Strickman (Eds.).
26. Muller P., Rossier J.-C. Solvent effects on the steric course of the solvolysis of tertiary acyclic derivatives. J. Chem. Soc. Perkin Trans. 2; Phys. Org. Chem. 2000, 11:2232-2237.
27. Nerio L.S., Olivero-Verbel J., Stashenko E. Repellent activity of essential oils: a review. Bioresour. Technol. 2010, 101:372-378.
28. Omolo M.O., Okinyo D., Ndiege I.O., Lwande W., Hassanali A. Repellency of essential oils of some Kenyan plants against Anopheles gambiae. Phytochemistry 2004, 65:2797-2802.
29. Oritani T., Yamashita K. Microbial resolution of (+)-acyclic alcohols. Agr. Biol. Chem. 1973, 37:1923-1928.
30. Papachristos D.P., Kimbaris A.C., Papadopoulos N.T., Polissiou M.G. Toxicity of citrus essential oils against Ceratitis capitata (Diptera: Tephritidae) larvae. Ann. Appl. Biol. 2009, 155:381-389.
31. Rahuman A.A., Venkatesan P., Gopalakrishnan G. Mosquito larvicidal activity of oleic and linoleic acids isolated from Citrullus colocynthis (Linn.) Schrad. Parasitol. Res. 2008, 103:1383-1390.
32. Robbins P., Cherniack M.G. Review of the biodistribution and toxicity of the insect repellent N/N-diethyl-m-toluamide (DEET). J. Toxicol. Environ. Health 1986, 18:503-523.
33. Santos S.R.L., Melo M.A., Cardoso A.V., Santos R.L.C., de Sousa D.P., Cavalcanti S.C.H. Structure-activity relationships of monoterpenes and derivatives against Aedes aegypti Linn. Chemosphere 2011, 84:150-153.
34. Shaalan E., Canyon D., Younes M.W.F., Abdel-Wahab H., Mansour A. A review of botanical phytochemicals with mosquitocidal potential. Environ. Int. 2005, 31:1149-1166.
35. Shaalan E., Canyon D., Bowden B., Younes M., Abdel-Wahad H., Mansour A. Efficacy of botanical extracts from Callitris glaoucophylla against Aedes aegypti and Culex annulirostris mosquitoes. Trop. Biomed. 2006, 23:180-185.
36. Shapiro H., Micucci S. Pesticide use for West Nile virus. Can. Med. Assoc. J. 2003, 168:1427-1430.
37. Simas N.K., Lima E.D., Conceicao S.D., Kuster R.M., Filho A.M. Natural products for dengue transmission control-larvicidal activity of Myroxylon Balsamum (red oil) and of terpenoids and phenylpropanoids. Quim. Nova 2004, 27:46-49.
38. Sivakumar R., Jebanesan A., Govindarajan M., Rajasekar P. Larvicidal and repellent activity of tetradecanoic acid against Aedes aegypti (Linn.) and Culex quinquefasciatus (Say.) (Diptera: Culicidae). Asian Pac. J. Trop. Med. 2011, 4:706-710.
39. Sukumar K., Perich M.J., Boobar L.R. Botanical derivatives in mosquito control: a review. J. Am. Mosq. Control Assoc. 1991, 7:210-237.
40. Syed Z., Leal W.S. Mosquitoes smell and avoid the insect repellent DEET. Proc. Natl. Acad. Sci. 2008, 105:13598-13603.
41. Tietze L.F., Shiemann K., Christoph W. Synthesis of enantiopure homoallylic alcohols and ethers by diastereoselective allylation of aldehydes. Chem. Eur. J. 1996, 29:1164-1172.
42. Trumble J.T. Caveat emptor: safety considerations for natural products used in arthropod control. Am. Entomol. 2002, 48:7-13.
43. United States, 2009. Office of the Federal Register. Code of the federal regulations. 21, Food and drugs, Part 170-199, Washington.
44. Waliwitiya R., Kennedy C.J., Lowenberger C.A. Larvicidal and oviposition-altering activity of monoterpenoids, trans-anethole and rosemary oil to the yellow fever mosquito Aedes aegypti (Diptera: Culicidae). Pest Manage. Sci. 2009, 65:241-248.
45. WHO, 2005. Guidelines for laboratory and field testing of mosquito larvicides communicable disease control, prevention and eradication. Pesticide Evaluation Scheme (WHOPES). Geneva, pp. 1-41.
46. Wiberg K.B., Fox A.S. The mechanisms of permanganate oxidation. Oxidation of tertiary hydrogens. J. Am. Chem. Soc. 1963, 85:3487-3491.
47. Zahran H.M., Abdelgaleil S.A.M. Insecticidal and developmental inhibitory properties of monoterpenes on Culex pipiens L. (Diptera: Culicidae). J. Asia Pac. Entom. 2011, 14:46-51.