Structure-activity relationships of 33 piperidines as toxicants against female adults of Aedes aegypti (Diptera: Culicidae)

Journal of Medical Entomology

Volumn 44, Issue 2, 2007, Pages 263-269

  Pridgeon, Julia W ^a   Meepagala, Kumudini M ^b   Becnel, James J ^a   Clark, Gary G ^a   Pereira, Roberto M ^a   Linthicum, Kenneth J ^a  

^a CENTER FOR MEDICAL   (United States)

^b NATURAL PRODUCTS UTILIZATION RESEARCH UNIT   (United States)

Author keywords

Aedes aegypti; Dengue; Insecticide; Piperidine; Yellow fever

Indexed keywords

AEDES AEGYPTI; CULICIDAE; DIPTERA; HEXAPODA;

EID: 34247511604     PISSN: 00222585     EISSN: None     Source Type: Journal    
DOI: 10.1603/0022-2585(2007)44[263:sropat]2.0.co;2     Document Type: Article

References (38)

1. Aitken, T. H., W. G. Downs, and R. E. Shope. 1977. Aedes aegypti strain fitness for yellow fever virus transmission. Am, J. Trop. Med. Hyg. 26: 985-989.
2. Boger, M., D. Durr, L. Gsell, R. G. Hall, F. Karrer, O. Kristiansen, P. Maienfisch, A. Pascual, and A. Rindlisbacher. 2001. Synthesis and structure-activity relationships of benzophenone hydrazone derivatives with insecticidal activity. Pest Manag. Sci. 57: 191-202.
3. Brown, A. W., and R. Pal. 1971. Insecticide resistance in arthropods. Public Health Pap. 38: 1-491.
4. Coleman, J. C., and D. M. McLean. 1973. Dengue virus transmission by Aedes aegypti mosquitoes following intrathoracic inoculation. Am. J. Trop. Med. Hyg. 22: 124-129.
5. Creemer, L. C., H. A. Kirst, J. W. Paschal, and T. V. Worden. 2000. Synthesis and insecticidal activity of spinosyn analogs functionally altered at the 2′-,3′- and 4′-positions of the rhamnose moiety. J. Antibiot. (Tokyo) 53: 171-178.
6. de Filippis, A. M., R. M. Nogueira, H. G. Schatzmayr, D. S. Tavares, A. V. Jabor, S. C. Diniz, J. C. Oliveira, E. Moreira, M. P. Miagostovich, E. V. Costa, et al. 2002. Outbreak of jaundice and hemorrhagic fever in the Southeast of Brazil in 2001: detection and molecular characterization of yellow fever virus, J. Med. Virol. 68: 620-627.
7. Degallier, N., J. P. Herve, A. P. Travassos da Rosa, and G. C. Sa. 1988. Aedes aegypti (L.): importance of its bioecology in the transmission of dengue and other arboviruses. I. Bull Soc. Pathol. Exot. Filiales 81: 97-110.
8. Elliott, M., N. F. Janes, and B. C. Pearson. 1971. The pyrethrins and related compounds. XII. 5-substituted 3-furoates and 3-thenoates, intermediates for synthesis of insecticidal esters. J. Chem. Soc. (Perkin 1)14:2551-2557.
9. Fouque, F., and R. Carinci. 1996. Aedes aegypti in French Guiana. Some aspects of history, general ecology and vertical transmission of the dengue virus. Bull. Soc. Pathol. Exot. 89: 115-119.
10. Gbewonyo, W. S., and D. J. Candy. 1992. Separation of insecticidal components from an extract of the roots of male Piper guineense (west African black pepper) by gas chromatography. Toxicon 30: 1037-1042.
11. Gillett, J. D., and R. W. Ross. 1955. The laboratory transmission of yellow fever by Aedes (Stegomyia) aegypti (Linnaeus) from Malaya. Ann. Trop. Med. Parasitol. 49: 63-65.
12. Gubler, D. J. 1989. Aedes aegypti and Aedes aegypti-borne disease control in the 1990s: top down or bottom up. Charles Franklin Craig Lecture. Am. J. Trop. Med. Hyg. 40: 571-578.
13. Ito, M., H. Okui, H. Nakagawa, S. Mio, A. Kinoshita, T. Obayashi, T. Miura, J. Nagai, S. Yokoi, R. Ichinose, et al. 2002. Synthesis and insecticidal activity of N-oxydihydropyrroles: 4-hydroxy-3-mesityl-5,5-dimethyl derivatives with various substituents at the 1-position. Biosci. Biotechnol. Biochem. 66: 2406-2414.
14. Ito, M., H. Okui, H. Nakagawa, S. Mio, A. Kinoshita, T. Obayashi, T. Miura, J. Nagai, S. Yokoi, R. Ichinose, et al. 2003a. Synthesis and insecticidal activity of novel dihydropyrrole derivatives with N-sulfanyl, sulfinyl, and sulfonyl moieties. Bioorg. Med. Chem. 11: 489-494.
15. Ito, M., H. Okui, H. Nakagawa, S. Mio, A. Kinoshita, T. Obayashi, T. Miura, J. Nagai, S. Yokoi, R. Ichinose, et al. 2003b. Synthesis and insecticidal activity of novel N oxydihydropyrroles: 4-hydroxy-3-mesityl-1- methoxymethoxy derivatives with various substituents at the 5-position. Bioorg. Med. Chem. 11: 761-768.
16. Katritzky, A. R., D. A. Dobchev, I. Tulp, M. Karelson, and D. A. Carlson. 2006. QSAR study of mosquito repellents using Codessa Pro. Bioorg. Med. Chem. Lett. 16: 2306-2311.
17. Lee, S. E. 2000. Mosquito larvicidal activity of pipernonaline, a piperidine alkaloid derived from long pepper, Piper longum. J. Am. Mosq. Control Assoc. 16: 245-247.
18. Malavige, G. N., S. Fernando, D. J. Fernando, and S. L. Seneviratne. 2004. Dengue viral infections. Postgrad. Med. J. 80: 588-601.
19. Mattingly, P. F. 1967. Aedes aegypti and other mosquitos in relation to the dengue syndrome. Bull. World Health Organ. 36: 533-535.
20. Meegalla, S. K., D. Doller, R. Liu, D. Sha, Y. Lee, R. M. Soll, N. Wisnewski, G. M. Silver, and D. Dhanoa. 2006. Synthesis and insecticidal activity of fluorinated 2-(2,6-dichloro-4-trifluoromethylphenyl)-2,4,5,6- tetrahydrocyclopentapyrazoles. Bioorg. Med. Chem. Lett. 16: 1702-1706.
21. Onyango, C. O., A. A. Grobbelaar, G. V. Gibson, R. C. Sang, A.Sow, R. Swaneopel, and F.J. Burt. 2004a. Yellow fever outbreak, southern Sudan, 2003. Emerg. Infect. Dis. 10: 1668-1670.
22. Onyango, C. O., V. O. Ofula, R. C. Sang, S. L. Konongoi, A. Sow, K. M. De Cock, P. M. Tukei, F. A. Okoth, R. Swanepoel, F. J. Burt, et al. 2004b. Yellow fever outbreak, Imatong, southern Sudan. Emerg. Infect. Dis. 10: 1063-1068.
23. Park, I. K., S. G. Lee, S. C. Shin J. D. Park, and Y. J. Ahn. 2002. Larvicidal activity of isobutylamides identified in Piper nigrum fruits against three mosquito species. J. Agric. Food Chem. 50: 1866-1870.
24. Philip, C. B. 1962. Transmission of yellow fever virus by aged Aedes aegypti and comments on some other mosquitovirus relationships. Am. J. Trop. Med. Hyg. 11: 697-701.
25. Pinto Severo, O. 1955. [Campaign of eradication of Aedes aegypti in the Americas; its organization, development and results since December 1954.]. Bol. Of. Sanit. Panam. 38: 378-398.
26. Rathnawathie, M., and K. A. Buckle. 1983. Determination of pipeline in pepper (Piper nigrum) using high-performance liquid chromatography. J. Chromatogr. 264: 316-320.
27. Ribeiro, T. S., L. Freire-de-Lima, J. O. Previato, L. Mendonca-Previato, N. Heise, and M. E.de Lima. 2004. Toxic effects of natural piperine and its derivatives on epimas tigotes and amastigotes of Trypanosoma cruzi. Bioorg. Med. Chem. Lett. 14: 3555-3558.
28. Rudnick, A. 1967. Aedes aegypti and haemorrhagic fever. Bull World Health Organ. 36: 528-532.
29. Shaalan, E. A., D. Canyon, M. W. Younes, H. Abdel-Wahab, and A. H. Mansour. 2005. A review of botanical phytochemicals with mosquitocidal potential. Environ. Int. 31: 1149-1166.
30. Soper, F. L. 1967. Aedes aegypti and yellow fever. Bull. World Health Organ. 36: 521-527.
31. Srivastava, J. B. 1970. Insecticide & larvicide activity in the extract of Piper peepuloides Royle (Piperaceae). Indian J. Exp. Biol. 8: 224-225.
32. Sukumar, K.,M. J. Perich, and L.R. Boobar. 1991. Botanical derivatives in mosquito control: a review. J. Am. Mosq. Control Assoc. 7: 210-237.
33. Teixeira Mda, G., C. Costa Mda, M. L. Barreto, and E. Mota. 2005. Dengue and dengue hemorrhagic fever epidemics in Brazil: what research is needed based on trends, surveillance, and control experiences? Cad Saude Publica 21 : 1307-1315.
34. Valero, N. 2003. Yellow fever in Venezuela. Invest. Clin. 44: 269-71.
35. Vasconcelos, P. F., A. P. Rosa, S. G. Rodrigues, E. S. Rosa, H. A. Monteiro, A. C. Cruz, V. L. Barros, M. R. Souza, and J. F. Rosa. 2001. Yellow fever in Para State, Amazon region of Brazil, 1998-1999: entomologie and epidemiologic findings. Emerg. Infect. Dis. 7: 565-569.
36. Wang, Q., J. Cheng, and R. Huang. 2002. Synthesis and insecticidal evaluation of novel N-(S-amino)sulfenylated derivatives of diacylhydrazines. Pest Manag. Sci. 58: 1250-1253.
37. Wei, Y., and H. Xu. 1998. Laboratory evaluation of Piper chaba against Tribolium castaneum. Nongzikeji 2: 11-12.
38. Yang, Y. C., S. G. Lee, H. K. Lee, M. K. Kim, S. H. Lee, and H. S. Lee. 2002. A piperidine amide extracted from Piper longum L. fruit shows activity against Aedes aegypti mosquito larvae. J. Agric. Food Chem. 50: 3765-3767.