Synthesis of a combinatorial library of amides and its evaluation against the fall armyworm, Spodoptera frugiperda

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 9, 2011, Pages 4822-4827

  Castral, Thais C ^a   Matos, Andreia P ^a   Monteiro, Julia L ^a   Araujo, Fernanda M ^a   Bondancia, Tatiani M ^a   Batista Pereira, Luciane G ^a   Fernandes, João B ^a   Vieira, Paulo C ^a   Da Silva, M Fatima G F ^a   Corrâea, Arlene G ^a  

^a FEDERAL UNIVERSITY OF SÃO CARLOS   (Brazil)

Author keywords

Combinatorial library; Insecticidal activity; Lepidoptera; Piperamides; Spodoptera frugiperda

Indexed keywords

COMBINATORIAL LIBRARY; INSECTICIDAL ACTIVITY; LEPIDOPTERA; PIPERAMIDES; SPODOPTERA FRUGIPERDA;

AMIDES;

AMIDE; INSECTICIDE;

ANIMAL; ARMYWORM; ARTICLE; DRUG EFFECT; SYNTHESIS;

AMIDES; ANIMALS; INSECTICIDES; SPODOPTERA;

LEPIDOPTERA; SPODOPTERA FRUGIPERDA; ZEA MAYS;

EID: 79955690415     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf104903t     Document Type: Article

References (20)

1. Romanelli, G. P.; Virla, E. G.; Duchowicz, P. R.; Gaddi, A. L.; Ruiz, D. M.; Bennardi, D. O.; Ortiz, E. V.; Autino, J. C. Sustainable synthesis of flavonoid derivatives, QSAR study and insecticidal activity against the fall armyworm, Spodoptera frugiperda (Lep.: Noctuidae). J. Agric. Food Chem. 2010, 58, 6290-6295.
2. Tavares, W. S.; Cruz, I.; Petacci, F.; de Assis Junior, S. L.; Freitas, S. S.; Zanuncio, J. C.; Serrao, J. E. Potential use of Asteraceae extracts to control Spodoptera frugiperda (Lepidoptera: Noctuidae) and selectivity to their parasitoids Trichogramma pretiosum (Hymenoptera: Trichogram matidae) and Telenomus remus (Hymenoptera: Scelionidae). Ind. Crops Prod. 2009, 30, 384-388.
3. Tavares,W. S.;Cruz, I.; Fonseca, F.G.;Gouveia,N. L.; Serrao, J. E.; Zanuncio, J. C. Deleterious activity of natural products on postures of Spodoptera frugiperda (Lepidoptera: Noctuidae) and Diatraea saccharalis (Lepidoptera: Pyralidae). Z. Naturforsch., C 2010, 65, 412-418.
4. Storer, N. P.; Babcock, J. M.; Schlenz, M.; Meade, T.; Thompson, G. D.; Bing, J. W.; Huckaba, R. M. Discovery and characterization of field resistance to Bt maize: Spodoptera frugiperda (Lepidoptera: Noctuidae) in Puerto Rico. J. Econ. Entomol. 2010, 103, 1031-1038.
5. Negrisoli, A. S.; Garcia, M. S.; Negrisoli, C. R. C. B.; Bernardi, D.; Silva, A. Efficacy of entomopathogenic nematodes (Nematoda: Rhabditida) and insecticide mixtures to control Spodoptera frugiperda (Smith, 1797) (Lepidoptera: Noctuidae) in corn crops. Crop Prot. 2010, 29, 677-683.
6. Batista-Pereira, L. G.; Stein, K.; Paula, A. F.;Moreira, J. A.; Cruz, I.; Figueiredo, M. L. C.; Perri, J., Jr.; Correa, A. G. Isolation, identification, synthesis, and field evaluation of the sex pheromone of the Brazilian population of Spodoptera frugiperda. J. Chem. Ecol. 2006, 32, 1085-1099. (Pubitemid 43825160)
7. Matos, A. P.; Leite, A. C.; Batista-Pereira, L. G.; Vieira, P. C.; Fernandes, J. B.; da Silva, M. F. G. F. Effects of limonoids from Cipadessa fruticosa on fall armyworm. Z. Naturforsch., C 2009, 64, 441-446.
8. Kato,M. J.; Furlan,M. Chemistry and evolution of the Piperaceae. Pure Appl. Chem. 2007, 79, 529-538.
9. Dyer, L. A.; Dodson, C. D.; Stireman, J. O.; Tobler, M. A.; Smilanich, A. M.; Fincher, R. M.; Letourneau, D. K. Synergistic effects of three Piper amides on generalist and specialist herbivores. J. Chem. Ecol. 2003, 29, 2499-2514. (Pubitemid 37443173)
10. Richards, L. A.; Dyer, L. A.; Smilanich, A. M.; Dodson, C. D. Synergistic effects of amides from two piper species on generalist and specialist herbivores. J. Chem. Ecol. 2010, 36, 1105-1113.
11. de Castro, M. D. P.; da Silva, P. H. S.; Padua, L. E. D. Piper tuberculatum Jacq. (Piperaceae) extract activity on Spodoptera frugiperda (J. E. Smith). Rev. Cienc. Agron. 2008, 39, 437-442.
12. Batista-Pereira, L. G.; Castral, T. C.; Silva, M. T. M.; Amaral, B. R.; Fernandes, J. B.; Vieira, P. C.; Silva, M. F. G. F.; Correa, A. G. Insecticidal activity of synthetic amides on Spodoptera frugiperda. Z. Naturforsch., C 2006, 61, 196-202.
13. Smith, P. W.; Lai, J. Y. Q.; Whittington, A. R.; Cox, B.; Houston, J. G. Synthesis and biological evaluation of a library containing potentially 1600 amides esters - A strategy for rapid compound generation and screening. Bioorg. Med. Chem. Lett. 1994, 4, 2821-2824.
14. Estrela, J. L.V.; Guedes, R. N. C.; Maltha, C. R. A.; Fazolin, M. Toxicity of piperine amide analogs to larvae of Ascia monuste orseis Godart (Lepidoptera: Pieridae) and Spodoptera frugiperda (J.E. Smith) (Lepidoptera: Noctuidae). Neotrop. Entomol. 2003, 32, 343-346.
15. Ewete, F. K.; Arnason, J. T.; Durst, T.; Mackinnon, S. Toxicity of gedunin, piperine and crude extracts of their natural products on growth and development of Ostrinia nubilalis Hubner (Lepidoptera: Pyralidae). Discov. Innov. 2000, 12, 67-72.
16. Derdau, V.; Fey, T.; Atzrodt, J. Synthesis of isotopically labelled SGLT inhibitors and their metabolites. Tetrahedron 2010, 66, 1472-1482.
17. Kasten, P. J. R.; Precetti, A. A. C. M.; Parra, J. R. P. Dados biológicos comparativos de Spodoptera frugiperda (J. E. Smith, 1797) em duas dietas artificiais e substrato natural. Rev. Agric. 1978, 53, 68-78.
18. Parra, J. R. P. Criação de insetos para estudos com patógenos. In: Controle microbiano de insetos; Alves, S. B., Ed. Manole: SP, Brazil, 1986; pp 348-373.
19. Paula, V. F.; Barbosa, L. C.; Demuner, A. J.; Piló-Veloso, D.; Piçanco, M. C. Synthesis and insecticidal activity of new amide derivatives of piperine. Pest Manag. Sci. 2000, 56, 168-174. (Pubitemid 30123406)
20. Finney, D. J. Probit Analysis, 3rd ed.; Cambridge University Press: Cambridge, U.K., 1971.