Synthesis of 3-(4-bromobenzyl)-5-(aryl methylene)-5H-furan-2-ones and their activity as inhibitors of the photosynthetic electron transport chain

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 21, 2007, Pages 8562-8569

  Barbosa, Luiz C A ^a   Rocha, Marcelo E ^a   Teixeira, Róbson R ^a,b   Maltha, Célia R A ^a   Forlani, Giuseppe ^c  

^a FEDERAL UNIVERSITY OF VIÇOSA   (Brazil)

^b FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

^c UNIVERSITY OF FERRARA   (Italy)

Author keywords

Herbicides; Nostoclide analogues; Photosynthetic electron transport inhibitors; Solubility

Indexed keywords

DRUG DERIVATIVE; FURAN DERIVATIVE; GAMMA BUTYROLACTONE; HERBICIDE; LACTONE;

ARTICLE; CHEMISTRY; DRUG EFFECT; ELECTRON TRANSPORT; PHOTOSYNTHESIS; SYNTHESIS;

4-BUTYROLACTONE; ELECTRON TRANSPORT; FURANS; HERBICIDES; LACTONES; PHOTOSYNTHESIS;

SPINACIA OLERACEA;

EID: 35548938583     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf072120x     Document Type: Article

References (34)

1. Stetter, J.; Lieb, F. Innovation in crop protection: trends in research. Angew. Chem., Int. Ed. 2000, 39, 1724-1744.
2. Cobb, A. Herbicides and Plant Physiology; Chapman and Hall: London 1992.
3. Tomlin, C. The Pesticide Manual; Royal Society of Chemistry: Cambridge, U.K., 1994.
4. Heap, I. International survey of herbicide resistant weeds. http:// www.weedscience.org (accessed June 28, 2007).
5. Duke, S. O.; Rimando, A. M.; Baerson, S. R.; Scheffler, B. E.; Ota, E.; Belz, R. G. Strategies for the use of natural products for weed management. J. Pestic. Sci. 2002, 27, 298-306.
6. Macías, F. A.; Molinillo, J. M. G.; Varela, R. M.; Galindo, J. C. G. Allelopathy - a natural alternative for weed control. Pestic. Manage. Sci. 2007, 63, 327-348.
7. Short, P. L. Growing agchem R&D. Chem. Eng. News 2005, 83, 19-23.
8. Demuner, A. J.; Barbosa, L. C. A.; Veiga, T. A. M.; Barreto, R. W.; Diaz, B. K.; Hennssen, B. L. Phytotoxic constituents from Nimbya alternantherae. Biochem. Syst. Ecol. 2006, 34, 790-795.
9. Barbosa, L. C. A.; de Alvarenga, E. S.; Demuner, A. J.; Virtuoso, L. S.; Silva, A. A. Synthesis of new phytogrowth-inhibitory substituted aryl-p-benzoquinones. Chem. Biodiversity 2006, 3, 553-567.
10. Pignatello, J. J.; Porwoll, J.; Carlson, R. E.; Xavier, A.; Gleason, F. K. Structure of the antibiotic cyanobacterin, a chlorine-containing γ-lactone from the freshwater cyanobacterium Scytonema hofmanni. J. Org. Chem. 1986, 48, 4035-4043.
11. Gleason, F. K.; Baxa, C. A. Activity of the natural algicide, cyanobacterin, on eukaryotic microorganisms. FEMS Microbiol. Lett. 1986, 33, 85-88.
12. Gleason, F. K.; Case, D. E. Activity of the natural algicide, cyanobacterin, on angiosperms. Plant Physiol. 1986, 80, 834-837.
13. Gleason, F. K.; Paulson, J. L. Site of action of the natural algicide, cyanobacterin in the blue-green alga, Synechococcus sp. Arch. Microbiol. 1984, 138, 273-277.
14. Gleason, F. K. The natural herbicide, cyanobacterin, specifically disrupts thylakoid membrane structure in Euglena gracilis strain-Z. FEMS Microbiol. Lett. 1990, 68, 77-81.
15. Yang, X.; Shimizu, Y.; Steiner, J. R.; Clardy, J. Nostoclide I and II, extracellular metabolites from a symbiotic cyanobacterium, Nostoc sp., from the lichen Peltigera canina. Tetrahedron 1993, 34, 761-764.
16. Barbosa, L. C. A.; Costa, A. V.; Veloso, D. P.; Lopes, J. L. C.; Hernandez-Terrones, M. G. H.; King-Diaz, B.; Lotina-Hennsen, B. Phytogrowth-inhibitory lactones derivatives of glaucolide B. Z. Naturforsch. 2004, 59c, 803-810.
17. Lima, L. S.; Barbosa, L. C. A.; Alvarenga, E. S.; Demuner, A. J.; Silva, A. A. Synthesis and phytotoxicity evaluation of substituted para-benzoquinones. Aust. J. Chem. 2003, 36, 625-630.
18. Chaves, F. C.; Barbosa, L. C. A.; Demuner, A. J.; Silva, A. A. New helminthosporal analogues with plant-growth regulatory properties synthesized via oxyallyl cation. Z. Naturforsch. 2006, 61b, 1287-1294.
19. Barbosa, L. C. A.; Demuner, A. J.; Maltha, C. R. A.; Da Silva, P. S.; Silva, A. A. Síntese e avaliação da atividade fitotóxica de novos análogos oxigenados do ácido helmintospórico. Quim. Nova 2003, 26, 655-660.
20. Barbosa, L. C. A.; Demuner, A. J.; Alvarenga, E. S.; Oliveira, A.; King-Diaz, B.; Lotina-Hennsen, B. Phytogrowth- and photosynthesis-inhibiting properties of nostoclide analogues. Pestic. Manage. Sci. 2006, 62, 214-222.
21. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon: Oxford, U.K., 1988.
22. Mancuso, A. J.; Huang, S. L.; Swern, D. Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide "activated" by oxalyl chloride. J. Org. Chem. 1978, 43, 2480-2482.
23. Näsman, J. H. 3-Methyl-2(5H)-furanone-(2(5H)-furanone, 3-methyl). Org. Synth. 1990, 6, 162-174.
24. Lipton, M. F.; Sorensen, C. M.; Sadler, A. C.; Shapiro, R. H. A convenient method for the accurate estimation of concentrations of alkyllithium reagents J. Organomet. Chem. 1960, 186, 155-158.
25. Vicentini, C. B.; Guccione, S.; Giurato, L.; Ciaccio, R.; Mares, D.; Forlani, G. Pyrazole derivatives as photosynthetic electron transport inhibitors: new leads, and structure-activity relationship. J. Agric. Food Chem. 2005, 53, 3848-3855.
26. Vicentini, C. B.; Mares, D.; Tartari, A.; Manfrini, M; Forlani, G. Synthesis of pyrazole derivatives and their evaluation as photosynthetic electron transport inhibitors. J. Agric. Food Chem. 2004, 52, 1898-1906.
27. Näsman, J. H.; Kopola, N.; Pensar, G. Tetramethyldiamido phosphate directed β-lithiation of a π-excessive heterocycle; d[2]-synthon to 2-substituted butenolides. Tetrahedron Lett. 1986, 27, 1391-1394.
28. Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. The vinylogous aldol reaction: a valuable, yet understated carbon-carbon bond-forming maneuver. Chem. Rev. 2000, 100, 1929-1972.
29. Boukouvalas, J.; Lachance, N.; Ouellet, M.; Trudeau, M. Facile access to 4-aryl-2(5H)-furanones by Suzuki cross coupling: Efficient synthesis of rubrolides C and E. Tetrahedron Lett. 1998, 39, 7665-7668.
30. Kar, A.; Gogoi, S.; Argade, N. P. Synthesis of naturally occurring bioactive butyrolactones: maculalactones A-C and nostoclide I. Tetrahedron 2005, 61, 5297-5302.
31. Bellina, F.; Anselmi, C.; Rossi, R. Total synthesis of rubrolide M and some of its unnatural congeners. Tetrahedron Lett. 2002, 43, 2023-2027.
32. Dayan, F. E.; Vincent, A. C.; Romagni, J. G.; Allen, S. N.; Duke, S. O.; Duke, M. V.; Bowling, J. J.; Zjawiony, J.K. Amino- and urea-substituted thiazoles inhibit photosynthetic electron transfer. J. Agric. Food Chem. 2000, 48, 3689-3693.
33. Castaneda, P.; Mata, R.; Lotina-Hennsen, B. Effect of encecalin, euparin and demethylencecalin on thylakoid electron transport and photophosphorylation in isolated spinach chloroplasts. J. Sci. Food Agric. 1998, 78, 102-108.
34. Macias, M. L.; Rojas, I. S.; Mata, R.; Lotina-Hennsen, B. Effect of selected coumarins on spinach chloroplast photosynthesis. J. Agric. Food Chem. 1999, 47, 2137-2140.