Synthesis and herbicidal activity of N-oxide derivatives

Journal of Agricultural and Food Chemistry

Volumn 48, Issue 7, 2000, Pages 2995-3002

  Cerecetto, Hugo ^a   Dias, Eduardo ^a   Di Maio, Rossanna ^a   González, Mercedes ^a   Pacce, Sandra ^a   Saenz, Patricia ^a   Seoane, Gustavo ^a   Suescun, Leopoldo ^a   Mombrú, Alvaro ^a   Fernández, Grisel ^b   Lema, Marisa ^b   Villalba, Juana ^b  

^a UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

^b UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

Author keywords

1,2,5 oxadiazole N oxide; Benzo 1,2 c 1,2,5 oxadiazole N oxide; Herbicide; Quinoxaline N,N' dioxide

Indexed keywords

HERBICIDE; OXIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONFORMATION; DOSE RESPONSE; MODEL; PESTICIDE SPRAYING; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

DOSE-RESPONSE RELATIONSHIP, DRUG; HERBICIDES; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OXIDES;

TRITICUM AESTIVUM;

EID: 0033931470     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf9904766     Document Type: Article

References (35)

1. Albin, A.; Pietra, S. Heterocycles N-oxides; CRC Press: Boca Raton, FL, 1991.
2. Baker, N. R.; Percival, M. P. Herbicides and photosynthesis. In Herbicides. Topics in Photosynthesis; Baker, N. R., Percival, M. P., Eds.; Barber, J., General Ed.; Elsevier Science Publishers: Amsterdam, The Netherlands, 1990; Vol. 10, Chapter 9.4, pp 1-26.
3. Boulton, A. J.; Middleton, D. Furazans and Furazan oxides. V. Tropono[4,5-c]-, Thieno[2,3-c]-, and Biphenyleno[2,3-c]-furazan oxides. J. Org. Chem. 1974, 39, 2956-2962.
4. Boulton, A. J.; Katritzky, A. R.; Sewell, M. J.; Wallis, B. N-Oxides and related compounds. XXXI. The nuclear magnetic resonance spectra and tautomerism of some substituted benzofuroxans. J. Chem. Soc. B 1967, 9, 914-917.
5. Boyer, J. H.; Ellzey, S. E. Deoxygenation of aromatic o-Dinitroso derivatives by phosphines. J. Org. Chem. 1961, 26, 4684-4685.
6. Cahill, A.; White, I. N. Reductive activation of N-oxides to cause DNA strand breakage in cell lines in vitro. Biochem. Soc. Trans. 1991, 19 (2), 1275.
7. Calvino, R.; Di Stilo, A.; Fruttero, R.; Gasco, A. M.; Sorba, G.; Gasco, A. Pharmacochemistry of the furoxan ring: recent developments. Farmaco 1993, 48 (2), 321-334.
8. Cerecetto, H.; Di Maio, R.; Ibarruri, G.; Seoane, G.; Denicola, A.; Peluffo, G.; Quijano, C.; Paulino, M. Synthesis and antitrypanosomal activity of novel 5-Nitro-2-furaldehyde and 5-Nitrothiophene-2-carboxaldehyde semicarbazone derivatives. Farmaco 1998, 53 (2), 89-94.
9. Cerecetto, H.; Di Maio, R.; González, M.; Risso, M.; Saenz, P.; Seoane, G.; Denicola, A.; Peluffo, G.; Quijano, C.; Zinola, F.; Olea-Azar, C. 1,2,5-Oxadiazole N-oxide derivatives and related compounds as potential antitrypanosomal drugs. Structure-activity relationship. J. Med. Chem. 1999, 42, 1941-1950.
10. Cheeseman, G. W. H.; Cookson, R. F. Condensed Pyrazines; Wiley: New York, 1979.
11. Clark, R. D. Synthesis and QSAR of herbicidal 3-pyrazolyl α,α,α-trifluorotolyl ethers. J. Agric. Food Chem. 1996, 44, 3643-3652.
12. Edwards, M. L.; Bambury, R. E. 2,3-Dimethylquinoxaline-6-carboxaldehyde 1,4-dioxide. J. Heterocycl. Chem. 1975, 12 (5), 835-836.
13. Eussen, J. H. H.; Thus, J. L. G.; Wellinga, K.; Stork, B. 2-Pyrazolines with herbicidal activity. Pestic. Sci. 1990, 29, 101-108.
14. Fruttero, R.; Ferrarotti, B.; Serafino, A.; Di Stilo, A.; Gasco, A. Unsymmetrically substituted furoxans. Part 11[1]. Methylfuroxancarbaldehydes. J. Heterocycl. Chem. 1989, 26, 1345-1347.
15. Gasco, A.; Mortarini, V.; Ruà, G.; Nano, G. M.; Menziani, E. Synthesis and structure of some asymmetrically substituted furoxans. I. J. Heterocycl. Chem. 1972, 9, 577-580.
16. Gasco, A. M.; Fruttero, R.; Sorba, G.; Gasco A. Phenylfuroxancarbaldehydes and related compounds. Justus Liebigs Ann. Chem. 1991, 1211-1213.
17. Harris, R. K.; Katritzky, A. R.; Oksne, S.; Bailey, A. S.; Paterson, W. G. N-Oxides and related compounds. Part XIX. Proton resonance spectra and the structure of benzofuroxan and its nitro-derivatives. J. Chem. Soc. 1963, 197-203.
18. Hay, J. V. Chemistry of sulfonylurea herbicides. Pestic. Sci. 1990, 29, 247-261.
19. Howard, E.; Olszewski, W. F. The reaction of triphenylphosphine with some aromatic amine oxides. J. Am. Chem. Soc. 1959, 81, 1483-14847.
20. Joshi, K. C.; Jain, R.; Dandia, A.; Sharma, K.; Jain, S. C. Synthesis and pesticidal activities of certain fluorine-containing 9H-1,2,4-Triazolo[4,3-α]benzimidazoles. Pestic. Sci. 1990, 29, 143-149.
21. Karp, G. M.; Manfredi, M. C.; Guaciaro, M. A.; Ortlip, C. L.; Marc, P.; Szamosi, I. Synthesis and herbicidal activity of 1H-1,4-benzodiazepine-2,5-diones. J. Agric. Food Chem. 1997, 45, 493-500.
22. Kleschick, W. A.; Costales, M. J.; Dunbar, J, E.; Meikle, R. W.; Monte, W. T.; Pearson, N. R.; Snider, S. W.; Vinogradoff, A. P. New herbicidal derivatives of 1,2,4-triazolo[1,5-α]-pyrimidine. Pestic. Sci. 1990, 29, 341-355.
23. Ley, K.; Seng, F. Synthesis using benzofuroxanes. Synthesis 1975, 415-422.
24. Monge, A.; López de Ceráin, A.; Ezpeleta, O.; Cerecetto, H.; Dias, E.; Di Maio, R.; González, M.; Onetto, S.; Seoane, G.; Suescun, L.; Mariezcurrena, R. Synthesis and biological evaluation of 1,2,5-oxadiazole N-oxide derivatives as hypoxia-selective cytotoxins. Pharmazie 1998a, 53, 758-764.
25. Monge, A.; López de Ceráin, A.; Ezpeleta, O.; Cerecetto, H.; Dias, E.; Di Maio, R.; González, M.; Onetto, S.; Risso, M.; Seoane, G.; Zinola, F.; Olea-Azar C. 1,2,5-Oxadiazole N-oxide derivatives as hypoxia-selective cytotoxins. Structure-activity relationships. Pharmazie 1998b, 53, 698-702.
26. Monge, A.; Palop, J. A.; López de Ceráin, A.; Senador, V.; Martínez-Crespo, F. J.; Sáinz, Y.; Narro, S.; García, E.; de Miguel, C.; González, M.; Hamilton, E.; Barker, A. J.; Clarke, E. D.; Greenhow, D. T. Hypoxia-selective agents derived from quinoxaline 1,4-di-N-oxides. J. Med. Chem. 1995, 38, 1786-1792.
27. Nandihalli, U. B.; Duke, M. V.; Ashmore, J. A.; Musco, V. A.; Clark, R. D.; Duke, O. S. Enantioselectivity of protoporphyrinogen oxidase-inhibiting herbicides. Pestic. Sci. 1994, 40, 265-277.
28. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals; Pergamon Press: Oxford, U.K., 1988.
29. Sheldrick, G. M. Phase annealing in SHELX-90: direct methods for larger structures. Acta Crystallogr. 1990, A46, 467-473.
30. Sheldrick, G. M. SHELXL-97, Program for structure refinement. University of Göttingen, Germany, 1997.
31. Smith, P. A. S.; Boyer, J. H. Organic Syntheses Collective; Rabjohn, N., Ed.; Wiley: New York, 1963; Vol. 4, pp 75-78.
32. Tennant, G.; Mason, J. C. Synthesis of 1-hidroxyquinoxalin-2(1H)-one 4-oxides. J. Chem. Soc. D 1971, 586-587.
33. Theodoridis, G.; Hotzman, F. W.; Scherer, L. W.; Smith, B. A.; Tymonko, J. M.; Wyle, M. J. Synthesis and structure-activity relationships of 1-aryl-4-substituted-1,4-dihydro-5-H-tetrazol-5-ones, a novel class of pre- and post-emergence herbicides. Pestic. Sci. 1990, 30, 259-274.
34. Wepplo, P. Imidazolinone herbicides: synthesis and novel chemistry. Pestic. Sci. 1990, 39, 293-315.
35. Zsolnai, L.; Pritzkow, H. ZORTEP, An interactive ORTEP program. University of Heidelbelg, Germany, 1995.