N-difluoromethylation of phenylazoles

Journal of Fluorine Chemistry

Volumn 92, Issue 2, 1998, Pages 141-145

  Lyga, John W ^a   Patera, Russell M ^a  

^a FMC CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001348617     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-1139(98)00262-0     Document Type: Article

References (14)

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2. D. Cartwright, in: R.E. Banks, B.E. Smart, J.C. Tatlow (Eds.), Organofluorine Chemistry, Principles and Commercial Applications, Plenum Press, New York, 1994.
3. W.A. Van Saun, J.T. Bahr, G.A. Crosby, Z.A. Fore, H.L. Guscar, W.N. Harnish, R.S. Hooten, M.S. Marquez, D.S. Parrish, G. Theodoridis, J.M. Tymonko, K.R. Wilson, M.J. Wyle, Proc. Br. Crop Protection Conf., Weeds (1991) p. 77.
4. W.A. Van Saun, J.T. Bahr, L.J. Bourdouxhe, F.J. Gargantiel, F.W. Hotzman, S.W. Shires, N.A. Sladen, S.F. Tutt, K.R. Wilson, Proc. Br. Crop Protection Conf., Weeds (1993) p. 19.
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6. Sulfentrazone is 30 times more potent than the N-methyl analog in an in vitro herbicide assay. For a description of the assay see; J.W. Lyga, R.M. Patera, G. Theodoridis, B.P. Halling, F.W. Hotzman, M.J. Plummer, J. Agric. Food Chem. 39 (1991) 1667.
7. For comparison of the herbicidal potency of N-methyl and N-difluoromethyl analogs of aryltriazolinones see, G. Theodoridis, J.S. Baum, F.W. Hotzman, M.C. Manfredi, L.L. Maravetz, J.W. Lyga, J.M. Tymonko, K.R. Wilson, K.M. Poss, M.J. Wyle in Synthesis and Chemistry of Agrochemicals III, in: D.R. Baker, J.G. Fenyes, J.J. Steffens (Eds.), American Chemical Society, Washington, D.C., 1992, chap. 14.
8. V.G. Poludnenko, O.B. Didinskaia, A.F. Pozharski, Khim. Geterotsikl. Soedin., (1984) 520, CA 101:90879z.
9. Chen Q.-Y., Yang G.-Y., Wu S.-W. Chinese J. Chem. 10:1992;350.
10. Compounds similar to 4 are claimed as herbicides, A. Leone-Bay, E.D. Weil, J. Tomko, Eur. Pat. Appl., EP 180787, 1986, CAN 105:97471.
11. R.M. Patera, J.W. Lyga, unpublished results.
12. For a recent review on the synthesis of fluorocarbenes see, D.L.S. Brahms, W.P. Dailey, Chem. Rev. 96 (1996) 1585.
13. J. Catalan, J.L.M. Abboud, J. Elguero, in: A.R. Katritzky (Ed.), Advances in Heterocyclic Chemistry, vol. 41, Academic Press, Orlando, FL, 1987, p. 188.
14. Prepared according to the procedure by Y. Lin, S.A. Lang, M.F. Lovell, N.A. Perkinson, J. Org. Chem. 44 (1979) 4160.