The synthesis and biological activity of 1-alkyl-4-(3-azacyclobenzoyl)-5- hydroxypyrazole herbicides

Chimia

Volumn 57, Issue 11, 2003, Pages 720-724

  Benko, Zoltan ^a   Shinkle, Sharon ^a   Van Heertum, John ^a   Jackson, Johnny ^a   McQuiston, Jeffery ^a   Webster, Jeffery ^a   Turner, James ^a   Weimer, Monte ^a   Paterson, Eileen ^a  

^a DOW AGROSCIENCES LLC   (United States)

Author keywords

Benzoylpyrazoles; Herbicide; Hydroxyphenylpyruvate dioxygenase inhibitors; Morpholines; Piperidines

Indexed keywords

HERBICIDE; NITROGEN; PYRAZOLE DERIVATIVE;

ARTICLE; COOLING; GRASSLAND; HERBICIDAL ACTIVITY; SEASON; STRUCTURE ACTIVITY RELATION; SYNTHESIS; WHEAT;

EID: 0347624283     PISSN: 00094293     EISSN: None     Source Type: Journal    
DOI: 10.2533/000942903777678579     Document Type: Article

References (22)

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16. The lower yields are largely due to the competing formation of the corresponding pyrazolobenzpyran, in which the hydroxypyrazole cyclizes onto the C(2) of the benzoyl when there is a leaving group present.
17. Hydroxypiperidines were modified by standard methylation, oxidation and chlorination procedures.
18. D. Chassonnery, F. Chastrette, M. Chastrette, A. Blanc, G. Mattioda, 'Disproportionation reactions from glyoxal and difunctional basic molecules', Bull. Chim. Soc. Fr. 1994, 131, 188. Other two carbon, dielectrophiles such as methyl 2-bromoacetate, chloroacetaldehyde and glycolaldehyde dimer failed to give a reaction.
19. The use of dichloromethane as solvent for this reaction was important - no product was obtained in THF. In the examples presented in this paper, the lactols existed entirely in the closed form. Other researchers have found equilibrium mixtures in related systems: a) N.H. Cromwell, K. Tsou, J. Am. Chem. Soc. 1949, 71, 993; b) R.E. Lutz, R.H. Jordan, J. Am. Chem. Soc. 1949, 71, 996.
20. The use of dichloromethane as solvent for this reaction was important - no product was obtained in THF. In the examples presented in this paper, the lactols existed entirely in the closed form. Other researchers have found equilibrium mixtures in related systems: a) N.H. Cromwell, K. Tsou, J. Am. Chem. Soc. 1949, 71, 993; b) R.E. Lutz, R.H. Jordan, J. Am. Chem. Soc. 1949, 71, 996.
21. The syntheses of the corresponding oxazolidine, isoxazolidine and 1,4-oxazepine analogs were attempted following literature precedents, but they failed either at the cyclization or nucleophilic aromatic displacement step.
22. G.G. Gibson, P. Skett, 'Drug Metabolism', Chapman & Hall, New York, 1994.