Synthesis of new fluorinated Tebufenpyrad analogs with acaricidal activity through regioselective pyrazole formation.
In previous studies, our group has shown that the use of fluorinated alcohols such as trifluoroethanol (TFE) and hexafluoroisopropanol (HFIP) as solvents dramatically increases the regioselectivity in the pyrazole formation from 1,3-diketone with methylhydrazine. We have now applied this synthetic method to the preparation of new fluorinated pyrazoles, which have then been used as synthetic intermediates in the preparation of fluorinated analogs of Tebufenpyrad, a commercial acaricide. These compounds display a strong acaricidal activity that is either comparable to or better than that of the commercial compound.
Fustero
Santos
S
Departamento de Quimica Organica, Universidad de Valencia, E-46100 Burjassot, Spain. santos.fustero@uv.es
Román
Raquel
R
Sanz-Cervera
Juan F
JF
Simón-Fuentes
Antonio
A
Bueno
Jorge
J
Villanova
Salvador
S
D040041:Acaridae / Q000187:drug effects*; D000818:Animals; D054879:Halogenation; D010575:Pesticides / Q000138:chemical synthesis* / Q000494:pharmacology; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry*
D010575:Pesticides; D011720:Pyrazoles; C429623:4-chloro-N-((4-(1,1-dimethylethyl)phenyl)methyl)-3-ethyl-1-methyl-1H-pyrazole-5-carboxamide