Patent ES-8504138-A1 (ES)
Title: 1-Phenyl- or 1-benzhydryl-imidazole-5-carboxylic acid derivs.
IPC: C07D233/64
Filed: 1983-11-04
Abstract: In a new process for the prodn. of 1-phenyl or 1-benzhydryl-imidazole-5-carboxylic acid derivs. (I) from alpha-formyl-alpha -formamido-acetic acid esters (II) or their enoltantomers (IIa): (where X is O, S or N(R1); R1 is H, phenyl, 2-6C alkenyl, 1-12C alkyl (opt. substd. by up to 3 1-6C alkoxy or 1-3C dialkylamino groups or by halogen) or, when X is O or S, also a metal cation or ammonium; R2 is a residue (Ia), (Ib) or (Ic): R3 and R4 are 1-4C alkyl; R5 is H, 1-4C alkyl, 1-4C alkoxy and/or halogen; R6 is H, halogen, 1-4C alkoxy and/or 1-4C alkyl; and R7 is R1 other than H, metal or ammonium) by (A) reaction with a 1-3C carboxylic acid amide, advantageously in the presence of strong acids at 50-250 deg. C; (B) reaction with a 5- to 30-fold molar excess of ammonium acetate in the 5- to 50-molar amount of glacial acetic acid at 50-180 deg. C; or (C) reaction with ammonia or ammonium salts and nitromolecular condensation of the resulting alpha-aminomethylene cpd. at a temperature such that the product distils; the residue OR7 in the product opt. being subsequently modified or substituted by conventional methods. Products in which R2 is a group of formula (Ia) are new and claimed. - The products have fungicidal, herbicidal and plant growth regulant activity. They are suitable for use in plant protection, as well as in technical applications (e.g. as timber preservatives, or as preservatives in cutting or drilling oils or metal-working coolants and lubricants. Results of tests for fungicidal, herbicidal and cereal growth retardant activity are given in the specification. DEAB- DE3217094 C In a new process for the prodn. of 1-phenyl or 1-benzhydryl-imidazole-5-carboxylic acid derivs. (I) from alpha-formyl-alpha -formamido-acetic acid esters (II) or their enoltantomers (IIa): (where X is O, S or N(R1); R1 is H, phenyl, 2-6C alkenyl, 1-12C alkyl (opt. substd. by up to 3 1-6C alkoxy or 1-3C dialkylamino groups or by halogen) or, when X is O or S, also a metal cation or ammonium; R2 is a residue (Ia), (Ib) or (Ic): R3 and R4 are 1-4C alkyl; R5 is H, 1-4C alkyl, 1-4C alkoxy and/or halogen; R6 is H, halogen, 1-4C alkoxy and/or 1-4C alkyl; and R7 is R1 other than H, metal or ammonium) by (A) reaction with a 1-3C carboxylic acid amide, advantageously in the presence of strong acids at 50-250 deg. C; (B) reaction with a 5- to 30-fold molar excess of ammonium acetate in the 5- to 50-molar amount of glacial acetic acid at 50-180 deg. C; or (C) reaction with ammonia or ammonium salts and nitromolecular condensation of the resulting alpha-aminomethylene cpd. at a temperature such that the product distils; the residue OR7 in the product opt. being subsequently modified or substituted by conventional methods. Products in which R2 is a group of formula (Ia) are new and claimed. - The products have fungicidal, herbicidal and plant growth regulant activity. They are suitable for use in plant protection, as well as in technical applications (e.g. as timber preservatives, or as preservatives in cutting or drilling oils or metal-working coolants and lubricants. Results of tests for fungicidal, berbicidal and cereal growth retardant activity are given in the specification.  (26pp Dwg.No0/0) - DE3217094 C 1-Substd. imidazole-5-carboxylic acid derivs. of formula (I) are claimed, where X is O, S or N; and R1 is H, phenyl, 2-6C alkenyl or 1-12C alkyl opt. substd. by 1-3 1-6C alkoxy, 1-3C dialkylamino or halogen gps. When X = N there are two R1 gps., and when X = S or O, R1 may also be a metal ion or ammonium; R2 is a gp. of formula (II), where R3 and R4 are independently 1-4C alkyl, and R5 is H, 1-4C alkyl, 1-4C alkoxy or halogen.