New imidazolyl-methyl and triazolyl-methyl substd. O-tolyl-oxirane(s) - useful as broad spectrum fungicides to treat plants, seeds, soil and materials

    公开(公告)号:DE3930166A1

    公开(公告)日:1991-03-21

    申请号:DE3930166

    申请日:1989-09-09

    Applicant: BASF AG

    Abstract: Azolylmethyl-oxiranes (I) and their addn salts and metal complexes are new. A = 1-8C alkyl, phenyl, biphenyl, naphthyl, benzyl, tetrahydropyranyl or 3-8C cycloalkyl opt. mono-,di- or trisubstd. by halogen, nitro, phenoxy, amino or 1-4C alkyl, alkoxy or haloalkyl; X = CH or N. Starting materials (II) are also cl-aimed. L = nucleophilic leaving gp. USE/ADVANTAGE: Cpds (I) are broad spectrum fungicides used to treat plants, seeds, soil and materials, they are formulated conventionally and applied in amts. of 0.02-3 kg/ha. Cpds (I) have a better activity than the cpds. described in EP 94564 and EP 196038. 2 Cpds (I) i.e. 2-(1,2,4-triazol-1-ylmethyl) -2-(4-fluorophenyl)-3-)(2 -methylphenyl)-oxirane and the corrssp. 4-chlorophenyl cpd are claimed. In an example a) 2-methylbenzaldehyde was condensed with 4-fluorophenyl-acetaldehyde in the presence of NaOH and the prod was epoxidised (H2O2) and reduced (NaBH4) to give cis-2-hydroxymethyl-2) (4-fluorophenyl)-3-(2-methylphenyl) -oxirane which was converted (CH2SO2Cl) into cis-2-methanesulphonyl-methyl-2-)(4-fluorophenyl)-3-) (2-methylphenyl)-oxirane (II) b) 1,2,4-triazole (4.9g) in dimethylformamide (100 ml) was treated with K2CO3(16.4g), heated, cooled, treated with a soln of the prod from a) (20g) in dimethylformamide (50 ml) and stirred. The mixt was added to water, extracted and the extr-act was washed dired and concentrated to give (1,2,4-triazol-1-ylmethyl) -2-(4-fluorophenyl)-(3-(2-methyl-phenyl) -oxirane (I) (15g), m.pt 99-102 deg.C. (tert, butyl methyl ether/hexane). :(14pp Dwg.No. 0/0)

Patent Agency Ranking