New fungicidal imidazolyl-substd. di:phenyl-propyne cpds. - e.g. 3-(2,4-di:fluorophenyl)-3(1-imidazolyl)-3-phenyl-1-propyne

摘要

Imidazolyl-substd. diphenyl-propynes (I) and their addn. salts and metal salt complexes are new, where R1, R2 = H or fluorine; Y = halogen; 1-4C alkyl; 1-4C alkoxy; 1-4C alkylthio; 1-2C haloalkyl or haloalkoxy contg. 1-5 halogens; phenyl; or phenoxy; m = 0, 1, 2 or 3. Starting materials (II) are also claimed. USE/ADVANTAGE - Cpds. (I) are plant fungicides. They have a good plant tolerance and are esp. useful against fungal diseases on cereals and rice. Cpds. (I) can be formulated conventionally and can be used in concns. of 0.0001-1 wt.% to treat plants and 0.00001-0.1 wt.% to treat soil, and in amts. of 0.01-50 g/kg to treat seeds. Cpds. (I) have better activity than 3,3-diphenyl-3-(1-imidazolyl)-propyne known from DE2128700 and DE3307909. Starting materials (II). In an example, (i) 2,4-difluoro-benzophenone (VII) (20.3g) was converted in a metal-organic reaction using acetylene in the presence of potassium tert. butylate into 1-(2,4-difluorphenyl)-1-phenyl-2-propyn-1-ol (II) (22.8g) and (ii) acetic anhydride (14.5g) was added at 60-70 deg.C to a mixt. of the prod. from (i) and imidazole (45g). The mixt. was treated at 120 deg.C, cooled, taken up in dichloromethane, washed, dried and concd. Chromatography gave 3-(2,4-difluorophenyl)-3-(1-imidazolyl) -3-phenyl-1-propyne (I) (5.6g); m.pt. 100 deg.C.