Substituted imidazolylmethyloxiranes and substituted imidazolylpropenes, their preparation and fungicides containing them

A substituted imidaolylpropene of Formula I:

• ##STR19## wherein R.sub.1 and R.sub.2 are identical or different and each is C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.5 -C.sub.8 -cycloalkenyl, tetrahydropyranyl, norbornyl, pyridyl, naphthyl, biphenyl or phenyl, each of which is unsubstituted or mono- to trisubstituted by halogen, nitro, phenoxy, amino, alkyl, alkoxy or haloalkyl, each of 1 to 4 carbon atoms,
• D is a single bond,
• E is H, F, Cl or Br,
• X, Y and Z are identical or different and each is hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -haloalkyl, C.sub.1 -C.sub.3 -alkoxy, unsubstituted or C.sub.1 -C.sub.3 -alkyl- or C.sub.1 -C.sub.3 -acyl-substituted amino, unsubstituted or C.sub.1 -C.sub.3 -alkyl-substituted mercapto, C.sub.1 -C.sub.3 -acyl, C.sub.1 -C.sub.3 -alkoxycarbonyl, C.sub.1 -C.sub.3 -hydroxyalkyl or substituted or unsubstituted phenyl, with the proviso that X, Y and Z cannot simultaneously be hydrogen, and the acid addition salts and metal complexes thereof tolerated by plants.

A fungicidal composition, comprising:

• a fungicidally effective amount of an imidazolylmethyloxirane of Formula I:
• ##STR20## wherein R.sub.1 and R.sub.2 are identical or different and each is C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.5 -C.sub.8 -cycloalkenyl, tetrahydropyranyl, norbornyl, pyridyl, naphthyl, biphenyl or phenyl, each of which is unsubstituted or mono- to trisubstituted by halogen, nitro, phenoxy, amino, alkyl, alkoxy or haloalkyl, each of 1 to 4 carbon atoms,
• D is oxygen,
• E is H, F, Cl or Br,
• X, Y and Z are identical or different and each is hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.3 -haloalkyl, C.sub.1 -C.sub.3 -alkoxy, unsubstituted or C.sub.1 -C.sub.3 -alkyl- or C.sub.1 -C.sub.3 -acyl-substituted amino, unsubstituted or C.sub.1 -C.sub.3 -alkyl-substituted mercapto, C.sub.1 -C.sub.3 -acyl, C.sub.1 -C.sub.3 -alkoxycarbonyl, C.sub.1 -C.sub.3 -hydroxyalkyl or substituted or unsubstituted phenyl, with the proviso that X, Y and Z cannot simultaneously be hydrogen, or an acid addition salt or metal complex thereof tolerated by plants in combination with a carrier.

A method for combatting fungi, which comprises:

• applying to areas, plants or seeds threatened by fungus attack, a fungicidally effective amount of a substituted imidazolylmethyloxirane of Formula I:
• ##STR21## wherein R.sub.1 and R.sub.2 are identical or different and each is C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.5 -C.sub.8 -cycloalkenyl, tetrahydropyranyl, norbornyl, pyridyl, naphthyl, biphenyl or phenyl, each of which is unsubstituted or mono- to trisubstituted by halogen, nitro, phenoxy, amino, alkyl, alkoxy or haloalkyl, each of 1 to 4 carbon atoms,
• D is oxygen,
• E is H, F, Cl or Br,
• X, Y and Z are identical or different and each is hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.3 -haloalkyl, C.sub.1 -C.sub.3 -alkoxy, unsubstituted or C.sub.1 -C.sub.3 -alkyl- or C.sub.1 -C.sub.3 -acyl-substituted amino, unsubstituted or C.sub.1 -C.sub.3 -alkyl-substituted mercapto, C.sub.1 -C.sub.3 -acyl, C.sub.1 -C.sub.3 -alkoxycarbonyl, C.sub.1 -C.sub.3 -hydroxyalkyl or substituted or unsubstituted phenyl, with the proviso that X, Y and Z cannot simultaneously be hydrogen, and the acid addition salts and metal complexes thereof tolerated by plants.

A fungicidal composition, comprising:

• a fungicidally effective amount of an imidazolylpropene of Formula I:
• ##STR22## wherein R.sub.1 and R.sub.2 are identical or different and each is C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.5 -C.sub.8 -cycloalkenyl, tetrahydropyranyl, norbornyl, pyridyl, naphthyl, biphenyl or phenyl, each of which is unsubstituted or mono- to trisubstituted by halogen, nitro, phenoxy, amino, alkyl, alkoxy or haloalkyl, each of 1 to 4 carbon atoms,
• D is a single bond,
• E is H, F, Cl or Br,
• X, Y and Z are identical or different and each is hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -haloalkyl, C.sub.1 -C.sub.3 -alkoxy, unsubstituted or C.sub.1 -C.sub.3 -alkyl- or C.sub.1 -C.sub.3 -acyl-substituted amino, unsubstituted or C.sub.1 -C.sub.3 -alkyl-substituted mercapto, C.sub.1 -C.sub.3 -acyl, C.sub.1 -C.sub.3 -alkoxycarbonyl, C.sub.1 -C.sub.3 -hydroxyalkyl or substituted or unsubstituted phenyl, with the proviso that X, Y and Z cannot simultaneously be hydrogen, or an acid addition salt or metal complex thereof tolerated by plants in combination with a carrier.

A method for combatting fungi, which comprises:

• applying to areas, plants or seeds threatened by fungus attack, a fungicidally effective amount of a substituted imidazolylpropene of Formula I:
• ##STR23## wherein R.sub.1 and R.sub.2 are identical or different and each is C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.5 -C.sub.8 -cycloalkenyl, tetrahydropyranyl, norbornyl, pyridyl, naphthyl, biphenyl or phenyl, each of which is unsubstituted or mono- to trisubstituted by halogen, nitro, phenoxy, amino, alkyl, alkoxy or haloalkyl, each of 1 to 4 carbon atoms,
• D is a single bond,
• E is H, F, Cl or Br,
• X, Y and Z are identical or different and each is hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -haloalkyl, C.sub.1 -C.sub.3 -alkoxy, unsubstituted or C.sub.1 -C.sub.3 -alkyl- or C.sub.1 -C.sub.3 -acyl-substituted amino, unsubstituted or C.sub.1 -C.sub.3 -alkyl-substituted mercapto, C.sub.1 -C.sub.3 -acyl, C.sub.1 -C.sub.3 -alkoxycarbonyl, C.sub.1 -C.sub.3 -hydroxyalkyl or substituted or unsubstituted phenyl, with the proviso that X, Y and Z cannot simultaneously be hydrogen, and the acid addition salts and metal complexes thereof tolerated by plants.