1-halovinylazoles and fungicides containing them

DETAILED DESCRIPTION We claim: 1.
A compound selected from the group consisting of those of the formula I ##STR7## wherein A is 4-fluorophenyl and R is selected from the group consisting of phenyl, substituted phenyl, biphenylyl, substituted biphenylyl, naphthyl, and substituted naphthyl, wherein the substituents are 1 to 3 substituents selected from the group consisting of halo, nitro, phenoxy, amino, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, and haloalkyl of 1 to 4 carbon atoms; D is selected from the group consisting of chloro and bromo; and X is N; a plant tolerated acid addition salt thereof, and a metal complex thereof.
2.
A fungicidal composition containing a carrier and a fungicidally effective amount of a compound of claim 1.
3.
A process for combatting fungi wherein the fungi or the plant materials, plant areas, plants or seeds which are threatened by fungus attack are contacted with a fungicidally effective amount of a compound of claim 1.
4.
A compound of the formula ##STR8## wherein A is 4-fluorophenyl and R is selected from the group consisting of 2-fluorophenyl, 4-fluorophenyl, and 2-chlorophenyl, D is chloro or bromo, and X is N, or a plant tolerated acid addition salt or metal complex thereof.
5.
A compound of the formula I as set forth in claim 1, wherein D is Cl and R is 4-fluorophenyl.
6.
A compound of the formula I as set forth in claim 1, wherein D is Cl and R is 2-chlorophenyl.




Description:
The present invention relates to novel azole compounds, processes for their preparation and fungicides containing them.
It is known that 1-(1,2,4-triazol-1-yl)-2-(2-chlorophenyl)-2-(4-fluorophenyl)-ethene (European Patent 47057) can be used as a fungicide.
However, the fungicidal actions are not satisfactory in all cases.
We have found that 1-halovinylazoles of the general formula I ##STR2## where A and R are identical or different and are each phenyl, biphenyl, naphthyl or hetaryl, and these radicals may be monosubstituted to trisubstituted by halogen, nitro, phenoxy, amino, alkyl, alkoxy or haloalkyl, each of 1 to 4 carbon atoms, D is chlorine or bromine and X is CH or N, and their plant-tolerated acid addition salts or metal complexes have a better fungicidal action than known azole compounds