Process for the preparation of azolyl-vinyl ketones

A process for the preparation of an azolyl-vinyl ketone of the formula ##STR58## in which R.sup.1 represents straight-chain or branched alkyl with 1 to 6 carbon atoms, straight-chain or branched halogenoalkyl with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, or aryl which has 6 to 10 carbon atoms and optionally carries one or more substituents selected independently from halogen, straight-chain or branched alkyl with 1 to 4 carbon atoms, alkoxy and alkylthio with in either case 1 to 2 carbon atoms, halogenoalkyl with up to 2 carbon atoms and up to 5 identical or different halogen atoms, cyano, nitro, optionally halogen-substituted phenyl and optionally halogen-substituted phenoxy,

• R.sup.2 represents straight-chain or branched alkyl with 1 to 12 carbon atoms;
• straight-chain or branched halogenoalkyl with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms;
• aryl which has 6 to 10 carbon atoms and optionally carries one or more substituents selected independently from halogen, straight-chain or branched alkyl with 1 to 4 carbon atoms, halogenoalkyl with up to 2 carbons atoms and up to 5 identical or different halogen atoms, cyano, nitro, optionally halogen-substituted phenyl and optionally halogen-substituted phenoxy;
• cycloalkyl with 3 to 7 carbon atoms or cycloalkenyl with 5 to 7 carbon atoms, in either case optionally substituted by alkyl with 1 to 4 carbon atoms;
• cycloalkylalkyl which has 3 to 7 carbon atoms in the cycloalkyl part and 1 to 4 carbon atoms in the straight-chain or branched alkyl part and is optionally substituted by alkyl with 1 to 4 carbon atoms;
• cycloalkenylalkyl which has 5 to 7 carbon atoms in the cycloalkenyl part and 1 to 4 carbon atoms in the straight-chain or branched alkyl part and is optionally substituted by alkyl with 1 to 4 carbon atoms;
• furyl or thiophenyl which in either case is optionally substituted by halogen or straight-chain or branched alkyl with 1 to 4 carbon atoms;
• alkoxyalkyl or alkylmercaptoalkyl with in either case 1 to 4 carbon atoms in each alkyl part;
• optionally substituted straight-chain or branched alkenyl, alkynyl or alkenynyl with in each case up to 6 carbon atoms, the substituents being selected from hydroxyl, alkoxy with 1 to 4 carbon atoms and phenyl which is optionally substituted by halogen;
• indenyl or fluorenyl which in either case is optionally substituted by halogen, alkyl with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms;
• diphenyl- or triphenyl-methyl, wherein each phenyl optionally carries one or more substitutents selected independently from halogen, straight-chain or branched alkyl with 1 to 4 carbon atoms, alkoxy and alkylthio with in either case 1 to 2 carbon atoms, halogenoalkyl with up to 2 carbon atoms and up to 5 identical or different halogen atoms, cyano, nitro, optionally halogen-substituted phenyl and optionally halogen-substituted phenoxy;
• or the grouping ##STR59## R.sup.3 represents hydrogen, cyano, straight-chain or branched alkyl with 1 to 4 carbon atoms, akenyl or alkynyl with in either case 2 to 4 carbon atoms, or the grouping --CO.sub.2 R.sup.6, --CONR.sup.7 R.sup.8, --SO.sub.2 NR.sup.7 R.sup.8 or --SO.sub.3 H,
• R.sup.4 represents aryl which has 6 to 10 carbon atoms and optionally carries one or more substituents selected independently from halogen, straight-chain or branched alkyl with 1 to 4 carbon atoms, alkoxy and alkylthio with in either case 1 to 2 carbon atoms, halogenoalkyl with up to 2 carbon atoms and up to 5 identical or different halogen atoms, cyano, nitro, optionally halogen-substituted phenyl and optionally halogen-substituted phenoxy;
• furyl or thiophenyl which in either case is optionally substituted by halogen or alkyl with 1 to 4 carbon atoms;
• dioxolanyl or dithiolanyl which in either case is optionally substituted by alkyl with 1 to 4 carbon atoms, alkoxyalkyl with 1 to 4 carbon atoms in each alkyl part or benzyl;
• cyano, or the grouping --CO.sub.2 R.sup.6 or --SO.sub.2 R.sup.9,
• R.sup.5 represents hydrogen;
• straight-chain or branched alkyl with 1 to 4 carbon atoms;
• cycloalkyl which has 5 to 7 carbon atoms and is optionally substituted by alkyl with 1 to 2 carbon atoms;
• aryl which has 6 to 10 carbon atoms and optionally carries one or more substitutents selected independently from halogen, straight-chain or branched alkyl with 1 to 4 carbon atoms, alkoxy and alkylthio with in either case 1 to 2 carbon atoms, halogenoalkyl with up to 2 carbon atoms and up to 5 identical or different halogen atoms, cyano, nitro, optionally halogen-substituted phenyl and optionally halogen-substituted phenoxy;
• R.sup.6 represents hydrogen;
• straight-chain or branched alkyl with 1 to 4 carbon atoms;
• alkoxyalkyl with 1 to 4 carbon atoms in each alkyl part;
• or benzyl which optionally carries on the phenyl part one or more substitutents selected independently from halogen, straight-chain or branched alkyl with 1 to 4 carbon atoms, alkoxy and alkylthio with in either case 1 to 2 carbon atoms, halogenoalkyl with up to 2 carbon atoms and up to 5 identical or different halogen atoms, cyano, nitro, optionally halogen-substituted phenyl and optionally halogen-substituted phenoxy,
• R.sup.7 and R.sup.8 are identical or different and each represent straight-chain or branched alkyl with 1 to 4 carbon atoms,
• R.sup.9 represents straight-chain or branched alkyl with 1 to 4 carbon atoms;
• or phenyl which optionally carries one or more substitutents selected independently from halogen, straight chain or branched alkyl with 1 to 4 carbon atoms, alkoxy and alkylthio with in either case 1 to 2 carbon atoms, halogenoalkyl with up to 2 carbon atoms and up to 4 identical or different halogen atoms, cyano, nitro, optionally halogen-substituted phenyl and optionally halogen-substituted phenoxy, comprising reacting a keto-enamine of the formula ##STR60## in which R.sup.10 and R.sup.11 are identical or different and each
• represent alkyl with 1 to 4 carbon atoms, with an organometallic compound of the formula
• Z--R.sup.2
• in which
• Z represents the group Hal-Mg or an alkali metal or the grouping LiCuR.sup.2, and
• Hal represents halogen,
• in the presence of a solvent.