2,4,6-phenyl substituted cyclic ketoenols

A process for the preparation of compounds of formula (I)

• in which
• W represents alkoxy, halogenoalkoxy, alkoxyalkyloxy, alkoxy-bis-alkyloxy, or optionally substituted cycloalkylalkanediyloxy that is optionally interrupted by hetero atoms,
• X represents alkyl,
• Y represents chlorine, bromine, or iodine, and
• CKE represents a group
• in which
• A represents hydrogen;
• represents alkyl, alkenyl, alkoxyalkyl, or alkyl-thioalkyl, each of which is optionally substituted by halogen;
• represents saturated or unsaturated, optionally substituted cycloalkyl in which one or more ring atoms are optionally replaced by a hetero atom;
• or represents aryl, arylalkyl, or hetaryl, each of which is optionally substituted by halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, cyano, or nitro,
• B represents hydrogen, alkyl, or alkoxyalkyl, or
• A and B together with the carbon atom to which they are bonded represent a saturated or unsaturated, unsubstituted or substituted cycle that optionally contains one or more hetero atoms,
• D represents hydrogen;
• represents an optionally substituted radical selected from the series consisting of alkyl, alkenyl, alkynyl, alkoxyalkyl, and saturated or unsaturated cycloalkyl in which one or more ring members are optionally replaced by hetero atoms;
• or represents arylalkyl, aryl, hetarylalkyl, or hetaryl, or
• A and D together with the atoms to which they are bonded represent a saturated or unsaturated cycle that is unsubstituted or substituted in the A,D moiety and optionally contains one or more hetero atoms, and
• G represents hydrogen or a group
• in which
• E represents a metal ion equivalent or an ammonium ion,
• L represents oxygen or sulphur,
• M represents oxygen or sulphur,
• R1 represents alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, or poly-alkoxyalkyl, each of which is optionally substituted by halogen;
• represents cycloalkyl that is optionally interrupted by one or more hetero atoms and is optionally substituted by halogen, alkyl, or alkoxy;
• or represents optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl, or hetaryloxyalkyl, and
• R2 represents alkyl, alkenyl, alkoxyalkyl, or polyalkoxyalkyl, each of which is optionally substituted by halogen;
• or represents optionally substituted cycloalkyl, phenyl, or benzyl,
• R3 represents alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, or cycloalkyl-thio, each of which is optionally substituted by halogen;
• or represents optionally substituted phenyl, benzyl, phenoxy, or phenylthio,
• comprising
• (A) for compounds of formula (I-1-a)
• in which A, B, D, W, X, and Y have the meanings given for formula (I), subjecting to an intramolecular condensation reaction a compound of formula (II)
• in which
• A, B, D, W, X, and Y have the meanings given for formula (I), and
• R8 represents alkyl, in the presence of a diluent and in the presence of a base,
• or
• (B) for compounds of formula (I-2-a)
• in which A, B, W, X and Y have the meanings given for formula (I), subjecting to an intramolecular condensation reaction a compound of formula (III)
• in which A, B, W, X, Y, and R8 have the meanings given for formula (I), in the presence of a diluent and in the presence of a base.
• and
• (C) for compounds of formulas (I-1-b) to (I 2 b)
• in which A, B, D, R1, W, X, and Y have the meanings given for formula (I),
• reacting compounds of formulas (I-1-a) to (I 2 a) shown above in which A, B, D, W, X and Y have the meanings given for formula (I),
• (α) with an acid chloride of formula (XIII)
• in which
• R1 has the meanings given for formula (I), and
• Hal represents halogen, or
• (β) with a carboxylic anhydride of formula (XIV)
• R1—CO—O—CO—R1 (XIV)
• in which R1 has the meanings given for formula (I), optionally in the presence of a diluent and optionally in the presence of an acid-binding agent;
• (D) for compounds of formulas (I-1-c) to (I 2 c)
• in which
• A, B, D, R2, M, W, X, and Y have the meanings given for formula (I), and
• L represents oxygen, reacting compounds of formulas (I-1-a) to (I 2 a) shown above in which A, B, D, W, X and Y have the meanings given for formula (I), with a chloroformic ester or chloroformic thioester of formula (XV)
• R2-M-CO—CI (XV)
• in which R2 and M have the meanings given for formula (I), optionally in the presence of a diluent and optionally in the presence of an acid-binding agent;
• or
• (E)for compounds of formulas (I-1-c) to (I 2 c)
• in which
• A, B, D, R2,M, W, X, and Y have the meanings given for formula (I), and
• L represents sulphur,
• reacting compounds of formulas (I-1-a) to (I 2 a) shown above in which A, B, D, W, X and Y have the meanings given for formula (I), with a chloromonothioformic ester or chlorodithioformic ester of formula (XVI)
• in which R2 and M have the meanings given for formula (I), optionally in the presence of a diluent and optionally in the presence of an acid-binding agent;
• or
• (F) for compounds of formulas (I-1-d) to (I 2 d)
• in which A, B, D, R3, W, X and Y have the meanings given for formula (I),
• reacting compounds of formulas (I-1-a) to (I 2 a) shown above in which A, B, D, W, X and Y have the meanings given for formula (I),
• with a sulphonyl chloride of formula (XVII)
• R3—SO2—CI (XVII)
• in which R3 has the meanings given for formula (I), optionally in the presence of a diluent and optionally in the presence of an acid-binding agent;
• or
• (G) for compounds of formulas (I-1-f) to (I 2 f)
• in which A, B, D, E, W, X and Y have the meanings given for formula (I),
• reacting compounds of formulas (I-1-a) to (I 2 a) shown above in which A, B, D, W, X and Y have the meanings given for formula (I),
• (α) with a metal compound of formula (XIX)
• Me(OR10)t (XIX)
• in which
• Me represents a mono- or divalent metal, and
• t represents the number 1 or 2,
• optionally in the presence of a diluent, or
• (β) with an amine of formulae (XX)
• in which R10, R11 and R12 independently of one another represent
• hydrogen or alkyl,
• optionally in the presence of a diluent.