Method for producing beta ketoenol esters

A process as claimed in any of the preceding claims, wherein the 1,3-diketone of the formula III or its tautomers III′ and III″ are of the formula IIIa or IIIb:

• 17
• in which k is 0, 1 or 2 and the variables R1 to R6 are as defined below:
• R1, R5 independently of one another are hydrogen, C1-C4-alkyl or C1-C4-alkoxycarbonyl;
• R2, R4, R6 independently of one another are hydrogen, C1-C4-alkyl, C1-C4-alkylthio or C1-C4-alkoxy;
• R3 is hydrogen, halogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, di(C1-C6-alkoxy)methyl, (C1-C6-alkoxy)(C1-C6-alkylthio)methyl, di(C1-C6-alkylthio)methyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl;
• 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1,3-dithiolan-2-yl or 1,3-dithian-2-yl, where the six last-mentioned radicals may be substituted by one to three C1-C4-alkyl radicals;
• or
• R2 and R4 or R4 and R6 together form a π bond or a C1-C5-alkanediyl chain which may have a π bond and/or may carry one, two or three radicals from the following group:
• halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;
• or
• R5 and R6 together form a C1-C5-alkanediyl chain which may have a π bond and/or may carry one, two or three radicals from the following group:
• halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;
• or
• R2 and R6 together form a C1-C4-alkanediyl chain which may have a π bond and/or may carry one, two or three radicals from the following group:
• halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;
• or
• R3 and R4 together form a chain of the formula —O—(CH2)p—O—, —O—(CH2)p—S—, —S—(CH2 )p—S—, —O—(CH2)q— or —S—(CH2)q—, in which p is 2, 3, 4 or 5 and q is 2, 3, 4, 5 or 6 and which may be substituted by one, two or three radicals from the following group:
• halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;
• or
• R3 and R4 together with the carbon to which they are attached form a carbonyl or thiocarbonyl group.

A process as claimed in any of the preceding claims, wherein the aryl halide of the formula II is represented by the formula IIa:

• 18
• in which
• R1a and R4a independently of one another are hydrogen, halogen, in particular fluorine or chlorine, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, hydroxy-C1-C6-alkyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-haloalkylthio-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-haloalkylsulfonyl-C1-C6-alkyl, C1-C6-alkylamino-C1-C6-alkyl, or di(C1-C6-alkyl)amino-C1-C6-alkyl and
• R2a and R3a form a 5- or 6-membered saturated or unsaturated heterocycle which may have 1, 2 or 3 heteroatoms selected from the group consisting of N, S and O, where sulfur atoms in the heterocycle may also be present as sulfoxide or sulfone,
• nitrogen atoms and carbon atoms in the heterocycle have a hydrogen atom or a substituent selected from the group consisting of halogen, nitro, cyano, hydroxyl, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-aminoalkyl, C1-C6-alkylcarbonyl, C1-C6-alkylcarbonyloxy, C1-C6-alkyloxycarbonyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylcarbonyl-C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-hydroxyalkoxy, C1-C6-alkoxy-C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C8-cycloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-hydrokyalkylthio, C1-C6-alkoxy-C1-C6-alkylthio,
• phenyl, phenyl-C1-C6-alkyl, phenylcarbonyl, phenylcarbonyloxy, phenoxycarbonyl, 5-, 6- or 7-membered heterocyclyl, phenoxy, phenylamino, diphenylamino, heterocyclyl-C1-C6-alkyl, heterocyclyloxy, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclylcarbonyloxy, where the phenyl and heterocyclyl groups of the 14 last-mentioned radicals may for their part be partially of fully halogenated and/or may carry one, two or three substituents selected from the group consisting of nitro, cyano, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, C1-C6-alkylamino, di-C1-C6-alkylamino, C3-C6-cycloalkylamino, where the alkyl and cycloalkyl groups of the three last-mentioned radicals may be partially or fully halogenated and/or may carry one to three substituents selected from the group consisting of C1-C4-alkoxy or hydroxyl,
• where carbon ring members may also be present as carbonyl function, thiocarbonyl function, oxime or oxime ether function;
• or
• R1a and R2a or R3a and R4a form a 5- or 6-membered saturated or unsaturated heterocycle which may have 1, 2 or 3 heteroatoms selected from the group consisting of N, S and O, where the ring atoms of the heterocycle may be substituted in the manner described above;
• and
• the remaining radicals R1a, R2a, R3a and R4a independently of one another have the meanings mentioned for R1a, or
• R2a is hydrogen or 5-, 6- or 7-membered heterocyclyl which has 1, 2 or 3 hetero atoms selected from the group consisting of N, S and O, where the ring atoms of the heterocycle may be substituted in the manner described above;
• and
• R1a, R3a and R4a independently of one another have the meanings mentioned above for R1a.