Process for preparing imidazole derivatives

A process for preparing a compound of formula (II)

• wherein
• Q represents a structural element
• where the symbol # indicates the bond to the rest of the molecule and
• Q1 represents N or CR6,
• Q2 represents N or CR6,
• Q3 represents N or C,
• Q4 represents O, S, N, CR6 or NR7,
• Q5 represents N or C,
• Q6 represents N or CH and
• Q7 represents N or CH,
• where at most five of the variables Q1, Q2, Q3, Q4, Q5, Q6 and Q7 simultaneously represent nitrogen and Q3 and Q5 do not simultaneously represent N and
• R6 represents hydrogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-cyanoalkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkenyloxy-(C1-C4)-alkyl, (C2-C4)-haloalkenyloxy-(C1-C4)-alkyl, (C2-C4)-haloalkenyl, (C2-C4)-cyanoalkenyl, (C2-C4)-alkynyl, (C2-C4)-alkynyloxy-(C1-C4)-alkyl, (C2-C4)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C3-C6)-cycloalkyl, (C1-C4)-alkyl-(C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl or (C1-C4)-alkylcarbonyl-(C1-C4)-alkyl,
• R7 represents (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-cyanoalkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkenyloxy-(C1-C4)-alkyl, (C2-C4)-haloalkenyloxy-(C1-C4)-alkyl, (C2-C4)-haloalkenyl, (C2-C4)-cyanoalkenyl, (C2-C4)-alkynyl, (C2-C4)-alkynyloxy-(C1-C4)-alkyl, (C2-C4)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C3-C6)-cycloalkyl, (C1-C4)-alkyl-(C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl or (C1-C4)-alkylcarbonyl-(C1-C4)-alkyl and
• A represents hydrogen, cyano, halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C3-C6)-cycloalkyl, (C1-C4)-alkyl-(C3-C6)-cycloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkoxyimino, (C1-C4)-alkylthio, (C1-C4)-haloalkylthio, (C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl, (C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl, (C1-C4)-alkylsulfonyloxy, (C1-C4)-alkylcarbonyl, (C1-C4)-haloalkylcarbonyl, aminocarbonyl, (C1-C4)-alkylaminocarbonyl, di-(C1-C4)-alkylaminocarbonyl, (C1-C4)-alkylsulfonylamino, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, aminosulfonyl, (C1-C4)-alkylaminosulfonyl or di-(C1-C4)-alkylaminosulfonyl, or
• A represents —O—CF2—O— and, together with Q1 and the carbon atom to which it is attached, forms a five-membered ring where Q1 represents carbon,
• W represents halogen or S(O)nR8, where
• R8 represents (C1-C6)-alkyl, (C1-C6)-cyanoalkyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl or (C3-C8)-cycloalkyl and
• n represents 0, 1 or 2,
• V represents (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-cyanoalkyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C6)-haloalkoxy-(C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkenyloxy-(C1-C6)-alkyl, (C2-C6)-haloalkenyloxy-(C1-C6)-alkyl, (C2-C6)-haloalkenyl, (C2-C6)-cyanoalkenyl, (C2-C6)-alkynyl, (C2-C6)-alkynyloxy-(C1-C6)-alkyl, (C2-C6)-haloalkynyloxy-(C1-C6)-alkyl, (C2-C6)-haloalkynyl, (C2-C6)-cyanoalkynyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkyl-(C3-C8)-cycloalkyl, (C1-C6)-alkyl-(C3-C8)-cycloalkyl, halo-(C3-C8)-cycloalkyl, cyano-(C3-C8)-cycloalkyl, (C1-C6)-alkylthio-(C1-C6)-alkyl, (C1-C6)-haloalkylthio-(C1-C6)-alkyl, (C1-C6)-alkylsulfinyl-(C1-C6)-alkyl, (C1-C6)-haloalkylsulfinyl-(C1-C6)-alkyl, (C1-C6)-alkylsulfonyl-(C1-C6)-alkyl, (C1-C6)-haloalkylsulfonyl-(C1-C6)-alkyl, (C1-C6)-alkylcarbonyl-(C1-C6)-alkyl, (C1-C6)-haloalkylcarbonyl-(C1-C6)-alkyl, (C1-C6)-alkoxycarbonyl-(C1-C6)-alkyl or (C1-C6)-haloalkoxycarbonyl-(C1-C6)-alkyl and
• Y represents hydrogen, halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-haloalkylthio, (C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl, (C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl, SCN, (C1-C4)-alkylcarbonyl, (C1-C4)-haloalkylcarbonyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-haloalkoxycarbonyl, aminocarbonyl, (C1-C4)-alkylaminocarbonyl, di-(C1-C4)-alkylaminocarbonyl, (C1-C4)-haloalkylaminocarbonyl, (C3-C6)-cycloalkylaminocarbonyl, aminothiocarbonyl, (C1-C4)-alkylaminothiocarbonyl, di-(C1-C4)-alkylaminothiocarbonyl, (C1-C4)-haloalkylaminothiocarbonyl, (C3-C6)-cycloalkylaminothiocarbonyl, amino, (C1-C4)-alkylamino, (C1-C4)-haloalkylamino, di-(C1-C4)-alkylamino, (C3-C6)-cycloalkylamino, (C1-C4)-alkylsulfonylamino, (C1-C4)-alkylcarbonylamino, (C1-C4)-haloalkylcarbonylamino, (C1-C4)-alkylcarbonyl-(C1-C4)-alkylamino, (C1-C4)-haloalkylcarbonyl-(C1-C4)-alkylamino, (C3-C6)-cycloalkylcarbonylamino, (C3-C6)-cycloalkylcarbonyl-(C1-C4)-alkylamino, (C1-C4)-alkylthiocarbonylamino, (C1-C4)-haloalkylthiocarbonylamino, (C1-C4)-alkylthiocarbonyl-(C1-C4)-alkylamino, (C1-C4)-haloalkylthiocarbonyl-(C1-C4)-alkylamino, (C3-C6)-cycloalkylthiocarbonylamino, (C3-C6)-cycloalkylthiocarbonyl-(C1-C4)-alkylamino, (C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C2-C4)-cyanoalkenyl, (C3-C6)-cycloalkyl-(C2)-alkenyl, (C2-C4)-alkynyl or (C2-C4)-haloalkynyl,
• or represents (C3-C6)-cycloalkyl or (C5-C6)-cycloalkenyl, each of which is optionally mono- or polysubstituted by identical or different substituents, possible substituents being in each case:
• (C3-C6)-cycloalkyl, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, aminocarbonyl, aminothiocarbonyl, halogen or cyano,
• or represents aryl or hetaryl, each of which is optionally mono- or polysubstituted by identical or different substituents, where (in the case of hetaryl) optionally at least one carbonyl group may be present and where possible substituents in each case are as follows:
• cyano, carboxyl, halogen, nitro, acetyl, hydroxy, amino, SCN, SF5, tri-(C1-C4)-alkylsilyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C3-C6)-cycloalkyl, (C1-C4)-alkyl-(C3-C6)-cycloalkyl, (C1-C4)-haloalkyl-(C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, cyano-(C3-C6)-cycloalkyl, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-cyanoalkyl, (C1-C4)-hydroxyalkyl, hydroxycarbonyl-(C1-C4)-alkoxy, (C1-C4)-alkoxycarbonyl-(C1-C4)-alkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C2-C4)-cyanoalkenyl, (C3-C6)-cycloalkyl-(C2)-alkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkynyl, (C2-C4)-cyanoalkynyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-cyanoalkoxy, (C1-C4)-alkoxycarbonyl-(C1-C4)-alkoxy, (C1-C4)-alkoxy-(C1-C4)-alkoxy, (C1-C4)-alkoxyimino, (C1-C4)-haloalkoxyimino, (C1-C4)-alkylthio, (C1-C4)-haloalkylthio, (C1-C4)-alkoxy-(C1-C4)-alkylthio, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl, (C1-C4)-haloalkylsulfinyl, (C1-C4)-alkoxy-(C1-C4)-alkylsulfinyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl, (C1-C4)-alkoxy-(C1-C4)-alkylsulfonyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyloxy, (C1-C4)-haloalkylsulfonyloxy, (C1-C4)-alkylcarbonyl, (C1-C4)-haloalkylcarbonyl, (C1-C4)-alkylcarbonyloxy, (C1-C4)-alkoxycarbonyl, (C1-C4)-haloalkoxycarbonyl, aminocarbonyl, (C1-C4)-alkylaminocarbonyl, (C1-C4)-haloalkylaminocarbonyl, di-(C1-C4)-alkylaminocarbonyl, (C2-C4)-alkenylaminocarbonyl, di-(C2-C4)-alkenylaminocarbonyl, (C3-C6)-cycloalkylaminocarbonyl, (C1-C4)-alkylsulfonylamino, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C1-C4)-haloalkylamino, (C3-C6)-cycloalkylamino, aminosulfonyl, (C1-C4)-alkylaminosulfonyl, di-(C1-C4)-alkylaminosulfonyl, (C1-C4)-alkylsulfoximino, aminothiocarbonyl, (C1-C4)-alkylaminothiocarbonyl, di-(C1-C4)-alkylaminothiocarbonyl, (C1-C4)-haloalkylaminothiocarbonyl, (C3-C6)-cycloalkylaminothiocarbonyl, (C1-C4)-alkylcarbonylamino, (C1-C4)-haloalkylcarbonylamino, (C1-C4)-alkylcarbonyl-(C1-C4)-alkylamino, (C1-C4)-haloalkylcarbonyl-(C1-C4)-alkylamino, (C3-C6)-cycloalkylcarbonylamino, (C3-C6)-cycloalkylcarbonyl-(C1-C4)-alkylamino, (C1-C4)-alkylthiocarbonylamino, (C1-C4)-haloalkylthiocarbonylamino, (C1-C4)-alkylthiocarbonyl-(C1-C4)-alkylamino, (C1-C4)-haloalkylthiocarbonyl-(C1-C4)-alkylamino, (C3-C6)-cycloalkylthiocarbonylamino, (C3-C6)-cycloalkylthiocarbonyl-(C1-C4)-alkylamino, hetaryl, oxohetaryl, halohetaryl, halooxohetaryl, cyanohetaryl, cyanooxohetaryl, (C1-C4)-haloalkylhetaryl or (C1-C4)-haloalkyloxohetaryl,
• said process comprising, a) reacting a compound Q-H with an organozinc base of the structure (NR3R4)—Zn—R2 or (NR3R4)2—Zn in which
• R2 represents halogen or —O-pivaloyl and
• R3 and R4 together form a —(CH2)4—, —(CH2)5— or —(CH2)2O(CH2)2— group, where each of these groups may optionally be substituted by 1, 2, 3 or 4 R5 radicals and R5 is selected from the group consisting of methyl, ethyl, n-propyl and i-propyl,
• to give a compound of formula (IIIa) or formula (IIIb)
• and
• b) reacting said compound of formula (IIIa) or (IIIb) with a compound of formula (I)
• in the presence of a catalyst, to give the compound of formula (II).