Patent ID: 6646151
Filing Date: 2003-11-11
Classification: C07C

Abstract:
A process for the preparation of a compound of the formula and, where appropriate, their tautomers, in each case in the free form or salt form, in whicheither X is CH or N, Y is OR, and Z is O, or X is N, Y is NHR8 and Z is O, S or S(&boxH;O); R1 is C1-C4alkyl; R2 is H, C1-C4alkyl, halogeno-C1-C4alkyl, C3-C6cycloalkyl or C1-C4alkoxymethyl; R3 and R4 independently of one another are H, C1-C4alkyl, C1-C4alkoxy, OH, CN, NO2, a (C1-C4alkyl)3â€”Si group, where the alkyl groups can be identical or different, halogen, (C1-C4alkyl)S(&boxH;O)m, (halogeno-C1-C4alkyl)S(&boxH;O)m, halogeno-C1-C4alkyl or halogeno-C1-C4alkoxy; R5 is C1-C6alkyl, halogeno-C1-C6alkyl, C1-C6alkoxy, halogeno-C1-C6alkoxy, C1-C6alkylthio, halogen-C1-C6alkylthio, C1-C6alkylsulfinyl, halogeno-C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, halogeno-C1-C6alkylsulfonyl, C1-C6alkoxy-C1-C6alkyl, halogeno-C1-C6alkoxy-C1-C6alkyl, C1-C6alkylthio-C1-C6alkyl, halogeno-C1-C6alkylthio-C1-C6alkyl, C1-C6alkylsulfinyl-C1-C6alkyl, halogeno-C1-C6-alkylsulfinyl-C1-C6alkyl, C1-C6-alkylsulfonyl-C1-C6alkyl, halogeno-C1-C6-alkylsulfonyl-C1-C6alkyl, C1-C6-alkylcarbonyl, halogeno-C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, halogeno-C1-C6-alkoxycarbonyl, C1-C6-alkylaminocarbonyl, C1-C6-alkoxyiminomethyl; di(C1-C6alkyl)-aminocarbonyl, where the alkyl groups can be identical or different; C1-C6-alkylaminothiocarbonyl; di(C1-C6alkyl)aminothiocarbonyl, where the alkyl groups can be identical or different; C1-C6-alkylamino, di(C1-C6alkyl)-amino, where the alkyl groups can be identical or different; halogen, NO2, CN, SF5, thioamido, thiocyanatomethyl; an unsubstituted or mono- to tetrasubstituted C1-C4alkylenedioxy group, where the substituents are selected from the group consisting of C1-C4alkyl and halogen; or QR6, where, if n is greater than 1, the radicals R5 can be identical or different; R6 is C2-C6alkenyl or C2-C6 alkynyl, which are unsubstituted or substituted by 1 to 3 halogen atoms; (C1-C4alkyl)3Si, where the alkyl groups can be identical or different; CN or an unsubstituted or mono- to pentasubstituted C3-C6cycloalkyl, aryl or heterocyclyl group, where the substituents are selected from the group consisting of halogen, C1-C6alkyl, halogeno-C1-C6alkyl, C1-C6alkoxy, halogeno-C1-C6alkoxy, phenoxy, naphthoxy and CN; A is a direct bond, C1-C10alkylene, â€”C(&boxH;O)â€”, â€”C(&boxH;S)â€” or halogeno-C1-C10alkylene and R7 is a radical R10, or A is C1-C10alkylene, â€”C(&boxH;O)â€”, â€”C(&boxH;S)â€” or halogeno-C1-C10alkylene and R7 is OR10, N(R10)2, where the radicals R10 can be identical or different, or â€”S(&boxH;O)qR10; R8 is H or C1-C4alkyl; R9 is methyl, fluoromethyl or difluoromethyl; R10 is H; an unsubstituted or substituted C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl group, where the substituents are selected from the group consisting of halogen; (C1-C4alkyl)3Si, where the alkyl groups can be identical or different; C3-C6cyclo-alkyl, which is unsubstituted or substituted by halogen; C1-C6alkoxycarbonyl, which is unsubstituted or substituted by halogen; unsubstituted or substituted aryl, where the substituents are selected from the group consisting of halogen, halogeno-C1-C4alkyl and CN; a (C1-C6alkyl)3Si group, where the alkyl groups can be identical or different; C3-C6cycloalkyl, which is unsubstituted or substituted by halogen; C1-C6alkoxycarbonyl which is unsubstituted or substituted by halogen; or an unsubstituted or substituted aryl or heterocyclyl group, where the substituents are selected from the group consisting of halogen and halogeno-C1-C4alkyl; Q is a direct bond, C1-C8alkylene, C2-C6alkenylene, C2-C6alkynylene, O, O(C1-C6alkylene), (C1-C6alkylene)O, S(&boxH;O)p, S(&boxH;O)p(C1-C6alkylene) or (C1-C6alkylene)S(&boxH;O)p; m is 0, 1 or 2; n is 0, 1, 2, 3, 4 or 5; p is 0, 1 or 2; and q is 0, 1 or 2, and the C&boxH;N double bond marked with E has the E configuration, which comprises a2) reacting a compound of the formula â€ƒin which A, R2, R5, R7 and n are as defined for formula (I) and the C&boxH;N double bond marked with E has the E configuration, or a tautomer thereof, in each case in the free form or in the salt form, with a compound of the formula â€ƒin which X, Y, Z, R3, R4 and R9 are as defined for formula (I), or, if appropriate, a tautomer thereof, in each case in the free form or in salt form, wherein the compound of formula (IV) is obtained by b1) reacting a compound of the formula â€ƒin which R2, R5 and n are as defined for formula (I) and the C&boxH;N double bond marked with E has the E configuration, or a tautomer thereof, in each case in the free form or in salt form, with a compound of the formula R7â€”Aâ€”X2â€ƒâ€ƒ(VII), â€ƒin which A and R7 are as defined for formula (I) and X2 is a leaving group, wherein the compound of formula (VI) is obtained by c) reacting a compound of the formula â€ƒin which R2, R5 and n are as defined for formula (I), or a tautomer thereof, in each case in the free form or in salt form, with a C1-C6alkyl nitrite.