MX2007003057A

MX2007003057A - 5-heterocyclyl pyrimidines.

Info

Publication number: MX2007003057A
Application number: MX2007003057A
Authority: MX
Inventors: Herbert Gayer; Ulrich Heinemann; Peter Dahmen; Stefan Hillebrand; Karl-Heinz Kuck; Ulrike Wachendorff-Neumann; Stefan Herrmann; Olaf Gebauer; Ronald Ebbert; Kerstin Ilg
Original assignee: Bayer Cropscience Ag
Priority date: 2004-09-16
Filing date: 2005-09-15
Publication date: 2009-02-16
Also published as: KR20070052324A; BRPI0515385A; EP1791834A1; CA2580243A1; DE102004044829A1; WO2006029867A1; CN101023078A; JP2008513399A

Abstract

The invention relates to novel 5-heterocyclyl pyrimidines, several methods for the production thereof, and the use thereof for controlling unwanted microorganisms. The invention also relates to novel intermediate products and methods for the production thereof.

Description

5-HETEROCICLILPIRIMIDINAS FIELD OF THE INVENTION The present invention relates to new 5-heterocyclylpyrimidines, as well as to a process for their preparation and their use to combat unwanted microorganisms. The invention also relates to new intermediate products, as well as to processes for their preparation. BACKGROUND OF THE INVENTION It is already known that certain 5-phenylpyrimidines have fungicidal properties (see WO03 / 070721, WO02 / 074753, WO01 / 96314, WO03 / 43993). The action of these substances is good, but in many cases it leaves to be desired at low doses. However, because the ecological and economic requirements of modern fungicides increase continuously, for example with respect to the spectrum of action, toxicity, selectivity, dose, formation of residues and favorable productivity, and in addition they can appear, for example, problems of resistances , there is the continuous objective of developing new fungicides that at least have advantages in partial fields compared to the known ones. New 5-heterocyclylpyrimidines of formula were now discovered RER: 179816 wherein R1 represents hydrogen, Ci-C8 alkyl, C2-C8 alkenyl, C3-Cs alkynyl, C3-C3 cycloalkyl or C3-C8 cycloalkenyl, wherein R1 may be substituted with one to three Ra groups the same or different Ra represents halogen, hydroxy, cyano, C1-C4 alkoxy and / or C3-C6 cycloalkyl, or R1 represents a saturated, unsaturated or aromatic mono- or bicyclic heterocycle of five to ten members containing from one to four heteroatoms of group 0, N or S, wherein R1 may be substituted with one to two identical or different Rb groups, and Rb represents halogen, Ci-C6 alkyl, cyano, nitro, and / or C3-C6 cycloalkyl; R 2 represents hydrogen or C 1 -C 6 alkyl, or R 1 and R 2 represent together with the nitrogen atom to which are attached a saturated or unsaturated mono or bicyclic heterocycle of three to six members, in which the heterocycle may contain another heteroatom of the group 0, N or S and can be substituted with one to three identical or different Rc groups, and Rc represents halogen, C1-C6 alkyl and / or Ci-C6 haloalkyl, R3 represents a saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle of three to ten members containing from one to four heteroatoms' of the group 0, N or S, in which R3 may be substituted with one to four identical or different Rd groups, and Rd represents halogen, hydroxy, cyano, oxo, nitro, amino, mercapto, Ci-C6 alkyl, haloalkyl Ci ~ C6, C2-alkenyl C2-C5 alkynyl, C3-C6 cycloalkyl, Ci-C6 alkoxy, Ci-6-haloalkoxy, carboxyl, Ci-C7-alkoxycarbonyl, carbamoyl, Ci-C7 alkyl-aminocarbonyl, Ci alkyl -C6-Ci-C6alkylaminocarbonyl, morpholinocarbonyl, pyrrolidinocarbonyl, Ci-C7alkylaminocarbonylamino, Ci-Calkylamino, di- (Ci-C6alkylamino), Ci-C6 alkylthio, Ci-C6 alkyl -sulfinyl, Ci-C6-sulphonyl, hydroxysulfonyl, aminosulfonyl, Ci-C6-alkylsulfonyl and / or di- (Ci-CQ alkyl) aminosulfonyl; R 4 represents halogen or C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkyl, C 1 -C 8 alkylthio, C 1 -C 8 alkylsulfinyl, C 1 -C 8 alkylsulfonyl or cyano, R 5 represents a saturated mono or bicyclic heterocycle , unsaturated or aromatic of five or six members containing one to four heteroatoms of group 0, N or S, in wherein R5 may be substituted with one to four equal or different Re groups, and Re represents halogen, hydroxy, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3 cycloalkyl -C6, Ci-C6 alkoxy, C1-C6 haloalkoxy, carboxyl, Ci-C7 alkoxycarbonyl, carbamoyl, C1-C7 alkylaminocarbonyl, Ci-Cg alkyl Ci-C6 alkylcarbonyl, Ci-C6 alkyl thio, Ci alkyl -Cg-sulfinyl, Ci-C-sulphonyl, hydroxyimino-C1-C6 alkyl and / or C1-C6 alkyl-alkoxyimino C1-C6 alkyl. DETAILED DESCRIPTION OF THE INVENTION The compounds of formula I have a good efficacy against undesired microorganisms. The compounds of formula I can be obtained in different ways. In this sense, all definitions of remains have the meanings given above. 1) Reaction scheme 1 shows the synthesis of the compounds I ', in which R3 represents an N-linked heterocycle.

Reaction Scheme 1: Synthesis of the compounds (? ') (N-linked R3 heterocycle) Starting from thiourea (XIV), by cyclization with malonic esters of type XVII, pyrimidines of type XVI are obtained (method I)) or by cyclization with acetoacetates of type XIII pyrimidines of type XI (method i)). The alkylation of the thio group results in compounds of type XV (procedure k)) or type X (procedure h)). After the halogenation to give pyrimidines of type IX (process j) or g)) a reaction takes place to give the amines of type II (process f)). Oxidation provides compounds of type III (process a)) and the reaction with heterocycles containing N finally results in the compounds of formula I 'according to the invention (process b)). 2) The compounds of formula I1"" can be prepared analogously to the syntheses described on pages 3 to 4 of WO2004 / 103978 by first reacting the sulfopyrimidines of formula III (see reaction scheme 1) with hydrazine for give compounds of type XXI. Reaction scheme 2: The subsequent synthesis can take place as shown in the reaction scheme 3: Reaction scheme 3 Base The hydrazine compound XXI is condensed with a dicarbonyl compound XXII, in which the substituents R1, R2, R4, R5, R6 and Rd have the previously indicated meaning and R 'means an alkyl, aryl or benzyl group (see scheme 3) and thus the compounds of formula XXIII are obtained. The dicarbonyl compounds of formula XXII They know each other from Angew. Chem. Int. Ed. Engl. 1989 28, page 500. The condensation takes place as explained in more detail in DE19627002. The ring closure to give the compounds I "" according to the invention takes place, for example, in the presence of bases such as especially alkali metal alkoxylates. The reaction is explicitly described with sodium methylate (Synlett 1996, 667-8). In the presence of RdX alkylating agents, in which Rd has the aforementioned meaning and X represents a starting group such as halide or sulfate, and a strong base, such as for example sodium hydride or anhydrous potassium carbonate, the compounds are obtained i '"" according to the invention. 3) Reaction scheme 4 shows the synthesis of compounds I ", in which R3 represents a heterocycle linked by C.

Reaction Scheme 4: Synthesis of the compounds (I ") (R3 heterocycle linked by C) By cyclization of heterocyclicly substituted amidines (commercially available, for example, Chemstep company (www.chemstep.com)) of type XIX with malonic esters of type XVII, pyrimidines of type XX (p procedure) or acetoacetates of type XIII are obtained pyrimidines of type XVIII (procedure n)). In this regard, the amidines can also be used in the form of salts and released on a base in situ basis. Halogenation provides pyrimidines of type V (process o) or m)), which react with amines to give the compounds I "according to the invention (process c) 4) Pyrimidines of type I '" according to the invention substituted in R4 in the 6-position they are obtained by reaction of the halogenopyrimidines (I'a or I "a) with metal compounds of the type R4M1 or compounds of Grignard VIII (see reaction scheme 5). Reaction scheme 5: synthesis of the compounds (I '") It was now discovered that the 5-heterocyclylpyrimidines formula (I '), wherein R1, R2 and R5 have the meanings given above, R3 represents a heterocycle linked by N and R4 halogen, C1-C alkyl or haloCalkyl Ci_C4, can be prepared by oxidizing according to the process a) compounds of formula (II), wherein R1, R2 and R5 have the meanings given above, R4 represents halogen, C1-C alkyl or C1-C4 haloalkyl, and R6 represents Ci-C6 alkyl, with an oxidant, optionally in the presence of a diluent, and by reacting according to process b) the compounds of formula (III) thus obtained wherein R1, R2, R5 and R6 have the meanings given above, R4 represents halogen, C1-C alkyl or C1-C4 haloalkyl, and n is = 1 or 2, with a compound of formula R3-H (IV), in wherein R3 has the meanings indicated above, with the proviso that R3 has at least one nitrogen atom through which binding to the pyrimidine ring takes place in compounds of formula (I '), optionally in the presence of a diluent and given the case in the presence of a base. The 5-heterocyclylpyrimidines of formula (I1 1), wherein R1, R2 and R5 have the meanings indicated above, R3 represents a linked heterocycle by C and R 4 represents halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl, can be prepared by reacting according to process c) compounds of formula (V), wherein R3, R5 have the meanings indicated above, with the proviso that R3 is a heterocycle which is linked by a C atom to the pyrimidine ring in compounds of type (V), and R4 represents halogen, C1- alkyl C4 or C1-C4 haloalkyl, with a compound of formula HNR1R2 (VI), in which R1 and R2 have the meanings indicated above, optionally in the presence of a diluent, optionally in the presence of a catalyst and optionally in the presence of an acid acceptor. The 5-heterocyclylpyrimidines of formula (! '"), wherein R1, R2 and R5 have the meanings given above, R3 represents a heterocycle linked by N or C and R4 Ci-Ca alkyl, Ci-C8 alkoxy, Ci-C8 alkyl thio, Ci-C8 alkylsulfonyl or cyano , can be prepared by reacting compounds of formula (I'a) or (I "a) wherein R1, R2, R3 and R5 have the meanings given above and Hal represents halogen, or according to process d) with a compound of formula RMI1 (VII) in which R4 represents Ci-Cg alkoxy, Ci-alkyl; Cs-tio, Ci-alkyl Ce-sulfinyl, Ci-Cs-sulfonyl alkyl or cyano, and M1 represents sodium or potassium, optionally in the presence of a diluent, or according to process e) with Grignard compounds of formula R4-MgHal (VIII) in which R4 represents Ci-C8 alkyl and Hal represents chlorine or bromine, in the presence of a diluent and optionally in the presence of a catalyst. Finally it was discovered that the 5-heterocyclylpyrimidines of formula (I) are very suitable for combating unwanted microorganisms. They show above all a strong fungicidal efficacy and can be used both in the protection of plants and in the protection of materials. Surprisingly, the 5-heterocyclylpyrimidines of formula (I) according to the invention possess an essentially better microbicidal efficacy than previously known substances of the same action direction of similar constitution. The compounds of formula (I) according to the invention can optionally be present as mixtures of different possible isomeric forms, especially of stereoisomers such as E and Z, threo and erythro, as well as optical isomers such as R and S isomers or atropisomers. , but also the case of tautomers.

In the definitions of the symbols indicated in the preceding formulas, groups were used which generally represent representatively the following substituents: Halogen: fluorine, chlorine, bromine and iodine; halogen preferably represents chlorine or bromine, with particular preference chlorine; Alkyl: straight or branched chain hydrocarbon radicals with 1 to 4, 6 or 8 carbon atoms, for example Ci-C6 alkyl such as methyl, ethyl, propyl, 1- ^ methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-di-methylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1-2. dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1- ^ dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3 , 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl; Halogenoalkyl: straight or branched chain alkyl groups with 1 to 8 carbon atoms (as mentioned above), in which in these groups the hydrogen atoms may be partially or completely substituted with halogen atoms as mentioned above, 25 example C 1 -C 3 halogenoalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro- 2-fluoroethyl, 2-chloro-2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and 1,1-trifluoroprop-2-yl; Alkenyl: unsaturated hydrocarbon radicals, straight or branched chain with 2 to 4, 6 or 8 carbon atoms and a double bond at any position, for example C2-C6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methyl-1-methyl-1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl , 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-l-butenyl, 3-methyl-l-butenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2- methyl-3-butenyl, 3-methyl-3-butenyl, 1, l-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1- propenyl, l-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl - 1-pentenyl, 4-methyl-l-pentenyl, l-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, l-methyl-3 -pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl- 4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl , 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl , 2, 2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3, 3-dimethyl-l-butenyl , 3, 3-dimethyl-2-butenyl, 1-ethyl-l-butenyl, 1-ethyl-2-butenyl, l-ethyl-3-butenyl, 2-ethyl-l-butenyl, 2-ethyl-2-butenyl , 2-ethyl-3-butenyl, 1, 1, 2-trimethyl-2- ^ propenyl, l-ethyl-l-methyl-2-propenyl, l-ethyl-2-methyl-1-propenyl and l-ethyl- 2-methyl-2-propenyl; Alkynyl: straight or branched chain hydrocarbon groups with 2 to 4, 6 or 8 carbon atoms and a triple bond in any position, for example C2-C6 alkynyl ^ such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l- methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1- Hexinyl, 2- 20 Hexynyl, 3-Hexynyl, 4-Hexynyl, 5-Hexynyl, 1-Methyl-2-Pentylin, 1-Methyl-3-Pentynyl, 1-Methyl-4-Pentynyl, 2-Methyl-3-Pentynyl , 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1, 1-dimethyl-2-butynyl , 1, 1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3, 3-dimethyl-1-butynyl, l-ethyl-2-butynyl, l-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-l-methyl-2-propynyl; Cycloalkyl: monocyclic saturated hydrocarbon groups with 3 to 8 carbon ring members such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl; Cycloalkenyl: unsaturated saturated hydrocarbon groups with 3 to 8 carbon ring members with at least one double bond, such as cyclopenten-1-yl, cyclohexen-1-yl, cyclohepta-1,3-dien-1-yl; Alkoxycarbonyl: an alkoxy group with 1 to 6 carbon atoms (as mentioned above) which is attached to the backbone by a carbonyl group (-C0-); Oxyalkylene Oxide: unbranched divalent chains of 1 to 3 CH2 groups, in which both valences are attached to the skeleton by an oxygen atom, for example OCH20, OCH2CH20 and OCH2CH2CH20; Saturated or partially unsaturated heterocycle of five to ten members containing one to four heteroatoms of the oxygen, nitrogen or sulfur group: mono or bicyclic heterocycles (heterocyclyl) containing, in addition to carbon ring members, from one to three nitrogen atoms and / or an oxygen or sulfur atom or one or two oxygen and / or sulfur atoms; if the ring contains several oxygen atoms, then these are not directly contiguous; for example, oxiranyl, aziridinyl, 2-tetrahydrofuranyl, 3- tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetr. 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, pyrazolidinyl 4-, 5-pirazolidimlo, 2-oxazolidimlo, 4- oxazolidinyl, 5-oxazolidinyl, 2- thiazolidinyl, 4- thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4- imidazolidinyl, 1, 2, -oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1 2, 4-thiadiazolidin-3-yl, 1,2,4- ^ thiadiazolidin-5-yl, 1, 2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 2 3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2-dihydrofur-2-yl , 2, 4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3 ilo, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3- isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3 -isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-l-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazole -4-yl, 2,3- 25 dihydropyrazol-5-yl, 3, -dihydropyrazol-1-yl, 3,4- dihydro-pyrazol-3-yl, 3 -dihidropirazol-4-yl, 3,4-dihydro-5-yl-4, 5-dihydro-l-yl, 4,5-dihydro-pyrazol-3-yl, 5-dihidropirazol- 4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazole- 5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazole- 2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1, 3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1, 3, 5-hexahydro-triazin-2-yl and 1,2,4-hexahydrotriazin-3-yl; Aromatic heterocycle of five to ten members containing one to four heteroatoms of the oxygen, nitrogen or sulfur group: heteroaryl of one or two nuclei, for example 5-membered heteroaryl containing from one to four nitrogen atoms or from one to three Nitrogen atoms and a sulfur or oxygen atom: 5-ring heteroaryl groups which, in addition to the carbon atoms, may contain from one to four nitrogen atoms or from one to three nitrogen atoms and one sulfur atom or oxygen as a ring member, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, -isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl , 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1 , 2,4-oxadiazol-3-yl, 1, 2,4-oxadiazol-5-yl, 1, 2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1, 2 , 4-triazol-3-yl, 1, 3, 4-oxadiazol-2-yl, 1, 3, 4-thiadiazol-2-yl and 1,3,4-triazol-2-yl; Benzo-depleted 5-membered heteroaryl containing from one to three nitrogen atoms or a nitrogen atom and an oxygen or sulfur atom: 5-membered heteroaryl groups which, in addition to the carbon atoms, may contain from one to four nitrogen atoms or of one to three nitrogen atoms and a sulfur or oxygen atom as a ring member, and in which two adjacent carbon members or a nitrogen member and an adjacent carbon member can be bridged by a butadiene group. 1,3-dien-1,4-diyl in which one or two C atoms can be substituted with N atoms; 5-membered heteroaryl linked by nitrogen containing from one to four nitrogen atoms or benzo-condensed 5-membered heteroaryl by nitrogen containing from one to three nitrogen atoms: 5-membered heteroaryl groups which, in addition to the carbon atoms, may contain from one to four nitrogen atoms or from one to three nitrogen atoms as a ring member, and in which two adjacent carbon members or a nitrogen member and an adjacent carbon member they can be bridged by a buta-1,3-dien-l, 4-diyl group, in which one or two C atoms can be substituted with N atoms, in which one or two C atoms can be be substituted with N atoms, these rings being attached to the backbone by one of the ring members of nitrogen, for example, 1-pyrrolyl, 1-pyrazolyl, 1, 2,4-triazol-1-yl, 1-imidazolyl, 1,2,3-triazol-1-yl, 1,3,4-triazol-1-yl; 6-membered heteroaryl containing one to three or one to four nitrogen atoms: 6-membered heteroaryl groups which, in addition to the carbon atoms, may contain one to three or one to four nitrogen atoms as a member of ring, for example 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1, 3, 5-triazin-2-yl and 1, 2,4-triazin-3 ilo; The especially preferred embodiments of the intermediates with respect to the variables correspond to those of the radicals R1 to R5 of formula (I). For the final products of formula (I), as also correspondingly for the starting substances or intermediates necessary respectively for the In the preparation, the following meanings of the substituents are particularly preferred, and in particular, respectively, alone or in combination. Preference is given to compounds of formula (I) in which R 1 represents a radical of formula where # marks the union position. Especially preferred are compounds of formula (I) in which R 1 represents a radical Preference is given to compounds of formula (I) in which R2 represents hydrogen, methyl, ethyl or propyl.

Also preferred are compounds of formula (I) in which R1 and R2 represent together with the nitrogen atom to which pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, 3,6-dihydro-l (2H) -piperidinyl or tetrahydro are attached -1 (2H) -pyridazinyl, in which these radicals can be substituted with 1 to 3 fluorine atoms, 1 to 3 methyl and / or trifluoromethyl groups. Also preferred are compounds of formula (I) in which R 1 and R 2 represent, together with the nitrogen atom to which a radical of formula is attached wherein R7 represents hydrogen or methyl, R8 represents methyl, ethyl, fluorine, chlorine or trifluoromethyl, m represents the numbers 0, 1, 2 or 3, in which R8 represents the same or different residues, when m represents 2 or 3, R9 represents methyl, ethyl, fluorine, chlorine or trifluoromethyl, and represents the numbers 0, 1, 2 or 3, in which R9 represents identical or different residues, when n represents 2 or 3. Preference is given to compounds of formula (I) in which R3 is an aromatic heterocycle. In addition, compounds of formula (I) in which R3 is a three, five or six membered heterocycle, especially five membered, are preferred. Especially preferred are compounds of formula (I) wherein R3 is a nitrogen-containing heterocycle. In addition, compounds of formula (I) in which R3 is a heterocycle that is linked to the pyrimidine ring by nitrogen are preferred. Also preferred are compounds of formula (I) in which R 3 represents the following groups: pyrrole, pyrazole, imidazole, 1,2,4-triazole, 1,2,3-triazole, tetrazole, 1,2,3-triazine, 1, 2, 4-triazine, oxazole, isoxazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, furan, thiophene, thiazole, isothiazole, in which the heterocycle may be linked to the pyrimidine ring by C or N. In addition, compounds of formula (I) in which the R3 cycle represents pyridazine, pyrimidine or pyrazine are preferred.

Also preferred are compounds of formula (I) in which R 3 represents, if appropriate, pyrazole, pyrrole, imidazole, 1,2,3-triazole, 1,2,4-triazole, 1,3,4-oxadiazole, , 3,4-thiadiazole, tetrazole, 2-pyridine, 2-pyrimidine, pyrazine or 3- pyridazine substituted with up to four groups Rd. Also preferred are compounds of formula (I) in which R 3 represents, if appropriate, pyrazole, pyrrole, imidazole, 1,2,3-triazole, 1,2,4-triazole, , 3, 4-oxadiazole, 1,3,4-thiadiazole, tetrazole, 2-pyridine, 2-pyrimidine, pyrazine or 3-pyridazine substituted with up to three groups Rd. Especially preferred are compounds of formula (I) in which R 3 represents pyrazole, 1,2,3-triazole, 1,2,4-triazole or pyridazine. In addition, compounds of formula (I) in which the ring R3 is substituted with one to three Rd groups identical or different from the following are especially preferred: halogen, hydroxy, cyano, nitro, amino, mercapto, alkyl i ~ Ce, Ci-C6 haloalkyl, C2- alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, Ci-C6 alkoxy, Ci-C6 haloalkoxy, carboxyl, Ci-C7 alkoxycarbonyl, carbamoyl, Ci-C7 alkylaminocarbonyl, alkyl Ci-C6-Ci-C6-aminocarbonyl, morpholinocarbonyl, oxo, pyrrolidinocarbonyl, Ci-C6-alkylcarbonylamino, C1-C6-alkylamino, di- (Ci-C6 alkyl) amino, alkyl d-C6-thio, Ci alkyl -C6-sulfinyl, Ci-C6 alkylsulfonyl, hydroxysulfonyl, aminosulfonyl, Ci-C6 alkylsulphonyl or di- (Ci-Cs alkyl) aminosulfonyl. Particularly preferred are compounds of formula (I) in which the R3 cycle is substituted with one to three Rd groups equal to or different from the following: halogen, cyano, nitro, hydroxy, amino, alkylC, haloalkyl Ci-C6, alkoxy Ci-C6, carboxyl, alkoxy Ci-C7-carbonyl, carbamoyl, Ci-C7 alkyl -aminocarbonyl, di- (alkyl) Ci-C6) aminocarbonyl or Ci-C7 alkylcarbonylamino or oxo. Especially preferred are compounds of formula (I) in which R3 is unsubstituted or substituted once with halogen, cyano, nitro, methyl, hydroxy, oxo or methoxy. In addition, compounds of formula (I) in which R 4 are preferred are preferred. ^ represents halogen, Ci-C6 alkyl, C1-C6 haloalkyl or C1-C6 alkoxy, especially represents halogen. Especially preferred are compounds of formula (I) in which R 4 is chlorine. In addition, pyrimidines of formula (I) are preferred in the that R 5 represents pyridyl, which is attached at the 2 or 4 position and can be substituted equally or differently once to four times with fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl , hydroxymethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl. Also preferred are pyrimidines of formula (I) in which R 5 represents pyrimidyl, which is attached in the 2 or 4 position and may be substituted in the same or different manner from one to three times with fluorine, chlorine, bromine, 5 cyano , nitro, methyl, ethyl, methoxy, methylthio, hydroxymethyl, hydroxymethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl. Also preferred are pyrimidines of formula (I) in which R 5 represents thienyl, which is attached in the 2 or 3 position and can be substituted in the same or different way once to three times with fluorine, chlorine, bromine, cyano, nitro , methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroxymethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl. Also preferred are pyrimidines of formula (I) in which R 5 represents thiazolyl, which is attached in the 2, 4 or 5 position and can be substituted in the same or different way once to twice with fluorine, chlorine, bromine, cyano , nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroxymethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl. Especially preferred are, in terms of their use, the compounds I listed in the following tables. In addition, the groups mentioned in the tables for a substituent represent, considered in themselves, independently of the combination in which they are mentioned, a particularly preferred configuration of the substituent in question.

Table 1 Compounds of formula (1-1) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 2 Compounds of formula (1-1) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to one row of Table A. Table 3 Compounds of formula (1-1) in which R5 represents a com cpuese and the combination of the remains R1 and R2 for to corresponds respectively to a row of Table A. Table 4 Compounds of formula (1-1) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 5 Compounds of formula (1-1) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of the 15 table A. Table 6 Compounds of formula (1-1) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 7 Compounds of formula (1-1) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A. Table 8 Compounds of formula (1-1) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 9 Compounds of formula (1-1) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 10 Compounds of formula (1-1) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 11 Compounds of formula (1-1) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 12 Compounds of formula (1-1) in which R5 represents and the combination of the residues R1 and R for a compound corresponds respectively to a row of table A. Table 13 Compounds of formula (1-1) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 14 Compounds of formula (1-1) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 15 Compounds of formula (1-1) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of table A. Table 16 Compounds of formula (1-1) in which R5 represents and the combination of the remains R and R for a compound corresponds respectively to a row of table A. Table 17 Compounds of formula (1-1) in which R5 represents for a compound corresponds respectively to one of table A. Table 18 Compounds of formula (1-1) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 19 Compounds of formula (1-1) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 20 Compounds of formula (1-2) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 21 Compounds of formula (1-2) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 22 Compounds of formula (1-2) in which R5 represents a comapuesto: and the combination * of the remains R1 and R2 for corresponds respectively to a row of Table A. Table 23 Compounds of formula (1-2) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 24 Compounds of formula (1-2) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 25 Compounds of formula (1-2) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 26 Compounds of formula (1-2) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 27 Compounds of formula (1-2) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 28 Compounds of formula (1-2) in which R5 represents and the combination of the residues R1 and R for a compound corresponds respectively to a row of table A. Table 29 Compounds of formula (1-2) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 30 Compounds of formula (1-2) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 31 Compounds of formula (1-2) in which R5 represents and the combination of the radicals R.sub.1 and R.sub.2 for a compound corresponds respectively to one row of Table A. Table 32 Compounds of formula (1-2) in which R.sub.5 represents and the combination of the residues R1 and R2 for compound corresponds respectively to a row of table A. Table 33 Compounds of formula (1-2) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 34 Compounds of formula (1-2) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 35 Compounds of formula (1-2) in which R5 represents and the combination of the remains R and R for a The compound corresponds respectively to a row of table A. Table 36 Compounds of formula (1-2) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 37 Compounds of formula (1-2) in which R5 represents for a compound corresponds respectively to a row of table A. Table 38 Compounds of formula (1-2) in which R5 represents for a compound corresponds respectively to a row of table A.

Table 39 Compounds of formula (1-3) in which R 5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 40 Compounds of formula (1-3) in which R 5 represents a * "*: and the combination of the radicals R 1 and R 2 for a compound corresponds respectively to one row of table A. Table 41 Compounds of formula (1 -3) in which R5 represents Ne and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 42 Compounds of formula (1-3) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to one row of Table A. Table 43 Compounds of formula (1-3) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 44 Compounds of formula (1-3) in which R5 represents S and the combination of the radicals R.sub.1 and R.sub.2 for a compound correspond respectively to one row of Table A. Table 45 Compounds of formula (1-3) in which R.sub.5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 46 Compounds of formula (1-3) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 47 Compounds of formula (1-3) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 48 Compounds of formula (1-3) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 49 Compounds of formula (1-3) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 50 Compounds of formula (1-3) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 51 Compounds of formula (1-3) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 52 Compounds of formula (1-3) in which R5 represents c ° £ and the combination of the radicals R and R for a compound correspond respectively to a row of table A. Table 53 Compounds of formula (1-3) in which R 5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 54 Compounds of formula (1-3) in which R5 represents The compound corresponds respectively to a row of table A. Table 55 Compounds of formula (1-3) in which R5 represents and the combination of the remains R1 and R2 for a compound corresponds respectively to a row of table A. Table 56 Compounds of formula (1-3) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 57 Compounds of formula (1-3) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 58 Compounds of formula (1-4) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 59 Compounds of formula (1-4) in which R represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 60 Compounds of formula (1-4) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 61 Compounds of formula (1-4) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 62 Compounds of formula (1-4) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 63 Compounds of formula (1-4) in which R5 represents dS and the combination of the residues R1 and R2 for one compound correspond respectively to one row of table A. Table 64 Compounds of formula (1-4) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A. Table 65 Compounds of formula (1-4) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to one row of Table A. Table 66 Compounds of formula (1-4) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to one row of Table A. Table 67 Compounds of formula (1-4) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 68 Compounds of formula (1-4) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 69 Compounds of formula (1-4) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row in Table A. Table 70 Compounds of formula (1-4) in which R5 represents The compound corresponds respectively to a row of table A. Table 71 Compounds of formula (1-4) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 72 Compounds of formula (1-4) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 73 Compounds of formula (1-4) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of the Table A. Table 74 Compounds of formula (1-4) in which R5 represents a compound corresponds respectively to a row of table A. Table 75 Compounds of formula (1-4) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 76 Compounds of formula (1-4) in which R5 represents for a compound corresponds respectively to a row of table A. Table 77 Compounds of formula (1-5) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 78 Compounds of formula (1-5) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 79 Compounds of Formula (1-5) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 80 Compounds of formula (1-5) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 81 Compounds of Formula (1-5) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 82 Compounds of Formula (1-5) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 83 Compounds of Formula (1-5) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 84 Compounds of Formula (1-5) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 85 Compounds of formula (1-5) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 86 Compounds of formula (1-5) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 87 Compounds of Formula (1-5) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 88 Compounds of formula (1-5) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 89 Compounds of formula (1-5) in which R5 represents The compound corresponds respectively to a row of table A. Table 90 Compounds of formula (1-5) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 91 Compounds of formula (1-5) in which R represents and R for a compound corresponds respectively to a row of table A. Table 92 Compounds of formula (1-5) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of the table A. Table 93 Compounds of formula (1-5) in which R5 represents for a compound corresponds respectively to a row of table A. Table 94 Compounds of formula (1-5) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 95 Compounds of Formula (1-5) in which R5 represents for a compound corresponds respectively to a row of table A. Table 96 Compounds of formula. { 1-6) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 97 Compounds of formula (1-6) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 98 Compounds of formula (1-6) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 99 Compounds of formula (1-6) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 100 Compounds of formula (1-6) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 101 Compounds of formula (1-6) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 102 Compounds of formula (1-6) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to one row of Table A. Table 103 Compounds of formula (1-6) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 104 Compounds of formula (1-6) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 105 Compounds of formula (1-6) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 106 Compounds of formula (1-6) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 107 Compounds of formula (1-6) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 108 Compounds of formula (1-6) in which R5 represents The compound corresponds respectively to a row of table A. Table 109 Compounds of formula (1-6) in which R5 represents and the combination of the residues Ri and R? for a compound corresponds respectively to a row of table A. Table 110 Compounds of formula (1-6) in which R5 represents for a compound corresponds respectively to a row of table A. Table 111 Compounds of formula (1-6) in which R5 represents and the combination of the remains R and R for a The compound corresponds respectively to a row of table A. Table 112 Compounds of formula (1-6) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 113 Compounds of formula (1-6) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 114 Compounds of formula (1-6) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 115 Compounds of formula (1-7) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 116 Compounds of formula (1-7) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 117 Compounds of formula (1-7) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 118 Compounds of formula (1-7) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 119 Compounds of formula (1-7) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 120 Compounds of formula (1-7) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 121 Compounds of formula (1-7) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 122 Compounds of formula (1-7) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 123 Compounds of formula (1-7) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 124 Compounds of formula (1-7) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 125 Compounds of formula (1-7) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 126 Compounds of formula (1-7) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 127 Compounds of formula (1-7) in which R5 represents The compound corresponds respectively to a row of table A. Table 128 Compounds of formula (1-7) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 129 Compounds of formula (1-7) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 130 Compounds of formula (1-7) in which R5 represents and the combination of the remains R and R for a The compound corresponds respectively to a row of table A. Table 131 Compounds of formula (1-7) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 132 Compounds of formula (1-7) in which R5 represents for a compound corresponds respectively to a row of table A. Table 133 Compounds of formula (1-7) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 134 Compounds of formula (1-8) in which R5 represents C NXI and the combination of the residues R1 and R2 for a compound correspond respectively to a row of table A.

Table 135 Compounds of formula (1-8) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 136 Compounds of formula (1-8) in which R5 represents and the combination of the remains R1 and R2 for a compound corresponds respectively to a row of table A. Table 137 Compounds of formula (1-8) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 138 Compounds of formula (1-8) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 139 Compounds of formula (1-8) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 140 Compounds of formula (1-8) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 141 Compounds of formula (1-8) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 142 Compounds of formula (1-8) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 143 Compounds of formula (1-8) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 144 Compounds of formula (1-8) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 145 Compounds of formula (1-8) in which R5 represents The compound corresponds respectively to a row of table A. Table 146 Compounds of formula (1-8) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to one row of Table A. Table 147 Compounds of formula (1-8) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 148 Compounds of formula (1-8) in which R5 represents and the combination of the Ri and R2 moieties for a compound corresponds respectively to a row of table A. Table 149 Compounds of formula (1-8) in which R5 represents and the combination of the remains R and R for a compound corresponds respectively to a row of table A. Table 150 Compounds of formula (1-8) in which R5 represents for a compound corresponds respectively to a row of table A. Table 151 Compounds of formula (1-8) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one of Table A. Table 152 Compounds of formula (1-8) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 153 Compounds of formula (1-9) wherein R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 154 Compounds of formula (1-9) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 155 Compounds of formula (1-9) in which R5 represents and the combination of the remains R and R for a compound corresponds respectively to a row of table A. Table 156 Compounds of formula (1-9) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 157 Compounds of formula (1-9) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 158 Compounds of formula (1-9) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 159 Compounds of formula (1-9) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 160 Compounds of formula (1-9) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 161 Compounds of formula (1-9) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 162 Compounds of formula (1-9) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 163 Compounds of formula (1-9) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 164 Compounds of formula (1-9) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 165 Compounds of formula (1-9) in which R5 represents and the combination of the radicals R.sub.1 and R.sub.2 for a compound corresponds respectively to one row of Table A. Table 166 Compounds of formula (1-9) in which R.sub.5 represents for a compound corresponds respectively to a row of table A. Table 167 Compounds of formula (1-9) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 168 Compounds of formula (1-9) in which R5 represents and the combination of the residues R1 and R2 for a The compound corresponds respectively to a row of table A. Table 169 Compounds of formula (1-9) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 170 Compounds of formula (1-9) in which R5 represents for a compound corresponds respectively to one of table A. Table 171 Compounds of formula (1-9) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 172 Compounds of formula (1-10) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 173 Compounds of formula (1-10) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A. Table 174 Compounds of formula (1-10) in which R5 represents c Ne and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of the Table A. Table 175 Compounds of formula (1-10) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 176 Compounds of formula (1-10) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 177 Compounds of formula (1-10) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 178 Compounds of formula (1-10) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 179 Compounds of formula (1-10) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 180 Compounds of formula (1-10) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 181 Compounds of formula (1-10) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 182 Compounds of formula (1-10) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 183 Compounds of formula (1-10) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to one row of Table A. Table 184 Compounds of formula (1-10) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 185 Compounds of formula (1-10) in which R5 represents and R for a compound corresponds respectively to a row of table A. Table 186 Compounds of formula (1-10) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 187 Compounds of formula (1-10) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of the Table A. Table 188 Compounds of formula (1-10) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 189 Compounds of formula (1-10) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to one row of Table A. Table 190 Compounds of formula (1-10) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 191 Compounds of formula (1-11) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 192 Compounds of formula (1-11) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 193 Compounds of formula (1-11) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 194 Compounds of formula (1-11) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to one row of Table A. Table 195 Compounds of formula (1-11) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to one row of Table A. Table 196 Compounds of formula (1-11) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 197 Compounds of formula (1-11) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 198 Compounds of formula (1-11) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 199 Compounds of formula (1-11) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 200 Compounds of formula (1-11) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 201 Compounds of formula (1-11) in which R5 represents and the combination of the residues R 1 and R 2 for a compound corresponds respectively to a row of Table A. Table 202 Compounds of formula (1-11) in which R 5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 203 Compounds of formula (1-11) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 204 Compounds of formula (1-11) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 205 Compounds of formula (1-11) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 206 Compounds of formula (1-11) in which R5 represents and the combination of the remains R and R for a The compound corresponds respectively to a row of table A. Table 207 Compounds of formula (1-11) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 208 Compounds of formula (1-11) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 209 Compounds of formula (1-11) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 210 Compounds of formula (1-12) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 211 Compounds of formula (1-12) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 212 Compounds of formula (1-12) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 213 Compounds of formula (1-12) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 214 Compounds of formula (1-12) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 215 Compounds of formula (1-12) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 216 Compounds of formula (? -12) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 217 Compounds of formula (1-12) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to one row of Table A. Table 218 Compounds of formula (1-12) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 219 Compounds of formula (1-12) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 220 Compounds of formula (1-12) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 221 Compounds of formula (1-12) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 222 Compounds of formula (1-12) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 223 Compounds of formula (1-12) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 224 Compounds of formula (1-12) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 225 Compounds of formula (1-12) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of the Table A. Table 226 Compounds of formula (1-12) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 227 Compounds of formula (1-12) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 228 Compounds of formula (1-12) in which R5 represents for a compound corresponds respectively to a row of table A. Table 229 Compounds of formula (1-13) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 230 Compounds of formula (1-13) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 231 Compounds of formula (1-13) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 232 Compounds of formula (1-13) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 233 Compounds of formula (1-13) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 234 Compounds of formula (1-13) in which R5 represents S and the combination of the radicals R.sub.1 and R.sub.2 for a compound correspond respectively to one row of Table A. Table 235 Compounds of formula (1-13) in which R.sub.5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 236 Compounds of formula (1-13) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 237 Compounds of formula (1-13) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 238 Compounds of formula (1-13) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 239 Compounds of formula (1-13) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 240 Compounds of formula (1-13) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 241 Compounds of formula (1-13) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 242 Compounds of formula (1-13) in which R5 represents for a compound corresponds respectively to a row of table A. Table 243 Compounds of formula (1-13) in which R5 represents for a compound corresponds respectively to a row of table A. Table 244 Compounds of formula (1-13) in which R5 represents and the combination of the remains R and R for a The compound corresponds respectively to a row of table A. Table 245 Compounds of formula (1-13) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 246 Compounds of formula (1-13) in which R5 represents for a compound corresponds respectively to a row of table A. Table 247 Compounds of formula (1-13) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A.

Table 248 Compounds of formula (1-14) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 249 Compounds of formula (1-14) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 250 Compounds of formula (1-14) in which R5 represents cN and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A. Table 251 Compounds of formula (1-14) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 252 Compounds of formula (1-14) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 253 Compounds of formula (1-14) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 254 Compounds of formula (1-14) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 255 Compounds of formula (1-14) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 256 Compounds of formula (1-14) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 257 Compounds of formula (1-14) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 258 Compounds of formula (1-14) in which R5 represents for a compound corresponds respectively to a row of table A. Table 259 Compounds of formula (1-14) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 260 Compounds of formula (1-14) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 261 Compounds of formula (1-14) in which R5 represents for a compound corresponds respectively to a row of table A. Table 262 Compounds of formula (1-14) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 263 Compounds of formula (1-14) in which R5 represents and the combination of the residues R1 and R2 for compound corresponds respectively to a row of Table A. Table 264 Compounds of formula (1-14) in which R5 represents for a compound corresponds respectively to one of table A. Table 265 Compounds of formula (1-14) in which R5 represents for a compound corresponds respectively to a row of table A. Table 266 Compounds of formula (1-14) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 267 Compounds of formula (1-15) in which R5 represents a compound corresponds respectively to a row of table A.

Table 268 Compounds of formula (1-15) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 269 Compounds of formula (1-15) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 270 Compounds of formula (1-15) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 271 Compounds of formula (1-15) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 272 Compounds of formula (1-15) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 273 Compounds of formula (1-15) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 274 Compounds of formula (1-15) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 275 Compounds of formula (1-15) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 276 Compounds of formula (1-15) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 277 Compounds of formula (1-15) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 278 Compounds of formula (1-15) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 279 Compounds of formula (1-15) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 280 Compounds of formula (1-15) in which R5 represents and the combination of the R and R moieties for a compound corresponds respectively to a row of Table A. Table 281 Compounds of formula (1-15) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 282 Compounds of formula (1-15) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of the Table A. Table 283 Compounds of formula (1-15) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to one row of Table A. Table 284 Compounds of formula (1-15) in which R5 represents for a compound corresponds respectively to a row of table A. Table 285 Compounds of formula (1-15) in which R5 represents for a compound corresponds respectively to a row of table A. Table 286 Compounds of formula (1-15) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 287 Compounds of formula (1-15) in which R5 represents for a compound corresponds respectively to a row of table A. Table 288 Compounds of formula (1-15) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of table A.

Table 289 Compounds of formula (1-15) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to one row of Table A. Table 290 Compounds of formula (1-15) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 291 Compounds of formula (1-15) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 292 Compounds of formula (1-15) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to one row of Table A. Table 293 Compounds of formula (1-15) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 294 Compounds of formula (1-15) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to one row of Table A. Table 295 Compounds of formula (1-15) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 296 Compounds of formula (1-15) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 297 Compounds of formula (1-15) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of Table A. Table 298 Compounds of formula (1-15) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to one row of Table A. Table 299 Compounds of formula (1-15) in which R5 represents for a compound corresponds respectively to a row of table A. Table 300 Compounds of formula (1-15) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 301 Compounds of formula (1-15) in which R5 represents and the combination of the R1 and R2 moieties for a compound corresponds respectively to a row of the Table A. Table 302 Compounds of formula (1-15) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 303 Compounds of formula (1-15) in which R5 represents and the combination of the residues R1 and R2 for a compound corresponds respectively to a row of Table A. Table 304 Compounds of formula (1-15) in which R5 represents for a compound corresponds respectively to a row of table A.

Table A Suitable diluents in carrying out process a) according to the invention are acids, such as acetic acid, formic acid, alcohols such as methanol, water or halogenated hydrocarbons such as dichloromethane or chloroform. Mixtures of these solvents can also be used. Acetic acid or, in the case of Oxone as an oxidant, mixtures of methanol / water are preferred. Oxidants which are considered in the process a) according to the invention are, for example, hydrogen peroxide, perwolframic acid, peracetic acid, 3- chloroperbenzoic acid, perphthalic acid, chlorine, oxygen and Oxone (KHS05). The reaction temperatures can be varied over a larger range in the embodiment of process a) according to the invention. In general, the process is carried out at temperatures from 0 ° C to 100 ° C, preferably at temperatures of 10 ° C to 50 ° C (see WO02 / 074753 and the references cited therein). To carry out process b) according to the invention for preparing compounds of formula (I1), in general, 1 to 5 mol, preferably 1 to 2 mol, of compound of formula (IV) are used per mol of compound of formula (III). The compounds necessary as starting substances for carrying out process a) according to the invention are defined in general by formula (II). In this formula, R.sub.1, R.sub.2 and R.sub.5 preferably or especially have the meanings which have already been indicated as being preferred in relation to the description of the substances of formula (I) according to the invention, R.sub.4 represents halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 halogenalkyl -C4 and R6 Ci-C6 alkyl. The starting substances of formula (II) are new and also object of the invention. The compounds necessary as starting substances for carrying out process b) according to the invention are defined in general by formula (III). In this formula, R1, R2 and R5 preferably or especially have the meanings which have already been indicated as preferred in relation to the description of the substances of formula (I) according to the invention, R4 represents halogen, C1-C4 alkyl or C1-C4 haloalkyl and R6 Ci-C6 alkyl, n can be 1 or 2. As acid acceptors in carrying out process b) according to the invention, all usual inorganic or organic bases are considered for reactions of this type. Preferably, hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates of alkaline earth metals or alkaline metals can be used, such as, for example, sodium hydride, sodium amide, lithium diisopropylamide, sodium methylate, sodium ethylate, tert-butylate potassium, sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate and sodium hydrogencarbonate, and in addition to ammonium compounds such as ammonium hydroxide, ammonium acetate and ammonium carbonate, as well as tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethyl-benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, -dimethylaminopyridine, diazabiooctane (DABCO), diazabiononene (DBN) or diazabioundecene (DBU). For carrying out process b) according to the invention for preparing compounds of formula (I1) in general it is used per mole of compound of formula (III) from 1 to 5 mol, preferably from 1 to 2 mol of compound of formula (IV). The starting substances of formula (III) are new and also object of the invention. The starting substances also necessary for carrying out process b) according to the invention are defined by formula (IV). In this formula, R3 preferably has or especially meanings which have already been indicated as being preferred in relation to the description of the substances of formula (I) according to the invention, with the proviso that R3 has at least one nitrogen atom by which the binding to the pyrimidine ring takes place in compounds of formula (I1) · The starting substances of formula (IV) are known and / or can be prepared according to known methods. The starting substances of formula (II) are obtained when according to process f) compounds of formula wherein R4 represents halogen, C1-C4 alkyl or haloalkyl Ci-C4 and R6 Ci-C6 alkyl and Hal represents halogen, they react with a compound of the formula HNR1R2 (VI), in which R1 and R2 have the meanings indicated above, optionally in the presence of a diluent, optionally in presence of a catalyst and optionally in the presence of an acid acceptor. The compounds of formula (IX) are new and also object of the invention. The amines which are still necessary as starting substances for carrying out process f) according to the invention are generally defined by formula (VI). In this formula, R1 and R2 preferably have the meanings which have already been indicated as being preferred in relation to the description of the substances of formula (I) according to the invention for R1 and R2. The amines of formula (VI) are known or can be prepared according to known methods. Suitable diluents in the process f) according to the invention are all customary organic solvents. Preferably, halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, dichloroethane or trichloroethane; ethers as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; amides such as N, -dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; esters such as methyl ester of acetic acid or ethyl ester of acetic acid; sulfoxides such as dimethylsulfoxide; sulfones such as sulfolane, as well as alcohols such as for example ethanol. Suitable acid acceptors in the process f) according to the invention are all customary inorganic or organic bases for reactions of this type. Preferably, hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates of alkaline earth metals or alkaline metals can be used, such as, for example, sodium hydride, sodium amide, lithium diisopropylamide, sodium methylate, sodium ethylate, tert-butylate potassium, sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate and sodium hydrogencarbonate, and also ammonium compounds such as ammonium hydroxide, ammonium acetate and ammonium carbonate, as well as tertiary amines such as trimethylamine, triethylamine, tributylamine, , N-dimethylaniline, N, N-dimethyl-benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU). As catalysts in carrying out process f) according to the invention, all common reaction accelerators are considered for reactions of this type. Preferably, fluorides such as sodium fluoride, potassium fluoride or ammonium fluoride can be used. The reaction temperatures can be varied over a larger range in the embodiment of process f) according to the invention. In general, work is carried out at temperatures between 0 ° C and 150 ° C, preferably at temperatures between 0 ° C and 80 ° C. When carrying out process f) according to the invention, it is generally used per 1 mol of halogenopyrimidine of formula (IX) from 0.5 to 10 mol, preferably from 0.8 to 2 mol of amine of formula (VI). The treatment takes place according to usual procedures. The compounds of formula (IX), wherein R5 and R6 have the meanings indicated above and R4 represents C1-C4 alkyl or haloalkyl Ci ~ are obtained when according to the process g) compounds of formula wherein R 4 represents C 1 -C 4 alkyl or C 1 -C 4 haloalkyl and R 5 and R 6 have the meanings indicated above, react with a halogenating agent, optionally in the presence of an acid acceptor and optionally in the presence of a diluent. As a halogenating agent in carrying out process g) all the usual components for the replacement of hydroxy groups with halogen are considered. Preferably phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, phosphorus oxychloride, thionyl chloride, thionyl bromide or mixtures thereof or phosgene, di or triphosgene can be used. The corresponding fluorine compounds can be prepared from the chlorine or bromine compounds by reaction with potassium fluoride. Suitable diluents in the process g) according to the invention are all customary solvents for halogenations of this type. Preferably Aliphatic or halogenated aromatic hydrocarbons such as chlorobenzene can be used. However, the halogenating agent itself can also make a diluent, for example, phosphorus oxychloride or a mixture of halogenating agents. As acid acceptors in carrying out process g) according to the invention, all the usual organic bases are considered for reactions of this type. Preferably tertiary amines such as triethylamine, tri-n-butylamine and N, N-dimethylaniline can be used. The temperatures may also be varied over a larger interval in the performance of process g). In general, work is carried out at temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C. In carrying out process g), the compound of formula (X) generally reacts with an excess of halogenating agent. The treatment takes place according to usual procedures. The starting substances still necessary for carrying out process g) according to the invention are defined by formula (X). In this formula R 4 represents C 1 -C 4 alkyl or C 1 -C 4 haloalkyl, R 5 and R 6 have the meanings indicated above. The compounds of formula (X) are new and also object of the present invention.

The compounds of formula (X) in which R4 represents C1-C4 alkyl or C1-C haloalkyl and R5 has the meaning indicated above, are obtained by reacting according to process h) compounds of formula wherein R 4 represents C 1 -C 4 alkyl or C 1 -C 4 haloalkyl and R 5 has the meanings given above, with an alkylating agent of formula R 6 -X (XII), wherein R 6 represents Ci-C 6 alkyl and X a group of which can be dissociated by nucleophiles, optionally in a diluent in the presence of a base. The formula (XII) generally represents conventional alkylating agents such as C1-C6 alkyl halide, especially methyl chloride and methyl bromide, Ci-C6 dialkyl ester of sulfuric acid as dimethyl sulfate, or a Ci-C6 alkylic ester of the methanesulfonic acid as methanesulfonic acid methyl ester. As diluents in carrying out the procedure h) according to the invention, they are considered water; alcohols or dipolar aprotic solvents such as N, N-dimethylformamide (see US5,250,689). Acid acceptors in carrying out process h) according to the invention are hydroxides, hydrogen carbonates, carbonates and alcoholates of alkali metals or alkaline earth metals such as for example KOH, NaOH, NaHCO 3, Na 2 CO 3, sodium methylate and sodium ethylate, but also Nitrogen bases such as pyridine. The temperatures can also be varied over a longer interval in the performance of process h). In general, temperatures are between 0 ° C and 100 ° C, preferably between 10 ° C and 60 ° C. Normally the components are used in approximately stoichiometric ratio. However, it may be advantageous to use the alkylating agent (XII) in excess. The starting substances of formula (XII) are known and / or can be prepared according to known methods. The starting substances which are also still necessary for carrying out process h) according to the invention are defined by formula (XI). In this formula, R 4 represents C 1 -C 4 alkyl or C 1 -C 4 haloalkyl, R 5 has the meanings indicated above. The compounds of formula (XI) are new and also object of the present invention.

The compounds of formula (XI) in which R 4 represents C 1 -C 4 alkyl or C 1 -C 4 haloalkyl and R 5 has the meaning indicated above are obtained by reacting according to process i) compounds of formula wherein R 4 represents C 1 -C 4 alkyl or C 1 -C 4 haloalkyl, R 7 represents C 1 -C 4 alkyl, and R 5 has the meanings given above, with thiourea of formula if necessary in a diluent, if necessary in the presence of a base. Suitable diluents for carrying out process i) according to the invention are protic solvents, for example alcohols, especially ethanol. But aprotic solvents are also suitable, such as pyridine, N, N-dimethylformamide, N, N-dimethylacetamide or mixtures thereof (see US Pat. No. 4,331,590; Org. Prep, and Proced. Int.

Volume 10, pages 21-27 Heteroat. Chem., Volume 10, pages 17-23 (1999); Czech Chem. Common., Volume 58, pages 2215-2221).

Acid acceptors are hydroxides, hydrogen carbonates, carbonates and alcoholates of alkali metals or alkaline earth metals, such as for example KOH, NaOH, NaHCO 3, Na 2 CO 3, sodium methylate and sodium ethylate, but also nitrogen bases such as pyridine and tributylamine. The temperatures can also be varied over a larger interval in the carrying out of process i). In general, work is carried out at temperatures between 20 ° C and 250 ° C, preferably between 70 ° C and 220 ° C. Normally the components are used in approximately stoichiometric ratio. However, it may be advantageous to use thiourea (XIV) in excess. Thiourea is known (XIV). The starting substances of formula (XIII) are known (cf. EP-A-1002788; DE3942952) and / or can be prepared according to known methods. The compounds of formula (IX), in which R 5 represents a heterocycle linked by N and R 4 halogen, are obtained when according to process j) compounds of formula (XV), wherein R5 and R6 have the meanings indicated above, they react with a halogenating agent, optionally in the presence of an acid acceptor, and optionally in the presence of a diluent. The compounds of formula XV can also be present in the following form: As halogenating agents in carrying out process j) all the halogenation agents indicated for carrying out the process are considered g) · As diluents in carrying out procedure j) according to the invention, all the diluents indicated for carrying out the process are considered g). Acid acceptors in carrying out process j) according to the invention are all acid acceptors indicated for carrying out the procedure g). The temperatures may also be varied over a larger interval in the performance of process j). In general, work is carried out at temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C. In carrying out process j), the compound of formula (XV) generally reacts with an excess of halogenating agent. The treatment takes place according to usual procedures. The starting substances which are also still necessary for carrying out process j) according to the invention are defined by formula (XV). In this formula, R.sup.5 and R.sup.6 preferably or especially have the meanings already indicated as being preferred in relation to the description of the substances of formula (I) according to the invention. The compounds of formula (XV) are new and also object of the present invention. The compounds of formula (XV) in which R5 and R6 have the meanings indicated above are prepared according to process k) by reacting compounds of formula (XVI), wherein R 5 has the meaning indicated above, with an alkylating agent of formula R 6 -X (XII), wherein R 6 represents C 1 -C 6 alkyl and X a starting group which can be dissociated by a nucleophile, optionally in a diluent in the presence of an acid acceptor. The formula (XII) generally represents conventional alkylating agents such as C1-C6 alkyl halide, especially methyl chloride and methyl bromide, C1-C6 dialkyl ester of sulfuric acid as dimethyl sulfate, or a Ci-C6 alkyl ester of the methanesulfonic acid as methanesulfonic acid methyl ester. The compounds of formula XVI can also be present in the following form: (XVI) Diluents in carrying out process k) according to the invention are water, alcohols or bipolar aprotic solvents, such as N, N-dimethylformamide (see US Pat. No. 5,250,689). As acid acceptors in carrying out process k) according to the invention are considered hydroxides, hydrogen carbonates, carbonates and alcoholates of alkali metals or alkaline earth metals such as for example KOH, NaOH, NaHCO 3, Na 2 CO 3, methylate or sodium ethylate, but also bases of nitrogen as pyridine. The temperatures can also be varied over a larger interval in the procedure k). In general, temperatures are between 0 ° C and 100 ° C, preferably between 10 ° C and 60 ° C. Normally the components are used in approximately stoichiometric ratio. However, it may be advantageous to use the alkylating agent (XII) in excess. The starting substances of formula (XII) are known and / or can be prepared according to known methods. The starting substances which are also still necessary for carrying out process k) according to the invention are defined by formula (XVI). In this formula, R 5 preferably or especially has the meanings which have already been indicated as being preferred in relation to the description of the substances of formula (I) according to the invention.

The compounds of formula (XVI) are new and also object of the present invention. The compounds of formula (XVI) in which R 5 has the meanings indicated above are prepared according to process 1) by reacting compounds of formula (XVII) wherein R7 represents C1-C4 alkyl and R5 has the meanings given above, with thiourea of formula optionally in a diluent, optionally in the presence of an acid acceptor. Suitable diluents for carrying out process 1) according to the invention are protic solvents, for example alcohols, especially ethanol. But aprotic solvents such as pyridine, N, N-dimethylformamide, N, N-dimethylacetamide or mixtures thereof are also suitable (see US Pat. No. 4,331,590; Org. Prep, and Proced. Int., Tome 10, pages 21-27 Heteroat. Chem., Volume 10, pages 17- 23 (1999); Czech Chem. Commun., Volume 58, pages 2215-2221).

Acid acceptors are hydroxides, hydrogen carbonates, carbonates and alcoholates of alkali metals or alkaline earth metals such as KOH, NaOH, NaHCO 3 and Na 2 CO 3, but also nitrogen bases such as pyridine and tributylamine. The temperatures can also be varied over a larger interval in the realization of procedure 1). In general, work is carried out at temperatures between 20 ° C and 250 ° C, preferably between 70 ° C and 220 ° C. Normally the components are used in approximately stoichiometric ratio. However, it may be advantageous to use thiourea (XIV) in excess. Thiourea is known (XIV). The starting substances of formula (XVII) are known (see DE103575707) and / or can be prepared according to known methods. The starting substances of formula (XVII) with R 5 = (2-chloro or methyl) -thiophen-3-yl can be prepared according to the following reaction scheme 1: Reaction scheme 1 R "= Me R" = CI Analogously to the last two stages of the synthesis sequence, 2- (2-chloro-thiophen-3-yl) malonic acid dimethyl ester can also be prepared from acid (2-chloro) -thiophen-3-yl) acetic acid. Suitable diluents in the process c) according to the invention are all customary organic solvents. Preferably halogenated hydrocarbons can be used, such as for example chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, dichloroethane or trichloroethane; ether, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, -dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or acid triamide hexamethylphosphoric; esters such as methyl ester of acetic acid or ethyl ester of acetic acid; sulfoxides such as dimethylsulfoxide; sulfones such as sulfolane, as well as alcohols such as for example ethanol. Acid acceptors in carrying out process c) according to the invention are all customary inorganic or organic bases for reactions of this type. Preferably, hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates of alkaline earth metals or alkaline metals can be used, such as, for example, sodium hydride, sodium amide, lithium diisopropylamide, sodium methylate, sodium ethylate, tert-butylate potassium, sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate and sodium hydrogencarbonate, and also ammonium compounds such as ammonium hydroxide, ammonium acetate and ammonium carbonate, as well as tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, -dimethyl-benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, -dimethylamino-pyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU). As catalysts in carrying out process c) according to the invention, all accelerators of usual reactions for reactions of this type. Preferably, fluorides such as sodium fluoride, potassium fluoride or ammonium fluoride can be used. The reaction temperatures can be varied over a larger range in the embodiment of process c) according to the invention. In general, work is carried out at temperatures between 0 ° C and 150 ° C, preferably at temperatures between 0 ° C and 80 ° C. When carrying out process c) according to the invention, it is generally used per 1 mol of halogenopyrimidine of formula (V) from 0.5 to 10 mol, preferably from 0.8 to 2 mol of amine of formula (VI). The treatment takes place according to usual procedures. The compounds necessary as starting substances for carrying out process c) according to the invention are defined in general by formula (V). In this formula, R3, R4 and R5 and halogen have preferably or especially meanings which have already been indicated as being preferred in relation to the description of the substances of formula (I) according to the invention, with the proviso that the heterocyclic radical R3 is linked to one of its carbon atoms to the pyrimidine skeleton of formula (V). The starting substances of formula (V) are new and also object of the invention. The compounds of formula (V), in which R3 and R5 have the meanings indicated above, with the proviso that that the heterocyclic radical R3 is linked with one of its carbon atoms to the pyrimidine backbone of formula (V), and R4 represents C1-C alkyl or C1-C4 haloalkyl, are obtained by reacting according to process m) compounds of formula (XVIII) wherein R 4 represents C 1 -C 4 alkyl or C 1 -C 4 haloalkyl and R 3 and R 5 have the meanings given above, with the proviso that the heterocyclic radical R 3 is linked with one of its carbon atoms to the pyrimidine skeleton of formula (XVIII ), with a halogenating agent, optionally in the presence of an acid acceptor and optionally in the presence of a diluent. As halogenating agents in carrying out process m) all the halogenating agents indicated for carrying out the process are considered g) · As diluents in carrying out procedure m) according to the invention, all the diluents indicated for carrying out the process are considered. g).

Acid acceptors in carrying out process m) according to the invention are all acid acceptors listed for carrying out process g). The temperatures can also be varied over a larger interval in the performance of process m). In general, work is carried out at temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C. In carrying out process m), the compound of formula (XVIII) generally reacts with an excess of halogenating agent. The treatment takes place according to usual procedures. The starting substances also necessary for carrying out process m) according to the invention are defined by formula (XVIII). In this formula, R.sup.3, R.sup.4 and R.sup.5 preferably or especially have the meanings already indicated as being preferred in relation to the description of the substances of formula (I) according to the invention, with the proviso that the heterocyclic radical R3 is linked to one of its carbon atoms to the pyrimidine skeleton of formula (XVIII). The compounds of formula (XVIII) are new and also object of the present invention. The compounds of formula (XVIII) in which R 4 represents C 1 -C 4 alkyl or C 1 -C 4 haloalkyl and R 3 and R 5 have the meanings indicated above, with the proviso that the heterocyclic residue R3 is linked with one of its carbon atoms to the pyrimidine backbone of formula (XVIII), they are obtained by reacting according to process n) compounds of formula (XIII) wherein R 4 represents C 1 -C 4 alkyl or C 1 -C 4 haloalkyl, R 7 represents C 1 -C 4 alkyl, and R 5 has the meanings given above, with a compound of formula optionally in a diluent, optionally in the presence of an acid acceptor. Suitable diluents in the process n) according to the invention are protic solvents, for example alcohols, especially ethanol. But aprotic solvents such as pyridine, N, N- are also suitable. dimethylformamide, N, N-dimethylacetamide or mixtures thereof (see US Pat. No. 4,331,590; Org. Prep, and Proced. Int., Volume 10, pages 21-27 Heteroat. Chem., Volume 10, pages 17-23 (1999) ), Czech, Chem. Commun., Volume 58, pages 2215-2221).

Acid acceptors are hydroxides, hydrogen carbonates and carbonates of alkali or alkaline earth metals, such as KOH, NaOH, NaHCO3, Na2CC > 3, sodium methylate and sodium ethylate, but also nitrogen bases such as pyridine and tributylamine. The temperatures can also be varied over a larger interval in the performance of process n). In general, work is carried out at temperatures between 20 ° C and 250 ° C, preferably between 70 ° C and 220 ° C. Normally the components are used in an approximate stoichiometric ratio. However, it may be advantageous to use the compound of formula (XIX) in excess. The starting substances of formula (XIII) are known (see EP-A-1002788) and / or can be prepared according to known processes. The starting substances of formula (XIX) are known and / or can be prepared according to known methods. The compounds of formula (V) in which R3 and R5 have the meanings indicated above, with the proviso that the heterocyclic moiety R3 is linked with one of its carbon atoms to the pyrimidine backbone of formula (V), and R4 represent halogen, are obtained by reacting according to the process o) a compound of formula (XX), wherein R3 and R5 have the meanings indicated above, with the proviso that the heterocyclic moiety R3 is linked with one of its carbon atoms to the pyrimidine backbone of formula (XX), with a halogenating agent, optionally in presence of an acid acceptor and, if necessary, in the presence of a diluent. As the halogenating agent in carrying out the procedure, o) all the halogenating agents indicated for carrying out the process are considered g) · As diluents in carrying out the procedure o) according to the invention, all the diluents indicated for carrying out the process are considered g). Acid acceptors in carrying out the process o) according to the invention are all acid acceptors indicated for carrying out process g).

The temperatures may also be varied over a larger interval in the performance of the process o). In general, work is carried out at temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C. In carrying out process o), the compound of formula (XX) generally reacts with an excess of halogenating agent. The treatment takes place according to usual procedures. The starting substances still necessary for carrying out the process o) according to the invention are defined by the formula (XX). In this formula, R3 and R5 preferably or especially have the meanings already indicated as being preferred in relation to the description of the substances of formula (I) according to the invention, with the proviso that the heterocyclic radical R3 is linked to one of its carbon atoms to the pyrimidine skeleton of formula (XX). The compounds of formula (XX) are new and also object of the present invention. The compounds of formula (XX), in which R3 and R5 preferably or especially have the meanings already indicated as being preferred in relation to the description of the substances of formula (I) according to the invention, with the proviso that the remainder heterocyclic R3 is linked with one of its carbon atoms to the pyrimidine skeleton of formula (XX), are obtained by reacting according to the process p) compounds of formula wherein R7 represents C1-C4 alkyl and R5 has the meanings given above, with a compound of formula if necessary in a diluent, if necessary in the presence of a base. Suitable diluents for carrying out process p) according to the invention are protic solvents, for example alcohols, especially ethanol. But aprotic solvents such as pyridine, N, N-dimethylformamide, N, -dimethylacetamide or mixtures thereof are also suitable (see US Pat. No. 4,331,590, Org. Prep, and Proced. Int., Volume 10, pages 21-27 Heteroat. Chem., Volume 10, pages 17-23 (1999), Czech, Chem. Commun, volume 58, pages 2215-2221). As acid acceptors in carrying out the process p) according to the invention are hydroxides, hydrogen carbonates, carbonates and alcoholates of alkali or alkaline earth metals, such as for example KOH, NaOH, NaHCO3, Na2CC > 3, sodium methylate or ethylate, but also nitrogen bases such as pyridine or tri-n-butylamine. The temperatures can also be varied over a longer interval in the performance of process p). In general, work is carried out at temperatures between 20 ° C and 250 ° C, preferably between 70 ° C and 220 ° C. Normally the components are used in approximately stoichiometric ratio. However, it may be advantageous to use the compound of formula (XIX) in excess. The starting substances of formula (XVII) are known (cf. DE-103575707) and / or can be prepared according to known procedures. The starting substances of formula (XIX) are known and / or can be prepared according to known methods. The reaction temperatures can be varied over a larger range in the process d) according to the invention. In general, temperatures are from 0 ° C to 150 ° C, preferably at temperatures of 20 ° C to 100 ° C. For carrying out process d) according to the invention for preparing compounds of formula (I1"), it is generally used per mole of compound of formula (I'a) or (I" a) from 1 to 10 mol, preferably from 1 to 3 mol of compound of formula (VII). When carrying out process d) according to the invention, all solvents customary for Grignard reactions are considered as diluents. Preferably ethers, such as diethyl ether, or also tetrahydrofuran can be used. As catalysts in carrying out process e) according to the invention, all the reaction accelerators mentioned for process b) according to the invention are considered. The reaction temperatures can be varied within a certain range in the procedure of e) according to the invention. In general, work is carried out at temperatures between -20 ° C and 80 ° C, preferably between 0 ° C and 60 ° C. For carrying out process e) according to the invention for preparing compounds of formula (I '"') in general, it is used per mole of compound of formula (I'a) or (I" a) from 1 to 10 mol, preferably from 1 to 3 mol of compound of formula (VIII). The compounds of formula (I'a) and (I "a) used as starting substances for carrying out process d) according to the invention are obtained according to process b) or c) according to the invention. ) and (I "a), R1, R2, R3, R5 and Hal preferably or especially have the meanings that were already indicated as preferred in relation to with the description of the substances of formula (I) according to the invention. The starting substances which are also still necessary for carrying out process d) according to the invention are defined by formula (VII). In this formula, R 4 preferably has or especially the meanings which have already been indicated as being preferred in relation to the description of the substances of formula (I) according to the invention. The compounds of formula (VII) are known or can be prepared according to known methods. The starting substances which are also still necessary for carrying out process e) according to the invention are defined by formula (VIII). In this formula, R 4 preferably has or especially the meanings which have already been indicated as being preferred in relation to the description of the substances of formula (I) according to the invention. The compounds of formula (VIII) are known or can be prepared according to known procedures. The processes a) to n) according to the invention are generally carried out at atmospheric pressure. However, it is also possible to work at high pressure. The substances according to the invention inhibit the growth of tumor cells and analogous diseases in mammals and can be used as a drug. They are especially suitable for preparing drugs to fight cancer diseases.

The invention also relates to a method for the inhibition of the growth of cancerous tumor cells and analogous diseases in a mammal in need of this treatment. This method comprises administering an effective amount of a 5-phenylpyrimidine or a pharmaceutically effective salt thereof to a mammal. The invention further relates to a method for treating or preventing the growth of tumor cells and analogous diseases by interacting with tubulin and microtubules and enhancing the polymerization of microtubules by administering an effective amount of a 5-phenylpyrimidine or a pharmaceutically salt. effective of it to a mammal. The substances according to the invention have a strong microbicidal action and can be used to combat unwanted microorganisms, such as fungi and bacteria, in the protection of plants and in the protection of materials. Fungicides can be used in the protection of plants to combat plasmodioforomycetes, oomycetes, chytridiomycetes, zygomycetes, ascomycetes, basidiomycetes and deuteromycetes. The bactericides can be used in the protection of plants to fight pseudomonadales, rhizobiaceae, enterobacteria, corinebacteria and streptomycetes.

By way of example, but not in a limiting manner, mention must be made of some pathogenic agents of fungal and bacterial diseases that are found under the preambles listed above: Diseases caused by pathogenic agents of powdery mildew such as, for example, Blumeria species, such as, for example, Blumeria graminis; species of Podosphaera, such as, for example, Podosphaera leucotricha; Sphaerotheca species, such as Sphaerotheca fuliginea; Uncinula species, such as Uncinula necator; Diseases caused by pathogens of rust disease such as, for example, Gymnosporangium species, such as, for example, Gymnosporangium sabinae; Hemileia species, such as Hemileia vastatrix; Phakopsora species, such as Phakopsora pachyrhizi and Phakopsora meibomiae; Puccinia species, such as Puccinia recondi ta; Uromyces species, such as Uromyces appendiculatus; Diseases caused by pathogens of the oomycete group, for example, Bremia species, such as Bremia lactucae; Peronospora species, such as Peronospora pisi or P. brassicae; Phytophthora species, such as Phytophthora infestans; Plasmopara species, such as Plasmopara viticola; Pseudoperonospora species, such as Pseudoperonospora humuli or Pseudoperonospora cubensis; Pythium species, such as Pythium ultimum; Diseases of leaf spots and leaf wilt caused by, for example, Alternaria species, such as Alternaria solani; Cercospora species, such as Cercospora beticola; species of Cladíosporum, such as Cladiosporium cucumerínum; Cochliobolus species, such as Cochliobolus sativus (conidia form: Drechslera, synonym: Helminthosporium); species of Colletotrichum, as for example Colletotrichum lindemuthanium; Cycloconium species, such as Cycloconium oleaginum; Diaporthe species, such as Diaporthe citri; Elsinoe species, such as Elsinoe fawcettii; Gloeosporium species, such as Gloeosporium laeticolor; Glomerella species, such as Glomerella cingulata; Guignardia species, such as Guignardia bidwelli; Leptosphaeria species, such as Leptosphaeria maculans; Magnaporthe species, such as Magnaporthe grísea; Mycosphaerella species, such as Mycosphaerelle graminicola; Phaeosphaeria species, such as Phaeosphaeria nodorum; Pyrenophora species, such as Pyrenophora teres; Ramularia species, such as Ramularia collo-cygni; Rhynchosporium species, such as Rhynchosporium secalis; Septoria species, such as Septoria apii; Typhula species, such as Typhula incarnata; Venturia species, such as Venturia inaequalis; Diseases of the root and stem caused by, for example, Corticium species, such as Corticium graminasarum; Fusarium species, such as Fusarium oxysporum; Gaeumannomyces species, such as Gaeumannomyces graminis; Rhizoctonia species, such as Rhizoctonia solani; Tapesia species, such as Tapesia acuformis; Thielaviopsis species, such as Thielaviopsis basicola; Spike and panicle diseases (including corn cobs) caused by, for example, Alternaria species, such as, for example, Alternaria sp. Aspergillus species, such as Aspergillus flavus; Cladosporium species, such as Cladosporium sp.; Claviceps species, such as Claviceps purpurea; Fusarium species, such as Fusarium culmorum; Gibberella species, such as Gibberella zeae; Monographella species, such as, for example, Monographella nivalis; Diseases caused by coals such as, for example, Sphacelotheca species, such as Sphacelotheca reiliana; Tilletia species, such as Tilletia caries; Urocystis species, such as Urocystis occulta; Ustílago species, such as Ustilago nuda; Fruit rot caused by, for example, Aspergillus species, such as Aspergillus flavus; Botrytis species, such as Botrytis cinerea; Penicillium species, such as Penicillium expansum; Sclerotinia species, such as Sclerotinia sclerotiorum; Verticilium species, such as, for example, Verticilium alboa trum; Putrefaction and wilting transmitted by the seeds and soil, as well as diseases of seedlings caused by, for example, Fusarium species, such as Fusarium culmorum; Phytophthora species, such as Phytophthora cactorum; Pythium species, such as Pythium ultimum; Rhizoctonia species, such as Rhizoctonia solani; Sclerotium species, such as Sclerotium rolfsii; Carcinogenic diseases, gills and witches' brooms caused by, for example, Nectria species, such as Nectria galligena; Wilt diseases caused by, for example, Monilinia species, such as, for example, Monilinia laxa; Deformities of leaves, flowers and fruits caused by, for example, Taphrina species, such as Taphrina deformans; Degenerative diseases of woody plants caused by, for example, Esca species, such as, for example, Phaemoniella clamydospora; Diseases of flowers and seeds caused by, for example, Botrytis species, such as Botrytis cinerea; Diseases of the tubers of plants caused by, for example, Rhizoctonia species, such as, for example, Rhizoctonia solani; The active principles according to the invention also have a very good invigorating effect on plants. Therefore, they are suitable for mobilizing the plant's own defenses against pests of unwanted microorganisms. By plant invigorating substances (resistance inducers) should be understood in the present context those substances that can stimulate the immune system in such a way that the treated plants develop in the subsequent inoculation with unwanted microorganisms a broad resistance against these microorganisms. By undesired microorganisms, fungi, bacteria and phytopathogenic viruses should be understood in the present case. The substances according to the invention can also be used to protect plants within a certain period of time after the treatment against the plague of harmful pathogenic microorganisms mentioned. The period of time in which the protection takes place usually lasts from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the active ingredients. The good phytotolerance of the active ingredients in the concentrations necessary to combat plant diseases allows a treatment of aerial plant parts, of seedlings and seeds, and of the soil. In this regard, the active compounds according to the invention can be used with especially good results for controlling diseases of cereals, such as, for example, against fissile species, diseases in rice, for example against Pyricularia Oryza and diseases in viticulture, fruit growing and the cultivation of vegetables, such as against Botrytis, Venturia, Sphaerotheca and Podosphaera species. The active ingredients according to the invention are also suitable for increasing the harvest. In addition, they are less toxic and have good phytotolerance. The active compounds according to the invention can also be used, if appropriate in certain concentrations and doses, as herbicides for influencing plant growth, as well as for controlling animal pests. If necessary, they can also be used as intermediates and primary products for the synthesis of other active ingredients. All plants and plant parts can be treated according to the invention. In this case, plants are all plants and plant populations, such as plants. wild or cultivated plants desired and unwanted (including natural cultivated plants). Cultivated plants can be plants that can be obtained by conventional cultivation or optimization methods or by biotechnological and genetic technology methods or combinations of these procedures, including transgenic plants and including plant varieties that can be protected by plant variety rights or not. can protect themselves By plant parts should be understood all the aerial and underground parts and organs of the plants as an outbreak, leaf, flower and root, enumerating by way of example leaves, needles, stems, trunks, flowers, fruit bodies, fruits and seeds, as well as roots, tubers and rhizomes. The crop also belongs to the plant parts, as well as the material of vegetative and generative multiplication, for example, cuttings, tubers, rhizomes, cuttings and seeds. The treatment of the plants and plant parts according to the invention with the active ingredients takes place directly or by action on their environment, habitat or storage location according to the usual treatment methods, for example, by immersion, spraying, gasification, nebulization, dusted, coated and, in the case of multiplication material, especially seeds, also by wrapping aor several layers. In the protection of materials, substances according to the invention can be used to protect industrial materials from pests and from destruction by unwanted microorganisms. By industrial materials, non-living materials that have been prepared for use in the art should be understood in the present context. By way of example, they can be industrial materials, which must be protected by the active principles of microbial modification, adhesives, glues, paper and cardboard, textile products, leather, wood, coating materials and plastic articles, cooling lubricants and other materials. that can be attacked or disintegrated by microorganisms. In the framework of the materials to be protected, it is also necessary to mention parts of production plants, for example cooling water circuits that can be damaged by the multiplication of microorganisms. In the context of the present invention, industrial materials preferably include adhesives, glues, papers and boards, leather, wood, coating materials, cooling lubricants and heat transfer liquids, especially wood. As microorganisms that can produce a decomposition or a modification of industrial materials are to be mentioned, for example, bacteria, fungi, yeasts, algae and mucous organisms. The active ingredients according to the invention preferably act against fungi, especially mildew, wood-bleached fungi and wood destroyers (basidiomycetes), as well as against mucus organisms and algae. As an example, mention should be made of microorganisms of the following genera: Alternate, such as Alternaria tenuis, Aspergillus, Aspergillus niger, Chaetomium, Chaetomium globosum, Coníophora, Coníophora puetana, Lentínus, Lentínus tigrinus, Penicillium, Penicillium glaucum, Polyporus , such as Polyporus versicolor, Aureobasidium, such as Aureobasidium pullulans, Sclerophoma, such as Sclerophoma pityophila, Trichoderma, as Trichoderma viride, Escherichia, as Escherichia coli, Pseudomonas, as Pseudomonas aeruginosa, Staphylococcus, as Staphylococcus aureus. The active ingredients can be converted, depending on their respective physical and / or chemical properties, into the usual formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in seed wraps, as well as ULV cold and hot steam formulations. These formulations are prepared in a known manner, for example by mixing the active ingredients with diluents, ie liquid solvents, pressurized liquefied gases and / or solid carriers, possibly with the use of surfactants, ie emulsifiers and / or dispersants and / or foaming agents. In the case of the use of water as a diluent, for example, organic solvents can also be used as coadjuvants. Liquid solvents are essentially: aromatic compounds such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic compounds and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol , as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, as well as water. Liquefied gaseous diluents or vehicles refers to those liquids that at normal temperature and at normal pressure are gaseous, for example propellants for aerosols, such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide. As solid vehicles are considered: for example, natural mineral powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic mineral powders such as highly dispersed silicic acid, aluminum oxide and silicates. As solid carriers for granules are considered: for example, broken and fractionated natural rocks such as calcite, pumice, marble, sepiolite, dolomite, as well as synthetic granules of inorganic and organic powders, as well as granules of organic material such as sawdust, coconut shells , corn cobs and tobacco stalks. Suitable emulsifiers and / or foaming agents are, for example, non-ionogenic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty acid ethers, for example, alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, and hydrolysates. of proteins. Dispersants are considered: for example, residual sulphite with lignin and methylcellulose. Adherent agents such as carboxymethylcellulose, natural and synthetic polymers, powders, granules or latex-shaped gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, can be used in the formulations. synthetic phospholipids. Other additives can be oils minerals and vegetables. Dyes can be used as inorganic pigments, for example iron oxide, titanium oxide, ferrocyanide blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and micronutrients such as iron, manganese, boron, copper, cobalt, molybdenum salts and zinc. The formulations generally contain between 0.1 and 95 weight percent active ingredient, preferably between 0.5 and 90%. The active compounds according to the invention can be used as such or in their formulations in admixture with known fungicides, bactericides, acaricides, nematicides or insecticides in order to broaden the spectrum of action or to prevent the development of resistance. In this sense, in many cases synergistic effects are obtained, that is, the efficiency of the mixture is greater than the effectiveness of the individual components. The following compounds are considered as mixing components, for example: Fungicides: 1. Inhibition of nucleic acid synthesis Benalaxyl, benalaxyl-M, bupirimate, quiralaxyl, clozilacon, dimethirimol, etirimol, furalaxyl, himexazole, mefenoxam, metalaxyl, metalaxyl -M, ofurace, oxadixil, acid oxolinic 2. Inhibition of mitosis and cell division Benomyl, carbendazim, dietofencarb, fuberidazole, pencicuron, thiabendazole, thiophanate-methyl, zoxamide 5 3. Inhibition of the respiratory chain 3.1 Complex I Diflumetorim 3.2 Complex II Boscalid, carboxin, fenfuram, flutolanil, furametpir, ^ furmeciclox, mepronilo, oxycarboxina, pentiopirad, tifluzamida 3.3 Complex III Amisulbrom, azoxystrobin, ciazofamida, dimoxystrobin, enestrobina, famoxadona, fenamidona, fluoxastrobina, ^ kresoxim-methyl, metominostrobin, orisastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin 3.4 Decouplers Dinocap, fluazinam, metildinocap 3.5 Inhibition of ATP production 20 Fentin acetate, fentin chloride, fentin hydroxide, siltiofam 4. Inhibition of amino acid biosynthesis and proteins Andoprim, blasticidin-S, cyprodinil, kasugamycin, hydrated kasugamycin hydrochloride, mepanipyrim, pyrimethanil 5. Inhibition of signal transduction Fenpiclonil, fludioxonil, quinoxifene 6. Inhibition of synthesis of fats and membranes Clozolinate, iprodione, procymidone, vinclozolin Pirazophos, edifenfos, iprobenfos (PPI), isoprothiolane Tolclophos-methyl, biphenyl, Yodocarb, propamocarb, propamocarb hydrochloride 7. Inhibition of ergosterol biosynthesis Fenhexamide, Azaconazole, bitertanol, bromuconazole, ciproconazole, diclobutrazol, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flurprimidol, flusilazole, flutriafol, furconazole, furconazole-cis , hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazol, penconazole, propiconazole, protioconazole, pirifenox, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, voriconazole, Imazalil, imazalil sulfate, oxpoconazole, fenarimol, flurprimidol, nuarimol , pirifenox, triforina, pefurazoat or, prochloraz, triflumizol, triforin, viniconazole, Aldimorf, dodemorf, dodemorf acetate, fenpropidin, fenpropimorf, tridemorph, spiroxamine, Naftifine, pyributicarb, terbinafine 8. Inhibition of cell wall synthesis Bentiavalicarb, dimetomorf, flumorf, iprovalicarb, polyoxins, polioxorim, validamycin A 9. Inhibition of melamine biosynthesis Capropamide, diclocimet, phenoxanil, phthalide, pyroquilone, triciclazole 10. Induction of resistance Acibenzolar-S-methyl , probenazol, thiadinil 11. Multisite Bordeaux mixture, captafol, captan, chlorothalonil, copper salts such as: copper hydroxide, copper naphthenate, copper oxychloride, copper oxide, copper sulfate, oxina-copper and diclofluanide, dithianone, dodin, base without dodin, ferbam, fluorfolpet, folpet, guazatine, guazatin acetate, iminoctadine, iminoctadine albesylate, iminoctadine triacetate, mancobre, mancozeb, maneb, metiram, metiram zinc, propineb, sulfur and sulfur preparations containing poly (calcium sulfide), thiram, tolylfluanide, zineb, ziram 12. Unknown Amibromdol, benthiazole, betoxazin, capsimycin, carvone, quinomethionate, chloropicrin, cufraneb, ciflufenamide, cymoxanil, dazomet, debacarb, dichlorophene, diclomezine, dichloromethane, difenzoquat, difenzoquat methylsulfate, diphenylamine, ferimonate, flumetover, fluopicolid, fluoroimid, flusulfamide, fosetyl-aluminum, fosetyl-calcium, fosetyl- sodium, hexachlorobenzene, 8-hydroxyquinoline sulfate, irumamycin, metasulfocarb, methyl isothiocyanate, metrafenone, mildiomycin, natamycin, nickel dimethyldithiocarbamate, nitrotal-isopropyl, octylinone, oxamocarb, oxyfentiine, pentachlorophenol and salts, 2-phenylphenol and salts, phosphorous acid and salts, piperalin, propamocarb fosetilate, propanosine-sodium, proquinazid, pyrrolnitrin, quintozena, tecloftalam, tecnazene, triazoxide, triclamide, zarilamide and 2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide, 2-chloro-N - (2,3-dihydro-l, 1,3-trimethyl-lH-inden-4-yl) -3-pyridinecarboxamide, 3- [5- (4-chlorophenyl) -2, 3-dimethylisoxazolidin-3-yl] pyridine, cis-l- (4-chlorophenyl) -2- (1H-1, 2,4-triazol-1-yl) -cycloheptanol, 2,4-dihydro-5-methoxy-2-methyl-4- [[ [[1- [3- (trifluoromethyl) -phenyl] -ethylidene] -amino] -oxy] -methyl] -phenyl] -3H-1, 2, 3-triazol-3-one, 1- (2, 3- dihydro-2,2-dimethyl-lH-inden-l-yl) -lH-imidazole-5-carboxylic acid methyl ester, 2- [[[cyclopropyl [(4-methoxyphenyl) imino]] methyl] thio] methyl] phenyl} -3-methoxyacrylate methyl, 3- (4-chlorophenyl) -3-. { [N- (isopropoxycarbonyl) valyl] amino} methyl propanoate, 4-chloro-alpha-propynyloxy-N- [2- [3-methoxy-4- (2-propynyloxy) phenyl] ethyl] -benzacetamide, 2- (2- { [6- (3- chloro-2-methylphenoxy) -5-fluoropyrimidin-4-yl] oxy} phenyl) -2- (methoxyimino) -N-methylacetamide, (2S) -N- [2- [4- [[3- (4 chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2- [(methylsulfonyl) amino] -butanamide, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2, 4, 6-trifluorophenyl) [1, 2, 4] triazolo [1, 5-a] pyrimidine, 5-chloro-6 (2,4,6-trifluorophenyl) -N- [(IR) -1,2,2-trimethylpropyl] [1, 2, 4] triazolo [1,5-a] pyrimidine-7 -amine, 5-chloro-N [(1R) -1,2-dimethylpropyl] -6- (2,4,6-trifluorophenyl) [1, 2,] triazolo [1, 5-a] pyrimidin-7-amine, N- [l (5-bromo-3-chloropyridin-2-yl) ethyl] -2,4-dichloronicotinamide, N- (5-bromo-3-chloropyridin-2-yl) methyl-2,4-dichloronicotinamide, N- [1- (5-bromo-3-chloropyridin-2-yl) ethyl] -2-fluor- -yod-nicotinamide, 2-butoxy-6-yod-3-propyl-benzopyranon-4-one, N [2- (4- { [3- (4-chlorophenyl) prop-2-yn-l-yl] oxy} - 3-methoxyphenyl) ethyl] -N-2- (methylsulfonyl) valinamide, N- . { (Z) [(cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2, 3-difluorophenyl] methyl} -2-phenylacetamide, N- (4-chloro-2-nitrophenyl) -N-ethyl-4-methyl-benzosulfonamide, N- (3-ethyl-3,5,5-trimethyl-cyclohexyl) -3-formylamino-2-hydroxy -benzamide, 2 [[[[1- [3 (l-fluoro-2-phenylethyl) oxy] phenyl] ethylidene] amino] oxy] methyl] -alpha- (methoxyimino) -N-methyl-alpha-E-benzacetamide, N-. { 2- [3-chloro-5 (trifluoromethyl) pyridin-2-yl] ethyl} -2- (trifluoromethyl) benzamide, N- (31,41-dichloro-5-fluoro-biphenyl-2-yl) -3- (difluoromethyl) -l-methyl-1H-pyrazole-4-carboxamide, N (6-methoxy-3 -pyridinyl) -cyclopropanecarboxamide, l - [(4-methoxyphenoxy) methyl] -2,2-dimethylpropyl-lH-imidazole-l- carboxylic acid, 0- [1- [(4-methoxyphenoxy) methyl] -2,2-dimethylpropyl] -lH-imidazole-1-carbothioic acid, 2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine, 3, 4, 5-trichloro-2,6-pyridinedicarbonitrile, Bactericides: Bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octylinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations. Insecticides / acaricides / nematicides: 1. Acetylcholinesterase inhibitors (AChE) 1.1 Carbamates (eg alanicarb, aldicarb, aldoxicarb, alixicarb, aminocarb, azametifos, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxicarboxim, carbaryl, carbofuran, carbosulfan , cloetocarb, coumafos, cyanofenfos, cyanofos, dimetilan, etiofencarb, fenobucarb, fenotiocarb, formetanato, furatiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, triazamate, trimetacarb, XC , xylilcarb) 1. 2 Organophosphates (eg, acephate, azametifos, azinphos (-methyl, -ethyl), bromophosethyl, bromfenvinphos (-methyl), butathiophos, cadusafos, carbophenotion, chloretoxyphos, chlorfenvinphos, chloromides, chlorpyrifos (-methyl / -ethyl), coumaphos, cyanofenfos, cyanofos, chlorfenvinfos, demeton-S-methyl, demeton-S-metilsulfona, dialifos, diazinón, diclofention, dichlorvos / DDVP, dicrotofos, dimetoato, dimetilvinfos, dioxabenzofos, disulfoton, EPN, etión, etoprofos, etrimfos, famfur, fenamiphos, fenitrothion, fensulfothion, fention, flupirazophos, fonofos, formotion, fosmetilán, fostiazato, heptenofos, iodophenes, iprobenfos, isazofos, isofenfos, isopropyl O-salicylate, isoxatión, malatión, mecarbam, metacrofos, methamidophos, raetidatión, mevinfos, monocrotofós, naled, ometoate, oxydemeton-methyl, parathion (-methyl / -ethyl), fentoate, phorate, phosalone, phosmet, phosphamidon, phosphocarb, phoxim, pirimiphos (-methyl / -ethyl), profenofos, propafos, propetamfos, protiofos, protoato, pyraclofos, piridafention, piridation, quinalfos, sebufos, sulfotep, sulprofos, tebupirimfos, temefos, terbufos, tetrachlorovinfos, thiometon, triazofos, trichlorfon, vamidotión) 2. Modulators of the sodium channels / blockers of voltage-dependent sodium channels 2.1 Pyrethroids (eg, acrinatrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, isomer of bioallethrin-S-cyclopentyl, bioetanometrin, biopermethrin, bioresmethrin, clovaporrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocitrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, teta-, zeta-), cyphenothrin, DDT, deltamethrin, empentrin (IR isomer), esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenpiritrin, fenvalerate, flubrocitrinate, flucitrinate, flufenprox, flumethrin, fluvalinate, fubfenprox, gamma-cyhalothrin, imiprotrin, kadetrin, lambdacyhalothrin, metofluthrin, permethrin (cis-, trans-), phenothrin (IR-trans isomer), praletrin, profluthrin, protrifenbuto, piresmethrin, resmethrin, RU 15525, silafluofen, tau-fluvalinate, tefluthrin, ^ teralethrin, tetramethrin (IR isomer), tralometrine, transfluthrin, ZXI 8901, pyrethrins (pyrethrum)) 2.2 Oxadiazines (eg, indoxacarb) 3. Acetylcholine receptor agonists / antagonists ^ 3.1 Cloronicotinyl / neonicotinoid (eg, acetamiprid, clotianidin , dinotefuran, imidacloprid, nitenpyram, nitiazine, thiacloprid, thiamethoxam) 3.2 Nicotine, bensultap, cartap 4. Modulators of acetylcholine receptors 0 4.1 Spinosyns (eg spinosad) 5. Chloride channel antagonists controlled by GABA 5.1 Cyclodiene organochloride (eg, camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor 5. 2 Fiproles (eg, acetoprol, etiprole, fipronil, vaniliprole) 6. Chondroitin channel activators 6.1 Mectins (eg, abamectin, avermectin, emamectin, emamectin benzoate, ivermectin, milbemectin, milbemycin) 7. Juvenile hormone mimetics (eg, diofenolan, epofenonane, phenoxycarb, hydroprene, kinoprene, methoprene, pyriproxyfen, triprene) 8. Ecdysone agonists / disrupters 8.1 Diacylhydrazines (eg, chromafenozide, halofenozide, methoxyfenozide, tebufenozide) 9. Chitin biosynthesis inhibitors 9.1 Benzoylureas (for example, bistrifluron, clofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron) 9.2 Buprofezin 9.3 Ciromazine 10. Inhibitors of oxidative phosphorylation, ATP disruptors 10.1 Diafentiuron 10.2 Organotins (for example, azocyclotin, cyhexatin, fenbutatin oxides) 11. Optometers oxidative phosphorylation by interrupting proton gradients H 11.1 Pyrroles (eg, chlorfenapyr) 11.2 Dinitrophenols (eg, binapacryl, dinobutone, dinocap, DNOC) 12. Electron transport inhibitors to site I 12.1 METI (eg, fenazaquin, fenpyroximate, pyrimidifen , pyridaben, tebufenpyrad, tolfenpirad) 12.2 Hydramethylnones 12.3 Dicofol 13. Inhibitors of electron transport to site II 13.1 Rotenone 14. Inhibitors of electron transport to the site III 14.1 Acequinocyl, fluacripirim 15. Microbial disruptors of the intestinal membrane of insects Strains of Bacillus thuringiensis 16. Inhibitors of the synthesis of fats 16.1 Tetronic acids (eg spirodiclofen, spiromesifen) 16.2 Tetramic acids [eg, carbonates of 3- ( 2,5-dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl-ethyl (alias: carbonic acid, 3- (2,5-dimethylphenyl) -8 esters -methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl-ethylic, CAS registry number: 382608-10-8) and acid carbon, cis-3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl-ethyl esters (CAS registry number: 203313-25- 1)] 17. Carboxamides (eg, flonicamide) 18. Octopaminergic agonists (eg, amitraz) 19. Magnesium-stimulated ATPase inhibitors (eg, propargite) 20. Phthalamides (eg, N2- [1, 1 -dimethyl-2- (methylsulfonyl) ethyl] -3-yod-N1- [2-methyl-4- [1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl] phenyl] -1,2-benzenedicarboxamide (CAS registry number: 272451-65-7), flubendiamide) 21. Nereistoxin analogues (eg, thiocyclam-hydrogen-oxalates, thiosultap-sodium) 22. Biologicals, hormones, or pheromones (eg, azadirachtin, Bacillus spec, Beauveria spec, codlemone, Metarrhizium spec, Paecilomyces spec, Thuringiensin, Verticillium spec.) 23. Active ingredients with unknown or non-specific mechanisms of action 23.1 Fumigants (for example, aluminum phosphides) child, methyl bromides, sulfuryl fluorides) 23. 2 Selective antinutrient inhibitors (eg cryolite, flonicamide, pymetrozine) 23.3 Mite growth inhibitors (eg, clofentezine, etoxazole, hexythiazox) 23.4 Amidoflumet, benclotiaz, benzoximate, bifenazate, bromopropylate, buprofezin, quinomethionate, clordimeform, chlorobenzilate , chloropicrin, clotiazoben, cycloprene, ciflumetofen, dicyclanil, fenoxacrim, phentrifanil, flubenzimine, flufenerim, flutenzin, gossyplure, hydramethylnon, japoniluro, methoxadiazone, kerosene, piperonyl butoxide, potassium oleate, pyrafluprol, pyridyl, pyriprole, sulfluramide, tetradiphen, tetrasul , triaratene, verbutin, in addition, the compound 3-methyl-phenyl-propylcarbamate (Tsumacide Z), the compound 3- (5-chloro-3-pyridinyl) -8- (2, 2, 2-trifluoroethyl) -8-azabicyclo [3.2.1] octane-3-carbonitrile (CAS number 185982-80-3) and the corresponding 3-endo isomer (CAS number 185984-60-5) (see documents W096 / 37494, W098 / 25923 ) , as well as preparations containing insecticidally effective plant extracts, nematodes, fungi or viruses. Also possible as a mixture with other known active principles, such as herbicides, or with fertilizers and growth regulators, protectants or semiochemical products.

In addition, the compounds of formula (I) according to the invention also have very good antifungal effects. They have a very broad spectrum of antifungal action, especially against dermatophytes and yeasts, molds and diphasic fungi (for example, against Candida species such as Candida albicans, Candida glabrata), as well as Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trychophyton species such as Trychophyton mentagrophytes, Microsporon species such as Microsporon canis and Audouinii. The list of these fungi does not represent a limitation of the recordable fungal spectrum at all, but only has a clarifying character. The active ingredients can be applied as such, in the form of their formulations of the forms of application prepared therefrom as solutions, suspensions, powders for injection, pastes, soluble powders, dusts and ready-to-use granules. The application is carried out in a customary manner, for example by watering, spraying, spraying, dusting, dusting, foaming, painting, etc. In addition, it is possible to produce the active principles according to the ultra-low volume process or to inject the active ingredient preparation or the active principle itself into the soil. The seeds of the plants can also be treated. In the use of the active principles according to the invention as fungicides, the doses can be varied within a larger interval depending on the type of application. In the treatment of plant parts, the doses of active principle are between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the treatment of the seed, the doses of active principle are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the doses of active principle are in general between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha. As already mentioned above, all the plants and their parts can be treated according to the invention. In a preferred embodiment, plant species and plant varieties of wild origin or obtained by conventional biological culture methods such as hybridization or fusion of protoplasts, as well as their parts, are treated. In another preferred embodiment, transgenic plants and plant varieties were obtained by genetic technology methods, possibly in combination with conventional procedures (genetically modified organisms) and their parts were treated. The term "parts" or "parts of plants" or "plant parts" is explained above. It is preferred to treat especially according to the invention Plants of the vegetable varieties respectively commercially common or in use. Plant varieties are plants with new properties ("traits") that have been grown either by conventional culture, by mutagenesis or by recombinant DNA techniques. These can be breeds, breeds, biotypes and genotypes. Depending on the plant species or plant varieties, their habitat and growth conditions (soils, climate, vegetation periods, food), the effects ("synergistic") added can also appear through the treatment according to the invention. Thus, for example, decreased doses and / or amplifications of the action spectrum and / or a reinforcement of the action of the substances and agents that can be used according to the invention, better growth of the plants, high tolerance compared to high temperatures are possible. or low, high tolerance against dryness or against water content and salts in the soil, high capacity to flower, facilitated harvesting, acceleration of maturity, higher yields, higher quality and / or higher nutritional value of the harvesting products, higher capacity of conservation and / or machinability of the collection products, which exceed the effects that are really expected. To transgenic plants or plant varieties (obtained by genetic technology) to be treated according to the invention belong all the plants that were obtained by the modification of genetic technology of genetic material, which gives these plants especially advantageous valuable properties ("traits"). Examples of such properties are better plant growth, high tolerance compared to high or low temperatures, high tolerance against dryness or against water content and salts in the soil, high ability to flower, facilitated harvesting, acceleration of maturity, higher yields , higher quality and / or greater nutritional value of the collection products, greater storage capacity and / or machinability of the collection products. Other examples and especially outstanding of such properties are a high protection of plants against animal and microbial pests, such as against insects, mites, plant pathogenic fungi, bacteria and / or viruses, as well as a high tolerance of plants to certain active ingredients. herbicides. Examples of transgenic plants are important cultivated plants such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed, as well as fruit plants (with fruits such as apples, pears, citrus fruits and grapes), especially corn. , soybeans, potatoes, cotton, tobacco and rapeseed. As properties ("traits"), the high protection of plants against insects, arachnids, nematodes and snails by toxins formed in plants, especially those that, through the genetic material of Bacillus Thuringiensis (for example, by the genes CrylA (a), CrylA (b), CrylA (c), CryllA, CrylIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF, as well as their combinations), are generated in plants (hereinafter "Bt plants"). As properties ("traits"), the high protection of plants against fungi, bacteria and viruses by means of systematic acquired resistance (SAR), systemin, phytoalexins, elicitors, as well as resistant genes and correspondingly expressed proteins and toxins also stands out. As properties ("traits"), in particular, the high tolerance of the plants in comparison with certain herbicidal active ingredients, for example imidazolinones, sulfonylureas, glyphosates or phosphinothricin (for example, "PAT" gene), are particularly notable. The genes that respectively confer the desired properties ("traits") may also be present in combinations with each other in the transgenic plants. As examples of "Bt plants", mention may be made of varieties of maize, cotton varieties, varieties of soybeans and potato varieties marketed under the trade names YIELD GARD® (for example, corn, cotton, soybeans), KnockOut® ( for example, corn), StarLink® (for example, corn), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf (potatoes). Examples of herbicide tolerant plants are varieties of maize, cotton varieties and soybean varieties, which are marketed under the trade names Roundup Ready® (tolerance against glyphosate, for example maize, cotton, soybean), Liberty Link® (tolerance against phosphinothricin) , for example, rapeseed), IMI® (tolerance against imidazolinones) and STS® (tolerance against sulfonylureas, for example maize). As herbicide-resistant plants (conventionally cultivated with tolerance to herbicides), the varieties marketed under the name Clearfield® (for example, maize) are also to be mentioned. Obviously, these statements also serve for plant varieties developed or that will reach the market in the future with these genetic properties or developed in the future ("traits"). The listed plants can be treated in a particularly advantageous manner according to the invention with the compounds of general formula (I) or the mixtures of active principles according to the invention. The preferred ranges in the active principles or mixtures indicated above are also valid for the treatment of these plants. The treatment of plants with the compounds or mixtures specially enumerated in the present text stands out. The preparation and use of the active principles according to the invention derives from the following examples.

Preparation examples Example 1 [process 1) - k) - j) - f) - a) - b)] Step 1, procedure 1): 37.5 g (0.694 mol) of sodium methylate were dissolved in 330 g of methanol. At room temperature, 31.7 g (0.417 mol) of thiourea and then 59.5 g (0.278 mol) of 3-thienylmalonic acid dimethyl ester (DE3942952) were added. The mixture was refluxed 4 hours. It was acidified with dilute hydrochloric acid and stirred. The product was separated by filtration, washed with water and dried. 48 g of 2-mercapto-4,6-dihydroxy-5-thien-3-yl-pyrimidine were obtained. HPLC: log pa = -0.12 * (lambda maximums: 302, 246). 1 H NMR (DMSO-d 6, tetramethylsilane): d = 7.39-7.41 (1H); 7.52-7.53 (1H); 7.70-7.71 (1H) ppm. Stage 2, procedure k) dissolved 11.46 g (0.212 mol) of sodium methylate in 240 ml of ethanol. At 0 ° C, 48 g (0.212 mol) of 2-mercapto-4,6-dihydroxy-5-thien-3-yl-pyrimidine. Then 30.1 g (0.212 mol) of methyl iodide were added dropwise at 0 ° C. Refluxed for 30 minutes and then the reaction mixture was concentrated in vacuo. The residue was briefly boiled with water and then cooled to 0 ° C. The product was separated by filtration and dried. 37.9 g of 2-methylthio-4,6-dihydroxy-5-thien-3-yl-pyrimidine were obtained. HPLC: logp a = 1.10 * (lambda maximums: 304). 1 H NMR (DMSO-d 6, tetramethylsilane): d = 7.39-7.41 (1H); 7.70-7.71 (1H); 7.89-7.90 (1H) ppm. Stage 3, procedure j) 15 g (0.062 mol) of 2-methylthio-4,6-dihydroxy-5-thien-3-yl-pyrimidine were refluxed in 119.64 g (0.78 mol) of phosphorus oxychloride for 4 hours. The volatile components were distilled off at 10 Torr (1.33 kPa), the residue was taken up in acetic acid ethyl ester and washed first with water, then with dilute sodium hydrogencarbonate solution. The solvent was separated by distillation at 10 Torr (1.33 kPa). 11.3 g of 2-methylthio-4,6-dichloro-5-thien-3-yl-pyrimidine were obtained. HPTLC: log p a = 3.94 * (lammaxima: 270). 1N NMR (DMSO-d 6, tetramethylsilane): d = 2.58 (3H); 7.19-7.20 (1H); 7.68-7.70 (1 H); 7.72-7.73 (1H) ppm. Stage 4, procedure f) 6.19 g (0.031 mol) of 4-methylpiperidine in 75 ml of dichloromethane were previously placed. At 0 ° C, 7.5 g (0.031 mol) of 2-methylthio-4,6-dichloro-5-thien-3-yl-pyrimidine were added and then stirred for 12 hours at room temperature. The reaction mixture was concentrated to 10 Torr (1.33 kPa), the residue was taken up in ethyl acetate and washed successively with dilute hydrochloric acid, water and dilute sodium hydrogencarbonate solution. The solution was dried, the solvent was distilled off at 10 Torr (1.33 kPa) and 9.1 g of 2-methylthio-4-chloro-5-thien-3-yl-6- (4 '- methylpiperidin-1- il) pyrimidine. HPLC: log pa = 5.47 * (lammaximums NMR XH (DMS0-d6, tetramethylsilane): d = 4.01-4.06 (1H); 7.1 1-7.12 (1H); 51-7.52 (1H) ppm Step 5, procedure a) 6 g (0.018 mol) of 2-methylthio-4-chloro-5-thien-3-yl-6- (4'-methyl-piperidin-1-yl) pyrimidine were dissolved in 120 ml of dichloromethane. At 0 ° C, 8.67 g (0.035 mol) of 3-chloroperbenzoic acid were added in portions. The reaction mixture was stirred one hour at 0 ° C and 14 hours at room temperature. The solvent was distilled off, the residue was taken up in acetic acid ethyl ester and washed with 10% aqueous sodium hydrogencarbonate solution. The organic phase was dried and concentrated. The residue was purified by chromatography on silica gel in cyclohexane: acetic acid ethyl ester = 3: 1. 7.8 g of 2-methylsulfonyl-4-chloro-5-thien-3-yl-6- (4'-methylpiperidin-1-yl) were obtained. ) pyrimidine. HPLC: log pa = 3.53 * (lammaximums: 214, 278). X H NMR (DMS0-d 6, tetramethylsilane): d = 0.084-0.85 (3H); 0.97-1.07 (2H); 1.40-1.58 (3H); 2.74-2.81 (2H); 3.25 (3H); 3.84-3.87 (2H); 7.19-7.21 (1 H); 7.65-7.66 (1H); 7.73-7.75 (1H) ppm. CG-MS: retention index = 3014 (M = 371, 336, 256, 55). Stage 6, procedure b) (I'-l) Preferably 0.108 g (0.003 mol) of sodium hydride was placed in 20 ml of dimethylformamide. 0.18 g (0.003 mol) of pyrazole was added dropwise at 0 ° C and stirred for one hour. Then 1 g (0.003 mol) of 2-methylsulfonyl-4-chloro-5-thien-3-yl-6- (4'-methylpiperidin-1-yl) pyrimidine in dimethylformamide was added. It was stirred two hours at room temperature, the reaction mixture was poured into water and extracted with ethyl ester of acetic acid. The organic phase was dried, concentrated and the residue was washed with a mixture of diethyl ether and petroleum ether. It was separated by filtration and the product was dried. 0.9 g of 2- (pyrazol-1-yl-) -4-chloro-5-thien-3-yl-6- ('-methylpiperidin-1-yl) pyrimidine were obtained. HPLC: log p a = 4.37 * (lammaximums: 256). X H NMR (DMSO-d 6, tetramethylsilane): d = 0.84-0, 86 (3H); 1.01-1.24 (2H); 1.48-1.53 (3H); 3.90-3.94 (2H); 6.55-6.56 (1H); 7.17-7.19 (1 H); 7.59 (1H); 7.71 (1H); 7.81-7.82 (1H); 8.55-8.56 (1H) ppm. CG-MS: retention index = 2910 (M = 359, 344, 324, 310, 296, 280, 254, 227, 200, 186, 159, 133, 118, 98, 79, 55, 41, 27). The 5-heterocyclylpyrimidines of the formula listed in the following table B are also obtained according to the procedures indicated above.

Table B a The determination of the logP values took place according to directive 79/831 / CEE, annex V.A8 by means of HPLC (high resolution liquid chromatography) in reverse phase columns (C 18) with the following procedures: * Temperature: 40 ° C; mobile phase: 0.1% aqueous formic acid and acetonitrile; linear gradient of 10% acetonitrile to 95% acetonitrile. ** Temperature: 43 ° C; mobile phase: 0.1% aqueous phosphoric acid and acetonitrile; linear gradient of 10% acetonitrile to 95% acetonitrile. The calibration was performed respectively with unbranched alcan-2-ones (3 to 16 carbon atoms) with known logP values (determination of logP values by retention times by linear interpolation between two determined alkanones). The maximum lambda values were determined respectively at the maximums of the chromatography signals by UV spectra between 190 nm and 400 nm. Example 196 2- [4-Chloro-6- (1, 2-dimethyl-propylamino) -5- (3-methyl-thiophen-2-yl) -pyrimidin-2-yl] -4,5-dimethyl-2, 4-dihydro-pyrazol-3-one Stage 1 To a suspension of 5.6 g (0.0150 mol) of [6-chloro-2-methanesulfonyl-5- (3-methyl-thiophen-2-yl) -pyrimidin-4-yl] - (1,2- dimethyl-propyl) -amine in 75 mL of ethanol is added 1.9 g (0.0384 mol) of hydrazine hydrate. The mixture is heated to reflux 90 minutes and after cooling it is concentrated under reduced pressure. The residue is taken up in ethanol again, dried over sodium sulfate and concentrated to dryness. 6.0 g of [6-chloro-2-hydrazino-5- (3-methyl-thiophen-2-yl) -pyrimidin-4-yl] - (1,2-dimethyl-propyl) -amine are obtained. HPLC: log p = 2.26 Stage 2 To a mixture of 0.65 g (2.0 mmol) of [6-chloro-2-hydrazino-5- (3-methyl-thiophen-2-yl) -pyrimidin-4-yl] - (1,2- dimethyl-propyl) -amine and 0.29 g (2.2 mmol) of methyl 2-methyl-3-oxo-butyric acid in 6.5 ml of ethanol are added 6.5 ml of glacial acetic acid. The mixture is heated at reflux for 3 hours and, after cooling, it is concentrated under reduced pressure. The residue is purified by chromatography on silica gel in 2-methoxy-2-methylpropane: petroleum ether = 4: 1. 0.1 g of 2- [4-chloro-6- (1,2-dimethyl-propylamino) -5- (3-methyl-thiophen-2-yl) -pyrimidin-2-yl] -4.5 are obtained -dimethyl-2, 4-dihydro-pyrazol-3-one. HPLC: log p = 4.46 The 5-heterocyclylpyrimidines of formula listed in the following table B are also obtained according to the procedures indicated above. Table C a The determination of the logP values took place according to directive 79/831 / CEE, annex V.A8 by means of HPLC (high resolution liquid chromatography) in reverse phase columns (C 18) with the following procedures: * Temperature: 40 ° C; mobile phase: 0.1% aqueous formic acid and acetonitrile; linear gradient of 10% acetonitrile to 95% acetonitrile. ** Temperature: 43 ° C; mobile phase: 0.1% aqueous phosphoric acid and acetonitrile; linear gradient of 10% acetonitrile to 95% acetonitrile. The calibration was performed respectively with unbranched alcan-2-ones (3 to 16 carbon atoms) with known logP values (determination of the logP values by the retention times by linear interpolation between two determined alkanones). Dimethyl 2- (3-methyl-thiophen-2-yl) -malonic acid ester: Stage 1 Aluminum trichloride (163 g, 1.222 mol) was previously placed in 540 ml of dichloromethane, the mixture was cooled to 0 ° C and at this temperature 112 ml (150 g, 1.222 mol) of methyl ester chloride were added dropwise. oxalic acid. The mixture is then stirred at this temperature for 10 min, then 3-methylthiophene is added dropwise at 0 ° C and the reaction mixture is stirred at this temperature after being warmed to room temperature overnight. The hydrolysis carried out by discharging 2 1 of ice water, separating the organic phase, washing with sodium hydrogen carbonate solution and drying the organic phase over sodium sulphate provided after filtration separation of the desiccant and evaporation in a rotary evaporator 119, 5 g of (3-methyl-thiophen-2-yl) -oxo-acetic acid methyl ester. Yield: 57%. XH NMR (DMSO): d = 8.09 (d, 1 H), 7.19 (d, 1 H), 7.67 (dd, 1 H), 3.90 (s, 3 H), 2, 49 (s, 3 H).

Stage 2 A solution of 90 g (0.489 mol) of (3-methyl-thiophen-2-yl) -oxo-acetic acid methyl ester in 260 ml of diethylene glycol was slowly mixed with 112.5 ml (116 g, 2.312 mol) of hydrazine hydrate and the mixture was heated for 30 min at reflux. After cooling to 30-40 ° C, 82 g (1.246 mol) of potassium hydroxide were added in portions, which is accompanied by an increase in temperature to 70-80 ° C with simultaneous production of nitrogen. After this, it was heated slowly to reflux and in total it was stirred for 5 h at this temperature. After cooling to room temperature, the mixture was added to 2 1 of water, adjusted to pH = 1 with 250 ml of semi-concentrated hydrochloric acid and extracted with ethyl acetate. Drying of the organic phase over magnesium sulfate, separation by filtration and removal of the solvent gave 50 g of (3-methyl-thiophen-2-yl) -acetic acid. Yield: 66%. R N X H (DMSO): d = 7.25 (d, 1 H), 6.84 (d, 2 H), 3.67 (s, 2 H), 2.11 (s, 3 H).

Stage 3 A solution of 50 g (0.32 mol) of (3-methyl-thiophen-2-yl) -acetic acid in 500 ml of methanol was mixed with 5 ml of concentrated sulfuric acid and heated at reflux for 8 h. Then, the solvent was removed in a rotary evaporator and the residue was mixed with water and dichloromethane. Phase separation and re-extraction of the aqueous phase with dichloromethane yielded 42.5 g of (3-methyl-thiophen-2-yl) -acetic acid methyl ester after drying of the organic phase over sodium sulfate, separation by filtration and evaporation in rotavapor. Yield: 70%. NMR - "(DMSO): d = 7.30 (d, 1 H), 6.87 (d, 1 H), 3.82 (s, 2 H), 3.65 (s, 3 H), 2.13 (s, 3 H) Stage 4 Under argon, 311 ml (332 g, 3, 685 mol) of dimethyl carbonate were mixed with 14.7 g of sodium hydride (60% by weight). mineral oil) and heated to 80 ° C. At this temperature, a solution of 41 g (0.217 mol) of methyl (3-methyl-thiophen-2-yl) -acetic acid in 50 ml of toluene was added slowly and the mixture was stirred overnight at reflux. For the regeneration, it was diluted with approximately 200 ml of methanol, the mixture was added in ice water and adjusted acidic with dilute hydrochloric acid. Extraction with dichloromethane, drying of the organic phase over sodium sulfate, separation by filtration and removal of the solvent gave 43.6 g of 2- (3-methyl-thiophen-2-yl) -malonic acid dimethyl ester. . Yield: 88%. 1 H-NMR (DMSO): d = 7.42 (d, 1 H), 6.89 (d, 1 H), 5.27 (s, 1 H), 3.69 (s, 6 H), 2, 15 (s, 3 H). Spectroscopic data of the analogously prepared intermediates: Examples of uses Example A Test with Sphaerotheca (cucumber) / protector Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether To prepare an active compound preparation of 1 part by weight of active ingredient is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the protective efficacy, young plants are sprayed with the preparation of active principle in the indicated dose. After drying the projected layer, the plants are inoculated with an aqueous spore suspension of Sphaerotheca fuliginea. Then, the plants are placed in a greenhouse at approximately 23 ° C and a relative humidity of approximately 70%. 7 days after the inoculation the assessment takes place. Here 0% means an efficiency that corresponds to that of the controls, while an efficiency of 100% means that no pest is observed. In this test, the compounds according to the invention of the following numbers of examples show an efficiency of 70% or more at an active ingredient concentration of 100 ppm: eleven, 38, 70 Example B Test with Venturia (apple) / protector Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether To prepare an active ingredient preparation 1 part by weight of active ingredient is mixed appropriately with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the protective efficacy, they are sprayed young plants with the preparation of active principle in the indicated dose. After the projected layer is dried, the plants are inoculated with an aqueous suspension of conidia of the pathogen agent of the mange of Venturia inaequalis and then remain for 1 day in incubation cabins at approximately 20 ° C and 100% relative humidity. The plants are then placed in the greenhouse at about 21 ° C and a relative humidity of about 90%. 10 days after the inoculation, the assessment takes place. Here 0% means an efficiency that corresponds to that of the controls, while an efficiency of 100% means that no pest is observed. In this test, the compounds according to the invention of the following numbers of examples show an efficiency of 70% or more at an active ingredient concentration of 100 ppm: 11, 38, 70 Example C Test with Botrytxs (cucumber) / protector Solvent: 49 parts by weight of N, N-dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether To prepare an active ingredient preparation of 1 part by weight of active ingredient is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the protective efficacy, young cucumber plants are sprayed with the preparation of active principle in the indicated dose. 1 day after treatment, the plants are inoculated with a spore suspension of Botrytis cinerea and then left for 48 hours at a relative humidity of 100% and 20 ° C. Then the plants are left at a relative humidity of 96% and a temperature of 13 ° C. 5-6 days after the inoculation the evaluation takes place. Here 0% means an efficiency that corresponds to that of the controls, while an efficiency of 100% means that no pest is observed. In this test, the compounds according to the invention of the following numbers of examples show an efficiency of 70% or more at an active substance concentration of 500 ppm: 1-1, 134, 182, 214 It is noted that in relation to this date the best method known by the applicant to carry out the aforementioned invention is that which is clear from the present description of the invention.

Claims

CLAIMS Having described the invention above, the following claims are claimed as property: 1. Compounds of general formula characterized in that R1 represents hydrogen, Ci-Ce alkyl, C2-Cs alkenyl, C3-C8 alkynyl or C3-C8 cycloalkyl, wherein R1 may be substituted with one to three identical or different Ra groups and Ra represents halogen, hydroxy, cyano, C1-C4 alkoxy and / or C3-C6 cycloalkyl, or R1 represents a saturated, unsaturated or aromatic mono or bicyclic heterocycle of five to ten members containing from one to four heteroatoms of the group O, N or S, in which R1 may be substituted with one to two identical or different Rb groups, and Rb represents halogen, Ci-C6 alkyl, cyano, nitro and / or C3-C6 cycloalkyl; R 2 represents hydrogen or C 1 -C 6 alkyl, or R 1 and R 2 represent together with the nitrogen to which a saturated, unsaturated or aromatic mono or bicyclic heterocycle of three to six members are attached, wherein the heterocycle may contain another heteroatom of group 0, N or S and may be substituted with one to three identical Rc groups or various, and Rc represents halogen, Ci-C6 alkyl and / or Ci-C6 haloalkyl, R3 represents a saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle of three to ten members containing from one to four heteroatoms of group 0, N or S, wherein R3 may be substituted with one to four identical or different Rd groups, and Rd represents halogen, hydroxy, cyano, oxo, nitro, amino, mercapto, Ci-C6 alkyl, Ci-C6 haloalkyl, C2- alkenyl C6, C2-C6 alkynyl, C3-C6 cycloalkyl, Ci-C6 alkoxy, Ci-C6 haloalkoxy, carboxyl, Ci-C7 alkoxycarbonyl, carbamoyl, Ci-C7 alkyl aminocarbonyl, Ci-C6 alkyl Ci-C6 alkyl aminocarbonyl, morpholinocarbonyl, pyrrolidinocarbonyl, Ci-C7 alkylcarbonylamino or, Ci-C6-amino alkyl, di- (Ci-C6 alkyl) amino, Ci-C6 alkyl-thio, Ci-C6 alkylsulfinyl, Ci-C6 alkylsulfonyl, hydroxysulfonyl, aminosulfonyl, Ci-C6 alkyl aminosulfonyl and / or di- (alkyl Ci-) aminosulfonyl; R4 represents halogen or Ci-Cg alkyl, Ci-C8 alkoxy, Ci-C8 haloalkyl, Ci-Ce-thio alkyl, Ci-C8 alkyl sulfinyl, Ci-C8 alkylsulfonyl or cyano, R5 represents a saturated or unsaturated mono or bicyclic heterocycle of five or six members containing one to four heteroatoms of group 0, N or S, in which R5 may be substituted with from one to four Re groups same or different, and Re represents halogen, hydroxy, cyano, nitro, Ci-C6 alkyl, Ci-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-6 alkoxy C6, Ci-C6 halogenoalkoxy, carboxyl, Ci-C7 alkoxycarbonyl, carbamoyl, Ci-C7 alkylaminocarbonyl, Ci-C6 alkylCi-C6 alkylaminocarbonyl, Ci-C6 alkyl, Ci-Cg-sulfinyl alkyl, alkyl C1-C6-sulfonyl, hydroxyimino-C1-C6 alkyl and / or C1-C6 alkyl-alkoxyiminoCi-C6 alkyl. 2. Compounds of general formula characterized in that R1 represents hydrogen, Ci-C8 alkyl, C2-C8 alkenyl, C3-C8 alkynyl or C3-C8 cycloalkyl, wherein R1 may be substituted with one to three identical or different Ra groups and Ra represents halogen, hydroxy, cyano, C1-C4 alkoxy and / or C3-C6 cycloalkyl, or R1 represents a saturated, unsaturated or aromatic mono- or bicyclic heterocycle of five to ten members containing from one to four heteroatoms of group 0, N or S, in which R1 may be substituted with one to two identical or different Rb groups, and Rb represents halogen, CI-CÉ alkyl, cyano, nitro and / or C3-C6 cycloalkyl; R 2 represents hydrogen or C 1 -C 6 alkyl, or R 1 and R 2 represent together with the nitrogen atom to which a saturated or unsaturated mono or bicyclic heterocycle of three to six members are attached, in which the heterocycle may contain another heteroatom of the heterocycle. group 0, N or S and can be substituted with one to three identical or different Rc groups, and Rc represents halogen, Ci-C6 alkyl and / or Ci-C6 haloalkyl, R3 represents a saturated or partially unsaturated mono or bicyclic heterocycle or aromatic of three to ten members containing one to four heteroatoms of the group 0, N or S, in which R3 may be substituted with one to three identical or different Rd groups, and Rd represents halogen, hydroxy, cyano, oxo, nitro, amino, mercapto, Ci-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, Ci-alkoxy C6, C 1 -C 6 halogenoalkoxy, carboxyl, Ci-C 7 alkoxycarbonyl, carbamoyl, Ci-C 7 alkylaminocarbonyl, C 1 -C 6 alkyl-Ci-Cg-aminocarbonyl, morpholinocarbonyl, pyrrolidinocarbonyl, Ci-C 7 alkylcarbonylamino, C 1 alkyl -C6-amino, di- (Ci-C6 alkyl) amino, Ci-C6 alkyl thio, C1-C6 alkyl sulfinyl, Ci-C6 alkylsulfonyl, hydroxysulfonyl, aminosulfonyl, Ci-C6 alkylsulfonyl and / or di - (Ci-C6 alkyl) aminosulfonyl; R4 represents halogen or Ci-C8 alkyl, Ci-Ce alkoxy, Ci-C8 haloalkyl, Ci-C8 alkyl thio, Ci-Ca-sulfinyl alkyl, Ci-C8 alkylsulfonyl or cyano, R5 represents a saturated mono or bicyclic heterocycle , unsaturated or aromatic of five or six members containing one to four heteroatoms of the group 0, N or S, in which R5 can be substituted with one to four equal or different Re groups, and Re represents halogen, hydroxy, cyano , nitro, C 1 -C 6 alkyl, haloalkyl CI-C 0, C 2 -C 6 alkenyl, C 2 -C 2 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, carboxyl, C 1 -C 7 alkoxycarbonyl, carbamoyl, C 1 -C 7 -aminocarbonyl, C 1 -C 6 alkyl-Ci-C 6 alkyl-aminocarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 alkyl sulfinyl, C 1 -C 6 alkyl sulfonyl, hydroxyimino C 1 -C 6 alkyl and / or alkyl C1-C6-C1-C6 alkoxyiminoalkyl. 3. Compounds of formula (I) according to claim 1 or 2, characterized in that R1 represents a residue of formula where # marks the union position. 4. Compounds of formula (I) according to any of claims 1 to 3, characterized in that R1 represents a residue of formula 5. Compounds of formula (I) according to any of claims 1 to 4, characterized because R2 represents hydrogen, methyl, ethyl or propyl. 6. Compounds of formula (I) according to any of claims 1 to 4, characterized in that R1 and R2 together represent a nitrogen atom to which a radical of formula is attached wherein R7 represents hydrogen or methyl, R8 represents methyl, ethyl, fluorine, chlorine or trifluoromethyl, m represents the numbers 0, 1, 2 or 3, in which R8 represents the same or different residues, when m represents 2 or 3, R9 represents methyl, ethyl, fluorine, chlorine or trifluoromethyl, and I represents the numbers 0, 1, 2 or 3, in which R9 represents identical or different residues, when n represents 2 or 3. 7. Compounds of formula (I) of according to any of claims 1 to 4, characterized in that R1 and R2 represent together with the nitrogen to which pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, 3,6-dihydro-l (2H) -piperidinyl or tetrahydro-1 (2H) -pyridazinyl are attached, in which these moieties may be substituted with 1 to 3 atoms of fluorine, 1 to 3 methyl groups and / or trifluoromethyl. 8. Compounds of formula (I) according to any of claims 1 to 7, characterized in that R3 is a three, five or six membered heterocycle, especially of five members. 9. Compounds of formula (I) according to any of claims 1 to 8, characterized in that R3 is a heterocycle that is attached to the pyrimidine ring by nitrogen. 10. Compounds of formula (I) according to any of claims 1 to 9, characterized in that R3 represents, if appropriate, pyrazole, pyrrole, imidazole, 1,2,3-triazole, 1,2,4-triazole, 1, 3, 4-oxadiazole, 1,3,4-thiadiazole, tetrazole, 2-pyridine, 2-pyrimidine, pyrazine or 3-pyridazine substituted with up to four groups Rd. 11. Compounds of formula (I) in accordance with any of claims 1 to 9, characterized in that R3 represents, if appropriate, pyrazole, pyrrole, imidazole, 1,2,3-triazole, 1,2,4-triazole, 1,3,4-oxadiazole, 1,3, 4-thiadiazole, tetrazole, 2-pyridine, 2-pyrimidine, pyrazine or 3-pyridazine substituted with up to three Rd substituted groups. 12. Compounds of formula (I) according to any of claims 1 to 11, characterized in that R3 represents pyrazole, 1,2,3-triazole, 1,2-triazole or pyridazine in which the R 3 cycle is substituted with one to four Rd groups equal to or different from the following: halogen, hydroxy, cyano , nitro, amino, mercapto, alkyl CI-CÉ, halogeno C1-C6 alkyl, C2-C6 alkenyl, 2-5 alkynyl, C3-C6 cycloalkyl, Ci-C6 alkoxy, C1-C6 haloalkoxy, carboxyl, Ci-C7 alkoxy-carbonyl , carbamoyl, C 1 -C 7 -alkylaminocarbonyl, C 1 -C 6 alkyl-Ci-C 6 alkyl-aminocarbonyl, morpholinocarbonyl, pyrrolidinocarbonyl, C 1 -C 7 alkylcarbonylamino, Ci-C 6 alkylamino, di- (Ci-C 6 alkyl) amino, Ci-C6-thio alkyl, Ci-C6-sulfinyl alkyl, C1-C6-alkylsulfonyl, hydroxysulfonyl, aminosulfonyl, Ci-Cg-aminosulfonyl or di- (Ci-Cg alkyl) aminosulfonyl or oxo alkyl. 13. Compounds of formula (I) according to any of claims 1 to 11, characterized in that R3 represents pyrazole, 1,2,3-triazole, 1,2-triazole or pyridazine in which the R 3 cycle is substituted with from one to three groups Rd equal to or different from the following: halogen, hydroxy, cyano, nitro, amino, mercapto, Ci-C6 alkyl, Ci-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, Ci-C6 alkoxy, Ci-C6 haloalkoxy, carboxyl, Ci-C7 alkoxycarbonyl, carbamoyl, C1-C7 alkylaminocarbonyl, Ci-C6 alkyl-Ci-C6 alkyl-aminocarbonyl, morpholinocarbonyl, pyrrolidinocarbonyl, C 1 -C 7 alkylcarbonylamino, Ci-Cg-amino alkyl, di- (alkyl iCe) amino, Ci-C6 alkylthio, Ci-C6 alkyl sulfinyl, dC6 alkylsulfonyl, hydroxysulfonyl , aminosulfonyl, Ci-C6-5 alkyl aminosulfonyl or di- (Ci-C6 alkyl) aminosulfonyl or oxo. Compounds of formula (I) according to any of claims 1 to 13, characterized in that R 4 represents halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 1 -C 6 alkoxy. ^ 15. Compounds of formula (I) according to any of claims 1 to 13, characterized in that R4 means chlorine. 16. Compounds of formula (I) according to any of claims 1 to 15, characterized because R 5 represents pyridyl, which is attached at the 2 or 4 position and can be substituted equally or differently from once to four times, and Re represents fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroxymethyl, hydroxymethyl, methoximinomethyl, 20 methoxymethyl and / or trifluoromethyl. 17. Compounds of formula (I) according to any of claims 1 to 15, characterized in that R5 represents pyrimidyl, which is attached in the 2 or 4 position and can be substituted in the same or different manner from 25 once to three times with Re, and Re means fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroxymethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl. 18. Compounds of formula (I) according to any of claims 1 bis 15, characterized in that R5 represents pyrimidyl, which is attached in the 2 or 3 position and can be substituted in the same or different way from once to three times with Re, and Re means fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroxymethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl. 19. Compounds of formula (I) according to any of claims 1 to 15, characterized in that R5 represents thiazolyl, which is attached in the 2, 4 or 5 position and can be substituted in the same or different way from once to two. sometimes with Re, and Re means fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroxymethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl. 20. Compounds of general formula characterized in that R1, R2, R4 and R5 have the meanings according to claim 1 and R6 represents Ci-C6 alkyl. 21. Compounds of general formula characterized in that R1, R2, R4 and R5 have the meanings according to claim 1, n is = 1 or 2 and R6 represents Ci-c6 alkyl. 22. Compounds of general formula characterized in that R3, R4 and R5 have the meanings according to claim 1 and Hal represents halogen. 23. Compounds of general formula characterized in that R4 and R5 have the meanings according to claim 1, R6 represents C1-C6 alkyl and Hal represents halogen. 24. Compounds of general formula characterized in that R4 and R5 have the meanings according to claim 1 and R6 represents Ci-C6 alkyl. 25. Compounds of general formula characterized in that R4 and R5 have the meanings according to claim 1. 26. Compounds of the general formula (XVIII) characterized because R3, R4 and R5 have the meanings according to claim 1. 27. Compounds of general formula characterized in that R3 and R5 have the meanings according to claim 1. Process for preparing compounds of general formula wherein R1, R2 and R5 have the meanings according to claim 1, R3 represents a heterocycle linked by N and R4 halogen, Ci-C4 alkyl or Ci-C4 haloalkyl, characterized in that according to process a) compounds of formula (II), wherein R1, R2 and R5 have the meanings according to claim 1, R4 represents halogen, C1-C4 alkyl or Ci-C4 haloalkyl, and R6 represents Ci-C6 alkyl, with an oxidant, optionally in the presence of a diluent, and according to process b) the compounds of formula (III) thus obtained wherein R1, R2, R5 and R6 have the meanings given above, R4 represents halogen, C1-C4 alkyl or C1-C4 haloalkyl, and n is = 1 or 2, reacts with a compound of formula R3-H (IV), where R3 has the meanings indicated above, with the condition that R3 has at least one nitrogen atom through which binding to the pyrimidine ring takes place in compounds of formula (A '), optionally in the presence of a diluent and optionally in the presence of an acid acceptor . 29. Process for preparing compounds of general formula wherein R1, R2 and R5 have the meanings according to claim 1, R3 represents a heterocycle linked by C and R4 halogen, C1-C4 alkyl or C1-C4 haloalkyl, characterized in that according to the process c) compounds of formula ( V), in which R, R have the meanings indicated above, with the proviso that R 3 is a heterocycle that is linked by a C atom to the pyrimidine ring in compounds of type (V) and R4 represent halogen, C1-C4 alkyl or haloalkyl C1-C4, react with a compound of formula HNR1R2 (VI), in which R1 and R2 have the meanings indicated above, optionally in the presence of a diluent, optionally in the presence of a catalyst and optionally in the presence of an acid acceptor. 30. Process for preparing compounds of formula (I '"), wherein R1, R2 and R5 have the meanings according to claim 1, R3 represents a heterocycle linked by N or C and R4 Ci-Ca alkyl, Ci-C8 alkoxy, Ci-Csthio alkyl, Ci-C8 alkyl -sulphonyl or cyano, characterized in that compounds of formula (I'a) or (I "a) wherein R1, R2, R3 and R5 have the meanings given above and Hal represents halogen, react well according to process d) with a compound of formula R -M1 (VII) in which R4 represents Ci-C8 alkoxy, Ci alkyl -C8-thio, Ci-Ce-sulfinyl alkyl, Ci-Ce-sulfonyl alkyl or cyano, and M1 represents sodium or potassium, optionally in the presence of a diluent, or according to process e) with Grignard compounds of formula R4-MgHal (VIII) in which R4 represents Ci-Ce alkyl and Hal represents chlorine or bromine, in the presence of a diluent and optionally in the presence of a catalyst. 31. Agents for combating harmful organisms containing diluents and / or vehicles, and optionally surfactants, characterized by a content of at least one compound according to any of claims 1 to 19. 32. Process for combating harmful organisms, characterized because they act as compounds according to any of claims 1 to 19 or agents as defined in claim 31 in harmful organisms and / or their habitat. 33. Use of compounds of formula (I) according to one of claims 1 to 19 or agents according to claim 31 for combating unwanted microorganisms.