WO2009007187A1 - 5-hétarylpyrimidines substituées - Google Patents

5-hétarylpyrimidines substituées Download PDF

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WO2009007187A1
WO2009007187A1 PCT/EP2008/057193 EP2008057193W WO2009007187A1 WO 2009007187 A1 WO2009007187 A1 WO 2009007187A1 EP 2008057193 W EP2008057193 W EP 2008057193W WO 2009007187 A1 WO2009007187 A1 WO 2009007187A1
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alkyl
methyl
compounds
het
alkenyl
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PCT/EP2008/057193
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German (de)
English (en)
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Joachim Rheinheimer
Marianna Vrettou
Bernd Müller
Thomas Grote
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Definitions

  • the present invention relates to 5-hetarylpyrimidines and their salts and to the use of these compounds for controlling plant-damaging fungi, arthropods, plant pests and / or nematodes and as medicaments.
  • the invention also relates to crop protection agents and pharmaceutical compositions containing at least one such compound as an effective ingredient.
  • WO 2004/087678 and WO 2005/070899 disclose 5-phenylpyrimidines bearing an aliphatic, carbo- or heterocyclic radical bonded via C in the 4-position and their use for controlling phytopathogenic fungi (phytopathogenic fungi).
  • WO 01/96314 describes fungicidally active pyrimidines which may carry in the 4-position an aliphatic, carbo- or heterocyclic radical bonded via C and which may be substituted in the 5-position by phenyl, cycloalkyl or heteroaryl.
  • the substituted pyrimidines described herein always have a cyano-substituted amino group in the 2-position.
  • the 5-phenyl- and hetarylpyrimidines known from the prior art are in some cases unsatisfactory in terms of their fungicidal action or have undesirable properties, such as a low compatibility with crops.
  • WO 2005/030216 describes 5-phenylpyrimidines which are substituted in the 4-position by a secondary amino group or a cycloalkyl group and carry in the 2-position an amino group, a cyanamide group, an aryl or a hetaryl substituent. These compounds should be suitable for the treatment of cancer.
  • the 5-phenylpyrimidines known from the prior art are sometimes unsatisfactory in terms of their pharmaceutical activity and / or side effects.
  • the present invention is therefore based on the object of providing compounds with better fungicidal activity and / or a better crop tolerance.
  • Another object of the present invention is to provide novel pyrimidine compounds having a pharmacological action improved as compared with the pyrimidines of the prior art.
  • the present invention thus relates to the 5-hetarylpyrimidine compounds of the general formula I and salts
  • R 1 is d-Cio-alkyl, C 2 -C 0 alkenyl, C 2 -C 10 alkynyl, C 3 -C 0 cycloalkyl or C 3 -C 0 -
  • Cycloalkenyl and wherein the aliphatic, alicyclic groups of the radical definitions of R 1 may be partially or completely halogenated and / or 1, 2, 3 or 4 may carry identical or different substituents L R1 :
  • m is O, 1 or 2;
  • a 1, A 1a, A 2, A 2a, A 3 and A 4 are each independently H, -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 8 cycloalkyl C 3 -C 8 cycloalkenyl or phenyl;
  • a 4 additionally represents hydroxyl, amino, dC 8 -alkylamino or di- (CrC 8 - alkyl) amino may be;
  • R1 is phenyl, naphthyl, a 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or aromatic heterocycle containing 1, 2, 3 or 4 heteroatoms from the group O, N and S as ring members and may contain 1 or 2 carbonyl groups as ring members;
  • 0 cycloalkyl is C 3 -C, C 3 -C 0 bicycloalkyl, C 3 -C 0 - cycloalkoxy; saturated or partially unsaturated C 3 -C 0 - heterocyclyl or C 3 -C 0 -Heterocyclyloxy, 5- or ⁇ -membered hetaryl, hetaryloxy or hetarylthio, where the five last-mentioned radicals in each case 1, 2, 3 or 4 heteroatoms from the Group O, S and N as
  • ring members and 1 or 2 carbonyl groups as ring members can contain; Aryl, aryloxy, arylthio, aryl-Ci-C ⁇ -alkoxy or arylCrC 6 -alkyl, wherein the aryl radicals each have 6, 7, 8, 9 or 10 ring members; and where the cyclic systems may be substituted by 1, 2 or 3 identical or different Ci-C 6 alkyl or Ci-C 6 -Halogenalkylreste;
  • Z is O, S, NR 33 , NOR 34 or N-NR 35 R 36 ;
  • R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 32a , R 33 , R 34 , R 35 and R 36 are each independently hydrogen, Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 - alkynyl, C 3 -C 8 cycloalkyl or C 4 -C 8 cycloalkenyl;
  • R 23a has, except for hydrogen, one of the meanings given for R 21 ;
  • R 22 , R 28 and R 32 independently of one another may additionally also denote -CO-R 25 ;
  • R 22 can furthermore be -CO-OR 21 or -CO-NR 23 R 23b , where R 23b has one of the meanings given for R 21 ;
  • R 22 and R 23 or R 22 and R 23a also together with the nitrogen atom to which they are attached, a 4-, 5-, 6- or 7-membered saturated or partially unsaturated heterocycle, which may have an oxygen atom as a ring member, and or may contain a double bond, can form NEN;
  • R 31 , R 32 , R 32a , R 33 , R 34 or R 35 with a further radical R 21 , R 22 , R 23 , R 24 , R 25 or R 31 can also together form a C 1 -C 6 -alkylene group, which in the case of C 2 -C 6 -alkylene may have a double bond;
  • R 26 and R 22 , R 26 and R 27 , R 26 and R 28 or R 29 and R 30 may also together form a C 3 -C 6 alkylene group, wherein the ring obtained therefrom may have an oxygen atom as a ring member and / or may contain a double bond;
  • R 30 may also be a radical of the formula A-CO-OR 21 or -CO-NR 23 R 23b , where A is C 1 -C 4 -alkylene;
  • N C (R 25 ) NR 22 R 23 can stand;
  • R w is halogen, cyano, C r C 8 alkyl, C 2 -C 0 alkenyl, C 2 -C 10 alkynyl, C r C 6 alkoxy, C 2 -C 0 alkenyloxy, C 2 -C 0 - Alkynyloxy, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkenyl, C 3 -C 6 cycloalkoxy, or C 3 -C 6 cycloalkenyloxy; or
  • R 2 denotes a cyclic radical selected from C 3 -C 0 cycloalkyl, phenyl, 5-, 6- or 7-membered aromatic heterocycles and C-linked, 5-, 6- or 7-membered saturated or partially unsaturated heterocycles, wherein saturated, partially unsaturated or aromatic heterocycles having 1, 2, 3 or 4 heteroatoms from the group O, N and S and containing 1 or 2 carbonyl groups as ring members, the alicyclic, heterocyclic and aromatic groups the radical definitions of R 2 may be partially or completely halogenated and / or may have 1, 2 or 3 identical or different substituents L R2 :
  • L R2 is halogen, cyano, hydroxy, cyanato (OCN), nitro, Ci-Cio-alkyl, C 2 -C 0 -
  • R 5 are independently selected from hydrogen, -C 6 - alkyl, C 2 -Cio-alkenyl, C 2 -C 10 alkynyl, C 3 -C 6 cycloalkyl and C 3 -C 6 -
  • Cycloalkenyl where the 5 last-mentioned radicals 1, 2, 3 or 4 identical or different substituents selected from cyano, dC 4 - alkoximino, C 2 -C 4 -Alkenyloximino, C 2 -C 4 -Alkinyloximino and C 1 -C 4 - Alkoxy, may have;
  • B 1 is hydrogen, hydroxy, C 1 -C 8 -alkyl, amino, C 1 -C 8 -alkylamino or di- (C 1 -C 8 -alkyl) -amino;
  • n O, 1 or 2;
  • B 2 is C 2 -C 8 alkenyl, C r C 8 alkoxy, C 2 -C 0 alkenyloxy, C 2 -C 0 alkynyloxy or one of said at B 1 radicals;
  • B 3 and B 4 are independently dC 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 6 - cycloalkyl, C r C 8 alkoxy, C 2 -C 0 alkenyloxy, C 2 -C 0 - Alkynyloxy or a radical NR 10 R 11 ;
  • R 7, R 8, R 9, R 10, R 11 are independently selected from hydrogen, Ci-C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl or C 2 -C 6 - Alkynyl, where the four last-mentioned radicals 1, 2, 3, 4, 5 or 6 may have identical or different substituents R a ; or R 8 and R 9 and / or R 10 and R 11 together with the nitrogen atom to which they are attached form a 4-, 5- or 6-membered saturated or partially unsaturated ring which is 1, 2, 3 or 4 may have identical or different substituents R b ; in which
  • R a , R b independently of one another represent halogen, hydroxy, C 1 -C 8 -alkyl or C 1 -C 8 -alkoxy; and wherein the aliphatic, alicyclic, heterocyclic and aromatic groups of the radical definitions of L R2 in turn may be partially or fully halogenated;
  • R 3 is hydrogen, halogen, cyano, C r C 8 alkyl, C 2 -C 8 alkenyl or C 2 -C 8 alkynyl, where the latter three radicals may be partially or completely halogenated and / or 1, 2 or 3 substituents selected from nitro, cyano, hydroxy, C 1 -C 2 -alkoxy, C 1 -C 4 -alkoxycarbonyl, amino, C 1 -C 4 -alkylamino and di- (C 1 -C 4 -alkyl) -amino;
  • Het is a C- or N-linked, 5- or 6-membered aromatic heterocycle having 1, 2, 3 or 4 selected from N, O and S heteroatoms as ring members and which may be partially or fully halogenated and / or 1, 2, 3 or 4 may have the same or different substituents L:
  • L is halo, cyano, hydroxy, cyanato (OCN), nitro, Ci-Cio-alkyl, C 2 -C 0 -
  • R 55, R 66, R 55a, R 66a are independently selected from hydrogen, d-Ce-alkyl, C 2 -C 0 alkenyl, C 2 -C 10 alkynyl, C 3 -C 6 cycloalkyl and C 3 C 6 -Cycloalkenyl, wherein the aliphatic groups of the radical definitions of R 55 and / or R 66 may be partially or completely halogenated and / or 1, 2, 3 or 4 Cyanosubstituenten nen can nen; and wherein the aliphatic groups of the radical definitions of
  • R 55a and / or R 66a and the alicyclic radical definitions of R 55 , R 66 , R 55a and / or R 66a may be partially or completely halogenated and / or 1, 2, 3 or 4 identical or different substituents selected from cyano, may comprise -C 4 -Alkinyloximino and dC 4 alkoxy, Ci-C 4 -Alkoximino, C 2 -C 4 alkenyl oximino, C 2;
  • C 1 is hydrogen, hydroxy, C 1 -C 8 alkyl, amino, C 1 -C 8 alkylamino or di (C 1 -C 8 alkyl) amino;
  • r is O, 1 or 2;
  • C 3 and C 4 are each independently -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 6 - cycloalkyl, C r C 8 alkoxy, C 2 -C 0 alkenyloxy, C 2 -C 0 - Alkynyloxy or a radical NR 10a R 11a ;
  • R 77, R 88, R ", R 1oa, R 11a are independently selected from hydrogen, C r C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 -alkenyl and C 2 -C 6 - Alkynyl, where the last four radicals 1, 2, 3, 4, 5 or 6 may have the same or different substituents R aa , or R 88 and R 99 and / or R 10a and R 11a together with the nitrogen atom to which they are attached form a 4-, 5- or ⁇ -membered saturated or partially unsaturated ring which may have 1, 2, 3 or 4 identical or different substituents R bb ;
  • R aa , R bb independently represent halogen, hydroxy, C 1 -C 8 -alkyl or C 1 -C 8 -alkoxy;
  • the present invention also provides the use of 5-hetarylpyrimidines and their salts for controlling phytopathogenic fungi (harmful fungi).
  • the present invention furthermore relates to a crop protection agent which is particularly suitable for controlling phytopathogenic fungi (harmful fungi) comprising at least one compound of general formula I and / or an agriculturally acceptable salt thereof and at least one liquid or solid carrier.
  • a crop protection agent which is particularly suitable for controlling phytopathogenic fungi (harmful fungi) comprising at least one compound of general formula I and / or an agriculturally acceptable salt thereof and at least one liquid or solid carrier.
  • the present invention further provides a method of controlling phytopathogenic fungi, characterized in that the fungi or the materials, plants, the soil or seeds to be protected from fungal attack an effective amount of at least one compound of general formula I and / or an agriculturally acceptable salt of I treated.
  • the present invention further provides the use of 5-hetarylpyrimidines of the general formula I and / or an agriculturally acceptable salt of I for controlling arthropod plant pests and / or for controlling nematodes.
  • the present invention further provides an agent for controlling arthropod plant pests and / or for controlling nematodes, comprising at least one compound of general formula I and / or an agriculturally acceptable salt thereof and at least one liquid or solid carrier.
  • the present invention furthermore relates to a method for controlling arthropod plant pests and / or nematodes, in which the arthropod plant pests and / or nematodes or the plants, seeds, materials or soil to be protected against infestation with these harmful organisms with an effective amount of at least a compound of formula I and / or an agriculturally acceptable salt of I treated.
  • the present invention furthermore relates to a seed containing at least one 5-hetarylpyrimidine of the formula I and / or an agriculturally acceptable salt of I.
  • the present invention furthermore relates to the use of 5-hetarylpyrimidines of the general formula I and / or a pharmaceutically acceptable salt thereof as medicaments, or for the production of a medicament which is particularly suitable for the treatment of cancerous diseases.
  • the present invention furthermore relates to pharmaceutical compositions (medicaments or medicaments) containing at least one 5-hetarylpyrimidine of the general formula I and / or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.
  • the present invention furthermore relates to the use of 5-hetarylpyrimidines of the general formula I and / or their pharmaceutically acceptable salts for the production of a medicament for the treatment of cancers.
  • the present invention further provides a method for the treatment of cancers in mammals comprising administering to the mammal in need thereof an effective amount of a 5-hetaryl pyrimidine of general formula I and / or a pharmaceutically acceptable salt thereof.
  • the compounds of the formula I can have one or more centers of chirality and are then present as enantiomer or diastereomer mixtures.
  • the invention relates to both the pure enantiomers or diastereomers and mixtures thereof, for. B. racemates.
  • Suitable compounds of general formula I also include all possible stereoisomers (cis / trans isomers) and mixtures thereof.
  • Suitable agriculturally useful or suitable salts include, in particular, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the fungicidal activity of the compounds I. So come as cations in particular the ions of the alkali metals, preferably sodium and potassium, the alkaline earth metals, preferably calcium, magnesium and barium, and the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion, the desired one to four Ci-C4 Alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri (C 1 -C 4 -alkyl) sulfonium and sulfoxonium ions, preferably tri (C
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C 1 -C 4 alkanoic acids, preferably formate, acetate , Propionate and butyrate. They may be formed by reaction of I with an acid of the corresponding anion, preferably hydrochloric, hydrobromic, sulfuric, phosphoric or nitric acid.
  • Suitable pharmaceutically acceptable or suitable salts are, in particular, physiologically tolerated salts of compound I, in particular the acid addition salts with physiologically tolerated acids.
  • suitable organic and inorganic acids are hydrochloric acid, hydrobromic acid, phosphoric acid, nitric acid, sulfuric acid, C 1 -C 4 -alkylsulfonic acids, such as methanesulfonic acid, cycloaliphatic acid.
  • sulfonic acids such as S - (+) - 10-camphorsulfonic acid, aromatic sulfonic acids such as benzenesulfonic acid, cis- and cinnamic acid, furoic acid and toluenesulfonic acid, C 2 -C 10 -hydroxycarboxylic acids such as glycolic acid, di- and tri-C 2 -C 10 -carboxylic acids and hydroxycarboxylic acids such as oxalic, malonic, maleic, fumaric, lactic, tartaric, adipic, citric, mucic and benzoic acids.
  • physiologically tolerated salts of the compounds I can be present as mono-, bis-, tris- and tetrakis salts, ie they can have 1, 2, 3 or 4 of the abovementioned acid molecules per molecule of the formula I.
  • the acid molecules may be present in protonated form or as anions.
  • Halogen fluorine, chlorine, bromine and iodine
  • Haloalkyl straight-chain or branched alkyl groups having 1 to 2, 4, 6 or 8 carbon atoms (as mentioned above), in which groups the hydrogen atoms may be partially or completely replaced by halogen atoms as mentioned above: in particular C 1 -C 2 -haloalkyl, 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-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroe
  • C2-C6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 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-1-butenyl, 3 Methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl 3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl,
  • Alkadienyl diunsaturated, straight-chain or branched hydrocarbon radicals having 4 to 10 carbon atoms and two double bonds in any position, e.g. 1,3-butadienyl, 1-methyl-1,3-butadienyl, 2-methyl-1,3-butadienyl, penta-1,3-dien-1-yl, hexa-1,4-dien-1-yl, Hexa-1, 4-dien-3-yl, hexa-1, 4-dien-6-yl, hexa-1, 5-dien-1-yl, hexa-1, 5-dien-3-yl, hexa 1, 5-dien-4-yl, hepta-1, 4-dien-1-yl, hepta-1, 4-dien-3-yl, hepta-1, 4-dien-6-yl, hepta-1, 4-dien-3-yl, hepta-1, 4-dien-6-yl, hepta-1, 4-
  • Haloalkenyl unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 10 carbon atoms and a double bond in any position (as described above) called standing), wherein in these groups, the hydrogen atoms may be partially or completely replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine;
  • Alkynyl and the alkynyl moieties in alkynyloxy straight or branched hydrocarbon groups having 2 to 4, 2 to 6, 2 to 8 or 2 to 10 carbon atoms and one or two triple bonds in any position, e.g.
  • C 2 -C 6 -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, 1-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-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl 3-pentynyl, 2-methyl-4-p
  • Cycloalkyl and the cycloalkyl moieties in cycloalkoxy monocyclic saturated hydrocarbon groups having 3 to 8 carbon ring members such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl;
  • Cycloalkenyl monocyclic monounsaturated hydrocarbon groups having 3 to 8, preferably 5 to 6 carbon ring members such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl, cyclohexen-4-yl and the like ;
  • Bicycloalkyl bicyclic hydrocarbon radical having 5 to 10 carbon atoms such as bicyclo [2.2.1] hept-1-yl, bicyclo [2.2.1] hept-2-yl, bicyclo [2.2.1] hept-7-yl, bicyclo [2.2.2] oct-1-yl, bicyclo [2.2.2] oct-2-yl, bicyclo [3.3.0] octyl, bicyclo [4.4.0] decyl and the like;
  • CrC 4 -alkoxy for an oxygen-bonded alkyl group having 1 to 4 carbon atoms: z. Methoxy, ethoxy, n -propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy;
  • Ci-Cs-alkoxy for CrC 4 -Akoxy, as mentioned above, and z. Pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy,
  • C 1 -C 4 -haloalkoxy a C 1 -C 4 -alkoxy radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, preferably by fluorine, eg OCH 2 F, OCHF 2 , OCF 3 , OCH 2 Cl, OCHCl 2 , OCCl 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2- Chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC 2 F 5 , 2-fluoropropoxy, 3-fluor
  • Ci-Cs-haloalkoxy for Ci-C4-haloalkoxy, as mentioned above, and z. 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy;
  • Alkenyloxy Alkenyl as mentioned above, which is bonded via an oxygen atom, for. C 3 -C 6 alkenyloxy such as 1-propenyloxy, 2-propenyloxy, 1-methylethenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1-methyl-1-propenyloxy, 2-methyl-1-propenyloxy, 1 Methyl 2-propenyloxy, 2-methyl-2-propenyloxy, 1-pentenyloxy, 2-pentenyloxy, 3-pentenyloxy, 4-pentenyloxy, 1-methyl-1-butenyloxy, 2-methyl-1-butenyloxy, 3-methyl 1-butenyloxy, 1-methyl-2-butenyloxy, 2-methyl-2-butenyloxy, 3-methyl-2-butenyloxy, 1-methyl-3-butenyloxy, 2-methyl-3-butenyloxy, 3-methyl-3 -butenyloxy, 1, 1-dimethyl-2-propenyloxy
  • Alkynyloxy alkynyl as mentioned above, which is bonded via an oxygen atom, for.
  • B. C3-C6 alkynyloxy such as 2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-propynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy, 1-methyl-2-butynyloxy, 1- Methyl 3-butynyloxy, 2-methyl-3-butynyloxy, 1-ethyl-2-propynyloxy, 2-hexynyloxy, 3-hexynyloxy, 4-hexynyloxy, 5-hexynyloxy, 1-methyl-2-pentynyloxy, 1-methyl 3-pentynyloxy and the like;
  • Alkylthio Alkyl as defined above attached via an S atom.
  • Alkylsulfinyl alkyl as defined above bonded through an SO group.
  • Alkylsulfonyl Alkyl as defined above attached via an S (O) 2 group.
  • heterocyclyl Five- or six-membered saturated or partially unsaturated heterocycle (hereinafter also heterocyclyl) containing one, two, three or four heteroatoms from the group oxygen, nitrogen and sulfur as ring members: z.
  • B monocyclic saturated or partially unsaturated heterocycles containing in addition
  • Carbon ring members one to three nitrogen atoms and / or an oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, for.
  • Sulfur as ring members z. B. mono- and bicyclic heterocycles having seven ring members, containing in addition to carbon ring members one to three nitrogen atoms and / or an oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, for example tetra- and Hexahydroazepinyl as 2,3,4,5 Tetrahydro [1 H] azepine-1, -2, -3, -4, 5, 6 or 7-yl,
  • Alkylene divalent linear chains of 1 to 6 CH 2 groups, e.g. CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 CH 2 and CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 ;
  • Oxyalkylene divalent unbranched chains of 2 to 4 CH 2 groups, wherein a valence is bonded to the skeleton via an oxygen atom, for. OCH 2 CH 2 , OCH 2 CH 2 CH 2 and OCH 2 CH 2 CH 2 CH 2 ;
  • Oxyalkylenoxy divalent unbranched chains of 1 to 3 CH 2 groups, wherein both valences are bonded to the skeleton via an oxygen atom, for. OCH 2 O, OCH 2 CH 2 O and OCH 2 CH 2 CH 2 O.
  • R 1 is C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 3 -C 6 -cycloalkyl, C 5 -C 6 -cycloalkenyl.
  • R 1 may be partially or fully halogenated and / or carry one, two, three or four identical or different substituents L R1 , which are as defined above.
  • L R1 is preferably selected from halo -alkenyl gen, cyano, Ci -C 6 -alkyl, C 2 -C 6 -alkyl, C 2 -C 6 -alkyl kinyl, Ci-C 6 alkoxy, -C 6 - alkoxycarbonyl, Ci-Ce-alkoximino, C2 -Alkenyloximino -C 6, C 2 -C 6 -Alkinyloximino, C3-C6 - cycloalkyl, C5-C6 cycloalkenyl, wherein the aliphatic and / or alicyclic groups of the radical definitions of L for R1 may in turn be partially or fully halogenated and / or one, two or three substituents L 11 can carry.
  • R1 L carries at least one substituent L 11, L 11 is preferably selected from halogen, cyano, C-C6 alkyl, Ci-C 6 haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -Al kinyl, Ci-C 6 alkylcarbonyl, Ci-C 6 -haloalkylcarbonyl and Ci-C 6 -alkoxy.
  • R 1 is C 1 -C 6 -alkyl, in particular branched C 3 -C 8 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -alkylene, in particular branched C 3 -C 8 -alkynyl, C 3 -C 6 - Cycloalkyl, which may have a Ci-C4-alkyl group, or Cs-CerCycloalkenyl, which may have a Ci-C4-alkyl group.
  • R 1 is branched Cs-Cs-alkyl, such as isopropyl, sec-butyl, isobutyl, tert-butyl, 2- and 3-pentyl, 2- and 3-methylbutyl, 1, 1-dimethylpropyl, 2,2- Dimethylpropyl, 2- and 3-hexyl, 2-, 3- and 4-methylpentyl and the like.
  • the branching is not on the carbon atom through which the R 1 radical is attached to the pyrimidine ring. Examples of such alkyl radicals are isobutyl, 2- and 3-methylbutyl, 2,2-dimethylpropyl, 2-, 3- and 4-methylpentyl and the like.
  • R 1 particularly preferably represents C 1 -C 6 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 3 -C 8 -cycloalkyl, which is 1, 2, 3, 4 , 5 or 6 substituents selected from halogen and C 1 -C 4 -alkyl, or C 1 -C 8 -haloalkyl. More preferably, R 1 is Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkyl kinyl, CrC 8 -
  • R 2 is a 5-, 6- or 7-membered heteroaromatic radical. Particular preference is given to compounds I in which R 2 is selected from pyrrolyl, pyrazolyl, imidazolyl, 1, 2,3-triazolyl, 1, 2,4-triazolyl, tetrazolyl, oxazolyl, isoxazolyl, 1, 3,4-oxadiazolyl, 1, 2,4-oxadiazolyl, furyl, thienyl, thiazolyl, isothiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1, 2, 3-triazinyl, 1, 2,4-triazinyl and 1, 3,5-triazinyl, wherein the heterocyclic radical R 2 may be partially or completely halogenated, may contain 1 or 2 carbonyl groups as ring members and / or 1, 2 or 3 are the same or may have different substituents L R
  • the heterocyclic radical R 2 may be partially or completely halogenated.
  • R 2 is selected from pyrazol-1-yl, 3-aminopyrazol-1-yl, [1, 2,4] triazol-1-yl, 3-cyano- [1, 2, 4] triazol-1-yl, [1, 2,3] triazol-1-yl, 1, 2,4-oxadiazol-3-yl, 5-methyl-1,2,4-oxadiazol-3-yl, pyridine -2-yl, (6-methyl) -pyridin-2-yl, pyrimidin-2-yl, pyrazine-2-yl, pyridazin-3-yl, [1, 3] thiazol-2-yl, (4,5 -Dimethyl) - [1,3] thiazol-2-yl, 7-aminoindazol-1-yl, pyrazol-3-one-1-yl, 2-hydroxyimidazol-1-yl, 3-hydroxypyrazolin-1-yl and 5 -Hydroxy-1, 2,4
  • R 2 is an aromatic five-membered heterocycle which is bonded in particular via N and / or may be substituted by one, two or three substituents L R2 , where L 2 is in particular the meanings mentioned as being preferred having.
  • R 2 is pyrazol-1-yl, [1, 2,4] triazol-1-yl or [1, 2,3] triazol-1-yl, where the abovementioned radicals are unsubstituted or may be substituted by 1, 2 or 3 substituents L R2 .
  • R 2 is one of the following radicals:
  • NR 32 OR 21 such as N (C (OO) CH 3 ) ( O-C 1 -C 4 -alkyl)
  • radicals NR 32 NR 22 R 23 are NHNHC (OO) OCH 3 , NHNHC (OO) OC 2 H 5 , NHNHC (OO) OC 3 H 7 , NHNHC (OO) OC 4 H 9 .
  • R 3 is 4 alkyl or Ci-C 4 haloalkyl stands for halogen, cyano, Ci-C.
  • R 3 is halogen, cyano or C 1 -C 2 -alkyl, such as chlorine, fluorine, bromine, cyano, methyl and ethyl, in particular methyl.
  • R 3 is halogen and especially chlorine.
  • R 3 is methyl stands.
  • R 3 is cyano.
  • substituents L on Het are halogen, cyano, nitro, NH2, Ci-C 6 -alkylamino, di-d-Ce-alkylamino, Ci -C 6 alkyl-Al, -C 6 - haloalkyl, Ci-C 6 alkoxy, NH-C (O) -Ci-C 6 -alkyl, a radical C (S) C 2 and a radical C (O) C 2 .
  • C 2 has the abovementioned meanings and is in particular C 1 -C 4 -alkoxy, NH 2 , C 1 -C 4 -alkylamino or C 1 -C 4 -alkylamino.
  • Particularly preferred substituents L are independently selected from fluorine, chlorine, bromine,
  • substituents L in the ortho position are fluorine, chlorine, bromine, -C 2 - alkyl, such as methyl or ethyl, Ci-C 2 fluoroalkyl such as trifluoromethyl and Ci-C 2 alkoxy such as methoxy.
  • compounds of formula I wherein Het has at least one ring sulfur atom are further preferred.
  • particular preference is given to those compounds of the formula I in which the ring-sulfur atom is in the ortho position to the binding site of Het at the 5-position of the pyrimidine skeleton of the formula I.
  • Het is a 5-membered heteroaromatic radical which has at least one nitrogen atom and optionally 1 or 2 further heteroatoms selected from O, S and N as ring members.
  • these are compounds of the formula I in which Het is selected from pyrrolyl, pyrazolyl, imidazolyl, 1, 2,3-triazolyl, 1, 2,4-triazolyl, oxazolyl, thiazolyl, Isoxazolyl and isothiazolyl, wherein Het is unsubstituted or carries 1, 2 or 3 identical or different substituents L.
  • Het is in particular one of the radicals Het-1 to Het-31 given below:
  • R 1 C 1 -C 4 -alkyl, in particular methyl or ethyl
  • R ⁇ is C 1 -C 4 -alkyl, in particular methyl or ethyl; # denotes the point of attachment to the 5-position of the pyrimidine ring of the formula I; and
  • L1, L2 and L3 independently of one another represent hydrogen or have one of the meanings given for L.
  • the radicals L 1 , L 2 and L 3 are independently selected from hydrogen, halogen, nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, especially C 1 -C 2 -fluoroalkyl, C 1 -C 4 -alkoxy and C 1 C 4 alkoxycarbonyl.
  • L 1 , L 2 and L 3 are independently selected from hydrogen, nitro, cyano, fluoro, chloro, bromo, methyl, ethyl, isopropyl, trifluoromethyl, fluoromethyl, methoxy and methoxycarbonyl.
  • Het-1 examples are 3,5-dimethylpyrazol-1-yl, 3,5-diisopropylpyrazol-1-yl, 3-methyl-5-isopropyl-pyrazol-1-yl, 3-isopropyl-5-methyl-pyrazole 1 -yl, 3-ethyl-5-methyl-pyrazol-1-yl, 3,4,5-trimethyl-pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-methyl-pyrazole-1 yl, 3-methyl-4-chloro-pyrazol-1-yl, 3-trifluoromethylpyrazol-1-yl, 3-trifluoromethyl-5-methoxypyrazol-1-yl, 3-trifluoromethyl-5-methyl-pyrazole 1-yl, 3-methyl-5-methoxypyrazol-1-yl, 3,5-dichloro-4-methyl-pyrazol-1-yl, 3,5-dimethyl-4-chloro-pyrazol-1-yl, 3, 5-Ditrifluoromethyl
  • Het-2 are 1, 3-dimethylpyrazol-5-yl and 1-methyl-3-trifluoromethylpyrazol-5-yl.
  • Het-3 are 1, 5-dimethylpyrazol-3-yl and 1-methyl-5-methoxypyrazol-3-yl.
  • Het-4 examples include 1, 3-dimethylpyrazol-4-yl, 1, 5-dimethylpyrazol-4-yl, 1, 3,5-trimethylpyrazol-4-yl, 1-methyl-3-trifluoromethylpyrazol-4-yl and 1-methyl-5-trifluoromethylpyrazol-4-yl.
  • Het-5 are 1-methylpyrrol-2-yl, 1, 4-dimethylpyrrol-2-yl, 1-methyl-5-chloropyrrol-2-yl and 1-methyl-3,5- dichloropyrrole-2-yl.
  • Example of Het-6 is 1, 4-dimethylpyrrol-3-yl.
  • Het-7 examples include thiazol-4-yl, 2-methylthiazol-4-yl, 2-methyl-5-bromothiazol-4-yl, 2-methyl-5-chlorothiazol-4-yl and 2,5-dichloro-thiazol-4-yl.
  • Het-8 is thiazol-2-yl.
  • Het-9 is thiazol-5-yl.
  • Het-10 examples include 3-methyl-isothiazol-4-yl and 3-methyl-5-chloro-isothiazol-4-yl.
  • Het-1 1 is isothiazol-3-yl.
  • het-12 is isothiazol-5-yl.
  • Het-13 examples include isoxazol-4-yl, 3,5-dimethylisoxazol-4-yl, 3-methylisoxazole and 3-chloro-isoxazol-4-yl.
  • Het-14 is isoxazol-3-yl.
  • Het-15 is isoxazol-5-yl.
  • Het-16 examples include oxazol-4-yl, 2-methyl-oxazol-4-yl and 2,5-dimethyloxazol-4-yl.
  • Het-17 is oxazol-2-yl.
  • het-18 is oxazol-5-yl.
  • Het-19 examples include 4,5-dichloro-imidazol-1-yl and 4,5-dimethyl-imidazol-1-yl.
  • Het-20 is 1-methyl-imidazol-4-yl.
  • Het-21 is 1-methylimidazol-2-yl.
  • Het-22 is 1-methylimidazol-5-yl.
  • Examples of het-23 include 3-chloro-1, 2,4-triazol-1-yl, 3-fluoro-1, 2,4-triazol-1-yl, 3-bromo-1, 2,4-triazole 1 -yl, 3-trifluoromethyl-1, 2,4-triazol-1-yl, 3,5-dimethyl-1,2,4-triazol-1-yl, 3,5-dichloro-1, 2,4- triazol-1-yl, 3,5-dibromo-1, 2,4-triazol-1-yl, 3,5-difluoro-1, 2,4-triazol-1-yl and 3,5-ditrifluoromethyl-1, 2,4-triazole-1-yl.
  • Het-24 examples include 4,5-dimethyl-1,2,3-triazol-1-yl, 4,5-dichloro-1,2,3-triazol-1-yl, 4,5-dibromo-1, 2,3-triazol-1-yl, 4,5-difluoro-1,2,3-triazol-1-yl, 4,5-ditrifluoromethyl- 1, 2,3-triazol-1-yl, 5-methyl-1,2,3-triazol-1-yl, 5-chloro-1,2,3-triazol-1-yl, 5-fluoro-1, 2,3-triazol-1-yl, 5-bromo-1,2,3-triazol-1-yl and 5-trifluoromethyl-1,2,3-triazol-1-yl.
  • Het-25 is 1,2,3-triazol-2-yl.
  • Het-26 is 1-methyl-1,2,4-triazol-5-yl.
  • Het-27 is 1-methyl-1,2,3-triazol-5-yl.
  • Het-28 is 2-methyl-1,2,3-triazol-4-yl.
  • Het-29 is 1-methyl-1,2,4-triazol-3-yl.
  • Het-30 is 1-methyl-1,2,3-triazol-4-yl.
  • Het-31 is 2-methyl-1,2,3-triazol-5-yl.
  • Het is thyl which is unsubstituted or has 1, 2 or 3 identical or different substituents L. Accordingly, Het is one of the following residues Het-32 or Het-33, in which # denotes the point of attachment to the 5-position of the pyrimidine skeleton of the formula I and L 1 , L 2 , and L 3 independently of one another have previously been described for the formulas Het -1 to Het-31 have indicated meanings.
  • Het-32 are 5-methylthiophene-2-yl, 4-methylthiophene-2-yl, 5-chlorothiophene-2-yl, 3-cyanothiophene-2-yl, 5-acetylthiophene-2-yl, 5-bromothiophene 2-yl, 3,5-dichlorothiophene-2-yl, and 3,4,5-trichlorothiophene-2-yl.
  • Het-33 examples are 2-methylthiophen-3-yl, 2,5-dichlorothiophen-3-yl, 2,4,5-trichloro-thiophen-3-yl and 2,5-dibromothiophene-3-yl.
  • the radicals L 1 , L 2 and L 3 are preferably selected independently of one another from the meanings given for Het-1 to Het-31 as being preferred.
  • Het is furyl which is unsubstituted or has 1, 2 or 3 identical or different substituents L. Accordingly, Het is one of the following residues Het-34 or Het-35, wherein # denotes the attachment site and L 1 , L 2 , and L 3 independently of one another have the meanings given above for the formulas Het-1 to Het-31.
  • Het-34 examples include 2-furyl, 5-methyl-furan-2-yl, 5-chlorofuran-2-yl, 4-methyl-furan-2-yl, 3-cyanofuran-2-yl, 5-acetyl-furan-2-yl, 5-Bromo-furan-2-yl, 3,5-dichloro-furan-2-yl, 3,4,5-trichlorofuran-2-yl and 5-bromofuran-2-yl.
  • Het-35 are 3-furyl, 2-methylfuran-3-yl, 2,5-dimethylfuran-3-yl and 2,5-dibromofuran-3-yl.
  • the radicals L 1 , L 2 and L 3 are preferably selected independently of one another from the meanings given for Het-1 to Het-31 as being preferred.
  • a further preferred embodiment of the invention relates to compounds of the general formula I in which Het is a 6-membered heteroaromatic radical which has at least one nitrogen atom and optionally 1 or 2 further heteroatoms selected from O, S and N as ring members.
  • Het is selected from pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl or triazinyl, in particular pyridinyl, or pyrimidinyl, where Het is unsubstituted or carries 1, 2 or 3 identical or different substituents L.
  • Het is in particular a 6-membered heteroaromatic radical which has 1, 2 or 3 nitrogen atoms as ring members and which is unsubstituted or carries 1, 2 or 3 identical or different substituents L.
  • compounds of this embodiment particularly preferred are compounds of general formula I wherein Het is pyridinyl which is unsubstituted or carries 1, 2 or 3 identical or different substituents L.
  • compounds of the formula I in which Het is pyridin-2-yl which has 1 or 2 identical or different substituents L.
  • These include such links specifically, wherein one of the substituents L is located at the 5-position of the pyridinyl ring.
  • compounds I wherein one of the substituents L is located in the 3-position of the pyridinyl ring. In this case, L has the meanings previously specified as preferred.
  • compounds of the general formula I are furthermore particularly preferred in which Het is pyrimidinyl, in particular 2- or 4-pyrimidinyl, each having 1, 2 or 3 identical or different substituents L.
  • Het is pyrimidin-2-yl or pyrimidin-4-yl which has 1 or 2 identical or different substituents L.
  • particularly preferred are those compounds wherein one of the substituents L is located in the 5-position of the pyrimidinyl ring. In this case, L has the meanings previously specified as preferred.
  • compounds of the general formula I are furthermore particularly preferred in which Het is pyrazine-2-yl which has 1, 2 or 3 identical or different substituents L.
  • L has here in particular the meanings given above as preferred.
  • Het-36 to Het-41 examples of Especially Preferred Heterocyclic Groups Het of this embodiment are the following groups Het-36 to Het-41:
  • L 1 , L 2 , L 3 and L 4 independently of one another are hydrogen or have one of the meanings given for L.
  • Het-36 are 3-fluoro-pyridin-2-yl, 3-chloro-pyridin-2-yl, 3-bromo-2-pyridin-2-yl, 3-trifluoromethyl-pyridin-2-yl, 3 Methyl-pyridin-2-yl, 3-ethyl-pyridin-2-yl, 3,5-difluoro-pyridin-2-yl, 3,5-dichloro-pyridin-2-yl, 3,5-dibromopyridine 2-yl, 3,5-dimethyl-pyridin-2-yl, 3-fluoro-5-trifluoromethyl-pyridin-2-yl, 3-chloro-5-fluoro-pyridin-2-yl, 3-chloro-5 methyl-pyridin-2-yl, 3-fluoro-5-chloro-pyridin-2-yl, 3-fluoro-5-methyl-pyridin-2-yl, 3-fluoro-5-chloro-pyridin-2-yl, 3-flu
  • Het-37 2-chloro-pyridin-3-yl, 2-bromo-pyridin-3-yl, 2-fluoropyridin-3-yl, 2-methyl-pyridin-3-yl, 2,4-dichloro pyridin-3-yl, 2,4-dibromo-pyridin-3-yl, 2,4-difluoropyridin-3-yl, 2-fluoro-4-chloropyridin-3-yl, 2-chloro-4-fluoro-pyridine 3-yl, 2-chloro-4-methyl-pyridin-3-yl, 2-methyl-4-fluoro-pyridin-3-yl, 2-methyl-4-chloro-pyridin-3-yl, 2,4- Dimethyl-pyridin-3-yl, 2,4,6-trichloropyridin-3-yl, 2,4,6-tribromopyridin-3-yl,
  • het-38 examples include 3-chloro-pyridin-4-yl, 3-bromo-pyridin-4-yl, 3-methyl-pyrid-i-4-yl, 3,5-dichloro-pyridin-4-yl, 3,5-dibromo-pyridin-4-yl and 3,5-dimethyl-pyridin-4-yl.
  • het-39 examples include 5-chloropyrimidin-4-yl, 5-fluoropyrimidin-4-yl,
  • Het-40 examples include 4-methyl-pyrimidin-5-yl, 4,6-dimethyl-pyrimidin-5-yl, 2,4,6-trimethyl-pyrimidin-5-yl and 4-trifluoromethyl-6-methyl-pyrimidine. 5-yl.
  • Het-41 examples include 4,6-dimethylpyrimidin-2-yl, 4,5,6-trimethylpyrimidin-2-yl, 4,6-ditrifluoromethyl-pyrimidin-2-yl and 4,6-dimethyl-5-chloro pyrimidin-2-yl.
  • the radicals L 1, L 2, L 3 and L 4 are independently selected from hydrogen, halogen, nitro, cyano, Ci -C4 -alkyl, Ci-C 4 haloalkyl, especially Ci-C2-fluoroalkyl, CrC 4 -alkoxy and C 1 -C 4 -alkoxycarbonyl.
  • L 1 , L 2 , L 3 and L 4 are independently selected from hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, isopropyl, trifluoromethyl, fluoromethyl, methoxy and methoxycarbonyl.
  • R 5 , R 6 , R 55 , R 66 , R 55a and R 66a independently of one another are preferably hydrogen or C 1 -C 4 -alkyl.
  • R 7 , R 77 independently of one another preferably represent hydrogen or in particular d-Ce-alkyl.
  • R 8 , R 88 , R 9 and R "independently of one another preferably represent hydrogen or C 1 -C 6 -alkyl.
  • R 10 , R 10a , R 11 and R 11a are independently of one another preferably selected from hydrogen and C 1 -C 6 -alkyl .
  • B 1 , C independently of one another are preferably hydrogen, C 1 -C 6 -alkyl or amino.
  • B 2 , C 2 independently of one another preferably represent C 1 -C 4 -alkoxy, Nhb, C 1 -C 4 -alkylamino or C 1 -C 4 -alkylamino.
  • Z is preferably O, S or NOR 34 .
  • Z ' is preferably a direct bond.
  • R 21 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 and R 36 are each independently preferably hydrogen or Ci-C 4 -AlkVl.
  • R 22 is preferably hydrogen, C 1 -C 4 -alkyl, -CO-OR 21 or -COR 25 .
  • Het, R 1 and R 3 have the meanings given above, in particular the meanings mentioned as being preferred.
  • R B is C 1 -C 4 -alkyl, in particular methyl
  • R A and R A ' are each independently d-Gt-alkyl, in particular methyl.
  • the compounds I compiled in Tables 1 to 462 below are preferred.
  • the radicals mentioned in Tables 1 to 462 for a substituent Het independently of the combination in which they are mentioned, represent a particularly preferred embodiment of the substituent in question.
  • R 3 is methyl, and R 1 for a compound corresponds in each case to one row of Table A.
  • R 3 is methyl, and R 1 for a compound corresponds in each case to one row of Table A.
  • Methyl, and R 1 for a compound corresponds in each case to one row of Table A.
  • Methyl, and R 1 for a compound corresponds in each case to one row of Table A.
  • Methyl, and R 1 for a compound corresponds in each case to one row of Table A.
  • R 3 is methyl, and R 1 for a compound corresponds in each case to one row of Table A.
  • Methyl, and R 1 for a compound corresponds in each case to one row of Table A.
  • Methyl, and R 1 for a compound corresponds in each case to one row of Table A.
  • Methyl, and R 1 for a compound corresponds in each case to one row of Table A.
  • Table 1 13 Compounds of the formulas 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.1 1, 1.12, 1.13,
  • Table 1 18 Compounds of the formulas 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13,
  • Methyl, and R 1 for a compound corresponds in each case to one row of Table A.
  • Table 129 Compounds of the formulas 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.1.1, 1.12, 1.13,
  • R 3 is methyl, and R 1 for a compound corresponds in each case to one row of Table A.
  • R 3 is methyl, and R 1 for a compound corresponds in each case to one row of Table A.
  • Table 140 Compounds of the formulas 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.1.1, 1.12, 1.13,
  • Table 145 Compounds of the formulas 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13,
  • R 3 is methyl, and R 1 for a compound corresponds in each case to one row of Table A.
  • Table 151 Compounds of the formulas 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13,
  • novel compounds of the formula I can be prepared analogously to known processes of the prior art.
  • the compounds of the formula I can be prepared by reacting appropriately substituted 5-halopyrimidines II with correspondingly substituted organometallic compounds III (see Scheme 1).
  • R 3 is in particular hydrogen, alkyl, fluorine or chlorine; Hal is halogen, preferably bromine or iodine.
  • the reaction is carried out in the presence of catalytically active amounts of a transition metal of the 8th subgroup of the periodic table, z.
  • a transition metal of the 8th subgroup of the periodic table z.
  • Suitable catalysts are, for example, palladium-phosphine complexes such as tetrakis (triphenylphosphine) palladium (0), PdCl 2 (o-tolylsP) 2, bis (triphenylphosphine) -palladium (II) chloride, the [1, 1'-bis (diphenylphosphino) ferrocene] palladium (II) chloride-dichloromethane complex, bis [1,2-bis (diphenylphosphine) ethane] palladium (0) and [1,4-bis (diphenylphosphine) butane] palladium (II) chloride, palladium on activated carbon in the presence of phosphine compounds and
  • Hetaryllithium compounds can in turn be prepared by direct metallation of CH-acidic heteroaromatic compounds with lithium bases such as lithium diisopropylamide or butyllithium, or by lithiation of haloetharyl compounds with alkyllithium such as n-butyllithium.
  • the reaction then takes place under the conditions of a Kumada coupling, as described, for. From Kumada, Tetrahedron, 1982, 38, 3347 or A.C. Frisch, N. Shaikh, A. Zapf, M. Beller, Angew. Chem., 2002, 1 14, 4218-4221 are known.
  • the reaction then takes place under the conditions of a Negishi coupling, as described, for. From A. Lützen, M. Hapke, Eur. J. Org. Chem., 2002, 2292-2297.
  • Hetarylzinc compounds can be prepared in a manner known per se from the hetaryl lithium compounds or from the hetaryl magnesium compounds by reaction with zinc salts such as zinc chloride.
  • the reaction of II with the organometallic compound III takes place in particular in the case of Suzuki coupling under basic conditions.
  • Suitable bases are alkali metal carbonates and alkali metal bicarbonates, such as sodium carbonate, potassium carbonate, cesium carbonate and sodium bicarbonate, alkaline earth metal carbonates and I.
  • C N alkaline earth metal bicarbonates such as magnesium carbonate and magnesium hydrogen carbonate, or tertiary amines such as Trietyhlamin, trimethylamine, triisopropylamine and N-ethyl-N-diisopropylamine.
  • solvents organic solvents such as ethers, z. B.
  • the abovementioned solvents can also be used in a mixture with water, eg.
  • the ratio of organic solvent to water may range from 5: 1 to 1: 5.
  • R 1 , R 2 , R 3 and Hal have the meanings given above.
  • R 3 is in particular alkyl or halogen.
  • R stands for C 1 -C 6 -alkyl, and Hal is halo, preferably bromine or iodine.
  • the sulfones of the formula IV are reacted with compounds V usually under basic conditions. For practical reasons, it is possible to use directly the alkali metal, alkaline earth metal or ammonium salt of compound V. Alternatively, the addition of base is possible. This reaction typically takes place among the Conditions of nucleophilic substitution; Usually at 0 to 200 0 C, preferably at 10 to 150 0 C. If appropriate, it may be advantageous to react in the presence of a phase transfer catalyst, for. B. 18-crown-6, perform. The reaction is usually carried out in the presence of a dipolar aprotic solvent such as N, N-dialkylated carboxylic acid amides, for. N, N-dimethylformamide, cyclic ethers, e.g.
  • a dipolar aprotic solvent such as N, N-dialkylated carboxylic acid amides, for. N, N-dimethylformamide, cyclic ethers, e.g.
  • compounds IV and V are used in approximately stoichiometric amounts.
  • a base which can be used equimolar or in excess.
  • Suitable bases are alkali metal carbonates and bicarbonates, for example sodium carbonate and sodium bicarbonate, nitrogen bases such as triethylamine, tributylamine and pyridine, alkali metal alcoholates such as sodium methoxide or potassium tert-butoxide, alkali metal amides such as sodium amide or alkali metal hydrides such as lithium hydride or sodium hydride ,
  • Suitable solvents are halogenated hydrocarbons, ethers, such as diethyl ether, diisopropyl ether, tert-butyl ether, 1,2-dimethoxyethane, dioxane, anisole and tetrahydrofuran, and also dimethyl sulfoxide, N, N-dialkylated carboxamides, such as dimethylformamide or dimethylacetamide. Particularly preferred are ethanol, dichloromethane, acetonitrile and tetrahydrofuran. It is also possible to use mixtures of the solvents mentioned.
  • R 1 , R 3 , R 22 , R 23 have the meanings given above.
  • R 3 is in particular alkyl or halogen, Hal is halogen, preferably bromine or iodine.
  • the saponification of the nitrile II (R 2 is CN) is usually carried out in inert polar solvents such as water or alcohols, preferably with inorganic bases such as alkali metal or alkaline earth metal, in particular NaOH.
  • the saponification of the nitrile II is carried out by reaction with hydrogen peroxide under alkaline conditions.
  • the reaction of the acid II (R 2 is COOH) with the amine VI is advantageously carried out under the conditions known from Chem. And Pharm. Bull. 1982, Vol. 30, N12, page 4314.
  • carboxylic acids II which tend to decarboxylate, it may be advantageous not to isolate the free acid but their alkali metal salt directly with conventional halogenating agents, for example, transfer with oxalyl chloride in the acid chloride and the latter with the amine, if necessary in the presence of an auxiliary base.
  • the substituted hydroxylamines can be used as free base or preferably in the form of their acid addition salts. From practical The reasons are in particular the halides such as chlorides or sulfates into consideration.
  • Suitable alkylating agents are, for example, C 1 -C 6 -alkyl halides, di-C 1 -C 6 -alkyl sulfates or phenolsulfonic acid C 1 -C 6 -alkyl esters, where the phenyl radical optionally carries one or two radicals selected from nitro and C 1 -C 6 -alkyl.
  • the alkylation is carried out in the presence of a base.
  • Suitable bases are, for example, alkali metal or alkaline earth metal hydroxides such as sodium hydroxide, potassium hydroxide or lithium hydroxide.
  • R 1 , R 3 , R 22 , R 23 , R 34 have the meanings given above, R 3 is in particular alkyl or halogen, and Hal is halogen, preferably bromine or iodine.
  • OR 21 can be obtained by esterification of the compounds II (R 2 is COOH) under acidic or basic conditions.
  • R 1 , R 3 , R 22 , R 23 have the meanings given above.
  • R 3 is in particular alkyl or halogen
  • Hal is halogen, preferably bromine or iodine.
  • the cyano compound II is reacted in the presence of a solvent or diluent with hydrogen sulfide gas.
  • Suitable solvents or diluents are, for example, aromatic amines such as pyridine, substituted pyridines such as collidine and lutidine, or tertiary amines such as trimethylamine, triethylamine, triisopropylamine and N-methylpiperidine.
  • the resulting aminothiocarbonyl compounds II (R 2 is C (SS) NH 2 ) can then optionally be alkylated once or twice on the amide nitrogen.
  • suitable methods of alkylation reference is made to the above.
  • compounds II in which R 2 is C (SS) NR 22 R 23 are obtainable by sulfurization from the corresponding carboxylic acid amide compounds II (compounds II in which R 2 is C (OO) NR 22 R 23 ) ,
  • suitable sulfurizing agents are organophosphorus sulfides such as Lawesson's reagent,
  • R 1 and R 3 have the meanings given above.
  • R 3 is in particular alkyl or halogen.
  • Hal is halogen, preferably bromine or iodine, and R 'is C 1 -C 6 -alkyl.
  • Suitable oxidizing agents are, for example, hydrogen peroxide, selenium dioxide [cf. WO 02/88127] or organic carboxylic acids such as 3-chloroperbenzoic acid.
  • the oxidation is preferably carried out at 10 to 50 0 C in the presence of protic or aprotic solvents [cf. B. Cor. Chem. Soc., Vol. 16, pp. 489-492 (1995); Z. Chem., Vol. 17, p. 63 (1977)].
  • R 1 and R 3 have the meanings given above.
  • R 3 is in particular alkyl or halogen, R 'is C 1 -C 6 -alkyl.
  • Hal is halogen, preferably bromine or iodine.
  • Suitable halogenating agents are preferably chlorinating agents, brominating agents and iodinating agents.
  • a suitable chlorinating agent is, for example, N-chlorosuccinimide.
  • Suitable brominating agents are bromine and N-bromosuccinimide.
  • the bromination takes place in the presence of a solvent.
  • Suitable solvents for the bromination are, for example, carboxylic acids such as acetic acid.
  • Suitable iodinating agents are hydrogen iodide, chloroiodide or N-iodosuccinimide. The iodination is usually carried out in a solvent.
  • Suitable solvents are chlorinated hydrocarbons such as dichloromethane when using hydrogen iodide, C 1 -C 4 -alcohols such as methanol or carboxylic acids such as acetic acid when using chloroiodide and halogenated carboxylic acids such as trifluoromethane. fluoroacetic acid using N-iodosuccinimide. The halogenation is usually carried out between 10 0 C and the boiling temperature of the solvent.
  • Thioether compounds VIII can be prepared starting from 4-halopyrimidine compounds
  • R 1 and R 3 have the meanings given above.
  • R 3 is in particular halogen or alkyl
  • R ' is C 1 -C 6 -alkyl
  • Hal' is halogen, in particular chlorine.
  • the reaction conditions and catalysts mentioned there can be used.
  • the preferred organometallic compounds mentioned there can be used, wherein the radical Het mentioned therein is in each case replaced by the radical R 1 .
  • 4-Halogenpyrimidines IX, in which R 3 is alkyl, are advantageously obtained by reacting 4,6-dihalopyrimidines XI with a Grignard reagent R 3 -MgCl under the conditions of a Kumada coupling, as described in Scheme 6.
  • Hal ' are independently halogen, preferably chlorine, and R' is Ci-C 6 alkyl.
  • R' is Ci-C 6 alkyl.
  • 4,6-dihalopyrimidines XI are advantageously obtained by reacting 4,6-dihydroxypyrimidines XII with halogenating agents, in particular chlorinating agents or brominating agents; as described in Scheme 7.
  • Hal 'independently represents halogen, preferably chlorine, and R' represents Ci-C ⁇ -alkyl.
  • Suitable chlorinating agents for the conversion of the dihydroxy compound XII into the compounds X1 are, in particular, POCb, PCI3 / CI2 or PCI5, or mixtures of these reagents.
  • the reaction can be carried out in excess chlorinating agent (POCb) or an inert solvent, for example carboxylic acid nitriles, eg. For example, acetonitrile or propionitrile, aromatic hydrocarbons, eg. As toluene, chlorinated hydrocarbons, eg. B. 1, 2-dichloroethane, or chlorinated aromatic hydrocarbons such as chlorobenzene be performed.
  • the reaction is generally carried out between 10 and 180 0 C.
  • the process is advantageously with the addition of N, N-dimethylformamide in catalytic amounts or subkatalytician or nitrogen bases, such as carried out for example, N, N-dimethylaniline.
  • 4,6-dihydroxypyrimidines XII can be obtained by the route outlined in Scheme 8.
  • the malonic acid ester XIII is converted with thiourea into the 2-mercaptopyrimidine compound XIIIa.
  • the subsequent alkylation with an alkylating agent gives the compound XII.
  • alkylating agents come z.
  • the reaction of the maleic esters of the formula XIII with thiourea can be carried out in the presence or absence of solvents. It is advantageous to use those solvents to which the starting materials are largely inert and in which they are completely or partially soluble.
  • the malonic acid ester XIII can also be reacted with an S-alkylisothiourea to give directly the thioether XII; see Scheme 8.
  • R * is alkyl, preferably Ci-C 6 alkyl and R 'is d-Ce-alkyl.
  • R * is alkyl, preferably C 1 -C 6 -alkyl
  • R ' is C 1 -C 6 -alkyl
  • Hal' is halogen, preferably chlorine.
  • a ⁇ -ketoester of formula XIV is converted to a 2-thioether compound XV either by reaction with an S-alkylisothiourea or by reaction with thiourea and subsequent alkylation, as described in Scheme 8. Thereafter, the thioether XV is reacted with a halogenating agent under the conditions described in Scheme 7 to give a 4-halopyrimidine of the formula IX.
  • compounds of formula I can also be obtained as described in Schemes 10 and 11.
  • R 1 Het have the meanings given above, R * is alkyl, preferably C 1 -C 6 -alkyl, R 'is C 1 -C 6 -alkyl and Hal is halogen.
  • step i) hetarylmalonates of the general formula XVI are reacted with thiourea and subsequently with an alkylating agent to give the thioether XVII, or the hetarylmalonate XVI is reacted directly with the S-alkylisothiourea to give the compound XVIII.
  • the reaction takes place as described in Scheme 8.
  • the compounds XVII thus obtained can then be converted into the dihalogen compounds XVIII in step ii) by the processes described in Scheme 7.
  • the dihalogen compounds XVIII can then be converted to the thioether compound IXX in step iii) according to the procedures described in Scheme 5.
  • the thiolate group in the 2-position of the compound IXX is oxidized to the alkylsulfonyl group in step iv) according to the method described in Scheme 3 and thus converted into a good leaving group for further exchange reactions.
  • the introduction of the radical R 2 (step v) can be carried out, for example, as described in step 2.
  • R 1 Het have the abovementioned meaning
  • R * is alkyl, preferably C 1 -C 6 -alkyl
  • R ' is C 1 -C 6 -alkyl
  • Hal' is halogen.
  • the halopyridmidine compound of the formula IXX is converted in step vi) into the corresponding alkylpyrimidine compound XXI as described in scheme 6.
  • the thiolate group in the 2-position of compound XXI is oxidized to the alkylsulfonyl group in step vii) according to the procedure described in Scheme 3 and thus converted into a good leaving group for further exchange reactions.
  • Step viii can be done, for example, as described in Step 2.
  • step v) further transformations follow, as described above, for example in schemes 2a, 2b or 2c.
  • R 3 Het are as defined above, R * is alkyl, preferably d-Ce-alkyl, R 'is C 1 -C 6 -alkyl, and R 3 is alkyl.
  • step ix the substituted ⁇ -ketoester XXIII is reacted with thiourea and then with an alkylating agent to give the thioether XXIa, or the hetaryl substituted ⁇ -ketoester is reacted directly with the S-alkylisothiourea to give the compound XXIa.
  • the reactions are carried out as described in Scheme 9.
  • the reaction according to step x) to obtain the compound XXIb and its reaction in step xi) to obtain the compound XXI is carried out in an analogous manner as in Scheme 10 for the steps ii) or iii).
  • the cation M 1 in formula XXIV has little significance; For practical reasons, ammonium, tetraalkylammonium salts such as tetramethylammonium or tetraethylammonium salts or alkali or alkaline earth metal salts are usually preferred (Scheme 13).
  • the reaction temperature is usually 0 to 120 ° C., preferably 10 to 40 ° C. [cf. J. Heterocycl. Chem., Vol. 12, pp. 861-863 (1975)].
  • Suitable solvents include ethers such as dioxane, diethyl ether, methyl tert-butyl ether and preferably tetrahydrofuran, halogenated hydrocarbons such as chloromethane or dichloroethane, aromatic hydrocarbons such as toluene, and mixtures thereof.
  • the reaction is preferably carried out in the presence of catalytic or in particular at least equimolar amounts of transition metal salts and / or compounds, in particular in the presence of Cu salts such as Cu (l) halides and especially Cu (I) iodide.
  • the reaction is carried out in an inert organic solvent, for example one of the abovementioned ethers, in particular tetrahydrofuran, an aliphatic or cycloaliphatic hydrocarbon such as hexane, cyclohexane and the like, an aromatic hydrocarbon such as toluene or in a mixture of these solvents.
  • the temperatures required for this purpose are in the range of -100 to +100 0 C and especially in the range of -80 to +40 0 C. Processes are known, for. B. from WO 03/004465.
  • reaction mixtures are worked up in the usual way, for. B. by mixing with water, separation of the phases and optionally chromatographic purification of the crude products.
  • the intermediate and end products fall z. T. in the form of colorless or pale brownish, viscous oils, which are freed or purified under reduced pressure and at moderately elevated temperature of volatile fractions. If the intermediate and end products are obtained as solids, the purification can also be carried out by recrystallization or trituration.
  • Hetarylmalonates of the formula XVI can be prepared starting from hetaryl compounds of the formula XXV by reaction with one or two equivalents of a carbonic acid ester or a chloroformate (compound XXVI) in the presence of a strong base (see Scheme 14).
  • R z is hydrogen or a C 1 -C 4 alkoxycarbonyl group.
  • Q is halogen or C 1 -C 4 -alkoxy, in particular methoxy or ethoxy. Het has the abovementioned meanings and R is C 1 -C 4 -alkyl.
  • the reaction shown in Scheme 14 is usually in the presence of strong bases.
  • R z is hydrogen, it is usual to use alkali metal amides such as sodium amide or lithium diisopropylamide, or lithium organic compounds such as phenyl lithium or butyl lithium as base. In this case, the base will be used at least equimolar, based on the compound XXV, in order to achieve complete conversion.
  • R z is an alkoxycarbonyl group, it is preferable to use an alkali metal alcoholate, e.g. As sodium or potassium, sodium or potassium butoxide, sodium or potassium as a base.
  • reaction of XXV with XXVI can be carried out in one stage or in two separate stages, in which case the intermediate XXVI is obtained, in which R z is an alkoxycarbonyl group.
  • reaction of XXV with XXVI can be carried out in analogy to the method described in J. Med. Chem. 25, 1982, p. 745.
  • malonates of the formula XVI is also advantageously achieved by reaction of corresponding bromine-hetaryl compounds Br-Het with dialkylmalonates under Cu (I) catalysis [cf. Chemistry Letters, pp. 367-370, 1981; EP-A 10 02 788].
  • substituted .beta.-keto esters of the formula XXIII is advantageously achieved, for example, by reaction of corresponding bromo-hetaryl compounds Br-Het with unsubstituted .beta.-ketoesters under Cu (I) catalysis.
  • the compounds I are suitable as fungicides. They are distinguished by outstanding activity against a broad spectrum of phytopathogenic fungi from the classes of the Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes, in particular from the class of the Oomycetes. They are partially systemically effective and can be used in crop protection as foliar, pickling and soil fungicides.
  • Alternaria species on vegetables, oilseed rape, sugar beet and fruits and rice such as: A.solani or A alternata on potatoes and tomatoes,
  • Botrytis cinerea (gray mold) on strawberries, vegetables, flowers and vines
  • Drechslera species Pyrenophora species on corn, cereals, rice and turf, such as. D.teres to barley or D. tritici-repentis to wheat, • Esca to grapevine caused by Phaeoacremonium chlamydosporium,
  • Gaeumanomyces graminis on cereals • Gibberella species on cereals and rice (eg Gibberella fujikuroi on rice),
  • Mycosphaerella species on cereals, bananas and peanuts such as: M. graminicola on wheat or M.fijiensis on bananas,
  • Puccinia species on various plants such as P. triticina, P. striformins, P. hordei or P. graminis on cereals, or P. asparagi on asparagus,
  • Peronosporomycetes such as Peronospora species, Phytophthora species, Plasmopara viticola, Pseudoperonospora species and Pythium species.
  • the compounds according to the invention can also be used in cultures that are tolerant to insects or fungi by breeding, including genetic engineering methods.
  • the compounds I are also suitable for controlling harmful fungi in the protection of materials (eg wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
  • harmful fungi Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sciophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleu- rotus spp., Poria spp., Serpula spp.
  • Tyromyces spp. Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., moreover, in the protection of the following yeasts: Candida spp. and Saccharomyces cerevisae.
  • the compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally effective amount of the active ingredients.
  • the application can be done both before and after the infection of the materials, plants or seeds by the fungi.
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90 wt .-% of active ingredient.
  • the application rates in the application in crop protection depending on the nature of the desired effect between 0.01 and 2.0 kg of active ingredient per ha.
  • active ingredient in general, amounts of active ingredient of 1 to 1000 g / 100 kg, preferably 5 to 100 g / 100 kg of seed are needed.
  • the application rate of active ingredient depends on the type of application and the desired effect.
  • Usual Wall quantities are in the material protection, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of treated material.
  • the compounds of the formula I can be present in various crystal modifications which may differ in their biological activity. They are also the subject of the present invention.
  • the compounds I can be converted into the customary formulations, for. As solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the application form depends on the respective purpose; It should in any case ensure a fine and uniform distribution of the compound according to the invention.
  • the formulations are prepared in a known manner, for. B. by stretching the drug with solvents and / or carriers, if desired, under
  • Suitable solvents / auxiliaries are essentially:
  • solvent mixtures can also be used.
  • aromatic solvents eg Solvesso products, xylene
  • paraffins eg petroleum fractions
  • alcohols eg methanol, butanol, pentanol, benzyl alcohol
  • ketones eg cyclohexanone, gamma-butyrolactone
  • Pyrrolidones NMP, NOP
  • acetates glycols
  • dimethyl fatty acid amides fatty acids and fatty acid esters.
  • solvent mixtures can also be used
  • Excipients such as ground natural minerals (eg kaolins, clays, talc, chalk) and ground synthetic minerals (eg highly disperse silicic acid, silicates); Emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin liquors and methylcellulose.
  • ground natural minerals eg kaolins, clays, talc, chalk
  • ground synthetic minerals eg highly disperse silicic acid, silicates
  • Emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin liquors and methylcellulose.
  • the surface-active substances used are alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, and condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde , Condensation products of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphen
  • emulsions, pastes or oil dispersions come mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg. As toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, eg. As dimethyl sulfoxide, N-methylpyrrolidone or water into consideration.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg. As toluene, xylene, paraffin, tetrahydrona
  • Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
  • Granules, for. B. coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers.
  • Solid carriers are z.
  • mineral earths such as silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, milled plastics, fertilizers such.
  • Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • the formulations generally contain between 0.01 and 95 wt .-%, preferably between 0.1 and 90 wt .-% of the active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • B Dispersible Concentrates (DC) 10 parts by weight of the active ingredients are dissolved with 90 parts by weight of water or a water-soluble solvent. Alternatively, wetting agents or other adjuvants are added. When diluted in water, the active ingredient dissolves. This gives a formulation with 10 wt .-% active ingredient content.
  • DC Dispersible Concentrates
  • the active compounds 25 parts by weight of the active compounds are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
  • This mixture is added by means of an emulsifying machine (eg Ultraturax) in 30 parts by weight of water and brought to a homogeneous emulsion. Dilution in water results in an emulsion.
  • the formulation has an active ingredient content of 25% by weight.
  • E Suspensions 20 parts by weight of the active compounds are comminuted with the addition of 10 parts by weight of dispersing and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to give a fine active substance suspension. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • Water-dispersible and water-soluble granules 50 parts by weight of the active compounds are finely ground with the addition of 50 parts by weight dispersing and wetting agents and by means of technical equipment (eg extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble Granules produced. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the formulation has an active ingredient content of 50% by weight.
  • WP, SP, SS, WS Water-dispersible and water-soluble powders 75 parts by weight of the active compounds are ground in a rotor-stator mill with the addition of 25 parts by weight of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active ingredient content of the formulation is 75% by weight.
  • H gel formulations (GF) H gel formulations (GF)
  • I dusts (DP, DS) 5 parts by weight of the active ingredients are finely ground and intimately mixed with 95 parts by weight of finely divided kaolin. This gives a dust with 5 wt .-% active ingredient content.
  • J Granules 0.5 parts by weight of the active ingredients are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for direct application with 0.5 wt .-% active ingredient content.
  • LS water-soluble concentrates
  • FS suspensions
  • DS dusts
  • WS water-dispersible and water-soluble powders
  • ES emulsions
  • EC emulsifiable concentrates
  • gel formulations GF
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, for. B. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, atomizing, dusting, scattering or pouring are applied.
  • the forms of application depend entirely on the intended use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
  • the substances for the preparation of emulsions, pastes or oil dispersions, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier. But it can also be made of effective substance wetting, adhesion, dispersing or emulsifying and possibly solvent or oil concentrates, which are suitable for dilution with water.
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume
  • wetting agents To the active ingredients oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides, possibly also just immediately before use (tank mix), are added. These agents can be added to the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.
  • organically modified polysiloxanes eg. B. Break Thru S 240®
  • Alcohol alkoxylates eg. As Atplus 245 ®, Atplus MBA 1303 ®, Plurafac LF 300 ® and Lutensol ON 30 ®
  • EO-PO block polymers eg. B. Pluronic RPE 2035 ® and Genapol B ®
  • Alcohol ethoxylates eg. As Lutensol XP 80 ®
  • sodium dioctylsulfosuccinate e.g. B. Leophen RA ®.
  • compositions of the invention may also be present in the application form as fungicides together with other active ingredients, the z.
  • fungicides As with herbicides, insecticides, growth regulators, fungicides or with fertilizers.
  • the compounds (I) or the agents containing them When mixing the compounds (I) or the agents containing them with one or more further active compounds, in particular fungicides, for example, in many cases, the spectrum of action can be widened or development of resistance can be prevented. In many cases, synergistic effects are obtained.
  • the present invention therefore also relates to a combination of at least one compound of the formula I used according to the invention and / or a farmer acceptable salt thereof and at least one other fungicidal, insecticidal, herbicidal and / or growth-regulating active ingredient.
  • Azoxystrobin Dimoxystrobin, Enestroburin, Fluoxastrobin, Kresoxim-methyl, Metomi- nobrobin, Picoxystrobin, Pyraclostrobin, Trifloxystrobin, Orysastrobin, (2-Chloro-5- [1- (3-methylbenzyloxyimino) -ethyl] -benzyl) -carbamic acid methyl ester, (2 Methyl chloro-5- [1- (6-methylpyridin-2-ylmethoxyimino) ethyl] benzyl) carbamic acid, 2- (ortho- (2,5-dimethylphenyloxymethylene) phenyl) -3-methoxyacrylate;
  • Carboxylic acid morpholides Dimethomorph, Flumorph; Benzoic acid amides: flumetover, fluopicolide (picobenzamide), zoxamide;
  • bitertanol bromuconazoles, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fenbuconazole, flusilazole, fluquinconazole, flutriol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazo -
  • - imidazoles cyazofamide, imazalil, pefurazoate, prochloraz, triflumizole;
  • Benzimidazoles benomyl, carbendazim, fuberidazole, thiabendazole;
  • Pyridines fluazinam, pyrifenox, 3- [5- (4-chlorophenyl) -2,3-dimethylisoxazolidin-3-yl] pyridine;
  • Pyrimidines bupirimate, cyprodinil, ferimzone, fenarimol, mepanipyrim, nuarimol, pyrimethanil;
  • Dicarboximides iprodione, procymidone, vinclozolin; Other: acibenzolar-S-methyl, anilazine, captan, captafol, dazomet, diclomethine, fenoxanil, folpet, fenpropidin, famoxadone, fenamidone, octhilinone, probenazolase, proquinazide, pyroquilon, quinoxyfen, tricyclazole, 5-chloro-7- ( 4-methylpiperidin-1-yl) -6- (2 : 4 ! 6-trifluorophenyl) - [1 ! 2 ! 4] triazolo [1 !
  • Dithiocarbamates Ferbam, Mancozeb, Maneb, Metiram, Metam, Propineb, Thiram, Zineb, Ziram; Carbamates: diethofencarb, flubenthiavalicarb, iprovalicarb, propamocarb,
  • guanidines dodine, iminoctadine, guazatine
  • Organometallic compounds fentin salts
  • Sulfur-containing heterocyclyl compounds isoprothiolanes, dithianone;
  • Organophosphorus compounds edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, pyrazophos, tolclofos-methyl, phosphorous acid and their salts;
  • Organochlorine compounds thiophanates methyl, chlorothalonil, dichlofluanid, toiylfluanid, flusulfamides, phthalides, hexachlorobenzene, pencycuron, quintozene;
  • Nitrophenyl derivatives binapacryl, dinocap, dinobuton;
  • - Inorganic active substances Bordeaux broth, copper acetate, copper hydroxide, copper oxychloride, basic copper sulphate, sulfur;
  • the present invention further relates to the compositions listed in Table B, wherein in each case one row of Table B corresponds to a fungicidal composition comprising a compound of the formula I (component 1), which is in particular one of the compounds described herein as being preferred, and the further active ingredient (component 2) indicated in the respective line.
  • component 1 in each row of table B is in each case one of the compounds of the formula I which are specifically individualized in tables 1 to 462.
  • the active compounds II mentioned above as component 2 their preparation and their action against harmful fungi are generally known (cf.: http://www.hclrss.demon.co.uk/index.html); they are commercially available.
  • the compounds named after IUPAC, their preparation and their fungicidal action are also known and described, for example, in EP-A 226 917; EP-A 10 28 125; EP-A 10 35 122; EP-A 12 01 648; WO 98/46608; WO 99/24413; WO 03/14103; WO 03/053145; WO 03/066609 and WO 04/049804, to which reference is hereby made in their entirety.
  • the compounds of the formula I according to the invention are also suitable for controlling arthropod plant pests, in particular plant-damaging insects and arachnids. Furthermore, the compounds of the formula I according to the invention are suitable for controlling nematodes.
  • phytopathogenic arthropods are insects
  • Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustraena, Scrobipalpula absolutea, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera eridania, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumato poea pityocampa, Tortrix viridana, Trichoplusia n / and Zeiraphera canadensis,
  • Thysanoptera thrips
  • Athalia rosae Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomo ⁇ um pharaonis, Solenopsis geminata and Solenopsis invicta,
  • arachnids such as Acaria (Acarina), for example the families Argagridae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus , Boophilus decoloratus, Boophilus micro- plus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp.
  • Arachnoidea such as Acaria (Acarina)
  • Amblyomma americanum Amblyomma variegatum
  • Tetranychidae spp. Such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and Oligonychus pratensis.
  • the compounds of the formula I and their salts are also involved in the control of nematodes, for example root galls nematodes, for. Meloidogyne hapla, Melondogyne incognita, Meloidogyne javanica, cyst-forming nematodes, e.g. G., Globoderra rostochiensis, heterodera avenae, heterodera glycines, heterodera schachtii, heteroderma trifolii, stem and leaf nematodes, e.g. B.
  • Belonolaimus longicaudatus Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus eligatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus and Pratylenchus goodeyi.
  • the invention also relates to a method for controlling the aforementioned animal pests, which comprises treating the animal plant pests or the plants, seeds, materials or the soil to be protected against attack by these harmful organisms with an effective amount of the compounds of formula I or their salts ,
  • the application can be carried out both before and after the infestation of the materials, plants or seeds by the harmful organisms.
  • 5-hetarylpyrimidines of the general formula I in particular the 5-hetarylpyrimidines of the formula I described as preferred in the preceding description, and their pharmaceutically suitable salts effectively inhibit the growth and / or proliferation of tumor cells, as in standard tests on tumor cell lines, such as HeLa, MCF-7 and COLO 205 can be shown.
  • pyrimidines of the invention of formula I generally show ICso values ⁇ 10 "6 mol / l (ie ⁇ 1 uM), preferably ICso-values ⁇ 10" 7 mol / l (ie ⁇ 100 nM) for Zellzyklusinhi- btechnik in HeLa cells.
  • the 5-hetarylpyrimidines of the formula I are therefore for the treatment, inhibition or control of the growth and / or proliferation of tumor cells and associated therewith Diseases suitable. Accordingly, they are useful for cancer therapy in warm-blooded vertebrates, ie mammals. ren and birds, especially in humans, but also in other mammals, in particular domestic and domestic animals such as dogs, cats, pigs, ruminants (cattle, sheep, goats, bison etc.), horses and birds such as chicken, turkey, duck, Goose, guinea fowl and the like.
  • 5-hetarylpyrimidines of the formula I are suitable for the treatment of cancer or cancerous diseases of the following organs: breast, lung , Intestine, prostate, skin (melanoma), kidney, bladder, mouth, larynx, esophagus, stomach, ovaries, pancreas, liver and brain.
  • the invention furthermore relates to the pharmaceutical use of the 5-hetarylpyrimidines of the formula I and their pharmaceutically suitable salts, in particular the use of the 5-hetarylpyrimidines of the formula I described as preferred and their pharmaceutically suitable salts, and especially their use for the production of a medicament for Treatment of cancer.
  • the present invention relates to a pharmaceutical composition containing at least one 5-hetarylpyrimidine of the formula I and / or a pharmaceutically acceptable salt thereof and optionally at least one pharmaceutically acceptable carrier.
  • a pharmaceutical composition containing at least one 5-hetarylpyrimidine of the formula I and / or a pharmaceutically acceptable salt thereof and optionally at least one pharmaceutically acceptable carrier.
  • pharmaceutical compositions which contain at least one (that is to say novel) 5-hetarylpyrimidine of the formula I according to the invention and / or a pharmaceutically suitable salt thereof.
  • those pharmaceutical compositions which contain at least one previously mentioned as preferred 5-hetaryl-pyrimidine of the formula I and / or a pharmaceutically suitable salt thereof.
  • compositions according to the invention contain, in addition to a 5-hetarylpyrimidine of the formula I and / or a pharmaceutically suitable salt thereof, optionally at least one suitable carrier.
  • suitable carriers include, for example, the solvents, carriers, excipients, excipients and the like commonly used for pharmaceutical formulations, which are exemplified below for single modes of administration.
  • the compounds of the formula I according to the invention or used according to the invention can be administered in the usual way, for.
  • oral intravenous, intramuscular or subcutaneous.
  • the active ingredient may be mixed with an inert diluent or with an edible carrier; he can be embedded in a hard or soft gelatin capsule, pressed into tablets or mixed directly with the food / feed.
  • the active ingredient may be mixed with excipients and administered in the form of indigestible tablets, buccal tablets, troches, pills, capsules, suspensions, juices, syrups and the like.
  • Such preparations should contain at least 0.1% active ingredient.
  • the composition of the preparation may of course vary. It usually contains from 2 to 60% by weight of active compound, based on the total weight of the particular preparation (dosage unit).
  • Preferred preparations of the compound I according to the invention or used according to the invention contain 10 to 1000 mg of active ingredient per oral dosage unit.
  • the tablets, troches, pills, capsules and the like may also contain the following ingredients: binders such as tragacanth, acacia, corn starch or gelatin, excipients such as dicalcium phosphate, disintegrants such as corn starch, potato starch, alginic acid and the like, lubricants such as magnesium stearate, sweeteners, such as sucrose, lactose, or saccharin, and / or flavorants such as peppermint, vanilla, and the like.
  • binders such as tragacanth, acacia, corn starch or gelatin
  • excipients such as dicalcium phosphate, disintegrants such as corn starch, potato starch, alginic acid and the like
  • lubricants such as magnesium stearate
  • sweeteners such as sucrose, lactose, or saccharin
  • flavorants such as peppermint, vanilla, and the like.
  • Capsules may also contain a liquid carrier.
  • Syrups or juices may contain, in addition to the active ingredient, also sugar (or other sweetening agents), methyl or propylparaben preservatives, a dye and / or a flavoring agent.
  • sugar or other sweetening agents
  • methyl or propylparaben preservatives e.g. a dye and / or a flavoring agent.
  • the ingredients of the active ingredient formulations in the amounts used must be pharmaceutically pure and non-toxic.
  • the active compounds may be used as controlled-release preparations, e.g. B. as sustained-release preparations formulated.
  • the active substances can also be administered parenterally or intraperitoneally. Solutions or suspensions of the active compounds or their salts can be prepared with water using suitable wetting agents such as hydroxypropylcellulose. Dispersions can also be made with glycerin, liquid polyethylene glycols, and mixtures thereof in oils. Often these preparations also contain a preservative to prevent the growth of microorganisms.
  • Preparations for injections include sterile aqueous solutions and dispersions as well as sterile powders for the preparation of sterile solutions and dispersions.
  • the preparation must be sufficiently liquid so that it is injectable. It must be stable under the conditions of manufacture and storage and be protected against microbial contamination.
  • the carrier can be a solvent or a dispersion medium, e.g. For example, water, ethanol, polyols (eg. Glycerin, propylene glycol or liquid polyethylene glycol), mixtures thereof and / or vegetable oils.

Abstract

La présente invention concerne des 5-hétarylpyrimidines et leurs sels, ainsi que l'utilisation de ces composés pour lutter contre les champignons nuisibles aux plantes, les arthropodes nuisibles aux plantes et/ou les nématodes et comme médicaments. L'invention concerne également des produits phytosanitaires et des produits pharmaceutiques contenant l'un au moins de ces composés en tant que constituant actif.
PCT/EP2008/057193 2007-07-09 2008-06-10 5-hétarylpyrimidines substituées WO2009007187A1 (fr)

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Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2412657A1 (de) * 1974-03-14 1975-09-25 Schering Ag Neue nitroimidazolderivate und verfahren zu ihrer herstellung
WO1985000604A1 (fr) * 1983-07-25 1985-02-14 Sterling Drug Inc. Pyridinyl-2-pyrimidinamines utiles comme cardiotoniques et leur preparation
DD294255A5 (de) * 1990-05-14 1991-09-26 Adw Forschungsstelle Fuer Chemische Toxikologie,De Verfahren zur herstellung tetrazolylsubstituierter pyrimidinderivate
WO2004087678A1 (fr) * 2003-04-04 2004-10-14 Basf Aktiengesellschaft Pyrimidine substituee en 2
WO2005030216A1 (fr) * 2003-09-24 2005-04-07 Wyeth Holdings Corporation 5-arylpyrimidines utilisees comme agents anticancereux
WO2005070899A1 (fr) * 2004-01-23 2005-08-04 Bayer Cropscience Ag 5-phenylpyrimidines et leur utilisation comme microbicides
EP1749827A1 (fr) * 2004-03-30 2007-02-07 Kyowa Hakko Kogyo Co., Ltd. Agent anti tumoral
WO2007070606A2 (fr) * 2005-12-14 2007-06-21 E. I. Du Pont De Nemours And Company Isoxazolines destinees au controle des invertebres nuisibles
WO2007110418A2 (fr) * 2006-03-27 2007-10-04 Basf Se 5-hetaryl-4-aminopyrimidines substituees
WO2007113322A2 (fr) * 2006-04-05 2007-10-11 Basf Se 5-hétarylpyrimidines substituées

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2412657A1 (de) * 1974-03-14 1975-09-25 Schering Ag Neue nitroimidazolderivate und verfahren zu ihrer herstellung
WO1985000604A1 (fr) * 1983-07-25 1985-02-14 Sterling Drug Inc. Pyridinyl-2-pyrimidinamines utiles comme cardiotoniques et leur preparation
DD294255A5 (de) * 1990-05-14 1991-09-26 Adw Forschungsstelle Fuer Chemische Toxikologie,De Verfahren zur herstellung tetrazolylsubstituierter pyrimidinderivate
WO2004087678A1 (fr) * 2003-04-04 2004-10-14 Basf Aktiengesellschaft Pyrimidine substituee en 2
WO2005030216A1 (fr) * 2003-09-24 2005-04-07 Wyeth Holdings Corporation 5-arylpyrimidines utilisees comme agents anticancereux
WO2005070899A1 (fr) * 2004-01-23 2005-08-04 Bayer Cropscience Ag 5-phenylpyrimidines et leur utilisation comme microbicides
EP1749827A1 (fr) * 2004-03-30 2007-02-07 Kyowa Hakko Kogyo Co., Ltd. Agent anti tumoral
WO2007070606A2 (fr) * 2005-12-14 2007-06-21 E. I. Du Pont De Nemours And Company Isoxazolines destinees au controle des invertebres nuisibles
WO2007110418A2 (fr) * 2006-03-27 2007-10-04 Basf Se 5-hetaryl-4-aminopyrimidines substituees
WO2007113322A2 (fr) * 2006-04-05 2007-10-11 Basf Se 5-hétarylpyrimidines substituées

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
EIDEN, FRITZ ET AL: "Studies on pyrone derivatives. Part 80. Pyridone, pyrazole and pyrimidine derivatives from 3,5-diacyl-4-pyrones", ARCHIV DER PHARMAZIE (WEINHEIM, GERMANY) , 312(10), 863-72 CODEN: ARPMAS; ISSN: 0365-6233, 1979, XP009105783 *
FISCHER G W: "TETRAZOLE COMPOUNDS. 8 not 1 3/4 . SYNTHESIS OF TETRAZOLYLPYRIMIDINES FROM TETRAZOLYL-SUBSTITUTED ENAMINO KETONES", JOURNAL OF HETEROCYCLIC CHEMISTRY, HETEROCORPORATION. PROVO, US, vol. 30, no. 6, 1 December 1993 (1993-12-01), pages 1517 - 1519, XP000882466, ISSN: 0022-152X *
KONDO Y ET AL: "STUDIES ON PYRIMIDINE DERIVATIVES XLI. PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF HALOPYRIMIDINESWITH ARYL- AND VINYLTRIBUTYLSTANNANES", CHEMICAL AND PHARMACEUTICAL BULLETIN, PHARMACEUTICAL SOCIETY OF JAPAN, TOKYO, vol. 37, no. 10, 1 January 1989 (1989-01-01), pages 2814 - 2816, XP002933782, ISSN: 0009-2363 *
MIKHALEVA, M. A. ET AL: "Pyrimidines. 69. Syntheses from acetylpyrimidines. Bipyrimidines and pyrimidine analogs of chalcone", KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII , (5), 678-83 CODEN: KGSSAQ; ISSN: 0453-8234, 1979, XP009105788 *
RUFER, CLEMENS ET AL: "Chemotherapeutic nitroheterocycles. XIX. Synthesis of 5-nitroimidazoles substituted at position 2 by heterocycles", JUSTUS LIEBIGS ANNALEN DER CHEMIE , (7-8), 1465-77 CODEN: JLACBF; ISSN: 0075-4617, 1975, XP009105816 *
YOUSSEF M S K: "SYNTHESIS OF 1-(2,4-DINITROPHENYL)-3-METHYL-4-(SUBSTITUTED HETEROCYCLES)-2-PYRAZOLIN-5-ONE", ZEITSCHRIFT FUER NATURFORSCHUNG. TEIL B, ANORGANISCHE CHEMIE,ORGANISCHE CHEMIE, VERLAG DER ZEITSCHRIFT FUER NATURFORSCHUNG, TUEBINGEN, DE, vol. 39B, no. 1, 1 January 1984 (1984-01-01), pages 86 - 89, XP009041665, ISSN: 0340-5087 *

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