EP2001298A2 - 5-hetaryl-4-aminopyrimidines substituees - Google Patents

5-hetaryl-4-aminopyrimidines substituees

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Publication number
EP2001298A2
EP2001298A2 EP07727361A EP07727361A EP2001298A2 EP 2001298 A2 EP2001298 A2 EP 2001298A2 EP 07727361 A EP07727361 A EP 07727361A EP 07727361 A EP07727361 A EP 07727361A EP 2001298 A2 EP2001298 A2 EP 2001298A2
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EP
European Patent Office
Prior art keywords
sub
sup
het
alkyl
compounds
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EP07727361A
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German (de)
English (en)
Inventor
Joachim Rheinheimer
Thomas Grote
Bernd Müller
Wassilios Grammenos
Sarah Ulmschneider
Jens Renner
Reinhard Stierl
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BASF SE
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BASF SE
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Priority to EP07727361A priority Critical patent/EP2001298A2/fr
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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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 the use of 5-hetaryl-4-aminopyrimidines for controlling phytopathogenic fungi, novel 5-hetaryl-4-aminopyrimidines and pesticides containing at least one such compound as an active ingredient.
  • WO 01/96314, WO 02/074753, WO 03/070721, WO 03/043993, WO 2004/103978 and WO 2005/019187 disclose 5-phenyl-4-aminopyrimidines and their use for controlling phytopathogenic fungi (phytopathogenic fungi) known.
  • the 5-phenyl-4-aminopyrimidines known from the prior art are in some cases unsatisfactory with regard to their fungicidal action or have undesired properties, such as a low compatibility with crops.
  • WO 2006/029867 describes 5-heterocyclyl-4-aminopyrimidines which have a heterocyclic radical in the 2-position of the pyrimidine ring.
  • the compounds described there are unsatisfactory in terms of their fungicidal action.
  • the present invention is therefore based on the object of providing compounds with better fungicidal activity and / or a better crop tolerance.
  • the present invention thus relates to the use of 5-hetaryl-4-aminopyrimidine compounds of the general formula I.
  • Het is a 5- or 6-membered heteroaromatic radical having 1, 2, 3 or 4 selected from nitrogen, oxygen and sulfur heteroatoms as ring members, wherein the 5- or 6-membered heteroaromatic radical 1, 2, 3 or 4 may have the same or different substituents L, wherein
  • L is selected from halogen, cyano, hydroxy, cyanato (OCN), nitro, Cr C ⁇ alkyl, C 2 -Cio-alkenyl, C 2 -C 0 alkynyl, C r C 6 haloalkyl, C 2 -C 0 - haloalkenyl, -C 6 alkoxy, C 2 -C 0 alkenyloxy, C 2 -C 0 alkynyloxy, CrC 6 - haloalkoxy, C 3 -C 6 cycloalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 6 - cycloalkoxy, d-Ce-alkoxyiminoalkyl, C 2 -C 0 -Alkenyloximinoalkyl, C 2 -C 0 -Alkenyloximinoalkyl, C 2 -C 0 -Alkenyloximinoalky
  • R 5 , R 6 are independently selected from hydrogen, CrC 6 -
  • a 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;
  • a 2 is C 2 -C 8 alkenyl, C r C 8 alkoxy, C r C 6 haloalkoxy, C 2 -C 0 -
  • Alkenyloxy, C 2 -C alkynyloxy is 0 or one of said at A 1 groups;
  • a 3 and A 4 are each independently -C 8 alkyl, C 2 -C 8 alkenyl, -C 8 - haloalkyl, C 2 -C 8 haloalkenyl, C 3 -C 6 cycloalkyl, dC 8 alkoxy, CrC 6 - haloalkoxy, C 2 -C 0 alkenyloxy, 2 -C 10 are C 0 alkynyloxy or a group NR R 11;
  • R 7 , R 8 , R 9 , R 10 and R 11 are independently selected from hydrogen, C r 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 can have one, two, three, four, five or six radicals 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 four, five or six membered saturated or partially unsaturated ring, one, two, three or four, independently under R a may carry selected substituents;
  • R a is halo, OH, C r C 8 alkyl or C r C 8 alkoxy
  • R 1 is hydrogen, C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 5 -C -cycicycloalkyl, C 2 -C 8 -alkenyl, C 4 -Cio-alkadienyl, C 3 -C 6 -cycloalkenyl, C 2 -C 8 -alkenyl, phenyl, naphthyl or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle having one, two, three or four heteroatoms from the group O, N or S as ring members;
  • R 2 has one of the meanings mentioned for R 1, and can represent one of the following radicals: NH2, Ci-C 8 alkoxy, C 3 -C 8 -CyClOaI -alkoxy, C 2 -C 8 alkenyloxy, C 2 - C 8 alkynyloxy, C 1 -C 8 -alkylamino and di-C 1 -C 8 -alkylamino;
  • radicals R 1 and R 2 other than hydrogen can be partially or completely halogenated and / or can carry one, two, three or four identical or different groups R 21 :
  • R 21 is cyano, nitro, hydroxy, carboxyl, C 1 -C 6 -alkylcarbonyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-Cr C ⁇ -alkylamino, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 2 -
  • R 21 in which the aliphatic, alicyclic, heterocyclic and aromatic groups in R 21 may themselves be partially or completely halogenated or may carry one, two or three groups R 22 :
  • R 22 cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, alkyl, haloalkyl, alkenyl, alkadienyl, alkenyloxy, alkynyloxy, alkoxy, haloalkoxy, alkylthio, alkylamino, dialkylamino, formyl, alkylcarbonyl, alkylsulfonyl, alkylsulfoxyl, Alkoxycarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, the alkyl groups in these radicals containing from 1 to 6 carbon atoms and the alkenyl, alkadienyl or alkynyl groups mentioned in these radicals from 2 to 8
  • R 1 and R 2 can also form, together with the nitrogen atom to which they are attached, a five- or six-membered saturated, partially unsaturated or aromatic heterocycle which is bonded via N and which contains one, two or three further heteroatoms from Group O, N and S may have as ring member and / or one or more substituents from the group halogen,
  • Oxo, d-Ce-alkyl, Ci-C 6 haloalkyl, C 2 -C 6 -alkenyl -alkyl, C 2 -C 6 haloalkenyl, d-C ⁇ -alkoxy, Ci-C ⁇ alkoxycarbonyl, Ci-C ⁇ -haloalkoxy, C3-C6 alkenyloxy, C3-C6-haloalkenyloxy can carry and / or wherein two substituents bonded to adjacent ring atoms for Ci-C ⁇ -alkylene, OXy-C 2 -C 4 -AI alkylene or oxy-Ci-C3-alkylenoxy can stand ;
  • Ci-C ⁇ alkyl represents halogen, cyano, hydroxy, mercapto, N3, Ci-C ⁇ alkyl, C2-C8-alkenyl, C 2 -C 8 -alkyl kinyl, Ci-C 6 haloalkyl, Ci-C 6 alkoxy, C 3 - C 8 alkenyloxy, C 3 -C 8 - alkynyloxy, Ci-C 6 haloalkoxy, Ci-C 6 alkylthio, C 3 -C 8 -alkenylthio, C 3 -C 8 alkynylthio, Ci-C ⁇ -haloalkylthio, or for a rest of the formulas
  • Z is O, S, NR 53 , NOR 54 or N-NR 55 R 56 ;
  • X is a chemical bond, oxygen, a carbonyl group, a group
  • C2 -C6- alkynyl, C 3 -C 8 cycloalkyl or C 4 -C 8 cycloalkenyl are independently hydrogen, CRC6 alkyl, C 2 -C 6 alkenyl;
  • R 43a has, except for hydrogen, one of the meanings given for R 41 ;
  • R 42 , R 48 and R 52 may additionally denote -CO-R 45 ,
  • R 42 can furthermore be -CO-OR 41 or -CO-NR 43 R 43b , where R 43b has one of the meanings given for R 41 ,
  • R 42 and R 43 can also together form a C 3 -C 6 -alkylene group which may be interrupted by an oxygen atom or may have a double bond;
  • R 49 and R 50 may also together form a C 3 -C 6 alkylene group which may be interrupted by an oxygen atom or may have a double bond;
  • R 50 may also be a radical of the formula A-CO-OR 41 or -CO-NR 43 R 43b , where A is C 1 -C 4 -alkylene;
  • R w is halogen, cyano, C r C 8 alkyl, C 2 -C 0 alkenyl, C 2 -C 0 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, C 3 -C 6 cycloalkenyloxy;
  • the present invention further provides an agent for controlling harmful fungi, comprising at least one compound of general formula I and / or an agriculturally useful salt thereof and at least one liquid or solid carrier.
  • the present invention furthermore relates to novel 5-hetaryl-4-aminopyrimidines of the general formula I in which Het, R 1 , R 2 , R 3 and R 4 have the meanings given above, where at least one of the radicals R 1 and R 2 is different from hydrogen and wherein R 3 is not hydrogen or d-Cs-alkyl, when R 4 is chlorine, NH 2 or methyl.
  • the invention also provides the salts of 5-hetaryl-4-aminopyrimidines of the general formula, in particular their agriculturally useful salts but also their pharmaceutically suitable salts.
  • the present invention furthermore relates to the use of 5-hetaryl-4-aminopyrimidines of the general formula I and / or a pharmaceutically suitable salt thereof as medicaments, in particular for the treatment of cancers.
  • the present invention furthermore relates to pharmaceutical compositions comprising at least one 5-hetaryl-4-aminopyrimidine of the general formula I and / or a pharmaceutically suitable salt thereof and a pharmaceutically acceptable carrier.
  • the present invention furthermore relates to the use of 5-hetaryl-4-aminopyrimidines of the general formula I and / or pharmaceutically suitable salts thereof for the production of a medicament for the treatment of cancers.
  • the present invention furthermore relates to a method for the treatment of cancers in mammals, comprising administering to the mammal in need thereof an effective amount of a 5-hetaryl-4-aminopyrimidine of the 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.
  • Suitable compounds of general formula I also include all possible stereoisomers (cis / trans isomers) and mixtures thereof.
  • Agriculturally useful salts are, above all, 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.
  • 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 d -C 4 -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 tris (
  • 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 suitable salts are, in particular, physiologically tolerated salts of compound I, in particular the acid addition salts with physiologically tolerated acids.
  • suitable, physiologically acceptable 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 sulfonic acids such as S - (+) - 10-camphorsulfonic acid, aromatic sulfonic acids such as benzenesulfonic acid, cis- and cinnamic acid cis- , Fluorescein 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 acid, malonic acid, maleic acid, fumaric acid,
  • 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), where in these groups partially or completely the hydrogen atoms may be 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 ethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,
  • Alkenyl and the alkenyl moieties in alkenyloxy monounsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, 2 to 6, 2 to 8 or 2 to 10 carbon atoms and a double bond in any position, e.g.
  • 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-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-ethyl-1-propen
  • 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-1-yl, hepta-1, 4-dien-3-yl,
  • 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 C 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, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3- Methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2 Dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;
  • 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, as well as e.g. 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 example 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-butenyl, 1, 1-dimethyl-2-propeny
  • Alkynyloxy alkynyl as mentioned above, which is bonded via an oxygen atom, e.g. C 3 -C 6 -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;
  • C 3 -C 6 -alkynyloxy such as 2-propynyloxy, 2-butynyloxy, 3-buty
  • 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: for example, monocyclic saturated or partially unsaturated heterocycles containing one to three nitrogen atoms in addition to carbon ring members and / or an oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, eg 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4- isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl
  • Seven-membered saturated or partially unsaturated heterocycle containing one, two, three or four heteroatoms from the group consisting of oxygen, nitrogen and sulfur as ring members e.g. mono- and bicyclic heterocycles having 7 ring members containing, in addition to carbon ring members, one to three nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, for example tetra-.
  • hexahydroazepinyl such as 2,3,4,5-tetrahydro [1 H] azepine-1, -2, -3, -A, 5, 6 or 7-yl, 3,4, 5,6-Tetrahydro [2 H] azepine-2-, -3-, -A-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro [1 H] azepine-1 -, -2-, -3-, -A-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro [1 H] azepine-1, -2-, - 3-, -A-, -5-, -6- or -7-yl, hexahydroazepine-1, -2-, -3- or -4-yl, tetra-.
  • hexahydrooxepinyl such as 2,3,4,5-tetrahydro [1 H] oxepin-2, 3, -A, 5, 6 or 7-yl, 2, 3, 4, 7 Tetrahydro [1 H] oxepin-2-, - 3-, -A-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro [1H] oxepin-2, - 3-, -A-, -5-, -6- or -7-yl, hexahydroazepine-1, -2-, -3- or -4-yl, tetra-.
  • Alkylene divalent unbranched chains of 1 to 6 Chb groups, eg 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 Chb groups, wherein a valence is bonded to the skeleton via an oxygen atom, for example 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 Chb groups, wherein both valences are bonded to the skeleton via an oxygen atom, eg OCH 2 O, OCH 2 CH 2 O and OCH 2 CH 2 CH 2 O.
  • substituents L on Het are halogen, cyano, nitro, NH2, d-Ce-alkylamino, di-Ci-C 6 -alkylamino, Ci-C 6 alkyl, Ci-C 6 haloalkyl, Ci-C 6 alkoxy, Ci-Ce-alkylamino, di-Ci-C 6 -alkylamino, NH-C (O) -Ci-C 6 -alkyl, a group C (S) A 2 and a group C (O) A 2 .
  • a 2 has the abovementioned meanings and is preferably C 1 -C 4 -alkoxy, NH 2, C 1 -C 4 -alkylamino or C 1 -C 4 -alkylamino.
  • Particularly preferred L groups are independently selected from fluorine, chlorine, bromine, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4-
  • Alkoxycarbonyl particularly preferably fluorine, chlorine, Ci-C2-alkyl such as methyl or ethyl, Ci-C2-fluoroalkyl such as trifluoromethyl, Ci-C2-alkoxy such as methoxy or C1-C2 alkoxycarbonyl such as methoxycarbonyl.
  • At least one of the heteroatoms of the heteroaromatic radical Het and / or a substituent L is arranged in the ortho position to the point of attachment of Het to the pyrimidine skeleton.
  • Preferred substituents L in the ortho position are fluorine, chlorine, bromine, C 1 -C 2 -alkyl, such as methyl or ethyl, C 1 -C 2 -fluoroalkyl, such as trifluoromethyl and C 1 -C 2 -alkoxy, such as methoxy.
  • 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 and which is unsubstituted or 1, 2 or 3 substituents L. wearing.
  • Examples thereof 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, where Het is unsubstituted is or carries 1, 2 or 3 substituents L.
  • Het stands in particular for one of the radicals Het-1 to Het-31 given below:
  • L 1 , L 2 , and L 3 independently of one another are 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 are 3,5-dimethylpyazeazol-1-yl, 3,5-diisopropylpyrazol-1-yl, 3-methyl-5-isopropyl-pyrazol-1-yl, 3-isopropyl-5-methylpyrazole 1 -yl, 3-ethyl-5-methyl-pyrazol-1-yl, 3, 4,5-methyl-pyrazole-1-yl, 3-chloro-pyrazol-1-yl, 3-methyl-pyrazole-1 yl, 3-methyl-4-chloro-pyrazole-1-yl, 3-trifluoromethyl-pyrazol-1-yl, 3-trifluoromethyl-5-methoxy-pyrazol-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-pyrazole-1-yl, 3, 5-D
  • 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-trifluoromethylpyrazole-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.
  • Het-6 are 1, 4-dimethylpyrazol-3-yl and 1-methylpyrazol-3-yl.
  • het-7 examples include thiazol-4-yl, 2-methyl-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 include isoxazol-4-yl, 3,5-dimethyl-isoxazol-4-yl, 3-methyl-isoxazol-4-yl 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, 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-tiazol-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 thienyl which is unsubstituted or has 1, 2 or 3 substituents L. Accordingly, Het is one of the following residues Het-32 or Het-33, in which # 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-32 examples include 2-thienyl, 5-methylthiophene-2-yl, 4-methylthiophene-2-yl, 5-chlorothiophene-2-yl, 3-cyanothiophene-2-yl, 5-acetylthiophene-2-yl, 5-bromothiophen-2-yl, 3,5-dichlorothiophen-2-yl, 3,4,5-trichlorothiophen-2-yl and 5-bromothiophen-2-yl.
  • Het-33 examples are 3-thienyl, 2-methylthiophen-3-yl, 2,5-dichlorothiophene-3-yl, 2,4,5-trichloro-thiophen-3-yl and 2,5-dibromothiophene-3 yl.
  • Het is furyl which is unsubstituted or has 1, 2 or 3 substituents L. Accordingly, Het is one of the following residues Het-32 or Het-33, in which # 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.
  • 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 1, 2 or 3 nitrogen atoms as ring members and which is unsubstituted or carries 1, 2 or 3 substituents L.
  • Het is preferably pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl or triazinyl, in particular pyridinyl, or pyrimidinyl, which are independently unsubstituted or carry 1, 2, 3 or 4 substituents L.
  • compounds of general formula I wherein Het is pyridinyl, optionally having 1, 2, 3 or 4 substituents L are preferred.
  • Het is 2-pyridinyl which has 1 or 2 substituents L.
  • those compounds are particularly preferred in which one of the substituents L is located in the 5-position of the pyridinyl ring.
  • most preferred are compounds I wherein one of the substituents L is located in the 3-position of the pyridinyl ring.
  • L has in particular the meanings given as preferred.
  • Also preferred among the compounds of this embodiment are compounds of general formula I wherein Het is 3-pyridinyl, optionally having 1 or 2 substituents L. Among them, preferred are those having a substituent L in the 2-position and / or a substituent L in the 4-position of the pyridine ring. Also preferred compounds of this embodiment are compounds of general formula I wherein Het is 4-pyridinyl, optionally having 1 or 2 substituents L. Among them, preferred are compounds having a substituent L in the 3-position and / or a substituent L in the 5-position of the pyridine ring.
  • a further preferred embodiment of the invention relates to compounds of the general formula I in which Het is 2-pyrazinyl which optionally has 1, 2 or 3 substituents L.
  • a further preferred embodiment of the invention relates to compounds of the general formula I in which Het is 4-pyridazinyl which optionally has 1, 2 or 3 substituents L.
  • a further preferred embodiment of the invention relates to compounds of the general formula I in which Het is 1,3,5-triazinyl which optionally has 1 or 2 substituents L.
  • heterocyclic radicals Het of this embodiment are the radicals Het-36 to Het-41 given below:
  • L 1 , L 2 , L 3 and L 4 independently of one another are hydrogen or have one of the meanings given for L.
  • the radicals L 1, L 2, L 3 and L 4 are independently selected from hydrogen, halogen, nitro, cyano, -C 4 - alkyl, C r C 4 haloalkyl, especially C r C 2 fluoroalkyl, C r C 4 alkoxy and C r 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.
  • Het-36 examples are 2-pyridyl, 3-fluoro-pyridin-2-yl, 3-chloro-pyridin-2-yl, 3-bromo-2-pyridin-2-yl, 3-trifluoromethyl-pyridine-2-yl 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- Dibromo-pyridin-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-methyl-5-fluoro-pyridine-2-
  • Het-37 examples are 3-pyridyl, 2-chloro-pyridin-3-yl, 2-bromo-pyridin-3-yl, 2-methyl-pyridin-3-yl, 2,4-dichloro-pyridine-3 yl, 2,4-dibromopyridin-3-yl, 2,4-difluoropyrid i n-3-yl, 2-fluoro-4-chloropyridin-3-yl, 2-chloro-4-fluoropyridine 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, 2,4,6-trimethyl-pyridin-3-yl and 2,4 dichloro-6-methyl-pyridin-3-
  • Het-38 examples include 4-pyridyl, 3-chloro-pyridin-4-yl, 3-bromo-pyridin-4-yl, 3-methyl-pyridin-4-yl, 3,5-dichloro-pyridine-4 yl, 3,5-dibromo-pyridin-4-yl and 3,5-dimethyl-pyridin-4-yl.
  • Het-39 examples include 5-chloropyimidin-4-yl, 5-fluoropyrimidin-4-yl, 5-fluoro-6-chloropyrimidin-4-yl, 2-methyl-6-trifluoromethyl-pyrimidin-4-yl, 2, 5-Dimethyl-6-trifluoromethyl-pyrimidin-4-yl, 5-methyl-6-trifluoromethyl-pyrimidin-4-yl, 6-trifluoromethyl-pyrimidin-4-yl, 2-methyl-5-fluoro-pyrimidine-4 yl, 2-methyl-5-chloro-pyrimidin-4-yl, 5-chloro-6-methyl-pyrimidin-4-yl, 5-chloro-6-ethyl-pyrimidin-4-yl, 6-chloro-6-yl isopropyl pyrimidine ⁇ -yl, 5-bromo-6-methyl-pyrimidin-4-yl, 5-fluoro-6-methyl-pyrimidin-4-yl, 5-fluoro-6-fluoromethyl-
  • 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,
  • Vorzusgnite at least one of the two radicals R 1 or R 2 is different from hydrogen.
  • R 1 is in particular C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 3 -C 8 -cycloalkyl, which is 1, 2, 3 or 4 may be substituted by halogen or Ci-C4-alkyl, or Ci-C 8 -haloalkyl.
  • a particularly preferred embodiment relates to compounds of the general formula I in which R 1 is a group B:
  • Z 1 is hydrogen, fluorine or C 1 -C 4 -fluoroalkyl
  • R 12 is hydrogen or methyl.
  • radicals B are 2,2,2-trifluoroethyl, 1-methyl-2,2,2-trifluoroethyl, 2,2,3,3,3-pentafluoropropyl, 3,3,4,4,4-pentafluorobutyl, 2,2,3,3,3-pentafluoro-1-methylpropyl, and 2,3,3-trifluoro-2-propenyl.
  • a further preferred embodiment relates to compounds of the formula I in which R 1 represents branched C 3 -C 5 -alkyl, such as 1-methylpropyl, 1-methylbutyl, 2-methylpropyl, 1, 2-dimethylpropyl or 1,2,2-trimethylpropyl or C 3 -C 3 -alkyl.
  • Cs alkenyl such as 2-propenyl, 2-methyl-2-propenyl.
  • a further preferred embodiment relates to compounds of the formula I in which R 1 is C 3 -C 6 -cycloalkyl which may be substituted by C 1 -C 4 -alkyl.
  • R 2 is in particular hydrogen or C 1 -C 4 -alkyl, especially methyl or ethyl.
  • R 1 and R 2 together with the nitrogen atom to which they are bonded represent a saturated or monounsaturated, in particular 5 or 6-membered, nitrogen-bonded heterocyclic radical (heterocyclyl ) as defined above.
  • heterocyclyl nitrogen-bonded heterocyclic radical
  • R 1 and R 2 together with the nitrogen atom to which they are attached form an optionally substituted piperidinyl, morpholinyl or thiomorpholinyl ring, especially a piperidinyl ring.
  • heterocyclyl is unsubstituted or substituted by 1, 2 or 3 of the abovementioned substituents, with preferred substituents on heterocyclyl being selected from halogen, C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl.
  • substituents on heterocyclyl being selected from halogen, C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl.
  • R 1 and R 2 together with the nitrogen atom to which they are attached are a 4-methylpiperidine ring, a 4-trifluoromethylpiperidine ring, a morpholine ring or a 3,4-dimethylpiperidine ring and especially a 4-methylpiperidine ring or form a 3,4-dimethylpiperidine ring.
  • R 1 and R 2 together with the nitrogen atom to which they are bonded represent a 5- or 6-membered, nitrogen-bonded heteroaromatic radical (heteroaryl) as above defined, which may be unsubstituted or substituted, preferably by 1, 2 or 3 of the aforementioned substituents.
  • heteroaryl nitrogen-bonded heteroaromatic radical
  • the group NR 1 R 2 forms an N-linked pyrazole ring, optionally substituted in the manner previously described, and especially by 1 or 2 of the following Radicals: halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, in particular by 2 methyl groups or 2 trifluoromethyl groups in the 3,5-position.
  • R 1 is selected from: CH (CHa) -CH 2 CH 3 , CH (CH 3 ) -CH (CH 3 ) 2, CH (CH 3 ) -C (CH 3 3 ,
  • R 3 is different from hydrogen. Furthermore, preference is given to those compounds of the formula I in which R 3 is halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 2 -haloalkoxy. In particular, preference is given to compounds of the general formula I in which R 3 is halogen, C 1 -C 2 -alkyl, cyano or C 1 -C 2 -alkoxy, such as chlorine, fluorine, bromine, methyl, cyano, methoxy or ethoxy. In particular, compounds I are preferred in which R 3 is halogen and especially chlorine. Also preferred are compounds I in which R 3 is methoxy. Also preferred are compounds I in which R 3 is methyl. Also preferred are compounds I in which R 3 is cyano.
  • R 4 is chlorine, OH, NH 2 or methyl, in particular halogen, OH, NR 42 R 43a or Ci-Cs-alkyl, different.
  • R 4 is selected from CN
  • R 4 is one of the following radicals:
  • R 4 is one of the following radicals:
  • NR 52 OR 41 such as N (C (OO) CH 3 ) (O-C 1 -C 4 -alkyl),
  • radicals NR 52 NR 42 R 43 are NHNHC (OO) OCH 3 , NHNHC (OO) OC 2 H 5 ,
  • R 5 and R 6 are independently of one another preferably hydrogen or C 1 -C 4 -alkyl.
  • R 7 is preferably hydrogen or in particular C 1 -C 6 -alkyl.
  • R 8 and R 9 independently of one another preferably represent hydrogen or C 1 -C 6 -alkyl.
  • R 10 and R 11 are preferably independently selected from hydrogen or C 1 -C 6 -alkyl.
  • a 1 is preferably hydrogen, C 1 -C 6 -alkyl or amino.
  • the index n is preferably 0, 1 or 2.
  • a 2 is preferably C 1 -C 4 -alkoxy, NH 2 , C 1 -C 4 -alkylamino or C 1 -C 4 -alkylamino.
  • Z is preferably O, S or NOR 54 .
  • X is preferably a direct bond.
  • R 42 is preferably hydrogen, C 1 -C 4 -alkyl, -CO-OR 41 or -COR 45 .
  • R 1 , R 2 , R 3 and Het have the abovementioned meanings, in particular the meanings mentioned as being preferred.
  • R is C 1 -C 4 -alkyl, in particular methyl
  • Table 1 Compounds of the formulas 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10 and 1.11, in which Het 3-methyl- 5-isopropylpyrazol-1-yl and the combination of R 3 , R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • Table 2 Compounds of the formulas 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10 and 1.11, in which Het. Dimethylpyrazol-1-yl and the combination of R 3 , R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • Table 3 Compounds of the formulas 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10 and 1.11, in which Het 3-isopropyl- 5-methylpyrazol-1-yl and the combination of R 3 , R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • Table 4 Compounds of formulas 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10 and 1.11, in which Het 3-ethyl 5-methylpyrazol-1-yl and the combination of R 3 , R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • Table 5 Compounds of the formulas 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10 and 1.11, in which Neth Het 3-methyl-5-methoxypyrazol-1-yl and the combination of R 3 , R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • Table 7 Compounds of the formulas 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10 and 1.11, in which Het. Dimethyl-4-chloropyrazol-1-yl and the combination of R 3 , R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • Table 8 Compounds of formulas 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10 and 1.11, in which Het 3-chloropyrazole 1-yl and the combination of R 3 , R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • Table 9 Compounds of the formulas 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10 and 1.11, in which Het 3,4- Dichloro-5-trichloromethylpyrazol-1-yl and the combination of R 3 , R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • Het 3-methylpyrazol-1-yl and the combination of R 3 , R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • Table 1 Compounds of the formulas 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10 and 1.11, in which Het 3.5 Dichloro-4-methylpyrazol-1-yl and the combination of R 3 , R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • Table 12 Compounds of formulas 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10 and 1.11, in which Het 3-methyl- 4-chloropyrazol-1-yl and the combination of R 3 , R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • Table 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 and 1.11, in which Het 1, 3 Dimethylpyrazol-5-yl and the combination of R 3 , R 1 and R 2 for a connection corresponds in each case to one row of Table A.
  • R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • R 2 for a compound corresponds in each case to one row of Table A.
  • Table 101
  • 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 4-amino-5-halopyrimidines II with correspondingly substituted organometallic compounds III (see Scheme 1).
  • R 3 is in particular hydrogen, alkyl, alkoxy, 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 subgroup VIII of the Periodic Table (Group 10 according to IU-PAC), for.
  • a transition metal of subgroup VIII of the Periodic Table Group 10 according to IU-PAC
  • nickel palladium or platinum, especially in the presence of a palladium catalyst.
  • Suitable catalysts are for example palladium-phosphine complexes such as tetrakis (triphenylphosphine) palladium (0), PdCl2 (o-tolyl3P) 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 charcoal in the presence of phosphine compounds and palladium (II) compounds such as palladium (II) chloride or bis (acetonitrile) palladium (II) chloride, in the presence of phosphine compounds such as triphenylphosphine, 1,1 '
  • Hetaryllithium compounds can in turn be prepared by direct metallation of CH-acidic heteroaromatics with lithium bases such as lithium diisopropylamide or butyllithium, or by lithiation of halo-hetaryl compounds with alkyllithiums such as n-butyllithium.
  • the reaction then takes place under the conditions of a Stille coupling, as described, for example, by D. Milstein, JK Stille, J. Am. Chem. Soc. 1978, 100, pp. 3636-3638 or V. Farina, V. Krishnamurthy, WJ Scott, Org. React. 1997, 50, 1-652 are known.
  • Hetarylstannanes IM can be prepared in analogy to known processes by reacting hetaryllithium compounds with RaSnCl.
  • the reaction then takes place under the conditions of a Kumada coupling, as described, for. From Kumada, Tetrahedron, 1982, 38, 3347 or AC Frisch, N. Shaikh, A. Zapf, M. Beller, Angew. Chem., 2002, 1 14, 4218-4221 are known.
  • 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.
  • Suitable bases are alkali metal carbonates and alkali metal bicarbonates, such as sodium carbonate, potassium carbo- nant, cesium carbonate, sodium bicarbonate, alkaline earth metal carbonates and alkaline earth metal hydrogencarbonates, such as magnesium carbonate or magnesium hydrogencarbonate or tertiary amines, such as triethylamine, trimethylamine, triisopropylamine or N-ethyl-N-diisopropylamine.
  • the coupling of the compound II with the compound III takes place in a solvent.
  • solvents are organic solvents such as ethers, z. B. 1, 2-dimethoxyethane, cyclic ethers such as tetrahydrofuran or 1, 4-dioxane, polyalkylene glycols such as diethylene glycol, carbonitriles such as acetonitrile, propionitrile, Carbon Text- suitable as dimethylformamide or dimethylacetamide.
  • the aforementioned solvents can also be used in admixture with water, for.
  • the ratio of organic solvent to water may range from 5: 1 to 1: 5.
  • Scheme 2 :
  • R 1 , R 2 , R 3 and R 4 have the meanings given above.
  • R 3 is in particular alkyl or halogen.
  • R ' is Ci-C ⁇ -alkyl, and Hal is halogen, preferably bromine or iodine.
  • N, N-dimethylformamide, cyclic ethers e.g. As tetrahydrofuran or carbonitriles such as acetonitrile [cp. DE-A 39 01 084; Chimia, Vol. 50, pp. 525-530 (1996); Khim. Geterotsikl. Soedin, Vol. 12, pp. 1696-1697 (1998)].
  • compounds IV and V are used in approximately stoichiometric amounts.
  • Suitable bases are alkali metal carbonates and bicarbonates, for example sodium carbonate and sodium hydrogencarbonate, 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 , in question.
  • bases are alkali metal carbonates and bicarbonates, for example sodium carbonate and sodium hydrogencarbonate, 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 , in question.
  • 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 2 , R 3 , R 42 , R 43 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 is carried out by reaction with hydrogen peroxide under alkaline conditions.
  • 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 2 , R 3 , R 42 , R 43 , R 54 have the meanings given above, R 3 is in particular alkyl or halogen and Hal is halogen, preferably bromine or iodine.
  • R 1 , R 2 , R 3 , R 42 , R 43 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 used 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.
  • suitable methods of alkylation reference is made to the above.
  • suitable sulfurizing agents are organ- nophosphorus sulfides such as Lawesson's reagent, (2,2-bis- (4-methoxyphenyl) -1, 3,2,4-dithiodiphosphetane-2,4-disulfide, organotin sulfides such as bis (tricyclohexyltin) sulfide or phosphorus pentasulfide (see also J. Org. March, Advanced Organic Chemistry, 4th Ed., Wiley Interscience 1992, p.893f and the literature cited therein).
  • R 1 , R 2 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 from 10 to 50 ° 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 3 , R 1 and R 2 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.
  • the 4-aminopyridines VIII can be converted into the 4-amino-5-halopyrimidines VII by customary methods.
  • 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, chlorine iodide 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 trifluoroacetic acid when using N-iodosuccinimide.
  • the halogenation is usually carried out between 10 ° C and the boiling point of the solvent.
  • 4-aminopyrimidine compounds VIII can be prepared starting from 4-halopyrimidine compounds IX by reaction with a primary or secondary amine (compound X) (see Scheme 5).
  • R 3 , R 1 and R 2 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 is advantageously carried out at 0 to 70 ° C, preferably 10 to 35 ° C.
  • the reaction is usually carried out in an inert solvent, such as ethers, for.
  • ethers such as dioxane, tetrahydrofuran or diethyl ether, halogenated hydrocarbons such as dichloromethane, aromatic hydrocarbons, eg. As toluene, or carboxylic esters such as ethyl acetate.
  • ethers such as ethers, for.
  • halogenated hydrocarbons such as dichloromethane
  • aromatic hydrocarbons eg. As toluene
  • carboxylic esters such as ethyl acetate.
  • a base such as tertiary amines, for example triethylamine or inorganic bases such as alkali metal or alkaline earth metal carbonates, alkali metal or Erdalkalimetallhydrogencarbonate; also excess amine X can serve as base.
  • a base such as tertiary amines, for example triethylamine or inorganic bases such as alkali metal or alkaline earth metal carbonates, alkali metal or Erdalkalimetallhydrogencarbonate; also excess amine X can serve as base.
  • 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, see Scheme 6.
  • Hal ' are independently halogen, preferably chlorine.
  • 4,6-dihalopyrimidines XI are advantageously obtained by reacting 4,6-dihydroxypyrimidines XII with halogenating agents, in particular chlorinating agents or brominating agents; see Scheme 7.
  • Hal ' is halogen, preferably chlorine.
  • 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 of chlorinating agent (POCb) or an inert solvent such as carbonitriles, eg acetonitrile or propionitrile, aromatic hydrocarbons, e.g. As toluene, chlorinated hydrocarbons, eg. B. 1, 2- Dichloroethane or chlorinated aromatic hydrocarbons such as chlorobenzene.
  • the reaction usually takes place between 10 and 180 ° C.
  • the process is advantageously carried out with the addition of N, N-dimethylformamide in catalytic or sub-catalytic amounts or nitrogen bases, such as N, N-dimethylaniline.
  • 4,6-Dihydroxypyrimidines XII can be obtained, for example, by first converting malonic acid esters XIV with thiourea into the 2-mercaptopyrimidine compound XIIIa. The subsequent alkylation with an alkylating agent gives the compound XII.
  • alkylating agents come z.
  • the dihydroxypyrimidine compound XII can also be reacted directly with an S-alkylisothiourea to give directly the thioether XII; see Scheme 8.
  • Scheme 8 is R * is alkyl, preferably Ci-C ⁇ -alkyl and R 'is Ci-C ⁇ -alkyl.
  • R * is alkyl, preferably d-C ⁇ -alkyl
  • R ' is Ci-C ⁇ -alkyl
  • Hal' is halogen, preferably chlorine
  • the cation M 1 in formula XVI has little significance; For practical reasons, ammonium, tetraalkylammonium salts such as tetramethylammonium or tetraethylammonium salts or alkali metal or alkaline earth metal salts are usually preferred (Scheme 10).
  • the reaction temperature is 0 to 120 ° C, preferably at 10 to 40 0 C [cp. 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 dichloromethane or dichloroethane, aromatic hydrocarbons, such as toluene, and mixtures thereof.
  • R 3 is C 1 -C 5 -alkyl, C 1 -C 5 -haloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -haloalkenyl, C 2 -C 5 -alkynyl or C 2 -C 8 -haloalkynyl
  • R 3 is halogen, in particular chlorine
  • organometallic compounds X a -Mt wherein X a is C 1 -C 8 -alkyl, C 1 -C 12 -haloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl or C 2 -C 8 haloalkynyl and Mt is lithium, magnesium or zinc become.
  • the reaction preferably takes place 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 (I) 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 are in the range of -100 to +100 ° C and especially in the range of -80 ° C to +40 ° C. Procedures for this are known, for. B. from WO 03/004465
  • Step i) is carried out as described in Scheme 6.
  • Step ii) is carried out as described in Scheme 5.
  • Step iii) is carried out as described in Scheme 4.
  • Step iv) is carried out as described in Scheme 3.
  • Step v) is carried out as described in Scheme 2.
  • Step vi) is carried out as described in Scheme 2b.
  • Step vii) is carried out as described in Scheme 1.
  • the reaction mixtures are worked up in the usual way, e.g. by mixing with water, separation of the phases and optionally chromatographic purification of the crude products.
  • the intermediate and end products are 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 from volatile constituents. If the intermediate and end products are obtained as solids, the purification can also be carried out by recrystallization or trituration.
  • the compounds of the formula 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.
  • Botryosphaeria species Cylindrocarpon species, Eutypa lata, Neonectria liriodendri and Stereum hirsutum, which attack, among other things, the wood or the roots of grapevines.
  • Ascochyta species on cereals and vegetables e.g. Ascochyta tritici (leaf drought) on wheat, bipolar and Drechslera species on maize, cereals, rice and turf (e.g., D. maydis on corn, D. teres on barley, D. tritei-repentis on wheat),
  • Blumeria graminis (powdery mildew) on cereals (e.g., wheat or barley), Botrytis cinerea (gray horse) on strawberries, vegetables, flowers, wheat and vines, Bremia lactucae on lettuce, Cercospora species on corn, soybean, rice and sugar beet and e.g. Cercospora sojina (leaf spot) or Cercospora kikuchii (leaf spot) on soybeans ,
  • Colletotricum species on soybeans, cotton and other plants eg C. acutatum on various plants and eg Colletotrichum truncatum (Antracnose) on soybeans), Corynespora cassiicola (leaf spots) on soybeans, - Dematophora necatrix (root / stem rot) on soybeans, Diaporthe phaseolorum (Stalk disease) on soybeans, Drechslera species, Pyrenophora species on maize, cereals, rice and turf, barley (eg D. teres) and wheat (eg D. tritici-repentis), Esca on grapevine caused by Phaeoacremonium chlamydosporium, Ph Aleophilum, and Formitipora punctata (syn. Phellinus tenutatus),
  • F. graminearum or F. culmorum (root rot) on cereals e.g., wheat or
  • Gibberella species on cereals and rice e.g., Gibberella fujikuroi on rice
  • Michrodochium nivale on cereals for example wheat or barley
  • Microsphaera diffusa (powdery mildew) on soybeans, - Mycosphaerella species on cereals, bananas and peanuts (M. graminicola)
  • Peronospora species on cabbage e.g., P. brassicae
  • bulbous plants e.g., P. destructor
  • Peronospora manshurica downy mildew
  • Phytophthora species on various plants e.g. P. capsici on paprika, Phytophthora megasperma on blended soybeans, Phytophthora indans on potatoes and tomatoes,
  • Pseudoperonospora species on hops and cucurbits e.g., P. cubenis on cucumber or P. humili on hops
  • Puccinia species on various plants e.g. P. triticina, P. striformins, P. hordei or P. graminis on cereals (for example wheat or barley) or asparagus
  • Pyricularia grisea on lawn and cereals Pythium spp. on grass, rice, maize, cotton, oilseed rape, sunflowers, sugar beet, vegetables and other plants (eg P. ultiumum or P. aphanidermatum),
  • Ramularia collo-cygni (Ramularia / sunburn complex / Physiological leaf spots) on barley
  • Rhizoctonia species e.g., R. solani
  • Rhizoctonia solani root / stem rot
  • Rhizoctonia cerealis pointed eye spot
  • Sclerotinia species on oilseed rape, sunflowers and other plants e.g. Sclerotinia sclerotiorum (stalk disease) or Sclerotinia rolfsii (stalk disease) on soybeans,
  • Septoria glycines (leaf spots) on soybeans, - Septoria tritici and Stagonospora nodorum on wheat, Erysiphe (syn. Uncinulanecator) on grapevine, Setospaeria species on corn and turf, Sphacelotheca reilinia on corn, Stagonospora nodorum (ear septoria) on wheat, - Thievaliopsis species Soybeans and cotton, Tilletia species on cereals,
  • Typhula incarnata (snow column) on wheat or barley, Ustilago species on cereals, corn and sugar beet, and Venturia species (scab) on apple and pear (e.g., V. inaequalis on apple).
  • the compounds of the formula 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.
  • materials eg wood, paper, paint dispersions, fibers or fabrics
  • harmful fungi in particular are considered:
  • Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sciarophoma 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.
  • the compounds of the formula I are used by treating the fungi or the plants, seeds, materials or soil to be protected against fungal attack with a fungicidally effective amount of the active compounds. 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 application rates are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of material treated in the material protection.
  • 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 of the formula I can be converted into the customary formulations, for.
  • 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. By stretching the active ingredient with solvents and / or excipients, if desired using emulsifiers and dispersants.
  • Suitable solvents / auxiliaries are essentially:
  • 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
  • Acetate Glycol diacetate
  • glycols dimethyl fatty acid amides, fatty acids and fatty acid esters.
  • solvent mixtures can also be used, - carriers such as ground natural minerals (eg kaolins, clays, talc, chalk) and ground synthetic minerals (eg finely divided silica, silicates); Emulsifiers such as non-ionic and anionic emulsifiers (eg polyoxyethylene)
  • ground natural minerals eg kaolins, clays, talc, chalk
  • ground synthetic minerals eg finely divided silica, silicates
  • Emulsifiers such as non-ionic and anionic emulsifiers (eg polyoxyethylene)
  • 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 naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl
  • 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, ground 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).
  • a Water-soluble concentrates (SL, LS)
  • the active compounds 20 parts by weight are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant, e.g. Polyvinylpyrrolidone dissolved. Dilution in water results in a dispersion.
  • the active ingredient content is 20% by weight
  • 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 to water by means of an emulsifying machine (e.g., Ultraturax) in 30 parts by weight and made into a homogeneous emulsion. Dilution in water results in an emulsion.
  • the formulation has an active ingredient content of 25% by weight.
  • the active ingredients 20 parts by weight of the active ingredients are comminuted with the addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine active substance suspension. In the 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 of dispersing and wetting agents and prepared by means of industrial equipment (for example extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. 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.
  • 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.
  • 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
  • GF gel formulations
  • the active compounds may be used as such, in the form of their formulations or the forms of use prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, litter, granules by spraying, misting, dusting, scattering or pouring.
  • 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 as such or dissolved in an oil or solvent, 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 eg. 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.
  • Pluro- nic RPE 2035 ® and Genapol B ® Alcohol ethoxylates, eg. As Lutensol XP 80 ®; and sodium dioctylsulfosuccinate, e. B. Leophen RA ®.
  • the agents according to the invention in the form of application as fungicides, may also be present together with other active substances, e.g. with herbicides, insecticides, growth regulators, fungicides or with fertilizers.
  • other active substances e.g. with herbicides, insecticides, growth regulators, fungicides or with fertilizers.
  • Azoxystrobin dimoxystrobin, enestroburine, fluoxastrobin, kresoxim-methyl, metominostrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, orysastrobin, (2-chloro-5- [1- (3-methyl-benzyloxyimino) -ethyl] -benzyl) -carbamic acid methyl ester, (2-Chloro-5- [1- (6-methylpyridin-2-ylmethoxyimino) ethyl] benzyl) -carbamic acid methyl ester, 2- (ortho- (2,5-dimethylphenyl-oxymethylene) -phenyl) -3- methoxy-methyl acrylate;
  • 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, tetracona - zole, triadimenol, triadimefon, triticonazole;
  • - imidazoles cyazofamide, imazalil, pefurazoate, prochloraz, triflumizole;
  • Benzimidazoles benomyl, carbendazim, fuberidazole, thiabendazole; - Other: Ethaboxam, Etridiazole, Hymexazole;
  • Pyridines fluazinam, pyrifenox, 3- [5- (4-chlorophenyl) -2,3-dimethylisoxazolidin-3-yl] pyridine; Pyrimidines: bupirimate, cyprodinil, ferimzone, fenarimol, mepanipyrim, nuarimol, pyrimethanil;
  • Morpholines aldimorph, dodemorph, fenpropimorph, tridemorph;
  • Dicarboximides iprodione, procymidone, vinclozolin;
  • acibenzolar-S-methyl anilazine, captan, captafol, dazomet, diclomethine, fenoxanil, folpet, fenpropidin, famoxadone, fenamidone, octhilinone, probenazole, proquinazide, pyroquilon, quinoxyfen, tricyclazole, 5-chloro-7- ( 4-methyl-piperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine, 2-butoxy-6- iodo-3-propyl-chromen-4-one, 3- (3-bromo-6-fluoro-2-methylindol-1-sulfonyl) - [1, 2,4] triazole-1-sulfonic acid dimethylamide;
  • 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;
  • the compounds of the formula I according to the invention and their salts, in particular their agriculturally acceptable salts, are furthermore suitable for controlling arthropodic plant pests, in particular plant-damaging insects and arachnids. Furthermore, the compounds of the formula I according to the invention and their salts, in particular their agriculturally acceptable salts, are suitable for controlling nemathodes, in particular plant-damaging nematodes.
  • phytopathogenic arthropods are insects
  • the order Lepidoptera e.g. Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidal, Diatraea grandiosella, Earias insulana, Elasmapalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea,
  • the order Diptera e.g. Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomia bezziana, Chrysomya hominivorax, Chrysomia macellaria, Contarina sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis , Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodipis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola de
  • Thysanoptera e.g. Dichromothrips spp., Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci,
  • Hymenoptera e.g. Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta,
  • Heteroptera eg Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor,
  • the order Homoptera e.g. Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis cut, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Bemisa tabaci, Bemisa argentifolii, Brachycaudus cardui , Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia
  • the order Isoptera (termites), e.g. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus and Termes natalensis, and
  • the order Orthoptera e.g. Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina , Stauronotus maroccanus and Tachycines asynamorus.
  • the compounds of the formula I and their salts are also known to combat arachnids (Arachnoidea), such as Acaria (Acarina), for example the family 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 Eriophyida spp.
  • arachnoidea such as Acaria (Acarina)
  • Tetranychus cinabarinus Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and Oligonychus pratensis.
  • the compounds of formula I and their salts are also involved in the control of nematodes, for example root-gland nematodes, e.g. Meloidogyne hapla, Melodiognomy incognita, Meloidogyne javanica, cyst-forming nematodes, e.g. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hetodera trifolii, stem and leaf nematodes, e.g.
  • root-gland nematodes e.g. Meloidogyne hapla, Melodiognomy incognita, Meloidogyne javanica, cyst-forming nematodes, e.g. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schacht
  • 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.
  • pyrimidines of the general formula I in particular the pyrimidines 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 present invention of the formula I show IC 50 values generally ⁇ 10 "/ 6 mol l (ie ⁇ 1 uM), preferably IC 50 values ⁇ 10" 7 mol / l (ie ⁇ 100 nM) for Zellzyklusinhibi für in HeLa cells.
  • the pyrimidines of the formula I are therefore suitable for the treatment, inhibition or control of the growth and / or proliferation of tumor cells and associated diseases. Accordingly, they are for cancer therapy in warm-blooded vertebrates, ie of mammals and birds, especially in men, but also in other mammals, especially in domestic and domestic animals such as dog, cat, pig, ruminant (cattle, sheep, goat, bison etc.), horse and birds such as chicken, turkey, duck, goose, guinea fowl and the like.
  • pyrimidines of the formula I in particular the pyrimidines of the formula I according to the invention which are described as preferred in the preceding description, and their pharmaceutically suitable salts are suitable for the therapy of cancer or cancerous patients.
  • suitable diseases of the following organs breast, lung, intestine, prostate, skin (melanoma), kidney, bladder, mouth, larynx, esophagus, stomach, ovaries, pancreas, liver and brain.
  • the invention further relates to the pharmaceutical use of the pyrimidine compounds of the formula I and their pharmaceutically suitable salts, in particular the use of the pyrimidines of the formula I described as preferred and their pharmaceutically suitable salts, and especially their use for the production of a medicament for the treatment of cancer.
  • the present invention relates to a pharmaceutical composition containing at least one pyrimidine compound 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 pyrimidine compound of the formula I and / or a pharmaceutically acceptable salt thereof and optionally at least one pharmaceutically acceptable carrier.
  • compositions according to the invention contain, in addition to a pyrimidine compound 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 those used according to the invention can be administered in a customary manner, e.g. As oral, intravenous, intramuscular or subcutaneous.
  • the active ingredient may be mixed with an inert diluent or with an edible carrier; it 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.
  • compositions 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: excipients 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, sweetener, such as sucrose, lactose, or saccharin, and / or flavorants such as peppermint, vanilla, and the like.
  • Capsules may also contain a liquid carrier.
  • Other substances that change the nature of the dosing unit can also be used.
  • tablets, pills and capsules may be coated with shellac, sugar or mixtures thereof.
  • 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.
  • 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. As a 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, for. Water, ethanol, polyols (e.g., glycerol, propylene glycol, or liquid polyethylene glycol), mixtures thereof, and / or vegetable oils.
  • reaction mixture was concentrated in vacuo, suspended in 100 ml of ethyl acetate, washed three times with 50 ml of saturated sodium bicarbonate solution, dried over sodium sulfate, concentrated in vacuo and purified by trituration with diisopropyl ether to give 13.4 g of the title compound.
  • the product was purified by MPLC on RP material with acetonitrile / water and then by chromatography on silica gel-60 with cyclohexane / ethyl acetate to give 30 mg of the title compound as an oil.
  • the active ingredients were formulated separately as a stock solution in dimethylsulfoxide at a concentration of 10,000 ppm.
  • the stock solution is pipetted into a microtiter plate (MTP) and diluted with an aqueous malt-based fungal nutrient medium to the stated active substance concentration. This was followed by the addition of an aqueous spore suspension of Pyricularia oryzae.
  • MTP microtiter plate
  • the plates were placed in a steam saturated chamber at temperatures of 18 ° C. With an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation. The measured parameters were compared with the growth of the drug-free control variant and the fungus- and drug-free blank to determine the relative growth in% of the pathogens in the individual drugs.
  • the sample treated with 125 ppm of the compound of Example 2 showed 10% relative growth of the pathogen.

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Abstract

La présente invention concerne l'utilisation de 5-hétaryl-4-aminopyrimidines de formule I et de leurs sels pour lutter contre les champignons attaquant les plantes. L'invention concerne également de nouvelles 5-hétaryl-4-aminopyrimidines et un agent de protection des plantes contenant au moins un tel composé en tant que composant actif. Hét représente un hétérocycle aromatique éventuellement substitué ayant 5 ou 6 éléments, comprenant 1, 2, 3 ou 4 hétéroatomes cycliques choisis parmi l'azote, l'oxygène et le soufre, le radical hétéroaromatique à 5 ou 6 éléments pouvant comporter 1, 2, 3 ou 4 substituants L identiques ou différents, R1, R2 représentent entres autres l'hydrogène, un alkyle en C1-C8, un cycloalkyle en C3-C8, un bicycloalkyle en C5-C10, un alcényle en C2-C8, un alcanediényle en C4-C10, un cycloalcényle en C3-C6, un alcynyle en C2-C8, un phényle, un naphtyle ou un hétérocycle à cinq ou six éléments aromatique, saturé ou en partie insaturé, comportant un, deux, trois ou quatre hétéroatomes cycliques choisis dans le groupe comprenant O, N et S; ou forment ensemble un cycle; R3 représente entres autres l'hydrogène, OH, un halogène, un cyano, NR31R32, un alkyle en C1-C8, un alcoxy en C1-C8, un alkylthio en C1-C8, un alkylsulfinyle en C1-C8, un alkylsulfonyle en C1-C8, un alcényle en C2-C8 ou un alcynyle en C2-C8, et R4 représente un halogène, un cyano, un hydroxy, un mercapto, N3, un alkyle en C1-C6, un alcényle en C2-C8, un alcynyle en C2-C8, un halogénoalkyle en C1-C6, un alcoxy en C1-C6, un alcényloxy en C3-C8, un alcynyloxy en C3-C8, un halogénoalcoxy en C1-C6, un alkylthio en C1-C6, un alcénylthio en C3-C8, un alcynylthio en C3-C8, un halogénoalkylthio en C1-C6 ou un radical de formule C(=Z)OR41, C(=Z)NR42R43, C(=Z)NR44-NR42R43, C(=Z)R45, CR46R47-OR48, CR46R47-NR42R43, ON(=CR49R50), O-C(=Z)R45, NR42R43a, NR51(C(=Z)R45), NR51(C(=Z)OR41), NR51(C(=Z)-NR42R43), NR52a(N=CR49R50), NR52NR42R43, NR52OR41 ou C(=N-X-R45)SR41.
EP07727361A 2006-03-27 2007-03-26 5-hetaryl-4-aminopyrimidines substituees Withdrawn EP2001298A2 (fr)

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EP07727361A EP2001298A2 (fr) 2006-03-27 2007-03-26 5-hetaryl-4-aminopyrimidines substituees
PCT/EP2007/052888 WO2007110418A2 (fr) 2006-03-27 2007-03-26 5-hetaryl-4-aminopyrimidines substituees

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TWI385169B (zh) 2005-10-31 2013-02-11 Eisai R&D Man Co Ltd 經雜環取代之吡啶衍生物及含有彼之抗真菌劑
TW200841879A (en) * 2007-04-27 2008-11-01 Eisai R&D Man Co Ltd Pyridine derivatives substituted by heterocyclic ring and phosphonoamino group, and anti-fungal agent containing same
WO2009007187A1 (fr) * 2007-07-09 2009-01-15 Basf Se 5-hétarylpyrimidines substituées
US8513287B2 (en) * 2007-12-27 2013-08-20 Eisai R&D Management Co., Ltd. Heterocyclic ring and phosphonoxymethyl group substituted pyridine derivatives and antifungal agent containing same
EP2334666A1 (fr) * 2008-09-08 2011-06-22 Merck Canada Inc. Composes heteroaromatiques utilises en tant qu'inhibiteurs de la stearoyle-coenzyme a delta-9 desaturase

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DE19827611A1 (de) * 1997-07-25 1999-01-28 Basf Ag Verwendung von Arylalkylaminoderivaten als Insektizide
PL362551A1 (en) * 2000-06-13 2004-11-02 Basf Aktiengesellschaft Fungicidal 5-phenyl substituted 2-(cyanoamino) pyrimidines
SK11422003A3 (sk) * 2001-03-15 2004-04-06 Basf Aktiengesellschaft 5-Fenylpyrimidíny, spôsoby a medziprodukty na ich prípravu a ich použitie pri ničení škodlivých húb
JP4450625B2 (ja) * 2001-11-19 2010-04-14 ビーエーエスエフ ソシエタス・ヨーロピア ５−フェニルピリミジン類、その製造方法、これらを含む組成物及びこれらの使用
EP1504001B1 (fr) * 2002-02-21 2009-04-15 Basf Se 2-(2-pyridyl)-5-phenyl-6-aminopyrimidines, procedes et produits intermediaires permettant de les produire et leur utilisation pour lutter contre des champignons nuisibles
BRPI0410482A (pt) * 2003-05-20 2006-06-13 Basf Ag composto, processo para preparar o mesmo, agente adequado para combater fungos nocivos, e, processo para combater fungos nocivos fitopatogênicos
EP1651617A1 (fr) * 2003-07-24 2006-05-03 Basf Aktiengesellschaft Pyrimidines 2-substituees
JP2007506746A (ja) * 2003-09-24 2007-03-22 ワイス・ホールディングズ・コーポレイション 抗癌剤としての５−アリールピリミジン類
JP2008513401A (ja) * 2004-09-17 2008-05-01 ビーエーエスエフ ソシエタス・ヨーロピア 植物の線虫病に対処するための２−置換ピリミジンの使用

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US20110201496A1 (en) 2011-08-18
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CN101453893A (zh) 2009-06-10
TW200806180A (en) 2008-02-01
WO2007110418A3 (fr) 2008-11-20

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