EP1720879A2 - Composes azolopyrimidine et leur utilisation pour lutter contre des champignons nuisibles - Google Patents

Composes azolopyrimidine et leur utilisation pour lutter contre des champignons nuisibles

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Publication number
EP1720879A2
EP1720879A2 EP05715521A EP05715521A EP1720879A2 EP 1720879 A2 EP1720879 A2 EP 1720879A2 EP 05715521 A EP05715521 A EP 05715521A EP 05715521 A EP05715521 A EP 05715521A EP 1720879 A2 EP1720879 A2 EP 1720879A2
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EP
European Patent Office
Prior art keywords
compounds
general formula
hydrogen
alkyl
methyl
Prior art date
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Application number
EP05715521A
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German (de)
English (en)
Inventor
Anja Schwögler
Markus Gewehr
Bernd Müller
Thomas Grote
Wassilios Grammenos
Jordi Tormo I Blasco
Joachim Rheinheimer
Carsten Blettner
Peter Schäfer
Frank Schieweck
Oliver Wagner
Reinhard Stierl
Ulrich Schöfl
Siegfried Strathmann
Maria Scherer
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BASF SE
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BASF SE
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Publication of EP1720879A2 publication Critical patent/EP1720879A2/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Definitions

  • the present invention relates to new azolopyrimidine compounds and their use for combating harmful fungi and crop protection agents which contain such compounds as an active ingredient.
  • EP-A 71792, US 5,994,360, EP-A 550113, DE-A 10223917, WO 02/48151 and WO 03/080615 describe fungicidally active pyrazolo [1, 5-a] pyrimidines and triazolo [1, 5a] pyrimidines which carry an optionally substituted phenyl group in the 6-position of the azolopyrimidine ring and NH 2 or a primary or secondary amino group in the 7-position.
  • azolopyrimidines known from the prior art are sometimes unsatisfactory in terms of their fungicidal action or have undesirable properties, such as low crop plant tolerance.
  • the present invention is therefore based on the object of providing new compounds with better fungicidal activity and / or better crop tolerance.
  • A is N or CR 6 ;
  • X, Y independently of one another represent a chemical bond or oxygen, sulfur or a group NR 7 ;
  • R 1 , R 2 independently of one another for dC 10 alkyl, C 2 -C ⁇ 0 alkenyl, C 4 -C 10 alkadienyl, C 2 -C 10 alkynyl, C 3 -C 8 cycloalkyl, C 5 -C 8 -Cycloalkenyl, C 5 -C ⁇ o-bicycloalkyl, phenyl, phenyl-C C 4 -alkyl, naphthyl, naphthyl-CrC ⁇ alkyl, 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclyl or heterocyclyl-C C 4 - alkyl, each of which may have 1, 2 or 3 heteroatoms, selected from N, O and S, as ring members, where the radicals mentioned as R 1 , R 2 may be partially or completely halogenated or 1, 2, 3 or 4 R 8 may have, wherein
  • YR 1 with XR 2 together with the carbon atom to which they are attached can form a 5-, 6 or 7-membered, saturated or unsaturated carbo- or heterocycle, the latter having 1, 2, 3 or 4 heteroatoms, selected from Can have O, S and N as a ring member, the carbocycle and the heterocycle being partially or completely halogenated or having 1, 2, 3 or 4 of the radicals R 7 and / or R 8 ; in which
  • YR 1 and XR 2 can independently of one another also represent hydrogen, CN, NO 2 or halogen and one of the radicals YR 1 and XR 2 ; can also mean OH, SH or NH 2 ;
  • R 3 is C ⁇ -C 10 alkyl, C 2 -C 10 alkenyl, C 4 -C ⁇ 0 -alkadienyl, C 2 -C 10 alkynyl, C 3 -C 8 cycloalkyl, C 5 -C 8 cycloalkenyl, C 5 -C 10 bicycloalkyl, phenyl, phenyl-C C alkyl, naphthyl, a 5- or 6-membered, saturated, partially unsaturated or aromatic heterocycle, the 1, 2 or 3 heteroatoms selected from N, O and S. , may have ring members, where the radicals mentioned as R 3 may be partially or completely halogenated or may have 1, 2, 3 or 4 radicals R 9 ;
  • R 4 halogen, cyano, CC 6 alkyl, C Ce haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 5 -C 8 cycloalkenyl, OR 10 , SR, NR "R, CH 2 NR" R "or C (W) R 13 ;
  • R 0 denotes hydrogen, CC 6 alkyl, dC 6 haloalkyl, C 2 -C 6 alkenyl or C (W) R 13 ;
  • R 1 , R 12 independently of one another are hydrogen, dC 6 -alkyl, C 2 -C 6 -alkenyl, C 4 -C 6 -alkadienyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 5 - C 8 -cycloalkenyl, where the radicals mentioned as R 11 , R 12 may be partially or completely halogenated or may have 1, 2, 3 or 4 radicals R 8 , where R 11 also represents a group C (W) R 13 can stand and where
  • R 11 , R 12 together with the nitrogen atom to which they are attached can form a 5-, 6 or 7-membered, saturated or unsaturated heterocycle, which additionally 1, 2 or 3 further heteroatoms, selected from O, S and N, can have as a ring member, the heterocycle being partially or completely halogenated and / or having 1, 2, 3 or 4 of the radicals R 8 ;
  • R 13 represents hydrogen, OH, CC 6 alkyl, CC 6 alkoxy, dC 6 haloalkyl, dC 6 haloalkoxy, C 2 -C 6 alkenyl or NR 18 R 19 ;
  • R 15 represents hydrogen, OH, CC 6 alkyl, CC 6 alkoxy, dC 6 haloalkyl, dC 6 haloalkoxy, C 2 -C 6 alkenyl or NR 18 R 19 ;
  • R 14 independently of one another, is hydrogen or CC 6 alkyl
  • R 16 , R 17 independently of one another represent hydrogen, dC 6 -alkyl, CC 6 -alkoxy, NH 2 , dC 6 -alkylamino or di-C C 6 -alkylamino;
  • R 18 , R 19 independently of one another have the meanings given for R 11 and R 12 ; and W represents oxygen or sulfur;
  • the present invention thus relates to the azolopyrimidine compounds of the general formula I and their agriculturally acceptable salts.
  • the invention also relates to their tautomers and the agriculturally acceptable salts of these tautomers.
  • V represents a chemical bond or represents oxygen, sulfur or a group NR 7 ;
  • W a is O, S or a group NR 21 ;
  • R 20 has one of the meanings given for R 1 or R 2 in formula I;
  • R 21 has one of the meanings given for R 1 or R 2 in formula I, where R 21 can also represent hydrogen;
  • R 1a corresponds to the radical R 1 minus a hydrogen atom at the binding site.
  • R 1a with XR 2 and the carbon atom to which they are attached can also form a 5-, 6 or 7-membered, unsaturated carbo- or heterocycle, the latter 1, 2, 3 or 4 Heteroatoms, selected from O, S and N as a ring member, wherein the carbo- and the heterocycle can be partially or completely halogenated or can have 1, 2, 3 or 4 of the radicals R 7 and / or R 8 as substituents.
  • the present invention furthermore relates to agents for combating harmful fungi, comprising at least one compound of the general formula I, a tautomer of I and / or an agriculturally acceptable salt thereof or of its tautomer and at least one liquid or solid carrier.
  • the compounds of the formula I and their tautomers can have one or more centers of chirality and are then present as enantiomer or diastereomer mixtures.
  • the invention relates both to the pure enantiomers or diastereomers and to their mixtures.
  • Agriculturally useful 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 or their tautomers.
  • 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, as well as the ammonium ion, if desired one to four dC -alkyl substituents and / or can carry a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri (dC 4 -alkyl) sulfonium and sulfoxonium ions, preferably tri (dC 4 -alkyl) sulfoxonium into consideration.
  • the alkali metals preferably sodium and potassium
  • the alkaline earth metals preferably calcium, magnesium and barium
  • the transition metals preferably manganese, copper, zinc
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, as well as the anions of dC 4 -alkanoic acids, preferably formate, preferably formate Propionate and butyrate. They can be formed by reacting I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • Halogen fluorine, chlorine, bromine and iodine
  • -C-C 6 alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl , 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1 , 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2.2 Trimethylpropyl, 1-ethyl-1-methyl
  • 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-trichloroethyl, pentafluoroethyl and 1, 1, 1-trifluoroprop-2-yl;
  • Alkenyl monounsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, to 6, to 8 or to 10 carbon atoms and a double bond in any position, e.g. B. C 2 -C 6 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-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-
  • Alkadienyl double-unsaturated, straight-chain or branched hydrocarbon radicals with 4 to 10 carbon atoms and two double bonds in any position, e.g. B. 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-7-yl, Hepta-1, 5-dien-1-yl, Hepta-1, 5-dien-3-yl
  • Alkynyl straight-chain or branched hydrocarbon groups with 2 to 4, 2 to 6, 2 to 8 or 2 to 10 carbon atoms and a triple bond in any position, e.g. B. 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-
  • Cycloalkyl monocyclic, saturated hydrocarbon groups with 3 to 8, preferably up to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
  • Cycloalkenyl monocyclic, monounsaturated hydrocarbon groups with 5 to 8, preferably up to 6 carbon ring members, such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl and cyclohexen-4-yl;
  • Bicycloalkyl bicyclic hydrocarbon radical with 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,
  • Alkylamino for an alkyl group bonded via an NH group such as methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino and the like;
  • Dialkylamino for a radical of the formula N (alkyl) 2 in which alkyl represents one of the abovementioned alkyl radicals which generally have 1 to 6 and in particular 1 to 4 carbon atoms, for.
  • B. for dimethylamino, diethylamino, methylethylamino, N-methyl-N-propylamino and the like.
  • d-C ⁇ -alkoxy for d-C-alkoxy, as mentioned above, and z.
  • dC 4 -haloalkoxy for a dC -alkoxy radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, preferably by fluorine, that is, for. B.
  • dC 6 -haloalkoxy for -C-C -haloalkoxy, as mentioned above, and z.
  • B 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorhexoxy;
  • Alkenyloxy Alkenyl as mentioned above, which is bonded via an oxygen atom, e.g. B. C 2 -C 6 alkenyloxy such as vinyloxy, 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-d
  • Alkynyloxy alkynyl as mentioned above, which is bonded via an oxygen atom, e.g. B. 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-pentinyloxy and the like;
  • 5- or 6-membered saturated or monounsaturated heterocyclyl containing one to two nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms as ring members, e.g. B. 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-lsolidone, 3-lsolidone, 3-lsolidine 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidiny
  • a first embodiment of the invention relates to compounds of the general formula I, in which A is N. Such connections are also referred to below as connections 1A.
  • a second embodiment of the invention relates to compounds of the general formula I in which A is CR 6 . Such connections are also referred to below as connections IB.
  • R 1 and R 2 independently of one another represent dC 10 -alkyl dC 10 -haloalkyl, C 3 -C 10 -alkenyl, C 3 -C 10 -haloalkenyl, C 3 -C 8 -cycloalkyl, C 5 -C 8 -cycloalkenyl, C 3 -C 8 cycloalkyl-dC 10 alkyl, C 3 -C 8 cycloalkyl-C 2 -C 10 alkenyl, phenyl or benzyl, the 6 last-mentioned radicals can also carry 1, 2, 3 or 4 substituents selected from halogen, dC 4 -alkyl, dC 4 -haloalkyl and dC 4 -alkoxy, or a group XR 2 or YR 1 represents hydrogen or halogen, especially chlorine and the remaining R 2 or R 1 has the meanings given here as preferred.
  • R 1 and R 2 are explained in more detail below. The information given below for R 1 also applies accordingly to R 2 .
  • R 1 is preferably CC 4 alkyl, C 2 -C 6 alkenyl or dC 8 haloalkyl. If R 1 represents an alkyl, alkenyl or alkynyl group, this can have a branch on the ⁇ -C atom. In these cases, group R 1 corresponds to group C:
  • # represents the bond to the carbon atom of the imino group or to Y and R 1x dC 3 alkyl or dC 3 haloalkyl;
  • R 1y is hydrogen, CC 3 alkyl or CC 3 haloalkyl
  • R 1 is a 5- or 6-membered saturated or aromatic heterocycle containing one or two heteroatoms from the group N, O and S, which is substituted by one or two alkyl or haloalkyl groups can be.
  • Z 1 is hydrogen, fluorine or CC 6 fluoroalkyl
  • Z 2 is hydrogen or fluorine, or Z 1 and Z 2 together form a double bond
  • q is 0 or 1
  • R 22 is hydrogen or methyl.
  • compounds I are preferred in which R 1 is C 3 -C 6 -cycloalkyl, which may be substituted by dC -alkyl.
  • this cycle is preferably selected from 5-, 6- or 7-membered saturated or monounsaturated cycles, which optionally comprise a heteroatom as a ring member.
  • R 3 represents a phenyl ring which has 1, 2, 3 or 4, in particular 1, 2 or 3 of the radicals R 9 mentioned above or represents pentafluorophenyl. At least one of the radicals R 9 is preferably arranged in the ortho position to the binding site.
  • R 3 represents a group of the formula
  • ⁇ a1 is fluorine, chlorine, methyl or CF 3 ;
  • ⁇ a2 R a for hydrogen, chlorine or fluorine;
  • R a3 represents hydrogen, CN, NO 2 , fluorine, chlorine, dC 4 -alkyl, especially methyl, dC -alkoxy, especially methoxy or a group C (W) R 13a , where W stands for oxygen or sulfur and R 13a for CC -Alkoxy, NH 2 , CC -alkylamino or di-dC 4 -alkylamino, where the group C (W) R 13a is in particular C (O) OCH 3 , CONH 2 , C (S) OCH 3 ;; R a4 for hydrogen, chlorine or fluorine;
  • R a5 represents hydrogen, fluorine, chlorine or CC 4 alkyl.
  • R 3 is an optionally substituted hydrocarbon radical having 3 to 8 carbon atoms, and in particular is an optionally substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkylmethyl, C 3 -C 8 alkyl, CC 8 haloalkyl or benzyl and for example for propyl, isopropyl, isobutyl, 1-methylbutyl, tert-butyl, n-octyl, cyclopropyl, cyclopropylmethyl, cyclopentyl, cyclohexyl, 2,2,2-trifluoroethyl , Benzyl or 2-, 3- or 4-chlorophenylmethyl.
  • R 3 represents a 5- or 6-membered heteroaromatic radical which has 1, 2 or 3 heteroatoms selected from N, O and S as ring members and which 1, 2 , 3 or 4 radicals R 9 may have.
  • heterocyclic radicals on R 3 are 1-, 2- or 3-pyrazolyl, 2- or 3-thienyl, e.g. B. 4-thiazolyl, isothiazolyl, e.g. B. 4-isothiazolyl, oxazolyl, e.g. B. 4-oxazolyl, isoxazolyl, e.g. B. 4-isoxazolyl, pyrrolyl, e.g. B. 2-pyrrolyl, imidazolyl, e.g. B. 1-imidazolyl, pyridyl, e.g. B. 2-, 3-, or 4-pyridyl, pyrazinyl, e.g. B. 2-pyrazinyl, pyridazine, e.g. B.
  • radicals R 9 are halogen, nitro, cyano, dC 4 -alkyl, dC -haloalkyl, especially dC 2 -fluoroalkyl, CC 4 -alkoxy and dC -alkoxycarbonyl.
  • Preferred heteroaromatic radicals include the radicals Het-1 to Het-21 given below:
  • R b1 , R b2 , R b3 and R 4 are independently hydrogen or have the meanings given for R 9 .
  • R, R, R and R are preferably selected independently of one another from hydrogen, halogen, nitro, cyano, dC 4 -alkyl, CC 4 -haloalkyl, especially dC 2 -fluoroalkyl, dC -alkoxy and dC -alkoxycarbonyl.
  • R b1 , R b2 , R b3 and R 4 are independently selected from hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, isopropyl, trifluoromethyl, fluoromethyl, methoxy and methoxycarbonyl.
  • Het-1 examples include 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-trifluoromethyl-pyrazol-1-yl, 3-trifluoromethyl-5-methoxy pyrazol-1-yl, 3-trifluoromethyl-5-methyl-pyrazol-1-yl, 3-methyl-5-methoxypyrazol-1-yl, 3,5-dimethyl-4-chloropyrazol-1-yl and 3, 5-ditrifluoromethyl-pyrazol-1-yl.
  • Het-2 examples include 1, 3-dimethylpyrazol-5-yl and 1-methyl-3-trifluoromethylpyrazol-1-yl.
  • Het-3 examples include 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 examples include 2-thienyl, 5-methylthiophen-2-yl, 5-chlorothiophen-2-yl, 3,5-dichlorothiophen-2-yl, 3,4,5-trichlorothiophen-2-yl and 5- bromothiophene-2-yl.
  • Het-6 examples include 3-thienyl, 2-methylthiophen-3-yl, 2,5-dichlorothiophen-3-yl, 2,4,5-trichlorothiophen-3-yl and 2,5-dibromothiophene-3 yl.
  • Het-7 examples include thiazol-4-yl, 2-methylthiazol-4-yl, 2-methyl-5-chlorothiazol-4-yl and 2,5-dichlorothiazol-4-yl.
  • Het-8 examples include 3-methyl-isothiazol-4-yl and 3-methyl-5-chloro-isothiazol-4-yl.
  • Het-9 examples include oxazol-4-yl, 2-methyl-oxazol-4-yl and 2,5-dimethyloxazol-4-yl,
  • Het-10 examples include isoxazol-4-yl, 3,5-dimethyl-isoxazol-4-yl and 3-chloro-isoxazol-4-yl,
  • Het-11 examples include 1-methyl-pyrrol-2-yl, 1,4-dimethyl-pyrrol-2-yl, 1-methyl-5-chloropyrrol-2-yl and 1-methyl-3,5- dichloropyrrole-2-yl.
  • Het-12 examples include 4,5-dichloro-imidazol-1-yl and 4,5-dimethyl-imidazol-1-yl.
  • Het-13 examples include 2-pyridyl, 3-fluoropyridin-2-yl, 3,5-difluoropyridin-2-yl, 3,5-dichloropyridin-2-yl, 3-fluoro-5- trifluoromethyl-pyridin-2-yl, 3-trifluoromethyl-pyridin-2-yl, 5-nitro-pyridin-2-yl, 5-cyano-pyridin-2-yl, 5-methoxycarbonyl-pyhdin-2-yl, 5- Trifluoromethyl-pyridin-2-yl, 5-methyl-pyridin-2-yl, 4-methyl-pyridin-2-yl, 3-methyl-pyridin-2-yl, 3-ethyl-pyridin-2-yl and 6- methyl-pyridin-2-yl.
  • Het-14 is 3-pyridyl.
  • Het-15 is 4-pyridyl.
  • Het-16 is pyrazin-2-yl.
  • Het-17 examples include pyridazin-3-yl, 6-chloro-pyridazin-3-yl, 6-methoxy-pyridazin-3-yl
  • Het-18 examples include 5-chloropyrimidin-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-pyhmidin-4-yl, 6-trifluoromethyl-pyrimidin-4-yl, 2-methyl-5-fluoropyrimidin-4-yl yl, 2-methyl-5-chloro-pyrimidin-4-yl, 5-chloro-6-methyl-pyrimdin-4-yl, 5-chloro-6-ethyl-pyrimdin-4-yl, 5-chloro-6- isopropyl-pyrimdin-4-yl, 5-bromo-6-methyl-pyrimidin-4-yl, 5-fluoro-6-methyl-pyrimidin-4-yl, 5-fluoro-6-fluoromethyl-pyrimi
  • Het-19 examples include 4-methyl-pyrimidin-5-yl, 4,6-dimethyl-pyrimidin-5-yl, 2,4,6-trimethylpyrimidin-5-yl and 4-trifluoromethyl-6-methyl-pyrimidine. 5-yl.
  • Het-20 examples include 4,6-dimethylpyrimidin-2-yl, 4,5,6-trimethylpyrimidin-2-yl, 4,6-dithfluoromethyl-pyrimidin-2-yl and 4,6-dimethyl-5-chloro pyrimidin-2-yl.
  • Het-21 is 1, 3,5-triazin-2-yl.
  • R 4 in formula I is halogen, CN, dC -alkoxy, especially methoxy, or dC 4 -alkyl, especially methyl.
  • R 4 is halogen stands.
  • Compounds of the formula I in which R 4 represents methyl or methoxy are also preferred.
  • R 5 represents hydrogen, halogen, especially chlorine or fluorine, or dC-alkyl, especially methyl.
  • R 5 represents hydrogen.
  • R 6 preferably represents hydrogen, halogen, especially chlorine or fluorine, a group C (W) R 13b , where W represents oxygen or sulfur and R 3b represents dC 4 alkoxy, NH 2 , dC 4 alkylamino or di-C C 4 alkylamino, especially C (O) OCH 3 , CONH 2 , C (S) OCH 3 , or for CC 4 alkyl, especially methyl.
  • R 5 is different from hydrogen
  • R 6 is in particular hydrogen.
  • R 5 and R 6 are particularly preferably hydrogen.
  • At least one of the variables X or Y in formula I represents a chemical bond.
  • the other of these groups YR 1 or XR 2 has the meanings given above.
  • R 1 and R 2 then have one of the meanings given as preferred.
  • both variables X and Y stand for a chemical bond.
  • R 1 and R 2 then independently of one another have the meanings indicated above, and are especially selected from hydrogen, alkyl dC dC 10 10 haloalkyl, C 3 -C ⁇ 0 alkenyl, C 3 -C 10 haloalkenyl, C 3 -C 8 -Cycloalkyl, C 53 -C 8 -cycloalkenyl, d-Cs-cycloalkyl-d-do-alkyl, C 3 -C 8 -cycloalkyl-C 2 -C 10 -alkenyl, phenyl or benzyl, the 6 last-mentioned radicals also 1 , 2, 3 or 4 substituents, selected from halogen, dC 4 -alkyl, dC -haloalkyl and CC -alkoxy, one of the radicals R 1 or R 2 can also be halogen
  • R 7 in particular represents hydrogen or dC -alkyl.
  • one of the variables X or Y in formula I represents a group NR 7 .
  • R 1 stands in the group - (NR 7 ) -R 1 for dC 10 alkyl, C 2 -C 10 alkenyl, C 4 -C 10 alkadienyl, C 2 -C 10 alkynyl, C 3 -C 8 Cycloalkyl, C 5 -C 8 cycloalkenyl, C 5 -C 10 bicycloalkyl, phenyl,
  • Compounds of the formula I in which the group (NR 7 ) R 1 is dC 6 -alkylamino or di-dC 6 -alkylamino, especially dC 4 -alkylamino or di-C C 4 -alkylamino are very particularly preferred.
  • - (NR 7 ) -R 1 stands for N-linked 5- or 6-membered saturated heterocyclyl, which optionally has a further heteroatom selected from N, O and S as a ring atom and which optionally has 1, 2, 3 or 4 substituents R 8 carries, which are selected from halogen and dC 4 alkyl.
  • the group - (NR 7 ) -R 1 stands for pipehdin-1-yl, 4-methyl-1-piperidinyl, 1-pyrrolidinyl, 2,5-dihydropyrrol-1-yl, 4-morpholinyl or 4-thiomorpholinyl.
  • R 8 stands in particular for halogen, especially fluorine, CC 4 alkoxy or dC 4 alkyl.
  • R 10 stands in particular for H, dC 4 -alkyl, C (O) H or CC 4 -alkylcarbonyl.
  • OR 10 stands in particular for OH, CC 4 -alkoxy, OC (O) H or CC 4 -alkylcarbonyloxy.
  • SR 10 stands in particular for SH or SdC alkyl.
  • R 1 and R 12 are in particular H, dC 4 -alkyl, dC -alkylcarbonyl or d C -CC 44 --AAllkkyyll ((tthhiiooccaarrbboonnyyll)) .. IInnssbbeessoonnddeerree sstteehhtt NNRR 1111 IR 12 for NH 2 , NHCH 3 , NHC 2 H 5 , N (CH 3 ) 2 , N (C 2 H 5 ) CH 3 , NHC (O) CH 3 or NHC (O) H.
  • R 13 stands in particular for H, dC 4 alkyl, OH, NH 2 , NHCH 3 , NHC 2 H 5 , N (CH 3 ) 2 , N (C 2 H 5 ) CH 3 or CC 4 alkoxy.
  • R 14 is in particular C 1 -C 4 -alkyl.
  • R 15 is in particular C 1 -C 4 alkyl.
  • R 16 stands in particular for hydrogen or CC alkyl.
  • R 17 stands in particular for H, CC 4 alkyl or CC 4 alkoxy.
  • R 18 and R 19 are in particular H, dC -alkyl, dC -alkylcarbonyl or CC CC 4 --AAllkkyyll ((tthhiiooccaarrbboonnyyll)) .. IInnssbbeessoonnddeerree sstteehhtt NNRR 1188 R 19 for NH 2l NHCH 3 , NHC 2 H 5 , N ( CH 3 ) 2 , N (C 2 H 5 ) CH 3 , NHC (O) CH 3 or NHC (O) H.
  • Particularly preferred compounds of the general formula I are the triazolopyrimidines of the general formula IA, in which R 3 is 2-fluoro-6-chlorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-A1).
  • Examples of these are the compounds I-A1.1 to I-A1.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2,6-difluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-A2).
  • Examples of these are the compounds I-A2.1 to I-A2.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolo-pyrimidines of the general formula IA, in which R 3 is 2,6-dichlorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are have previously mentioned and in particular the meanings mentioned as preferred (compounds I-A3).
  • Examples of these are the compounds I-A3.1 to I-A3.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-fluoro-6-methylphenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are have previously mentioned and in particular the meanings mentioned as preferred (compounds I-A4).
  • Examples of these are the compounds I-A4.1 to I-A4.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Triazolopyrimidines of the general formula IA in which R 3 is 2,4,6-trifluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (Connections I-A5). Examples of these are the compounds I-A5.1 to I-A5.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2,6-difluoro-4-methoxyphenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-A6).
  • Examples of these are the compounds I-A6.1 to I-A6.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-chloro-6-methylphenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are have previously mentioned and in particular the meanings mentioned as preferred (compounds I-A7).
  • Examples of these are the compounds I-A7.1 to I-A7.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolo-pyrimidines of the general formula IA, in which R 3 is pentafluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-A8).
  • Examples of these are the compounds I-A8.1 to I-A8.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-methyl-4-fluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are have the abovementioned and in particular the meanings mentioned as preferred (compounds I-A9).
  • Examples of these are the compounds I-A9.1 to I-A9.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-trifluoromethylphenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-A10).
  • Examples of these are the compounds I-A10.1 to I-A10.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-methoxy-6-fluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are have previously mentioned and in particular have the meanings mentioned as preferred (compounds I-A11). Examples of these are the compounds I-A11.1 to I-A1 1.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-chlorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-A12).
  • Examples of these are the compounds I-A12.1 to I-A12.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolo-pyrimidines of the general formula IA, in which R 3 is 2-fluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-A13).
  • Examples of these are the compounds I-A13.1 to I-A13.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2,4-difluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-A14).
  • Examples of these are the compounds I-A14.1 to I-A14.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-fluoro-4-chlorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are have the abovementioned and in particular the meanings mentioned as preferred (compounds I-A15).
  • Examples of these are the compounds I-A15.1 to I-A15.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 4-fluoro-6-chlorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are have previously mentioned and in particular the meanings mentioned as preferred (compounds I-A16). Examples of these are the compounds I-A16.1 to I-A16.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2,3-difluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-A17).
  • Examples of these are the compounds I-A17.1 to I-A17.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolo-pyrimidines of the general formula IA, in which R 3 is 2,5-difluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are have previously mentioned and in particular have the meanings mentioned as preferred (compounds I-A18). Examples of these are the compounds I-A18.1 to I-A18.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2,3,4-trifluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are have previously mentioned and in particular the meanings mentioned as preferred (compounds I-A19). Examples of these are the compounds I-A19.1 to I-A19.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-methylphenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-A20).
  • Examples of these are the compounds I-A20.1 to I-A20.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2,4-dimethylphenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-A21).
  • Examples of these are the compounds I-A21.1 to I-A21.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-methyl-4-chlorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are have previously mentioned and in particular the meanings mentioned as preferred (compounds I-A22).
  • Examples of these are the compounds I-A22.1 to I-A22.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-fluoro-4-methylphenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-A23).
  • Examples of these are the compounds I-A23.1 to I-A23.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2,6-dimethylphenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-A24).
  • Examples of these are the compounds I-A24.1 to I-A24.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2,4,5-trimethylphenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are have the abovementioned and in particular the meanings mentioned as preferred (compounds I-A25).
  • Examples of these are the compounds I-A25.1 to I-A25.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2,6-difluoro-4-cyanophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R. 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-A26). Examples of these are the compounds I-A26.1 to I-A26.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2,6-difluoro-4-methylphenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R. 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-A27).
  • Examples of these are the compounds I-A27.1 to I-A27.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolo-pyrimidines of the general formula IA, in which R 3 is 2,6-difluoro-4-methoxycarbonylphenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-A28).
  • Examples of these are the compounds I-A28.1 to I-A28.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-trifluoromethyl-4-fluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are have the abovementioned and in particular the meanings mentioned as preferred (compounds I-A29).
  • Examples of these are the compounds I-A29.1 to I-A29.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-trifluoromethyl-5-fluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are have previously mentioned and in particular the meanings mentioned as preferred (compounds I-A30).
  • Examples of these are the compounds I-A30.1 to I-A30.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-trifluoromethyl-5-chlorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are have previously mentioned and in particular the meanings mentioned as preferred (compounds I-A31).
  • Examples of these are the compounds I-A31.1 to I-A31.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are the triazolopyrimidines of the general formula IA, in which R 3 is 2-fluoro-6-chlorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are those previously mentioned and in particular have the meanings mentioned as preferred (compounds I-A32).
  • Examples of these are the compounds I-A32.1 to I-A32.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolo-pyrimidines of the general formula IA, in which R 3 is 2,6-difluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are have previously mentioned and in particular the meanings mentioned as preferred (compounds I-A33).
  • Examples of these are the compounds I-A33.1 to I-A33.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2,6-dichlorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds
  • I-A34 examples of these are the compounds I-A34.1 to I-A34.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-fluoro-6-methylphenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are have the abovementioned and in particular the meanings mentioned as preferred (compounds I-A35).
  • Examples of these are the compounds I-A35.1 to I-A35.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2,4,6-trifluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are have the abovementioned and in particular the meanings mentioned as preferred (compounds I-A36).
  • Examples of these are the compounds I-A36.1 to I-A36.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2,6-difluoro-4-methoxyphenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R. 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-A37).
  • Examples of these are the compounds I-A37.1 to I-A37.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolo-pyrimidines of the general formula IA, in which R 3 is 2-chloro-6-methylphenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-A38).
  • Examples of these are the compounds I-A38.1 to I-A38.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is pentafluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds
  • I-A39 examples of these are the compounds I-A39.1 to I-A39.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-methyl-4-fluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are have the abovementioned and in particular the meanings mentioned as preferred (compounds I-A40).
  • Examples of these are the compounds I-A40.1 to I-A40.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-trifluoromethylphenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-A41).
  • Examples of these are the compounds I-A41.1 to I-A41.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-methoxy-6-fluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are have the abovementioned and in particular the meanings mentioned as preferred (compounds I-A42).
  • Examples of these are the compounds I-A42.1 to I-A42.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolo-pyrimidines of the general formula IA, in which R 3 is 2-chlorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-A43).
  • Examples of these are the compounds I-A43.1 to I-A43.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-fluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular - Specifically have the meanings mentioned as preferred (compounds I-A44). Examples of these are the compounds I-A44.1 to I-A44.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2,4-difluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-A45).
  • Examples of these are the compounds I-A45.1 to I-A45.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-fluoro-4-chlorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are have the abovementioned and in particular the meanings mentioned as preferred (compounds I-A46).
  • Examples of these are the compounds I-A46.1 to I-A46.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 4-fluoro-6-chlorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are have previously mentioned and in particular the meanings mentioned as preferred (compounds I-A47). Examples of these are the compounds I-A47.1 to I-A47.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolo-pyrimidines of the general formula IA, in which R 3 is 2,3-difluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are have the abovementioned and in particular the meanings mentioned as preferred (compounds I-A48).
  • Examples of these are the compounds I-A48.1 to I-A48.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2,5-difluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds
  • I-A49 examples of these are the compounds I-A49.1 to I-A49.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2,3,4-trifluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are have the abovementioned and in particular the meanings mentioned as preferred (compounds I-A50).
  • Examples of these are the compounds I-A50.1 to I-A50.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-methylphenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-A51).
  • Examples of these are the compounds I-A51.1 to I-A51.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2,4-dimethylphenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-A51).
  • Examples of these are the compounds I-A51.1 to I-A51.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolo-pyrimidines of the general formula IA, in which R 3 is 2-methyl-4-chlorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-A52).
  • Examples of these are the compounds I-A52.1 to I-A52.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-fluoro-4-methylphenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are have the abovementioned and in particular the meanings mentioned as preferred (compounds I-A53).
  • Examples of these are the compounds I-A53.1 to I-A53.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2,6-dimethylphenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-A54).
  • Examples of these are the compounds I-A54.1 to I-A54.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2,4,5-trimethylphenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are have the abovementioned and in particular the meanings mentioned as preferred (compounds I-A55).
  • Examples of these are the compounds I-A55.1 to I-A55.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2,6-difluoro-4-cyanophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-A56).
  • Examples of these are the compounds I-A56.1 to I-A56.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolo-pyrimidines of the general formula IA, in which R 3 is 2,6-difluoro-4-methylphenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 has the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-A57).
  • Examples of these are the compounds I-A57.1 to I-A57.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2,6-difluoro-4-methoxycarbonylphenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 has the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-A58).
  • Examples of these are the compounds I-A58.1 to I-A58.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-trifluoromethyl-4-fluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are have the abovementioned and in particular the meanings mentioned as preferred (compounds I-A59).
  • Examples of these are the compounds I-A59.1 to I-A59.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-trifluoromethyl-5-fluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are have the abovementioned and in particular the meanings mentioned as preferred (compounds I-A60).
  • Examples of these are the compounds I-A60.1 to I-A60.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the triazolopyrimidines of the general formula IA, in which R 3 is 2-trifluoromethyl-5-chlorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are have previously mentioned and in particular the meanings given as preferred (compounds I-A61).
  • Examples of these are the compounds I-A61.1 to I-A61.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are the pyrazolopyrimidines of the general formula IB, in which R 3 is 2-fluoro-6-chlorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B1).
  • Examples of these are the compounds I-B1.1 to I-B1.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2,6-difluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are have previously mentioned and in particular the meanings mentioned as preferred (compounds I-B2).
  • Examples of these are the compounds I-B2.1 to I-B2.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2,6-dichlorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are have previously mentioned and in particular the meanings mentioned as preferred (compounds I-B3).
  • Examples of these are the compounds I-B3.1 to I-B3.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2-fluoro-6-methylphenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B4).
  • Examples of these are the compounds I-B4.1 to I-B4.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2,4,6-trifluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B5).
  • Examples of these are the compounds I-B5.1 to I-B5.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2,6-difluoro-4-methoxyphenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 has the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B6).
  • Examples of these are the compounds I-B6.1 to I-B6.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2-chloro-6-methylphenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B7).
  • Examples of these are the compounds I-B7.1 to I-B7.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is pentafluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-B8).
  • Examples of these are the compounds I-B8.1 to I-B8.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2-methyl-4-fluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B9).
  • Examples of these are the compounds I-B9.1 to I-B9.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2-trifluoromethylphenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-B10).
  • Examples of these are the compounds I-B10.1 to I-B10.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2-methoxy-6-fluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B11).
  • Examples of these are the compounds I-B11.1 to I-B11.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2-chlorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-B12).
  • Examples of these are the compounds I-B12.1 to I-B12.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2-fluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-B13).
  • Examples of these are the compounds I-B13.1 to I-B13.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2,4-difluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are have previously mentioned and in particular the meanings mentioned as preferred (compounds I-B14).
  • Examples of these are the compounds I-B14.1 to I-B14.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2-fluoro-4-chlorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B15).
  • Examples of these are the compounds I-B15.1 to I-B15.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 4-fluoro-6-chlorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B16).
  • Examples of these are the compounds I-B16.1 to I-B16.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2,3-difluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are have the abovementioned and in particular the meanings mentioned as preferred (compounds I-B17).
  • Examples of these are the compounds I-B17.1 to I-B17.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2,5-difluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are have previously mentioned and in particular the meanings mentioned as preferred (compounds I-B18). Examples of these are the compounds I-B18.1 to I-B18.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2,3,4-trifluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B19).
  • Examples of these are the compounds I-B19.1 to I-B19.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2-methylphenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-B20).
  • Examples of these are the compounds I-B20.1 to I-B20.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2,4-dimethylphenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 are have previously mentioned and in particular the meanings mentioned as preferred (compounds I-B21).
  • Examples of these are the compounds I-B21.1 to I-B21.41, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2-methyl-4-chlorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B22).
  • Examples of these are the compounds I-B22.1 to I-B22.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2-fluoro-4-methylphenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B23).
  • Examples of these are the compounds I-B23.1 to I-B23.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyridines of the general formula IB in which R 3 is 2,6-dimethylphenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B24).
  • Examples of these are the compounds I-B24.1 to I-B24.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2,4,5-trimethylphenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B25). Examples of these are the compounds I-B25.1 to I-B25.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2,6-difluoro-4-cyanophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 has the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B26).
  • Examples of these are the compounds I-B26.1 to I-B26.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2,6-difluoro-4-methylphenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 has the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B27).
  • Examples of these are the compounds I-B27.1 to I-B27.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2,6-difluoro-4-methoxycarbonylphenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B28).
  • Examples of these are the compounds I-B28.1 to I-B28.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2-trifluoromethyl-4-fluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B29).
  • Examples of these are the compounds I-B29.1 to I-B29.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2-trifluoromethyl-5-fluorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B30).
  • Examples of these are the compounds I-B30.1 to I-B30.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2-trifluoromethyl-5-chlorophenyl, R 4 is chlorine, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B31).
  • Examples of these are the compounds I-B31.1 to I-B31.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are the pyrazolopyrimidines of the general formula IB in which R 3 is 2-fluoro-6-chlorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B32).
  • Examples of these are the compounds I-B32.1 to I-B32.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2,6-difluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are have previously mentioned and in particular the meanings mentioned as preferred (compounds I-B33).
  • Examples of these are the compounds I-B33.1 to I-B33.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2,6-dichlorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are have the aforementioned and in particular the meanings mentioned as preferred (compounds I-B34).
  • Examples of these are the compounds I-B34.1 to I-B34.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2-fluoro-6-methylphenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B35).
  • Examples of these are the compounds I-B35.1 to I-B35.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2,4,6-trifluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B36).
  • Examples of these are the compounds I-B36.1 to I-B36.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2,6-difluoro-4-methoxyphenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 has the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B37).
  • Examples of these are the compounds I-B37.1 to I-B37.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2-chloro-6-methylphenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R and R 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B38).
  • Examples of these are the compounds I-B38.1 to I-B38.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is pentafluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-B39).
  • Examples of these are the compounds I-B39.1 to I-B39.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2-methyl-4-fluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B40).
  • Examples of these are the compounds I-B40.1 to I-B40.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2-trifluoromethylphenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-B41).
  • Examples of these are the compounds I-B41.1 to I-B41.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2-methoxy-6-fluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B42).
  • Examples of these are the compounds I-B42.1 to I-B42.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2-chlorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are the aforementioned and in particular have the meanings mentioned as preferred (compounds I-B43).
  • Examples of these are the compounds I-B43.1 to I-B43.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2-fluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are have previously mentioned and in particular the meanings mentioned as preferred (compounds I-B44).
  • Examples of these are the compounds I-B44.1 to I-B44.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2,4-difluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are have the abovementioned and in particular the meanings mentioned as preferred (compounds I-B45).
  • Examples of these are the compounds I-B45.1 to I-B45.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2-fluoro-4-chlorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B46).
  • Examples of these are the compounds I-B46.1 to I-B46.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 4-fluoro-6-chlorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B47).
  • Examples of these are the compounds I-B47.1 to I-B47.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2,3-difluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are have previously mentioned and in particular the meanings mentioned as preferred (compounds I-B48). Examples of these are the compounds I-B48.1 to I-B48.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2,5-difluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are have the abovementioned and in particular the meanings mentioned as preferred (compounds I-B49).
  • Examples of these are the compounds I-B49.1 to I-B49.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2,3,4-trifluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B50).
  • Examples of these are the compounds I-B50.1 to I-B50.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2-methylphenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R and R 2 are the abovementioned and in particular have the meanings mentioned as preferred (compounds I-Bs).
  • Examples of these are the compounds I-B51.1 to I-B51.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2,4-dimethylphenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R and R 2 are the same mentioned and in particular have the meanings mentioned as preferred (compounds I-B51).
  • Examples of these are the compounds I-B51.1 to I-B51.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2-methyl-4-chlorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B52).
  • Examples of these are the compounds I-B52.1 to I-B52.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2-fluoro-4-methylphenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B53).
  • Examples of these are the compounds I-B53.1 to I-B53.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2,6-dimethylphenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 are have the abovementioned and in particular the meanings mentioned as preferred (compounds I-B54).
  • Examples of these are the compounds I-B54.1 to I-B54.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2,4,5-trimethylphenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B55). Examples of these are the compounds I-B55.1 to I-B55.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2,6-difluoro-4-cyanophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 has the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B56).
  • Examples of these are the compounds I-B56.1 to I-B56.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2,6-difluoro-4-methylphenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 has the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B57).
  • Examples of these are the compounds I-B57.1 to I-B57.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2,6-difluoro-4-methoxycarbonylphenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B58).
  • Examples of these are the compounds I-B58.1 to I-B58.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2-trifluoromethyl-4-fluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B59).
  • Examples of these are the compounds I-B59.1 to I-B59.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB in which R 3 is 2-trifluoromethyl-5-fluorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B60).
  • Examples of these are the compounds I-B60.1 to I-B60.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • Particularly preferred compounds of the general formula I are also the pyrazolopyrimidines of the general formula IB, in which R 3 is 2-trifluoromethyl-5-chlorophenyl, R 4 is methyl, R 5 is hydrogen and X, Y, R 1 and R are 2 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds I-B61).
  • Examples of these are the compounds I-B61.1 to I-B61.414, in which XR 2 and YR 1 together each have the meanings given in one row of Table A.
  • tautomers of the formula II relate to tautomers of the formula II.
  • those compounds are preferred in which W a is O or S.
  • V preferably represents a chemical bond.
  • Preferred radicals R 20 are those which are indicated in formula I as preferred radicals for R 1 or R 2 .
  • R 20 represents a radical of the formulas C or B as indicated for R or R 2 .
  • Preferred tautomers II are in particular the compounds of the formulas II-A and II-B
  • R 3 , R 4 , R 5 , R 6 and R 20 have the meanings given above.
  • R 3 is 2-fluoro-6-chlorophenyl
  • R 4 is chlorine
  • R 5 is hydrogen
  • R 6 is hydrogen
  • R 20 is the aforementioned and in particular have the meanings mentioned as preferred (compounds II-A1 and II-B1).
  • Examples of these are the compounds II-A1.1 to II-A1.39 and II-B1.1 to II-B1.39, in which R 20 has the meaning given in one row of Table B.
  • R 3 is 2,6-difluorophenyl
  • R 4 is chlorine
  • R 5 is hydrogen
  • R 8 is hydrogen
  • R 20 is also the aforementioned and in particular have the meanings mentioned as preferred (compounds II-A2 and II-B2).
  • examples of these are the compounds II-A2.1 to II-A2.39 and II-B2.1 to II-B2.39, in which R 20 has the meaning given in one row of Table B.
  • R 3 is 2,6-dichlorophenyl
  • R 4 is chlorine
  • R 5 is hydrogen
  • R 6 is hydrogen
  • R 20 is the aforementioned and in particular have the meanings mentioned as preferred (compounds II-A3 and II-B3).
  • R has the abovementioned and in particular the meanings mentioned as preferred (compounds II-A5 and II-B5). Examples of these are the compounds II-A5.1 to II-A5.39 and II-B5.1 to II-B5.39, in which R 20 has the meaning given in one row of Table B.
  • R 3 is 2,6-difluoro-4-methoxyphenyl
  • R 4 is chlorine
  • R 5 is hydrogen
  • R 6 is hydrogen
  • R 20 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds II-A6 and II-B6).
  • examples games for this are the compounds II-A6.1 to II-A6.39 and II-B6.1 to II-B6.39, in which R 20 has the meaning given in one row of Table B.
  • R6 is hydrogen and R 20 has the meanings mentioned above and in particular the meanings mentioned as preferred (compounds II-A17 and II-B17). Examples for this are the compounds II-A17.1 to II-A17.39 and II-B17.1 to II-B17.39, in which R 20 has the meaning given in one row of Table B.
  • R 3 is 2,3,4-trifluorophenyl
  • R 4 is chlorine
  • R 5 is hydrogen
  • R 6 is hydrogen
  • R 20 is the same as above mentioned and in particular have the meanings mentioned as preferred (compounds II-A19 and II-B19).
  • examples of these are the compounds II-A19.1 to II-A19.39 and II-B19.1 to II-B19.39, in which R 20 has the meaning given in one row of Table B.
  • R 3 is 2,6-difluoro-4-cyanophenyl
  • R 4 is chlorine
  • R 5 is hydrogen
  • R 6 is hydrogen
  • R 20 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds II-A26 and II-B26).
  • examples of these are the compounds II-A26.1 to II-A26.39 and II-B26.1 to II-B26.39, in which R 20 has the meaning given in one row of Table B.
  • R 3 is 2,6-difluoro-4-methoxycarbonylphenyl
  • R 4 is chlorine
  • R 5 is hydrogen
  • R 6 is hydrogen
  • R 20 have the meanings mentioned above and in particular the meanings mentioned as preferred (compounds II-A28 and II- B28).
  • examples of these are the compounds II-A28.1 to II-A28.39 and II-B28.1 to II-B28.39, in which R 20 has the meaning given in one row of Table B.
  • R 3 is 2-trifluoromethyl-4-fluorophenyl
  • R 4 is chlorine
  • R 5 is hydrogen
  • R 6 is hydrogen
  • R 20 is the same mentioned and in particular have the meanings mentioned as preferred (compounds II-29 and II-B29).
  • examples of these are the compounds II-A29.1 to II-A29.39 and II-B29.1 to II-B29.39, in which R 20 has the meaning given in one row of Table B.
  • R 3 is 2,6-difluorophenyl
  • R 4 is methyl
  • R 5 is hydrogen
  • R 6 is hydrogen
  • R 20 is also those mentioned above and in particular have the meanings mentioned as preferred (compounds II-A33 and II-B33).
  • examples of these are the compounds II-A33.1 to II-A33.39 and II-B33.1 to II-B33.39, in which R 20 has the meaning given in one row of Table B.
  • R 3 is 2,6-dichlorophenyl
  • R 4 is methyl
  • R 5 is hydrogen
  • R 6 is hydrogen
  • R 20 is the abovementioned and in particular have the meanings mentioned as preferred (compounds II-A34 and II-B34).
  • examples of these are the compounds II-A34.1 to II-A34.39 and II-B34.1 to II-B34.39, in which R 20 has the meaning given in one row of Table B.
  • R 20 has the meaning given in one row of Table B.
  • the compounds of the formula I according to the invention can be prepared in analogy to methods known per se from the prior art, starting from 7-aminoazolopyrimidines of the general formula III or 7-haloazolopyrimidines of the formula IV
  • R 1c and R 2c independently of one another represent hydrogen or have the meanings given for R 1 or R 2 or R 1c forms with R 2c and with the carbon atom to which they are attached a 5-, 6 or 7-membered group, saturated or unsaturated carbo- or heterocycle, the latter having 1, 2, 3 or 4 heteroatoms selected from O, S and N as a ring member, the carbo- and heterocycle being partially or completely halogenated, or 1, 2, 3 or 4 of the radicals R 7 and / or R 8 can have.
  • R 1 and R 2b are independently hydrogen or have the meanings given for R 1 or R 2 or R 1b forms a 5-, 6 or 7- with R 2b and with the carbon atom to which they are attached membered, saturated or unsaturated carbo- or heterocycle, the latter having 1, 2, 3 or 4 heteroatoms selected from O, S and N as a ring member, the carbo- and heterocycle being partially or completely halogenated, or 1, 2 , 3 or 4 of the radicals R 7 and / or R 8 may have.
  • R represents aryl such as phenyl, which is optionally substituted, for example with 1, 2 or 3 substituents selected from halogen, alkyl or alkoxy.
  • halogenating agents [Hai] are phosphorus halides and sulfur halide compounds such as phosphorus oxybromide, phosphorus oxychloride, phosphorus pentachloride, thionyl chloride, thionyl bromide or sulfuryl chloride.
  • the reaction can be carried out in bulk or in the presence of a solvent. In one embodiment, the reaction is carried out in the presence of a tertiary amine such as triethylamine or pyridine as the base.
  • reaction is carried out in an aromatic hydrocarbon such as toluene in the presence of catalytic amounts of an amide such as dimethylformamide.
  • aromatic hydrocarbon such as toluene
  • amide such as dimethylformamide.
  • the halogen compounds I in which YR 1 (or XR 2 ) is halogen, can in turn be converted into the corresponding compounds I, in which Y is oxygen, by reacting them with an alcohol of the formula R 1 --OH according to that of Stevens et al., J. Am. Chem. Soc. 1953, 75, pp. 657-660 et al. implement the method described.
  • the compounds I in which X is oxygen are obtained in an analogous manner from the compounds I in which XR 2 is halogen.
  • the compounds of the formula I in which X is a bond and Y is a group R 7 can be prepared in an analogous manner by reaction with secondary amines of the formula R 1 -NH-R 7 .
  • one can analogously by reaction with thioalcohols of the form mel R 1 -SH produce the compounds of the formula I in which X is a bond and Y is S (see Scheme 3).
  • tertiary amines such as triethylamine or pyridine compounds, and / or dehydrating agents, for.
  • compounds of the formula II in which V is O or S can be obtained by reacting III with derivatives of carbonic acid or thiocarbonic acid, eg. B. chloroformates or carbonates.
  • Compounds II, in which V is NH can be prepared by reacting III with isocyanates or isothiocyanates.
  • Suitable solvents are water, aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether , Dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and
  • the reaction mixtures are worked up in a conventional manner, for. B. by mixing with water, separation of the phases and optionally chromatographic purification of the raw products.
  • the intermediate and end products fall z. T. in the form of colorless or slightly brownish, viscous oils, which are freed from volatile components or cleaned under reduced pressure and at a moderately elevated temperature. If the intermediate and end products are obtained as solids, they can also be purified by recrystallization or digesting.
  • isomer mixtures are obtained in the synthesis, however, a separation is generally not absolutely necessary, since the individual isomers can partially convert into one another during preparation for use or during use (e.g. under the action of light, acid or base) , Corresponding conversions can also take place after use, for example during treatment of plants in the treated plant or in the harmful fungus to be controlled.
  • the compounds I are suitable as fungicides. They are distinguished by their excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes. Some of them are systemically effective and can be used in plant protection as leaf and soil fungicides.
  • Podospha herpotrichoides on wheat and barley Pseudoperonospora species on hops and cucumbers, Puccinia A en on cereals, Pyricularia oryzae on rice, Rhizoctonia species on cotton, rice and lawn, Septoria tritici and Stagonospora nodorum on wheat, Uncinula necator on vines, Ustilago -A s on cereals and sugar cane, and Venturia arias (scab) on apples and pears.
  • the compounds I are also suitable for combating harmful fungi such as Paecilomyces variotii in the protection of materials (for example wood, paper, dispersions for painting, fibers or fabrics) and in the protection of stored products.
  • 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 active amount of the active compounds.
  • the application can take place 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% by weight of active ingredient.
  • the application rates in crop protection are between 0.01 and 2.0 kg of active ingredient per ha.
  • active ingredient 0.001 to 0.1 g, preferably 0.01 to 0.05 g, per kg of seed are generally required.
  • the amount of active ingredient applied depends on the type of application and the desired effect. Usual application rates in material protection are, 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 I can be converted into the usual formulations, for. B. solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the form of application depends on the respective purpose; in any case, it should ensure a fine and uniform distribution of the compound according to the invention.
  • the formulations are prepared in a known manner, e.g. B. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants.
  • solvents and auxiliaries The following are essentially considered as solvents / auxiliaries:
  • aromatic solvents e.g. Solvesso products, xylene
  • paraffins e.g. petroleum fractions
  • alcohols e.g. methanol, butanol, pentanol, benzyl alcohol
  • ketones e.g. cyclohexanone, gamma-butryolactone
  • pyrrolidones NMP, NOP
  • acetates glycols, diethyl fatty acid amides, fatty acids and fatty acid esters.
  • solvent mixtures can also be used, - Carriers such as natural powdered rock (e.g. kaolins, clays, talc, chalk) and synthetic powdered rock (e.g.
  • Emulsifiers such as non-ionic and anionic emulsifiers (e.g. polymer lyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
  • non-ionic and anionic emulsifiers e.g. polymer lyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates
  • dispersants such as lignin sulfite waste liquors and methyl cellulose.
  • Suitable surfactants are alkali metal, alkaline earth metal salts, sulfonic acid ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfonic fattechnisch fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products naphthalene or naphthalene sulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol,
  • mineral oil fractions from medium to high boiling points such as kerosene or diesel oil, also coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. B. toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, e.g. B. dimethyl sulfoxide, N-methylpyrrolidone or water.
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. B. coating, impregnation and homogeneous granules can be prepared by binding the active ingredients to solid carriers.
  • Solid carriers are e.g. B. mineral soils, 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 as. B. 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.
  • B. mineral soils such as silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium s
  • the formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight of the active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
  • examples of formulations include products for dilution in water, e.g. B.
  • TLC Dispersible concentrates
  • Emulsifiable concentrates 15 parts by weight of a compound according to the invention are dissolved in xylene with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (5% each). Dilution in water results in an emulsion;
  • D Emulsions (EW, EO): 40 parts by weight of a compound according to the invention are dissolved in xylene with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (5% each). This mixture is introduced into water using an emulsifying machine (Ultraturax) and brought to a homogeneous emulsion. Dilution in water results in an emulsion,
  • E suspensions 20 parts by weight of a compound according to the invention are comminuted in a stirred ball mill to form a fine active ingredient suspension with the addition of dispersing and wetting agents and water or an organic solvent. Dilution in water results in a stable suspension of the active ingredient;
  • Water-dispersible and water-soluble granules 50 parts by weight of a compound according to the invention are finely ground with the addition of dispersing and wetting agents and produced as technical-grade equipment (e.g. 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;
  • H dusts (DP) 5 parts by weight of a compound according to the invention are finely ground and intimately mixed with 95% finely divided kaolin. This gives a dusting agent;
  • I Granules (GR, FG, GG, MG): 0.5 part by weight of a compound according to the invention is finely ground and combined with 95.5% carriers. Common processes are extrusion, spray drying or fluidized bed. This gives granules for direct application;
  • J ULV solutions (UL); 10 parts by weight of a compound according to the invention are in an organic solvent, for. B. xylene dissolved. This gives you a product for direct application.
  • the application forms depend entirely on the purposes of 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.
  • emulsions, pastes or oil dispersions the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • the active ingredient concentrations in the ready-to-use preparations can be varied over a wide range. 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 process (ULV), it being possible to apply formulations with more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume process
  • Oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides can be added to the active compounds, if appropriate also only immediately before use (tank mix). These agents can be added to the agents according to the invention in a weight ratio of 1:10 to 10: 1.
  • the agents according to the invention can also be present in the use form as fungicides together with other active ingredients which, for. B. with herbicides, insecticides, growth regulators, fungicides or with fertilizers. Mixing the compounds I or the compositions containing them in the use form as fungicides with other fungicides results in an enlargement of the fungicidal spectrum of action in many cases.
  • Acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl,
  • Amine derivatives such as aldimorph, dodine, dodemorph, fenpropimorph, fenpropidine, guazatine, iminoctadine, spiroxamine, tridemorph • anilinopyrimidines such as pyrimethanil, mepanipyrim or cyrodinyl,
  • Antibiotics such as cycloheximide, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin,
  • azoles such as bitertanol, bromoconazole, cyproconazole, difenoconazole, Dinitrocona- zol, epoxiconazole, fenbuconazole, Fluquiconazol, flusilazole, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, prochloraz, prothioconazole, tebuconazole, triadimefon, triadimenol, triflumizole, triticonazole,
  • Dicarboximides such as iprodione, myclozolin, procymidone, vinclozolin,
  • Dithiocarbamates such as Ferbam, Nabam, Maneb, Mancozeb, Metam, Metiram, Propineb, Polycarbamat, Thiram, Ziram, Zineb, Heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim, carboxin, oxycarboxin, cyazofamid, dazomet, dithianon, famoxadone, fenamidon, fenarimol, fuberidazole, flutolanil, furametpyr, isoprothiolan, mepronazidolomolol, probolil, probolil, nuarol, probolil, probolil Quinoxyfen, silthiofam, thiabenzazole, thifluzamide, thiophanate methyl, tiadinil, tricyclazole, triforins,
  • Copper fungicides such as Bordeaux broth, copper acetate, copper oxychloride, basic copper sulfate,
  • Nitrophenyl derivatives such as binapacryl, dinocap, dinobuton, nitrophthal-isopropyl
  • fungicides such as acibenzolar-S-methyl, benthiavalicarb, carpropamide, chlorothalonil, cyflufenamid, cymoxanil, Dazomet, diclomezin, diclocymet, Diethofen-carb, edifenphos, ethaboxam, fenhexamide, fentin acetate, fennosetanyl, ferim Fosetyl aluminum, iprovalicarb, hexachlorobenzene, metrafenone, pencycuron, propamocarb, phthalide, toloclofos-methyl, quintozene, zoxamide
  • Strobilurins such as azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin or trifloxystrobin,
  • Sulfenic acid derivatives such as captafol, captan, dichlofluanid, folpet, tolylfluanid
  • Cinnamic acid amides and analogues such as dimethomorph, flumetover or flumorph.
  • the active ingredients were prepared separately as a stock solution with 0.25% by weight of active ingredient in acetone or DMSO. 1% by weight of the emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) was added to this solution and diluted with water to the desired concentration.
  • emulsifier Uniperol® EL wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • Leaves of potted tomato plants were sprayed to runoff point with an aqueous suspension in the active compound concentration given below. The following day, the leaves were infected with an aqueous spore suspension of Phytophthora infestans. The plants were then placed in a water vapor-saturated chamber at temperatures between 18 and 20 ° C. After 6 days, the blight on the untreated but infected control plants had developed so strongly that the infestation could be determined visually in%. In this test, the plants treated with 250 ppm of the active ingredient from Example 5 showed an infection of less than or equal to 15%, while the untreated plants were 70% infected.
  • Example of use 4 Protective activity against rice blight caused by Pyricularia oryzae in the microtiter test.
  • the active substances were formulated separately as a stock solution and with a concentration of 10000 ppm in DMS ⁇ .
  • the active substances were diluted with water in accordance with the stated concentration.
  • microtiter plate 50 ⁇ l of the required active ingredient concentration were pipetted into a microtiter plate (MTP). The inoculation was then carried out with 50 ⁇ l of an aqueous spore suspension from Pyricularia oryzae. The plates were placed in a steam-saturated chamber at temperatures of 18 ° C. The microtiter plates were measured on the 7th day after the inoculation at 405 nm with an absorption photometer.
  • the measured parameter was calculated with the growth of the drug-free control and blank value in order to determine the relative growth in% of the pathogens in the individual active ingredients.

Abstract

L'invention concerne des composés azolopyrimidine de formule générale (I) dans laquelle : A représente N ou C-R<6> ; Y et X désignent indépendamment l'un de l'autre un composé chimique ou représentent oxygène, soufre ou un groupe N-R<7> ; les variables R<1>, R<2>, R<3>, R<4>, R<5>, R<6> et R<7> sont telles que définies dans les revendications et la description. Cette invention concerne également les tautomères des composés de formule (I), ainsi que les sels, compatibles avec l'agriculture, des composés (I) et de leurs tautomères. La présente invention se rapporte en outre à l'utilisation des composés azolopyrimidine de formule générale (I), de leurs tautomères et de leurs sels compatibles avec l'agriculture pour lutter contre des champignons phytopathogènes (champignons nuisibles), à un procédé pour lutter contre des champignons nuisibles phytopathogènes, ainsi qu'à un produit pour lutter contre des champignons nuisibles, ce produit renfermant au moins un composé de formule (I), un tautomère de (I) et/ou un sel compatible avec l'agriculture du composé de formule (I) ou de son tautomère, ainsi qu'au moins un support liquide ou solide.
EP05715521A 2004-02-25 2005-02-24 Composes azolopyrimidine et leur utilisation pour lutter contre des champignons nuisibles Withdrawn EP1720879A2 (fr)

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WO2014143240A1 (fr) 2013-03-15 2014-09-18 Vertex Pharmaceuticals Incorporated Dérivés de pyrazolopyrimidine fusionnés utiles en tant qu'inhibiteurs de la kinase atr
EP2970289A1 (fr) 2013-03-15 2016-01-20 Vertex Pharmaceuticals Inc. Composés utiles en tant qu'inhibiteurs de la kinase atr
US8969360B2 (en) 2013-03-15 2015-03-03 Vertex Pharmaceuticals Incorporated Compounds useful as inhibitors of ATR kinase
SI3077397T1 (sl) 2013-12-06 2020-02-28 Vertex Pharmaceuticals Inc. 2-amino-6-fluoro-N-(5-fluoro-piridin-3-IL)pirazolo(1,5-A)pirimidin-3- karboksamidna spojina, koristna kot inhibitor kinaze ATR, njena priprava, različne trdne oblike in njeni radioaktivno označeni derivati
PL3152212T3 (pl) 2014-06-05 2020-06-15 Vertex Pharmaceuticals Inc. Radioznakowane pochodne związku 2-amino-6-fluoro-n-[5-fluoro-piridyn-3-ylo]-pirazolo[1,5-a]pirymidino-3-karboksamidu przydatne jako inhibitor kinazy atr, wytwarzanie tego związku i jego różnych postaci stałych
SI3157566T1 (sl) 2014-06-17 2019-08-30 Vertex Pharmaceuticals Incorporated Postopek za zdravljenje raka z uporabo kombinacije inhibitorjev CHK1 in ATR
WO2017059357A1 (fr) 2015-09-30 2017-04-06 Vertex Pharmaceuticals Incorporated Méthode de traitement du cancer utilisant une association d'agents endommageant l'adn et d'inhibiteurs de l'atr

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3130633A1 (de) * 1981-08-01 1983-02-17 Basf Ag, 6700 Ludwigshafen 7-amino-azolo(1,5-a)pyrimidine und diese enthaltende fungizide
TW224044B (fr) * 1991-12-30 1994-05-21 Shell Internat Res Schappej B V
US5593996A (en) * 1991-12-30 1997-01-14 American Cyanamid Company Triazolopyrimidine derivatives
EP0819001A1 (fr) * 1995-04-05 1998-01-21 Byk Gulden Lomberg Chemische Fabrik GmbH Utilisation de composes de piperidine ou de pyrrolidine substitues pour le traitement de maladies modulees par un recepteur sigma
ATE282040T1 (de) * 2000-12-11 2004-11-15 Basf Ag 6-phenyl-pyrazolpyrimidine
DK1414302T3 (da) * 2001-07-26 2007-06-18 Basf Ag 7-aminotriazolopyrimidiner til bekæmpelse af skadelige svampe
DE10223917A1 (de) * 2002-05-29 2003-12-11 Bayer Cropscience Ag Pyrazolopyrimidine

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2005080396A2 *

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