EP2049498A1 - Composés de pyrimidine pour la lutte contre les champignons nuisibles et le cancer - Google Patents

Composés de pyrimidine pour la lutte contre les champignons nuisibles et le cancer

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Publication number
EP2049498A1
EP2049498A1 EP07788154A EP07788154A EP2049498A1 EP 2049498 A1 EP2049498 A1 EP 2049498A1 EP 07788154 A EP07788154 A EP 07788154A EP 07788154 A EP07788154 A EP 07788154A EP 2049498 A1 EP2049498 A1 EP 2049498A1
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EP
European Patent Office
Prior art keywords
alkyl
formula
alkoxy
group
haloalkyl
Prior art date
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Application number
EP07788154A
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German (de)
English (en)
Inventor
Jochen Dietz
Bernd Müller
Jan Klaas Lohmann
Jens Renner
Sarah Ulmschneider
Marianna Vrettou
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BASF SE
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BASF SE
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Priority to EP07788154A priority Critical patent/EP2049498A1/fr
Publication of EP2049498A1 publication Critical patent/EP2049498A1/fr
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings

Definitions

  • the present invention relates to the use of 5- (het) arylpyrimidines for controlling harmful fungi, novel 5- (het) arylpyrimidines and fungicidal or pharmaceutical agents containing at least one such compound as an active ingredient.
  • Fungicidally active 5-phenyl- and 5-hetarylpyrimidines bearing an amino group, a (thio) ether group or an aliphatic, carbo- or heterocyclic radical bonded via C in the 6-position are generally known and are described, for example, in US Pat WO 01/96314, WO 03/043993, WO 03/070721, WO 2004/087678, WO 2004/103978, WO 2005/012261, WO 2005/019187 and WO 2005/070899.
  • WO 2005/030216 describes 5-phenylpyrimidines which carry on the phenyl ring a hydroxyalkoxy, aminoalkoxy, hydroxyalkylthio, aminoalkylthio, hydroxyalkylamino or aminoalkylamino group which are substituted in the 6-position by a secondary amino group or a cycloalkyl group and in US Pat the 2-position carry an amino group, a cyanamide group, an aryl or a hetaryl substituent. These compounds should be suitable for the treatment of cancer. A use in crop protection is not mentioned.
  • fungicides pyrimidine compounds are partially unsatisfactory in terms of their fungicidal activity or have undesirable properties, such as a low Nutzessever joskeit.
  • novel pyrimidine compounds are to be provided with a pharmacological effect enhanced as compared to the pyrimidines of the prior art.
  • the object is surprisingly achieved by pyrimidine compounds of the general formula I defined below and by the agriculturally acceptable salts of the compounds I.
  • the present invention thus relates to the use of pyrimidine compounds of the formula I.
  • R 1 is Ci-Cio-alkyl, C 2 -Cio-alkenyl, C 2 -Cio-alkynyl, C 3 -Cio-cycloalkyl, C 3 -C 0 -cycloalkenyl, phenyl, naphthyl or a saturated or unsaturated, aromatic or non-aromatic 5-, 6-, 7-, 8-, 9- or 10-membered heterocycle, wherein the heterocycle contains 1, 2, 3 or 4 heteroatoms selected from O, S and N as ring members and also 1 or 2 CO groups may contain as ring members, wherein R 1 may be partially or completely halogenated and / or 1, 2, 3 or 4 may carry identical or different substituents L 3 ; or
  • R 2 is phenyl or a 5- or 6-membered heteroaromatic radical, wherein the heteroaromatic radical contains 1, 2, 3 or 4 heteroatoms selected from O, S and N, as ring members, wherein phenyl or the heteroaromatic radical is a Substituents L 1 and optionally 1, 2, 3 or 4 bear identical or different substituents L 2 ;
  • R 3 represents halogen, hydroxy, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C 2 -Cio-alkenyl, C 2 -C 0 - haloalkenyl, C 2 -Cio-alkynyl, C 2 -Cio-haloalkynyl, Ci Cio-alkoxy, C 1 -C 10 -haloalkoxy, C 1 -C 10 -alkylthio, C 1 -C 10 -haloalkylthio, C 1 -C 10 -alkylsulfinyl, C 1 -C 10 -alkylsulfonyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, cyano Ci-C4-alkyl or cyano;
  • R 4 is halogen, cyano, hydroxyl, mercapto, N 3 , C 1 -C 6 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 1 -C 6 -alkoxy, C 3 -C 8 -alkenyloxy , C 3 -C 8 alkynyloxy, Ci-C 6 alkylthio, C 3 -C 8 - alkenylthio, C 3 -C 8 alkynylthio, Ci-C 6 alkylsulfinyl, Ci-C6 alkylsulfonyl, Hydroxysul- fonyl, Aminosulfonyl, C 1 -C 6 -alkylaminosulfonyl, di-C 1 -C 6 -alkylaminosulfonyl, Cs -do-cycloalkyl, phenyl, naphthyl,
  • W is O, S, NR d or NNR d R e ;
  • X 1 is O or NR f ;
  • R a , R b , R c , R d , R e , R f independently of one another are hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 1 -C 4 -alkyl 6 alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-Ce-alkylcarbonyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkenyl, C 3 -C 6 - cycloalkoxy, aryl, Aryl-C 1 -C 4 -alkyl or 5-, 6-, 7-, 8-, 9- or 10-membered heterocyclyl having 1, 2, 3 or 4 heteroatoms selected from O,
  • R a , R b , R c are directly bonded to an oxygen atom, they are not hydroxy, C 1 -C 6 -alkoxy or C 3 -C 6 -cycloalkoxy;
  • Ra is independently defined as R a or is halo or cyano
  • X 11 is independently defined as X 1 ; or two of R a , R b , R c , R d , R e , R f , R ⁇ together form a C 2 -C 4 alkylene group which may be interrupted by an oxygen atom and / or may comprise a CC double bond .
  • R x is cyano, nitro, amino, aminocarbonyl, aminothiocarbonyl, hydroxy,
  • R x may be unsubstituted or may carry 1, 2 or 3 radicals R y , wherein
  • R y is cyano, nitro, halogen, hydroxy, amino, aminocarbonyl, aminothiocarbonyl, -C 6 alkyl, -C 6 -haloalkyl, CrC 6 -
  • R ⁇ , R ⁇ are independently hydrogen or C 1 -C 6 -alkyl
  • R 5 is H, d-Cio-alkyl, C 2 -Cio-hydroxyalkyl, C 2 -Cio-alkenyl, C 2 -Cio-alkynyl, C 4 -C 0 - alkadienyl, Cs-do-cycloalkyl, Ci-CIO alkoxy, C 2 -C 0 alkenyloxy, C 2 -C 0 -
  • R 5 wherein the aliphatic, alicyclic, aromatic and / or heterocyclic groups in R 5 may be partially or fully halogenated and / or may carry 1, 2, 3 or 4 identical or different substituents R a1 ;
  • R 6 is independently defined as R 5 , with the proviso that R 5 and R 6 are not simultaneously H, or a group # -CR 61 R 62 - (CR 63 R 64 ) q - (CR 65 R 66 ) P -YZ stands in which
  • # is the point of attachment to the nitrogen atom
  • R 61 , R 62 , R 63 , R 64 , R 65 and R 66 are each independently hydrogen, Ci-C 8 -
  • R 61 with R 62 , R 63 with R 64 , R 65 with R 66 in each case also together for the formation of carbonyl groups mean oxygen and to form spiro groups a C 2 -C 5 -alkylene, C 2 -Cs-alkenylene or C 2 -C 5 alkynylene chain which may be interrupted by one, two or three heteroatoms from the group O, N and S;
  • R 5 and R 61 together with atoms to which they are attached, a 5-, 6-,
  • 7-, 8-, 9- or 10-membered saturated or partially unsaturated heterocycle can form, in addition to carbon atoms, one, two or three further heteroatoms from the group O, N and S may contain as a ring member;
  • R 61 to R 66 may each independently be partially or completely halogenated and / or may carry one, two, three or four identical or different groups R a1 ;
  • each R a1 is independently cyano, nitro, hydroxy, carboxyl, C 1 -C 6 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 8 - cycloalkenyl, Ci-Ce alkoxy, C 2 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C 3 -C 6 -CyCl oa I koxy, C3-C6-cycloalkenyloxy, Ci-C6-alkylthio, amino, Ci-C ⁇ -alkylamino,
  • Groups in the aforementioned groups R a1 and R ⁇ may in turn be partially or fully halogenated and / or may carry one, two or three groups R b1 ;
  • each R b1 are independently cyano, nitro, hydroxy, mercapto, amino, carbo- xyl, Ci-Ce-alkyl, C2-C8 alkenyl, Ci-C 6 alkoxy, C 2 -C 8 alkenyloxy, C 2 C 8 -alkynyloxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di (C 1 -C 6 -alkyl) -amino, formyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkyl Alkylsulfinyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkoxycarbonyloxy, aminocarbonyl, aminothiocarbonyl, C 1 -C 6
  • p 0, 1, 2, 3, 4 or 5;
  • q is 0 or 1
  • Y is oxygen or sulfur
  • Z is hydrogen, carboxyl, formyl, C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 8 -cycloalkenyl, C ( O) R ⁇ , C (O) OR ⁇ , C (S) OR ⁇ , C (O) SR ⁇ , C (S) SR ⁇ , C (NR A ) SR ⁇ , C (S) R ⁇ , C ( NR ⁇ ) NR A R B , C (NR ⁇ ) R A , C (NR ⁇ ) OR A , C (O) NR A R B , C (S) NR A R B , C (S) NR A R B , C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylthio, C 1 -
  • R A and R B independently of one another are hydrogen, C 2 -alkenyl, C 2 -alkynyl or one of the groups mentioned for R ⁇ ; or
  • R A and R B together with the nitrogen atom to which they are attached, or R A and R ⁇ together with the carbon and hetero atoms through which they are attached, a five- or six-membered saturated, partially unsaturated or aromatic Ring can form, in addition to carbon atoms one, two or three further heteroatoms from the group O, N and S as a ring member and / or can carry one or more substituents R a1 ;
  • Z can also form with R 64 or R 66 a five- or six-membered saturated or partially unsaturated ring which, in addition to carbon atoms and Y, may contain one or two further heteroatoms from the group O, N and S as ring member and / or one or more substituents R a1 can carry;
  • group Z may be partially or completely halogenated and / or may carry one, two or three groups R b1 ;
  • R 5 and R 6 together with the nitrogen atom to which they are attached form a saturated or unsaturated aromatic or non-aromatic 5-, 6-, 7- or ⁇ -membered heterocycle, where the heterocycle additionally contains 1, 2 or 3 Heteroatoms which are selected from O, S and N, and / or may contain 1 or 2 CO groups as ring members and wherein the heterocycle may carry 1, 2 or 3 substituents which are selected from halogen, hydroxy, cyano, nitro, carboxyl, Ci-Cs alkyl, Ci-Cs-haloalkyl, C 2 -C 8 hydroxyalkyl, Ci-C8-alkoxy, CrC 8 - haloalkoxy, Ci-C 8 - alkylthio, Ci-C8-haloalkylthio, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8-alkenyloxy, C2-C8 haloalkenyloxy, C2-C8 alkyny
  • R 7 and R 8 independently of one another represent hydrogen, C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl,
  • L 1 represents a group of the formula -Y 1 -Y 2 -T, wherein
  • Y 1 is CR h R ', C (O) O, C (O) NR h , O, NR h or S (O) r ;
  • T 3 is where T 1 is O or NR h ; T 2 is O, S or NR h ; T 3 is R h , OR h , SR h or NR h R '; each R h and R 1 are independently H, C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl,
  • each L 2 is independently halogen, hydroxy, mercapto (SH), cyano, cyanato (OCN), nitro, carboxyl (COOH), Ci-Cio-alkyl, Ci-Cio-haloalkyl, C 2 -Cio-hydroxyalkyl, Ci-Cio alkoxy, Ci-Cio-haloalkoxy, Ci-Cio-alkylthio, C 2 -Cio-alkenyl, C 2 -C 0 - haloalkenyl, C 2 -C 0 alkenyloxy, C 2 -C 0 alkynyl, C3-CIO Haloalkynyl, C 2 -Ci 0 -
  • RJ, R k, R 1, R m, R n, R 0, RP, Ri, R r are each independently H, Ci-C8 -alkyl, CrC 8 - haloalkyl, C2-C8 hydroxyalkyl, C2 C 8 alkenyl, C2-C8 haloalkenyl,
  • R m and R n , R 0 and RP and / or R ⁇ and R r together with the nitrogen atom to which they are attached form a four-, five- or six-membered saturated or partially unsaturated ring, the one, two , three or four independently selected from L 5 substituents can carry;
  • a 1 represents hydrogen, hydroxy, C 1 -C 8 -alkyl, amino, C 1 -C 8 -alkylamino or
  • a 2 is C 2 -C 8 alkenyl, C 8 alkoxy, d-Ce-haloalkoxy, C 2 -Cio-alkenyloxy,
  • n O, 1 or 2;
  • each L 3 is independently defined as L 2 or is phenyl, naphthyl or a saturated or unsaturated, aromatic or non-aromatic 5-, 6-, 7-, 8-, 9- or 10-membered heterocycle, wherein the heterocycle 1, 2 , 3 or 4 heteroatoms selected from O, S and N, containing as ring members and also containing 1 or 2 CO groups as ring members, wherein the aliphatic, alicyclic, aromatic and heterocyclic groups in L 3 in turn may be partially or completely halogenated and / or may carry 1, 2 or three substituents L 4 ;
  • each L 4 is independently cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 8 -alkenyl, C 4 -C 8 -alkadienyl, C 2 -C 8 alkenyloxy, C 2 -C 8 alkynyloxy, Ci-C 6 alkoxy, -C 6 - haloalkoxy, d-C ⁇ alkylthio, CrC ⁇ -alkylamino, di- (CRC6-alkyl) amino, formyl, CrCe- Alkylcarbonyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylcarbonyloxy, C 1
  • each L 5 is independently selected from hydroxy, cyano, nitro, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 2 -C 8 hydroxyalkyl, C 1 -C 8 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 8 alkylthio , C 2 -C 8 -alkenyl -alkyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkenyloxy, C 2 -C 8 - alkynyl, C 2 -C 8 alkynyloxy, C3-C 8 -cycloalkyl, amino , Ci-C 8 alkylamino and
  • the present invention accordingly also provides novel pyrimidine compounds of the formula I, which are described in more detail below, and fungicidal or pharmaceutical agents which contain these compounds and / or their agriculturally or pharmaceutically acceptable salts and also suitable carriers. Suitable agriculturally or pharmaceutically acceptable carriers are described below.
  • the invention provides the use of the novel pyrimidine compounds for the manufacture of a medicament for the treatment of cancer.
  • An object of the invention are novel pyrimidine compounds of the formula I, wherein the variables have the general meanings or the meanings mentioned below, except for compounds in which R 1 is NR 5 R 6 , wherein R 5 is H and R 6 is C 3 -C 6 -haloalkyl, or represents C 3 -C 0 -cycloalkyl and simultaneously
  • R 2 is phenyl which has a substituent L 1 of the formula -Y 1 -Y 2 -T, wherein Y 1 is O, NR h or S, Y 2 is C 1 -C 4 -alkylene and T is OR h or NR h R ', and optionally one or two substituents L 2 , which are selected from halogen, R 3 is halogen and
  • R 4 is NR a R b , NR is a -CN, phenyl, naphthyl or 5- to 10-membered hetaryl.
  • the invention further pyrimidine compounds of the formula I, wherein R 1 , R 3 and R 4 are the above general or mentioned below preferred Have meanings and R 2 is a 5- or ⁇ -membered heteroaromatic radical, wherein the heteroaromatic radical contains 1, 2, 3 or 4 heteroatoms selected from O, S and N, as ring members, a substituent L 1 and optionally 1, 2, 3 or 4 bear identical or different substituents L 2 , wherein L 1 and L 2 have the general or preferred meanings mentioned above.
  • the invention furthermore relates to pyrimidine compounds of the formula I in which R 1 , R 2 , R 3 and R 4 have the abovementioned general or preferred meanings mentioned below, but where L 1 is a radical L 11 or L 13 .
  • L 11 and L 13 are defined below.
  • the invention further pyrimidine compounds of the formula I, wherein R 1 , R 2 and R 3 have the general meanings given above or below, and R 4 for 3-, 4-, 5-, 6-, 7-, 8 -, 9- or 10-membered saturated or partially unsaturated heterocyclyl having 1, 2, 3 or 4 heteroatoms, which are selected from O, N and S, and optionally 1 or 2 carbonyl groups as ring members, wherein the heterocyclyl partially or be fully halogenated and / or have 1, 2 or 3 substituents R x and R x has the general meanings given above or below.
  • the invention furthermore relates to pyrimidine compounds of the formula I in which R 2 , R 3 and R 4 have the abovementioned general or below preferred meanings and R 1 is C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl , Phenyl, naphthyl or a saturated or unsaturated, aromatic or mecanicalomati- see 5-, 6-, 7-, 8-, 9- or 10-membered heterocycle, wherein the heterocycle 1, 2, 3 or 4 heteroatoms selected are O, S and N, as ring members and may also contain 1 or 2 CO groups as ring members, where R 1 may be partially or fully halogenated and / or 1, 2, 3 or 4 equal or different may carry different substituents L 3 , where L 3 has the general meanings given above or below preferred meanings.
  • the invention also pyrimidine compounds of the formula I, wherein R 2 , R 3 and R 4 have the general meanings given above or below and R 1 is a radical of the formula NR 5 R 6 , where R 5 and R 6 is the have the above general or preferred meanings given below, with the proviso that neither R 5 nor R 6 are H.
  • the invention furthermore relates to pyrimidine compounds of the formula I in which R 2 , R 3 and R 4 have the abovementioned general or below preferred meanings and R 1 is a radical of the formula OR 7 or SR 8 , where R 7 and R 8 have the general or preferred meanings mentioned above.
  • the compounds of the formula I can have one or more centers of chirality and are then present as enantiomer or diastereomer mixtures.
  • the invention provides both the pure enantiomers or diastereomers and mixtures thereof or the inventive use of the pure enantiomers or diastereomers of the compound I or mixtures thereof.
  • Suitable compounds of the general formula I also include all possible stereoisomers (cis / trans isomers) and mixtures thereof.
  • Suitable agriculturally useful salts are, in particular, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the fungicidal activity of the compounds I. So come as cations in particular the ions of the alkali metals, preferably sodium and potassium, the alkaline earth metals, preferably calcium, magnesium and barium, and the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion, the desired one to four Ci -C 4 -alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri (C 1 -C 4 -alkyl) sulfonium and sulfoxonium ions, preferably tris
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C 1 -C 4 -alkanoic acids, preferably formate, acetate, propionate and butyrate. They may be formed by reaction of I with an acid of the corresponding anion, preferably hydrochloric, hydrobromic, sulfuric, phosphoric or nitric acid.
  • Suitable pharmaceutically acceptable salts are, in particular, physiologically tolerated salts of compound I, in particular the acid addition salts with physiologically tolerated acids.
  • suitable organic and inorganic acids are hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, C 1 -C 4 -alkylsulfonic acids, such as methanesulfonic acid, aromatic sulfonic acids, such as benzenesulfonic acid and toluenesulfonic acid, oxalic acid, maleic acid, fumaric acid, lactic acid, tartaric acid, adipic acid and benzoic acid.
  • suitable acids are described, for example, in Fort Whitney der Arzneistoffforschung, Volume 10, pages 224 et seq., Birkhäuser Verlag, Basel and Stuttgart, 1966, to which reference is hereby made in their entirety.
  • Halogen fluorine, chlorine, bromine and iodine
  • Ci-C2-alkyl is methyl or ethyl.
  • C 1 -C 4 -alkyl is, for example, propyl, isopropyl, butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl) or 1, 1-dimethylethyl (tert-butyl).
  • C 1 -C 6 -alkyl is, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, hexyl , 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-methylpropyl, or 1-ethyl-2-methylpropyl.
  • d-Cs-alkyl is, for example, heptyl, octyl, 2-ethylhexyl and positional isomeric go away.
  • C 1 -C 10 -alkyl is, for example, nonyl, decyl and positional isomers thereof.
  • Branched Cs-Cs-alkyl is an alkyl group of 3 to 8 carbon atoms, at least one of which is a secondary or tertiary carbon atom. Examples thereof are isopropyl, tert-butyl, 2-butyl, isobutyl, 2-pentyl, 2-hexyl, 3-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1-methyl-1-ethylpropyl and the like.
  • Haloalkyl straight-chain or branched alkyl groups having 1 to 2, 1 to 4, 1 to 6, 1 to 8 or 1 to 10 carbon atoms (as mentioned above), wherein in these groups partially or completely the hydrogen atoms may be replaced by halogen atoms as mentioned above in particular C 1 -C 3 -haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromethyl, 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-trich
  • C 1 -C 10 -hydroxyalkyl straight-chain or branched alkyl groups having 1 to 2, 1 to 4, 2 to 4, 1 to 6, 2 to 6, 1 to 8 2 to 8, 1 to 10 or 2 to 10 carbon atoms (as mentioned above ), wherein at least one of the hydrogen atoms is replaced by a hydroxy group, as in 2-hydroxyethyl or 3-hydroxypropyl.
  • C2-C6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3 Methyl 1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl 3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propen
  • Alkadienyl diunsaturated, straight-chain or branched hydrocarbon radicals having 4 to 6, 4 to 8 or 4 to 10 carbon atoms and two double bonds in any position, but preferably not cumulated, eg. B. 1, 3-butadienyl, 1-methyl-1,3-butadienyl, 2-methyl-1,3-butadienyl, penta-1,3-dien-1-yl, hexa-1,4-diene-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, hep- ta-1, 4-dien-7-yl, h
  • Haloalkenyl and the haloalkenyl moieties in haloalkenyloxy, haloalkenylcarbonyl and the like unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, 2 to 6, 2 to 8 or 2 to 10 carbon atoms and a double bond in any position (as mentioned above), wherein these groups, the hydrogen atoms may be partially or completely replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, z. Chloro vinyl, chloroallyl and the like;
  • C 2 -C 6 -alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl 2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2- methyl-3-pentynyl, 2-methyl-4-
  • Halogenoalkynyl and the haloalkynyl moieties in haloalkynyloxy, haloalkynylcarbonyl and the like unsaturated, straight-chain or branched hydrocarbon radicals having 3 to 4, 3 to 6, 3 to 8 or 3 to 10 carbon atoms and one or two triple bonds in any position (as mentioned above), in these groups, the hydrogen atoms may be partially or completely replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine;
  • Halocycloalkyl and the halocycloalkyl moieties in halocycloalkoxy, halo-cycloalkylcarbonyl and the like monocyclic, saturated hydrocarbon groups having 3 to 6, 3 to 8 or 3 to 10 carbon ring members (as mentioned above), in which the hydrogen atoms are partially or completely substituted by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, may be replaced;
  • Cycloalkyl-Ci-C4-alkyl Ci-C4-alkyl (as defined above), wherein a hydrogen atom is replaced by a cycloalkyl group, for. Cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl and the like.
  • Cycloalkenyl monocyclic, monounsaturated hydrocarbon groups with 3 to
  • ring members such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl, cyclohexen-4-yl and the like;
  • Halocycloalkenyl monocyclic, monounsaturated hydrocarbon groups having 3 to 10, 3 to 8, 3 to 6, preferably 5 to 6 carbon ring members (as mentioned above), wherein the hydrogen atoms are partially or completely halogenated as mentioned above, in particular fluorine, chlorine and Bromine, can be replaced;
  • Bicycloalkyl bicyclic hydrocarbon radical having 5 to 10 carbon atoms, such as bicyclo [2.2.1] hept-1-yl, bicyclo [2.2.1] hept-2-yl, bicyclo [2.2.1] hept-7-yl, Bicyclo [2.2.2] oct-1-yl, bicyclo [2.2.2] oct-2-yl, bicyclo [3.3.0] octyl, bicyclo [4.4.0] decyl, decalin and the like;
  • Ci-C2-alkoxy is methoxy or ethoxy.
  • C 1 -C 4 -alkoxy is, for example, n-propoxy, 1-methylethoxy (isopropoxy), butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1, 1-dimethylethoxy (tert-butoxy).
  • d-C ⁇ -alkoxy is, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1- Methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1, 2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy.
  • C 1 -C 8 -alkoxy represents, for example, heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof.
  • C 1 -C 10 -alkoxy is, for example, nonyloxy, decyloxy and positional isomers thereof.
  • Haloalkoxy for an alkoxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, preferably by fluorine.
  • Ci-C 2 haloalkoxy is z.
  • OCH 2 F, OCHF 2 , OCF 3 , OCH 2 Cl, OCHCl 2 , OCCl 3 chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy , 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or OC 2 Fs ci C 4 -haloalkoxy more
  • C 1 -C 6 -haloalkoxy is, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.
  • Alkenyloxy Alkenyl as mentioned above, which is bonded via an oxygen atom, for. C 3 -C 6 alkenyloxy such as 1-propenyloxy, 2-propenyloxy, 1-methylethenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1-methyl-1-propenyloxy, 2-methyl-1-propenyloxy, 1 Methyl 2-propenyloxy, 2-methyl-2-propenyloxy, 1-pentenyloxy, 2-pentenyloxy, 3-pentenyloxy, 4-pentenyloxy, 1-methyl-1-butenyloxy, 2-methyl-1-butenyloxy, 3-methyl 1-butenyloxy, 1-methyl-2-butenyloxy, 2-methyl-2-butenyloxy, 3-methyl-2-butenyloxy, 1-methyl-3-butenyloxy, 2-methyl-3-butenyloxy, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyloxy, 1,
  • 3-methyl-1-pentenyloxy 4-methyl-1-pentenyloxy, 1-methyl-2-pentenyloxy, 2-methyl-2-pentenyloxy, 3-methyl-2-pentenyloxy, 4-methyl-2-pentenyloxy, 1 - Methyl 3-pentenyloxy, 2-methyl-3-pentenyloxy, 3-methyl-3-pentenyloxy, 4-methyl-3-pentenyloxy, 1-methyl-4-pentenyloxy, 2-methyl-4-pentenyloxy, 3-methyl-4 pentenyloxy, 4-methyl-4-pentenyloxy, 1, 1-dimethyl-2-butenyloxy,
  • Haloalkenyloxy an alkenyloxy radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, preferably by fluorine.
  • Alkynyloxy alkynyl as mentioned above, which is bonded via an oxygen atom, for.
  • B. C3-C6 alkynyloxy such as 2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-propynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy, 1-methyl-2-butynyloxy, 1 - Methyl-3-butynyloxy, 2-methyl-3-butynyloxy, 1-ethyl-2-propynyloxy, 2-hexynyloxy, 3-hexynyloxy, 4-hexynyloxy, 5-hexynyloxy, 1-methyl-2-pentynyloxy, 1-methyl 3-pentynyloxy and the like;
  • Haloalkynyloxy an alkynyloxy radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, preferably by fluorine.
  • Cycloalkoxy Cycloalkyl as mentioned above, which is bonded via an oxygen atom, for. C3-Cio-cycloalkoxy or Cs-Cs-cycloalkoxy such as cyclopropoxy, cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy and the like; Cycloalkenyloxy: Cycloalkenyl as mentioned above, which is bonded via an oxygen atom, for.
  • Alkoxyalkyl alkyl as defined above having from 1 to 8, 1 to 6 or 1 to 4, especially 1 to 3 carbon atoms, wherein a hydrogen atom is replaced by an alkoxy group having 1 to 8, 1 to 6 or 1 to 4 carbon atoms, e.g. , Methoxymethyl, 2-methoxyethyl, ethoxymethyl, 3-methoxypropyl, 3-ethoxypropyl and the like.
  • Cyanoalkyl alkyl as defined above having from 1 to 8, 1 to 6 or 1 to 4, especially 1 to 3 carbon atoms, wherein a hydrogen atom is replaced by a cyano group;
  • Alkylcarbonyl group of the formula R-CO-, wherein R is an alkyl group as defined above, e.g. B. C 1 -C 8 -alkyl, C 1 -C 8 -alkyl, C 1 -C 6 -alkyl, C 1 -C 4 -alkyl or C 1 -C 2 -alkyl. Examples are acetyl, propionyl and the like.
  • Alkylthiocarbonyl group of the formula R-CS-, wherein R is an alkyl group as defined above, e.g. B. C 1 -C 6 -alkyl, C 1 -C 8 -alkyl, C 1 -C 6 -alkyl, C 1 -C 4 -alkyl or C 1 -C 2 -alkyl. Examples are thioacetyl, thiopropionyl and the like.
  • Haloalkylcarbonyl group of the formula R-CO-, wherein R is a haloalkyl group as defined above, e.g. B. for Ci-Cio-haloalkyl, Ci-C 8 -haloalkyl, Ci-C ⁇ -haloalkyl, Ci-C4-haloalkyl or Ci-C2-haloalkyl. Examples are trifluoroacetyl, trifluoropropionyl and the like.
  • Haloalkylthiocarbonyl group of the formula R-CS-, wherein R is a haloalkyl group as defined above, e.g. B. for Ci-Cio-haloalkyl, Ci-C 8 -haloalkyl, Ci-C 6 -haloalkyl, Ci-C4-haloalkyl or Ci-C2-haloalkyl. Examples are trifluorothioacetyl, trifluorothiopropionyl and the like.
  • Alkenylcarbonyl group of the formula R-CO-, wherein R is an alkenyl group as defined above, e.g. B. for C 2 -C alkenyl, C 2 -C 8 alkenyl, C 2 -C 6 alkenyl or C 2 -C 4 alkenyl.
  • Alkenylthiocarbonyl group of the formula R-CS-, wherein R is an alkenyl group as defined above, e.g. B. for C 2 -C alkenyl, C 2 -C 8 alkenyl, C 2 -C 6 alkenyl or C 2 -C 4 alkenyl.
  • Haloalkenylcarbonyl group of the formula R-CO-, wherein R is a haloalkenyl group as defined above, e.g. B. for C 2 -C 10 haloalkenyl, C 2 -C 8 haloalkenyl, C 2 -C 6 haloalkenyl or C 2 -C 4 haloalkenyl.
  • Haloalkenylthiocarbonyl group of the formula R-CS-, wherein R is a haloalkenyl group as defined above, e.g. B. for C 2 -C 10 haloalkenyl, C 2 -C 8 haloalkenyl, C 2 -C 6 haloalkenyl or C 2 -C 4 haloalkenyl.
  • Alkynylcarbonyl group of the formula R-CO-, wherein R is an alkynyl group as defined above, e.g. B. for C 2 -Cio-alkynyl, C 2 -C 8 -alkynyl, C 2 -C 6 -alkynyl or C 2 -C 4 - alkynyl.
  • Alkynylthiocarbonyl group of the formula R-CS- in which R is an alkynyl group as defined above, eg. Kinyl B. C 2 -Cio-alkynyl, C 2 -Cs-Al kinyl, C 2 -C 6 alkynyl or C 2 -C 4 -alkyl.
  • Haloalkynylcarbonyl group of the formula R-CO-, wherein R is a haloalkynyl group as defined above, e.g. B. for C 2 -Cio-haloalkynyl, C 2 -Cs haloalkynyl, C 2 -C 6 -haloalkynyl or C 2 -C 4 -haloalkynyl.
  • Haloalkynylthiocarbonyl group of the formula R-CS-, wherein R is a haloalkynyl group as defined above, e.g. B. for C 2 -Cio-haloalkynyl, C 2 -Cs haloalkynyl, C 2 -C 6 -haloalkynyl or C 2 -C 4 -haloalkynyl.
  • Cycloalkylcarbonyl group of the formula R-CO-, wherein R is a cycloalkyl group as defined above, e.g. B. for C3-Cio-cycloalkyl, C3-Cs-cycloalkyl, C3-C6-cycloalkyl or Cs-C ⁇ -cycloalkyl.
  • Cycloalkylthiocarbonyl group of the formula R-CS-, wherein R is a cycloalkyl group as defined above, e.g. B. for C3-Cio-cycloalkyl, C3-Cs-cycloalkyl, C3-C6-cycloalkyl or Cs-C ⁇ -cycloalkyl.
  • Cycloalkenylcarbonyl group of the formula R-CO-, in which R stands for a cycloalkenyl group as defined above, eg. B. for C3-Cio-cycloalkenyl, C3-Cs-cycloalkenyl, C3-C6-cycloalkenyl or Cs-C ⁇ -cycloalkenyl.
  • Cycloalkenylthiocarbonyl group of the formula R-CS-, wherein R is a cycloalkenyl group as defined above, e.g. For C3-Cio-cycloalkenyl, Cs-Cs-cycloalkenyl, C3-C6-cycloalkenyl or Cs-C ⁇ -cycloalkenyl.
  • Alkylcarbonyloxy group of the formula R-CO-O-, wherein R is an alkyl group as defined above, e.g. B. C 1 -C 8 -alkyl, C 1 -C 8 -alkyl, C 1 -C 6 -alkyl, C 1 -C 4 -alkyl or C 1 -C 2 -alkyl. Examples are acetyloxy, propionyloxy and the like.
  • Alkylthiocarbonyloxy group of the formula R-CS-O-, wherein R is an alkyl group as defined above, e.g. B. C 1 -C 6 -alkyl, C 1 -C 8 -alkyl, C 1 -C 6 -alkyl, C 1 -C 4 -alkyl or C 1 -C 2 -alkyl. Examples are thioacetyloxy, thiopropionyloxy and the like.
  • Haloalkylcarbonyloxy group of the formula R-CO-O- in which R is a haloalkyl group as defined above, e.g. B. for Ci-Cio-haloalkyl, Ci-Cs haloalkyl, Ci-C ⁇ -haloalkyl, Ci-C4-haloalkyl or Ci-C2-haloalkyl. Examples are trifluoroacetyloxy, trifluopropionyloxy and the like.
  • Halogenoalkylthiocarbonyloxy group of the formula R-CS-O-, wherein R is a haloalkyl group as defined above, e.g. B. for Ci-Cio-haloalkyl, Ci-Cs haloalkyl, Ci-C 6 -haloalkyl, Ci-C4-haloalkyl or Ci-C2-haloalkyl. Examples are trifluorothioacetyloxy, trifluorothiopropionyloxy and the like.
  • Alkenylcarbonyloxy group of the formula R-CO-O-, wherein R is an alkenyl group as defined above, e.g. B. for C 2 -C alkenyl, C 2 -C 8 alkenyl, C 2 -C 6 alkenyl or C 2 -C 4 alkenyl.
  • Alkenylthiocarbonyloxy group of the formula R-CS-O-, wherein R is an alkenyl group as defined above, e.g. For example, C2-Cio-alkenyl, C2-Cs-alkenyl, C2-C6-alkenyl or C2-C4-alkenyl.
  • Haloalkenylcarbonyloxy group of the formula R-CO-O- in which R is a haloalkenyl group as defined above, e.g. B. C2-Cio-haloalkenyl, C2-C8 haloalkenyl, C2-C6-haloalkenyl or C2-C4 haloalkenyl.
  • Haloalkenylthiocarbonyloxy group of the formula R-CS-O-, wherein R is a haloalkenyl group as defined above, e.g. B. for C2-Cio-haloalkenyl, C2-C8-haloalkenyl, C2-C6-haloalkenyl or C2-C4-haloalkenyl.
  • Alkynylcarbonyloxy group of the formula R-CO-O-, wherein R is an alkynyl group as defined above, e.g. B. for C 2 -C 10 -alkynyl, C 2 -C 8 -alkynyl, C 2 -C 6 -alkynyl or C 2 -C 4 -alkynyl.
  • Alkynylthiocarbonyloxy group of the formula R-CS-O-, wherein R is an alkynyl group as defined above, e.g. Kinyl for example, C2-Cio-alkynyl, C 2 -Cs-Al kinyl, C2-C6-alkinyl or C 2 -C 4 -alkyl.
  • Haloalkynylcarbonyloxy group of the formula R-CO-O-, in which R stands for an as defined above halogenoalkynyl group, for. B. for C 2 -Cio-haloalkynyl, C 2 -Cs haloalkynyl, C 2 -C 6 -haloalkynyl or C 2 -C 4 -haloalkynyl.
  • Haloalkynylthiocarbonyloxy group of the formula R-CS-O-, wherein R is a haloalkynyl group as defined above, e.g. B. for C 2 -Cio-haloalkynyl, C 2 -Cs haloalkynyl, C 2 -C 6 -haloalkynyl or C 2 -C 4 -haloalkynyl.
  • Cycloalkylcarbonyloxy group of the formula R-CO-O-, wherein R is a cycloalkyl group as defined above, e.g. B. for C3-Cio-cycloalkyl, C3-Cs-cycloalkyl, C3-C6-cycloalkyl or Cs-C ⁇ -cycloalkyl.
  • Cycloalkylthiocarbonyloxy group of the formula R-CS-O-, wherein R is a cycloalkyl group as defined above, e.g. B. C3-Cio-cycloalkyl, C3-Cs-cycloalkyl, C 3 -C 6 -CyCl oa I kyl or C 5 -C 6 cycloalkyl.
  • Cycloalkenylcarbonyloxy group of the formula R-CO-O-, wherein R is a cycloalkenyl group as defined above, e.g. B. for C3-Cio-cycloalkenyl, C3-C8-cycloalkenyl, Cs-C ⁇ -cycloalkenyl or Cs-C ⁇ -cycloalkenyl.
  • Cycloalkenylthiocarbonyloxy group of the formula R-CS-O-, in which R stands for a cycloalkenyl group as defined above, eg. B. for C3-Cio-cycloalkenyl, C3-C8-cycloalkenyl, Cs-C ⁇ -cycloalkenyl or Cs-C ⁇ -cycloalkenyl.
  • Alkoxycarbonyl group of the formula R-CO-, wherein R is an alkoxy group as defined above, e.g. B. for C 1 -C 10 -alkoxy, C 1 -C 5 -alkoxy, C 1 -C 6 -alkoxy, C 1 -C 4 -alkoxy or C 1 -C 2 -alkoxy.
  • R is an alkoxy group as defined above, e.g. B. for C 1 -C 10 -alkoxy, C 1 -C 5 -alkoxy, C 1 -C 6 -alkoxy, C 1 -C 4 -alkoxy or C 1 -C 2 -alkoxy.
  • R is an alkoxy group as defined above, e.g. B. for C 1 -C 10 -alkoxy, C 1 -C 5 -alkoxy, C 1 -C 6 -alkoxy, C 1 -C 4 -alkoxy or C 1 -C 2 -
  • Alkoxythiocarbonyl group of the formula R-CS-, wherein R is an alkoxy group as defined above, e.g. B. for Ci-Cio-alkoxy, d-Cs-alkoxy, Ci-C ⁇ -alkoxy, CrC 4 - Alkoxy or Ci-C2-alkoxy. Examples are methoxythiocarbonyl, ethoxythiocarbonyl and the like.
  • Haloalkoxycarbonyl group of the formula R-CO-, wherein R is a haloalkoxy group as defined above, e.g. B. for Ci-Cio-haloalkoxy, Ci-Cs-
  • Haloalkoxy Ci-C ⁇ -haloalkoxy, Ci-C4-haloalkoxy or Ci-C2-haloalkoxy. Examples are trifluoromethoxycarbonyl, trifluoroethoxycarbonyl and the like.
  • Haloalkoxythiocarbonyl group of the formula R-CS- in which R is a haloalkoxy group as defined above, e.g. for Ci-Cio-haloalkoxy, Ci-Cs-
  • Haloalkoxy Ci-C ⁇ -haloalkoxy, Ci-C4-haloalkoxy or Ci-C2-haloalkoxy. Examples are trifluoromethoxythiocarbonyl, trifluoroethoxythiocarbonyl and the like.
  • Alkenyloxycarbonyl group of the formula R-CO- in which R is an alkenyloxy group as defined above, eg. For C2-Cio-alkenyloxy, C2-Cs-alkenyloxy, C2-C6-alkenyloxy or C2-C4-alkenyloxy.
  • Alkenyloxythiocarbonyl group of the formula R-CS-, wherein R is an alkenyloxy group as defined above, e.g. For C2-Cio-alkenyloxy, C2-Cs-alkenyloxy, C2-C6-alkenyloxy or C2-C4-alkenyloxy.
  • Haloalkenyloxycarbonyl group of the formula R-CO-, wherein R is a haloalkenyloxy group as defined above, e.g. B. for C2-Cio-haloalkenyloxy, C2-Cs-haloalkenyloxy, C2-C6-haloalkenyloxy or C2-C4-haloalkenyloxy.
  • Haloalkenyloxythiocarbonyl group of the formula R-CS-, wherein R is a haloalkenyloxy group as defined above, e.g. B. for C2-Cio-haloalkenyloxy, C2-Cs-haloalkenyloxy, C2-C6-haloalkenyloxy or C2-C4-haloalkenyloxy.
  • Alkynyloxycarbonyl group of the formula R-CO-, wherein R is an alkynyloxy group as defined above, e.g. B. for C2-Cio-alkynyloxy, C2-Cs-alkynyloxy, C2-C6-alkynyloxy or C2-C4-alkynyloxy.
  • Alkynyloxythiocarbonyl group of the formula R-CS-, wherein R is an alkynyloxy group as defined above, e.g. B. for C2-Cio-alkynyloxy, C2-Cs-alkynyloxy, C2-C6-alkynyloxy or C2-C4-alkynyloxy.
  • Haloalkynyloxycarbonyl group of the formula R-CO- in which R is a haloalkynyloxy group as defined above, e.g. B. for C2-Cio-haloalkynyloxy, C2-C8-haloalkynyloxy, C2-C6-haloalkynyl or C2-C4-haloalkynyloxy.
  • Haloalkynyloxythiocarbonyl group of the formula R-CS- in which R is a haloalkynyloxy group as defined above, e.g. B. for C2-Cio-haloalkynyloxy, C2-C8-haloalkynyloxy, C2-C6-haloalkynyl or C2-C4-haloalkynyloxy.
  • Cycloalkyloxycarbonyl group of the formula R-CO-, wherein R is a cycloalkyloxy group as defined above, e.g. B. for C3-Cio-cycloalkyloxy, C3-C8-cycloalkyloxy, Cs-C ⁇ -cycloalkyloxy or Cs-C ⁇ -cycloalkyloxy.
  • Cycloalkyloxythiocarbonyl group of the formula R-CS-, wherein R is a cycloalkyloxy group as defined above, e.g. B. for C3-Cio-cycloalkyloxy, C3-C8-cycloalkyloxy, Cs-C ⁇ -cycloalkyloxy or Cs-C ⁇ -cycloalkyloxy.
  • Cycloalkenyloxycarbonyl group of the formula R-CO-, wherein R is a cycloalkenyloxy group as defined above, e.g. B. for C3-Cio-cycloalkenyloxy, C3-C8-cycloalkenyloxy, Cs-C ⁇ -cycloalkenyloxy or Cs-C ⁇ -cycloalkenyloxy.
  • Cycloalkenyloxythiocarbonyl group of the formula R-CS-, wherein R is a cycloalkenyloxy group as defined above, e.g. B. for C3-Cio-cycloalkenyloxy, C3-C8-cycloalkenyloxy, Cs-C ⁇ -cycloalkenyloxy or Cs-C ⁇ -cycloalkenyloxy.
  • Alkoxycarbonyloxy group of the formula R-CO-O-, wherein R is an alkoxy group as defined above, e.g. B. for Ci-Cio-alkoxy, Ci-Cs-alkoxy, Ci-C ⁇ -alkoxy, C1-C4-alkoxy or Ci-C2-alkoxy. Examples are methoxycarbonyl, ethoxycarbonyl and the like.
  • Alkoxythiocarbonyloxy group of the formula R-CS-O-, wherein R is an alkoxy group as defined above, e.g. B. for Ci-Cio-alkoxy, Ci-Cs-alkoxy, Ci-C ⁇ -alkoxy, CrC 4 -alkoxy or Ci-C2-alkoxy. Examples are methoxycarbonyl, ethoxycarbonyl and the like.
  • Haloalkoxycarbonyloxy group of the formula R-CO-O- in which R is a haloalkoxy group as defined above, e.g. B. for Ci-Cio-haloalkoxy, Ci-Cs haloalkoxy, Ci-C ⁇ -haloalkoxy, Ci-C4-haloalkoxy or Ci-C2-haloalkoxy. Examples are trifluoromethoxycarbonyl, trifluoroethoxycarbonyl and the like.
  • Haloalkoxythiocarbonyloxy group of the formula R-CS-O-, wherein R is a haloalkoxy group as defined above, e.g. B.
  • Ci-Cio-haloalkoxy for Ci-Cio-haloalkoxy, Ci-Cs haloalkoxy, Ci-C ⁇ -haloalkoxy, Ci-C4-haloalkoxy or Ci-C2-haloalkoxy.
  • Examples are trifluoromethoxycarbonyl, trifluoroethoxycarbonyl and the like.
  • Alkenyloxycarbonyloxy group of the formula R-CO-O-, wherein R is an alkenyloxy group as defined above, e.g. B. for C 2 -C alkenyloxy, C 2 -C 8 alkenyloxy, C 2 -C 6 alkenyloxy or C 2 -C 4 alkenyloxy.
  • Alkenyloxythiocarbonyloxy group of the formula R-CS-O-, wherein R is an alkenyloxy group as defined above, e.g. B. for C 2 -C alkenyloxy, C 2 -C 8 alkenyloxy, C 2 -C 6 alkenyloxy or C 2 -C 4 alkenyloxy.
  • Haloalkenyloxycarbonyloxy group of the formula R-CO-O- in which R is a haloalkenyloxy group as defined above, eg. B. for C 2 -C 10 haloalkenyloxy, C 2 -C 8 haloalkenyloxy, C 2 -C 6 haloalkenyloxy or C 2 -C 4 haloalkenyloxy.
  • Haloalkenyloxythiocarbonyloxy group of the formula R-CS-O-, wherein R is a haloalkenyloxy group as defined above, e.g. B. for C 2 -C 10 haloalkenyloxy, C 2 -C 8 haloalkenyloxy, C 2 -C 6 haloalkenyloxy or C 2 -C 4 haloalkenyloxy.
  • Alkynyloxycarbonyloxy group of the formula R-CO-O-, wherein R is an alkynyloxy group as defined above, e.g. B. for C2-Cio-alkynyloxy, C2-Cs-alkynyloxy, C2-C6-alkynyloxy or C2-C4-alkynyloxy.
  • Alkynyloxythiocarbonyloxy group of the formula R-CS-O-, wherein R is an alkynyloxy group as defined above, e.g. B. for C 2 -C 10 -alkynyloxy, C 2 -C 8 -alkynyloxy, C 2 -C 6 -alkynyloxy or C 2 -C 4 -alkynyloxy.
  • Haloalkynyloxycarbonyloxy group of the formula R-CO-O- in which R is a haloalkynyloxy group as defined above, e.g. B. for C2-Cio-haloalkynyloxy, C2-C8-haloalkynyloxy, C2-C6-haloalkynyl or C2-C4-haloalkynyloxy.
  • Haloalkynyloxythiocarbonyloxy group of the formula R-CS-O- in which R is a haloalkynyloxy group as defined above, e.g. B. for C 2 -C 10 haloalkynyloxy, C 2 -C 8 haloalkynyloxy, C 2 -C 6 haloalkynyl or C 2 -C 4 haloalkynyloxy.
  • Cycloalkyloxycarbonyloxy group of the formula R-CO-O-, wherein R is a cycloalkyloxy group as defined above, e.g. B. for C3-Cio-cycloalkyloxy, C3-C8-cycloalkyloxy, Cs-C ⁇ -cycloalkyloxy or Cs-C ⁇ -cycloalkyloxy.
  • Cycloalkyloxythiocarbonyloxy group of the formula R-CS-O-, wherein R is a cycloalkyloxy group as defined above, e.g. B. for C3-Cio-cycloalkyloxy, C3-C8-cycloalkyloxy, Cs-C ⁇ -cycloalkyloxy or Cs-C ⁇ -cycloalkyloxy.
  • Cycloalkenyloxycarbonyloxy group of the formula R-CO-O- in which R is a cycloalkenyloxy group as defined above, eg. B. for C3-Cio-cycloalkenyloxy, Cs-Cs-cycloalkenyloxy, Cs-C ⁇ -cycloalkenyloxy or Cs-C ⁇ -cycloalkenyloxy.
  • Cycloalkenyloxythiocarbonyloxy group of the formula R-CS-O-, wherein R is a cycloalkenyloxy group as defined above, e.g. B. for C3-Cio-cycloalkenyloxy, Cs-Cs-cycloalkenyloxy, Cs-C ⁇ -cycloalkenyloxy or Cs-C ⁇ -cycloalkenyloxy.
  • Alkylamino group of the formula RHN-, in which R stands for an alkyl group as defined above.
  • Dialkylamino group of the formula RRN-, wherein each R is independently an alkyl group as defined above.
  • Alkylaminocarbonyl group of the formula RHN-CO-, wherein R is an alkyl group as defined above.
  • Dialkylaminocarbonyl group of the formula RRN-CO-, wherein each R is independently an alkyl group as defined above.
  • Alkylaminothiocarbonyl group of the formula RHN-CS- in which R stands for an alkyl group as defined above.
  • Dialkylaminothiocarbonyl group of the formula RRN-CS- wherein each R is independently an alkyl group as defined above.
  • Alkylaminocarbonyloxy group of the formula RHN-CO-O- in which R is an alkyl group as defined above.
  • Dialkylaminocarbonyloxy group of the formula RRN-CO-O-, wherein each R is independently an alkyl group as defined above.
  • Alkylaminothiocarbonyloxy group of the formula RHN-CS-O- in which R is an alkyl group as defined above.
  • Dialkylaminothiocarbonyloxy group of the formula RRN-CS-O- wherein each R is independently an alkyl group as defined above.
  • Alkylthio Alkyl as defined above attached via an S atom.
  • Haloalkylthio haloalkyl, as defined above, which is bonded via an S atom.
  • Alkylsulfinyl (also sometimes referred to as alkylsulfoxyl): Alkyl as defined above which is bonded through an SO group.
  • Alkylsulfonyl Alkyl as defined above attached via an S (O) 2 group.
  • Aryl carbocyclic aromatic radical having 6 to 14 carbon atoms, such as phenyl, naphthyl, anthracenyl or phenanthrenyl.
  • C ⁇ -C-io-Arvl is phenyl or naphthyl.
  • Aryloxy O-linked carbocyclic aromatic radical having 6 to 14 carbon atoms, such as phenoxy, naphthyloxy, anthracenyloxy or phenanthrenyloxy.
  • C ⁇ -Cio-Aryloxy is phenoxy or naphthoxy.
  • Arylthio carbons bonded via S carbocyclic aromatic radical having 6 to 14 carbon atoms, such as phenylthio, naphthylthio, anthracenylthio or Phenanthrenylthio.
  • Ce-Cio-arylthio stands for phenylthio or naphthylthio.
  • Arylalkyl alkyl (as defined above), e.g. C 1 -C 8 -alkyl, C 1 -C 6 -alkyl or C 1 -C 4 -alkyl, where a hydrogen atom is replaced by an aryl group, such as benzyl, phenethyl and the like.
  • Arylalkoxy alkoxy (as defined above), e.g., C 1 -C 8 -alkoxy, C 1 -C 6 -alkoxy or C 1 -C 4 -alkoxy, where one hydrogen atom has been replaced by an aryl group, such as benzyloxy, phenethyloxy and the like.
  • heterocyclyl tri-, tetra-, penta- or six-membered saturated or partially unsaturated heterocycle (hereinafter also heterocyclyl) containing one, two, three or four
  • B. C-linked 5-membered heteroaryl containing one to three nitrogen atoms or one or two nitrogen atoms and one sulfur or oxygen atom as ring members such as 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3 -Pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl,
  • Alkylene divalent branched or preferably unbranched chains of 1 to 8 carbon atoms, e.g. CH 2 , CH 2 CH 2 , -CH (CH 3 ) -, CH 2 CH 2 CH 2 , CH (CH 3 ) CH 2 , CH 2 CH (CH 3 ), CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 and CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 ;
  • Oxyalkylene divalent unbranched chains of 2 to 4 CH 2 groups, wherein a valence is bonded to the skeleton via an oxygen atom, for. OCH 2 CH 2 , OCH 2 CH 2 CH 2 and OCH 2 CH 2 CH 2 CH 2 ;
  • Oxyalkylenoxy divalent unbranched chains of 1 to 3 CH 2 groups, wherein both valences are bonded via an oxygen atom to the skeleton, z. OCH 2 O, OCH 2 CH 2 O and OCH 2 CH 2 CH 2 O;
  • compounds of the general formula IR 1 preferably have a radical R 1 'which is selected from C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 3 -C 10 -cycloalkyl, C 3 -Cio-cycloalkenyl, phenyl, naphthyl and a saturated or unsaturated, aromatic or non-aromatic, preferably C-bonded, 5-, 6-, 7-, 8-, 9- or 10-membered heterocycle, wherein the heterocycle 1, 2, 3 or 4 heteroatoms selected from O, S and N as ring members and also containing 1 or 2 CO groups as ring members, where R 1 'may be partially or fully halogenated and / or 1, 2, 3 or 4 may bear the same or different substituents L 3 , which are as defined above.
  • R 1 ' which is selected from C 1 -C 10 -alkyl, C 2 -C 10 -al
  • R 1 ' is Ci-Cio-alkyl, C 3 -C 8 alkenyl, C 3 -C 8 -alkyl is kinyl, C 3 - C ⁇ cycloalkyl, Cs-C ⁇ cycloalkenyl, wherein the two latter groups, a C1 -C4 alkylidene group, or for a 5- or 6-membered saturated or aromatic heterocycle, which is bonded via carbon.
  • R 1 ' may be partially or fully halogenated or may carry one, two, three or four identical or different L 3 groups as defined above.
  • L 3 is preferably selected from halogen, cyano, C 1 -C 6 -alkyl, C 2 -C 6 alkenyl, C 2 -C 6 -alkyl kinyl, Ci-C 6 alkoxy, Ci-C 6 alkoxycarbonyl, Ci-C ⁇ -alkoximino, C2-C6 Alkenyloximino, C 2 -C 6 Alkinyloximino, C 3 - C6-cycloalkyl, Cs-C 6 - cycloalkenyl, wherein the aliphatic or alicyclic groups for their part may be partially or fully halogenated or one, two or three groups L can wear. 4
  • L 4 is preferably selected from halo- gen, cyano, Ci -C 6 -alkyl, C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 -Al kinyl, -C 6 - alkylcarbonyl, CrCerHalogenalkylcarbonyl and Ci-C 6 alkoxy.
  • R 1 is alkyl of Ci -Ce-Al, in particular branched C3 -Cs alkyl, Ci-C 6 haloalkyl, C 3 -Cs-alkenyl, in particular branched C 3 -Cs-Al -alkenyl, C 3 -C 6 - Cycloalkyl, which may have a Ci-C4-alkyl group, or Cs-C ⁇ -cycloalkenyl, which may have a Ci-C4-alkyl group.
  • R 1 ' is branched C 3 -C 8 -alkyl, such as isopropyl, sec-butyl, isobutyl, tert-butyl, 2- and 3-pentyl, 2- and 3-methylbutyl, 1, 1-dimethylpropyl, 2, 2-dimethylpropyl, 2- and 3-hexyl, 2-, 3- and 4-methylpentyl and the like.
  • the branch is not on the carbon atom through which the radical R 1 'is attached to the pyrimidine ring. Examples of such alkyl radicals are isobutyl, 2- and 3-methylbutyl, 2,2-dimethylpropyl, 2-, 3- and 4-methylpentyl and the like.
  • IR 1 is preferably a group NR 5 R 6 .
  • R 5 is preferably C 1 -C 6 -alkyl, C 1 -C 5 -haloalkyl, C 1 -C -hydroxyalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 5 -alkyl which carries a substituent selected from is COOH, C 1 -C 4 -alkoxycarbonyl, aminocarbonyl, C 1 -C 5 -alkylaminocarbonyl, di- (C 1 -C 8 -alkyl) aminocarbonyl and C 1 -C 4 -alkylcarbonyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-ci C4-alkyl or phenyl which optionally carries 1, 2 or 3 substituents which are selected from halogen, Ci-C4-alkoxy and Ci-C4-alkyl.
  • R 5 particularly preferably represents linear or branched C 1 -C 8 -alkyl or linear or branched C 1 -C 8 -haloalkyl, with linear or branched C 3 -C 5 -alkyl and linear or branched C 2 -C 8 -haloalkyl being more preferred. Even more preferably R 5 is branched Cs-C ⁇ -alkyl, linear C 2 -C 6 -haloalkyl or branched C 3 -C 6 -haloalkyl.
  • Branched Cs-C ⁇ -alkyl is for example isopropyl, sec-butyl, isobutyl, tert-butyl, 1-methylpropyl, 2- and 3-pentyl, 2- and 3-methylbutyl, 1, 1-dimethylpropyl, 2,2- Dimethylpropyl, 1,2-dimethylpropyl, 2- and 3-hexyl, 2-, 3- and 4-methylpentyl, 1, 2,2-trimethylpropyl and the like.
  • the branched has
  • C 3 -C 6 -alkyl radical is a branch in the 1-position of the (starting from the nitrogen atom to which the radical R 5 is bonded) longest carbon chain of the alkyl radical, ie in ⁇ -position to the nitrogen atom, and optionally a further branching at a further carbon atom the alkyl group, especially in the 2-position of the longest carbon chain of the alkyl group.
  • examples of these are isopropyl, sec-butyl, tert-butyl, 1-methylpropyl, 2-pentyl, 2-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2-hexyl, 2-methylpentyl, 1, 2,2 Trimethylpropyl and the like.
  • the linear or branched C 2 -C 8 -haloalkyl radical is preferably a fluorinated C 2 -C 8 -alkyl radical.
  • the fluorinated C 2 -C 5 -alkyl radical preferably has 1, 2, 3, 4, 5 or 6 fluorine atoms, more preferably 1, 2 or 3 and especially 2 or 3 fluorine atoms.
  • the fluorine atoms are not attached to the carbon atom of the haloalkyl radical attached to directly the nitrogen atom bearing the R 5 radical.
  • the fluorine atoms are particularly preferably bonded in the 2- and / or 3-position of the longest carbon chain of the haloalkyl radical (starting from the nitrogen atom to which the radical R 5 is bonded).
  • the branched C3-C8 haloalkyl group has a branch at the 1-position of the (starting from the nitrogen atom is bound to the R 5) the longest carbon chain of the haloalkyl radical, that is, if appropriate, a further in ⁇ -position to the nitrogen atom, and Branching on another carbon atom of the haloalkyl group, for.
  • the longest carbon chain of the haloalkyl radical In the 2- and / or 3-position of the longest carbon chain of the haloalkyl radical.
  • the linear or branched C 2 -C 8 haloalkyl radical is a fluorinated C 2 -C 3 alkyl radical, e.g. For example, 2-fluoroethyl, 2,2-difluoroethyl,
  • 2,2,2-trifluoroethyl 2-fluoro-1-methylethyl, 2,2-difluoro-1-methylethyl, 1-methyl-2,2,2-trifluoroethyl, bis (fluoromethyl) methyl, bis (difluoromethyl) methyl, Bis (trifluoromethyl) methyl and the like.
  • R 6 is preferably H or has one of the invention or the preferred meanings given for R 5 in.
  • R 6 is particularly preferably H or C 1 -C 4 -alkyl, more preferably H, methyl or ethyl and in particular H or methyl. In a specific embodiment of the invention, R 6 is H.
  • R 6 stands for
  • R 61 preferably represents straight-chain or branched C 1 -C 6 -alkyl, C 3 -C 8 -alkenyl or C 5 -C 6 -cycloalkyl, particularly preferably C 1 -C 6 -alkyl or C 3 -C 6 -cycloalkyl, for example
  • methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, sec-pentyl, cyclopropyl or cyclopentyl preferably isopropyl, isobutyl, tert-butyl, sec-pentyl, cyclopropyl or cyclopentyl and in particular tert-butyl.
  • R 61 is other than hydrogen or methyl.
  • the group R 61 has a branch on the ⁇ -carbon atom.
  • the group R 61 is substituted by heteroatom-bonded groups, such as halogen, alkoxy, alkylthio, amino, alkylamino, dialkylamino or formyl, carboxyl, alkoxycarbonyl, alkoxythiocarbonyl or alkenyl, alkynyl groups or C 2 -C 8 -alkylene, wherein both valences are bonded to the same carbon atom.
  • the group R 61 is substituted by Cs-C ⁇ -cycloalkyl or Cs-Cs-cycloalkenyl.
  • the group R 61 is C (O) R A , C (O) OR A , C (S) OR A , C (O) NR A R B , C (S) NR A R B , C (NR A ) R B , C (O) SR ⁇ or C (S) SR ⁇ substituted.
  • R ⁇ here preferably denotes C 1 -C 6 -alkyl or C 5 -C 6 -cycloalkyl, where these groups may be partially or completely halogenated.
  • the group R 61 is represented by a five, six, seven, eight, nine or ten-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S, substituted.
  • R 62 is hydrogen, straight-chain or branched C 1 -C 8 -alkyl or C 5 -C 6 -cycloalkyl, in particular hydrogen, C 1 -C 6 -alkyl or C 3 -C 6 -cycloalkyl, preferably hydrogen, isopropyl or tert-butyl. If R 62 is an alkyl group, R 62 preferably has the same meaning as R 61 .
  • R 61 and R 62 together form a Cs-C ⁇ -alkylene, in particular a C 3 -C 4 -alkylene group, wherein the carbon chains may be substituted by heteroatom-bonded groups, such as halogen, alkoxy, alkylthio, amino, alkylamino , Dialkylamino or alkoxycarbonyl.
  • R 61 and R 62 together form a C 3 -C 6 -alkylene, in particular a C 3 -C 4 -alkylene group, wherein the carbon chains are interrupted by one or two heteroatoms from the group O, N and S and by heteroatoms bonded groups, such as halogen, alkoxy, alkylthio, amino, alkylamino, dialkylamino or alkoxycarbonyl.
  • R 62 , R 63 , R 64 , R 65 and R 66 are each hydrogen or C 1 -C 4 -alkyl, preferably hydrogen, methyl or ethyl, in particular hydrogen.
  • the substitution of the groups R 62 , R 63 , R 64 , R 65 and R 66 preferably corresponds to that of the group R 61 .
  • R 61 and R 63 together form a C 3 -C 6 -alkylene, Cs-C ⁇ -oxyalkylene or C 2 -C 5 -oxyalkyleneoxy, in particular a C 3 -C 4 -alkylene group.
  • R 63 and R 64 and / or R 65 and R 66 each together form a Cs-C ⁇ -alkylene, Cs-C ⁇ -oxyalkylene or C 2 -C 5 -oxyalkyleneoxy, in particular a C 3 -C 4 -alkylene group ,
  • the index q is zero or one.
  • the index p is zero or 1, in particular zero.
  • R 63 and R 64 are preferably hydrogen, provided that the index p is zero.
  • R 65 is other than hydrogen and R 66 is hydrogen unless the index p is equal to zero.
  • the index p has the value zero or 1 and the index q the value 1.
  • R 65 and R 66 are preferably hydrogen. In an alternative preferred embodiment, R 65 is other than hydrogen and R 66 is hydrogen.
  • Y is oxygen
  • Z represents a monovalent group.
  • Z is selected from C 1 -C 4 -alkylcarbonyl, in particular acetyl, n-propan-1-one, 2-methylpropan-1-one or butan-1-one, hydrogen, carboxyl, formyl, C 1 -C 8 - alkyl, d-Cs-haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 -Halogenalke- nyl, C 2 -C 8 -alkyl kinyl, C 2 -C 8 haloalkynyl, C 3 -C 6 cycloalkyl , C 3 -C 8 cycloalkenyl, C (O) R ⁇ , C (O) OR ⁇ , C (S) OR ⁇ , C (O) SR ⁇ , C (S) SR ⁇ , C (NR A ) SR ⁇ , C (S) R ⁇ , C (NR ⁇ )
  • the abovementioned groups Z can be substituted by one or more groups R b1 .
  • the group Z is substituted by one, two, three or four groups R b1 , such as halogen, or basic or acidic groups, such as NR A R B , guanidyl, amidyl, hydroxy, carboxyl or sulfonic acids , Specifically, Z is selected from H, formyl, C 1 -C 4 alkylcarbonyl and Cs-C ⁇ cycloalkylcarbonyl.
  • the groups R A and R B is hydrogen, Ci-C 4 alkyl or -C 4 - haloalkyl, in particular hydrogen and methyl.
  • R ⁇ preferably 4 alkyl or Ci-C 4 haloalkyl is C, in particular methyl.
  • R 61 is H or C 1 -C 4 -alkyl
  • R 62 is H
  • R 63 is H or C 1 -C 4 -alkyl
  • R 64 is H
  • q is 0 or 1 in particular 1
  • p is 0,
  • Y is O and Z is H, C 1 -C 4 -Al kyl, formyl, Ci-C 4 -alkylcarbonyl or Cs-C ⁇ -cycloalkylcarbonyl.
  • R 5 is preferably H, C 1 -C 8 -alkyl or C 1 -C 5 -synyl haloalkyl, more preferably H, -C 4 - alkyl or Ci-C4-haloalkyl and in particular H or Ci-C 4 alkyl.
  • the group NR 5 R 6 is in each case bound via N ethylglycinol, leucineol, tert-leucinol, valinol, norvalinol, methioninol, phenylalanine, lysinol, argininol, histidinol, asparaginol, glutaminol, serinol, isoleucinol , Cysteinol, hydroxymethylpiperidine, cis-2-hydroxymethyl-4-methylpiperidine, trans-2-hydroxymethyl-4-methylpiperidine, cyclohexylglycinol, cyclopentylglycinol, butylglycinol, pentylglycinol, cis-2-aminocyclohexanol, trans-2-aminocyclohexanol , cis-2-aminocyclopentanol, trans-2-aminocyclopentanol, trans-2-a
  • neither R 5 nor R 6 is H, ie the radical R 1 is a tertiary amine.
  • R 5 and R 6 together with the nitrogen atom to which they are attached form a saturated or unsaturated 5-, 6-, 7- or 8-membered, preferably 5-, 6- or 7- in particular 6- or 7-membered heterocycle, wherein the heterocycle may additionally contain a heteroatom or a heteroatom-containing group as ring member, which is selected from O, N and NR '", wherein R"' for H, Ci-C 8 alkyl, Ci-C 8 haloalkyl or C 2 - C ⁇ -hydroxyalkyl and in particular H or Ci-C ⁇ -alkyl, and wherein the heterocycle 1, 2 or 3 substituents may carry, which are selected from halogen,
  • the heterocycle is saturated.
  • R 5 and R 6 together with the nitrogen atom to which they are attached form a saturated 5-, 6- or 7-membered, and in particular a 6 or 7-membered heterocycle, wherein the heterocycle additionally a heteroatom or a heteroatom-containing group may contain as a ring member, which is selected from O and NR '", wherein R'" for H, Ci-C 8 -Al kyl, Ci-Cs-haloalkyl or C 2 -Cs- H yd roxya I kyl and is in particular H or Ci-C ⁇ -alkyl, and wherein the heterocycle may bear 1 or 2 substituents selected from halogen, hydroxy, Ci-C 8 alkyl-Al, Ci-C8 haloalkyl, C 2 -C 8 -hydroxyalkyl, C 1 -C -alkoxy and C 1 -C -haloalkoxy.
  • the heterocycle in addition to the nitrogen atom which carries the radicals R 5 and R 6 , no further heteroatoms as ring members.
  • substituents these are preferably selected from halogen, C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl and in particular from C 1 -C 4 -alkyl.
  • the heterocycle is unsubstituted or carries a C 1 -C 4 -alkyl substituent, eg a methyl substituent.
  • R 1 is a radical OR 7 . In a further alternative preferred embodiment of the invention, R 1 is a radical SR 8 .
  • R 7 and R 8 are not H. They are preferably C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 2 -C 6 -cycloalkyl. With particular preference they are C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 1 -C 6 -haloalkyl which are each branched in the ⁇ -position. Alternatively, they are particularly preferably C 1 -C 4 -haloalkyl.
  • they are ethyl, propyl, isopropyl, 1, 2-dimethylpropyl, 1, 2,2-trimethylpropyl, 1-methyl-2,2,2-trifluoroethyl or 2,2,2-trifluoroethyl.
  • R 1 is a
  • R 1 'or a group NR 5 R 6 wherein R 1 ', R 5 and R 6 preferably have the preferred meanings given above.
  • R 1 is a group NR 5 R 6 , wherein R 5 and R 6 preferably have the preferred meanings given above.
  • the radical R 2 is phenyl, pyridinyl, z. B. 2-, 3- or 4-pyridinyl, pyrimidinyl, z. B. 2-, 4- or 5-pyrimidinyl, pyrazinyl, z. 2-pyrazinyl, pyridazinyl, e.g. B. 3- or 4-pyridazinyl, triazinyl, furyl, z. B. 2- or 3-furyl, thienyl, z. B. 2- or 3-thienyl, pyrrolyl, z. B. 2- or 3-pyrrolyl, Pyrazo- IyI, z.
  • the radical R 2 is phenyl, pyridinyl, z. B. 2-, 3- or 4-pyridinyl, pyrimidinyl, especially 4- or 5-pyrimidinyl, pyrazinyl, z. 2-pyrazinyl, pyridazinyl, e.g. B. 3- or 4-pyridazinyl, furyl, z. B. 2- or 3-furyl, thienyl, z. B. 2- or 3-thienyl, pyrazolyl, especially 1- or 5-pyrazolyl, imidazolyl, especially 1-, 2- or 5-imidazolyl, oxazolyl, z. B.
  • R 2 is substituted by a radical L 1, and 0, 1, 2, 3 or 4, preferably 1 or 2, especially 2 radicals L 2 is substituted phenyl.
  • L 2 halogen, such as fluorine or chlorine; cyano; nitro; alkoxycarbonyl; aminocarbonyl; C 1 -C 4 -alkyl, such as methyl; CrC 4 - haloalkyl, such as trifluoromethyl; CrC 4 -alkoxy, such as methoxy.
  • halogen such as fluorine or chlorine
  • cyano nitro
  • alkoxycarbonyl aminocarbonyl
  • C 1 -C 4 -alkyl such as methyl
  • CrC 4 - haloalkyl such as trifluoromethyl
  • CrC 4 -alkoxy such as methoxy.
  • Preferred embodiments of the radical R 2 relate in particular to phenyl groups which may have the following substitution in addition to the group L 1 (for the position numbering see the following diagram):
  • Position 2 fluorine, chlorine, methyl; Position 3: hydrogen, fluorine, methoxy; Position 4: hydrogen, fluorine, chlorine, methyl, methoxy, cyano, nitro, alkoxycarbonyl, aminocarbonyl, haloalkyl, particularly preferably fluorine, chlorine, methyl, methoxy, cyano; Position 5: hydrogen, fluorine, chlorine, methyl; particularly preferably hydrogen, fluorine; Position 6: hydrogen, fluorine, chlorine, methyl; particularly preferably hydrogen, fluorine.
  • the group L 1 is preferably in the positions 3, 4 or 5, particularly preferably 3 or 4 and in particular 4, based on the 1-position of the binding site to the pyrimidine ring.
  • R 2 is one of the groups A or B.
  • L 2 preferably represents one of the following substituent combinations: 2-CI; 2-F; 2-CH 3 ; 2,6-F 2 ; 2,6-Cl 2 ; 2-F, 6-CH 3 ; 2,4,6-F 3 ; 2,6-F 2 -4-OCH 3 ; 2-CI-4-OCH 3 ; 2-CH 3 -4 F; 2-CF 3 ; 2-OCH 3 , 6-F; 2,4-F 2 ; 2-F-4-CI; 2-F-6-CI; 2-CI.4-F; 2-CI.5-F; 2,3-F 2 ; 2,5-F 2 ; 2,3,4-F 3 ; 2-CH 3 ; 2,4- (CH 3 ) 2 ; 2-CH 3 -4-CI; 2-CH 3 , 5-F; 2-F, 4-CH 3 ; 2,6- (CH 3 ) 2 ; 2,4,6- (CH 3 ) 3 ; 2,6-F 2 , 4-CH 3 .
  • L 2 particularly preferably represents one of the following substituent combinations: 2-F; 2-CI; 2-CH 3
  • Group A is particularly preferred.
  • R 2 is a 5-membered heteroaryl which is substituted by a radical L 1 and optionally by 1, 2 or 3 radicals L 2.
  • the 5-membered heteroaryl ring is preferably under thienyl, eg. B. 2- or 3-thienyl, pyrazolyl, z. 1-, 3-, 4- or 5-pyrazolyl, and thiazolyl, e.g. B. 2-, 4- or 5-thiazolyl selected.
  • R 2 is a 6-membered heteroaryl which is substituted by a radical L 1 and optionally by 1, 2 or 3 radicals L 2 and contains one to three nitrogen atoms.
  • the 6-membered heteroaryl ring is preferably under pyridinyl, z. B. 2-, 3- or 4-pyridinyl, pyrimidinyl, z. B. 2-, 4- or 5-pyrimidinyl, pyrazinyl, z. 2-pyrazinyl and pyridazinyl, e.g. For example, 3- or 4-pyridazinyl.
  • R 2 is pyridyl which is bonded to the pyrimidine ring in the 2, 3 or 4 position and 1, 2 or 3 are identical or different.
  • substituents L 2 are preferably selected from fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • a preferred embodiment of such compounds are those of the formulas I. C
  • R 2 is pyrimidyl which is bonded to the pyrimidine ring in the 2- or 4-position and can carry 1 or 2 identical or different substituents L 2 , which is preferably fluorine, chlorine, bromine, cyano , Nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • substituents L 2 which is preferably fluorine, chlorine, bromine, cyano , Nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • L 2 which is preferably fluorine, chlorine, bromine, cyano , Nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl
  • R 2 is thienyl, which is bonded to the pyrimidine ring in the 2- or 3-position and can carry 1 or 2 identical or different substituents L 2 , which is preferably fluorine, chlorine, bromine, cyano , Nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • substituents L 2 which is preferably fluorine, chlorine, bromine, cyano , Nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • L 2 which is preferably fluorine, chlorine, bromine, cyano , Nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl
  • R 2 is thiazolyl which is bonded to the pyrimidine ring in the 2-, 4- or 5-position and can carry a substituent L 2 which is preferably fluorine, chlorine, bromine or cyano , Nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoxymomethyl, methoximinoethyl and trifluoromethyl.
  • L 2 is preferably fluorine, chlorine, bromine or cyano , Nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoxymomethyl, methoximinoethyl and trifluoromethyl.
  • a preferred embodiment of such compounds are those of the formulas 1.1 and IJ.
  • R 2 is imidazolyl which is bonded in the 4- or 5-position to the pyrimidine ring and can carry 1 or 2 identical or different substituents L 2 , which is preferably fluorine, chlorine, bromine, cyano , Nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • substituents L 2 which is preferably fluorine, chlorine, bromine, cyano , Nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • L 2 is preferably fluorine, chlorine, bromine, cyano , Nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydro
  • R 2 is pyrazolyl which is bonded to the pyrimidine ring in the 1, 3, 4 or 5 position and can carry 1 or 2 identical or different substituents L 2 , which are preferably fluorine , Chloro, bromo, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, chloro, bromo, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • substituents L 2 which are preferably fluorine , Chloro, bromo, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and trifluoromethyl.
  • R 2 is oxazolyl which is bonded to the pyrimidine ring in the 2-, 3- or 4-position and can carry a substituent L 2 which is preferably fluorine, chlorine, bromine or cyano , Nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoxymomethyl, methoximinoethyl and trifluoromethyl.
  • L 2 which is preferably fluorine, chlorine, bromine or cyano , Nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoxymomethyl, methoximinoethyl and trifluoromethyl.
  • a preferred embodiment of such compounds are those of the formulas I. P and I. Q.
  • At least one group L 2 is ortho to the point of attachment of the group R 2 with the pyrimidine skeleton, in particular chlorine, fluorine or methyl.
  • a heteroatom of the heteroaromatic radical R 2 is ortho to the point of attachment.
  • the index m is preferably from 1 to 4, where the groups L 2 may be identical or different.
  • the heteroaromatic groups R 2 carry, in addition to a group L 1, further substituents L 2 , these are preferably selected from: fluorine, chlorine, methyl, methoxy, cyano, nitro, alkoxycarbonyl, aminocarbonyl and haloalkyl.
  • the optional substituents L 2 are selected from fluorine, chlorine, methyl and methoxy.
  • the optional substituents L 2 are selected from chlorine, methyl and methoxy.
  • Another embodiment relates to heteroaromatic groups R 2 , which are substituted by chlorine in addition to a group L 1 .
  • the radical R 2 is phenyl or pyridinyl, especially 2-pyridinyl, where these are a substituent L 1 and 0, 1, 2, 3 or 4, preferably 0, 1 or 2, in particular in particular carry 1 or 2 substituents L 2 , wherein L 1 and L 2 are as defined above or as described below.
  • R 2 is phenyl or 2-pyridinyl
  • these rings preferably carry the substituent L 1 in the 3- or in particular 4-position (based on the 1-position of the bond to the pyrimidine ring, ie L 1 is particularly preferably meta or especially para-linked to this binding site).
  • the phenyl or the 2-pyridinyl ring optionally have 1 or 2 further substituents L 2 .
  • these are in the 2- and / or 6-position of the phenyl ring (based on the 1-position of the bond to the pyrimidine ring), ie ortho-constantly to the point of attachment to the pyrimidine ring, and in the 2-pyridine ring preferably in the 6-position (referred bonded to the 1-position of the bond to the pyrimidine ring).
  • R 2 is phenyl.
  • the radical L 1 is in the 4-position of the phenyl ring, relative to the 1-position of the phenyl ring to the bond of the pyrimidine ring bound.
  • the phenyl ring also carries 1 or 2, preferably 2 substituents L 2 , which are preferably bonded in the 2- or 2.6-position. Preferred substituents L 2 are mentioned above; more preferably L 2 is F.
  • the substituent L 1 of the radical R 2 is a radical L 11 of the formula wherein A ⁇ is C 1 -C 4 -alkylene; Y TM 1 , Y TM 2 are each independently O, S or NR hCt ; "T is OR h ⁇ , SR h ⁇ or NR hCt R ' ⁇ ; each R h ⁇ and R' ⁇ independently is H or Ci-C 4 -AlkVl and a is 1, 2, 3 or 4.
  • Ci-C 4 -alkylene in A ⁇ is preferably methylene, 1, 2-ethylene, 1, 2 or 1, 3-propylene or 1, 4-n-butylene.
  • a ⁇ is preferably methylene, 1, 2-ethylene, 1, 2-propylene or 1, 3-propylene and in particular methylene or 1, 2-ethylene.
  • Y 0 " 1 and Y TM 2 are preferably O or NR h ⁇ , and when Y 0 " 1 is O, Y TM 2 is preferably O.
  • T ⁇ is OR h ⁇ . If Y TM 1 stands for NR hCt R ' ⁇ and at the same time Y TM denotes 2 O, in this case T ⁇ preferably stands for OR h ⁇ .
  • T ⁇ is preferably OR hCt or NR hCt R ' ⁇ .
  • R h ⁇ and R ' ⁇ independently of one another preferably represent H, methyl or ethyl.
  • a is preferably 1, 2 or 3.
  • the substituent L 1 of the radical R 2 is a radical L 12 of the formula
  • T 3 ⁇ is R h ⁇ , OR h ⁇ or NR h ⁇ R l ⁇ ; HSS and LSS each R and R is independently H, C -C -alkyl 8 -alkyl, C 2 -C 8 alkenyl, C 2 -C 8 kinyl -alkyl, C 3 -C 6 - cycloalkyl, Cs-C ⁇ -cycloalkenyl, Phenyl or a 5- or ⁇ -membered heteroaromatic radical, wherein the heteroaromatic radical contains 1, 2, 3 or 4 heteroatoms, which are selected from O, S and N, as ring members, wherein
  • Phenyl and the heteroaromatic radical may carry 1, 2 or 3 substituents which are selected from halogen, hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy, or R h and R 1 together with the nitrogen atom to which they are bonded in the radical NR h R 'form a 5- or 6-membered, saturated, partially unsaturated or aromatic heterocycle which has 1, 2 or 3 further heteroatoms which are selected under N, O and S, and / or may contain 1 or 2 carbonyl groups as ring members and / or may carry 1, 2 or 3 substituents which are selected from halogen, hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy.
  • Y ß is CH 2 or O, especially O.
  • a ⁇ is preferably C 1 -C 6 -alkylene, particularly preferably C 1 -C 4 -alkylene, in particular 1, 2-ethylene or 1, 3-propylene and especially 1, 3-propylene.
  • R h ⁇ and R ' ⁇ independently of one another preferably represent H, C 1 -C 6 -alkyl, phenyl, or a 5- or 6-membered heteroaromatic radical, where the heteroaromatic radical has 1, 2, 3 or 4 heteroatoms selected from O , S and N, as ring members, where phenyl and the heteroaromatic radical can carry 1, 2 or 3 substituents which are selected from halogen, hydroxyl, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 - AIkOXy and Ci-C 4 haloalkoxy; or R h and R 1 together with the nitrogen atom to which they are bonded in the radical NR h R 'form a 5- or 6-membered, saturated, partially unsatur
  • R h ⁇ and R ' ⁇ are particularly preferably each independently H, C 1 -C 6 -alkyl or a 5- or 6-membered heteroaromatic radical, the heteroaromatic radical being 1, 2 or 3 heteroatoms selected from O, S and N containing as ring members, wherein the heteroaromatic radical may carry 1, 2 or 3 substituents which are selected from halogen, hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -alkyl 4 -haloalkoxy; or R h and R 1 together with the nitrogen atom to which they are bonded in the radical NR h R 'form a 5- or 6-membered, saturated, partially unsaturated or aromatic heterocycle which contains 1, 2 or 3 further heteroatoms are selected from N, O and S, and / or contain 1 or 2 carbonyl groups as ring members and / or can carry 1, 2 or 3 substituent
  • R h ⁇ and R ' ⁇ are independently H, Ci-C ⁇ -alkyl or a 5- or ⁇ -membered heteroaromatic radical, wherein the heteroaromatic radical contains 1, 2 or 3 nitrogen atoms as ring members, wherein the heteroaromatic radical 1 or May carry 2 substituents which are selected from halogen, hydroxy, Ci- C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; or R h ⁇ and R l ⁇ together with the nitrogen atom to which they are bonded in the radical NR h R 'form a 5- or 6-membered, saturated or aromatic heterocycle which has 1 or 2 further nitrogen atoms and / or 1 or 2 carbonyl groups may contain as ring members and / or carry 1, 2 or 3 substituents which are selected from halogen, hydroxy, C 1 -C 4 -alkyl, C 1 -C
  • R h ⁇ is preferably H, C 1 -C 4 -alkyl or a 5- or 6-membered heteroaromatic radical, where the heteroaromatic radical is 1, 2 or 3 nitrogen atoms. contains me as ring members, wherein the heteroaromatic radical can carry 1 or 2 substituents which are selected from halogen, hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy.
  • R h ⁇ is methyl, ethyl, pyridyl or pyrimidinyl, wherein pyridyl and pyrimidyl can carry 1 or 2 substituents which are selected from halogen, hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and Ci-C 4 haloalkoxy.
  • R h ⁇ and R l ⁇ preferably represent H or C 1 -C 4 -alkyl, wherein preferably both are not H, or together with the nitrogen atom to which they are attached in the radical NR h R ', a 5- or 6-membered, saturated or aromatic heterocycle which may contain 1 or 2 further nitrogen atoms and / or 1 or 2 carbonyl groups as ring members and / or may carry 1, 2 or 3 substituents which are selected from halogen, hydroxy, Ci-C 4 alkyl, -C 4 - haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • R h ⁇ is preferably H or C 1 -C 4 -alkyl, in particular methyl.
  • T 3 ⁇ is preferably OR h ⁇ , where R h ⁇ is preferably H or C 1 -C 6 -alkyl.
  • the substituent L 1 of the radical R 2 is a radical L 13 of the formula wherein Y 17 is -CONR h ⁇ or -COO;
  • a ⁇ is C 2 -C 6 alkylene
  • T 3 ⁇ is R h ⁇ , OR h ⁇ or NR h ⁇ R ' ⁇ ; and each R h ⁇ and R ' ⁇ is independently H or C 1 -C 4 alkyl.
  • the substituent L 1 is the radical R 2 is a radical L 11 or L 12 and L in particular for 12th
  • L 2 is preferably halogen, Ci-Ce-Al kyl, z. B. Ci-C 4 -alkyl, Ci-Ce-haloalkyl, z. B. Ci-C 4 -haloalkyl, Ci-C 8 -alkoxy, z. For example, C 1 -C 4 -alkoxy, or C 1 -C 8 -haloalkoxy, z. B. Ci-C 4 haloalkoxy.
  • L 2 is particularly preferably halogen or C 1 -C 4 -alkyl and especially halogen, such as chlorine or fluorine, or methyl. More specifically, L 2 is fluorine.
  • R 3 is preferably halogen, C 1 -C 10 -alkyl, especially C 1 -C 6 -alkyl, C 1 -C 10 -haloalkyl, especially C 1 -C 5 -haloalkyl, C 1 -C 10 -alkoxy, especially C 1 -C 5 -alkoxy, Ci-Cio-haloalkoxy, especially Ci-Cs-haloalkoxy, or CN, particularly preferably halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, CrC 4 -alkoxy, Ci-C4-haloalkoxy or CN, more preferably for Halogen, Ci-C4-alkyl, especially Ci-C2-alkyl, or C1-C4-haloalkyl, especially Ci-C2-haloalkyl.
  • R 3 is halogen, especially chlorine, or C 1 -C 4 -alkyl, especially C 1 -C 2 -alkyl, in
  • R 4 is a radical R 4a , which in turn represents a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered, preferably 5- or 6- a saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2, 3 or 4 heteroatoms selected from O, N and S, and optionally 1 or 2 carbonyl groups as ring members, the heterocyclic ring being partially or completely halogenated and / or 1, 2 or 3 radicals R x , wherein R x is as defined above.
  • the 5- or 6-membered heterocycles are preferably selected from pyrrolyl, such as 1-, 2- and 3-pyrrolyl; Pyrrolinyl, such as 1-, 2-, and 3-pyrrolinyl; Pyrrolinonyl, pyrrolidinyl, such as 1-, 2-, and 3-pyrrolidinyl; Pyrrolidonyl such as 1-, 3-, 4- and 5-pyrrolidin-2-onyl and 1-, 2-, 4- and 5-pyrrolidin-3-onyl; Pyrrolidinedione, such as 1-pyrrolidine-2,5-dionyl; Pyrazolyl such as 1-, 3-, 4- and 5-pyrazolyl; Pyrazolinyl, white, 3-, 4- and 5-pyrazolinyl; Pyrazolidinyl such as 1-, 2-, 3- and 4-pyrazolidinyl; Pyrazolidinonyl; Imidazolyl such as 1-, 2-, 4- and 5-imidazolyl; Imidazolinyl such as 1-, 2-,
  • the heterocyclic ring is unsubstituted or carries 1 or 2 substituents R x , which are selected from halogen, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl,
  • the radical R 4a is a 5- or 6-membered heteroaromatic ring containing one nitrogen atom and optionally one or two further heteroatoms selected from O, N and S as ring members and being partially or completely halogenated and / or 1, 2 or 3 radicals R x , where R x has the abovementioned inventive or preferred meanings (radical R 4aa ).
  • R 4aa is pyrrolyl, such as 1-, 2- and 3-pyrrolyl; Pyrazolyl such as 1-, 3-, 4- and 5-pyrazolyl; Imidazolyl such as 1-, 2-, 4- and 5-imidazolyl; Triazolyl such as 1- and 2- [1,3,5] - (IH) -triazolyl, 1- [1,2,3] - (1H) -triazolyl, 2- [1,2,3] - ( 2H) -triazolyl and 1-, 3- and 5- [1,2,4] - (1H) -triazolyl; Tetrazolyl, such as 1- and 5- [1,2,3,4] - (1H) -tetrazolyl; Thiazolyl such as 2-, 4- and 5-thiazolyl; Isothiazolyl, such as 3-, 4- and 5-isothiazolyl; Oxazolyl such as 2-, 4- and 5-oxazolyl; Isoxazolyl, such as 3-, 4- and 5-isoxazoly
  • R 4aa is pyrazolyl, especially 1- and 3-pyrazolyl; Triazolyl, especially 1- and 2- [1, 2,4] - (1 H) -triazolyl, 4- [1, 2,4] - (4H) -triazolyl, 1- [1, 2,3 ] - (1H) -triazolyl and 2- [1,2,3] - (2H) -triazolyl; Thiazolyl, especially 2-thiazolyl; Pyridyl, especially 2-pyridyl; Pyridazinyl, especially 3-pyridazinyl; or pyrazinyl, and especially for pyrazolyl, especially 1- and 3-pyrazolyl; Triazolyl, especially 1- [1,2,4] - (1H) -triazolyl, 4- [1, 2,4] - (4H) -triazolyl, 1- [1,2,3] - (1H ) Triazolyl and 2- [1,2,3] - (2H) -triazolyl; Pyridazinyl; Tri
  • R 4aa particularly preferably represents a 5-membered, aromatic N-bonded heterocycle which contains 1, 2 or 3, preferably 2 or 3, nitrogen atoms as ring members, in particular 1-pyrazolyl, 1 - [1, 2,4] - (1H) -triazolyl, 4- [1, 2,4] - (4H) -triazolyl, 1- [1,2,3] - (1H) -triazolyl and 2- [1,2,3] - (2H) -triazolyl.
  • R 4aa is unsubstituted or bears 1 or 2 identical or different substituents R x , which are as defined above or are preferably selected from halogen, nitro, C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl and in particular from nitro and C 1 -C 4 4- alkyl, especially methyl.
  • the radical R 4a is a 5- or 6-membered saturated or partially unsaturated heterocyclic ring containing one nitrogen atom and optionally one or two further heteroatoms selected from O, N and S, and / or or contains two carbonyl groups as ring members and may be partially or fully halogenated and / or carry 1, 2 or 3 radicals R x , where R x has the abovementioned inventive or preferred meanings (radical R 4ab ).
  • R 4ab is a saturated heterocyclic radical selected from pyrrolidinyl such as 1-, 2- and 3-pyrrolidinyl; Pyrrolidonyl such as 1-, 3-, 4- and 5-pyrrolidin-2-onyl and 1-, 2-, 4- and 5-pyrrolidin-3-onyl; Pyrrolidinedione, such as 1-pyrrolidine-2,5-dionyl; Pyrazolidinyl such as 1-, 2-, 3- and 4-pyrazolidinyl; Pyrazolidinonyl; Imidazolidinyl such as 1-, 2- and 4-imidazolidinyl; Imidazolidinonyl, such as 1- and
  • R 4ab is a partially unsaturated heterocyclic radical.
  • partially unsaturated (nonaromatic) heterocycles are pyrrolinyl, such as 1-, 2-, and 3-pyrrolinyl; Pyrrolinonyl, pyrazolinyl such as 1-, 3-, 4- and 5-pyrazolinyl; Imidazolinyl such as 1-, 2-, 4- and 5-imidazolinyl; Thiazolinyl such as 2-, 4- and 5-thiazolinyl; Isothiazolinyl, such as 3-, 4- and 5-isothiazolinyl; Oxazolinyl such as 2-, 4- and 5-oxazolinyl; Isoxazolinyl, such as 3-, 4- and 5-isoxazolinyl; Dihydropyridyl such as 1,4-dihydropyrid-1, 2-, 3- and 4-yl; Dihydropyridinonyl such as 1-, 3-, 4-, 5- and 6-
  • the heterocyclic radicals in R 4ab can be partially or completely halogenated and / or can carry 1, 2 or 3 radicals R x , where R x has the abovementioned or preferred meanings according to the invention or preferred below.
  • R 4ab particularly preferably represents pyrrolidonyl, such as 1-, 3-, 4- and 5-pyrrolidin-2-onyl, and also 1-, 2-, 4- and 5-pyrrolidin-3-onyl; Imidazolidinonyl such as 1- and 4-imidazolidin-2-onyl and 1-, 2-, 3- and 5-imidazolidin-4-onyl; Oxazolidinonyl, such as 3, 4 and 5
  • Oxazolidin-2-onyl Isoxazolidinonyl such as 2-, 4- and 5-isoxazolidin-3-onyl; or dihydropyridinonyl, such as 1-, 3-, 4-, 5- and 6- (1,2-dihydro) -pyridin-2-onyl, where the heterocyclic rings are partially or fully halogenated and / or 1, 2 or 3 radicals R x may carry, wherein R x has the above or below mentioned invention or preferred meanings.
  • R 4ab is unsubstituted or carries 1 or 2 identical or different substituents R x , which are as defined above or are preferably selected from halogen, C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl and in particular from C 1 -C 4 -alkyl all methyl.
  • R 4ab is pyrrolidinonyl, especially pyrrolidin-2-one-1-yl, which is unsubstituted or carries 1 or 2 identical or different substituents R x , which are preferably selected from halogen, Ci-C4-alkyl and Ci-C4- Haloalkyl and in particular C 1 -C 4 -alkyl, especially methyl.
  • R 4b R a , R b , R c , R d , R e and R f are preferably selected from H, hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxy and phenyl, where phenyl may bear 1 or 2 substituents selected from halogen, Ci-C4-alkyl, Ci-C 4 - haloalkyl, Ci-C4-alkoxy and Ci-C4 haloalkoxy, wherein for the case that R a , R b , R c or R d are bonded directly to an oxygen atom, they are not hydroxy or C 1 -C 4 alkoxy.
  • R 4b R a , R b and R c are selected from H, hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxy and phenyl, where phenyl is 1 or 2 substituents can carry, which are selected from halogen, Ci-C4-alkyl, Ci-C 4 - haloalkyl, Ci-C4-alkoxy and Ci-C4 haloalkoxy, wherein for the case that R a, R b or R c are directly attached to an oxygen atom, they do not represent hydroxy or C 1 -C 4 -alkoxy, and R d , R e and R f are selected from H and C 1 -C 4 -alkyl.
  • X 2 is preferably a bond or -CO- and in particular a bond.
  • X 2 is a single bond, -CO-, -CONH-, -COO-, -O- or -NR f , wherein the left part of the bivalent radicals is bonded to the nitrogen atom;
  • R a is hydrogen, hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkylcarbonyl;
  • R b , R c , R d , R e and R f are independently hydrogen, hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or phenyl, where phenyl may carry 1 or 2 substituents which are selected halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, -C 4 - alkoxy and Ci-C4 haloalkoxy, wherein for the case that R a, R b, R c or R d directly to an oxygen atom they are not hydroxy or C 1 -C 4 alkoxy.
  • R 4ba R b and R c is selected from H, hydroxy, -C 4 - alkyl, Ci-C 4 alkoxy and phenyl, where phenyl may bear 1 or 2 substituents are selected from halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy, and R a is selected from H, hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl and Ci-C4-alkoxy, where in the case that R a , R b or R c are directly attached to an oxygen atom, they are not hydroxy or Ci-C4-alkoxy, and R d , R e and R f are selected under H, Ci-C4-alkyl and Ci-C4-Alkoxy.
  • X 2 is preferably a bond or -CO- and in particular a bond.
  • R 4 is a radical R 4c of the formula -NR a R b , -NR c NR a R b , -NR a -CN, -CR a R b -OR c , -CR a R b -SR c or -CR a R b -NR c R d , wherein R a , R b , R c and R d are as defined above.
  • R a , R b , R c and R d are preferably independently H, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy and in particular H or C 1 -C 4 -alkyl.
  • R 4 is a radical R 4d of the formula
  • x is 0 or 1
  • X 1 and X 11 are independently oxygen or NR f ;
  • Q is C (H) -R ', CR', NN (H) -R f or NR f ;
  • ilii stands for a single bond or a double bond
  • R a , R b , R c , R f independently of one another are hydrogen, C 1 -C 6 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 5 -C 6 -cycloalkyl or C 4 -C 6 -cycloalkenyl, or
  • R v is halogen, cyano, C 1 -C 8 -alkyl, C 2 -C 10 -alkenyl, C 2 -Cio-alkynyl,
  • R 4 is a radical R 4e of the formula
  • X 2 is a single bond, -CO-, -CONH-, -COO-, -O- or -NR f -, wherein the left part of the bivalent radicals is bonded to the nitrogen atom;
  • R f is hydrogen, methyl or C 1 -C 4 alkylcarbonyl
  • R b is hydrogen, methyl, benzyl, trifluoromethyl, allyl, propargyl or methoxymethyl;
  • R b # , R d # are independently hydrogen, C 1 -C 6 -alkyl or C 2 -C 6 -alkynyl;
  • W is S or NR d # ; wherein the aliphatic groups in the radicals R b , R b # , R d and / or R f can carry one or two substituents R w ; in which
  • R w is halogen, OR Z , NHR Z , C 1 -C 6 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -acyl-amino, [1, 3] dioxolane-C 1 -C 4 -alkyl or [ 1, 3] dioxane-Ci-C 4 alkyl, wherein R z is hydrogen, methyl, AIIyI or propargyl.
  • a particular embodiment of the invention relates to compounds of the formula 1.1
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 and in particular a radical L 11 or L 12 ;
  • L 2a, L 2b are each independently H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy and preferably H, halogen or Ci-C 4 -Alkyl, wherein preferably at least one of the radicals is not H;
  • R 3 represents halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C 4 alkyl or cyano, in particular Halogen is;
  • R 4a has the meanings given above and preferably a radical
  • R 4aa or R 4ab is;
  • R 5 and R 6 have the meanings given above, preferably the meanings given as preferred.
  • Another particular embodiment of the invention relates to compounds of the formula I.2
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 and in particular a radical L 11 or L 12 ;
  • L 2a , L 2b independently of one another are H, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl,
  • Ci-C 4 -alkoxy or Ci-C 4 haloalkoxy are H, wherein preferably at least one of the radicals does not represent H;
  • R 3 represents halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C 4 alkyl or cyano, in particular Halogen is;
  • R 4b ' is CN or a radical R 4b which has the abovementioned general or preferably preferred meanings, and preferably represents CN or a radical R 4ba ;
  • R 5 and R 6 have the meanings given above, preferably the meanings given as preferred.
  • Another particular embodiment of the invention relates to compounds of the formula 1.3
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 and in particular a radical L 11 or L 12 ;
  • L 2a, L 2b are each independently H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy and preferably H, halogen or Ci-C 4 -Alkyl, wherein preferably at least one of the radicals is not H;
  • R 3 represents halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C 4 alkyl or cyano, in particular Halogen is;
  • R 4c has the general or preferably preferred meanings given above.
  • R 5 and R 6 have the meanings given above, preferably the meanings given as preferred.
  • Another particular embodiment of the invention relates to compounds of the formula 1.4 wherein
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 and in particular a radical L 11 or L 12 ;
  • L 2a, L 2b are each independently H, halogen, Ci-C 4 -alkyl, Ci-C4-haloalkyl, -C 4 -alkoxy or Ci-C 4 haloalkoxy and are preferably H, halogen or Ci-C 4 alkyl wherein preferably at least one of the radicals is not H;
  • R 3 represents halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C 4 alkyl or cyano, in particular Halogen is;
  • R 4d has the general or preferably preferred meanings given above.
  • R 5 and R 6 have the meanings given above, preferably the meanings given as preferred.
  • Another particular embodiment of the invention relates to compounds of the formula 1.5
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 and in particular a radical L 11 or L 12 ;
  • L 2a, L 2b are each independently H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy and preferably H, halogen or Ci-C 4 -Alkyl, wherein preferably at least one of the radicals is not H;
  • R 3 represents halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C 4 alkyl or cyano, in particular Halogen is;
  • R 4e has the general or preferably preferred meanings given above; and R 5 and R 6 have the meanings given above, preferably the meanings given as preferred.
  • Another particular embodiment of the invention relates to compounds of the formula 1.6
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 and in particular a radical L 11 or L 12 ;
  • L 2a , L 2b independently of one another are H, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl,
  • Ci-C 4 -alkoxy or Ci-C 4 haloalkoxy are H, wherein preferably at least one of the radicals does not represent H;
  • R 1 has the meanings given above, preferably the meanings given as preferred;
  • R 3 represents halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C 4 alkyl or cyano, in particular Halogen is;
  • R 4a has the abovementioned meanings and preferably represents a radical R 4aa or R 4ab .
  • Another particular embodiment of the invention relates to compounds of the formula I.7
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 and in particular a radical L 11 or L 12 ;
  • L 2a, L 2b are each independently H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy and preferably H, halogen or Ci-C 4 -Alkyl, wherein preferably at least one of the radicals is not H;
  • R 1 has the meanings given above, preferably the meanings given as preferred;
  • R 3 is halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy or cyano, preferably halogen, C 1 -C 4 -alkyl or cyano, in particular halogen;
  • R 4b ' is CN or a radical R 4b which has the abovementioned general or preferably preferred meanings, and preferably represents CN or a radical R 4ba .
  • Another particular embodiment of the invention relates to compounds of the formula 1.8
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 and in particular a radical L 11 or L 12 ;
  • L 2a , L 2b independently of one another are H, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy and preferably H, halogen or C 1 -C 4 -alkyl, where preferably at least one of the radicals is not H;
  • R 1 has the meanings given above, preferably the meanings given as preferred;
  • R 3 is halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy or cyano, preferably halogen, C 1 -C 4 -alkyl or cyano, in particular halogen; and
  • R 4c has the general or preferably preferred meanings given above.
  • Another particular embodiment of the invention relates to compounds of the formula 1.9
  • L 1 is as defined above and preferably represents a radical of L 11, L 12 or L 13 and in particular a radical L 11 or L 12;
  • L 2a, L 2b are each independently H, halogen, Ci-C 4 -alkyl, Ci-C4-haloalkyl, -C 4 -alkoxy or Ci-C 4 haloalkoxy and are preferably H, halogen or Ci-C 4 alkyl wherein preferably at least one of the radicals is not H;
  • R 1 'preferably having the meanings given above as being preferred meanings indicated;
  • R 3 represents halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C 4 alkyl or cyano, in particular Halogen is;
  • R 4d has the abovementioned general or preferably preferred meanings.
  • Another particular embodiment of the invention relates to compounds of the formula 1.10
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 and in particular a radical L 11 or L 12 ;
  • L 2a, L 2b are each independently H, halogen, Ci-C4-alkyl, Ci-C 4 haloalkyl,
  • R 1 'preferably having the meanings given above as being preferred meanings indicated;
  • R 3 represents halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C 4 alkyl or cyano, in particular Halogen is;
  • R 4e has the general or preferably preferred meanings given above.
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 and in particular a radical L 11 or L 12 ;
  • L 2a is H, halogen, C -C alkyl 4 -alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy or -C 4 - haloalkoxy, preferably H, halogen or Ci-C 4 alkyl, and in particular halogen or C 1 -C 4 -alkyl;
  • R 3 represents halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C 4 alkyl or cyano, in particular Halogen is;
  • R 4a has the meanings given above and preferably a radical
  • R 5 and R 6 have the meanings given above, preferably the meanings given as preferred.
  • Another particular embodiment of the invention relates to compounds of the formula 1.12
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 and in particular a radical L 11 or L 12 ;
  • L 2a is H, halogen, Ci-C 4 -alkyl, C-4 haloalkyl, Ci-C4-alkoxy or Ci-C 4 -
  • Haloalkoxy preferably H, halogen or C 1 -C 4 -alkyl and in particular halogen or C 1 -C 4 -alkyl;
  • R 3 represents halogen, Ci-C alkyl 4 -alkyl, Ci-C 4 haloalkyl, Ci-C4-alkoxy, Ci-C alkyl 4 -haloalkoxy or cyano, preferably halogen, Ci-C 4 -alkyl or cyano, in particular halogen;
  • R 4b ' is CN or a radical R 4b which has the abovementioned general or preferably preferred meanings, and preferably represents CN or a radical R 4ba ; and R 5 and R 6 have the meanings given above, preferably the meanings given as preferred.
  • Another particular embodiment of the invention relates to compounds of the formula 1.13 wherein
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 and in particular a radical L 11 or L 12 ;
  • L 2a is H, halogen, Ci -C4 -alkyl, Ci-C 4 haloalkyl, Ci-C 4 -alkoxy or CrC 4 -
  • Haloalkoxy preferably H, halogen or C 1 -C 4 -alkyl and in particular halogen or C 1 -C 4 -alkyl;
  • R 3 represents halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C 4 alkyl or cyano, in particular Halogen is;
  • R 4c has the general or preferably preferred meanings given above.
  • R 5 and R 6 have the meanings given above, preferably the meanings given as preferred.
  • Another particular embodiment of the invention relates to compounds of the formula 1.14
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 and in particular a radical L 11 or L 12 ;
  • L 2a is H, halogen, Ci-C 4 -alkyl, C-4 haloalkyl, Ci-C 4 -alkoxy or CrC 4 -
  • Haloalkoxy preferably H, halogen or C 1 -C 4 -alkyl and in particular halogen or C 1 -C 4 -alkyl;
  • R 3 represents halogen, -C 4 alkyl, -C 4 haloalkyl, -C 4 alkoxy, -C 4 -haloalkoxy or cyano, preferably halogen, -C 4 alkyl or cyano, in particular halogen;
  • R 4d has the general or preferably preferred meanings given above; and R 5 and R 6 have the meanings given above, preferably the meanings given as preferred.
  • Another particular embodiment of the invention relates to compounds of the formula 1.15
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 and in particular a radical L 11 or L 12 ;
  • L 2a is H, halogen, Ci -C4 -alkyl, Ci-C 4 haloalkyl, Ci-C4-alkoxy or Ci-C 4 -
  • Haloalkoxy preferably H, halogen or C 1 -C 4 -alkyl and in particular halogen or C 1 -C 4 -alkyl;
  • R 3 represents halogen, Ci-C alkyl 4 -alkyl, Ci-C 4 haloalkyl, Ci-C4-alkoxy, Ci-C alkyl 4 -haloalkoxy or cyano, preferably halogen, Ci-C 4 -alkyl or cyano, in particular halogen;
  • R 4e has the general or preferably preferred meanings given above; and R 5 and R 6 have the meanings given above, preferably the meanings given as preferred.
  • Another particular embodiment of the invention relates to compounds of the formula 1.16
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 and in particular a radical L 11 or L 12 ;
  • L 2a is H, halogen, Ci-C alkyl 4 -alkyl, Ci-C 4 haloalkyl, Ci-C4-alkoxy or Ci-C 4 - haloalkoxy, preferably H, halogen or Ci-C 4 -alkyl and in particular halogen or Ci-C 4 -alkyl is alkyl;
  • R 1 has the meanings given above, preferably the meanings given as preferred;
  • R 3 represents halogen, Ci-C alkyl 4 -alkyl, Ci-C 4 haloalkyl, Ci-C4-alkoxy, Ci-C alkyl 4 -haloalkoxy or cyano, preferably halogen, Ci-C 4 -alkyl or cyano, in particular halogen; and R 4a has the abovementioned meanings and preferably represents a radical R 4aa or R 4ab .
  • Another particular embodiment of the invention relates to compounds of the formula I.17
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 and in particular a radical L 11 or L 12 ;
  • L 2a is H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C 4 -
  • Haloalkoxy preferably H, halogen or C 1 -C 4 -alkyl and in particular halogen or C 1 -C 4 -alkyl;
  • R 1 has the meanings given above, preferably the meanings given as preferred;
  • R 3 represents halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or cyano, preferably halogen, Ci-C 4 alkyl or cyano, in particular Halogen is;
  • R 4b ' is CN or a radical R 4b which has the abovementioned general or preferably preferred meanings, and preferably represents CN or a radical R 4ba .
  • Another particular embodiment of the invention relates to compounds of the formula 1.18
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 and in particular a radical L 11 or L 12 ;
  • L 2a is H, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C 4 -alkoxy or CrC 4 -
  • Haloalkoxy preferably H, halogen or C 1 -C 4 -alkyl and in particular halogen or C 1 -C 4 -alkyl;
  • R 1 has the meanings given above, preferably the meanings given as preferred;
  • R 3 is halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy or cyano, preferably halogen, C 1 -C 4 -alkyl or cyano, in particular halogen; and
  • R 4c has the general or preferably preferred meanings given above.
  • Another particular embodiment of the invention relates to compounds of the formula 1.19
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 and in particular a radical L 11 or L 12 ;
  • L 2a is H, halogen, Ci -C4 -alkyl, Ci-C 4 haloalkyl, Ci-C 4 -alkoxy or CrC 4 -
  • Haloalkoxy preferably H, halogen or Ci-C4-alkyl and in particular halogen or Ci-C4-alkyl;
  • R 1 has the meanings given above, preferably the meanings given as preferred;
  • R 3 is halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy or cyano, preferably halogen, C 1 -C 4 -alkyl or cyano, in particular halogen; and
  • R 4d has the general or preferably preferred meanings given above.
  • Another particular embodiment of the invention relates to compounds of the formula I.20
  • L 1 is as defined above and is preferably a radical L 11 , L 12 or L 13 and in particular a radical L 11 or L 12 ;
  • L 2a is H, halogen, Ci-C 4 -alkyl, C-4 haloalkyl, Ci-C4-alkoxy or Ci-C 4 -
  • Haloalkoxy preferably H, halogen or Ci-C4-alkyl and in particular halogen or Ci-C4-alkyl;
  • R 1 ' has the meanings given above, preferably the meanings given as preferred;
  • R 3 represents halogen, Ci-C 4 -alkyl, Ci-C4-haloalkyl, -C 4 -alkoxy, C is 4 -haloalkoxy or cyano, preferably halogen, Ci-C 4 alkyl or cyano, in particular halogen; and
  • R 4e has the general or preferably preferred meanings given above.
  • the substituent L 1 in compounds 1.1 to 1.10 is preferably bonded in the 3- or in particular 4-position, based on the binding site of the phenyl ring to the pyrimidine ring in the 1-position, ie L 1 is preferably meta or especially para-stable bound to the pyrimidine ring with respect to the binding site.
  • the radical L 1 is preferably bonded in the 4, 5 or 6, in particular in the 5-position, based on the binding site of the pyridyl ring to the pyrimidine ring in the 2-position.
  • Examples of preferred compounds of the general formula I are those of the formulas I.a, I.b, I. c and l.d
  • Table 8 Compounds of the formula La, in which R 3 is chlorine, L 21 is H, L 22 is H, L 1 is - (OCH 2 ) 2-OH, R 4 is thiazol-2-yl and the Combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A.
  • Table 12 Compounds of the formula La in which R 3 is chlorine, L 21 is H, L 22 is H, L 1 is - (OCH 2 ) 2-OH, R 4 is pyridazin-3-yl and the combination of R 5 and R 6 for each compound corresponds to one row of Table a.
  • Tables 36 to 70 Compounds of the formula La in which R 3 , R 4 , L 21 and L 22 are combined as defined in one of Tables 1 to 35, the combination of R 5 and R 6 for a compound of one row of the table A is and L 1 is - (OCH 2 ) 2 -OCH 3 instead of - (OCH 2 ) 2 -OH.
  • Tables 71 to 105 Compounds of the formula La in which R 3 , R 4 , L 21 and L 22 are combined as defined in one of Tables 1 to 35, the combination of R 5 and R 6 for a compound of one row of the table A is and L 1 is - (OCH 2 ) 2 -OCH 3 instead of - (OCH 2 ) 2 -OH.
  • Tables 176 to 210 Compounds of the formula Ia in which R 3 , R 4 , L 21 and L 22 are combined as defined in one of Tables 1 to 35, the combination of R 5 and R 6 for a compound of one row of the table A is and L 1 is - (OCH 2 ) 3 -OC 2 H 5 instead of - (OCH 2 ) 2 -OH.
  • Tables 1 to 35 are defined, the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A and L 1 is -O-CH 2 CH 2 -OC 2 H 5 instead of - (OCH 2 ) 2 -OH.
  • Tables 316 to 350 Compounds of the formula Ia in which R 3 , R 4 , L 21 and L 22 are combined as defined in one of Tables 1 to 35, the combination of R 5 and R 6 for a compound of one row of the table A is and L 1 is - (O-CH 2 CH 2 ) 2 -OH instead of - (OCH 2 ) 2 -OH.
  • Tables 491 to 525 Compounds of the formula Ia in which R 3 , R 4 , L 21 and L 22 are combined as defined in one of Tables 1 to 35, the combination of R 5 and R 6 for a compound of one row of the table A is and L 1 is -O-CH 2 CH 2 -NHC 2 Hs instead of - (OCH 2 ) 2 -OH.
  • Tables 526 to 560 Compounds of the formula Ia in which R 3 , R 4 , L 21 and L 22 are combined as defined in one of Tables 1 to 35, the combination of R 5 and R 6 for a compound of one row of the table A is and L 1 is -O-CH 2 CH 2 -NHC 2 Hs instead of - (OCH 2 ) 2 -OH.
  • Tables 631 to 665 Compounds of the formula Ia in which R 3 , R 4 , L 21 and L 22 are combined as defined in one of Tables 1 to 35, the combination of R 5 and R 6 for each compound of one row of the table A is and L 1 is -O-CH 2 CH 2 CH 2 -NHCl 2 H 5 instead of - (OCH 2 ) 2 -OH.
  • Tables 1 to 35 are defined, the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A and L 1 is -O-CH 2 CH 2 CH 2 CH 2 -N (CH 2 ) 2 instead of - (OCH 2 ) 2 -OH.
  • Tables 771 to 805 Compounds of the formula Ia in which R 3 , R 4 , L 21 and L 22 are combined as defined in one of Tables 1 to 35, the combination of R 5 and R 6 for each compound of one row of the table A is and L 1 is -O-CH 2 CH 2 CH 2 CH 2 -NHCl 2 H 5 instead of - (OCH 2 ) 2 -OH.
  • Tables 946 to 980 Compounds of the formula Ia in which R 3 , R 4 , L 21 and L 22 are combined as defined in one of Tables 1 to 35, the combination of R 5 and R 6 for a compound of one row of the table A is and L 1 is -O-CH 2 CH 2 CH 2 -O- (pyridin-2-yl) instead of - (OCH 2 ) 2 -OH.
  • Tables 981 to 1015 Compounds of the formula Ia in which R 3 , R 4 , L 21 and L 22 are combined as defined in one of Tables 1 to 35, the combination of R 5 and R 6 for a compound of one row of the table A is and L 1 is -O-CH 2 CH 2 CH 2 -O- (pyridin-2-yl) instead of - (OCH 2 ) 2 -OH.
  • Tables 981 to 1015 Compounds of the formula Ia in which R 3 , R 4 , L 21 and L 22 are combined as defined in one of Tables 1
  • Tables 1086 to 1120 Compounds of the formula La in which R 3 , R 4 , L 21 and L 22 are combined as defined in one of Tables 1 to 35, the combination of R 5 and R 6 for a compound of one row of the table A is and L 1 is -O-CH 2 CH 2 CH 2 CH 2 - ([1, 2,3] - (1 H) -triazol-1-yl) instead of - (OCH 2 ) 2-OH.
  • Tables 1 to 35 are defined, the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A and L 1 is -O-CH 2 CH 2 CH 2 - (pyrrolidin-2-one-1-yl) instead of - (OCH 2 ) 2 -OH.
  • Tables 1226 to 1260 Compounds of the formula La, in which R 3 , R 4 , L 21 and L 22 are combined as defined in one of Tables 1 to 35, the combination of R 5 and R 6 for a compound of one row of the table A is and L 1 is -O-CH 2 CH 2 CH 2 -Cl instead of - (OCH 2 ) 2 -OH.
  • Tables 1436 to 1470 Compounds of the formula La in which R 3 , R 4 , L 21 and L 22 are combined as defined in one of Tables 1 to 35, the combination of R 5 and R 6 for a compound
  • Tables 10291 to 11760 Compounds of the formula Ia in which R 3 , R 4 and L 1 are combined as defined in one of Tables 1 to 1470, the combination of R 5 and R 6 for a compound corresponds in each case to one row of Table A, L 21 is chlorine and L 22 is chlorine.
  • the compounds of the general formula I can be prepared in various ways in analogy to prior art processes known per se for the preparation of substituted pyrimidines.
  • the compounds of the formula I can be obtained, for example, starting from correspondingly substituted pyrimidine compounds of the formula II by nucleophilic substitution according to the synthesis shown in Scheme 1:
  • R 1 , R 3 , R 4 , L 1 and L 2 have the abovementioned meanings, m is 0, 1, 2, 3 or 4, LG 1 is a nucleophilically exchangeable group such as halogen, for example fluorine, and v - represents phenyl or a 5- or 6-membered heteroaromatic radical, wherein the heteroaromatic radical contains 1, 2, 3 or 4 heteroatoms selected from O, S and N as ring members.
  • the reaction of II with III is carried out, for example, according to the method described in WO 20005/030775 and is advantageously carried out in the presence of strong bases.
  • Suitable bases are, for example, alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide, alkali metal carbonates, such as sodium carbonate or potassium carbonate, alkaline earth metal carbonates, such as calcium or magnesium carbonate, or alkali metal hydrides, such as lithium or sodium hydride.
  • the reaction can be carried out in the presence of a solvent.
  • Suitable solvents are aprotic solvents, for example N, N-disubstituted amides, such as N, N-dimethylformamide, N, N-dimethylacetamide or N-methylpyrrolidone, sulfoxides, such as dimethyl sulfoxide, or ethers, such as diethyl ether, diisopropyl ether, tert-butyl ether, 1 , 2-dimethoxyethane, tetrahydrofuran, dioxane or anisole.
  • the reaction is usually carried out at temperatures ranging from 0 ° C. to the boiling point of the solvent.
  • T in the group L 1 is OH or a primary or secondary amino group, it is advantageous to protect the hydroxyl group or the amino group.
  • a suitable protecting group for the hydroxy group is, for example, the benzyl group which optionally bears a methoxy group in the 4-position of the phenyl ring.
  • the protective group for the hydroxy group can be removed, for example, by catalytic hydrogenolysis or by means of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).
  • a suitable protective group for primary and secondary amino groups is, for example, the tert-butoxycarbonyl group (Boc), which is usually removed again with trifluoroacetic acid or p-toluenesulfonic acid.
  • 5-phenylpyrimidines of the formula II are known from the literature and are described, for example, in EP 407899, WO 01/68614, WO 02/074753, WO 03/070721, WO 03/043993, US Pat.
  • 5-Hetarylpyrimidines of the formula II are likewise known in the literature and are described, for example, in WO 01/68614, WO 2006/029867, WO 2006/005571 and EP 06006255.1 and in the literature cited therein, to which reference is hereby fully made.
  • Compounds II which are not described herein can be prepared in analogy to the processes described therein.
  • v - represents phenyl or a 5- or 6-membered heteroaromatic radical, the heteroaromatic radical having 1, 2, 3 or 4 heteroatoms selected from O, S and N, contains as ring members.
  • the compound IV is reacted with a Lewis acid, such as aluminum trichloride or iron (III) chloride, to obtain the phenolic compound V.
  • a Lewis acid such as aluminum trichloride or iron (III) chloride
  • the ether cleavage takes place in an organic solvent, for example in an aromatic hydrocarbon such as benzene, toluene or xylene.
  • the introduction of the group L 1 is carried out by nucleophilic substitution of the hydroxy group under basic conditions as described in Scheme 1.
  • R 1 , R 3 , R 4 , R e , R f , Y 2 and L 2 have the meanings given above, m is 0, 1, 2, 3 or 4 and ( ⁇ T- ⁇ ) is Phenyl or a 5- or 6-membered heteroaromatic radical, wherein the heteroaromatic radical 1, 2, 3 or 4 heteroatoms, which are selected from O, S and N, as ring members.
  • Amino carries which may be accessible from the corresponding nitro-substituted compounds by reduction.
  • L is a nucleophilic cleavable group.
  • halides especially chlorides or bromides
  • carboxylic anhydrides eg. As acetic anhydride, or carboxylic acid chlorides, z.
  • acetyl chloride used.
  • Carboxylic acids are typically used in conjunction with coupling reagents such as dicyclohexylcarbodiimide or with strong acids such as HCl.
  • reaction conditions which are suitable for the etherification or esterification are generally known to the person skilled in the art and are described, for example, in Organikum, VEB Deutscher Verlag dermaschineen, Berlin (1981), which is hereby incorporated by reference in its entirety.
  • R 7 has the abovementioned meanings, R * and R 'independently of one another are alkyl, preferably C 1 -C 6 -alkyl.
  • Hal is halogen, preferably chlorine or bromine.
  • R 2 * is R 2 or a precursor of R 2 .
  • a precursor of R 2 is understood here and below to mean a group R 2 which bears no substituent L 1 . It goes without saying that the conversion of the group R 2 'into a group R 2 can be carried out at any stage of the synthesis of the compounds of the formula I. Optionally, it may be necessary, the hydroxy group or the amino group in L 1 to protect. With regard to suitable protective groups, reference is made to the above.
  • the malonic ester VII can be reacted with thiourea and an alkylating agent or with an S-alkylisothiourea to form the dihydroxy compound VIII.
  • alkylating agents come z.
  • the reaction is usually carried out in the presence of a solvent which is inert under the given reaction conditions.
  • the compound VIII is converted by reaction with a halogenating agent [HAL] in the dihalo compounds of the formula IX.
  • the halogenating agent used is advantageously a phosphorus oxyhalide or a phosphorus (V) halide, such as phosphorus pentachloride, phosphorus oxybromide or phosphorus oxychloride or a mixture of phosphorus oxychloride and phosphorus pentachloride.
  • a hydrohalide of a tertiary amine, for. B. triethylamine hydrochloride can be added as cocatalyst.
  • This reaction of VIII with the halogenating agent is usually carried out at 0 0 C to 150 0 C, preferably at 80 0 C to 125 0 C (also EP-A-770 615 see FIG.).
  • the reaction may be carried out in bulk or in an inert solvent, e.g. Example, a halogenated hydrocarbon such as dichloromethane, dichloroethane or an aromatic hydrocarbon such as toluene, xylene and the like or in a mixture of the aforementioned solvents.
  • a halogenated hydrocarbon such as dichloromethane, dichloroethane or an aromatic hydrocarbon such as toluene, xylene and the like or in a mixture of the aforementioned solvents.
  • the compound X can be obtained by reacting the compound IX with an alcohol R 7 OH.
  • Such reactions are known in principle, for example from JACS, 69, 1947, 1204f.
  • the reaction is usually carried out in the presence of a base.
  • Suitable bases are alkali metal hydrides such as sodium hydride or potassium hydride, alkali metal alkoxides or alkaline earth metal alkoxides such as sodium t-butylate or potassium t-butylate, tertiary amines such as triethylamine or pyridine.
  • the reaction can be carried out in excess alcohol or in an inert solvent such as carboxylic acid amides.
  • Compounds XI can be prepared, for example, by oxidation of the thioethers X.
  • Suitable oxidizing agents are, for example, hydrogen peroxide, selenium dioxide (cf., WO 02/88127) or organic carboxylic acids, such as 3-chloroperbenzoic acid.
  • the oxidation is preferably carried out at 10 to 50 0 C in the presence of protic or aprotic solvent shear (cf. B. Kor Chem Soc, Vol 16, pp 489-492 (1995);.... Z. Chem., 17, p. 63 (1977)).
  • the radical R 4 is a radical which can be introduced nucleophilic
  • the compound of the formula I is prepared by reacting the sulfon of the formula XI with compounds R 4 -H.
  • the reaction takes place under basic conditions.
  • the alkali metal, alkaline earth metal or ammonium salt of the compound R 4 -H can be used directly.
  • the addition of bases is possible.
  • This reaction typically occurs under the conditions of nucleophilic substitution; usually at 0 to 200 0 C, preferably at 10 to 150 0 C. It may be advantageous to the implementation in the presence of a phase transfer catalyst, eg. B. 18-crown-6, perform.
  • reaction takes place in the presence of a dipolar aprotic solvent such as N, N-dialkylated carboxylic acid amides, for. N, N-dimethylformamide, cyclic ethers, e.g. B. Tetrahydrofuran or carbonitriles such as acetonitrile (see DE-A 39 01 084, Chimia, Vol 50, pp 525-530 (1996); Khim Geterotsikl Soedin, Vol 12, p 1696-1697 (1998). ).
  • a dipolar aprotic solvent such as N, N-dialkylated carboxylic acid amides, for. N, N-dimethylformamide, cyclic ethers, e.g. B. Tetrahydrofuran or carbonitriles such as acetonitrile (see DE-A 39 01 084, Chimia, Vol 50, pp 525-530 (1996); Khim Geterotsikl Soedin, Vol 12, p 1696-1697 (1998).
  • the compounds XI and R 4 -H are used in approximately stoichiometric amounts. However, it may be advantageous to use the nucleophile of the formula R 4 -H in excess, for example in an up to 10-fold, in particular up to 3-fold excess, based on the compound XI.
  • Suitable bases are alkali metal carbonates and bicarbonates, for example sodium carbonate and sodium hydrogencarbonate, nitrogen bases, such as triethylamine, tributylamine and pyridine, alkali metal alcoholates, such as sodium methoxide or potassium tert-butoxide, alkali metal amides, such as sodium amide or alkali metal hydrides, such as lithium hydride or sodium hydride , in question.
  • bases are alkali metal carbonates and bicarbonates, for example sodium carbonate and sodium hydrogencarbonate, nitrogen bases, such as triethylamine, tributylamine and pyridine, alkali metal alcoholates, such as sodium methoxide or potassium tert-butoxide, alkali metal amides, such as sodium amide or alkali metal hydrides, such as lithium hydride or sodium hydride , in question.
  • Suitable solvents are halogenated hydrocarbons, ethers such as diethyl ether, diisopropyl ether, tert-butyl ether, 1, 2-dimethoxyethane, dioxane, anisole and tetrahydrofuran, and also dimethyl sulfoxide, N, N-dialkylated carboxamides, such as dimethylformamide or dimethylacetamide. Particular preference is given to using ethanol, dichloromethane, acetonitrile or tetrahydrofuran. It is also possible to use mixtures of the solvents mentioned.
  • (Het) Arylmalonates of the formula VII can be prepared starting from (Het) aryl compounds of the formula XII by reaction with one or two equivalents of a carbonic acid ester or a chloroformate (compound XIII) in the presence of a strong base (see Scheme 6).
  • R z is hydrogen or a C 1 -C 4 alkoxycarbonyl group.
  • Q is halogen or C 1 -C 4 -alkoxy, in particular methoxy or ethoxy.
  • R 2 * has the abovementioned meanings and R is C 1 -C 4 -alkyl.
  • the reaction shown in Scheme 6 is usually carried out in the presence of strong bases.
  • R z is hydrogen, it is usual to use alkali metal amides such as sodium amide or lithium diisopropylamide, or lithium organic compounds such as phenyl lithium or butyl lithium as base. In this case, the base will be used at least equimolar, based on the compound XII, in order to achieve complete conversion.
  • R z is an alkoxycarbonyl group, it is preferable to use an alkali metal alcoholate, e.g. As sodium or potassium, sodium or potassium butoxide, sodium or potassium as a base.
  • reaction of XII with XIII can be carried out in one stage or in two separate stages, in which case the compound VII is obtained as intermediate in which R z is an alkoxycarbonyl group.
  • reaction of XII with XIII can be carried out analogously to the method described in J. Med. Chem. 25, 1982, p. 745.
  • malonates of the formula VII is also advantageously achieved by reaction of corresponding bromine (Het) aryl compounds Br-R 2 * with dialkyl malonates under Cu (I) catalysis (compare Chemistry Letters, pp. 367-370, 1981, EP-A -1,002,788).
  • the reaction of IX with an amine HNR 5 R 6 is usually carried out in an inert solvent such as ethers, for. As dioxane, tetrahydrofuran or diethyl ether, halogenated hydrocarbons such as dichloromethane, aromatic hydrocarbons, eg. As toluene, or carboxylic acid esters such as ethyl acetate. [see. WO 98/46608].
  • ethers such as dioxane, tetrahydrofuran or diethyl ether, halogenated hydrocarbons such as dichloromethane, aromatic hydrocarbons, eg. As toluene, or carboxylic acid esters such as ethyl acetate.
  • a base such as tertiary amines, for example triethylamine, or inorganic bases, such as alkali metal or alkaline earth metal carbonates, alkali metal or alkaline earth metal hydrogencarbonates; Excess amine can also serve as a base.
  • a base such as tertiary amines, for example triethylamine, or inorganic bases, such as alkali metal or alkaline earth metal carbonates, alkali metal or alkaline earth metal hydrogencarbonates; Excess amine can also serve as a base.
  • Amines of the formulas HNR 5 R 6 are known in the literature, can be prepared by known methods or are commercially available.
  • R * is alkyl, preferably d-C 6 alkyl.
  • Hal is halogen, preferably chlorine or bromine.
  • R 2 * is R 2 or a precursor of R 2 .
  • the reactions shown in Scheme 8 can be carried out analogously to the reactions explained in Scheme 5.
  • R 1 and R 3 are independently alkyl.
  • R 2 * is R 2 or a precursor of R 2 .
  • the reactions shown in Scheme 9 can be carried out in analogy to the reactions explained in Scheme 5.
  • the cation M 1 in formula XXIV has little significance; For practical reasons, ammonium, tetraalkylammonium salts such as tetramethylammonium or tetraethylammonium salts or alkali or alkaline earth metal salts are usually preferred (Scheme 10).
  • the reaction temperature is 0 to 120 ° C, preferably at 10 to 40 ° C [see FIG. J. Heterocycl. Chem., Vol. 12, pp. 861-863 (1975)].
  • Suitable solvents include ethers, such as dioxane, diethyl ether, methyl tert-butyl ether and, preferably, tetrahydrofuran, halogenated hydrocarbons, such as dichloromethane or dichloroethane, aromatic hydrocarbons, such as toluene, and mixtures thereof.
  • R 3 is C 1 -C 5 -alkyl, C 1 -C 5 -haloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -haloalkenyl, C 2 -C 5 -alkynyl or C 2 -C 8 -haloalkynyl
  • R 3 represents halogen
  • organometallic compounds R 3a -mt wherein R 3a is C 8 - alkyl, Ci-Cs-haloalkyl, C 2 -C 8 - Alkenyl, C 2 -C 8 -haloalkenyl, C 2 -C 8 -alkynyl or C 2 -C 8 -haloalkynyl and Mt represents lithium, magnesium or zinc.
  • the reaction is preferably carried out in the presence of catalytic or in particular at least equimolar amounts of transition metal salts and / or compounds, in particular in the presence of Cu salts such as Cu (l) halides and especially Cu (I) iodide.
  • the reaction is carried out in an inert organic solvent, for example one of the abovementioned ethers, in particular tetrahydrofuran, an aliphatic or cycloaliphatic hydrocarbon such as hexane, cyclohexane and the like, an aromatic hydrocarbon such as toluene or in a mixture of these solvents.
  • the temperatures required for this purpose are in the range of -100 to +100 0 C and especially in the range of -80 0 C to +40 0 C. Processes are known, for. B. from the cited prior art or from WO 03/004465.
  • R 4 is a heterocyclic substituent
  • a corresponding heterocyclic amidine which are known in the art or can be prepared from the corresponding heterocyclic nitriles, reacted with a malonic acid ester to the pyrimidine ring (see also WO 2003/070721).
  • the reaction mixtures are worked up in the usual way, for. B. by mixing with water, separation of the phases and optionally chromatographic purification of the crude products.
  • the intermediate and end products fall z. T. in the form of colorless or pale brownish, viscous oils, which are freed or purified under reduced pressure and at moderately elevated temperature of volatile fractions. If the intermediate and end products are obtained as solids, the purification can also be carried out by recrystallization or trituration.
  • isomeric mixtures are involved in the synthesis, separation is generally not necessary because some of the isomers may partially interconvert during processing for use or in use (eg, by exposure to light, acid, or base). Corresponding conversions can also take place after use, for example in the 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 outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Deuteromycetes, Basidiomycetes and Peronosporomycetes (syn. Oomycetes). They are partially systemically effective and can be used in crop protection as foliar, pickling and soil fungicides.
  • the compounds I are suitable for controlling the plant diseases mentioned below:
  • the compounds I are suitable for controlling Alternaria species on vegetables, oilseed rape, sugar beets and fruits and rice such. BA solani or A. alternata on potatoes and tomatoes.
  • the compounds I are suitable for controlling Aphanomyces species on sugar beets and vegetables.
  • the compounds I are suitable for controlling Ascochyta species on cereals and vegetables.
  • the compounds I are suitable for controlling Bipolaris and Drechslera species on corn, cereals, rice and turf, such as. B. D. maydis on corn.
  • the compounds I are suitable for controlling Blumeria graminis (powdery mildew) on cereals.
  • the compounds I are suitable for controlling Botrytis cinerea (gray mold) on strawberries, vegetables, flowers and grapevines.
  • the compounds I are suitable for controlling Bremia lactucae on lettuce.
  • the compounds I are suitable for controlling Cercospora species on corn, soybeans, rice and sugar beet.
  • the compounds I are suitable for controlling Cochliobolus species on corn, cereals, rice, such as. Cochliobolus sativus on cereals, Cochliobolus miyabeanus on rice.
  • the compounds I are suitable for controlling Colletotricum species on soybeans and cotton.
  • the compounds I are suitable for controlling Drechslera species, Pyrenophora species on corn, cereals, rice and turf, such as. B. teres on barley or D. tritici- repentis on wheat.
  • the compounds I are suitable for controlling Esca on grapevine, caused by Phaeoacremonium chlamydosporium, Ph. Aleophilum, and Formitipora punctata (syn. Phellinus punctatus).
  • the compounds I are suitable for controlling Exserohilum species on maize.
  • the compounds I are suitable for controlling Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits.
  • the compounds I are suitable for controlling Fusarium and Verticillium species on various plants such. B. F. graminearum or F. culmorum on cereal or F. oxysporum on a variety of plants, such as. As tomatoes.
  • the compounds I are suitable for controlling Gaeumanomyces graminis
  • the compounds I are suitable for controlling Gibberella species on cereals and
  • Rice eg Gibberella fujikuroi on rice.
  • the compounds I are suitable for controlling grainstaining complex in rice.
  • the compounds I are suitable for controlling Helminthosporium species on corn and rice.
  • the compounds I are suitable for combating Michrodochium nivale on cereals.
  • the compounds I are suitable for controlling Mycosphaerella species on cereals, bananas and peanuts, such as. BM graminicola on wheat or M. fijiensis on bananas.
  • the compounds I are suitable for controlling Peronospora species on cabbage and bulbous plants, such as. B. P. brassicae on cabbage or P. destructor on onion.
  • the compounds I are suitable for controlling Phakopsara pachyrhizi and Phokopsara meibomiae on soybeans.
  • the compounds I are suitable for controlling Phomopsis species on soybeans and sunflowers.
  • the compounds I are suitable for controlling Phytophthora infestans on potatoes and tomatoes.
  • the compounds I are suitable for controlling Phytophthora species on various plants such. B. P. capsici to paprika.
  • the compounds I are suitable for controlling Plasmopara viticola on grapevines.
  • the compounds I are suitable for controlling Podosphaera leucotricha on apple.
  • the compounds I are suitable for controlling Pseudocercosporella herpotriodides on cereals.
  • the compounds I are suitable for controlling Pseudoperonospora on various plants such. P. cubensis on cucumber or P. humili on hops.
  • the compounds I are suitable for controlling Puccinia species on various plants such. P. triticina, P. striformins, P. hordei or P. graminis on cereals, or P. asparagi on asparagus.
  • the compounds I are suitable for controlling Pyricularia oryzae, Corticium sakiisi, Sarocladium oryzae, S. attenuatum, Entyloma oryzae, on rice.
  • the compounds I are suitable for controlling Pyricularia grisea on lawns and cereals.
  • the compounds I are suitable for controlling Pythium spp. on lawn, rice, corn, cotton, oilseed rape, sunflowers, sugar beet, vegetables and other plants, such as. P.ultiumum on various plants, P. aphanidermatum on lawn.
  • the compounds I are suitable for controlling Rhizoctonia species on cotton, rice, potatoes, lawn, corn, oilseed rape, sugar beets, vegetables and various plants such. B. R. solani on turnips and various plants.
  • the compounds I are suitable for controlling Rhynchosporium secalis on barley, rye and triticale.
  • the compounds I are suitable for controlling Sclerotinia species on rape and sunflowers.
  • the compounds I are suitable for controlling Septoria tritici and Stagonospora nodorum on wheat.
  • the compounds I are suitable for controlling Erysiphe (syn. Uncinula) necator on grapevine.
  • the compounds I are suitable for controlling Setospaeria species on maize and turf.
  • the compounds I are suitable for controlling Sphacelotheca reilinia on maize.
  • the compounds I are suitable for controlling Thievaliopsis species on soybeans and cotton.
  • the compounds I are suitable for controlling Tilletia species on cereals.
  • the compounds I are suitable for controlling Ustilago species on cereals, maize and sugar cane, such as. B. U. maydis on corn.
  • the compounds I are suitable for controlling Venturia species (scab) on apples and pears such as. z. B. V. inaequalis to apple.
  • the compounds of the invention may also be used in cultures tolerant of insect or fungal growth by breeding, including genetic engineering methods.
  • the compounds I are also suitable for controlling harmful fungi in the protection of materials (eg wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
  • harmful fungi ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sciophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleu- rotus spp., Poria spp., Serpula spp.
  • Tyromyces spp. Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., moreover, in the protection of the following yeasts: Candida spp. and Saccharomyces cerevisae.
  • the compounds according to the invention and / or their agriculturally acceptable salts are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally effective amount of the active compounds.
  • the application can be done both before and after the infection of the materials, plants or seeds by the fungi.
  • Another object of the invention is therefore a method for controlling phytopathogenic fungi, which is characterized in that the fungi or the fungal infection to be protected materials, plants, the soil or seeds with an effective amount of at least one compound I according to the invention and / or an agriculturally acceptable salt thereof.
  • Another object of the invention is an agent for controlling phytopathogenic fungi, comprising at least one compound of the invention and / or an agriculturally acceptable salt thereof and at least one solid or liquid carrier.
  • the fungicidal compositions generally contain between 0.1 and 95 wt .-%, preferably between 0.5 and 90 wt .-% of active ingredient.
  • the application rates in the application in crop protection depending on the nature of the desired effect between 0.01 and 2.0 kg of active ingredient per ha.
  • active ingredient in general, amounts of active ingredient of 1 to 1000 g / 100 kg, preferably 5 to 100 g / 100 kg of seed are needed.
  • the application rate of active ingredient depends on the type of application and the desired effect. Usual application rates 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 material treated.
  • the compounds of the formula I can be present in various crystal modifications, which may differ in their biological activity. They are also the subject of the present invention.
  • the compounds I can be converted into the customary formulations, for.
  • solutions emulsions, suspensions, dusts, powders, pastes and granules.
  • the application form 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, for. By stretching the active ingredient with solvents and / or excipients, if desired using emulsifiers and dispersants.
  • Suitable solvents / auxiliaries are essentially:
  • solvents eg Solvesso products, xylene
  • paraffins eg petroleum fractions
  • alcohols eg methanol, butanol, pentanol, benzyl alcohol
  • Ketones eg cyclohexanone, gamma-butyrolactone
  • pyrrolidones NMP, NOP
  • acetates glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters.
  • solvent mixtures may also be used, - excipients such as ground natural minerals (eg kaolins, clays, talc, crayons) and ground synthetic minerals (eg highly disperse silicic acid, silicates);
  • Emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.
  • nonionic and anionic emulsifiers for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates
  • dispersants such as lignin-sulphite liquors and methylcellulose.
  • the surface-active substances used are alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, and condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde , Condensation products of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylpheny
  • emulsions, pastes or oil dispersions come mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg. As toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, eg. As dimethyl sulfoxide, N-methylpyrrolidone or water into consideration. Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
  • Granules, for. B. coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers.
  • Solid carriers are z.
  • mineral earths such as silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such.
  • 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 NMR spectrum).
  • a Water-soluble concentrates (SL, LS)
  • DC Dispersible Concentrates 20 parts by weight of the active compounds are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant, for.
  • a dispersant for.
  • polyvinylpyrrolidone dissolved. Dilution in water gives a dispersion.
  • the active ingredient content of the concentrate is 20% by weight.
  • the active compounds 25 parts by weight of the active compounds are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
  • This mixture is added by means of an emulsifying machine (eg Ultraturax) in 30 parts by weight of water and brought to a homogeneous emulsion. Dilution in water results in an emulsion.
  • the formulation has an active ingredient content of 25% by weight.
  • the active ingredients 20 parts by weight of the active ingredients are dispersed with the addition of 10 parts by weight of dispersing and Wetting agents and 70 parts by weight of water or an organic solvent in an agitating ball mill to a fine suspension of active ingredient crushed. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • Water-dispersible and water-soluble granules 50 parts by weight of the active compounds are finely ground with the addition of 50 parts by weight dispersing and wetting agents and by means of technical equipment (eg extrusion, spray tower, fluidized bed) as water-dispersible or produced water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the formulation has an active ingredient content of 50% by weight.
  • Water-dispersible and water-soluble powders 75 parts by weight of the active compounds are ground in a rotor-stator mill with the addition of 25 parts by weight of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active ingredient content of the formulation is 75% by weight.
  • 0.5 part by weight of the active ingredients are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for direct application with 0.5 wt .-% active ingredient content.
  • LS water-soluble concentrates
  • FS suspensions
  • DS water-dispersible and water-soluble powders
  • WS water-dispersible and water-soluble powders
  • ES emulsifiable concentrates
  • GF gel formulations
  • the active compounds can be used as such, in the form of their formulations or the application forms prepared therefrom, eg. B. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, atomizing, dusting, scattering or pouring are applied.
  • the forms of application depend entirely on the intended use; In any case, they should ensure as far as possible the finest distribution of the active compounds according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
  • the substances may be dissolved as such or in an oil or solvent, by means of wetting, adhesive,
  • Dispersing or emulsifying agent are homogenized in water. But it can also be made of active substance, wetting agents, adhesives, dispersants or emulsifiers and possibly solvents or oil concentrates which are suitable for dilution with water.
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume
  • wetting agents eg. B. Break Thru S 240® ; Alcohol alkoxylates, eg. As Atplus 245 ®, Atplus MBA 1303 ®, Plurafac LF 300 ® and Lutensol ON 30 ®; EO-PO block polymers, eg. B.
  • Pluronic RPE 2035 ® and Genapol B ® Alcohol ethoxylates, eg. As Lutensol XP 80 ®; and sodium dioctylsulfosuccinate, e.g. B. Leophen RA ®.
  • the compounds of the invention may also be present in the application form as fungicides together with other active ingredients, the z. As with herbicides, insecticides, growth regulators, fungicides or with fertilizers.
  • fungicides for example, in many cases the activity spectrum can be broadened or development of resistance can be prevented. In many cases, synergistic effects are obtained.
  • Another object of the invention is therefore a combination of at least one compound of the invention and / or an agriculturally acceptable salt thereof and at least one further fungicidal, insecticidal, herbicidal and / or growth-regulating active ingredient.
  • Azoxystrobin dimoxystrobin, enestroburine, fluoxastrobin, kresoxim-methyl, metominostrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, orysastrobin, (2-chloro-5- [1- (3-methyl-benzyloxyimino) -ethyl] -benzyl) -carbamic acid methyl ester, (2-Chloro-5- [1- (6-methylpyridin-2-ylmethoxyimino) ethyl] benzyl) -carbamic acid methyl ester, 2- (ortho- (2,5-dimethylphenyl-oxymethylene) -phenyl) -3- methoxy-methyl acrylate;
  • Fenhexamide flutolanil, furametpyr, metalaxyl, ofurace, oxadixyl, oxycarboxine, penthiopyrad, thifluzamide, tiadinil, 4-difluoromethyl-2-methyl-thiazole-5-carboxylic acid (4'-bromo-biphenyl-2-yl) -amide , 4-Difluoromethyl-2-methyl-thiazole-5-carboxylic acid (4 '-trifluoromethyl-biphenyl-2-yl) -amide, 4-difluoromethyl-2-methyl-thiazole-5-carboxylic acid (4' -chloro) 3'-fluoro-biphenyl-2-yl) -amide, 3-difluoromethyl-1-methyl-pyrazole-4-carboxylic acid (3 ', 4'-dichloro-4-fluoro-biphenyl-2-yl) -amide, 3 Difluor
  • Benzoic acid amides flumetover, fluopicolide (picobenzamide), zoxamide;
  • Other carboxamides carpropamide, diclocymet, mandipropamide, N- (2- (4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-methanesulfonylamino 3-methyl-butyramide, N- (2- (4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxy-phenyl) -ethyl) -2-ethanesulfonyl-amino-3-methyl- butyramide;
  • bitertanol bromuconazoles, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fenbuconazole, flusilazole, fluquinconazole, flutriol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazo - Ie, triadimenol, triadimefon, triticonazole;
  • - imidazoles cyazofamide, imazalil, pefurazoate, prochloraz, triflumizole;
  • Benzimidazoles benomyl, carbendazim, fuberidazole, thiabendazole;
  • Pyridines fluazinam, pyrifenox, 3- [5- (4-chlorophenyl) -2,3-dimethylisoxazolidin-3-yl] pyridine;
  • Pyrimidines bupirimate, cyprodinil, ferimzone, fenarimol, mepanipyrim, nuarimol, pyrimethanil; - piperazines: triforins;
  • Dicarboximides iprodione, procymidone, vinclozolin;
  • acibenzolar-S-methyl anilazine, captan, captafol, dazomet, diclomethine, fenoxanil, folpet, fenpropidin, famoxadone, fenamidone, octhilinone, probenazole, proquinazide, pyroquilon, quinoxyfen, tricyclazole, 5-chloro-7- ( 4-methyl-piperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine, 2-butoxy-6- iodo-3-propyl-chromen-4-one, 3- (3-bromo-6-fluoro-2-methylindol-1-sulfonyl) - [1, 2,4] triazole-1-sulfonic acid dimethylamide;
  • Dithiocarbamates Ferbam, Mancozeb, Maneb, Metiram, Metam, Propineb, Thiram, Zineb, Ziram; Carbamates: diethofencarb, flubenthiavalicarb, iprovalicarb, propamocarb, 3- (4-chlorophenyl) -3- (2-isopropoxycarbonylamino-3-methyl-butyrylamino) -propionic acid methyl ester, N- (1 - (1 - (4-cyanophenyl) ethanesulfonyl) -but-2-yl) carbamic acid (4-fluorophenyl) ester;
  • guanidines dodine, iminoctadine, guazatine
  • Organometallic compounds fentin salts
  • Sulfur-containing heterocyclyl compounds isoprothiolanes, dithianone
  • Organophosphorus compounds edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, pyrazophos, tolclofos-methyl, phosphorous acid and their salts;
  • Organochlorine compounds thiophanates methyl, chlorothalonil, dichlofluanid, toiylfluanid, flusulfamides, phthalides, hexachlorobenzene, pencycuron, quintozene; Nitrophenyl derivatives: binapacryl, dinocap, dinobuton;
  • the present invention further relates to the compositions listed in Table C, wherein in each case one row of Table C corresponds to a fungicidal composition comprising a compound of formula I (component 1), which is preferably one of the compounds described herein as preferred, and the each additional active ingredient (component 2) indicated in the respective line.
  • component 1 in each row of table C is in each case one of the compounds of the formula I which are specifically individualized in tables 1 to 22848.
  • the active compounds II mentioned above as component 2 their preparation and their action against harmful fungi are generally known (cf.: http://www.hclrss.demon.co.uk/index.html); they are commercially available.
  • the compounds named after IUPAC, their preparation and their fungicidal action are also known and described, for example, in EP-A 226 917; EP-A 10 28 125; EP-A 10 35 122; EP-A 12 01 648; WO 98/46608; WO 99/24413; WO 03/14103; WO 03/053145; WO 03/066609 and WO 04/049804, to which reference is hereby made in their entirety.
  • the present invention relates to a pharmaceutical composition containing at least one pyrimidine compound according to the invention and / or a pharmaceutically acceptable salt thereof and optionally at least one pharmaceutically acceptable carrier.
  • the invention also relates to the pharmaceutical use of the (novel) pyrimidines of the formula I according to the invention, in particular the (novel) pyrimidines of the formula I described in the preceding description, and / or the pharmaceutically acceptable salts thereof, in particular their use for the preparation of a medicament for the treatment of cancer.
  • pyrimidines of the formula I according to the invention in particular the pyrimidines of the formula I described in the preceding description, and / or their pharmaceutically acceptable salts, effectively inhibit the growth and / or proliferation of tumor cells, as in standard tests on tumor cell lines, such as HeLa , MCF-7 and COLO 205 can be shown.
  • pyrimidines of the invention of formula I generally show ICso values ⁇ 10 "6 mol / l (ie ⁇ 1 uM), preferably ICso-values ⁇ 10" 7 mol / l (ie ⁇ 100 nM) for Zellzyklusinhibi für in HeLa cells.
  • the pyrimidines of the formula I according to the invention are suitable for the treatment, Inhibition or control of the growth and / or proliferation of tumor cells and associated diseases suitable. Accordingly, they are for the treatment of cancer in warm-blooded vertebrates, ie of mammals and birds, especially in humans, but also in other mammals, especially useful and skin animals, such as dog, cat, pig, ruminant (cattle, sheep, goat, bison, etc .), Horse and birds such as chicken, turkey, duck, goose, guinea fowl and the like.
  • the pyrimidines of the formula I according to the invention are suitable for the treatment of cancer or cancerous diseases of the following organs: breast, lung, intestine , Prostate, skin (melanoma), kidney, bladder, mouth, larynx, esophagus, stomach, ovaries, pancreas, liver and brain.
  • compositions according to the invention contain, in addition to the pyrimidine compound I according to the invention and / or its pharmaceutically acceptable salt, at least optionally a suitable carrier.
  • suitable carriers include, for example, the solvents, carriers, excipients, excipients and the like commonly used for pharmaceutical formulations, which are exemplified below for single modes of administration.
  • the compounds I according to the invention can be administered in the usual way, eg. As oral, intravenous, intramuscular or subcutaneous.
  • the active ingredient may be mixed with an inert diluent or with an edible carrier; it can be embedded in a hard or soft gelatin capsule, pressed into tablets or mixed directly with the food / feed.
  • the active ingredient may be mixed with excipients and administered in the form of indigestible tablets, buccal tablets, troches, pills, capsules, suspensions, juices, syrups and the like.
  • Such preparations should contain at least 0.1% active ingredient.
  • the composition of the preparation may of course vary. It usually contains from 2 to 60% by weight of active compound, based on the total weight of the particular preparation (dosage unit).
  • Preferred formulations of the compound I according to the invention contain 10 to 1000 mg of active ingredient per oral dosage unit.
  • the tablets, troches, pills, capsules and the like may also contain the following ingredients: excipients such as tragacanth, acacia, corn starch or gelatin, excipients such as dicalcium phosphate, disintegrants such as corn starch, potato starch, alginic acid and the like, lubricants such as magnesium stearate, sweetener, as Sucrose, lactose, or saccharin, and / or flavoring agents such as peppermint, vanilla, and the like.
  • the capsules may also contain a liquid carrier. Other substances that change the nature of the dosing unit can also be used. For example, tablets, pills and capsules may be coated with shellac, sugar or mixtures thereof.
  • Syrups or juices may contain, in addition to the active ingredient, also sugar (or other sweetening agents), methyl or propylparaben preservatives, a dye and / or a flavoring agent.
  • sugar or other sweetening agents
  • methyl or propylparaben preservatives e.g., a dye and / or a flavoring agent.
  • the ingredients of the active ingredient formulations in the amounts used must be pharmaceutically pure and non-toxic.
  • the active compounds can be used as controlled-release preparations, eg. As a sustained-release preparations formulated.
  • the active substances can also be administered parenterally or intraperitoneally. Solutions or suspensions of the active compounds or their salts can be prepared with water using suitable wetting agents such as hydroxypropylcellulose. Dispersions can also be made with glycerin, liquid polyethylene glycols, and mixtures thereof in oils. Often these preparations also contain a preservative to prevent the growth of microorganisms.
  • Preparations for injections include sterile aqueous solutions and dispersions as well as sterile powders for the preparation of sterile solutions and dispersions.
  • the preparation must be sufficiently liquid so that it is injectable. It must be stable under the conditions of manufacture and storage and be protected against microbial contamination.
  • the carrier can be a solvent or a dispersion medium, for.
  • water, ethanol, polyols eg., Glycerol, propylene glycol or liquid polyethylene glycol
  • mixtures thereof / or vegetable oils.
  • reaction mixture was added to a saturated aqueous sodium hydrogencarbonate solution on crushed ice, the phases were separated and the aqueous phase was extracted three times with 50 ml portions of ethyl acetate. The combined organic phases were washed twice with 20 ml of saturated common salt solution. After removing the solvent under reduced pressure, the crude product was purified by flash chromatography (silica gel, acetonitrile-water 60:40) to give the title compound as a colorless oil (700 mg, 42% of theory).
  • step b) 4-Chloro-2- (N-methoxyamidine) -5- (2,6-difluoro-4- (3- (N- (tert-butyloxycarbonyl) amino) -propoxy) -phenyl) -6- (4- methylpiperidin-1-yl) pyrimidine
  • sodium methoxide 4.03 g, 0.02 mmol
  • O-methylhydroxylamine hydrochloride 22 mg, 0.27 mmol
  • the active ingredients were formulated separately as a stock solution in dimethylsulfoxide at a concentration of 10,000 ppm.
  • the stock solution was pipetted into a microtiter plate (MTP) and diluted with an aqueous malt-based fungus nutrient medium to the stated active compound concentration. This was followed by the addition of an aqueous spore suspension of Botrytis cinerea.
  • MTP microtiter plate
  • the plates were placed in a water vapor-saturated chamber at temperatures of 18 0 C.
  • the MTP's were measured at 405 nm on the 7th day after inoculation.
  • the stock solution was pipetted into a microtiter plate (MTP) and diluted to the indicated drug concentration with a malt-based aqueous mushroom nutrient medium. This was followed by the addition of an aqueous spore suspension of Pyricularia oryzae.
  • HeLa B cells were contained in DMEM (Life Technologies Cat No. 21969-035.) Containing fetal calf serum, in 180 cm 2 (FCS, Life Technologies Cat No. 10270-106.) - containers at 37 0 C, 92% Moisture and 7% CO 2 cultured.
  • DMEM Life Technologies Cat No. 21969-035.
  • FCS Life Technologies Cat No. 10270-106.
  • the supernatant solution was removed and the cells were lysed with 0.5 ml of RNase buffer (10 mM sodium citrate, 0.1% Nonidet NP40, 50 ⁇ g / ml RNase, 10 ⁇ g / ml propidium iodide) per well.
  • RNase buffer 10 mM sodium citrate, 0.1% Nonidet NP40, 50 ⁇ g / ml RNase, 10 ⁇ g / ml propidium iodide
  • the ratio of cells in the Go / Gi phase to those in the G2 / M phase was calculated and compared with the value for the control (DMSO).
  • the results are given in the following Table 2 as IC 50 values calculated from the concentration curve versus the cell cycle ratio; they indicate the concentration at which 50% of the cells are inhibited in their cell cycle.

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Abstract

La présente invention concerne l'utilisation de composés de pyrimidine de la formule (I), dans laquelle les variables ont la signification donnée dans les revendications et dans la description, pour la lutte contre les champignons nuisibles ; l'invention concerne également de nouveaux composés de pyrimidine de la formule (I) ainsi que des fongicides et des produits pharmaceutiques les contenant.
EP07788154A 2006-08-02 2007-08-01 Composés de pyrimidine pour la lutte contre les champignons nuisibles et le cancer Withdrawn EP2049498A1 (fr)

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EP06118350 2006-08-02
EP07788154A EP2049498A1 (fr) 2006-08-02 2007-08-01 Composés de pyrimidine pour la lutte contre les champignons nuisibles et le cancer
PCT/EP2007/057989 WO2008015250A1 (fr) 2006-08-02 2007-08-01 Composés de pyrimidine pour la lutte contre les champignons nuisibles et le cancer

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AR064852A1 (es) * 2007-01-11 2009-04-29 Basf Ag Pirimidinas sustituidas en posicion 2
BRPI0815979A2 (pt) 2007-08-28 2017-06-13 Irm Llc compostos e composições com inibidores de quinase, bem como uso dos mesmos
PE20091236A1 (es) 2007-11-22 2009-09-16 Astrazeneca Ab Derivados de pirimidina como immunomoduladores de tlr7
EP2092824A1 (fr) 2008-02-25 2009-08-26 Bayer CropScience AG Hétérocyclyl-pyrimidines
PE20100087A1 (es) 2008-06-25 2010-02-08 Irm Llc Compuestos y composiciones como inhibidores de cinasa
US8445505B2 (en) 2008-06-25 2013-05-21 Irm Llc Pyrimidine derivatives as kinase inhibitors
GB0908772D0 (en) 2009-05-21 2009-07-01 Astrazeneca Ab New salts 756
SG175796A1 (en) 2009-05-21 2011-12-29 Astrazeneca Ab Novel pyrimidine derivatives and their use in the treatment of cancer and further diseases
BR112013014484A2 (pt) * 2010-12-13 2016-07-19 Viamet Pharmaceuticals Inc compostos inibidores de metaloenzimas
JP5978225B2 (ja) 2010-12-16 2016-08-24 大日本住友製薬株式会社 治療に有用なイミダゾ［４，５−ｃ］キノリン−１−イル誘導体
AU2013261267B2 (en) 2012-05-18 2017-06-29 Sumitomo Pharma Co., Ltd. Carboxylic acid compounds
CN111187220B (zh) * 2020-01-19 2022-08-02 郑州大学 含席夫碱结构单元的三氟甲基嘧啶类衍生物及其制备方法和用途

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MXPA02012073A (es) * 2000-06-13 2003-04-25 Basf Ag 2-(cianoamino)pirimidinas substituidas con 5-fenilo fungicidas.
EP1373222A2 (fr) * 2001-03-15 2004-01-02 Basf Aktiengesellschaft 5-phenylpyrimidines, procede et produits intermediaires utilises pour les produire et leur utilisation pour lutter contre des champignons nuisibles
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CA2467683C (fr) * 2001-11-19 2011-09-27 Basf Aktiengesellschaft 5-phenylpyrimidines, procede pour les produire, agents les contenant et leur utilisation
ATE428705T1 (de) * 2002-02-21 2009-05-15 Basf Se 2-(2-pyridyl)-5-phenyl-6-aminopyrimidine, verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen
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BRPI0410482A (pt) * 2003-05-20 2006-06-13 Basf Ag composto, processo para preparar o mesmo, agente adequado para combater fungos nocivos, e, processo para combater fungos nocivos fitopatogênicos
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JP2009545567A (ja) 2009-12-24
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UY30520A1 (es) 2008-02-29
TW200823191A (en) 2008-06-01
PE20080420A1 (es) 2008-07-10
CL2007002231A1 (es) 2008-04-11
CN101522640A (zh) 2009-09-02
US20090264447A1 (en) 2009-10-22
AR062179A1 (es) 2008-10-22

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