EP1987011A1 - Pyrimidines substituées en position 2 et leur utilisation comme pesticides - Google Patents

Pyrimidines substituées en position 2 et leur utilisation comme pesticides

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Publication number
EP1987011A1
EP1987011A1 EP07704400A EP07704400A EP1987011A1 EP 1987011 A1 EP1987011 A1 EP 1987011A1 EP 07704400 A EP07704400 A EP 07704400A EP 07704400 A EP07704400 A EP 07704400A EP 1987011 A1 EP1987011 A1 EP 1987011A1
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EP
European Patent Office
Prior art keywords
methyl
alkyl
compounds
chlorine
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP07704400A
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German (de)
English (en)
Inventor
Joachim Rheinheimer
Thomas Grote
Bernd Müller
Wassilios Grammenos
Sarah Ulmschneider
Jens Renner
Reinhard Stierl
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BASF SE
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BASF SE
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Priority to EP07704400A priority Critical patent/EP1987011A1/fr
Publication of EP1987011A1 publication Critical patent/EP1987011A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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

Definitions

  • the present invention relates to the use of pyrimidines of the formula I.
  • X is NR 1 R 2 , OR 3 , SR 3 or C 1 -C 8 -alkyl which may contain one, two, three or four identical or different substituents R a ;
  • R 1 , R 2 , R 3 mean:
  • R 1, R 2 are independently hydrogen, Ci-Cs-alkyl, Ci-C8-halo-alkyl, C 2 -C 8 -alkenyl -alkyl, C 2 -C 8 haloalkenyl, C 2 -C 8 -alkyl kinyl, C 2 -C 8 -
  • C5-Cio-bicycloalkyl NH 2 , C 1 -C 8 -alkylamino, di-C 1 -C 8 -alkylamino, phenyl, naphthyl or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four Heteroatoms from the group O, N and S,
  • R 1 and R 2 may also together with the nitrogen atom to which they are attached form a five-, six- or seven-membered saturated or partially unsaturated heterocycle containing one, two or three further heteroatoms from the group O, N and S as Ring members may contain, where
  • R 1 and / or R 2 or a heterocycle formed from R 1 and R 2 may carry one, two, three or four identical or different groups R a and / or two substituents for C 1 -C 8 -butyryl bonded to the same or adjacent atoms or ring atoms.
  • Alkylene, OxV-C 2 -C 4 - alkylene or oxy-Ci-C3-alkylenoxy can stand;
  • R a means:
  • R a is halogen, cyano, nitro, hydroxy, carboxyl, C -C -alkyl 8 -alkyl, Ci-C 8 -HaIo- genalkyl, C 2 -C 8 -alkenyl -alkyl, C 2 -C 8 haloalkenyl, C 2 -C 8 -Al kinyl, C 2 -C 8 -HaIo- genalkinyl, C4-Cio-alkadienyl, C 8 alkoxy, Ci-C 8 haloalkoxy, C 2 -C 8 - alkenyloxy, C 2 -C 8 haloalkenyloxy , C 2 -C 8 alkynyloxy, C 2 -C 8 alkynyloxy-halo, C3-C8 cycloalkyl, C3-C8-halocycloalkyl, C3-C8 cycloalkenyl,
  • R a may in turn carry one, two or three identical or different groups R b :
  • R b is halogen, cyano, nitro, hydroxy, mercapto, Ci-C 8 alkyl, C 2 -C 8 alkene yl, C 2 -C 8 kinyl -alkyl, C 4 -Cio-alkadienyl, C 3 -C 8 Cycloalkyl, C 3 -C 8 cycloalkenyl,
  • C 5 -Cio bicycloalkyl C 8 alkoxy, C 2 -C 8 alkenyloxy, C 2 -C 8 alkynyloxy, C 3 - C 8 cycloalkoxy, C3-C8-cycloalkenyloxy, aminothiocarbonyl, Ci-C 8 alkyl- carbonyloxy, Ci-C 8 -Alkylaminothiocarbonyl, di-Ci-C 8 -alkylaminothio- carbonyl, Ci-C8 alkylthio, Ci-C8-alkylsulfinyl, Ci-C 8 alkylsulfonyl, C 6 -C 4 - aryl, C 6 -Ci4-aryloxy, C6-arylthio -Ci4, Ce-Cu-aryl-Ci-Ce-alkoxy, C 6 -C 4 aryl
  • n 0, 1 or 2;
  • A, A ', A "independently of one another hydrogen, Ci-C 8 alkyl, C 2 -C 8 alkene yl, C 2 -C 8 -alkyl kinyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl , Phenyl, where the organic radicals may be partially or completely halogenated and / or mono- or polysubstituted by nitro, cyanato, cyano, C 1 -C 4 -alkoxy, A and A may also be used together with the atoms to which they are attached for a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group consisting of O, N and S;
  • Y is (C 2 -C) -alkenyl, (C 2 -C 10) -alkynyl, (C 3 -C 10) -cycloalkenyl, five-, six-, seven-, eight-, nine- or ten-membered partially unsaturated heterocycle, which is a contains two or three heteroatoms from the group O, N and S as ring members, or an imino group; where Y can carry one, two, three or four identical or different groups R u and / or two substituents bound to the same or adjacent atoms or ring atoms for C 1 -C 6 -alkylene, oxy-C 2 -C 4 -alkylene or
  • R u are independently halogen, cyano, nitro, Ci-C 8 alkyl, Ci-C 8 -HaIo- genalkyl, Ci-C8-alkoxy-Ci-C 8 alkyl, C 2 -C 8 alkenyl, C 2 C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C 4 -C 10 alkadienyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halo genocycloalkyl, C 4 -C 6 cycloalkenyl, C4-C6 halocycloalkenyl, Cs-Cio-bicyclo alkyl, Ci-C8-alkoxy, Ci-C 8 haloalkoxy, C 2 -C 8 alkenyloxy, C 2 -C 8 alkenyloxy-halo, C 2 -C 8 alkynyl
  • R u may carry one, two, three or four identical or different groups R a , wherein R a is as defined above;
  • R 4 is a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S, where R 4 may be partially or completely halogenated and / or may carry one, two, three or four identical or different groups R v :
  • R 4 can mean:
  • R c , R d , R f , R 9 independently of one another represent hydrogen, C 1 -C 6 -alkyl, C 2 -C ⁇ -
  • R w wherein the aliphatic and / or alicyclic groups of the radical definitions of R c , R d , R f , R s, R y and R z are in turn partially or completely halogenated and / or carry one, two, three or four identical or different groups R w can:
  • R w is halogen, cyano, Ci-C 8 -alkyl, C 2 -Cio-alkenyl, C 2 -Cio-alkynyl, C 3 -C 6 -
  • Cycloalkyl C 3 -C 6 cycloalkenyl, C 1 -C 6 alkoxy, C 2 -C alkenyloxy, C 2 -C 10 alkynyloxy, C 3 -C 6 cycloalkoxy, C 3 -C 6 cycloalkenyloxy;
  • R 5 is hydrogen, hydroxy, halogen, cyano, azido, Ci-C 8 alkyl, Ci-Cs-haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 kinyl -alkyl, C 2 -C 8 haloalkynyl, C 4 -C 8 - alkadienyl, C3-C8 cycloalkyl, C3-C8-halocycloalkyl, Ci-C8-alkoxy, Ci-C 8 - haloalkoxy, C2-C8-alkenyloxy,
  • the present invention relates to novel pyrimidines and their use for controlling phytopathogenic fungi, a method for controlling plant-pathogenic fungi, comprising the treatment of the fungi and / or the materials, plants, soil and / or seeds to be protected from fungal attack an effective amount of at least one pyrimidine of formula I, and a method of controlling animal pests. Furthermore, the present invention provides pesticidal agents containing at least one of the compounds of the present invention, methods and intermediates for the preparation of the novel pyrimidines.
  • the pyrimidines I according to the invention can have one or more chiral centers and are then present as enantiomer or diastereomer mixtures.
  • the invention provides both the pure enantiomers or diastereomers or rotamers and mixtures thereof.
  • Suitable compounds of the formula I also include all possible stereoisomers (cis / trans isomers) and mixtures thereof.
  • the compounds according to the invention can be present in various crystal modifications which may differ in their biological activity. They are also the subject of the present invention.
  • WO 01/096314 WO 02/074753, WO 03/043993, WO 04/103978.
  • WO 2005/019207 relates to fungicidal pyrimidine derivatives which contain a heteroaromatic ring in the 4-position and are substituted in the 5-position by halogen, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl, which are optionally halogenated.
  • the salts which can be used as agriculturally acceptable salts are, in particular, the salts of those cations or the acid addition salts of those acids Consider whose cations or anions do not adversely affect the pesticidal activity of the pyrimidines of the invention.
  • the ions of the alkali metals preferably sodium or potassium, the alkaline earth metals, preferably calcium, magnesium or barium, the transition metals, preferably manganese, copper, zinc or iron, or the ammonium ion, the desired one to four (Ci C4) -alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri- (C 1 -C 4) -alkylsulfonium and sulfoxonium ions, preferably tri (Ci-C4) -alkylsulfoxonium, into consideration.
  • the alkali metals preferably sodium or potassium
  • the alkaline earth metals preferably calcium, magnesium or barium
  • the transition metals preferably manganese, copper, zinc
  • Anions of advantageously usable acid addition salts are, for example, chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate,
  • They can be formed by reaction of the compounds according to the invention with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • the compounds of the invention can be obtained in various ways. For example, they can be prepared on the basis of syntheses described in the literature cited above for substituted pyrimidines.
  • compounds according to the invention can be prepared starting from compounds 2
  • Hal 1 and Hal 2 each independently are halogen, in particular fluorine, chlorine or bromine, preferably chlorine, and R 1 and R 2 have the meanings and, preferably, ferred meanings, as defined for formula I.
  • Compounds 2 are known or accessible analogously to the known substances.
  • Hal 3 is halogen, in particular fluorine, chlorine or bromine, preferably bromine.
  • R 4 (as defined for the compounds of the formula I according to the invention)
  • the (C 1 -C 6 -alkylthio) group in the compounds 4 can be converted under generally known conditions to alkylsulfonyl (C 1 -C 6 -alkyl-S) O] 2 -) - group (compound 4a) are oxidized, creating a leaving group for further exchange reactions:
  • hydrogen peroxide or peracids of organic carboxylic acids have proven to be suitable as oxidizing agents; advantageously, MCPBA (metachloroperbenzoic acid) can be used.
  • MCPBA metalachloroperbenzoic acid
  • the oxidation can also be carried out, for example, with selenium dioxide.
  • compounds 4a By reacting compounds 4a with a cyanide such as potassium cyanide in the presence of a crown ether (eg, 18-crown-6), compounds 4b can be prepared wherein R 4 is thus cyano
  • hydrolysis of the nitrile takes place, for example, in the presence of hydrogen peroxide.
  • Amidines are formed, for example, directly from the nitrile with ammonia or an amine or can also be prepared starting from the iminoester by reaction with ammonia or an amine. The reaction can be carried out by methods known in the art (see also Cesar, J .; Sollner, M., Synth.Commun., 2000, 30 (22), 4147-4158).
  • the heterocycle can be reacted directly with an alkylsulfonyl compound (compound 4a) (such as, for example, pyrazole, triazole).
  • an auxiliary base is usually used.
  • an azole may be introduced by first deprotonating it with a suitable base such as an alkali metal alcoholate, hydroxide or sodium hydride, and then in a suitable solvent, such as tetrahydrofuran, dioxane or dimethylformamide, is reacted with the alkylsulfonyl compound.
  • heterocyclic substituents can also be introduced via the structure of the pyrimidine ring, for example.
  • a corresponding heterocyclic amidine which is known to the person skilled in the art or can be prepared from the corresponding heterocyclic nitriles, is reacted with a malonic acid ester to give the pyrimidine ring (see also WO 2003/070721).
  • R 5 represents an alkyl group.
  • An alkyl group (R 5 ) can be introduced by means of organometallic compounds of the formula (R 5 ) n -M, where M is, for example, magnesium, zinc or lithium, for example at the stage of the compound 4 or 4a.
  • M is, for example, magnesium, zinc or lithium
  • R 5 is a cyano group or an alkoxy substituent
  • the radical R 5 can be introduced by reaction with alkali metal cyanides or alkali metal alcoholates.
  • Halogen fluorine, chlorine, bromine and iodine
  • Haloalkyl Alkyl as mentioned above, wherein in these groups partially or completely the hydrogen atoms are replaced by halogen atoms as mentioned above.
  • the alkyl groups are substituted at least once or completely by a particular halogen atom, preferably fluoro, chloro or bromo.
  • the alkyl groups are partially or completely halogenated by various halogen atoms; for mixed halogen substitutions, the combination of chlorine and fluorine is preferred.
  • (C 1 -C 4) -haloalkyl more preferably (C 1 -C 2) -haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1 Fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2, 2,2-trichloroethyl, pentafluoroethyl or 1,1,1-trifluoroprop-2-yl;
  • Hydroxyalkyl Alkyl as mentioned above, wherein one or more hydrogen atoms are replaced by hydroxy (OH) groups.
  • Alkenyl and the alkenyl moieties in assembled groups such as alkenyloxy: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, 2 to 6, 2 to 8 or 2 to 10 carbon atoms and one or two, preferably one, double bonds in any position.
  • alkenyl groups such as (C 2 -C 4) -alkenyl
  • larger alkenyl groups such as (C 2 -C 8 -alkenyl
  • suitable alkenyl groups are, for example, C 2 -C 6 -alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl , 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pent-enyl, 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-2-butenyl, 2-methyl-2-butenyl, 3-
  • Haloalkenyl alkenyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;
  • Alkadienyl unsaturated, 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;
  • Alkinyl and the alkynyl moieties in the form of compound groups straight-chain or branched hydrocarbon groups having 2 to 4, 2 to 6, 2 to 8 or 2 to 10 carbon atoms and one or two, preferably one, triple bonds in any position, for example 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-he
  • Haloalkynyl alkynyl, as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms, as described above under haloalkyl, in particular fluorine, chlorine or bromine;
  • Cycloalkyl and the cycloalkyl moieties in assembled groups mono- or bi-cyclic, saturated hydrocarbon groups having in particular 3 to 6 or 3 to 8 carbon ring members, e.g. C3-C6 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl;
  • Halogencycloalkyl cycloalkyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;
  • Cycloalkenyl monocyclic, monounsaturated hydrocarbon groups having preferably 3 to 10, 3 to 8 or 4 to 6, in particular 5 to 6 carbon ring members, such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexene-3 yl, cyclohexene-4-yl and the like;
  • Halocycloalkenyl cycloalkenyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;
  • Alkoxy for an oxygen-bonded alkyl group as defined above, preferably having 1 to 8, more preferably 2 to 6 carbon atoms. According to the invention, it may be preferable to use small alkoxy groups such as (C 1 -C 4) -alkoxy, on the other hand It may also be preferred to use larger alkoxy groups such as (Cs-Cs) -alkoxy.
  • Examples of preferred alkoxy groups are: methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy; and also, 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;
  • Haloalkoxy alkoxy, as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms, as described above under haloalkyl, in particular fluorine, chlorine or bromine.
  • it may be preferable to use short-chain haloalkoxy groups such as (C 1 -C 4) -haloalkoxy, or it may be preferable to use longer-chain haloalkoxy groups such as (C 5 -C 6) -haloalkoxy
  • preferred haloalkoxy groups are 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-triflu
  • Alkenyloxy Alkenyl as defined above, which is bonded via an oxygen atom. Preferred are (C 2 -C 8) alkenyloxy, more preferably (C 3 -C 6) alkenyloxy. In the present invention, it may be preferable to use short-chain alkenyloxy groups such as (C 2 -C 4) alkenyloxy, but on the other hand, it may also be preferable to use longer-chain alkenyloxy groups such as (C 5 -C 8) alkenyloxy;
  • Alkylene divalent linear chains of CH 2 groups. Preference is given to (C 1 -C 6) -alkylene, more preferably (C 2 -C 4) -alkylene, and furthermore it may be preferred to use (C 1 -C 3 ) -alkylene groups.
  • Examples of preferred alkylene radicals are CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 (CH 2 ) 2 CH 2 , CH 2 (CH 2 ) 3 CH 2 and CH 2 (CH 2 ) 4 CH 2 ;
  • Oxyalkylene Alkylene, as defined above, preferably having 2 to 4 CH 2 groups, wherein a valence is bonded to the skeleton via an oxygen atom.
  • examples for preferred oxyalkylene radicals are OCH 2 , OCH 2 CH 2 , OCH 2 CH 2 CH 2 and OCH 2 (CH 2 ) 2 CH 2 ;
  • Oxyalkylenoxy Alkylene, as defined above, preferably having 1 to 3 CH 2 groups, wherein both valences are bonded to the skeleton via an oxygen atom.
  • Examples of preferred oxyalkyleneoxy radicals are OCH 2 O, OCH 2 CH 2 O and OCH 2 CH 2 CH 2 O;
  • Alkylthio alkyl as defined above attached via an S atom
  • Alkylsulfinyl alkyl as defined above which is bonded through an SO group
  • Alkylsulfonyl alkyl as defined above attached through an S (O) 2 group;
  • the respective heterocycle may be attached via a carbon atom or via a nitrogen atom, if present. It may be preferred according to the invention that the respective heterocycle is bonded via carbon, on the other hand it may also be preferred that the heterocycle is bonded via nitrogen.
  • the heterocycle means in particular:
  • heterocyclyl containing one, two or three nitrogen atoms and / or an oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, wherein the heterocyclyl can be attached via C or N; 5-membered heteroaryl containing one, two, three or four nitrogen atoms or one, two or three nitrogen atoms and / or a sulfur or oxygen atom which may be attached via C or N; or
  • 6-membered heteroaryl containing one, two, three or four, preferably one, two or three, nitrogen atoms which may be attached via C or N;
  • 5-membered heteroaryl containing one, two, three or four nitrogen atoms or one, two or three nitrogen atoms and / or a sulfur or oxygen atom, which heteroaryl may be attached via C or N, if present: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and / or one sulfur or oxygen atom as ring members, eg Furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (1,2,3-; 1,2,4-triazolyl), tetrazolyl, oxazolyl, isoxazolyl, 1,3,4-oxadiazolyl, thiazolyl, isothiazolyl and thiadiazolyl, in particular 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl,
  • 6-membered heteroaryl containing one, two, three or four, preferably one, two or three nitrogen atoms, wherein the heteroaryl can be attached via C or N, if present: 6-membered ring heteroaryl groups which contain, in addition to carbon atoms, one to four or may contain one to three nitrogen atoms as ring members, eg Pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1, 2,3-triazinyl, 1, 2,4-triazinyl, 1, 3,5-triazinyl, especially 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4 Pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1, 3,5-triazin-2-yl and 1, 2,4-triazin-3-yl.
  • 6-membered ring heteroaryl groups which contain, in addition
  • X is NR 1 R 2 . It may be preferred if R 2 is hydrogen. In one embodiment of the present invention, R 2 is hydrogen and R 1 is other than hydrogen. Furthermore, it may be preferable that at least one of R 1 and R 2 is other than hydrogen. Equally preferred are compounds of the formula I in which R 1 and R 2 are different from hydrogen. Preferred among these are compounds of the formula I in which R 2 is (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl or (C 1 -C 4) -alkoxy, especially methyl, ethyl or methoxy, in particular methyl or ethyl.
  • R 1 is straight-chain or branched, unsubstituted or substituted (Ci-Cs) -AlkVl, (Ci-Cs) -haloalkyl, (C 2 -C 8) -alkenyl, (C 2 -C 8) -alkynyl , (C 3 -C 8) -cycloalkyl, unsubstituted or substituted phenyl or naphthyl or an unsubstituted or substituted five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S.
  • R 1 is in particular (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, where these radicals 1 , 2, 3, 4 or 5 times may be substituted by halogen, (C 1 -C 6) -alkyl or (C 1 -C 6) -haloalkyl.
  • R 1 denotes (C 3 -C 6) -cycloalkyl which may be substituted by (C 1 -C 4) -alkyl or (C 3 -C 6) -cycloalkyl- (C 1 -C 4) -alkyl.
  • R 1 and R 2 together with the nitrogen atom to which they are attached represent unsubstituted or substituted saturated or partially unsaturated heterocyclyl as defined above.
  • heterocyclyl is substituted or substituted by 1, 2 or 3 substituents R a , preferred substituents R a of heterocyclyl being selected from halogen, (C 1 -C 4) -alkyl and (C 1 -C 4) -haloalkyl.
  • preferred heterocyclyl rings are 2-methylpyrrolidinyl, 4-methylpiperidinyl, 4-trifluoromethylpiperidinyl, 3,4-dimethylpiperidinyl, 5-methylperhydro-1, 2-oxazinyl and 6-methylperhydro- (1, 2) -oxazinyl.
  • X is OR 3 .
  • X is SR 3 .
  • R 3 is preferably in each case C 1 -C 6 -alkyl, in particular C 1 -C 4 -alkyl, C 1 -C 6 -haloalkyl, in particular C 1 -C 4 -haloalkyl, C 2 -C 6 -alkenyl, in particular C 2 -C 4 -alkenyl, C 2 -C 6 -cycloalkyl Alkynyl, in particular C 2 -C 4 -alkynyl, or C 3 -C 6 -cycloalkyl.
  • R 3 is branched in the ⁇ -position, branched C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 1 -C 6 -haloalkyl.
  • R 3 is ethyl, propyl, i-propyl, 1, 2-dimethylpropyl, 1, 2,2-trimethylpropyl, 1-methyl-2,2,2-trifluoroethyl or 2,2,2 - trifluoroethyl.
  • X is optionally substituted by R a substituted Ci-Cs-alkyl.
  • Y is (C 2 -C 10) alkenyl, preferably (C 2 -C 6) alkenyl. According to another preferred embodiment, Y is (C 2 -C 10) -alkynyl, preferably (C 2 -C 6) -alkynyl.
  • Y may each carry one, two, three or four identical or different groups R u , where R u is as defined in the claims and preferably each independently selected from: halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 - Haloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogeno-cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy and -Si ( C6 alkyl).
  • R u is as defined in the claims and preferably each independently selected from: halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 - Haloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloal
  • Y is an unsubstituted or substituted by R u , as defined above, (C3-Cio) -cycloalkenyl, preferably (C5-C7) -cycloalkenyl group.
  • the cycloalkenyl group preferably has one or two double bonds. Examples of cycloalkenyl groups as substituent Y are cyclopent-1-en-1-yl, cyclohex-1-en-1-yl, which according to the invention may be substituted by R u , as defined above.
  • Y is an unsubstituted or substituted five-, six-, seven-, eight-, nine- or ten-membered partially unsaturated heterocycle containing one, two or three heteroatoms from the group O, N and S as ring members
  • Y preferably represents an unsubstituted or substituted five- or six-membered partially unsaturated heterocycle which contains one, two or three nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms.
  • the heterocyclyl ring may be bonded to the pyrimidine skeleton via C or N, respectively.
  • the heterocycle contains one or two nitrogen atoms.
  • Partially unsaturated means that the heterocycle does not form an aromatic system, wherein the heterocycle preferably contains one or two double bonds.
  • Y is a group (A)
  • Z is CR 7 R 8 , wherein R 6 , R 7 and R 8 are as defined in the claims and preferably independently of one another are hydrogen, halogen, cyano, nitro, C 1 -C 8 -alkyl , Ci-C8-haloalkyl, Ci-C8-alkoxy-Ci- C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 -alkyl kinyl, C 2 - C 8 haloalkynyl, C 4 - Cio-alkadienyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 4 -C 6 -cycloalkenyl, C 4 -C 6 -halocycloalkenyl,
  • R 6 , R 7 and / or R 8 may carry one, two, three or four identical or different groups R a , where m, A, A ', A "and R a have the meanings and preferred meanings, as described above are defined.
  • R 7 and R 8 are preferably independently selected from hydrogen, halogen, such as fluoro, chloro and bromo; Ci-C ⁇ -alkyl, in particular methyl, ethyl, n-propyl and iso-propyl; C 1 -C 6 -haloalkyl, in particular trichloromethyl, trifluoromethyl, 1,1,1-trifluoroethyl; Ci-C ⁇ -alkoxy, in particular methoxy, ethoxy and propoxy; or C 1 -C 6 -haloalkoxy, for example trichloromethoxy, trifluoromethoxy and 1,1,1-trifluoroethoxy.
  • halogen such as fluoro, chloro and bromo
  • Ci-C ⁇ -alkyl in particular methyl, ethyl, n-propyl and iso-propyl
  • C 1 -C 6 -haloalkyl in particular trichloromethyl, trifluoromethyl,
  • one of the substituents is selected from hydrogen, halogen, such as fluorine, chlorine and bromine, and Ci-C6-alkyl, in particular methyl, ethyl and iso-propyl; and the other substituent is selected from halogen such as fluorine, chlorine and bromine; Ci-C ⁇ -alkyl, in particular methyl, ethyl; C 1 -C 6 -haloalkyl, in particular trichloromethyl, trifluoromethyl, 1,1,1-trifluoromethane I; and Ci-C ⁇ -alkoxy, in particular methoxy, ethoxy and propoxy.
  • halogen such as fluorine, chlorine and bromine
  • Ci-C ⁇ -alkyl in particular methyl, ethyl
  • C 1 -C 6 -haloalkyl in particular trichloromethyl, trifluoromethyl, 1,1,1-trifluoromethane I
  • Ci-C ⁇ -alkoxy in particular methoxy,
  • R 6 is preferably hydrogen, halogen, Ci-C8-alkoxy, Ci-C 8 alkyl, C 8 - haloalkyl, Ci-C 8 alkoxy-Ci-C 8 alkyl, C 2 -C 8 - Alkenyl, C 1 -C 6 -alkylamino or di (C 1 -C 6 -alkyl) amino.
  • R 6 is halogen, such as fluorine, chlorine and bromine; Ci-C ⁇ -alkyl, in particular methyl, ethyl, n-propyl and iso-propyl; Ci-C ⁇ -haloalkyl, in particular trichloromethyl, trifluoromethyl, 1,1,1-trifluoroethyl; Ci-C ⁇ -alkoxy, in particular methoxy, ethoxy and propoxy; or Ci-C ⁇ -haloalkoxy, such as trichloro-methoxy, trifluoromethoxy and 1, 1, 1-trifluoroethoxy. It may be preferred that R 6 is different from hydrogen.
  • Ci-C ⁇ -alkyl in particular methyl, ethyl, n-propyl and iso-propyl
  • Ci-C ⁇ -haloalkyl in particular trichloromethyl, trifluoromethyl, 1,1,1-trifluoroethyl
  • Ci-C ⁇ -alkoxy in particular me
  • Z is NR 9 .
  • R 9 has the meanings as defined above for R 6 , R 7 and R 8 , wherein R 6 and R 9 can form a corresponding cyclus or heterocycle and R 6 and / or R 9 or one of R 6 and R 9 formed cyclus or heterocycle may be substituted accordingly.
  • R 9 is hydrogen, halogen, such as fluorine, chlorine and bromine; Ci-C ⁇ -alkyl, in particular methyl, ethyl, n-propyl and iso-propyl; d-C ⁇ haloalkyl, especially trichloromethyl, trifluoromethyl, 1,1,1-trifluoroethyl; Ci-C ⁇ -alkoxy, in particular methoxy, ethoxy and propoxy; or Ci-C ⁇ -halo-alkoxy, such as trichloromethoxy, trifluoromethoxy and 1, 1, 1-trifluoroethoxy.
  • R 6 has the preferred meanings as stated above. It may be preferred that R 6 and / or R 9 are different from hydrogen.
  • R 4 is a five- or six-membered aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S, where R 4 is partially or completely halogenated and / or one, two, three or four identical or different groups R v can carry.
  • R 4 is not pyridin-2-yl.
  • R 4 is a five-membered aromatic heterocycle, according to another embodiment of the invention for a six-membered aromatic heterocycle, but R 4 is preferably not pyridin-2-yl.
  • Examples of preferred five-membered aromatic heterocycles are pyrrolyl, pyrazolyl (in particular pyrazol-1-yl), imidazolyl, [1, 2,3] -triazolyl (in particular [1, 2,3] -triazol-1-yl), [ 1,2,4] triazolyl (especially [1, 2,4] triazol-1-yl), tetrazolyl, oxazolyl, isoxazolyl, [1, 3,4] oxadiazolyl, furyl, thienyl, thiazolyl and isothiazolyl, especially preferably pyrazolyl, [1,2,3] triazolyl and [1,2,4] triazolyl.
  • Examples of preferred six-membered aromatic heterocycles are pyridin-3-yl, pyridin-4-yl, pyrimidinyl, pyrazinyl, pyridazinyl, [1, 2,3] triazinyl and [1,2,4] triazinyl, preferably pyrimidinyl and pyridazinyl.
  • R 4 is an unsubstituted or substituted five- or six-membered saturated or partially unsaturated heterocycle.
  • R 4 in the compounds of the formula I is preferably 1-pyridine- (1, 2-dihydro) -2-onyl, 1-pyrrolidone, imidazolidinone, isoxazolidinone or oxazolidinone, in particular 2-pyrrolidon-1-yl, imidazolidinone-1 yl, isoxazolidin-3-one-2-yl or oxazolidin-2-one-3-yl.
  • the above-defined heterocycle may each be unsubstituted or substituted with one, two or three substituents R v and, unless otherwise indicated, each be bound to the pyrimidine skeleton via C or N.
  • R c, R d, R f, R 9 are independently hydrogen, Ci-C 6 -alkyl, C 2 -C 6 alkenyl, C 2 -
  • R w wherein the aliphatic and / or alicyclic groups of the radical definitions of R c , R d , R f , R s, R y and R z are in turn partially or completely halogenated and / or carry one, two, three or four identical or different groups R w can:
  • R w is halogen, cyano, d-C ⁇ -alkyl, C2 -Cio-alkenyl, C 3 -C 6 cycloalkyl, C 3 -C 6 - cycloalkenyl, Ci-C6 alkoxy;
  • R 5 represents halogen, cyano, CrC 6 - kinyl -Al 6 alkyl, d-Ce-haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C, C 2 -C 6 - haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, Ci-C 6 alkoxy, -C 6 - haloalkoxy, C 2 -C 6 alkenyloxy, C3-C4-alkynyloxy, Ci -Cs Alkylthio, C 1 -C 6 -alkylamino, di- (C 1 -C 6 -alkyl) amine, where the aliphatic and alicyclic groups of the radical definitions of R 5, in turn, independently contain one, two, three or four substituents selected from halogen,
  • R 5 is halogen, cyano, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy, in particular halogen.
  • suitable R 5 are chloro, cyano, methoxy and trifluoromethoxy.
  • R 5 is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, in particular methyl, ethyl or trifluoromethyl.
  • Particularly preferred compounds according to the present invention are the compounds I compiled in the following tables.
  • R 6 is chlorine
  • R 7 is bromine
  • R 8 is bromine
  • X is NR 1 R 2 and R 1 and R 2 for a particular compound correspond in each case to one row of Table A.
  • Table 7 Compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13,
  • R 6 is chlorine
  • R 7 is methyl
  • R 8 is chlorine
  • X is NR 1 R 2 and R 1 and R 2 for a particular compound correspond in each case to one row of Table A.
  • Table 10 Compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13,
  • Table 12 Compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.1 1, 1.12, 1.13, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, I.20, 1.21, I.22, I.23 and I.24, in which R 5 is chlorine, R 6 is chlorine, R 7 is methyl, R 8 is methoxy, X is NR 1 R 2 and R 1 and R 2 for a particular compound correspond in each case to one row of Table A.
  • Table 13 Compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13, 1.14, 1.15 , 1.16 1.17 1.18 1.19 I.20, 1.21 I.22, I.23 and I.24, wherein R 5 is chloro, R 6 represents chlorine, R 7 is methoxy, R 8 is chlorine, X is NR 1 R 2 and R 1 and R 2 for a particular compound corresponds in each case to one row of Table A.
  • Table 14 Compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13, 1.14, 1.15 , 1.16 1.17 1.18 1.19 I.20, 1.21 I.22, I.23 and I.24, wherein R 5 is chloro, R 6 represents chlorine, R 7 is methoxy, R 8 is bromo, X is NR 1 R 2 and R 1 and R 2 for a particular compound corresponds in each case to one row of Table A.
  • Table 15 Compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13, 1.14, 1.15 , 1.16 1.17 1.18 1.19 I.20, 1.21 I.22, I.23 and I.24, where R 5 is chlorine R 6 is chlorine, R 7 is methoxy, R 8 is methyl, X is NR 1 R 2 and R 1 and R 2 for a particular compound corresponds in each case to one row of Table A.
  • Table 16 Compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13, 1.14, 1.15 , 1.16 1.17 1.18 1.19 I.20, 1.21 I.22, I.23 and I.24, wherein R 5 is chloro, R 6 represents chlorine, R 7 is methoxy, R 8 is methoxy, X is NR 1 R 2 and R 1 and R 2 for a particular compound corresponds in each case to one row of Table A.
  • Table 17 Compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13,
  • R 6 , R 7 , R 8 are each bromine, X is NR 1 R 2 and R 1 and R 2 for a particular compound correspond in each case to one row of Table A.
  • Table 23
  • R 5 is chlorine
  • R 6 is bromine
  • R 7 is bromine
  • R is 8 methoxy
  • X is NR 1 R 2 and R 1 and R 2 is a particular compound in each case one row of the table
  • R 6 is bromine
  • R 7 is methyl
  • R 8 is bromine
  • X is NR 1 R 2 and R 1 and R 2 for a particular compound correspond in each case to one row of Table A.
  • Table 27 Compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13,
  • Table 28 Compounds of the formula 1.1, I.2, I.3, I.4, I.5, I .6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, I.20, 1.21, I.22, I.23 and I .24, wherein R 5 is chlorine, R 6 is bromine, R 7 is methyl, R 8 is methoxy, X is NR 1 R 2 and R 1 and R 2 for a particular compound corresponds in each case to one row of Table A Table 29 compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13, 1.14, 1.15, 1.16 1.17 1.18 1.19 I.20, 1.21 I.22, I.23 and I.24, wherein R 5 is chloro, R 6 is bromine, R 7 is methoxy, R 8 is chlorine, X NR 1
  • A corresponds to Table 31 compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12,
  • R 5 is chlorine
  • R 6 is bromine
  • R 7 is methoxy
  • X is NR 1 R 2 and R 1 and R 2 are a particular compound of one row of the table
  • A corresponds to Table 32 compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12,
  • R 6 is methyl
  • R 7 is chlorine
  • R 8 is chlorine
  • X is NR 1 R 2 and R 1 and R 2 for a particular compound correspond in each case to one row of Table A.
  • Table 34 Compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13,
  • R 1 and R 2 correspond for a particular compound in each case one row of Table A.
  • R 6 is methyl
  • R 7 is methyl
  • R 8 is chlorine
  • X is NR 1 R 2 and R 1 and R 2 for a particular compound correspond in each case to one row of Table A.
  • Table 42 Compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13,
  • R 6 is methoxy
  • R 7 is chlorine
  • R 8 is chlorine
  • X is NR 1 R 2 and R 1 and R 2 for a particular compound correspond in each case to one row of Table A.
  • Table 50 Compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13,
  • R 6 is methoxy
  • R 7 is bromine
  • R 8 is methoxy
  • X is NR 1 R 2 and R 1 and R 2 for a particular compound correspond in each case to one row of Table A.
  • Table 57 Compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13,
  • R 6 is methoxy
  • R 7 is methoxy
  • R 8 is methyl
  • X is NR 1 R 2 and R 1 and R 2 for a particular compound correspond in each case to one row of Table A.
  • Table 64 Compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.1 1, 1.12, 1.13,
  • Chlorine, R 6 is methyl, R 9 is methoxy, X is NR 1 R 2 and R 1 and R 2 for a particular compound corresponds in each case to one row of Table A.
  • R 6 is chlorine
  • R 7 is chlorine
  • R 8 is bromine
  • X is a particular organic compound
  • R 6 is chlorine
  • R 7 is chlorine
  • R 8 is methyl
  • X is a particular organic radical
  • R 6 is chlorine
  • R 7 is chlorine
  • R 8 is methoxy
  • X for a particular compound corresponds in each case to one row of Table B Table 78
  • R 6 is chlorine, R 7 is bromine, R 8 is chlorine and X is a particular
  • R 6 is chlorine, R 7 is bromine, R 8 is bromine and X is a particular
  • R 6 is chlorine, R 7 is bromine, R 8 is methyl and X is a certain
  • R 6 is chlorine
  • R 7 is bromine
  • R 8 is methoxy
  • X for a particular compound corresponds in each case to one row of Table B Table 82
  • R 6 is chlorine, R 7 is methyl, R 8 is chlorine and X is a particular
  • R 6 is bromine, R 7 is chlorine, R 8 is methyl and X is a particular
  • R 6 is bromine
  • R 7 is chlorine
  • R 8 is methoxy
  • X for a particular compound corresponds in each case to one row of Table B Table 94
  • R 6 is bromine
  • R 7 is bromine
  • R 8 is chlorine
  • X is a certain
  • R 6 , R 7 , R 8 are each bromine and X for a particular compound corresponds in each case to one row of Table B corresponds to Table 96
  • R 6 is bromine
  • R 7 is bromine
  • R 8 is methyl
  • X is a particular
  • R 6 is bromine
  • R 7 is bromine
  • R 8 is methoxy
  • X for a particular compound corresponds in each case to one row of Table B corresponds to Table 98
  • R 6 is bromine, R 7 is methyl, R 8 is chlorine and X is a particular
  • R 6 is bromine
  • R 7 is methyl
  • R 8 is bromine
  • X is a particular
  • Table 109 Compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13,
  • Table 1 11 compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13,
  • Table 1 14 compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13,
  • Table 1 15 compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13,
  • R 6 is methyl
  • R 7 is methyl
  • R 8 is methoxy
  • X for a particular compound corresponds in each case to one row of Table B.
  • R 6 is methyl
  • R 7 is methoxy
  • R 8 is chlorine
  • X for a particular compound corresponds in each case to one row of Table B.
  • R 6 is methyl
  • R 7 is methoxy
  • R 8 is bromine
  • X for a particular compound corresponds in each case to one row of Table B.
  • R 6 is methyl
  • R 7 is methoxy
  • R 8 is methyl
  • X for a particular compound corresponds in each case to one row of Table B.
  • R 6 is methyl
  • R 7 is methoxy
  • R 8 is methoxy
  • X for a particular compound corresponds in each case to one row of Table B.
  • R 6 is methoxy
  • R 7 is chlorine
  • R 8 is chlorine
  • X for a particular compound corresponds in each case to one row of Table B.
  • R 6 is methoxy
  • R 7 is chlorine
  • R 8 is bromine
  • X for a particular compound corresponds in each case to one row of Table B.
  • R 6 is methoxy
  • R 7 is chlorine
  • R 8 is methyl
  • X for a particular compound corresponds in each case to one row of Table B.
  • Table 125
  • Table 135 Compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13,
  • Chlorine, R 6 is bromine, R 9 is methyl and X for a particular compound corresponds in each case to one row of Table B.
  • Chlorine, R 6 is methyl, R 9 is methyl and X for a particular compound corresponds in each case to one row of Table B.
  • Chlorine, R 6 is chlorine, R 9 is chlorine and X for a particular compound corresponds in each case to one row of Table B.
  • Chlorine, R 6 is bromine, R 9 is chlorine and X for a particular compound corresponds in each case to one row of Table B.
  • Chlorine, R 6 is methyl, R 9 is chlorine and X for a particular compound corresponds in each case to one row of Table B.
  • R 5 is methyl
  • R 6 is bromine
  • R 7 is chlorine
  • R 8 is bromine
  • X is NR 1 R 2 and R 1 and R 2 for a particular compound correspond in each case to one row of Table A, Table 165
  • R 5 is methyl
  • R 6 is methyl
  • R 7 is methoxy
  • R 8 is methyl
  • X is NR 1 R 2 and R 1 and R 2 for a particular compound correspond in each case to one row of Table A in accordance with Table 194
  • R 5 is methyl
  • R 6 is methoxy
  • R 7 is methyl
  • R 8 is methyl
  • X for NR 1 R 2 and R 1 and R 2 for a particular compound correspond in each case to one row of Table A, Table 206
  • Methyl, R 6 is bromine, R 9 is methoxy, X is NR 1 R 2 and R 1 and R 2 for a particular compound correspond to one row of Table A, respectively
  • Table 220 Compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13,
  • R 5 is methyl
  • R 6 , R 7 , R 8 are each chlorine and X for a particular compound corresponds in each case to one row of Table B.
  • Table 240 Compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13,
  • R 5 is methyl
  • R 6 , R 7 , R 8 are each bromine and X is a each compound corresponds to one row of Table B.
  • Table 245 Compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13,
  • Table 268 Compounds of the formula 1.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, 1.10, 1.11, 1.12, 1.13,
  • the compounds of the formula I or I 'and I "and / or the agriculturally acceptable salts thereof are suitable as active compounds, in particular as fungicides, and are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from US Pat Class of Ascomycetes, Basidiomycetes, Deuteromycetes and Peronosporomycetes (syn. Oomycetes), some of which are systemically active and can be used in crop protection as foliar, pickling and soil fungicides.
  • Botrytis cinerea (gray mold) on strawberries, vegetables, flowers and vines, • Bremia lactucae on salad,
  • Cochliobolus species on corn, cereals, rice e.g. Cochliobolus sativus on cereals, Cochliobolus miyabeanus on rice,
  • Fusarium and Verticillium species on various plants e.g. F. graminearum or F. culmorum on cereal or F. oxysporum on a variety of plants such as e.g. Tomatoes,
  • Gaeumanomyces graminis on cereals Gibberella species on cereals and rice (e.g., Gibberella fujikuroi on rice),
  • Mycosphaerella species on cereals, bananas and peanuts e.g. M. granicola on wheat or M.fijiensis on bananas,
  • Peronospora species on cabbage and bulbous plants such as P. brassicae on cabbage or P. destructor on onion,
  • Phytophthora species on various plants e.g. P.capsici on paprika, • Plasmopara viticola on vines,
  • Pseudoperonospora on various plants e.g. P. cubensis on cucumber or P. humili on hops
  • Puccinia species on various plants e.g. P. triticina, P. striformins, P. hordei or P. graminis on cereals, or P. asparagi on asparagus
  • Rhizoctonia species on cotton, rice, lawn, corn, oilseed rape, potatoes, sugar beet, vegetables and various plants such as e.g. R.solani on turnips and various plants,
  • 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 of the invention may also be used in cultures tolerant of insect or fungal growth by breeding, including genetic engineering methods.
  • the compounds of the invention and / or their agriculturally acceptable salts are used by treating the fungi and / or the plants, seeds, materials and / or the soil to be protected against fungal attack with a fungicidally effective amount of these 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 present invention is therefore a method for controlling phytopathogenic fungi, comprising the treatment of fungi and / or to be protected from fungal attack materials, plants, soils and / or seeds with an effective amount of at least one pyrimidine invention and / or a agriculturally acceptable salt thereof.
  • a further subject matter of the present invention is a method for controlling animal pests in agriculture, comprising the treatment of the pests and / or the materials, plants, soils and / or seeds to be protected from them with an effective amount of at least one pyrimidine according to the invention and / or an agriculturally acceptable salt thereof.
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90 wt .-% of active ingredient.
  • the application rates in the application in crop protection depending on the nature of the desired effect between 0.01 and 2.0 kg of active ingredient per ha.
  • seed treatment in general, amounts of active ingredient of 1 to 1000 g / 100 kg of seed, preferably 1 to 200 g / 100 kg, in particular 5 to 100 g / 100 kg are used.
  • Seed treatment can be carried out by a person skilled in the art. te techniques such as Seed Dressing, Seed Coating, Seed Dusting, Seed Soaking and Seet Pelleting.
  • Another object of the present invention is therefore seed, comprising a compound of the invention in an amount of 1 to 1000 g per 100 kg.
  • the application rate of active ingredient depends on the type of application and the desired effect. Usual application rates are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of material treated in the material protection.
  • Another object of the present invention is an agent, in particular a fungicidal composition comprising at least one compound of the invention and / or an agriculturally acceptable salt thereof and at least one solid or liquid carrier.
  • the agent may further contain at least one other fungicidal, insecticidal and / or herbicidal active ingredient, as set out in more detail below.
  • the compounds according to the invention and / or their agriculturally acceptable salts can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the application form depends on the respective purpose; It should in any case ensure a fine and uniform distribution of the compound according to the invention.
  • the formulations are prepared in a known manner, for example by stretching the active ingredient with solvents and / or excipients, if desired using emulsifiers and dispersants.
  • Suitable solvents / hydrogens are essentially:
  • solvents for example Solvesso products, xylene
  • paraffins for example petroleum fractions
  • alcohols for example methanol, butanol, pentanol, benzyl alcohol
  • ketones for example cyclohexanone, gamma-butyrolactone
  • pyrrolidones NMP, NOP
  • acetates glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters.
  • solvent mixtures can also be used, carriers such as ground natural minerals (for example kaolins, clays,
  • 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.
  • the surface-active substances 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, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, Nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ether
  • 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, for example toluene, xylene , Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, for example dimethylsulfoxide, N-methylpyrrolidone or water into consideration.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene , Paraffin, tetrahydronaphthalene, alkylated
  • Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
  • Granules for example coated, impregnated and homogeneous granules, can be prepared by binding the active compounds to solid carriers.
  • Solid carriers are, for example, mineral earths, such as silica gels, silicates, talc, kaolin, ataclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cornmeal, tree bark, wood and nutshell flour, cellulosic powder and other solid carriers.
  • mineral earths such as silica gels, silicates, talc, kaolin, ataclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such
  • Seed treatment formulations may additionally contain binders and / or gelling agents and optionally dyes.
  • Binders can be added to increase adhesion of the active ingredients to the seed after treatment.
  • Suitable binders are, for example, EO / PO block copolymer surfactants, but also polyvinyl alcohols, polyvinylpyrrolidones, polyacrylates, polymethacrylates, polybutenes, polyisobutylenes, polystyrenes, polyethylene amines, polyethylene amides, polyethyleneimines (Lupasol®, Polymin®), polyethers, polyurethanes, Polyvinyl acetates, Tylose and copolymers of these polymers.
  • a suitable gelling agent is, for example, carrageenan (Satiagel®).
  • the formulations generally contain between 0.01 and 95 wt .-%, preferably between 0.1 and 90 wt .-% of the active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • 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
  • the formulations in question give, after dilution of from two to ten times, active compound concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations.
  • formulations according to the invention are: 1. Products for dilution in water
  • a Water-soluble concentrates (SL, LS)
  • a compound according to the invention 20 parts by weight of a compound according to the invention are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant, e.g. Polyvinylpyrrolidone dissolved. Dilution in water gives a dispersion.
  • a dispersant e.g. Polyvinylpyrrolidone dissolved. Dilution in water gives a dispersion.
  • the active ingredient content is 20% by weight
  • Emulsifiable Concentrates 15 parts by weight of a compound according to the invention are dissolved in 75 parts by weight of xylene with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution in water results in an emulsion.
  • the formulation has an active ingredient content of 15% by weight.
  • a compound according to the invention 25 parts by weight of a compound according to the invention are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5% by weight). Parts) solved.
  • 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.
  • a compound according to the invention 20 parts by weight of a compound according to the invention are comminuted with the addition of 10 parts by weight dispersing and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine active ingredient suspension. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • Water-dispersible and Water-soluble Granules 50 parts by weight of a compound according to the invention are finely ground with the addition of 50 parts by weight of dispersing and wetting agents and by means of technical equipment (eg extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble Granules produced. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the formulation has an active ingredient content of 50% by weight.
  • Water-dispersible and water-soluble powders 75 parts by weight of a compound according to the invention are ground in a rotor-stator mill with the addition of 25 parts by weight of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active ingredient content of the formulation is 75% by weight.
  • 0.5 parts by weight of a compound according to the invention 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 an active ingredient content of 0.5 wt .-%.
  • a compound according to the invention 10 parts by weight of a compound according to the invention are dissolved in 90 parts by weight of an organic solvent, for example xylene.
  • an organic solvent for example xylene.
  • LS water-soluble concentrates
  • FS suspensions
  • DS dusts
  • WS water-dispersible and water-soluble powders
  • ES emulsions
  • EC emulsifiable concentrates
  • GF gel formulations
  • These formulations may be applied to the seed undiluted or, preferably, diluted. The application can be done before sowing.
  • FS formulations for seed treatment.
  • such formulations contain 1 to 800 g / l active ingredient, 1 to 200 g / l surfactants, 0 to 200 g / l antifreeze, 0 to 400 g / l binder, 0 to 200 g / l dyes and solvents, preferably water ,
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, atomizing, dusting , Scattering or pouring are applied.
  • the forms of application depend entirely on the intended use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
  • the substances as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, tackifiers, dispersants or emulsifiers. But it can also be effective substance wetting, adhesion, dispersing or emulsifying agents and possibly
  • Solvent or oil concentrates are prepared, which are suitable for dilution with water.
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume
  • wetting agents eg. Break Thru S 240 ®
  • Alcohol alkoxylates eg. As Atplus 245 ®, Atplus MBA 1303 ®, Plurafac LF 300 ® and Lutensol ON 30 ®
  • EO-PO block polymers eg. B.
  • Pluro- nic RPE 2035 ® and Genapol B ® Alcohol ethoxylates, eg. As Lutensol XP 80 ®; and sodium dioctylsulfosuccinate, e. B. Leophen RA ®.
  • the agents according to the invention may also be present together with other active substances, for example with herbicides, pesticides (such as insecticides and acaricides), growth regulators, fungicides or else with fertilizers.
  • other active substances for example with herbicides, pesticides (such as insecticides and acaricides), growth regulators, fungicides or else with fertilizers.
  • Another object of the present invention is a combination of at least one inventive pyrimidine I and / or an agriculturally acceptable salt thereof and at least one further fungicidal, insecticidal, herbicidal and / or growth-regulating active ingredient.
  • a further subject matter of the present invention is a pesticidal composition
  • a pesticidal composition comprising at least one pyrimidine I, in particular a pyrimidine of the formula I described as preferred in the preceding description and / or an agriculturally acceptable salt thereof and at least one solid or liquid carrier.
  • a pesticidal agent may contain at least one other fungicidal, insecticidal and / or herbicidal active ingredient.
  • Azoxystrobin Dimoxystrobin, Enestroburin, Fluoxastrobin, Kresoxim-methyl, Metominostrobin, Picoxystrobin, Pyraclostrobin, Trifloxystrobin, Orysastrobin, (2-Chloro-5- [1- (3-methyl-benzyloxyimino) -ethyl] -benzyl) -carbamic acid methyl ester,
  • Carboxylic acid amides - carboxylic anilides benalaxyl, benodanil, boscalid, carboxin, mepronil, fenofuram, fenhexamide, flutolanil, furametpyr, metalaxyl, ofurace, oxadixyl, oxycarboxine, penthiopyrad, thifluzamide, tiadinil, 4-difluoromethyl-2-methyl- thiazol-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-methylthiazole-5-carboxylic acid (4'-chloro-3'-fluorobiphenyl-2-yl) -amide, 3-difluoromethyl-1-methyl
  • Carboxylic acid morpholides Dimethomorph, Flumorph; Benzoic acid amides: flumetover, fluopicolide (picobenzamide), zoxamide; Other carboxylic acid amides: carpropamide, diclocymet, mandipropamide, N- (2- (4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-methanesulfonyl-amino 3-methylbutyramide, N- (2- [4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-ethanesulfonylamino-3-methyl butyramide;
  • Triazoles bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole,
  • Imidazoles cyazofamide, imazalil, pefurazoate, prochloraz, triflumizole;
  • Benzimidazoles benomyl, carbendazim, fuberidazole, thiabendazole; - Other: ethaboxam, etridiazole, hymexazole;
  • Pyridines fluazinam, pyrifenox, 3- [5- (4-chloro-phenyl) -2,3-dimethyl-isoxazolidin-3-yl] -pyridine;
  • Pyrimidines bupirimate, cyprodinil, ferimzone, fenarimol, mepanipyrim, nuarimol, pyrimethanil;
  • Morpholine aldimorph, dodemorph, fenpropimorph, tridemorph
  • Dicarboximides iprodione, procymidone, vinclozolin; - others: acibenzolar-S-methyl, anilazine, captan, captafol, dazomet, diclo mezine, fenoxanil, folpet, fenpropidin, famoxadone, fenamidone, octhilinone,
  • Guanidines dodin, iminoctadine, guazatine
  • Antibiotics Kasugamycin, Polyoxins, Streptomycin, Validamycin A; Organometallic compounds: fentin salts; Sulfur-containing heterocyclyl compounds: isoprothiolane, dithianone;
  • Organophosphorus compounds edifenphos, fosetyl, fosetyl-aluminum, iprobenefos, pyrazophos, tolclofos-methyl, phosphorous acid and their salts;
  • Organochlorine compounds thiophanates methyl, chlorothalonil, dichlofluanid, tolylfluanid, flusulfamide, phthalides, hexachlorobenzene, pencycuron, quintozene; Nitrophenyl derivatives: binapacryl, dinocap, dinobuton;
  • Inorganic active substances Bordeaux broth, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;
  • the present invention relates to the pharmaceutical use of the pyrimidines I according to the invention, in particular the pyrimidines of the formula I described in the preceding description, and / or the pharmaceutically acceptable salts thereof, in particular their use for the treatment of tumors in mammals such as in humans ,
  • reaction mixture was concentrated in vacuo, taken up in 250 ml of ethyl acetate, washed three times with 100 ml of water, dried over sodium sulfate and concentrated in vacuo and purified by chromatography on silica gel with cyclohexane / methyl tert-butyl ether. Yield 17.6 g.
  • the active compounds were prepared separately as a stock solution with 25 mg of active ingredient, which was mixed with a mixture of acetone and / or DMSO and the emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenyls) in the volume ratio solvent- Emulsifier from 99 to 1 ad 10 ml was filled. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the drug concentration given below.
  • Uniperol® EL wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenyls
  • the active ingredients were formulated separately as stock solution with a concentration of 10,000 ppm in DMSO.
  • the stock solution is pipetted into a microtiter plate (MTP) and diluted with an aqueous malt-based mushroom nutrient medium to the stated active substance concentration. This was followed by the addition of an aqueous spore suspension of Pyricularia oryzae.
  • MTP microtiter plate
  • the plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. With an absorbance photometer, the MTP's were measured at 405 nm on the 7th day after inoculation.
  • the measured parameters were compared with the growth of the drug-free control variant and the fungus- and drug-free blank to determine the relative growth in% of the pathogens in the individual drugs.
  • the stock solution is pipetted into a microtiter plate (MTP) and diluted to the indicated drug concentration with an aqueous, pea-based, mushroom nutrient medium. This was followed by the addition of an aqueous zoospore suspension of Phytophthora infestans.
  • MTP microtiter plate
  • the plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. With an absorbance photometer, the MTP's were measured at 405 nm on the 7th day after inoculation.
  • Control variant and the fungus-free and drug-free blank to calculate the relative growth in% of the pathogens in the individual drugs.

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  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
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Abstract

La présente invention concerne l'utilisation de pyrimidines substituées en position 2, de formule (I), dans laquelle les substituants ont les significations définies dans la description, comme fongicides, ces nouvelles pyrimidines, des procédés et des produits intermédiaires permettant de les produire, ainsi que des produits les contenant.
EP07704400A 2006-02-15 2007-02-07 Pyrimidines substituées en position 2 et leur utilisation comme pesticides Withdrawn EP1987011A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP07704400A EP1987011A1 (fr) 2006-02-15 2007-02-07 Pyrimidines substituées en position 2 et leur utilisation comme pesticides

Applications Claiming Priority (3)

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EP06003084 2006-02-15
PCT/EP2007/051142 WO2007093527A1 (fr) 2006-02-15 2007-02-07 Pyrimidines substituées en position 2 et leur utilisation comme pesticides
EP07704400A EP1987011A1 (fr) 2006-02-15 2007-02-07 Pyrimidines substituées en position 2 et leur utilisation comme pesticides

Publications (1)

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EP1987011A1 true EP1987011A1 (fr) 2008-11-05

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US (1) US20090069180A1 (fr)
EP (1) EP1987011A1 (fr)
JP (1) JP2009532327A (fr)
CN (1) CN101384562A (fr)
AR (1) AR059507A1 (fr)
CA (1) CA2639888A1 (fr)
TW (1) TW200804306A (fr)
WO (1) WO2007093527A1 (fr)

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ES2587232T3 (es) 2010-07-20 2016-10-21 Vestaron Corporation Triazinas y pirimidinas insecticidas
WO2012103051A2 (fr) * 2011-01-25 2012-08-02 Dow Agrosciences Llc Acides et esters 6-amino-2-substitués-5-vinylsilylpyrimidine-4-carboxyliques et acides et esters 4-amino-6-substitutés-3-vinylsilylpyridine-2-carboxyliques utilisés en tant qu'herbicides
US11178871B2 (en) * 2016-07-26 2021-11-23 Basf Se Herbicidal pyrimidine compounds

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US5622954A (en) * 1994-05-11 1997-04-22 Fmc Corporation 5[W(substituted aryl)alkenylene and alkynylene]-2,4-diaminopyrimidines as pesticides
AU1546197A (en) * 1996-02-05 1997-08-28 Basf Aktiengesellschaft Pyrimidine derivatives, process and intermediate products for their preparation and pesticides or fungicides containing these derivatives
GB9806739D0 (en) * 1998-03-28 1998-05-27 Univ Newcastle Ventures Ltd Cyclin dependent kinase inhibitors
EE200300448A (et) * 2001-03-15 2004-02-16 Basf Aktiengesellschaft 5-fenüülpürimidiinid, meetodid ja vaheühendid nende valmistamiseks ning nende kasutamine patogeensete seente tõrjeks
HUP0402385A3 (en) * 2001-11-19 2005-10-28 Basf Ag 5-phenylpyrimidines, fungicide compositions comprising the same, method for producing and use thereof
JP2005523286A (ja) * 2002-02-21 2005-08-04 ビーエーエスエフ アクチェンゲゼルシャフト ２−（２−ピリジル）−５−フェニル−６−アミノピリミジン、それを調製するための方法及び中間生成物、並びに、有害な真菌を防除するためのそれの使用
CA2525762A1 (fr) * 2003-05-20 2004-12-02 Basf Aktiengesellschaft Pyrimidines substituees en position 2
DE502005003473D1 (de) * 2004-05-19 2008-05-08 Basf Se 2-substituierte pyrimidine und ihre verwendung als pestizide

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WO2007093527A1 (fr) 2007-08-23
US20090069180A1 (en) 2009-03-12
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CA2639888A1 (fr) 2007-08-23
AR059507A1 (es) 2008-04-09
JP2009532327A (ja) 2009-09-10

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