EP1711474A1 - 5-phenylpyridines et leur utilisation comme microbicides - Google Patents

5-phenylpyridines et leur utilisation comme microbicides

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Publication number
EP1711474A1
EP1711474A1 EP05700906A EP05700906A EP1711474A1 EP 1711474 A1 EP1711474 A1 EP 1711474A1 EP 05700906 A EP05700906 A EP 05700906A EP 05700906 A EP05700906 A EP 05700906A EP 1711474 A1 EP1711474 A1 EP 1711474A1
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EP
European Patent Office
Prior art keywords
formula
compounds
alkyl
halogen
hydrogen
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.)
Withdrawn
Application number
EP05700906A
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German (de)
English (en)
Inventor
Olaf Gebauer
Herbert Gayer
Ulrich Heinemann
Stefan Herrmann
Stefan Hillebrand
Ronald Ebbert
Peter Dahmen
Karl-Heinz Kuck
Ulrike Wachendorff-Neumann
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Bayer CropScience AG
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Bayer CropScience AG
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Publication of EP1711474A1 publication Critical patent/EP1711474A1/fr
Withdrawn legal-status Critical Current

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    • 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
    • A01N43/48—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
    • A01N43/64—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
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • C07D239/38—One sulfur 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
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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

Definitions

  • the present invention relates to new 5-phenylpyrimidines, several processes for their preparation and their use for controlling unwanted microorganisms.
  • the invention also relates to new intermediates and processes for their production.
  • the object of the present invention was therefore to find further compounds with good activity against microorganisms, in particular with fungicidal activity.
  • R a for halogen, alkylamino, alkylhydrazino, cyano, oxo, nitro, Ci-C ⁇ -alkylthio, dC ß- alkyl, CC 6 -haloalkyl, tri (-C-C 4 alkyl) silyl, and / or CC 6 alkoxy and / or unsubstituted by halogen, C ⁇ -C4 alkyl or C ⁇ -C 4 - halogenoalkyl substituted C 3 -C 6 cycloalkyl,
  • R 2 represents a three- to ten-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle containing one to four heteroatoms from the group O, N or S, where R 2 is substituted by one to three identical or different groups
  • R b can, and R for halogen, hydroxy, cyano, oxo, nitro, amino, mercapto, -CC 6 alkyl, CC 6 - haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl ; C 3 -C 6 -cycloalkyl, CC 6 -alkoxy, CC 5 -haloalkoxy, carboxyl, -C-C 7 -alkoxycarbonyl, carbamoyl, CC 7 - alkylaminocarbonyl, C] -C 6 -alkyl-C ⁇ -C6-alkylamine carbonyl, - Mo holinocarbonyl, pyrrol
  • R 3 represents halogen or CC 8 -alkyl, CC 8 -alkoxy, dQ-haloalkyl, CC 8 -alkylthio, dC 8- alkylsulfmyl, Cl-C 8 -alkylsulfonyl, or cyano,
  • R 4 are each independently hydrogen, halogen, C ö alkyl, CC are 6 haloalkyl or Ci-C ⁇ -alkoxy,
  • R 5 , R 7 independently of one another are hydrogen, halogen, CC 6 alkyl, dC 6 haloalkyl, unsubstituted or substituted by halogen or dC 6 alkyl, C 3 -C 6 cycloalkyl, phenyl, phenoxy or phenylthio, where R 5 and R 7 in the meaning phenyl, phenoxy or phenylthio may be substituted by one to three identical or different groups R c and
  • R c represents halogen, cyano, nitro, CC 6 -alkyl, CC 6 -halogenallcyl, CC 6 -alkoxy and or C 3 -C 6 -cycloalkyl,
  • R 6 is hydrogen, halogen, cyano, nitro, dC 6 -alkyl, C 6 haloalkyl, dC 6 alkoxy, C 3 -C 6 cycloalkoxy, -C 6 haloalkoxy, C ⁇ -C6 alkoxycarbonyl, dC 6 - Haloalkoxycarbonyl, unsubstituted or substituted by halogen or Ci-C ⁇ -alkyl - substituted C 3 -C 6 cycloalkyl, aminocarbonyl, -C-C 6 alkylcarbonyl, -C-C 6 alkylamino.
  • R d represents halogen, cyano, nitro, CC 6 alkyl, CC ⁇ haloalkyl, C r C 6 alkoxy and / or C 3 -C 6 cycloalkyl,
  • the compounds of the formula I have a higher activity against undesired microorganisms than the compounds known from the prior art.
  • R, R, R, R, R and R have the meanings given above and Hai represents halogen
  • R, R, R, R, R, R 5 R and R have the meanings given above and Hai represents halogen
  • R 1 has the meanings given above and
  • M 1 for lithium, sodium, potassium, dihydroxyboranyl, a radical of the formula
  • 5-phenylpyrimidines of the formula I in which R 2 is a N- or C-linked heterocycle and R 3 is CC 8 -alkyl, CC 8 -alkoxy, CC 8 -alkylthio, dC 8 -alkylsulfmyl, CC 8: alkylsulfonyl or Cyano can be prepared by (process c))
  • R, R, R, R, R, R, R, R and have the meanings given above and shark represents halogen
  • R 3 is CC 8 -alkoxy, -CC 8 -alkylthio 5 d ' -d-alkylsulfinyl, -C-C 8 alkylsulfonyl, or cyano, and
  • M ⁇ stands for sodium or potassium, if appropriate in the presence of a diluent, or
  • Hai represents chlorine or bromine, in the presence of a diluent and optionally in the presence of a catalyst.
  • 5-phenylpyrimidines of the formula I (compounds of the formula (I IV )) in which R 2 is an N- or C-bonded heterocycle and R 3 is C 1 -C 8 -alkyl or CC 8 -haloalkyl can alternatively be used by using (method d)),
  • R, R, R, R, R, R, R and R have the meanings given above, with a halogenating agent, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, and
  • R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 have the meanings given above and Hai represents halogen, with a compound of the formula
  • R 1 has the meanings given above and
  • M 1 for lithium, sodium, potassium, dihydroxyb ⁇ ranyl, a radical of the formula
  • Hai represents chlorine, bromine or iodine, if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst.
  • the 5-phenylpyrimidines of the formula (I) are very suitable for controlling unwanted microorganisms. Above all, they show a strong fungicidal activity and can be used both in crop protection and in material protection.
  • the compounds of the formula (I) according to the invention can optionally be in the form of mixtures of various possible isomeric forms, in particular stereoisomers such as E and Z, threo and erythro and optical isomers such as R and S isomers or atropisomers. but if tautomers are also present.
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkyl saturated, straight-chain or branched hydrocarbon radicals with 1 to 4, 6 or 8 carbon atoms, for example CC 6 alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1- Dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, l-methylpentyl, 2- Methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-di
  • Haloalkyl straight-chain or branched alkyl groups with 1 to 8 carbon atoms (as * mentioned above), it being possible for part or all of the hydrogen atoms in these groups to be replaced by halogen atoms as mentioned above, for example 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, 2nd -Chloro-2-fluoroethyl, 2-chloro, 2-di-fluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-
  • Alkenyl unsaturated, straight-chain or branched hydrocarbon radicals with 2 to 4, 6 or 8 carbon atoms and a double bond in any position, 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-pentenyl, 4-pentenyl, 1-methyl-1 -butenyl, '2-methyl-l -butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3 -Methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, l,
  • Cycloalkyl monocyclic, saturated hydrocarbon groups are divided up to 6 carbon ring with 3 ⁇ such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
  • Cycloalkenyl monocyclic, non-aromatic hydrocarbon groups having 3 to 8 carbon ring members with at least one double bond, such as cyclopenten-1-yl, cyclohexen-1-yl, cyclohepta-1,3-dien-1-yl;
  • Alkoxycarbonyl an alkoxy group with 1 to 6 carbon atoms (as mentioned above) which is bonded to the skeleton via a carbonyl group (-CO-);
  • Oxyalkyleneoxy divalent unbranched chains of 1 to 3 CH 2 groups, both valences being bound to the skeleton via an oxygen atom, for example OCH 2 O, OCH 2 CH 2 O and OCH 2 CH 2 CH 2 O; three to ten-membered saturated or partially unsaturated heterocycle, containing one to four heteroatoms from the group consisting of oxygen, nitrogen or sulfur: mono- or bicyclic heterocycles (heterocyclyl) containing, in addition to carbon ring members, one to three nitrogen atoms and / or an oxygen or sulfur atom or one or two oxygen and / or sulfur atoms; if the ring contains melteric oxygen atoms, these are not directly adjacent; e.g.
  • oxiranyl aziridinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidine -Isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl ; 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, l, 2,4-oxadiazolidin-5-yl, l, 2,4-thiadiazoli
  • 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom: 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members, for example 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, 2- ' oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-.
  • 5-membered benzo-fused heteroaryl containing one to three nitrogen atoms or one nitrogen atom and one oxygen or sulfur atom 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members, and in which two adjacent carbon ring members or one nitrogen and one adjacent beard carbon member can be bridged by a buta- 1,3-diene-1,4-diyl group in which one or two carbon atoms can be replaced by nitrogen atoms; nitrogen linked 5-membered heteroaryl, containing one to four nitrogen atoms, or nitrogen bonded benzo-fused 5-gliederiges heteroaryl, containing one to three nitrogen atoms: 5-membered heteroaryl groups which, in addition Kohlenstoff expertsomen one to four nitrogen atoms or one to three nitrogen atoms as' Ring members can contain, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member can be bridged by
  • 6-membered heteroaryl containing one to three or one to four nitrogen atoms 6-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three or one to four nitrogen atoms as ring members, e.g. 3-pyridazinyl, 4-pyridazmyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, l, 3,5-triazin-2-yl and 1,2,4-triazin-3-yl;
  • Preferred compounds of the formula I are those in which R 1 for C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, or for a three to ten-membered group saturated, mono- or bicyclic C-bonded heterocycle, containing a hetero atom from the group O, N or S, where R 1 can be substituted by one to three identical or different groups R a .
  • R 1 is substituted by one to three identical or different of the following groups R a :
  • R a is particularly preferred as a substituent when R a is halogen, C 1 -C 4 -alkyl, CC 4 -alkoxy or cyano.
  • R 2 is a three, five or six-membered, in particular a five-membered, heterocycle.
  • R 2 represents the following groups: pyrrole, pyrazole, hnidazole, 1,2,4-triazole, 1,2,3-triazole, tetrazole, 1,2,3-triazine , 1,2,4-triazine, oxazole, isoxazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, furan, thiophene, thiazole, isothiazole, it being possible for the heterocycle to be bonded to the pyrimidine ring via C or N ,
  • R 2 is optionally substituted by up to three groups R b substituted pyrazole, pyrrole, imidazole, .l, 2,3-triazole, 1,2,4-triazole, 1,3 , 4-oxadiazole, 1,3,4-thiadiazole, tetrazole, 2-pyridine, 2-pyrimidine, pyrazine or 3-pyridazine.
  • R 3 represents halogen, CC 6 -alkyl, CC 6 -haloalkyl or C] -C 6 -alkoxy, in particular halogen.
  • R 5 and R 7 are identical or different and are hydrogen or halogen.
  • R 6 is hydrogen, halogen, C 1 -C 4 -alkyl, CC 4 -alkoxy, CC 4 -haloalkoxy, CC 4 -alkoxycarbonyl, CC 4 - haloalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, CC - Alkylcarbonyl, -CC 4 -Al seeminglyo, -CC 4 -Alkylsulf -nyl, CC -Alkylsulfonyl, alkylaminosulfonyl or dialkylaminosulfonyl is.
  • the compounds I compiled in the tables below are preferred.
  • the groups mentioned for a substituent in the tables also represent a particularly preferred embodiment of the substituent in question, regardless of the
  • R 1 for a compound corresponds in each case to a radical specified in Table A.
  • R 1 for a compound corresponds in each case to a radical specified in Table A.
  • R 1 for a compound corresponds in each case to a radical specified in Table A.
  • Table 48 Compounds of the formula 1-4, in which R 8 and R 4 are chlorine and R 5 , R 6 and R 7 are hydrogen and R 1 for each compound corresponds to a radical specified in Table A.
  • Table 51 Compounds of the formula 1-4, in which R 8 and R 4 are fluorine, R 5 and R 7 are hydrogen and R 6 are methoxy and R 1 for each compound corresponds to a radical specified in Table A.
  • R 1 for a compound corresponds in each case to a radical specified in Table A.
  • R 1 for a compound corresponds in each case to a radical specified in Table A.
  • Suitable diluents for carrying out process a) according to the invention are acids, such as acetic acid, formic acid, alcohols such as methanol, water or halogenated hydrocarbons such as dichloromethane or chloroforum. Mixtures of these solvents can also be used. Acetic acid or, in the case of oxones, methanol / water mixtures are preferred as the oxidizing agent.
  • Suitable oxidizing agents for carrying out process a) according to the invention are, for example, hydrogen peroxide, tungsten acid, peracetic acid, 3-chloroperbenzoic acid, perphthalic acid, chlorine, oxygen and Oxone® (KHSO5).
  • Suitable acid acceptors for carrying out process a) according to the invention are all inorganic and organic bases customary for such reactions.
  • Alkaline earth metal or alkali metal hydroxides, acetates, carbonates, hydrogen carbonates or phosphates such as, for example, sodium hydroxide, potassium hydroxide, sodium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate, cesium carbonate or silver phosphate, can preferably be used.
  • reaction temperatures can be varied within a substantial range when carrying out process a) according to the invention. In general, temperatures from 0 ° C to 100 ° C, preferably at temperatures from 10 ° C to 50 ° C (cf. WO 02/074753 and literature cited therein).
  • R 2 preferably or in particular has those meanings which have already been given as preferred in connection with the description of the substances of the formula (I) according to the invention.
  • the starting materials of the formula (IV) are known and / or can be prepared by known methods.
  • R 1 has the meanings given above and
  • M 1 for lithium, sodium, potassium, dihydroxyboranyl, a radical of the formula or MgHal stands in what
  • the metal compounds of the formula (VI) are known or can be prepared by known methods.
  • the compounds of the formula (XI) are likewise known (cf. WO 02/074753) or can be prepared by known methods.
  • Suitable diluents for carrying out process e) according to the invention are all inert organic solvents which are customary for such reactions.
  • Ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole can preferably be used;
  • Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide.
  • Suitable catalysts for carrying out process e) according to the invention are all reaction accelerators customary for such reactions.
  • Palladium, nickel, copper or iron salts or complexes are preferably usable. Examples include copper (I) chloride, copper (I) bromide, copper (I) iodide, copper (I) cyanide, iron (III) acetate, iron (III) acetylacetonate, tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) ) - Palladium dichloride and 1, 1 'bis (diphenylphosphmo) ferrocene palladium (H) chloride.
  • Palladium or nickel complexes which are generated in the reaction mixture by adding a palladium or a nickel salt and a substance which functions as a complex ligand to the reaction mixture separately are also preferably usable.
  • ligand formers are:
  • reaction temperatures can be varied within a substantial range when carrying out the first stage of process e) according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably at temperatures between 0 ° C and 80 ° C.
  • Suitable diluents for carrying out process b) according to the invention are all inert organic solvents which are customary for such reactions.
  • Ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole can preferably be used;
  • Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide.
  • Suitable catalysts for carrying out process b) according to the invention are all reaction accelerators customary for such reactions.
  • Palladium, nickel, copper or iron salts or complexes are preferably usable. Examples include copper (r) chloride, copper (I) bromide, copper (I) iodide, copper (I) cyamd, iron (i ⁇ ) acetate, iron (IH) acetylacetonate, tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) ) - Palladium dichloride and 1, 1 , -Bis (diphenylphos ⁇ hmo) ferrocene palladium (H) chloride.
  • Palladium or nickel complexes which are produced in the reaction mixture by adding a palladium or a nickel salt and a substance which functions as a complex ligand to the reaction mixture separately are also preferably usable.
  • ligand formers are:
  • reaction temperatures can be varied within a substantial range when carrying out the first stage of process b) according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably at temperatures between 0 ° C and 80 ° C.
  • the metal compounds of the formula (VI) are known or can be prepared by known methods.
  • the compounds of formula (V) are also known (cf. WO 02/074753) or can be prepared by known methods.
  • Suitable diluents for carrying out process cl) according to the invention are conventional organic solvents.
  • Ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole can preferably be used;
  • Nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide;
  • Sulfoxides such as dimethyl sulfoxide;
  • Sulfones such as sulfolane, alcohols such as methanol, ethanol, isopropanol,
  • reaction temperatures can be varied within a substantial range when carrying out process cl) according to the invention. In general, temperatures from 0 ° C to 150 ° C, preferably at temperatures from 20 ° C to 100 ° C.
  • reaction temperatures can be varied within a certain range when carrying out process c2) according to the invention. In general, temperatures between -20 ° C and 80 ° C, preferably between 0 ° C and 60 ° C.
  • R 1 has , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 and shark preferably or in particular those meanings which have already been given as preferred in connection with the description of the substances of the formula (I) according to the invention.
  • R 3 preferably or in particular has those meanings which have already been given as preferred in connection with the description of the substances of the formula (I) according to the invention.
  • the compounds of the formula (VH) are known or can be prepared by known methods.
  • the starting materials which are also required for carrying out process c2) according to the invention are defined by the formula (VHI).
  • R 3 preferably or in particular has those meanings which have already been given as preferred in connection with the description of the substances of the formula (I) according to the invention.
  • the compounds of the formula (Vffl) are known or can be prepared by known methods.
  • Suitable halogenating agents for carrying out process dl) are all components customary for the replacement of hydroxyl groups by halogen.
  • Phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, phosphorus oxychloride, thionyl chloride, thionyl bromide or mixtures thereof or phosgene, di- or triphosgene are preferably usable.
  • chlorine is added to the halogenating agents mentioned or their mixtures.
  • the corresponding fluorine compounds can be prepared from the chlorine or bromine compounds by reaction with potassium fluoride.
  • Suitable diluents for carrying out process dl) according to the invention are all solvents customary for such halogenations.
  • Halogenated aliphatic or aromatic hydrocarbons such as chlorobenzene
  • the halogenating agent itself for example phosphorus oxychloride or a mixture of halogenating agents, can also act as the diluent.
  • Suitable acid acceptors when carrying out process dl) according to the invention are all inorganic and organic bases customary for such reactions.
  • Alkaline earth metal or alkali metal hydroxides, acetates, carbonates, hydrogen carbonates or phosphates such as, for example, sodium hydroxide, potassium hydroxide, sodium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate, cesium carbonate or silver phosphate, can preferably be used.
  • the temperatures can also be varied within a substantial range when carrying out process dl). In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
  • Formula (IX) defines the starting materials which are also required for carrying out process dl) according to the invention.
  • R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and shark preferably or in particular have those meanings which have already been given as preferred in connection with the description of the substances of the formula (I) according to the invention.
  • the compounds of the formula (LX) are known (cf. WO 02/074753) or can be prepared by known methods.
  • Suitable diluents for carrying out process d2) according to the invention are all inert organic solvents which are customary for such reactions.
  • Ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole can preferably be used;
  • Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide.
  • Suitable catalysts for carrying out process d2) according to the invention are all reaction accelerators customary for such reactions.
  • Palladium, nickel, copper or iron salts or complexes are preferably usable. May be mentioned as an example Copper (I) chloride, copper ( ⁇ ) bromide, copper (I) iodide, copper (I) cyanide, iron (IH) acetate, iron (i ⁇ ) acetylacetonate, tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium dichloride and 1, 1 'bis (diphenylphosphino) ferrocene palladium ( ⁇ ) chloride.
  • Palladium or nickel complexes which are produced in the reaction mixture by adding a palladium or a nickel salt and a substance which functions as a complex ligand to the reaction mixture separately are also preferably usable.
  • ligand formers are:
  • reaction temperatures can be varied within a substantial range. In general, temperatures between 0 ° C and 150 ° C, preferably at temperatures between 0 ° C and 80 ° C.
  • the metal compounds of the formula (VT) are known or can be prepared by known methods.
  • the substances according to the invention inhibit the growth of tumor cells and related diseases in mammals and can be used as medicaments.
  • they are suitable for the production of drugs for combating cancer.
  • the invention further relates to a method for inhibiting the growth of cancerous
  • Tumor cells and related diseases in a mammal in need of this treatment involves administering an effective amount of a 5-phenylpyrimidine or a pharmaceutically active salt thereof to a mammal.
  • the invention relates further a method of treating or preventing the growth of tumor cells and related diseases by interacting with tubulin and microtubules and promoting the polymerization of microtubules by administering an effective amount of a 5-phenylpyrimidine or a pharmaceutically active salt thereof to a mammal.
  • the substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.
  • Fungicides can be used in crop protection to combat Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, * Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • Xanthomonas species such as, for example, Xanthomonas campestris pv. Oryzae;
  • Pseudomonas species such as, for example, Pseudomonas syringae pv. Lachrymans;
  • Erwinia species such as, for example, Erwinia amylovora;
  • Pythium species such as, for example, Pythium ultimum
  • Phytophthora species such as Phytophthora infestans
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or
  • Plasmopara species such as, for example, Plasmopara viticola
  • Bremia species such as, for example, Bremia lactucae
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae;
  • Erysiphe species such as, for example, Erysiphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca fuliginea
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Venturia species such as, for example, Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Cochliobolus species such as, for example, Cochliobolus sativus
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Puccinia species such as, for example, Puccinia recondita
  • Sclerotinia species such as, for example, Sclerotinia sclerotiorum
  • Tilletia species such as, for example, Tilletia caries
  • Ustilago species such as, for example, Ustilago nuda or Ustilago avenae;
  • Pellicularia species such as, for example, Pellicularia sasakü;
  • Pyricularia species such as, for example, Pyricularia oryzae
  • Fusarium species such as, for example, Fusarium culmorum
  • Botrytis species such as, for example, Botrytis cinerea
  • Septoria species such as, for example, Septoria nodorum
  • Leptosphaeria species such as, for example, Leptosphaeria nodorum;
  • Cercospora species such as, for example, Cercospora canescens
  • Alternaria species such as, for example, Alternaria brassicae;
  • Pseudocercosporella species such as, for example, Pseudocercosporella herpotrichoides.
  • the active compounds according to the invention also have a very good strengthening effect in plants. They are therefore suitable for mobilizing the plant's own defenses against attack by unwanted microorganisms.
  • Plant-strengthening (resistance-inducing) substances are to be understood in the present context as substances which are able to stimulate the defense system y of plants in such a way that the treated plants develop extensive resistance to these microorganisms when subsequently inoculated with undesired microorganisms.
  • Undesired microorganisms are to be understood in the present case as phytopathogenic fungi, bacteria and viruses.
  • the substances according to the invention can thus be used to protect plants against attack by the pests mentioned within a certain period of time after the treatment.
  • the period of time within which protection is brought about generally extends from 1 to 10 days, preferably 1 to 7 days, after the plants have been treated with the active compounds.
  • the active compounds according to the invention can be used with particularly good success for combating cereal diseases, for example against Erysiphe species, for diseases in wine, fruit and vegetable cultivation, for example against Botrytis, Venturia, Sphaerotheca and Podosphaera species ,
  • the active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance.
  • the active compounds according to the invention can also be used in certain concentrations and application rates as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of further active compounds.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, Needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and • rhizomes are listed.
  • the plant parts also include crops, and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space using the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular in the case of seeds, furthermore by coating in one or more layers.
  • the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
  • technical materials are understood to mean non-living materials that have been prepared for use in technology.
  • technical materials which are to be protected against microbial change or destruction by active substances according to the invention can be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which can be attacked or decomposed by microorganisms , Parts of production facilities are also part of the materials to be protected; For example, called cooling water circuits, which can be affected by the multiplication of microorganisms.
  • technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer liquids, particularly preferably wood.
  • Bacteria, fungi, yeasts, algae and slime organisms may be mentioned as microorganisms which can bring about a degradation or a change in the technical materials.
  • the active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • Microorganisms of the following genera may be mentioned, for example:
  • Alternaria such as Alternaria tenuis
  • Aspergillus such as Aspergillus niger
  • Chaetomium like Chaetomium globosum, Coniophora, such as Coniophora puetana,
  • Lentinus such as Lentinus tigrinus
  • Penicillium such as Penicillium glaucum
  • Polyporus such as Polyporus versicolor
  • Aureobasidium such as Aureobasidium pullulans
  • Sclerophoma such as Sclerophoma pityophila
  • Trichoderma like Trichoderma viride
  • Escherichia such as Escherichia coli
  • Pseudomonas such as Pseudomonas aeruginosa
  • Staphylococcus such as Staphylococcus aureus.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV -Cold and warm mist formulations.
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents , If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents .
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents
  • organic solvents can, for example, also be used as auxiliary solvents.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • Solid carrier materials are suitable: for example natural rock flour, such as kaolins, Clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, such as highly disperse silica, aluminum oxide and silicates. Solid carriers for granules are possible: e.g.
  • emulsifiers and / or foaming agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • Possible dispersants are: eg lignin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to to broaden the spectrum of activity or to prevent the development of resistance.
  • fungicides bactericides
  • acaricides nematicides or insecticides
  • synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Dagger G debacarb; dichlofluanid; dichlone; dichlorophen; diclocymet; Diclomezine; dicloran; diethofencarb; Difenoconazole; diflumetorim; dimethirimol; dimethomorph; dimoxystrobin; diniconazole; Diniconazole-M; dinocap; diphenylamines; Dipyrithione; Ditalimfos; dithianon; dodine; Drazoxolon;
  • edifenphos epoxiconazole; ethaboxam; ethirimol; etridiazole;
  • famoxadone fenamidone; Fenapanil; fenarimol; Fenbuconazole; fenfuram; fenhexamid; Fenitropan; fenoxanil; fenpiclonil; fenpropidin; fenpropimorph; ferbam; fluazinam; Flubenzimine; fludioxonil; flumetover; flumorph; fluoromides; fluoxastrobin; fluquinconazole; flurprimidol; flusilazole; flusulfamide; flutolanil; flutriafol; folpet; Fosetyl-Al; Fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; Furcarbanil; Furmecyclox; ••
  • Iminoctadine t ⁇ is (albesil; Iodocarb; Ipconazole; Iprobefos; Iprodione; Iprovalicarb; Irumamycin; Isoprothiolane; Isovaledione;
  • mancozeb maneb; Meferimzone; mepanipyrim; mepronil; metalaxyl; Metalaxyl-M; Metconazole; methasulfocarb; Methfuroxam; metiram; metominostrobin; Metsulfovax; mildiomycin; myclobutanil; myclozoline; natamycin; nicobifen; Nitro Thal-isopropyl; Noviflumuron; nuarimol;
  • tebuconazole tecloftalam; Tecnazene; Tetcyclacis; tetraconazole; thiabendazole; Thicyofen; Thifluzamide; Thiophanate-methyl; thiram; Tioxymid; Tolclofos-methyl; tolylfluanid; triadimefon; triadimenol; Triazbutil; triazoxide; Tricyclamide; Tricyclazole; tridemorph; trifloxystrobin; triflumizole; triforine; triticonazole;
  • copper salts and preparations such as Bordeaux mixture; copper; Copper naphthenate; copper oxychloride; Copper sulfate; Cufraneb; copper; mancopper; Oxine-copper.
  • Benzoximate beta-cyfluthrin, beta-cypermethrin, bifenazate, bifenthrin, binapacryl, bioallethrin, bioallethrin-S-cyclopentyl-isomer, bioethanomethrin, biopermethrin, bioresmethrin, bistrifluron, BPMC, bromopropyl, bromine-pro-bromine, bromine-pro-bromine, bromine-pro-bromine, bromine-pro-bromine-methyl-bromine-pro-bromine-bromine-bromine-pro-bromine-pro-bromine-pro-bromine-pro ), BTG-504, BTG-505, Bufencarb, Buprofezin, Butathiofos, Butocarboxim, Butoxycarboxim, Butyl-pyridaben,
  • IKA-2002 Imidacloprid, Imiprothrin, Indoxacarb, Iodofenphos, Iprobefos, Isazofos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin,
  • Mecarbam Mesulfenfos, Metaldehyde, Metam-sodium, Methacrifos, Methamidophos, Metharhician anisopliae, Metharhician flavoviride, Methidathione, Methiocarb, Methomyl, Methoprene, Methoxychlor, Methoxyfenozide, Metolcarb, Metoxadiazone, MilevinephinI, Mevincinin MKB, Mevincinin MK5 MON-45700, Monocrotophos, Moxidectin, MTI-800,
  • NC-104 NC-170, NC-184, NC-194, NC-196, Niclosamide, Nicotine, Nitenpyram, Nithiazine, NNI-0001, NNI-0101, NNI-0250, NNI-9768, Novaluron, Noviflumuron,
  • insecticidal plant extracts ⁇ ematodes, fungi or viruses.
  • preparations containing insecticidal plant extracts, ⁇ ematodes, fungi or viruses are also possible.
  • active compounds such as herbicides or with fertilizers and growth regulators, safeners or semiochemicals, is also possible.
  • the compounds of the formula (I) according to the invention also have very good antimycotic effects. They have a very broad spectrum of antifungal effects, especially against dermatophytes and shoot fungi, mold and diphasic fungi (eg against Candida species such as Candida albicans, Candida glabrata) as well as Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillichophytonus fumigatus fumigatus such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii.
  • Candida species such as Candida albicans, Candida glabrata
  • Epidermophyton floccosum Aspergillus species such as Aspergillus niger and Aspergillichophytonus fumigatus fumigatus
  • Microsporon species such as Microsporon canis and audouinii.
  • the list of these fungi is in no way a limitation of the detectable
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering, dusting, foaming, aeration stress etc. It is furthermore possible, "the active compounds by the ultra-low volume method or to apply the active compound preparation or the active compound to inject yourself into the soil. The seeds of the plants can also be treated.
  • the application rates can be varied within a relatively wide range, depending on the type of application.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.
  • the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the application rates of active compound are generally between 0.1 and 10,000 g / ha, preferably between • 1 and 5000 g / ha.
  • plants and their parts can be treated.
  • wild plant species or plant species and their parts obtained by conventional biological breeding methods such as crossing or protoplast fusion
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods if appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated.
  • the term “parts” or “parts of plants” or “parts of plants” was explained above. Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention. Plant cultivars are understood to mean plants with new properties (“traits”) which have been grown by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, breeds, bio- and genotypes.
  • the treatment according to the invention can also cause superadditive (“synergistic”) effects.
  • superadditive for example, reduced application rates and / or widening the spectrum of action and / or an increase in the effect of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the effects to be actually expected.
  • the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous valuable properties (“traits”). Examples of such properties are better plant cultivation. Growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or processability of the harvested products. Further and particularly emphasized examples of such properties are, an increased 'defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / ode Viruses and increased tolerance of plants.
  • the important crop plants such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes) are mentioned as examples of transgenic plants, with corn, soybeans , Potato, cotton, tobacco and rapeseed are highlighted.
  • the traits are particularly emphasized as the increased defense of the plants against insects, arachnids, namatodes and snails by toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (eg by the genes Cry ⁇ A (a) , CryIA (b), Cry ⁇ A (c), CryHA, CrylUA, CryIDB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
  • Bacillus thuringiensis eg by the genes Cry ⁇ A (a) , CryIA (b), Cry ⁇ A (c), CryHA, CrylUA, CryIDB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations
  • j traits which are also particularly increased defense highlighted by plants to fungi, bacteria and viruses by systemic acquired resistance '(SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expri--optimized proteins and toxins.
  • SAR systemic acquired resistance
  • properties are also particularly emphasized the increased tolerance of the plants to certain herbicidal active ingredients, for example imidazolinones, sulfonylureas; Glyphosate or phosphinotricin (eg; "PAT” gene).
  • the genes conferring the desired properties (“traits”) can also be found in combinations with one another in the transgenic plants.
  • Bt plants include corn varieties, cotton varieties, soy varieties and potato varieties which are marketed under the trade names YIELD GARD® ( For example, maize, cotton, soy), KnockOut® (eg maize), StarLink® (eg maize), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato) are examples of herbicide-tolerant plants
  • Herbicide-resistant plants are also those sold under the name Clearfield® Varieties (e.g. maize) mentioned. Of course, these statements also apply to
  • plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active compound mixtures according to the invention.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • aqueous phase is extracted with further ethyl acetate.
  • the combined organic phases are dried over sodium sulfate and concentrated under reduced pressure.
  • logP values were determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid).
  • Solvent 24.5 parts by weight of acetone, 24.5 parts by weight of dimethylacetamide
  • Emulsifier - 1 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Evaluation takes place -10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • the substances according to the invention show a very high efficiency at an application rate of 100 g / ha.

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Abstract

L'invention concerne de nouvelles 5-phénylpyrimidines de formule (I), dans laquelle R<2> représente un hétérocycle, ainsi que leur utilisation pour lutter contre des micro-organismes indésirables. L'invention concerne en outre de nouveaux produits intermédiaires ainsi que des procédés pour leur production.
EP05700906A 2004-01-23 2005-01-14 5-phenylpyridines et leur utilisation comme microbicides Withdrawn EP1711474A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004003493A DE102004003493A1 (de) 2004-01-23 2004-01-23 5-Phenylpyrimidine
PCT/EP2005/000304 WO2005070899A1 (fr) 2004-01-23 2005-01-14 5-phenylpyrimidines et leur utilisation comme microbicides

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EP1711474A1 true EP1711474A1 (fr) 2006-10-18

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US (1) US20050182073A1 (fr)
EP (1) EP1711474A1 (fr)
JP (1) JP2007522120A (fr)
BR (1) BRPI0507063A (fr)
DE (1) DE102004003493A1 (fr)
WO (1) WO2005070899A1 (fr)

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TW200637556A (en) * 2005-01-31 2006-11-01 Basf Ag Substituted 5-phenyl pyrimidines I in therapy
CL2007002231A1 (es) * 2006-08-02 2008-04-11 Basf Ag Uso de compuestos derivados de 5-(het) arilpirimidina para combatir hongos daninos; compuestos derivados de 5-(het) arilpirimidina; agente fungicida; y agente farmaceutico.
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JP2007522120A (ja) 2007-08-09
DE102004003493A1 (de) 2005-08-11
BRPI0507063A (pt) 2007-06-19
WO2005070899A1 (fr) 2005-08-04

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