EP2331524A1 - Heterozyklisch substituierte anilinopyrimidine als fungizide - Google Patents

Heterozyklisch substituierte anilinopyrimidine als fungizide

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Publication number
EP2331524A1
EP2331524A1 EP09778015A EP09778015A EP2331524A1 EP 2331524 A1 EP2331524 A1 EP 2331524A1 EP 09778015 A EP09778015 A EP 09778015A EP 09778015 A EP09778015 A EP 09778015A EP 2331524 A1 EP2331524 A1 EP 2331524A1
Authority
EP
European Patent Office
Prior art keywords
methyl
hydrogen
substituted
unsubstituted
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.)
Withdrawn
Application number
EP09778015A
Other languages
German (de)
English (en)
French (fr)
Inventor
Jörg Nico GREUL
Oliver Gaertzen
Hendrik Helmke
Stefan Hillebrand
Kerstin Ilg
Amos Mattes
Pierre Wasnaire
Carl Friedrich Nising
Ulrike Wachendorff-Neumann
Arnd Voerste
Peter Dahmen
Ruth Meissner
Christoph Andreas Braun
Martin Kaussmann
Hiroyuki Hadano
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
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Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to EP09778015A priority Critical patent/EP2331524A1/de
Publication of EP2331524A1 publication Critical patent/EP2331524A1/de
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C07D403/12—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 linked by a chain containing hetero atoms as chain links
    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links
    • 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
    • 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
    • C07D403/10—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 linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the invention relates to diaminopyrimidines and their agrochemically active salts, their use and methods and compositions for controlling phytopathogenic harmful fungi in and / or on plants or in and / or on seeds of plants, processes for the preparation of such agents and treated seeds and their use for controlling of phytopathogenic harmful fungi in agriculture, horticulture and forestry, in animal health, in the protection of materials as well as in the area of household and hygiene.
  • the present invention further relates to a process for the preparation of heterocyclic substituted anilinopyrimidines.
  • heterocyclyl-substituted anilinopyrimidines solve the stated objects, at least in some aspects, and are suitable as crop protection agents, in particular as fungicides.
  • the invention provides compounds of the formula (I)
  • R 1 to R 5 are independently hydrogen, OH, halogen, cyano, Ci-C 4 alkyl, QC 4 - alkoxy, C r C 4 haloalkyl, NMe 2, SCH 3 or C r C 2 haloalkoxy,
  • Z is sulfur or oxygen
  • Li is an unsubstituted or substituted C 1 -C 4 -alkylene or C 2 -C 4 -alkenyl chain, where double bonds do not occur cumulatively and
  • L 2 is an unsubstituted or substituted C r to C 4 alkylene, a C 2 to C 4 alkenyl chain or a 1,3-linked cyclopentyl (3-oxo-2-azabicyclo [2.2.1] hept 2-yl) or a C 1 to C interrupted by a heteroatom selected from oxygen, sulfur or nitrogen
  • R 6 is hydrogen, Me, C r C 4 alkylcarbonyl, CHO, C, -C 4 alkoxy-C, -C 4 alkylcarbonyl, C 1 - C 4 alkoxy-C] -C 4 -alkyl 5 unbranched or branched C r C 4 alkoxycarbonyl, COOBn, C r C 4 haloalkylcarbonyl, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, C, -C 4 alkyl-sulfinyl, C 1 -C 4 - alkyl sulfonyl, unsubstituted or substituted benzyl, Q-Gi trialliyl, C 1 -C 4 trialkyl silyl ethyl or C 1 -C 4 dialkyl mono-phenyl silyl, wherein the substituents are independently selected from hydrogen, halogen, nitro, Ci-C4-alkyl, Ci-
  • R 7 is hydrogen, cyano, C r C 3 alkyl or C r C 3 haloalkyl
  • R 8 is halogen, cyano, Ci-C 2 haloalkyl, methyl, SMe, SOMe or SO 2 Me,
  • R 9 is hydrogen, straight-chain or branched C 1 -C 3 -alkyl, 2-methoxyethane-1-yl, prop-2-en-1-yl, C 1 -C 4 -alkoxy (C 1 -C 4 ) -alkyl, unbranched or branched (C r C 4 - alkyl) carbonyl, (Ci-C 4 haloalkyl) carbonyl, unsubstituted or substituted benzyl, Q-C6 trialkyl-silyl, C r C 4 trialkyl-silyl-ethyl, C r C 4 Dialkyl-mono-phenyl-silyl, (C 1 -C 4 -alkoxy) carbonyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, CpC ⁇ -haloalkylsulfinyl or d-Ce-halo
  • substituents are independently selected from hydrogen, halogen, nitro, Ci-C 4 alkyl, C r C 4 alkoxy, hydroxy, C r C 4 haloalkyl or cyano,
  • R 10 is unbranched or branched, unsubstituted or substituted C 1 -C 7 -alkyl, unbranched or branched, unsubstituted or substituted C 2 -C 7 -haloalkyl, unsubstituted or substituted C 3 -C 7 -cycloalkyl, unbranched or branched, unsubstituted or substituted C 3 -C 7 -cycloalkyl (C 1 -C 3 ) -alkyl, unbranched or branched, unsubstituted or substituted C 3 -C 7 -alkenyl, unbranched or branched, unsubstituted or substituted C 3 -C 7 -alkynyl, unbranched or branched, unsubstituted or substituted C 1 -C 4 alkoxy (C 1 -C 4) alkyl, straight or branched, unsubstituted or substituted Ci-C4 haloalk
  • R 9 and R 10 together with the nitrogen atom to which they are attached form an unsubstituted or substituted 3-7 membered, saturated cycle which may contain up to another heteroatom selected from oxygen, sulfur or nitrogen,
  • substituents in R 10 are independently selected from methyl, ethyl, iso-propyl, cyclopropyl, fluorine, chlorine and / or bromine atoms, methoxy, ethoxy, methylmercapto, ethylmercapto, cyano, hydroxy or CF 3 ,
  • Diaminopyrimidines of the formula (I) according to the invention and their agrochemically active salts are very suitable for controlling phytopathogenic harmful fungi.
  • the aforementioned Compounds of the invention show, above all, a strong fungicidal activity and can be used both in crop protection, in the household and hygiene sector and in the protection of materials.
  • the compounds of the formula (I) can be used both in pure form and as mixtures of various possible isomeric forms, in particular of stereoisomers, such as E and Z, threo and erythro, and also optical isomers, such as R and S radicals. Isomers or atropisomers, unbranched or else present by tautomers. Both the E and the Z isomers, as well as the threo and erythro, and the optical isomers, any mixtures of these isomers, as well as the possible tautomeric forms claimed.
  • stereoisomers such as E and Z, threo and erythro
  • optical isomers such as R and S radicals.
  • R 1 to R 5 are each independently hydrogen, OH, Cl, F, Br, CH 3 , CF 3, ethyl, OCH 3, SCH 3, OCF 2 H, or OCF 3 ,
  • Y is a direct bond or -CH 2 -, -CH 2 CH 2 -, -CH (CH 3 ) CH 2 -, -CH 2 CH (CH 3 ) -, -CHMe-,
  • Z is sulfur or oxygen
  • Li is an unsubstituted or substituted Q to C 4 alkylene or a C 2 to G 9 alkenyl chain
  • the individual carbon atoms can carry one or more substituents independently selected from the following list: Hydrogen, methyl, ethyl, hydroxy, oxo, methoxy, OCH 2 CH 3 , OC (CH 3 ) 3 , OCH (CH 3 ) 2 , O-propyl, O-butyl, COOCH 3 , COOCH 2 CH 3 , COOC (CH 3 ) 3 , COOPr, COOCH (CH 3 ) 2 , CH 2 OH, CH 2 OCH 3 , CH 2 OCH 2 CH 3 , CH 2 CH (CH 3 ) 2 , CH 2 C (CH 3 ) 3 , phenyl or benzyl .
  • substituents independently selected from the following list: Hydrogen, methyl, ethyl, hydroxy, oxo, methoxy, OCH 2 CH 3 , OC (CH 3 ) 3 , OCH (CH 3 ) 2 , O-propyl, O-butyl, COOC
  • L 2 is an unsubstituted or substituted C 1 to C 4 alkylene, a C 2 to C 4 alkenyl chain or a 1,3-linked cyclopentyl (3-oxo-2-azabicyclo [2.2.1] hept 2-yl) or a C r to Q-alkylene chain interrupted by a heteroatom selected from oxygen, sulfur or nitrogen,
  • R 7 is hydrogen, cyano, methyl, CF 3 or CFH 2
  • R 8 is chlorine, bromine, fluorine, iodine, cyano, CF 3, CFH 2 , CF 2 H, CCl 3 , methyl, SMe, SOMe or SO 2 Me,
  • R 9 is hydrogen, methyl, ethyl, propyl, propan-2-yl, 2-methoxyethane-1-yl, prop-2-en-1-yl, CH 2 OCH 3 , COMe, COOMe, COOEt, COOtertBu, COCF 3 or benzyl,
  • R 10 is unbranched or branched, unsubstituted or substituted Q-Ce-alkyl, unbranched or branched, unsubstituted or substituted C 3 -C 6 -cycloalkyl (C 1 -C 2 ) -alkyl, unsubstituted or substituted Q-C ⁇ -cycloalkyl, unbranched or branched, unsubstituted or substituted C 3 -C 4 -alkenyl, unbranched or branched, unsubstituted or substituted C 3 -C 4 -alkynyl, unbranched or branched, unsubstituted or substituted C 2 -C 4 -haloalkyl, unbranched or branched, unsubstituted or substituted C r C 2 alkoxy (C 1 -C 4 ) alkyl, unbranched or branched, unsubstituted or substituted C 1 -C 2 -alkylmercap
  • substituents in R 10 are independently selected from methyl, ethyl, iso-propyl, cyclopropyl, fluorine, chlorine and / or bromine atoms, methoxy, ethoxy, methylmercapto, ethylmercapto, cyano, hydroxy or CF 3 ,
  • R 9 and R 10 together with the nitrogen atom to which they are attached form an azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl, azepanyl, 4-methylpiperazin-1-yl, 2 Methylpiperidin-1-yl, 2-methylpyrrolidin-1-yl, 2-methylazetidin-1-yl or thiomorpholinyl ring,
  • R 1 to R 5 are independently hydrogen, OH, Cl, F, CH 3 , CF 3> ethyl, OCH 3 or OCF 3 ,
  • Z is sulfur or oxygen
  • Li is an unsubstituted or substituted Q to C 4 alkylene or a C 2 to C 4 alkenyl chain
  • L 2 is an unsubstituted or substituted C r to C 4 alkylene or a C 2 -Ms C 4 alkenyl chain or a 1,3-linked cyclopentyl (3-oxo-2-azabicyclo [2.2.1] hept 2-yl) or one interrupted by a heteroatom selected from oxygen, sulfur or nitrogen
  • R 7 is hydrogen, cyano, methyl, CF 3 or CFH 2
  • R 8 is chlorine, bromine, fluorine, iodine, cyano, CF 3, CFH 2 , CF 2 H, CCl 3 , methyl, SMe, SOMe or SO 2 Me
  • R 9 is hydrogen, methyl, ethyl, propyl, propan-2-yl, 2-methoxyethane-1-yl, prop-2-en-1-yl, CH 2 OCH 3 , COMe, COOMe, COOEt, COOtertBu, COCF 3 or benzyl,
  • R 10 is methyl, ethyl, propyl, cyclopropyl, cyclopropylmethyl, 1-cyclopropyleth-1-yl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,2-dimethylprop-1-yl, tert-butyl, cyclobutyl, 2-methyl-cyclobut -l-yl, 3-methyl-cyclobut-1-yl, butyl, 3-methylbut-1-yl, 2-methylbut-1-yl, 2-methylprop-1-yl, 1-fluoroprop-2-yl, cyclopentyl , Propan-2-yl, pentan-3-yl, pentan-2-yl, pentyl, prop-2-en-1-yl, prop-2-yn-1-yl, butan-2-yl, 2,2 , 2-trifluoroethyl, 2,2-difluoroethyl, 2-methoxyethane-1-yl, 2-methylmercap
  • R 9 and R 10 together with the nitrogen atom to which they are attached form an azetidinyl, pyrrolidinyl, piperidinyl, monochlorinyl, azepanyl, 4-methylpiperazin-1-yl, 2-methylpiperidin-1-yl, 2-methylpyrrolidin-1-yl, 2-methylazetidin-1-yl or
  • R 1 to R 5 are independently hydrogen, OH, Cl, F, CH 3 or OCF 3 ,
  • R 2 or R 3 is a group of the formula El, E 2 or E 3 , in which
  • Z is sulfur or oxygen
  • Li is an unsubstituted or substituted C 2 -C 3 -alkylene or C 2 -C 3 -alkenyl chain
  • L 2 is an unsubstituted or substituted C 2 to C 3 alkylene or a C 2 to C 3 alkenyl chain or a 1,3-linked cyclopentyl (3-oxo-2-azabicyclo [2.2.1] hept-2-yl) or a C r to C 2 alkylene chain interrupted by a heteroatom selected from oxygen, sulfur or nitrogen,
  • R 6 is hydrogen, Me, COMe, CHO or COCH 2 OCH 3 ,
  • R 7 is hydrogen
  • R 8 is chlorine, bromine, fluorine, iodine, cyano, CF 3 , SMe, SOMe or SO 2 Me,
  • R 9 is hydrogen, methyl, ethyl, propyl, propan-2-yl, 2-methoxyethane-1-yl or prop-2-en-1-yl,
  • R 10 is methyl, ethyl, propyl, cyclopropyl, cyclopropylmethyl, 1-cyclopropyleth-1-yl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,2-dimethylprop-1-yl, tert-butyl,
  • R 9 and R ! O together with the nitrogen atom to which they are attached, form an azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl, azepanyl, 4-methylpiperazin-1-yl, 2-methylpiperidin-1-yl , 2-methylpyrrolidin-1-yl, 2-methylazetidin-1-yl or thiomorpholinyl ring,
  • R 1 is hydrogen or OH
  • R 2 is hydrogen, (2,5-dioxopyrrolidin-1-yl) methyl, (2-oxopyrrolidin-1-yl) carbonyl, (3-methyl-2-oxopyrrolidin-1-yl) methyl, 1 - (2.5 Dioxopyrrolidin-1-yl) -2,2,2-trifluoroethyl, (2R) -2- (ethoxycarbonyl) -5-oxopyrrolidin-1-yl, (2S) -2- (ethoxycarbonyl) -5-oxopyrrolidin-1-yl, 2- (ethoxycarbonyl) -5-oxopyrrolidin-1-yl, (2R) -2- (hydroxymethyl) -5-oxopyrrolidin-1-yl, (2S) -2- (hydroxymethyl) -5-oxopyrrolidin-1-yl, 2- (hydroxymethyl) -5-oxopyrrolidin-1-yl, 2,5-dio
  • R 3 is hydrogen, 2-oxo-1,3-oxazolidin-3-yl, 2-oxopyrrolidin-1-yl, 4-methyl-2-oxo-1,3-oxazolidin-3-yl, OCF 3 fluoro, methyl or chlorine,
  • R 3 can only have one of the following meanings:
  • R 4 is hydrogen or CH 3 ,
  • R 5 is hydrogen
  • R 6 is hydrogen, Me, COMe, CHO or COCH 2 OCH 3 ,
  • R 7 is hydrogen
  • R 8 is chlorine, bromine, fluorine, iodine, cyano, CF 3 , SMe, SOMe or SO 2 Me,
  • R 9 is hydrogen, methyl, ethyl, propyl, propan-2-yl, 2-methoxyethane-1-yl or prop-2-en-i-yl,
  • R 10 is methyl, ethyl, propyl, cyclopropyl, cyclopropylmethyl, 1-cyclopropyleth-1-yl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,2-dimethylprop-1-yl, tert-butyl, cyclobutyl, 2-butyl, 3 -Methylbut-1-yl, 2-methylbut-1-yl, 2-methylprop-1-yl, 1
  • R 9 and R 10 together with the nitrogen atom to which they are attached form an azetidinyl, pyrrolidinyl, piperidinyl, monochlorinyl, azepanyl, 4-methylpiperazin-1-yl, 2-methylpiperidin-1-yl, 2-methylpyrrolidin-1-yl, 2-methylazetidin-1-yl or thiomethylquinyl ring.
  • R 1 is hydrogen
  • R 2 is hydrogen, (2,5-dioxopyrrolidin-1-yl) methyl, (2-oxopyrrolidin-1-yl) carbonyl, (3
  • R 3 is hydrogen, 2-oxo-1,3-oxazolidin-3-yl, 2-oxopyrrolidin-1-yl, 4-methyl-2-oxo-1,3-oxazolidin-3-yl, OCF 3 fluoro, methyl or chlorine,
  • R 3 can only have one of the following meanings:
  • R 4 is hydrogen
  • R 5 is hydrogen
  • R 6 is hydrogen, Me, COMe, CHO or COCH 2 OCH 3 ,
  • R 7 is hydrogen
  • R 8 is chlorine, bromine, fluorine, iodine, cyano or CF 3 ,
  • R 9 is hydrogen or methyl
  • R 10 is methyl, ethyl, cyclopropyl, cyclopropylmethyl, 2,2-dimethylcyclopropyl, cyclobutyl, cyclopentyl, propan-2-yl, prop-2-en-1-yl, butan-2-yl, 2,2,2-trifluoroethyl , 2,2-Difluoroethyl, 1-methoxypropan-2-yl2-methyl-1- (methylsulfanyl) propan-2-yl, oxetan-3-yl or 2,2,3,3,3-pentafluoropropyl,
  • R 9 and R 10 together with the nitrogen atom to which they are attached form an azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl, azepanyl or thiomorpholinyl ring.
  • R 2 is a group of the formula El, E 2 or E 3 ,
  • Y is a direct bond
  • C O or one by unbranched or branched QC 4 -
  • Z is sulfur or oxygen
  • Li is an unsubstituted or substituted C r to C 4 -alkylene or a C 2 to C 4 alkenyl chain
  • L 2 is an unsubstituted or substituted Q to C 4 alkylene or a C 2 to C 4 alkenyl chain or a 1,3-linked cyclopentyl (3-oxo-2-azabicyclo [2.2.1] hept -2-yl) or one C 1 -C 4 -alkylene chain interrupted by a heteroatom selected from oxygen, sulfur or nitrogen,
  • R 3 is a group of the formula E1, E2 or E3,
  • Y is a direct bond
  • C O or one by unbranched or branched QC 4 -
  • Z is sulfur or oxygen
  • Li is an unsubstituted or substituted C r to C 4 -alkylene or a C 2 to C 4 alkenyl chain
  • the individual carbon atoms can carry one or more substituents independently selected from the following list: Hydrogen, hydroxy, unbranched or branched C 1 -C 4 -alkyl, unbranched or branched C 1 -C 4 -alkoxyalkyl, unbranched or branched C 1 -C 4 -alkoxycarbonyl, unbranched or branched C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, unsubstituted or substituted phenyl or benzyl,
  • L 2 is an unsubstituted or substituted Cpbis C 4 -alkylene or a C 2 to C 4 alkenyl chain or a 1,3-linked cyclopentyl (3-oxo-2-azabicyclo [2.2.1] hept-2 -yl) or a C r to C 4 -alkylene chain interrupted by a heteroatom selected from oxygen, sulfur or nitrogen,
  • Li an unsubstituted or substituted C r to C 4 alkylene or a C 2 to C 4 alkenyl chain
  • Z is sulfur or oxygen
  • L 2 is an unsubstituted or substituted C 1 -C 4 -alkylene, a C 2 -C 4 -alkenyl chain or a 1,3-linked cyclopentyl (3-oxo-2-azabicyclo [2.2.1] hept- 2-yl) or a C 1 -C 4 -alkylene chain interrupted by a heteroatom selected from oxygen, sulfur or nitrogen,
  • Z is sulfur or oxygen
  • Li is an unsubstituted or substituted Cpbis C 4 -alkylene or a C 2 to Gj-alkenyl chain
  • substituents are independently selected from the following list: Hydrogen, halogen, CN, SCH 3 , NO 2 , optionally branched C 1 -C 4 -alkyl, optionally branched C 1 -C 4 -alkoxy, optionally branched C 1 -C 4 -alkylcarbonyl, optionally branched C 1 -C 4 -haloalkyl or optionally branched C 1 -G t -haloalkoxy,
  • R 2 is one of the following radicals:
  • (2,5-dioxopyrrolidin-1-yl) methyl (2-oxopyrrolidin-1-yl) carbonyl, (3-methyl-2-oxopyrrolidin-1-yl) methyl, 1- (2,5-dioxopyrrolidin-1-one) yl) -2,2,2-trifluoroethyl, (2R) -2- (ethoxycarbonyl) -5-oxopyrrolidin-1-yl, (2S) -2- (ethoxycarbonyl) -5-oxopyrrolidin-1-yl, 2-
  • R 3 is methoxy
  • R 4 is methoxy
  • R 6 is one of the following radicals:
  • R 10 is one of the following radicals:
  • R 1 and R 5 are both hydrogen, the remaining substituents having one or more of the meanings mentioned above, and the agrochemically active salts thereof.
  • R7 is hydrogen, the remaining substituents having one or more of the meanings mentioned above, and the agrochemically active salts thereof.
  • R 8 represents chlorine, bromine, fluorine, iodine, cyano or CF 3 , where the other substituents have one or more of the meanings mentioned above, and the agrochemically active salts thereof.
  • R 9 is H or Me, where the other substituents have one or more of the meanings given above, and the agrochemically active salts thereof.
  • R 1 , R 5 , R 6 and R 7 are hydrogen
  • R 10 is methyl, ethyl, propyl, cyclopropyl, cyclopropylmethyl, 1-cyclopropyleth-1-yl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,2-dimethylprop-1-yl, tert-butyl, cyclobutyl, butyl, 3-methylbut -l-yl, 2-methylbut-1-yl, 2-methylprop-1-yl, 1-fluoroprop-2-yl, cyclopentyl, propan-2-yl, pentan-3-yl, pentan-2-yl, pentyl , Prop-2-en-1-yl, prop-2-in
  • inorganic acids examples include hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulfuric acid, phosphoric acid and nitric acid and acid salts such as NaHSO 4 and KHSO 4 .
  • Suitable organic acids are, for example, formic acid, carbonic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), Arylsulfonic acids or - disulfonic acids (aromatic radicals such as phenyl and naphthyl which carry one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids with straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylphosphonic acids or - diphosphonic acids (aromatic radicals such as phenyl and naphthyl which one or two Carrying phosphonic acid residues),
  • the metal ions are, in particular, the ions of the elements of the second main group, in particular calcium and magnesium, the third and fourth main groups, in particular aluminum, tin and lead, and the first to eighth transition groups, in particular chromium, manganese, iron, cobalt, nickel, copper, Zinc and others into consideration. Particularly preferred are the metal ions of the elements of the fourth period.
  • the metals can be present in the various valences that belong to them.
  • Substituted groups may be monosubstituted or polysubstituted, with multiple substituents the substituents may be the same or different.
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkyl saturated, straight-chain or branched hydrocarbon radicals having 1 to 10 carbon atoms, such as (but not limited to) methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1,1-dimethylethyl, Pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylburyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2 Ethyl butyl, 1, 1, 2-tri
  • Haloalkyl straight-chain or branched alkyl groups having 1 to 4 carbon atoms (as mentioned above), in which groups the hydrogen atoms may be partially or completely replaced by halogen atoms as mentioned above, for example (but not limited to) Q-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-difluoroethyl, 2,2-dichloro 2-fluoroethyl, 2,2,2-trichloroethyl
  • Alkenyl unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 16 carbon atoms and at least one double bond in any position, such as (but not limited to) C 2 -C 6 alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1 Methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2- butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-prop
  • Alkynyl straight-chain or branched hydrocarbon groups having 2 to 16 carbon atoms and at least one triple bond in any position, such as (but not limited to) C 2 -C 6 alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2- Methyl 3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5- Hexynyl, 1-methyl-2-pent
  • Alkoxy saturated, straight or branched chain alkoxy having from 1 to 4 carbon atoms such as (but not limited to) C r C 4 alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy , 1, 1-dimethylethoxy;
  • Haloakoxy straight-chain or branched alkoxy groups having 1 to 4 carbon atoms (as mentioned above), wherein in these groups partially or completely the hydrogen atoms may be replaced by halogen atoms as mentioned above, such as (but not limited to) C 1 -C 2 -haloalkoxy, for example Chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-
  • Thioalkyl saturated, straight-chain or branched alkylthio radicals having 1 to 6 carbon atoms, such as (but not limited to) C 1 -C 6 -alkylthio, such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio , 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1, 2-dimethylpropylthio, 1 Methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,
  • Thiohaloalkyl straight-chain or branched alkylthio groups having 1 to 6 carbon atoms (as mentioned above), wherein in these groups partially or completely the hydrogen atoms may be replaced by halogen atoms as mentioned above, such as (but not limited to) C 1 -C 2 -haloalkylthio, for example Chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoro-methylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2- Trifluoroethylthio, 2-chloro-2-fluoroeth
  • Cycloalkyl mono-, bi- or tricyclic, saturated hydrocarbon groups having 3 to 12 carbon ring members, such as e.g. (but not limited to) cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, bicyclo [l, o, l] butane, decalinyl norbornyl;
  • Cylcoalkenyl mono-, bi- or tricyclic, non-aromatic hydrocarbon groups having 5 to 15 carbon ring members having at least one double bond, such as (but not limited to) cyclopenten-1-yl, cyclohexen-1-yl, cyclohepta-1,3-diene - 1-yl, norbornen-1-yl; (Alkoxy) carbonyl: an alkoxy group having 1 to 4 carbon atoms (as mentioned above) which is bonded to the skeleton via a carbonyl group (-CO-);
  • Heterocyclyl three- to fifteen-membered saturated or partially unsaturated heterocycle containing one to four heteroatoms from the group oxygen, nitrogen or sulfur: mono-, bi- or tricyclic heterocycles containing in addition to carbon ring members one to three nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms; if the ring contains several oxygen atoms, these are not directly adjacent; such as, but not limited to, oxiranyl, aziridinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3 Isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidiny
  • Hetaryl unsubstituted or unbranched or substituted, 5 to 15-membered, partially or completely unsaturated mono-, bi- or tricyclic ring system, wherein at least one of the rings of the ring system is completely unsaturated, containing one to four heteroatoms from the group oxygen, nitrogen or Sulfur, if the ring contains several oxygen atoms, these are not directly adjacent; for example (but not limited to)
  • 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom 5-membered heteroaryl groups, which besides carbon atoms can contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members. eg 2-furyl, 3
  • benzo-fused 5-membered heteroaryl containing one to three nitrogen atoms or a nitrogen atom and an oxygen or sulfur atom 5-membered heteroaryl groups which may contain, besides carbon atoms, 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 carbon ring member may be bridged by a buta-1,3-di-1,4-diyl group in which one or two C atoms may be replaced by N atoms; e.g. Benzindolyl, benzimidazolyl, benzothiazolyl, benzopyrazolyl, benzofuryl;
  • Nitrogen atoms, or nitrogen-bonded benzo-fused 5-membered heteroaryl, containing one to three nitrogen atoms 5-membered ring heteroaryl groups which may contain one to four nitrogen atoms or one to three nitrogen atoms as ring members in addition to carbon atoms, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member through a buta-1, 3-diene
  • 1,4-diyl group may be bridged in which one or two C atoms may be replaced by N atoms in which one or two C atoms may be replaced by N atoms, said rings via one of the nitrogen ring members to the Scaffold are bound, eg 1-pyrrolyl, 1-pyrazolyl, 1,2,4-triazol-1-yl, 1-imidazolyl, 1,2,3-triazol-1-yl, 1,3,4-triazol-1-yl;
  • Ring heteroaryl groups which, in addition to carbon atoms, may contain one to three or one to four nitrogen atoms as ring members, for example 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; Not included are those combinations which contradict the laws of nature and which the expert would have excluded because of his expertise. For example, ring structures with three or more adjacent O atoms are excluded.
  • a further subject of the present invention relates to a process for preparing the diaminopyrimidines of the formulas (I) according to the invention
  • Scheme 1 shows a possibility for the synthesis of the intermediates of formula (V).
  • alkylamino compounds of the formula (H) are either commercially available or can be prepared according to literature specifications.
  • a method for preparing suitable cyclopropyl amino compounds of type (H) is, for example, the rearrangement of suitable carboxylic acid derivatives to the corresponding amino compounds (for example described in J. Am. Chem. Soc. 1961, 83, 3671-3678).
  • Other methods for example for the preparation of cyclobutyl-amino compounds of type (II) include the hydroboration of suitable cyclobutenes and subsequent treatment with NH 2 SO 3 H (eg Tetrahedron 1970, 26, 5033-5039), the reductive amination of cyclobutanones (for example described in US Pat Chem.
  • a method for preparing suitable halogen-substituted amino compounds (D) is, for example, the reduction of corresponding carboxamides (for example described in EP30092) or corresponding oximes or azides (for example described in Chem. Ber. 1988, 119, 2233) or nitro compounds (eg Chem., 1953, 75, 5006)
  • Another possibility is the treatment of corresponding aminocarboxylic acids with SF 4 in HF (eg described in J. Org. Chem. 1962, 27, 1406).
  • the ring opening of substituted aziridines by means of HF is described in J. Org. Chem. 1981, 46, 4938.
  • halogen-substituted amino compounds (II) include the cleavage of corresponding phthalimides according to Gabriel (eg described in DE 3429048), aminolysis of suitable haloalkyl halides (eg described in US2539406) or the degradation of corresponding carboxylic acid azides (eg described in DE3611 195).
  • Aminoaldehydes or ketones can be converted by means of suitable fluorinating reagents (eg DAST) into the corresponding difluoroalkylamines (WO2008008022), while aminoalcohols form the corresponding monofluoroalkylamines (eg WO2006029115).
  • suitable fluorinating reagents eg DAST
  • aminoalcohols form the corresponding monofluoroalkylamines (eg WO2006029115).
  • from amino alcohols by means of suitable chlorinating and brominating chloro and Bromalkylamines are obtained (J. Org. Chem. 2005
  • R 8 CF 3 : J. Fluorine Chem. 1996, 77, 93; see also WO 2000/047539.
  • One way to represent Compound (V) is shown in Scheme 1.
  • inorganic salts such as NaHCO 3 , Na 2 CO 3 or K 2 CO 3 , organometallic compounds such as LDA or NaHMDS or amine bases such
  • Ethyldiisopropylamine, DBU, DBN or tri-n-butylamine may also be carried out as described, for example, in Org. Lett. 2006, 8, 395, with the aid of a suitable transition metal catalyst, for example palladium, together with a suitable ligand, for example triphenylphosphine or xanthphos.
  • a suitable transition metal catalyst for example palladium
  • a suitable ligand for example triphenylphosphine or xanthphos.
  • the substituted aromatic amines are either commercially available or can be prepared by methods known from the literature from commercially available precursors.
  • Aromatic amines bearing one or more of the same or different substituents in the aromatic moiety can be prepared by a variety of methods described in the pertinent literature. Below are examples of some of the methods mentioned.
  • Cyclic, N-bonded radicals R 1 to R 5 can be prepared, for example, by condensation of nitroaminoaromatics with haloalkylcarbonyl halides or diesters or diester equivalents or lactones; the subsequent reduction of the nitro group provides the desired aromatic amine.
  • the intermediate (V) is reacted in the presence of Brönsted acids, e.g. anhydrous hydrochloric acid, camphorsulfonic acid or p-toluenesulfonic acid in a suitable solvent such as dioxane, THF, DMSO, DME, 2-methoxyethanol, n-butanol or acetonitrile at a temperature of 0 ° C-140 ° C over a period of 1-48 h reacted with an aromatic amine (TV).
  • Brönsted acids e.g. anhydrous hydrochloric acid, camphorsulfonic acid or p-toluenesulfonic acid in a suitable solvent such as dioxane, THF, DMSO, DME, 2-methoxyethanol, n-butanol or acetonitrile
  • a suitable solvent such as dioxane, THF, DMSO, DME, 2-methoxyethanol, n-butanol or
  • reaction of (V) and (IV) to (I) may also be base catalysis, that is carried out using, for example, carbonates such as potassium carbonate, alcoholates such as potassium ter / .Butylat or hydrides such as sodium hydride, thereby also the catalytic use of a Transition metal such as palladium may be useful together with a suitable ligand such as xanthophos.
  • base catalysis that is carried out using, for example, carbonates such as potassium carbonate, alcoholates such as potassium ter / .Butylat or hydrides such as sodium hydride, thereby also the catalytic use of a Transition metal such as palladium may be useful together with a suitable ligand such as xanthophos.
  • a suitable Lewis acid or a suitable base at a temperature of -15 ° C to 100 0 C in a suitable inert solvent such as 1,4-dioxane, diethyl ether, THF, n-butanol, tert-butanol, Dichloroethane or dichloromethane an aniline (TV) with a 2,4-dihalopyrimidine (III) for a period of 1-24 h reacted.
  • a suitable inert solvent such as 1,4-dioxane, diethyl ether, THF, n-butanol, tert-butanol, Dichloroethane or dichloromethane an aniline (TV) with a 2,4-dihalopyrimidine (III) for a period of 1-24 h reacted.
  • inorganic salts such as NaHCC> 3 , Na 2 CO 3 or K 2 CO 3 , organometallic compounds such as LDA or NaHMDS or amine bases such as ethyldiisopropylamine, DBU, DBN or tri-n-butylamine can be used.
  • organometallic compounds such as LDA or NaHMDS
  • amine bases such as ethyldiisopropylamine, DBU, DBN or tri-n-butylamine
  • Lewis acid for example (but not limited to) halides of the metals zinc (eg ZnCl 2 ), magnesium, copper, tin or titanium can be used (see, for example, US 2005/0256145 or WO 2005/023780 and references cited therein).
  • One way to represent Compound (I) is shown in Scheme 4.
  • the intermediate (VT) is then used in the presence of bases such as, for example, carbonates such as potassium carbonate, alcoholates such as potassium tert-butylate or hydrides such as sodium hydride in a suitable solvent such as, for example, dioxane, THF, DMSO, DME, 2-methoxyethanol, n-butanol or acetonitrile at a temperature of 0 0 C-HO 0 C over a period of 1-48 h with amines of the formula (H) are reacted, thereby also the catalytic use of a transition metal for example, palladium may be useful together with a suitable ligand such as triphenylphosphine or xanthphos.
  • bases such as, for example, carbonates such as potassium carbonate, alcoholates such as potassium tert-butylate or hydrides such as sodium hydride in a suitable solvent such as, for example, dioxane
  • cyclic carbamate-substituted aromatic amines are either commercially available, can be prepared by methods known from the literature from commercially available precursors or are described below:
  • the intermediate (V) is in the presence of Bronsted acids such as anhydrous hydrochloric acid, camphorsulfonic acid or p-toluenesulfonic acid in a suitable solvent such as dioxane, THF, DMSO, DME, 2-methoxyethanol, n-butanol or acetonitrile at a temperature of 0 0 C-HO 0 C over a period of 1-48 h with an aromatic amine (FVa) reacted.
  • Bronsted acids such as anhydrous hydrochloric acid, camphorsulfonic acid or p-toluenesulfonic acid in a suitable solvent such as dioxane, THF, DMSO, DME, 2-methoxyethanol, n-butanol or acetonitrile
  • a suitable solvent such as dioxane, THF, DMSO, DME, 2-methoxyethanol, n-butanol or acetonitrile
  • reaction of (V) and (TVa) to (Ia) may also be base catalysed, that is, using, for example, carbonates such as potassium carbonate, alcoholates such as potassium ter / .Butylat or hydrides such as sodium hydride be carried out, thereby also the catalytic use of a Transition metal such as palladium may be useful together with a suitable ligand such as xanthophos.
  • the products (Ia) can be prepared by a copper-catalyzed cross-coupling between oxazolidinones (VTTT) and aryl halides (VII) in the presence of a copper source, a ligand, and a
  • Base can be prepared in different solvents and at different temperatures .
  • Various copper sources can be used, usually CuI, CuSO 4 , Cu powder are used.
  • Numerous ligands such as 1,2-diaminocyclohexane or MeNHCH 2 CH 2 NHMMe can be used.
  • the bases used are, for example, K 2 CO 3 , K 3 PO 4 , Cs 2 CO 3 .
  • These reactions can also be carried out under microwave conditions.
  • a suitable Lewis acid or a suitable base at a temperature of -15 ° C to 100 0 C in a suitable inert solvent such as 1,4-dioxane, diethyl ether, THF, n-butanol, tert-butanol, Dichloroethane or dichloromethane an aniline (TVa) with a 2,4-dihalopyrimidine (111) for a period of 1-24 h reacted.
  • a suitable inert solvent such as 1,4-dioxane, diethyl ether, THF, n-butanol, tert-butanol, Dichloroethane or dichloromethane an aniline (TVa) with a 2,4-dihalopyrimidine (111) for a period of 1-24 h reacted.
  • inorganic salts such as NaHCOa, Na 2 CO 3 or K 2 CO 3 , organometallic compounds such as LDA or NaHMDS or amine bases such as ethyldiisopropylamine, DBU, DBN or tri-n-butylamine can be used.
  • organometallic compounds such as LDA or NaHMDS
  • amine bases such as ethyldiisopropylamine, DBU, DBN or tri-n-butylamine
  • Lewis acid for example (but not limited to) halides of the metals zinc (eg ZnCl 2 ), magnesium, copper, tin or titanium can be used (see, for example, US 2005/0256145 or WO 2005/023780 and references cited therein).
  • the intermediate (VIa) in the presence of bases such as carbonates such as potassium carbonate, alcoholates such as potassium tert-butylate or hydrides such as sodium hydride in a suitable solvent such as dioxane, THF, DMSO, DME , 2-methoxyethanol, n-butanol or acetonitrile at a temperature of 0 0 C-140 0 C over a period of 1-48 h with amines of the formula (H) is reacted, thereby also the catalytic use of a transition metal such
  • palladium may be useful together with a suitable ligand such as triphenylphosphine or xanthphos.
  • the intermediate (V) is in the presence of Bronsted acids such as anhydrous hydrochloric acid, camphorsulfonic acid or p-toluenesulfonic acid in a suitable solvent such as dioxane, THF, DMSO, DME, 2-methoxyethanol, n-butanol or acetonitrile at a temperature of 0 0 C-HO 0 C over a period of 1-48 h with an aromatic amine (TX) reacted.
  • Bronsted acids such as anhydrous hydrochloric acid, camphorsulfonic acid or p-toluenesulfonic acid
  • a suitable solvent such as dioxane, THF, DMSO, DME, 2-methoxyethanol, n-butanol or acetonitrile
  • reaction of (V) with (IX) to (Ia) can also be carried out under base catalysis, e.g. Example, using carbonates, potassium carbonate, alkoxides, wei potassium tert-butylate, or hydrides, such as. B, sodium hydride, the synthesis of compounds of formula (IX) and the ring closure to the oxazolidinone under basic conditions is described for example in Tetrahedron Lett. 1988, 29, 5095, or DE3704632)
  • the intermediates of formula (FVa) can be prepared via a copper-catalyzed cross-coupling between oxazolidinones (VTII) and aryl halides (X) in the presence of a copper source, a ligand, and a base in various solvents and at various temperatures.
  • Various copper sources can be used are usually using CuI, CuSO 4 , Cu powder.
  • Numerous ligands such as 1, 2-diaminocyclohexane or, MeNHCH 2 CH 2 NHMMe can be used.
  • the bases used are, for example, K 2 CO 3 , K 3 PO 4 , Cs 2 CO 3 .
  • Zyclic carbamates (oxazolidinones) of the formula (VTH) are either commercially available or can be prepared from commercially available precursors by methods known from the literature.
  • Oxazolidinones of the formula (VHT) can be prepared, for example, from aminoalcohol derivatives, open-chain carbamates, epoxides or aziridines (Review: Chem. Rev. 1996, 96, 835; for individual examples, see also Synthesis 2007, 3111, J. Org , 2006, 71, 5023, WO 2005/033095 A1, J. An. Chem. 1989, 111, 2211 and references cited therein.
  • lactam-substituted aromatic amines (IVb) are either commercially available, can be prepared by methods known from the literature from commercially available precursors or are described below:
  • the intermediate (V) is in the presence of Bronsted acids such as anhydrous hydrochloric acid, camphorsulfonic acid or p-toluenesulfonic acid in a suitable solvent such as dioxane, THF, DMSO, DME, 2-methoxyethanol, n-butanol or acetonitrile at a temperature of O 0 C-HO 0 C over a period of 1-48 h with an aromatic amine (TVb) reacted.
  • Bronsted acids such as anhydrous hydrochloric acid, camphorsulfonic acid or p-toluenesulfonic acid in a suitable solvent such as dioxane, THF, DMSO, DME, 2-methoxyethanol, n-butanol or acetonitrile
  • a suitable solvent such as dioxane, THF, DMSO, DME, 2-methoxyethanol, n-butanol or acetonitrile
  • reaction of (V) and (FVb) to (Ib) may also be base catalysed, that is, carried out using, for example, carbonates such as potassium carbonate, alcoholates such as potassium tert-butylate or hydrides such as sodium hydride, including the catalytic use of a transition metal for example, palladium may be useful together with a suitable ligand such as xanthphos.
  • Thiolactams of the formula (Ib-IT) can be prepared, for example, by sulfurization of lactams of the formula (Ib-I) in the presence of suitable reagents such as "Lawesson'reagent.” This reaction can be carried out in various solvents, for example toluene, xylene, THF or Pyridine and at various temperatures, even under microwave conditions (see Synthesis 2006, 2327; Eur. J. Org. Chem 2005, 505; Synthesis 1994, 993).
  • thiolactams from the corresponding lactams are widely described in the literature and can be carried out using P 4 S 10 , boron sulfide, ethylaluminum sulfide or similar reagents. see J. Org Chem 2003, 68, 5792, tetrahedron Lett., 2001, 57, 9635).
  • the products of formula (Ib) can be prepared via a copper-catalyzed cross-coupling between oxazolidinones (XI) and aryl halides (VTT) in the presence of a copper source, a
  • Ligands and a base can be prepared in various solvents and at various temperatures.
  • Various copper sources can be used, usually containing CuI,
  • Cu powder can be used.
  • Numerous ligands such as 1,2-
  • Diaminocyclohexane or, MeNHCH 2 CH 2 NHMMe can be used.
  • the bases used are, for example, K 2 CO 3 , K 3 PO 4 , Cs 2 CO 3 . These reactions can also take place
  • the anilinopyrimidines of the type (Ib-HT) can be protected with suitable reagents on the aniline-NH in the event that R 6 is hydrogen.
  • suitable reagents on the aniline-NH for example, benzyl halides can be benzylated with variously substituted benzyl halides in the presence of a base in various solvents and at various temperatures (see WO 07/073117).
  • the methylation at this point succeeds, for example, with methyl iodide and sodium thyrdide as base, as for example in WO 05/005438; Chem. Pharm. Bull. 2000, 48, 1504; or J. Med. Chem. 1993, 36, 1993 described in various solvents and at different temperatures.
  • Carbamate protections are usually carried out on such systems with BOC 2 O, optionally with a suitable catalyst such as DMAP, optionally with a base in various solvents and at different temperatures (see, for example, WO 04/087698).
  • the anilinopyrimidines of the type (Ib-IV) can be prepared under microwave conditions, by Pd-catalyzed aminocarbonylation of halogen-substituted compounds of type (VII) and the corresponding cyclic lactams (XI) in various solvents such as
  • Mo (CO) 6 as a carbon monoxide source
  • a base such as DBU
  • a Pd source such as
  • the aminocarbonylation can also be carried out without microwave support under classical thermal conditions. Carbon monoxide and other carbon monoxide sources such as DMF can be used as well. Nickel can also be used instead of Pd. (See: J. Org. Chem., 2002, 67, 6232; Angew Chem. Int. Ed., 2007, 46, 8460; Org. Lett., 2007, 9, 4615).
  • the nitro compounds of the type (XTT) can be reduced by various methods to the corresponding anilines of the type (TVb).
  • the reduction can be carried out for example by catalytic hydrogenation with PdZC 7 , PtO 2 , Raney Ni and hydrogen or using Pd / C with NH 4 HCO 2 in various solvents such as MeOH, EtOH, THF or dioxane (see: 5 / Org. Chem., 1990, 55, 3195)., Org. Chem., 1990, 55, 3195)., Org. Chem., 1991, 34, 2954, J. Med.
  • the reduction can also be carried out with metals such as Zn, Sn or iron in the presence of acids such as AcOH, HCl.
  • metals such as Zn, Sn or iron
  • acids such as AcOH, HCl.
  • other reducing agents such as SnCl 2 or TiCl 3 can also be used (see: J. Am.Chem.Soc., 2006, 128, 1162, Bioorg.Med.Chem.Lett. 2004, 14, 2905, J. Med. Chem. 1989, 32, 1612)
  • the products of formula (TVb) can be prepared via a copper-catalyzed cross-coupling between lactams (XI) and halogenated anilines of type (X) in the presence of a copper source, a ligand and a base in various solvents and at different temperatures Copper sources can be used, usually CuI, CuSO 4 , Cu powder are used. Numerous ligands such as 1,2-diaminocyclohexane or MeNHCH 2 CH 2 NHMMe can be used. The bases used are, for example, K 2 CO 3 , K 3 PO 4 , Cs 2 CO 3 . These reactions can also be carried out under microwave conditions. For general reviews, see: Chem. Rev.
  • halogenated anilines of type (X) are either commercially available or obtainable by literature methods from commercially available precursors.
  • the cyclic lactams of the type (XT) are either commercially available or can be prepared by methods known from the literature, such as Beckmann rearrangement of aldoximes or ketoximes, intramolecular cyclization of amino acids or amino esters (see Tetrahedron Lett., 1980, 21, 243, J. Med. 1996, 39, 1898), intramolecular cyclization catalyzed by Metals such as Pd (J. Org. Chem. 2000, 65, 6249), intramolecular radical cyclization (J Org. Chem. 1998, 63, 804), aminolysis of cyclic esters (WO 2007/127688 A2, WO 2005/113504 Al J. Org. Chem. 1991, 56, 5982).
  • lactam-substituted nitro compounds of the type (XIIa) is the reaction of corresponding nitroanilines of the type (XXI) with lactones of the type (XIa), for example in hydrochloric acid (see Indian J. Chem. Section B 1986, 25B, 395):
  • Nitro compounds of type (XV) can be converted into the corresponding adducts of type (XVI) in the presence of a base such as, for example, K 2 CO 3 or NaH by a Michael addition to ⁇ , ⁇ -unsaturated carbonyl compounds of the type (XTV).
  • a base such as, for example, K 2 CO 3 or NaH
  • the nitroesters of type (XVI) can be reduced by numerous methods (see Scheme 16), spontaneously cyclizing to the corresponding lactams (XI).
  • nitro compounds of type (XV) are either commercially available or can be prepared by methods known from the literature (see: Org., Read, 1962, 12, 101; J. Org. Chem. 2006, 71, 4585; J. Org. Chem 1989, 54, 5783).
  • oxo-substituted cyclic carbamates-substituted aromatic amines are either commercially available, can be prepared by methods known from the literature from commercially available precursors or are described below.
  • the intermediate (V) is in the presence of Bronsted acids such as anhydrous hydrochloric acid, camphorsulfonic acid or p-toluenesulfonic acid in a suitable solvent such as dioxane, THF, DMSO, DME, 2-methoxyethanol, n-butanol or acetonitrile at a temperature of 0 0 C-140 0 C over a period of 1-48 h with an aromatic amine (TVc) reacted.
  • Bronsted acids such as anhydrous hydrochloric acid, camphorsulfonic acid or p-toluenesulfonic acid in a suitable solvent such as dioxane, THF, DMSO, DME, 2-methoxyethanol, n-butanol or acetonitrile
  • a suitable solvent such as dioxane, THF, DMSO, DME, 2-methoxyethanol, n-butanol or acetonitrile
  • reaction of (V) and (TVc) to (Ic) may also be base catalysed, that is, carried out using, for example, carbonates such as potassium carbonate, alcoholates such as potassium tert-butylate or hydrides such as sodium hydride, wherein thereby also the catalytic use of a transition metal for example, palladium may be useful together with a suitable ligand such as xanthphos.
  • carbonates such as potassium carbonate
  • alcoholates such as potassium tert-butylate
  • hydrides such as sodium hydride
  • nitro compounds of the type (XIX) can be reduced to the corresponding anilines of the type (TVc) by numerous methods (see also Scheme 16).
  • the nitro compounds of type (XIX) can also be prepared via Cu-catalyzed couplings between nitroanilines and the corresponding succinimides (see Synthesis 2006, 1868).
  • Oxo-substituted thiolactams of the formula (XIXb) can be prepared, for example, by sulfurization of oxo-substituted lactams of the formula (XIXa) in the presence of suitable reagents, such as "Lawesson'reagent.” This reaction can be carried out in various solvents, for example toluene, xylene, THF or pyridine and at various temperatures, even under microwave conditions (see Synthesis 1996, 1485).
  • compounds of the formula (I) can also be prepared, for example, by sequential nucleophilic addition of an aliphatic amine (U) and a (hetero) aromatic amine (TV) to a suitable substituted pyrimidine (HI), as outlined below in Scheme 25:
  • Each A is independently representative of a suitable leaving group, for example for a halogen atom (F, Cl, Br, I), SMe, SO 2 Me, SOMe or triflate (CF 3 SO 2 O: in pyrimidines known from WO2005095386).
  • a halogen atom F, Cl, Br, I
  • SMe SMe
  • SO 2 Me SO 2 Me
  • SOMe SOMe
  • triflate CF 3 SO 2 O: in pyrimidines known from WO2005095386.
  • Suitable reaction auxiliaries are unbranched or the usual inorganic or organic bases or acid acceptors. These include, preferably, alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkoxides, such as, for example, sodium, potassium or calcium acetate, lithium, sodium, Potassium or calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium bicarbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, ethanolate, n- or -propanolate, n-, -is, -s or t-butanolate; furthermore also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexyl
  • Suitable diluents are virtually all inert organic solvents. These include preferably aliphatic and aromatic, unbranched or halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl, methyl isopropyl or methyl isobutyl ketone, esters such as methyl acetate or ethyl
  • reaction temperatures can be varied within a substantial range in the processes according to the invention. In general, one works at temperatures between 0 0 C and 25O 0 C, preferably at temperatures between 10 0 C and 185 ° C.
  • the processes according to the invention are generally carried out under normal pressure. However, it is also possible to work under elevated or reduced pressure.
  • the starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use one of the components used in each case in a larger excess.
  • the work-up is carried out in the inventive method in each case by customary methods (cf., the preparation examples).
  • R 7 is hydrogen
  • R 8 is CF 3 , CFH 2 or CF 2 H
  • R 9 is hydrogen, ethyl, propyl, propan-2-yl, 2-methoxyethane-1-yl, prop-2-en-1-yl, CH 2 OCH 3 , COMe, COOMe, COOEt, COOtertBu, COCF 3 or benzyl .
  • R 10 is ethyl, propyl, cyclopropyl, cyclopropylmethyl, 1-cyclopropyleth-1-yl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,2-dimethylprop-1-yl, tert-butyl,
  • Cyclobutyl 2-methyl-cyclobut-1-yl, 3-methyl-cyclobut-1-yl, butyl, 3-methylbut-1-yl, 2-methylbut-1-yl, 2-methylprop-1-yl, 1 - Fluoroprop-2-yl, cyclopentyl, propan-2-yl, pentan-3-yl, pentan-2-yl, pentyl, prop-2-en-1-yl, butan-2-yl, 2,2,2- Trifluoroethyl, 2,2-difluoroethyl, 2-methoxyethane-1-yl, 2-methylmercaptoethane-1-yl, 2-fluoroethane-1-yl, 2-chloroethane-1-yl, 2-cyanoethane-1-yl, Methoxypropan-2-yl, 3-methoxypropan-1-yl, 1-
  • Methylmercaptopropan-2-yl 2-methyl-1- (methylsulfanyl) -propan-2-yl, oxetan-3-yl, 1,1,1-trifluoropropan-2-yl, 2,2,3,3,3-pentafluoropropyl , l, l, l-trifluoropropan-3-yl, 1,1,1-trifluorobutan-2-yl, l, l, l-trifluorobutan-3-yl, 2-methylprop-2-en-l-yl or 1 Fluoropropane-2-yl,
  • R 9 and R 10 together with the nitrogen atom to which they are attached form an unsubstituted or substituted 3-7 membered, saturated cycle, which may contain up to another heteroatom,
  • substituents are independently selected from methyl, fluoro, chloro and / or bromine, cyano, hydroxy, methoxy, CF 3
  • heteroatoms are selected from oxygen, sulfur or nitrogen New are compounds of the formula (V) in which
  • R 7 is hydrogen
  • R 8 stands for iodine
  • R 9 is hydrogen, methyl, ethyl, propyl, propan-2-yl, 2-methoxyethane-1-yl, prop-2-en-1-yl, CH 2 OCH 3 , COMe, COOMe, COOEt, COOtertBu, COCF 3 or benzyl,
  • R 10 is methyl, ethyl, propyl, cyclopropyl, cyclopropylmethyl, 1-cyclopropyleth-1-yl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,2-dimethylprop-1-yl, tert-butyl,
  • Cyclobutyl 2-methyl-cyclobut-1-yl, 3-methyl-cyclobut-1-yl, butyl, 3-methylbut-1-yl, 2-methylbut-1-yl, 2-methylprop-1-yl, 1 - Fluo ⁇ rop-2-yl, cyclopentyl, propan-2-yl, pentan-3-yl, pentan-2-yl, pentyl, prop-2-en-1-yl, butan-2-yl, 2,2,2- Trifluoroethyl, 2,2-difluoroethyl, 2-methoxyethane-1-yl, 2-methylmercaptoethane-1-yl, 2-fluoroethane-1-yl, 2-chloroethane-1-yl, 2-cyanoethane-1-yl, Methoxypropan-2-yl, 3-methoxypropan-1-yl, 1-
  • Methylmercaptopropan-2-yl 2-methyl-1- (methylsulfanyl) -propan-2-yl, oxetan-3-yl, 1,1,1-trifluoropropan-2-yl, 2,2,3,3,3-pentafluoropropyl , l, l, l-trifluoropropan-3-yl, 1,1,1-trifluorobutan-2-yl, l, l, l-trifluorobutan-3-yl, 2-methylprop-2-en-l-yl or 1 -Fluoropropan-2-yl,
  • R 9 and R 10 taken together with the nitrogen atom to which they are attached, form an unsubstituted or substituted 3-7 membered, saturated cycle which may contain up to another heteroatom,
  • substituents are independently selected from methyl, fluorine, chlorine and / or bromine atoms, cyano, hydroxy, methoxy, CF 3 ,
  • heteroatoms are selected from oxygen, sulfur or nitrogen New are compounds of the formula (V) in which
  • R 7 is hydrogen
  • R 8 is SMe, SOMe or SO 2 Me
  • R 9 is hydrogen, methyl, ethyl, propyl, propan-2-yl, 2-methoxyethane-1-yl, prop-2-en-1-yl, CH 2 OCH 3 , COMe, COOMe, COOEt, COOtertBu, COCF 3 or benzyl,
  • R 10 is ethyl, propyl, cyclopropyl, cyclopropylmethyl, 1-cyclopropyleth-1-yl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,2-dimethylprop-1-yl, tert-butyl,
  • Methylbut-1-yl 2-methylprop-1-yl, 1-fluoroprop-2-yl, cyclopentyl, propan-2-yl, pentan-3-yl, pentan-2-yl, pentyl, prop-2-ene 1-yl, butan-2-yl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2-
  • Methoxyethane-1-yl 2-methylmercaptoethane-1-yl, 2-fluoroethane-1-yl, 2-chloroethane-1-yl, 2-cyanoethane-1-yl, 1-methoxypropan-2-yl, 3-methoxypropane l-yl, 1-
  • Trifluorobutan-2-yl 1, 1, 1-trifluorobutan-3-yl, 2-methylprop-2-en-1-yl or 1-fluoropropane-2
  • R 9 and R 10 taken together with the nitrogen atom to which they are attached, form an unsubstituted or substituted 3-7 membered, saturated cycle which may contain up to another heteroatom,
  • substituents are independently selected from methyl, fluoro, chloro and / or bromine, cyano, hydroxy, methoxy, CF 3
  • heteroatoms are selected from oxygen, sulfur or nitrogen New are compounds of the formula (V) in which
  • R 7 is hydrogen
  • R 8 stands for cyano
  • R 9 is hydrogen, methyl, propyl, propan-2-yl, 2-methoxyethane-1-yl, prop-2-en-1-yl, CH 2 OCH 3 , COMe, COOMe, COOEt, COOtertBu, COCF 3, or Benzyl stands,
  • R 10 is propyl, cyclopropylmethyl, 1-cyclopropyleth-1-yl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,2-dimethylprop-1-yl, tert-butyl, cyclobutyl, 2-methyl-cyclobut-1-yl, 3 Methyl-cyclobut-1-yl, 3-methylbut-1-yl, 2-methylbut-1-yl, 1-fluoroprop-2-yl,
  • R 7 is hydrogen
  • R 9 is hydrogen
  • R 10 is propyl, 2-methylcyclopropyl, 3-methylcyclobutyl, 2-ethylcyclopropyl,
  • R 1 to R 8 have the abovementioned general, preferred, particularly preferred, very particularly preferred and especially preferred meanings and
  • Hal is fluorine, chlorine, bromine or iodine.
  • Hal is bromine or iodine
  • R 1 and R 5 are equal to hydrogen
  • R 3 and R 6 to R 10 have the abovementioned general, preferred, particularly preferred, very particularly preferred and especially preferred meanings.
  • Hal is bromine or iodine
  • R 1 and R 5 are equal to hydrogen
  • R 2 and R 6 to R 10 have the general, preferred, particularly preferred, most preferred and especially preferred meanings given above.
  • Another object of the invention relates to the non-medical use of diaminopyrimidines according to the invention or mixtures thereof for controlling unwanted microorganisms.
  • Another object of the invention relates to an agent for controlling unwanted microorganisms, comprising at least one diaminopyrimidine according to the present invention. Moreover, the invention relates to a method for controlling unwanted microorganisms, characterized in that the diaminopyrimidines according to the invention are applied to the microorganisms, and / or in their habitat.
  • the substances according to the invention have a strong microbicidal action and can be used for combating unwanted microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.
  • the diaminopyrimidines of the formula (I) according to the invention have very good fungicidal properties and can be employed in crop protection, for example for controlling Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be used in crop protection, for example, to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • the fungicidal compositions according to the invention can be used curatively or protectively for controlling phytopathogenic fungi.
  • the invention therefore also relates to curative and protective methods for controlling phytopathogenic fungi by the use of the active compounds or agents according to the invention, which is applied to the seed, the plant or plant parts, the fruits or the soil in which the plants grow.
  • compositions of the invention for controlling phytopathogenic fungi in crop protection comprise an effective but non-phytotoxic amount of the active compounds according to the invention.
  • effective but non-phytotoxic amount is meant an amount of the agent of the invention sufficient to control or completely kill fungal disease of the plant and at the same time not cause any significant phytotoxicity symptoms It depends on several factors, for example on the fungus to be controlled, the plant, the climatic conditions and the ingredients of the agents according to the invention.
  • plants and parts of plants can be treated.
  • plants are understood as meaning 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 varieties which can or can not be protected by plant variety protection rights.
  • Under plant parts all aboveground and underground parts and organs of the plants, such as shoot, leaf, Flowering and root are understood, with examples of leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds and roots, tubers and rhizomes are listed.
  • the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
  • plants which can be treated according to the invention mention may be made of the following: cotton, flax, grapevine, fruits, vegetables, such as Rosaceae sp. (for example, pome fruits such as apple and pear, but also drupes such as apricots, cherries, almonds and peaches and soft fruits such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Mwaceae sp.
  • Rosaceae sp. for example, pome fruits such as apple and pear, but also drupes such as apricots, cherries, almonds and peaches and soft fruits such as strawberries
  • Rosaceae sp. for example, pome fruits such as apple and pe
  • Rubiaceae sp. for example, coffee
  • Theaceae sp. Sterculiceae sp.
  • Rutaceae sp. for example, lemons, organs and grapefruit
  • Solanaceae sp. for example tomatoes
  • Liliaceae sp. Asteraceae sp.
  • Umbelliferae sp. for example, Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (for example cucumber), Alliaceae sp. leek, onion), Papilionaceae sp.
  • Main crops such as Gramineae sp. (for example corn, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale), Asteraceae sp. (for example sunflower), Brassicaceae sp. (for example, white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, rapeseed, mustard, horseradish and cress). Fabacae sp. (for example, bean, peanuts), Papilionaceae sp. (for example, soybean), Solanaceae sp. (for example potatoes), Chenopodiaceae sp. (for example, sugar beet, fodder beet, Swiss chard, beet); Useful plants and ornamental plants in the garden and forest; and each genetically modified species of these plants.
  • crop plants are treated according to the invention.
  • Blumeria species such as Blumeria graminis
  • Podosphaera species such as Podosphaera leucotricha
  • Sphaerotheca species such as Sphaerotheca fuliginea
  • Uncinula species such as Uncinula necator
  • Gymnosporangium species such as Gymnosporangium sabinae
  • Hemileia species such as Hemileia vastatrix
  • Phakopsora species such as Phakopsora pachyrhizi and Phakopsora meibomiae
  • Puccinia species such as Puccinia recondita or Puccinia triticina
  • Uromyces species such as Uromyces appendiculatus
  • Diseases caused by agents of the group of Oomycetes such as Bremia species, such as Bremia lactucae
  • Peronospora species such as Peronospora pisi or P.
  • Phytophthora species such as Phytophthora infestans
  • Plasmopara species such as Plasmopara viticola
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis
  • Pythium species such as Pythium ultimum
  • Phaeosphaeria species such as Phaeosphaeria nodorum
  • Pyrenophora species such as, for example, Pyrenophora teres
  • Ramularia species such as Ramularia collo-cygni
  • Rhynchosporium species such as Rhynchosporium secalis
  • Septoria species such as Septoria apii
  • Typhula species such as Typhula incarnata
  • Venturia species such as Venturia inaequalis
  • Ear and panicle diseases caused by e.g. Alternaria species, such as Alternaria spp .; Aspergillus species, such as Aspergillus flavus; Cladosporium species, such as Cladosporium cladosporioides; Claviceps species, such as Claviceps purpurea; Fusarium species such as Fusarium culmorum; Gibberella species, such as Gibberella zeae; Monographella species, such as Monographella nivalis; Septoria species such as Septoria nodorum;
  • Alternaria species such as Alternaria spp .
  • Aspergillus species such as Aspergillus flavus
  • Cladosporium species such as Cladosporium cladosporioides
  • Claviceps species such as Claviceps purpurea
  • Fusarium species such as Fusarium culmorum
  • Gibberella species such as Gibberella
  • Sphacelotheca species such as Sphacelotheca reiliana
  • Ti lletia species such as Tilletia caries, T. controversa
  • Urocystis Species such as Urocystis occulta
  • Ustilago species such as Ustilago nuda, U. nuda tritici
  • Verticilium species such as Verticilium alboatrum
  • Nectria species such as Nectria galligena
  • Botrytis species such as Botrytis cinerea
  • Rhizoctonia species such as Rhizoctonia solani
  • Helminthosporium species such as Helminthosporium solani
  • Xanthomonas species such as Xanthomonas campestris pv. Oryzae
  • Pseudomonas species such as Pseudomonas syringae pv. Lachrymans
  • Erwinia species such as Erwinia amylovora
  • the following diseases of soybean beans can be controlled:
  • Alternaria leaf spot (Alternaria spec. Atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), Brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)), Dactuliophora leaf spot (Dactuliophora glycines), Downy Mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), Frogeye leaf spot (Cercospora sojina), Leptosphaerulina leaf spot (Leptosphaerulina trifolii), Phyllostica leaf spot (Phyllosticta sojaecola), Pod and
  • Phytophthora red (Phytophthora megasperma), Brown Stem Red (Phialophora gregata), Pythium Red (Pythium aphanidermatum, Pythium irregular, Pythium Debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Red, Stem Decay, and Damping Off (Rhizoctonia solani), Sclerotinia Stem Decay (Sclerotinia sclerotiorum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Red (Thielaviopsis basicola).
  • Undesirable microorganisms in the present case are phytopathogenic fungi and bacteria.
  • the substances according to the invention can therefore be used to protect plants within a certain period of time after the treatment against the infestation by the said pathogens.
  • the period of time within which protection is afforded generally extends from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the active ingredients.
  • the good plant tolerance of the active ingredients in the necessary concentrations for controlling plant diseases allows treatment of above-ground parts of plants, planting and seed, and the soil.
  • the active compounds according to the invention can be used to combat cereal diseases, for example Erysiphe species, Puccinia and Fusarium species, rice diseases such as Pyricularia and Rhizoctonia and diseases in wine, fruit and vegetable cultivation , for example, against Botrytis, Venturia, Sphaerotheca and Podosphaera species use.
  • the active compounds according to the invention are also suitable for increasing crop yield. They are also low toxicity and have good plant tolerance.
  • the compounds of the invention may be unbranched or in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as anti-MLO agents (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism). They can also be used as intermediates or precursors for the synthesis of other active ingredients.
  • 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, as insecticide. They can be used unbranched or as intermediates and precursors for the synthesis of other active ingredients.
  • the active compounds according to the invention are suitable for good plant tolerance, favorable warm-blood toxicity and good environmental compatibility for the protection of plants and plant organs, for increasing crop yields, improving the quality of the crop in agriculture, in horticulture, in animal breeding, in forests, in gardens and Adventureal facilities, in the storage and material protection and on the hygiene sector occur. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the treatment according to the invention of the plants and plant parts with the active ingredients or agents is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, (spraying), (spraying), sprinkling, vaporizing, spraying, atomizing, (sprinkling), foaming, brushing, spreading, drenching, drip irrigation and propagating material, especially in seeds by dry pickling, wet pickling, slurry pickling, encrusting, single or multi-layer coating, etc. It is also possible to apply the active ingredients by the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient itself into the soil.
  • mycotoxins include: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2 and HT2 toxin, fumonisins, zearalenone, moniliformin, fusarin, diaceotoxyscirpenol (DAS) , Beauvericin, enniatine, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids and aflatoxins, which may be caused, for example, by the following fungi: Fusarium spec., Such as Fusarium acuminatum, F.
  • the active compounds or compositions according to the invention can also be used in the protection of materials for the protection of industrial materials against attack and destruction by undesired microorganisms, such as e.g. Mushrooms, are used.
  • Technical materials as used herein mean non-living materials that have been prepared for use in the art.
  • technical materials to be protected from microbial change or destruction by the active compounds of the invention may be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastics, coolants, and other materials that may be infested or degraded by microorganisms
  • the materials to be protected also include parts of production plants, for example cooling water circuits, which may be adversely affected by the proliferation of microorganisms.
  • technical materials which may be mentioned are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer fluids, particularly preferably wood.
  • the active compounds or compositions according to the invention can prevent adverse effects such as decay, deterioration, decomposition, discoloration or mold.
  • Storage Goods are understood natural substances of plant or animal origin or their processing products, which were taken from nature and for long-term protection is desired
  • Storage goods of plant origin such as plants or plant parts, such as stems, leaves, tubers, seeds , Fruits, grains, can be protected in freshly harvested condition or after processing by (pre-) drying, wetting, crushing, grinding, pressing or roasting
  • Storage Goods also includes timber, whether unprocessed, such as timber, power poles and barriers, or in the form of finished products, such as furniture, storage goods of animal origin are, for example, skins, leather, furs and hair.
  • the active compounds according to the invention can prevent disadvantageous effects such as decay, deterioration, disintegration, discoloration or mold.
  • microorganisms that can cause degradation or a change in the technical materials, for example, bacteria, fungi, yeasts, algae and mucus organisms may be mentioned.
  • the active compounds according to the invention preferably act against fungi, in particular molds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • microorganisms of the following genera Alternaria, such as Alternaria tenuis; Aspergillus, such as Aspergillus niger; Chaetomium, like Chaetomium globosum; Coniophora, like Coniophora puetana; Lentinus, like Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor; Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila; Trichoderma, such as Trichoderma viride; Escherichia, like Escherichia coli; Pseudomonas, such as Pseudomonas aeruginosa; Staphylococcus, such as Staphylococcus aureus.
  • Alternaria such as Alternaria tenuis
  • Aspergillus such as Asper
  • the present invention further relates to an agent for controlling unwanted microorganisms comprising at least one of the diaminopyrimidines according to the invention.
  • an agent for controlling unwanted microorganisms comprising at least one of the diaminopyrimidines according to the invention.
  • Preference is given to fungicidal compositions which contain agriculturally useful auxiliaries, solvents, carriers, surface-active substances or extenders.
  • the carrier means a natural or synthetic, organic or inorganic substance with which the active ingredients for better applicability, v. A. for application to plants or plant parts or seeds, mixed or combined.
  • the carrier which may be solid or liquid, is generally inert and should be useful in agriculture.
  • Suitable solid carriers are: e.g. Ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and silicates, as solid carriers for granules are suitable: e.g. crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as paper, sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: e.g.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates;
  • suitable dispersants are non-ionic and / or ionic substances, e.g.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, solvents. powder, soluble granules, granulated granules, suspension emulsion concentrates, active substance-impregnated natural substances, active substance-impregnated synthetic substances, fertilizers and superfine encapsulations in polymeric substances.
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom, such as ready-to-use solutions, emulsions, water- or oil-based suspensions, powders, wettable powders, pastes, soluble powders, dusts, soluble granules, scattering granules, suspension emulsion concentrates, Active substance-impregnated natural products, active ingredient-impregnated synthetic substances, fertilizers and Feinstverkapselitch be applied in polymeric materials.
  • the application is done in the usual way, e.g. by pouring, spraying, spraying, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient itself into the soil. It can also be the seed of the plants to be treated.
  • the formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active compounds with at least one customary diluent, diluent or diluent, emulsifier, dispersing and / or binding or fixing agent, wetting agent, water repellent, unbranched or siccative and UV stabilizers and unbranched or dyestuffs and pigments, Defoamers, preservatives, secondary thickeners, adhesives, gibberellins and other processing aids.
  • compositions according to the invention comprise not only formulations which are already ready for use and which can be applied to the plant or the seed with a suitable apparatus, but also commercial concentrates which have to be diluted with water before use.
  • the active compounds according to the invention can be used as such or in their (commercially available) formulations and in the formulations prepared from these formulations in admixture with other (known) active ingredients, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides , Fertilizers, safeners or semiochemicals.
  • active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides , Fertilizers, safeners or semiochemicals.
  • Excipients which can be used are those which are suitable for imparting special properties to the composition itself and / or preparations derived therefrom (for example spray liquor, seed dressing), such as certain technical properties and / or specific biological properties.
  • Typical auxiliaries are: extenders, solvents and carriers.
  • Suitable extenders include, for example, water, polar and non-polar organic chemical liquids, for example from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulfones and sulfoxides (such as dimethyl sulfoxide).
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyols which may also be substituted, etherified and
  • liquefied gaseous diluents or carriers are meant those liquids which are gaseous at normal temperature and under normal pressure, e.g. Aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex polymers may be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholipids.
  • Other additives may be mineral and vegetable oils.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g.
  • Petroleum fractions 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.
  • alcohols such as butanol or glycol
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide
  • the agents of the invention may additionally contain other ingredients, e.g. surfactants.
  • Suitable surface-active substances are emulsifying and / or foam-forming agents, dispersants or wetting agents having ionic or nonionic properties or mixtures of these surface-active substances.
  • Examples thereof are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of the compounds containing sulphates, sulphonates and phosphates, eg Alkylarylpoly- glycol ether, alkyl sulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignin Sulf ⁇ tablaugen and methylcellulose.
  • the presence of a surfactant is necessary when one of the active ingredients
  • Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and trace nutrients, may be used. how salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • additives may be fragrances, mineral or vegetable unbranched or modified oils, waxes and nutrients (also micronutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present.
  • additional components e.g. protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration enhancers, stabilizers, sequestering agents, complexing agents.
  • the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes.
  • the formulations generally contain from 0.05 to 99 wt .-%, 0.01 and 98 wt .-%, preferably between 0.1 and 95 wt .-%, particularly preferably between 0.5 and 90% active ingredient, completely more preferably between 10 and 70 weight percent.
  • formulations described above can be used in a method according to the invention for controlling unwanted microorganisms, in which the diaminopyrimidines according to the invention are applied to the microorganisms and / or their habitat.
  • the active compounds according to the invention can also be used in admixture with known fungicides, bactericides, acaricides, nematicides or insecticides, so as to obtain e.g. to broaden the spectrum of action or to prevent development of resistance.
  • Suitable mixing partners are, for example, known fungicides, insecticides, acaricides, nematicides or bactericides (see also Pesticide Manual, 13th ed.) In question.
  • the application is done in a custom forms adapted to the application.
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules.
  • the application is done in the usual way, e.g. by pouring, spraying, spraying, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient itself into the soil. It can also be the seed of the plants to be treated.
  • the application rates can be varied within a relatively wide range, depending on the mode of administration.
  • the application rate of the active compounds according to the invention is
  • Leaves from 0.1 to 10,000 g / ha, preferably from 10 to 1,000 g / ha, more preferably from 50 to 300 g / ha (when used by pouring or drop, the application rate can even be reduced, especially if inert substrates such as rockwool or perlite are used);
  • seed treatment from 2 to 200 g per 100 kg of seed, preferably from 3 to 150 g per 100 kg of seed, more preferably from 2.5 to 25 g per 100 kg of seed, most preferably from 2.5 to 12, 5 g per 100 kg of seed;
  • the compounds according to the invention can be used to protect against fouling of objects, in particular hulls, sieves, nets, structures, quay systems and signal systems, which come into contact with seawater or brackish water.
  • the compounds according to the invention can be used alone or in combinations with other active substances as antifouling agents.
  • the treatment method of the invention may be used for the treatment of genetically modified organisms (GMOs), e.g. As plants or seeds are used.
  • GMOs genetically modified organisms
  • Genetically modified plants are plants in which a heterologous gene has been stably integrated into the genome.
  • heterologous gene essentially means a A gene which is provided or assembled outside the plant and which, when introduced into the nuclear genome, the chloroplast genome or the hypochondriacoma genome of the transformed plant, imparts new or improved agronomic or other properties by expressing a protein or polypeptide of interest or another gene present in the plant or down-regulating or shutting down other genes present in the plant (for example by means of antisense technology, cosuppression technology or RNAi technology [RNA Interference]).
  • a heterologous gene present in the genome is also referred to as a transgene.
  • a transgene defined by its specific presence in the plant genome is referred to as a transformation or transgenic event.
  • the treatment according to the invention can also lead to over-additive (“synergistic”) effects.
  • over-additive additive
  • the following effects are possible, which go beyond the expected effects: reduced application rates and / or extended spectrum of activity and / or increased efficacy of the active ingredients and compositions that can be used erf ⁇ ndungsdorf, better plant growth, increased tolerance to high or low Temperatures, increased tolerance to drought or water or soil salinity, increased flowering, harvest relief, ripening, higher yields, larger fruits, greater plant height, intense green color of the leaf, earlier flowering, higher quality and / or higher nutritional value of the harvested products, higher sugar concentration in the fruits, better storage and / or processability of the harvested products.
  • phytopathogenic fungi, bacteria and viruses are understood to be undesirable phytopathogenic fungi and / or microorganisms and / or viruses.
  • the substances according to the invention can therefore be employed for the protection of plants against attack by the mentioned pathogens within a certain period of time after the treatment.
  • the period of time over which a protective effect is achieved generally extends from 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active substances.
  • Plants and plant varieties which are preferably treated according to the invention include all plants which have genetic material which gives these plants particularly advantageous, useful features (regardless of whether this was achieved by breeding and / or biotechnology).
  • Plants and plant varieties which are also preferably treated according to the invention are resistant to one or more biotic stress factors, ie these plants have an improved defense against animal and microbial pests such as nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and / or viroids .
  • Plants and plant varieties which can also be treated according to the invention are those plants which are resistant to one or more abiotic stress factors.
  • Abiotic stress conditions may include, for example, drought, cold and heat conditions, osmotic stress, waterlogging, increased soil salinity, increased exposure to minerals, ozone conditions, high light conditions, limited availability of nitrogen nutrients, limited availability of phosphorous nutrients, or avoidance of shade.
  • Plants and plant varieties which can also be treated according to the invention are those plants which are characterized by increased yield properties.
  • An increased yield can in these plants z. B. based on improved plant physiology, improved plant growth and improved plant development, such as water efficiency, water retention efficiency, improved nitrogen utilization, increased carbon assimilation, improved photosynthesis, increased germination and accelerated Abreife.
  • the yield may be further influenced by improved plant architecture (under stress and non-stress conditions), including early flowering, flowering control for hybrid seed production, seedling vigor, plant size, internode count and spacing, root growth, seed size, fruit size, Pod size, pod or ear number, number of seeds per pod or ear, seed mass, increased seed filling, reduced seed drop, reduced pod popping and stability.
  • Other yield-related traits include seed composition such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction of nontoxic compounds, improved processability, and improved shelf life.
  • Plants which can be treated according to the invention are hybrid plants which already express the properties of heterosis or hybrid effect, which generally leads to higher yield, higher vigor, better health and better resistance to biotic and abiotic stress factors.
  • Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossbred partner).
  • the hybrid seed is typically harvested from the male sterile plants and sold to propagators.
  • Pollen sterile plants can sometimes be produced (eg in maize) by delaving (ie mechanical removal of the male reproductive organs or the male flowers); however, it is more common for male sterility to be due to genetic determinants in the plant genome.
  • a ribonuclease such as a barnase is selectively expressed in the tapetum cells in the stamens.
  • the fertility can then be restorated by expression of a ribonuclease inhibitor such as barstar in the tapetum cells.
  • Plants or plant cultivars obtained by plant biotechnology methods such as genetic engineering) which can be treated according to the invention are herbicide-tolerant plants, d. H. Plants tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation or by selection of plants containing a mutation conferring such herbicide tolerance.
  • Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, i. H. Plants tolerant to the herbicide glyphosate or its salts.
  • glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS).
  • EPSPS 5-enolpyruvylshikimate-3-phosphate synthase
  • EPSPS 5-enolpyruvylshikimate-3-phosphate synthase
  • EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium, the CP4 gene of the bacterium Agrobacterium sp., The genes for a EPSPS from the petunia, for a EPSPS from the tomato or for a Encoding EPSPS from Eleusine.
  • Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate oxidoreductase enzyme. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme. Glyphosate-tolerant plants can also be obtained by selecting plants which select for naturally occurring mutations of the above mentioned genes.
  • herbicide-resistant plants are, for example, plants which have been tolerated to herbicides which inhibit the enzyme glutamine synthase, such as bialaphos, phosphinotricin or glufosinate.
  • Such plants can be obtained by expressing an enzyme which detoxifies the herbicide or a mutant of the enzyme glutamine synthase, which is resistant to inhibition.
  • an effective detoxifying enzyme is, for example, an enzyme encoding a phosphinotricin acetyltransferase (such as the bar or pat Protein from Streptomyces species). Plants expressing an exogenous phosphinotricin acetyltransferase have been described.
  • hydroxyphenylpyruvate dioxygenase HPPD
  • the hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogentisate.
  • Plants tolerant to HPPD inhibitors can be transformed with a gene encoding a naturally occurring resistant HPPD enzyme or a gene encoding a mutant HPPD enzyme.
  • Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding certain enzymes that allow the formation of homogentisate despite inhibition of the native HPPD enzyme by the HPPD inhibitor.
  • the tolerance of plants to HPPD inhibitors can also be improved by transforming plants with a gene coding for a prephenate dehydrogenase enzyme in addition to a gene coding for an HPPD-tolerant enzyme.
  • ALS inhibitors include sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides.
  • ALS also known as acetohydroxy acid synthase, AHAS
  • AHAS acetohydroxy acid synthase
  • plants tolerant to imidazolinone and / or sulfonylurea can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutation breeding.
  • Plants or plant varieties obtained by plant biotechnology methods such as genetic engineering which can also be treated according to the invention are insect-resistant transgenic plants, ie plants which have been made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such insect resistance.
  • insect-resistant transgenic plant as used herein includes any plant containing at least one transgene comprising a coding sequence encoding:
  • an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal part thereof such as the insecticidal crystal proteins described online at: http://www.lifesci.sussex.ac.uk/Home/Neil Crickmore / Bt /, or insecticidal parts thereof, eg Proteins of the cry protein classes CrylAb, CrylAc, CrylF, Cry2Ab, Cry3Ae or Cry3Bb or insecticidal parts thereof; or
  • a Bacillus thuringiensis crystal protein or a part thereof which is insecticidal in the presence of a second crystal protein other than Bacillus thuringiensis or a part thereof, such as the binary toxin consisting of the crystal proteins Cy34 and Cy35; or
  • an insecticidal hybrid protein comprising parts of two different insecticidal crystal proteins from Bacillus thuringiensis, such as a hybrid of the
  • Proteins of 1) above or a hybrid of the proteins of 2) above e.g.
  • an insecticidal secreted protein from Bacillus thuringiensis or Bacillus cereus or an insecticidal part thereof, such as the vegetative insecticidal proteins (VEP) available at http://www.lifesci.sussex.ac.uk/home/ Neil_Crickmore / Bt / vip.html are cited, e.g. B. Proteins of protein class VEP3Aa; or
  • a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus, such as the binary toxin consisting of the proteins VEPlA and VEP2A.
  • a hybrid insecticidal protein comprising parts of various secreted proteins of Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins of 1) or a hybrid of the proteins of 2) above; or
  • insect-resistant transgenic plants in the present context also include any plant comprising a combination of genes encoding the proteins of any of the above classes 1 to 8.
  • an insect-resistant plant contains more than one transgene encoding a protein of any one of the above 1 to 8 in order to extend the spectrum of the corresponding target insect species or to delay the development of resistance of the insects to the plants by use different proteins which are insecticidal for the same target insect species, but have a different mode of action, such as binding to different receptor binding sites in the insect.
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are tolerant of abiotic stressors. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such stress resistance. Particularly useful plants with stress tolerance include the following:
  • PARP poly (ADP-ribose) polymerase
  • Plants which contain a stress tolerance-enhancing transgene encoding a plant-functional enzyme of the nicotinamide adenine dinucleotide salvage biosynthetic pathway including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic acid mono- Nucleotide adenyltransferase, nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyltransferase.
  • Plants or plant varieties obtained by plant biotechnology methods such as genetic engineering which can also be treated according to the invention have a changed amount, quality and / or storability of the harvested product and / or altered characteristics of certain components of the harvested product, such as:
  • Transgenic plants that synthesize a modified starch, with respect to their physicochemical properties, in particular the amylose content or the amylose / amylopectin ratio, the degree of branching, the average chain length, the distribution of side chains, the viscosity behavior, the gel strength, the starch grain size and / or starch grain morphology is altered in comparison to the synthesized starch in wild-type plant cells or plants, so that this modified starch is better suited for certain applications.
  • physicochemical properties in particular the amylose content or the amylose / amylopectin ratio, the degree of branching, the average chain length, the distribution of side chains, the viscosity behavior, the gel strength, the starch grain size and / or starch grain morphology is altered in comparison to the synthesized starch in wild-type plant cells or plants, so that this modified starch is better suited for certain applications.
  • Transgenic plants that synthesize non-starch carbohydrate polymers or non-starch carbohydrate polymers whose properties are altered compared to wild-type plants without genetic modification. Examples are plants that produce polyfructose, particularly of the inulin and levan type, plants that produce alpha-1,4-glucans, plants that produce alpha-1,6-branched alpha-1,4-glucans, and plants that produce Produce alternan.
  • Plants or plant varieties obtained by plant biotechnology methods such as genetic engineering, which can also be treated according to the invention, are plants such as cotton plants with altered fiber properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered fiber properties; these include:
  • plants such as cotton plants containing an altered form of cellulose synthase genes
  • plants such as cotton plants, containing an altered form of rsw2 or rsw3 homologous nucleic acids
  • plants such as cotton plants having increased expression of sucrose phosphate synthase
  • plants such as cotton plants with increased expression of sucrose synthase
  • plants such as cotton plants with modified reactivity fibers, e.g. B. by
  • N-acetylglucosamine transferase gene including nodC, and chitin synthase genes.
  • Plants or plant varieties obtained by plant biotechnology methods such as genetic engineering which can also be treated according to the invention are plants such as oilseed rape or related Brassica plants with altered oil composition properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered oil properties; these include:
  • plants such as oilseed rape plants, which produce oil of high oleic acid content
  • plants such as oilseed rape plants, which produce oil with a low linolenic acid content.
  • plants such as rape plants that produce oil with a low saturated fatty acid content.
  • transgenic plants which can be treated according to the invention are plants with one or more genes coding for one or more toxins, the transgenic plants offered under the following commercial names: YIELD GARD® (for example maize, cotton, Soybeans), KnockOut® (for example corn), BiteGard® (for example maize), BT-Xtra® (for example corn), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (for example corn), Protecta® and NewLeaf® (potato).
  • YIELD GARD® for example maize, cotton, Soybeans
  • KnockOut® for example corn
  • BiteGard® for example maize
  • BT-Xtra® for example corn
  • StarLink® for example maize
  • Bollgard® cotton
  • Nucotn® cotton
  • Nucotn 33B® cotton
  • NatureGard® for example corn
  • Protecta® and NewLeaf® pot
  • Herbicide-tolerant crops to be mentioned are, for example, corn, cotton and soybean varieties sold under the following tradenames: Roundup Ready® (glyphosate tolerance, for example corn, cotton, soybean), Liberty Link® (phosphinotricin tolerance, for example rapeseed) , IMI® (imidazolinone tolerance) and SCS® (sylphonylurea tolerance), for example corn.
  • Herbicide-resistant plants (plants traditionally grown for herbicide tolerance) to be mentioned include the varieties sold under the name Clearfield® (for example corn).
  • transgenic plants that can be treated according to the invention are plants that contain transformation events, or a combination of transformation events, and that are listed, for example, in the files of various national or regional authorities (see, for example, http: // /gmoinfo.jrc.it/gmp browse.aspx and http://www.agbios.com/dbase.php).
  • the listed plants can be treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active substance mixtures according to the invention.
  • the preferred ranges given above for the active compounds or mixtures also apply to the treatment of these plants. Particularly emphasized is the treatment of plants with the compounds or mixtures specifically mentioned in the present text.
  • the active compounds or compositions according to the invention can therefore be used to protect plants within a certain period of time after the treatment against attack by the mentioned pathogens.
  • the period of time within which protection is afforded generally ranges from 1 to 28 days, preferably from 1 to 14 days, more preferably from 1 to 10 days, most preferably from 1 to 7 days after treatment of the plants with the active ingredients or up to 200 days after seed treatment.
  • V-7 2,5-dichloro-N-cyclopropylpyrimidin-4-amine (V-7) (logP (pH 2.3): 1.79);
  • V-32 4- (2,5-dichloropyrimidin-4-yl) thiomorpholine (V-32) (logP (pH 2.3): 2.84);
  • reaction solution is poured into 500 ml of ice water with 50 ml of dilute hydrochloric acid and the mixture is stirred for 30 minutes.
  • the precipitate is then filtered off, washed three times thoroughly with 300 ml of water and stirred with 50 ml of tert-butyl methyl ether.
  • the solid is filtered off with suction again and stirred with 80 ml of water.
  • the mixture is neutralized with saturated NaHCO3 solution, stirred for one hour at 20 0 C and the solid was filtered off. Finally, this solid is stirred with 80 ml of isopropanol and again filtered off with suction. This gives 2.1 g of the desired product (logP (pH 7): 2.54).

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EP09778015A 2008-09-03 2009-08-21 Heterozyklisch substituierte anilinopyrimidine als fungizide Withdrawn EP2331524A1 (de)

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PT2576541T (pt) 2010-06-04 2016-07-08 Hoffmann La Roche Derivados de aminopirimidina como moduladores de lrrk2
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ES2812605T3 (es) 2013-12-20 2021-03-17 Signal Pharm Llc Compuestos de diaminopirimidilo sustituidos, composiciones de los mismos y procedimientos de tratamiento con ellos
US10710983B2 (en) 2016-06-27 2020-07-14 Rigel Pharmaceuticals, Inc. 2,4-diamino-pyrimidine compounds and method for making and using the compounds
CN113200989B (zh) * 2021-05-18 2022-06-21 云南民族大学 一种色酮生物碱类化合物的制备方法及其应用
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ES2314106T3 (es) * 2001-10-17 2009-03-16 BOEHRINGER INGELHEIM PHARMA GMBH & CO.KG Derivados de pirimidina, agentes farmaceuticos que contiene dichos compuestos, uso y metodo para su obtencion.
WO2004048343A1 (en) * 2002-11-28 2004-06-10 Schering Aktiengesellschaft Chk-, pdk- and akt-inhibitory pyrimidines, their production and use as pharmaceutical agents
DE102007010801A1 (de) * 2007-03-02 2008-09-04 Bayer Cropscience Ag Diaminopyrimidine als Fungizide
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US20110245242A1 (en) 2011-10-06
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