EP0687262A1 - Pyrimidin-derivate als pestizide - Google Patents

Pyrimidin-derivate als pestizide

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Publication number
EP0687262A1
EP0687262A1 EP94908333A EP94908333A EP0687262A1 EP 0687262 A1 EP0687262 A1 EP 0687262A1 EP 94908333 A EP94908333 A EP 94908333A EP 94908333 A EP94908333 A EP 94908333A EP 0687262 A1 EP0687262 A1 EP 0687262A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
hydrogen
halogen
cyano
unsubstituted
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.)
Ceased
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EP94908333A
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English (en)
French (fr)
Inventor
Harald Walter
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
Novartis AG
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Publication date
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Publication of EP0687262A1 publication Critical patent/EP0687262A1/de
Ceased legal-status Critical Current

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    • 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
    • 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
    • A01N43/62—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms three- or four-membered rings or rings with more than six members
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • 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
    • C07D401/14—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 three or more hetero rings
    • 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
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • 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
    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

Definitions

  • the invention relates to novel pesticidally active compounds of the formula I
  • Rj is hydrogen, C 1 -C alkyl, C r C 4 alkoxy, halo-C 1 -C 4 alkyl having 1, 2 or 3 halogen atoms or C 1 -C 4 alkylthio;
  • R and R 3 independently of one another are hydrogen, C 1 -C alkyl, halo-C 1 -C 4 alkyl having 1, 2 or 3 halogen atoms, C 1 -C 2 alkoxy-C 1 -C 4 alkyl, nitro-C 1 -C alkyl, cyano-C r C 4 alkyl, C 1 -C 4 alkanoyl-C 1 -C alkyl, C 1 -C 4 alkoxycarbonyl-C 1 -C 4 alkyl, C 1 -C 2 alkylthio-C 1 -C 4 alkyl, C 1 -C 2 alkanesulfinyl-C 1 -C 4 alkyl, C 1 -C 2 alkanesulfonyl-C 1 -C alkyl, C 2 -C 4 alkenyl, halo- C 2 -C 4 alkenyl having 1, 2 or 3 halogen atoms, C 2 -C 4 alkyny
  • R 5 and R 6 independently of one another are hydrogen, C]-C alkyl, halo-C 1 -C alkyl having 1, 2 or 3 halogen atoms, C r C 2 alkoxy-C r C 4 alkyl, nitro-C 1 -C 4 alkyl, C 1 -C 4 alkoxycarbonyl-C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl, which is unsubstituted or substituted by one or two substituents chosen from the group comprising halogen and C r C 2 alkyl;
  • R 7 , R 8 and R independently of one another are hydrogen, halogen, C r C 4 alkyl, halo-C 1 -C 4 alkyl having 1, 2 or 3 halogen atoms, C 1 -C 2 alkoxy-C 1 -C 4 alkyl,
  • X is OR 10 , SR 10 or N(R ⁇ )R 12 ;
  • Y is a group -CH(R 13 )-, oxygen, sulfur or a group -N(R 14 )-;
  • R 10 is hydrogen, an unsubstituted or substituted, open-chain, saturated or unsaturated hydrocarbon radical containing up to 12 carbon atoms, an unsubstituted or substituted cyclic saturated or unsaturated hydrocarbon radical containing up to 10 carbon atoms or unsubstituted or substituted benzyl; or an unsubstituted or substituted heterocyclyl radical;
  • R n is hydrogen, an open-chain saturated or unsaturated hydrocarbon radical which contains up to 8 carbon atoms and is unsubstituted or substituted by 1-5 halogen atoms,
  • C r C 4 alkoxycarbonyl a cyclic saturated or unsaturated hydrocarbon radical containing up to 10 carbon atoms or benzyl, in which the carbocyclic radical is unsubstituted or mono- to disubstituted by halogen, C j -C ⁇ alkyl, halomethyl, nitro or cyano, or heterocyclyl, which is unsubstituted or mono- to trisubstituted by identical or different substituents from the group comprising C j -C 2 alkyl, halogen, halomethyl, nitro and cyano;
  • R 12 is hydrogen or C 1 -C 4 alkyl
  • R ⁇ and R 12 together with the nitrogen atom to which they are bonded, are a heterocyclic radical which is unsubstituted or mono- to trisubstituted by identical or different substituents from the group comprising halogen, C r C 2 alkyl, halomethyl and nitro;
  • R 13 is hydrogen or C C 4 alkyl
  • Rj 4 is hydrogen, C r C 4 alkyl, C j -C 4 alkanoyl, benzoyl, the phenyl group of which is unsubstituted or substituted by one, two or three substituents chosen from the group comprising halogen, C
  • the invention furthermore relates to the preparation of these compounds, agrochemical compositions which comprise at least one of these compounds as the active compound, and the use of the active compounds or compositions for pest control, in particular as microbicides in agriculture and in horticulture.
  • the compounds I and, where appropriate, their tautomers can be in the form of salts. Since the compounds I have at least one basic centre, they can form, for example, acid addition salts. These are formed, for example, with mineral acids, for example sulfuric acid, a phosphoric acid or a hydrogen halide, with organic carboxylic acids, for example acetic acid or oxalic, malonic, maleic, fumaric or phthalic acid, with hydroxycarboxylic acids, for example ascorbic, lactic, malic, tartaric or citric acid, or with benzoic acid, or with organic sulfonic acids, for example methane- or p-toluenesulfonic acid.
  • mineral acids for example sulfuric acid, a phosphoric acid or a hydrogen halide
  • organic carboxylic acids for example acetic acid or oxalic, malonic, maleic, fumaric or phthalic acid
  • hydroxycarboxylic acids for example ascorbic, lactic, mal
  • Suitable salts with bases are, for example, metal salts, such as alkali metal or alkaline earth metal salts, for example sodium salts, potassium salts or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower alkylamine, for example ethyl-, diethyl-, triethyl- or dimethyl-propyl-amine, or a mono-, di- or trihydroxy-lower alkylamine, for example mono-, di- or triethanolamine.
  • Corresponding internal salts furthermore may be formed, where appropriate. Agrochemically advantageous salts are preferred in the context of the invention.
  • Alkyl groups are straight-chain or branched, depending on the number of carbon atoms, and are, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec -butyl, iso-butyl, tert-butyl, sec-amyl, tert-amyl, 1-hexyl or 3-hexyl.
  • Alkenyl is to be understood as meaning straight-chain or branched alkenyl, for example allyl, methallyl, 1-methylvinyl or but-2-en-l-yl. Alkenyl radicals having a chain length of 3 to 4 carbon atoms are preferred.
  • Alkynyl can likewise be straight-chain or branched, depending on the number of carbon atoms, for example propargyl, but-1-yn-l-yl and but-l-yn-3-yl. Propargyl is preferred.
  • Unsaturated hydrocarbon radicals are alkenyl, alkynyl or alkenynyl groups having not more than 3 multiple bonds, for example butadienyl, hexatrienyl or 2-penten-4-ynyl.
  • Halogen and halo are fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine.
  • Haloalkyl can contain identical or different halogen atoms, and examples would be fluoromethyl, difluoromethyl, difluorochloromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2,2,2-trichloroethyl and 3,3,3-trifluoropropyl.
  • Alkoxy is, for example, methoxy, ethoxy, propyloxy, i-propyloxy, n-butyloxy, iso-butyl- oxy, sec-butyloxy and tert-butyloxy; preferably methoxy and ethoxy.
  • Haloalkoxy is, for example, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy and 2,2-difluoroethoxy.
  • Cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, depending on the ring size.
  • Cyclic unsaturated hydrocarbon radicals can be aromatic, for example phenyl and naphthyl, or non-aromatic, for example cyclopentenyl, cyclohexenyl, cycloheptenyl and cyclooctadienyl, or partly aromatic, for example tetrahydronaphthyl and indanyl.
  • Alkanoyl is either straight-chain or branched, in each case taking into account the number of carbon atoms it contains from case to case, and examples would be formyl, acetyl, propionyl, butyryl, pivaloyl or octanoyl.
  • alkoxy-, alkylthio-, alkanesulfinyl-, alkanesulfonyl-, nitro- or cyano-substituted carbon-containing groups and compounds such as alkoxyalkyl, alkylthioalkyl, alkanesulfinylalkyl, alkanesulfonylalkyl, nitroalkyl, cyanoalkyl and cyanoalkanesulfonyl, one of the hydrogen atoms present in the unsubstituted basic structure on which they are based is replaced by alkoxy, alkylthio, alkanesulfinyl, alkanesulfonyl, nitro or, respectively, cyano.
  • a heterocyclyl radical is understood as meaning a 5- or 6-membered aromatic or non-aromatic ring having the hetero atoms N, O and/or S.
  • An unsubstituted or substituted benzo group furthermore can be fused onto such a heterocyclyl radical bonded to the remainder of the molecule.
  • heterocyclyl groups are pyridyl, pyrimidinyl, imidazolyl, thiazolyl, 1,3,4-thiadiazolyl, triazolyl, thienyl, furanyl, pyrrolyl, morpholinyl, oxazolyl and the corresponding partly or totally hydrogenated rings.
  • heterocyclyl groups with a fused-on benzo group examples include quinolyl, isoquinolyl, benzoxazolyl, quinoxalinyl, benzothiazolyl, benzimidazolyl, indolyl, indolinyl.
  • R 1( ) is an open-chain saturated or unsaturated hydrocarbon radical which contains up to 8 carbon atoms and is unsubstituted or substituted by 1-5 halogen atoms, C ⁇ -C 2 alkoxy, hydroxyl, nitro, cyano, C j - alkanoyl, halo-C r C 4 alkanoyl or C j - alkoxycarbonyl, a cyclic saturated or unsaturated hydrocarbon radical containing up to 10 carbon atoms or benzyl, in which the carbocyclic radical is unsubstituted or mono- to disubstituted by halogen, halomethyl, nitro or cyano, or heterocyclyl, which is unsubstituted or mono- to trisubstituted by identical or different substituents from the group comprising halogen, C r C 2 alkyl, halomethyl, nitro and cyano, or a 5- to 7-membered lactone ring; and in
  • RJ O is hydrogen, an open-chain saturated or unsaturated hydrocarbon radical which contains up to 12 carbon atoms and is unsubstituted or substituted by tri-(C 1 -C alkyl)-silyl or an epoxy group; or the group
  • U is hydrogen, C ] -C alkyl, cyano, or C r C 6 alkoxycarbonyl
  • W is C r C 6 alkoxy, C 3 -C 6 cycloalkoxy, or the group -N(T ⁇ )T 2 ; m is 0, 1 or 2 and
  • T j and T 2 independently of one another are hydrogen, C r C 6 alkyl, which is unsubstituted or substituted by 1-3 halogen atoms, C j -C 2 alkoxy, hydroxyl, nitro, cyano, C C 4 alkanoyl, halo-C r C 4 alkanoyl or C ] -C 4 alkoxycarbonyl, C r C 6 alkenyl which is unsubstituted or substituted by 1-3 halogen atoms, C r C 6 alkynyl which is unsubstituted or substituted by
  • halogen atoms a cyclic saturated or unsaturated hydrocarbon radical containing up to
  • R 10 is hydrogen, an open-chain saturated or unsaturated hydrocarbon radical containing up to 6 carbon atoms, which is unsubstituted or substituted by tri-(C j -C 4 alkyl)-silyl or an epoxy group; or the group
  • W is Cj-C 6 alkoxy, C 3 -C 6 cycloalkoxy or the group -N(T j )T 2 ;
  • Tj and T 2 independently of one another are hydrogen, C ⁇ -C 6 alkyl, halo-C 1 -C 6 alkyl having
  • halogen atoms C 3 -C 6 cycloalkyl, phenyl, halophenyl having 1-3 halogen atoms, pyridyl or naphthyl, or
  • Tj and T 2 together with the nitrogen atom to which they are bonded, are piperidine, piperazine, morpholine or 2,6-dimethylmorpholine.
  • R ] is hydrogen, C r C 4 alkyl, C C 4 alkoxy, halo-C]-C 4 alkyl having 1, 2 or 3 halogen atoms or C r C 4 alkylthio;
  • R 2 and R 3 independently of one another are hydrogen, Cj-Qalkyl, halo-C C 4 alkyl having 1, 2 or 3 halogen atoms, C ] -C alkoxy-C C 4 alkyl, nitro-Cj-C alkyl, cyano-Cj-C 4 alkyl, C r C 4 alkanoyl-C r C 4 alkyl, C r C 4 alkoxycarbonyl-C r C 4 alkyl, C 1 -C 2 alkylthio-C 1 -C 4 alkyl, C 1 -C 2 alkanesulf ⁇ nyl-C 1 -C 4 alkyl, C r C 2 alkanesulfonyl-C r C 4 alkyl, C 2 -C 4 alkenyl, halo- C 2 -C 4 alkenyl having 1, 2 or 3 halogen atoms, C 2 -C 4 alkynyl, C 3 -C 7 cycl
  • R 5 and R 6 independently of one another are hydrogen, C ⁇ -C 4 alkyl, halo-C 1 -C 4 alkyl having 1, 2 or 3 halogen atoms, C 1 -C 2 alkoxy-C 1 -C 4 alkyl, nitro-C r C 4 alkyl, cyano-C 1 -C 4 alkyl, C r C 4 alkoxycarbonyl-C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl, which is unsubstituted or substituted by one or two substituents chosen from the group comprising halogen and
  • R , Rg and R9 independently of one another are hydrogen, halogen, C j -Qalkyl, halo-C ⁇ -C 4 alkyl having 1, 2 or 3 halogen atoms, C 1 -C 2 alkoxy-C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C r C 4 alkoxy, halo-C r C 4 alkoxy with 1, 2 or 3 halogen atoms, C 3 -C 7 cycloalkoxy, C r C 4 alkylthio, halo-C C 4 alkylthio having 1, 2 or 3 halogen atoms, cyano, nitro, phenyl, phenoxy and phenylthio, the phenyl groups in phenyl, phenoxy and phenylthio being unsubstituted or substituted by one, two or three substituents chosen from the group comprising halogen, C !
  • R 7 , Rg or R 9 is unsubstituted or substituted phenyl, substituted phenoxy or substituted phenylthio;
  • X is OR 10 , SR 10 or N(R n )R 12 ;
  • Y is a group -CH(R 13 )-, oxygen, sulfur or a group -N(R ⁇ 4 )-;
  • R 10 is C j -Cgalkyl, halo-C j -Cg-alkyl having 1 to 5 halogen atoms, C C 2 alkoxy- C r Cgalkyl, hydroxy-C j -Cgalkyl, nitro-C j -Cgalkyl, cyano-Cj-Cgalkyl, ⁇ alkanoyl- C r C 8 alkyl, halo-C 1 -C 4 alkanoyl-C 1 -C 8 alkyl, C 1 -C 4 alkoxycarbonyl-C 1 -C 8 alkyl, C 3 -C 5 cycloalkyl, benzyl, phenyl, which is unsubstituted or mono- to disubstituted by halogen, C ⁇ -C 2 alkyl, halomethyl,
  • R ⁇ and R 12 together with the nitrogen atom to which they are bonded are a heterocyclic radical, which is unsubstituted or mono- to trisubstituted by identical or different substituents from the group comprising halogen, C ⁇ -C 2 alkyl, halomethyl and nitro;
  • R 13 is hydrogen or C r C 4 alkyl
  • R 14 is hydrogen, Cj-C 4 alkyl, - alkanoyl, benzoyl, the phenyl group of which is unsubstituted or substituted by one, two or three substituents chosen from the group comprising halogen, C C alkyl, nitro and cyano, Cj- alkylsulfonyl or aminosulfonyl, the nitrogen atom of which is unsubstituted or mono- or disubstituted by C 1 -C alkyl; n is 1 or 2; or, where appropriate, a tautomer thereof, in each case in the free form or in salt form.
  • Rj is hydrogen or C 1 -C 4 alkyl
  • R 2 and R 3 independently of one another are hydrogen, C C alkyl, halo-C j - -alkyl having 1, 2 or 3 halogen atoms, C 1 -C 2 alkoxy-C 1 -C 4 alkyl, C 2 -C 4 alkynyl, C 3 -C 5 cycloalkyl, hydroxyl or halogen;
  • R 4 is hydrogen, C ⁇ -C 4 alkyl, C 3 -C 5 cycloalkyl or benzyl;
  • R 5 and R 6 independentiy of one another are hydrogen, C r C 4 alkyl, halo-C r C alkyl having
  • R 7 , R 8 and R 9 independently of one another are hydrogen, halogen or C r C 4 alkyl
  • X is OR 10 , SR 10 or N(R 11 )R 12 ;
  • Y is a group -CH(R ⁇ 3 )-, oxygen, sulfur or a group -N(R 14 )-;
  • RJO is Cj-C 4 alkyl, halo-C ⁇ -C 4 -alkyl having 1, 2 or 3 halogen atoms, Ci-C ⁇ alkoxy- hydroxy-C j -C alkyl, nitro-C ⁇ -C 4 alkyl, cyano-C r C alkyl, C r C 4 alkanoyl-
  • C r C 4 alkyl C 1 -C 4 alkoxycarbonyl-C ⁇ -C 4 alkyl, C 3 -C 5 cycloalkyl, benzyl, phenyl, which is unsubstituted or mono- to disubstituted by halogen, Cj- alkyl, halomethyl, nitro or cyano, heterocyclyl, which is unsubstituted or mono- to trisubstituted by identical or different substituents from the group comprising halogen, halomethyl, nitro and cyano, or a 5- to 7-membered lactone ring;
  • R n is hydrogen, C r C 4 alkyl, halo- ⁇ -alkyl having 1, 2 or 3 halogen atoms,
  • R 12 is hydrogen or - alkyl
  • R j j and R 12 together with the nitrogen atom to which they are bonded, are a heterocyclyl radical, which is unsubstituted or mono- to trisubstituted by identical or different substituents from the group comprising halogen, C]-C 2 alkyl, halomethyl and nitro;
  • R 13 is hydrogen;
  • R 14 is hydrogen, C C 4 alkyl, C ⁇ -C 4 alkanoyl, benzoyl, the phenyl group of which is unsubstituted or substituted by one, two or three substituents chosen from the group comprising halogen, C 1 -C 2 alkyl, nitro and cyano, -C 4 alkylsulfonyl or aminosulfonyl, the nitrogen atom of which is unsubstituted or mono- or disubstituted by C ⁇ Qalkyl; n is 1 or 2;
  • Rj is hydrogen; or C C 4 alkyl
  • R 2 is hydrogen, C r C 4 alkyl, halo-C r C -alkyl having 1, 2 or 3 halogen atoms,
  • R 3 is fluorine or chlorine
  • R 4 is hydrogen or C 1 -C 4 alkyl
  • R 5 is C r C 4 alkyl
  • R 6 is hydrogen
  • R 7 , Rg and Rg independently of one another are hydrogen or halogen
  • Y is a group -CH(R 13 )-, oxygen, sulfur or a group -N(R 14 )-;
  • R ]0 is C 1 -C 4 alkyl, halo-C r C 4 -alkyl having 1, 2 or 3 halogen atoms, C r C 2 alkoxy-
  • R ⁇ is hydrogen, C j ⁇ alkyl, halo-C r C 4 -alkyl having 1, 2 or 3 halogen atoms,
  • R 12 is hydrogen or C C 4 alkyl
  • R n and R 1 together with the nitrogen atom to which they are bonded, are pyrrolidine, piperidine, piperazine, morpholine or 2,6-dimethylmo holine; R 13 is hydrogen;
  • R 14 is hydrogen, Cj-Qalkyl, C ⁇ -C 4 alkanoyl or benzoyl, the phenyl group of which is unsubstituted or substituted by one, two or three substituents chosen from the group comprising halogen, C ⁇ -C 2 alkyl, nitro and cyano; n is 1 or 2.
  • R ! is hydrogen; or C r C 4 alkyl
  • R 2 is hydrogen, C r C alkyl, halo-C 1 -C 4 -alkyl having 1, 2 or 3 halogen atoms,
  • R 3 is chlorine
  • R 4 is hydrogen or C r C 4 alkyl
  • R 5 is C r C 4 alkyl
  • R 6 is hydrogen
  • R 7 , Rg and R 9 independently of one another are hydrogen or halogen
  • X is OR 10 , SR 10 or N(R ⁇ )R 12 ;
  • Y is a group -CH(R 13 )-, oxygen, sulfur or a group -N(R ⁇ 4 )-;
  • R 10 is C 1 -C 4 alkyl, halo-Cj-Q-alkyl having 1, 2 or 3 halogen atoms, C r C 2 alkoxy-
  • C r C 4 alkyl C 1 -C 4 alkoxycarbonyl-C 1 -C 4 alkyl, C 3 -C 5 cycloalkyl, benzyl, phenyl, which is unsubstituted or mono- to disubstituted by halogen, C]-C 2 alkyl, nitro or cyano, pyridine, pyrimidine or triazine, in which these heterocyclic radicals in each case are unsubstituted or mono- to trisubstituted by identical or different substituents from the group comprising halogen, C C 2 alkyl, trifluoromethyl and cyano, or a 5-membered lactone ring;
  • R n is hydrogen, C r C 4 alkyl, halo-C r C -alkyl having 1, 2 or 3 halogen atoms,
  • R 12 is hydrogen or C r C 4 alkyl
  • R n and R 1 together with the nitrogen atom to which they are bonded, are pyrrolidine, piperidine, piperazine, morpholine or 2,6-dimethylmorpholine;
  • R 13 is hydrogen
  • R 14 is hydrogen, C j -Cialkyl, C r C 4 alkanoyl or benzoyl, the phenyl group of which is unsubstituted or substituted by one, two or three substituents chosen from the group comprising halogen, C r C 2 alkyl, nitro and cyano; n is 1 or 2.
  • R 10 is Cj- alkyl, halo-C r C 2 -alkyl having 1, 2 or 3 halogen atoms, C 1 -C 2 alkyl, hydroxy- ⁇ - alkyl, acetyl-C 1 -C 2 alkyl, tert-butyloxycarbonyl-C ⁇ -C 2 alkyl, benzyl, phenyl, which is unsubstituted or mono- to disubstituted by halogen, C j -C ⁇ alkyl, nitro or cyano, pyridine, pyrimidine or triazine, in which these heterocyclic radicals in each case are unsubstituted or mono- to trisubstituted by identical or different substituents from the group comprising halogen, C C 2 alkyl, trifluoromethyl and cyano, or a 5-membered lactone ring.
  • R ⁇ is hydrogen, C 1 -C 4 alkyl, halo- -C ⁇ alkyl having 1, 2 or 3 halogen atoms, nitro-C C 4 alkyl, cyano-C 1 -C 2 alkyl, acetyl-C 1 -C 2 alkyl, tert-butyloxycarbonyl-Ci-C ⁇ alkyl, C 3 -C 5 cycloalkyl, benzyl or phenyl, which is unsubstituted or mono- to disubstituted by halogen, C ⁇ -C 2 alkyl, nitro or cyano, R 12 is hydrogen or C ⁇ -C alkyl; or
  • R ⁇ and R 12 together with the nitrogen atom to which they are bonded, are pyrrolidine, piperidine, piperazine, morpholine or 2,6-dimethylmorpholine.
  • R 2 is hydrogen, methyl or ethyl
  • R 3 is fluorine or chlorine
  • R 5 is methyl or ethyl
  • R 8 and R 9 independently of one another are hydrogen or fluorine
  • R 10 is methyl, ethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, cyanomethyl, tert-butyloxycarbonylmethyl, allyl, 2-propynyl, cyclohexyl, cyclohexenyl, pyridine, pyrimidine or triazine, in which these heterocyclic radicals in each case are unsubstituted or mono- to trisubstituted by identical or different substituents from the group comprising halogen, -C ⁇ alkyl, trifluoromethyl and cyano;
  • R ⁇ is hydrogen, C C 4 alkyl, halo- ⁇ -alkyl having 1, 2 or 3 halogen atoms, hydroxy-
  • R 12 is hydrogen
  • R n and R 12 together with the nitrogen atom to which they are bonded, are pyrrolidine, piperidine, piperazine, morpholine or 2,6-dimethylmorpholine.
  • R is hydrogen, methyl or ethyl
  • R 3 is fluorine or chlorine
  • R 5 is methyl or ethyl
  • R 8 and R 9 independendy of one another are hydrogen or fluorine
  • X is OR 10 , SR 10 or N(R n )R ⁇ 2 ;
  • R JO is methyl, ethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, cyanomethyl,tert-butyloxycarbonylmethyl, allyl, 2-propynyl, cyclohexyl, cyclohexenyl, pyridine, pyrimidine or triazine, in which these heterocyclic compounds in each case are unsubstituted or mono- to trisubstituted by identical or different substituents from the group comprising halogen, C j -C 2 alkyl, trifluoromethyl and cyano;
  • R n is hydrogen, C r C alkyl, halo-C 1 -C 4 -alkyl having 1, 2 or 3 halogen atoms, hydroxy-
  • C r C 4 alkyl cyano-C r C 4 alkyl, allyl, 2-propynyl, cyclohexyl, cyclohexenyl, cyclopropyl, benzyl or phenyl;
  • R 12 is hydrogen; or R JJ and R 12 , together with the nitrogen atom to which they are bonded, are pyrrolidine, piperidine, piperazine, morpholine or 2,6-dimethylmorpholine.
  • R 2 is hydrogen, methyl or ethyl
  • R 3 is fluorine or chlorine
  • R 5 is methyl or ethyl
  • R 8 and R independently of one another are hydrogen or fluorine
  • X is OR 10 , SR 10 or N(R n )R 12 ;
  • Rio is methyl, ethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, cyanomethyl.tert-butyloxycarbonylmethyl, allyl, 2-propynyl, cyclohexyl, cyclohexenyl, pyridine, pyrimidine or triazine, in which these heterocyclic radicals in each case are unsubstituted or mono- to trisubstituted by identical or different substituents from the group comprising halogen, C r C 2 alkyl, trifluoromethyl and cyano;
  • R ⁇ is hydrogen, C r C 4 alkyl, halo-C r C 4 -alkyl having 1, 2 or 3 halogen atoms, hydroxy-
  • R J2 is hydrogen
  • Rn and R 12 together with the nitrogen atom to which they are bonded, are pyrrolidine, piperidine, piperazine, morpholine or 2,6-dimethylmorpholine.
  • R 2 is hydrogen, methyl or ethyl
  • R 3 is fluorine or chlorine
  • R 5 is methyl or ethyl
  • R 8 and R 9 independently of one another are hydrogen or fluorine
  • X is OR 10 , SR 10 or N(R 11 )R 12 ;
  • R 10 is methyl, ethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, cyanomethyl.tert-butyloxycarbonylmethyl, allyl, 2-propynyl, cyclohexyl, cyclohexenyl, pyridine, pyrimidine or triazine, in which these heterocyclic radicals in each case are unsubstituted or mono- to trisubstituted by identical or different substituents from the group comprising halogen, C C 2 alkyl, trifluoromethyl and cyano;
  • R n is hydrogen, C r C 4 alkyl, halo-C r C -alkyl having 1, 2 or 3 halogen atoms, hydroxy-
  • R 12 is hydrogen
  • R ⁇ and R 12 together with the nitrogen atom to which they are bonded, are pyrrolidine, piperidine, piperazine, morpholine or 2,6-dimethylmorpholine.
  • R 2 is hydrogen, methyl or ethyl
  • R 3 is fluorine or chlorine
  • R 5 is methyl or ethyl
  • R 8 and R 9 independendy of one another are hydrogen or fluorine
  • X is OR 10 , SR 10 or N(R n )R 12 ;
  • R 10 is methyl, ethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, cyanomethyl,tert-butyloxycarbonylmethyl, allyl, 2-propynyl, cyclohexyl, cyclohexenyl, pyridine, pyrimidine or triazine, in which these heterocyclic radicals in each case are unsubstituted or mono- to trisubstituted by identical or different substituents from the group comprising halogen, Cj-Qzalkyl, trifluoromethyl and cyano;
  • R ⁇ is hydrogen, C r C 4 alkyl, halo-C r C 4 -alkyl having 1, 2 or 3 halogen atoms, hydroxy-
  • R 12 is hydrogen
  • R ⁇ and R 12 together with the nitrogen atom to which they are bonded, are pyrrolidine, piperidine, piperazine, morpholine or 2,6-dimethylmorpholine.
  • R 2 is hydrogen, methyl or ethyl
  • R 3 is fluorine or chlorine
  • R ⁇ is methyl or ethyl
  • R 8 and R 9 independently of one another are hydrogen or fluorine
  • X is OR ⁇ SRuj or N Rj Ri
  • R 10 is methyl, ethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, cyanomethyl.tert-butyloxycarbonylmethyl, allyl, 2-propynyl, cyclohexyl, cyclohexenyl, pyridine, pyrimidine or triazine, in which these heterocyclic radicals in each case are unsubstituted or mono- to trisubstituted by identical or different substituents from the group comprising halogen, C r C 2 alkyl, trifluoromethyl and cyano;
  • R n is hydrogen, C r C 4 alkyl, halo-C C 4 -alkyl having 1, 2 or 3 halogen atoms, hydroxy-
  • C r C 4 alkyl cyano-C r C 4 alkyl, allyl, 2-propynyl, cyclohexyl, cyclohexenyl, cyclopropyl, benzyl or phenyl;
  • R 12 is hydrogen
  • R ⁇ and R 1 together with the nitrogen atom to which they are bonded, are pyrrolidine, piperidine, piperazine, morpholine or 2,6-dimethylmorpholine.
  • R 2 is methyl or ethyl
  • X is OR 10 or SR 10 ;
  • R 10 is C r C 6 alkyl, halo- - alkyl having 1-3 halogen atoms,
  • W is C r C 6 alkoxy, C 3 -C 6 cycloalkoxy, or the group -NCI ⁇ yi ⁇ ;
  • T j and T independently of one another are hydrogen, C C 6 alkyl, halo- -Cgalkyl having 1-3 halogen atoms, C ⁇ Cgcycloalkyl, phenyl, halophenyl having 1-3 halogen atoms, pyridyl or naphthyl, or
  • T ! and T 2 together with the nitrogen atom to which they are bonded, are piperidine, piperazine, morpholine or 2,6-dimethylmorpholine.
  • R 2 is methyl or ethyl
  • X is OR 10 or SRio ;
  • R 10 is C 1 -C 6 alkyl, halo-C ⁇ Cgalkyl having 1-3 halogen atoms,
  • W is C r C 6 alkoxy, C 3 -C 6 cycloalkoxy, or die group -N(T j )T 2 ;
  • T l and T 2 independently of one another are hydrogen, C C 6 alkyl, halo-C r C 6 alkyl having
  • halogen atoms C ⁇ Cgcycloalkyl, phenyl, halophenyl having 1-3 halogen atoms, pyridyl or naphthyl, or
  • Tj and T 2 together with the nitrogen atom to which they are bonded, are piperidine, piperazine, morpholine or 2,6-dimethylmorpholine.
  • R 2 is methyl or ethyl
  • X is OR 10 or SR 10 ;
  • R 10 is C r C 6 alkyl, halo-C j - alkyl having 1-3 halogen atoms,
  • W is C C 6 alkoxy, C 3 -C 6 cycloalkoxy, or the group -N(T])T 2 ;
  • T j and T 2 independently of one another are hydrogen, C 1 -C 6 alkyl, halo-C r C 6 alkyl having
  • halogen atoms C 3 -C 6 cycloalkyl, phenyl, halophenyl having 1-3 halogen atoms, pyridyl or naphthyl, or
  • T l and T 2 together with the nitrogen atom to which they are bonded, are piperidine, piperazine, morpholine or 2,6-dimethylmorpholine.
  • a particular group of compounds are furthermore those in which, in formula I, X is SR 10 .
  • the invention furthermore relates to a process for the preparation of compounds of the formula I and, where appropriate, their tautomers, in each case in the free form or in salt form, for example, which comprises reacting:
  • R 10 is as defined for formula I and Z is a nucleofugic radical which can easily be split off; preferably in the presence of a base, particularly preferably by first reacting a compound of the formula II with a base and then reacting a compound of the formula III; or
  • M is hydrogen, Li + , Na + , K + , l/2Mg 2+ or a quaternary ammonium ion;
  • X is ORio or N(Rn)R 12 , and wherein
  • R 10 , R j j and R 12 are as defined for formula I; if appropriate in the presence of a base; or c) for the preparation of a compound of the formula I in which R and R J are as defined for formula I but are other than hydrogen: a compound of die formula I in which R 4 and R 14 are hydrogen with a compound of the formula R 4 '-Z' or R 14 '-Z ⁇ in which R 4 ' and R ⁇ ' are as defined in formula I for R 4 and
  • R 14 but are other than hydrogen, and Z' is a nucleofugic radical which can easily be split off; preferably in die presence of a base.
  • Another process for the preparation of a compound of the formula I comprises reacting a compound of die formula VII
  • M is hydrogen, Li + , Na + , K + , l/2Mg 2+ or a quaternary ammonium ion;
  • X' is OR 10 , SR 10 or N(R n )R 12 , and in which R 10 , R ⁇ and R 12 are as defined for formula I; if appropriate in the presence of a base.
  • reaction described above and below are carried out in a manner known per se, for example in the absence or usually in the presence of a suitable solvent or diluent or a mixture thereof, the reaction being carried out, as required, by cooling, at room temperature or by heating, for example in a temperature range from about -80°C up to the boiling point of the reaction medium, preferably from about -20°C up to about +150°C, and, if necessary, in a closed vessel, under pressure, in an inert gas atmosphere and/or under anhydrous conditions.
  • Typical reaction conditions can be found in die examples.
  • Nucleofugic radicals Z and Z' are, for example: fluorine, chlorine, bromine, iodine, C r C 8 alkylthio, such as methylthio, ethylthio or propylthio, -Cgalkanoyloxy, such as acetoxy, (halo)C ⁇ -Cgalkanesulfonyloxy, such as methanesulfonyloxy, ethanesulfonyloxy or trifluoromethanesulfonyloxy, or unsubstituted or substituted phenylsulfonyloxy, such as benzenesulfonyloxy or p-toluenesulfonyloxy, and furthermore also hydroxyl.
  • Suitable bases are, for example, alkali metal or alkaline earth metal hydroxides, hydrides, amides, alkanolates, carbonates, dialkylamides or alkylsilylamides, alkylamines, alkylenediamines, non-alkylated or N-alkylated, saturated or unsaturated cycloalkylamines, basic heterocyclic compounds, ammonium hydroxides and carbocyclic amines.
  • Examples are sodium hydroxide, hydride, amide, methanolate and carbonate, potassium tert-butanolate and carbonate, lithium diisopropylamide, potassium bis(trimethylsilyl)amide, calcium hydride, triethylamine, triethylenediamine, cyclohexylamine, N-cyclohexyl-N,N-dimethylamine, N,N-diethylaniline, pyridine, 4-(N,N-dimethylamino)pyridine, N-methylmorpholine, benzyl-trimethyl-ammonium hydroxide and l,8-diazabicyclo[5.4.0]undec-5-ene (DBU).
  • DBU diazabicyclo[5.4.0]undec-5-ene
  • reaction partners can be reacted with one another as such, i.e. without addition of a solvent or diluent, for example in the melt.
  • solvents or diluents which may be mentioned are: aromatic, aliphatic and alicyclic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, chlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane, methylene chloride, chloroform, dichloroethane or trichloroethane; ethers, such as diethyl ether, ten-butyl methyl ether, tetrahydrofuran or dioxane; ketones, such as acetone or methyl ethyl ketone; alcohols, such as methanol, ethanol, propanol,
  • the reaction is advantageously ca ⁇ ied out in a temperature range of about 0°C to about +180°C, preferably about +20°C to about +130°C, in many cases at the reflux temperature of the solvent used.
  • reaction can be ca ⁇ ied out under phase transfer catalysis in an organic solvent, for example methylene chloride or toluene, in the presence of an aqueous basic solution, for example sodium hydroxide solution, and a phase transfer catalyst, for example tetrabutylammonium hydrogen sulfate.
  • organic solvent for example methylene chloride or toluene
  • a phase transfer catalyst for example tetrabutylammonium hydrogen sulfate.
  • a compound I obtainable according to the process or in another manner or, where appropriate, a tautomer thereof can be converted into another compound I in a manner known per se by replacing one or more substituents of the starting compound I by another substituent in the customary manner.
  • - substituents which do not contain halogen or non-halogenated aromatic or heteroaromatic ring part structures can be halogenated to halo-containing substituents or halogenated aromatic or heteroaromatic ring part structures;
  • - halogen substituents can be replaced by other substituents, such as cyano, alkylthio or alkoxy substituents;
  • N- N-hydrogen can be replaced by N-alkyl, N-benzyl, N-aryl, N-heteroaryl, N-alkanoyl, N-benzoyl or N-sulfonyl;
  • - sulfides can be oxidized to sulfoxides and sulfones
  • - carbonyl groups can be sulfated to thiocarbonyl groups.
  • Salts of compounds I can be prepared in a manner known per se.
  • acid addition salts of compounds I are obtained by treatment with a suitable acid or a suitable ion exchanger reagent
  • salts with bases can be obtained by treatment with a suitable base or a suitable ion exchanger reagent.
  • Salts of compounds I can be converted into the free compounds I in the customary manner, acid addition salts for example by treatment with a suitable basic agent or a suitable ion exchanger reagent and salts with bases for example by treatment with a suitable acid or a suitable ion exchanger reagent
  • Some of the compounds I can be in the form of one of the possible isomers or as mixtures thereof, for example as pure isomers or as isomer mixtures, such as enantiomer mixtures, for example racemates, diastereomer mixtures or racemate mixtures, depending on the number of and absolute relative configuration of die asymmetric carbon atoms; the invention relates both to the pure isomers and to all die possible isomer mixtures and is in each case to be understood accordingly above and below, although stereochemical details are not mentioned specifically in each case.
  • Diastereomer mixtures and racemate mixtures of compounds I obtainable according to the process or by another means can be separated into the pure diastereomers or racemates in a known manner on the basis of the physico-chemical differences of the constituents, for example by fractional crystallization, distillation and/or chromatography.
  • the invention likewise relates to novel starting substances and intermediates used for the preparation of die compounds of the formula I, their use and processes for their preparation.
  • the compounds of the formula II can be prepared, for example, by reacting a compound of the formula V
  • R R and R 3 have the meanings given for formula I and Z is a nucleofugic radical which can easily be split off, with a compound of the formula VI
  • Another possibility for the preparation of compounds of die formula II comprises reacting a compound of the formula VII with a thionating agent, preferably with phosphorus pentasulfide or with 4-methoxyphenylthiophosphonic acid cyclodithioanhydride ("Lawesson reagent"), if appropriate in a solvent.
  • a thionating agent preferably with phosphorus pentasulfide or with 4-methoxyphenylthiophosphonic acid cyclodithioanhydride ("Lawesson reagent")
  • Pyrimidines which are amino-substituted in the 4-position are already known, for example from the Patent Application WO 92/08704.
  • the compounds I of the present invention differ from these known compounds structurally in a characteristic manner; furthermore, the compounds of the formula I of the present invention show an unexpectedly high microbicidal, insecticidal, nematicidal and acaricidal activity. Protection of plants can occur here either by direction action on the pests or by activation and stimulation of the plant's own defence system (immunization).
  • the compounds of the formula I of the present invention are stable at room temperature to slightly elevated temperature and can easily be stored. They can be used in the agricultural sector and related fields preventively and/or curatively as active compounds for control of plant pests.
  • the active compounds of the formula I according to the invention are distinguished not only by an outstanding action - even at low use concentrations - but also by a good agricultural acceptability. They have very good advantageous properties, in particular systemic properties, and can be used for protection of numerous crop plants.
  • the pests which occur on plants or parts of plants (fruit, blossom, foliage, stems, tubers, roots) of various crops of useful plants can be checked or destroyed with the active compounds of formula I, parts of plants which grow later also remaining spared, for example from phytopathogenic microorganisms.
  • the compounds I are active, for example, against phytopathogenic fungi belonging to the following classes: Fungi imperfecti (for example Botrytis, Pyricularia, Helminthosporium, Fusarium, Septoria, Cercospora and Altemaria) and Basidiomycetes (for example Rhizoctonia, Hemileia, Puccinia). They furthermore have an action against the classes of Ascomycetes (for example Venturia and Erysiphe, Podosphaera, Monilinia, Uncinula) and Oomycetes (for example Phytophthora, Pythium, Plasmopara).
  • Fungi imperfecti for example Botrytis, Pyricularia, Helminthosporium, Fusarium, Septoria, Cercospora and Altemaria
  • Basidiomycetes for example Rhizoctonia, Hemileia, Puccinia
  • They furthermore have an action against the classes of Ascomycetes (for example Venturia and
  • the compounds I furthermore can be used as dressing agents for the treatment of seed (fruit, tubers, grains) and plant seedlings for protection from fungal infections and against phytopathogenic fungi which occur in the soil.
  • the compounds I according to the invention are also useful active compounds in the control of pests of the order Acarina and of the insects and nematode classes on crop and ornamental plants in agriculture, in particular in cotton, vegetable and fruit plantations, in forestry, in the field of protection of stored products and materials, and in the hygiene sector for control of animal pests, in particular on domestic animals and productive livestock. They are active against various stages of development. They can display tiieir action here in the immediate mortality of the pests or only after some time, for example during moulting, or in a significantly reduced oviposition and/or hatching rate.
  • the order of the Acarina includes, for example, Boophilus spp. and Tetranychus Spp.; this list is not limiting.
  • the invention also relates to the compositions which comprise compounds of the formula I, as the active compound, together with a carrier material, in particular crop protection compositions, and to their use in the agricultural sector and related fields.
  • the invention furthermore also includes the preparation of these compositions, which comprises intimately mixing the active substance with one or more of the extenders and distributing agents described below.
  • the invention also includes a method for the treatment of plants, which comprises application of the novel compounds I or of the novel compositions.
  • Target crops for the crop protection use in die context of the invention are, for example, the following plant species: cereals (wheat, barley, rye, oats, rice, maize, sorghum and related species); beet (sugar-beet and feed beet); pome, stone and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); leguminous plants (beans, lentils, peas, soya); oil crops (rape, mustard, poppy, olive, sunflower, coconut, castor, cacao, groundnut); Cucurbitaceae (squash, cucumbers, melons); fibre plants (cotton, flax, hemp, jute); citrus fruits (oranges, lemons, grapefruit, mandarins); vegetable varieties (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); laurel plants (avocado, cinnamonium, camphor) and plants such as tobacco, nuts,
  • Active compounds I are usually used in the form of compositions and can be applied to the area or plants to be treated at the same time as or successively with other active compounds.
  • These other active compounds can be, for example, fertilizers, trace element mediators or other preparations which influence plant growth.
  • Selective herbicides and insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations together with, where appropriate, further carriers, surfactants or other application-promoting additives customary in formulation technology can also be used here.
  • Suitable carriers and additives can be solid or liquid and are the substances used for this purpose in formulation technology, for example naturally occurring or regenerated mineral substances, solvents, dispersants, wetting agents, tackifying agents, thickeners, binders or fertilizers.
  • a preferred process for application of an active compound of the formula I or of an agrochemical composition which comprises at least one of these active compounds is application to the foliage (foliar application).
  • the application frequency and rate of application depend here on the risk of infection by the pathogen in question.
  • the active compounds I can also enter the plant through the root system via the soil (systemic action), by soaking the locus of the plant with a liquid composition or incorporating the substances into the soil in solid form, for example in the form of granules (soil application). In the case of paddy rice crops, such granules can be metered into the flooded rice field.
  • die compounds I can also be applied to seed grains (coating) by either soaking the grains in a liquid composition of die active compound or coating them with a solid formulation.
  • the compounds I are employed here in unchanged form or, preferably, together with the auxiliaries customary in formulation technology.
  • they are advantageously processed in a known manner, for example, to emulsion concentrates, spreadable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts or granules, for example by encapsulation in, for example, polymeric substances.
  • the methods of application such as spraying, atomizing, dusting, scattering, coating or pouring, like the nature of the compositions, are chosen according to the intended aims and the given circumstances.
  • Favourable rates of application are in general 5 g to 2 kg of active substance (AS) per hectare (ha), preferably 10 g to 1 kg of AS/ha, in particular 20 g to 600 g of AS/ha. Dosages of 10 mg to 1 g of active substance per kg of seed are advantageously employed for use as seed dressing compositions.
  • compositions, formulations or preparations comprising the active compound of the formula I and, where appropriate, a solid or liquid additive
  • extenders such as solvents, solid carriers and, if appropriate, surface-active compounds (surfactants).
  • Solvents are: aromatic hydrocarbons, preferably C 8 to C 12 fractions, such as xylene mixtures or substituted naphthalenes, phthalic acid esters, such as dibutyl or dioctyl phthalate, aliphatic hydrocarbons, such as cyclohexane or paraffins, alcohols and glycols and ethers and esters thereof, such as ethanol, ethylene glycol and ethylene glycol monomethyl or -ethyl ether, ketones, such as cyclohexanone, strongly polar solvents, such as N-methyl-2-pyrrolidone, dimediyl sulfoxide or dimethylformamide, and, if appropriate, epoxidized vegetable oils, such as epoxidized coconut oil or soya oil, and water.
  • aromatic hydrocarbons preferably C 8 to C 12 fractions, such as xylene mixtures or substituted naphthalenes, phthalic acid esters, such as dibutyl or
  • the solid carriers used are as a rule naturally occurring rock powders, such as calcite, talc, kaolin, montmorillonite or attapulgite. Highly disperse silicic acid or highly disperse absorbent polymers can also be added to improve the physical properties.
  • Granular, adsorptive granule carriers are porous types, such as pumice, broken bricks, sepiolite or bentonite, and non-sorptive carrier materials are, for example, calcite or sand.
  • Surface-active compounds are nonionic, canonic and or anionic surfactants having good emulsifying, dispersing and wetting properties, depending on the nature of the active compound of die formula I to be formulated.
  • Surfactants are also to be understood as meaning surfactant mixtures.
  • Suitable anionic surfactants can be either so-called water-soluble soaps or water-soluble synthetic surface-active compounds.
  • nonionic surfactants are nonylphenolpolyethoxyethanols, castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts, tributyphenoxypoly- ethylene-ethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.
  • surfactants are also fatty acid esters of polyoxyethylene-sorbitan, such as polyoxyethylene-sorbitan trioleate.
  • the cationic surfactants are, in particular, quaternary ammonium salts which contain at least one alkyl radical having 8 to 22 C atoms as N substituents and contain lower, optionally halogenated alkyl, benzyl or lower hydroxyalkyl radicals as further substituents.
  • the agrochemical compositions as a rule comprise 0.1 to 99 per cent by weight, in particular 0.1 to 95 per cent by weight, of active compound of the formula 1, 99.9 to 1 per cent by weight, in particular 99.8 to 5 per cent by weight, of a solid or liquid additive and 0 to 25 per cent by weight, in particular 0.1 to 25 per cent by weight, of a surfactant.
  • compositions tend to be preferred as commercial goods, the end user as a rule uses dilute compositions.
  • compositions can also comprise further additives, such as stabilizers, foam suppressants, viscosity regulators, binders or tackifiers, as well as fertilizers or other active compounds, in order to achieve specific effects.
  • further additives such as stabilizers, foam suppressants, viscosity regulators, binders or tackifiers, as well as fertilizers or other active compounds, in order to achieve specific effects.
  • Example H-la 0.96 g of NaH in oil ( ⁇ 55%) in 15 ml of anhydrous tetrahydrofuran is initially introduced into a sulfonating flask at room temperature.
  • a solution of 6.97 g of 6-[l-(5-chloro-6-ethylpyrimidin-4-ylamino)ethyl]-2H-l,4-benzoxazine-3-thione in 35 ml of absolute tetrahydrofuran is tiien added dropwise under an N 2 atmosphere in the course of about 10 minutes.
  • 3.12 g of methyl iodide are added at room temperature and the mixture is then stirred at about 25°C for 4 hours.
  • Example H- lb 1.0 g of 6-[l-(5-chloro-6-ethylpyrimidin-4-ylamino)ethyl]-3-methylthio- 2H-l,4-benzoxazine (H-la) and 1.5 g of sodium methylate (30% solution in methanol) in 15 ml of absolute methanol are initially introduced into a sulfonating flask at room temperature. The mixture is kept under reflux for 3 hours and the solvent is then stripped off under a water pump vacuum. The residue is purified by column chromatography over silica gel (mobile phase: n-hexane/ethyl acetate 2:1). 0.9 g of
  • Example H-lc 0.14 g of NaH in oil ( " 55%) in 5 ml of anhydrous tetrahydrofuran is initially introduced into a sulfonating flask at room temperature. Thereafter, a solution of 1.05 g of 6-[l-(5-chloro-6-ethylpyrimidin-4-ylamino)ethyl]-2H-l,4-benzoxazine-3-thione in 25 ml of absolute tetrahydrofuran is added dropwise under an N 2 atmosphere in the course of about 10 minutes. The mixture is stirred at 60-65 °C for 15 minutes for complete salt formation, and 0.45 g of allyl bromide is then added.
  • Tributylphenol polyethylene glycol ether (30 mol ethylenoxy units) - 12% 4%
  • Emulsions of any desired dilution can be prepared from these emulsion concentrates with water.
  • Example F-2 Emulsion concentrate
  • Emulsions of any desired dilution can be prepared from this emulsion concentrate with water.
  • wheat plants are sprayed to drip point with an aqueous spray liquor prepared from a wettable powder of the active compound (0.02% of active substance), and 24 hours later are infected with a uredosporc suspension of the fungus. After an incubation time of 48 hours (conditions: 95 to 100 per cent relative atmospheric humidity at 20°), the plants are placed in a greenhouse at 22°. Evaluation of the development of rust pustules 12 days after infection leads to die assessment of die action of die active substance.
  • the wheat plants are watered with an aqueous spray liquor prepared from a wettable powder of the active compound (0.006% of active substance, based on the soil volume). Care is taken that the spray liquor does not come into contact with the parts of plants above the ground. 48 hours later, the plants are infected with a uredosporc suspension of the fungus. After an incubation time of 48 hours (conditions: 95 to 100 per cent relative atmospheric humidity at 20°), die plants are placed in a greenhouse at 22°. Evaluation of the development of rust pustules 12 days after infection gives die assessment of the action of die active substance.
  • Example B-2 Action against Phytophthora infestans on tomatoes a) Residual protective action
  • tomato plants After growing for three weeks, tomato plants arc watered witii an aqueous spray liquor prepared from a wettable powder of the active compound (0.006% of active substance, based on the soil volume). Care is taken that the spray liquor does not come into contact with the parts of plants above the ground. After 48 hours, die plants are infected with a sporangia suspension of the fungus. Evaluation of die fungal attack 5 days after infection, during which 90 to 100 per cent relative atmospheric humidity and a temperature of 20° are maintained, gives the assessment of die action of active substance.
  • Example B-3 Residual protective action against Cercospora arachidicola on groundnuts
  • Groundnut plants 10 to 15 cm high are sprayed to drip point witii an aqueous spray liquor prepared from a wettable powder of die active compound (0.02% of active substance), and 48 hours later are infected with a conidia suspension of the fungus.
  • the plants are incubated at 21° under a high atmospheric humidity for 72 hours and dien placed in a greenhouse until die typical leaf spots occur.
  • the action of the active substance is evaluated 12 days after infection on the basis of the number and size of the leaf spots.
  • Example B-4 Action against Plasmopara viticola on vines
  • Vine seedlings in the 4 to 5 leaf stage are sprayed to drip point with an aqueous spray liquor prepared from a wettable powder of the active compound (0.02% of active substance), and 24 hours later are infected with a sporangia suspension of die fungus. Evaluation of the fungal attack 6 days after infection, during which 95 to 10 per cent relative atmospheric humidity and a temperature of 20° are maintained, gives the assessment of the action of the active substance.
  • Active compounds from Tables 1-8 show a good action against Plasmopara viticola on vines.
  • compounds 1.2, 1.3, 1.6, 3.3, 3.5, 3.11, 3.42, 5.2, 5.3, 5.5, 5.13, 5.52, 5.104, 5.107, 5.108, 5.110, 5.142 and 5.237 reduce fungal attack to 0-20%.
  • untreated, infected control plants show a fungal attack of 100%.
  • Example B-5 Action against Colletotrichum lagenarium on cucumbers After growing for 2 weeks, cucumber plants are sprayed with a spray liquor prepared from a wettable powder of the active compound (concentration 0.002%). After 2 days, die plants are infected with a spore suspension (1.5x10 s spores/ml) of the fungus and incubated at 23 °C under high atmospheric humidity for 36 hours. The incubation is then continued under normal atmospheric humidity at about 22°C. The fungal attack which has occurred is evaluated 8 days after the infection.
  • Example B-6 Residual protective action against Venturia inaequalis on apples Apple seedlings with fresh shoots 10 to 20 cm long are sprayed to drip point with an aqueous spray liquor prepared from a wettable powder of the active compound (0.02% of active substance), and 24 hours later are infected witii a conidia suspension of the fungus.
  • the plants arc incubated at 90 to 100 per cent relative atmospheric humidity for 5 days and are placed in a greenhouse at 20 to 24° for a further 10 days. Evaluation of the scab attack 15 days after infection gives the assessment of the action of die active substance.
  • Active compounds from Tables 2, 5 and 6 show a good residual protective action against Venturia inaequalis on apples.
  • Example B-7 Action against Erysiphe graminis on barley a) Residual protective action
  • Barley plants approximately 8 cm high are watered with an aqueous spray liquor prepared from a wettable powder of die active compound (0.002% of active substance, based on the soil volume). Care is taken that the spray liquor does not come into contact with the parts of plants above the ground. 48 hours later, the plants arc dusted with conidia of die fungus. The infected plants are placed in a greenhouse at 22°. Evalution of the fungal attack 10 days after infection gives die assessment of die action of die active substance. Compounds from Tables 1-8 show a good action.
  • compounds 1.2, 1.3, 1.6, 3.3, 3.5, 3.11, 3.42, 5.2, 5.3, 5.5, 5.13, 5.52, 5.104, 5.107, 5.108, 5.110, 5.142 and 5.237 reduce fungal attack to 0-20%.
  • untreated, infected control plants show a fungal attack of 100%.
  • Example B-8 Action against Podosphaera leucotricha on apple shoots Apple seedlings witii fresh shoots about 15 cm long are sprayed with a spray liquor (0.06% of active substance). After 24 hours, the treated plants are infected with a conidia suspension of the fungus and placed in a climatically controlled chamber at 70 % relative atmospheric humidity and 20°C. The fungal attack is evaluated 12 days after infection. Active compounds from Tables 1-8, for example compounds 3.42, 5.2, 5.3, 5.5 and 5.61, show a good action against apple mildew.
  • Young bean plants are populated with a mixed population of Tetranychus urticae, and one day later are sprayed with an aqueous emulsion spray liquor which comprises 400 ppm of the active compound. The plants are then incubated at 25 °C for 6 days and subsequently evaluated. The percentage reduction in the population (% action) is determined by comparison of the number of dead eggs, larvae and adults on the treated plants with respect to those on the untreated plants.
  • the compounds of Tables 1, 3 and 5 show a good action against Tetranychus urticae in this test.
  • compounds 1.2, 1.3, 1.6, 3.3, 3.5, 3.11, 3.42, 5.2, 5.3, 5.5, 5.13, 5.52, 5.104, 5.107, 5.108, 5.110, 5.142 and 5.237 show an action of above 90%.
  • Rice plants are treated with an aqueous emulsion spray liquor which comprises 400 ppm of the active compound. After the spray coating has dried on, die rice plants are populated with cicada larvae of the 2nd and 3rd stage. They are evaluated 21 days later. The percentage reduction in population (% action) is determined by comparing the number of surviving cicadas on the treated plants with respect to those on d e untreated plants.
  • B-l 1 Action on a mixed population of Tetranychus cinnabarinus.
  • Dwarf beans in the 2-leaf stage are populated witii a mixed population (eggs, larvae/nymphs, adults) of an OP-tolerant Tetranychus cinnabarinus strain. 24 hours after the infection, die products are applied to the plants in dosages of 200, 100 and 50 mg of
  • Compounds of Tables 1 to 8 show a mortality of more than 70% in dilutions of up to 50 mg AS/litre.
  • Rice plants are treated with an aqueous emulsion spray liquor which comprises 400 ppm of the active compound. After the spray coating has dried on, the rice plants are populated with cicada larvae of the 2nd and 3rd stage. They are evaluated 21 days later. The percentage reduction in population (% action) is determined by comparing the number of surviving cicadas on the treated plants with respect to those on the untreated plants.
  • Young cabbage plants are sprayed witii an aqueous emulsion spray mixture which comprises 400 ppm of the active compound. After the spray coating has dried on, die cabbage plants are populated with 10 caterpillars of the 3rd stage of Plutella xylostella and placed in a plastic container. They are evaluated 3 days later. The percentage reduction in population or the percentage reduction in feeding damage (% action) is determined by comparison of the number of dead caterpillars and die eating damage on the trcated plants with respect to those on the untreated plants.
  • Example B-l 4 Action against Musca domestica
  • a sugar cube is treated with a solution of die test substance such that the concentration of the test substance, after drying overnight, in the sugar is 250 ppm.
  • This treated cube is placed with a wet cotton-wool pad and 10 adult Musca domestica of an OP-resistant strain on an aluminium dish, covered witii a glass beaker and incubated at 25°C. The mortality rate is determined after 24 hours.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
EP94908333A 1993-03-02 1994-02-17 Pyrimidin-derivate als pestizide Ceased EP0687262A1 (de)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
CH617/93 1993-03-02
CH61793 1993-03-02
CH1788/93 1993-06-16
CH178893 1993-06-16
PCT/EP1994/000455 WO1994020490A1 (en) 1993-03-02 1994-02-17 Pyrimidine derivatives useful as pesticides

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EP0687262A1 true EP0687262A1 (de) 1995-12-20

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EP (1) EP0687262A1 (de)
JP (1) JPH08507500A (de)
AU (1) AU6141294A (de)
IL (1) IL108817A0 (de)
WO (1) WO1994020490A1 (de)

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Publication number Priority date Publication date Assignee Title
AU1631699A (en) * 1997-12-18 1999-07-05 E.I. Du Pont De Nemours And Company Cyclohexylamine arthropodicides and fungicides
WO2011146882A1 (en) 2010-05-21 2011-11-24 Intellikine, Inc. Chemical compounds, compositions and methods for kinase modulation
AR091790A1 (es) 2011-08-29 2015-03-04 Infinity Pharmaceuticals Inc Derivados de isoquinolin-1-ona y sus usos
US9481667B2 (en) 2013-03-15 2016-11-01 Infinity Pharmaceuticals, Inc. Salts and solid forms of isoquinolinones and composition comprising and methods of using the same

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Publication number Priority date Publication date Assignee Title
US4895849A (en) * 1986-10-08 1990-01-23 Ube Industries, Ltd. Aralkylaminopyrimidine compounds which are useful as for producing thereof and insecticides
US4931455A (en) * 1988-01-07 1990-06-05 Ube Industries, Ltd. Alkylaminopyrimidine derivative and insecticide, acaricide and fungicide containing the same as active ingredient
EP0470600B1 (de) * 1990-08-10 1997-05-07 Novartis AG Naphthylalkylaminopyrimidin-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Schädlingsbekämpfungsmittel
US5378708A (en) * 1990-11-19 1995-01-03 E. I. Du Pont De Nemours And Company Insecticidal, acaricidal and fungicidal aminopyrimidines
EP0519211A1 (de) * 1991-05-17 1992-12-23 Hoechst Schering AgrEvo GmbH Substituierte 4-Aminopyrimidine, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel
EP0555183A1 (de) * 1992-02-07 1993-08-11 Ciba-Geigy Ag Schädlingsbekämpfungsmittel
DE4208254A1 (de) * 1992-03-14 1993-09-16 Hoechst Ag Substituierte pyrimidine, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel und fungizid

Non-Patent Citations (1)

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Title
See references of WO9420490A1 *

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JPH08507500A (ja) 1996-08-13
WO1994020490A1 (en) 1994-09-15
IL108817A0 (en) 1994-06-24
AU6141294A (en) 1994-09-26

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