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EP1367893A1 - Pyridylpyrimidines en tant qu'agents de lutte contre les parasites - Google Patents

Pyridylpyrimidines en tant qu'agents de lutte contre les parasites

Info

Publication number
EP1367893A1
EP1367893A1 EP02701270A EP02701270A EP1367893A1 EP 1367893 A1 EP1367893 A1 EP 1367893A1 EP 02701270 A EP02701270 A EP 02701270A EP 02701270 A EP02701270 A EP 02701270A EP 1367893 A1 EP1367893 A1 EP 1367893A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
butyl
chlorine
fluorine
aryl
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Withdrawn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
EP02701270A
Other languages
German (de)
English (en)
Inventor
Thomas Bretschneider
Mazen Es-Sayed
Rüdiger Fischer
Fritz Maurer
Christoph Erdelen
Peter Lösel
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
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1367893A1 publication Critical patent/EP1367893A1/fr
Withdrawn legal-status Critical Current

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
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    • 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
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    • 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
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • 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
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
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    • 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
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three 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
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • 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
    • 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
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms 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
    • C07D413/14—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
    • C07D417/14—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

Definitions

  • the present invention relates to new pyridylpyrimidines, several processes for their preparation and their use as pesticides.
  • R 1 and R 2 independently of one another are hydrogen, halogen, roitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkenyl,
  • R 1 and R 2 also together represent alkylene or alkenylene, the carbon chain being formed by 1 to 3 heteroatoms from the series nitrogen and acid. material can be interrupted and the ring thus formed can in turn optionally be substituted by halogen or alkyl,
  • X for halogen, nitro, cyano, hydroxy, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkenyl, alkynyl, alkenyloxy, haloalkenoxy, alkynyloxy, haloalkynyloxy, -S (O) p R3, -NR 4 R 5 , -COR 6 , -CO 2 R 7 , -CSR 6 , -CONR4R5, -NHCO 2 R 8 , cycloalkyl, aryl, arylalkyl, saturated or unsaturated heterocyclyl with 1 to 4 heteroatoms from the series consisting of nitrogen, oxygen and sulfur;
  • two adjacent radicals X together also represent alkylene or alkenylene, where the carbon chain can be interrupted by 1 or 2 heteroatoms from the series nitrogen and oxygen,
  • n stands for 0, 1, 2, 3 or 4, where X stands for the same or different radicals if n stands for 2, 3 or 4,
  • Y stands for a direct bond, oxygen, -S (O) p - or -NR 9 -,
  • p 0, 1 or 2
  • r represents 1, 2, 3, 4, 5 or 6,
  • t and w independently of one another represent 0, 1, 2, 3 or 4,
  • A represents oxygen, sulfur or NR 15 ,
  • E stands for -OR 16 , -SR 16 , -OM, -S " M or -NR 1 ? Rl 8,
  • M represents ammonium which is optionally substituted by alkyl, aryl or arylalkyl or an alkali metal ion,
  • M also stands for an alkaline earth metal ion, two molecules each one
  • R 3 represents hydrogen, alkyl, haloalkyl, cycloalkyl, cycloalkylalkyl; or for aryl, arylalkyl, saturated or unsaturated heterocyclyl or heterocyclylalkyl with 1 to 4 heteroatoms from the series nitrogen, oxygen and sulfur, optionally substituted by halogen, alkyl, haloalkyl, alkoxy, halogenoalkoxy, alkylthio, haloalkylthio,
  • R 4 represents hydrogen, alkyl, haloalkyl, cycloalkyl or alkylcarbonyl
  • R 5 represents hydrogen, amino, formyl, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, alkoxy, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, oxamoyl
  • R 4 and R 5 also together for alkylidene; or represent benzylidene optionally substituted by halogen, nitro, alkyl, haloalkyl;
  • R 4 and R 5 together with the nitrogen atom to which they are attached also represent a saturated or unsaturated heterocycle which may optionally contain a further nitrogen, oxygen or sulfur atom and which may optionally be substituted by alkyl,
  • R 6 represents hydrogen, alkyl, haloalkyl or arylalkyl
  • R 7 represents hydrogen, alkyl, haloalkyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
  • R 8 represents alkyl or haloalkyl
  • R 9 represents hydrogen, alkyl, haloalkyl, cycloalkyl, cycloalkylalkyl; or for aryl, arylalkyl, saturated or unsaturated heterocyclyl or heterocyclylalkyl with 1 to 4 heteroatoms from the series nitrogen, oxygen and sulfur, optionally substituted by halogen, alkyl, haloalkyl, alkoxy, halogenoalkoxy, alkylthio, haloalkylthio,
  • R 10 represents halogen, alkyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyl, cycloalkylalkyl; or represents aryl or arylalkyl, which in turn can be substituted by halogen or alkyl in the aryl part,
  • R 1 1 represents hydrogen or alkyl
  • R 12 and R 13 independently of one another represent hydrogen, hydroxy, alkyl or alkoxy
  • R 14 represents hydrogen, alkyl or haloalkyl
  • R 15 represents hydrogen, alkyl, alkoxy, cyano or dialkylamino
  • R 16 also stands for optionally substituted aryl, arylalkyl, cycloalkyl, cycloalkylalkyl, saturated or unsaturated heterocyclyl or heterocyclylalkyl with 1 to 4 heteroatoms from the series nitrogen, oxygen and sulfur, the substituents in addition to those mentioned above from hydroxy and nitro can be selected
  • R 1 7 represents hydrogen or alkyl
  • R 18 represents hydrogen, hydroxy, amino, alkyl, alkenyl; or for in each case optionally substituted by halogen, hydroxy, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, oxyalkyleneoxy, cycloalkylalkyl, aryl, arylalkyl, heteroaryl or heteroarylalkyl having 1 to 4 heteroatoms from the series nitrogen, oxygen and sulfur; or represents -S (O) p R 3 , -OR14 or -NR 4 R 5 ,
  • R 18 also for in each case the same or different by halogen, amino,
  • R 18 also stands for optionally substituted cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl or heteroarylalkyl with 1 to 4 heteroatoms from the series nitrogen, oxygen and sulfur, where the substituents can be selected from nitro and alkoxycarbonyl in addition to those mentioned above,
  • R 17 and R 18 together with the nitrogen atom to which they are attached, for a 5- or 6-membered saturated or unsaturated heterocycle which may contain 1 or 2 further heteroatoms from the series nitrogen, oxygen and sulfur and which, if appropriate, by Alkyl can be substituted,
  • radicals R 1] may have the same or different meanings if they occur more than once in the same heterocyclic grouping
  • n 0, 1, 2 or 3 where the repeating unit - (CHR 14 ) - within the side chain of a heterocyclic grouping can have the same or different meanings if m represents 2 or 3,
  • G oxygen or sulfur
  • R 19 and R 20 independently of one another represent hydrogen, alkyl or together represent alkylene,
  • R 21 represents hydrogen, alkyl optionally substituted by alkylcarbonyloxy or alkoxy; or represents aryl optionally substituted by halogen, cyano, alkyl, haloalkyl, alkylcarbonyl, alkoxycarbonyl, alkylene,
  • R 22 represents hydrogen, alkyl or alkoxyalkyl
  • R 23 represents hydrogen, amino, alkyl or alkoxyalkyl.
  • the compounds of the formula (I) can optionally be used as geometric and / or optical isomers or
  • R 1 , R 2 , X, n, Z and A have the meanings given above and
  • E 1 represents -OR 16 , -SR 16 or -NR 17 R 18 ,
  • R 1 , R 2 , Z, A and E 1 have the meanings given above and
  • L represents Sn (alkyl) 3 , Sn (aryl) 3 , ZnBr or ZnCl,
  • R 1 , R 2 , X, n, Z and A have the meanings given above and
  • E 2 stands for -NR 17 R 18 ,
  • R 1 , R 2 , X, n, Z and A have the meanings given above and
  • E 3 represents -OR 16 , where R 16 has the meanings given above,
  • R 1 , R 2 , X, n, Z and A have the meanings given above,
  • R 17 and R 18 have the meanings given above, if appropriate in the presence of a diluent and in the presence of a water-absorbing reagent,
  • R 1 , R 2 , X, n, Z and R have the meanings given above and
  • Y 1 represents -SO- or -SO 2 -
  • R 1 , R 2 , X, n, Z and R have the meanings given above, oxidized with an oxidizing agent, if appropriate in the presence of a diluent, if appropriate in the presence of an acid binder and if appropriate in the presence of a catalyst, or
  • R 1 , R 2 , X, n, Z and R 9 have the meanings given above and
  • R a stands for one of the following groupings
  • R 1 has the meanings given above,
  • R 1 , R 2 , X and n have the meanings given above,
  • R 1 , R 2 , X, n, Z and R a have the meanings given above, obtained by
  • R 1 , R 2 , X and n have the meanings given above,
  • R 1 , R 2 , X, n, Z and R a have the meanings given above,
  • R 1 , R 2 , X and n have the meanings given above,
  • Y 2 represents a direct bond, oxygen, sulfur or -NR 9 -,
  • E 4 stands for -OM or -S ⁇ M
  • R 1 , R 2 , X, n, Z, A and M have the meanings given above,
  • R 1 , R 2 , X, n, Y 2 , Z and A have the meanings given above,
  • R 1 , R 2 , X, n, Y and Z have the meanings given above and
  • R b stands for one of the following groupings
  • R 1 , R 2 , X, n and Z have the meanings given above
  • trialkyltin azides if appropriate in the presence of a diluent, or
  • R 1 , R 2 , X, n, Y 2 and Z have the meanings given above,
  • R 1 , R 2 , X, n, Y 2 and Z have the meanings given above,
  • R 1 , R 2 , X, n, Y 2 and Z have the meanings given above,
  • R 1 , R 2 , X, n, Y 2 and Z have the meanings given above,
  • Formula (I) generally defines the pyridylpyrimidines according to the invention.
  • R 1 and R 2 independently of one another preferably represent hydrogen, halogen, nitro, cyano, C r C 6 alkyl, C r C 6 haloalkyl, C r C 6 alkoxy, C r C 6
  • R 1 and R 2 also together preferably represent C 3 -C 5 alkylene or C 3 -C 4 -
  • Alkenylene where the carbon chain can be interrupted by 1 or 2 heteroatoms, which can be 0 to 2 nitrogen atoms and / or 0 or 1 oxygen atom, and the ring formed thereby in turn, if appropriate, once or several times, identically or differently, by halogen or C j -C 6 - alkyl may be substituted.
  • X preferably represents halogen, nitro, cyano, hydroxy, C ] -C 6 -alkyl, C ] -C 6 - haloalkyl, C r C 6 - alkoxy, Cj-Cg-haloalkoxy, C ] -C 6 - alkylthio, C r C 6 haloalkylthio, C 2 -C 6 alkenyl, C -C 6 alkynyl, C 2 -C 6 alkenyloxy, C 2 - Cg haloalkenyloxy, C 2 -Cg alkynyloxy, C 2 -C 6 haloalkynyloxy .
  • two adjacent radicals X together also preferably represent C 3 -C 5 alkylene or C 3 -C 4 alkenylene, the carbon chain being composed of 1 or 2 heteroatoms which contain 0 to 2 nitrogen atoms and / or can be 0 or 1 oxygen atom, can be interrupted.
  • n is preferably 0, 1, 2 or 3, where X is the same or different
  • Residues is when n is 2 or 3.
  • Y preferably represents a direct bond, oxygen, -S (O) p - or -NR 9 -.
  • p is preferably 0, 1 or 2. preferably stands for - (CH 2 ) r -, - (CH 2 ) t - (CHR 10 ) - (CH 2 > W »
  • r is preferably 1, 2, 3, 4, 5 or 6.
  • t and w independently of one another are preferably 0, 1, 2, 3 or 4.
  • R preferably stands for the grouping
  • A preferably represents oxygen, sulfur or NR * 5 .
  • E preferably represents -OR 16 , -SR 16 , -O ⁇ M, -S ⁇ M or -NR 17 R ⁇ 8 .
  • M preferably represents ammonium which is optionally monosubstituted to tetrasubstituted, identically or differently, by C 1 -C 6 -alkyl, aryl or aryl-C 1 -C 6 -alkyl, or a lithium cation (Li + ), a sodium cation (Na + ) or a potassium cation (K + ).
  • M also preferably represents a magnesium cation (Mg 2+ ) or a calcium cation (Ca 2+ ), where two molecules of a compound each form a salt with such an ion.
  • R 3 preferably represents hydrogen, C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 7
  • Cycloalkyl C 1 -C 4 -cycloalkyl-Ci-Cg-alkyl; or in each case optionally monosubstituted or polysubstituted by identical or different halogen, Cj-Cg-alkyl, C j -CG haloalkyl, C Cg alkoxy, Cj-C6 haloalkoxy, C j -C 6 - alkylthio, CJ C 6 -haloalkylthio substituted aryl, aryl-C j -Cg-alkyl, 5- or 6-membered, saturated or unsaturated heterocyclyl or
  • Heterocyclyl-C j -Cg-alkyl each of which contains 0 to 4 nitrogen atoms, 0 to 2 non-adjacent oxygen atoms and / or 0 to 2 non-adjacent sulfur atoms.
  • R 4 preferably represents hydrogen, C r C 6 alkyl, C ] -C 6 haloalkyl, C 3 -C 7 -
  • R 5 preferably represents hydrogen, amino, formyl, C j -Cg alkyl, C -C6 alkenyl, C 2 -C 6 alkynyl, C r C 6 haloalkyl, C 3 -C 7 cycloalkyl, C 1 - C 6 -alkoxy, "C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C2-C 6 -alkylcarbonyl, C r C 6 -alkoxycarbonyl,
  • R 4 and R 5 also together preferably represent C j -Cg alkylidene; or for benzylidene which is optionally mono- or polysubstituted, identically or differently, by halogen, nitro, C] -C 6 -alkyl, C j -C 6 -haloalkyl.
  • R 4 and R 5 together with the nitrogen atom to which they are attached are preferably a 5- or 6-membered, saturated or unsaturated
  • Heterocycle which may optionally contain a further nitrogen, oxygen or sulfur atom and which may optionally be mono- or polysubstituted, identically or differently, by Cj-Cg-alkyl.
  • R 6 preferably represents hydrogen, C 1 -C 6 -alkyl, C] -C 6 -haloalkyl or aryl-C r C 6 -alkyl.
  • R 7 preferably represents hydrogen, C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkyl-C r C 6 alkyl, aryl or aryl-C j -C 6 alkyl.
  • R 8 preferably represents C j -Cg alkyl or C j -Cg haloalkyl.
  • R 9 preferably represents hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkyl-Cj-C 6 alkyl; or for each optionally one or more times, the same or different, by halogen, C j -Cg-alkyl, C r C 6 -haloalkyl, Cj-Cg-alkoxy, Cj-Cg-haloalkoxy, C r C 6 -alkylthio, Ci-Cg -Halogenalkylthio substituted aryl, aryl-C ] -C 6 -alkyl, 5- or 6-membered, saturated or unsaturated heterocyclyl or heterocyclyl-Ci-Cg-alkyl, each having 0 to 4 nitrogen atoms, 0 to 2 non-adjacent oxygen atoms and / or contain 0 to 2 non-adjacent
  • R 1 0 preferably represents halogen, C j -C 6 alkyl, C j -C 6 alkylcarbonyl, C j -C 6 alk 'oxycarbonyl, C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkyl -C r C 6 alkyl; or for aryl or aryl-Cj-Cö-alkyl, which in turn can be substituted one or more times, in the aryl part, identically or differently by halogen or C Cg-alkyl.
  • R u preferably represents hydrogen or C -C 6 alkyl.
  • R 12 and R 13 independently of one another preferably represent hydrogen, hydroxy, C r C 6 alkyl or C r C 6 alkoxy.
  • R 14 preferably represents hydrogen, C r C 6 alkyl or C r C 6 haloalkyl.
  • R 15 preferably represents hydrogen, C ] -C 6 alkyl, C 1 -C 6 alkoxy, cyano or di (C ] -Cg alky ⁇ amino.
  • R 16 preferably represents hydrogen; for in each case optionally single or multiple, identical or different by halogen, amino, hydroxy, cyano,
  • R 16 also preferably represents aryl, aryl-Cj-Cö-alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C] -C 6 - which are optionally mono- or polysubstituted by identical or different substituents.
  • R 17 preferably represents hydrogen or C j -C 6 alkyl.
  • R 18 preferably represents hydrogen, hydroxy, amino, C ] -C 6 alkyl, C 2 -C 6 alkenyl; or for each optionally one or more times, identically or differently, by halogen, hydroxyl, Cj-Cg-alkyl, C j -C 6 -haloalkyl, C j -Cg-alkoxy, C ] -C 6 -haloalkoxy, C r C 6 - Alkylthio, C r C 6 haloalkylthio, oxy (C ] -C 6 alkylene) oxy substituted C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkyl-
  • C j -Cg-alkyl, aryl, aryl-Cj-Cg-alkyl, heteroaryl or heteroaryl-C j -Cg-alkyl which each contain 0 to 4 nitrogen atoms, 0 to 2 non-adjacent oxygen atoms and / or 0 to 2 non-adjacent sulfur atoms ; or for -S (O) p R 3 , -OR 14 or -NR 4 R 5 .
  • R 18 also preferably represents in each case single or multiple, identical or different by halogen, amino, hydroxy, cyano, nitro, C j -C 6 -alkoxy, C r C 6 -haloalkoxy, Cj-Cg-alkylthio, Cj-C 6 -Halogenalkylthio, C r C 6 alkoxycarbonyl, C 2 -C 6 alkenyloxycarbonyl substituted C j -C 6 alkyl or C 2 - C 6 alkenyl.
  • R 18 also preferably represents in each case optionally mono- or polysubstituted, identically or differently substituted C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C j -Cg-alkyl, aryl, aryl-C Cg-alkyl, heteroaryl or heteroaryl-C ⁇ -C 6 alkyl which are each 0 to 4 nitrogen atoms, 0 to 2 nonadjacent oxygen atoms and / or contain 0 to 2 nonadjacent sulfur atoms, where the substituents selected in addition to the above from nitro and C j -Cg- alkoxycarbonyl can be.
  • R 17 and R 18 together with the nitrogen atom to which they are attached, preferably represent a 5- or 6-membered saturated or unsaturated heterocycle which may contain 1 or 2 further heteroatoms which contain 0 to 2 nitrogen atoms, 0 or 1 Can be oxygen atom and / or 0 or 1 sulfur atom, and which can optionally be substituted one or more times, identically or differently, by Cj-Cg-alkyl.
  • Q preferably represents one of the following groupings
  • R 1 * radicals can have the same or different meanings if they occur more than once in the same heterocyclic grouping.
  • n preferably represents 0, 1, 2 or 3, it being possible for the repeating unit - (CHR 14 ) - within the side chain of a heterocyclic grouping to have the same or different meanings if m is 2 or 3.
  • G preferably represents oxygen or sulfur.
  • R 19 and R 20 independently of one another preferably represent hydrogen, C j -CG alkyl or together represent C 2 alkylene -C4-.
  • R 21 preferably represents hydrogen, represents optionally mono- or polysubstituted by identical or different substituents from Cj-Cg-alkylcarbonyloxy or C j C j -Cg- alkoxy -Cg- alkyl; or optionally monosubstituted or polysubstituted by identical or different halogen, cyano, Cj-Cg alkyl, C j -CG-halo- genalkyl, C] -CG-alkylcarbonyl, Cj-C] o-alkoxycarbonyl, C 3 -C 5 -Alkylene substituted aryl.
  • R 22 preferably represents hydrogen, Cj-Cg-alkyl or Ci-Cg-alkoxy-C j -Cg-alkyl.
  • R 23 preferably represents hydrogen, amino, C j -Cg-alkyl or C j -Cg-alkoxy-C j -
  • R 1 and R 2 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C ] -C - alkyl, C ] -C 4 haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms , Cj-C 4 -alkoxy, Cj-C 4 -haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms, C ⁇ -C-alkylthio, C ⁇ -C 4 -haloalkylthio with 1 to 9 fluorine, chlorine - and / or bromine atoms, C - C 4 alkenyl, C 2 -C 4 alkynyl, -S (O) p R 3 , -NR 4 R 5 , -COR 6 , -CO 2 R 7 , -CSR6, - CONR 4 R 5 , -NHCO 2 R 8 , C 3 -C 6 cycloal
  • R 1 and R 2 furthermore together particularly preferably represent C 3 -C 5 ⁇ alkylene or C 3 -C 4 alkenylene, wherein the carbon chain by 1 or 2 hetero atoms, which may be 0 to 2 nitrogen atoms and / or 0 or 1 oxygen atom, can be interrupted and the ring thus formed can in turn be optionally substituted one to four times, identically or differently, by fluorine, chlorine, bromine or C ] -C 4 -alkyl.
  • X particularly preferably represents fluorine, chlorine, bromine, nitro, cyano, hydroxy, C ] -C - alkyl, C] -C 4 -haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, C ⁇ ⁇ C - Alkoxy, C] -C -haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms, Cj-C - alkylthio, C ] -C -haloalkylthio with 1 to 9 fluorine, chlorine and / or bromine atoms, C 2 -C alkenyl, C 2 -C 4 alkynyl, -S (O) p R 3 , -NR 4 R 5 , -COR6, -CO 2 R 7 , -CSR6, -CONR 4 R5, -NHCO 2 R 8 , C 3 - Cg-cycloalkyl, aryl, aryl-
  • two adjacent radicals X also together - "sa particularly preferably for C 3 -C 4 alkylene or C 3 -C 4 alkenylene, the carbon chain being composed of 1 or 2 heteroatoms which have 0 to 2 nitrogen atoms and / or can be 0 or 1 oxygen atom, can be interrupted.
  • n particularly preferably represents 0, 1 or 2, where X represents the same or different radicals if n represents 2.
  • Y particularly preferably represents a direct bond, oxygen, -S (O) p - or -NR 9 -.
  • r particularly preferably represents 1, 2, 3 or 4.
  • t and w independently of one another are particularly preferably 0, 1, 2, 3 or 4.
  • R particularly preferably stands for the grouping
  • E particularly preferably represents -OR 16 . -SR! 6. -QM _S-M or -NR 17 ⁇ ? 18
  • M particularly Favor g t is optionally monosubstituted to tetrasubstituted by identical or different C r C 4 - alkyl, phenyl, benzyl or phenylethyl substituted ammonium, or a sodium cation (Na +) or potassium cation (K +).
  • M also particularly preferably stands for a magnesium cation (Mg 2+ ) or a calcium cation (Ca 2+ ), two molecules of a compound each forming a salt with such an ion.
  • R 3 particularly preferably represents hydrogen, C -C 4 - alkyl, C ⁇ -C 4 -haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -CG-cycloalkyl, C 3 cycloalkyl -Cg- Cj-C4 alkyl; or represents in each case optionally mono- to tetrasubstituted by identical or different fluorine, chlorine, bromine, C j -C 4 alkyl, C r C 4 -Halo- genalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, C ] - C4-haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms, C ] -C4-
  • R 4 particularly preferably represents hydrogen, CJ-C 4 -alkyl, C ] -C4-haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -Cg-cycloalkyl, C ] -C 4 -alkylcarbonyl.
  • R 5 particularly preferably represents hydrogen, amino, formyl, C ⁇ -C4-alkyl, C 2 - C 4 - alkenyl, C 2 -C 4 alkynyl, C r C 4 haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -C 6 cycloalkyl, C ⁇ -C 4 alkoxy, Ci ⁇ alkoxy-C! - C4-alkyl, C1-C4- alkylcarbonyl, C1-C4- alkoxycarbonyl, oxamoyl.
  • R 4 and R 5 together also particularly preferably represent CJ-C4-alkylidene; or for optionally up to fourfold, identical or different by fluorine, chlorine, bromine, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, substituted benzylidene.
  • R 4 and R 5 together with the nitrogen atom to which they are attached, particularly preferably represent a 5- or 6-membered, saturated or unsaturated saturated heterocycle which may optionally contain a further nitrogen, oxygen or sulfur atom and which may optionally be monosubstituted to tetrasubstituted by identical or different substituents by C1-C4-alkyl.
  • R 6 particularly preferably represents hydrogen, -CC 4 -alkyl, C ] -C 4 -haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms or aryl -CC-C4-alkyl.
  • R 7 particularly preferably represents hydrogen, -CC 4 alkyl, C j -C haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -Cg cycloalkyl, C 3 -Cg cycloalkyl-C r C 4 alkyl, aryl or aryl C 1 -C 4 alkyl.
  • R 8 particularly preferably represents C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms.
  • R 9 particularly preferably represents hydrogen, Cj-C4-alkyl, C ] -C 4 -haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -Cg-cycloalkyl, C 3 -Cg-cycloalkyl-C ⁇ -C alkyl; or for each optionally single to fourfold, identical or different by fluorine, chlorine, bromine, C ] -C4-alkyl, C j ⁇ -haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, C ] -C4 alkoxy , C ] - C4-haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms, C1-C4-
  • R 10 particularly preferably represents fluorine, chlorine, bromine, iodine, C1-C4-alkyl, C j -C4-
  • R 1 ! particularly preferably represents hydrogen or C j -C 4 alkyl.
  • R 12 and R 13 independently of one another particularly preferably represent hydrogen, hydroxyl, -CC alkyl or C ] -C alkoxy.
  • R 14 particularly preferably represents hydrogen, C 1 -C 4 -alkyl or C ] -C -halogenoalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms.
  • R 15 particularly preferably represents hydrogen, Cj-C-alkyl, C ] -C4-alkoxy, cyano or di (C ] -C4-alkyl) amino.
  • R 16 particularly preferably represents hydrogen; for in each case optionally up to four times, identically or differently, by fluorine, chlorine, bromine, amino, hydroxy, cyano, nitro, C r C 4 -alkoxy, C r C 4 -haloalkoxy with 1 to 9 fluorine, chlorine and / or Bromine atoms, -CC alkylthio, C j -C halogeno-alkylthio with 1 to 9 fluorine, chlorine and / or bromine atoms, C j -C - alkoxycarbonyl, C 2 -C 4 - alkenyloxycarbonyl, C r C 4 - Alkylcarbonyloxy, C 2 -C alkylene carbonyloxy, oxy (-C 4 alkylene) oxy, oxetanyl, dioxanyl, oxazolidinyl, dioxolanyl, aryloxy, haloaryloxy, -CONR 4 R
  • R 16 also particularly preferably represents in each case up to the maximum possible number, identical or different C 1 -C 6 -alkyl, decyl, dodecyl, tetradecyl, hexadecyl, C 2 -Cg-alkenyl, decenyl substituted by fluorine, chlorine and / or bromine, C -C 4 alkynyl.
  • R 16 also particularly preferably represents aryl, aryl-C ] -C 4 -alkyl, C 3 - Cg-cycloalkyl, C3-C 6 -cycloalkyl-C] -C 4 -alkyl which are optionally mono- to tetrasubstituted, identically or differently, in each case , 4- to 6-membered, saturated or unsaturated, heterocyclyl or heterocyclyl-C ] -C 4 -alkyl, each of which contains 0 to 3 nitrogen atoms, 0 to 2 non-adjacent oxygen atoms and / or 0 to 2 non-adjacent sulfur atoms, the Substituents can be selected from hydroxy and nitro in addition to those mentioned above.
  • R 17 particularly preferably represents hydrogen or C ] -C 4 -alkyl.
  • R 18 particularly preferably represents hydrogen, hydroxy, amino, C ] -C alkyl, C 2 -C 4 alkenyl; or for each optionally single to fourfold, identical or different by fluorine, chlorine, bromine, hydroxyl, C 1 -C 4 -alkyl, C ] ⁇ - haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C j -C4 -
  • R 18 also particularly preferably represents in each case one to four times, the same or different, fluorine, chlorine, bromine, amino, hydroxyl, cyano, nitro,
  • Bromine atoms C r C 4 -alkylthio, C 1 -C -haloalkylthio with 1 to 9 fluorine, Chlorine and / or bromine atoms, Cj-C 4 alkoxycarbonyl, C 2 -C alkenyloxycarbonyl substituted C Cr alkyl or C -C 4 alkenyl; or for each optionally up to the maximum possible number, identically or differently, substituted by fluorine, chlorine and / or bromine, substituted by C 4 -alkyl or C 2 -C 4 -alkenyl.
  • R 18 also particularly preferably represents in each case monosubstituted to tetrasubstituted, identically or differently substituted C 3 -Cg-cycloalkyl, C -Cg-cycloalkyl-C-C4-alkyl, aryl, aryl-Cj-C 4 -alkyl, heteroaryl or heteroaryl - C ] -C4-alkyl, each containing 0 to 3 nitrogen atoms, 0 to 2 non-adjacent oxygen atoms and / or 0 to 2. non-adjacent sulfur atoms, the substituents being selected from nitro and C Cg-alkoxycarbonyl in addition to the above can.
  • R 17 and R 18 together with the nitrogen atom to which they are attached, particularly preferably represent a 5- or 6-membered saturated or unsaturated heterocycle which may contain 1 or 2 further heteroatoms which contain 0 to 2 nitrogen atoms, 0 or 1 oxygen atom and / or 0 or 1 sulfur atom, and which may optionally be mono- to trisubstituted, identically or differently, by C] -C4 ⁇ alkyl.
  • radicals R 1] can have the same or different meanings if they occur more than once in the same heterocyclic grouping.
  • n particularly preferably represents 0, 1, 2 or 3, it being possible for the repeating unit - (CHR 14 ) - within the side chain of a heterocyclic grouping to have the same or different meanings if m is 2 or 3.
  • G particularly preferably represents oxygen or sulfur.
  • R 19 and R 20 independently of one another particularly preferably represent hydrogen, C 1 -C alkyl or together represent C 2 -C 3 alkylene.
  • R 21 particularly preferably represents hydrogen, optionally monosubstituted to disubstituted by identical or different Cj ⁇ alkylcarbonyloxy or C j -
  • Alkyl C 1 -C 4 haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C j ⁇ alkylcarbonyl, Cj-Cg alkoxycarbonyl, C 3 -C 5 alkylene substituted aryl.
  • R 22 particularly preferably represents hydrogen, C1-C4-alkyl or -CC 4 alkoxy- C r C 4 alkyl.
  • R 23 particularly preferably represents hydrogen, amino, Cj-C - alkyl or C j -C - alkoxy-C j-C4 alkyl.
  • R 1 and R 2 independently of one another very particularly preferably represent
  • X very particularly preferably represents fluorine, chlorine, bromine, nitro, cyano, hydroxy, methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, -CF 3 , -CC1 3 , -CHF 2 , -CC1F 2 , -CHC1 2 , -CF 2 CHFC1, -CF 2 CH 2 F, -CF 2 CC1 3 , -CH 2 CF 3 , -CF 2 CHFCF 3 , -CH 2 CF 2 H, -CH 2 CF 2 CF 3 , -CF 2 CF 2 H, -CF 2 CHFCF 3 , methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, trifluoromethoxy, trichloromethoxy, -OCH 2 CF 3 , -SCF 3
  • X also very particularly preferably represents methylthio, ethylthio, n-propylthio, i-propylthio.
  • n very particularly preferably represents 0, 1 or 2, where X represents the same or different radicals when n represents 2.
  • Y very particularly preferably represents a direct bond, oxygen, -S (O) p - or -NR 9 -.
  • p very particularly preferably represents 0, 1 or 2.
  • R very particularly preferably stands for the grouping
  • E very particularly preferably represents -OR 16 , -SR 16 , -O ⁇ M or -NR 17 R ] 8 .
  • M very particularly preferably stands for tetrabutylammonium, trimethylbenzylammonium or for a sodium cation (Na + ) or a potassium cation (K + ).
  • M also very particularly preferably represents a magnesium cation (Mg + ) or a calcium cation (Ca 2+ ), two molecules of a compound each forming a salt with such an ion.
  • R 4 very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, -COMe.
  • R 5 very particularly preferably represents hydrogen, amino, formyl, methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, vinyl, propargyl, methoxy, methoxymethyl, COMe, -COEt, t-butoxycarbonyl, oxamoyl.
  • R 4 and R 5 also together very particularly preferably represent ethylidene, i-propylidene, s-butylidene, nitrobenzylidene.
  • R 4 and R 5 together with the nitrogen atom to which they are attached, very particularly preferably represent a 5- or 6-membered saturated or unsaturated heterocycle from the series morpholine, piperidine, thiomorpholine, pyrrolidine, tetrahydropyridine, which, if appropriate can be substituted once or twice by methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl.
  • R 8 very particularly preferably represents methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, -CF 3 , -CC1 3 , -CHF 2 , -CC1F 2 , -CHC1 2 , -CF 2 CHFC1, -CF 2 CH 2 F, -CF 2 CC1 3 , -CH 2 CF 3 , -CF 2 CHFCF 3 , -CH 2 CF 2 H, -CH 2 CF 2 CF 3 , -CF 2 CF 2 H or for -CF 2 CHFCF 3 .
  • R 9 very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, -CH 2 CF 3 , -CH 2 CF 2 H, -CH 2 CF 2 CF 3 , cyclopropyl, cyclopentyl or cyclohexyl.
  • R 10 very particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, -COMe, -COEt, -CO 2 Me, -CO 2 Et, cyclohexyl; Phenyl or benzyl, which in turn can be substituted one to four times in the aryl part, the same or different, by fluorine, chlorine, bromine or methyl.
  • R 1 1 very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl.
  • R 14 very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl or t-butyl.
  • R 15 very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl or cyano.
  • R 16 very particularly preferably represents hydrogen; for each optionally single to triple, identical or different by fluorine, chlorine, bromine, amino, hydroxy, cyano, nitro, methoxy, ethoxy, i-propoxy, trifluoromethoxy, -OCH 2 CF 3 , trichloromethoxy, difluoromethoxy, methylthio, trifluoromethylthio , Methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, t-butoxycarbonyl, methylcarbonyloxy, vinylcarbonyloxy, -O- (CH 2 ) 2 -0-,
  • Oxetanyl, dioxanyl, oxazolidinyl, dioxolanyl ,. Phenoxy, fluorophenoxy, -CONR R5, _NR 4 R5, -0NR 4 R5, -CH N-OCH 3 substituted methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, n-pentyl, isopentyl, siamyl, hexyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, Vinyl, allyl, butenyl, 2-isopentenyl, hexenyl, n-decenyl, ethynyl, propynyl, butynyl; or for each optionally single to triple, identical or different, by flu
  • Triazinyl triazolyl, tetrahydropyranyl, thietanyl, thietane dioxide, oxetanylmethyl, oxazolanylmethyl, dioxanylmethyl, dioxolanylmethyl, furylmethyl,
  • R 16 also very particularly preferably represents phenyl, benzyl, phenylethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylethyl, cyclobutylethyl, cyclopentylethyl, cyclohexyl Oxetanyl, oxazolanyl, dioxanyl, dioxolanyl, furyl, thienyl, pyrrolyl, oxazolyl, isoxazyl, imidazolyl, pyrazyl ,. Thiazolyl, pyridinyl, pyrimidinyl, pyridazyl, triazinyl,
  • R 17 very particularly preferably represents hydrogen, methyl or ethyl.
  • R 18 very particularly preferably represents hydrogen, hydroxyl, amino, methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, vinyl, allyl; or for each optionally single to triple, identical or different, by fluorine, chlorine, hydroxyl, methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, trifluoromethyl, trichloromethyl, Methoxy, ethoxy, trifluoromethoxy, methylthio, trifluoromethylthio, -O-CH 2 -O- substituted cyclopropyl, cyclopropylmethyl, cyclohexyl, phenyl, benzyl, phenylethyl, pyri- dinyl, pyridin
  • R 18 also very particularly preferably represents in each case optionally one to three times, identically or differently, by fluorine, chlorine, bromine, amino,
  • R 18 also very particularly preferably represents cyclopropyl, cyclopropylmethyl, cyclohexyl, phenyl, benzyl, phenylethyl, pyridinyl, pyridinylmethyl, pyridinylethyl, furyl, furfuryl, each of which is monosubstituted to trisubstituted in the same or different ways, the substituents being in addition to the "above" Nitro, methoxycarbonyl and ethoxycarbonyl can be selected.
  • R 17 and R 18 together with the nitrogen atom to which they are attached, very particularly preferably represent a 5- or 6-membered saturated heterocycle from the series piperazine, morpholine, piperidine, pyrrolidine, which are, if appropriate, simple to triple, same or different through
  • Methyl, ethyl, n-propyl or i-propyl can be substituted.
  • Q very particularly preferably represents one of the following groupings
  • radicals R 1] can have the same or different meanings if they occur more than once in the same heterocyclic grouping.
  • n very particularly preferably represents 0, 1, 2 or 3, where the repeating unit - (CHR 14 ) - within the side chain of a heterocyclic grouping can have the same or different meanings if m represents 2 or 3.
  • G very particularly preferably represents oxygen or sulfur.
  • R 19 and R 20 independently of one another very particularly preferably represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, or together for - (CH 2 ) 2 - or - (CH 2 ) 3 -.
  • R 21 very particularly preferably represents hydrogen, in each case methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl which is optionally substituted by t-butylcarbonyloxy or methoxy; or for each optionally mono- or disubstituted, identically or differently, by chlorine, cyano, methyl, ethyl, t-butyl, trifluoromethyl, s-butyloxycarbonyl, t-butyloxycarbonyl, n-octyloxycarbonyl, - (CH 2 ) 4 - substituted phenyl.
  • R 22 very particularly preferably represents hydrogen, methyl, ethyl or methoxymethyl.
  • R 23 very particularly preferably represents hydrogen, amino, methyl, ethyl, n-
  • R 1 , R 2 , X, n, p, Z and R have the meanings given above.
  • R 1 , R 2 , X, n, Z, R and R 9 have the meanings given above.
  • R 1 , R 2 , X, n, Z and R have the meanings given above.
  • X represents methyl, ethyl, chlorine, bromine, -CF 3 , methoxy or trifluoromethoxy
  • n 0, 1 or 2
  • X stands for identical or different radicals if n stands for 2
  • Y stands for -S- or -NR 9 -
  • Z represents -CH 2 - or - (CH 2 ) 2 -
  • E represents hydroxy, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, -NH-SO 2 Me or -NH-SO 2 Et,
  • R 9 represents hydrogen, methyl or ethyl.
  • Saturated hydrocarbon residues such as alkyl can, also in combination with
  • Heteroatoms e.g. in alkoxy, where possible, be straight-chain or branched.
  • Formula (II) provides a general definition of the thiols required as starting materials when carrying out process (A) according to the invention.
  • R 1 , R 2 , X and n are preferably, particularly preferably or very particularly preferably those meanings which, in connection with the description of the substances of the formula (I) according to the invention, are preferred, particularly preferred, etc. for these radicals . were called.
  • R 1 , R 2 , X and n have the meanings given above with the proviso that at least one of the radicals R 1 , R 2 or X is not hydrogen,
  • thiourea if appropriate in the presence of a diluent (for example methanol, water) and if appropriate in the presence of a base (for example sodium hydroxide, sodium ethanolate), or
  • R 1 , R 2 , X and n have the meanings given above,
  • a base e.g. sodium hydroxide, sodium ethanolate
  • an acid e.g. hydrochloric acid or trifluoroacetic acid
  • Pyridine derivatives are generally defined by the formulas (X) and (XI).
  • R 1 , R 2 , X and n are preferably, particularly preferably or very particularly preferably those meanings which, in connection with the description of the substances of the formula (I) according to the invention, are preferred, particularly preferred, etc. for these radicals . were called.
  • E 1 preferably stands for -OR 16 , -SR 16 or -NR 17 R 18 , particularly preferably for -OR 16 or -SR 16 , where R 16 , R 17 and R 18 are each preferred, particularly preferred or very particularly preferred for are those meanings which have already been mentioned as preferred, particularly preferred, etc. for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • Shark 1 preferably represents chlorine, bromine or iodine, particularly preferably chlorine or bromine.
  • Halogen compounds of the formula (III) are known and / or can be prepared by known processes.
  • Suitable diluents for carrying out process (A) according to the invention are all customary inert, organic solvents.
  • optionally halogenated aliphatic, alicyclic or 'aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane,
  • Acetonitrile or dimethylformamide are particularly preferably used.
  • Suitable acid binders for carrying out process (A) according to the invention are in each case all of the inorganic and organic bases customary for such reactions.
  • Alkaline earth or alkali metal hydroxides such as sodium hydroxide, calcium hydroxide, potassium hydroxide, or also ammonium hydroxide
  • alkali metal hydrides such as sodium hydride
  • alkali metal carbonates such as sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate, alkali metal or alkaline earth metal acetate, such as sodium acetate, potassium acetate, are preferably usable.
  • tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).
  • Alkali metal carbonates or hydrides are particularly preferably used, very particularly preferably potassium carbonate.
  • reaction temperatures can be varied within a substantial range when carrying out process (A) according to the invention.
  • temperatures between -20 ° C and 200 ° C, preferably between 0 ° C and 150 ° C, most preferably between 20 ° C and 100 ° C.
  • Formula (IV) provides a general definition of the halopyrimidines required as starting materials when carrying out process (B) according to the invention.
  • R 1 , R 2 , Z and A are preferred, particularly preferred or very particularly preferred for those meanings which, in connection with the description of the substances of the formula (I) according to the invention, are preferred for these radicals, particularly preferred etc. were called.
  • E 1 preferably stands for -OR 16 , -SR 16 or -NR 17 R 18 , particularly preferably for -OR 16 or -SR 16 , where R 16 , R 17 and R 18 are each preferred, particularly preferred or very particularly preferred for are those meanings which have already been mentioned as preferred, particularly preferred etc.
  • Shark 2 preferably represents fluorine, chlorine, bromine or iodine, particularly preferably chlorine, bromine or iodine, very particularly preferably chlorine or bromine.
  • halopyrimidines of the formula (IV) are known in some cases and / or can be prepared by known processes (cf. US 3,910,910).
  • E 1 stands for methoxy and Hai 2 stands for chlorine are new.
  • Formula (V) provides a general definition of the pyridine compounds required as starting materials when carrying out process (B) according to the invention.
  • X and n are preferably, particularly preferably or very particularly preferably, those meanings which have already been mentioned as preferred, particularly preferred, etc. for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • L preferably represents Sn (n-Bu) 3 , Sn (Me) 3 , Sn (phenyl) 3 , ZnBr or ZnCl, particularly preferably Sn (n-Bu) 3 , Sn (Me) 3 , Sn (phenyl) 3 or ZnBr, very particularly preferably for Sn (n-Bu) 3 , Sn (Me) 3 or ZnBr.
  • Pyridine compounds of the formula (V) are known and / or can be prepared by known processes.
  • Suitable diluents for carrying out process (B) according to the invention are all customary inert, organic solvents.
  • Halogenated aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; Chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether,
  • Dioxane tetrahydrofuran, 1, 2-dimethoxyethane, 1,2-diethoxyethane or anisole
  • Nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile
  • Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide.
  • Aromatic hydrocarbons are particularly preferably used, very particularly preferably benzene,
  • a palladium catalyst is generally used, which in turn can be used with or without the addition of further ligands.
  • Triarylphosphines, trialkylphosphines or arsines are suitable as ligands.
  • Dppf, PPh 3 , P (t-Bu) 3 , Pcy 3 or AsPh 3 are preferably used, particularly preferably dppf.
  • reaction temperatures can be varied over a wide range when carrying out process (B) according to the invention. In general, temperatures between -20 ° C and 200 ° C, preferably between
  • Formula (Ic) generally defines the pyridylpyrimidines required as starting materials when carrying out process (C) according to the invention.
  • R 1 , R 2 , X, n, Z and A are preferred, particularly preferred or very particularly preferred for those meanings which are already preferred for these radicals in connection with the description of the substances of the formula (I) according to the invention , particularly preferred, etc. were mentioned.
  • E 3 preferably stands for -OR 16 , where R 16 preferably, particularly preferably or very particularly preferably stands for those meanings which are already associated with the Description of the substances of the formula (I) according to the invention for these radicals as being preferred, particularly preferred etc. have been mentioned.
  • the pyridylpyrimidines of the formula (I-c) fall under the definition of the compounds of the formula (I) according to the invention and are prepared by one of the processes (A) or (B).
  • Formula (Id) generally defines the pyridylpyrimidines formed as intermediates when carrying out process (C) according to the invention.
  • R 1 , R 2 , X, n, Z and A are preferred, particularly preferred or very particularly preferred for those meanings which are already preferred for these radicals in connection with the description of the substances of the formula (I) according to the invention , particularly preferred, etc. were mentioned.
  • Formula (VI) provides a general definition of the amines required as starting materials when carrying out process (C) according to the invention.
  • R 17 and R 18 are preferably, particularly preferably or very particularly preferably, those meanings which have already been mentioned as preferred, particularly preferred, etc. for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • Amines of the formula (VI) are known and / or can be prepared by known processes.
  • Suitable diluents for carrying out process (C) according to the invention are all customary protic solvents.
  • Water or alcohols such as methanol, ethanol; Nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Esters such as methyl acetate or ethyl acetate.
  • Water or alcohols are particularly preferably used, very particularly preferably methanol or ethanol.
  • All customary dehydration reagents are suitable as water-absorbing reagents when carrying out process (C) according to the invention.
  • Carbodiimides can preferably be used. Dicyclohexylcarbodiimide (DCC) or N- (3-dimethylaminopropyl) -N'-ethyl-carbodiimide (EDC) is particularly preferably used.
  • Suitable bases for carrying out process (C) according to the invention are all inorganic and organic bases customary for such reactions.
  • Alkaline earth or alkali metal hydroxides such as sodium hydroxide, calcium hydroxide, potassium hydroxide, or else ammonium hydroxide, can preferably be used.
  • reaction temperatures can be varied over a wide range when carrying out process (C) according to the invention.
  • temperatures between -20 ° C and 200 ° C, preferably between 0 ° C and 150 ° C, most preferably between 20 ° C and 100 ° C.
  • 1 mol of compound of the formula (Ic) is generally first treated with a base in the first stage and in the second stage with 1 mol or a slight excess of the compound of formula (VI), as well as 1-1.5 mol% of water-absorbing reagent.
  • the reaction components in other ratios.
  • the processing takes place according to usual methods. In general, the reaction mixture is concentrated and the crude product is freed of any impurities which may be present using customary methods, such as chromatography or recrystallization.
  • Formula (If) provides a general definition of the pyridylpyrimidines required as starting materials when carrying out process (D) according to the invention.
  • R 1 , R 2 , X, n, Z and R are preferably, particularly preferably or very particularly preferably for those meanings which are already related with the description of the substances of the formula (I) according to the invention were mentioned as preferred, particularly preferred etc. for these radicals.
  • the pyridylpyrimidines of the formula (I-f) fall under the definition of the compounds of the formula (I) according to the invention and are, for example, according to one of the
  • Suitable oxidizing agents for carrying out process (D) according to the invention are all customary oxidizing agents which can be used for sulfur oxidation. Hydrogen peroxide, organic peracids such as peracetic acid, m-chloroperbenzoic acid, p-nitroperbenzoic acid or atmospheric oxygen are particularly suitable.
  • Inert organic solvents are also suitable as diluents for carrying out process (D) according to the invention.
  • Hydrocarbons such as gasoline, benzene, toluene, hexane or petroleum ether, are preferably used; chlorinated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride or chlorobenzene; Ethers, such as diethyl ether, dioxane or tetrahydrofuran; Carboxylic acids such as acetic acid or propionic acid; or dipolar aprotic solvents such as acetonitrile, acetone, ethyl acetate or dimethylformamide.
  • process (D) according to the invention can be carried out in the presence of an acid binder.
  • acid binder All commonly used organic and inorganic acid binders are suitable as such.
  • process (D) according to the invention can be carried out in the presence of a suitable catalyst.
  • a suitable catalyst All metal salt catalysts customarily used for such sulfur oxidations are suitable as such. Examples include ammonium molybdate and sodium tungstate.
  • reaction temperatures can be varied within a substantial range when carrying out process (D) according to the invention. In general, temperatures between -20 ° C and + 70 ° C, preferably at temperatures between 0 ° C and + 50 ° C.
  • 0.8 mol to 1.2 mol, preferably equimolar amounts, of oxidizing agent are generally employed per mol of compound of the formula (If), if one wishes to interrupt the oxidation of the sulfur at the sulfoxide stage .
  • 1.8 to 3.0 mol, preferably double molar amounts, of oxidizing agent are generally used per mol of compound of the formula (I-f).
  • the reaction, working up and isolation of the end products is carried out according to customary methods.
  • Formula (VII) provides a general definition of the methylsulfonylpyrimidines required as starting materials when carrying out process (E) according to the invention.
  • R 1 , R 2 , X and n are preferred, particularly preferred or very particularly preferred for those meanings which, in connection with the description of the substances of the formula (I) according to the invention, are preferred, particularly preferred, etc. for these radicals . were called.
  • the methylsulfonylpyrimidines of the formula (VII) are new. They can be made by
  • R 1 , R 2 , X and n have the meanings given above,
  • oxidizing agent e.g. m-chloroperbenzoic acid
  • diluent e.g. dichloromethane
  • Formula (XVI) provides a general definition of the methylthio derivatives required as starting materials when carrying out process (c).
  • R 1 , R 2 , X and n are preferably, particularly preferably or very particularly preferably those meanings which, in connection with the description of the substances of the formula (I) according to the invention, are preferred, particularly preferred, etc. for these radicals . were called.
  • Methylthio derivatives of the formula (XVI) are new. They can be made by
  • R 1 , R 2 , X and n have the meanings given above with a methylating reagent (eg iodomethane), if appropriate in the presence of a diluent (for example acetonitrile) and if appropriate in the presence of an acid binder (for example potassium carbonate).
  • a methylating reagent eg iodomethane
  • a diluent for example acetonitrile
  • an acid binder for example potassium carbonate
  • Formula (VIII) provides a general definition of the amines required as starting materials when carrying out process (E) according to the invention.
  • Z and R 9 are preferably, particularly preferably or very particularly preferably, those meanings which have already been mentioned as preferred, particularly preferred, etc. for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • Amines of the formula (VIII) are known and / or can be prepared by known processes.
  • Suitable diluents for carrying out process (E) according to the invention are all customary inert, organic solvents.
  • Nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile can preferably be used;
  • Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide;
  • Ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole;
  • Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide or sulfones such as
  • the bases used in carrying out process (E) according to the invention are in each case all of the inorganic and organic bases customary for such reactions into consideration.
  • Alkaline earth or alkali metal hydroxides such as sodium hydroxide, calcium hydroxide, potassium hydroxide, or also ammonium hydroxide
  • alkali metal hydrides such as sodium hydride
  • alkali metal carbonates such as sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate, alkali metal or alkaline earth metal acetate, potassium acetate, sodium acetate, sodium acetate, sodium acetate, sodium acetate, sodium acetate, sodium acetate, sodium acetate, sodium acetate, sodium acetate, sodium acetate, sodium acetate, sodium acetate, sodium acetate, sodium acetate, sodium acetate, are preferably used.
  • tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).
  • Alkali metal carbonates or hydrides are particularly preferably used, very particularly preferably potassium carbonate or sodium hydride.
  • reaction temperatures can be varied within a substantial range when carrying out process (E) according to the invention.
  • temperatures between -20 ° C and 200 ° C, preferably between 0 ° C and 150 ° C, most preferably between 20 ° C and 100 ° C.
  • Formula (VII) The methylsulfonylpyrimidines of the formula (VII) required as starting materials when carrying out process (F) according to the invention have already been described when carrying out process (E).
  • Formula (IX) provides a general definition of the hydroxy compounds required as starting materials when carrying out process (F) according to the invention.
  • Z is preferably, particularly preferably or very particularly preferably those meanings which have already been mentioned as preferred, particularly preferred, etc. for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • Hydroxy compounds of the formula (IX) are known and / or can be prepared by known processes.
  • Suitable diluents for carrying out process (F) according to the invention are all customary inert, organic solvents.
  • Nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile can preferably be used;
  • Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide;
  • Esters such as methyl acetate or ethyl acetate;
  • Sulfoxides such as dimethyl sulfoxide or sulfones, such as sulfolane.
  • Nitriles, amides or sulfoxides are particularly preferably used, very particularly preferably acetonitrile, dimethylformamide or dimethyl sulfoxide.
  • Suitable bases for carrying out process (F) according to the invention are all inorganic and organic bases customary for such reactions.
  • Alkaline earth or alkali metal hydroxides such as sodium hydroxide, calcium hydroxide, potassium hydroxide, or also ammonium hydroxide, alkali metal hydrides, such as sodium hydride, alkali metal carbonates, such as, are preferably usable
  • Sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate, alkali or alkaline earth metal acetates such as sodium acetate, potassium acetate, calcium acetate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylamine
  • DABCO Diazabicyclooctane
  • DBN Diazabicyclonon.en
  • reaction temperatures can be varied over a wide range when carrying out process (F) according to the invention. In general, temperatures between -20 ° C and 200 ° C, preferably between 0 ° C and 150 ° C, most preferably between 20 ° C and 100 ° C.
  • Formula (XII) provides a general definition of the amidines required as starting materials when carrying out process (G) according to the invention.
  • Z is preferably, particularly preferably or very particularly preferably those meanings which have already been mentioned as preferred, particularly preferred, etc. for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • Amidines of the formula (XII) are known and / or can be prepared by known processes.
  • Suitable diluents for carrying out process (G) according to the invention are all customary protic solvents.
  • Water or alcohols such as methanol, ethanol; Nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Esters such as methyl acetate or ethyl acetate.
  • Water or alcohols are particularly preferably used, very particularly preferably methanol or ethanol.
  • Suitable bases for carrying out process (G) according to the invention are all inorganic and organic bases customary for such reactions.
  • Those preferably utilizable are alkaline earth or alkali metal hydroxides such as sodium hydroxide, calcium hydroxide, potassium hydroxide, or ammonium hydroxide, alkali metal hydrides such as sodium hydride, alkali metal carbonates such as sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate, alkali metal or alkaline earth metal acetates such as sodium acetate, potassium acetate, calcium ciumacetat, alkali metal alkoxides such as Sodium methoxide, sodium ethoxide.
  • Alkali metal alcoholates are particularly preferably used, very particularly preferably sodium methoxide.
  • reaction temperatures can in each case be varied within a relatively wide range. In general, temperatures between - 20 ° C and 200 ° C, preferably between 0 ° C and 150 ° C, most preferably between 20 ° C and 100 ° C.
  • Formula (Ik) provides a general definition of the pyridylpyrimidines required as starting materials when carrying out process (H) according to the invention.
  • R 1 , R 2 , X, n, Z and A are preferred, particularly preferred or very particularly preferred for those meanings which are already preferred for these radicals in connection with the description of the substances of the formula (I) according to the invention , particularly preferred, etc. were mentioned.
  • Y 2 preferably represents a direct bond, sulfur, oxygen or NR 9 .
  • Pyridylpyrimidines of the formula (I-k) are also compounds according to the invention which can be prepared, for example, by
  • R 1 , R 2 , X, n, Y 2 , A and E 3 have the meanings given above,
  • a base e.g. sodium hydroxide
  • a diluent e.g. methanol
  • Pyridylpyrimidines of formula (Iu) are also part of this invention and can be prepared via process (A) or (B).
  • Formula (XIII) provides a general definition of the hydroxides required as starting materials when carrying out process (H) according to the invention.
  • M is preferably, particularly preferably or very particularly preferably those meanings which have already been mentioned as preferred, particularly preferred, etc. for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • Hydroxides of the formula (XIII) are known and / or can be prepared by known processes.
  • Suitable diluents for carrying out the process (H) according to the invention are all customary protic solvents.
  • Water or alcohols such as methanol, ethanol; Nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile. Water or alcohols are particularly preferably used.
  • reaction temperatures can be varied within a substantial range when carrying out process (H) according to the invention.
  • temperatures between 0 ° C and 200 ° C, preferably between 0 ° C and 150 ° C, most preferably between 20 ° C and 100 ° C.
  • Formula (XIV) provides a general definition of the nitriles required as starting materials when carrying out process (J) according to the invention.
  • R 1 , R 2 , X, n, Y and Z are preferred, particularly preferred or very particularly preferred for those meanings which are already preferred for these radicals in connection with the description of the substances of the formula (I) according to the invention , particularly preferred, etc. were mentioned.
  • Nitriles of the formula (XIV) are new. They can be made by
  • R 1 , R 2 , X and n have the meanings given above,
  • Formula (XVII) provides a general definition of the chlorinated nitriles required as starting materials in carrying out process (f).
  • Z is preferably, particularly preferably or very particularly preferably those meanings which have already been mentioned as preferred, particularly preferred, etc. for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • trialkyltin azides required for carrying out process (J) according to the invention are known. Trimethyltin azide or is preferably used
  • Suitable diluents for carrying out process (J) according to the invention are all customary inert, organic solvents.
  • Halogenated aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin, may optionally be used; Chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole;
  • Nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate; Sulfoxides, such as dimethyl sulfoxide or sulfones, such as sulfolane. Toluene is particularly preferably used.
  • Formula (In) provides a general definition of the pyridylpyrimidines required as starting materials when carrying out process (K) according to the invention.
  • R 1 , R 2 , X, n and Z are preferred, particularly preferred or very particularly preferred for those meanings which, in connection with the description of the substances of the formula (I) according to the invention, are preferred for these radicals, particularly preferred etc. were mentioned.
  • Y 2 preferably represents a direct "bond, sulfur, oxygen or NR. 9
  • Pyridylpyrimidines of the formula (I-n) are new. They can be made by
  • Z has the meanings given above, Y 3 represents oxygen, sulfur or -NR 9 -, where R 9 has the meanings given above, or
  • R 1 , R 2 , X and n have the meanings given above,
  • the compounds required as starting materials in carrying out process (g) are generally defined by the formulas (XVIII) and (XIX).
  • Z is preferably, particularly preferably or very particularly preferably those meanings which have already been mentioned as preferred, particularly preferred, etc. for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • Suitable diluents for carrying out process (K) according to the invention are all customary inert, organic solvents.
  • Nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile can preferably be used;
  • Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide;
  • Ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole;
  • Esters such as methyl acetate or ethyl acetate;
  • Sulfoxides such as dimethyl sulfoxide or sulfones,
  • catalysts customary for a hydrogenation reaction are used as the catalyst.
  • Palladium or platinum catalysts can preferably be used, particularly preferably palladium / activated carbon.
  • reaction temperatures can be varied over a wide range when carrying out process (K) according to the invention. In general one works at temperatures between -20 ° C and 200 ° C, preferably between 0 ° C and 150 ° C.
  • Formula (XV) provides a general definition of the keto compounds required as starting materials when carrying out process (L) according to the invention.
  • R 1 , R 2 , X, n and Z are preferred, particularly preferred or very particularly preferred for those meanings which, in connection with the description of the substances of the formula (I) according to the invention, are particularly preferred for these radicals preferred etc. were mentioned.
  • Y 2 preferably represents a direct bond, sulfur, oxygen or NR 9 .
  • Keto compounds of formula (XV) are new. They can be made by
  • a diluent for example tetrahydrofuran
  • an acid binder for example triethylamine
  • R 1 , R 2 , X and n have the meanings given above,
  • a ner thinner e.g. tetrahydrofuran
  • an acid binder e.g. triethylamine
  • Formula (XX) provides a general definition of the compounds required as starting materials in carrying out process (h).
  • R 1 , R 2 , X and n are preferably, particularly preferably or very particularly preferably those meanings which, in connection with the description of the substances of the formula (I) according to the invention, are preferred, particularly preferred, for these radicals. trains etc. were mentioned.
  • Y 3 preferably represents sulfur, oxygen or ⁇ R 9 .
  • Formula (XXI) provides a general definition of the methyl ketones required as starting materials when carrying out process (h).
  • Z is preferably, particularly preferably or very particularly preferably those meanings which have already been mentioned as preferred, particularly preferred, etc. for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • Methyl ketones of the formula (XXI) are known.
  • the methylsulfonylpyrimidines of the formula (VII) required as starting materials when carrying out process (i) have already been described when carrying out process (E).
  • Suitable diluents for carrying out the process (L) according to the invention are all customary inert, organic solvents.
  • Halogenated aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; Chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether,
  • the procedure is generally carried out under atmospheric pressure. However, it is also possible to work under increased or reduced pressure.
  • the active compounds according to the invention are suitable for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stocks and materials and in the hygiene sector, with good plant tolerance and favorable warm-blood toxicity. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the pests mentioned above include:
  • Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber. From the order of the Diplopoda e.g. Blaniulus guttulatus.
  • Thysanura e.g. Lepisma saccharina.
  • Phthiraptera for example Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp ..
  • Thysanoptera for example Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.
  • Hofmannophila pseudospretella Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae.
  • Anthrenus spp. Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Oscinella frit Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp ..
  • Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp.,
  • the compounds of the formula (I) according to the invention are distinguished in particular by an excellent action against caterpillars, beetle larvae, spider mites, aphids and leaf miners. If appropriate, the compounds according to the invention can also be used in certain concentrations or application rates as herbicides and microbicides, for example as fungicides, antifungals and bactericides. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesirable wild plants or crop plants (including naturally occurring crop plants).
  • Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and parts of plants with the active compounds takes place directly or by acting on their surroundings, living space or storage space according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and in the case of propagation material, in particular in the case of seeds, furthermore by single- or multi-layer coating.
  • the active compounds according to the invention can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances .
  • These formulations are prepared in a known manner, for example by mixing the active compounds according to the invention with extenders, that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents.
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as
  • Chlorobenzenes chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Ammonium salts and natural rock meals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock meals, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems;
  • Possible emulsifiers and / or foam-generating agents are: for example nonionogenic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • emulsifiers and / or foam-generating agents are: for example nonionogenic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • dispersants for example lignin sulfate leachate and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can be used in commercially available formulations and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides, attractants, sterilants, bactericides,
  • Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
  • Iodocarb Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaldione,
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazole, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin, Nickel-dimethyldithiochalamopropyl, Nitrile
  • Tridemorph triflumizole, triforin, triticonazole, uniconazole,
  • Dagger G OK-8705, OK-8801, ⁇ - (1, 1-dimethylethyl) -ß- (2-phenoxyethyl) - 1 H- 1, 2,4-triazole-1-ethanol, - (2,4- Dichlorophenyl) -ß-fluoro-ß-propyl-1 H-1, 2,4-triazole-1-ethanol, ⁇ - (2,4-dichlorophenyl) -ß-methoxy- ⁇ -methyl-1 H-1, 2 , 4-triazole-1-ethanol, ⁇ - (5-yl-l, 3-dioxan-5-yl) -ß - [[4- (trifluoromemyl) -phenyl] -me len] -lH-1,2 , 4-triazole-1-ethanol,
  • Fenamiphos Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate,
  • Fipronil fluazuron, flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,
  • Granuloseviruses Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
  • Metolcarb Metoxadiazone, Mevinphos, Milbemectin, Monocrotophos,
  • Paecilomyces fumosoroseus Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A,
  • Pirimiphos M Profenofos, Promecarb, Propoxur, Prothiofos, Prothoat, Pymetrozine,
  • Tefluthrin Temephos, Temivinphos, Terbufos, Tetrachlorvinphos, Theta-cyper-methrin, Thiamethoxam, Thiapronil, Thiatriphos, Thiocyclam hydrogen oxalate, Thiodicarb, Thiofanox, Thuringiensin, Tralocythrin, Tralometene-trinone, Tralomate- nehrin Triflumuron, trimethacarb, Vamidothion, Vaniliprole, Verticillium lecanii
  • the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds which increase the activity of the active compounds according to the invention without the added synergist itself having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • the active ingredient When used against hygiene pests and pests of stored products, the active ingredient is distinguished by an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates.
  • plants and their parts can be treated according to the invention.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods are treated.
  • Organisms and their parts treated.
  • plants of the plant cultivars which are in each case commercially available or in use are particularly preferably treated.
  • Plant cultivars are understood to mean plants with certain properties (“traits”) which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, bio- and genotypes.
  • the treatment according to the invention can also give rise to additive ("synergistic") effects.
  • additive for example, reduced application rates and / or widening the spectrum of action and / or an increase in the effect of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher
  • Nutritional value of the harvested products higher shelf life and / or workability of the harvested products possible, which go beyond the expected effects.
  • the preferred transgenic (genetically preserved) plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification which gives these plants particularly advantageous valuable properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or Workability of the harvested products Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or V iren as well as an increased tolerance of the plants to certain herbicidal active ingredients.
  • microbial pests such as against insects, mites, phytopathogenic fungi, bacteria and / or V iren as well as an increased tolerance of the plants to certain herbicidal active ingredients.
  • transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes and cotton and rapeseed are highlighted.
  • the properties (“traits”) which are particularly emphasized are the plants' increased defense against insects by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), Cry ⁇ A (b), Cry ⁇ A (c), CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
  • Bt plants The increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins are also particularly emphasized as properties (“traits”).
  • Plant plants are corn varieties, cotton varieties, soy varieties and potato varieties that are sold under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato).
  • herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example corn,
  • the herbicide-resistant plants include the varieties sold under the name Clearf ⁇ eld® (eg maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties (“traits”).
  • the plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active compound mixtures according to the invention. The preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • the active substances according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as shield ticks, leather ticks, space mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, Hairlooms, featherlings and fleas.
  • animal parasites ectoparasites
  • shield ticks leather ticks
  • space mites space mites
  • running mites running mites
  • flies stinging and licking
  • parasitic fly larvae lice, Hairlooms, featherlings and fleas.
  • Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediedulus spp., Phtirus spp., Solenopotes spp ..
  • Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota ., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Glossina spp., Calliphora spp., Glossina spp.,
  • Xenopsylla spp. Ceratophyllus spp .. From the order of the Heteropterida, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp ..
  • Actinedida Prostigmata
  • Acaridida e.g. Acarapis spp., Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp. Pterolichus spp., Psoroptes spp., Chorioptes spp.,
  • Otodectes spp. Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp ..
  • the active compounds of the formula (I) according to the invention are also suitable for combating arthropods which are agricultural animals, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as dogs, cats, house birds, aquarium fish and so-called experimental animals such as hamsters, guinea pigs, rats and mice.
  • arthropods are agricultural animals, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as dogs, cats, house birds, aquarium fish and so-called experimental animals such as hamsters, guinea pigs, rats and mice.
  • the active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, through nasal
  • dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing, powdering and with the help of shaped articles containing active ingredients, such as collars, ear tags, tail tags , Limb straps, holsters, marking devices etc.
  • active ingredients such as collars, ear tags, tail tags , Limb straps, holsters, marking devices etc.
  • the active compounds of the formula (I) according to the invention can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds according to the invention in an amount of 1 to 80% by weight, apply directly or after 100 to 10,000-fold dilution or use it as a chemical bath.
  • formulations for example powders, emulsions, flowable agents
  • insects may be mentioned by way of example and preferably, but without limitation:
  • Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwinisis, Zootermopsis nevadensis, Coptotermes formosanus.
  • Bristle tails such as Lepisma saccharina.
  • non-living materials such as preferably plastics, adhesives, glues, papers and cartons, leather, wood, wood processing products and paints.
  • the one to be protected against insect attack is very particularly preferably
  • Wood and wood processing products which can be protected by the agent according to the invention or mixtures containing it are to be understood as examples:
  • the active compounds according to the invention can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
  • the formulations mentioned can be prepared in a manner known per se, for example by mixing the active compounds according to the invention with at least a solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments and other processing aids.
  • the insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active compound according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
  • the amount of the agents or concentrates used depends on the type and occurrence of the insects and on the medium. The optimal amount can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.
  • organic-chemical solvent or solvent mixture and / or an oily or oily or low-volatility organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agents.
  • the organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
  • Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.
  • Mineral oils with a boiling range of 170 to 220 ° C, test gasoline with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C are advantageous.
  • Turpentine oil and the like liquid aliphatic hydrocarbons with a boiling range from 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range from 180 to 220 ° C. and / or spindle oil and / or monochloronaphthalene, preferably ⁇ -monochloronaphthalene, are used.
  • organic non-volatile oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.
  • Solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture replaced.
  • the known organic-chemical binders are synthetic resins which are known to be water-dilutable and / or soluble or dispersible or emulsifiable in the organic-chemical solvents used and / or binding drying oils, in particular binders consisting of or containing an acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders on the Base of a natural and / or synthetic resin used.
  • binders consisting of or containing an acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-cou
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellants, odor correctors and inhibitors or anticorrosive agents and the like can be used.
  • At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder.
  • Alkyd resins having an oil content of more than 45% by weight, preferably 50 to, are preferred according to the invention
  • binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).
  • the plasticizers originate from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexy ⁇ ) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate or higher, glycolic ether , Glycerol ester and p-toluenesulfonic acid ester.
  • phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate
  • phosphoric acid esters such as tributyl phosphate
  • adipic acid esters such as di- (2-ethylhexy ⁇ ) adipate
  • stearates such as butyl stearate or amyl stea
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
  • Water is also particularly suitable as a solvent or diluent, if appropriate in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
  • a particularly effective wood protection is achieved by industrial impregnation processes, e.g. vacuum, double vacuum or pressure processes.
  • the ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides.
  • insecticides and fungicides mentioned in WO 94/29 268 are preferably suitable as additional admixing partners.
  • the compounds mentioned in this document are an integral part of the present application.
  • Insecticides such as chloropyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, delta-methrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthrin, thiaphenoxidur, and trifluoropuron, triaphenoluron, and methaclopronid, triaphenoluron, as well as trifluoromethane, as well as trifluoride and trifluoromethane, as well as trifluoride and trifluoride, as well Fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyconconazole, metconazole, imazalil, dichlorofluoride, tolylfluanid, 3-iodo-2-propynyl buty
  • the compounds according to the invention can be used to protect objects, in particular ship hulls, sieves, nets, structures, quay systems and signaling systems which come into contact with sea or brackish water.
  • heavy metals such as e.g. in bis (trialkyltin) sulfides, tri-M-butyltin laurate, tri-n-butyltin chloride, copper (I) oxide, triethyltin chloride, tri-n-butyl (2-phenyl-4-chlorophenoxy) tin, tributyltin oxide, Molybdenum disulfide, antimony oxide, polymeric butyl titanate, phenyl (bispyridine) bismuth chloride, tri-butyltin fluoride, manganese ethylene bisthiocarbamate,
  • heavy metals such as e.g. in bis (trialkyltin) sulfides, tri-M-butyltin laurate, tri-n-butyltin chloride, copper (I) oxide, triethyltin chloride, tri-n-butyl (2-phenyl-4-chlorophenoxy) tin,
  • the ready-to-use antifouling paints may also contain other active ingredients, preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.
  • Suitable combination partners for the antifouling agents according to the invention are preferably:
  • Algicides such as 2-tert-butylamino-4-cyclopropylamino-6-methylthio-1, 3,5-triazine, dichlorophene,
  • the antifouling agents used contain the active compound according to the invention of the compounds according to the invention in a concentration of 0.001 to 50% by weight, in particular of 0.01 to 20% by weight.
  • the 'inventive antifouling compositions contain the customary components such as those described in Ungerer, Chem. Ind., 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973..
  • antifouling paints contain in particular binders.
  • Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system, in particular in an aqueous system, vinyl chlorine-vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene / styrene / acrylonitrile rubbers, drying agents Oils such as linseed oil, resin esters or modified hard resins in combination with tar or bitumen, asphalt and epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.
  • Paints may also contain inorganic pigments, organic pigments or dyes, which are preferably insoluble in sea water. Paints may also contain materials such as rosin to enable controlled release of the active ingredients. The paints may also contain plasticizers, modifiers affecting theological properties, and other conventional ingredients.
  • the compounds according to the invention or those mentioned above can also be used in self-polishing antifouling systems
  • the active substances according to the invention are also suitable for controlling animal pests, in particular insects, arachnids and mites, which live in closed spaces, such as, for example, apartments, factories, offices, vehicle cabins and the like. occurrence. To combat these pests, they can be used alone or in combination with other active ingredients and auxiliaries in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:
  • Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Omithodorus moubat, Rhipi- cephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermato- phagoides pteronissimus, Dermatophagoides forinae.
  • Opiliones e.g. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
  • Isopoda e.g. Oniscus asellus, Porcellio scaber.
  • Diplopoda e.g. Blaniulus guttulatus, Polydesmus spp ..
  • Musca domestica Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa.
  • Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
  • Ctenocephalides canis Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • the specified logP values were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 43 ° C.
  • Eluents for determination in the acidic range 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile.
  • the calibration was carried out using unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive alkanones).
  • the lambda maximums were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
  • Solvent 30 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • Cotton leaves which are heavily infested with the cotton aphid (Aphis gossypii), are treated by dipping into the active ingredient preparation of the desired concentration.
  • the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • Active substances Active ingredient Degree of kill concentration in% after 6 d in ppm
  • Solvent 3 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • Cucumber plants (Cucumis sativus), which are heavily affected by all stages of the thrips (Franklinella occidentalis), are sprayed with an active ingredient preparation of the desired concentration.
  • the effect is determined in%. 100% means that all thrips have been killed; 0% means that no thrips have been killed.
  • Vessels are filled with sand, active ingredient solution, Meloidogyne incognita egg larva suspension and lettuce seeds.
  • the lettuce seeds germinate and the plantlets develop.
  • the galls develop at the roots.
  • the nematicidal effect is determined in% using the formation of bile. 100% means that no galls were found; 0% means that the number of galls on the treated plants corresponds to that of the untreated control.
  • Solvent 30 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • Active substances Active substance Degree of killing concentration in% after 14 d in pm
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 2 parts by weight of alkylaryl polyglycol ether
  • Cabbage leaves (Brassica oleracea), which are heavily infested with peach aphids (Myzus persicae), are treated by being dipped into the preparation of active compound of the desired concentration.
  • the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • Solvent 30 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • Active substances Active ingredient Degree of kill concentration in% after 6 d in ppm
  • Active substances Active ingredient Degree of kill concentration in% after 6 d in ppm
  • Active substances Active ingredient Degree of kill concentration in% after 6 d in ppm
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 2 parts by weight of alkylaryl polyglycol ether
  • Active substances Active ingredient Degree of kill concentration in% after 6 d in ppm
  • Active substances Active ingredient Degree of kill concentration in% after 6 d in ppm
  • Active substances Active ingredient Degree of kill concentration in% after 6 d in ppm
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with larvae of the horseradish leaf beetle (Phaedon cochleariae) while the leaves are still moist.
  • the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
  • Solvent 30 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 2 parts by weight of alkylaryl polyglycol ether
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the army worm (Spodoptera fmgiperda) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Amount of emulsifier and dilute the concentrate with water to the desired concentration is required.
  • the active ingredient preparation is poured onto the floor.
  • the concentration of the active ingredient in the preparation is practically irrelevant, the only decisive factor is the amount of active ingredient per unit volume of soil, which is given in ppm (mg / 1). You fill the bottom in 0.25 1 pots and let them stand at 20 ° C.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Soybean shoots (Glycine max) of the Roundup Ready variety (trademark of Monsanto Comp. USA) are treated by dipping into the preparation of active compound of the desired concentration and populated with the tobacco bud caterpillar Heliothis virescens while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne de nouvelles pyridylpyrimidines de formule (I), dans laquelle R1, R2, X, n, Y, Z et R ont les significations indiquées dans la description, plusieurs procédés pour produire ces substances et leur utilisation pour lutter contre les parasites, ainsi que de nouveaux produits intermédiaires et procédés de production associés.
EP02701270A 2001-02-22 2002-02-11 Pyridylpyrimidines en tant qu'agents de lutte contre les parasites Withdrawn EP1367893A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10108481A DE10108481A1 (de) 2001-02-22 2001-02-22 Pyridylpyrimidine
DE10108481 2001-02-22
PCT/EP2002/001403 WO2002067684A1 (fr) 2001-02-22 2002-02-11 Pyridylpyrimidines en tant qu'agents de lutte contre les parasites

Publications (1)

Publication Number Publication Date
EP1367893A1 true EP1367893A1 (fr) 2003-12-10

Family

ID=7675082

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EP02701270A Withdrawn EP1367893A1 (fr) 2001-02-22 2002-02-11 Pyridylpyrimidines en tant qu'agents de lutte contre les parasites

Country Status (9)

Country Link
US (1) US7238697B2 (fr)
EP (1) EP1367893A1 (fr)
JP (1) JP2004524310A (fr)
KR (1) KR20030076642A (fr)
CN (1) CN1856249A (fr)
BR (1) BR0207768A (fr)
DE (1) DE10108481A1 (fr)
TW (1) TWI228126B (fr)
WO (1) WO2002067684A1 (fr)

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ATE521353T1 (de) * 2000-10-23 2011-09-15 Glaxosmithkline Llc Neues trisubstitutiertes 8h-pyridoä2,3- düpyrimidin-7-onderivat zur behandlung von durch csbp/p38kinase vermittelten krankheiten
US6818631B1 (en) 2003-08-15 2004-11-16 Nippon Soda Co. Ltd. Fungicidal pyrimidine derivatives
AR053346A1 (es) * 2005-03-25 2007-05-02 Glaxo Group Ltd Compuesto derivado de 8h -pirido (2,3-d) pirimidin -7 ona 2,4,8- trisustituida composicion farmaceutica y uso para preparar una composicion para tratamiento y profilxis de una enfermedad mediada por la quinasa csbp/ rk/p38
CN101495475A (zh) * 2005-03-25 2009-07-29 葛兰素集团有限公司 制备吡啶并[2,3-d]嘧啶-7-酮和3,4-二氢嘧啶并[4,5-d]嘧啶-2(1H)-酮衍生物的方法
EP2129663A2 (fr) * 2007-02-28 2009-12-09 Ranbaxy Laboratories Limited Antagonistes des récepteurs muscariniques
EP2246335A1 (fr) 2009-02-17 2010-11-03 Bayer CropScience AG Aminopyridineamides en tant que pesticides
CA2759385A1 (fr) * 2009-04-27 2010-11-04 Dow Agrosciences, Llc Composes pyridine insecticides
GB0916881D0 (en) * 2009-09-25 2009-11-11 Electrophoretics Ltd Mass labels
WO2017164108A1 (fr) * 2016-03-25 2017-09-28 住友化学株式会社 Composé hétérocyclique
US11149027B2 (en) 2016-03-31 2021-10-19 Sumitomo Chemical Company, Limited Heterocyclic compound
EP3444239B1 (fr) 2016-04-06 2020-11-04 Sumitomo Chemical Company, Limited Composés hétérocycliques pour lutter contre les arthropodes
AU2017302980A1 (en) * 2016-07-25 2019-01-03 Basf Se Herbicidal pyrimidine compounds
EP3549933B1 (fr) * 2016-12-01 2022-02-16 Sumitomo Chemical Company, Limited Composé hétérocyclique et agent de lutte contre les arthropodes nuisibles le contenant
RU2019142439A (ru) * 2017-06-26 2021-06-21 Ниппон Сода Ко., Лтд. Гетероарил-пиримидиновое соединение и средство для борьбы с вредителями
CN118985624B (zh) * 2024-07-05 2025-10-10 云南大学 一种嘧啶类化合物在制备防治植物根结线虫制剂中的应用

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WO1996033972A1 (fr) * 1995-04-28 1996-10-31 Glaxo Group Limited Procedes de synthese de divers ensembles de pyridines, pyrimidines, derives 1,4-dihydro de ces composes et derives de piperidine
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Also Published As

Publication number Publication date
DE10108481A1 (de) 2002-10-24
KR20030076642A (ko) 2003-09-26
US7238697B2 (en) 2007-07-03
TWI228126B (en) 2005-02-21
JP2004524310A (ja) 2004-08-12
CN1856249A (zh) 2006-11-01
BR0207768A (pt) 2004-03-09
US20040077641A1 (en) 2004-04-22
WO2002067684A1 (fr) 2002-09-06

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