EP0759909A1 - Derives d'heterocyclylamino-cycloalcoyle et d'heterocyclyloxy-cycloalcoyle, leur preparation et leur utilisation comme pesticides et comme fongicides - Google Patents

Derives d'heterocyclylamino-cycloalcoyle et d'heterocyclyloxy-cycloalcoyle, leur preparation et leur utilisation comme pesticides et comme fongicides

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Publication number
EP0759909A1
EP0759909A1 EP95919376A EP95919376A EP0759909A1 EP 0759909 A1 EP0759909 A1 EP 0759909A1 EP 95919376 A EP95919376 A EP 95919376A EP 95919376 A EP95919376 A EP 95919376A EP 0759909 A1 EP0759909 A1 EP 0759909A1
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EP
European Patent Office
Prior art keywords
formula
alkyl
oxygen
compound
hydrogen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP95919376A
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German (de)
English (en)
Inventor
Wolfgang Schaper
Rainer Preuss
Peter Braun
Werner Knauf
Burkhard Sachse
Anna Waltersdorfer
Manfred Kern
Peter Lümmen
Werner Bonin
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Bayer CropScience AG
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Hoechst Schering Agrevo GmbH
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Publication of EP0759909A1 publication Critical patent/EP0759909A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/88—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/94—Nitrogen atoms

Definitions

  • Heterocyclylamino and heterocyclyloxy-cycloalkyl derivatives their preparation and their use as pesticides and fungicides
  • residues and groups are defined as below, which, with good plant tolerance and favorable warm-blood toxicity, are very good for combating animal pests, such as insects, arachnids, nematodes, helminths and molluscs, for combating endo- and ectoparasites in the veterinary field and for combat harmful fungi.
  • the invention therefore relates to compounds of the formula I in which
  • R 1 is hydrogen, halogen, (C r C 4 ) alkyl or (C 3 -C 5 ) cycloalkyl;
  • R 2 and R 3 are the same or different and are each hydrogen, (C r C 4 ) alkyl, (C r C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl , (C 2 -C 4 ) alkynyl, (C 2 -C 4 ) haloalkynyl, (C r C 4 ) alkoxy, (C r C 4 ) haloalkoxy, (C r C 4 ) alkoxy- (C r C 4 ) -alkyl, (C r C 4 ) -haloalkoxy- (C r C 4 ) -alkyl, (C r C 4 ) -haloalkoxy- (C r C 4 )
  • R 2 and R 3 together with the carbon atoms to which they are attached form an unsaturated 5- or 6-membered isocyclic ring which, if it is a 5-ring, instead of CH 2 is an oxygen or sulfur atom or which, if it is a 6-ring, can contain one or two nitrogen atoms instead of one or two CH units and which is optionally substituted by 1, 2 or 3 identical or different radicals and these radicals (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, preferably trifluoromethyl, halogen, (CC 4 ) alkoxy or (C 1 -C 4 ) haloalkoxy; or
  • R 2 and R 3 together with the carbon atoms to which they are attached form a saturated 5-, 6- or 7-membered isocyclic ring which may contain oxygen and / or sulfur instead of one or two CH 2 groups and which is optionally substituted by 1, 2 or 3 (C r C 4 ) alkyl groups;
  • A represents CH or N
  • X represents NH, oxygen or sulfur
  • E represents a direct bond or a straight-chain or branched (C r C 4 ) alkanediyl group, preferably a direct bond; n is an integer from 2 to 7; R 4 represents hydrogen or (C r C 4 ) alkyl;
  • Y represents oxygen or a direct bond
  • W represents oxygen or sulfur, preferably oxygen
  • Z represents a radical DR 5 or NR 5 R 6 ;
  • D represents oxygen, sulfur or a direct bond, preferably oxygen or a direct bond
  • R 5 and R 6 are the same or different and are hydrogen, alkyl, alkenyl,
  • Alkynyl, aryl or heterocyclyl mean, where the aryl or heterocyclyl radicals listed may be unsubstituted or may be provided with up to three, in the case of fluorine, up to the maximum number of the same of the different radicals and in the alkyl, alkenyl or alkynyl radicals mentioned.
  • Residues one or more, preferably up to three, non-adjacent saturated carbon units by a carbonyl group or by heteroatom units, such as oxygen, S (O) x , with x 0, 1 or 2, NR 9 or SiR 7 R 8 can be replaced, where R 9 is hydrogen, (C 1 -C 4 ) alkyl, (C r C 4 ) alkoxy or (C r C 4 ) alkanoyl and R 7 and R 8 (C r C 4 ) - Alkyl, preferably methyl, mean; and in which, in addition, 3 to 12 atoms of these hydrocarbon radicals, optionally modified as above, can form a cycle, and these hydrocarbon radicals with or without the stated variations, optionally with one or more, preferably up to three, in the case of fluorine, up to the maximum number on identical or different radicals from the series halogen, aryl, aryloxy, arylthio, cycloalkoxy, cycloalkylthio
  • R 7 and R 10 are the same or different and each represent hydrogen, alkyl, haloalkyl, alkoxy, alkylthio, phenylalkyl or phenyl and the phenyl groups are unsubstituted or provided with up to three, in the case of fluorine, up to the maximum number of identical or different substituents can and their salts, preferably acid addition salts,
  • R 5 and R 6 are hydrogen, (C r C 20 ) -alkyl, (C 2 -C 20 ) -alkenyl, (C 2 -C 20 ) -alkynyl, aryl, heterocyclyl, and in the case where U is a direct bond represents furthermore hydroxyl, cyano, thiocyano, nitro or halogen, where the aryl or heterocyclyl radicals listed can be unsubstituted or can be provided with up to three, in the case of fluorine, up to the maximum number of identical or different radicals, and one or more, preferably up to, in the alkyl, alkenyl or alkynyl radicals mentioned to three non-adjacent saturated carbon units can be replaced by a carbonyl group or by heteroatom units, such as oxygen, S (O) x , with x 0, 1 or 2, NR 9 or SiR 7 R 8 , where R 9 Is hydrogen, _C r C 4 -alkyl
  • R 7 and R 8 are the same or different and are each hydrogen, (CC 8 ) alkyl, (C r C 4 ) haloalkyl, (C r C 4 ) alkoxy, (C r C 4 ) alkylthio, phenyl ( C 1 -C 4 ) alkyl or phenyl and the phenyl groups may be unsubstituted or may be provided with up to three, in the case of fluorine also up to the maximum number of identical or different substituents, and these substituents preferably from the group (C 1 -C 4) - alkyl, (C r C 4) haloalkyl, (C r C4) alkoxy, (C r C4) - haloalkoxy, (C 1 -C 4) -alkylthio and halogen are selected;
  • W are preferably cis to each other and take positions 1 and 4 on the cyclohexane ring.
  • R 1 represents hydrogen
  • R 2 is (C r C 4 ) alkyl, cyclopropyl, (CC 4 ) haloalkyl or methoxymethyl;
  • R 3 represents hydrogen, methyl, ethyl, methoxy, ethoxy, halogen or cyano; or R 2 and R 3 together with the carbon atoms to which they are attached form an unsaturated 5- or 6-membered ring which, in the case of the 5- May contain a sulfur atom instead of a CH 2 unit or
  • R 2 and R 3 together with the carbon atoms to which they are attached form a saturated 5-membered or 6-membered ring which instead of a
  • CH 2 unit may contain a sulfur or an oxygen atom;
  • A represents CH or N;
  • X represents NH or oxygen;
  • E stands for a direct bond;
  • R 4 represents hydrogen or (C r C 4 ) alkyl;
  • Y represents oxygen or a direct bond;
  • W represents oxygen;
  • Z represents a radical DR 5 or NR 5 R 6 ; and
  • D represents oxygen or a direct bond; especially such connections for the
  • R 2 represents (C r C 3 ) alkyl, cyclopropyl, trifluoromethyl or methoxymethyl;
  • R 3 represents methyl, ethyl, methoxy, halogen or cyano; or
  • Z represents a radical DR 5 or NR 5 R 6 ;
  • Compounds of the formula I in which R 1 is hydrogen are particularly preferred;
  • R 2 represents ethyl, propyl, isopropyl or methoxymethyl
  • R 3 represents fluorine, chlorine, bromine or methoxy
  • Form quinazoline system which can be substituted with fluorine, chlorine, bromine and / or methyl; or R 2 and R 3 together with the pyrimidine ring the 5,6,7,8-tetrahydroquinazoline
  • Form system A means CH or N; X represents NH;
  • R 4 represents hydrogen; n represents the number 4 or 5;
  • Y represents oxygen or a direct bond
  • Z represents DR 5 or NR 5 R 6 ;
  • D means oxygen or a direct bond and W means oxygen.
  • R 1 represents hydrogen
  • R 2 is methoxymethyl and R 3 is methoxy or chlorine
  • R 2 is ethyl, propyl, isopropyl and R 3 is chlorine or the bromine; or R 2 and R 3 together with the carbon atom to which they are attached, the
  • Form quinazoline system A represents CH or N; X represents NH; E stands for a direct bond; R 4 represents hydrogen; n represents the number 4 or 5;
  • Y represents a direct bond
  • Z represents DR 5 or NR 5 R 6 ;
  • D means oxygen or a direct bond and W means oxygen.
  • R 1 represents hydrogen
  • R 2 is methoxymethyl and R 3 is methoxy; or R 2 is ethyl and R 3 is chlorine or bromine; or R 2 and R 3 together with the carbon atoms to which they are attached, that
  • Form quinazoline system A represents nitrogen; X NH means E is a direct bond; R 4 represents hydrogen; n denotes the number 5 and the residues are in the 1, 4 position and are cis to one another; Y represents a direct bond; W represents oxygen; Z means DR 5 ; D represents oxygen or a direct bond; and among the groups DR 5, those are highlighted in which R 5 is hydrogen, (C r C 12 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -cycloalkyl-
  • Aryl may be substituted; or Z denotes NR 5 R 6 and R 5 here is preferably (C 1 -C 4 ) alkyl and R 6 here is preferably (C 1 -C 12 ) alkyl, (C 3 -C 8 ) cycloalkyl, phenyl or phenyl -
  • halogen means a fluorine, chlorine, bromine or iodine atom, preferably a fluorine, chlorine or bromine atom; under the expression an unbranched or branched hydrocarbon radical having 1 to 4 carbon atoms, such as, for example, the methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radical; under the expression the aforementioned alkyl radicals, such as, for example, the pentyl, 2-methylbutyl or the 1, 1-dimethylpropyl radical, the hexyl, heptyl, octyl, 1, 1, 3,3-tetramethylbutyl, nonyl, 1-decyl , 2-decyl, undecyl, Dodecyl, pentadecyl or eicosyl radical; under the expression " (C 1 -C 4 ) haloalkyl
  • Alkyl in which one or more hydrogen atoms are replaced by the above halogen atoms, preferably chlorine or fluorine, such as the trifluoromethyl group, the 1-fluoroethyl group, the
  • Difluoromethyl group or the 1, 1, 2,2-tetrafluoroethyl group under the expression "(C 1 -C 2 ) fluoroalkyl", for example the 1-fluoroethyl, 2-fluoroethyl,
  • cycloalkyl preferably (C 3 -C 8 ) cycloalkyl
  • cycloalkoxy preferably (C 3 -C 8 ) cycloalkoxy
  • cycloalkylthio preferably (C 3 -C 8 ) cycloalkylthio
  • (C 3 -C 5 ) cycloalkyl the cyclopropyl, cyclobutyl or
  • Cyclopentyl group under the expression "(C 3 -C 8 ) cycloalkyl” the radicals mentioned above under (C 3 -C 5 ) cycloalkyl ", such as the cyclohexyl, cycloheptyl or cyclooctyl radical; under the expression” (C 3 - C 5 ) -Halogencycloalkyl "one of those listed above
  • Chlorine are replaced, such as the 2,2-difluoro or
  • Halogen atoms preferably fluorine or chlorine, are replaced; under the expression "(C r C4) -hydroxyalkyl", for example the hydroxymethyl,
  • Halogen atoms preferably fluorine or chlorine, are replaced; under the term "cyano (C 1 -C 4 ) alkyl" a cyanoalkyl group whose
  • Decyloxycarbonyl or dodecyloxycarbonyl group under the expression "(C 1 -C 4 ) haloalkoxycarbonyl" a (C r C 4 ) -
  • Alkoxycarbonyl group in which one or more, in the case of fluorine, if appropriate also all hydrogen atoms, are replaced by halogen, preferably fluorine or chlorine; under the expression "(C 1 -C 4 ) alkylthio" an alkylthio group, the
  • Hydrogen atoms of the hydrocarbon part through halogen in particular
  • Chlorine or fluorine are replaced;
  • Halogenoalkylsulfonyl "(C 1 -C 4 ) alkylsulfinyl and sulfonyl radicals with the meanings given above, in which one or more, in the case of fluorine, optionally also all the hydrogen atoms of the hydrocarbon part
  • Halogen especially chlorine or fluorine are replaced; under the terms “fluoromethylsulfinyl” and “fluoromethylsulfonyl” the
  • Halogen hydrocarbon radical has the meaning given under the expression “(C 1 -C 4 ) haloalkyl”; under the expression “(C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl” for example one
  • Halogen preferably chlorine or fluorine are replaced; the term "(C l -C 4) alkylthio (C 1 -C 4) alkyl", for example,
  • aryl is an isocyclic aromatic radical having preferably 6 to 14, in particular 6 to 12 carbon atoms, such as phenyl, naphthyl or biphenylyl, preferably phenyl; under the expression “heterocyclyl” a heteroaromatic or heteroaliphatic ring system, under “heteroaromatic ring system” an aryl radical in which at least one CH group is replaced by N and / or at least two adjacent CH groups are replaced by S, NH or O.
  • aryloxycarbonyl e.g. the phenoxycarbonyl
  • Hydrogen atoms of the hydrocarbon part through halogen in particular
  • Cycloheptanoyloxy group under the expression "(C 3 -C 8 ) cycloalkyl (C 1 -C 4 ) alkanoyloxy" for example the
  • Butane or hexanesulfonyloxy group under the term "arylsulfonyloxy” e.g. the phenylsulfonyloxy or the
  • the substituents with which the various aliphatic, aromatic and heterocyclic ring systems can be provided include, for example, halogen, (C r C 4 ) -alkyl, (C r C 4 ) -trialkylsilyl, (C r C 4 ) -haloalkyl, (C r C 4 ) alkoxy, (C r C 4 ) haloalkoxy, (C r C 4 ) alkoxy- (C r C 4 ) alkyl, (C r C 2 ) alkoxy- [CH 2 CH 2 ] 1 2 -ethoxy, (C r C4) alkylthio, (C r C4) alkylsulfinyl, (C r C4) - alkylsulfonyl, phenyl, benzyl, phenoxy, halophenoxy, (C 1 -C 4) -Alkylphenoxy, ( C r C 4 ) -alk
  • Alkoxyalkyl radicals such as e.g. the methoxymethyl, methoxyethyl or
  • Alkoxy-alkoxy-alkyl radicals such as e.g. the methoxy or the ethoxy ethoxyethyl
  • Alkylthioalkyl residues e.g. the methyl or the ethylthioethyl group;
  • Alkylsulfinyl-alkyl residues e.g. the methyl or ethylsulfinylethyl group
  • Alkylsulfonyl-alkyl radicals such as e.g. the methyl or ethylsulfonylethyl group; or
  • Alkyl-dialkylsilyl-alkyl preferably alkyl-dimethylsilyl-alkyl radicals, such as e.g. the
  • Trimethylsilylmethyl or the trimethylsilylethyl group Trimethylsilylmethyl or the trimethylsilylethyl group
  • Trialkylsilyl preferably alkyldimethylsilyl, e.g. the trimethylsilyl,
  • Aryldialkylsilyl preferably aryldimethylsilyl residues such as e.g.
  • Arylalkyl dialkylsilyl preferably aryldimethylsilyl residues such as e.g. the
  • Alkanoylalkyl residues such as e.g. the acetylmethyl or the pivaloylmethyl group; or
  • Cycloalkanoylalkyl residues such as e.g. the cyclopropylcarbonylmethyl or the
  • Halogenalkanoylalkyl residues such as e.g. the trifiuor- or trichloroacetylmethyl
  • Aroylalkyl residues such as e.g. the benzoyl or naphthoylalkyl residues such as e.g. the
  • Heterocyclylcarbonylalkyl residues such as e.g. the thienyl or pyridylacetylmethyl
  • Aryl-alkyl residues e.g. the benzyl, the 2-phenylethyl, the 1-phenylethyl, the
  • Heterocyclylalkyl residues e.g. the thienylmethyl, pyridylmethyl, furfuryl,
  • Aryloxyalkyl radicals such as e.g. the phenoxymethyl or naphthoxymethyl group.
  • Cycloalkyl residues monocyclic such as e.g. the cyclopropyl, cyclobutyl,
  • Alkyl-cycloalkyl residues such as e.g. the 4-methyl or the 4-tert-butylcyclohexyl
  • the present invention relates to the compounds of formula I in the form of the free base or an acid addition salt.
  • Acids which can be used for salt formation are inorganic acids such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid or organic acids such as formic acid, acetic acid, propionic acid, malonic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid, methanesulfonic acid, benzenesulfonic acid or toluene .
  • the compounds of the formula I have one or more asymmetric carbon atoms or stereoisomers on double bonds. Enantiomers or diastereomers can therefore occur.
  • the invention encompasses both the pure isomers and their mixtures.
  • the mixtures of diasteromers can be prepared using conventional methods, e.g. be separated into the components by selective crystallization from suitable solvents or by chromatography. Racemates can be separated into the enantiomers by conventional methods, e.g. by salt formation with an optically active acid, separation of the diastereomeric salts and release of the pure enantiomers using a base.
  • the invention further relates to a process for the preparation of compounds of formula I, which is characterized in that a compound of formula IV
  • A, R 1 , R 2 and R 3 have the meanings given under formula I and L is a leaving group, for example halogen, alkylthio, alkanesulfonyloxy or arylsulfonyloxy, alkylsulfonyl or arylsulfonyl, with a nucleophile of the formula V.
  • the substitution reaction described above is known in principle.
  • the leaving group Z can be varied within wide limits and can mean, for example, a halogen atom such as fluorine, chlorine, bromine or iodine or alkylthio such as methyl or ethylthio, or alkanesulfonyloxy such as methane, trifluoromethane or ethanesulfonyloxy or arylsulfonyloxy such as benzenesulfonyloxy or toluenesulfonyloxy or alkylsulfonyl such as Methyl or ethyl sulfonyl or aryl sulfonyl such as phenyl or toluenesulfonyl.
  • a halogen atom such as fluorine, chlorine, bromine or iodine or alkylthio such as methyl or ethylthio
  • the aforementioned reaction is carried out in a temperature range from 20-150 ° C., advantageously in the presence of a base and optionally in an inert organic solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidin-2-one, Dioxane, tetrahydrofuran, 4-methyl-2-pentanone, methanol, ethanol, butanol, ethylene glycol,
  • an inert organic solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidin-2-one, Dioxane, tetrahydrofuran, 4-methyl-2-pentanone, methanol, ethanol, butanol, ethylene glycol,
  • Suitable bases for the case where X is oxygen are, for example, alkali or alkaline earth metal carbonates, bicarbonates, amides or hydrides such as sodium carbonate, sodium bicarbonate, potassium carbonate, sodium amide or sodium hydride; if X is NH, these are, for example, alkali - Or alkaline earth metal carbonates, hydrogen carbonates, hydroxides, amides or hydrides such as sodium carbonate, sodium hydrogen carbonate, potassium carbonate, sodium hydroxide, sodium amide or sodium hydride or organic bases such as triethylamine or pyridine.
  • a second equivalent of an amine V can also be used as an auxiliary base.
  • the invention further relates to a process for the preparation of compounds of formula I for which n is 5, in particular of derivatives of pyridine for which E is a direct bond, characterized in that a compound of formula IV with a nucleophile of formula VI converted to a compound of formula VII and the compounds I obtained from the latter by hydrogenation of the phenyl radical.
  • the reaction to the compounds VII is carried out analogously to the preparation of the compounds of the formula I from the starting materials IV and V.
  • the hydrogenation of VII is carried out by known methods (cf., for example, F. Zymalkowski, Catalytic Hydrogenation, p. 1 91, Enke Verlag, Stuttgart , 1 965) and leads to cis / trans mixtures on the cyclohexyl side chain which can be separated by crystallization or chromatography.
  • the invention further relates to a process for the preparation of compounds of the formula I for which X is NH, in particular derivatives of pyridine, characterized in that a compound of the formula VIII in which R 1 , R 2 , R 3 and A is the above have the meanings given, with an alkylating agent of the formula IX, in which E, n, R 4 , Y, W and z have the meanings given for the formula I and L is a leaving group with the meaning given for formula IV, to give a compound of the formula X. implemented and the latter subsequently reductively converted into the compounds of formula I.
  • the alkylation to the compounds of the formula X is carried out analogously to the preparation of the compounds of the formula I from the compounds of the formula IV.
  • the reductive cleavage of the intermediates X is carried out analogously to known methods (cf. R. Huisgen et al. B. 101, 2559 ( 1 968), CH. Rayburn, WR Harlau, HR Haumer Am. Soc. 72, 1 721 (1 950)).
  • the preparation of the educts VIII is described in DOS 4,331,179.
  • the invention further relates to a process for the preparation of compounds of the formula I for which A is CH and R 2 and R 3 together with the carbon atoms to which they are bonded form a saturated 6-membered ring (5,6,7,8- Tetrahydroquinolines), characterized in that a compound of the formula I for which A is CH and R 2 and R 3 together with the carbon atoms to which they are attached form an unsaturated 6-membered ring (quinolines) in the presence of a noble metal catalyst .
  • the hydrogenation is carried out analogously to known methods (cf. J.Z. Ginos, J. Org. Chem. 40, 1191, (1975).
  • the invention further relates to a process for the preparation of compounds of the formula I for which Y is oxygen, characterized in that a compound of the formula XI
  • R 1 , R 2 , R 3 , R 4 , X and E have the meanings given for the formula I and the sum of the indices o and p is equal to the number (n-1), where n is the formula I has the meaning given, reduced with a suitable reducing agent to a compound of the formula XII
  • R 1 , R 2 , R 3 , R 4 , E and A have the meanings given for the formula I and o and p have the meaning given for the formula XI and this compound of the formula XII then with an acylating agent of the general formula LCZ in the W and Z are those given for formula I.
  • REPLACEMENT SHEET (RULE 2 $) Has meanings and L is a leaving group with the meanings given for formula IV, acylated on the OH group.
  • reducing agents are complex hydrides, such as lithium aluminum hydride, sodium borohydride and in the case of the cyclohexyl derivatives complex hydrides with bulky substituents on the central atom such as lithium tri-sec-butylborohydride (L-Selectride ®) or lithium trisiamylborhydrid (LS-Selectride ®) the in the reduction give the preferred derivatives with cis configuration with respect to the 1,4-substituents.
  • complex hydrides such as lithium aluminum hydride, sodium borohydride
  • L-Selectride ® lithium tri-sec-butylborohydride
  • LS-Selectride ® lithium trisiamylborhydrid
  • the subsequent acylation reaction is carried out analogously to known methods for the esterification of alcohols with activated carboxylic acid derivatives, for example by the compounds XII with a carboxylic acid chloride Z-C-Cl in one
  • inert solvents such as dichloroethane, trichloroethane, ether or tetrahydrofuran in the presence of a base such as e.g. Triethylamine or pyridine or the base itself (pyridine) used as a solvent.
  • a base such as e.g. Triethylamine or pyridine or the base itself (pyridine) used as a solvent.
  • the invention further relates to a process for the preparation of the intermediates of the formula XII, characterized in that a compound of the general formula IV is reacted with a nucleophile of the general formula XIII
  • DeSATZBLA ⁇ (RULE 26)
  • the compounds of the formula I synthesized by the processes described above can be selected from the grouping -YCZ by known methods
  • nucleophiles of the formula V required as starting products for the case where X is oxygen can be prepared by known processes, for example by reducing a carbonyl group with a suitable reducing agent, for example a complex metal hydride or, in the case of an aldehyde or ketone, also with hydrogen and a Hydrogenation catalyst.
  • a suitable reducing agent for example a complex metal hydride or, in the case of an aldehyde or ketone, also with hydrogen and a Hydrogenation catalyst.
  • suitable substituted phenols can also be reacted with hydrogen in the presence of a hydrogenation catalyst.
  • the nucleophiles of the formula V required as starting products can be prepared by known processes, for example by reducing an oxime or a nitrile with a suitable reducing agent, for example a complex metal hydride or hydrogen in the presence of a hydrogenation catalyst, reductive amination or Leuckart-Wallach reaction of an aldehyde or ketone or Gabriel reaction of an alkyl halide or tosylate.
  • a suitable reducing agent for example a complex metal hydride or hydrogen in the presence of a hydrogenation catalyst
  • reductive amination or Leuckart-Wallach reaction of an aldehyde or ketone or Gabriel reaction of an alkyl halide or tosylate reductive amination or Leuckart-Wallach reaction of an aldehyde or ketone or Gabriel reaction of an alkyl halide or tosylate.
  • suitable substituted anilines can also be reacted with hydrogen in the presence of a hydrogenation catalyst.
  • the active ingredients are suitable for good plant tolerance and cheaper
  • Hygiene sector occur. They are effective against normally sensitive and resistant species as well as all or individual stages of development.
  • Pests include:
  • Rhipicephalus spp. Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa,
  • Eurygaster spp. Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp .. From the order of Homoptera z.
  • Euscelis bilobatus Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. , Psylla spp .. From the order of the Lepidoptera z. B.
  • 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.
  • Nematodes e.g. B. those of the genera Meloidogyne, Heterodera, Ditylenchus,
  • Galba spp. Succinea spp., Biomphalaria spp., Bulinus spp., Oncomelania spp ..
  • the invention also relates to compositions, in particular insecticidal and acaricidal compositions, which contain the compounds of the formula I in addition to suitable formulation auxiliaries.
  • the agents according to the invention generally contain the active ingredients of the formula I in an amount of 1 to 95% by weight.
  • WP Wettable powder
  • EC emulsifiable concentrates
  • SL aqueous solutions
  • SC oil or water-based dispersions
  • SE suspoemulsions
  • SE suspoemulsions
  • DP dusts
  • mordants granules in the form of , Spray, elevator and adsorption granules
  • WG water-dispersible granules
  • ULV formulations microcapsules, waxes or baits.
  • the necessary formulation aids such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in:
  • combinations with other pesticidally active substances, fertilizers and / or growth regulators can also be prepared, e.g. B. in the form of a finished formulation or as a tank mix.
  • Spray powders are preparations which are uniformly dispersible in water.
  • REPLACEMENT SHEET (REG & 26 Alkylphenol sulfonates and dispersants, e.g. B. ligninsulfonic acid sodium, 2,2'-dinaphthylmethane-6, 6'-disulfonic acid sodium.
  • Emulsifiable concentrates are obtained by dissolving the active ingredient in an organic solvent, e.g. B. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers.
  • emulsifiers may be used, for example: calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol esters.
  • calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate
  • nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid ester or polyoxyethylene
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. B. talc, natural clays such as kaolin, bentonite, pyrophyllite or diatomaceous earth.
  • Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, e.g. As polyvinyl alcohol, sodium polyacrylic acid or mineral oils, on the surface of carriers such as sand, kaolinite or granulated inert material.
  • Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers.
  • the active ingredient concentration is e.g. B. about 10 to 90 wt .-% the rest of 100 wt .-% consists of conventional formulation ingredients.
  • the active substance concentration can be approximately 5 to 80% by weight.
  • Dust-like formulations usually contain 5 to 20 wt .-% of active ingredient, sprayable solutions about 2 to 20 wt .-%.
  • the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulation aids, fillers, etc. are used.
  • the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers.
  • the concentrates present in the commercial form are optionally diluted in the customary manner, for. B. with wettable powders, emulsifiable concentrates, dispersions and sometimes also with microgranules using water. Dust-like and granulated preparations as well as sprayable solutions are usually no longer diluted with other inert substances before use.
  • the required application rate varies. It can fluctuate within wide limits, e.g. B. between 0.0005 and 10.0 kg / ha or more of active substance, but it is preferably between 0.001 and 5 kg / ha.
  • the active compounds according to the invention can be present in their commercially available formulations and in the use forms prepared from these formulations in mixtures with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • the pesticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin compounds, substances produced by microorganisms and the like. a .. Preferred mixing partners are
  • the active substance content of the use forms prepared from the commercially available formulations can be from 0.00000001 to 95% by weight of active substance, preferably between 0.00001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • the active compounds according to the invention are also suitable for combating endoparasites and ectoparasites in the veterinary field or in the field of animal husbandry.
  • the active compounds according to the invention are used here in a known manner, such as by oral use in the form of, for example, tablets, capsules, drinkers, granules, by dermal use in the form of, for example, dipping (dipping), spraying (spraying), pouring on (pour-on and spot) -on) and powdering and by parenteral use in the form of, for example, injection.
  • novel compounds of the formula I according to the invention can accordingly also be used particularly advantageously in animal husbandry (for example cattle, sheep, pigs and poultry such as chickens, geese, etc.).
  • animal husbandry for example cattle, sheep, pigs and poultry such as chickens, geese, etc.
  • the animals are given the new compounds, if appropriate in suitable formulations (see above) and if appropriate with the drinking water or feed orally. Since excretion in the faeces is effective, the development of insects in the faeces of the animals can be prevented very easily in this way.
  • the appropriate dosages and formulations depend in particular on the type and stage of development of the livestock and also on the infestation pressure and can be easily determined and determined using the usual methods.
  • the new compounds in cattle z. B. in doses of 0.01 to 1 mg / kg body weight.
  • the compounds of the formula I according to the invention are also notable for an excellent fungicidal action. Fungal pathogens that have already penetrated into the plant tissue can be successfully combated curatively. This is particularly important and advantageous in the case of those fungal diseases which can no longer be effectively combated with the usual fungicides after infection has occurred.
  • the spectrum of activity of the claimed compounds covers various
  • REPLACEMENT SHEET (RULE 2 $) economically important, phytopathogenic fungi, such as. B. Plasmopara viticola, Erysiphe graminis and Puccinia recondita.
  • the compounds according to the invention are also suitable for use in technical fields, for example as wood preservatives, as preservatives in paints, in cooling lubricants for metalworking or as preservatives in drilling and cutting oils.
  • the active compounds according to the invention can be used in their commercially available formulations either alone or in combination with other fungicides known from the literature.
  • fungicides known from the literature which can be combined according to the invention with the compounds of the formula I are, for example to name the following products: aldimorph, andoprim, anilazine, BAS 480F, BAS 450F, benalaxyl, benodanil, benomyl, binapacryl, bitertanol, bromuconazole, buthiobate, captafol, captan, carbendazim, carboxin, CGA 1 73506, cyprofuram, dichlofluanrazide, diclobzinazol, diclobrazine dicl , Diethofencarb, Difenconazole (CGA 1 69374), Difluconazole, Dimethirimol, Dimethomorph, Diniconazole, Dinocap, Dithianon, Dodemorph, Dodine, Edifenfos, Ethirimol, Etridiazol, Fenarimol, Fenfuram,
  • REPLACEMENT SHEET (RULE 26 ⁇ Thiram, Toiclofos-methyl, Tolylfluanid, Triadimefon, Triadimenol, Tricyclazole, Tridemorph, Triflumizol, Triforine, Validamycin, Vinchlozolin, XRD 563, Zineb, Sodium Dodecylsulfonate, Sodium-Dodecyl-Sulfate, Sodium-Alkaline, Sodium-C1-3-C1-Sodium-C1- / Sodium-C1- / Sodium-C1- / C1-Sodium-C1- / Sodium-C1-3 -cetostearyl phosphate ester, dioctyl sodium sulfosuccinate, sodium isopropyl naphthalenesulfonate, sodium methylenebisnaphthalenesulfonate, cetyl trimethyl ammonium chloride, salts of long-chain primary, secondary or tert
  • the above-mentioned combination partners are known active ingredients, which are largely in Ch.R Worthing, S.B. Walker, The Pesticide Manual, 7th edition (1,983), British Crop Protection Council.
  • 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 0.0001 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.
  • a dusting agent is obtained by mixing 10 parts by weight of active ingredient and 90 parts by weight of talc as an inert substance and comminuting them in a hammer mill.
  • a wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight of active compound, 65 parts by weight of kaolin-containing quartz as the inert substance, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium as the wetting agent. and dispersant mixes and grinds in a pin mill.
  • a dispersion concentrate which is easily dispersible in water is prepared by mixing 40 parts by weight of active compound with 7 parts by weight of a sulfosuccinic acid half-ester, 2 parts by weight of a lignosulfonic acid sodium salt and 51 parts by weight of water and in a attritor ground to a fineness of less than 5 microns.
  • An emulsifiable concentrate can be prepared from 1 5 parts by weight of active ingredient, 75 parts by weight of cyclohexane as solvent and 10 parts by weight of oxyethylated nonylphenol (10 AeO) as emulsifier.
  • Granules can be produced from 2 to 15 parts by weight of active ingredient and an inert granule carrier material such as attapulgite, pumice granules and / or quartz sand.
  • a suspension of the wettable powder from example b) having a solids content of 30% is expediently used and sprayed onto the surface of an attapulgite granulate, dried and mixed intimately.
  • the proportion by weight of the wettable powder is approximately 5% and that of the inert carrier material approximately 95% of the finished granulate.
  • Example No. 82, 83 At 250 mg active ingredient / I spray liquor, the following substances show complete suppression of infection: Example No. 82, 83.
  • the plants were inoculated with an aqueous spore suspension of Puccinia recondita.
  • the plants were dripping wet for about 1 6 hours in a climate chamber at 20 ° C and about 100% rel. Humidity set. Then they were in a greenhouse at a temperature of 22 to 25 ° C and 50 to 70% rel. Humidity continued to be cultivated.
  • Example No. 82 Erysiphe graminis
  • Barley plants were strongly inoculated in the 3-leaf stage with conidia of barley mildew (Erysiphe graminis f. Sp. Hordei) and in a greenhouse at 20 ° C and a rel. Humidity of 90 to 95% set up. 24 hours after inoculation, the plants were uniformly wetted with the compounds listed in Table 1 in the stated active compound concentrations. After an incubation period of 10 days, the plants were examined for infestation with barley mildew. The degree of infestation was expressed in% infested leaf area, based on untreated, 100% infected control plants.
  • Spray powder concentrate with a concentration of 250 ppm (based on
  • Example 5 the compounds according to Examples 70 and 82 produced 100% mortality in the test animals.
  • Larvae (L3) of the Southern Corn Rootworm (Diabrotica undecimpunctata) were placed on filter paper discs, which were impregnated with 1 ml of an acetone dilution of a wettable powder in a concentration of 250 ppm based on active ingredient. After the acetone had been evaporated off, the dishes were closed, stored for 3 days at 28 ° C. and then the mortality of the larvae was determined.
  • Petri dishes half of which were poured out on an artificial feed diet, were populated with L3 larvae of the Egyptian cottonworm Spodoptera littoralis and sprayed with an aqueous suspension of a wettable powder concentrate which contains 250 ppm of active ingredient. After closing the shells, they were examined for mortality of the larvae after 5 days.
  • Field beans (Vicia faba) heavily infested with customer bean aphid (Aphis craccivora) were sprayed with aqueous dilutions of wettable powder concentrates with an active substance content of 250 ppm until the stage at which dripping started. The aphid mortality was determined after 3 days. A 100% kill could be achieved with the compounds according to Examples 68, 82 and 83.
  • the active compounds were dissolved 10% (w / v) in a mixture consisting of dimethylformamide (85 g), nonylphenol polyglycol ether (3 g) and ethoxylated castor oil (7 g), and the emulsion concentrates thus obtained were dissolved in water diluted a test concentration of 500 ppm.
  • the hydrochloride of the carboxylic acid chloride is prepared from 700 mg (2.5 mmol) of carboxylic acid from Example D analogously to Example E. This is introduced into a solution of 350 mg 1, 2,3,4-tetrahydroisoquinoline and 500 mg triethylamine in 25 ml methylene chloride. The mixture is stirred at room temperature for 4 h, the mixture is stirred with water, the organic phase is separated off, dried and concentrated. 0.7 g (70.2% of theory) of a yellow oil are obtained, which crystallizes on standing. Mp: 98-99 ° C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Plural Heterocyclic Compounds (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

L'invention concerne des dérivés d'hétérocyclylamino-cycloalcoyle et d'hétérocyclyloxy-cycloalcoyle, ainsi que leurs sels, leur préparation et leur utilisation comme pesticides et fongicides. Dans la formule (a), Ar désigne pyridyl-4 ou pyrimidinyl-4 le cas échéant substitués; X désigne NH, O ou S; E désigne une liaison ou alcandiyl; n vaut 2 à 7; R4 désigne H ou alcoyle, Y désigne O ou une liaison; et Ac désigne acyl. L'invention concerne en outre un procédé de préparation de ces dérivés, des agents les contenant et leur utilisation comme pesticides et fongicides.
EP95919376A 1994-05-17 1995-05-03 Derives d'heterocyclylamino-cycloalcoyle et d'heterocyclyloxy-cycloalcoyle, leur preparation et leur utilisation comme pesticides et comme fongicides Withdrawn EP0759909A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4417163 1994-05-17
DE4417163A DE4417163A1 (de) 1994-05-17 1994-05-17 Heterocyclylamino- und Heterocyclyloxy-cycloalkyl-Derivate, ihre Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel und Fungizide
PCT/EP1995/001666 WO1995031441A1 (fr) 1994-05-17 1995-05-03 Derives d'heterocyclylamino-cycloalcoyle et d'heterocyclyloxy-cycloalcoyle, leur preparation et leur utilisation comme pesticides et comme fongicides

Publications (1)

Publication Number Publication Date
EP0759909A1 true EP0759909A1 (fr) 1997-03-05

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US (1) US5691321A (fr)
EP (1) EP0759909A1 (fr)
JP (1) JPH10500115A (fr)
KR (1) KR970703322A (fr)
CN (1) CN1148383A (fr)
AU (1) AU703538B2 (fr)
BR (1) BR9507647A (fr)
CA (1) CA2190495A1 (fr)
DE (1) DE4417163A1 (fr)
HU (1) HUT76722A (fr)
IL (1) IL113737A0 (fr)
MX (1) MX9605658A (fr)
TR (1) TR28488A (fr)
WO (1) WO1995031441A1 (fr)
ZA (1) ZA953957B (fr)

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DE19511562A1 (de) * 1995-03-29 1996-10-02 Hoechst Schering Agrevo Gmbh Cyclohexylamino- und alkoxy-Stickstoff-Heterocyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel und Fungizide
DE19603576A1 (de) * 1996-02-01 1997-08-07 Bayer Ag Acylierte 4-Amino und 4-Hydrazinopyrimidine
US6281221B1 (en) 1996-06-27 2001-08-28 Hoechst Scering Agrevo Gmbh Substituted 1,3-dioxan-5-ylamino-hererocyclic compounds, processes for their preparation and their use as pest control compositions
DE19741654A1 (de) * 1997-09-22 1999-03-25 Hoechst Schering Agrevo Gmbh Substituierte Triazine, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel und Fungizide
GB9810860D0 (en) * 1998-05-20 1998-07-22 Hoechst Schering Agrevo Gmbh Substituted pyridine and pyrimidines, processes for their preparation and their use as pesticides
GB9816729D0 (en) * 1998-08-01 1998-09-30 Hoechst Schering Agrevo Gmbh Substituted cyclohexylaminopyrimidines
US6759428B2 (en) 2001-12-04 2004-07-06 Roche Palo Alto Llc Indole nitriles
MXPA04005263A (es) 2001-12-04 2004-10-11 Hoffmann La Roche 2-amino-cicloalcanocarboxamidas substituidas y su uso como inhibidores de cisteina proteasa.
WO2003093231A2 (fr) * 2002-04-29 2003-11-13 Merck & Co., Inc. Modulateurs de l'activite des recepteurs des chimiokines a base de tetrahydropyranyl cyclopentyl tetrahydroisoquinoline
WO2004054581A2 (fr) * 2002-12-13 2004-07-01 Smithkline Beecham Corporation Composes de cyclohexyle utiles en tant qu'antagonistes du ccr5
EP1464335A3 (fr) * 2003-03-31 2007-05-09 Taisho Pharmaceutical Co. Ltd. Derivés de quinolines, tetrahydroquinolines et pyrimidines comme antagonistes du MCH
NZ549673A (en) * 2004-03-30 2010-03-26 Taisho Pharmaceutical Co Ltd Pyrimidine derivatives and methods of treatment related to the use thereof
CN101155406B (zh) * 2006-09-29 2010-10-27 华为技术有限公司 一种资源分配的指示方法及装置

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PH20344A (en) * 1981-01-29 1986-12-04 Sankyo Co Aminopyrimidine derivatives, processes for their preparation, and fungicidal, insecticidal and acaricidal compositions containing them
JPS6242974A (ja) * 1985-08-20 1987-02-24 Ube Ind Ltd ピリミジニルオキシアルカン酸アミド誘導体および除草剤
US4895849A (en) * 1986-10-08 1990-01-23 Ube Industries, Ltd. Aralkylaminopyrimidine compounds which are useful as for producing thereof and insecticides
HUT65124A (en) * 1990-11-19 1994-04-28 Du Pont Insecticidal, acaricidal and fungicidal aminopyrimidines, compositions comprising the copounds and process for using thereof
AU2303992A (en) * 1991-06-24 1993-01-25 Walter Allen Clifford Further improved gate valves
DE4208254A1 (de) * 1992-03-14 1993-09-16 Hoechst Ag Substituierte pyrimidine, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel und fungizid
JPH05320143A (ja) * 1992-03-18 1993-12-03 Mochida Pharmaceut Co Ltd 新規ピリミジン誘導体
US5439911A (en) * 1992-12-28 1995-08-08 Shionogi & Co., Ltd. Aminopyrimidine derivatives and their production and use
DE4408404A1 (de) * 1994-03-12 1995-09-14 Huels Chemische Werke Ag Verfahren zur Herstellung von Chlorpyrimidinen

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KR970703322A (ko) 1997-07-03
CN1148383A (zh) 1997-04-23
WO1995031441A1 (fr) 1995-11-23
MX9605658A (es) 1998-02-28
DE4417163A1 (de) 1995-11-23
BR9507647A (pt) 1997-09-09
AU703538B2 (en) 1999-03-25
HUT76722A (en) 1997-10-28
JPH10500115A (ja) 1998-01-06
CA2190495A1 (fr) 1995-11-23
ZA953957B (en) 1996-01-19
TR28488A (tr) 1996-08-12
AU2523595A (en) 1995-12-05
HU9603196D0 (en) 1997-01-28
US5691321A (en) 1997-11-25
IL113737A0 (en) 1995-08-31

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