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WO1992005159A1 - 2-phenyl-pyrimidines, process for producing the same, agents containing the same and their use as fungicides - Google Patents

2-phenyl-pyrimidines, process for producing the same, agents containing the same and their use as fungicides Download PDF

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Publication number
WO1992005159A1
WO1992005159A1 PCT/EP1991/001790 EP9101790W WO9205159A1 WO 1992005159 A1 WO1992005159 A1 WO 1992005159A1 EP 9101790 W EP9101790 W EP 9101790W WO 9205159 A1 WO9205159 A1 WO 9205159A1
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WIPO (PCT)
Prior art keywords
alkyl
optionally substituted
alkoxy
alkylthio
halo
Prior art date
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PCT/EP1991/001790
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German (de)
French (fr)
Inventor
Klemens Minn
Peter Braun
Burkhard Sachse
Heinrich Wicke
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Hoechst AG
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Hoechst AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

Definitions

  • 2-PhenyI-pyrimidines process for their preparation, compositions containing them and their use as fungicides.
  • the present invention therefore relates to compounds of the formula
  • R 1 , R 2 , R 3 independently of one another hydrogen, halogen, hydroxy, amino, nitro, cyano, thiocyano, (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylarnino, (C 1 -C 4 ) dialkylamino, (C 1 -C 4 ) alkylcarbonylamino, halo (C 1 -C 4 ) alkyl,
  • (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl,
  • Phenoxy- (C 1 -C 4 ) alkyl optionally substituted phenylketo- (C 1 -C 4 ) alkyl, optionally substituted phenyloxycarbonyl- (C 1 -C 4 ) alkyl,
  • Phenoxyphenyl- (C 1 -C 4 ) alkyl, where optionally substituted is to be understood that the phenyl part up to three times by halogen, ester, (C 1 -C 4 ) alkyl,
  • R 1 , R 2 and / or R 3 optionally together form a saturated, partially unsaturated or aromatic carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members,
  • R 4 hydrogen, halogen, (C 1 -C 4 ) alkyl, hydroxy- (C 1 -C 4 ) alkyl, dihydroxy- (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl, halo - (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl,
  • (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl,
  • Phenoxy- (C 1 -C 4 ) alkyl optionally substituted phenylmercapo - (C 1 -C 4 ) alkyl, optionally substituted 5- or 6-membered heteroaromatic, optionally substituted phenylcarbonyl, optionally substituted phenylketo (C 1 -C 4 ) alkyl , optionally substituted phenyloxycarbonyl- (C 1 -C 4 ) alkyl, optionally substituted phenylamino- (C 1 -C 4 ) alkyl, optionally substituted
  • Phenoxyphenyl- (C 1 -C 4 ) alkyl, where optionally substituted is to be understood that the phenyl part (heteroaromatic) up to three times by halogen, ester,
  • R 5 halogen, (C 1 -C 4 ) alkyl, (C 1 -C 9 ) alkoxy, hydroxy- (C 1 -C 4 ) alkyl,
  • Phenyloxycarbonyl- (C 1 -C 4 ) alkyl optionally substituted
  • Phenylamino (C 1 -C 4 ) alkyl optionally substituted
  • Phenoxyphenyl- (C 1 -C 4 ) alkyl whereby optionally substituted is to be understood that the phenyl part is substituted up to three times by halogen, ester, (C 1 -C 4 ) alkyl,
  • Phenyloxycarbonyl- (C 1 -C 4 ) alkyl optionally substituted
  • Phenoxy- (C 1 -C 4 ) alkyl optionally substituted phenyl- (C 1 -C 4 ) alkyl,
  • Phenoxyphenyl- (C 1 -C 4 ) alkyl optionally substituted
  • Phenylmercapto- (C 1 -C 4 ) alkyl where optionally substituted is to be understood that the phenyl part is substituted up to three times by halogen, ester, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy or can be simply substituted by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms,
  • R 5 and R 6 optionally together a saturated, partially unsaturated or
  • R 7 , R 8 independently of one another hydrogen, hydroxy, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy,
  • R 9 , R 10 independently of one another hydrogen, (C 1 -C 9 ) alkyl, cyano- (C 1 -C 4 ) alkyl,
  • phenylamino (C 1 -C 4 ) alkyl optionally substituted phenoxyphenyl- (C 1 -C 4 ) alkyl, which is to be understood as being optionally substituted. that the phenyl part up to three times by halogen, ester, (C 1 -C 4 ) alkyl,
  • Carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members and n a number from 0 to 8, and their acid addition salts.
  • R 1 , R 2 , R 3 preferably independently of one another are hydrogen, halogen, hydroxy, amino, nitro.
  • (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylcarbonyl,
  • optionally substituted phenyl optionally substituted phenoxy, optionally substituted phenyl- (C 1 -C 4 ) alkyl, optionally substituted phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenylketo (C 1 -C 4 ) alkyl, wherein under optionally Substituted is to be understood that the phenyl part up to three times by halogen, ester, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio,
  • R 2 , R 2 and / or R 3 together can be a saturated, partially unsaturated or
  • R 1 , R 2 , R 3 are, in particular independently of one another, hydrogen, chlorine, bromine, nitro or (C 1 -C 4 ) alkoxy, particularly preferably hydrogen, chlorine, bromine or OCH 3 .
  • R 4 preferably denotes hydrogen, halogen, (C 1 -C 4 ) alkyl, hydroxy- (C 1 -C 4 ) alkyl, Dihydroxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio, perhalo (C 1 -C 4 ) alkylthio, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, ( C 1 -C 4 ) alkylamino (C 1 -C 4 ) alkyl,
  • (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, optionally substituted phenyl, optionally substituted 5- or 6-membered Heteroaromatic, for example pyrimidine, pyridine or thiophene, optionally substituted phenylcarbonyl, where optionally substituted means that the phenyl ring
  • R 4 is in particular hydrogen, iodine, bromine, dialkylamino (C 1 -C 4 ) alkyl,
  • phenyl or pyridinyl particularly preferably hydrogen.
  • R 5 preferably denotes halogen, (C 1 -C 4 ) alkyl, (C 1 -C 9 ) alkoxy, hydroxy- (C 1 -C 4 ) alkyl,
  • optionally substituted phenyl- (C 1 -C 4 ) alkoxy where optionally substituted is understood to mean that the phenyl part is substituted up to three times by halogen, ester, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl,
  • (C 1 -C 4 ) haloalkoxy or simply substituted by nitro or cyano and R 5 is in particular halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, phenyl- (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkynyloxy, (C 1 -C 4 ) Alkylmercapto or (C 1 -C 4 ) alkylsulfonyl, particularly preferably Cl, Br, OCH 3 or OC 2 H 5 .
  • R 6 preferably denotes hydrogen, halogen, (C 1 -C 4 ) alkyl, hydroxy- (C 1 -C 4 ) alkyl,
  • R 6 is in particular hydrogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl or
  • (C 1 -C 4 ) alkoxycarbonyl particularly preferably hydrogen or -O-CH 2 -CH 2 .
  • R 5 and R 6 together can be a saturated, partially unsaturated or aromatic
  • R 9 , R 10 are independently hydrogen, (C 1 -C 9 ) alkyl or by halogen,
  • R 9 and R 10 together can form a saturated or partially unsaturated carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10, in particular 5 or 6, ring members, n is preferably a number from 0 to 4, in particular a number of 0 up to 2
  • Halo in the substituents is substituted one or more times by halogen atoms.
  • hydrohalic acids such as hydrochloric acid or
  • Hydrobromic acid phosphoric acid, nitric acid, sulfuric acid, mono- or
  • bifunctional carboxylic acids and hydroxycarboxylic acids such as acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid or lactic acid, as well as sulfonic acids such as p-toluenesulfonic acid or 1,5-naphthalenedisulfonic acid.
  • the acid addition compounds of the formula I can be prepared in a simple manner, e.g. be obtained by dissolving a compound of formula I in a suitable organic solvent and adding the acid and in a known manner, e.g. by filtration, isolated and optionally cleaned by washing with an inert organic solvent.
  • the pyrimidines of the formula I can be prepared by various multistage processes.
  • suitable 3-ketocarboxylic acid esters with benzamidines, where they can be used in pure form or in situ, released from their salts, without solvent or in a suitable aprotic or protic solvent, for example water or lower alcohols, at temperatures from 0 ° C to 160 ° C, preferably at temperatures between room temperature and the boiling point of the solvent, in the presence of a suitable base, such as alkali metal carbonates, Na 2 CO 3 or K 2 CO 3 , or
  • Alkali alcoholates e.g. NaOMe or NaOEt
  • 4-pyrimidinones e.g. NaOMe or NaOEt
  • Literature regulations Beilstein, 3rd / 4th supplement, volume 25, p. 279 can be produced in two stages in a one-pot process.
  • an inert solvent such as toluene, THF, dioxane or diethyl ether, corresponding carboxylic acid derivatives with a suitable base, generally with an alkali metal hydride, preferably NaH, or
  • Alkaline alcoholate preferably NaOMe, anionized, then formylated with an ant ester.
  • the subsequent condensation can be carried out with benzamidines, these being used in pure form or in situ, using bases, for example with alcoholates such as NaOMe, released from their salts.
  • Protic solvents in particular lower alcohols, have proven particularly suitable for the condensation.
  • the reaction can be carried out in protic solvents, such as water or alcohols, at room temperature, at elevated temperatures or at
  • Boiling temperature of the solvent take place, where appropriate an auxiliary base such as alkali metal carbonates or alkali metal alcoholates can be used.
  • Solvent in a solvent inert to POCl 3 (POBr 3 ) or in a basic solvent such as DMF without or with an acid scavenger such as
  • the halogen atom against alcoholates of the corresponding Exchange alkynols (formula V), prepared from the corresponding alkinol and a base, preferably NaH (see. Comprehensive Heterocyclic Chemistry, AR Katritzky, CW Rees, Pergamon Press, Oxford, New York, 1984, Vol.3, p. 100).
  • HCl HBr
  • a base e.g. Triethylamine
  • Solvents can be used at temperatures from 25 ° C to the boiling point of
  • Solvent preferably from 40 ° C to 60 ° C. with base addition, preferably
  • Alkaline alcoholates Pyrimidine carboxylic acid salts obtained as condensation products.
  • alkynyl function Another example of a subsequent modification is the halogenation of the alkynyl function.
  • alkynes, di- and polyynes, allenes, cumulenes / methods of organic chemistry / (Houben / Weyl)
  • aprotic solvent such as THF or dioxane
  • bases e.g. n-Butyllithium, which abstracts the terminal proton of the ethynyl derivative and then a halogen, for example iodine or bromine, is introduced.
  • the compounds of formula I according to the invention can be used to protect various crop plants against pathogenic microorganisms, in particular fungi, and are distinguished by a particularly high crop plant tolerance. They have advantageous preventive and systemic properties, and fungal pathogens that have already penetrated the plant tissue can also be successfully combated. By spraying, dusting or other applications with active ingredients of the formula I, plants and existing or growing parts of plants can be protected from pests which occur. They are also suitable as mordants for the treatment of Seeds and cuttings to protect against fungal infections and pathogenic fungi occurring in the soil.
  • 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
  • the invention also relates to 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.
  • Formulation options are therefore possible: wettable powder (WP), emulsifiable concentrates (EC), aqueous dispersions based on oil or water (SC), suspoemulsions (SC), dusts (DP), mordants, granules in the form of water-dispersible
  • WP wettable powder
  • EC emulsifiable concentrates
  • SC aqueous dispersions based on oil or water
  • SC suspoemulsions
  • DP dusts
  • mordants granules in the form of water-dispersible
  • Granules WG
  • ULV Granules
  • microcapsules microcapsules
  • waxes 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:
  • 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 and which, in addition to the active substance, are also a wetting agent, in addition to a diluent or inert substance.
  • Alkylphenols polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates and
  • Dispersants e.g. B. sodium lignosulfonic acid
  • Emulsifiable concentrates are obtained by dissolving the active ingredient in an organic solvent, e.g. B. butanol,
  • Hydrocarbons produced with the addition of one or more emulsifiers Hydrocarbons produced with the addition of one or more emulsifiers.
  • emulsifiers examples include: alkylarylsulfonic acid
  • Calcium salts such as Ca-dodecylbenzenesulfonate or non-ionic emulsifiers such as
  • Fatty acid polyglycol esters Fatty acid polyglycol esters, alkylaryl polyglycol solvents, fatty alcohol polyglycol ethers, Propylene oxide-ethylene oxide-sorbitan fatty acid ester, polyoxethylene sorbitan fatty acid ester or polyoxethylene sorbitol ester.
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. B. talc, natural clays such as kaolin, bentonite, poryphillite or diatomaceous earth.
  • Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying
  • Active substance concentrates using adhesives e.g. polyvinyl alcohol, polyacrylic acid
  • Sodium 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 appropriate in a mixture with fertilizers.
  • the active ingredient concentration in wettable powders is 10 to 90% by weight, the remainder 100% by weight consists of customary formulation components.
  • the active substance concentration can be 5 to 80% by weight.
  • Dust-like formulations usually contain 5 to 20% by weight.
  • the active ingredient content depends in part on whether the active compound is liquid or solid and which compound is liquid or solid 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.
  • Dust-like and granulated preparations as well as sprayable solutions are usually no longer diluted with other inert substances before use
  • the application rate required varies with the external conditions such as temperature, humidity and others. It can fluctuate within wide limits, e.g. B. from 0.005 to 10.0 kg / ha, preferably it is in the range of 0.01 to 5 kg / ha.
  • the active compounds according to the invention can be used either alone or in combination with other fungicides known from the literature
  • Triadimenol Fluotrimazole, tridemorph, dodemorph, fenpropimorph, falimorph,
  • active ingredients which are largely in CH. R. Worthing, USB Walker, The Pesticide Manual, 7th edition (1983), British Crop Protection Council.
  • active compounds according to the invention in particular those of the examples listed, can be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • Insecticides 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:
  • Pirimiphos-methyl Profenofos, Prothiofos, Sulprofos, Triazophos, Trichlorphon.
  • Allethrin Alphamethrin, bioallethrin, bioresmethrin, cycloprothrin, cyfluthrin, cyhalothrin. Cypermethrin, deltamethrin, 2,2-dimethyl-3- 2-chloro-2-trifluoromethylvinyI) -cyclopropanecarboxylic acid- (alpha-cyano-3-phenyl-2-methyl-benzyI) ester (FMC 54800), fenpropathrin, fenfluthrin, fenvalerate. Flucythrinate, flumethrin, fluvalinate, permethrin, resmethrin, tralomethrin.
  • Application forms can vary within a wide range, the active compound concentration of the use forms can be from 0.0001 to 100% by weight of active compound, preferably from 0.001 to 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • a dispersion concentrate which is easily dispersible in water is prepared by mixing 40 parts by weight of active ingredient 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 ground in a attritor to a fineness of less than 5 microns.
  • An emulsifiable concentrate can be prepared from 15 parts by weight of active ingredient, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated
  • 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.
  • the corresponding ethanolate solution was prepared from 27.6 g of sodium and 480 ml of ethanol and 67.6 g of mucochloric acid were dissolved in 120 ml of ethanol.
  • Half the amount of the ethanolate solution was added dropwise to 156.6 g of benzamidine hydrochloride (80-85%, technical quality, containing about 15% water) in 80 ml of ethanol, and the mixture was heated to 55-60 ° C. and dripped at this temperature first half of the muccochloric acid solution to the reaction mixture, dropwise added the second half of the ethanolate and then the rest of the muccochloric acid solution.
  • the mixture was stirred for a further hour at 55-60 ° C., cooled and filtered off.
  • the mother liquor was adjusted to a pH of 2 with 2N hydrochloric acid and filtered again.
  • the examples with the suffix A are the acid addition salts of the respective parent compound; The acid is then indicated in the "physical constant" column and the associated melting or decomposition point.
  • the salts can also contain water of crystallization in individual cases.
  • the plants were inoculated with a spore suspension (1.5 million spores / ml) of Botrytis cinerea (BCM-resistant strain).
  • the plants were in a climatic chamber at 20-22 ° C. and approx. 99% rel. Humidity continued to be cultivated.
  • the infection of the plants manifests itself in the formation of black spots on leaves and stems.
  • the tests were evaluated approximately 1 week after inoculation.
  • the plants were inoculated with a spore suspension (1.5 million spores / ml) of Botrytis cinerea (BCM-resistant strain).
  • the plants were in a climatic chamber at 20 - 22 ° C and approx. 99% rel. Humidity continued to be cultivated.
  • the infection of the plants manifests itself in the formation of black spots on leaves and stems.
  • the tests were evaluated approximately 1 week after inoculation.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Compounds have formula (I), in which R?1, R2, R3¿ represent independently from each other hydrogen, chlorine, bromine, nitro or (C¿1?-C4)alkoxy; R?4¿ represents hydrogen, iodine, bromine, (C¿1?-C4)alkyl, dialkylamino-(C1-C4)alkyl, phenyl-(C1-C4)alkyl(C1-C4)alkylamino-(C1-C4)alkyl, phenyl or pyridinyl eventually substituted in the phenyl (heteroaromatic) moiety by halogen, (C1-C4)alkyl, (C1-C4)alkoxy or perhalo-(C1-C4)alkyl; R?5¿ represents halogen, (C¿1?-C4)alkyl, (C1-C4)alkoxy, phenyl-(C1-C4)alkoxy, (C1-C4)alkinyloxy, (C1-C4)alkylmercapto or (C1-C4)alkylsulfonyl; R?6¿ represents hydrogen, (C¿1?-C4)alkyl, (C1-C4)alkoxy-(C1-C4)alkyl or (C1-C4)alkoxy-carbonyl; R?5 and R6¿ if necessary form together a saturated or insaturated ring moiety with 5 or 6 members, in which a carbon can be substituted by an S; X represents C=O or NH; Y represents O or NH when X represents C=O; Y is absent when X represents O or NH; and n is a number from 0 to 2. These compounds have advantageous pesticide properties, in particular against fungus pests. A process for producing compounds having formula (I) is also disclosed.

Description

Beschreibung  description

2-PhenyI-pyrimidine, Verfahren zu ihrer Herstellung, sie enthaltene Mittel und ihre Verwendung als Fungizide. 2-PhenyI-pyrimidines, process for their preparation, compositions containing them and their use as fungicides.

Anwendungen von 2-Phenyl-pyrimidinen im Agrarsektor sind beschrieben (z.B. EP 136976, DE 2734 827, EP 323757, EP 112280, JP 61/012206). Man findet aber nur wenige Applications of 2-phenyl-pyrimidines in the agricultural sector have been described (e.g. EP 136976, DE 2734 827, EP 323757, EP 112280, JP 61/012206). But there are only a few

Hinweise auf fungizide Wirkung bei dieser Substanzklasse (Yakugaku Zasshi, 109(7) (1989), 464-473; EP 323 757, DD 246295, DD 238 791, DE 18 00709).  Indications of fungicidal activity in this class of substances (Yakugaku Zasshi, 109 (7) (1989), 464-473; EP 323 757, DD 246295, DD 238 791, DE 18 00709).

Es wurden 2-Phenylpyrimidin-Derivate gefunden, die vorteilhafte Wirkungen bei der There have been found 2-phenylpyrimidine derivatives which have advantageous effects in the

Bekämpfung eines breiten Spektrums phytopatogener Pilze, insbesondere bei niedrigen Dosierungen, aufweisen und keine Schädigung der Nutzpflanzen verursachen.  Combat a wide range of phytopatogenic fungi, especially at low doses, and do not cause damage to crops.

Gegenstand der vorliegenden Erfindung sind daher Verbindungen der Formel The present invention therefore relates to compounds of the formula

Figure imgf000003_0001
Figure imgf000003_0001

worin wherein

R1, R2, R3 = unabhängig voneinander Wasserstoff, Halogen, Hydroxy, Amino, Nitro, Cyano, Thiocyano, (C1-C4)Alkyl, Cyano-(C1-C4)alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylarnino, (C1-C4)Dialkylamino, (C1-C4)Alkylcarbonylamino, Halo-(C1-C4)alkyl, R 1 , R 2 , R 3 = independently of one another hydrogen, halogen, hydroxy, amino, nitro, cyano, thiocyano, (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylarnino, (C 1 -C 4 ) dialkylamino, (C 1 -C 4 ) alkylcarbonylamino, halo (C 1 -C 4 ) alkyl,

Hydroxy-(C1-C4)alkyl, Dihydroxy-(C1-C4)alkyl, (C1-C4)Alkoxy-(C1-C4)alkyl, Hydroxy- (C 1 -C 4 ) alkyl, dihydroxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl,

Halo(C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)Alkylthio, Halo-(C1-C4)alkylthio, Halo (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio, halo (C 1 -C 4 ) alkylthio,

Halo-(C1-C4)alkylthio-(C1-C4)alkyl, (C1-C4)Alkylthio-(C1-C4)allcyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C1-C4)Alkyla mino-(C1-C4)alkyl, Halo (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) allcyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 1 -C 4 ) alkylamino- (C 1 -C 4 ) alkyl,

(C1-C4)Dialkylarnino-(C1-C4)alkyl, (C3-C9)Cycloalkyla mino-(C1-C4)alkyl, (C3-C9)Cycloalkyl, (C3-C9)Cycloalkyl-(C1 -C4)alkyl, (C 1 -C 4 ) dialkylarnino- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) cycloalkylamino- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) cycloalkyl, (C 3 -C 9 ) cycloalkyl- (C 1 -C 4 ) alkyl,

(C3-C9)Heterocycloalkyl-(C1-C4)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C1-C4)AlkyI substituiert sein können, (C1-C4)Alkoxycarbonyl-(C1-C4)alkyl, (C1-C4)Alkylaminocarbonyl-(C1-C4)alkyl, (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl, where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl,

(C1-C4)Dialkylamincarbonyl-(C1-C4)alkyl, (C1-C4)Alkylcarbonyl, (C 1 -C 4 ) dialkylamine carbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylcarbonyl,

(C1-C4)Haloalkylcarbonyl, (C1-C4)Alkoxycarbonyl, (C1-C4)Haloalkoxycarbonyl, (C1-C4)Alkylthiocarbonyl, (C1-C4)Haloalkylihiocarbonyl, Aminocarbonyl, (C 1 -C 4 ) haloalkylcarbonyl, (C 1 -C 4 ) alkoxycarbonyl, (C 1 -C 4 ) haloalkoxycarbonyl, (C 1 -C 4 ) alkylthiocarbonyl, (C 1 -C 4 ) haloalkylihiocarbonyl, aminocarbonyl,

(C1-C4)Alkylaminocarbonyl, (C1-C4)Haloalkylaminocarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenyl-(C1-C4)alkyl, gegebenenfalls substituiertes (C 1 -C 4 ) alkylaminocarbonyl, (C 1 -C 4 ) haloalkylaminocarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenyl- (C 1 -C 4 ) alkyl, optionally substituted

Phenoxy-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylketo-(C1-C4)alkyl, gegebenenfalls substituiertes Phenyloxycarbonyl-(C1-C4)alkyl, Phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenylketo- (C 1 -C 4 ) alkyl, optionally substituted phenyloxycarbonyl- (C 1 -C 4 ) alkyl,

Phenylmercapto-(C1-C4)alkyl, Phenylamino-(C 1-C4 )alkyl, Phenylmercapto- (C 1 -C 4 ) alkyl, phenylamino- (C 1 -C 4 ) alkyl,

Phenoxyphenyl-(C1-C4)aIkyl, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil bis zu dreifach durch Halogen, Ester, (C1-C4)Alkyl, Phenoxyphenyl- (C 1 -C 4 ) alkyl, where optionally substituted is to be understood that the phenyl part up to three times by halogen, ester, (C 1 -C 4 ) alkyl,

(C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl, (C1-C4)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy or can be simply substituted by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms,

R1,R2 und/oder R3 gegebenenfalls zusammen einen gesättigten, teilweise ungesättigten oder aromatischen Carbocyclus oder Heterocyclus mit den Heteroatomen O, N, S, Si oder P mit 4 bis 10 Ringgliedem, R 1 , R 2 and / or R 3 optionally together form a saturated, partially unsaturated or aromatic carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members,

R4 = Wasserstoff, Halogen, (C1-C4)Alkyl, Hydroxy-(C1-C4)alkyI, Dihydroxy-(C1-C4)alkyl, Cyano-(C1-C4)alkyl, Halo-(C1-C4)alkyl, (C1-C4)Alkoxy-(C1-C4)alkyl, R 4 = hydrogen, halogen, (C 1 -C 4 ) alkyl, hydroxy- (C 1 -C 4 ) alkyl, dihydroxy- (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl, halo - (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl,

Halo(C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)Alkylthio, Halo-(C1-C4)alkylthio, Halo (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio, halo (C 1 -C 4 ) alkylthio,

Halo-(C1-C4)alkylthio-(C1-C4)alkyl, (C1-C4)Alkylthio-(C1-C4)alkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C1-C4)Alkylamino-(C1-C4)alkyl, Halo (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 1 -C 4 ) alkylamino- (C 1 -C 4 ) alkyl,

(C1-C4)Dialkylamino-(C1-C4)alkyl, (C3-C9)Cycloalkylamino-(C1-C4)alkyl, (C 1 -C 4 ) dialkylamino- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) cycloalkylamino- (C 1 -C 4 ) alkyl,

(C3-C9)Cycloalkyl, (C3-C9)Cycloalkyl-(C1 -C4)alkyl, (C 3 -C 9 ) cycloalkyl, (C 3 -C 9 ) cycloalkyl- (C 1 -C 4 ) alkyl,

(C3-C9)Heterocycloalkyl-(C1-C4)aIkyl, wobei die cyclischen Reste bis zu dreifach durch (C1-C4)Alkyl substituiert sein können, (C1-C4)Alkoxycarbonyl-(C1-C4)alkyl, (C1-C4) Alkylaminocarbonyl-(C1-C4)alkyl, (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl, where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl,

(C1-C4)Dialicylaminocarb onyl-(C1-C4)alkyl, (C1-C4)Alkylcarbonyl, (C1-C4)Haloalkylcarbonyl, (C1-C4)Alkoxycarbonyl, (C1-C4)Haloalkoxycarbonyl, (C1-C4)Alkylthiocarbonyl, (C1-C4)Haloalkylthiocarbonyl, Aminocarbonyl, (C 1 -C 4 ) dialicylaminocarb onyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylcarbonyl, (C 1 -C 4 ) haloalkylcarbonyl, (C 1 -C 4 ) alkoxycarbonyl, (C 1 -C 4 ) haloalkoxycarbonyl, (C 1 -C 4 ) alkylthiocarbonyl, (C 1 -C 4 ) haloalkylthiocarbonyl, aminocarbonyl,

(C1-C4)Alkylaminocarbonyl, (C1-C4)Haloalkylaminocarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenyl-(C1-C4)alkyl, gegebenenfalls substituiertes (C 1 -C 4 ) alkylaminocarbonyl, (C 1 -C 4 ) haloalkylaminocarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenyl- (C 1 -C 4 ) alkyl, optionally substituted

Phenoxy-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylmercapo -(C1-C4)alkyl, gegebenenfalls substituierter 5- oder 6-gliedriger Heteroaromat, gegebenenfalls substituiertes Phenylcarbonyl, gegebenenfalls substituiertes Phenylketo-(C1-C4)alkyl, gegebenenfalls substituiertes Phenyloxycarbonyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylamino-(C1-C4)alkyl, gegebenenfalls substituiertes Phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenylmercapo - (C 1 -C 4 ) alkyl, optionally substituted 5- or 6-membered heteroaromatic, optionally substituted phenylcarbonyl, optionally substituted phenylketo (C 1 -C 4 ) alkyl , optionally substituted phenyloxycarbonyl- (C 1 -C 4 ) alkyl, optionally substituted phenylamino- (C 1 -C 4 ) alkyl, optionally substituted

Phenoxyphenyl-(C1-C4)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil (Heteroaromat) bis zu dreifach durch Halogen, Ester, Phenoxyphenyl- (C 1 -C 4 ) alkyl, where optionally substituted is to be understood that the phenyl part (heteroaromatic) up to three times by halogen, ester,

(C1-C4)AIkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)HaloaIkyl, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl,

(C1-C4)Haloalkoxy oder einfach durch Nitro oder Cyano substituert sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann, (C 1 -C 4 ) haloalkoxy or simply substituted by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms,

R5 = Halogen, (C1-C4)Alkyl, (C1-C9)Alkoxy, Hydroxy-(C1-C4)alkyl, R 5 = halogen, (C 1 -C 4 ) alkyl, (C 1 -C 9 ) alkoxy, hydroxy- (C 1 -C 4 ) alkyl,

Dihydroxy-(C1-C4)alkyl, Cyano-(C1-C4)alkyl, Halo-(C1-C4)alkyl, Dihydroxy- (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl, halo- (C 1 -C 4 ) alkyl,

(C1-C4)Alkoxy-(C1-C4)alkyl, Halo(C1-C4 )alkoxy-(C1-C4)alkyl, (C1-C4)Alkylthio, Halo-(C1-C4)alkylthio, Halo-(C1-C4)alkylthio-(C1-C4)alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, halo (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio, halo- (C 1 -C 4 ) alkylthio, halo (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl,

(C1-C4)Alkylthio-(C1-C4)alkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C1-C4)Alkylamino, (C1-C4)Dialkylamino, (C3-C9)Cycloalkylamino, (C1-C4)Alkylamino-(C1-C4)alkyl, (C1-C4)Dialtylamino-(C1-C4)alkyl, (C3-C9)Cycloalkylamino-(C1-C4)alkyl, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 1 -C 4 ) alkylamino, (C 1 -C 4 ) dialkylamino, (C 3 -C 9 ) cycloalkylamino, (C 1 -C 4 ) alkylamino- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) dialtylamino- (C 1 -C 4 ) alkyl, ( C 3 -C 9 ) cycloalkylamino- (C 1 -C 4 ) alkyl,

(C3-C9)Cycloalkyl, (C3-C9)Cycloalkyl-(C1 -C4)alkyl, (C 3 -C 9 ) cycloalkyl, (C 3 -C 9 ) cycloalkyl- (C 1 -C 4 ) alkyl,

(C3-C9)Heterocycloalkyl-(C1-C4)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C1-C4)Alkyl substituiert sein können, (C1-C4)Alkoxycarbonyl-(C1-C4)alkyl, (C1-C4)Alkylaminocarbonyl-(C1-C4)alkyl, (C 3 -C 9 ) heterocycloalkyl- (C 1 - C4 ) alkyl, where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 - C 4 ) alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl,

(C1-C4)Dialkylaminocarbonyl-(C1-C4)alkyl, (C1-C4)Alkylcarbonyl, (C 1 -C 4 ) dialkylaminocarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylcarbonyl,

(C1-C4)Haloalkylcarbonyl, (C1-C4)Alkoxycarbonyl, (C1-C4)Haloalkoxycarbonyl, (C1-C4)Alkylthiocarbonyl, (C1-C4)Haloalkylthiocarbonyl, Aminocarbonyl, (C 1 -C 4 ) haloalkylcarbonyl, (C 1 -C 4 ) alkoxycarbonyl, (C 1 -C 4 ) haloalkoxycarbonyl, (C 1 -C 4 ) alkylthiocarbonyl, (C 1 -C 4 ) haloalkylthiocarbonyl, aminocarbonyl,

(C1-C4)Alkylaminocarbonyl, (C1-C4)Haloalkylaminocarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenoxy-(C1-C4)alkyl, gegebenenfalls substituiertes Phenyl-(C1-C4)alkoxy, gegebenenfalls substituiertes Phenylketo-(C1-C4)alkyl, (C 1 -C 4 ) alkylaminocarbonyl, (C 1 -C 4 ) haloalkylaminocarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenyl- (C 1 -C 4 ) alkyl, optionally substituted Phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenyl- (C 1 -C 4 ) alkoxy, optionally substituted phenylketo- (C 1 -C 4 ) alkyl,

Phenyloxycarbonyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenyloxycarbonyl- (C 1 -C 4 ) alkyl, optionally substituted

Phenylamino-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylamino (C 1 -C 4 ) alkyl, optionally substituted

Phenoxyphenyl-(C1-C4)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil bis zu dreifach durch Halogen, Ester, (C1-C4)Alkyl, Phenoxyphenyl- (C 1 -C 4 ) alkyl, whereby optionally substituted is to be understood that the phenyl part is substituted up to three times by halogen, ester, (C 1 -C 4 ) alkyl,

(C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl , (C1-C4)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann, asserstoff, Halogen, (C1-C4)Alkyl, Hydroxy-(C1-C4)alkyl, Dihydroxy-(C1-C4)aIkyl, Cyano-(C1-C4)alkyl, Halo-(C1-C4)alkyl, (C1-C4)Alkoxy-(C1-C4)alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy or can be simply substituted by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms, aerogen, halogen, (C 1 -C 4 ) alkyl, hydroxy- (C 1 -C 4 ) alkyl, dihydroxy- (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl, halo (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl,

Halo-(C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)Alkylthio, Halo-(C1-C4)alkylthio, Halo (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio, halo- (C 1 -C 4 ) alkylthio,

Halo-(C1-C4)alkylthio-(C1-C4)alkyl, (C1-C4)Alkylthio-(C1-C4)alkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C1-C4)Alkylamino, (C1-C4)Dialkylamino, Halo (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 1 -C 4 ) alkylamino, (C 1 -C 4 ) dialkylamino,

(C3-C9)Cycloalkylamino, (C1-C4)Alkylamino-(C1-C4)alkyl, (C 3 -C 9 ) cycloalkylamino, (C 1 -C 4 ) alkylamino- (C 1 -C 4 ) alkyl,

(C1-C4)Dialkylaιmno-(C1-C4)alkyl, (C3-C9)Cycloalkylamino-(C1-C4)alkyl, (C 1 -C 4 ) Dialkylaιmno- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) cycloalkylamino- (C 1 -C 4 ) alkyl,

(C3-C9)Cycloalkyl, (C3-C9)CycloalkyI-(C1 -C4)alkyl, (C 3 -C 9 ) cycloalkyl, (C 3 -C 9 ) cycloalkyI- (C 1 -C 4 ) alkyl,

(C3-C9)Heterocycloalkyl-(C1-C4)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C1-C4)Alkyl substituiert sein können, (C1-C4)Alkoxycarbonyl-(C1-C4)alkyl. (C1-C4) Alkylaminocarbonyl-(C1-C4)alkyl, (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl, where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 -C 4 ) alkyl. (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl,

(C1-C4)Dialkylaminocarbonyl-(C1-C4)alkyl, (C1-C4)Alkylcarbonyl, (C 1 -C 4 ) dialkylaminocarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylcarbonyl,

(C2 -C4)Haloalkylcarbonyl, (C1-C4) Alkyloxycarbonyl, (C1-C4)Haloalkyloxycarbonyl, (C1-C4)Alkylthiocarbonyl, (C1-C4)HaloalkylthiocarbonyI, Aminocarbonyl, (C 2 -C 4 ) haloalkylcarbonyl, (C 1 -C 4 ) alkyloxycarbonyl, (C 1 -C 4 ) haloalkyloxycarbonyl, (C 1 -C 4 ) alkylthiocarbonyl, (C 1 -C 4 ) haloalkylthiocarbonyI, aminocarbonyl,

(C1-C4)Alkylaminocarbonyl, (C1-C4)HaloaIkylaminocarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenylketo-(C1-C4)alkyl, gegebenenfalls substituiertes (C 1 -C 4 ) alkylaminocarbonyl, (C 1 -C 4 ) haloalkylaminocarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenylketo (C 1 -C 4 ) alkyl, optionally substituted

Phenyloxycarbonyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenyloxycarbonyl- (C 1 -C 4 ) alkyl, optionally substituted

Phenoxy-(C1-C4)alkyl, gegebenenfalls substituiertes Phenyl-(C1-C4)alkyl, Phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenyl- (C 1 -C 4 ) alkyl,

gegebenenfalls substituiertes Phenylmercapto-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylamino-(C1-C4)alkyl, gegebenenfalls substituiertes optionally substituted phenylmercapto (C 1 -C 4 ) alkyl, optionally substituted phenylamino (C 1 -C 4 ) alkyl, optionally substituted

Phenoxyphenyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenoxyphenyl- (C 1 -C 4 ) alkyl, optionally substituted

Phenylmercapto-(C1-C4)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil bis zu dreifach durch Halogen, Ester, (C1-C4)Alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl, (C1-C4)Haloalkoxy oder einfach durch Nitro oder Cyano substituert sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann, Phenylmercapto- (C 1 -C 4 ) alkyl, where optionally substituted is to be understood that the phenyl part is substituted up to three times by halogen, ester, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy or can be simply substituted by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms,

R5 und R6 gegebenenfalls zusammen einen gesättigten, teilweise ungesättigten oder R 5 and R 6 optionally together a saturated, partially unsaturated or

aromatischen Carbocyclus oder Heterocyclus mit den Heteroatomen O, N, S, Si oder P mit 4 bis 10 Ringgliedem,  aromatic carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members,

X = O, S, NH, N-(C1-C4)Alkyl, C=O, C=S oder CR7R8 X = O, S, NH, N- (C 1 -C 4 ) alkyl, C = O, C = S or CR 7 R 8

R7, R8 = unabhängig voneinander Wasserstoff, Hydroxy, (C1-C4)Alkyl oder (C1-C4)Alkoxy, R 7 , R 8 = independently of one another hydrogen, hydroxy, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy,

Y = O, NH, N-(C1-C4)Alkyl oder CR9R10, wenn X = Y = O, NH, N- (C 1 -C 4 ) alkyl or CR 9 R 10 if X =

C = O, C = S oder CR7R8 bedeutet, oder CR9R10 oder entfällt, wenn X = O, S, NH oder N-(C1-C4)Alkyl bedeutet, C = O, C = S or CR 7 R 8 , or CR 9 R 10 or is absent if X = O, S, NH or N- (C 1 -C 4 ) alkyl,

R9, R10 = unabhängig voneinander Wasserstoff, (C1-C9)Alkyl, Cyano-(C1-C4)alkyl, R 9 , R 10 = independently of one another hydrogen, (C 1 -C 9 ) alkyl, cyano- (C 1 -C 4 ) alkyl,

Halo-(C1-C4)alkyl, Hydroxy-(C1-C4)alkyl, Dihydroxy-(C1-C4)alkyl, Halo (C 1 -C 4 ) alkyl, hydroxy (C 1 -C 4 ) alkyl, dihydroxy (C 1 -C 4 ) alkyl,

(C1-C4)Alkoxy-(C1-C4)alkyl, Halo(C1-C4)alkoxy-(C1-C4)alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, halo (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl,

Halo-(C1-C4)alkylthio-(C1-C4)alkyl, (C1-C4)Alkylthio-(C1-C4)alkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C1-C4)Alkylamino-(C1-C4)alkyl, Halo (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 1 -C 4 ) alkylamino- (C 1 -C 4 ) alkyl,

(C1-C4)Dialkylarnino-(C1-C4)alkyl, (C3-C9)Cycloalkyla mino-(C1-C4)alkyl, (C 1 -C 4 ) dialkylarnino- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) cycloalkylamino- (C 1 -C 4 ) alkyl,

(C3-C9)Cycloalkyl, (C3-C9)Cycloalkyl-(C1-C4)alkyl (C 3 -C 9 ) cycloalkyl, (C 3 -C 9 ) cycloalkyl- (C 1 -C 4 ) alkyl

(C3-C9)Heterocycloalkyl-(C1-C4)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C1-C4)Alkyl substituiert sein können, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl, where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted

Phenyl-(C1-C4)alkyl, gegebenenfalls substituierter Phenoxy-(C1-C4)alkyl, Phenyl- (C 1 -C 4 ) alkyl, optionally substituted phenoxy- (C 1 -C 4 ) alkyl,

gegebenenfalls substituiertes Phenylamino-(C1-C4)alkyl, gegebenenfalls substituiertes Phenoxyphenyl-(C1-C4)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist. daß der Phenylteil bis zu dreifach durch Halogen, Ester, (C1-C4)Alkyl, optionally substituted phenylamino (C 1 -C 4 ) alkyl, optionally substituted phenoxyphenyl- (C 1 -C 4 ) alkyl, which is to be understood as being optionally substituted. that the phenyl part up to three times by halogen, ester, (C 1 -C 4 ) alkyl,

(C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl, (C1-C4)Haloalkoxy oder einfach durch Nitro oder Cyano substituert sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann, R9 und R10 gegebenenfalls zusammen einen gesättigten oder teilweise ungesättigten (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy or can be simply substituted by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms, R 9 and R 10 optionally together a saturated or partially unsaturated

Carbocyclus oder Heterocyclus mit den Heteroatomen O, N, S, Si oder P mit 4 bis 10 Ringgliedern und n = eine Zahl von 0 bis 8 bedeuten, sowie deren Säureadditionssalze.  Carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members and n = a number from 0 to 8, and their acid addition salts.

In Formel I bedeutet In formula I means

R1, R2, R3 bevorzugt unabhängig voneinander Wasserstoff, Halogen, Hydroxy, Amino, Nitro. R 1 , R 2 , R 3 preferably independently of one another are hydrogen, halogen, hydroxy, amino, nitro.

Cyano, Thiocyano, (C1-C4)Alkyl, Cyano-(C1-C4)alkyl, (C1-C4)Alkoxy, Cyano, thiocyano, (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy,

(C1-C4)Alkylamino, (C1-C4)Dialkylamino, Halo-(C1-C4)alkyl, Hydroxy-(C1-C4)alkyl. (C1-C4)Alkoxy-(C1-C4)alkyl, Halo-(C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)Alkylthio, Halo-(C1-C4)alkylthio, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C 1 -C 4 ) alkylamino, (C 1 -C 4 ) dialkylamino, halo (C 1 -C 4 ) alkyl, hydroxy (C 1 -C 4 ) alkyl. (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, halo- (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio, halo- ( C 1 -C 4 ) alkylthio, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl,

(C1-C4)Alkylaιruno-(C1-C4)alkyl, (C1-C4)Dialkylammo-(C1-C4)alkyl, (C 1 -C 4 ) alkylauno (C 1 -C 4 ) alkyl, (C 1 -C 4 ) dialkylammo (C 1 -C 4 ) alkyl,

(C3-C9)Cycloalkylamino-(C1-C4)alkyl, (C3-C9)Cycloalkyl, (C 3 -C 9 ) cycloalkylamino- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) cycloalkyl,

(C3-C9)Heterocycloalkyl-(C1-C4)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C1-C4)Alkyl substituiert sein können, (C1-C4)Alkoxycarbonyl-(C1-C4)alkyl, (C1-C4)Alkylaminocarbonyl-(C1-C4)alkyl, (C1-C4)Alkylcarbonyl, (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl, where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylcarbonyl,

(C1-C4)Alkoxycarbonyl, Aminocarbonyl, (C1-C4)Alkylarmnocarbonyl, (C 1 -C 4 ) alkoxycarbonyl, aminocarbonyl, (C 1 -C 4 ) alkylarmnocarbonyl,

gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenoxy-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylketo-(C1-C4)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil bis zu dreifach durch Halogen, Ester, (C1-C4)Alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenyl- (C 1 -C 4 ) alkyl, optionally substituted phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenylketo (C 1 -C 4 ) alkyl, wherein under optionally Substituted is to be understood that the phenyl part up to three times by halogen, ester, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio,

(C1-C4)Haloalkyl, (C1-C4)Haloalkoxy oder einfach durch Nitro oder Cyano substituert sein kann. (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy or simply substituted by nitro or cyano.

R2,R2 und/oder R3 können zusammen einen gesättigten, teilweise ungesättigten oder R 2 , R 2 and / or R 3 together can be a saturated, partially unsaturated or

aromatischen Carbocyclus oder Heterocyclus mit den Heteroatomen O, N oder S mit 4 bis 10 Ringgliedem bilden.  Form aromatic carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10 ring members.

R1, R2, R3 sind insbesondere unabhängig voneinander Wasserstoff, Chlor, Brom, Nitro oder (C1-C4)Alkoxy, besonders bevorzugt Wasserstoff, Chlor, Brom oder OCH3. R 1 , R 2 , R 3 are, in particular independently of one another, hydrogen, chlorine, bromine, nitro or (C 1 -C 4 ) alkoxy, particularly preferably hydrogen, chlorine, bromine or OCH 3 .

R4 bedeutet bevorzugt Wasserstoff, Halogen, (C1-C4)Alkyl, Hydroxy-(C1-C4)alkyl, Dihydroxy-(C1-C4)alkyl, (C1-C4)Alkylthio, Perhalo-(C1-C4)alkylthio, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C1-C4)Alkylamino-(C1-C4)alkyl, R 4 preferably denotes hydrogen, halogen, (C 1 -C 4 ) alkyl, hydroxy- (C 1 -C 4 ) alkyl, Dihydroxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio, perhalo (C 1 -C 4 ) alkylthio, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, ( C 1 -C 4 ) alkylamino (C 1 -C 4 ) alkyl,

(C1-C4)Dialkylammo-(C1-C4)aIkyl, (C3-C9)Cycloalkylamino-(C1-C4)alkyl, (C 1 -C 4 ) dialkylammo- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) cycloalkylamino- (C 1 -C 4 ) alkyl,

(C3-C9)Cycloalkyl, (C3-C9)Cycloalkyl-(C1 -C4)alkyl, (C 3 -C 9 ) cycloalkyl, (C 3 -C 9 ) cycloalkyl- (C 1 -C 4 ) alkyl,

(C3-C9)Heterocycloalkyl-(C1-C4)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C1-C4)Alkyl substituiert sein können, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituierter 5- oder 6-gliedriger Heteroaromat, beispielsweise Pyrimidin, Pyridin oder Thiophen, gegebenenfalls substituiertes Phenylcarbonyl, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylring (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl, where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, optionally substituted phenyl, optionally substituted 5- or 6-membered Heteroaromatic, for example pyrimidine, pyridine or thiophene, optionally substituted phenylcarbonyl, where optionally substituted means that the phenyl ring

(Heteroaromat) bis zu dreifach durch Halogen, Ester, (C1-C4)Alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl, (C1-C4)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann. (Heteroaromatic) up to three times by halogen, ester, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) Haloalkoxy or simply substituted by nitro or cyano.

R4 ist insbesondere Wasserstoff, Jod, Brom, Dialkylamino-(C 1-C4)alkyl, R 4 is in particular hydrogen, iodine, bromine, dialkylamino (C 1 -C 4 ) alkyl,

Phenyl-(C1-C4)alkyl-(C1-C4)alkylamino-(C1-C4)alkyl, im Phenylteil (Heteroaromat) durch Halogen, (C1-C4)Alkyl, (C1-C4)Alkoxy oder Perhalo-(C1-C4)alkyl Phenyl- (C 1 -C 4 ) alkyl- (C 1 -C 4 ) alkylamino- (C 1 -C 4 ) alkyl, in the phenyl part (heteroaromatic) by halogen, (C 1 -C 4 ) alkyl, (C 1 - C 4 ) alkoxy or perhalo (C 1 -C 4 ) alkyl

gegebenenfalls substituiertes Phenyl oder Pyridinyl, besonders bevorzugt Wasserstoff.  optionally substituted phenyl or pyridinyl, particularly preferably hydrogen.

R5 bedeutet bevorzugt Halogen, (C1-C4)Alkyl, (C1-C9)Alkoxy, Hydroxy-(C1-C4)alkyl, R 5 preferably denotes halogen, (C 1 -C 4 ) alkyl, (C 1 -C 9 ) alkoxy, hydroxy- (C 1 -C 4 ) alkyl,

Dihydroxy-(C1-C4)alkyl, Cyano-(C1-C4)alkyl, Halo-(C1-C4)alkyl, Dihydroxy- (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl, halo- (C 1 -C 4 ) alkyl,

(C1-C4)Alkoxy-(C1-C4)alkyl, Halo(C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)Alkylthio, Halo-(C1-C4)alkylthio, Halo-(C1-C4)alkylthio-(C1-C4)alkyl, (C2-C6)Alkenyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, halo (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio, halo- (C 1 -C 4 ) alkylthio, halo (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 2 -C 6 ) alkenyl,

(C2-C6)Alkinyl. (C1-C4)Alkylamino, (C1-C4)Dialkylamino, (C3-C9)Cycloalkylamino, (C1-C4)Alkylamino-(C1-C4)alkyl, (C1-C4)Dialkylamino-(C1-C4)alkyl, (C 2 -C 6 ) alkynyl. (C 1 -C 4 ) alkylamino, (C 1 -C 4 ) dialkylamino, (C 3 -C 9 ) cycloalkylamino, (C 1 -C 4 ) alkylamino- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) dialkylamino- (C 1 -C 4 ) alkyl,

(C3-C9)Cycloalkylamino-(C1-C4)alkyl, (C3-C9)Cycloalkyl, (C 3 -C 9 ) cycloalkylamino- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) cycloalkyl,

(C3-C9)Cycloalkyl-(C1-C4)alkyl, (C3-C9)Heterocycloalkyl-(C1-C4)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C1-C4)Alkyl substituiert sein können, (C 3 -C 9 ) cycloalkyl- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl, the cyclic radicals being up to threefold by (C 1 -C 4 ) Alkyl can be substituted,

(C1-C4)Alkylcarbonyl, (C1-C4)Alkoxycarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes (C 1 -C 4 ) alkylcarbonyl, (C 1 -C 4 ) alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted

Phenyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenoxy-(C1-C4)alkyl, Phenyl- (C 1 -C 4 ) alkyl, optionally substituted phenoxy- (C 1 -C 4 ) alkyl,

gegebenenfalls substituiertes Phenyl-(C1-C4)alkoxy, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil bis zu dreifach durch Halogen, Ester, (C1-C4)Alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl, optionally substituted phenyl- (C 1 -C 4 ) alkoxy, where optionally substituted is understood to mean that the phenyl part is substituted up to three times by halogen, ester, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl,

(C1-C4)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann und R5 ist insbesondere Halogen, (C1-C4)AIkyl, (C1-C4)Alkoxy, Phenyl-(C1-C4)alkoxy, (C1-C4)Alkinyloxy, (C1-C4)Alkylmercapto oder (C1-C4) Alkylsulfonyl, besonders bevorzugt Cl, Br, OCH3 oder OC2H5. (C 1 -C 4 ) haloalkoxy or simply substituted by nitro or cyano and R 5 is in particular halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, phenyl- (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkynyloxy, (C 1 -C 4 ) Alkylmercapto or (C 1 -C 4 ) alkylsulfonyl, particularly preferably Cl, Br, OCH 3 or OC 2 H 5 .

R6 bedeutet bevorzugt Wasserstoff, Halogen, (C1-C4)Alkyl, Hydroxy-(C1-C4)alkyl, R 6 preferably denotes hydrogen, halogen, (C 1 -C 4 ) alkyl, hydroxy- (C 1 -C 4 ) alkyl,

Perhalo-(C1-C4)alkyl, (C1-C4)Alkoxy-(C1-C4)alkyl, Perhalo (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkyl,

Halo-(C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)Alkylthio, (C1-C4)Alkylthio-(C1-C4)alkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C1-C4)Alkylamino, (C1-C4)Dialkylamino, (C3-C9)Cycloalkylamino, (C1-C4)Alkylamino-(C1-C4)alkyl, Halo (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 1 -C 4 ) alkylamino, (C 1 -C 4 ) dialkylamino, (C 3 -C 9 ) cycloalkylamino, (C 1 -C 4 ) alkylamino - (C 1 -C 4 ) alkyl,

(C1-C4)Dialkylamino-(C1-C4)alkyl, (C3-C9)Cycloalkylamino-(C1-C4)alkyl, (C 1 -C 4 ) dialkylamino- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) cycloalkylamino- (C 1 -C 4 ) alkyl,

(C3-C9)Cycloalkyl, (C3-C9)Cycloalkyl-(C1-C4)alkyl, (C 3 -C 9 ) cycloalkyl, (C 3 -C 9 ) cycloalkyl- (C 1 -C 4 ) alkyl,

(C3-C9)Heterocycloalkyl-(C1-C4)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C1-C4)Alkyl substituiert sein können, (C1-C4)Alkylcarbonyl, (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl, where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylcarbonyl,

(C1-C4)Alkoxycarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenylketo-(C1-C4)alkyl, gegebnenfalls substituiertes Phenoxycarbonyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenyl-(C1-C4)alkyl, gegebenenfalls substituiertes (C 1 -C 4 ) alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenylketo (C 1 -C 4 ) alkyl, optionally substituted phenoxycarbonyl- (C 1 -C 4 ) alkyl, optionally substituted phenyl- (C 1 -C 4 ) alkyl, optionally substituted

Phenoxy-(C1-C4)alkyl, gegebenenfalls substituiertes Phenoxyphenyl-(C1-C4)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil bis zu dreifach durch Halogen, Ester, (C1-C4)Alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl, (C1-C4)Haloalkoxy oder einfach durch Nitro oder Cyano substituert sein kann. Phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenoxyphenyl- (C 1 -C 4 ) alkyl, whereby optionally substituted is understood to mean that the phenyl part is substituted up to three times by halogen, ester, (C 1 -C 4 ) Alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy or can simply be substituted by nitro or cyano.

R6 ist insbesondere Wasserstoff, (C1-C4)Alkyl, (C1-C4)Alkoxy-(C1-C4)alkyl oder R 6 is in particular hydrogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl or

(C1-C4)Alkoxycarbonyl, besonders bevorzugt Wasserstoff oder -O-CH2-CH2. (C 1 -C 4 ) alkoxycarbonyl, particularly preferably hydrogen or -O-CH 2 -CH 2 .

R5 und R6 können zusammen einen gesättigten, teilweise ungesättigten oder aromatischenR 5 and R 6 together can be a saturated, partially unsaturated or aromatic

Carbocyclus oder Heterocyclus mit den Heteroatomen O, N oder S, insbesondere mit 4 bis 10, insbesondere 5 oder 6 Ringgliedern bilden. Form carbocycle or heterocycle with the heteroatoms O, N or S, in particular with 4 to 10, in particular 5 or 6, ring members.

Bevorzugt stehen X für O, NH, N-(C1-C4)Alkyl, S, C=O, C=S oder CR7R8, insbesondere für C=O, O oder NH und R7, R8 sind bevorzugt unabhängig voneinander für Wasserstoff, Hydroxy, (C1-C4)Alkyl oder (C1-C4)Alkoxy, X is preferably O, NH, N- (C 1 -C 4 ) alkyl, S, C = O, C = S or CR 7 R 8 , in particular C = O, O or NH and R 7 , R 8 are preferably independently of one another hydrogen, hydroxyl, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy,

Y ist vorzugsweise O, NH, N-(C1-C4)Alkyl oder CR9R10, insbesondere O oder NH, wenn X = Y is preferably O, NH, N- (C 1 -C 4 ) alkyl or CR 9 R 10 , in particular O or NH, if X =

C=O, C=S oder CR7R8, oder Y = CR9R10 oder entfallt, insbesondere entfällt Y, wenn X = O, S, NH oder N-(C1-C4)Alkyl ist, C = O, C = S or CR 7 R 8 , or Y = CR 9 R 10 or omitted, in particular Y is omitted if X = O, S, NH or N- (C 1 -C 4 ) alkyl,

R9, R10 sind unabhängig voneinander Wasserstoff, (C1-C9)Alkyl oder durch Halogen, R 9 , R 10 are independently hydrogen, (C 1 -C 9 ) alkyl or by halogen,

(C1-C4)Alkyl oder (C1-C4)Alkoxy gegebenenfalls substituiertes Phenyl, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy optionally substituted phenyl,

R9 und R10 können zusammen einen gesättigten oder teilweise ungesättigten Carbocyclus oder Heterocyclus mit den Heteroatomen O, N oder S mit 4 bis 10, insbesondere 5 oder 6 Ringgliedern bilden, n ist vorzugsweise eine Zahl von 0 bis 4, insbesondere eine Zahl von 0 bis 2 R 9 and R 10 together can form a saturated or partially unsaturated carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10, in particular 5 or 6, ring members, n is preferably a number from 0 to 4, in particular a number of 0 up to 2

Halo bedeutet in den Substituenten ein- oder mehrfach durch Halogenatome substituiert. Halo in the substituents is substituted one or more times by halogen atoms.

Zur Herstellung der Säureadditionssalze der Verbindungen der Formel I kommen folgende Säuren in Frage: Halogenwasserstoffsäuren wie Chlorwasserstoffsäure oder The following acids are suitable for the preparation of the acid addition salts of the compounds of the formula I: hydrohalic acids such as hydrochloric acid or

Bromwasserstoffsäure, Phosphorsäure, Salpetersäure, Schwefelsäure, mono- oder Hydrobromic acid, phosphoric acid, nitric acid, sulfuric acid, mono- or

bifunktionelle Carbonsäuren und Hydroxycarbonsäuren wie Essigsäure, Maleinsäure, Bernsteinsäure, Fumarsäure, Weinsäure, Citronensäure, Salicylsäure, Sorbinsäure oder Milchsäure, sowie Sulfonsäuren wie p-Toluolsulfonsäure oder 1,5-Naphthalindisulfonsäure Die Säureadditionsverbindungen der Formel I können in einfacher Weise nach den üblichen Salzbildungsmethoden, z.B. durch Lösen einer Verbindung der Formel I in einem geeigneten organischen Lösungsmittel und Hinzufügen der Säure erhalten werden und in bekannter Weise, z.B. durch Abfϊltrieren, isoliert und gegebenenfalls durch Waschen mit einem inerten organischen Lösungsmittel gereinigt werden. bifunctional carboxylic acids and hydroxycarboxylic acids such as acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid or lactic acid, as well as sulfonic acids such as p-toluenesulfonic acid or 1,5-naphthalenedisulfonic acid. The acid addition compounds of the formula I can be prepared in a simple manner, e.g. be obtained by dissolving a compound of formula I in a suitable organic solvent and adding the acid and in a known manner, e.g. by filtration, isolated and optionally cleaned by washing with an inert organic solvent.

Die Pyrimidine der Formel I können nach verschiedenen mehrstufigen Verfahren hergestellt werden. Man erhält die Verbindungen der Formel I, worin Y = O, NH oder N-(C1-C4)Alkyl und X = C=O, C=S oder CR7R8 bedeuten, indem man Verbindungen der Formel II The pyrimidines of the formula I can be prepared by various multistage processes. The compounds of the formula I in which Y = O, NH or N- (C 1 -C 4 ) alkyl and X = C = O, C = S or CR 7 R 8 are obtained by using compounds of the formula II

Figure imgf000012_0001
worin
Figure imgf000012_0001
wherein

Hal = Chlor oder Brom bedeutet,  Hal = chlorine or bromine means

mit Verbindungen der Formel III with compounds of formula III

HY- (CH2)n - C≡C— R 4 (III) oder, falls in der Formel I Y = CR9R10 oder entfällt und X = O, S, NH oder N-(C1-C4)Alkyl bedeutet, indem man Verbindungen der Formel IV HY- (CH 2 ) n - C≡C— R 4 (III) or, if in the formula IY = CR 9 R 10 or is absent and X = O, S, NH or N- (C 1 -C 4 ) alkyl means by using compounds of formula IV

Figure imgf000012_0002
Figure imgf000012_0002

worin wherein

Hal = Chlor oder Brom bedeutet,  Hal = chlorine or bromine means

mit Verbindungen der Formel V

Figure imgf000013_0002
with compounds of formula V
Figure imgf000013_0002

umsetzt, sowie gegebenenfalls, wenn R4 = H bedeutet, den Wasserstoff gegen Halogen austauscht. converts, and optionally, if R 4 = H, exchanges the hydrogen for halogen.

Durch Kondensation geeigneter 3-Ketocarbonsäureester mit Benzamidinen, wobei sie in reiner Form oder in situ, aus ihren Salzen freigesetzt, eingesetzt werden können, ohne Lösungsmittel oder in einem geeigneten aprotischen oder protischen Lösungsmittel z.B. Wasser oder niedere Alkohole, bei Temperaturen von 0°C bis 160 °C, bevorzugt bei Temperaturen zwischen Raumtemperatur und der Siedetemperatur des Lösungsmittel, in Gegenwart einer geeigneten Base, wie Alkalicarbonate, Na2CO3 oder K2CO3, oder By condensation of suitable 3-ketocarboxylic acid esters with benzamidines, where they can be used in pure form or in situ, released from their salts, without solvent or in a suitable aprotic or protic solvent, for example water or lower alcohols, at temperatures from 0 ° C to 160 ° C, preferably at temperatures between room temperature and the boiling point of the solvent, in the presence of a suitable base, such as alkali metal carbonates, Na 2 CO 3 or K 2 CO 3 , or

Alkalialkoholate, z.B. NaOMe oder NaOEt, zu entsprechenden 4-Pyrimidinonen.  Alkali alcoholates, e.g. NaOMe or NaOEt, to corresponding 4-pyrimidinones.

Figure imgf000013_0001
Figure imgf000013_0001

Die Verfahren sind aus der Literatur (vergl. Comprehensive Heterocyclic Chemistry, A.R. Katritzky, C.W. Rees, Pergamon Press, Oxford, New York, 1984, Vol.3, S.113) bekannt, die Edukte sind käuflich oder können nach literaturbekannten Verfahren hergestellt werden. The processes are known from the literature (cf. Comprehensive Heterocyclic Chemistry, AR Katritzky, CW Rees, Pergamon Press, Oxford, New York, 1984, Vol.3, p.113), the starting materials are commercially available or can be prepared by processes known from the literature .

4-Pvrirnidinone mit R6 = Wasserstoff können in Anlehnung an entsprechende 4-Pvrirnidinone with R 6 = hydrogen can be based on corresponding

Literaturvorschriften (Beilstein, 3./4. Ergänzungswerk, Band 25, S. 279) 2-stufig in einem Eintopfverfahren hergestellt werden. Zunächst werden in einem inerten Lösungsmittel, wie Toluol, THF, Dioxan oder Diethylether, entsprechende Carbonsäurederivate mit einer geeigneten Base, im allgemeinen mit einem Alkalihydrid, vorzugsweise NaH, oder Literature regulations (Beilstein, 3rd / 4th supplement, volume 25, p. 279) can be produced in two stages in a one-pot process. First, in an inert solvent such as toluene, THF, dioxane or diethyl ether, corresponding carboxylic acid derivatives with a suitable base, generally with an alkali metal hydride, preferably NaH, or

Alkalialkoholat, vorzugsweise NaOMe, anionisiert, dann mit einem Ameisenester formyliert. Die anschließende Kondensation kann mit Benzamidinen erfolgen, wobei diese in reiner Form oder in situ, mittels Basen, z.B. mit Alkoholaten wie NaOMe, aus Ihren Salzen freigesetzt, eingesetzt werden. Als besonders geeignet für die Kondensation haben sich protische Lösungsmittel, insbesondere niedere Alkohole, erwiesen. Alkaline alcoholate, preferably NaOMe, anionized, then formylated with an ant ester. The subsequent condensation can be carried out with benzamidines, these being used in pure form or in situ, using bases, for example with alcoholates such as NaOMe, released from their salts. Protic solvents, in particular lower alcohols, have proven particularly suitable for the condensation.

Figure imgf000014_0001
Figure imgf000014_0001

Bei genügendem Überschuß an Ameisenester erhält man das 6-H-Derivat bei guter With a sufficient excess of ants, the 6-H derivative is obtained with a good one

Selektivität  selectivity

Die Edukte, bei denen R5 und R6 = Wasserstoff bedeuten, können in Anlehnung an die oben genannten Methoden durch Umsetzung von Natriumformylessigsäureestern (Beilstein, Hauptwerk, Band 3, S. 627) mit Benzamidinen hergestellt werden, wobei diese in reiner Form oder in situ, mittels Basen, z.B. mit Alkoholaten wie NaOMe, aus ihren Salzen freigesetzt, eingesetzt werden. Die Reaktion kann in protischen Lösungsmittel, wie Wasser oder Alkoholen, bei Raumtemperatur, erhöhten Temperaturen oder auch bei der The starting materials, in which R 5 and R 6 = hydrogen, can be prepared based on the methods mentioned above by reacting sodium formylacetic acid esters (Beilstein, Hauptwerk, Volume 3, p. 627) with benzamidines, these in pure form or in situ, by means of bases, for example with alcoholates such as NaOMe, released from their salts. The reaction can be carried out in protic solvents, such as water or alcohols, at room temperature, at elevated temperatures or at

Siedetemperatur des Lösungsmittels erfolgen, wobei gegebenenfalls eine Hilfsbase wie Alkalicarbonate oder Alkalialkoholate eingesetzt werden können.  Boiling temperature of the solvent take place, where appropriate an auxiliary base such as alkali metal carbonates or alkali metal alcoholates can be used.

Figure imgf000014_0002
Figure imgf000014_0002

Die Modifizierung bekannter Pyrimidinone, insbesondere zur Herstellung von Verbindungen der Formel I mit R5 = Halogen, erfolgt durch Umsetzung der entsprechenden 4-Pyιimidinone mit elementaren Halogenen, beispielsweise Chlor oder Brom, in einem aprotischen oder protischen Lösungsmittel wie Essigsäure (vergl. Comprehensive Heterocyclic Chemistry, A.R. Katritzky, C.W. Rees, Pergamon Press, Oxford, New York, 1984, Vol.3, S.70). The modification of known pyrimidinones, in particular for the preparation of compounds of the formula I with R 5 = halogen, is carried out by reacting the corresponding 4-pyimidinones with elemental halogens, for example chlorine or bromine, in an aprotic or protic solvent such as acetic acid (see Comprehensive Heterocyclic Chemistry, AR Katritzky, CW Rees, Pergamon Press, Oxford, New York, 1984, Vol.3, p.70).

Figure imgf000015_0002
Figure imgf000015_0002

Die so erhaltenen 4-Pyrimidinone können mit überschüssigem POCl3 (POBr3) ohne The 4-pyrimidinones thus obtained can with excess POCl 3 (POBr 3 ) without

Lösungsmittel, in einem gegen POCl3 (POBr3) inertem Lösungsmittel oder in einem basischen Lösungsmittel wie DMF ohne oder mit einem Säurefänger wie Solvent, in a solvent inert to POCl 3 (POBr 3 ) or in a basic solvent such as DMF without or with an acid scavenger such as

N,N-Dimethylanilin in 0,001 bis 2 Moläquivalenten, im allgemeinen 0,02 Äquivalenten, bei Temperaturen von 50°C bis 110°C, bevorzugt bei der Siedetemperatur des POCl3 (POBr3), in die entsprechenden 4-Halogenpyrimidine der Formel (IV) überführt werden (vergl. N, N-dimethylaniline in 0.001 to 2 molar equivalents, generally 0.02 equivalents, at temperatures from 50 ° C. to 110 ° C., preferably at the boiling point of POCl 3 (POBr 3 ), into the corresponding 4-halopyrimidines of the formula ( IV) are transferred (cf.

Comprehensive Heterocyclic Chemistry, A.R. Katritzky, C.W. Rees, Pergamon Press, Oxford, New York, 1984, Vol.3, S.89). Comprehensive Heterocyclic Chemistry, A.R. Katritzky, C.W. Rees, Pergamon Press, Oxford, New York, 1984, Vol.3, p.89).

Figure imgf000015_0001
Figure imgf000015_0001

In Abhängigkeit von der Reaktivität der Derivate kann man bei den 4-Halogenpyrimidinen in einem inerten Lösungsmittel beispielsweise Toluol oder THF bei einer Temperatur von 0°C bis 150°C, vorzugsweise von 25°C bis 50°C, das Halogenatom gegen Alkoholate der entsprechenden Alkinole (Formel V), hergestellt aus dem entsprechenden Alkinol und einer Base, vorzugsweise NaH, austauschen (vergl. Comprehensive Heterocyclic Chemistry, A.R. Katritzky, C.W. Rees, Pergamon Press, Oxford, New York, 1984, Vol.3, S. 100). Depending on the reactivity of the derivatives, in the case of the 4-halopyrimidines in an inert solvent, for example toluene or THF at a temperature of from 0 ° C. to 150 ° C., preferably from 25 ° C. to 50 ° C., the halogen atom against alcoholates of the corresponding Exchange alkynols (formula V), prepared from the corresponding alkinol and a base, preferably NaH (see. Comprehensive Heterocyclic Chemistry, AR Katritzky, CW Rees, Pergamon Press, Oxford, New York, 1984, Vol.3, p. 100).

In analoger Weise kann man auch entsprechende Amine (Formel V) Corresponding amines (formula V)

Figure imgf000016_0002
Figure imgf000016_0002

in geeigneten Lösungsmitteln, wie DMF, Acetonitril oder DMSO, mit 4-Halogenpyrimidinen umsetzen, wobei hier die entstehende HCl (HBr) mit einer Base, z.B. Triethylamin, abgefangen werden sollte. in suitable solvents, such as DMF, acetonitrile or DMSO, with 4-halopyrimidines, the resulting HCl (HBr) with a base, e.g. Triethylamine, should be trapped.

Pyrimidine der Formel I, worin Y = O, NH oder N-(C1-C4)Alkyl bedeutet, können durch Reaktion von Mucobrom(chlor)säure erhalten werden (vergl. Comprehensive Heterocyclic Chemistry, A.R. Katritzky, C.W. Rees, Pergamon Press, Oxford, New York, 1984, Vol.3, S. 127). Überträgt man diese Reaktionsfolge auf Benzamidine oder deren Salze, so erhält man Pyrimidinium-Salze (vergl. Beilstein, Hauptwerk, Band 25, S. 141). In protischen Pyrimidines of the formula I, in which Y = O, NH or N- (C 1 -C 4 ) alkyl, can be obtained by reaction of mucobromo (chloro) acid (cf. Comprehensive Heterocyclic Chemistry, AR Katritzky, CW Rees, Pergamon Press , Oxford, New York, 1984, Vol.3, p. 127). If this reaction sequence is transferred to benzamidines or their salts, pyrimidinium salts are obtained (cf. Beilstein, Hauptwerk, volume 25, p. 141). In protic

Lösungsmitteln kann man bei Temperaturen von 25°C bis zur Siedetemperatur des Solvents can be used at temperatures from 25 ° C to the boiling point of

Lösungsmittels, vorzugsweise von 40°C bis 60°C. unter Basenzusatz, vorzugsweise Solvent, preferably from 40 ° C to 60 ° C. with base addition, preferably

Alkalialkoholate. Pyrimidincarbonsäure-Salze als Kondensationsprodukte erhalten. Alkaline alcoholates. Pyrimidine carboxylic acid salts obtained as condensation products.

Figure imgf000016_0001
Figure imgf000016_0001

Die nachfolgende Chlorierung der Carbonsäure mit Chlorierungsreagenzien, z.B.  The subsequent chlorination of the carboxylic acid with chlorination reagents, e.g.

Thionylchlorid, ergibt die enstprechenden aktivierten Säure-Derivate.

Figure imgf000017_0001
Thionyl chloride, gives the corresponding activated acid derivatives.
Figure imgf000017_0001

Die Umsetzung der 4-Pyrimidincarbonsäurechloride mit entsprechenden Alkoholen, Alkoholaten oder Aminen, die jeweils bereits eine Dreifachbindung tragen, in protischen oder aprotischen Lösungsmitteln, führt unter Standardbedingungen zu entsprechenden Estern oder Amiden.  The reaction of the 4-pyrimidinecarboxylic acid chlorides with corresponding alcohols, alcoholates or amines, each of which already has a triple bond, in protic or aprotic solvents leads to corresponding esters or amides under standard conditions.

Figure imgf000017_0002
Figure imgf000017_0002

Entsprechend können Verbindungen der Formel II, in denen X eine andere Bedeutung als C=O hat, hergestellt werden.  Correspondingly, compounds of the formula II in which X has a meaning other than C = O can be prepared.

Als Beispiel für eine nachträgliche Modifizierung sei eine Übergangsmetall-katalysierte Arylierung der Alkinylfunktion (vergl. M. Fieser, L.F. Fieser, Reagents for Organic An example of a subsequent modification is a transition metal-catalyzed arylation of the alkynyl function (see M. Fieser, L.F. Fieser, Reagents for Organic

Synthesis, John Wiley and Sons, New York, Chichester 1977, Vol.6, Seite 59 ff.) genannt So kann man beispielsweise in Mischungen aus inerten und basischen Lösungsmitteln oder in basischen Lösungsmitteln beispielsweise Triethylamin, Alkine mit halogenierten, z.B.  Synthesis, John Wiley and Sons, New York, Chichester 1977, Vol.6, page 59 ff.). For example, in mixtures of inert and basic solvents or in basic solvents, for example triethylamine, alkynes with halogenated, e.g.

jodierten) Aromaten oder Heteroaromaten zur Reaktion bringen, wobei bevorzugt modifizierte Pd-Katalysatoren verwendet werden.

Figure imgf000018_0001
bring iodinated) aromatics or heteroaromatics to reaction, preferably using modified Pd catalysts.
Figure imgf000018_0001

Als weiteres Beispiel für eine nachträgliche Modifizierung sei die Halogenierung der Alkinyl-Funktion genannt. In Abwandlung liteiaturbekannter Methoden ("Alkine, Di- und Polyine, Allene, Kumulene" / Methoden der organischen Chemie/(Houben/Weyl), Another example of a subsequent modification is the halogenation of the alkynyl function. In a variation of methods known from the literature ("alkynes, di- and polyynes, allenes, cumulenes" / methods of organic chemistry / (Houben / Weyl),

Thieme-Verlag, Stuttgart, 1977, Band 5,2a: S. 600 ff.) kann in einem geeigneten aprotischen Lösungsmittel, wie THF oder Dioxan, mit Basen, z.B. n-Butyllithium, das terminale Proton des Ethinyl-Derivates abstrahiert und anschließend ein Halogen, beispielsweise Jod oder Brom, eingeführt werden. Thieme-Verlag, Stuttgart, 1977, volume 5,2a: p. 600 ff.) Can in a suitable aprotic solvent, such as THF or dioxane, with bases, e.g. n-Butyllithium, which abstracts the terminal proton of the ethynyl derivative and then a halogen, for example iodine or bromine, is introduced.

Figure imgf000018_0002
Figure imgf000018_0002

Die erfindungsgemäßen Verbindungen der Formel I können zum Schutz verschiedener Kulturpflanzen gegen pathogene Mikroorganismen, insbesondere Fungi, eingesetzt werden, wobei sie sich durch eine besonders hohe Kulturpflanzenverträglichkeit auszeichnen. Sie besitzen vorteilhafte präventive und systemische Eigenschaften, bereits in das pflanzliche Gewebe eingedrungene pilzliche Krankheitserreger lassen sich auch erfolgreich kurativ bekämpfen. Durch Besprühen, Bestäuben oder andere Applikationen mit Wirkstoffen der Formel I können Pflanzen und bestehende oder zuwachsende Pflanzenteile vor auftretenden Schädlingen geschützt werden. Sie eignen sich auch als Beizmittel zur Behandlung von Saatgut und Stecklingen zum Schutz vor Pilzinfektionen sowie im Erdboden auftretende pathogene Pilze. Das Wirkungsspektrum der beanspruchten Verbindungen erfaßt eine Vielzahl verschiedener wirtschaftlich bedeutender, phytopathogener Pilze, wie Alternaria mali, Botrytis cinerea, Benzimidazol- und Dicarboximid- sensible und resistente Stämme, Sclerotinia sclerotiorum sowie weitere Grauschimmelarten, Cercospora The compounds of formula I according to the invention can be used to protect various crop plants against pathogenic microorganisms, in particular fungi, and are distinguished by a particularly high crop plant tolerance. They have advantageous preventive and systemic properties, and fungal pathogens that have already penetrated the plant tissue can also be successfully combated. By spraying, dusting or other applications with active ingredients of the formula I, plants and existing or growing parts of plants can be protected from pests which occur. They are also suitable as mordants for the treatment of Seeds and cuttings to protect against fungal infections and pathogenic fungi occurring in the soil. The spectrum of activity of the claimed compounds covers a large number of different economically important phytopathogenic fungi, such as Alternaria mali, Botrytis cinerea, benzimidazole- and dicarboximide- sensitive and resistant strains, Sclerotinia sclerotiorum and other gray mold species, Cercospora

beticola, Ceratobasidium cerealis, Erysiphe graminis, Erysiphe graminis hordei, Erysiphe chichoracearum sowie andere Echte Mehltauarten, Fusarium culmorum und andere  beticola, Ceratobasidium cerealis, Erysiphe graminis, Erysiphe graminis hordei, Erysiphe chichoracearum and other powdery mildew species, Fusarium culmorum and others

Fusariumarten, Moniliniaarten, Leptosphaeria nodorum sowie andere Septoriaarten und Blattfleckenverursachende Arten, Pellicularia sasakii, Pyricularia oryzae und andere  Fusarium species, Monilinia species, Leptosphaeria nodorum as well as other Septoria species and leaf spot causing species, Pellicularia sasakii, Pyricularia oryzae and others

Reispilzsarten, Phytophthora infestans, Phytophtora capsici und verschiedene andere Kraut- und Knollenfäulepilze, Plasmopara viticola, Pseudoperonospora cubensis und weitere Pernospora oder Falsche Mehltauarten, Pseudocercosporella herpotrichoides und  Rice mushroom species, Phytophthora infestans, Phytophtora capsici and various other herb and tuber rot fungi, Plasmopara viticola, Pseudoperonospora cubensis and other Pernospora or downy mildew species, Pseudocercosporella herpotrichoides and

verschiedene andere Augenflecken bzw. Halmbruch verursachende Pilzarten, Puccinia recondita und verschiedene andere Rostpilze, Pyrenophora teres und andere Drechsleraarten, Ustilagoarten, Venturia inaequalis und Schorfarten, wobei jedoch die Wirkung gegen Ascomyceten und Deuteromyceten und insbesondere gegen BCM-resistente  various other eye spots or stalks causing fungus, Puccinia recondita and various other rust fungi, Pyrenophora teres and other woodturning species, Ustilago species, Venturia inaequalis and scab species, but the effect against Ascomycetes and Deuteromycetes and especially against BCM-resistant

Pseudocercosporella herpotrichoides-Stämme hervorzuheben ist.  Pseudocercosporella herpotrichoides strains should be emphasized.

Die erfindungsgemäßen Verbindungen eignen sich daneben auch für den Einsatz in technischen Bereichen, beispielsweise als Holzschutzmittel, als Konservierungsmittel in Anstrichfarben, in Kühlschmiermittel für die Metallbearbeitung oder als 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

Konservierungsmittel in Bohr- und Schneidölen. Preservative in drilling and cutting oils.

Gegenstand der Erfindung sind auch Mittel, die die Verbindungen der Formel I neben geeigneten Formulierungshilfsmitteln enthalten. Die erfindungsgemäßen Mittel enthalten die Wirkstoffe der Formel I im allgemeinen zu 1 bis 95 Gew.-%. The invention also relates to 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.

Sie können auf verschiedene Art formuliert werden, je nachdem wie es durch die They can be formulated in different ways, depending on how it is done by the

biologischen und chemisch-physikalischen Parameter vorgegeben ist. Als biological and chemical-physical parameters is specified. As

Formulierungsmöglichkeiten kommen daher in Frage: Spritzpulver (WP), emulgierbare Konzentrate (EC), wäßrige Dispersionen auf Öl- oder Wasserbasis (SC), Suspoemulsionen (SC), Stäubemittel (DP), Beizmittel, Granulate in Form von wasserdispergierbaren Formulation options are therefore possible: wettable powder (WP), emulsifiable concentrates (EC), aqueous dispersions based on oil or water (SC), suspoemulsions (SC), dusts (DP), mordants, granules in the form of water-dispersible

Granulaten (WG), ULV-Formulierungen, Mikrokapseln, Wachse oder Köder. Diese einzelnen Formulierungstypen sind im Prinzip bekannt und werden beispielsweise beschrieben in: Granules (WG), ULV formulations, microcapsules, waxes or baits. These individual types of formulation are known in principle and are described, for example, in:

Winnacker-Küchler, "Chemische Technologie", Band 7, CHauser Verlag München, 4. Aufl. 1986; van Falkenberg, "Pesticides Formulations", Marcel Dekker N.Y., 2nd Ed. 1972-73; K. Martens, "Spray Drying Handbook", 3rd Ed. 1979, G. Goodwin Ltd. London.  Winnacker-Küchler, "Chemical Technology", Volume 7, CHauser Verlag Munich, 4th ed. 1986; van Falkenberg, "Pesticides Formulations", Marcel Dekker N.Y., 2nd Ed. 1972-73; K. Martens, "Spray Drying Handbook", 3rd Ed. 1979, G. Goodwin Ltd. London.

Die notwendigen Formulierungshilfsmittel wie Inertmaterialien, Tenside, Lösungsmittel und weitere Zusatzstoffe sind ebenfalls bekannt und werden beispielsweise beschrieben in: The necessary formulation aids such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in:

Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J.; H.v.Olphen, "Introduction to Clay Colloid Chemistry, 2nd Ed., J. Wiley & Sons, N.Y.; Marsden, "Solvents Guide", 2nd Ed., Interscience, N.Y. 1950; Mc Cutcheon's, "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood, N.J.; Sisley and Wood. "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte", Wiss. Verlagsgesell., Stuttgart 1976; Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J .; HvOlphen, "Introduction to Clay Colloid Chemistry, 2nd Ed., J. Wiley & Sons, NY; Marsden," Solvents Guide ", 2nd Ed., Interscience, NY 1950; Mc Cutcheon's," Detergents and Emulsifiers Annual ", MC Publ Corp., Ridgewood, NJ; Sisley and Wood. "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; Schönfeldt, "Interface-active Ethylene Oxide Adducts", Wiss. Verlagsgesellschaft., Stuttgart 1976;

Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hauser Verlag München, 4. Aufi. 1986. Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986.

Auf der Basis dieser Formulierungen lassen sich auch Kombinationen mit anderen pestizid wirksamen Stoffen, Düngemitteln und/oder Wachstumsregulatoren herstellen, z. B. in Form einer Fertigformulierung oder als Tankmix. On the basis of these formulations, 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.

Spritzpulver sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer einem Verdünnungs- oder Inertstoff noch Netzmittel, z. B. polyoxethylierte Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, are also a wetting agent, in addition to a diluent or inert substance. B. polyoxethylated

Alkylphenole, polyoxethylierte Fettalkohole, Alkyl- oder Alkylphenol-sulfonate und Alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates and

Dispergiermittel, z. B. ligninsulfonsaures Natrium, Dispersants, e.g. B. sodium lignosulfonic acid,

2,2'-dinaphthyl-methan-6,6'-disulfonsaures Natrium, dibutylnaphthalin-sulfonsaures Natrium oder auch oleoylmethyltaurinsaures Natrium enthalten. Emulgierbare Konzentrate werden durch Auflösen des Wirkstoffes in einem organischen Lösungsmittel, z. B. Butanol,  2,2'-dinaphthyl-methane-6,6'-disulfonic acid sodium, dibutylnaphthalene-sulfonic acid sodium or oleoylmethyl tauric acid sodium. Emulsifiable concentrates are obtained by dissolving the active ingredient in an organic solvent, e.g. B. butanol,

Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten oder Cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or

Kohlenwasserstoffen unter Zusatz von einem oder mehreren Emulgatoren hergestellt. Hydrocarbons produced with the addition of one or more emulsifiers.

Als Emulgatoren können beispielsweise verwendet werden: Alkylarylsulfonsaure Examples of emulsifiers that can be used are: alkylarylsulfonic acid

Calcium-Salze wie Ca-dodecylbenzolsulfonat oder nichtionogene Emulgatoren wie Calcium salts such as Ca-dodecylbenzenesulfonate or non-ionic emulsifiers such as

Fettsäurepolyglykolester, Alkylarylpolyglykoleüier, Fettalkoholpolyglykolether, Propylenoxid-Ethylenoxid-Sorbitanfettsäureester, Polyoxethylensorbitan-Fettsäureester oder Polyoxethylensorbitester. Fatty acid polyglycol esters, alkylaryl polyglycol solvents, fatty alcohol polyglycol ethers, Propylene oxide-ethylene oxide-sorbitan fatty acid ester, polyoxethylene sorbitan fatty acid ester or polyoxethylene sorbitol ester.

Stäubemittel erhält man durch Vermählen des Wirkstoffes mit fein verteilten festen Stoffen, z. B. Talkum, natürlichen Tonen wie Kaolin, Bentonit, Poryphillit oder Diatomeenerde. Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. B. talc, natural clays such as kaolin, bentonite, poryphillite or diatomaceous earth. Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying

Wirkstoffkonzentraten mittels Klebemitteln, z, B. Polyvinylalkohol, polyacrylsaurem  Active substance concentrates using adhesives, e.g. polyvinyl alcohol, polyacrylic acid

Natrium oder auch Mineralölen, auf die Oberfläche von Trägerstoffen wie Sand, Kaolinite oder von granuliertem Inertmaterial. Auch können geeignete Wirkstoffe in der für die Herstellung von Düngemittelgranulaten üblichen Weise - gegebenenfalls in Mischung mit Düngemitteln - granuliert werden.  Sodium 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 appropriate in a mixture with fertilizers.

In Spritzpulvem beträgt die Wirkstoffkonzentration 10 bis 90 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei emulgierbaren Konzentraten kann die Wirkstoffkonzentration 5 bis 80 Gew.-% betragen. Staubförmige Formulierungen enthalten meistens 5 bis 20 Gew.-%. Bei Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welche Verbindung flüssig oder fest vorliegt und welche Granulierhilfsmittel, Füllstoffe usw. verwendet werden. The active ingredient concentration in wettable powders is 10 to 90% by weight, the remainder 100% by weight consists of customary formulation components. In the case of emulsifiable concentrates, the active substance concentration can be 5 to 80% by weight. Dust-like formulations usually contain 5 to 20% by weight. In the case of granules, the active ingredient content depends in part on whether the active compound is liquid or solid and which compound is liquid or solid and which granulation aids, fillers etc. are used.

Daneben enthalten die genannten Wirkstofformulierungen gegebenenfalls die jeweils üblichen Haft-, Netz-, Dispergier-, Emulgier-, Penetrations-, Lösungsmittel, Füll- oder Trägerstoffe. In addition, the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers.

Zur Anwendung werden die in handelsüblicher Form vorliegenden Konzentrate The concentrates available in commercial form are used

gegebenenfalls in üblicher Weise verdünnt, z. B. bei Spritzpulvern, emulgierbaren optionally diluted in a conventional manner, e.g. B. with wettable powders, emulsifiable

Konzentraten, Dispersionen und teilweise auch bei Mikrogranulaten mittels Wasser. Concentrates, dispersions and sometimes also in the case of microgranules using water.

Staubförmige und granulierte Zubereitungen sowie versprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt Dust-like and granulated preparations as well as sprayable solutions are usually no longer diluted with other inert substances before use

Mit den äußeren Bedingungen wie Temperatur, Feuchtigkeit u. a. variiert die erforderliche Aufwandmenge. Sie kann innerhalb weiter Grenzen schwanken, z. B. von 0,005 bis 10,0 kg/ha, vorzugsweise liegt sie im Bereich von 0,01 bis 5 kg/ha. Die erfindungsgemäßen Wirkstoffe können in ihren handelsüblichen Formulierungen entweder allein oder in Kombination mit weiteren, literaturbekannten Fungiziden The application rate required varies with the external conditions such as temperature, humidity and others. It can fluctuate within wide limits, e.g. B. from 0.005 to 10.0 kg / ha, preferably it is in the range of 0.01 to 5 kg / ha. In their commercially available formulations, the active compounds according to the invention can be used either alone or in combination with other fungicides known from the literature

angewendet werden. be applied.

Als literaturbekannte Fungizide, die erfindungsgemäß mit den Verbindungen der Formel I kombiniert werden können, sind beispielsweise folgende Produkte zu nennen: The following products may be mentioned as examples of fungicides known from the literature which can be combined according to the invention with the compounds of the formula I:

Imazalil, Prochloraz, Fenapanil, SSF 105, Triflumizol, PP 969, Flutriafol, BAY-MEB 6401. Propiconazol, Etaconazol, Diclobutrazol, Tebuconazole, Bitertanol, Triadimefon, Imazalil, Prochloraz, Fenapanil, SSF 105, Triflumizol, PP 969, Flutriafol, BAY-MEB 6401. Propiconazole, Etaconazole, Diclobutrazol, Tebuconazole, Bitertanol, Triadimefon,

Triadimenol, Fluotrimazol, Tridemorph, Dodemorph, Fenpropimorph, Falimorph, Triadimenol, fluotrimazole, tridemorph, dodemorph, fenpropimorph, falimorph,

Dimethomorph, S-32165, Chlobenzthiazone, Parinol, Buthiobat, Fenpropidin, Triforine, Fenarimol, Nuarimol, Triarimol, Ethirimol, Dimethirimol, Bupirimate, Rabenzazole, Tricyclazole, Fluobenzimine, Pyroxyfur, NK-483, PP-389, Pyroquilon, Hymexazole, Fenitropan, UHF-8227, Cymoxanil, Dichloflunamd, Captafol, Captan, Folpet, Tolylfluanid, Chloroüialonil, Etridiazol, Iprodione, Procymidon, Vinclozolin, Metomeclan, Myclozolin, Dichlozolinate, Fluorimide, Drazoxolan, Chinomethionate, Nitrothahsopropyl, Dithianon, Dinocap, Binapacrvl, Fentinacetate, Fentinhydroxide, Carboxin, Oxycarboxin, Pyracarbolid, Methfuroxam, Fenfuram, Furmecyclox, Benodanil, Mebenil, Mepronil, Hutolanil, Dimethomorph, S-32165, Chlobenzthiazone, Parinol, Buthiobat, Fenpropidin, Triforine, Fenarimol, Nuarimol, Triarimol, Ethirimol, Dimethirimol, Bupirimate, Rabenzazole, Tricyclazole, Fluobenzimine, Pyroxyfur, PP-38zolitone, 38-Nazon, 38-N3 UHF-8227, Cymoxanil, Dichloflunamd, Captafol, Captan, Folpet, Tolylfluanid, Chloroüialonil, Etridiazol, Iprodione, Procymidon, Vinclozolin, Metomeclan, Myclozolin, Dichlozolinate, Fluorimide, Drazoxolin, Fidomethapinentinylin, Ditridomethinapinate, Fitrate Carboxin, oxycarboxin, pyracarbolide, methfuroxam, fenfuram, furmecyclox, benodanil, mebenil, mepronil, hutolanil,

Fuberidazole, Thiabendazole, Carbendazim, Benomyl, Thiophanate, Thiophanatemethyvl, CGD-95340 F, IKF-1216, Mancozeb, Zineb, Nabam, Tbiram, Propineb, Prothiocarb, Propamocarb, Dodine, Guazatine, Dicloran, Quintozene, Chloroneb, Tecnazene, Biphenyl, Anilazine, 2-Phenylphenol, Kupferverbindungen wie Cu-oxychlorid, Oxine-Cu, Cu-oxide, Schwefel, Fosethylaluminium, Natrium-dodecylbenzolsulfonat, Natrium-dodecylsulfat, Natrium-C13/C15-alkoholethersulfonat, Natriumcetostearylphosphatester, Fuberidazole, Thiabendazole, Carbendazim, Benomyl, Thiophanate, Thiophanatemethyvl, CGD-95340 F, IKF-1216, Mancozeb, Zineb, Nabam, Tbiram, Propineb, Prothiocarb, Propamocarb, Dodine, Guazatine, Tecniphenyl, Quinobenzene, Dicenezhenyl, Quinobenzene, Dicene, Chlorobenzone, Dicene, Chlorobenzone, Dicene, Chlorobenzene , 2-phenylphenol, copper compounds such as Cu-oxychloride, oxine-Cu, Cu-oxide, sulfur, fosethyl aluminum, sodium dodecylbenzenesulfonate, sodium dodecylsulfate, sodium C13 / C15 alcohol ether sulfonate, sodium cetostearyl phosphate ester,

Dioctyl-natriumsulfosuccinat, Natrium-isopropylnaphthalinsulfonat, Dioctyl sodium sulfosuccinate, sodium isopropylnaphthalenesulfonate,

Natrium-methylenbisnaphthalinsulfonat, Cetyl-trimethyl-ammoniumchlorid, Sodium methylene bisnaphthalene sulfonate, cetyl trimethyl ammonium chloride,

Salze von langkettigen primären, sekundären oder tertiären Aminen, Alkyl-propylenamine, Lauryl-pyridinium-bromid, ethoxilierte quaternierte Fettamine, Salts of long-chain primary, secondary or tertiary amines, alkyl propylene amines, lauryl pyridinium bromide, ethoxylated quaternized fatty amines,

Alkyl-dimethyl-benzylammoniumchlorid und 1-Hydroxyethyl-2-alkyl-imidazolin. Alkyl-dimethyl-benzylammonium chloride and 1-hydroxyethyl-2-alkyl-imidazoline.

Die oben genannten Kombinationspaitner stellen bekannte Wirkstoffe dar, die zum großen Teil in CH. R. Worthing, U.S.B. Walker, The Pesticide Manual, 7. Auflage (1983), British Crop Protection Council, beschrieben sind. Darüber hinaus können die erfindungsgemäßen Wirkstoffe, insbesondere die der aufgeführten Beispiele, in ihren handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit anderen Wirkstoffen, wie Insektiziden, Lockstoffen, Sterilantien, Akariziden, Nematiziden, Fungiziden, wachstumsregulierenden Stoffen oder Herbiziden vorliegen. Zu den Insektiziden zählen beispielsweise The above-mentioned combination partners are known active ingredients, which are largely in CH. R. Worthing, USB Walker, The Pesticide Manual, 7th edition (1983), British Crop Protection Council. In addition, the active compounds according to the invention, in particular those of the examples listed, can be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. Insecticides include, for example

Phosphorsäureester, Carbamate, Carbonsäureester, Formamidine, Zinnverbindungen, durch Mikroorganismen hergestellte Stoffe u. a.. Bevorzugte Mischungspartner sind:  Phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin compounds, substances produced by microorganisms and the like. a .. Preferred mixing partners are:

1. aus der Gruppe der Phosphorsäureester 1. from the group of phosphoric acid esters

Azinphos-ethyl,Azinphosmethyl, 1-(4-Chlorphenyl)-4-(O-ethyl,  Azinphos-ethyl, azinphosmethyl, 1- (4-chlorophenyl) -4- (O-ethyl,

S-propyl)phosphoryloxypyrazol (TIA-230), Chlorpyrifos, Coumaphos, Demeton,  S-propyl) phosphoryloxypyrazole (TIA-230), Chlorpyrifos, Coumaphos, Demeton,

Demeton-S-methyl, Diazinon, Dichlorvos, Dimethoat, Ethoprophos, Etrimfos, Fenitrothion, Fenthion, Heptenophos, Parathion, Parathionmethyl, Phosalon, Pirimiphos-ethyl,  Demeton-S-methyl, Diazinon, Dichlorvos, Dimethoat, Ethoprophos, Etrimfos, Fenitrothion, Fenthion, Heptenophos, Parathion, Parathionmethyl, Phosalon, Pirimiphos-ethyl,

Pirimiphos-methyl, Profenofos, Prothiofos, Sulprofos, Triazophos, Trichlorphon.  Pirimiphos-methyl, Profenofos, Prothiofos, Sulprofos, Triazophos, Trichlorphon.

2. aus der Gruppe der Carbamate 2. from the group of carbamates

Aldicarb, Bendiocarb, BPMC (2-(1-Methylpropyl)phenylmethylcarbamat), Butocarboxim, Butoxicarboxim, Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Isoprocarb, Methomyl, Oxamyl. Pirimicarb, Promecarb, Propoxur, Thiodicarb.  Aldicarb, Bendiocarb, BPMC (2- (1-methylpropyl) phenylmethylcarbamate), Butocarboxim, Butoxicarboxim, Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Isoprocarb, Methomyl, Oxamyl. Pirimicarb, Promecarb, Propoxur, Thiodicarb.

3. aus der Gruppe der Carbonsäureester 3. from the group of carboxylic acid esters

Allethrin. Alphamethrin, Bioallethrin, Bioresmethrin, Cycloprothrin, Cyfluthrin, Cyhalothrin. Cypermethrin, Deltamethrin, 2,2-Dimethyl-3- 2-chlor-2-trifluormethylvinyI)-cyclopropancarbonsäure-(alpha- cyano-3-phenyl-2-methyl-benzyI)ester (FMC 54800), Fenpropathrin, Fenfluthrin, Fenvalerat. Flucythrinate, Flumethrin, Fluvalinate, Permethrin, Resmethrin, Tralomethrin.  Allethrin. Alphamethrin, bioallethrin, bioresmethrin, cycloprothrin, cyfluthrin, cyhalothrin. Cypermethrin, deltamethrin, 2,2-dimethyl-3- 2-chloro-2-trifluoromethylvinyI) -cyclopropanecarboxylic acid- (alpha-cyano-3-phenyl-2-methyl-benzyI) ester (FMC 54800), fenpropathrin, fenfluthrin, fenvalerate. Flucythrinate, flumethrin, fluvalinate, permethrin, resmethrin, tralomethrin.

4. aus der Gruppe der Formamidine 4. from the group of formamidines

Amitraz, Chlordimeform. Amitraz, chlorordime form.

5. aus der Gruppe der Zinn Verbindungen 5. from the group of tin compounds

Azocyclotin, Cyhexatin, Fenbutatinoxid 6. Sonstige Azocyclotin, Cyhexatin, Fenbutatinoxid 6. Other

Abamektin, Bacillus thuringiensis, Bensultap, Binapacyl, Bromopropylate, Buprofecin Camphechlor, Cartap, Chlorobenzilate, Chlorfluazuron,  Abamectin, Bacillus thuringiensis, Bensultap, Binapacyl, Bromopropylate, Buprofecin Camphechlor, Cartap, Chlorobenzilate, Chlorfluazuron,

2-(4-Chlorphenyl)-4,5-diphenylthiophen (UBI-T 930), Chlofentezine, 2- (4-chlorophenyl) -4,5-diphenylthiophene (UBI-T 930), chlorofentezine,

Cyclopropancarbonsäure(2-naphthylmethyl)-ester (Ro 12-0470), Cyromacin, DDT, Dicofol. N-(3,5-Dichlor-4-(1,1,2, 2-tetrafluoroethoxy)phenylammo)carbonyl)-2,6-difluor-berizamide (XRD 473), Diflubenzuron, N-(2,3-Dihydro-3-methyl-1,2-thiazol-2-ylidene)2,4-xylidene, Dinobuton, Dinocap, Endosulfan, Fenoxycarb, Fenthiocarb, Hubenziinine, Flufenoxuron, Gamma-HCH, Hexythiazox, Hydramethylnon (AC 217300), Ivermectin, Cyclopropanecarboxylic acid (2-naphthylmethyl) ester (Ro 12-0470), cyromacin, DDT, dicofol. N- (3,5-dichloro-4- (1,1,2, 2-tetrafluoroethoxy) phenylammo) carbonyl) -2,6-difluoro-berizamide (XRD 473), diflubenzuron, N- (2,3-dihydro- 3-methyl-1,2-thiazol-2-ylidene) 2,4-xylidene, dinobutone, dinocap, endosulfan, fenoxycarb, fenthiocarb, hubenziinine, flufenoxuron, gamma-HCH, hexythiazox, hydramethylnon (AC 217300), ivermectin,

2-Nitro-methyl-4,5-dihydro-6H-thiazin (SD 52618), 2-Nitromethyl-3,4-dihydrothiazol (SD 35651), 2-Nittomethylene-1,3-ttaazinon-3yl-carbamaldehyde (WL 108477), Propargite, Teflubenzuron, Tetradifon, Tetrasul, Thicyclam, Trifiumaron, Kempolyeder- und 2-nitro-methyl-4,5-dihydro-6H-thiazine (SD 52618), 2-nitromethyl-3,4-dihydrothiazole (SD 35651), 2-nitroethylene-1,3-ttaazinone-3yl-carbamaldehydes (WL 108477 ), Propargite, Teflubenzuron, Tetradifon, Tetrasul, Thicyclam, Trifiumaron, Kempolyeder- and

Granuloseviren. Granulosis viruses.

Der Wirkstoffgehalt der aus den handelsüblichen Formulierungen bereiteten The active substance content of those prepared from the commercially available formulations

Anwendungsformen kann in weiten Bereich variieren, die Wirkstoffkonzentration der Anwendungsformen kann von 0,0001 bis zu 100 Gew.-% Wirkstoff, vorzugsweise von 0,001 bis 1 Gew.-%, liegen. Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichen Weisen. Application forms can vary within a wide range, the active compound concentration of the use forms can be from 0.0001 to 100% by weight of active compound, preferably from 0.001 to 1% by weight. The application takes place in a customary manner adapted to the application forms.

Nachfolgende Beispiele dienen zur Erläuterung der Erfindung. The following examples serve to explain the invention.

A. Formulierungsbeispiele a) Ein Stäubemittel wird erhalten, indem man 10 Gew.-Teile Wirkstoff und 90 Gew.-Teile Talkum als Ineitstoff mischt und in einer Schlagmühle zerkleinert b) Ein in Wasser leicht dispergierbares, benetzbares Pulver wird erhalten, indem man 25 Gew.-Teile Wirkstoff, 65 Gew.-Teile kaolinhaltigen Quarz als Inertstoff, 10 Gew.-Teile ligninsulfonsaures Kalium und 1 Gew.-Teil oleoylmethyltaurinsaures Natrium als Netz- und Dispergiermittel mischt und in einer Stiftmühle mahlt c) Ein in Wasser leicht dispergierbares Dispersionskonzentrat stellt man her, indem man 40 Gew.-Teile Wirkstoff mit 7 Gew.-Teilen eines Sulfobemsteinsäurehalbesters, 2 Gew.-Teilen eines Ligninsulfonsäure-Natriumsalzes und 51 Gew.-Teilen Wasser mischt und in einer Reibkugelmühle auf eine Feinheit von unter 5 Mikron vermahlt. d) Ein emulgierbares Konzentrat läßt sich herstellen aus 15 Gew.-Teilen Wirkstoff, 75 Gew.-Teilen Cyclohexanon als Lösungsmittel und 10 Gew.-Teilen oxethyliertem A. Formulation examples a) 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 in a beater mill. B) A wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight . Parts of active ingredient, 65 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight sodium oleoylmethyl taurine as a wetting and dispersing agent and ground in a pin mill c) A dispersion concentrate which is easily dispersible in water is prepared by mixing 40 parts by weight of active ingredient 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 ground in a attritor to a fineness of less than 5 microns. d) An emulsifiable concentrate can be prepared from 15 parts by weight of active ingredient, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated

Nonylphenol (10 AeO) als Emulgator. e) Ein Granulat läßt sich herstellen aus 2 bis 15 Gew.-Teilen Wirkstoff und einem inerten Granulatträgermaterial wie Attapulgit, Bimsgranulat und/oder Quarzsand. Nonylphenol (10 AeO) as an emulsifier. e) 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.

Zweckmäßigerweise verwendet man eine Suspension des Spritzpulvers aus Beispiel b) mit einem Feststoffanteil von 30 % und spritzt diese auf die Oberfläche eines Attapulgitgranulats, trocknet und vermischt innig. Dabei beträgt der Gewichtsanteil des Spritzpulvers ca. 5 % und der des inerten Trägermaterials ca. 95 % des fertigen Granulats. 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.

B. Chemische Beispiele Beispiel 1: 5-Methoxy-2-phenyl-4-(3-propmyloxy)-pyrimidin B. Chemical Examples Example 1: 5-methoxy-2-phenyl-4- (3-propmyloxy) pyrimidine

Verbindung Nr. 1.1

Figure imgf000026_0001
Compound No. 1.1
Figure imgf000026_0001

Zu 33 g NaH (80% in Mineralöl) in 500 ml abs. THF tropfte man 15 % einer Mischung aus 118 g Ameisensäureethylester und 104 g Methoxyessigsäuremethylester und erwärmte das Reaktionsgemisch gelinde bis eine Wasserstoffentwicklung festzustellen war. Den restlichen Anteil der obigen Mischung tropfte man anschließend so zu, daß die Reaktionstemperatur bei 35 - 40 °C lag und ein mittlere Wasserstoffentwicklung beobachtet wurde. Hierbei bildete sich ein schwer rührbares Reaktionsgemisch. Das Gemisch wurde 16 Stunden  To 33 g NaH (80% in mineral oil) in 500 ml abs. THF was added dropwise to 15% of a mixture of 118 g of ethyl formate and 104 g of methyl methoxyacetate and the reaction mixture was gently warmed until hydrogen evolution was observed. The remaining portion of the above mixture was then added dropwise so that the reaction temperature was 35-40 ° C. and an average evolution of hydrogen was observed. A reaction mixture which was difficult to stir formed. The mixture was 16 hours

stehengelassen. Anschließend gab man 500 ml Isopropanol, 51,3 g Natriummethanolat und 195.7 g Benzamidinhydrochlorid (80 - 85 %, techn. Qualität, ca. 15 % Wasser enthaltend) hinzu und erhitzte dieses Reaktionsgemisch 120 Minuten unter Rückfluß, wobei das THF teilweise abdestilliert wurde. Anschließend destillierte man die Lösungsmittel ab und nahm den Rückstand in Wasser auf, säuerte mit Essigsäure an und erhielt nach dem Abfiltrieren 145 g (72%) 5-Methoxy-2-phenyl-4-(1H)-pyrimidinon, Smp.: 203-205 °C. ditched. Then 500 ml of isopropanol, 51.3 g of sodium methoxide and 195.7 g of benzamidine hydrochloride (80-85%, technical grade, containing approx. 15% water) were added and this reaction mixture was heated under reflux for 120 minutes, the THF being partially distilled off. The solvent was then distilled off and the residue was taken up in water, acidified with acetic acid and, after filtering off, 145 g (72%) of 5-methoxy-2-phenyl-4- (1H) -pyrimidinone, mp: 203- 205 ° C.

In 600 ml POCl3 und 10 ml N,N-Dimethylanilin erhitzte man 151 g 151 g were heated in 600 ml of POCl 3 and 10 ml of N, N-dimethylaniline

5-Methoxy-2-phenyl-4-(1H)-pyrimidinon unter Rückfluß. Nach vollständiger Lösung des Pyrimidinons ( ca. 60 Minuten ) destillierte man bei ca.200 mm Hg das POCl3 ab, nahm in Methylenchlorid auf und hydrolysierte, wusch die organische Phase neutral, trocknete diese, destillierte das Lösungsmittel ab und erhielt 155 g (95 % ) 5-methoxy-2-phenyl-4- (1H) pyrimidinone under reflux. After the pyrimidinone had completely dissolved (approx. 60 minutes), the POCl 3 was distilled off at approx. 200 mm Hg, taken up in methylene chloride and hydrolyzed, the organic phase was washed neutral, dried, the solvent was distilled off and 155 g (95 %)

4-Chlor-5-methoxy-2-phenylpyrimidin, Smp.: 163-167 °C. 4-chloro-5-methoxy-2-phenylpyrimidine, m.p .: 163-167 ° C.

Zu 3,9 g NaH (80% in Mineralöl) in 200 ml abs. THF tropfte man 7,3 g Propinylalkohol, rührte eine Stunde und gab dann 22,1 g 4-Chlor-5-memoxy-2-phenylpyrimidin hinzu. Nach 16 Stunden hydrolysierte man, extrahierte mit Essigester oder Methylenchlorid, wusch die organische Phase, trocknete diese, destillierte das Lösungsmittel ab und erhielt 23 g ( 96 % ) 5-Memoxy-2-phenyl-4-propinyloxypyrimidin, Smp.: 113 °C, Sdp.: 145 °C/ 0,05 mbar. To 3.9 g NaH (80% in mineral oil) in 200 ml abs. THF was added dropwise to 7.3 g of propynyl alcohol, stirred for one hour and then 22.1 g of 4-chloro-5-memoxy-2-phenylpyrimidine was added. To The mixture was hydrolyzed for 16 hours, extracted with ethyl acetate or methylene chloride, the organic phase was washed, dried, the solvent was distilled off and 23 g (96%) of 5-memoxy-2-phenyl-4-propynyloxypyrimidine were obtained, mp: 113 ° C., Bp: 145 ° C / 0.05 mbar.

Beispiel 2: 5-Memoxy-2-phenyl-4-(1-(4-tolyl)-3-propinyloxy)-pyrimidin Example 2: 5-Memoxy-2-phenyl-4- (1- (4-tolyl) -3-propynyloxy) pyrimidine

Verbindung Nr. 1.43 Compound No. 1.43

Figure imgf000027_0001
Figure imgf000027_0001

In 30 ml Triethylamin wurden 2,4 g 5-Memoxy-2-phenyl-4-propinyloxypyrirnidin, 0,07 g Bis-(triphenylphosphin)-palladiumdichlorid und 0,01 g Kupfer-(I)-jodid vorgelegt und 2,8 g 4-Jodtoluol zu getropft Nach 16 Stunden wurde die Hauptmenge Triethylamin abdestilliert, der Rückstand in Methylenchlorid aufgenommen und mit Wasser gewaschen, getrocknet und eingeengt. Nach Reinigung mittels Säulenchromatographie, mit Essigester und Heptan (1:1) als Laufrnittel, erhielt man 1,9 g (58 %)  2.4 g of 5-memoxy-2-phenyl-4-propynyloxypyrirnidine, 0.07 g of bis (triphenylphosphine) palladium dichloride and 0.01 g of copper (I) iodide were placed in 30 ml of triethylamine, and 2.8 g 4-iodotoluene added dropwise After 16 hours, the main amount of triethylamine was distilled off, the residue was taken up in methylene chloride and washed with water, dried and concentrated. After purification by column chromatography, using ethyl acetate and heptane (1: 1) as the running medium, 1.9 g (58%) were obtained.

5-Methoxy-2-phenyl-4-(1-(4-tolyl)-3-propinyloxy)-pyrimidin, 5-methoxy-2-phenyl-4- (1- (4-tolyl) -3-propynyloxy) pyrimidine,

Smp.: 103 - 105 °C. M.p .: 103-105 ° C.

Beispiel 3: Example 3:

5-Methoxy-2-phenyl-4-(1-jodo-3-propinyloxy)-pyrimidin 5-methoxy-2-phenyl-4- (1-iodo-3-propynyloxy) pyrimidine

Figure imgf000028_0001
Figure imgf000028_0001

Unter N2- Atmosphäre legte man 4,8 g 5-Memoxy-2-phenyl-4-propinyloxypyrimidin in 100 ml THF vor, kühlte auf -78 °C ab, gab 14 ml 1,6 m n-Butyllithiumlösung in Hexan hinzu. Nach ca. 1 Stunde gab man 5,6 g Jod dazu, ließ das Gemisch auf Raumtemperatur erwärmen und hydrolysierte nach ca. 30 Minuten. Man nahm in Methylenchlorid auf, wusch mit Wasser, destillierte das Lösungsmittel ab, und erhielt nach säulenchromatographischer Reinigung, mit Essigester und Heptan (3:7) als Laufmittel, 6,0 g Under an N 2 atmosphere, 4.8 g of 5-memoxy-2-phenyl-4-propynyloxypyrimidine were placed in 100 ml of THF, cooled to -78 ° C., and 14 ml of 1.6 m of n-butyllithium solution in hexane were added. After about 1 hour, 5.6 g of iodine were added, the mixture was allowed to warm to room temperature and hydrolyzed after about 30 minutes. The mixture was taken up in methylene chloride, washed with water and the solvent was distilled off, and 6.0 g was obtained after purification by column chromatography, with ethyl acetate and heptane (3: 7) as the eluent

5-Methoxy-2-phenyl-4-(1-jodo-3-propmyloxy)-pyrimidin, Smp.: 148 - 150 °C. 5-methoxy-2-phenyl-4- (1-iodo-3-propmyloxy) pyrimidine, m.p .: 148-150 ° C.

Beispiel 4: Example 4:

5-Brom-2-phenyl-4-(3-propmyloxy)-pyrimidin 5-bromo-2-phenyl-4- (3-propmyloxy) pyrimidine

Verbindung Nr. 1.96

Figure imgf000028_0002
Compound No. 1.96
Figure imgf000028_0002

In 300 ml Wasser rührte man 3 -4 Tage 95 g Benzamidinhydrochlorid (80 - 85 %, techn. Qualität ca. 15 % Wasser enthaltend) und 70 g Natriumformylessigsäureethylester, säuerte mit Essigsäure leicht an und erhielt nach dem Abfiltrieren 33 g (38 %) 95 g of benzamidine hydrochloride (80-85%, technical grade containing approx. 15% water) and 70 g of ethyl sodium formylacetate were gently stirred in 300 ml of water for 3-4 days, and acidified slightly with acetic acid and 33 g (38%) were obtained after filtering off

2-Phenyl-4-(1H)-pyrimidinon, Smp.: 198 - 203 °C. Zu 70,8 g 2-Phenyl-4-(1H)-pyrimidinon in 250 ml Essigsäure tropfte man 65,5 g (20,9 ml) Brom, rührte 5 Stunden und ließ das Reaktionsgemisch 18 Stunden stehen, gab auf eine 2 kg Eis/Wassermischung und erhielt nach dem Abfiltrieren 102,8 g (99 %) 2-phenyl-4- (1H) pyrimidinone, mp: 198-203 ° C. 65.5 g (20.9 ml) of bromine were added dropwise to 70.8 g of 2-phenyl-4- (1H) -pyrimidinone in 250 ml of acetic acid, the mixture was stirred for 5 hours and the reaction mixture was left to stand for 18 hours, giving 2 kg Ice / water mixture and obtained after filtering off 102.8 g (99%)

5-Brom-2-phenyl-4-(1H)-pyrimidinon, Smp.: 230 - 235 °C.  5-bromo-2-phenyl-4- (1H) -pyrimidinone, m.p .: 230-235 ° C.

In 300 ml POCl3 und 10 ml N,N-Dimethylanilin erhitzte man 102,8 g 102.8 g was heated in 300 ml of POCl 3 and 10 ml of N, N-dimethylaniline

5-Brom-2-phenyl-4-(1H)-pyrimidinon zum Rückfluß. Nach vollständiger Lösung des Pyrimidinons ( ca. 60 Minuten ) destillierte man bei ca.200 mm Hg das POCl3 ab, nahm in Methylenchlorid auf und hydrolysierte, wusch die organische Phase neutral, trocknete diese und erhielt nach dem Abdestillieren des Lösungsmittels 89,2 g (83 % ) 5-Bromo-2-phenyl-4- (1H) pyrimidinone at reflux. After the pyrimidinone had completely dissolved (approx. 60 minutes), the POCl 3 was distilled off at approx. 200 mm Hg, taken up in methylene chloride and hydrolyzed, the organic phase was washed neutral, dried and, after the solvent had been distilled off, 89.2 g were obtained (83%)

5-Brom-4-chlor-2-phenylpyrimidin, Smp.: 96 - 101 °C.  5-bromo-4-chloro-2-phenylpyrimidine, m.p .: 96-101 ° C.

Zu 1.1 g NaH (80 % in Mineralöl) in 50 ml abs. THF tropfte man 2,1 g Propinylalkohol, rührte eine Stunde und gab dann 6,7 g 5-Brom-4-chlor-2-phenylpyrimidin hinzu. Nach 16 Stunden hydrolysierte man, extrahierte mit Essigester, wusch die organische Phase, trocknete diese und destillierte das Lösungsmittel ab. Nach säulenchromatographischer Reinigung, mit Essigester und Heptan (3:7) als Lauftnittel, erhielt man 4,2 g (58 %) To 1.1 g NaH (80% in mineral oil) in 50 ml abs. THF was dropped in 2.1 g of propynyl alcohol, stirred for one hour and then 6.7 g of 5-bromo-4-chloro-2-phenylpyrimidine was added. After 16 hours, the mixture was hydrolyzed, extracted with ethyl acetate, the organic phase was washed, dried and the solvent was distilled off. After purification by column chromatography, using ethyl acetate and heptane (3: 7) as running agent, 4.2 g (58%) were obtained.

5-Brom-2-phenyl-4-(3-propmyloxy)-pyrimidin,  5-bromo-2-phenyl-4- (3-propmyloxy) pyrimidine,

Smp.: 98 - 99 °C.  M.p .: 98-99 ° C.

Beispiel 5: 5-Brom-2-phenyl-4-(3-propiynyllamino)-pyrimidin Example 5: 5-bromo-2-phenyl-4- (3-propynyllamino) pyrimidine

Verbindung Nr. 1.142

Figure imgf000029_0001
Compound No. 1.142
Figure imgf000029_0001

In 100 ml Dimethylformamid wurden 6,7 g 5-Brom-4-chlor-2-phenyl-pyrimidin und 1,7 g (2,1 ml) Propinylamin vorgelegt und 4,0 g (5,5 ml) Triethylamin zugetropft Nach 1 Stunde Rühren des Gemisches bei Raumtemperatur erhitzte man 3 Stunden auf 80 - 90°C 6.7 g of 5-bromo-4-chloro-2-phenyl-pyrimidine and 1.7 g were placed in 100 ml of dimethylformamide (2.1 ml) of propynylamine and 4.0 g (5.5 ml) of triethylamine were added dropwise. After stirring the mixture at room temperature for 1 hour, the mixture was heated at 80-90 ° C. for 3 hours

Innentemperatur (DC-Umsatzkontrolle), hydrolysierte, neutralisierte nach Abkühlung und extrahierte mit Methylenchlorid. Nach dem Waschen und Trocknen der organischen Phase, Abdestillation des Lösungsmittels und Reinigung durch Säulenchromatographie, mit Essigester und Heptan (3:7) als Laufmittel, erhielt man 5,6 g (78 %) Internal temperature (DC conversion control), hydrolyzed, neutralized after cooling and extracted with methylene chloride. After washing and drying the organic phase, distilling off the solvent and purifying by column chromatography, using ethyl acetate and heptane (3: 7) as the eluent, 5.6 g (78%) were obtained.

5-Brom-2-phenyl-4-propmyla minopyrimidin, Smp.: 103 - 105 °C. 5-bromo-2-phenyl-4-propmyla minopyrimidine, m.p .: 103-105 ° C.

Beispiel 6: Example 6:

2-(4-Benzoesäurenitril)-5-meth oxy-4-propmyloxy-pyrimidin 2- (4-benzoicitrile) -5-meth oxy-4-propmyloxypyrimidine

Verbindung Nr. 1.10 Compound No. 1.10

Figure imgf000031_0001
Figure imgf000031_0001

und Beispiel 7:  and Example 7:

2-(4-Benzoesäurenitril)-5-methoxy-6-methoxymemylen-4-(3 -propmyloxy)-pyrimidin 2- (4-benzoicitrile) -5-methoxy-6-methoxymemylene-4- (3-propyloxy) pyrimidine

Verbindung Nr. 1.68 Compound No. 1.68

Figure imgf000031_0002
Figure imgf000031_0002

Zu 2,0 g NaH (80% in Mineralöl) in 50 ml abs. Diethylether tropfte man eine Mischung von 7,4 g Ameisensäureethylester und 6,2 g Methoxyessigsäuremethylester und erwärmte das Reaktionsgemisch gelinde bis eine Wasserstoffentwicklung festzustellen ist Hierbei bildete sich ein schwer rührbares Reaktionsgemisch. Nach Stehenlassen des Gemisches über 16 Stunden gab man 50 ml Methanol, 11,4 ml 30 % Natriummethanolat-Lösung in Methanol und 12 g 4-Aminobenzamidhydrochlorid hinzu und erhitzte dieses Reaktionsgemisch 120 Minuten unter Rückfluß, wobei der Diethylether abdestilliert wurde. Anschließend destilherte man die Lösungsmittel ab und nahm den Rückstand in Wasser auf, säuert mitTo 2.0 g NaH (80% in mineral oil) in 50 ml abs. Diethyl ether was added dropwise to a mixture of 7.4 g of ethyl formate and 6.2 g of methyl methoxyacetate and the reaction mixture was warmed gently until evolution of hydrogen was observed. A reaction mixture which was difficult to stir formed. After the mixture had been left to stand for 16 hours, 50 ml of methanol, 11.4 ml of 30% sodium methoxide solution in methanol and 12 g of 4-aminobenzamide hydrochloride were added and this reaction mixture was heated under reflux for 120 minutes, during which the diethyl ether was distilled off. Subsequently the solvents were distilled off and the residue was taken up in water and acidified

Essigsäure an und erhielt nach Abfiltrieren 11,7 g eines Gemisches aus Acetic acid and, after filtering off, obtained 11.7 g of a mixture

2-(4-Benzoesäureamid)-5-methoxy-4-(1H)-pyri midinon und  2- (4-benzoic acid amide) -5-methoxy-4- (1H) -pyrimidinone and

2-(4-Benzoesäureamid)-5-methoxy-6-methoxymethylen-4-(1H)- pyrimidinon.  2- (4-benzoic acid amide) -5-methoxy-6-methoxymethylene-4- (1H) -pyrimidinone.

In 100 ml POCl3 und 3 ml N,N-Dimethylanilin erhitzte man 11,7 g des Gemisches aus 2-(4-Benzoesäurearnid)-5-methoxy-4-(1H)-pyrimidinon und In 100 ml of POCl 3 and 3 ml of N, N-dimethylaniline, 11.7 g of the mixture of 2- (4-benzoic acid amide) -5-methoxy-4- (1H) -pyrimidinone and was heated

2-(4-Benzoesäureamid)-5-methoxy-6-methoxymethylen-4-(1H)- pyrimidinon unter Rückfluß. Nach vollständiger Lösung der Pyrimidinone (ca. 60 Minuten) destillierte man bei ca. 200 mm Hg das POCl3 ab, nahm in Methylenchlorid auf und hydrolysierte, wusch die organische Phase neutral, trocknete diese und nach Abdestillieren des Lösungsmittels erhielt man 9 g eines Gemisches aus 2-(4-Benzoesäurenitril)-4-chlor-5-methoxy-pyri midin und 2- (4-benzoic acid amide) -5-methoxy-6-methoxymethylene-4- (1H) -pyrimidinone under reflux. After the pyrimidinones had completely dissolved (approx. 60 minutes), the POCl 3 was distilled off at approx. 200 mm Hg, taken up in methylene chloride and hydrolyzed, the organic phase was washed neutral, dried and 9 g of a mixture were obtained after the solvent had been distilled off from 2- (4-benzonitrile) -4-chloro-5-methoxy-pyrimidine and

2-(4-Benzoesäurenitril)-4-chlor-5-methoxy-6-methoxymethylen-pyrimidin. 2- (4-benzoicitrile) -4-chloro-5-methoxy-6-methoxymethylene pyrimidine.

Zu 1,1 g NaH (80 % in Mineralöl) in 100 ml abs. THF tropfte man 2,0 g Propinylalkohol, rührte eine Stunde und gab dann 4,9 g des Gemisches aus To 1.1 g NaH (80% in mineral oil) in 100 ml abs. THF was dropped 2.0 g of propynyl alcohol, stirred for one hour and then 4.9 g of the mixture was discharged

2-(4-Benzoesäurenitril)-4-chlor-5-meth oxy-pyrimidin und 2- (4-benzoacrylonitrile) -4-chloro-5-meth oxypyrimidine and

2-(4-Benzoesäurenitril)-4-chlor-5-methoxy-6-methoxymethylen- pyrimidin hinzu. Nach 16 Stunden hydrolysierte man, extrahierte mit Essigester oder Methylenchlorid, wusch die organische Phase, trocknete diese und erhielt nach säulenchromatographischer Trennung, mit Essigester und Heptan 3:7 als Laufmittel, 0,2 g  2- (4-Benzo-acrylonitrile) -4-chloro-5-methoxy-6-methoxymethylene-pyrimidine was added. After 16 hours, the mixture was hydrolyzed, extracted with ethyl acetate or methylene chloride, the organic phase was washed, dried and, after separation by column chromatography, with ethyl acetate and heptane 3: 7 as the eluent, 0.2 g

2-(4-Benzoesäurenitril)-5-methoxy-6-methoxymethylen-4-(3- propinyloxy)-pyrimidin (4 %), Smp.: 164 °C und 0,4 g 2-(4-Benzoesäuremtril)-5-methoxy-4-(3-propinyloxy)-pyrimidin (8%), Smp.: 183-185 °C.  2- (4-benzoic acid nitrile) -5-methoxy-6-methoxymethylene-4- (3-propynyloxy) pyrimidine (4%), mp .: 164 ° C and 0.4 g of 2- (4-benzoic acid tril) -5 -methoxy-4- (3-propynyloxy) pyrimidine (8%), mp .: 183-185 ° C.

Beispiel 8: Example 8:

2-Phenyl-4-propinyloxy-7,8-dihydro-6H-thiopyrano-[2,3-d]- pyrimidin Verbindung Nr. 3.28

Figure imgf000033_0001
2-phenyl-4-propynyloxy-7,8-dihydro-6H-thiopyrano- [2,3-d] pyrimidine Compound No. 3.28
Figure imgf000033_0001

In 200 ml Wasser wurden 37,7 g 2,4,5,6-Tetrahydro-thiopyran-3-on-2-carbonsäureethylester. 40,0 g Benzamidinhydrochlorid (80 - 85 %, techn. Qualität ca. 15 % Wasser enthaltend) und 21,3 g wasserfreies Natriumcarbonat 4 Tage gerührt. Bei neutralem pH- Wert saugte man ab und erhielt 48,5 g (99%) 2-Phenyl-l,6,7,8-tetrahydro-thiopyrano-[2,3-d]- pyrimidin-4-on, Smp.: > 260 °C. 37.7 g of 2,4,5,6-tetrahydro-thiopyran-3-one-2-carboxylic acid ethyl ester were added to 200 ml of water. 40.0 g of benzamidine hydrochloride (80 - 85%, technical quality containing approx. 15% water) and 21.3 g of anhydrous sodium carbonate stirred for 4 days. At neutral pH was suctioned off and 48.5 g (99%) of 2-phenyl-l, 6,7,8-tetrahydro-thiopyrano- [2,3-d] - pyrimidin-4-one, mp. :> 260 ° C.

In 300 ml POCl3 und 5 ml N,N-Dimethylanilin erhitzte man 48,5 g 48.5 g was heated in 300 ml of POCl 3 and 5 ml of N, N-dimethylaniline

2-Phenyl-1,6,7,8-tetrahydro-thiopvrano-[2,3-d]-pyrimidin-4-on unter Rückfluß. Nach vollständiger Lösung des Pyrimidinons (ca. 60 Minuten) destillierte man bei ca. 200 mm Hg das POCl3 ab, nahm in Methylenchlorid auf und hydrolysierte, wusch die organische Phase neutral, trocknet diese und destillierte das Lösungsmittel ab. Nach 2-phenyl-1,6,7,8-tetrahydro-thiopvrano- [2,3-d] pyrimidin-4-one under reflux. After the pyrimidinone had completely dissolved (about 60 minutes), the POCl 3 was distilled off at about 200 mm Hg, taken up in methylene chloride and hydrolyzed, the organic phase was washed neutral, dried, and the solvent was distilled off. To

säulenchromatographischer Reinigung, mit Essigester und Heptan (1:1) als Laufmittel, erhielt man 49.6 g (99 %) 4-Cmor-2-phenyl-7,8-dmydro-6H-thiopvrano-[2,3-d]-pyrimidin, purification by column chromatography, using ethyl acetate and heptane (1: 1) as the eluent, gave 49.6 g (99%) of 4-cmor-2-phenyl-7,8-dmydro-6H-thiopvrano- [2,3-d] pyrimidine ,

Smp.: 135-137 °C. M.p .: 135-137 ° C.

Zu 1,1 g NaH (80 % in Mineralöl) in 100 ml abs. THF tropfte man 2,0 g Propinylalkohol. rührte eine Stunde und gab dann 6,6 g To 1.1 g NaH (80% in mineral oil) in 100 ml abs. THF was added dropwise to 2.0 g of propynyl alcohol. stirred for an hour and then gave 6.6 g

4-Chlor-phenyl-7,8-dihydro-6H-tMopyrano-[2,3-d]-pyrimidin hinzu. Nach 16 Stunden hydrolysierte man, extrahierte mit Essigester, wusch die organische Phase, trocknete diese, destillierte das Lösungsmittel ab und erhielt 6,7 g (95 %)  4-Chlorophenyl-7,8-dihydro-6H-tMopyrano- [2,3-d] pyrimidine was added. After 16 hours, the mixture was hydrolyzed, extracted with ethyl acetate, the organic phase was washed, dried, the solvent was distilled off and 6.7 g (95%) were obtained.

2-Phenyl-4-propinyloxy-7,8-dihydro-6H-thiopyrano-[2,3-d]-pyrimidin, Smp.: 91 - 93 °C. 2-phenyl-4-propynyloxy-7,8-dihydro-6H-thiopyrano- [2,3-d] pyrimidine, m.p .: 91-93 ° C.

Beispiel 9: Example 9:

5-Chlor-2-phenyl-4-pyrimidincarbonsäurepropinylester Verbindung Nr. 2.1

Figure imgf000034_0001
5-chloro-2-phenyl-4-pyrimidinecarboxylic acid propinyl ester Compound No. 2.1
Figure imgf000034_0001

Aus 27,6 g Natrium und 480 ml Ethanol stellte man die entsprechende Ethanolat-Lösung her und löste 67,6 g Mucochlorsäure in 120 ml Ethanol. Zu 156,6 g Benzamidinhydrochlorid (80 - 85 %, techn. Qualität, ca. 15 % Wasser enthaltend) in 80 ml Ethanol tropfte man die halbe Menge der Ethanolat-Lösung, erwärmte auf 55 - 60 °C und tropfte bei dieser Temperatur die erste Hälfte der Muccochlorsäure-Lösung zum Reaktionsgemisch, tropfte die zweite Hälfte des Ethanolats und dann den Rest der Muccochlorsäure-Lösung hinzu. Man rührte noch eine Stunde bei 55 - 60 °C, kühlte und filtrierte ab. Bei der Mutterlauge stellte man mit 2n Salzsäure einen pH-Wert von 2 ein und filtrierte emeut ab.  The corresponding ethanolate solution was prepared from 27.6 g of sodium and 480 ml of ethanol and 67.6 g of mucochloric acid were dissolved in 120 ml of ethanol. Half the amount of the ethanolate solution was added dropwise to 156.6 g of benzamidine hydrochloride (80-85%, technical quality, containing about 15% water) in 80 ml of ethanol, and the mixture was heated to 55-60 ° C. and dripped at this temperature first half of the muccochloric acid solution to the reaction mixture, dropwise added the second half of the ethanolate and then the rest of the muccochloric acid solution. The mixture was stirred for a further hour at 55-60 ° C., cooled and filtered off. The mother liquor was adjusted to a pH of 2 with 2N hydrochloric acid and filtered again.

Ein Teil des Filtrats (40,7 g) wurde in 150 ml Thionylchlorid und 5 ml DMF 2 Stunden unter Rückfluß erhitzt. Nach dem Abdestillieren des Lösungsmittel erhielt man nach Destillation des Rückstandes über einen Abtreiber 18,8 g  A portion of the filtrate (40.7 g) was refluxed in 150 ml of thionyl chloride and 5 ml of DMF for 2 hours. After the solvent had been distilled off, 18.8 g were obtained after distilling off the residue via a stripper

5-Chlor-2-phenyl-4-pyrirnidincarbonsäurechlorid. 5-chloro-2-phenyl-4-pyrirnidinecarboxylic acid chloride.

Zu 2,5 g NaH (80 % in Mineralöl) in 100 ml abs. THF tropfte man 4,7 g Propinylalkohol, rührte eine Stunde und gab dann 18,2 g 5-Chlor-2-phenyl-4-pyrimidincarbonsäurechlorid hinzu. Nach 16 Smnden hydrolysierte man, extrahierte mit Methylenchlorid, wusch die organische Phase, trocknete diese und erhielt nach Abdestillation des Lösungsmittels und Umkristallisieren aus Essigester und Heptan 12,8 g (63%) To 2.5 g NaH (80% in mineral oil) in 100 ml abs. THF was dropped with 4.7 g of propynyl alcohol, stirred for one hour and then 18.2 g of 5-chloro-2-phenyl-4-pyrimidinecarboxylic acid chloride were added. After 16 hours, the mixture was hydrolyzed, extracted with methylene chloride, the organic phase was washed, dried and, after the solvent had been distilled off and recrystallized from ethyl acetate and heptane, 12.8 g (63%) were obtained.

5-Chlor-2-phenyl-4-pyrimidincarbonsäurepropinylester, Smp.: 82 - 84 °C. 5-chloro-2-phenyl-4-pyrimidinecarboxylic acid propinyl ester, m.p .: 82-84 ° C.

Beispiel 10: Example 10:

5-Chlor-2-phenyl-4-pyrimidincarbo nsäure-1-(3-cWor-5-trifluor-memyl-2-pyridinyl)-3- propinylester Verbindung Nr. 2.11 5-Chloro-2-phenyl-4-pyrimidinecarboxylic acid 1- (3-cWor-5-trifluoromemyl-2-pyridinyl) -3-propinyl ester Compound No. 2.11

Figure imgf000035_0001
Figure imgf000035_0001

In 100 ml Triethylamin wurden 8,6 g 5-Chlor-2-phenyl-4-pyrimidincarbonsäurepropinylester, 0,14 g Bis-(triphenylphosphin)-palladiumdichlorid und 0,02 g Kupfer-(I)-jodid vorgelegt und 7,8 g 3-Chlor-2-jod-5-trifluormethylpyridin zugetropft Nach 16 Smnden wurde die 8.6 g of 5-chloro-2-phenyl-4-pyrimidinecarboxylic acid propinyl ester, 0.14 g of bis (triphenylphosphine) palladium dichloride and 0.02 g of copper (I) iodide were placed in 100 ml of triethylamine, and 7.8 g 3-Chloro-2-iodo-5-trifluoromethylpyridine was added dropwise

Hauptmenge Triethylamin abdestilliert, der Rückstand in Methylenchlorid aufgenommen und mit Wasser gewaschen, getrocknet und eingeengt. Nach Reinigung mittels Most of the triethylamine was distilled off, the residue was taken up in methylene chloride and washed with water, dried and concentrated. After cleaning with

Säulenchromatographie, mit Essigester und Heptan (3:7) als Laufmittel, erhielt man 5,0 g (40%) 5-Chlor-2-phenyl-4-pyrimidincarbonsäure- 1 -(3-chlor-5-trifluor-methyl-2-pyridinyl)-3- propinylester, Smp.: 108 - 110°C. Column chromatography, with ethyl acetate and heptane (3: 7) as the eluent, gave 5.0 g (40%) of 5-chloro-2-phenyl-4-pyrimidinecarboxylic acid 1 - (3-chloro-5-trifluoromethyl-2 -pyridinyl) -3- propynyl ester, m.p .: 108-110 ° C.

Entsprechend der oben aufgeführten Beispielen können die in Tabelle 1 According to the examples listed above, those in Table 1

genannten Verbindungen hergestellt werden. mentioned connections are made.

Bei den Beispielen mit dem Suffix A handelt es sich um die Säureadditionssalze der jeweiligen Stammverbindung; in der Spalte "physikalische Konstante" ist dann die Säure angegeben und der zugehörende Schmelz- oder Zersetzungspunkt Die Salze können im Einzelfall auch noch Kristallwasser enthalten.

Figure imgf000036_0001
The examples with the suffix A are the acid addition salts of the respective parent compound; The acid is then indicated in the "physical constant" column and the associated melting or decomposition point. The salts can also contain water of crystallization in individual cases.
Figure imgf000036_0001

Figure imgf000037_0001
Figure imgf000037_0001

e e

Figure imgf000038_0001
Figure imgf000038_0001

Figure imgf000039_0001
Figure imgf000039_0001

Figure imgf000040_0001
Figure imgf000040_0001

Figure imgf000042_0001
Figure imgf000042_0001

Figure imgf000043_0001
Figure imgf000043_0001

Figure imgf000044_0001
Figure imgf000044_0001

Figure imgf000045_0001
Figure imgf000045_0001

Figure imgf000046_0001
Figure imgf000046_0001

Figure imgf000047_0001
Figure imgf000047_0001

Figure imgf000048_0001
Figure imgf000048_0001

Figure imgf000049_0001
Figure imgf000049_0001

Figure imgf000050_0001
Figure imgf000050_0001

Figure imgf000051_0001
Figure imgf000051_0001

Figure imgf000052_0001
Figure imgf000052_0001

Figure imgf000053_0001
Figure imgf000053_0001

Figure imgf000054_0001
Figure imgf000054_0001

Figure imgf000055_0001
Figure imgf000055_0001

Figure imgf000056_0001
Figure imgf000056_0001

Figure imgf000057_0001
Figure imgf000057_0001

Figure imgf000058_0001
Figure imgf000058_0001

Figure imgf000059_0001
Figure imgf000059_0001

Figure imgf000060_0001
Figure imgf000060_0001

Figure imgf000061_0001
Figure imgf000061_0001

Figure imgf000062_0001
Figure imgf000062_0001

Figure imgf000063_0001
Figure imgf000063_0001

Figure imgf000064_0001
Figure imgf000064_0001

Figure imgf000065_0001
Figure imgf000065_0001

Figure imgf000066_0001
Figure imgf000066_0001

Figure imgf000067_0001
Figure imgf000067_0001

θ θ

Figure imgf000068_0001
Figure imgf000068_0001

Figure imgf000069_0001
Figure imgf000069_0001

< <

Figure imgf000070_0001
Figure imgf000070_0001

Figure imgf000071_0001
Figure imgf000071_0001

Figure imgf000072_0001
Figure imgf000072_0001

Figure imgf000073_0001
Figure imgf000073_0001

Figure imgf000074_0001
Figure imgf000074_0001

Figure imgf000075_0001
Figure imgf000075_0001

C. Biologische Beispiele C. Biological examples

Beispiel 1 example 1

Weizenpflanzen der Sorte "Diplomat" wurden ca.4. Wochen nach Aussaat mit wäßrigen Wheat plants of the "Diplomat" variety were grown approx. Weeks after sowing with aqueous

Suspensionen der erfindungsgemäßen Verbindungen tropfnaß behandelt Suspensions of the compounds according to the invention treated to runoff

Nach dem Antrocknen des Spritzbelages wurden die Pflanzen mit einer wäßrigen After the spray coating had dried on, the plants were washed with an aqueous

Sporensuspension von Pseudocercosporella herpotrichoides inokuliert. Die Pflanzen wurden danach bei 16 - 18 °C und ca. 90 - 100 % rel. Luftfeuchte gehalten. Spore suspension of Pseudocercosporella herpotrichoides inoculated. The plants were then at 16-18 ° C and about 90-100% rel. Humidity kept.

Nach einer Inkubationszeit von ca. 4 Wochen konnte die Befallsauswertung der After an incubation period of approx. 4 weeks, the infection evaluation of the

Versuchspflanzen vorgenommen werden. Der Wirkungsgrad wurde aus dem Befallsgrad im Vergleich zu den unbehandelten, infizierten Kontrollpflanzen ermittelt und ist in Tabelle 2 wiedergegeben. Trial plants are made. The efficiency was determined from the degree of infestation in comparison to the untreated, infected control plants and is shown in Table 2.

Tabelle 2 : Table 2:

Verbindungen Wirkungsgrad gegenüber Pseudocercosporella herpotrichoides gem. Beispiel in % bei ppm Wirkstoff Compounds efficiency compared to Pseudocercosporella herpotrichoides acc. Example in% at ppm active ingredient

Figure imgf000076_0001
Figure imgf000077_0002
Figure imgf000076_0001
Figure imgf000077_0002

unbehandelte,  untreated,

infizierte Pflanzen 0  infected plants 0

Beispiel 2:  Example 2:

Ca. 14 Tage alte Ackerbohnen der Sorte "Ηarz Freya" oder "Frank's Ackerperle" wurden mit wässrigen Suspensionen der beanspruchten Verbindungen tropfhaß behandelt Approximately 14 day old broad beans of the variety "Ηarz Freya" or "Frank's Ackerperle" were treated to run-off with aqueous suspensions of the claimed compounds

Nach Antrocknen des Spritzbelages wurden die Pflanzen mit einer Sporensuspension (1.5 Mio Sporen/ml) von Botrytis cinerea (BCM-resistenter Stamm) inokulierL Die Pflanzen wurden in einer Klimakammer bei 20 - 22 °C und ca. 99 % rel. Luftfeuchte weiterkultiviert. Die Infektion der Pflanzen äußert sich in der Bildung schwarzer Flecke auf Blättern und Stengeln. Die Auswertung der Versuche erfolgte ca. 1 Woche nach Inokulation.  After the spray coating had dried on, the plants were inoculated with a spore suspension (1.5 million spores / ml) of Botrytis cinerea (BCM-resistant strain). The plants were in a climatic chamber at 20-22 ° C. and approx. 99% rel. Humidity continued to be cultivated. The infection of the plants manifests itself in the formation of black spots on leaves and stems. The tests were evaluated approximately 1 week after inoculation.

Der Wirkungsgrad der Prüfsubstanzen wurde prozentual zur unbehandelten, infizierten Kontrolle bonitiert und ist in Tabelle 3 wiedergegeben.  The efficiency of the test substances was rated as a percentage of the untreated, infected control and is shown in Table 3.

Tabelle 3 : Table 3:

Verbindungen Wirkungsgrad gegenüber Botrytis cinerea Compounds efficiency against botrytis cinerea

gem. Beispiel in % bei ppm Wirkstoff  acc. Example in% at ppm active ingredient

Figure imgf000077_0001
Figure imgf000077_0001

unbehandelte,  untreated,

infizierte Pflanzen 0 C. Biologische Beispiele infected plants 0 C. Biological examples

Beispiel 1 example 1

Weizenpflanzen der Sorte "Diplomat" wurden ca.4. Wochen nach Aussaat mit wäßrigen Wheat plants of the "Diplomat" variety were grown approx. Weeks after sowing with aqueous

Suspensionen der erfindungsgemäßen Verbindungen tropfnaß behandelt. Suspensions of the compounds according to the invention treated to runoff.

Nach dem Antrocknen des Spritzbelages wurden die Pflanzen mit einer wäßrigen After the spray coating had dried on, the plants were washed with an aqueous

Sporensuspension von Pseudocercosporella herpotrichoides inokuliert. Die Pflanzen wurden danach bei 16 - 18 °C und ca. 90 - 100 % rel. Luftfeuchte gehalten.  Spore suspension of Pseudocercosporella herpotrichoides inoculated. The plants were then at 16-18 ° C and about 90-100% rel. Humidity kept.

Nach einer Inkubationszeit von ca.4 Wochen konnte die Befallsauswertung der After an incubation period of approx. 4 weeks, the infection evaluation of the

Versuchspflanzen vorgenommen werden. Der Wirkungsgrad wurde aus dem Befallsgrad im Vergleich zu den unbehandelten, infizierten Kontrollpflanzen emüttelt und ist in Tabelle 2 wiedergegeben.  Trial plants are made. The efficiency was shaken from the degree of infestation in comparison to the untreated, infected control plants and is shown in Table 2.

Tabelle 2: Table 2:

Verbindungen Wirkungsgrad gegenüber Pseudocercosporella herpotrichoides gem. Beispiel in % bei ppm Wirkstoff  Compounds efficiency compared to Pseudocercosporella herpotrichoides acc. Example in% at ppm active ingredient

Figure imgf000078_0001
Beispiel 2:
Figure imgf000078_0001
Example 2:

Ca. 14 Tage alte Ackerbohnen der Sorte "Harz Freya" oder "Frank's Ackerperle" .wurden mit wäßrigen Suspensionen der beanspruchten Verbindungen tropfnaß behandelt Approximately 14 day old field beans of the "Harz Freya" or "Frank's field pearl" variety were treated to runoff with aqueous suspensions of the claimed compounds

Nach Antrocknen des Spritzbelages wurden die Pflanzen mit einer Sporensuspension (1,5 Mio Sporen/ml) von Botrytis cinerea (BCM-resistenter Stamm) inokuliert. Die Pflanzen wurden in einer Klimakammer bei 20 - 22 °C und ca. 99 % rel. Luftfeuchte weiterkultiviert. Die Infektion der Pflanzen äußert sich in der Bildung schwarzer Flecke auf Blättern und Stengeln. Die Auswertung der Versuche erfolgte ca. 1 Woche nach Inokulation. After the spray coating had dried on, the plants were inoculated with a spore suspension (1.5 million spores / ml) of Botrytis cinerea (BCM-resistant strain). The plants were in a climatic chamber at 20 - 22 ° C and approx. 99% rel. Humidity continued to be cultivated. The infection of the plants manifests itself in the formation of black spots on leaves and stems. The tests were evaluated approximately 1 week after inoculation.

Der Wirkungsgrad der Prüfsubstanzen wurde prozentual zur unbehandelten, infizierten Kontrolle bonitiert und ist in Tabelle 3 wiedergegeben. The efficiency of the test substances was rated as a percentage of the untreated, infected control and is shown in Table 3.

Tabelle 3: Table 3:

Verbindungen Wirkungsgrad gegenüber Botrytis cinerea Compounds efficiency against botrytis cinerea

gem. Beispiel in % bei ppm Wirkstoff  acc. Example in% at ppm active ingredient

Figure imgf000079_0001
Figure imgf000079_0001

Claims

Patentansprüche: Claims: 1. Verbindungen der Formel I, 1. Compounds of the formula I
Figure imgf000080_0001
Figure imgf000080_0001
 worin wherein R1, R2, R3 = unabhängig voneinander Wasserstoff, Halogen, Hydroxy, Amino, Nitro, Cyano, Thiocyano, (C1-C4)Alkyl, Cyano-(C1-C4)alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylamino, (C1-C4)Dialkylamino, (C1-C4)Alkylcarbonylamino, Halo-(C1-C4)aIkyl, R 1 , R 2 , R 3 = independently of one another hydrogen, halogen, hydroxy, amino, nitro, cyano, thiocyano, (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylamino, (C 1 -C 4 ) dialkylamino, (C 1 -C 4 ) alkylcarbonylamino, halo- (C 1 -C 4 ) alkyl, Hydroxy-(C1-C4)alkyl, Dihydroxy-(C1-C4)alkyl, (C1-C4)Alkoxy-(C1-C4)alkyl, Halo(C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)Alkylthio, Halo-(C1-C4)alkylthio, Hydroxy- (C 1 -C 4 ) alkyl, dihydroxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, halo (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio, halo (C 1 -C 4 ) alkylthio, Halo-(C1-C4)alkylthio-(C1-C4)alkyl, (C1-C4)Alkylthio-(C1-C4)alkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C1-C4)Alkylamino-(C1-C4)alkyl, Halo (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 1 -C 4 ) alkylamino- (C 1 -C 4 ) alkyl, (C1-C4)Dialkylamino-(C1-C4)alkyl, (C3-C9)Cycloalkylamino-(C1-C4)alkyl, (C 1 -C 4 ) dialkylamino- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) cycloalkylamino- (C 1 -C 4 ) alkyl, (C3-C9)Cycloalkyl, (C3-C9 )Cycloalkyl-(C1 -C4)alkyl, (C 3 -C 9 ) cycloalkyl, (C 3 -C 9 ) cycloalkyl- (C 1 -C 4 ) alkyl, (C3-C9)Heterocycloalkyl-(C1-C4)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C1-C4)Alkyl substituiert sein können, (C1-C4)Alkoxycarbonyl-(C1-C4)alkyl, (C1-C4)Alkylaminocarbonyl-(C1-C4)alkyl, (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl, where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl, (C1-C4)Dialkylaminocarbonyl-(C1-C4)alkyl, (C1-C4)Alkylcarbonyl, (C 1 -C 4 ) dialkylaminocarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylcarbonyl, (C1-C4)Haloalkylcarbonyl, (C1-C4)Alkoxycarbonyl, (C1-C4)Haloalkoxycarbonyl, (C1-C4)Alkylthiocarbonyl, (C1-C4)Haloalkylthiocarbonyl, Aminocarbonyl, (C 1 - C4) haloalkylcarbonyl, (C 1 -C 4) alkoxycarbonyl, (C 1 -C 4) haloalkoxycarbonyl, (C 1 -C 4) alkylthiocarbonyl, (C 1 -C 4) Haloalkylthiocarbonyl, aminocarbonyl, (C1-C4)Alkylaminocarbonyl, (C1-C4)Haloalkylaminocarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenyl-(C1-C4)alkyl, gegebenenfalls substituiertes (C 1 -C 4 ) alkylaminocarbonyl, (C 1 -C 4 ) haloalkylaminocarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenyl- (C 1 -C 4 ) alkyl, optionally substituted Phenoxy-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylketo-(C1-C4)alkyl, gegebenenfalls substituiertes Phenyloxycarbonyl-(C1-C4)alkyl, Phenylmercapto-(C1-C4)alkyl, Phenylamino-(C1-C4)alkyl, Phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenylketo- (C 1 -C 4 ) alkyl, optionally substituted phenyloxycarbonyl- (C 1 -C 4 ) alkyl, Phenylmercapto- (C 1 -C 4 ) alkyl, phenylamino- (C 1 -C 4 ) alkyl, Phenoxyphenyl-(C1-C4)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil bis zu dreifach durch Halogen, Ester, (C1-C4)Alkyl, Phenoxyphenyl- (C 1 -C 4 ) alkyl, whereby optionally substituted is to be understood that the phenyl part is substituted up to three times by halogen, ester, (C 1 -C 4 ) alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl, (C1-C4)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy or can be simply substituted by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms, R1, R2 und/oder R3 gegebenenfalls zusammen einen gesättigten, teilweise ungesättigten oder aromatischen Carbocyclus oder Heterocyclus mit den Heteroatomen O, N, S, Si oder P mit 4 bis 10 Ringgliedem, R 1 , R 2 and / or R 3 optionally together form a saturated, partially unsaturated or aromatic carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members, R4 = Wasserstoff, Halogen, (C1-C4)Alkyl, Hydroxy-(C1-C4)alkyl, Dihydroxy-(C1-C4)alkyl, Cyano-(C1-C4)alkyl, Halo-(C1-C4)alkyl, (C1-C4)Alkoxy-(C1-C4)alkyl, R 4 = hydrogen, halogen, (C 1 -C 4 ) alkyl, hydroxy- (C 1 -C 4 ) alkyl, dihydroxy- (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl, halo - (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, Halo(C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)Alkylthio, Halo-(C1-C4)alkylthio, Halo (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio, halo (C 1 -C 4 ) alkylthio, Halo-(C1-C4)alkylthio-(C1-C4)alkyl, (C1-C4)Alkylthio-(C1-C4)alkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C1-C4)Alkylamino-(C1-C4)alkyl, Halo (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 1 -C 4 ) alkylamino- (C 1 -C 4 ) alkyl, (C1-C4)Dialkylaιnino-(C1-C4)alkyl, (C3-C9)Cycloalkylam ino-(C1-C4)alkyl, (C 1 -C 4 ) Dialkylaιnino- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) cycloalkylamino (C 1 -C 4 ) alkyl, (C3-C9)Cycloalkyl, (C3-C9)Cycloalkyl-(C1 -C4)alkyl, (C 3 -C 9 ) cycloalkyl, (C 3 -C 9 ) cycloalkyl- (C 1 -C 4 ) alkyl, (C3-C9)Heterocycloalkyl-(C1-C4)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C1-C4)Alkyl substituiert sein können, (C1-C4)Alkoxycarbonyl-(C1-C4)alkyl, (C1-C4)Alkylaminocarbonyl-(C1-C4)alkyl, (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl, where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl, (C1-C4)Dialkylarninocarbonyl-(C1-C4)alkyl, (C1-C4)Alkylcarbonyl, (C 1 -C 4 ) dialkylarninocarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylcarbonyl, (C1-C4)Haloalkylcarbonyl, (C1-C4)Alkoxycarbonyl, (C1-C4)Haloalkoxycarbonyl, (C1-C4)AIkylthiocarbonyl, (C1-C4)Haloalkylthiocarbonyl, Aminocarbonyl, (C 1 -C 4 ) haloalkylcarbonyl, (C 1 -C 4 ) alkoxycarbonyl, (C 1 -C 4 ) haloalkoxycarbonyl, (C 1 -C 4 ) alkylthiocarbonyl, (C 1 -C 4 ) haloalkylthiocarbonyl, aminocarbonyl, (C1-C4)Alkylaminocarbonyl, (C1-C4)Haloalkylaminocarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls (C 1 -C 4 ) alkylaminocarbonyl, (C 1 -C 4 ) haloalkylaminocarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituiertes Phenyl-(C1-C4)alkyl, gegebenenfalls substituiertes substituted phenyl- (C 1 -C 4 ) alkyl, optionally substituted Phenoxy-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylmercapto-(C1-C4)alkyl, gegebenenfalls substituierter 5- oder 6-gliedriger Heteroaromat, gegebenenfalls substituiertes Phenylcarbonyl, gegebenenfalls substituiertes Phenylketo-(C1-C4)alkyl, gegebenenfalls substituiertes Phenyloxycarbonyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylamino-(C1-C4)alkyl, gegebenenfalls substituiertes Phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenylmercapto- (C 1 -C 4 ) alkyl, optionally substituted 5- or 6-membered heteroaromatic, optionally substituted phenylcarbonyl, optionally substituted phenylketo (C 1 -C 4 ) alkyl , optionally substituted phenyloxycarbonyl- (C 1 -C 4 ) alkyl, optionally substituted phenylamino- (C 1 -C 4 ) alkyl, optionally substituted Phenoxyphenyl-(C1-C4)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil (Heteroaromat) bis zu dreifach durch Halogen, Ester, (C1-C4)Alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl, (C1-C4)Haloalkoxy oder einfach durch Nitro oder Cyano substituert sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann, Phenoxyphenyl- (C 1 -C 4 ) alkyl, where optionally substituted is to be understood that the phenyl part (heteroaromatic) up to three times by halogen, ester, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy or simply by nitro or cyano may be substituted, and halo in the substituents may be substituted one or more times by halogen atoms, R5 = Halogen, (C1-C4)Alkyl, (C1-C9)Alkoxy, Hydroxy-(C1-C4)alkyl, R 5 = halogen, (C 1 -C 4 ) alkyl, (C 1 -C 9 ) alkoxy, hydroxy- (C 1 -C 4 ) alkyl, Dihydroxy-(C1-C4)alkyl, Cyano-(C1-C4)alkyl, Halo-(C1-C4)alkyl, Dihydroxy- (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl, halo- (C 1 -C 4 ) alkyl, (C1-C4)Alkoxy-(C1-C4)alkyl, Halo(C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)Alkylthio, Halo-(C1-C4 )alkylthio, Halo-(C 1-C4 )alkylthio-(C1-C)4alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, halo (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio, halo- (C 1 -C 4 ) alkylthio, halo (C 1 -C 4 ) alkylthio- (C 1 -C) 4 alkyl, (C1-C4)Alkylthio-(C1-C4)alkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C1-C4)Alkylamino. (C1-C4)Dialkylamino, (C3-C9)Cycloalkylamino, (C1-C4)Alkylamino-(C1-C4)alkyl, (C1-C4)Dialkylamino-(C1-C4 )alkyl, (C3-C9)Cycloalkylamino-(C1-C4)alkyl, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 1 -C 4 ) alkylamino. (C 1 -C 4 ) dialkylamino, (C 3 -C 9 ) cycloalkylamino, (C 1 -C 4 ) alkylamino- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) dialkylamino- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) cycloalkylamino- (C 1 -C 4 ) alkyl, (C3-C9)Cycloalkyl, (C3-C9)Cycloalkyl-(C1 -C4)alkyl, (C 3 -C 9 ) cycloalkyl, (C 3 -C 9 ) cycloalkyl- (C 1 -C 4 ) alkyl, (C3-C9)Heterocycloalkyl-(C1-C4)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C1-C4)Alkyl substituiert sein können, (C1-C4)Alkoxycarbonyl-(C1-C4)alkyl, (C1-C4)Alkylaminocarbonyl-(C1-C4)alkyl, (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl, where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl, (C1-C4)Dialkylaminocarbonyl-(C1-C4 )alkyl, (C1-C4)Alkylcarbonyl, (C 1 -C 4 ) dialkylaminocarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylcarbonyl, (C1-C4)Haloalkylcarbonyl, (C1-C4)Alkoxycarbonyl, (C1-C4)Haloalkoxycarbonyl, (C1-C4)Alkylthiocarbonyl, (C1-C4)Haloalkylthiocarbonyl, Aminocarbonyl, (C 1 -C 4 ) haloalkylcarbonyl, (C 1 -C 4 ) alkoxycarbonyl, (C 1 -C 4 ) haloalkoxycarbonyl, (C 1 -C 4 ) alkylthiocarbonyl, (C 1 -C 4 ) haloalkylthiocarbonyl, aminocarbonyl, (C1-C4)Alkylaminocarbonyl, (C1-C4)Haloalkylaminocarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenyl-(C1-C4)alkyl, gegebenenfalls substituiertes (C 1 -C 4 ) alkylaminocarbonyl, (C 1 -C 4 ) haloalkylaminocarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenyl- (C 1 -C 4 ) alkyl, optionally substituted Phenoxy-(C1-C4 )alkyl, gegebenenfalls substituiertes Phenyl-(C1-C4) alkoxy, gegebenenfalls substituiertes Phenylketo-(C1-C4)alkyl, Phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenyl- (C 1 -C 4 ) alkoxy, optionally substituted phenylketo- (C 1 -C 4 ) alkyl, Phenyloxycarbonyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenyloxycarbonyl- (C 1 -C 4 ) alkyl, optionally substituted Phenylamino-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylamino (C 1 -C 4 ) alkyl, optionally substituted Phenoxyphenyl-(C1-C4)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil bis zu dreifach durch Halogen, Ester, (C1-C4)Alkyl, Phenoxyphenyl- (C 1 -C 4 ) alkyl, whereby optionally substituted is to be understood that the phenyl part is substituted up to three times by halogen, ester, (C 1 -C 4 ) alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl , (C1-C4)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy or can be simply substituted by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms, R6 = Wasserstoff, Halogen, (C1-C4)Alkyl, Hydroxy-(C1-C4)alkyl, Dihydroxy-(C1-C4)alkyl. R 6 = hydrogen, halogen, (C 1 -C 4 ) alkyl, hydroxy (C 1 -C 4 ) alkyl, dihydroxy (C 1 -C 4 ) alkyl. Cyano-(C1-C4)alkyl, Halo-(C1-C4)alkyl, (C1-C4)Alkoxy-(C1-C4)alkyl, Halo-(C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)Alkylthio, Halo-(C1-C4)alkylthio, Cyano- (C 1 -C 4 ) alkyl, halo (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, Halo (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio, halo- (C 1 -C 4 ) alkylthio, Halo-(C1-C4)alkylthio-(C1-C4)alkyl, (C1-C4)Alkylthio-(C1-C4)alkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C1-C4)Alkylamino-, (C1-C4)Dialkylamino, Halo (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 1 -C 4 ) alkylamino, (C 1 -C 4 ) dialkylamino, (C3-C9)Cycloalkylamino, (C1-C4)Alkylamino-(C1-C4)alkyl, (C 3 -C 9 ) cycloalkylamino, (C 1 -C 4 ) alkylamino- (C 1 -C 4 ) alkyl, (C1-C4)Dialkylamino-(C1-C4)alkyl, (C3-C9)Cycloalkylamino-(C1-C4)alkyl, (C 1 -C 4 ) dialkylamino- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) cycloalkylamino- (C 1 -C 4 ) alkyl, (C3-C9)CycloaIkyl, (C3-C9)Cycloalkyl-( C1 -C4)alkyl, (C 3 -C 9 ) cycloalkyl, (C 3 -C 9 ) cycloalkyl- (C 1 -C 4 ) alkyl, (C3-C9)Heterocycloalkyl-(C1-C4)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C1-C4)Alkyl substituiert sein können, (C1-C4)Alkoxycarbonyl-(C1-C4)alkyl, (C1-C4)Alkylaminocarbonyl-(C1-C4)alkyl, (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl, where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl, (C1-C4)Dialkylarrdnorarbonyl-(C1-C4)alkyl, (C1-C4)Alkylcarbonyl, (C 1 -C 4 ) dialkylarrnnorarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylcarbonyl, (C1-C4)Haloalkylcarbonyl, (C1-C4)Alkyloxycarbonyl, (C1-C4)Haloalkyloxycarbonyl, (C1-C4)Alkylthiocarbonyl, (C1-C4)Haloalkylthiocarbonyl, Aminocarbonyl, (C 1 -C 4 ) haloalkylcarbonyl, (C 1 -C 4 ) alkyloxycarbonyl, (C 1 -C 4 ) haloalkyloxycarbonyl, (C 1 -C 4 ) alkylthiocarbonyl, (C 1 -C 4 ) haloalkylthiocarbonyl, aminocarbonyl, (C1-C4)Alkylaminocarbonyl, (C1-C4)Haloalkylaminocarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenylketo-(C1-C4)alkyI, gegebenenfalls substituiertes (C 1 -C 4 ) alkylaminocarbonyl, (C 1 -C 4 ) haloalkylaminocarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenylketo (C 1 -C 4 ) alkyl, optionally substituted Phenyloxycarbonyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenyloxycarbonyl- (C 1 -C 4 ) alkyl, optionally substituted Phenoxy-(C1-C4)alkyl, gegebenenfalls substituiertes Phenyl-(C1-C4)alkyl, Phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenyl- (C 1 -C 4 ) alkyl, gegebenenfalls substituiertes Phenylmercapto-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylamino-(C1-C4)alkyI, gegebenenfalls substituiertes optionally substituted phenylmercapto (C 1 -C 4 ) alkyl, optionally substituted phenylamino (C 1 -C 4 ) alkyl, optionally substituted Phenoxyphenyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenoxyphenyl- (C 1 -C 4 ) alkyl, optionally substituted Phenylmercapto-(C1-C4)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil bis zu dreifach durch Halogen, Ester, (C1-C4)Alkyl, Phenylmercapto- (C 1 -C 4 ) alkyl, where optionally substituted is to be understood that the phenyl part is substituted up to three times by halogen, ester, (C 1 -C 4 ) alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl, (C1-C4)Haloalkoxy oder einfach durch Nitro oder Cyano substituert sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy or can be simply substituted by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms, R5 und R6 gegebenenfalls zusammen einen gesättigten, teilweise ungesättigten oder R 5 and R 6 optionally together a saturated, partially unsaturated or aromatischen Carbocyclus oder Heterocyclus mit den Heteroatomen O, N, S, Si oder P mit 4 bis 10 Ringgliedern,  aromatic carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members, X = O, S, NH, N-(C1-C4)Alkyl, C=O, C=S oder CR7R8, X = O, S, NH, N- (C 1 -C 4 ) alkyl, C = O, C = S or CR 7 R 8 , R7, R8 = unabhängig voneinander Wasserstoff, Hydroxy, (C1-C4)Alkyl oder (C1-C4)Alkoxy, Y = O, NH, N-(C1-C4)Alkyl oder CR9R10, wenn X = R 7 , R 8 = independently of one another hydrogen, hydroxy, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy, Y = O, NH, N- (C 1 -C 4 ) alkyl or CR 9 R 10 if X = C = O, C = S oder CR7R8 bedeutet, oder CR9R10 oder entfällt, wenn X = O, S, NH oder N-(C1-C4)Alkyl bedeutet, C = O, C = S or CR 7 R 8 , or CR 9 R 10 or is absent if X = O, S, NH or N- (C 1 -C 4 ) alkyl, R9, R10 = unabhängig voneinander Wasserstoff, (C1-C9)AIkyl, Cyano-(C1-C4)alkyl, R 9 , R 10 = independently of one another hydrogen, (C 1 -C 9 ) alkyl, cyano- (C 1 -C 4 ) alkyl, Halo-(C1-C4)alkyl, Hydroxy-(C1-C4)aIkyl, Dihydroxy-(C1-C4)alkyl, Halo (C 1 -C 4 ) alkyl, hydroxy (C 1 -C 4 ) alkyl, dihydroxy (C 1 -C 4 ) alkyl, (C1-C4)Alkoxy-(C1-C4)alkyl, Halo(C1-C4)alkoxy-(C1-C4)alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, halo (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, Halo-(C1-C4)alkylthio-(C1-C4)alkyl, (C1-C4)Alkylthio-(C1-C4)alkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C1-C4)Alkylamino-(C1-C4)alkyl, Halo (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 1 -C 4 ) alkylamino- (C 1 -C 4 ) alkyl, (C1-C4)Dialkylamino-(C1-C4)alkyl, (C3-C9)Cycloalkylamino-(C1-C4)alkyl, (C 1 -C 4 ) dialkylamino- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) cycloalkylamino- (C 1 -C 4 ) alkyl, (C3-C9)Cycloalkyl, (C3-C9)Cycloalkyl-(C1-C4)alkyl, (C 3 -C 9 ) cycloalkyl, (C 3 -C 9 ) cycloalkyl- (C 1 -C 4 ) alkyl, (C3-C9)Heterocycloalkyl-(C1-C4)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C1-C4)Alkyl substituiert sein können, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl, where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted Phenyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenoxy-(C1-C4)alkyl, Phenyl- (C 1 -C 4 ) alkyl, optionally substituted phenoxy- (C 1 -C 4 ) alkyl, gegebenenfalls substituiertes Phenylamino-(C1-C4)alkyl, gegebenenfalls substituiertes Phenoxyphenyl-(C1-C4)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil bis zu dreifach durch Halogen, Ester, (C1-C4)Alkyl, optionally substituted phenylamino- (C 1 -C 4 ) alkyl, optionally substituted phenoxyphenyl- (C 1 -C 4 ) alkyl, whereby optionally substituted is to be understood that the phenyl part is substituted up to three times by halogen, ester, (C 1 -C 4 ) alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl, (C1-C4)Haloalkoxy oder einfach durch Nitro oder Cyano substituert sein kann, und mit Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy or can simply be substituted by nitro or cyano, and with halo in the Substituents can be substituted one or more times by halogen atoms, R9 und R10 gegebenenfalls zusammen einen gesättigten oder teilweise ungesättigten R 9 and R 10 optionally together a saturated or partially unsaturated Carbocyclus oder Heterocyclus mit den Heteroatomen O, N, S, Si oder P mit 4 bis 10 Ringgliedern und n = eine Zahl von 0 bis 8 bedeuten, sowie deren Säureadditionssalze.  Carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members and n = a number from 0 to 8, and their acid addition salts. 2. Verbindungen der Formel I gemäß Anspruch 1, worin 2. Compounds of formula I according to claim 1, wherein R1, R2, R3 = unabhängig voneinander Wasserstoff, Halogen, Hydroxy, Amino, Nitro, Cyano, Thiocyano, (C1-C4)Alkyl, Cyano-(C1-C4)alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylamino, (C1-C4)Dialkylamino, Halo-(C1-C4)alkyl, Hydroxy-(C1-C4)alkyl, R 1 , R 2 , R 3 = independently of one another hydrogen, halogen, hydroxy, amino, nitro, cyano, thiocyano, (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylamino, (C 1 -C 4 ) dialkylamino, halo (C 1 -C 4 ) alkyl, hydroxy- (C 1 -C 4 ) alkyl, (C1-C4)Alkoxy-(C1-C4)alkyl, Halo-(C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)Alkylthio, Halo-(C1-C4)alkylthio, (C1-C4)Alkenyl, (C2-C6)Alkinyl, (C1-C4)Alkylamino-(C1-C4)alkyl, (C1-C4)Dialkyla mino-(C1-C4)alkyl, (C3-C9)Cycloalkylamino-(C1-C4)alkyl, (C3-C9)Cycloalkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, halo- (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio, halo- ( C 1 -C 4 ) alkylthio, (C 1 -C 4 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 1 -C 4 ) alkylamino- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) dialkyla mino- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) cycloalkylamino- (C 1 - C 4 ) alkyl, (C 3 -C 9 ) cycloalkyl, (C3-C9)Heterocycloalkyl-(C1-C4)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C1-C4)Alkyl substituiert sein können, (C1-C4)Alkoxycarbonyl-(C1-C4)alkyl, (C1-C4)Alkylaminocarbonyl-(C1-C4)alkyl, (C1-C4)Alkylcarbonyl, (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl, where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylcarbonyl, (C1-C4)Alkoxycarbonyl, Ammocarbonyl,(C1-C4)Alkylammocarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenyl-(C1-C4)alkyl, gegebenenfalls substituiertes (C 1 -C 4 ) alkoxycarbonyl, ammocarbonyl, (C 1 -C 4 ) alkylammocarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenyl- (C 1 -C 4 ) alkyl, optionally substituted Phenoxy-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylketo-(C1-C4)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil bis zu dreifach durch Halogen, Ester, (C1-C4)Alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, Phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenylketo (C 1 -C 4 ) alkyl, where optionally substituted is understood to mean that the phenyl part is substituted up to three times by halogen, ester, (C 1 -C 4 ) Alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C1-C4)Haloalkyl, (C1-C4)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy or can be simply substituted by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms, R1, R2 und/oder R3 gegebenenfalls zusammen einen gesättigten, teilweise ungesättigten oder aromatischen Carbocyclus oder Heterocyclus mit den Heteroatomen O, N, oder S mit 4 bis 10 Ringgliedem, R 1 , R 2 and / or R 3 optionally together form a saturated, partially unsaturated or aromatic carbocycle or heterocycle with the heteroatoms O, N, or S with 4 to 10 ring members, R4 = Wasserstoff, Halogen, (C1-C4)Alkyl, Dihydroxy-(C1-C4)alkyl, Hydroxy-(C1-C4)alkyl, (C1-C4)Alkylthio, Perhalo-(C1-C4)alkylthio, (C2-C6)Alkenyl, (C2-C6) Alkinyl, (C1-C4)Alkylamino-(C1-C4)alkyl, (C1-C4)Dialkylamino-(C1-C4)alkyl, R 4 = hydrogen, halogen, (C 1 -C 4 ) alkyl, dihydroxy- (C 1 -C 4 ) alkyl, hydroxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio, perhalo- ( C 1 -C 4 ) alkylthio, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 1 -C 4 ) alkylamino- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) Dialkylamino (C 1 -C 4 ) alkyl, (C3-C9)Cycloalkylamino-(C1-C4)alkyl, (C3-C9)Cycloalkyl, (C 3 -C 9 ) cycloalkylamino- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) cycloalkyl, (C3-C9)Cycloalkyl-(C1-C4)alkyl, (C3-C9)Heterocycloalkyl-(C1-C4)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C1-C4)Alkyl substituiert sein können, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenylcarbonyl, gegebenenfalls substituierter 5- oder 6-gliedriger Heteroaromat, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil (Heteroaromat) bis zu dreifach durch Halogen, Ester, (C1-C4)Alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl, (C1-C4)Haloalkoxy oder einfach durch Nitro oder Cyano (C 3 -C 9 ) cycloalkyl- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl, the cyclic radicals being up to threefold by (C 1 -C 4 ) Alkyl may be substituted, optionally substituted phenyl, optionally substituted phenylcarbonyl, optionally substituted 5- or 6-membered heteroaromatic, whereby optionally substituted is understood to mean that the phenyl part (heteroaromatic) is substituted up to three times by halogen, ester, (C 1 - C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy or simply by nitro or cyano substituiert sein kann, und Halo in den Substituenten ein- oder mehrfach durch  can be substituted, and halo in the substituents one or more times Halogenatome substituiert bedeuten kann,  Halogen atoms may be substituted, R5 = Halogen, (C1-C4)Alkyl, (C1-C9)Alkoxy, Hydroxy-(C1-C4)alkyl, Dihydroxy-(C1-C4)alkyl, Cyano-(C1-C4)alkyl, Halo-(C1-C4)alkyl, R 5 = halogen, (C 1 -C 4 ) alkyl, (C 1 -C 9 ) alkoxy, hydroxy- (C 1 -C 4 ) alkyl, Dihydroxy- (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl, halo- (C 1 -C 4 ) alkyl, (C1-C4)Alkoxy-(C1-C4)aIkyl, Halo(C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)Alkylthio, Halo-(C1-C4)alkylthio, Halo-(C1-C4)alkylthio-(C1-C4)alkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C1-C4)Alkylamino, (C1-C4) Dialkylamino, (C3-C9)Cycloalkylamino. (C1-C4)Alkylanιino-(C1-C4)alkyl, (C1-C4)Dialkylarnino-(C1-C4)alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, halo (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio, halo- (C 1 -C 4 ) alkylthio, halo (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 1 -C 4 ) alkylamino, (C 1 -C 4 ) dialkylamino, (C 3 -C 9 ) cycloalkylamino. (C 1 -C 4 ) alkylanιino- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) dialkylarnino- (C 1 -C 4 ) alkyl, (C3-C9)CycloaIkylamino-(C1-C4)alkyl, (C3-C9)Cycloalkyl, (C 3 -C 9 ) cycloalkylamino- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) cycloalkyl, (C3-C9)Cycloalkyl-(C1-C4)alkyl, (C3-C9)Heterocycloalkyl-(C1-C4)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C1-C4)Alkyl substituiert sein können, (C1-C4)Alkylcarbonyl, (C1-C4)Alkoxycarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes (C 3 -C 9 ) cycloalkyl- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl, the cyclic radicals being up to threefold by (C 1 -C 4 ) Alkyl may be substituted, (C 1 -C 4 ) alkylcarbonyl, (C 1 -C 4 ) alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted Phenyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenoxy-(C1-C4)alkyl, Phenyl- (C 1 -C 4 ) alkyl, optionally substituted phenoxy- (C 1 -C 4 ) alkyl, gegebenenfalls substituiertes Phenyl- (C1-C4)alkoxy, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil bis zu dreifach durch Halogen, Ester, (C1-C4)Alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl, optionally substituted phenyl- (C 1 -C 4 ) alkoxy, where optionally substituted is understood to mean that the phenyl part is substituted up to three times by halogen, ester, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl, (C1-C4)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann, R6= Wasserstoff, Halogen, (C1-C4) Alkyl, Hydroxy-(C1-C4)alkyl, Perhalo-(C1-C4)alkyl , (C1-C4)Alkoxy-(C1-C4)alkyl, Halo-(C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)Alkylthio, (C1-C4)Alkylthio-(C1-C4)alkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C1-C4)Alkylamino. (C1-C4)Dialkylamino, (C3-C9)Cycloalkylamino, (C1-C4)Alkylamino-(C1-C4)alkyl, (C1-C4)Dialkylamino-(C1-C4)alkyl, (C3-C9)Cycloalkylammo-(C1-C4)alkyl, (C 1 -C 4 ) haloalkoxy or can be simply substituted by nitro or cyano and halo in the substituents can be substituted one or more times by halogen atoms, R 6 = hydrogen, halogen, (C 1 -C 4 ) alkyl, hydroxy- (C 1 -C 4 ) alkyl, perhalo (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, halo- (C 1 -C 4 ) alkoxy- ( C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) Alkynyl, (C 1 -C 4 ) alkylamino. (C 1 -C 4 ) dialkylamino, (C 3 -C 9 ) cycloalkylamino, (C 1 -C 4 ) alkylamino- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) dialkylamino- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) cycloalkylammo- (C 1 -C 4 ) alkyl, (C3-C9)Cycloalkyl, (C3-C9)Cycloalkyl-(C1 -C4)alkyl, (C 3 -C 9 ) cycloalkyl, (C 3 -C 9 ) cycloalkyl- (C 1 -C 4 ) alkyl, (C3-C9)Heterocycloalkyl-(C1-C4)alkyl, wobei die cyclischen Reste bis zu dreifach durch (C1-C4)Alkyl substituiert sein können, (C1-C4)Alkylcarbonyl, (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl, where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylcarbonyl, (C1-C4)Alkoxycarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebnenfalls substituiertes Phenylketo-(C1-C4)alkyl, gegebenenfalls substituiertes Phenoxycarbonyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenyl-(C1-C4)alkyl, gegebenenfalls substituiertes (C 1 -C 4 ) alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenylketo (C 1 -C 4 ) alkyl, optionally substituted phenoxycarbonyl- (C 1 -C 4 ) alkyl, optionally substituted phenyl- (C 1 -C 4 ) alkyl, optionally substituted Phenoxy-(C1-C4)alkyl, gegebenenfalls substituiertes Phenyl-(C1-C4)alkyl, Phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenyl- (C 1 -C 4 ) alkyl, gegebenenfalls substituiertes Phenoxyphenyl-(C1-C4)alkyl, wobei unter optionally substituted phenoxyphenyl- (C 1 -C 4 ) alkyl, wherein under gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil bis zu dreifach durch Halogen, Ester, (C1-C4)Alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl, (C1-C4)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann, optionally substituted is to be understood that the phenyl moiety up to three times by halogen, ester, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) Haloalkyl, (C 1 -C 4 ) haloalkoxy or can be substituted simply by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms, R5 und R6 gegebenenfalls zusammen einen gesättigten, teilweise ungesättigten oder R 5 and R 6 optionally together a saturated, partially unsaturated or aromatischen Carbocyclus oder Heterocyclus mit den Heteroatomen O, N oder S mil 4 bis 10 Ringgliedern,  aromatic carbocycle or heterocycle with the heteroatoms O, N or S mil 4 to 10 ring members, X = O, NH, N-(C1-C4)Alkyl, S, C=O, C=S oder CR7R8, X = O, NH, N- (C 1 -C 4 ) alkyl, S, C = O, C = S or CR 7 R 8 , R7, R8 = unabhängig voneinander Wasserstoff, Hydroxy, (C1-C4)Alkyl oder (C1-C4)Alkoxy , R 7 , R 8 = independently of one another hydrogen, hydroxy, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy, Y = O, NH, N-(C1-C4)Alkyl oder CR9R10, wenn X = C=O, C=S oder CR7R8 bedeutet oder CR9R10 oder entfällt, wenn X = O, S, NH oder N-(C1-C4)Alkyl bedeutet, Y = O, NH, N- (C 1 -C 4 ) alkyl or CR 9 R 10 if X = C = O, C = S or CR 7 R 8 or CR 9 R 10 or not applicable if X = O , S, NH or N- (C 1 -C 4 ) alkyl, R9, R10 = unabhängig voneinander Wasserstoff, (C1-C9)Alkyl oder durch Halogen, R 9 , R 10 = independently of one another hydrogen, (C 1 -C 9 ) alkyl or through halogen, (C1-C4)Alkyl oder (C1-C4)Alkoxy gegebenenfalls substituiertes Phenyl, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy optionally substituted phenyl, R9 und R10 gegebenenfalls zusammen einen gesättigten oder teilweise ungesättigten R 9 and R 10 optionally together a saturated or partially unsaturated Carbocyclus oder Heterocyclus mit den Heteroatomen O, N oder S mit 4 bis 10 Ringgliedern, n = eine Zahl von 0 bis 4 bedeuten, sowie deren Säureadditionssalze.  Carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10 ring members, n = a number from 0 to 4, and their acid addition salts. 3. Verbindungen der Formel I gemäß den Ansprüchen 1 oder 2, worin 3. Compounds of formula I according to claims 1 or 2, wherein R1, R2, R3 = unabhängig voneinander Wasserstoff, Chlor, Brom, Nitro oder (C1-C4)Alkoxy, R 1 , R 2 , R 3 = independently of one another hydrogen, chlorine, bromine, nitro or (C 1 -C 4 ) alkoxy, R4 = Wasserstoff, Jod, Brom, (C1-C4)Alkyl, Dialkylamino-(C1-C4)alkyl, R 4 = hydrogen, iodine, bromine, (C 1 -C 4 ) alkyl, dialkylamino- (C 1 -C 4 ) alkyl, Phenyl-(C1-C4)alkyl-(C1-C4)alkylamino-(C1-C4)alkyl, im Phenylteil (Heteroaromat ) durch Halogen, (C1-C4)Alkyl, (C1-C4)Alkoxy oder Perhalo-(C1-C4)alkyl Phenyl- (C 1 -C 4 ) alkyl- (C 1 -C 4 ) alkylamino- (C 1 -C 4 ) alkyl, in the phenyl part (heteroaromatic) by halogen, (C 1 -C 4 ) alkyl, (C 1 - C 4 ) alkoxy or perhalo (C 1 -C 4 ) alkyl gegebenenfalls substituiertes Phenyl oder Pyridinyl,  optionally substituted phenyl or pyridinyl, R5 = Halogen, (C1-C4)Alkyl, (C1-C4)Alkoxy, Phenyl-(C1-C4)alkoxy, (C1-C4)Alkinyloxy. R 5 = halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, phenyl- (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkynyloxy. (C1-C4)Alkylmercapto oder (C1-C4)Alkylsulfonyl, R6 = Wasserstoff, (C1-C4)Alkyl, (C1-C4)Alkoxy-(C1-C4)alkyl oder (C 1 -C 4 ) alkylmercapto or (C 1 -C 4 ) alkylsulfonyl, R 6 = hydrogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl or (C1-C4)AlkoxycarbonyI, (C 1 -C 4 ) alkoxycarbonyl, R5 und R6 gegebenenfalls zusammen einen Teil eines gesättigten oder ungesättigten Cyclus mit 5 oder 6 Ringgliedem, bei dem ein Kohlenstoff durch ein S substituiert sein kann, R 5 and R 6 optionally together form part of a saturated or unsaturated cycle with 5 or 6 ring members, in which a carbon can be substituted by an S, X = C=O, O oderNH, X = C = O, O or NH, Y = O oder NH, wenn X = C=O isL Y = O or NH if X = C = O isL Y = entfällL wenn X = O oder NH ist und n = eine Zahl von 0 bis 2 bedeuten. Y = not applicable if X = O or NH and n = a number from 0 to 2. 4. Verbindungen der Formel I gemäß einem oder mehreren der Ansprüche 1 bis 3, worin R1, R2, R3 = unabhängig voneinander Wasserstoff, Cl, Br oder OCH3, R4 = 4. Compounds of formula I according to one or more of claims 1 to 3, wherein R 1 , R 2 , R 3 = independently of one another hydrogen, Cl, Br or OCH 3 , R 4 = Wasserstoff, R5 = Cl, Br, OCH3 oder OC2H5, R6 = Wasserstoff oder -OCH2-CH2, X = C=O, O oder NH und Y = O oder NH, wenn X = C=O oder entfällt, wenn X = O oder NH bedeuten. Hydrogen, R 5 = Cl, Br, OCH 3 or OC 2 H 5 , R 6 = hydrogen or -OCH 2 -CH 2 , X = C = O, O or NH and Y = O or NH if X = C = O or not applicable if X = O or NH. 5. Verfahren zur Herstellung von Verbindungen der Formel I, gemäß einem oder 5. A process for the preparation of compounds of formula I, according to one or mehreren der Ansprüche 1 bis 4, worin Y = O, NH oder N(C1-C4)Alkyl und X =several of claims 1 to 4, wherein Y = O, NH or N (C 1 -C 4 ) alkyl and X = C=O, C=S oder CR7R8 bedeuten, dadurch gekennzeichnet, daß man Verbindungen der Formel II C = O, C = S or CR 7 R 8 , characterized in that compounds of the formula II ,
Figure imgf000088_0001
.
Figure imgf000088_0001
 worin Hal = Chlor oder Brom bedeutet, mit Verbindungen der Formel III HY— CH2 - C≡C - R 4 (III)where Hal = chlorine or bromine, with compounds of the formula III HY— CH 2 - C≡C - R 4 (III)
Figure imgf000089_0003
Figure imgf000089_0003
 umsetzL oder, falls in der Formel l Y=C R9R10 bedeutet oder Y entfallt und X = O, S, NH oder N-(C1-C4)Alkyl bedeutet, Verbindungen der Formel IV react L or, in the formula I means Y = CR 9 R 10 or Y is omitted and X = O, S, NH or N- (C 1 -C 4 ) alkyl, compounds of the formula IV
Figure imgf000089_0001
Figure imgf000089_0001
 worin Hal = Chlor oder Brom bedeutet, mit Verbindungen der Formel V  where Hal = chlorine or bromine, with compounds of formula V
Figure imgf000089_0002
umsetzt, und wenn R4 = H bedeutet, den Wasserstoff gegebenenfalls gegen Halogen austauscht.
Figure imgf000089_0002
converts, and if R 4 = H, the hydrogen optionally exchanged for halogen. 6. Fungizide Mittel, dadurch gekennzeichnet, daß sie eine wirksame Menge einer Verbindung der Formel I gemäß einem oder mehreren der Ansprüche 1 bis 4 enthalten. 6. Fungicidal compositions, characterized in that they contain an effective amount of a compound of formula I according to one or more of claims 1 to 4. 7. Verwendung von Verbindungen der Formel I gemäß einem oder mehreren der 7. Use of compounds of formula I according to one or more of the Ansprüche 1 bis 4 zur Bekämpfung von Schadpilzen.  Claims 1 to 4 for combating harmful fungi. 8. Verfahren zur Bekämpfung von Schadpilzen, dadurch gekannzeichnet, daß man auf diese oder die von ihnen befallenen Pflanzen, Flächen oder Substrate eine wirksame Menge einer Verbindung der Formel I gemäß einem oder mehreren der Ansprüche 1 bis 4 appliziert 8. Process for combating harmful fungi, characterized in that an effective one on these or the plants, surfaces or substrates attacked by them Amount of a compound of formula I according to one or more of claims 1 to 4 applied
PCT/EP1991/001790 1990-09-19 1991-09-19 2-phenyl-pyrimidines, process for producing the same, agents containing the same and their use as fungicides Ceased WO1992005159A1 (en)

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