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WO1992005158A1 - 4-anilino-pyrimidines, process for producing the same, agents containing the same and their use as fungicides - Google Patents

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

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Publication number
WO1992005158A1
WO1992005158A1 PCT/EP1991/001791 EP9101791W WO9205158A1 WO 1992005158 A1 WO1992005158 A1 WO 1992005158A1 EP 9101791 W EP9101791 W EP 9101791W WO 9205158 A1 WO9205158 A1 WO 9205158A1
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Prior art keywords
alkyl
optionally substituted
alkoxy
alkylthio
halo
Prior art date
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PCT/EP1991/001791
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German (de)
French (fr)
Inventor
Klemens Minn
Peter Braun
Burkhard Sachse
Heinrich Wicke
Original Assignee
Hoechst Aktiengesellschaft
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Publication of WO1992005158A1 publication Critical patent/WO1992005158A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • 4-anilino-pyrimidine derivatives are known to be effective components in fungicidal compositions
  • New 4-anilino-pyrimidine derivatives have been found which have advantageous effects in combating a broad spectrum of phytopatogenic fungi, in particular at low doses, and do not cause damage to useful plants.
  • the present invention therefore relates to compounds of the formula I
  • R 1 , R 2 independently of one another hydrogen, (C 1 -C 9 ) alkyl, cyano- (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 5- or 6-membered heteroaromatic, optionally substituted Phenyl, optionally substituted phenoxy, optionally substituted phenyl- (C 1 -C 4 ) alkyl, optionally substituted phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenylmercapto- (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,
  • (C 1 -C 4 ) can be haloalkoxy or simply substituted by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms, R 1 and R 2 optionally together a saturated or partially unsaturated
  • R 3 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,
  • Phenyl- (C 1 -C 4 ) alkyl optionally substituted phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenylmercapto- (C 1 -C 4 ) alkyl, 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,
  • (C 1 -C 4 ) can be haloalkoxy or simply substituted by niuo or cyano, and can mean halo in the substituents substituted one or more times by halogen atoms,
  • R 4 , R 5 , R 6 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- (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
  • 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 ) 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,
  • R 4 , R 5 and / or R 6 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 7 hydrogen, formyl, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, halo (C 1 -C 4 ) alkoxy,
  • (C 1 -C 4 ) alkoxycarbonyl optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenyl- (C 1 -C 4 ) alkyl, optionally substituted phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenylmercapto- (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 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,
  • R 7 and R 4 and / or R 5 optionally together a saturated or partially
  • R 8 , R 9 independently of one another hydrogen, halogen, (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 phenylmercapto- (C 1 -C 4 ) alkyl, 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 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,
  • R 8 and R 9 optionally together a saturated, partially unsaturated or
  • R 1 , R 2 preferably independently of one another are hydrogen, (C 1 -C 9 ) alkyl, in the phenyl part by halogen, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy optionally substituted phenyl, in particular hydrogen or (C 1 -C 4 ) alkyl, particularly preferably hydrogen, R 1 and R 2 together can form a saturated or partially unsaturated carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10 ring members, in particular with 5 or 6 ring members, and
  • R 3 preferably denotes hydrogen, halogen, (C 1 -C 4 ) alkyl, hydroxy- (C 1 -C 4 ) alkyl,
  • (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, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted 5- to 6-membered heteroaromatic, for example pyridm, thiophene, where optionally substituted is to be understood to mean that the phenyl part (heteroaromatic) is substituted up to three times by halogen, ester , (C 1 -C 4 ) alkyl, (C !
  • R 3 is in particular hydrogen or halogen, particularly preferably hydrogen.
  • R 4 , R 5 , R 6 are preferably independently of one another hydrogen, halogen, hydroxyl,
  • (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,
  • R 4 , R 5 and / or R 6 together can be a saturated, partially unsaturated or
  • R 4 , R 5 , R 6 are in particular independently of one another hydrogen, halogen,
  • R 7 preferably denotes hydrogen, (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, halo- (C 1 -C 4 ) alkoxy, amino (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylamino (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkoxy, amino, (C 1 -C 4 ) alkylamino ,
  • R 7 and R 4 and / or R 5 together can form a saturated or partially unsaturated carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10 ring members.
  • R 7 in particular denotes hydrogen or (C 1 -C 4 ) alkyl, particularly preferably hydrogen.
  • R 8 , R 9 are preferably independently of one another hydrogen, halogen, (C 1 -C 4 ) alkyl,
  • (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
  • 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,
  • R 8 in particular denotes hydrogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, phenyl- (C 1 -C 4 ) alkoxy or halogen, particularly preferably hydrogen, Cl or OCH 3 .
  • R 8 and R 9 together can form a saturated, partially unsaturated or aromatic carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10 ring members.
  • R 9 in particular denotes hydrogen, (C 1 -C 4 ) alkyl, perhalo (C 1 -C 4 ) alkyl,
  • X is preferably oxygen or sulfur and n is a number from 0 to 4, in particular 0 or 1, particularly preferably 0.
  • Halo in the individual substituents is to be understood as being 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, and also sulfonic acids such as p-toluenesulfonic acid or 1,5-naphthalenedisulfonic acid.
  • the acid addition compounds of the formula I can be obtained in a simple manner by the customary salt formation methods, for example by dissolving a compound of the formula I in a suitable organic solvent and adding the acid, and can be isolated in a known manner, for example by filtration, and optionally by washing with an inert solvent organic solvents can be cleaned.
  • the pyrimidines of the formula I can be prepared by various multistage processes.
  • R 10 in this and in the following formula schemes stands for S, S- (C 1 -C 4 ) alkyl, im
  • R 11 represents (C 1 -C 4 ) alkyl or im
  • the subsequent condensation can take place with thiourea or S-alkylated thioureas, which can be used in pure form or in situ, using bases (alcoholates such as NaOMe) released from their salts.
  • bases alcoholates such as NaOMe
  • Protic solvents in particular lower alcohols, have proven particularly suitable for the condensation.
  • the known pyrimidinones or mercaptopyrimidinones are modified with an alkylating agent, such as alkyl halides (for example methyl iodide) or alkyl acid esters (for example dimethyl sulfate, trimethyl phosphoric acid), in particular propynyl halides, using a base such as NaOH, NaH or triethylamine in a suitable protic or aprotic solvent (DMF, acetonitrile , Water) at temperatures from 0 ° C to 260 ° C, preferably in the temperature range from 50 ° C to the boiling point of
  • the 4-pyrimidinones thus obtained can be treated with excess POCl 3 (POBr 3 ) without 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-dimethylaniline in 0.001 to 2 molar equivalents, preferably 0.02 equivalents, at temperatures from 50 ° C. to 110 ° C., preferably at the boiling point of POCl 3 (POBr 3 ), are converted into the corresponding 4-halopyrimidines (cf. Beilstein, Hauptwerk, volume 25, p. 372, Beilstein, 3rd / 4th supplement, volume 23, p. 2471).
  • he anilines of formula IV are mostly known compounds or can in can be produced in a manner analogous to those skilled in the art.
  • the reaction of II with IV takes place depending on the reactivity of the derivatives in an inert solvent (water / acetone, toluene, THF) at temperatures from 0 ° C. to 150 ° C., preferably from 50 ° C. to 100 ° C.
  • the exchange can be promoted by adding catalytic to equimolar bases, but in general it has proven to be advantageous to catalyze the reaction with acid, in particular with hydrochloric acid.
  • R 12 is a radical with a triple bond, the expected addition of the aniline to the triple bond does not take place.
  • the sulfur-bearing group can be oxidized with corresponding 2-alkylmercaptopyrimidines.
  • suitable oxidizing agents such as peroxides (e.g.
  • R 13 represents halogen, in particular chlorine, * *> * R 4
  • the sulfonyl group can be exchanged for alcohols.
  • an inert solvent toluene, THF
  • THF inert solvent
  • halogenation of the alkynyl function may be mentioned as an example of a further modification of starting materials for the preparation of compounds of the formula I.
  • alkynes, di- and polyynes, allenes, cumulenes methods of organic chemistry (Houben / Weyl) Thieme- Verlag, 1977, volume 5.2a, Stuttgart, pp. 600 ff.)
  • a suitable aprotic solvent such as THF or dioxane
  • bases such as n-butyllithium, for example iodine or bromine.
  • R 3 represents X, which represents halogen, in particular bromine or iodine.
  • 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. It is also possible to successfully combat curative pathogens that have already penetrated the plant tissue. 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 dressing agents for the treatment of seeds and plantings for protection against fungal infections and pathogenic fungi occurring in the soil.
  • the spectrum of activity of the claimed compounds encompasses a large number of different economically important phytopathogenic fungi, such as Altemaria mali, Botrytis cinerea, benzimidazole- and / or dicarboximide-sensitive and resistant strains, Sclerotinia sclerotiorum as well as other gray mold species, Cercospora beticola, Ceratheisisipium, Ceratheisisisipa, Ceratheisisisipa, Ceratheisisipasola, Ceratheisisipium, Ceratheisisipasola, Ceratheisisisipa, Ceratheisisipa, Ceratheisisipa graminis hordei, Erysiphe
  • 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
  • compositions which include the compounds of the formula I contain suitable formulation aids.
  • 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 formulations, microcapsules, waxes or baits.
  • the necessary formulation aids such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in:
  • z. 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. ligmnsulfonic acid sodium,
  • Emulsifiable concentrates are obtained by dissolving the active ingredient in an organic solvent, e.g. B. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers.
  • organic solvent e.g. B. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers.
  • Alkylarylsulfonic acid calcium salts such as Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers,
  • Fatty alcohol polyglycol ether propylene oxide-ethylene oxide-sorbitan fatty acid ester,
  • Polyoxethylene sorbitan fatty acid ester or polyoxethylene sorbitol 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, pyrophyllite or diatomaceous earth.
  • Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying
  • Active ingredient concentrates by means of adhesives, e.g. As polyvinyl alcohol, sodium polyacrylic acid or mineral oils, on the surface of carriers such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if appropriate in a mixture with fertilizers.
  • adhesives e.g. As polyvinyl alcohol, sodium polyacrylic acid or mineral oils
  • 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 substance concentration in wettable powders is 10 to 90% by weight, the rest 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.
  • the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers.
  • a conventional manner e.g. B. with wettable powders, emulsifiable Concentrates, dispersions and sometimes also in the case of microgranules using water.
  • Dust-like and granulated preparations and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the required application rate varies. It can fluctuate within wide limits, e.g. B. from 0.005 to 10.0 kg / ha or more of active substance, but is preferably in the range of 0.01 to 5 kg / ha.
  • the active compounds according to the invention can be used in their commercially available formulations either alone or in combination with other fungicides known from the literature.
  • Tebuconazole fluotrimazole, tridemorph, dimethomorph, dodemorph, fenpropimorph, Falimorph, S-32165, Chlobenzthiazone, Parinol, buthiobate, fenpropidin, triforine, fenarimol, .Nuarimol, triarimol, ethirimol, dimethirimol, Bupirimate, Rabenzazole, Tricyclazole, Fluobenzimine, Pyroxyfur, NK -483, PP-389, Pyroquilon, Hymexazole, Fenitropan, UHF-8227, Cymoxanil, Dichlorfunanid, Captafol, Captan, Folpet, Tolyfluanid.
  • 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.
  • active compounds 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:
  • Demeton-S-methyl diazinon, dichlorvos, dimethoate, ethoprophos, etrimfos, fenitrothion.
  • Fenthion Heptenophos, Parathion, Parathionmethyl, Phosalon, Pirimiphos-ethyl,
  • Pirimiphos-methyl Profenofös, Prothiofos, Sulprofos, Triazophos, Trichlorphon.
  • Cyclopropanecarboxylic acid (2-naphthylmethyl) ester (Ro 12-0470), cyromacin, DDT, dicofol, N- (3,5-dichloro-4- (1,1,2, 2-tetrafluoroethoxy) phenylamino) carbonyl) -2, 6-difluoro-benzamide (XRD 473), diflubenzuron, N- (2,3-dihydro-3-methyl-1,2-thiazol-2-ylidenes) 2,4-xylidenes, dinobutone, dinocap, endosulfane, fenoxycarb, fenthiocarb , Flubenzimine, flufenoxuron.
  • Forms of use can vary widely, the active substance concentration of the forms of use can be from 0.0001 to 100% by weight of active substance, preferably from 0.001 to 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • a dusting agent is obtained by mixing 10 parts by weight of active compound and 90 parts by weight of talc as an inert substance and comminuting them in a hammer mill.
  • a wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight of active compound, 65 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium as the wetting agent. and dispersant mixes and grinds in a pin mill.
  • a dispersion concentrate which is readily dispersible in water is prepared by mixing 40 parts by weight of active compound with 7 parts by weight of a sulfosuccinic acid half-ester, 2 parts by weight of a lignosulfonic acid sodium salt and 51 parts by weight of water and in a attritor milled 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 this is sprayed onto the surface of a
  • Attapulgite granules dry and mix 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.
  • Tri (C 8 / C 10 ) alkylmethylammonium chloride stirred for about 1 hour, then dripped 34 ml
  • Propinyl bromide (80% solution in toluene) was added and the mixture was heated under reflux for about 6 hours. After cooling and concentrating the reaction mixture, the mixture was taken up in 300 ml of water, neutralized with acetic acid and, after filtering off, 46 g (98%) were obtained.
  • Tri (C 8 / C 10 ) alkyl methyl ammonium chloride stirred for about 1 hour, then dripped 50 ml
  • the examples with the suffix A are the acid addition salts of the respective parent compound; the acid and the associated melting or decomposition point are then given in the "physical constant" column.
  • the salts can also contain water of crystallization.
  • 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 comb 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 again placed in the climatic chamber overnight in order to stimulate the sporulation of the fungus. The infestation was then assessed. The degree of infestation was expressed in% infested leaf area in comparison to the control plants.

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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)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Compounds have the formula (I), in which R1, R2 represent independently from each other hydrogen or (C¿1?-C4)alkyl; R?1 and R2¿ if necessary form together a saturated or partially unsaturated carbocyclic or heterocyclic moiety with the heteroatoms O, N or S and 5 or 6 cyclic members; R3 represents hydrogen or halogen; R?4, R5, R6¿ represent independently from each other hydrogen, halogen, (C¿1?-C4)alkyl, (C1-C4)alkoxy or phenoxy eventually substituted in the phenyl moiety by halogen, (C1-C4)alkyl or (C1-C4)alkoxy; R?4, R5 and R6¿ form together a saturated, partially insaturated or aromatic carbocyclic or heterocyclic moiety with the heteroatoms O, N or S and 5 to 7 cyclic members; R7 is hydrogen or (C¿1?-C4)alkyl; R?8¿ is hydrogen, (C¿1?-C4)alkyl, (C1-C4)alkoxy, phenyl-(C1-C4)alkoxy or halogen; R?9¿ is hydrogen, (C¿1?-C4)alkyl, perhalo-(C1-C4)alkyl, (C1-C4)alkoxy-(C1-C4)alkyl or phenyl-(C1-C4)alkyl; R?8 and R9¿ if necessary form together a saturated or partially unsaturated carbocycle or heterocycle with the heteroatoms O, N or S and 5 to 6 cyclic members; X is oxygen or sulphur and n equals 0 or 1. 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
4-Anilino-pyrimidine, Verfahren zu ihrer Herstellung, sie enthaltene Mittel und ihre 4-Anilino-pyrimidines, process for their preparation, agents and their
Verwendung als Fungizide. Use as a fungicide.
4-Anilino-pyrimidin-Derivate sind bekannt als wirksame Komponenten in fungiziden Mitteln4-anilino-pyrimidine derivatives are known to be effective components in fungicidal compositions
(vergl. z.B. JP 01/093575, JP 63/238068, DE 3644799, EP 248 349, DE 36 18353,(see e.g. JP 01/093575, JP 63/238068, DE 3644799, EP 248 349, DE 36 18353,
JP 58/198472; J. Environ. Sei. Health, Part B, B 18(4-5), (1983), S. 599-610; DE 3205 638,JP 58/198472; J. Environ. Be. Health, Part B, B 18 (4-5), (1983) pp 599-610; DE 3205 638,
JP 54/147921, Indian. J. Chem., SecL B, 16B(10), (1978), S.932-3; DE 2654090, JP 54/147921, Indian. J. Chem., SecL B, 16B (10), (1978), p.932-3; DE 2654090,
GB 1 394 817; Boll. Chim. Farm., 105(9), (1966), S. 660-5).  GB 1,394,817; Boll. Chim. Farm., 105 (9), (1966), pp. 660-5).
Es gibt allerdings nur sehr wenige Hinweise auf Verbindungen, die in der 2-Position des Pyrimidins Reste mit Dreifachbindungen tragen, beispielsweise ist ein However, there is very little evidence of compounds that have residues with triple bonds in the 2-position of the pyrimidine, for example, is
2.3-Dimethylphenyl-4-aminopyrimidin beschrieben (US 3,974,162). 2,3-Dimethylphenyl-4-aminopyrimidine described (US 3,974,162).
Außerdem ist die mikrobiocide Wirkung von Nitrophenyl-Derivaten (EP 139 613, GB 2 137In addition, the microbiocidal action of nitrophenyl derivatives (EP 139 613, GB 2 137
991) bekannt. 991).
Die Wirkung dieser Derivate ist jedoch - insbesondere bei niedrigen Aufwandmengen - nicht immer befriedigend, häufig ist auch das Artenspektnim nicht ausreichend. Außerdem ist eine Schädigung der Nutzpflanzen durch diese Derivate möglich. However, the effect of these derivatives is not always satisfactory, especially at low application rates, and the species spectrum is often also insufficient. In addition, these derivatives can damage crops.
Es wurden neue 4-Anilino-pyrimidin-Derivate gefunden, die vorteilhafte Wirkungen bei der Bekämpfung eines breiten Spektrums phytopatogener Pilze, insbesondere bei niedrigen Dosierungen, aufweisen und keine Schädigung von Nutzpflanzen verursachen. New 4-anilino-pyrimidine derivatives have been found which have advantageous effects in combating a broad spectrum of phytopatogenic fungi, in particular at low doses, and do not cause damage to useful plants.
Gegenstand der vorliegenden Erfindung sind daher Verbindungen der Formel I, The present invention therefore relates to compounds of the formula I
Figure imgf000004_0001
Figure imgf000004_0001
worin wherein
R1, R2 = unabhängig voneinander Wasserstoff, (C1-C9)Alkyl, Cyano-(C1-C4)alkyl, R 1 , R 2 = 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)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 substituierter 5- oder 6-gliedriger Heteroaromat, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenoxy-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylmercapto-(C1-C4)alkyl, 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 5- or 6-membered heteroaromatic, optionally substituted Phenyl, optionally substituted phenoxy, optionally substituted phenyl- (C 1 -C 4 ) alkyl, optionally substituted phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenylmercapto- (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 (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)Alkyl, (C1-C4)Alkoxy, (C1-C4) Alkylthio, (C1-C4)Haloalkyl , (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 substituen sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann, R1 und R2 gegebenenfalls zusammen einen gesättigten oder teilweise ungesättigten (C 1 -C 4 ) can be haloalkoxy or simply substituted by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms, R 1 and R 2 optionally together a saturated or partially unsaturated
Carbocyclus oder Heterocyclus mit den Heteroatomen O, N, S, Si oder P mit 4 bis 10 Ringgliedem,  Carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members,
R3 = 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 3 = 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)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)Alkylcaιbonyl, (C 1 -C 4 ) dialkylaminocarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylcabonyl,
(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 substituierter 5- oder 6-gliedriger Heteroaromat, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes (C 1 -C 4 ) alkylaminocarbonyl, (C 1 -C 4 ) haloalkylaminocarbonyl, optionally substituted 5- or 6-membered heteroaromatic, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted
Phenyl-(C1-C4)-alkyl, gegebenenfalls substituiertes Phenoxy-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylmercapto-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylketo-(C1-C4)alkyl, gegebenenfalls substituiertes Phenyl- (C 1 -C 4 ) alkyl, optionally substituted phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenylmercapto- (C 1 -C 4 ) alkyl, optionally substituted phenylketo- (C 1 -C 4 ) alkyl , optionally substituted
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 (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)Alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl, (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 Niuo oder Cyano substituen sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann, (C 1 -C 4 ) can be haloalkoxy or simply substituted by niuo or cyano, and can mean halo in the substituents substituted one or more times by halogen atoms,
R4, R5, R6 = 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)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, R 4 , R 5 , R 6 = 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- (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)alk ylt hio-(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 ) alk ylt hio- (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)Dialk ylamin o-(C1-C4)alkyl, (C3-C9)Cycloalklamino-(C1-C4)alkyl, (C 1 -C 4 ) dialkylamine o- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) cycloalklamino- (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, (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,
(C1-C4)Alkylaminocarbonyl-(C1-C4)alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl,
(C1-C4)Dialkylaminoca rbonyl-(C1-C4)alkyl, (C1-C4)Alkylcarbonyl, (C 1 -C 4 ) dialkylaminocarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylcarbonyl,
(C1-C4)Haloalkylcaιbonyl, (C1-C4)Alkoxycarbonyl, (C 1 -C 4 ) haloalkylcaιbonyl, (C 1 -C 4 ) alkoxycarbonyl,
(C1-C4)Alkoxycarbonyl-(C1-C4)alkyl, (C1-C4)Alkylamin ocarbonyl-(C1-C4)alkyl, (C1-C4)Haloalkoxycarbonyl, (C1-C4)Alkylthiocarbonyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkoxycarbonyl, (C 1 - C 4 ) alkylthiocarbonyl,
(C1-C4)Haloalkylthiocarbonyl, Aminocarbonyl, (C1-C4)Alkylaminocarbonyl, (C1-C4)Haloalk ylaminocarbonyl, gegebenenfalls substituierter 5- oder 6-gliedriger Heteroaromat, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenoxy-(C1-C4)alkyl, gegebenenfalls substituiertes (C 1 -C 4 ) haloalkylthiocarbonyl, aminocarbonyl, (C 1 -C 4 ) alkylaminocarbonyl, (C 1 -C 4 ) haloalkylaminocarbonyl, optionally substituted 5- or 6-membered heteroaromatic, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted Phenyl- (C 1 -C 4 ) alkyl, optionally substituted Phenoxy- (C 1 -C 4 ) alkyl, optionally substituted
Phenylmercapto-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylketo-(C1-C4)alkyl, gegebenenfalls substituiertes Phenyloxycarbonyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylamino-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylmercapto- (C 1 -C 4 ) alkyl, 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)Alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl , (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, (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,
R4,R5 und/oder R6 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 4 , R 5 and / or R 6 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,
R7 = Wasserstoff, Formyl, (C1-C4)Alkyl, (C1-C4)Alkoxy, Halo-(C1-C4)alkoxy, R 7 = hydrogen, formyl, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, halo (C 1 -C 4 ) alkoxy,
Amino(C1-C4)alkoxy, (C1-C4)Alkylamino(C1-C4)alkoxy, Amino (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylamino (C 1 -C 4 ) alkoxy,
(C1-C4)Alkoxy(C1-C4)alkoxy, Amino, (C1-C4)Alkylamino, (C1-C4)Dialkylamino, Hydroxy-(C1-C4)alkyl, Dihydroxy-(C1-C4)alkyl, Cyano-(C1-C4)alkyl, (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkoxy, amino, (C 1 -C 4 ) alkylamino, (C 1 -C 4 ) dialkylamino, Hydroxy- (C 1 -C 4 ) alkyl, dihydroxy- (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) 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, Halo-(C1-C4)alkylthio-(C1-C4)alkyl, (C1-C4)Alkylthio-(C1-C4)alkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, 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- (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,
(C1-C4)Alkylam ino-(C1-C4)al kyl, (C1-C4)Dialkylamino-(C1-C4)alkyl, (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) Cyclαalkyl, (C 3 -C 9 ) cycloalkylamino- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) cyclαalkyl,
(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)Alkoxyc arbonyl-(C1-C4)alkyl, (C1-C4)Alkylaminocarbonyl-(C1-C4)alkyl, (C1-C4)Dialkylaminocarbonyl-(C1-C4)alkyl, (C1-C4)Alkylcarbonyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl, (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, (C 1 -C 4 ) alkylaminocarbonyl, (C 1 -C 4 ) haloalkylaminocarbonyl,
(C1-C4)Alkoxycarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenoxy-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylmercapto-(C1-C4)alkyl, gegebenenfalls substituiertes (C 1 -C 4 ) alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenyl- (C 1 -C 4 ) alkyl, optionally substituted phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenylmercapto- (C 1 -C 4 ) alkyl, optionally substituted
Phenylketo-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylketo (C 1 -C 4 ) alkyl, optionally substituted
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 substituen 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 substituted simply by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms,
R7 und R4 und/oder R5 gegebenenfalls zusammen einen gesättigten, oder teilweise R 7 and R 4 and / or R 5 optionally together a saturated or partially
ungesättigten Carbocyclus oder Heterocyclus mit den Heteroatomen O, N, S, Si oder P mit 4 bis 10 Ringgliedem,  unsaturated carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members,
R8, R9 = unabhängig voneinander Wasserstoff, Halogen, (C1-C4)Alkyl, R 8 , R 9 = independently of one another hydrogen, halogen, (C 1 -C 4 ) alkyl,
Hydroxy-(C1-C4)alkyl, Dihydroxy-( C1-C4)alkyl, Cyano-(C1-C4)alkyl, Hydroxy- (C 1 -C 4 ) alkyl, dihydroxy- (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl,
Halo-(C1-C4)alkyl, (C1-C4)Alkoxy, (C1-C4)Alkoxy-(C1-C4)alkyl, Halo (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (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)Alkylaniino-(C1-C4)alkyl, (C 3 -C 9 ) cycloalkylamino-, (C 1 -C 4 ) alkylaniino- (C 1 -C 4 ) alkyl,
(C1-C4)Dia lkylamino-(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)eycloalkyl, (C1-C9)Cycloalkyl-(C1 -C4)alkyl, (C 3 -C 9 ) cycloalkyl, (C 1 -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)Dialkylammocarbonyl-(C1-C4)alkyl, (C1-C4)Alkylcarbonyl, (C 1 -C 4 ) dialkylammocarbonyl- (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 Phenylmercapto-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylketo-(C1-C4)alkyl, gegebenenfalls substituiertes Phenyloxycarbonyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenylmercapto- (C 1 -C 4 ) alkyl, optionally substituted phenylketo- (C 1 -C 4 ) alkyl, optionally substituted 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,
R8 und R9 gegebenenfalls zusammen einen gesättigten, teilweise ungesättigten oder R 8 and R 9 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 = Sauerstoff oder Schwefel und n = eine Zahl von 0 bis 8 bedeuten, sowie deren Säureadditionssalze. X = oxygen or sulfur and n = a number from 0 to 8, and their acid addition salts.
In Formel I bedeuten In formula I mean
R1, R2 bevorzugt unabhängig voneinander Wasserstoff, (C1-C9)Alkyl, im Phenylteil durch Halogen, (C1-C4)Alkyl oder (C1-C4)Alkoxy gegebenenfalls substituiertes Phenyl, insbesondere Wasserstoff oder (C1-C4)Alkyl, besonders bevorzugt Wasserstoff, R1 und R2 können zusammen einen gesättigten oder teilweise ungesättigten Carbocyclus oder Heterocyclus mit den Heteroatomen O, N oder S mit 4 bis 10 Ringgliedern, insbesondere mit 5 oder 6 Ringgliedern bilden, und R 1 , R 2 preferably independently of one another are hydrogen, (C 1 -C 9 ) alkyl, in the phenyl part by halogen, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy optionally substituted phenyl, in particular hydrogen or (C 1 -C 4 ) alkyl, particularly preferably hydrogen, R 1 and R 2 together can form a saturated or partially unsaturated carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10 ring members, in particular with 5 or 6 ring members, and
R3 bedeutet bevorzugt Wasserstoff, Halogen, (C1-C4)Alkyl, Hydroxy-(C1-C4)alkyl, R 3 preferably denotes hydrogen, halogen, (C 1 -C 4 ) alkyl, hydroxy- (C 1 -C 4 ) alkyl,
Dihydroxy-(C1-C4)alkyl, (C1-C4)Alkylthio, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C1-C4)Alkylamino-(C1-C4)alkyl, (C1-C4)Dialkylamino-(C1-C4)alkyl, Dihydroxy- (C 1 -C 4 ) alkyl, (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)Cycloalkylaιnino-(C1-C4)alk yl, (C3-C9)Cycloalkyl, (C 3 -C 9 ) Cycloalkylaιnino- (C 1 -C 4 ) alk yl, (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 Phenoxy, gegebenenfalls substituierter 5- bis 6-gliedriger Heteroaromat, beispielsweise Pyridm, Thiophen, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil (Heteroaromat) bis zu dreifach durch Halogen, Ester, (C1-C4)Alkyl, (C!-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl , (C1-C4)Haloalkoxy oder einfach durch Nitro oder Cyano substituert sein kann. (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, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted 5- to 6-membered heteroaromatic, for example pyridm, thiophene, where optionally substituted is to be understood to mean that the phenyl part (heteroaromatic) is substituted up to three times by halogen, ester , (C 1 -C 4 ) alkyl, (C ! -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy or simply by nitro or Cyano can be substituted.
R3 bedeutet insbesondere Wasserstoff oder Halogen, besonders bevorzugt Wasserstoff. R 3 is in particular hydrogen or halogen, particularly preferably hydrogen.
R4, R5, R6 bedeuten bevorzugt unabhängig voneinander Wasserstoff, Halogen, Hydroxy,R 4 , R 5 , R 6 are preferably independently of one another hydrogen, halogen, hydroxyl,
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)a lkyl, (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, 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) a lkyl, (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)Alkylamino-(C1-C4)alkyl, (C1-C4)Dialkylamino-(C1-C4)alkyl, (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)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)Alkylaminocarbonyl, (C 1 -C 4 ) alkoxycarbonyl, aminocarbonyl, (C 1 -C 4 ) alkylaminocarbonyl,
gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, 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, (C1-C4)Haloalkyl, (C1-C4)Haloalkoxy oder einfach durch Nitro oder Cyano substituiert sein kann. optionally substituted phenyl, optionally substituted phenoxy, 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, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) Haloalkoxy or simply substituted by nitro or cyano.
R4,R5 und/oder R6 können zusammen einen gesättigten, teilweise ungesättigten oder R 4 , R 5 and / or R 6 together can be a saturated, partially unsaturated or
aromatischen Carbocyclus oder Heterocyclus mit den Heteroatomen O, N, oder S mit 4 bis 10 Ringgliedern bilden,  form an aromatic carbocycle or heterocycle with the heteroatoms O, N, or S with 4 to 10 ring members,
R4,R5,R6 bedeuten insbesondere unabhängig voneinander Wasserstoff, Halogen, R 4 , R 5 , R 6 are in particular independently of one another hydrogen, halogen,
(C1-C4)Alkyl, (C1-C4)Alkoxy oder im Phenylteil durch Halogen, (C1-C4)Alkyl oder (C1-C4)Alkoxy gegebenenfalls substituiertes Phenoxy, besonders bevorzugt (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy or phenoxy optionally substituted by halogen, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy, particularly preferred
Wasserstoff, Cl, F oder OCH3, Hydrogen, Cl, F or OCH 3 ,
R7 bedeutet bevorzugt Wasserstoff, (C1-C4)Alkyl, Cyano-(C1-C4)alkyl, (C1-C4)Alkoxy, Halo-(C1-C4)alkoxy, Amino(C1-C4)alkoxy, (C1-C4)Alkylamino(C1-C4)alkoxy, (C1-C4)Alkoxy(C1-C4)alkoxy, Amino, (C1-C4)Alkylamino, R 7 preferably denotes hydrogen, (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, halo- (C 1 -C 4 ) alkoxy, amino (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylamino (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkoxy, amino, (C 1 -C 4 ) alkylamino ,
(C1-C4)Alkoxy-(C1-C4)alkyl, (C1-C4)Alkylthio, Perhalo-(C1-C4 )alkylthio, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio, perhalo (C 1 -C 4 ) alkylthio,
(C1-C4)Alkylamino-(C1-C4)alkyl, (C1-C4)Di alkylamino-(C1-C4)alkyl, (C 1 -C 4 ) alkylamino- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) di alkylamino- (C 1 -C 4 ) alkyl,
(C3-C9)Cycloalkylamino-(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)Alkoxycarbonyl-(C1-C4)alkyl, (C1-C4)Alkylcarbonyl, (C 3 -C 9 ) cycloalkylamino- (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, (C 1 -C 4 ) alkoxycarbonyl- (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, 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, (C 1 -C 4 ) alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, 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. (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy or can simply be substituted by nitro or cyano.
R7 und R4 und/oder R5 können zusammen einen gesättigten oder teilweise ungesättigten Carbocyclus oder Heterocyclus mit den Heteroatomen O, N oder S mit 4 bis 10 Ringgliedern bilden. R 7 and R 4 and / or R 5 together can form a saturated or partially unsaturated carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10 ring members.
R7 bedeutet insbesondere Wasserstoff oder (C1-C4)Alkyl, besonders bevorzugt Wasserstoff. R 7 in particular denotes hydrogen or (C 1 -C 4 ) alkyl, particularly preferably hydrogen.
R8, R9 sind bevorzugt unabhängig voneinander Wasserstoff, Halogen, (C1-C4)Alkyl, R 8 , R 9 are preferably independently of one another hydrogen, halogen, (C 1 -C 4 ) alkyl,
Hydroxy-( C1-C4)alkyl, Perhalo-(C1-C4)alkyl, (C1-C4)Alkoxy, Hydroxy- (C 1 -C 4 ) alkyl, perhalo (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy,
(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, (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,
(C1-C4)Alkylamino, (C1-C4)Dialkylamino, (C3-C9)Cycloalkylamino, (C 1 -C 4 ) alkylamino, (C 1 -C 4 ) dialkylamino, (C 3 -C 9 ) cycloalkylamino,
(C1-C4)Alkylamino-(C1-C4)alkyl, (CI-C4)Dialkylamino-(C1-C4)alkyl, (C 1 -C 4 ) alkylamino- (C 1 -C 4 ) alkyl, (C I -C 4 ) dialkylamino- (C 1 -C 4 ) alkyl,
(C3-C9)Cycloalkylamino-(C1-C4)aikyl, (C3-C9)Cycloalkyl, (C 3 -C 9 ) cycloalkylamino- (C 1 -C 4 ) aikyl, (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
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. (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.
R8 bedeutet insbesondere Wasserstoff, (C1-C4)Alkyl, (C1-C4)Alkoxy, Phenyl-(C1-C4)alkoxy oder Halogen, besonders bevorzugt Wasserstoff, Cl oder OCH3. R 8 in particular denotes hydrogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, phenyl- (C 1 -C 4 ) alkoxy or halogen, particularly preferably hydrogen, Cl or OCH 3 .
R8 und R9 können zusammen einen gesättigten, teilweise ungesättigten oder aromatischen Carbocyclus oder Heterocyclus mit den Heteroatomen O, N oder S mit 4 bis 10 Ringgliedem bilden. R 8 and R 9 together can form a saturated, partially unsaturated or aromatic carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10 ring members.
R9 bedeutet insbesondere Wasserstoff, (C1-C4)Alkyl, Perhalo-(C1-C4)alkyl, R 9 in particular denotes hydrogen, (C 1 -C 4 ) alkyl, perhalo (C 1 -C 4 ) alkyl,
(C1-C4)Alkoxy-(C1-C4)alkyl oder Phenyl-(C1-C4)alkyl, besonders bevorzugt (C 1 -C 4 ) Alkoxy- (C 1 -C 4 ) alkyl or phenyl- (C 1 -C 4 ) alkyl, particularly preferred
Wasserstoff oder CH3. Hydrogen or CH 3 .
X ist bevorzugt Sauerstoff oder Schwefel und n ist eine Zahl von 0 bis 4, insbesondere 0 oder 1, besonders bevorzugt 0. X is preferably oxygen or sulfur and n is a number from 0 to 4, in particular 0 or 1, particularly preferably 0.
Unter Halo ist in den einzelnen Substituenten ein- oder mehrfach durch Halogenatome substituiert zu verstehen. Halo in the individual substituents is to be understood as being 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 Abfiltrieren, 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, and also sulfonic acids such as p-toluenesulfonic acid or 1,5-naphthalenedisulfonic acid. The acid addition compounds of the formula I can be obtained in a simple manner by the customary salt formation methods, for example by dissolving a compound of the formula I in a suitable organic solvent and adding the acid, and can be isolated in a known manner, for example by filtration, and optionally by washing with an inert solvent organic solvents can be cleaned.
Die Pyrimidine der Formel I können nach verschiedenen mehrstufigen Verfahren hergestellt werden. The pyrimidines of the formula I can be prepared by various multistage processes.
Man erhält die erfmdungsgemäßen Verbindungen, indem man Verbindungen der Formel II The compounds according to the invention are obtained by using compounds of the formula II
SΛ S Λ
Figure imgf000012_0001
R
Figure imgf000012_0001
R
worin Hal = Cl oder Br und R12 = (C1-C4)Alkylthio, im Phenylteil durch Halogen, where Hal = Cl or Br and R 12 = (C 1 -C 4 ) alkylthio, in the phenyl part by halogen,
(C1-C4)Alkyl oder (C1-C4)Alkoxy gegebenenfalls substituiertes Phenyl(C1-C4)alkylthio oder den Rest III (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy optionally substituted phenyl (C 1 -C 4 ) alkylthio or the radical III
Figure imgf000012_0002
Figure imgf000012_0002
bedeuten, mit Verbindungen der Formel IV mean with compounds of formula IV
Figure imgf000012_0003
Figure imgf000012_0003
umsetzt und, falls R12 eine von der Formel III abweichende Bedeutung hat, anschließend die erhaltenen Verbindungen im Rest R12 oxidien und die entstandenen Oxidationsprodukte mit Verbindungen der Formel V implements and, if R 12 has a meaning deviating from the formula III, then the Compounds obtained in the radical R 12 oxidize and the resulting oxidation products with compounds of formula V.
Figure imgf000013_0001
Figure imgf000013_0001
zu den Endprodukten der Formel I mit R12 -= Rest der Formel III umsetzt sowie to the end products of formula I with R 12 - = radical of formula III and
gegebenenfalls, wenn R3 = H, den Wasserstoff gegen Halogen in bekannter Weise austauscht. optionally, when R 3 = H, the hydrogen is replaced by halogen in a known manner.
Die Ausgangsstoffe der Formel I erhält man nach einer Anzahl literaturbekannter Verfahren. The starting materials of formula I are obtained by a number of processes known from the literature.
Durch Kondensation geeigneter 3-Ketocarbonsäureester mit Thiohamstoff oder S-alkylierten Thiohamstoffen, 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 (Wasser, niedere Alkohole), bei Temperaturen von 0°C bis 160ºC, 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 thiourea or S-alkylated thioureas, where they can be used in pure form or in situ, released from their salts, without solvents or in a suitable aprotic or protic solvent (water, lower alcohols) 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 carbonates (Na 2 CO 3 or K 2 CO 3 ) or
Alkalialkoholate (NaOMe oder NaOEt), zu entsprechenden 4-Pyrimidinonen.  Alkaline alcoholates (NaOMe or NaOEt), to corresponding 4-pyrimidinones.
Figure imgf000013_0002
Figure imgf000013_0002
R10 steht in diesem und in den folgenden Formelschemata für S, S-(C1-C4)AIkyl, im R 10 in this and in the following formula schemes stands for S, S- (C 1 -C 4 ) alkyl, im
Phenylteil durch Halogen, (C1-C4)Alkyl oder (C1-C4)Alkoxy gegebenenfalls substituiertes S-(C1-C4)Alkyl-phenyl. Phenyl part with halogen, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy optionally substituted S- (C 1 -C 4 ) alkylphenyl.
Die Verfahren sind in der Literatur bekannt, die Edukte sind käuflich oder können nach literaturbekannten Verfahren (z.B. Beilstein 3./4. Ergänzungswerk, Band 25, S.50, S.472) hergestellt werden. Für die Herstellung der Pyrimidine der Formel II mit R8 = Halogen ist die Umsetzung geeigneter 4-Pyrimidinone mit elementaren Halogenen in einem aprotischen oder protischcr. Lösungsmittel wie Essigsäure bevorzugt. (Beilstein, 3./4. Ergänzungswerk, Band 25, S. 56). The processes are known in the literature, the starting materials are commercially available or can be prepared by processes known from the literature (for example Beilstein 3rd / 4th Supplement, Volume 25, p.50, p.472). For the preparation of the pyrimidines of the formula II with R 8 = halogen, the reaction of suitable 4-pyrimidinones with elemental halogens in an aprotic or protic. Preferred solvents such as acetic acid. (Beilstein, 3rd / 4th supplement, volume 25, p. 56).
Figure imgf000014_0001
Figure imgf000014_0001
Hai  Shark
R11 steht in diesem und in den folgenden Foimelschemata für (C1-C4)Alkyl oder im In this and the following Foimel schemes, R 11 represents (C 1 -C 4 ) alkyl or im
Phenylteil durch Halogen, (C1-C4)Alkyl, (C1-C4) Alkoxy oder im Phenylteil durch Halogen, (C1-C4)Alkyl oder (C1-C4)Alkoxy gegebenenfalls substituiertes (C1-C4)Alkyl-phenyl oder Phenyl part by halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy or in the phenyl part by halogen, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy optionally substituted (C 1 - C 4 ) alkyl-phenyl or
Figure imgf000014_0002
Figure imgf000014_0002
Verbindungen der Formel II mit R9 = Wasserstoff können in Anlehnung an entsprechende Literaturvorschriften (Beilstein, 3./4. Ergänzungswerk, Band 25, S. 279) 2-stufig in einem Einiopfverfahren hergestellt werden. Zunächst werden in einem inerten Lösungsmittel wie Toluol, THF, Dioxan oder Diethylether entsprechende Carbonsäurederivate mit einer geeigneten Base, zumeist einem Alkalihydrid (NaH) oder Alkalialkoholat (NaOMe) anionisiert und dann mit einem Ameisensäureester formyliert. Compounds of the formula II with R 9 = hydrogen can be prepared in two stages in a single-step process based on corresponding literature regulations (Beilstein, 3rd / 4th Supplement, Volume 25, p. 279). In an inert solvent such as toluene, THF, dioxane or diethyl ether, corresponding carboxylic acid derivatives are first anionized with a suitable base, usually an alkali metal hydride (NaH) or alkali metal alcoholate (NaOMe) and then formylated with a formic acid ester.
Die anschließende Kondensation kann mit Thiohamstoff oder S-alkylierten Thioharnstoffen erfolgen, wobei diese in reiner Form oder in situ, mittels Basen (Alkoholate wie NaOMe) aus ihren Salzen freigesetzt, eingesetzt werden können. Als besonders für die Kondensation geeignet haben sich protische Lösungsmittel, insbesondere niedere Alkohole, erwiesen. The subsequent condensation can take place with thiourea or S-alkylated thioureas, which can be used in pure form or in situ, using bases (alcoholates such as NaOMe) released from their salts. Protic solvents, in particular lower alcohols, have proven particularly suitable for the condensation.
Figure imgf000015_0001
Figure imgf000015_0001
Die Modifizierung bekannter Pyrimidinone oder Mercaptopyrimidinone erfolgt mit einem Alkylierungsmittel, wie Alkylhalogenide (z.B. Methyljodid) oder Alkylsäureester (z.B. Dimethylsulfat, Phosphorsäuretrimethylester), insbesondere Propinylhalogenide, unter Verwendung einer Base wie NaOH, NaH oder Triethylamin in einem geeigneten protischen oder aprotischen Lösungsmittel (DMF, Acetonitril, Wasser) bei Temperaturen von 0°C bis 260°C, bevorzugt im Temperaturbereich von 50°C bis zu der Siedetemperatur des  The known pyrimidinones or mercaptopyrimidinones are modified with an alkylating agent, such as alkyl halides (for example methyl iodide) or alkyl acid esters (for example dimethyl sulfate, trimethyl phosphoric acid), in particular propynyl halides, using a base such as NaOH, NaH or triethylamine in a suitable protic or aprotic solvent (DMF, acetonitrile , Water) at temperatures from 0 ° C to 260 ° C, preferably in the temperature range from 50 ° C to the boiling point of
Lösungsmittels.  Solvent.
Figure imgf000015_0002
Figure imgf000015_0002
Die so erhaltenen 4-Pyrimidinone können mit überschüssigem POCl3 (POBr3) ohne Lösungsmittel, in einem gegen POCl3 (POBr3) inerten Lösungsmittel oder in einem basischen Lösungsmittel wie DMF ohne oder mit einem Säurefanger, wie The 4-pyrimidinones thus obtained can be treated with excess POCl 3 (POBr 3 ) without 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, vorzugsweise 0,02 Äquivalenten, bei Temperaturen von 50°C bis 110°C, vorzugsweise bei der Siedetemperatur des POCl3 (POBr3) in die entsprechenden 4-Halogenpyrimidine überführt werden (vergl. Beilstein, Hauptwerk, Band 25, S. 372, Beilstein, 3./4. Ergänzungswerk, Band 23, S. 2471). N, N-dimethylaniline in 0.001 to 2 molar equivalents, preferably 0.02 equivalents, at temperatures from 50 ° C. to 110 ° C., preferably at the boiling point of POCl 3 (POBr 3 ), are converted into the corresponding 4-halopyrimidines (cf. Beilstein, Hauptwerk, volume 25, p. 372, Beilstein, 3rd / 4th supplement, volume 23, p. 2471).
Figure imgf000015_0003
Figure imgf000015_0003
ie Aniline der Formel IV sind größtenteils bekannte Verbindungen bzw. können in analoger, dem Fachmann geläufiger Weise hergestellt werden. he anilines of formula IV are mostly known compounds or can in can be produced in a manner analogous to those skilled in the art.
Die Umsetzung von II mit IV erfolgt in Abhängigkeit von der Reaktivität der Derivate in einem inerten Lösungsmittel, (Wasser/Aceton, Toluol, THF) bei Temperaturen von 0°C bis 150°C, vorzugsweise von 50°C bis 100°C. Der Austausch kann durch katalytischen bis äquimolaren Basenzusatz begünstigt werden, im allgemeinen hat es sich jedoch als vorteilhaft erwiesen, die Reaktion mit Säure, insbesondere mit Salzsäure, zu katalysieren. The reaction of II with IV takes place depending on the reactivity of the derivatives in an inert solvent (water / acetone, toluene, THF) at temperatures from 0 ° C. to 150 ° C., preferably from 50 ° C. to 100 ° C. The exchange can be promoted by adding catalytic to equimolar bases, but in general it has proven to be advantageous to catalyze the reaction with acid, in particular with hydrochloric acid.
Ist R12 ein Rest mit einer Dreifachbindung, so findet die erwartete Addition des Anilin an die Dreifachbindung nicht statt. If R 12 is a radical with a triple bond, the expected addition of the aniline to the triple bond does not take place.
Sofern die zur Synthese der erfindungsgemäßen Verbindungen benötigten, den Rest -CR 1R2-(CH2)n-C≡CR3 enthaltenden Pyrimidin-Derivate der Formel II nicht zur Verfügung stehen, kann man diesen Rest nachträglich in die zunächst erhaltenen Umsetzungsprodukte von II (mit R12 = Rest der Formel III) und IV einführen. Hierzu kann bei entsprechenden 2-Alkylmercaptopyrimidinen die schwefeltragende Gruppe oxidiert werden. Die Oxidation kann nach üblichen Verfahren mit geeigneten Oxidationsmitteln, wie Peroxide (z.B. H2O2), Permanganat, Perbenzoesäuren, oder mit einem Gemisch aus Kaliumperoxomonosulfat, 2KHSO5, KHSO4, und K2SO4 in einem Lösungsmittel oder Lösungsmittelgemisch (z.B. Wasser, Essigsäure, Methanol) durchgeführt werden (vergl. Comprehensive Heteroeyclic Chemistry, A.R. Katritzky, C.W. Rees, Pergamon Press, Oxford, New York, 1984, Vol.3, S. 96; DJ. Brown, B.T. England; J.Chem.Soc.(C), (1971), S. 256). Die Oxidation kann auch mittels Katalysatoren gestartet oder beschleunigt werden. If the pyrimidine derivatives of the formula II required for the synthesis of the compounds according to the invention and containing the radical -CR 1 R 2 - (CH 2 ) n -C≡CR 3 are not available, this radical can subsequently be converted into the reaction products of Introduce II (with R 12 = radical of formula III) and IV. For this purpose, the sulfur-bearing group can be oxidized with corresponding 2-alkylmercaptopyrimidines. The oxidation can be carried out by customary methods using suitable oxidizing agents, such as peroxides (e.g. H 2 O 2 ), permanganate, perbenzoic acids, or using a mixture of potassium peroxomonosulfate, 2KHSO 5 , KHSO 4 , and K 2 SO 4 in a solvent or solvent mixture (e.g. water , Acetic acid, methanol) (see Comprehensive Heteroeyclic Chemistry, AR Katritzky, CW Rees, Pergamon Press, Oxford, New York, 1984, Vol.3, p. 96; DJ. Brown, BT England; J.Chem.Soc . (C), (1971), p. 256). The oxidation can also be started or accelerated using catalysts.
Figure imgf000016_0001
Figure imgf000016_0001
In diesem und den weiteren Formelschemata steht R13 für Halogen, insbesondere für Chlor, **>* R4 In this and the other formula schemes, R 13 represents halogen, in particular chlorine, * *> * R 4
oder für
Figure imgf000017_0001
or for
Figure imgf000017_0001
Im nächsten Schritt kann der Austausch der Sulfonylgruppe gegen Alkohole erfolgen. In Abhängigkeit von der Reaktivität der Derivate kann man in einem inerten Lösungsmittel (Toluol, THF) bei 0°C bis 150 °C, im allgemeinen bei 25°C bis 50ºC arbeiten, wobei die Sulfonylgruppe gegen Alkolate der entsprechenden Alkinole, hergestellt aus dem In the next step, the sulfonyl group can be exchanged for alcohols. Depending on the reactivity of the derivatives, one can work in an inert solvent (toluene, THF) at 0 ° C to 150 ° C, generally at 25 ° C to 50 ° C, the sulfonyl group against alkolates of the corresponding alkynols, prepared from the
entsprechenden Alkinol und einer Base, im allgemeinen NaH, austauschen. Hierbei sind zur Vermeidung von Nebenreaktionen, insbesondere für Verbindungen der Formel I mit R13= Halogen, möglichst niedrige Temperaturen anzustreben; auch sollte ein Überschuß an Alkoholat vermieden werden. Der Austausch von Sulfonylmethylgruppen bei Pyrimidinen isi bekannt (Vergl. Comprehensive Heteroeyclic Chemistry, A.R. Katritzky, C.W. Rees, Pergamon Press, Oxford, New York, 1984, Vol.3, S. 97), die Anwendung der Reaktion auf hier beschriebene Systeme dagegen ist neu. exchange the corresponding alkinol and a base, generally NaH. In order to avoid side reactions, in particular for compounds of the formula I where R 13 = halogen, temperatures should be as low as possible; an excess of alcoholate should also be avoided. The exchange of sulfonylmethyl groups in pyrimidines is known (see Comprehensive Heteroeyclic Chemistry, AR Katritzky, CW Rees, Pergamon Press, Oxford, New York, 1984, Vol.3, p. 97), but the application of the reaction to the systems described here is against it New.
Figure imgf000018_0001
Figure imgf000018_0001
Wie bereits beschrieben, kann für den Fall, daß R13 = Halogen ist, das Halogen anschließend gegen Anilin ausgetauscht werden. As already described, in the event that R 13 = halogen, the halogen can then be exchanged for aniline.
Als Beispiel für eine weitere Modifizierung von Edukten zur Herstellung von Verbindungen der Formel I sei die Halogenierung der Alkinylfunktion genannt In Abwandlung literaturbekannter Methoden ("Alkine, Di- und Polyine, Allene, Kumulene", Methoden der organischen Chemie (Houben/Weyl) Thieme-Verlag, 1977, Band 5,2a, Stuttgart, S.600 ff.) kann in einem geeigneten aprotischen Lösungsmittel, wie THF oder Dioxan, mit Basen, wie n-Butyllithium, das terminale Proton des Ethinyl-Derivates abstrahiert und anschließend ein Halogen, beispielsweise Jod oder Brom, eingeführt werden. The halogenation of the alkynyl function may be mentioned as an example of a further modification of starting materials for the preparation of compounds of the formula I. In modification of methods known from the literature ("alkynes, di- and polyynes, allenes, cumulenes", methods of organic chemistry (Houben / Weyl) Thieme- Verlag, 1977, volume 5.2a, Stuttgart, pp. 600 ff.) Can abstract the terminal proton of the ethynyl derivative and then a halogen in a suitable aprotic solvent, such as THF or dioxane, with bases, such as n-butyllithium, for example iodine or bromine.
Figure imgf000018_0002
In diesem Beispiel steht dann R3 für X, stellvertretend für Halogen, insbesondere für Brom oder Jod.
Figure imgf000018_0002
In this example, R 3 represents X, which represents halogen, in particular bromine or iodine.
Die erfϊndungsgemäßen 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 püzliche 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 Stecküngen zum Schutz vor Pilzinfektionen sowie im Erdboden auftretende pathogene Pilze. Das Wirkungsspektrum der beanspruchten Verbindungen erfaßt eine Vielzahl verschiedener wirtschaftlich bedeutender, phytopathogener Pilze, wie Altemaria mali, Botrytis cinerea, Benzimidazol- und/oder Dicarboximid- sensible und resistente Stämme, Sclerotinia sclerotiorum sowie weitere Grauschimmelarten, Cercospora beticola, Ceratobasidium cerealis, Erysiphe graminis, Erysiphe graminis hordei, Erysiphe 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. It is also possible to successfully combat curative pathogens that have already penetrated the plant tissue. 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 dressing agents for the treatment of seeds and plantings for protection against fungal infections and pathogenic fungi occurring in the soil. The spectrum of activity of the claimed compounds encompasses a large number of different economically important phytopathogenic fungi, such as Altemaria mali, Botrytis cinerea, benzimidazole- and / or dicarboximide-sensitive and resistant strains, Sclerotinia sclerotiorum as well as other gray mold species, Cercospora beticola, Ceratheisisipium, Ceratheisisisipa, Ceratheisisisipa, Ceratheisisipasola, Ceratheisisipium, Ceratheisisipasola, Ceratheisisisipa, Ceratheisisipa, Ceratheisisipa graminis hordei, Erysiphe
chichoracearum sowie andere Echte Mehltauarten, Fusarium culmorum und andere  chichoracearum and other powdery mildew species, Fusarium culmorum and others
Fusariumarten, Moniliniaarten, Leptosphaeria nodorum sowie andere Septoriaaiten und Blattfleckenverursachende Arten, Pellicularia sasakii, Pyricularia oryzae und andere Reispilzsarten, Phytophthora infestans, Phytophtora capsici und verschiedene andere Kraut- und Knollenfaulepilze, Plasmopara viticola, Pseudopemospora cubensis und weitere Peronospora oder Falsche Mehltauarten, Pseudocercosporella herpotrichoides und 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 insbesonders gegen BCM-resistente Fusarium species, Monilinia species, Leptosphaeria nodorum as well as other Septoriaaiten and leaf spot-causing species, Pellicularia sasakii, Pyricularia oryzae and other rice mushroom types, Phytophthora infestans, Phytophtora capsici and various other herb and tuber rotten fungus and pollen moths, Popularoporasporonuspora, Pompopoparodispora, False, Pommoporospora, and others various other types of fungi causing eye breakage or stalks, Puccinia recondita and various other rust fungi, Pyrenophora teres and other woodturning species, Ustilago species, Venturia inaequalis and scab species, but the activity against Ascomycetes and Deuteromycetes and especially against BCM-resistant
Pseudocercosporella heφotrichoides-Stämme hervorzuheben ist. Pseudocercosporella heφotrichoides 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 include the compounds of the formula I contain suitable formulation aids. 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 given 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. Granules (WG), ULV formulations, microcapsules, waxes or baits.
Diese einzelnen Formulierungstypen sind bekannt und werden beispielsweise beschrieben in: Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hauser 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. These individual types of formulation are known and are described, for example, in: Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hauser Verlag Munich, 4th Edition 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 Carrier", 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 Carrier," 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. Aufl. 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, On the basis of these formulations, combinations with other pesticidally active substances, fertilizers and / or growth regulators can also be produced,
z. B. in Form einer Fertigformulierung oder als Tankmix. z. 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. ligmnsulfonsaures Natrium, Dispersants, e.g. B. ligmnsulfonic acid sodium,
2,2'-dinaphthyl-methan-6,6'-disulfonsaures Natrium, dibutylnaphthalin-sulfonsaures Natrium oder auch oleylmethyltaurinsaures Natrium enthalten. Emulgierbare Konzentrate werden durch Auflösen des Wirkstoffes in einem organischen Lösungsmittel, z. B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten oder Kohlenwasserstoffen unter Zusatz von einem oder mehreren Emulgatoren hergestellt. 2,2'-dinaphthyl-methane-6,6'-disulfonic acid sodium, dibutylnaphthalene sulfonic acid sodium or contain sodium oleylmethyl tauric acid. Emulsifiable concentrates are obtained by dissolving the active ingredient in an organic solvent, e.g. B. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers.
Als Emulgatoren können beispielsweise verwendet werden: The following can be used as emulsifiers:
Alkylarylsulfonsaure Calciumsalze wie Ca-dodecylbenzolsulfonat oder nichtionogene Emulgatoren wie Fettsäurepolyglykolester, Alkylarylpolyglykolether, Alkylarylsulfonic acid calcium salts such as Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers,
Fettalkoholpolyglykolether, Propylenoxid-Ethylenoxid-Sorbitanfettsäureester,  Fatty alcohol polyglycol ether, propylene oxide-ethylene oxide-sorbitan fatty acid ester,
Polyoxethylensorbitan-Fettsäureester oder Polyoxethylensorbitester.  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, Pyrophyllit oder Diatomeenerde. Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfahiges, 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, pyrophyllite 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 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. Active ingredient concentrates by means of adhesives, e.g. As polyvinyl alcohol, sodium polyacrylic acid or mineral oils, on the surface of carriers such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if appropriate in a mixture with fertilizers.
In Spritzpulvern beträgt die Wirkstoffkonzentration 10 bis 90 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei emulgierbaren Konzentrater, 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 substance concentration in wettable powders is 10 to 90% by weight, the rest 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 Konzentraten, Dispersionen und teilweise auch bei Mikrogranulaten mittels Wasser. optionally diluted in a conventional manner, e.g. B. with wettable powders, emulsifiable Concentrates, dispersions and sometimes also in the case of microgranules using water.
Staubfbrmige und granulierte Zubereitungen sowie versprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt. Dust-like and granulated preparations and 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 oder mehr Aktivsubstanz, vorzugsweise liegt sie jedoch in Bereichen von 0,01 bis 5 kg/ha. With the external conditions such as temperature, humidity and. a. the required application rate varies. It can fluctuate within wide limits, e.g. B. from 0.005 to 10.0 kg / ha or more of active substance, but is preferably in the range of 0.01 to 5 kg / ha.
Die erfindungsgemäßen Wirkstoffe können in ihren handelsüblichen Formulierungen entweder allein oder in Kombination mit weiteren, literaturbekannten Fungiziden angewendet werden. The active compounds according to the invention can be used in their commercially available formulations either alone or in combination with other fungicides known from the literature.
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, Huttiafol, BAY-MEB 6401, Propiconazol, Etaconazol, Diclobutrazol, Bitertanol, Triadimefon, Triadimenol, Imazalil, Prochloraz, Fenapanil, SSF 105, Triflumizol, PP 969, Huttiafol, BAY-MEB 6401, Propiconazole, Etaconazole, Diclobutrazol, Bitertanol, Triadimefon, Triadimenol,
Tebuconazole, Fluotrimazol, Tridemorph, Dimethomorph, Dodemorph, Fenpropimorph, Falimorph, 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, Dichlorfunanid, Captafol, Captan, Folpet, Tolyfluanid. Chlorothalonil, Etridiazol, Iprodione, Procymidon, Vinclozolin, Metomeclan, Myclozolin. Dichlozolinate, Fluorimide, Drazoxolon, Chinomethionate, Nitrothalisopropyl, Dithianon, Dinocap, Binapacrvl, Fentinacetate, Fentinhydroxide, Carboxin, Oxycarboxin, Pyracarolid, Methfuroxam, Fenfura, Furmecyclos, Benodanil, Mebenil, Mepronil, Flutalanil, Tebuconazole, fluotrimazole, tridemorph, dimethomorph, dodemorph, fenpropimorph, Falimorph, S-32165, Chlobenzthiazone, Parinol, buthiobate, fenpropidin, triforine, fenarimol, .Nuarimol, triarimol, ethirimol, dimethirimol, Bupirimate, Rabenzazole, Tricyclazole, Fluobenzimine, Pyroxyfur, NK -483, PP-389, Pyroquilon, Hymexazole, Fenitropan, UHF-8227, Cymoxanil, Dichlorfunanid, Captafol, Captan, Folpet, Tolyfluanid. Chlorothalonil, Etridiazole, Iprodione, Procymidon, Vinclozolin, Metomeclan, Myclozolin. Dichlozolinate, fluorimide, drazoxolone, quinomethionate, nitrothalisopropyl, dithianon, dinocap, binapacrvl, fentinacetate, fentin hydroxides, carboxin, oxycarboxin, pyracarolide, methfuroxam, fenfura, furmecyclos, benodananone, mebenilil, mebenil
Fuberidazole, Thiabendazole, Carbendazim, Benomyl, Thiophanate, Thiophanatemethyl, CGD-95340 F, KF-1216, Mancozeb, Zineb, Nabam, Thiram, Probineb, 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, Thiophanatemethyl, CGD-95340 F, KF-1216, Mancozeb, Zineb, Nabam, Thiram, Probineb, Prothiocarb, Propamocarb, Dodine, Guazatine, Dicloran, Bebecylazene, Quintozhenazene, Quintozhen, Quintozhen , 2-phenylphenol, copper compounds such as Cu-oxychloride, oxine-Cu, Cu-oxide, sulfur, fosethyl aluminum, sodium dodecylbenzenesulfonate, sodium dodecyl sulfate, sodium C13 / C15 alcohol ether sulfonate, sodium cetostearyl phosphate ester,
Dioctyl-natriumsulfosuccinat, Natrium-isopropylnaphthalinsulfonat, Dioctyl sodium sulfosuccinate, sodium isopropylnaphthalenesulfonate,
Natrium-methylenbisnaphth-tünsulfonat, Cetyl-trimethyl-ammomumchlorid, Salze von langkettigen primären, sekundären oder tertiären Aminen, Alkyl-propylenamine, Lauryl-pyridinium-bromid, ethoxilierte quatemierte Fettamine, Sodium methylene bisnaphthene sulfonate, cetyl trimethyl ammonium chloride, 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 Kombinationspartner stellen bekannte Wirkstoffe dar, die zum großen Teil in C. R. Worthing, U.S.B. Walker, The Pesticide Manual, 7. Auflage (1983), British Crop Protection Council, beschrieben sind. The combination partners mentioned above are known active ingredients, which are largely in C. R. Worthing, U.S.B. Walker, The Pesticide Manual, 7th edition (1983), British Crop Protection Council.
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 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, dimethoate, ethoprophos, etrimfos, fenitrothion. Fenthion, Heptenophos, Parathion, Parathionmethyl, Phosalon, Pirimiphos-ethyl,
Pirimiphos-methyl, Profenofös, Prothiofos, Sulprofos, Triazophos, Trichlorphon. Pirimiphos-methyl, Profenofös, 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, Carbofiiran, Carbosulfan, Cloethocarb, Isoprocarb, Methomyl, Oxamyl, Pirimicarb, Promecarb, Propoxur, Thiodicarb.  Aldicarb, Bendiocarb, BPMC (2- (1-methylpropyl) phenylmethylcarbamate), Butocarboxim, Butoxicarboxim, Carbaryl, Carbofiiran, 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-trifluormethylvinyl)-cyclopropancarbonsäure-(alpha- cyano-3-phenyl-2-methyl-benzyl)ester (FMC 54800), Fenpropathrin, Fenfluthrin, Fenvalerat. Flucythrinate, Flumethrin, Fluvalinate, Permethrin, Resmethrin, Tralomethrin. 4. aus der Gruppe der Formamidine Allethrin, Alphamethrin, Bioallethrin, Bioresmethrin, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cypermethrin, Deltamethrin, 2,2-Dimethyl-3- (2-chloro-2-trifluoromethylvinyl) -cyclopropanecarboxylic acid- (alpha-cyano-3-phenyl-2-methyl -benzyl) ester (FMC 54800), fenpropathrin, fenfluthrin, fenvalerate. Flucythrinate, flumethrin, fluvalinate, permethrin, resmethrin, tralomethrin. 4. from the group of formamidines
Amitraz, Chlordimeform. Amitraz, chlorordime form.
5. aus der Gruppe der Zinnverbindungen 5. from the group of tin compounds
Azocyclotin, Cyhexatin, Fenbutatinoxid Azocyclotin, Cyhexatin, Fenbutatinoxid
6. Sonstige 6. Other
Abamektin, Bacillus thuringiensis, Bensultap, Binapacryl, Bromopropylate, Buprofecin Camphechlor, Cartap, Chlorbenzilate, Chlorfluazuron,  Abamectin, Bacillus thuringiensis, Bensultap, Binapacryl, Bromopropylate, Buprofecin Camphechlor, Cartap, Chlorbenzilate, 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)phenyIamino)carbonyl)-2,6-difluor-benzamide (XRD 473), Diflubenzuron, N-(2,3-Dihydro-3-methyl-1,2-thiazol-2-ylidene)2,4-xylidene, Dinobuton, Dinocap, Endosulfan, Fenoxycarb, Fenthiocarb, Flubenzimine, Flufenoxuron. Gamma-HCH, Hexythiazox, Hydramethylnon (AC 217 300), Ivermectin, Cyclopropanecarboxylic acid (2-naphthylmethyl) ester (Ro 12-0470), cyromacin, DDT, dicofol, N- (3,5-dichloro-4- (1,1,2, 2-tetrafluoroethoxy) phenylamino) carbonyl) -2, 6-difluoro-benzamide (XRD 473), diflubenzuron, N- (2,3-dihydro-3-methyl-1,2-thiazol-2-ylidenes) 2,4-xylidenes, dinobutone, dinocap, endosulfane, fenoxycarb, fenthiocarb , Flubenzimine, flufenoxuron. Gamma-HCH, hexythiazox, hydramethylnon (AC 217 300), ivermectin,
2-Nitro-methyl-4,5-dihydro-6H-thiazin (SD 52618), 2-Nitromethyl-3,4-dihydrothiazol (SD 35651), 2-Nitromethylene-1,3-thiazinon-3yl-carbamaldehyde (WL 108477), Propargite, Teflubenzuron, Tetradifon, Tetrasul, Thicyclam, Triflumuron, Kempolyeder- und 2-nitro-methyl-4,5-dihydro-6H-thiazine (SD 52618), 2-nitromethyl-3,4-dihydrothiazole (SD 35651), 2-nitromethylene-1,3-thiazinon-3yl-carbamaldehydes (WL 108477 ), Propargite, Teflubenzuron, Tetradifon, Tetrasul, Thicyclam, Triflumuron, 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 Bereichen 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. Forms of use can vary widely, the active substance concentration of the forms of use can be from 0.0001 to 100% by weight of active substance, 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 Inertstoff mischt und in einer Schlagmühle zerkleinert. A. Formulation Examples a) A dusting agent is obtained by mixing 10 parts by weight of active compound and 90 parts by weight of talc as an inert substance and comminuting them in a hammer mill.
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 vermählt. d) Ein emulgierbares Konzentrat läßt sich herstellen aus 15 Gew.-Teilen Wirkstoff, 75 Gew.-Teilen Cyclohexanon als Lösungsmittel und 10 Gew.-Teilen oxethyliertem b) A wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight of active compound, 65 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium as the wetting agent. and dispersant mixes and grinds in a pin mill. c) A dispersion concentrate which is readily dispersible in water is prepared by mixing 40 parts by weight of active compound with 7 parts by weight of a sulfosuccinic acid half-ester, 2 parts by weight of a lignosulfonic acid sodium salt and 51 parts by weight of water and in a attritor milled 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 A suspension of the wettable powder from example b) having a solids content of 30% is expediently used and this is sprayed onto the surface of a
Attapulgitgranulats, trocknet und vermischt innig. Dabei beträgt der Gewichtsanteil des Spritzpulvers ca. 5 % und der des inerten Trägermaterials ca. 95 % des fertigen Granulats. Attapulgite granules, dry and mix 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: 4-Methyl-N-phenyl-2-(3-propinyloxy)-6-pyrimidinamin B. Chemical Examples Example 1: 4-Methyl-N-phenyl-2- (3-propynyloxy) -6-pyrimidinamine
Vebindung Nr.1
Figure imgf000026_0001
Connection No.1
Figure imgf000026_0001
Zu 324 g wasserfreiem Natriumcarbonat in 1600 ml Wasser gab man 416 g  416 g were added to 324 g of anhydrous sodium carbonate in 1600 ml of water
Acetessigsäureethylester und anschließend 445 g S-Methylisothioharnstoffsulfat, rührte ca. 96 Stunden bei Raumtemperatur und stellte dann mit Essigsäure einen pH- Wert von 5,5 bis 6 ein. Nach Abfiltrieren und Trocknung des Produkts erhielt man 485 g (97%) Ethyl acetoacetate and then 445 g of S-methylisothiourea sulfate, stirred for about 96 hours at room temperature and then adjusted to a pH of 5.5 to 6 with acetic acid. After filtering off and drying the product, 485 g (97%) were obtained.
6-Methyl-2-methylmercapto-1H-pyrimidin-4-on. 6-methyl-2-methylmercapto-1H-pyrimidin-4-one.
Smp.: 180 - 185 °C. M.p .: 180-185 ° C.
In 500 ml POCl3 und 15 ml N,N-Dimethylanilin erhitzte man 425 g 425 g were heated in 500 ml of POCl 3 and 15 ml of N, N-dimethylaniline
6-Methyl-2-methylmercapto-1H-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, hydrolysierte und wusch die organische Phase neutral, trocknete diese und destillierte (Sdp.: 63-66°C/0,2 mmHg). Man erhielt 397 g (83 % ) 6-methyl-2-methylmercapto-1H-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, hydrolyzed and washed the organic phase until neutral, dried and distilled (bp: 63-66 ° C. / 0.2 mmHg). 397 g (83%) were obtained
4-Chlor-6-methyl-2-methylthiopyrimidin, Smp.: 38-40 °C. 4-chloro-6-methyl-2-methylthiopyrimidine, m.p .: 38-40 ° C.
Man suspendierte 461 g eines Gemisches aus Kaliumperoxomonosulfat, 2 KHSO5, KHSO4 und K2SO4 in einer Mischung aus jeweils 300 ml Methanol, Wasser und Essigsäure und gah unter Rühren 87,3 g 4-Chlor-6-methyl-2-methylthiopyrimidin hinzu. Nach Abklingen der exothermen Reaktion (ca. 1 Stunde) extrahierte man mit reichlich Methylenchlorid, wusch die organische Phase, trocknete diese und destillierte das Lösungsmittel ab. Man erhielt 67 g (65 %) 4-Chlor-6-methyl-2-methylsulfonyl-pyrimidin, Smp.: 81-84 °C. 461 g of a mixture of potassium peroxomonosulfate, 2 KHSO 5 , KHSO 4 and K 2 SO 4 were suspended in a mixture of 300 ml each of methanol, water and acetic acid, and 87.3 g of 4-chloro-6-methyl-2- methylthiopyrimidine added. After the exothermic reaction had subsided (about 1 hour), the mixture was extracted with plenty of methylene chloride, the organic phase was washed, dried and the solvent was distilled off. 67 g (65%) of 4-chloro-6-methyl-2-methylsulfonyl-pyrimidine were obtained, mp: 81-84 ° C.
Zu 3,2 g NaH (80% in Mineralöl) in 150 ml abs. THF tropfte man 5,9 g Propinylalkohol, rührte eine Stunde und gab dann 20,7 g 4-Chlor-6-methyl-2-methylthiopyrimidin hinzu. Nach 16 Stunden hydrolysierte man, extrahierte mit Essigester oder Methylenchlorid, wusch die organische Phase, trocknete diese und erhielt nach Abdestillation des Lösungsmittels 13,4 g (74 %) 4-Chlor-6-methyl-2-propinyloxypyrimidin, To 3.2 g NaH (80% in mineral oil) in 150 ml abs. THF was added dropwise to 5.9 g of propynyl alcohol, stirred for one hour and then 20.7 g of 4-chloro-6-methyl-2-methylthiopyrimidine were added. To The mixture was hydrolyzed for 16 hours, extracted with ethyl acetate or methylene chloride, the organic phase was washed, dried and, after the solvent had been distilled off, 13.4 g (74%) of 4-chloro-6-methyl-2-propynyloxypyrimidine were obtained,
Sdp.: 85-95°C/0,05-0,01 mbar.  Bp: 85-95 ° C / 0.05-0.01 mbar.
Zu 80 ml Wasser gab man eine Lösung von 13,4 g 4-Chlor-6-methyl-2-propinyloxypyrimidin in 20 ml Aceton,gab dann 6,8 g Anilin sowie ca. 1,5 ml konz. Salzsäure hinzu und erhitzte ca. 1 Stunde unter Rückfluß. Nach Abkühlen des Reaktionsgemisches gab man ca. 100 ml Wasser zum Reaktionsgemisch, stellte mit 2 n NaOH das Gemisch leicht alkalisch ein und extrahierte mit Methylenchlorid. Nach Waschen der organischen Phase trocknete man und destillierte das Lösungsmittel ab. Man erhielt ein festes Rohprodukt, welches aus A solution of 13.4 g of 4-chloro-6-methyl-2-propynyloxypyrimidine in 20 ml of acetone was added to 80 ml of water, then 6.8 g of aniline and about 1.5 ml of conc. Hydrochloric acid added and heated under reflux for about 1 hour. After the reaction mixture had cooled, about 100 ml of water were added to the reaction mixture, the mixture was made slightly alkaline with 2N NaOH and extracted with methylene chloride. After washing the organic phase, the mixture was dried and the solvent was distilled off. A solid crude product was obtained, which consists of
Benzin/Essigester-Mischungen umkristallisiert werden konnte. Nach der Umkristallisation erhielt man 16,4 g (94 %) 4-Methyl-N-phenyl-2-(3-propinyloxy)-6-pyrirnidinamin , Smp.: 94-97°C.  Gasoline / ethyl acetate mixtures could be recrystallized. After recrystallization, 16.4 g (94%) of 4-methyl-N-phenyl-2- (3-propynyloxy) -6-pyrirnidinamine, mp: 94-97 ° C.
Beispiel 2: Example 2:
4-Methyl-N-methyl-2-propinyloxy-N-phenyl-6-aminopyrimidin 4-methyl-N-methyl-2-propynyloxy-N-phenyl-6-aminopyrimidine
Verbindung Nr. 61
Figure imgf000027_0001
Compound No. 61
Figure imgf000027_0001
Zu 80 ml Wasser gab man eine Lösung von 17,6 g 4-Chlor-6-methyl-2-methylthiopyrimidin in 20 ml Aceton, gab dann 10,7 g N-Methylanilin sowie ca. 1-5 ml konz. Salzsäure hinzu und erhitzte ca. 1 Stunde unter Rückfluß. Nach Abkühlen des Reaktionsgemisches gab man ca. 100 ml Wasser zum Reaktionsgemisch, stellte mit 2 n NaOH das Gemisch leicht alkalisch ein und extrahierte mit Methylenchlorid. Nach Waschen der organischen Phase, Trocknung, Abdestillation des Lösungsmittels und Umkristallisation des Produkts aus einer  A solution of 17.6 g of 4-chloro-6-methyl-2-methylthiopyrimidine in 20 ml of acetone was added to 80 ml of water, then 10.7 g of N-methylaniline and about 1-5 ml of conc. Hydrochloric acid added and heated under reflux for about 1 hour. After the reaction mixture had cooled, about 100 ml of water were added to the reaction mixture, the mixture was made slightly alkaline with 2N NaOH and extracted with methylene chloride. After washing the organic phase, drying, distilling off the solvent and recrystallizing the product from a
Heptan/Essigestermischung erhielt man 16,3 g (66 %) Heptane / ethyl acetate mixture gave 16.3 g (66%)
4-Methyl-N-memyl-2-memylthio-N-phenyl-6-pyrimidinamin, 4-methyl-N-memyl-2-memylthio-N-phenyl-6-pyrimidinamine,
Smp.: 88-89 °C. Man suspendierte 46 g eines Gemisches aus Kaliumperoxomonosulfat, 2 KHSO5, KHSO4 und K2SO4 in einer Mischung aus jeweils 100 ml Methanol, Wasser und Essigsäure und gab unter Rühren 12.3 g 4-Methyl-N-methyl-2-methylthio-N-phenyl-6-pyrimidinamin hinzu. Nach Abklingen der exothermen Reaktion (ca. 1 Stunde) extrahierte man mit reichlich Methylenchlorid, wusch die organische Phase und erhielt nach Trocknung und Abdestillation des Lösungsmittels 9,2 g (66 %) M.p .: 88-89 ° C. 46 g of a mixture of potassium peroxomonosulfate, 2 KHSO 5 , KHSO 4 and K 2 SO 4 were suspended in a mixture of 100 ml each of methanol, water and acetic acid, and 12.3 g of 4-methyl-N-methyl-2-methylthio- N-phenyl-6-pyrimidinamine added. After the exothermic reaction had subsided (about 1 hour), the mixture was extracted with plenty of methylene chloride, the organic phase was washed and, after drying and distilling off the solvent, 9.2 g (66%) were obtained.
4-Methyl-N-meΛyl-2-methylsulfonyl-N-phenyl-6-pyrimidinamin,  4-methyl-N-meΛyl-2-methylsulfonyl-N-phenyl-6-pyrimidinamine,
Smp.: 166-167 °C M.p .: 166-167 ° C
Zu 1,1 g NaH (80% in Mineralöl) in 50 ml abs. THF tropfte man 1,9 g Propinylalkohol, rührte eine Stunde und gab dann 7,0 g To 1.1 g NaH (80% in mineral oil) in 50 ml abs. THF was added dropwise with 1.9 g of propynyl alcohol, stirred for one hour and then given with 7.0 g
4-Methyl-N-methyl-2-methylsulfonyl-N-phenyl-6-pyriπtidinamin hinzu. Nach 16 Stunden hydrolysierte man, extrahierte mit Essigester oder Methylenchlorid, wusch die organische Phase, trocknete diese und erhielt nach Abdestillieren des Lösungsmittels und  4-Methyl-N-methyl-2-methylsulfonyl-N-phenyl-6-pyriπtidinamine added. After 16 hours, the mixture was hydrolyzed, extracted with ethyl acetate or methylene chloride, the organic phase was washed, dried and, after the solvent had been distilled off, and
säulenchromatographischer Reinigung des Produkts, mit Essigester und Heptan (1:1) als Laufmittel, 5,4 g (85 %) 4-Methyl-N-methyl-2-propinyloxy-N-phenyl-6- am inopyrimidin, Smp.: 88-90 °C. column chromatographic purification of the product, using ethyl acetate and heptane (1: 1) as the eluent, 5.4 g (85%) 4-methyl-N-methyl-2-propynyloxy-N-phenyl-6-am inopyrimidine, mp: 88 -90 ° C.
Beispiel 3: Example 3:
2-(1-Jod-3-propinyloxy)-4-methyl-N-methyl-N-phenyl-6-aminopyrimidin 2- (1-iodo-3-propynyloxy) -4-methyl-N-methyl-N-phenyl-6-aminopyrimidine
Verbindung Nr. 63
Figure imgf000028_0001
Compound No. 63
Figure imgf000028_0001
Unter N2-Atmosphäτe legte man 3,2 g 3.2 g were placed under an N 2 atmosphere
4-Methyl-N-methyl-2-propinyloxy-N-phenyl-6-aminopyri midin in 60 ml THF vor, kühlte auf -78 °C und gab 8,5 ml 1,6 molare n-Butyllithiumlösung in Hexan hinzu. Nach ca. 1 Stunde gab man 3,5 g jod zu, ließ die Lösung auf Raumtemperatur erwärmen und hydrolysierte nach ca. 30 Minuten. Man nahm in Methylenchlorid auf, wusch mit Wasser, trocknete die Lösung, destillierte das Lösungsmittel ab und erhielt nach säulenchromatographischer Reinigung des Produkts, mit Essigester und Heptan (1:1) als Laufmittel, 3,4 g (73%) Pre-4-methyl-N-methyl-2-propynyloxy-N-phenyl-6-aminopyrimine in 60 ml of THF, cooled -78 ° C and added 8.5 ml of 1.6 molar n-butyllithium solution in hexane. After about 1 hour, 3.5 g of iodine were added, the solution was allowed to warm to room temperature and hydrolyzed after about 30 minutes. The mixture was taken up in methylene chloride, washed with water, the solution was dried, the solvent was distilled off and, after purification of the product by column chromatography, with ethyl acetate and heptane (1: 1) as the eluent, 3.4 g (73%)
2-(1-jod-3-propinyloxy)-4-methyl-N-methyl-N-phenyl-6-amin opyrimidin, Smp.: 177-180°C.  2- (1-iodo-3-propynyloxy) -4-methyl-N-methyl-N-phenyl-6-amine opyrimidine, m.p .: 177-180 ° C.
Beispiel 4: Example 4:
4-(3-Chloran ilino)-2-(3-(1-propinyl)-thio)-6-trifluormethyl-pyrimidin  4- (3-chloroanilino) -2- (3- (1-propynyl) thio) -6-trifluoromethyl-pyrimidine
Verbindung Nr.118
Figure imgf000029_0001
Compound No.118
Figure imgf000029_0001
Zu einer frisch hergestellten Natriumethanolatlösung aus 46 g Natrium und 1000 ml Ethanol gab man 107 g Thiohamstoff und danach 184 g Trifluoressigsäureethylester, erhitzte dann 6 Stunden unter Rückfluß, destillierte das Lösungsmittel ab und nahm in Eiswasser auf. Nach der Zugabe von ca. 120 ml konz. Salzsäure stellte man mit Essigsäure einen pH-Wert zwischen 5 und 6 ein, und erhielt nach dem Abfiltrieren 162 g (83%) 107 g of thiourea and then 184 g of ethyl trifluoroacetate were added to a freshly prepared sodium ethanolate solution consisting of 46 g of sodium and 1000 ml of ethanol, then heated under reflux for 6 hours, the solvent was distilled off and the residue was taken up in ice water. After adding about 120 ml of conc. Hydrochloric acid was adjusted to a pH between 5 and 6 with acetic acid, and 162 g (83%) were obtained after filtering off
2-Mercapto-4-trifluormethyl-1,3-dihydro-4-pyrimidinon. 2-mercapto-4-trifluoromethyl-1,3-dihydro-4-pyrimidinone.
Zu 6 g Natriumhydrid (80 % in Mineralöl) in 200 ml Acetonitril gab man 39,3 g 39.3 g were added to 6 g of sodium hydride (80% in mineral oil) in 200 ml of acetonitrile
2-Mercapto-4-trifluormethyl-1,3-dihydro-4-pyrimidinon und 1 ml 2-mercapto-4-trifluoromethyl-1,3-dihydro-4-pyrimidinone and 1 ml
Tri(C8/C10)alkylmethylammoniumchlorid, rührte ca. 1 Stunde, tropfte dann 34 ml Tri (C 8 / C 10 ) alkylmethylammonium chloride, stirred for about 1 hour, then dripped 34 ml
Propinylbromid (80 %-Lösung in Toluol) hinzu und erhitzte ca.6 Stunden unter Rückfluß. Nach Abkühlung und Einengung des Reaktionsgemisches nahm man in 300 ml Wasser auf, neutralisierte mit Essigsäure und erhielt nach dem Abfiltrieren 46 g (98%) Propinyl bromide (80% solution in toluene) was added and the mixture was heated under reflux for about 6 hours. After cooling and concentrating the reaction mixture, the mixture was taken up in 300 ml of water, neutralized with acetic acid and, after filtering off, 46 g (98%) were obtained.
2-(3-(1-Propinyl)-thio)-6-trifluormethyl-1H-4-pyrimidinon, Smp.: 158 - 163 ºC. 2- (3- (1-propynyl) thio) -6-trifluoromethyl-1H-4-pyrimidinone, m.p .: 158-163 ° C.
In 200 ml POCl3 und 5 ml N,N-Dimethylanilin erhitzte man 46 g 46 g were heated in 200 ml of POCl 3 and 5 ml of N, N-dimethylaniline
2-(3-(1-Propinyl)-thio)-6-trifluormethyl-1H-4-pyrimidinon unter Rückfluß. Nach 2- (3- (1-Propynyl) thio) -6-trifluoromethyl-1H-4-pyrimidinone under reflux. To
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, destillierte (Sdp.: 56-57°C/ 0,02 mm Hg) und erhielt 39,2 g (78 % ) 4-Chlor-2-(3-(1-propinyl)-thio)-6-trifluormethyl-pyrimidin. complete solution of the pyrimidinone (approx. 60 minutes) was distilled at approx. 200 mm Hg the POCl 3 was removed, taken up in methylene chloride and hydrolyzed, the organic phase was washed neutral, dried, distilled (bp .: 56-57 ° C./0.02 mm Hg) and obtained 39.2 g (78%) of 4-chlorine -2- (3- (1-propynyl) thio) -6-trifluoromethyl-pyrimidine.
Zu 40 ml Wasser gab man eine Lösung von 5,1 g A solution of 5.1 g was added to 40 ml of water
4-Chlor-2-(3-(1-propinyl)-thio)-6-trifluormethyl-pyrimidin in 10 ml Aceton, gab dann 2.6 g Anilin sowie ca. 1 ml konz. Salzsäure hinzu und erhitzte ca.2 Stunden unter Rückfluß. Nach Abkühlen des Reaktionsgemisches gab man ca. 50 ml Wasser zum Reaktionsgemisch, stellte mit 2 n NaOH das Gemisch leicht alkalisch ein und extrahierte mit Methylenchlorid. Nach Waschen der organischen Phase, trocknete man, destillierte das Lösungsmittel ab und erhielt nach säulenchromatographischer Reinigung, mit Essigester und Heptan (3:7) als Laufmittel, 0,8 g (12 %) 4-(3-Chloranilino)-2-(3-(1-propmyl)-thio)-6-trifluormethyl -pyrimidin, Smp.: 4-chloro-2- (3- (1-propynyl) thio) -6-trifluoromethyl-pyrimidine in 10 ml acetone, then gave 2.6 g aniline and approx. 1 ml conc. Hydrochloric acid and heated under reflux for about 2 hours. After the reaction mixture had cooled, about 50 ml of water were added to the reaction mixture, the mixture was made slightly alkaline with 2N NaOH and extracted with methylene chloride. After washing the organic phase, it was dried, the solvent was distilled off and, after purification by column chromatography, with ethyl acetate and heptane (3: 7) as the eluent, 0.8 g (12%) of 4- (3-chloroanilino) -2- ( 3- (1-propmyl) -thio) -6-trifluoromethyl-pyrimidine, m.p .:
85-87 °C. 85-87 ° C.
Beispiel 5: 4-Amhno-5-methoxy-2-(3-(1-propmyl)-thio)-pyrimidin Example 5: 4-Amhno-5-methoxy-2- (3- (1-propmyl) thio) pyrimidine
Verbindung Nr. 249
Figure imgf000030_0001
Compound No. 249
Figure imgf000030_0001
Zu 33 g NaH (80% in Mineralöl) in 600 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. Nach Stehenlassen über 16 Stunden gab man 600 ml Isopropanol und 76 g Thiohamstoff 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 (92%) To 33 g NaH (80% in mineral oil) in 600 ml abs. 15% of a mixture of 118 g of ethyl formate and 104 g of methyl methoxyacetate were added dropwise to THF, and the reaction mixture was warmed gently 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. After standing for 16 hours, 600 ml of isopropanol and 76 g of thiourea were added and this reaction mixture was heated under reflux for 120 minutes, the THF being partially distilled off. The solvents were then distilled off and the residue was taken up in water, acidified with acetic acid and, after filtering off, 145 g (92%) were obtained.
5-Methoxy-2-thio-1,3-dihydro-4-pyrimidinon, Smp.: 275-278 °C Zu 12 g Natriumhydrid (80 % in Mineralöl) in 200 ml Acetonitril gab man 47,4 g 5-methoxy-2-thio-1,3-dihydro-4-pyrimidinone, m.p .: 275-278 ° C 47.4 g were added to 12 g of sodium hydride (80% in mineral oil) in 200 ml of acetonitrile
5-Methoxy-2-thio-1,3-dihydro-4-pyrimidinon und 1 ml  5-methoxy-2-thio-1,3-dihydro-4-pyrimidinone and 1 ml
Tri(C8/C10)alkylmethylammomumchlorid, rührte ca. 1 Stunde, tropfte dann 50 ml Tri (C 8 / C 10 ) alkyl methyl ammonium chloride, stirred for about 1 hour, then dripped 50 ml
Propinylbromid (80 %-Lösung in Toluol) hinzu und erhitzte ca. 6 Stunden unter Rückfluß. Nach Abkühlung und Einengung des Reaktionsgemisches nahm man in 300 ml Wasser auf, neutralisierte mit Essigsäure und erhielt nach dem Abfiltrieren 44 g (75%)  Propinyl bromide (80% solution in toluene) was added and the mixture was heated under reflux for about 6 hours. After cooling and concentrating the reaction mixture, the mixture was taken up in 300 ml of water, neutralized with acetic acid and 44 g (75%) were obtained after filtering off
5-Methoxy-2-(3-(1-propinyl)-thio)-1H-4-pyrimidinon, Smp.: 158 ºC.  5-methoxy-2- (3- (1-propynyl) thio) -1H-4-pyrimidinone, m.p .: 158 ° C.
In 200 ml POCl3 und 5 ml N,N-Dimeftyla n ilin erhitzte man 44 g 44 g was heated in 200 ml of POCl 3 and 5 ml of N, N-dimeftylamine
5-Methoxy-2-(3-(1-propinyl)-thio)-1H-4-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 und erhielt nach Abdestillieren des Lösungsmittel 24,8 g (52 %) 5-methoxy-2- (3- (1-propynyl) thio) -1H-4-pyrimidinone 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, after the solvent had been distilled off, 24.8 g ( 52%)
4-Chlor-5-methoxy-2-(3-(1-propinyl)-thio)-pyrimidin,  4-chloro-5-methoxy-2- (3- (1-propynyl) thio) pyrimidine,
Smp.: 70-72 °C.  M.p .: 70-72 ° C.
Zu 40 ml Wasser gab man eine Lösung von 5,4 g A solution of 5.4 g was added to 40 ml of water
4-Chlor-5-methoxy-2-(3-(1-propinyl)-thio)-pyrimidin in 10 ml Aceton, gab dann 2,3 g Anilin sowie ca. 1 ml konz. Salzsäure hinzu und erhitzte ca. 2 Stunden zum Rückfluß. Nach  4-chloro-5-methoxy-2- (3- (1-propynyl) thio) pyrimidine in 10 ml acetone, then gave 2.3 g aniline and approx. 1 ml conc. Hydrochloric acid added and heated to reflux for about 2 hours. To
Abkühlen des Reaktionsgemisches gab man ca. 50 ml Wasser zum Reaktionsgemisch, stellte mit 2 n NaOH das Gemisch leicht alkalisch ein und extrahierte mit Methylenchlorid. Nach Waschen der organischen Phase, Trocknen, Abdestillation des Lösungsmittels und säulenchromatographischer Reinigung des Produkts, mit Essigester und Heptan (7:3) als Laufmittel, erhielt man 5,2 g (77 %) 4-Anilino-5-methoxy-2-(3-(1-propinyl)-thio)-pyrimidin, Smp.: 95-96 °C.  Cooling of the reaction mixture, about 50 ml of water were added to the reaction mixture, the mixture was made slightly alkaline with 2N NaOH and extracted with methylene chloride. After washing the organic phase, drying, distilling off the solvent and purifying the product by column chromatography, using ethyl acetate and heptane (7: 3) as the eluent, 5.2 g (77%) of 4-anilino-5-methoxy-2- ( 3- (1-propynyl) thio) pyrimidine, m.p .: 95-96 ° C.
Die Ausbeuten der angegebenen Beispiele wurden nicht optimiert. Entsprechend der oben aufgeführten Beispiele können die in der Tabelle 1 genannten Verbindungen hergestellt werden. The yields of the examples given were not optimized. According to the examples listed above, the compounds mentioned in Table 1 can be prepared.
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 imgf000032_0001
Figure imgf000033_0001
Figure imgf000034_0001
Figure imgf000035_0001
Figure imgf000036_0001
The examples with the suffix A are the acid addition salts of the respective parent compound; the acid and the associated melting or decomposition point are then given in the "physical constant" column. In individual cases, the salts can also contain water of crystallization.
Figure imgf000032_0001
Figure imgf000033_0001
Figure imgf000034_0001
Figure imgf000035_0001
Figure imgf000036_0001
Figure imgf000037_0001
Figure imgf000037_0001
Figure imgf000038_0001
Figure imgf000038_0001
Figure imgf000039_0001
Figure imgf000039_0001
Figure imgf000040_0001
Figure imgf000041_0001
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000040_0001
Figure imgf000041_0001
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000045_0001
Figure imgf000046_0001
Figure imgf000047_0001
Figure imgf000048_0001
Figure imgf000049_0001
Figure imgf000044_0001
Figure imgf000045_0001
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Figure imgf000047_0001
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Figure imgf000055_0001
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Figure imgf000056_0001
Figure imgf000056_0001
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Figure imgf000063_0001
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Figure imgf000064_0001
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Figure imgf000070_0001
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Figure imgf000073_0001
Figure imgf000067_0001
Figure imgf000068_0001
Figure imgf000069_0001
Figure imgf000070_0001
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Figure imgf000073_0001
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Figure imgf000075_0001
Figure imgf000076_0001
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Figure imgf000075_0001
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Figure imgf000077_0001
Figure imgf000077_0001
Figure imgf000078_0001
Figure imgf000078_0001
--
- -
Figure imgf000079_0001
Figure imgf000079_0001
Figure imgf000080_0001
Figure imgf000080_0001
Figure imgf000081_0001
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Figure imgf000082_0001
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Figure imgf000083_0001
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Figure imgf000084_0001
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Figure imgf000086_0001
Figure imgf000086_0001
Figure imgf000087_0001
Figure imgf000087_0001
Figure imgf000088_0001
Figure imgf000088_0001
00 —i 00 -i
Figure imgf000089_0001
Figure imgf000089_0001
Figure imgf000090_0001
Figure imgf000091_0001
Figure imgf000090_0001
Figure imgf000091_0001
Beispiel 2: Example 2:
Ca. 14 Tage alte Ackerbohnen der Sorte "Ηarz Freya" oder Trank's Ackerperle" wurden mit wässrigen Suspensionen der beanspruchten Verbindungen tropfnaß behandelt Approximately 14 day old field beans of the variety "Ηarz Freya" or Trank's field pearl "were treated to runoff with aqueous suspensions of the claimed compounds
Nach Antrocknen des Spritzbelages wurden die Pflanzen mit einer Sporcnsuspension (1.5 Mio Sporen/ml) von Botrytis cinerea (BCM-resistenter Stamm) inokuliert. Die Pflanzen wurden in einer K limakamm er 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 comb 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.
Figure imgf000092_0001
Beispiel 3:
Figure imgf000092_0001
Example 3:
Weinsämlinge der Sorten "Riesling/Ehrenfelder" wurden ca. 6 Wochen nach der Aussaat mit wässrigen Suspensionen der beanspruchten Verbindungen tropfnaß behandelt Nach dem Antrocknen des Spriubelages wurden die Pflanzen mit einer Zoosporangiensuspension von Plasmopara viticola inokuliert und tropfnaß in eine Klimakammer mit 23 °C und 80 - 90 % rel. Luftfeuchte gestellt. Wine seedlings of the "Riesling / Ehrenfelder" cultivars were treated to runoff with aqueous suspensions of the claimed compounds about 6 weeks after sowing - 90% rel. Humidity set.
Nach einer Inkubationszeit von 7 Tagen wurden die Pflanzen nochmals über Nacht in die Klimakammer gestellt, um die Sporulation des Pilzes anzuregen. Anschlieβend erfolgte die Befallsauswertung. Der Befallsgrad wurde in % befallene Blattfläche im Vergleich zu den Kontrollpflanzen ausgedrückt. After an incubation period of 7 days, the plants were again placed in the climatic chamber overnight in order to stimulate the sporulation of the fungus. The infestation was then assessed. The degree of infestation was expressed in% infested leaf area in comparison to the control plants.
Bei 500 mg Wirkstoff/l Spritzbrühe zeigten die folgenden entsprechend der Beispielnumme 017, 077, 153A, 155, 164A, 166, 166A, 179A, 195, 301A, 303A, 320, 320A, 321A, 322A, 323A, 349, 351 eine vollständige Befallsunterdrückung. At 500 mg active ingredient / l spray mixture, the following, according to the example number 017, 077, 153A, 155, 164A, 166, 166A, 179A, 195, 301A, 303A, 320, 320A, 321A, 322A, 323A, 349, 351, showed a complete one Infestation suppression.
Figure imgf000094_0001
Figure imgf000094_0001

Claims

Patentansprüche: 1. Verbindungen der Formel I Claims: 1. Compounds of formula I.
Figure imgf000095_0001
Figure imgf000095_0001
worin wherein
R1, R2 = unabhängig voneinander Wasserstoff, (C1-C9)Alkyl, Cyano-(C1-C4)alkyl, R 1 , R 2 = independently of one another hydrogen, (C 1 -C 9 ) alkyl, cyano- (C 1 -C 4 ) alkyl,
Ha lo-(C1-C4)alkyl, Hydroxy-(C1-C4)alkyl, Dihydroxy-(C1-C4)alkyl, Ha lo- (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)Di alkylamino-(C1-C4)alkyl, (C3-C9)Cycloalkylamino-(C1-C4)alkyl, (C 1 -C 4 ) di alkylamino- (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 substituierter 5- oder 6-gliedriger Heteroaromat, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenyl-(C1-C4)aIkyl, gegebenenfalls substituiertes Phenoxy-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylm ercapto-(C1-C4)alkyl, 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 5- or 6-membered heteroaromatic, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenyl, (C 1 -C 4) -alkyl, optionally substituted phenoxy (C 1 -C 4) alkyl, optionally substituted Phenylm ercapto- (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 (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)Alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl , (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 substituen sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann, (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 can mean
R1 und R2 gegebenenfalls zusammen einen gesättigten oder teilweise ungesättigten R 1 and R 2 optionally together a saturated or partially unsaturated
Carbocyclus oder Heterocyclus mit den Heteroatomen O, N, S, Si oder P mit 4 bis 10 Ringgliedem,  Carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members,
R3 = 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 3 = 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)a lkyl, (C1-C4)Alkylthio, Halo-(C1-C4)aIkylthio, 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)alkyI, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C1-C4)Alk ylamino-(C1-C4)alkyl, Halo (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyI, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 1 -C 4 ) alk ylamino- (C 1 -C 4 ) alkyl,
(C1-C4)Dialkylamino-(C1-C4)alkyl, (C3-C9)Cycloalkylamin o-(C1-C4 )alkyl, (C 1 -C 4 ) dialkylamino- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) cycloalkylamine o- (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)HaloalkyIthiocarbonyl, 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 ) haloalkyIthiocarbonyl, aminocarbonyl,
(C1-C4)Alkylaminocarbonyl, (C1-C4)Haloalkylaminocarbonyl, gegebenenfalls substituierter 5- oder 6-gliedriger Heteroaromat, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes (C 1 -C 4 ) alkylaminocarbonyl, (C 1 -C 4 ) haloalkylaminocarbonyl, optionally substituted 5- or 6-membered heteroaromatic, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted
Phenyl-(C1-C4)-alkyl, gegebenenfalls substituiertes Phenoxy-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylmercapto-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylketo-(C1-C4)alkyl, gegebenenfalls substituiertes Phenyl- (C 1 -C 4 ) alkyl, optionally substituted phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenylmercapto- (C 1 -C 4 ) alkyl, optionally substituted phenylketo- (C 1 -C 4 ) alkyl , optionally substituted
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 (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)Alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl, (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 substituen sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann, (C 1 -C 4 ) can be haloalkoxy or simply substituted by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms,
R4, R5, R6 = 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)alkyl, R 4 , R 5 , R 6 = 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-C4)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 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 4 ) 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, (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,
(C1-C4)Alkylaminocarbonyl-(C1-C4)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, (C 1 -C 4 ) haloalkylcarbonyl, (C 1 -C 4 ) alkoxycarbonyl,
(C1-C4)Alkoxycarbonyl-(C1-C4)al kyl, (C1-C4)Alkylaminocarbonyl-(C1-C4)alkyl, (C1-C4)Haloalkoxycarbonyl, (C1-C4)Alkyltlιiocarbonyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkoxycarbonyl, (C 1 - C 4 ) alkyltlιiocarbonyl,
(C1-C4)Haloalkylthiocarbonyl, Aminocarbonyl, (C1-C4)Alkylaminocarbonyl, (C1-C4)Haloalkylaminocarbonyl, gegebenenfalls substituierter 5- oder 6-gliedriger Heteroaromat, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenoxy-(C1-C4)alkyl, gegebenenfalls substituiertes (C 1 -C 4 ) haloalkylthiocarbonyl, aminocarbonyl, (C 1 -C 4 ) alkylaminocarbonyl, (C 1 -C 4 ) haloalkylaminocarbonyl, optionally substituted 5- or 6-membered heteroaromatic, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenyl - (C 1 -C 4 ) alkyl, optionally substituted phenoxy- (C 1 -C 4 ) alkyl, optionally substituted
Phenylmercapto-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylketo-(C1-C4)alkyl, gegebenenfalls substituiertes Phenyloxycarbonyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylamino-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylmercapto- (C 1 -C 4 ) alkyl, 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)Alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl , (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, (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,
R4,R5 und/oder R6 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 4 , R 5 and / or R 6 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,
R7 = Wasserstoff, Formyl, (C1-C4)Alkyl, (C1-C4)Alkoxy, Halo-(C1-C4)alkoxy, Amino(C1-C4)alkoxy, (C1-C4)Alkylamino(C1-C4)alkoxy, R 7 = hydrogen, formyl, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, halo (C 1 -C 4 ) alkoxy, Amino (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylamino (C 1 -C 4 ) alkoxy,
(C1-C4)Alkoxy(C1-C4)alkoxy, Amino, (C1-C4)Alkylamino, (C1-C4)Dialkylamino, Hydroxy-(C1-C4)alkyl, Dihydroxy-(C1-C4)alkyl, Cyano-(C1-C4)alkyl, (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkoxy, amino, (C 1 -C 4 ) alkylamino, (C 1 -C 4 ) dialkylamino, hydroxy- (C 1 -C 4 ) alkyl, dihydroxy- (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) 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, Halo-(C1-C4)alkylthio-(C1-C4)alkyl, (C1-C4)Alkylthio-(C1-C4)alkyl, (C2-C6)Alkenyl, (C2-C6)AIkinyl, 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- (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,
(C1-C4)Alk ylamin o-(C1-C4)alkyl, (C1-C4)Dialkylamino-(C1-C4)alkyl, (C 1 -C 4 ) alkylamine o- (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)Alkoxycarbonyl-(C1-C4)alkyl, (C1-C4)Alkylam inocarbonyl-(C1-C4)alkyl, (C1-C4)Dialkylaminocarbonyl-(C1-C4)alkyl, (C1-C4)AlkyIcarbonyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl, (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)Haloalkylthiocaιbonyl, 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 ) haloalkylthiocaιbonyl, aminocarbonyl,
(C1-C4)Alkylaminocarbonyl, (C1-C4)Haloalkylaminocarbonyl, (C 1 -C 4 ) alkylaminocarbonyl, (C 1 -C 4 ) haloalkylaminocarbonyl,
(C1-C4)Alkoxycarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenyl-(C1-C4)alkyl, (C 1 -C 4 ) alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenyl- (C 1 -C 4 ) alkyl,
gegebenenfalls substituiertes Phenoxy-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylmercapto-(C1-C4)alkyl, gegebenenfalls substituiertes optionally substituted phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenylmercapto- (C 1 -C 4 ) alkyl, optionally substituted
Phenylketo-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylketo (C 1 -C 4 ) alkyl, optionally substituted
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 substituen 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 substituted simply by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms,
R7 und R4 und/oder R5 gegebenenfalls zusammen einen gesättigten, oder teilweise R 7 and R 4 and / or R 5 optionally together a saturated or partially
ungesättigten Carbocyclus oder Heterocyclus mit den Heteroatomen O, N, S, Si oder P mit 4 bis 10 Ringgliedern,  unsaturated carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members,
R8, R9 = unabhängig voneinander Wasserstoff, Halogen, (C1-C4)Alkyl, R 8 , R 9 = independently of one another hydrogen, halogen, (C 1 -C 4 ) alkyl,
Hydroxy-(C1-C4)alkyI, Dih ydroxy-(C1-C4)alkyl, Cyano-(C1-C4)alkyl, Hydroxy- (C 1 -C 4 ) alkyl, dihydroxy- (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl,
Halo-(C1-C4)alkyl, (C1-C4)Alkoxy, (C1-C4)Alkoxy-(C1-C4)alkyl, Halo(C1-C4)alkoxy-(C1-C4)alk yl, (C1-C4 )Alkylthio, Halo-(C1-C4)alkylthio, Halo (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, Halo (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alk yl, (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)Dialkylam ino-(C1-C4)alkyl, (C3-C9)Cycloa lkylam ino-(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)Heterocycloal kyl-(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 Phenylmercapto-(C1-C4)alkyl, gegebenenfalls substituiertes Phenylketo-(C1-C4)alkyl, gegebenenfalls substituiertes Phenyloxycarbonyl-(C1-C4)alkyl, gegebenenfalls substituiertes Phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenylmercapto- (C 1 -C 4 ) alkyl, optionally substituted phenylketo- (C 1 -C 4 ) alkyl, optionally substituted 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,
R8 und R9 gegebenenfalls zusammen einen gesättigten, teilweise ungesättigten oder R 8 and R 9 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 = Sauerstoff oder Schwefel und n = eine Zahl von 0 bis 8 bedeuten, sowie deren Säureadditionssalze. X = oxygen or sulfur and n = a number from 0 to 8, and their acid addition salts.
2. Verbindungen der Formel I, worin 2. Compounds of formula I, wherein
R1, R2 = unabhängig voneinander Wasserstoff, (C1-C9)Alkyl, im Phenylteil durch Halogen. (C1-C4)Alkyl oder (C1-C4)Alkoxy gegebenenfalls substituiertes Phenyl, R 1 , R 2 = independently of one another hydrogen, (C 1 -C 9 ) alkyl, in the phenyl part by halogen. (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy optionally substituted phenyl,
R1 und R2 gegebenenfalls zusammen einen gesättigten oder teilweise ungesättigten R 1 and R 2 optionally together a saturated or partially unsaturated
Carbocyclus oder Heterocyclus mit den Heteroatomen O, N oder S mit 4 bis 10 Ringgliedem,  Carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10 ring members,
R3 = Wasserstoff, Halogen, (C1-C4)Alkyl, Hydroxy-(C1-C4)alkyl, Dihydroxy-(C1-C4)alkyl, (C1-C4)Alkylthio, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C1-C4)Al kylamino-(C1-C4)alkyl, (C1-C4)Dialkylamino-(C1-C4)alkyl, (C3-C9)Cycloalkylamino-(C1-C4)alkyl, R 3 = hydrogen, halogen, (C 1 -C 4 ) alkyl, hydroxy- (C 1 -C 4 ) alkyl, dihydroxy- (C 1 -C 4 ) alkyl, (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, (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 substituierter 5- oder (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 5- or
6-gliedriger Heteroaromat, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil (Heteroaromat) bis zu dreifach durch Halogen, Ester,  6-membered heteroaromatic, where optionally substituted is to be understood that the phenyl part (heteroaromatic) up to three times by halogen, ester,
(C1-C4)Alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl , (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl,
(C1-C4)HaIoalkoxy oder einfach durch Nitro oder Cyano substituen sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann, Can be (C 1 -C 4 ) haloalkoxy or simply substituted by nitro or cyano, and can mean halo in the substituents substituted one or more times by halogen atoms,
R4, R5, R6 = unabhängig voneinander Wasserstoff, Halogen, Hydroxy, Amino, Nitro, Cyano. R 4 , R 5 , R 6 = independently of one another hydrogen, 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, 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, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (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) Alkylamino-(C1-C4)alkyl, (C1-C4)Dialkylamino-(C1-C4)alkyl, (C 1 -C 4 ) alkylamino- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) dialkylamino- (C 1 -C 4 ) alkyl,
(C3-C9)Cyclo alkyl amino-(C1-C4)a lkyl, (C3-C9)Cycloalkyl, (C 3 -C 9) cyclo alkyl amino- (C 1 -C 4) a lkyl, (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)Alkylaminocarbonyl, (C 1 -C 4 ) alkoxycarbonyl, aminocarbonyl, (C 1 -C 4 ) alkylaminocarbonyl,
gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, gegebenenfalls substituiertes Phenylketo-(C1-C4)alkyl, wobei unter gegebenenfalls substituiert zu verstehen ist, daß der Phenylteil bis zu dreifach durch Halogen, Estef. (C1-C4)Alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl, (C1-C4)Haloalkoxy oder einfach durch Nitro oder Cyano substituen sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenylketo (C 1 -C 4 ) alkyl, where optionally substituted is to be 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 ) can be haloalkoxy or simply substituted by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms,
R4,R5 und/oder R6 gegebenenfalls zusammen einen gesättigten oder teilweise ungesättigten oder aromatischen Carbocyclus oder Heterocyclus mit den Heteroatomen O, N, oder S mit 4 bis 10 Ringgliedem, R 4 , R 5 and / or R 6 optionally together a saturated or partially unsaturated or aromatic carbocycle or heterocycle with the heteroatoms O, N, or S with 4 to 10 ring members,
R7 = Wasserstoff, (C1-C4)Alkyl, Cyano-(C1-C4)alkyl, (C1-C4)Alkoxy, Halo-(C1-C4)alkox.y, Amino-(C1-C4)a-koxy, (C1-C4)Alkylamino-(C1-C4)--lkoxy, R 7 = hydrogen, (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, halo- (C 1 -C 4 ) alkox.y, amino- ( C 1 -C 4 ) a-koxy, (C 1 -C 4 ) alkylamino (C 1 -C 4 ) lkoxy,
(C1-C4)Alkoxy-(C1-C4)alkoxy, Amino, (C1-C4)Alkylamino, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkoxy, amino, (C 1 -C 4 ) alkylamino,
(C1-C4)Alkoxy-(C1-C4)alkyl, (C1-C4)Alkylthio, Perhalo-(C1-C4)alkylthio, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio, perhalo (C 1 -C 4 ) alkylthio,
(C1-C4)Alkylamino-(C1-C4)alkyl, (C1-C4)Dialkylamino-(C1-C4)alkyl, (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)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)Alkylcarbonyl, (C 3 -C 9 ) cycloalkylamino- (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, (C 1 -C 4 ) alkoxycarbonyl- (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 sein, 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 substituiert sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann, (C 1 -C 4 ) alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, 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, (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,
R7 und R4 und/oder R5 gegebenenfalls zusammen einen gesättigten, teilweise ungesättigten Carbocyclus oder Heterocyclus mit den Heteroatomen O, N oder S mit 4 bis 10R 7 and R 4 and / or R 5 optionally together form a saturated, partially unsaturated carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10
Ringgliedern, Ring links,
R8, R9 = unabhängig voneinander Wasserstoff, Halogen, (C1-C4)Alkyl, R 8 , R 9 = independently of one another hydrogen, halogen, (C 1 -C 4 ) alkyl,
Hydroxy-(C1-C4)alkyl, Perhalo-(C1-C4)alkyl, (C1-C4)Alkoxy-(C1-C4)alkyl, Hydroxy (C 1 -C 4 ) alkyl, perhalo (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkyl,
(C1-C4)Alkoxy, Halo(C1-C4)-alkoxy-(C1-C4)alkyl, (C1-C4)Alkylthio, (C 1 -C 4 ) alkoxy, halo (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio,
(C1-C4)Alkylthio-(C1-C4)alkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C1-C4)Alkylamin o, (C1-C4)Dialkylamino, (C3-C9)Cycloalkylamino, (C1-C4)Alkylamino-(C1-C4)alkyl, (C1-C4)Dial kylamino-(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 ) alkylamine o, (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, (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 ) cycloalkyl, (C 3 -C 9 ) cycloalkyl- (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 ) alkylcarbonyl,
(C1-C4)Alkoxycarbonyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Phenoxy, 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 substituiert sein kann, und Halo in den Substituenten ein- oder mehrfach durch Halogenatome substituiert bedeuten kann, (C 1 -C 4 ) alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenoxyphenyl- (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, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy or simply substituted by nitro or cyano can be, and can mean halo in the substituents substituted one or more times by halogen atoms,
R8 und R9 gegebenenfalls zusammen einen gesättigten, teilweise ungesättigten oder R 8 and R 9 optionally together a saturated, partially unsaturated or
aromatischen Carbocyclus oder Heterocyclus mit den Heteroatomen O, N oder S mit 4 bis 10 Ringgliedern,  aromatic carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10 ring members,
X = Sauerstoff oder Schwefel und n = eine Zahl von 0 bis 4 bedeuten, sowie deren Säureadditionssalze. X = oxygen or sulfur and 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 unabhängig voneinander Wasserstoff oder (C1-C4)Alkyl, R 1 , R 2 independently of one another are hydrogen or (C 1 -C 4 ) alkyl,
R3 und R2 gegebenenfalls zusammen einen Teil eines gesättigten oder teilweise ungesättigten Carbocyclus oder Heterocyclus mit den Heteroatomen O, N oder S mit 5 oder 6 Ringgliedem, R 3 and R 2 optionally together form part of a saturated or partially unsaturated carbocycle or heterocycle with the heteroatoms O, N or S with 5 or 6 ring members,
R3 Wasserstoff oder Halogen, R 3 is hydrogen or halogen,
R4,R5.R6 unabhängig voneinander Wasserstoff, Halogen, (C1-C4)Alkyl, (C1-C4)Alkoxy oder im Phenylteil durch Halogen, (C1-C4)Alkyl oder (C1-C4)Alkoxy gegebenenfalls substituiertes Phenoxy, R 4 , R 5 .R 6 independently of one another are hydrogen, halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy or in the phenyl part by halogen, (C 1 -C 4 ) alkyl or (C 1 - C 4 ) alkoxy optionally substituted phenoxy,
R4,R5 und R6 zusammen einen oder einen Teil eines gesättigten, teilweise ungesättigten oder aromatischen Carbocyclus oder Heterocyclus mit den Heteroatomen O, N oder S mit 5 bis 7 Ringgliedern, R7 = Wasserstoff oder (C1-C4)Alkyl, R 4 , R 5 and R 6 together form one or a part of a saturated, partially unsaturated or aromatic carbocycle or heterocycle with the heteroatoms O, N or S with 5 to 7 ring members, R 7 = hydrogen or (C 1 -C 4 ) alkyl,
R8 = Wasserstoff, (C1-C4)Alkyl, (C1-C4)Alkoxy, Phenyl-(C1-C4)alkoxy oder Halogen, R 8 = hydrogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, phenyl- (C 1 -C 4 ) alkoxy or halogen,
R9 = Wasserstoff, (C1-C4)Alkyl, Perhalo-(C1-C4)alkyl, (C1-C4)Alkoxy-(C1-C4)alkyl oder Phenyl-(C1-C4)alkyl, R 9 = hydrogen, (C 1 -C 4 ) alkyl, perhalo (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl or phenyl- (C 1 -C 4 ) alkyl,
R8 und R9 gegebenenfalls zusammen einen gesättigten oder teilweise ungesättigten R 8 and R 9 optionally together a saturated or partially unsaturated
Carbocyclus oder Heterocyclus mit den Heteroatomen O, N oder S und mit 5 bis 6 Ringgliedern,  Carbocycle or heterocycle with the heteroatoms O, N or S and with 5 to 6 ring members,
X = Sauerstoff oder Schwefel und n = 0 oder 1 bedeuten. X = oxygen or sulfur and n = 0 or 1.
4. Verbindungen der Formel I gemäß einem oder mehreren der Ansprüche 1 bis 3, worin R1 4. Compounds of formula I according to one or more of claims 1 to 3, wherein R 1
R2, R3, R7 = Wasserstoff, R4, R5, R6 = unabhängig voneinander Wasserstoff, CI, F oder OCH3, R8 = Wasserstoff, CI oder OCH3, R9 = Wasserstoff oder CH3, X = Sauerstoff oder Schwefel und n = 0 bedeuten. R 2 , R 3 , R 7 = hydrogen, R 4 , R 5 , R 6 = independently of one another hydrogen, CI, F or OCH 3 , R 8 = hydrogen, CI or OCH 3 , R 9 = hydrogen or CH 3 , X = Oxygen or sulfur and n = 0 mean.
5. Verfahren zur Herstellung von Verbindungen der Formel I gemäß einem oder mehreren der Ansprüche 1 bis 4, dadurch gekennzeichnet, daß man Verbindungen der Formel I I 5. A process for the preparation of compounds of the formula I according to one or more of claims 1 to 4, characterized in that compounds of the formula I I
Figure imgf000103_0001
Figure imgf000103_0001
worin  wherein
Hal = CI oder Br und Hal = CI or Br and
R12 = (C1-C4)Alkylthio, im Phenylteil durch Halogen, (C1-C4)Alkyl oder (C1-C4)Alkoxy gegebenenfalls substituiertes Phenyl(C1-C4)alkylthio oder den Rest III (CH2)-n C≡C- R 3 (III)R 12 = (C 1 -C 4 ) alkylthio, in the phenyl part by halogen, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy optionally substituted phenyl (C 1 -C 4 ) alkylthio or the radical III (CH 2 ) - n C≡C- R 3 (III)
Figure imgf000104_0001
bedeuten, mit Verbindungen der Formel TV
Figure imgf000104_0001
mean with compounds of the formula TV
Figure imgf000104_0002
Figure imgf000104_0002
umsetzt und, falls R12 eine von der Formel III abweichende Bedeutung hat, anschließend die erhaltenen Verbindungen im Rest R12 oxidiert und die entstandenen Oxidationsprodukte mit Verbindungen der Formel V implemented and, if R 12 has a meaning deviating from the formula III, then the compounds obtained are oxidized in the radical R 12 and the resulting oxidation products with compounds of the formula V
HX (CH2)-n C Ξ C- R3 (V)
Figure imgf000104_0003
HX (CH 2 ) - n C Ξ C- R 3 (V)
Figure imgf000104_0003
zu den Endprodukten der Formel I, worin R12 = Rest der Formel III bedeutet, umsetzt und, wenn R3 = H bedeutet, den Wasserstoff gegebenenfalls austauscht to the end products of the formula I, in which R 12 = radical of the formula III, and, if R 3 = H, optionally exchanges the hydrogen
Fungizide Mittel, dadurch gekennzeichnet, daß sie eine wirksame Menge einer Verbindung der Formel I gemäß einem oder mehreren der Ansprüche 1 bis 4 enthalten. 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.
Verwendung von Verbindungen der Formel I gemäß einem oder mehreren der Ansprüche 1 bis 4 zur Bekämpfung von Schadpilzen. Use of compounds of formula I according to one or more of claims 1 to 4 for controlling harmful fungi.
Verfahren zur Bekämpfung von Schadpilzen, dadurch gekennzeichnet, 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 Process for combating harmful fungi, characterized in that an effective amount of a compound of the formula I according to one or more of claims 1 to 4 is applied to these or the plants, areas or substrates affected by them
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WO2011032656A1 (en) 2009-09-18 2011-03-24 Bayer Cropscience Ag 5-fluor-2-thio-substituted pyrimidine derivatives
CN113754633A (en) * 2021-09-26 2021-12-07 中国农业大学 1- (6-substituted pyrimidine-4-yl) -1,2,3, 4-tetrahydroquinoline compound and preparation method and application thereof
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