EP0518862A1 - Pyrimidine derivatives, process for making them, agents containing them and their use as fungicides - Google Patents

Pyrimidine derivatives, process for making them, agents containing them and their use as fungicides

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Publication number
EP0518862A1
EP0518862A1 EP90916261A EP90916261A EP0518862A1 EP 0518862 A1 EP0518862 A1 EP 0518862A1 EP 90916261 A EP90916261 A EP 90916261A EP 90916261 A EP90916261 A EP 90916261A EP 0518862 A1 EP0518862 A1 EP 0518862A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
phenyl
alkoxy
alkylthio
halogen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP90916261A
Other languages
German (de)
French (fr)
Inventor
Wolfgang Giencke
Burkhard Sachse
Heinrich Wicke
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Hoechst AG
Hoechst Schering Agrevo GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hoechst AG, Hoechst Schering Agrevo GmbH filed Critical Hoechst AG
Publication of EP0518862A1 publication Critical patent/EP0518862A1/en
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • 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

Definitions

  • the present invention relates to new pyrimidine derivatives, processes for their preparation, compositions containing them and their use as fungicides.
  • Pyrimidine derivatives are already known as effective components in fungicidal compositions (cf. EP-A-270 362,
  • the present invention therefore relates to
  • R 1 hydrogen, (C 1 -C 6 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 2 -C 6 ) alkenyl,
  • (C 1 -C 4 ) alkyl where the latter two radicals in the cycloalkyl part can be substituted up to three times by (C 1 -C 4 ) alkyl, phenyl,
  • Phenoxy- (C 1 -C 4 ) alkyl Phenoxy- (C 1 -C 4 ) alkyl, phenylmercapto (C 1 -C 4 ) alkyl, phenyl- (C 1 -C 4 ) alkyl, phenoxy-phenoxy (C 1 -C 4 ) alkyl, the five last-mentioned radicals in Phenyl part up to three times by halogen, nitro, (C 1 -C 4 ) alkyl,
  • (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl or (C 1 -C 4 ) haloalkoxy may be substituted
  • R 5 hydrogen, (C 1 -C 4 ) alkyl, (C 3 -C 7 ) cycloalkyl,
  • (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl or (C 1 -C 4 ) haloalkoxy may be substituted, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) alkynyloxy,
  • (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkylthio R 6 hydrogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 2 -C 6 ) - alkenyloxy, (C 2 -C 6 ) alkynyloxy, (C 1 -C 4 ) alkylthio,
  • the alkyl, alkenyl or alkynyl radicals can be both straight-chain and branched.
  • Halogen means F, Cl, Br, J, preferably F, Cl and Br.
  • the prefix "halo" in the designation of a substituent means here and below that this substituent can occur once or several times with the same or different meaning.
  • the prefix "halo” includes fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine.
  • Examples of haloalkyl are: CF 3 , CF 2 CHF 2 , CF 2 CF 3 , CCl 3 , CCl 2 F, CF 2 CF 2 CF 3 , CF 2 CHFCF 3 and (CF 2 ) 3 CF 3 .
  • Examples of haloalkoxy are OCF 3 , OCF 2 CHF 2 or OCF 2 CF 2 CF 3 .
  • R 1 hydrogen, (C 1 -C 6 ) alkyl, phenyl, phenyl- (C 1 -C 2 ) -alkyl, phenoxy-phenoxy- (C 1 -C 2 ) alkyl, phenoxy- (C 1 -C 2 ) - alkyl, the four latter radicals in
  • (C 1 -C 4 ) alkyl may be substituted; (C 1 -C 3 ) alkoxy- (C 1 -C 2 ) alkyl,
  • R 7 , R 3 independently of one another hydrogen, (C 1 -C 3 ) alkyl,
  • Phenyl where the phenyl radical can be substituted up to three times by halogen or (C 1 -C 4 ) alkyl
  • R 4 hydrogen
  • R 5 hydrogen, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl,
  • R 6 hydrogen, (C 1 -C 4 ) alkyl, halogen, phenyl or
  • 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 Hydrobromic acid, also phosphoric acid,
  • Nitric acid sulfuric acid, monofunctional or bifunctional carboxylic acids and hydroxycarboxylic acids such as acetic acid,
  • Citric acid Citric acid, salicylic acid, sorbic acid or
  • Lactic acid and sulfonic acids such as p-toluenesulfonic acid or 1,5-naphthalenedisulfonic acid.
  • Acid addition salts of the compounds of formula I can in a simple manner by conventional salt formation methods, for. B. by dissolving a compound of formula I in a suitable organic solvent and adding the
  • Acid are obtained and in a known manner, e.g. B. by filtration, isolated and optionally cleaned by washing with an inert organic solvent
  • the present invention also relates to a
  • Dehalogenation can be carried out with hydrogen in the presence of catalysts (e.g. palladium / carbon) in an inert solvent e.g. Water, lower alcohol (such as methanol and ethanol), ethyl acetate or toluene, or mixtures thereof. That is advantageous
  • alkali metal are sodium, potassium and
  • the reaction can be carried out between 0 ° C and 130 ° C within 0.5 h to 72 h.
  • Alkali metal compound (II) can be used in an amount of 1 to 2 mol equivalents based on 1 equivalent of
  • Halopvrimidins (I) can be used.
  • the reaction is usually carried out in the presence of a solvent
  • Alkali metal compound R 5 Y is used, in which R 5 is for (C 1 -C 4 ) alkylthio, phenoxy, phenylmercapto,
  • (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkylthio becomes an ether (e.g. diethyl ether, dioxane or
  • Tetrahydrofuran Tetrahydrofuran
  • a nitrile e.g. acetonitrile
  • an aromatic hydrocarbon e.g. toluene or xylene
  • (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy may be substituted by reacting corresponding ones
  • the Grignard connection such as, for example, 1,2-bis (diphenylphosphino) -ethane-nickel- (II) - chloride or 1,3-bis- (diphenylphosphino) propane-nickel- (II) chloride can be obtained (cf. Chem. Pharm. Bull. 16, 2160 (1978)).
  • R 5 MgX (III) can be used in amounts of 1-2.5 molar equivalents based on 1 equivalent of halopyrimidine (I).
  • Suitable solvents are ethers such as
  • Phosphorus tribromide can be used.
  • the reactions can in a solvent, but also without
  • the halogenating agent can be used in amounts of 1 to 4
  • Hydroxypyrimidins (I) can be used. The reactions can take place in a temperature range of 25-160 ° C
  • solvents e.g.
  • aromatic hydrocarbons e.g. benzene or toluene, etc.
  • halogenated hydrocarbons e.g.
  • Chlorobenzene used.
  • the hydroxypyrimidines (I) can be condensed by
  • X is halogen (eg chlorine, bromine, iodine) and R 13 is lower alkyl radicals such as methyl, ethyl or propyl.
  • the reactions are carried out in the temperature range of 20-110 ° C or at the boiling point of the solvent within 2-72 h.
  • the ⁇ -oxocarboxylate V can in
  • Amidine derivative IV can be used.
  • the reaction is carried out in the presence of a base and a solvent
  • bases e.g. inorganic bases such as alkali metal hydroxides and carbonates or organic bases such as sodium alkoxides, trialkylamines and
  • N, N-dialkylanilines can be used.
  • a solvent lower alcohols (such as methanol and ethanol), cyclic ethers (such as dioxane and THF), pyridine, N, N-dimethylformamide, water or mixtures thereof are suitable.
  • the amidine derivatives IV and the ⁇ -oxocarboxylates V can be prepared by processes known per se (cf. J. Org. Chem. 32, 1591 (1967) or Synthesis 1982, 451 and Organikum 1986, 516 ff.).
  • the compounds of the formula I according to the invention are notable for an excellent fungicidal action.
  • the compounds of the invention are also suitable for use in technical fields, for example as wood preservatives, as preservatives in
  • the invention also relates to means which
  • the agents according to the invention generally contain the active ingredients of the formula I in an amount of 1 to 95% by weight.
  • WP Wettable powder
  • EC emulsifiable concentrates
  • SC aqueous solutions
  • emulsions sprayable solutions
  • SC Oil or water-based dispersions
  • SC suspoemulsions
  • DP dusts
  • pickling agents granules in the form of micro, spray, elevator and adsorption granules
  • WG water-dispersible granules
  • ULV water-dispersible granules
  • the necessary formulation aids such as
  • Manufacture fertilizers and / or growth regulators e.g. 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 ingredient, contain a wetting agent, e.g. polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates and dispersants, e.g.
  • Emulsifiable concentrates are made by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers.
  • organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons.
  • emulsifiers e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons.
  • Alkylarylsulfonic acid calcium salts such as
  • Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers,
  • Fatty alcohol polyglycol ether Fatty alcohol polyglycol ether, propylene oxide-ethylene oxide condensation products, sorbitan fatty acid esters,
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. Talc, natural clays such as kaolin, bentonite, pyrophillite or diatomaceous earth.
  • Finely divided solid substances e.g. Talc, natural clays such as kaolin, bentonite, pyrophillite or diatomaceous earth.
  • Granules can either by spraying the active ingredient onto adsorbable, granulated inert material
  • Active ingredient concentrates using adhesives e.g.
  • Mineral oils on the surface of carriers such as sand, kaolinite or granulated inert material.
  • Suitable active ingredients can also be used in the production of Fertilizer granules in the usual way - if desired in a mixture with fertilizers - are granulated.
  • the active substance concentration in wettable powders is e.g. about 10 to 90 wt .-%, the rest of 100 wt .-% consists of conventional formulation components. In the case of emulsifiable concentrates, the active substance concentration can be approximately 5 to 80% by weight. Dust-like formulations usually contain 5 to 20 wt .-% of active ingredient, sprayable
  • the active ingredient content depends in part on whether the active ingredient
  • Connection is liquid or solid and which
  • Granular auxiliaries, fillers, etc. can be used.
  • the active ingredient formulations mentioned may contain the usual adhesive, wetting,
  • Dispensing emulsifying, penetrating, solvent, fillers or carriers.
  • solvent emulsifying, penetrating, solvent, fillers or carriers.
  • 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. between 0.005 and 10.0 kg / ha or more of active substance, but is preferably between 0.01 and 5 kg / ha.
  • the active compounds according to the invention can in their
  • fungicides known from the literature which can be combined according to the invention with the compounds of the formula I are, for example to name the following products:
  • Fentin acetates fentin hydroxides, carboxin, oxycarboxin,
  • Oxine-Cu Cu-oxides
  • sulfur fosethyl aluminum
  • Cetyl-trimethyl-ammonium chloride salts of long-chain primary, secondary or tertiary amines, alkyl-propylene amines, lauryl-pyridinium bromide, ethoxylated guaternized fatty amines, alkyl-dimethyl-benzyl-ammonium chloride and 1-hydroxyethyl-2-alkyl-imidazoline.
  • the above-mentioned combination partners are known active ingredients, which are largely in C.R. Worthing,
  • active compounds according to the invention in particular those of the examples listed, 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,
  • Insecticides include, for example
  • Phosphoric acid esters carbamates, carboxylic acid esters,
  • Pirimiphos-methyl Profenofos, Prothiofos, Sulprofos, Triazophos, Trichlorphon.
  • Chlorobenzylates chlorofluazuron, 2- (4-chlorophenyl) - 4,5-diphenylthiophene (UBI-T 930), chlofentezine,
  • Triflumaron, nuclear polyhedron and granuloviruses Triflumaron, nuclear polyhedron and granuloviruses.
  • the active ingredient content from the commercially available
  • Formulations of use forms prepared can vary widely, the concentration of the active ingredient
  • Application forms can range from 0.0001 to 100% by weight
  • Active ingredient preferably between 0.001 and 1 wt .-%.
  • 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,
  • Dispersion concentrate is prepared by mixing 40 parts by weight of active ingredient with 7 parts by weight of one
  • 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 one
  • Granulate carrier material such as attapulgite, pumice granulate and / or quartz sand.
  • a suspension of the wettable powder from example b) with a solids content of 30% is expediently used and this is sprayed onto the
  • Carrier material approx. 95% of the finished granulate.
  • a sodium methylate solution is obtained by dissolving 0.184 g (0.008 mol) sodium in 40 ml abs. Made methanol. 1.30 g (0.0044 mol) of 4-benzyl-2- (6-methyl-pyridin-2-yl) -6-chloro-pyrimidine are added to this solution and the mixture is boiled for 3 hours
  • Example 1 Rice plants of the "Ballila” variety, about 5 weeks old, were sprayed with 0.05% gelatin solution at the concentration indicated below
  • Barley plants were strongly inoculated in the 2-leaf stage with conidia of barley mildew (Erysiphe graminis hordei) and in a greenhouse at 20 ° C and a relative
  • Humidity incubated in a climatic chamber Humidity incubated in a climatic chamber.
  • the efficiency is a percentage of the untreated
  • Trial plants can be made.
  • the degree of infestation was in% affected leaf area compared to

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Environmental Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Health & Medical Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

Abstract

Des procédés ayant la formule (I) dans laquelle R1 représente un hydrogène, alkyle, alkoxyalkyle, alkylthioalkyle, alkényle, alkinyle, cycloalkyle, cycloalkylalkyle, les deux derniers résidus précités pouvant être substitués dans la partie cycloalkyle, ainsi que les résidus phényle, phénoxyalkyle, phénylmercaptoalkyle, phénylalkyle, phénoxy-phénoxyalkyle, ces résidus pouvant être substitués dans la partie phényle, R2, R3, R4, représentent, indépendamment les uns des autres, un hydrogène, alkyle, phényle (substitué), R5 est un hydrogène, alkyle, cycloalkyle, cycloalkylalkyle, ces deux résidus pouvant être substitués dans la partie cycloalkyle, ainsi que les résidus halo-alkyle, alkoxy, alkylthio, alkoxyalkyle, alkylthioalkyle, halogène, alkényle, alkinyle, phényle, phénoxy, phénylalkyle, phénoxyalkyle, phénylmercaptoalkyle, phénylmercapto, phénylalkoxy ou phénylalkylthio, ces résidus pouvant être substitués dans la partie phényle, ainsi que les résidus alkényloxy, alkinyloxy, haloalkoxy, alkoxyalkoxy, alkylthioalkylthio, R6 est un hydrogène, alkyle, alkoxy, alkényloxy, alkinyloxy, alkylthio, halogène, phényl, le résidu phényle pouvant être substitué, R7, R8, R9, R10 représentent, indépendamment les uns des autres, un hydrogène, nitro, cyano, alkyle, alkoxy, alkylthio, haloalkyle ou haloalkoxy, R11, R12 sont, indépendamment les uns des autres, un hydrogène ou un alkyle, et n = 1 - 3, ainsi que leurs sels d'addition d'acide, possèdent des propriétés fongicides avantageuses.Processes having the formula (I) in which R1 represents a hydrogen, alkyl, alkoxyalkyl, alkylthioalkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, the last two abovementioned residues possibly being substituted in the cycloalkyl part, as well as the phenyl, phenoxyalkyl residues, phenylmercaptoalkyl, phenylalkyl, phenoxy-phenoxyalkyl, these residues which may be substituted in the phenyl part, R2, R3, R4, represent, independently of each other, a hydrogen, alkyl, phenyl (substituted), R5 is a hydrogen, alkyl, cycloalkyl , cycloalkylalkyl, these two residues possibly being substituted in the cycloalkyl part, as well as the halo-alkyl, alkoxy, alkylthio, alkoxyalkyl, alkylthioalkyl, halogen, alkenyl, alkinyl, phenyl, phenoxy, phenylalkyl, phenoxyalkyl, phenylmercaptoalkyl, phenylmercaptoxy or phenylmercaptoalkyl, phenylmercapto, phenylalkylthio, these residues possibly being substituted in the phenyl part, as well as alkenyloxy, alkinyloxy, haloalkoxy residues , alkoxyalkoxy, alkylthioalkylthio, R6 is hydrogen, alkyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, halogen, phenyl, the phenyl residue possibly being substituted, R7, R8, R9, R10 represent, independently of each other, a hydrogen, nitro , cyano, alkyl, alkoxy, alkylthio, haloalkyl or haloalkoxy, R11, R12 are, independently of each other, hydrogen or alkyl, and n = 1 - 3, as well as their acid addition salts, have advantageous fungicidal properties.

Description

Beschreibung description
Pyrimidin-Derivate, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Fungizide Pyrimidine derivatives, processes for their preparation, compositions containing them and their use as fungicides
Die vorliegende Erfindung betrifft neue Pyrimidin-Derivate, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Fungizide. The present invention relates to new pyrimidine derivatives, processes for their preparation, compositions containing them and their use as fungicides.
Pyrimidin-Derivate sind bereits als wirksame Komponenten in fungiziden Mitteln bekannt (vgl. EP-A-270 362, Pyrimidine derivatives are already known as effective components in fungicidal compositions (cf. EP-A-270 362,
EP-A-259 139, EP-A 234 104). Die Wirkung dieser Pyrimidin- Derivate ist jedoch insbesondere bei niedrigen EP-A-259 139, EP-A 234 104). However, the effect of these pyrimidine derivatives is particularly low
Aufwandmengen nicht immer befriedigend. Application rates are not always satisfactory.
Es wurden neue Pyrimidin-Derivate gefunden, die New pyrimidine derivatives have been found that
vorteilhafte Wirkungen bei der Bekämpfung eines breiten Spektrums phytopathogener Pilze insbesondere bei niedrigen Dosierungen aufweisen. have advantageous effects in combating a broad spectrum of phytopathogenic fungi, especially at low doses.
Gegenstand der vorliegenden Erfindung sind daher die The present invention therefore relates to
Verbindungen der Formel I, Compounds of the formula I,
worin wherein
R1 = Wasserstoff, (C1-C6)Alkyl, (C1-C4)Alkoxy- (C1-C4)alkyl, (C1-C4)Alkylthio-(C1-C4)alkyl, (C2-C6)Alkenyl, R 1 = hydrogen, (C 1 -C 6 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 2 -C 6 ) alkenyl,
(C2-C6)Alkinyl, (C3-C7)Cycloalkyl, (C3-C7)Cycloalkyl-(C 2 -C 6 ) alkynyl, (C 3 -C 7 ) cycloalkyl, (C 3 -C 7 ) cycloalkyl-
(C1-C4)alkyl, wobei die beiden letztgenannten Reste im Cycloalkylteil bis zu dreifach durch (C1-C4)Alkyl substituiert, sein können, Phenyl, (C 1 -C 4 ) alkyl, where the latter two radicals in the cycloalkyl part can be substituted up to three times by (C 1 -C 4 ) alkyl, phenyl,
Phenoxy-(C1-C4)alkyl, Phenylmercapto(C1-C4) alkyl, Phenyl-(C1-C4) alkyl, Phenoxy-phenoxy(C1-C4) alkyl, wobei die fünf letztgenannten Reste im Phenylteil bis zu dreifach durch Halogen, Nitro, (C1-C4)Alkyl, Phenoxy- (C 1 -C 4 ) alkyl, phenylmercapto (C 1 -C 4 ) alkyl, phenyl- (C 1 -C 4 ) alkyl, phenoxy-phenoxy (C 1 -C 4 ) alkyl, the five last-mentioned radicals in Phenyl part up to three times by halogen, nitro, (C 1 -C 4 ) alkyl,
(C1-C4)Alkoxy, (C1-C4) Alkylthio, (C1-C4)Haloalkyl oder (C1-C4)Haloalkoxy substituiert sein können, R2, R3, R4 = unabhängig voneinander Wasserstoff, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl or (C 1 -C 4 ) haloalkoxy may be substituted, R 2 , R 3 , R 4 = independently of one another Hydrogen,
(C1-C6)Alkyl, Phenyl, wobei der Phenylrest bis zu dreifach durch Halogen, Nitro, (C1-C4)Alkyl, (C 1 -C 6 ) alkyl, phenyl, the phenyl radical being up to triple by halogen, nitro, (C 1 -C 4 ) alkyl,
(C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl oder (C1-C4)Haloalkoxy substituiert sein kann, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl or (C 1 -C 4 ) haloalkoxy may be substituted,
R5 = Wasserstoff, (C1-C4) Alkyl, (C3-C7)Cycloalkyl, R 5 = hydrogen, (C 1 -C 4 ) alkyl, (C 3 -C 7 ) cycloalkyl,
(C3-C7) Cycloalkyl- (C2-C4) alkyl, wobei die beiden letztgenannten Reste im Cycloalkylteil bis zu dreifach durch (C1-C4)Alkyl substituiert sein können, (C 3 -C 7 ) cycloalkyl- (C 2 -C 4 ) alkyl, where the latter two radicals in the cycloalkyl part can be substituted up to three times by (C 1 -C 4 ) alkyl,
(C1-C4)Haloalkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Alkoxy- (C1-C4) alkyl, (C1-C4)Alkylthio- (C1-C4)alkyl, Halogen, (C2-C6)Alkenyl, (C2-C5)Alkinyl, Phenyl, Phenoxy, Phenyl (C1-C4)alkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, halogen, (C 2 -C 6 ) alkenyl, (C 2 -C 5 ) alkynyl, phenyl, phenoxy, phenyl (C 1 -C 4 ) alkyl,
Phenoxy-(C1-C4)alkyl, Phenylmercapto-(C1-C4)alkyl, Phenylmercapto, Phenyl-(C1-C4)alkoxy oder Phenoxy- (C 1 -C 4 ) alkyl, phenylmercapto- (C 1 -C 4 ) alkyl, phenylmercapto, phenyl- (C 1 -C 4 ) alkoxy or
Phenyl-(C1-C4)alkylthio, wobei die acht Phenyl- (C 1 -C 4 ) alkylthio, the eight
letztgenannten Reste im Phenylteil bis zu dreifach durch Halogen, Nitro, Cyano, (C1-C4)Alkyl, the latter radicals in the phenyl moiety up to three times by halogen, nitro, cyano, (C 1 -C 4 ) alkyl,
(C1-C4)Alkoxy, (C1-C4) Alkylthio, (C1-C4)Haloalkyl oder (C1-C4)Haloalkoxy substituiert sein können, (C2-C4)Alkenyloxy, (C2-C4)Alkinyloxy, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl or (C 1 -C 4 ) haloalkoxy may be substituted, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) alkynyloxy,
(C1-C4)Haloalkoxy, (C1-C4)Alkoxy-(C1-C4)alkoxy, (C 1 -C 4) haloalkoxy, (C 1 -C 4) alkoxy, alkoxy (C 1 -C 4),
(C1-C4)Alkylthio-(C1-C4)alkylthio R6 = Wasserstoff, (C1-C4)Alkyl, (C1-C4)Alkoxy, (C2-C6)- Alkenyloxy, (C2-C6)Alkinyloxy, (C1-C4)Alkylthio, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkylthio R 6 = hydrogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 2 -C 6 ) - alkenyloxy, (C 2 -C 6 ) alkynyloxy, (C 1 -C 4 ) alkylthio,
Halogen, Phenyl, wobei der Phenylrest bis zu dreifach durch Halogen, Nitro, Cyano, (C1-C4)Alkyl, (C1-C4)- Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl oder Halogen, phenyl, the phenyl radical being up to three times by halogen, nitro, cyano, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl or
(C1-C4)Haloalkoxy substituiert sein kann, R7, R8, R9, R10 = unabhängig voneinander Wasserstoff, (C 1 -C 4 ) haloalkoxy can be substituted, R 7 , R 8 , R 9 , R 10 = independently of one another hydrogen,
Halogen, Nitro, Cyano, (C1-C4)Alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl oder Halogen, nitro, cyano, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl or
(C1-C4)Haloalkoxy, R11, R12 = unabhängig voneinander Wasserstoff oder (C 1 -C 4 ) haloalkoxy, R 11 , R 12 = independently of one another hydrogen or
(C1-C4)Alkyl und n = 1 - 3 bedeuten, sowie deren Säureadditionssalze. (C 1 -C 4 ) alkyl and n = 1 - 3, and their acid addition salts.
Dabei können die Alkyl-, Alkenyl- oder Alkinylreste sowohl geradkettig als auch verzweigt sein. Halogen bedeutet F, Cl, Br, J, bevorzugt F, Cl und Br. Die Vorsilbe "Halo" in der Bezeichnung eines Substituenten bedeutet hier und im folgenden, daß dieser Substituent einfach oder mehrfach bei gleicher oder verschiedener Bedeutung auftreten kann. Die Vorsilbe "Halo" beinhaltet Fluor, Chlor, Brom oder Jod, insbesondere Fluor, Chlor oder Brom. Als Beispiele für Halogenalkyl seien genannt: CF3, CF2CHF2, CF2CF3, CCl3, CCl2F, CF2CF2CF3, CF2CHFCF3 und (CF2)3CF3. Beispiele für Haloalkoxy sind OCF3, OCF2CHF2 oder OCF2CF2CF3. The alkyl, alkenyl or alkynyl radicals can be both straight-chain and branched. Halogen means F, Cl, Br, J, preferably F, Cl and Br. The prefix "halo" in the designation of a substituent means here and below that this substituent can occur once or several times with the same or different meaning. The prefix "halo" includes fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine. Examples of haloalkyl are: CF 3 , CF 2 CHF 2 , CF 2 CF 3 , CCl 3 , CCl 2 F, CF 2 CF 2 CF 3 , CF 2 CHFCF 3 and (CF 2 ) 3 CF 3 . Examples of haloalkoxy are OCF 3 , OCF 2 CHF 2 or OCF 2 CF 2 CF 3 .
Bevorzugt unter den Verbindungen der Formel I sind solche, worin R1 = Wasserstoff, (C1-C6) Alkyl, Phenyl, Phenyl-(C1-C2)- alkyl, Phenoxy-phenoxy-(C1-C2)alkyl, Phenoxy-(C1-C2) - alkyl, wobei die vier letztgenannten Reste im Preferred among the compounds of the formula I are those in which R 1 = hydrogen, (C 1 -C 6 ) alkyl, phenyl, phenyl- (C 1 -C 2 ) -alkyl, phenoxy-phenoxy- (C 1 -C 2 ) alkyl, phenoxy- (C 1 -C 2 ) - alkyl, the four latter radicals in
Phenylteil bis zu dreifach durch Halogen oder  Phenyl part up to three times by halogen or
(C1-C4)Alkyl substituiert sein können; (C1-C3)Alkoxy- (C1-C2) alkyl, (C 1 -C 4 ) alkyl may be substituted; (C 1 -C 3 ) alkoxy- (C 1 -C 2 ) alkyl,
R7, R3 = unabhängig voneinander Wasserstoff, (C1-C3) Alkyl,R 7 , R 3 = independently of one another hydrogen, (C 1 -C 3 ) alkyl,
Phenyl, wobei der Phenylrest bis zu dreifach durch Halogen oder (C1-C4)Alkyl substituiert sein kann, Phenyl, where the phenyl radical can be substituted up to three times by halogen or (C 1 -C 4 ) alkyl,
R4 = Wasserstoff, R 4 = hydrogen,
R5 = Wasserstoff, (C1-C6)Alkyl, (C3-C6)Cycloalkyl, R 5 = hydrogen, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl,
(C5-C6) Cycloalkyl-(C1-C3)alkyl, Phenyl, (C 5 -C 6 ) cycloalkyl- (C 1 -C 3 ) alkyl, phenyl,
Phenyl-(C1-C2)alkylthio, Phenyl-(C1-C2) alkyl, wobei die drei letztgenannten Reste im Phenylteil bis zu dreifach durch Halogen, (C1-C4)Alkyl, (C1-C3)Haloalkyl oder (C1-C4)Alkoxy substituiert sein können, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C2-C4)Alkenyloxy, Phenyl- (C 1 -C 2 ) alkylthio, phenyl- (C 1 -C 2 ) alkyl, the three latter radicals in the phenyl part being up to threefold by halogen, (C 1 -C 4 ) alkyl, (C 1 -C 3 ) Haloalkyl or (C 1 -C 4 ) alkoxy can be substituted, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 2 -C 4 ) alkenyloxy,
(C2-C4)Alkinyloxy, (C2-C3)Alkenyl, (C2-C4)Alkinyl oder (C1-C4)Alkoxy-(C1-C4)alkoxy (C 2 -C 4 ) alkynyloxy, (C 2 -C 3 ) alkenyl, (C 2 -C 4 ) alkynyl or (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkoxy
R6 = Wasserstoff, (C1-C4) Alkyl, Halogen, Phenyl oder R 6 = hydrogen, (C 1 -C 4 ) alkyl, halogen, phenyl or
(C1-C3)Alkoxy R7, R8, R9, R 10 = unabhängig voneinander Wasserstoff, (C 1 -C 3 ) alkoxy R 7 , R 8 , R 9 , R 10 = independently of one another hydrogen,
Halogen, (C1-C4)Alkyl, (C1-C4)Haloalkyl oder Halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl or
(C1-C4)Alkylthio (C 1 -C 4 ) alkylthio
R11, R12 = Wasserstoff und n = 1 bedeuten, sowie deren Säureadditionssalze. Zur Herstellung der Säureadditionssalze der Verbindungen der Formel I kommen folgende Säuren in Frage: R 11 , R 12 = hydrogen and n = 1, and their acid addition salts. The following acids are suitable for the preparation of the acid addition salts of the compounds of the formula I:
Halogenwasserstoffsäuren wie Chlorwasserstoffsäure oder Bromwasserstoffsäure, ferner Phosphorsäure, Hydrohalic acids such as hydrochloric acid or Hydrobromic acid, also phosphoric acid,
Salpetersäure, Schwefelsäure, mono- oder bifunktionelle Carbonsäuren und Hydroxycarbonsäuren wie Essigsäure, Nitric acid, sulfuric acid, monofunctional or bifunctional carboxylic acids and hydroxycarboxylic acids such as acetic acid,
Maleinsäure, Bernsteinsäure, Fumarsäure, Weinsäure, Maleic acid, succinic acid, fumaric acid, tartaric acid,
Citroncnsäυre, Salicylsäure, Sorbinsäure oder Citric acid, salicylic acid, sorbic acid or
Milchsäure, sowie Sulfonsäuren wie p-Toluolsulfonsäure oder 1,5-Naphthalindisulfonsäure. Die  Lactic acid, and sulfonic acids such as p-toluenesulfonic acid or 1,5-naphthalenedisulfonic acid. The
Säureadditionssalze der Verbindungen der Formel I können in einfacher Weise nach üblichen Salzbildungsmethoden, z. B. durch Lösen einer Verbindung der Formel I in einem geeigneten organischen Lösemittel und Hinzufügen der  Acid addition salts of the compounds of formula I can in a simple manner by conventional salt formation methods, for. B. by dissolving a compound of formula I in a suitable organic solvent and adding the
Säure erhalten werden und in bekannter Weise, z. B. durch Abfiltrieren, isoliert und gegebenenfalls durch Waschen mit einem inerten organischen Lösemittel gereinigt Acid are obtained and in a known manner, e.g. B. by filtration, isolated and optionally cleaned by washing with an inert organic solvent
werden. become.
Gegenstand der vorliegenden Erfindung ist auch ein The present invention also relates to a
Verfahren zur Herstellung der. Verbindungen der Formel I. Die neuen Pyrimidin-Derivate der Formel (I) können nach den folgenden Methoden dargestellt werden: Process for the preparation of the. Compounds of the formula I. The new pyrimidine derivatives of the formula (I) can be prepared by the following methods:
1) Pyrimidin-Derivate der Formel I mit R5 = H können durch reduktive Dehalogenierung von entsprechenden 1) Pyrimidine derivatives of formula I with R 5 = H can be obtained by reductive dehalogenation of the corresponding
Halopyrimidinen der Formel I, in denen R5 für HalogenHalopyrimidines of the formula I in which R 5 is halogen
(Cl, Br, J) steht und die restlichen Substituenten wie in Formel I definiert sind, erhalten werden. Die (Cl, Br, J) and the remaining substituents as defined in formula I are obtained. The
Dehalogenierung kann mit Wasserstoff in Gegenwart von Katalysatoren (z.B. Palladium/Kohle) in einem inerten Lösungsmittel z.B. Wasser, niederer Alkohol (wie Methanol und Ethanol), Ethylacetat oder Toluol oder Gemischen derselben durchgeführt werden. Vorteilhaft ist die  Dehalogenation can be carried out with hydrogen in the presence of catalysts (e.g. palladium / carbon) in an inert solvent e.g. Water, lower alcohol (such as methanol and ethanol), ethyl acetate or toluene, or mixtures thereof. That is advantageous
Zugabe von Basen wie Alkali- oder Erdalkalihydroxide bzw. -carbonate. Die Reaktion wird vorteilhaft im  Add bases such as alkali or alkaline earth metal hydroxides or carbonates. The reaction is advantageous in
Bereich von 15-60°C unter einem Druck von 1 bis 5 bar durchgeführt . 2) Pyrimidin-Derivate der Formel I, worin R5 für Range of 15-60 ° C carried out under a pressure of 1 to 5 bar. 2) Pyrimidine derivatives of the formula I, in which R 5 is
(C1-C4)Alkoxy, (C1-C4)Alkylthio, Phenoxy, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, phenoxy,
Phenylmercapto, Phenyl- (C1-C4)alkoxy oder Phenylmercapto, phenyl- (C 1 -C 4 ) alkoxy or
Phenyl-(C1-C4)alkylthio, wobei die 4 letztgenannten Phenyl- (C 1 -C 4 ) alkylthio, the 4 last mentioned
Reste im Phenylteil bis zu dreifach durch Halogen,  Residues in the phenyl part up to three times due to halogen,
Nitro, Cyano, (C1-C4)Alkyl, (C1-C4)Alkoxy, Nitro, cyano, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy,
(C1-C4)Alkylthio, (C1-C4)Haloalkyl oder (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl or
(C1-C4)Haloalkoxy substituiert sein können, (C 1 -C 4 ) haloalkoxy can be substituted,
(C2-C4)Alkenyloxy, (C2-C4)Alkinyloxy, (C1-C4)Haloalkoxy, (C1-C4)Alkoxy-(C1-C4)alkoxy oder (C 2 -C 4) alkenyloxy, (C 2 -C 4) alkynyloxy, (C 1 -C 4) haloalkoxy, (C 1 -C 4) alkoxy- (C 1 -C 4) alkoxy or
(C1-C4)Alkylthio-(C1-C4)alkylthio steht, können durch Reaktion von entsprechenden Halopyrimidinen der Formel (I) mit R5 = Halogen mit einer AlkalimetallVerbindung der Formel R5-Y (II), worin R5 wie oben angegeben definiert ist und Y für ein Alkalimetall steht, erhalten werden. Beispiele für Alkalimetall sind Natrium, Kalium und (C 1 -C 4 ) Alkylthio- (C 1 -C 4 ) alkylthio, can by reaction of corresponding halopyrimidines of the formula (I) with R 5 = halogen with an alkali metal compound of the formula R 5 -Y (II), in which R 5 is as defined above and Y is an alkali metal. Examples of alkali metal are sodium, potassium and
Lithium.  Lithium.
Die Reaktion kann zwischen 0°C und 130°C innerhalb von 0,5 h bis 72 h durchgeführt v/erden. Die The reaction can be carried out between 0 ° C and 130 ° C within 0.5 h to 72 h. The
Alkalimetallverbindung (II) kann in Menge von 1 bis 2 Moläσuivalenten bezogen auf 1 Äguivalent des  Alkali metal compound (II) can be used in an amount of 1 to 2 mol equivalents based on 1 equivalent of
Halopvrimidins (I) eingesetzt werden. Die Reaktion wird gewöhnlich in Gegenwart eines Lösungsmittels  Halopvrimidins (I) can be used. The reaction is usually carried out in the presence of a solvent
durchgeführt.  carried out.
In den Fällen, in denen eine Alkalimetallverbindung R5-Y eingesetzt wird, worin R5 für (C1-C4)Alkoxy, In cases where an alkali metal compound R 5 -Y is used, in which R 5 is for (C 1 -C 4 ) alkoxy,
(C2-C4)Alkenyloxy, (C2-C4)Alkinyloxy, (C1-C4)Haloalkoxy oder (C1-C4)Alkoxy- (C1-C4)alkoxy steht, wird (C 2 -C 4) alkenyloxy, (C 2 -C 4) alkynyloxy, (C 1 -C 4) haloalkoxy or (C 1 -C 4) alkoxy is (C 1 -C 4) alkoxy, is
zweckmäßigerweise der korrespondierende Alkohol R5OH oder ein Ether (z.B. Diethylether, Dioxan oder expediently the corresponding alcohol R 5 OH or an ether (for example diethyl ether, dioxane or
Tetrahydrofuran) oder eine Mischung derselben als  Tetrahydrofuran) or a mixture thereof as
Lösungsmittel benutzt. In den Fällen, in denen eine  Solvent used. In cases where a
Alkalimetallverbindung R5Y eingesetzt wird, worin R5 für (C1-C4)Alkylthio, Phenoxy, Phenylmercapto, Alkali metal compound R 5 Y is used, in which R 5 is for (C 1 -C 4 ) alkylthio, phenoxy, phenylmercapto,
Phenyl-(C1-C4)alkoxy, Phenyl-(C1-C4)alkylthio oder Phenyl- (C 1 -C 4 ) alkoxy, phenyl- (C 1 -C 4 ) alkylthio or
(C1-C4)-Alkylthio-(C1-C4)alkylthio steht, wird ein Ether (z.B. Diethylether, Dioxan oder (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkylthio, becomes an ether (e.g. diethyl ether, dioxane or
Tetrahydrofuran), ein Nitril (z.B. Acetonitril), ein aromatischer Kohlenv/asserstoff (z.B. Toluol oder Xylol) oder eine Mischung derselben als Lösungsmittel  Tetrahydrofuran), a nitrile (e.g. acetonitrile), an aromatic hydrocarbon (e.g. toluene or xylene) or a mixture thereof as a solvent
verwendet.  used.
3) Pyrimidin-Derivate der Formel (I), worin R5 für 3) Pyrimidine derivatives of the formula (I), in which R 5 is
(C1-C6)Alkyl, (C3-C7)Cycloalkyl, (C3-C7)Cycloalkyl- (C1-C4)alkyl, (C1-C4)Alkoxy-(C1-C4)alkyl, (C 1 -C 6 ) alkyl, (C 3 -C 7 ) cycloalkyl, (C 3 -C 7 ) cycloalkyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl,
(C1-C4)Alkylthio-(C1-C4)alkyl oder Phenyl steht, wobei der letztgenannte Rest bis zu dreifach durch (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl or phenyl, the latter radical being up to threefold
(C1-C4)Alkyl oder (C1-C4)Alkoxy substituiert sein kann, können durch Umsetzung von entsprechenden (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy may be substituted by reacting corresponding ones
Halopyrimidinen der Formel (I) mit R5 = Halogen mit Halopyrimidines of formula (I) with R 5 = halogen with
Grignard-Verbindungen R5MgX (III), wobei R5 wie oben angegeben definiert ist und X für Halogen (Cl, Br, J) steht, in Gegenwart von Nickel-Phosphin-Komplexen wie z.B. 1,2-Bis-(diphenylphosphino)-ethan-nickel-(II)- chlorid oder 1,3-Bis-(diphenylphosphino)-propan-nickel- (II)-chlorid erhalten werden (vgl. Chem. Pharm. Bull. 16, 2160 (1978)). Die Reaktion kann zwischen 0°C und 80°C bzw. bei dem Siedepunkt des Lösungsmittels innerhalb von 2-48 h durchgeführt werden. Die Grignard-Verbindung Grignard compounds R 5 MgX (III), where R 5 is as defined above and X represents halogen (Cl, Br, J), in the presence of nickel-phosphine complexes such as, for example, 1,2-bis (diphenylphosphino) -ethane-nickel- (II) - chloride or 1,3-bis- (diphenylphosphino) propane-nickel- (II) chloride can be obtained (cf. Chem. Pharm. Bull. 16, 2160 (1978)). The reaction can be carried out between 0 ° C and 80 ° C or at the boiling point of the solvent within 2-48 h. The Grignard connection
R5MgX (III) kann in Mengen von 1-2,5 Moläquivalenten bezogen auf 1 Äquivalent Halopyrimidin (I) eingesetzt werden. Als Lösungsmittel eignen sich Ether wie z.B. R 5 MgX (III) can be used in amounts of 1-2.5 molar equivalents based on 1 equivalent of halopyrimidine (I). Suitable solvents are ethers such as
Diethylether, THF, Dioxan, Dimethoxyethan.  Diethyl ether, THF, dioxane, dimethoxyethane.
Die Halopyrimidine I (R5 = Halogen) können durch The halopyrimidines I (R 5 = halogen) can by
Umsetzung der entsprechenden Hydroxypyrimidine I (R5 = OH), worin R1-R , R6-R12 und n wie in der allgemeinen Formel (I) definiert sind, mit Halogenierungsagens erhalten werden. Als Halogenierungsagens können z.B. Reaction of the corresponding hydroxypyrimidines I (R 5 = OH), in which R 1 -R, R 6 -R 12 and n are as defined in the general formula (I), are obtained with halogenating agents. As a halogenating agent, for example
Thionylchlorid, Phosgen, Phosphoroxychlorid,  Thionyl chloride, phosgene, phosphorus oxychloride,
Phosphorpentachlorid, Phorphoroxybromid oder  Phosphorus pentachloride, phosphorus oxybromide or
Phosphortribromid eingesetzt werden. Die Reaktionen können in einem Lösungsmittel, aber auch ohne Phosphorus tribromide can be used. The reactions can in a solvent, but also without
Lösungsmittel durchgeführt werden. Solvents are carried out.
Das Halogenierungsagens kann in Mengen von 1 bis 4 The halogenating agent can be used in amounts of 1 to 4
Äquivalenten bezogen auf 1 Äquivalent des Equivalents based on 1 equivalent of
Hydroxypyrimidins (I) eingesetzt werden. Die Reaktionen können in einem Temperaturbereich von 25-160°C  Hydroxypyrimidins (I) can be used. The reactions can take place in a temperature range of 25-160 ° C
durchgeführt werden. Als Lösungsmittel werden z.B. be performed. As solvents e.g.
aromatische Kohlenwasserstoffe (z.B. Benzol oder Toluol, u.a.) oder halogenierte Kohlenwasserstoffe (z.B. aromatic hydrocarbons (e.g. benzene or toluene, etc.) or halogenated hydrocarbons (e.g.
Chlorbenzol) eingesetzt. Chlorobenzene) used.
Die Hydroxypyrimidine (I) können durch Kondensation der The hydroxypyrimidines (I) can be condensed by
Amidin-Derivate (IV) mit β-Oxocarboxylaten (V) Amidine derivatives (IV) with β-oxocarboxylates (V)
dargestellt werden, being represented,
•HX • HX
NH2 NH 2
IV V IV V
worin R1-R4, R6-R12 und n wie in Formel I definiert wherein R 1 -R 4 , R 6 -R 12 and n as defined in formula I.
sind, X für Halogen (z.B. Chlor, Brom, Jod) und R13 für niedere Alkylreste wie z.B. Methyl, Ethyl oder Propyl stehen. are, X is halogen (eg chlorine, bromine, iodine) and R 13 is lower alkyl radicals such as methyl, ethyl or propyl.
Die Reaktionen werden im Temperaturbereich von 20-110°C bzw. bei dem Siedepunkt des Lösungsmittels innerhalb von 2-72 h durchgeführt. Das β-Oxocarboxylat V kann in The reactions are carried out in the temperature range of 20-110 ° C or at the boiling point of the solvent within 2-72 h. The β-oxocarboxylate V can in
Mengen von 1-1,5 Äquivalenten bezogen auf 1 Äquivalent Amounts of 1-1.5 equivalents based on 1 equivalent
Amidin-Derivat IV eingesetzt werden. Die Reaktion wird in Gegenwart einer Base und eines Lösungsmittels Amidine derivative IV can be used. The reaction is carried out in the presence of a base and a solvent
durchgeführt. Als Basen können z.B. anorganische Basen wie Alkalimetallhydroxide und -carbonate oder organische Basen wie Natriumalkoxide, Trialkylamine und carried out. As bases e.g. inorganic bases such as alkali metal hydroxides and carbonates or organic bases such as sodium alkoxides, trialkylamines and
N,N-Dialkylaniline eingesetzt werden. Als Lösungsmittel eignen sich niedere Alkohole (wie z.B. Methanol und Ethanol), cyclische Ether (wie Dioxan und THF), Pyridin, N,N-Dimethylformamid, Wasser oder Gemische derselben. Die Amidin-Derivate IV und die ß-Oxocarboxylate V können nach an sich bekannten Verfahren hergestellt werden (vgl. J. Org. Chem. 32, 1591 (1967) bzw. Synthesis 1982, 451 und Organikum 1986, 516 ff.). Die erfindungsgemäßen Verbindungen der Formel I zeichnen sich durch eine hervorragende fungizide Wirkung aus. N, N-dialkylanilines can be used. As a solvent lower alcohols (such as methanol and ethanol), cyclic ethers (such as dioxane and THF), pyridine, N, N-dimethylformamide, water or mixtures thereof are suitable. The amidine derivatives IV and the β-oxocarboxylates V can be prepared by processes known per se (cf. J. Org. Chem. 32, 1591 (1967) or Synthesis 1982, 451 and Organikum 1986, 516 ff.). The compounds of the formula I according to the invention are notable for an excellent fungicidal action.
Bereits in das pflanzliche Gewebe eingedrungene pilzliche Krankheitserreger lassen sich erfolgreich kurativ Fungal pathogens that have already penetrated the plant tissue can be successfully curated
bekämpfen. Dies ist besonders wichtig und vorteilhaft bei solchen Pilzkrankheiten, die nach eingetretener Infektion mit den sonst üblichen Fungiziden nicht mehr wirksam bekämpft werden können. Das Wirkungsspektrum der fight. This is particularly important and advantageous in the case of those fungal diseases which can no longer be effectively combated with the usual fungicides after infection has occurred. The spectrum of effects of
beanspruchten Verbindungen erfaßt eine Vielzahl claimed compounds covered a variety
verschiedener wirtschaftlich bedeutender, phytopathogener Pilze, wie z.B. Piricularia oryzae, Venturia inaequalis, Cercospora beticola, Echte Mehltauarten, Fusariumarten, Plasmopora viticola, Pseudoperonospora cubensis, various economically important phytopathogenic fungi, e.g. Piricularia oryzae, Venturia inaequalis, Cercospora beticola, powdery mildew species, Fusarium species, Plasmopora viticola, Pseudoperonospora cubensis,
Leptosphaeria nodorum, Drechslera, verschiedene Rostpilze und Pseudocercosporella herpotrichoides. Besonders gut werden Benzimidazol- und Dicarboximid-sensible und Leptosphaeria nodorum, Drechslera, various rust fungi and Pseudocercosporella herpotrichoides. Benzimidazole- and dicarboximide-sensitive and are particularly good
-resistente Botrytis cinerea Stämme erfaßt. -resistant botrytis cinerea strains detected.
Die erfindungsgemäßen Verbindungen eignen sich daneben auch für den Einsatz in technischen Bereichen, beispielsweise als Holzschutzmittel, als Konservierungsmittel in The compounds of the invention are also suitable for use in technical fields, for example as wood preservatives, as preservatives in
Anstrichfarben, in Kühlschmiermitteln für die  Paints, in cooling lubricants for the
Metallbearbeitung oder als Konservierungsmittel in Bohr- und Schneidölen. Gegenstand der Erfindung sind auch Mittel, die die Metalworking or as a preservative in drilling and cutting oils. The invention also relates to means which
Verbindungen der Formel I neben geeigneten  Compounds of formula I in addition to suitable
Formulierungshilfsmitteln enthalten. Die erfindungsgemäßen Mittel enthalten die Wirkstoffe der Formel I im allgemeinen zu 1 bis 95 Gew.-%. Formulation aids included. 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 biologischen und/oder chemischphysikalischen Parameter vorgegeben ist. Als They can be formulated in different ways, depending on how it is specified by the biological and / or chemical-physical parameters. As
Formulierungsmöglichkeiten kommen daher in Frage: Formulation options are therefore possible:
Spritzpulver (WP), emulgierbare Konzentrate (EC), wäßrige Lösungen (SC), Emulsionen, versprühbare Lösungen, Wettable powder (WP), emulsifiable concentrates (EC), aqueous solutions (SC), emulsions, sprayable solutions,
Dispersionen auf Öl- oder Wasserbasis (SC), Suspoemulsionen (SC), Stäubemittel (DP), Beizmittel, Granulate in Form von Mikro-, Sprüh-, Aufzugs- und Adsorptionsgranulaten, Oil or water-based dispersions (SC), suspoemulsions (SC), dusts (DP), pickling agents, granules in the form of micro, spray, elevator and adsorption granules,
wasserdispergierbare Granulate (WG), ULV-Formulierungen, Mikrokapseln, Wachse oder Köder. water-dispersible granules (WG), ULV formulations, microcapsules, waxes or baits.
Diese einzelnen Formulierungstypen sind im Prinzip bekannt und werden beispielsweise beschrieben in: These individual types of formulation are known in principle and are described, for example, in:
Winnacker-Küchler, "Chemische Technologie", Band 7,  Winnacker-Küchler, "Chemical Technology", Volume 7,
C. Hauser Verlag München, 4. Aufl. 1986; van Falkenberg, "Pesticides Formulations", Marcel Dekker N.Y., 2nd Ed.  C. Hauser Verlag Munich, 4th ed. 1986; van Falkenberg, "Pesticides Formulations", Marcel Dekker N.Y., 2nd Ed.
1972-73; K. Martens, "Spray Drying Handbook", 3rd Ed. 1979, G. Goodwin Ltd. London.  1972-73; K. Martens, "Spray Drying Handbook", 3rd Ed. 1979, G. Goodwin Ltd. London.
Die notwendigen Formulierungshilfsmittel wie The necessary formulation aids such as
Inertmaterialien, Tenside, Lösungsmittel und weitere  Inert materials, surfactants, solvents and others
Zusatzstoffe sind ebenfalls bekannt und werden  Additives are also known and will be
beispielsweise beschrieben in: Watkins, "Handbook of described for example in: Watkins, "Handbook of
Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J.; H.v.Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, N.Y.;  Insecticide Dust Diluents and Carriers ", 2nd Ed., Darland Books, Caldwell N.J .; H.v. Olphen," Introduction to Clay Colloid Chemistry ", 2nd Ed., J. Wiley & Sons, N.Y .;
Marsden, "Solvents Guide", 2nd Ed., Interscience, N.Y.  Marsden, Solvents Guide, 2nd Ed., Interscience, N.Y.
1950; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood,  1950; McCutcheon'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  "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Interface Active
Äthylenoxidaddukte", Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler, "Chemische Technologie", Band 7,  Äthylenoxidaddukte ", Wiss. Verlagsgesellschaft., Stuttgart 1976; Winnacker-Küchler," Chemical Technology ", Volume 7,
C. Hauser Verlag München, 4. Aufl. 1986. Auf der Basis dieser Formulierungen lassen sich auch C. Hauser Verlag Munich, 4th edition 1986. On the basis of these formulations can also
Kombinationen mit anderen pestizid wirksamen Stoffen, Combinations with other pesticidal substances,
Düngemitteln und/oder Wachstumsregulatoren herstellen, z.B. in Form einer Fertigformulierung oder als Tankmix. Manufacture fertilizers and / or growth regulators, e.g. 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 Verdünnungsoder Inertstoff noch Netzmittel, z.B. polyoxethylierte Alkylphenole, polyoxethylierte Fettalkohole, Alkyl- oder Alkylphenol-sulfonate und Dispergiermittel, z.B. Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active ingredient, contain a wetting agent, e.g. polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates and dispersants, e.g.
ligninsulfonsaures Natrium, 2,2'-dinaphthylmethan-6,6'- disulfonsaures Natrium, dibutylnaphthalin-sulfonsaures Natrium oder auch oleylmethyltaurinsaures Natrium sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalene-sulfonic acid sodium or oleylmethyl tauric acid sodium
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. Als Emulgatoren können beispielsweise verwendet werden: contain. Emulsifiable concentrates are made by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers. The following can be used as emulsifiers:
Alkylarylsulfonsäure Calzium-Salze wie Alkylarylsulfonic acid calcium salts such as
Ca-dodecylbenzolsulfonat oder nichtionische Emulgatoren wie Fettsäurepolyglykolester, Alkylarylpolyglykolether,  Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers,
Fettalkoholpolyglykolether, Propylenoxid-Ethylenoxid- Kondensationsprodukte, Sorbitanfettsäureester,  Fatty alcohol polyglycol ether, propylene oxide-ethylene oxide condensation products, sorbitan fatty acid esters,
Polyoxyethylensorbitan-Fettsäureester oder  Polyoxyethylene sorbitan fatty acid esters or
Polyoxethylensorbitester.  Polyoxethylene sorbitol ester.
Stäubemittel erhält man durch Vermählen des Wirkstoffes mit fein verteilten festen Stoffen, z.B. Talkum, natürlichen Tonen wie Kaolin, Bentonit, Pyrophillit oder Diatomeenerde. Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. Talc, natural clays such as kaolin, bentonite, pyrophillite or diatomaceous earth. Granules can either by spraying the active ingredient onto adsorbable, granulated inert material
hergestellt werden oder durch Aufbringen von  be produced or by applying
Wirkstoffkonzentraten mittels Klebemitteln, z.B.  Active ingredient concentrates using adhesives, e.g.
Polyvinylalkohol, polyacrylsaurem Natrium oder auch  Polyvinyl alcohol, polyacrylic acid sodium or also
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 - gewünschtenfalls in Mischung mit Düngemitteln - granuliert werden. Mineral oils on the surface of carriers such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be used in the production of Fertilizer granules in the usual way - if desired in a mixture with fertilizers - are granulated.
In Spritzpulvern beträgt die Wirkstoffkonzentration z.B. etwa 10 bis 90 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei emulgierbaren Konzentraten kann die Wirkstoffkonzentration etwa 5 bis 80 Gew.-% betragen. Staubförmige Formulierungen enthalten meistens 5 bis 20 Gew.-% an Wirkstoff, versprühbare The active substance concentration in wettable powders is e.g. about 10 to 90 wt .-%, the rest of 100 wt .-% consists of conventional formulation components. In the case of emulsifiable concentrates, the active substance concentration can be approximately 5 to 80% by weight. Dust-like formulations usually contain 5 to 20 wt .-% of active ingredient, sprayable
Lösungen etwa 2 bis 20 Gew.-%. Bei Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame Solutions about 2 to 20 wt .-%. In the case of granules, the active ingredient content depends in part on whether the active ingredient
Verbindung flüssig oder fest vorliegt und welche Connection is liquid or solid and which
Granulicrhilfsmittel, Füllstoffe usw. verwendet werden. Daneben enthalten die genannten Wirkstofformulierugen gegebenenfalls die jeweils üblichen Haft-, Netz-, Granular auxiliaries, fillers, etc. can be used. In addition, the active ingredient formulations mentioned may contain the usual adhesive, wetting,
Dispcrgier-, Emulgior-, Penetrations-, Lösungsmittel, Füll- oder Trägerstoffe. Zur Anwendung werden die in handelsüblicher Form Dispensing, emulsifying, penetrating, solvent, fillers or carriers. To be used in the commercial form
vorliegenden Konzentrate gegebenenfalls in üblicher Weise verdünnt, z.B. bei Spritzpulvern, emulgierbaren existing concentrates, if appropriate, diluted in a conventional manner, e.g. with wettable powders, emulsifiable
Konzentraten, Dispersionen und teilweise auch bei Concentrates, dispersions and sometimes also at
Mikrogranulaten mittels Wasser. Staubförmige und Microgranules using water. Dusty and
granulierte Zubereitungen sowie versprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt. 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. zwischen 0,005 und 10,0 kg/ha oder mehr Aktivsubstanz, vorzugsweise liegt sie jedoch zwischen 0,01 und 5 kg/ha. Die erfindungsgemäßen Wirkstoffe können in ihren With the external conditions such as temperature, humidity, etc. the required application rate varies, it can fluctuate within wide limits, e.g. between 0.005 and 10.0 kg / ha or more of active substance, but is preferably between 0.01 and 5 kg / ha. The active compounds according to the invention can in their
handelsüblichen Formulierungen entweder allein oder in Kombination mit weiteren, literaturbekannten Fungiziden angewendet werden. commercial formulations either alone or in Combination with other fungicides known from the literature can be used.
Als literaturbekannte Fungizide, die erfindungsgemäß mit den Verbindungen der Formel I kombiniert werden können, sind z.B. folgende Produkte zu nennen: Examples of fungicides known from the literature which can be combined according to the invention with the compounds of the formula I are, for example to name the following products:
Imazalil, Prochloraz, Fenapanil, SSF 105, Triflumizol, Imazalil, Prochloraz, Fenapanil, SSF 105, Triflumizol,
PP 969, Flutriafol, BAY-MEB 6401, Propiconazol, Etaconazol, Diclobutrazol, Bitertanol, Triadimefon, Triadimenol, PP 969, flutriafol, BAY-MEB 6401, propiconazole, etaconazole, diclobutrazole, bitertanol, triadimefon, triadimenol,
Fluotrimazol, Tridemorph, Dodemorph, Fenpropimorph, Fluotrimazole, tridemorph, dodemorph, fenpropimorph,
Falimorph, S-32165, Chlobenzthiazone, Parinol, Buthiobat, Fenpropidin, Triforine, Fenarimol, Nuarimol, Triarimol, Ethirimol, Dimethirimol,  Falimorph, S-32165, Chlobenzthiazone, Parinol, Buthiobat, Fenpropidin, Triforine, Fenarimol, Nuarimol, Triarimol, Ethirimol, Dimethirimol,
Bupirimate, Rabenzazole, Tricyclazole, Fluobenzimine, Bupirimate, Rabenzazole, Tricyclazole, Fluobenzimine,
Pyroxyfur, NK-483, PP-389, Pyroquilon, Hymexazole, Pyroxyfur, NK-483, PP-389, Pyroquilon, Hymexazole,
Fenitropan, UHF-8227, Cymoxanil, Dichlorfluanid, Captafol, Captan, Folpet, Tolylfluanid, Chlorothalonil, Etridiazol, Iprodione (Formel II), Procymidon, Vinclozolin, Metomeclan, Myclozolin, Dichlozolinate, Fluorimide, Drazoxolan,  Fenitropan, UHF-8227, Cymoxanil, Dichlorfluanid, Captafol, Captan, Folpet, Tolylfluanid, Chlorothalonil, Etridiazol, Iprodione (Formula II), Procymidon, Vinclozolin, Metomeclan, Myclozolin, Dichlozolinate, Fluorimide, Drazoxolanan
Chinomethionate, Nitrothalisopropyl, Dithianon, Dinocap, Binapacryl, Quinomethionates, nitrothalisopropyl, dithianon, dinocap, binapacryl,
Fentinacetate, Fentinhydroxide, Carboxin, Oxycarboxin,  Fentin acetates, fentin hydroxides, carboxin, oxycarboxin,
Pyracarbolid, Methfuroxam, Fenfuram, Furmecyclox, Benodanil, Mebenil, Mepronil, Flutalanil, Fuberidazole, Thiabendazole, Carbendazim, Benomyl, Thiophanate, Thiophanatemethyl,  Pyracarbolide, methfuroxam, fenfuram, furmecyclox, benodanil, mebenil, mepronil, flutalanil, fuberidazole, thiabendazole, carbendazim, benomyl, thiophanate, thiophanate methyl,
CGD- 94340 F, IKF-1216,  CGD-94340 F, IKF-1216,
Mancozeb, Maneb, Zineb, Nabam, Thiram, Probineb,  Mancozeb, Maneb, Zineb, Nabam, Thiram, Probineb,
Prothiocarb, Propamocarb, Dodine, Guazatine, Dicloran, Quintozene, Chloroneb, Tecnazene, Biphenyl, Anilazine, 2-Phenylphenol, Kupferverbindungen wie Cu-oxychlorid,  Prothiocarb, propamocarb, dodine, guazatine, dicloran, quintozene, chloroneb, tecnazene, biphenyl, anilazine, 2-phenylphenol, copper compounds such as Cu oxychloride,
Oxine-Cu, Cu-oxide, Schwefel, Fosethylaluminium,  Oxine-Cu, Cu-oxides, sulfur, fosethyl aluminum,
Natrium-dodecylbenzolsulfonat, Sodium dodecylbenzenesulfonate,
Natrium-dodecylsulfat,  Sodium dodecyl sulfate,
Natrium-C13/C15-alkoholethersulfonat,  Sodium C13 / C15 alcohol ether sulfonate,
Natrium-cetostearylphosphatester,  Sodium cetostearyl phosphate ester,
Dioctyl-natriumsulfosuccinat, Natrium-isopropylnaphthalinsulfonat, Dioctyl sodium sulfosuccinate, Sodium isopropylnaphthalenesulfonate,
Natrium-methylenbisnaphthalinsulfonat, Sodium methylene bisnaphthalene sulfonate,
Cetyl-trimethyl-ammoniumchlorid, Salze von langkettigen primären, sekundären oder tertiären Aminen, Alkyl-propylenamine, Lauryl-pyridinium-bromid, ethoxilierte guaternierte Fettamine, Alkyl-dimethyl-benzyl- ammoniumchlorid und 1-Hydroxyethyl-2-alkyl-imidazolin. Die oben genannten Kombinationspartner stellen bekannte Wirkstoffe dar, die zum großen Teil in C.R. Worthing, Cetyl-trimethyl-ammonium chloride, salts of long-chain primary, secondary or tertiary amines, alkyl-propylene amines, lauryl-pyridinium bromide, ethoxylated guaternized fatty amines, alkyl-dimethyl-benzyl-ammonium chloride and 1-hydroxyethyl-2-alkyl-imidazoline. The above-mentioned combination partners are known active ingredients, which are largely in C.R. Worthing,
S.B. Walker, The Pesticide Manual, 7. Auflage (1983), S.B. Walker, The Pesticide Manual, 7th edition (1983),
British Crop Protection Council beschrieben sind. Darüberhinaus 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, British Crop Protection Council. In addition, the active compounds according to the invention, in particular those of the examples listed, 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,
Sterilantien, Akariziden, Nematiziden, Fungiziden, Sterilants, acaricides, nematicides, fungicides,
wachstumsregulierenden Stoffen oder Herbiziden vorliegen. Zu den Insektiziden zählen beispielsweise growth regulating substances or herbicides. Insecticides include, for example
Phosphorsäureester, Carbamate, Carbonsäureester, Phosphoric acid esters, carbamates, carboxylic acid esters,
Formamidine, Zinnverbindungen, durch Mikroorganismen hergestellte Stoffe u.a.. Bevorzugte Mischungspartner sind: Formamidines, tin compounds, substances produced by microorganisms etc. Preferred mixing partners are:
1. aus der Gruppe der Phosphorsäureester 1. from the group of phosphoric acid esters
Azinphos-ethyl, Azinphos-methyl, 1-(4-Chlorphenyl)-4- (O-ethyl, S-propyl)phosphoryloxypyrazol (TIA-230),  Azinphos-ethyl, azinphos-methyl, 1- (4-chlorophenyl) -4- (O-ethyl, S-propyl) phosphoryloxypyrazole (TIA-230),
Chlorpyrifos, Coumaphos, Demeton, Demeton-S-methyl, Chlorpyrifos, Coumaphos, Demeton, Demeton-S-methyl,
Diazinon, Dichlorvos, Dimethoat, Ethoprophos, Etrimfos, Fenitrothion, Fenthion, Heptenophos, Parathion, Diazinon, Dichlorvos, Dimethoat, Ethoprophos, Etrimfos, Fenitrothion, Fenthion, Heptenophos, Parathion,
Parathion-methyl, Phosalon, Pirimiphos-ethyl,  Parathion-methyl, phosalon, pirimiphos-ethyl,
Pirimiphos-methyl, Profenofos, Prothiofos, Sulprofos, Triazophos, Trichlorphon.  Pirimiphos-methyl, Profenofos, Prothiofos, Sulprofos, Triazophos, Trichlorphon.
2. aus der Gruppe der Carbamate 2. from the group of carbamates
Aldicarb, Bendiocarb, BPMC (2-(1-Methylpropyl)phenyl- methylcarbamat), Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Isoprocarb, Aldicarb, bendiocarb, BPMC (2- (1-methylpropyl) phenyl- methyl carbamate), butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, cloethocarb, isoprocarb,
Methomyl, Oxamyl, Pirimicarb, Promecarb, Propoxur,  Methomyl, oxamyl, pirimicarb, promecarb, propoxur,
Thiodicarb.  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-trifluormethyl- vinyl)cyclopropancarbonsäure-(alpha-cyano-3-phenyl-2- methyl-benzyl)ester (FMC 54800), Fenpropathrin,  Allethrin, Alphamethrin, Bioallethrin, Bioresmethrin, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cypermethrin, Deltamethrin, 2,2-Dimethyl-3- (2-chloro-2-trifluoromethyl-vinyl) cyclopropanecarboxylic acid- (alpha-cyano-3-phenyl-2-) methyl-benzyl) ester (FMC 54800), fenpropathrin,
Fenfluthrin, Fenvalerat, Flucythrinate, Flumethrin,  Fenfluthrin, fenvalerate, flucythrinate, flumethrin,
Fluvalinate, Permethrin, Resmethrin, Tralomethrin. 4. aus der Gruppe der Formamidine  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,  Abamectin, Bacillus thuringiensis, Bensultap, Binapacryl, Bromopropylate, Buprofecin, Camphechlor, Cartap,
Chlorbenzilate, Chlorfluazuron, 2-(4-Chlorphenyl)- 4,5-diphenylthiophen (UBI-T 930), Chlofentezine,  Chlorobenzylates, chlorofluazuron, 2- (4-chlorophenyl) - 4,5-diphenylthiophene (UBI-T 930), chlofentezine,
Cyclopropancarbonsäure(2-naphthylmethyl)ester (Ro  Cyclopropanecarboxylic acid (2-naphthylmethyl) ester (Ro
12-0470), Cyromacin, DDT, Dicofol, N-(3,5-Dichlor-4- (1,1,2,2-tetrafluoroethoxy)phenylamino)carbonyl)-2,6- difluorbenzamide (XRD 473), Diflubenzuron, N-(2,3- Dihydro-3-methyl-1,3-thiazol-2-ylidene)2,4-xylidine, 12-0470), cyromacin, DDT, dicofol, N- (3,5-dichloro-4- (1,1,2,2-tetrafluoroethoxy) phenylamino) carbonyl) -2,6-difluorobenzamide (XRD 473), diflubenzuron, N- (2,3-dihydro-3-methyl-1,3-thiazol-2-ylidenes) 2,4-xylidines,
Dinobuton, Dinocap, Endosulfan, Fenoxycarb, Fenthiocarb, Flubenzimine, Flufenoxuron, Gamma-HCH, Hexythiazox, Hydramethylnon (AC 217 300) Ivermectin, 2-Nitromethyl- 4,5-dihydro-6H-thiazin (SD 52618), 2-Nitromethyl-3,4- dihydrothiazol (SD 35651), 2-Nitromethylene-1,3- thiazinon-3-yl-carbamaldehyde (WL 108 477), Propargite, Teflubenzuron, Tetradifon, Tetrasul, Thiocyclam, Dinobutone, dinocap, endosulfan, fenoxycarb, fenthiocarb, flubenzimine, flufenoxuron, gamma-HCH, hexythiazox, hydramethylnon (AC 217 300) ivermectin, 2-nitromethyl-4,5-dihydro-6H-thiazine (SD 52618), 2-nitromethyl- 3,4-dihydrothiazole (SD 35651), 2-nitromethylene-1,3-thiazinon-3-yl-carbamaldehyde (WL 108 477), propargite, teflubenzuron, tetradifone, tetrasul, thiocyclam,
Triflumaron, Kernpolyeder- und Granuloseviren. Der Wirkstoffgehalt der aus den handelsüblichen Triflumaron, nuclear polyhedron and granuloviruses. The active ingredient content from the commercially available
Formulierungen bereiteten Anwendungsformen kann in weiten Bereichen variieren, Die Wirkstoffkonznetration der Formulations of use forms prepared can vary widely, the concentration of the active ingredient
Anwendungsformen kann von 0,0001 bis zu 100 Gew.-% Application forms can range from 0.0001 to 100% by weight
Wirkstoff, vorzugsweise zwischen 0,001 und 1 Gew.-% liegen. Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichen Weisen. Active ingredient, preferably between 0.001 and 1 wt .-%. The application takes place in a customary manner adapted to the application forms.
Nachfolgende Beispiele dienen zur Erläuterung der Erfindung. A. Formuliorungsbeispiele a) Ein Stäubemittel wird erhalten, indem man 10 Gew.-Teile Wirkstoff und 90 Gew.-Teile Talkum als Inertstoff mischt und in einer Schlagmühle zerkleinert. b) Ein in Wasser leicht dispergierbr.res, benetzbares Pulver wird erhalten, indem man 25 Gew.-Teile Wirkstoff, The following examples serve to explain the invention. 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) A wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight of active compound,
65 Gew.-Teile kaolinhaltigen Quarz als Inertstoff,  65 parts by weight of kaolin-containing quartz as an inert substance,
10 Gew.-Teile ligninsulfonsaures Kalium und 1 Gew.-Teil oleoylmethyltaurinsaures Natrium als Netz- und  10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium as wetting and
Dispergiermittel mischt und in einer Stiftmühle mahlt. c) Ein in Wasser leicht dispergierbares  Mixes dispersant and grinds in a pin mill. c) An easily dispersible in water
Dispersionskonzentrat stellt man her, indem man 40 Gew.- Teile Wirkstoff mit 7 Gew.-Teilen eines  Dispersion concentrate is prepared by mixing 40 parts by weight of active ingredient with 7 parts by weight of one
Sulfobernsteinsäurehalbesters, 2 Gew.-Teilen eines  Sulfosuccinic acid half-ester, 2 parts by weight of one
Ligninsulfonsäure-Natriumsalzes und 51 Gew.-Teilen  Ligninsulfonic acid sodium salt and 51 parts by weight
Wasser mischt und in einer Reibkugelmühle auf eine  Mixes water and in a grater on a
Feinheit von unter 5 Mikron vermahlt. d) Ein emulgierbares Konzentrat läßt sich herstellen aus 15 Gew.-Teilen Wirkstoff, 75 Gew.-Teilen Cyclohexanon als Lösungsmittel und 10 Gew.-Teilen oxethyliertem  Fineness of less than 5 microns ground. 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 Nonylphenol (10 AeO) as an emulsifier. e) Granules can be produced from 2 to 15 parts by weight of active ingredient and an inert one
Granulatträgermaterial wie Attapulgit, Bimsgranulat und/oder Quarzsand. Zweckmäßigerweise verwendet man eine Suspension des Spritzpulvers aus Beispiel b) mit einem Feststoffanteil von 30 % und spritzt diese auf die  Granulate carrier material such as attapulgite, pumice granulate and / or quartz sand. A suspension of the wettable powder from example b) with a solids content of 30% is expediently used and this is sprayed onto the
Oberfläche eines Λttapulgitgranulats, trocknet und vermischt innig. Dabei beträgt der Gewichtsanteil des Spritzpulvers ca. 5 % und der des inerten  Surface of Λttapulgite granules, dries and mixes intimately. The proportion by weight of the wettable powder is about 5% and that of the inert
Trägermaterials ca. 95 % des fertigen Granulats.  Carrier material approx. 95% of the finished granulate.
B. Chemische Beispiele B. Chemical examples
4-Benzyl-2-(6-methyl-pyridin-2-yl)-pyrimidin 4-benzyl-2- (6-methyl-pyridin-2-yl) pyrimidine
(Beipsiel-Nr.: 1) (Example number: 1)
Zu einer Lösung von 1,48 g (0,005 mol) 4-Benzyl-2-(6- methyl-pyridin-2-yl)-6-chlor-pyrimidin in 50 ml Ethanol fügt man 0,2 g 5 % Palladium/Kohle. Unter einem Druck von 3 bar und bei einer Temperatur von 60°C bringt man dieses Gemisch unter starkem Rühren 2 h in Kontakt mit 0.2 g of 5% palladium / carbon is added to a solution of 1.48 g (0.005 mol) of 4-benzyl-2- (6-methyl-pyridin-2-yl) -6-chloro-pyrimidine in 50 ml of ethanol . Under a pressure of 3 bar and at a temperature of 60 ° C, this mixture is brought into contact with vigorous stirring for 2 hours
Wasserstoff. Anschließend wird der Katalysator abfiltriert und das Filtrat im Vakuum eingeengt. Der Rückstand wird in Wasser aufgenommen, mit Matriumbicarbonat gesättigt und mit CIi2Cl2 extrahiert. Die organische Phase wird über Na2SO4 getrocknet und eingeengt. Man erhält 1,25 g (95,7 %) eines farblosen Öls. Hydrogen. The catalyst is then filtered off and the filtrate is concentrated in vacuo. The residue is taken up in water, saturated with sodium bicarbonate and extracted with CIi 2 Cl 2 . The organic phase is dried over Na 2 SO 4 and concentrated. 1.25 g (95.7%) of a colorless oil are obtained.
4-Bcnzyl-2-(6-methyl-pyridin-2-yl)-6-rethoxy-pyrimidin (Beispiel-Nr.: 2) 4-Bcnzyl-2- (6-methyl-pyridin-2-yl) -6-rethoxy-pyrimidine (example no .: 2)
Eine Natriummethylat-Lösung wird durch Auflösen von 0,184 g (0,008 mol) Natrium in 40 ml abs. Methanol hergestellt. Zu dieser Lösung fügt man 1,30 g (0,0044 mol) 4-Benzyl-2-(6- methyl-pyridin-2-yl)-6-chlor-pyrimidin und kocht 3 h amA sodium methylate solution is obtained by dissolving 0.184 g (0.008 mol) sodium in 40 ml abs. Made methanol. 1.30 g (0.0044 mol) of 4-benzyl-2- (6-methyl-pyridin-2-yl) -6-chloro-pyrimidine are added to this solution and the mixture is boiled for 3 hours
Rückfluß. Danach wird eingeengt, der Rückstand mit Wasser versetzt und mit Methylenchlorid extrahiert. Die organische Phase wird mit Na2SO4 getrocknet und eengeengt. Man erhält 1,16 g (90,5 %) eines gelblichen Öls. 4-Benzyl-2-(6-methyl-pyridin-2-yl)-6-methylmercapto-pyrimidin (Beispiel-Nr.: 3) Reflux. It is then concentrated, the residue with water added and extracted with methylene chloride. The organic phase is dried with Na 2 SO 4 and concentrated. 1.16 g (90.5%) of a yellowish oil are obtained. 4-benzyl-2- (6-methyl-pyridin-2-yl) -6-methylmercapto-pyrimidine (example no .: 3)
Zu einer Lösung von 1,3 g (0,0044 mol) 4-Benzyl-2-(6-methyl- ρyridin-2-yl)-6-chlor-pyrimidin in 50 ml abs. Acetonitril fügt man 0,45 g (0,0065 mol) Natriumthiomethylat hinzu und läßt 4 h am Rückfluß kochen. Dann wird abfiltriert und eingeengt. Der Rückstand wird in Wasser aufgenommen und mit Methylenchlorid extrahiert. Man trocknet über Na2SO4, engt im Vakuum ein und erhält 1,13 g (83,5 %) eines gelblichen Öls. To a solution of 1.3 g (0.0044 mol) of 4-benzyl-2- (6-methyl-ρyridin-2-yl) -6-chloro-pyrimidine in 50 ml of abs. Acetonitrile is added to 0.45 g (0.0065 mol) of sodium thiomethylate and the mixture is refluxed for 4 h. Then it is filtered off and concentrated. The residue is taken up in water and extracted with methylene chloride. It is dried over Na 2 SO 4 and concentrated in vacuo to give 1.13 g (83.5%) of a yellowish oil.
Analog zu diesen Beispielen lassen sich die Verbindungen der Tabelle A herstellen. Abkürzungen : Me = Methyl The compounds of Table A can be prepared analogously to these examples. Abbreviations: Me = methyl
Et = Ethyl  Et = ethyl
Pr = Propyl  Pr = propyl
Bu = Butyl Bu = butyl
C. Biologische Beispiele C. Biological examples
Beispiel 1 Etwa 5 Wochen alte Reispflanzen der Sorte "Ballila" wurden nach Vorspritzen mit 0,05 %iger Gelatinelösung mit der unten angegebenen .Konzentration der beanspruchten Example 1 Rice plants of the "Ballila" variety, about 5 weeks old, were sprayed with 0.05% gelatin solution at the concentration indicated below
Verbindungen behandelt. Nach Antrocknen des Spritzbelages wurden die Pflanzen mit einer Sporensuspension von  Connections handled. After the spray coating had dried on, the plants were treated with a spore suspension of
Piricularia oryzae gleichmäßig inokuliert und 48 h in eine dunkel gehaltene Klimakammer mit einer Temperatur von 25°C und 100 % rel. Luftfeuchte gestellt. Danach wurden die Reispflanzen in einem Gewächshaus mit einer Temperatur von 25°C und 80 % rel. Luftfeuchte weiterkultiviert. Nach 5 Tagen erfolgte die Befallsauswertung. Der Befallsgrad wurde in % befallener Blattfläche im Vergleich zu unbehandelten, infizierten Kontrollpflanzen ausgedrückt. Die Ergebnisse sind in Tabelle 1 zusammengestellt.  Piricularia oryzae evenly inoculated and 48 h in a dark climate chamber with a temperature of 25 ° C and 100% rel. Humidity set. Then the rice plants were in a greenhouse with a temperature of 25 ° C and 80% rel. Humidity continued to be cultivated. The infestation was evaluated after 5 days. The degree of infestation was expressed in% infested leaf area in comparison to untreated, infected control plants. The results are summarized in Table 1.
Beispiel 2 Example 2
Gerstenpflanzen wurden im 2-Blattstadium mit Konidien des Gerstenmehltaus (Erysiphe graminis hordei) stark inokuliert und in einem Gewächshaus bei 20°C und einer relativen Barley plants were strongly inoculated in the 2-leaf stage with conidia of barley mildew (Erysiphe graminis hordei) and in a greenhouse at 20 ° C and a relative
Luftfeuchte von ca. 50 % weiterkultiviert. 1 Tag nach  Humidity of approx. 50% cultivated further. 1 day after
Inokulation wurden die Pflanzen mit den in Tabelle 2 aufgeführten Verbindungen in der angegebenen  The plants were inoculated with the compounds listed in Table 2 in the given
Wirkstoffkonzentration gleichmäßig benetzt. Nach einer Inkubationszeit von 7-9 Tagen wurden die Pflanzen auf  Active ingredient concentration evenly wetted. After an incubation period of 7-9 days, the plants were opened
Befall mit Gerstenmehltau untersucht. Der Befallsgrad wird ausgedrückt in % befallener Blattfläche, bezogen auf unbehandelte, infizierte Kontrollpflanzen (= 100 % Befall). Das Ergebniss ist in Tabelle 2 zusammengefaßt.  Infestation with barley mildew examined. The degree of infestation is expressed in% infested leaf area, based on untreated, infected control plants (= 100% infestation). The result is summarized in Table 2.
Beispiel 3 Example 3
Ca. 14 Tage alte Ackerbohnen der Sorten "Herz Freya" oder "Frank's Ackerperle" wurden mit wäßrigen Suspensionen der beanspruchten Verbindungen tropfnaß behandelt. Nach Antrocknen des Spritzbelages wurden die Pflanzen mit einer Sporensuspension (1,5 Mio. Sporen/ml) von Botrytis cinerea inokuliert. Die Pflanzen wurden in einer Approximately 14 day old beans of the varieties "Herz Freya" or "Frank's Ackerperle" were treated to runoff with aqueous suspensions of the claimed compounds. After the spray coating had dried on, the plants were inoculated with a spore suspension (1.5 million spores / ml) of Botrytis cinerea. The plants were in a
Klimakammer bei 20-22 °C und ca. 99 % rel. Luftfeuchte weiterkultiviert. Die Infektion der Pflanzen äußert sich in der Bildung schwarzer Flecken auf Blättern und Stengeln. Die Auswertung der Versuche erfolgte ca. 1 Woche nach  Climatic chamber at 20-22 ° C and approx. 99% rel. Humidity continued to be cultivated. The infection of the plants manifests itself in the formation of black spots on leaves and stems. The tests were evaluated about 1 week after
Inokulation. Der Wirkungsgrad der PrüfSubstanzen wurde prozentual zur unbehandelten, infizierten Kontrolle bonitiert und ist in Tabelle 3 wiedergegeben.  Inoculation. The efficiency of the test substances was rated as a percentage of the untreated, infected control and is shown in Table 3.
Beispiel 4 Example 4
Weizenpflanzen der Sorte "Jubilar" wurden im 2-Blattstadium mit wäßrigen Suspensionen der in Tabelle 4 angegebenen Präparate tropfnaß behandelt. Nach dem Antrocknen des Spritzbelages wurden die Pflanzen mit einer wäßrigen Pyknosporen-Suspension von Leptosphaeria nodorum inokuliert und mehrere Stunden bei 100 % rel. Wheat plants of the "Jubilar" variety were treated to runoff point in the 2-leaf stage with aqueous suspensions of the preparations shown in Table 4. After the spray coating had dried on, the plants were inoculated with an aqueous pycnospore suspension of Leptosphaeria nodorum and kept at 100% rel.
Luftfeuchte in einer Klimakammer inkubiert. Bis zur  Humidity incubated in a climatic chamber. To
Symptomausprägung wurden die Pflanzen im Gewächshaus bei ca. 90 % rel. Luftfeuchte weiterkultiviert.  The symptoms were expressed in the plants in the greenhouse at approx. 90% rel. Humidity continued to be cultivated.
Der Wirkungsgrad ist prozentual zur unbehandelten, The efficiency is a percentage of the untreated,
infizierten Kontrolle ausgedrückt und wird in Tabelle 4 wiedergegeben.  infected control and is shown in Table 4.
Beispiel 5 Example 5
Weizen der Sorte "Jubilar" wurde im 2-Blattstadium mit wäßrigen Suspensionen der beanspruchten Verbindungen tropfnaß behandelt. Nach dem Antrocknen des Spritzbelages wurden die Pflanzen mit einer wäßrigen Sporensuspension von Puccinia recondita inokuliert. Die Pflanzen wurden für ca. 16 Stunden tropfnaß in eine Klimakammer mit 20 °C und ca. 100 % rel. Luftfeuchte gestellt. Anschließend wurden die infizierten Pflanzen in einem Gewächshaus bei einer Wheat of the "Jubilar" variety was treated to runoff point in the 2-leaf stage with aqueous suspensions of the claimed compounds. After the spray coating had dried on, the plants were inoculated with an aqueous spore suspension of Puccinia recondita. The plants were dripping wet for about 16 hours in a climate chamber at 20 ° C and about 100% rel. Humidity set. The infected plants were then in a greenhouse at a
Temperatur von 22-25 °C und 50-70 % rel. Luftfeuchte weiterkultiviert.  Temperature of 22-25 ° C and 50-70% rel. Humidity continued to be cultivated.
Nach eine Inkubationszeit von ca. 2 Wochen sporuliert der Pilz auf der gesamten Blattoberfläche der nicht behandelten Kontrollpflanzen, so daß eine Befallsauswertung der After an incubation period of about 2 weeks, the fungus sporulated on the entire leaf surface of the untreated control plants, so that an evaluation of the infection of the
Versuchspflanzen vorgenommen werden kann. Der Befallsgrad wurde in % befallener Blattfläche im Vergleich zu  Trial plants can be made. The degree of infestation was in% affected leaf area compared to
unbehandelten, infizierten Kontrollpflanzen ausgedrückt und ist in Tabelle 5 wiedergegeben.  untreated, infected control plants and is shown in Table 5.

Claims

Patentansprüche: Claims:
1. Verbindungen der Formel I 1. Compounds of formula I.
worin wherein
R 1 = Wasserstoff, (C1-C6)Alkyl, (C1-C4)Alkoxy- (C1-C4)alkyl, (C1-C4)Alkylthio-(C1-C4)alkyl, (C2-C6)Alkenyl, R 1 = hydrogen, (C 1 -C 6 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, (C 2 -C 6 ) alkenyl,
(C2-C6)Alkinyl, (C3-C7)Cycloalkyl, (C3-C7)Cycloalkyl- (C1-C4) alkyl, wobei die beiden letztgenannten Reste im Cycloalkylteil bis zu dreifach durch (C1-C4)Alkyl substituiert sein können, Phenyl, (C 2 -C 6 ) alkynyl, (C 3 -C 7 ) cycloalkyl, (C 3 -C 7 ) cycloalkyl- (C 1 -C 4 ) alkyl, the latter two radicals in the cycloalkyl part being up to triple by (C 1 -C 4 ) alkyl can be substituted, phenyl,
Phenoxy-(C1-C4)alkyl, Phenylmercapto(C1-C4)alkyl, Phenyl-(C1-C4)alkyl, Phenoxy-phenoxy(C1-C4)alkyl, wobei die fünf letztgenannten Reste im Phenoxy- (C 1 -C 4 ) alkyl, phenylmercapto (C 1 -C 4 ) alkyl, phenyl- (C 1 -C 4 ) alkyl, phenoxy-phenoxy (C 1 -C 4 ) alkyl, the five last-mentioned radicals in
Phenylteil bis zu dreifach durch Halogen, Nitro, (C1-C4)Alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, Phenyl moiety up to three times by halogen, nitro, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio,
(C1-C4)Haloalkyl oder (C1-C4)Haloalkoxy substituiert sein können, R2, R3, R4 = unabhängig voneinander Wasserstoff, (C 1 -C 4 ) haloalkyl or (C 1 -C 4 ) haloalkoxy can be substituted, R 2 , R 3 , R 4 = independently of one another hydrogen,
(C1-C6)Alkyl, Phenyl, wobei der Phenylrest bis zu dreifach durch Halogen, Nitro, (C1-C4)Alkyl, (C 1 -C 6 ) alkyl, phenyl, the phenyl radical being up to triple by halogen, nitro, (C 1 -C 4 ) alkyl,
(C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl oder (C2-C4)Haloalkoxy substituiert sein kann, R5 = Wasserstoff, (C1-C8)Alkyl, (C3-C6)Cycloalkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl or (C 2 -C 4 ) haloalkoxy may be substituted, R 5 = hydrogen, (C 1 -C 8 ) alkyl, (C 3 -C 6 ) cycloalkyl,
(C3-C7) Cycloalkyl- (C1-C4) alkyl, wobei die beiden letztgenannten Reste im Cycloalkylteil bis zu dreifach durch (C1-C4)Alkyl substituiert sein können, (C 3 -C 7 ) cycloalkyl- (C 1 -C 4 ) alkyl, where the latter two radicals in the cycloalkyl part can be substituted up to three times by (C 1 -C 4 ) alkyl,
(C1-C4)Haloalkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Alkoxy-(C1-C4)alkyl, (C1-C4)Alkylthio- (C1-C4)alkyl, Halogen, (C2-C6)Alkenyl, (C2-C6)Alkinyl, Phenyl, Phenoxy, Phenyl(C1-C4)alkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl, halogen, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, phenyl, phenoxy, phenyl (C 1 -C 4 ) alkyl,
Phenoxy-(C1-C4)alkyl, Phenylmercapto-(C1-C4) alkyl, Phenylmercapto, Phenyl-(C1-C4)alkoxy oder Phenoxy- (C 1 -C 4 ) alkyl, phenylmercapto- (C 1 -C 4 ) alkyl, phenylmercapto, phenyl- (C 1 -C 4 ) alkoxy or
Phenyl-(C1-C4)alkylthio, wobei die acht Phenyl- (C 1 -C 4 ) alkylthio, the eight
letztgenannten Reste im Phenylteil bis zu dreifach durch Halogen, Nitro, Cyano, (C1-C4)Alkyl, the latter radicals in the phenyl moiety up to three times by halogen, nitro, cyano, (C 1 -C 4 ) alkyl,
(C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl oder (C1-C4)Haloalkoxy substituiert sein können, (C1-C4)Alkenyloxy, (C2-C4)Alkinyloxy, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl or (C 1 -C 4 ) haloalkoxy can be substituted, (C 1 -C 4 ) alkenyloxy, (C 2 -C 4 ) alkynyloxy,
(C1-C4)Kaloalkoxy, (C1-C4)Alkoxy-(C1-C4)alkoxy, (C 1 -C 4) Kaloalkoxy, (C 1 -C 4) alkoxy, alkoxy (C 1 -C 4),
(C1-C4)Alkylthio-(C1-C4)alkylthio R6 = Wasserstoff, (C1-C4)Alkyl, (C1-C4)Alkoxy, (C2-C6)- Alkenyloxy, (C2-C6)Alkinyloxy, (C1-C4)Alkylthio, Halogen, Phenyl, wobei der Phenylrest bis zu dreifach durch Halogen, Nitro, Cyano, (C1-C4)Alkyl, (C1-C4) Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl oder (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkylthio R 6 = hydrogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 2 -C 6 ) - alkenyloxy, (C 2 -C 6 ) alkynyloxy, (C 1 -C 4 ) alkylthio, halogen, phenyl, the phenyl radical being up to three times by halogen, nitro, cyano, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) Alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl or
(C1-C4) Haloalkoxy substituiert sein kann, (C 1 -C 4 ) haloalkoxy can be substituted,
R7, R8, R9, R10 = unabhängig voneinander Wasserstoff, R 7 , R 8 , R 9 , R 10 = independently of one another hydrogen,
Halogen, Nitro, Cyano, (C1-C4)Alkyl, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C1-C4)Haloalkyl oder Halogen, nitro, cyano, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl or
(C1-C4)Haloalkoxy, (C 1 -C 4 ) haloalkoxy,
R11, R12 = unabhängig voneinander Wasserstoff oder R 11 , R 12 = independently of one another hydrogen or
(C1-C4)Alkyl und n = 1 - 3 bedeuten, sowie deren Säureadditionssalze. (C 1 -C 4 ) alkyl and n = 1 - 3, and their acid addition salts.
2. Verbindungen der Formel I von Anspruch 1, worin 2. Compounds of formula I of claim 1, wherein
R1 = Wasserstoff, (C1-C6) Alkyl, Phenyl, Phenyl-(C1-C2)- alkyl, Phenoxy-phenoxy-(C1-C2)alkyl, Phenoxy-(C1-C2)- alkyl, v;obei die vier letztgenannten Reste im R 1 = hydrogen, (C 1 -C 6 ) alkyl, phenyl, phenyl- (C 1 -C 2 ) -alkyl, phenoxy-phenoxy- (C 1 -C 2 ) alkyl, phenoxy- (C 1 -C 2 ) - alkyl, v; obei the latter four residues in
Phenylteil bis zu dreifach durch Halogen oder  Phenyl part up to three times by halogen or
(C1-C4)Alkyl substituiert sein können; (C1-C3)Alkoxy- (C1-C2) alkyl, R2, R3 = unabhängig voneinander Wasserstoff, (C1-C3)Alkyl, Phenyl, wobei der Phenylrest bis zu dreifach durch Halogen oder (C1-C4)Alkyl substituiert sein kann, (C 1 -C 4 ) alkyl may be substituted; (C 1 -C 3 ) alkoxy- (C 1 -C 2 ) alkyl, R 2 , R 3 = independently of one another hydrogen, (C 1 -C 3 ) alkyl, phenyl, the phenyl radical being up to triple by halogen or (C 1 -C 4 ) alkyl can be substituted,
R4 Wasserstoff, R 4 is hydrogen,
R5 = Wasserstoff, (C1-C6)Alkyl, (C3-C6)Cycloalkyl, R 5 = hydrogen, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl,
(C5-C6)Cycloalkyl-(C1-C3)alkyl, Phenyl, (C 5 -C 6 ) cycloalkyl- (C 1 -C 3 ) alkyl, phenyl,
Phenyl-(C1-C2)alkylthio, Phenyl-(C1-C2)alkyl, wobei die drei letztgenannten Reste im Phenylteil Phenyl- (C 1 -C 2 ) alkylthio, phenyl- (C 1 -C 2 ) alkyl, the three last-mentioned radicals in the phenyl part
bis zu dreifach durch Halogen, (C1-C4)Alkyl, up to three times by halogen, (C 1 -C 4 ) alkyl,
(C1-C3)Haloalkyl oder (C1-C4)Alkoxy substituiert sein können, (C1-C4)Alkoxy, (C1-C4)Alkylthio, (C 1 -C 3 ) haloalkyl or (C 1 -C 4 ) alkoxy can be substituted, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio,
(C2-C4)Alkenyloxy, (C2-C4)Alkinyloxy, (C2-C3)Alkenyl, (C2-C4)Alkinyl oder (C1-C4)Alkoxy-(C1-C4)alkoxy (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) alkynyloxy, (C 2 -C 3 ) alkenyl, (C 2 -C 4 ) alkynyl or (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkoxy
R6 = Wasserstoff, (C1-C4)Alkyl, Halogen, Phenyl oder R 6 = hydrogen, (C 1 -C 4 ) alkyl, halogen, phenyl or
(C1-C3)Alkoxy R7, R8, R9, R10 = unabhängig voneinander Wasserstoff, (C 1 -C 3 ) alkoxy R 7 , R 8 , R 9 , R 10 = independently of one another hydrogen,
Halogen, (C1-C4)Alkyl, (C1-C4)Haloalkyl oder Halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl or
((C1-C4)Alkylthio ((C 1 -C 4 ) alkylthio
R11, R12 = Wasserstoff und n = 1 bedeuten, sowie deren Säureadditionssalze. R 11 , R 12 = hydrogen and n = 1, and their acid addition salts.
3. Verfahren zur Herstellung von Verbindungen der Formel I gemäß Anspruch 1 oder 2, dadurch gekennzeichnet, daß man a) für Verbindungen mit R5 = Wasserstoff ein entsprechendes Halopyrimidin der Formel I mit R5 = Halogen und allen übrigen Substituenten in den genannten Bedeutungen reduktiv dehalogeniert oder b) für Verbindungen der Formel I, worin R5 für 3. A process for the preparation of compounds of the formula I according to claim 1 or 2, characterized in that a) for compounds with R 5 = hydrogen, a corresponding halopyrimidine of the formula I with R 5 = halogen and all other substituents in the meanings mentioned reductively dehalogenated or b) for compounds of the formula I in which R 5 is
(C1-C4)Alkoxy, (C1-C4)Alkylthio, Phenoxy, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, phenoxy,
Phenylmercapto, Phenyl-(C1-C4)alkoxy oder Phenylmercapto, phenyl- (C 1 -C 4 ) alkoxy or
Phenyl-(C1-C4)alkylthio, wobei die 4 letztgenannten Reste im Phenylteil bis zu dreifach durch Halogen, Nitro, Cyano, (C1-C4)Alkyl, (C1-C4)Alkoxy, Phenyl- (C 1 -C 4 ) alkylthio, the 4 last-mentioned radicals in the phenyl part being up to three times by halogen, nitro, cyano, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy,
(C1-C4)Alkylthio, (C1-C4)Haloalkyl oder (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl or
(C1-C4)Haloalkoxy substituiert sein können, (C 1 -C 4 ) haloalkoxy can be substituted,
(C2-C4)Alkenyloxy, (C2-C4)Alkinyloxy, (C1-C4)Haloalkoxy, (C1-C4)Alkoxy-(C1-C4)alkoxy oder (C 2 -C 4) alkenyloxy, (C 2 -C 4) alkynyloxy, (C 1 -C 4) haloalkoxy, (C 1 -C 4) alkoxy- (C 1 -C 4) alkoxy or
(C1-C4)Alkylthio-(C1-C4)alkylthio steht, ein (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkylthio
entsprechendes Halopyrimidin der F'ormel I mit R5 = corresponding halopyrimidine of formula I with R 5 =
Halogen mit einer Alkalimetallverbindung der Formel II  Halogen with an alkali metal compound of the formula II
R5 - Y (II), worin R5 die obengenannte Bedeutung besitzt und Y für ein Alkalimetall steht, umsetzt oder c) für Verbindung der Formel I worin R5 für R 5 - Y (II), in which R 5 has the abovementioned meaning and Y represents an alkali metal, or c) for compound of the formula I in which R 5 is
(C1-C6) Alkyl, (C3-C7)Cycloalkyl, (C3-C7)Cycloalkyl- (C1-C4) alkyl, (C1-C4)Alkoxy-(C1-C4)alkyl, (C 1 -C 6 ) alkyl, (C 3 -C 7 ) cycloalkyl, (C 3 -C 7 ) cycloalkyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl,
(C1-C4)Alkylthio-(C1-C4)alkyl oder Phenyl steht, wobei der letztgenannte Rest bis zu dreifach durch (C 1 -C 4 ) alkylthio- (C 1 -C 4 ) alkyl or phenyl, the latter radical being up to threefold
(C1-C4)Alkyl oder (C1-C4)Alkoxy substituiert sein kann, ein entsprechendes Halopyrimidin der Formel I mit R5 = Halogen mit einer Grignardverbindung der Formel III R5 - MgX (lll), worin R5 die obengenannte Bedeutung besitzt und X = Halogen bedeutet, in Gegenwart von Nickel-Phosphin- Komplexen umsetzt. (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy may be substituted, a corresponding halopyrimidine of the formula I with R 5 = halogen with a Grignard compound of the formula III R 5 - MgX (III), wherein R 5 has the abovementioned meaning and X = halogen, in the presence of nickel-phosphine complexes.
4. Fungizide Mittel, dadurch gekennzeichent, daß sie eine wirksame Menge einer Verbindung der Formel I gemäß Anspruch 1 oder 2 enthalten. 4. Fungicidal compositions, characterized in that they contain an effective amount of a compound of formula I according to claim 1 or 2.
5. Verwendung von Verbindungen der Formel I gemäß Anspruch 1 oder 2 zur Bekämpfung von Schadpilzen. 5. Use of compounds of formula I according to claim 1 or 2 for combating harmful fungi.
6. Verfahren zur Bekämpfung von Schadpilzen, dadurch gekennzeichnet, daß man auf die von ihnen befallenen 6. A method of combating harmful fungi, characterized in that one of those infested by them
Pflanzen, Flächen oder Substrate eine wirksame Menge einer Verbindung der Formel I gemäß Anspruch 1 oder 2 appliziert. Plants, areas or substrates applied an effective amount of a compound of formula I according to claim 1 or 2.
EP90916261A 1989-11-09 1990-11-07 Pyrimidine derivatives, process for making them, agents containing them and their use as fungicides Withdrawn EP0518862A1 (en)

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DE3937284 1989-11-09
DE3937284A DE3937284A1 (en) 1989-11-09 1989-11-09 PYRIMIDINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, THE AGENTS CONTAINING THEY AND THEIR USE AS FUNGICIDES

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EP0518862A1 true EP0518862A1 (en) 1992-12-23

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EP (1) EP0518862A1 (en)
JP (1) JPH05501550A (en)
KR (1) KR927003569A (en)
CN (1) CN1051559A (en)
AU (1) AU6638990A (en)
BR (1) BR9007833A (en)
CA (1) CA2068328A1 (en)
DE (1) DE3937284A1 (en)
HU (1) HUT62287A (en)
IL (1) IL96271A0 (en)
MX (1) MX23260A (en)
PT (1) PT95831A (en)
WO (1) WO1991007400A1 (en)
YU (1) YU212990A (en)
ZA (1) ZA908958B (en)

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GB9024873D0 (en) * 1990-11-15 1991-01-02 Ici Plc Fungicidal compounds
WO1992010490A1 (en) * 1990-12-05 1992-06-25 Hoechst Aktiengesellschaft Pyridyl-pyrimidin-derivates, process for producing the same, agents containing the same and their use as fungicides
DE4105751A1 (en) * 1991-02-23 1992-08-27 Bayer Ag SUBSTITUTED PYRIDYLPYRIMIDINE, THEIR PRODUCTION AND THEIR USE AND NEW INTERMEDIATE PRODUCTS
WO1993014080A1 (en) * 1992-01-15 1993-07-22 E.I. Du Pont De Nemours And Company Bridged heterocyclic fungicides
MXPA03008121A (en) 2001-03-15 2003-12-12 Basf Ag 5-phenylpyrimidine, methods and intermediate products for the production thereof and use of the same for controlling pathogenic fungi.
BRPI0406757A (en) * 2003-02-06 2005-12-20 Basf Ag Pyrimidine, process for preparing same, intermediate product, pesticidal agent, and process for combating harmful phytopathogenic fungi

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DE3675197D1 (en) * 1985-12-03 1990-11-29 Sumitomo Chemical Co PYRIDINYLPYRIMIDINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THESE PLANT DISEASES PROTECTIVE CONTAINING THE ACTIVE SUBSTANCE.
CA1288433C (en) * 1986-12-03 1991-09-03 Tsuguhiro Katoh Pyridinylpyrimidine derivatives, method for production thereof and a fungicide containing them as the active ingredient

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Title
See references of WO9107400A1 *

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CA2068328A1 (en) 1991-05-10
HU9201543D0 (en) 1992-09-28
PT95831A (en) 1991-09-13
YU212990A (en) 1992-09-07
KR927003569A (en) 1992-12-18
IL96271A0 (en) 1991-08-16
ZA908958B (en) 1991-08-28
WO1991007400A1 (en) 1991-05-30
JPH05501550A (en) 1993-03-25
MX23260A (en) 1993-06-01
BR9007833A (en) 1992-09-22
CN1051559A (en) 1991-05-22
AU6638990A (en) 1991-06-13
HUT62287A (en) 1993-04-28
DE3937284A1 (en) 1991-05-16

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