WO1992005159A1 - 2-phenyl-pyrimidines, leur procede de production, agents les contenant et leur utilisation comme fongicides - Google Patents

2-phenyl-pyrimidines, leur procede de production, agents les contenant et leur utilisation comme fongicides Download PDF

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Publication number
WO1992005159A1
WO1992005159A1 PCT/EP1991/001790 EP9101790W WO9205159A1 WO 1992005159 A1 WO1992005159 A1 WO 1992005159A1 EP 9101790 W EP9101790 W EP 9101790W WO 9205159 A1 WO9205159 A1 WO 9205159A1
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Prior art keywords
alkyl
optionally substituted
alkoxy
alkylthio
halo
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PCT/EP1991/001790
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German (de)
English (en)
Inventor
Klemens Minn
Peter Braun
Burkhard Sachse
Heinrich Wicke
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Hoechst Aktiengesellschaft
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Publication of WO1992005159A1 publication Critical patent/WO1992005159A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

Definitions

  • 2-PhenyI-pyrimidines process for their preparation, compositions containing them and their use as fungicides.
  • the present invention therefore relates to compounds of the formula
  • R 1 , R 2 , R 3 independently of one another hydrogen, halogen, hydroxy, amino, nitro, cyano, thiocyano, (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylarnino, (C 1 -C 4 ) dialkylamino, (C 1 -C 4 ) alkylcarbonylamino, halo (C 1 -C 4 ) alkyl,
  • (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl,
  • Phenoxy- (C 1 -C 4 ) alkyl optionally substituted phenylketo- (C 1 -C 4 ) alkyl, optionally substituted phenyloxycarbonyl- (C 1 -C 4 ) alkyl,
  • Phenoxyphenyl- (C 1 -C 4 ) alkyl, where optionally substituted is to be understood that the phenyl part up to three times by halogen, ester, (C 1 -C 4 ) alkyl,
  • R 1 , R 2 and / or R 3 optionally together form a saturated, partially unsaturated or aromatic carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members,
  • R 4 hydrogen, halogen, (C 1 -C 4 ) alkyl, hydroxy- (C 1 -C 4 ) alkyl, dihydroxy- (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl, halo - (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl,
  • (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl,
  • Phenoxy- (C 1 -C 4 ) alkyl optionally substituted phenylmercapo - (C 1 -C 4 ) alkyl, optionally substituted 5- or 6-membered heteroaromatic, optionally substituted phenylcarbonyl, optionally substituted phenylketo (C 1 -C 4 ) alkyl , optionally substituted phenyloxycarbonyl- (C 1 -C 4 ) alkyl, optionally substituted phenylamino- (C 1 -C 4 ) alkyl, optionally substituted
  • Phenoxyphenyl- (C 1 -C 4 ) alkyl, where optionally substituted is to be understood that the phenyl part (heteroaromatic) up to three times by halogen, ester,
  • R 5 halogen, (C 1 -C 4 ) alkyl, (C 1 -C 9 ) alkoxy, hydroxy- (C 1 -C 4 ) alkyl,
  • Phenyloxycarbonyl- (C 1 -C 4 ) alkyl optionally substituted
  • Phenylamino (C 1 -C 4 ) alkyl optionally substituted
  • Phenoxyphenyl- (C 1 -C 4 ) alkyl whereby optionally substituted is to be understood that the phenyl part is substituted up to three times by halogen, ester, (C 1 -C 4 ) alkyl,
  • Phenyloxycarbonyl- (C 1 -C 4 ) alkyl optionally substituted
  • Phenoxy- (C 1 -C 4 ) alkyl optionally substituted phenyl- (C 1 -C 4 ) alkyl,
  • Phenoxyphenyl- (C 1 -C 4 ) alkyl optionally substituted
  • Phenylmercapto- (C 1 -C 4 ) alkyl where optionally substituted is to be understood that the phenyl part is substituted up to three times by halogen, ester, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy or can be simply substituted by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms,
  • R 5 and R 6 optionally together a saturated, partially unsaturated or
  • R 7 , R 8 independently of one another hydrogen, hydroxy, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy,
  • R 9 , R 10 independently of one another hydrogen, (C 1 -C 9 ) alkyl, cyano- (C 1 -C 4 ) alkyl,
  • phenylamino (C 1 -C 4 ) alkyl optionally substituted phenoxyphenyl- (C 1 -C 4 ) alkyl, which is to be understood as being optionally substituted. that the phenyl part up to three times by halogen, ester, (C 1 -C 4 ) alkyl,
  • Carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members and n a number from 0 to 8, and their acid addition salts.
  • R 1 , R 2 , R 3 preferably independently of one another are hydrogen, halogen, hydroxy, amino, nitro.
  • (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylcarbonyl,
  • optionally substituted phenyl optionally substituted phenoxy, optionally substituted phenyl- (C 1 -C 4 ) alkyl, optionally substituted phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenylketo (C 1 -C 4 ) alkyl, wherein under optionally Substituted is to be understood that the phenyl part up to three times by halogen, ester, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio,
  • R 2 , R 2 and / or R 3 together can be a saturated, partially unsaturated or
  • R 1 , R 2 , R 3 are, in particular independently of one another, hydrogen, chlorine, bromine, nitro or (C 1 -C 4 ) alkoxy, particularly preferably hydrogen, chlorine, bromine or OCH 3 .
  • R 4 preferably denotes hydrogen, halogen, (C 1 -C 4 ) alkyl, hydroxy- (C 1 -C 4 ) alkyl, Dihydroxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio, perhalo (C 1 -C 4 ) alkylthio, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, ( C 1 -C 4 ) alkylamino (C 1 -C 4 ) alkyl,
  • (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, optionally substituted phenyl, optionally substituted 5- or 6-membered Heteroaromatic, for example pyrimidine, pyridine or thiophene, optionally substituted phenylcarbonyl, where optionally substituted means that the phenyl ring
  • R 4 is in particular hydrogen, iodine, bromine, dialkylamino (C 1 -C 4 ) alkyl,
  • phenyl or pyridinyl particularly preferably hydrogen.
  • R 5 preferably denotes halogen, (C 1 -C 4 ) alkyl, (C 1 -C 9 ) alkoxy, hydroxy- (C 1 -C 4 ) alkyl,
  • optionally substituted phenyl- (C 1 -C 4 ) alkoxy where optionally substituted is understood to mean that the phenyl part is substituted up to three times by halogen, ester, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) haloalkyl,
  • (C 1 -C 4 ) haloalkoxy or simply substituted by nitro or cyano and R 5 is in particular halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, phenyl- (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkynyloxy, (C 1 -C 4 ) Alkylmercapto or (C 1 -C 4 ) alkylsulfonyl, particularly preferably Cl, Br, OCH 3 or OC 2 H 5 .
  • R 6 preferably denotes hydrogen, halogen, (C 1 -C 4 ) alkyl, hydroxy- (C 1 -C 4 ) alkyl,
  • R 6 is in particular hydrogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl or
  • (C 1 -C 4 ) alkoxycarbonyl particularly preferably hydrogen or -O-CH 2 -CH 2 .
  • R 5 and R 6 together can be a saturated, partially unsaturated or aromatic
  • R 9 , R 10 are independently hydrogen, (C 1 -C 9 ) alkyl or by halogen,
  • R 9 and R 10 together can form a saturated or partially unsaturated carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10, in particular 5 or 6, ring members, n is preferably a number from 0 to 4, in particular a number of 0 up to 2
  • Halo in the substituents is substituted one or more times by halogen atoms.
  • hydrohalic acids such as hydrochloric acid or
  • Hydrobromic acid phosphoric acid, nitric acid, sulfuric acid, mono- or
  • bifunctional carboxylic acids and hydroxycarboxylic acids such as acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid or lactic acid, as well as sulfonic acids such as p-toluenesulfonic acid or 1,5-naphthalenedisulfonic acid.
  • the acid addition compounds of the formula I can be prepared in a simple manner, e.g. be obtained by dissolving a compound of formula I in a suitable organic solvent and adding the acid and in a known manner, e.g. by filtration, isolated and optionally cleaned by washing with an inert organic solvent.
  • the pyrimidines of the formula I can be prepared by various multistage processes.
  • suitable 3-ketocarboxylic acid esters with benzamidines, where they can be used in pure form or in situ, released from their salts, without solvent or in a suitable aprotic or protic solvent, for example water or lower alcohols, at temperatures from 0 ° C to 160 ° C, preferably at temperatures between room temperature and the boiling point of the solvent, in the presence of a suitable base, such as alkali metal carbonates, Na 2 CO 3 or K 2 CO 3 , or
  • Alkali alcoholates e.g. NaOMe or NaOEt
  • 4-pyrimidinones e.g. NaOMe or NaOEt
  • Literature regulations Beilstein, 3rd / 4th supplement, volume 25, p. 279 can be produced in two stages in a one-pot process.
  • an inert solvent such as toluene, THF, dioxane or diethyl ether, corresponding carboxylic acid derivatives with a suitable base, generally with an alkali metal hydride, preferably NaH, or
  • Alkaline alcoholate preferably NaOMe, anionized, then formylated with an ant ester.
  • the subsequent condensation can be carried out with benzamidines, these being used in pure form or in situ, using bases, for example with alcoholates such as NaOMe, released from their salts.
  • Protic solvents in particular lower alcohols, have proven particularly suitable for the condensation.
  • the reaction can be carried out in protic solvents, such as water or alcohols, at room temperature, at elevated temperatures or at
  • Boiling temperature of the solvent take place, where appropriate an auxiliary base such as alkali metal carbonates or alkali metal alcoholates can be used.
  • Solvent in a solvent inert to POCl 3 (POBr 3 ) or in a basic solvent such as DMF without or with an acid scavenger such as
  • the halogen atom against alcoholates of the corresponding Exchange alkynols (formula V), prepared from the corresponding alkinol and a base, preferably NaH (see. Comprehensive Heterocyclic Chemistry, AR Katritzky, CW Rees, Pergamon Press, Oxford, New York, 1984, Vol.3, p. 100).
  • HCl HBr
  • a base e.g. Triethylamine
  • Solvents can be used at temperatures from 25 ° C to the boiling point of
  • Solvent preferably from 40 ° C to 60 ° C. with base addition, preferably
  • Alkaline alcoholates Pyrimidine carboxylic acid salts obtained as condensation products.
  • alkynyl function Another example of a subsequent modification is the halogenation of the alkynyl function.
  • alkynes, di- and polyynes, allenes, cumulenes / methods of organic chemistry / (Houben / Weyl)
  • aprotic solvent such as THF or dioxane
  • bases e.g. n-Butyllithium, which abstracts the terminal proton of the ethynyl derivative and then a halogen, for example iodine or bromine, is introduced.
  • the compounds of formula I according to the invention can be used to protect various crop plants against pathogenic microorganisms, in particular fungi, and are distinguished by a particularly high crop plant tolerance. They have advantageous preventive and systemic properties, and fungal pathogens that have already penetrated the plant tissue can also be successfully combated. By spraying, dusting or other applications with active ingredients of the formula I, plants and existing or growing parts of plants can be protected from pests which occur. They are also suitable as mordants for the treatment of Seeds and cuttings to protect against fungal infections and pathogenic fungi occurring in the soil.
  • the compounds according to the invention are also suitable for use in technical fields, for example as wood preservatives, as preservatives in paints, in cooling lubricants for metalworking or as
  • the invention also relates to compositions which contain the compounds of the formula I in addition to suitable formulation auxiliaries.
  • the agents according to the invention generally contain the active ingredients of the formula I in an amount of 1 to 95% by weight.
  • Formulation options are therefore possible: wettable powder (WP), emulsifiable concentrates (EC), aqueous dispersions based on oil or water (SC), suspoemulsions (SC), dusts (DP), mordants, granules in the form of water-dispersible
  • WP wettable powder
  • EC emulsifiable concentrates
  • SC aqueous dispersions based on oil or water
  • SC suspoemulsions
  • DP dusts
  • mordants granules in the form of water-dispersible
  • Granules WG
  • ULV Granules
  • microcapsules microcapsules
  • waxes waxes or baits.
  • the necessary formulation aids such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in:
  • fertilizers and / or growth regulators can also be prepared, e.g. B. in the form of a finished formulation or as a tank mix.
  • Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, are also a wetting agent, in addition to a diluent or inert substance.
  • Alkylphenols polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates and
  • Dispersants e.g. B. sodium lignosulfonic acid
  • Emulsifiable concentrates are obtained by dissolving the active ingredient in an organic solvent, e.g. B. butanol,
  • Hydrocarbons produced with the addition of one or more emulsifiers Hydrocarbons produced with the addition of one or more emulsifiers.
  • emulsifiers examples include: alkylarylsulfonic acid
  • Calcium salts such as Ca-dodecylbenzenesulfonate or non-ionic emulsifiers such as
  • Fatty acid polyglycol esters Fatty acid polyglycol esters, alkylaryl polyglycol solvents, fatty alcohol polyglycol ethers, Propylene oxide-ethylene oxide-sorbitan fatty acid ester, polyoxethylene sorbitan fatty acid ester or polyoxethylene sorbitol ester.
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. B. talc, natural clays such as kaolin, bentonite, poryphillite or diatomaceous earth.
  • Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying
  • Active substance concentrates using adhesives e.g. polyvinyl alcohol, polyacrylic acid
  • Sodium or mineral oils on the surface of carriers such as sand, kaolinite or granulated inert material.
  • Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if appropriate in a mixture with fertilizers.
  • the active ingredient concentration in wettable powders is 10 to 90% by weight, the remainder 100% by weight consists of customary formulation components.
  • the active substance concentration can be 5 to 80% by weight.
  • Dust-like formulations usually contain 5 to 20% by weight.
  • the active ingredient content depends in part on whether the active compound is liquid or solid and which compound is liquid or solid and which granulation aids, fillers etc. are used.
  • the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers.
  • Dust-like and granulated preparations as well as sprayable solutions are usually no longer diluted with other inert substances before use
  • the application rate required varies with the external conditions such as temperature, humidity and others. It can fluctuate within wide limits, e.g. B. from 0.005 to 10.0 kg / ha, preferably it is in the range of 0.01 to 5 kg / ha.
  • the active compounds according to the invention can be used either alone or in combination with other fungicides known from the literature
  • Triadimenol Fluotrimazole, tridemorph, dodemorph, fenpropimorph, falimorph,
  • active ingredients which are largely in CH. R. Worthing, USB Walker, The Pesticide Manual, 7th edition (1983), British Crop Protection Council.
  • active compounds according to the invention in particular those of the examples listed, can be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • Insecticides include, for example
  • Phosphoric acid esters carbamates, carboxylic acid esters, formamidines, tin compounds, substances produced by microorganisms and the like. a .. Preferred mixing partners are:
  • Pirimiphos-methyl Profenofos, Prothiofos, Sulprofos, Triazophos, Trichlorphon.
  • Allethrin Alphamethrin, bioallethrin, bioresmethrin, cycloprothrin, cyfluthrin, cyhalothrin. Cypermethrin, deltamethrin, 2,2-dimethyl-3- 2-chloro-2-trifluoromethylvinyI) -cyclopropanecarboxylic acid- (alpha-cyano-3-phenyl-2-methyl-benzyI) ester (FMC 54800), fenpropathrin, fenfluthrin, fenvalerate. Flucythrinate, flumethrin, fluvalinate, permethrin, resmethrin, tralomethrin.
  • Application forms can vary within a wide range, the active compound concentration of the use forms can be from 0.0001 to 100% by weight of active compound, preferably from 0.001 to 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • a dispersion concentrate which is easily dispersible in water is prepared by mixing 40 parts by weight of active ingredient with 7 parts by weight of a sulfosuccinic acid half-ester, 2 parts by weight of a lignosulfonic acid sodium salt and 51 parts by weight of water and ground in a attritor to a fineness of less than 5 microns.
  • An emulsifiable concentrate can be prepared from 15 parts by weight of active ingredient, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated
  • Granules can be produced from 2 to 15 parts by weight of active ingredient and an inert granule carrier material such as attapulgite, pumice granules and / or quartz sand.
  • a suspension of the wettable powder from example b) having a solids content of 30% is expediently used and sprayed onto the surface of an attapulgite granulate, dried and mixed intimately.
  • the proportion by weight of the wettable powder is approximately 5% and that of the inert carrier material approximately 95% of the finished granulate.
  • the corresponding ethanolate solution was prepared from 27.6 g of sodium and 480 ml of ethanol and 67.6 g of mucochloric acid were dissolved in 120 ml of ethanol.
  • Half the amount of the ethanolate solution was added dropwise to 156.6 g of benzamidine hydrochloride (80-85%, technical quality, containing about 15% water) in 80 ml of ethanol, and the mixture was heated to 55-60 ° C. and dripped at this temperature first half of the muccochloric acid solution to the reaction mixture, dropwise added the second half of the ethanolate and then the rest of the muccochloric acid solution.
  • the mixture was stirred for a further hour at 55-60 ° C., cooled and filtered off.
  • the mother liquor was adjusted to a pH of 2 with 2N hydrochloric acid and filtered again.
  • the examples with the suffix A are the acid addition salts of the respective parent compound; The acid is then indicated in the "physical constant" column and the associated melting or decomposition point.
  • the salts can also contain water of crystallization in individual cases.
  • the plants were inoculated with a spore suspension (1.5 million spores / ml) of Botrytis cinerea (BCM-resistant strain).
  • the plants were in a climatic chamber at 20-22 ° C. and approx. 99% rel. Humidity continued to be cultivated.
  • the infection of the plants manifests itself in the formation of black spots on leaves and stems.
  • the tests were evaluated approximately 1 week after inoculation.
  • the plants were inoculated with a spore suspension (1.5 million spores / ml) of Botrytis cinerea (BCM-resistant strain).
  • the plants were in a climatic chamber at 20 - 22 ° C and approx. 99% rel. Humidity continued to be cultivated.
  • the infection of the plants manifests itself in the formation of black spots on leaves and stems.
  • the tests were evaluated approximately 1 week after inoculation.

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

Abstract

Des composés ont la formule (I), dans laquelle R?1, R2, R3¿ désignent indépendamment les uns des autres hydrogène, chlore, brome, nitro ou (C¿1?-C4)alcoxy; R?4¿ désigne hydrogène, iode, brome (C¿1?-C4)alkyle, dialkylamino-(C1-C4)alkyle, phényl-(C1-C4)alkyl-(C1-C4)alkylamino-(C1-C4)alkyle, phényle ou pyridinyle éventuellement substitués dans la fraction phényle (hétéroaromatique) par halogène, (C1-C4)alkyle, (C1-C4)alcoxy ou perhalo-(C1-C4)alkyle; R?5¿ désigne halogène, (C¿1?-C4)alkyle, (C1-C4)alcoxy, phényl-(C1-C4)alcoxy, (C1-C4)alcinyloxy, (C1-C4)alkylmercapto ou (C1-C4)alkylsulfonyle; R?6¿ désigne hydrogène, (C¿1?-C4)alkyle, (C1-C4)alcoxy-(C1-C4)alkyle ou (C1-C4)alcoxy-carbonyle; R?5 et R6¿ forment ensemble le cas échéant une partie d'un cycle saturé ou insaturé avec 5 ou 6 éléments cycliques, dans lequel un carbone peut être substitué par S; X désigne C=O ou NH; Y désigne O ou NH, lorsque X désigne C=O; Y est absent lorsque X désigne O ou NH et n est un nombre entre 0 et 2. Ces composés ont des propriétés pesticides avantageuses, notamment pour détruire des champignons nuisibles. L'invention concerne également un procédé de production de composés ayant la formule (I).
PCT/EP1991/001790 1990-09-19 1991-09-19 2-phenyl-pyrimidines, leur procede de production, agents les contenant et leur utilisation comme fongicides WO1992005159A1 (fr)

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DE4029654A DE4029654A1 (de) 1990-09-19 1990-09-19 2-phenyl-pyrimidine, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung als fungizide
DEP4029654.7 1990-09-19

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002006246A1 (fr) 2000-07-19 2002-01-24 Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. Acides carboxyliques de dihydroxypyrimidine utilises comme inhibiteurs de polymerases virales
JP2002530385A (ja) * 1998-11-19 2002-09-17 アベンティス・ファーマ・ドイチユラント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング 置換４−アミノ−２−アリールシクロペンタ［ｄ］ピリミジン、それらの製造、それらの使用およびそれらを含有する医薬製剤
WO2005047233A1 (fr) * 2003-10-31 2005-05-26 Syngenta Participations Ag Nouveaux herbicides
JP2007501258A (ja) * 2003-08-05 2007-01-25 バーテックス　ファーマシューティカルズ　インコーポレイテッド 電位依存型イオンチャネルの阻害剤としての縮合ピリミジン化合物
JP2008502674A (ja) * 2004-06-17 2008-01-31 アデックス ファーマ ソシエテ アノニム 代謝調節型グルタミン酸レセプタのモジュレータとしての新規アルキニル誘導体
WO2008081017A1 (fr) * 2007-01-03 2008-07-10 Bayer Cropscience Ag Nouveaux dérivés de n-alkynylcarboxamide
US7863220B2 (en) 2003-12-19 2011-01-04 David Alan Clark Herbicidal pyrimidines
US8198442B2 (en) 2005-05-06 2012-06-12 E.I. Du Pont De Nemours And Company Method for preparation of optionally 2-substituted 1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acids

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EP1238586A1 (fr) 2001-03-09 2002-09-11 Basf Aktiengesellschaft 2-alkynyl-pyri(mi)dines herbicides
PL212914B1 (pl) 2001-10-26 2012-12-31 Angeletti P Ist Richerche Bio N-podstawione hydroksypirymidynonokarboksyamidy jako inhibitory integrazy HIV

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JP4695262B2 (ja) * 1998-11-19 2011-06-08 サノフィ−アベンティス・ドイチュラント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング 置換４−アミノ−２−アリールシクロペンタ［ｄ］ピリミジン、それらの製造、それらの使用およびそれらを含有する医薬製剤
JP2002530385A (ja) * 1998-11-19 2002-09-17 アベンティス・ファーマ・ドイチユラント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング 置換４−アミノ−２−アリールシクロペンタ［ｄ］ピリミジン、それらの製造、それらの使用およびそれらを含有する医薬製剤
US6627628B1 (en) 1998-11-19 2003-09-30 Aventis Pharma Deutschland, Gmbh Substituted 4-amino-2-aryl-cyclopenta[d]pyrimidines, their production and use and pharmaceutical preparations containing same
JP2004504304A (ja) * 2000-07-19 2004-02-12 イステイチユート・デイ・リチエルケ・デイ・ビオロジア・モレコラーレ・ピ・アンジエレツテイ・エツセ・ピー・アー ウィルスポリメラーゼ阻害薬としてのジヒドロキシピリミジンカルボン酸類
WO2002006246A1 (fr) 2000-07-19 2002-01-24 Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. Acides carboxyliques de dihydroxypyrimidine utilises comme inhibiteurs de polymerases virales
AU2001272530B2 (en) * 2000-07-19 2006-08-03 Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A Dihydroxypyrimidine carboxylic acids as viral polymerase inhibitors
US7091209B2 (en) 2000-07-19 2006-08-15 Merck & Co., Inc. Dihydroxypyridmidine carboxylic acids as viral polymerase inhibitors
JP2007501258A (ja) * 2003-08-05 2007-01-25 バーテックス　ファーマシューティカルズ　インコーポレイテッド 電位依存型イオンチャネルの阻害剤としての縮合ピリミジン化合物
JP4808156B2 (ja) * 2003-08-05 2011-11-02 バーテックス ファーマシューティカルズ インコーポレイテッド 電位依存型イオンチャネルの阻害剤としての縮合ピリミジン化合物
JP2011207914A (ja) * 2003-08-05 2011-10-20 Vertex Pharmaceuticals Inc 電位依存型イオンチャネルの阻害剤としての縮合ピリミジン化合物
WO2005047233A1 (fr) * 2003-10-31 2005-05-26 Syngenta Participations Ag Nouveaux herbicides
US7863220B2 (en) 2003-12-19 2011-01-04 David Alan Clark Herbicidal pyrimidines
US8802597B2 (en) 2003-12-19 2014-08-12 E I Du Pont De Nemours And Company Herbicidal pyrimidines
JP2008502674A (ja) * 2004-06-17 2008-01-31 アデックス ファーマ ソシエテ アノニム 代謝調節型グルタミン酸レセプタのモジュレータとしての新規アルキニル誘導体
JP2012051937A (ja) * 2004-06-17 2012-03-15 Addex Pharma Sa 代謝調節型グルタミン酸レセプタのモジュレータとしての新規アルキニル誘導体
US8674106B2 (en) 2004-06-17 2014-03-18 Addex Pharma Sa Alkynyl derivatives as modulators of metabotropic glutamate receptors
US8883826B2 (en) 2004-06-17 2014-11-11 Addex Pharma Sa Alkynyl derivatives as modulators of metabotropic glutamate receptors
US8198442B2 (en) 2005-05-06 2012-06-12 E.I. Du Pont De Nemours And Company Method for preparation of optionally 2-substituted 1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acids
WO2008081017A1 (fr) * 2007-01-03 2008-07-10 Bayer Cropscience Ag Nouveaux dérivés de n-alkynylcarboxamide

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