WO1992005158A1 - 4-anilino-pyrimidines, leur procede de production, agents les contenant et leur utilisation comme fongicides - Google Patents

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

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

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • 4-anilino-pyrimidine derivatives are known to be effective components in fungicidal compositions
  • New 4-anilino-pyrimidine derivatives have been found which have advantageous effects in combating a broad spectrum of phytopatogenic fungi, in particular at low doses, and do not cause damage to useful plants.
  • the present invention therefore relates to compounds of the formula I
  • R 1 , R 2 independently of one another hydrogen, (C 1 -C 9 ) alkyl, cyano- (C 1 -C 4 ) alkyl,
  • (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, optionally substituted 5- or 6-membered heteroaromatic, optionally substituted Phenyl, optionally substituted phenoxy, optionally substituted phenyl- (C 1 -C 4 ) alkyl, optionally substituted phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenylmercapto- (C 1 -C 4 ) alkyl, optionally substituted
  • Phenylamino (C 1 -C 4 ) alkyl optionally substituted
  • Phenoxyphenyl- (C 1 -C 4 ) alkyl, where optionally substituted is to be understood that the phenyl part (heteroaromatic) up to three times by halogen, ester,
  • (C 1 -C 4 ) can be haloalkoxy or simply substituted by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms, R 1 and R 2 optionally together a saturated or partially unsaturated
  • R 3 hydrogen, halogen, (C 1 -C 4 ) alkyl, hydroxy- (C 1 -C 4 ) alkyl, dihydroxy- (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl, halo - (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl,
  • (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl,
  • Phenyl- (C 1 -C 4 ) alkyl optionally substituted phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenylmercapto- (C 1 -C 4 ) alkyl, optionally substituted phenylketo- (C 1 -C 4 ) alkyl , optionally substituted
  • Phenyloxycarbonyl- (C 1 -C 4 ) alkyl optionally substituted
  • Phenylamino (C 1 -C 4 ) alkyl optionally substituted
  • Phenoxyphenyl- (C 1 -C 4 ) alkyl, where optionally substituted is to be understood that the phenyl part (heteroaromatic) up to three times by halogen, ester,
  • (C 1 -C 4 ) can be haloalkoxy or simply substituted by niuo or cyano, and can mean halo in the substituents substituted one or more times by halogen atoms,
  • R 4 , R 5 , R 6 independently of one another hydrogen, halogen, hydroxy, amino, nitro, cyano, thiocyano, (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylamino, (C 1 -C 4 ) dialkylamino, (C 1 -C 4 ) alkylcarbonylamino, halo (C 1 -C 4 ) alkyl, Hydroxy- (C 1 -C 4 ) alkyl, dihydroxy- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, halo (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl- (C 1 -C 4 ) alkylthio, halo (C 1
  • Phenoxyphenyl- (C 1 -C 4 ) alkyl, where optionally substituted is to be understood that the phenyl part (heteroaromatic) up to three times by halogen, ester,
  • (C 1 -C 4 ) haloalkoxy or can be substituted simply by nitro or cyano, and halo in the substituents can be substituted one or more times by halogen atoms,
  • R 4 , R 5 and / or R 6 optionally together form a saturated, partially unsaturated or aromatic carbocycle or heterocycle with the heteroatoms O, N, S, Si or P with 4 to 10 ring members,
  • R 7 hydrogen, formyl, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, halo (C 1 -C 4 ) alkoxy,
  • (C 1 -C 4 ) alkoxycarbonyl optionally substituted phenyl, optionally substituted phenoxy, optionally substituted phenyl- (C 1 -C 4 ) alkyl, optionally substituted phenoxy- (C 1 -C 4 ) alkyl, optionally substituted phenylmercapto- (C 1 -C 4 ) alkyl, optionally substituted
  • Phenyloxycarbonyl- (C 1 -C 4 ) alkyl optionally substituted
  • Phenylamino (C 1 -C 4 ) alkyl optionally substituted
  • Phenoxyphenyl- (C 1 -C 4 ) alkyl whereby optionally substituted is to be understood that the phenyl part is substituted up to three times by halogen, ester, (C 1 -C 4 ) alkyl,
  • R 7 and R 4 and / or R 5 optionally together a saturated or partially
  • R 8 , R 9 independently of one another hydrogen, halogen, (C 1 -C 4 ) alkyl,
  • (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl,
  • Phenoxy- (C 1 -C 4 ) alkyl optionally substituted phenylmercapto- (C 1 -C 4 ) alkyl, optionally substituted phenylketo- (C 1 -C 4 ) alkyl, optionally substituted phenyloxycarbonyl- (C 1 -C 4 ) alkyl, optionally substituted
  • Phenylamino (C 1 -C 4 ) alkyl optionally substituted
  • Phenoxyphenyl- (C 1 -C 4 ) alkyl whereby optionally substituted is to be understood that the phenyl part is substituted up to three times by halogen, ester, (C 1 -C 4 ) alkyl,
  • R 8 and R 9 optionally together a saturated, partially unsaturated or
  • R 1 , R 2 preferably independently of one another are hydrogen, (C 1 -C 9 ) alkyl, in the phenyl part by halogen, (C 1 -C 4 ) alkyl or (C 1 -C 4 ) alkoxy optionally substituted phenyl, in particular hydrogen or (C 1 -C 4 ) alkyl, particularly preferably hydrogen, R 1 and R 2 together can form a saturated or partially unsaturated carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10 ring members, in particular with 5 or 6 ring members, and
  • R 3 preferably denotes hydrogen, halogen, (C 1 -C 4 ) alkyl, hydroxy- (C 1 -C 4 ) alkyl,
  • (C 3 -C 9 ) cycloalkyl- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl, the cyclic radicals being up to threefold by (C 1 -C 4 ) Alkyl can be substituted, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted 5- to 6-membered heteroaromatic, for example pyridm, thiophene, where optionally substituted is to be understood to mean that the phenyl part (heteroaromatic) is substituted up to three times by halogen, ester , (C 1 -C 4 ) alkyl, (C !
  • R 3 is in particular hydrogen or halogen, particularly preferably hydrogen.
  • R 4 , R 5 , R 6 are preferably independently of one another hydrogen, halogen, hydroxyl,
  • (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl where the cyclic radicals can be substituted up to three times by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxycarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylaminocarbonyl- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylcarbonyl,
  • R 4 , R 5 and / or R 6 together can be a saturated, partially unsaturated or
  • R 4 , R 5 , R 6 are in particular independently of one another hydrogen, halogen,
  • R 7 preferably denotes hydrogen, (C 1 -C 4 ) alkyl, cyano- (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, halo- (C 1 -C 4 ) alkoxy, amino (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkylamino (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkoxy, amino, (C 1 -C 4 ) alkylamino ,
  • R 7 and R 4 and / or R 5 together can form a saturated or partially unsaturated carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10 ring members.
  • R 7 in particular denotes hydrogen or (C 1 -C 4 ) alkyl, particularly preferably hydrogen.
  • R 8 , R 9 are preferably independently of one another hydrogen, halogen, (C 1 -C 4 ) alkyl,
  • (C 3 -C 9 ) cycloalkyl- (C 1 -C 4 ) alkyl, (C 3 -C 9 ) heterocycloalkyl- (C 1 -C 4 ) alkyl, the cyclic radicals being up to threefold by (C 1 -C 4 ) Alkyl may be substituted, (C 1 -C 4 ) alkylcarbonyl, (C 1 -C 4 ) alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted
  • Phenoxyphenyl- (C 1 -C 4 ) alkyl whereby optionally substituted is to be understood that the phenyl part is substituted up to three times by halogen, ester, (C 1 -C 4 ) alkyl,
  • R 8 in particular denotes hydrogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, phenyl- (C 1 -C 4 ) alkoxy or halogen, particularly preferably hydrogen, Cl or OCH 3 .
  • R 8 and R 9 together can form a saturated, partially unsaturated or aromatic carbocycle or heterocycle with the heteroatoms O, N or S with 4 to 10 ring members.
  • R 9 in particular denotes hydrogen, (C 1 -C 4 ) alkyl, perhalo (C 1 -C 4 ) alkyl,
  • X is preferably oxygen or sulfur and n is a number from 0 to 4, in particular 0 or 1, particularly preferably 0.
  • Halo in the individual substituents is to be understood as being substituted one or more times by halogen atoms.
  • hydrohalic acids such as hydrochloric acid or
  • Hydrobromic acid phosphoric acid, nitric acid, sulfuric acid, mono- or
  • bifunctional carboxylic acids and hydroxycarboxylic acids such as acetic acid, maleic acid, Succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid or lactic acid, and also sulfonic acids such as p-toluenesulfonic acid or 1,5-naphthalenedisulfonic acid.
  • the acid addition compounds of the formula I can be obtained in a simple manner by the customary salt formation methods, for example by dissolving a compound of the formula I in a suitable organic solvent and adding the acid, and can be isolated in a known manner, for example by filtration, and optionally by washing with an inert solvent organic solvents can be cleaned.
  • the pyrimidines of the formula I can be prepared by various multistage processes.
  • R 10 in this and in the following formula schemes stands for S, S- (C 1 -C 4 ) alkyl, im
  • R 11 represents (C 1 -C 4 ) alkyl or im
  • the subsequent condensation can take place with thiourea or S-alkylated thioureas, which can be used in pure form or in situ, using bases (alcoholates such as NaOMe) released from their salts.
  • bases alcoholates such as NaOMe
  • Protic solvents in particular lower alcohols, have proven particularly suitable for the condensation.
  • the known pyrimidinones or mercaptopyrimidinones are modified with an alkylating agent, such as alkyl halides (for example methyl iodide) or alkyl acid esters (for example dimethyl sulfate, trimethyl phosphoric acid), in particular propynyl halides, using a base such as NaOH, NaH or triethylamine in a suitable protic or aprotic solvent (DMF, acetonitrile , Water) at temperatures from 0 ° C to 260 ° C, preferably in the temperature range from 50 ° C to the boiling point of
  • the 4-pyrimidinones thus obtained can be treated with excess POCl 3 (POBr 3 ) without solvent, in a solvent inert to POCl 3 (POBr 3 ) or in a basic solvent such as DMF without or with an acid scavenger such as
  • N, N-dimethylaniline in 0.001 to 2 molar equivalents, preferably 0.02 equivalents, at temperatures from 50 ° C. to 110 ° C., preferably at the boiling point of POCl 3 (POBr 3 ), are converted into the corresponding 4-halopyrimidines (cf. Beilstein, Hauptwerk, volume 25, p. 372, Beilstein, 3rd / 4th supplement, volume 23, p. 2471).
  • he anilines of formula IV are mostly known compounds or can in can be produced in a manner analogous to those skilled in the art.
  • the reaction of II with IV takes place depending on the reactivity of the derivatives in an inert solvent (water / acetone, toluene, THF) at temperatures from 0 ° C. to 150 ° C., preferably from 50 ° C. to 100 ° C.
  • the exchange can be promoted by adding catalytic to equimolar bases, but in general it has proven to be advantageous to catalyze the reaction with acid, in particular with hydrochloric acid.
  • R 12 is a radical with a triple bond, the expected addition of the aniline to the triple bond does not take place.
  • the sulfur-bearing group can be oxidized with corresponding 2-alkylmercaptopyrimidines.
  • suitable oxidizing agents such as peroxides (e.g.
  • R 13 represents halogen, in particular chlorine, * *> * R 4
  • the sulfonyl group can be exchanged for alcohols.
  • an inert solvent toluene, THF
  • THF inert solvent
  • halogenation of the alkynyl function may be mentioned as an example of a further modification of starting materials for the preparation of compounds of the formula I.
  • alkynes, di- and polyynes, allenes, cumulenes methods of organic chemistry (Houben / Weyl) Thieme- Verlag, 1977, volume 5.2a, Stuttgart, pp. 600 ff.)
  • a suitable aprotic solvent such as THF or dioxane
  • bases such as n-butyllithium, for example iodine or bromine.
  • R 3 represents X, which represents halogen, in particular bromine or iodine.
  • the compounds of formula I according to the invention can be used to protect various crop plants against pathogenic microorganisms, in particular fungi, and are distinguished by a particularly high crop plant tolerance. They have advantageous preventive and systemic properties. It is also possible to successfully combat curative pathogens that have already penetrated the plant tissue. By spraying, dusting or other applications with active ingredients of the formula I, plants and existing or growing parts of plants can be protected from pests which occur. They are also suitable as dressing agents for the treatment of seeds and plantings for protection against fungal infections and pathogenic fungi occurring in the soil.
  • the spectrum of activity of the claimed compounds encompasses a large number of different economically important phytopathogenic fungi, such as Altemaria mali, Botrytis cinerea, benzimidazole- and / or dicarboximide-sensitive and resistant strains, Sclerotinia sclerotiorum as well as other gray mold species, Cercospora beticola, Ceratheisisipium, Ceratheisisisipa, Ceratheisisisipa, Ceratheisisipasola, Ceratheisisipium, Ceratheisisipasola, Ceratheisisisipa, Ceratheisisipa, Ceratheisisipa graminis hordei, Erysiphe
  • the compounds according to the invention are also suitable for use in technical fields, for example as wood preservatives, as preservatives in paints, in cooling lubricants for metalworking or as
  • compositions which include the compounds of the formula I contain suitable formulation aids.
  • the agents according to the invention generally contain the active ingredients of the formula I in an amount of 1 to 95% by weight.
  • Formulation options are therefore possible: wettable powder (WP), emulsifiable concentrates (EC), aqueous dispersions based on oil or water (SC), suspoemulsions (SC), dusts (DP), mordants, granules in the form of water-dispersible
  • WP wettable powder
  • EC emulsifiable concentrates
  • SC aqueous dispersions based on oil or water
  • SC suspoemulsions
  • DP dusts
  • mordants granules in the form of water-dispersible
  • Granules (WG), ULV formulations, microcapsules, waxes or baits.
  • the necessary formulation aids such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in:
  • z. B. in the form of a finished formulation or as a tank mix.
  • Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, are also a wetting agent, in addition to a diluent or inert substance.
  • Alkylphenols polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates and
  • Dispersants e.g. B. ligmnsulfonic acid sodium,
  • Emulsifiable concentrates are obtained by dissolving the active ingredient in an organic solvent, e.g. B. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers.
  • organic solvent e.g. B. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers.
  • Alkylarylsulfonic acid calcium salts such as Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers,
  • Fatty alcohol polyglycol ether propylene oxide-ethylene oxide-sorbitan fatty acid ester,
  • Polyoxethylene sorbitan fatty acid ester or polyoxethylene sorbitol ester Polyoxethylene sorbitan fatty acid ester or polyoxethylene sorbitol ester.
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. B. talc, natural clays such as kaolin, bentonite, pyrophyllite or diatomaceous earth.
  • Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying
  • Active ingredient concentrates by means of adhesives, e.g. As polyvinyl alcohol, sodium polyacrylic acid or mineral oils, on the surface of carriers such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if appropriate in a mixture with fertilizers.
  • adhesives e.g. As polyvinyl alcohol, sodium polyacrylic acid or mineral oils
  • carriers such as sand, kaolinite or granulated inert material.
  • Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if appropriate in a mixture with fertilizers.
  • the active substance concentration in wettable powders is 10 to 90% by weight, the rest 100% by weight consists of customary formulation components. In the case of emulsifiable concentrates, the active substance concentration can be 5 to 80% by weight. Dust-like formulations usually contain 5 to 20% by weight. In the case of granules, the active ingredient content depends in part on whether the active compound is liquid or solid and which compound is liquid or solid and which granulation aids, fillers etc. are used.
  • the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers.
  • a conventional manner e.g. B. with wettable powders, emulsifiable Concentrates, dispersions and sometimes also in the case of microgranules using water.
  • Dust-like and granulated preparations and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the required application rate varies. It can fluctuate within wide limits, e.g. B. from 0.005 to 10.0 kg / ha or more of active substance, but is preferably in the range of 0.01 to 5 kg / ha.
  • the active compounds according to the invention can be used in their commercially available formulations either alone or in combination with other fungicides known from the literature.
  • Tebuconazole fluotrimazole, tridemorph, dimethomorph, dodemorph, fenpropimorph, Falimorph, S-32165, Chlobenzthiazone, Parinol, buthiobate, fenpropidin, triforine, fenarimol, .Nuarimol, triarimol, ethirimol, dimethirimol, Bupirimate, Rabenzazole, Tricyclazole, Fluobenzimine, Pyroxyfur, NK -483, PP-389, Pyroquilon, Hymexazole, Fenitropan, UHF-8227, Cymoxanil, Dichlorfunanid, Captafol, Captan, Folpet, Tolyfluanid.
  • active compounds according to the invention in particular those of the examples listed, can be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • active compounds include, for example
  • Phosphoric acid esters carbamates, carboxylic acid esters, formamidines, tin compounds, substances produced by microorganisms and the like. a .. Preferred mixing partners are:
  • Demeton-S-methyl diazinon, dichlorvos, dimethoate, ethoprophos, etrimfos, fenitrothion.
  • Fenthion Heptenophos, Parathion, Parathionmethyl, Phosalon, Pirimiphos-ethyl,
  • Pirimiphos-methyl Profenofös, Prothiofos, Sulprofos, Triazophos, Trichlorphon.
  • Cyclopropanecarboxylic acid (2-naphthylmethyl) ester (Ro 12-0470), cyromacin, DDT, dicofol, N- (3,5-dichloro-4- (1,1,2, 2-tetrafluoroethoxy) phenylamino) carbonyl) -2, 6-difluoro-benzamide (XRD 473), diflubenzuron, N- (2,3-dihydro-3-methyl-1,2-thiazol-2-ylidenes) 2,4-xylidenes, dinobutone, dinocap, endosulfane, fenoxycarb, fenthiocarb , Flubenzimine, flufenoxuron.
  • Forms of use can vary widely, the active substance concentration of the forms of use can be from 0.0001 to 100% by weight of active substance, preferably from 0.001 to 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • a dusting agent is obtained by mixing 10 parts by weight of active compound and 90 parts by weight of talc as an inert substance and comminuting them in a hammer mill.
  • a wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight of active compound, 65 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium as the wetting agent. and dispersant mixes and grinds in a pin mill.
  • a dispersion concentrate which is readily dispersible in water is prepared by mixing 40 parts by weight of active compound with 7 parts by weight of a sulfosuccinic acid half-ester, 2 parts by weight of a lignosulfonic acid sodium salt and 51 parts by weight of water and in a attritor milled to a fineness of less than 5 microns.
  • An emulsifiable concentrate can be prepared from 15 parts by weight of active ingredient, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated
  • Granules can be produced from 2 to 15 parts by weight of active ingredient and an inert granule carrier material such as attapulgite, pumice granules and / or quartz sand.
  • a suspension of the wettable powder from example b) having a solids content of 30% is expediently used and this is sprayed onto the surface of a
  • Attapulgite granules dry and mix intimately.
  • the proportion by weight of the wettable powder is approximately 5% and that of the inert carrier material approximately 95% of the finished granulate.
  • Tri (C 8 / C 10 ) alkylmethylammonium chloride stirred for about 1 hour, then dripped 34 ml
  • Propinyl bromide (80% solution in toluene) was added and the mixture was heated under reflux for about 6 hours. After cooling and concentrating the reaction mixture, the mixture was taken up in 300 ml of water, neutralized with acetic acid and, after filtering off, 46 g (98%) were obtained.
  • Tri (C 8 / C 10 ) alkyl methyl ammonium chloride stirred for about 1 hour, then dripped 50 ml
  • the examples with the suffix A are the acid addition salts of the respective parent compound; the acid and the associated melting or decomposition point are then given in the "physical constant" column.
  • the salts can also contain water of crystallization.
  • the plants were inoculated with a spore suspension (1.5 million spores / ml) of Botrytis cinerea (BCM-resistant strain).
  • the plants were in a climatic comb at 20-22 ° C. and approx. 99% rel. Humidity continued to be cultivated.
  • the infection of the plants manifests itself in the formation of black spots on leaves and stems.
  • the tests were evaluated approximately 1 week after inoculation.
  • the plants were again placed in the climatic chamber overnight in order to stimulate the sporulation of the fungus. The infestation was then assessed. The degree of infestation was expressed in% infested leaf area in comparison to the control plants.

Abstract

Des composés ont la formule (I), dans laquelle R1, R2 représentent indépendamment l'un de l'autre hydrogène ou (C¿1?-C4)alkyle; R?1 et R2¿ forment éventuellement ensemble une fraction d'un carbocycle ou hétérocycle saturé ou partiellement insaturé avec les hétéroatomes O, N ou S avec 5 ou 6 chaînons cycliques; R3 représente hydrogène ou halogène; R?4, R5, R6¿ représentent indépendamment les uns des autres hydrogène, halogène, (C¿1?-C4)alkyle, (C1-C4)alcoxy ou phénoxy éventuellement substitué dans la fraction phényle par halogène, (C1-C4)alkyle ou (C1-C4)alcoxy; R?4, R5 et R6¿ forment ensemble une fraction d'un carbocycle ou d'un hétérocycle saturé, partiellement insaturé ou aromatique avec les hétéroatomes O, N ou S avec 5 à 7 chaînons cycliques; R7 représente hydrogène ou (C¿1?-C4)alkyle; R?8¿ représente hydrogène, (C¿1?-C4)alkyle, (C1-C4)alcoxy, phényl-(C1-C4)alcoxy ou halogène; R?9¿ représente hydrogène, (C¿1?-C4)alkyle, perhalo-(C1-C4)alkyle, (C1-C4)alcoxy-(C1-C4)alkyle ou phényl-(C1-C4)alkyle; R?8 et R9¿ forment éventuellement ensemble un carbocycle ou hétérocycle saturé ou partiellement insaturé avec les hétéroatomes O, N ou S et avec 5 à 6 chaînons cycliques; X représente oxygène ou soufre; et n est égal à 0 ou 1. 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/EP1991/001791 1990-09-19 1991-09-19 4-anilino-pyrimidines, leur procede de production, agents les contenant et leur utilisation comme fongicides WO1992005158A1 (fr)

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DE4029648A DE4029648A1 (de) 1990-09-19 1990-09-19 4-anilino-pyrimidine, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung als fungizide
DEP4029648.2 1990-09-19

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WO2003084953A1 (fr) * 2002-04-04 2003-10-16 B & C Biopharm Derives de 6-(anilino-4-substitue)pyrimidine, procede de preparation de ces derives et composition pharmaceutique antivirale les contenant
JP2007524637A (ja) * 2003-07-03 2007-08-30 ミリアド ジェネティクス， インコーポレイテッド カスパーゼの活性化因子およびアポトーシスの誘発因子としての４−アリールアミノ−キナゾリン
WO2007109045A1 (fr) * 2006-03-16 2007-09-27 Novartis Ag composes organiques
WO2011032656A1 (fr) 2009-09-18 2011-03-24 Bayer Cropscience Ag Dérivés de pyrimidine à substitution 5-fluor-3-thio
US7989462B2 (en) 2003-07-03 2011-08-02 Myrexis, Inc. 4-arylamin-or-4-heteroarylamino-quinazolines and analogs as activators of caspases and inducers of apoptosis and the use thereof
US8258145B2 (en) 2005-01-03 2012-09-04 Myrexis, Inc. Method of treating brain cancer
US8309562B2 (en) 2003-07-03 2012-11-13 Myrexis, Inc. Compounds and therapeutical use thereof
CN113754633A (zh) * 2021-09-26 2021-12-07 中国农业大学 1-（6-取代嘧啶-4-基）-1,2,3,4-四氢喹啉类化合物及其制备方法和应用
CN114644596A (zh) * 2022-03-31 2022-06-21 青岛科技大学 一种含氟嘧啶芳胺类化合物及其用途

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DE19533023B4 (de) 1994-10-14 2007-05-16 Basf Ag Neue Carbonsäurederivate, ihre Herstellung und Verwendung
DE10019291C2 (de) * 2000-04-19 2002-04-04 Sueddeutsche Kalkstickstoff 2-Alkoxy-5-methoxypyrimidine bzw. deren tautomere Formen sowie Verfahren zu deren Herstellung
CZ20033053A3 (en) * 2001-05-14 2004-05-12 Bristol@Myersásquibbápharmaácompany Substituted pyrazinones, pyridines and pyrimidines as corticotropin releasing factor ligands

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WO2003084953A1 (fr) * 2002-04-04 2003-10-16 B & C Biopharm Derives de 6-(anilino-4-substitue)pyrimidine, procede de preparation de ces derives et composition pharmaceutique antivirale les contenant
US7276501B2 (en) 2002-04-04 2007-10-02 B & C Biopharm 6-(4-substituted-anilino)pyrimidine derivatives, method for preparation thereof and antiviral pharmaceutical composition comprising the same
JP2007524637A (ja) * 2003-07-03 2007-08-30 ミリアド ジェネティクス， インコーポレイテッド カスパーゼの活性化因子およびアポトーシスの誘発因子としての４−アリールアミノ−キナゾリン
US7989462B2 (en) 2003-07-03 2011-08-02 Myrexis, Inc. 4-arylamin-or-4-heteroarylamino-quinazolines and analogs as activators of caspases and inducers of apoptosis and the use thereof
US8309562B2 (en) 2003-07-03 2012-11-13 Myrexis, Inc. Compounds and therapeutical use thereof
US8258145B2 (en) 2005-01-03 2012-09-04 Myrexis, Inc. Method of treating brain cancer
WO2007109045A1 (fr) * 2006-03-16 2007-09-27 Novartis Ag composes organiques
WO2011032656A1 (fr) 2009-09-18 2011-03-24 Bayer Cropscience Ag Dérivés de pyrimidine à substitution 5-fluor-3-thio
CN113754633A (zh) * 2021-09-26 2021-12-07 中国农业大学 1-（6-取代嘧啶-4-基）-1,2,3,4-四氢喹啉类化合物及其制备方法和应用
CN114644596A (zh) * 2022-03-31 2022-06-21 青岛科技大学 一种含氟嘧啶芳胺类化合物及其用途
CN114644596B (zh) * 2022-03-31 2024-01-30 青岛科技大学 一种含氟嘧啶芳胺类化合物及其用途

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