EP0705253A1 - Aralkylaminoquinazolines - Google Patents

Aralkylaminoquinazolines

Info

Publication number
EP0705253A1
EP0705253A1 EP94918866A EP94918866A EP0705253A1 EP 0705253 A1 EP0705253 A1 EP 0705253A1 EP 94918866 A EP94918866 A EP 94918866A EP 94918866 A EP94918866 A EP 94918866A EP 0705253 A1 EP0705253 A1 EP 0705253A1
Authority
EP
European Patent Office
Prior art keywords
ethyl
alkyl
methyl
formula
carbon atoms
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Withdrawn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
EP94918866A
Other languages
German (de)
English (en)
Inventor
Roland Andree
Heinz-Wilhelm Dehne
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 AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of EP0705253A1 publication Critical patent/EP0705253A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/94—Nitrogen atoms

Definitions

  • the invention relates to new aralkylaminoquinazolines, a process for their preparation and their use as fungicides.
  • n the numbers 1, 2, 3 or 4,
  • R 1 for hydrogen, halogen, cyano, nitro, carboxy, carbamoyl or for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, dialkylamino, dialkylamino carbonyl or dialkylaminosulfonyl each having up to 6 carbon atoms in the alkyl radicals,
  • R 2 represents hydrogen or alkyl having up to 6 carbon atoms
  • R 3 represents hydrogen, alkyl or in each case optionally substituted by halogen alkylcarbonyl or alkylsulfonyl, each with up to 6
  • R 4 represents hydrogen or alkyl optionally substituted by halogen with up to 6 carbon atoms
  • R 5 represents halogen, cyano, nitro or alkyl optionally substituted by halogen with up to 6 carbon atoms,
  • the aralkylaminoquinazolines of the formula (I) according to the invention have a considerably better fungicidal activity than the constitutionally most similar previously known active ingredients.
  • aralkylaminoquinazolines according to the invention are generally defined by the formula (I).
  • m preferably represents the numbers 0, 1, 2 or 3.
  • n preferably represents the numbers 1, 2 or 3.
  • R preferably represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, carboxy, carbamoyl or in each case optionally by fluorine and / or
  • R 2 preferably represents hydrogen or alkyl having 1 to 4 carbon atoms.
  • R 3 preferably represents hydrogen, alkyl or alkylcarbonyl or alkylsulfonyl with 1 to 4 carbon atoms in the alkyl groups which are optionally substituted by fluorine and / or chlorine.
  • R 4 preferably represents hydrogen or alkyl having 1 to 4 carbon atoms which is optionally substituted by fluorine and / or chlorine.
  • R 5 preferably represents fluorine, chlorine, bromine, iodine, cyano, nitro or, where appropriate, alkyl having 1 to 4 carbon atoms which is substituted by fluorine and / or chlorine.
  • n particularly preferably represents the numbers 0, 1 or 2.
  • n particularly preferably represents the numbers 1 or 2.
  • R 1 particularly preferably represents hydrogen, fluorine, chlorine, bromine, cyano or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by fluorine and / or chlorine , Methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl,
  • R 2 particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl.
  • R 3 particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, acetyl, propionyl, chloroacetyl, dichloroacetyl, trichloroacetyl, fluoroacetyl, difluoroacetyl, trifluoroacetyl, methylsulfonyl, ethyl - sulfonyl or trifluoromethylsulfonyl.
  • R 4 particularly preferably represents hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by fluorine and / or chlorine.
  • R 5 particularly preferably represents fluorine, chlorine, bromine, cyano, nitro or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine and / or chlorine.
  • a very particularly preferred group of compounds of the formula (I) are the chlorine-substituted aralkylaminoquinazolines of the formula
  • n 0, 1 or 2
  • R 1 represents fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, R represents hydrogen, methyl, ethyl, n- or i-propyl,
  • R 3 represents hydrogen, methyl or ethyl
  • R 4 represents hydrogen, methyl or ethyl
  • Another very particularly preferred group of substances according to the invention are the compounds of the formula
  • n 0, 1 or 2
  • R 1 represents fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,
  • R 2 represents hydrogen, methyl, ethyl, n- or i-propyl
  • R 3 represents hydrogen, methyl or ethyl
  • R 4 represents hydrogen, methyl or ethyl
  • Another very particularly preferred group of substances according to the invention are the compounds of the formula
  • n 0, 1 or 2
  • R 1 represents fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,
  • R 2 represents hydrogen, methyl, ethyl, n- or i-propyl
  • R 3 represents hydrogen, methyl or ethyl
  • R 4 represents hydrogen, methyl or ethyl
  • Preferred substances according to the invention are also addition products of acids and those aralkylaminoquinazolines of the formula (I) in which n, m, R 1 , R 2 , R 3 , R 4 and R 5 have the meanings given as preferred.
  • the acids which can be added preferably include hydrohalic acids, such as, for example, hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, furthermore phosphoric acid, nitric acid, sulfuric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, such as, for example, acetic acid, maleic acid, succinic acid, Fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid and lactic acid as well as sulfonic acids such as p-toluenesulfonic acid, 1,5-naphthalenedisulfonic acid or camphorsulfonic acid, saccharin and thiosaccharin.
  • hydrohalic acids such as, for example, hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, furthermore phosphoric acid, nitric acid, sulfuric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, such as, for example, acetic acid
  • preferred compounds according to the invention are addition products from salts of metals of the II. To IV. Main group and of I. and II. As well as IV. To VIII. Subgroup of the Periodic Table of the Elements and those aralkylaminoquinazolines of the formula (I) in which n, m, R 1 , R 2 , R 3 , R 4 and R have the meanings given as preferred.
  • Salts of copper, zinc, manganese, magnesium, tin, iron and nickel are particularly preferred.
  • Anions of these salts are those which are derived from acids which lead to physiologically tolerable addition products.
  • Particularly preferred such acids in this connection are the hydrogen halide acids, e.g. hydrochloric acid and hydrobromic acid, also phosphoric acid, nitric acid and sulfuric acid.
  • the compounds of the formula (I) according to the invention optionally contain an asymmetrically substituted carbon atom in the aralkyl radical and can then be present in various enantiomeric forms.
  • the invention then relates both to the possible individual enantiomers and to the various possible - and therefore possibly also the racemic - mixtures of these enantiomers.
  • Formula (II) provides a general definition of the aralkylamines to be used as starting materials in the process according to the invention for the preparation of compounds of the formula (I).
  • m, R, R and R preferably or particularly preferably have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as preferred or as particularly preferred for m, R 1 , R 2 and R 3 were given.
  • the starting materials of the formula (II) are known and / or can be prepared by processes known per se (cf. DE-OS 2348801, DE-OS 2441651, DE-OS 2442845, DE-OS 2851039, EP-A 355351, EP-A 489682, Indian J. Chem. 13 (1975) 631).
  • Formula (III) provides a general definition of the haloquinazolines to be used as starting materials in the process according to the invention for the preparation of compounds of the formula (I).
  • n, R 4 and R 5 preferably or particularly preferably have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as preferred or as particularly preferred for n, R 4 and R 5 were given.
  • X preferably represents fluorine, chlorine or bromine, particularly preferably chlorine.
  • the starting materials of the formula (III) are known and / or can be prepared by processes known per se (cf. J. Am. Chem. Soc. 68 (1946), 1299-1301, J. Chem. Soc. 1962, 561- 572, Z. Naturforsch. 37b (1982), 907-911).
  • diluents Practically all inert organic solvents can be used as diluents. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl - And dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, esters such as methyl and ethyl acetate, nitriles such as, for example Aceton
  • Alkali metal hydroxides such as e.g. Sodium and potassium hydroxide, alkaline earth metal hydroxides such as e.g.
  • alkali (hydrogen) carbonates and alcoholates such as sodium, potassium (hydrogen) carbonate, sodium and potassium tert-butoxide, furthermore aliphatic, aromatic or heterocyclic amines, for example triethylamine, trimethylamine, dimethylaniline, dimethylbenzyl amine, pyridine, l, 5-diazabicyclo [4,3,0] non-5-ene (DBN), 1,8-diazabicyclo [5,4,0] undec-7-ene (DBU) and l , 4-diazabicyclo [2,2,2] octane (DABCO).
  • DBN 5-diazabicyclo [4,3,0] non-5-ene
  • DBU 1,8-diazabicyclo [5,4,0] undec-7-ene
  • DBU 4-diazabicyclo [2,2,2] octane
  • aralkylamines of the formula (II) used as starting materials can also serve as acid acceptors when used in a corresponding excess.
  • reaction temperatures can be varied within a wide range in the process according to the invention. Generally one works at tempe- temperatures between 0 ° C and 150 ° C, preferably at temperatures between 20 ° C and 120 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
  • the starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use one of the two components used in each case in a larger excess.
  • the reactions are generally carried out in a suitable diluent, if appropriate in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the temperature required in each case.
  • Working up in the process according to the invention is carried out in each case by customary methods (cf. the preparation examples).
  • aralkylaminoquinazolines of the formula (I) according to the invention can be converted into acid addition salts or metal salt complexes.
  • the acid addition salts of the compounds of formula (I) can be easily prepared by conventional salt formation methods, e.g. by dissolving a compound of formula (I) in a suitable inert solvent and adding the acid, e.g. Hydrochloric acid can be obtained and in a known manner, e.g. by filtration, isolated and, if necessary, cleaned by washing with an inert organic solvent.
  • a suitable inert solvent e.g. Hydrochloric acid
  • metal salt complexes of the compounds of formula (I) For the preparation of metal salt complexes of the compounds of formula (I), preference is given to those salts of metals which are already in the In connection with the description of the metal salt complexes according to the invention were mentioned as preferred metal salts.
  • the metal salt complexes of the compounds of formula (I) can be obtained in a simple manner by conventional methods, e.g. by dissolving the metal salt in alcohol, e.g. Ethanol and addition to compounds of formula (I).
  • Metal salt complexes can be prepared in a known manner, e.g. by filtering, isolating and, if necessary, cleaning by recrystallization.
  • the active compounds according to the invention have a strong microbicidal action and can be used practically to combat unwanted microorganisms.
  • the active ingredients are suitable for use as crop protection agents, in particular as fungicides.
  • Fungicidal agents in crop protection are used to control Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.
  • Pythium species such as, for example, Pythium ultimum
  • Phytophthora species such as, for example, Phytophthora infestans
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;
  • Plasmopara species such as, for example, Plasmopara viticola
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae;
  • Erysiphe species such as, for example, Erysiphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca fuliginea
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Venturia species such as, for example, Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Cochliobolus species such as, for example, Cochliobolus sativus
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Puccinia species such as, for example, Puccinia recondita
  • Tilletia species such as, for example, Tilletia caries
  • Ustilago species such as, for example, Ustilago nuda or Ustilago avenae;
  • Pellicularia species such as, for example, Pellicularia sasakii;
  • Pyricularia species such as, for example, Pyricularia oryzae
  • Fusarium species such as, for example, Fusarium culmorum
  • Botrytis species such as, for example, Botrytis cinerea
  • Septoria species such as, for example, Septoria nodorum
  • Leptosphaeria species such as, for example, Leptosphaeria nodorum;
  • Cercospora species such as, for example, Cercospora canescens
  • Alternaria species such as, for example, Alternaria brassicae
  • Pseudocercosporella species such as, for example, Pseudocercosporella herpotricoids.
  • the active compounds according to the invention are particularly suitable for the protective control of Plasmopara species on grapevines; they also show good effects e.g. against Erisyphe graminis, Septoria nodorum, Cochliobolus sativus and Pyrenophora teres.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active substance-impregnated natural and synthetic substances, very fine encapsulations in polymeric substances and in coating compositions for seeds, and also in Formulations with fuel sets, such as smoking cartridges, cans, spirals, etc., as well as ULV cold and warm mist formulations.
  • customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active substance-impregnated natural and synthetic substances, very fine encapsulations in polymeric substances and in coating compositions for seeds, and also in Formulations with fuel sets, such as smoking cartridges, cans, spirals, etc., as well as ULV cold and warm mist formulations.
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents Means. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents Means.
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents Means.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • liquid solvents aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as wenches thylformamide and dimethyl sulfoxide, as well as water;
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellant, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide;
  • Solid carrier materials are suitable: for example aerosol
  • Adhesives such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can be mixed with known fungicides, bactericides, acaricides, nematicides or
  • Insecticides are used to broaden the spectrum of activity or prevent development of resistance. In some cases synergism also occurs, which means that the effect of the mixture is greater than the sum of the effects of the individual components.
  • the mixing partners are e.g. the following substances in question:
  • Oxadixyl Oxamocarb, Oxycarboxin, Pefurazoat, Penconazol, Pencycuron, Phosdiphen, Pimaricin, Piperalin, Polyoxin,
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenothionx, Fhrionophon, Fufionophon, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fuf
  • Imidacloprid Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivemectin, Lamda-cyhalothrin, Lufenuron,
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet,
  • Phosphamdon, Phoxim, Pirimicarb, Pirimiphos M Primiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophos, Pyradaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyrphithionof, Siliproxif, Sulfiproxyfif, Sulfiproxyfon, Pyriphronium, Quinphosphorus, Quinophosphorus , Sulfotep, Sulprofos, Tebufenozid, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin7 Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Tri XMC, xylylcarb, YI 530
  • the active substances as such in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, Spray powder, pastes, soluble powders, dusts and granules can be used. They are used in the customary manner, for example by watering, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume process or to prepare the active ingredient or the active ingredient itself to inject the soil. The seeds of the plants can also be treated.
  • the active compound concentrations in the use forms can be varied within a substantial range. They are generally between 1 and 0.001% by weight, preferably between 0.5 and 0.001%.
  • active ingredient concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02%, are required at the site of action.
  • Solvent 4.7 parts by weight of acetone emulsifier: 0.3 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • young plants are sprayed with the preparation of active compound to runoff. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Plasmopara viticola and then remain in a moist chamber at 20 to 22 ° C. and 100% relative atmospheric humidity for 1 day. The plants are then placed in a greenhouse at 21 ° C. and about 90% humidity for 5 days. The plants are then moistened and placed in a moist chamber for 1 day.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material 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

De nouvelles aralkylaminoquinazolines ont la formule (I), dans laquelle m vaut 0, 1, 2, 3 ou 4; n vaut 1, 2, 3 ou 4; R1 désigne hydrogène, halogène, cyano, nitro, carboxy, carbamoyle ou alkyle, alcoxy, alkylthio, alkylsulfinyle, alkylsulfonyle, dialkylamino, dialkylaminocarbonyle ou dialkylaminosulfonyle substitués le cas échéant par halogène ayant jusqu'à 6 atomes de carbone dans les résidus alkyle; R2 désigne hydrogène ou alkyle ayant jusqu'à 6 atomes de carbone; R3 désigne hydrogène, alkyle ou alkylcarbonyle ou alkylsulfonyle substitués le cas échéant par halogène ayant jusqu'à 6 atomes de carbone dans les groupes alkyle; R4 désigne hydrogène ou alkyle substitué le cas échéant par halogène ayant jusqu'à 6 atomes de carbone; et R5 désigne halogène, cyano, nitro ou alkyle substitué le cas échéant par halogène ayant jusqu'à 6 atomes de carbone. L'invention concerne également les sels d'addition d'acide et les complexes de sels métalliques de ces composés, à l'exception des composés S-(+)-7-chloro-N-(1-phényl-éthyl)-4-quinazolinamine et R-(-)-7-chloro-N-(1-phényl-éthyl)-4-quinazolinamine, ainsi que leur procédé de préparation et leur utilisation comme fongicides.
EP94918866A 1993-06-24 1994-06-13 Aralkylaminoquinazolines Withdrawn EP0705253A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19934321029 DE4321029A1 (de) 1993-06-24 1993-06-24 Aralkylaminochinazoline
DE4321029 1993-06-24
PCT/EP1994/001910 WO1995000496A1 (fr) 1993-06-24 1994-06-13 Aralkylaminoquinazolines

Publications (1)

Publication Number Publication Date
EP0705253A1 true EP0705253A1 (fr) 1996-04-10

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP94918866A Withdrawn EP0705253A1 (fr) 1993-06-24 1994-06-13 Aralkylaminoquinazolines

Country Status (5)

Country Link
EP (1) EP0705253A1 (fr)
JP (1) JPH08511786A (fr)
AU (1) AU7000494A (fr)
DE (1) DE4321029A1 (fr)
WO (1) WO1995000496A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2769897A (en) * 1996-05-07 1997-11-26 Basf Aktiengesellschaft Imidazoquinazolines, agents containing them and their use to combat fungi and animal pests

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL89028A0 (en) * 1988-01-29 1989-08-15 Lilly Co Eli Quinoline,quinazoline and cinnoline derivatives
IL89027A (en) * 1988-01-29 1993-01-31 Lilly Co Eli Quinazoline derivatives, process for their preparation and fungicidal, insecticidal and miticidal compositions containing them
US5141941A (en) * 1988-11-21 1992-08-25 Ube Industries, Ltd. Aralkylamine derivatives, and fungicides containing the same
EP0424125A3 (en) * 1989-10-18 1991-10-09 Ube Industries, Ltd. Aralkylamine derivatives, preparation method thereof and fungicides containing the same

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9500496A1 *

Also Published As

Publication number Publication date
JPH08511786A (ja) 1996-12-10
WO1995000496A1 (fr) 1995-01-05
AU7000494A (en) 1995-01-17
DE4321029A1 (de) 1995-01-05

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