WO1997046537A1 - Amides d'acide pyrimidino-4-carboxylique - Google Patents

Amides d'acide pyrimidino-4-carboxylique Download PDF

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Publication number
WO1997046537A1
WO1997046537A1 PCT/EP1997/002848 EP9702848W WO9746537A1 WO 1997046537 A1 WO1997046537 A1 WO 1997046537A1 EP 9702848 W EP9702848 W EP 9702848W WO 9746537 A1 WO9746537 A1 WO 9746537A1
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Prior art keywords
alkyl
alkoxy
haloalkoxy
haloalkyl
halogen
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PCT/EP1997/002848
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German (de)
English (en)
Inventor
Regina Luise Hill
Karl Eicken
Frank Wetterich
Eberhard Ammermann
Siegfried Strathmann
Gisela Lorenz
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Basf Aktiengesellschaft
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Priority to EP97927098A priority Critical patent/EP0912525A1/fr
Publication of WO1997046537A1 publication Critical patent/WO1997046537A1/fr

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    • 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
    • C07D239/02—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
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/38—One sulfur atom

Definitions

  • the present invention relates to pyrimidine-4-carboxamides of the formula I.
  • R 1 Ci-Ca-alkyl where these radicals may be partially or fully halogenated halo- and / or may carry one to three of the following groups: cyano, C 4 alkoxyalkyl, C ⁇ -C4 haloalkyl, C ⁇ -C 4 -Alkoxy, C -.- C 4 -haloalkoxy, -C-C 4 alkylthio, C 1 -C 4 alkoxycarbonyl, C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkenyl, aryl, aryloxy and heteroaryl, where the cyclic radicals ih ⁇ hand, one to three of the following substituents: halogen, cyano, C 4 -alkyl, C 4 alkoxyalkyl, C ⁇ -C4 haloalkyl, C ⁇ ⁇ C 4 -alkoxy, C 4 -haloalkoxy, C 1 -C 4 -alkylthio,
  • Aryl where this radical may carry one or independently two or three of the following groups: halogen, cyano, G 4 -alkyl, C 4 ⁇ alkoxyalkyl, C ⁇ -C. 4 haloalkyl, C ⁇ ⁇ C 4 alkoxy, C 1 -C 4 haloalkoxy, C ⁇ -C 4 alkylthio,
  • C 1 -C 4 alkoxycarbonyl, aryl, aryloxy and heteroaryl in which the cyclic substituents in turn can carry one or, independently of one another, two or three of the following substituents: halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 -Alkoxy- alkyl, -CC 4 -haloalkyl, -C-C 4 -alkoxy, -C-C 4 -haloalkoxy, -C-C 4 -alkylthio and C C-C 4 -alkoxycarbonyl;
  • n 0, 1 or 2;
  • R 2 is hydrogen, hydroxy, halogen, -CC 8 alkyl, -C 8 -halo-alkyl, Ci-C ⁇ -alkoxy, -C 8 -haloalkoxy;
  • R 3 is hydrogen, hydroxy, halogen, -CC 8 alkyl, -C 8 -haloalkylene, C ! -C 8 -alkoxy, C 8 haloalkoxy,
  • R 4 is hydrogen or optionally partially or optionally fully halogenated C 1 -C 8 -alkyl or optionally partially or optionally fully halogenated C 3 -C 7 -cycloalkyl;
  • R 5 C 1 -C 8 -alkyl, these radicals being partially or completely halogenated and / or one or, independently of one another, being able to carry two or three of the following groups: cyano, C 1 -C 4 -alkoxyalkyl, C 1 -C 4 - haloalkyl, C ⁇ -C 4 -alkoxy, C 4 haloalkoxy, C ⁇ -C 4 alkylthio, C 1 -C 4 -alkoxycarbonyl, C 3 -C 7 cycloalkyl, C 3 -C 7 -cycloalkenyl, aryl, aryloxy and heteroaryl which can carry where the cyclic radicals in turn one or independently two or three of the following Substi ⁇ tuenten: halogen, cyano, ⁇ C 4 alkyl, C 1 -C 4 alkoxyalkyl, C ⁇ -C 4 haloalkyl, C 1 -C 4 -alkoxy, C
  • C 3 -C 7 cycloalkyl this radical being able to carry one or, independently of one another, two or three of the following groups: halogen, C ⁇ -C 4 -alkyl, C ⁇ -C 4 ⁇ haloalkyl and C ⁇ -C 4 alkoxy or
  • cyclic substituents in turn can carry one or, independently of one another, two or three of the following substituents: halogen, Cyano, C ⁇ -C 4 -alkyl, C ⁇ -C 4 -alkoxy- alkyl, C ⁇ -C 4 -haloalkyl, C ⁇ -C 4 -alkoxy, C ⁇ -C 4 -haloalkoxy, C ⁇ -C 4 -alkylthio and C ⁇ -C 4 -Alkoxycarbonyl.
  • the invention relates to compositions containing the compounds I and to the use of the compounds I and the compositions for controlling harmful fungi.
  • the present invention was therefore based on new pyrimidine-4-carboxamides with improved properties, above all a higher activity and, in addition, a broad spectrum of activity in the control of harmful fungi as a task.
  • the compounds I can be prepared in a manner known per se or analogously to known methods, as is shown by way of example in the following three preparation processes.
  • R 1 methyl
  • R 2 chlorine
  • R 3 hydrogen
  • amines VI are known or can easily be obtained (cf. Houben-Weyl, Methods of Organic Chemistry, Georg Thieme Verlag, Stuttgart, Volume XI / 1, 4th edition, 1957, page 24 to page 262 and page 360 to page 409).
  • the reaction of the amines VI with the compounds V is preferably carried out in a solvent such as dichloromethane, tetrahydrofuran or toluene.
  • the amines VI themselves can serve as bases, usually being recovered from the crude product.
  • Suitable oxidizing agents are, for example, hydrogen peroxide, organic peroxides such as acetic acid peroxide, trifluoroacetic acid peroxide, m-chloroperbenzoic acid, tert-butyl hydroperoxide and tert-butyl hypochloride, and also inorganic compounds such as sodium methoxide, chromic acid and nitric acid.
  • organic peroxides such as acetic acid peroxide, trifluoroacetic acid peroxide, m-chloroperbenzoic acid, tert-butyl hydroperoxide and tert-butyl hypochloride
  • inorganic compounds such as sodium methoxide, chromic acid and nitric acid.
  • Hydrogen peroxide organic peroxides such as acetic acid peroxide, trifluoroacetic acid peroxide and m-chloroperbenzoic acid are particularly suitable for complete oxidation of the sulfur, and also inorganic oxidizing agents such as potassium permanganate. If inorganic oxidizing agents are used, the addition of a catalyst, e.g. Tungsten, be conducive to the course of the reaction.
  • a catalyst e.g. Tungsten
  • a mixture of sodium tungstate and hydrogen peroxide has proven particularly useful.
  • the reaction is carried out in an inert solvent, depending on the oxidizing agent, e.g. organic acids such as acetic acid, trichloroacetic acid and propionic acid, chlorinated hydrocarbons such as methylene chloride, chloroform and 1, 2-dichloroethane, aromatic hydrocarbons or halogenated hydrocarbons such as benzene, chlorobenzene and toluene, protic solvents such as methanol and ethanol, or water are usable.
  • organic acids such as acetic acid, trichloroacetic acid and propionic acid
  • chlorinated hydrocarbons such as methylene chloride, chloroform and 1, 2-dichloroethane
  • aromatic hydrocarbons or halogenated hydrocarbons such as benzene, chlorobenzene and toluene
  • protic solvents such as methanol and ethanol, or water are usable.
  • Mixtures of the solvents mentioned are also suitable.
  • the reaction temperature is generally from (- 30) ° C to the boiling point of the respective reaction mixture, for partial oxidation of the sulfur rather in the lower temperature range, for complete oxidation, however, preferably at 10 ° C to the boiling point. It is particularly preferred to work at 0 to 40 ° C.
  • the compounds of the formula I can also be converted into their N-oxides in a manner known per se (see, for example, A. Albini and S. Pietra, Heterocyclic N-Oxides, CRC-Press Inc., Boca Raton, USA 1991; HS Mosher et al., Org. Synth. Coil. Vol. IV 1963, page 828; EC Taylor et al., Org. Synth. Coil. Vol. IV 1963, page 704; TW Bell et. Al., Synth. 69, 226 (1990)).
  • oxidizing agents customary for oxidation are peracetic acid, trifluoroperacetic acid, perbenzoic acid, m-chloroperbenzoic acid, monopermaleic acid, magnesium monoperphthalate b lat, sodium perborate, Oxone® (contains peroxodisulfate), per tungstic acid and hydrogen peroxide.
  • Suitable solvents are e.g. Water, sulfuric acid, carboxylic acids such as acetic acid and trifluoroacetic acid as well as halogenated hydrocarbons such as dichloromethane and chloroform.
  • the oxidation is usually successful at temperatures from 0 ° C to the boiling point of the reaction mixture.
  • the oxidizing agent is normally used in at least equimolar amounts, based on the starting compound. In general, however, a large excess of oxidizing agent has proven to be particularly advantageous.
  • R 1 methyl
  • R 2 hydrogen
  • R 3 bromine
  • the compounds of the formula I can optionally be in the form of geometric and / or optical isomers or isomer mixtures. Both the pure isomers and the mixtures of the isomers have the fungicidal activity.
  • the invention also includes the salts of the acid-resistant compounds I which contain basic centers, especially basic nitrogen atoms, in particular with mineral acids such as sulfuric acid and phosphoric acid or Lewis acids such as zinc chloride.
  • basic centers especially basic nitrogen atoms
  • mineral acids such as sulfuric acid and phosphoric acid or Lewis acids such as zinc chloride.
  • the type of salt is not important.
  • Such salts which are suitable for agricultural purposes are particularly important.
  • the salts of the compounds I are accessible in a manner known per se, above all by reacting the corresponding compounds I with the acids mentioned in water or an inert organic solvent at temperatures from (-80) to 120, preferably 0 to 60 ° C. 2
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkyl straight-chain or branched alkyl groups with 1 to 8 carbon atoms, e.g. Ci-Ce-alkyl such as methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3- Methylbutyl, 1, 1-dimethylpropyl, 2, 2-dimethylpropyl, 1, 2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethyl butyl, 2,2-dimethylbutyl, 3, 3-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 3-dimethylbutyl, 1-ethylbutyl,
  • Haloalkyl or partially or completely halogenated alkyl straight-chain or branched alkyl groups with 1 to 4 or 8
  • C 1 -C 2 -haloalkyl such as chloromethyl, dichloromethyl,
  • Alkoxy straight-chain or branched alkoxy groups with 1 to 4 carbon atoms, for example C ⁇ -C 3 alkoxy such as methyloxy, ethyloxy, propyloxy and 1-methylethyloxy;
  • Alkoxyalkyl straight-chain or branched alkyl groups with 1 to 8 carbon atoms (as mentioned above), which in any position carry a straight-chain or branched alkoxy group (as mentioned above) with 1 to 4 carbon atoms in the case of C 1 -C 4 -alkoxyalkyl, such as methoxymethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl, 1-methoxyethyl, 2-methoxyethyl, 1-ethoxyethyl, 2-ethoxyethyl, 2-n-propoxyethyl and 2-butoxyethyl;
  • Haloalkoxy straight-chain or branched alkoxy groups with 1 to 4 carbon atoms (as mentioned above), where the hydrogen atoms in these groups can be partially or completely replaced by halogen atoms (as mentioned above), for example C 1 -C 2 -haloalkoxy such as chloromethyloxy, dichloromethyloxy, tri - chloromethyloxy, fluoromethyloxy, difluoromethyloxy, trifluoromethyloxy, chlorofluoromethyloxy, dichlorofluoromethyloxy, chlorodifluoromethyloxy, 1-fluoroethyloxy, 2-fluoroethyloxy, 2, 2-difluoroethyloxy, 2,2, 2-trifluoroethyloxy, 2-chloro-2-fluoroethyloxy, 2- Chloro-2, 2-difluoroethyloxy, 2, 2-dichloro-2-fluoroethyloxy, 2, 2, 2-trichloroethyloxy and pentaflu
  • Alkylthio straight-chain or branched alkyl groups with 1 to 4 carbon atoms (as mentioned above) which are bonded to the skeleton via a sulfur atom (-S-), for example C 1 -C 4 -alkyl thio such as methylthio, ethylthio, propylthio, 1- Methyl ethylthio, n-butylthio and tert-butylthio;
  • Alkoxycarbonyl straight-chain or branched alkoxy groups with 1 to 4 carbon atoms (as mentioned above), which are bonded to the skeleton via a carbonyl group (-C0-);
  • Alkenyl straight-chain or branched alkenyl groups with 2 to 8 carbon atoms and a double bond in any position, for example C 2 -C 6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-l-propenyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 2-methyl-l-propenyl, l-methyl-2- propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-
  • Alkynyl straight-chain or branched alkynyl groups with 2 to
  • C 2 -C 6 alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, l-methyl-2-propynyl, 1 Pentinyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1 -Dimethyl-2-propynyl, l-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, l-methyl-2-pentynyl, l-methyl-3-pentynyl , l-
  • Cycloalkyl monocyclic alkyl groups with 3 to 7 carbon ring members, for example C 3 -C 7 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl;
  • Cycloalkenyl monocyclic alkyl groups with 5 to 7 carbon ring members that contain one or more double bonds, for example Cs-C 7 cycloalkenyl such as cyclopentenyl, cyclohexenyl and cycloheptenyl, *
  • Aryl monocyclic or polycyclic aromatic groups with 6 to 10 carbon atoms, such as phenyl and naphthyl;
  • Arylalkyl aryl groups (as mentioned above) which, in the case of aryl (C 1 -C 4 ) alkyl, are bonded to the skeleton via alkyl groups having 1 to 4 carbon atoms (as mentioned above), for example phenyl (-C ⁇ - C 4 ) alkyl such as benzyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl, 1-phenylethyl, 1-phenylpropyl and 1-phenylbutyl;
  • Aryloxy aryl groups (as mentioned above) which are bonded to the structure via an oxygen atom (-O-), such as phenoxy, 1-naphthoxy and 2-naphthoxy;
  • Heteroaryl aromatic mono- or polycyclic radicals which, in addition to carbon ring members, additionally 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and one oxygen or one
  • 5-membered heteroaryl containing 1 to 3 nitrogen atoms 5-ring heteroaryl groups which, in addition to carbon atoms, can contain 1 to 3 nitrogen atoms as ring members, for example 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 1, 2, 4-triazol-3-yl and 1, 3, 4-triazol-2-yl;
  • 5-membered heteroaryl containing 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and 1 sulfur atom or oxygen atom or 1 oxygen or 1 sulfur atom 5-ring heteroaryl groups which, in addition to carbon atoms, contain 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and 1 May contain sulfur or oxygen atom or 1 oxygen or sulfur atom as ring members, for example 2-furyl, 3-furyl,
  • 5-ring heteroaryl groups which, in addition to carbon atoms, contain 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms and 1 sulfur or oxygen atom or Can contain 1 oxygen or a sulfur atom as ring members, and in which 2 adjacent carbon ring members or 1 nitrogen and 1 adjacent carbon ring member can be bridged by a buta-1,3-diene-1,4-diyl group;
  • 5-ring heteroaryl groups which in addition to carbon atoms can contain 1 to 4 nitrogen atoms or 1 to 3 nitrogen atoms as ring members, and in which 2 adjacent carbon ring members or a nitrogen and an adjacent carbon ring member by a buta- 1, 3 -diene-1,4-diyl group can be bridged, these rings being connected to the frame via one of the nitrogen ring members;
  • nitrogen atoms 6-ring heteroaryl groups which, in addition to carbon atoms, contain 1 to 3 or 1 to 4 nitrogen atoms
  • 6-ring heteroaryl groups in which 2 adjacent carbon ring members can be bridged by a buta-1, 3-diene-1, 4-diyl group, e.g. Quinoline, isoquinoline, quinazoline and quinoxaline.
  • R 1 is methyl
  • R 2 hydroxy, optionally substituted -CC 8 alkoxy, especially hydrogen, chlorine, methoxy;
  • R 3 hydroxy, optionally substituted Ci-C ⁇ -alkoxy, especially hydrogen, bromine, methoxy;
  • R 4 is hydrogen
  • R 5 is optionally substituted Ci-C ⁇ alkyl, cyclohexyl, in particular optionally substituted phenyl;
  • R 5 corresponds to one row of Table A for each connection.
  • R 5 corresponds to one row of Table A for each connection.
  • R 5 corresponds to one row of Table A for each connection.
  • R 5 corresponds to one row of Table A for each connection.
  • R 5 corresponds to one row of Table A for each connection.
  • R 5 corresponds to one row of Table A for each connection.
  • R 5 corresponds to one row of Table A for each connection.
  • R 5 corresponds to one row of Table A for each connection.
  • R 5 corresponds to one row of Table A for each connection.
  • the compounds I are suitable for controlling harmful fungi.
  • Suitable formulation aids are e.g. solid or liquid carriers, surface-active agents and adhesives.
  • Liquid carrier materials are understood to mean liquid solvents such as water and organic solvents, the latter having the function of an auxiliary solvent, especially when water is used as the solvent.
  • organic solvents aromatics such as xylene, toluene and alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes and methylene chloride, aliphatic hydrocarbons such as cyclohexane and paraffins, e.g.
  • Mineralol fractions alcohols such as butanol, iso-butanol, cyclohexanol and glycol and the associated ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, aprotic dipolar solvents such as dimethylformamide, N-methyl-2-pyrrolidone and Dimethyl sulfoxide.
  • alcohols such as butanol, iso-butanol, cyclohexanol and glycol and the associated ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone
  • aprotic dipolar solvents such as dimethylformamide, N-methyl-2-pyrrolidone and Dimethyl sulfoxide.
  • Solid carrier materials that can be considered are, for example: natural rock powders and mineral earths such as silica, silicates, kaolins, clays, boluses, loess, talc, chalk, limestone, lime, dolomite, magnesium oxide, quartz, attapulgite, montmorillonite and diatomaceous earth; synthetic rock flour such as highly disperse silicic acid or flour of synthetic aluminum oxide and synthetic silicates.
  • natural rock powders and mineral earths such as silica, silicates, kaolins, clays, boluses, loess, talc, chalk, limestone, lime, dolomite, magnesium oxide, quartz, attapulgite, montmorillonite and diatomaceous earth
  • synthetic rock flour such as highly disperse silicic acid or flour of synthetic aluminum oxide and synthetic silicates.
  • Solid carrier materials which are particularly suitable for granules are, for example: broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite; synthetic granules from inorganic and organic flours; Granules made of organic material such as sawdust, coconut shells, corn cobs or tobacco stalks.
  • Suitable surface-active agents are nonionic and anionic emulsifiers / foam-generating agents and dispersants:
  • Fatty acid polyoxyethylene esters such as lauryl alcohol polyoxyethylene ether acetate, i ⁇
  • Alkyl polyoxyethylene or polyoxypropylene ether for example of iso-tridecyl alcohol and fatty alcohol polyoxyethylene ether, alkylaryl alcohol polyoxyethylene ether such as octylphenol polyoxyethylene ether, - tributylphenol polyoxyethylene ether, ethoxylated iso-octyl, octyl or nonylphenol or castor oil,
  • arylsulfonic acids e.g. Lignin, phenol, naphthalene and dibutylnaphthalene sulfonic acid, alkyl sulfonic acids, alkylarylsulfonic acids, alkyl, lauryl ether and fatty alcohol sulfuric acids, fatty acids, sulfated
  • Suitable adhesives are: carboxymethyl cellulose; natural and synthetic powdery, granular or latex-shaped polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, natural phospholipids such as cephalins and lecithins, synthetic phospholipids.
  • the agents can contain one or more representatives of the following groups of substances: dyes, other known active substances, trace nutrients and other additives.
  • dyes come e.g. inorganic pigments such as iron oxide, titanium oxide, ferrocyan blue, and also organic pigments such as Alizarin, azo and metal phthalocyanine dyes.
  • active ingredients include other fungicides as well as insecticides, acaricides, herbicides and growth regulators.
  • Trace nutrients are, for example, salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Mineral and vegetable oils for example, are suitable as further additives.
  • the agents can moreover be mixed with other, practically significant mixing partners such as fertilizers or other finished agents containing active ingredients. 10
  • the agents are produced in a manner known per se, namely depending on the chemical and physical properties of the substances used, e.g. by mixing, grinding together, spraying, extruding, granulating or dissolving in water, the latter optionally with the aid of an organic solvent. Powders, sprinkles and dusts are e.g. obtainable by mixing or grinding the compounds I together with a solid carrier.
  • the agents are e.g. solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols or very fine encapsulations in polymeric substances or in seed coating compositions.
  • the agents which are generally available as concentrates are, if appropriate, dissolved, diluted, etc., as usual, in the case of wettable powders, water-dispersible granules, emulsifiable concentrates, dispersions and in some cases also in the case of microgranules, normally using water. Dust-like and granulated preparations and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the agents are applied in a manner known per se, for example by spraying, atomizing, dusting, scattering or
  • the plants are usually sprayed or dusted with the agents. Alternatively or additionally, the seeds of the plants are treated in a manner known per se.
  • V a mixture, ground in a hammer mill, of 80 parts by weight of a compound I according to the invention, 3 parts by weight of the sodium salt of diisobutylnaphthalene-1-sulfonic acid, 10 parts by weight of the sodium salt of a lignin sulfonic acid from a sulfite waste liquor and 7 parts by weight Splitting powdered silica gel: by finely distributing the mixture in water, a spray mixture is obtained;
  • IX a stable oily dispersion of 20 parts by weight of a compound I according to the invention, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde Condensates and 68 parts by weight of a paraffinic mineral oil.
  • the compounds I and the agents according to the invention are distinguished by excellent activity against a broad spectrum of harmful fungi (phytopathogenic fungi), in particular from the class of
  • the compounds I, their salts and N-oxides and the agents according to the invention are used by adding a fungicidally effective amount of the agents or the.
  • the application can take place before or after the infestation by the fungi.
  • the agents according to the invention and the compounds I are particularly suitable for controlling the following plant diseases:
  • Erysiphe graminis in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin plants, Podosphaera leucotricha on apples, Uncinula necator on vines, Puccinia species on cereals, Rhizoctonia species on cotton, rice and lawn, cereals and sugar cane, Ustilago , Venturia inaequalis (scab) on apples, Helminthosporium species on cereals, Septoria nodorum on wheat, Botrytis cinerea (gray mushrooms) on strawberries, vines, ornamental plants and vegetables, Cercospora arachidicola on peanuts, Pseudocercosporella herpotsteoides on wheat , Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Fusarium and Verticillium species on various plants, Plasmopara viticola on vines, Pseu
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.
  • the application rates are between 0.01 and 2.0 kg of active ingredient per ha.
  • active ingredient 0.001 to 0.1 g, preferably 0.01 to 0.05 g, per kg of seed are generally required.
  • agents according to the invention can also be present in the use form as fungicides together with other active ingredients, which e.g. with herbicides, insecticides, growth regulators, fungicides or also with fertilizers.
  • Sulfur, dithiocarbamates and their derivatives such as ferridimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylene bisdithiocarbamate, manganese-zinc-ethylenediamine-bis-dithiocarbamate, tetramethylthiuric-bis-dithiocarbamate, ammonium -diamid-dithi-carbamate, ammonium -diamid-dithi-carbamate, , Ammonia complex of zinc (N, N'-propylene-bis-dithiocarbamate), zinc (N, N '-propylene-bis-dithiocarbamate), N, N' -polypropylene-bis- (thiocarba - moyl) disulfide;
  • Nitroderivatives such as dinitro- (1-methylheptyl) phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl-3, 3-dimethylacrylate, 2-sec-butyl-4, 6-di-nitrophenyl-iso-propyl carbonate, 5 -Nitro-iso-phthalic acid di-isopropyl ester;
  • heterocyclic substances such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6- (o-chloroanilino) -s-triazine, 0,0-diethyl-phthalimidophosphonothioate, 5-amino-l- [bis- (dimethylamino) phosphinyl] -3-phenyl-l, 2, 4-triazole, 2,3-dicyano-l, 4-dithioanthraquinone, 2-thio-l, 3-dithiolo- [4, 5-b] - quinoxaline, 1- (butylcarbamoyl) -2-benzimidazole-carbamic acid methyl ester, 2-methoxycarbonylamino-benzimidazole, 2- (furyl- (2)) benzimidazole, 2- (thiazolyl- (4)) benzimidazole, N- (1,1,2,2-tetrachloroethylthi
  • fungicides such as dodecylguanidine acetate, 3- [3- (3,5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl)] glutarimide, hexachlorobenzene, DL-methyl-N- (2,6-dimethylphenyl) -N-furoyl (2) alaninate, DL-N- (2, 6-dimethylphenyl) -N- (2 '-methoxyacetyDalanin-methyl ester, N- (2, 6-dimethylphenyl) -N-chloroacetyl-D , L-2-aminobutyrolactone, DL-N- (2,6-dimethylphenyl) -N- (phenylacetyl) alanine methyl ester, 5-methyl-5-vinyl-3- (3,5-dichlorophenyl) -2,4- dioxo-l, 3-oxazolidine, 3- [3, 5-
  • Strobilurins such as methyl-E-methoximino- [a- (o-tolyloxy) -o-tolyl] acetate, methyl-E-2- ⁇ 2- [6- (2-cyanophenoxy) pyrimidine-4-yloxy] -phenyl ⁇ -3-methoxyacrylate, methyl-E-methoxy 15 mino- [a- (2-phenoxyphenyl)] acetamide, methyl-E-methoxy-mino- [a- (2, 5-dimethylphenoxy) -o-tolyl] acetamide.
  • Anilinopyrimidines such as N- (4, 6-dimethylpyrimidin-2-yl) aniline, N- [4-methyl-6- (1-propynyl) pyrimidin-2-yl] aniline, N- (4-methyl-6- cyclopropyl-pyrimidin-2-yl) aniline.
  • Phenylpyrroles such as 4- (2, 2-difluoro-1,3-benzodioxol-4-yl) pyrrole-3-carbonitrile.
  • Cinnamic acid amides such as 3- (4-chlorophenyl) -3- (3, 4-dimethoxyphenyl) acrylic acid morpholide.
  • Uniperol® EL non-ionic emulsifier based on ethoxylated castor oil
  • the desired active ingredient concentrations were set by diluting this emulsion with water. The extent of the disease was determined visually.

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Abstract

L'invention concerne des amides d'acide pyrimidino-4-carboxylique de formule (I) ainsi que leurs sels. Dans la formule, R1 représente alkyle, aryle éventuellement substitués; n vaut 0, 1 ou 2; R2 représente hydrogène, hydroxy, halogène, alkyle, halogénure d'alkyle, alcoxy, halogénure d'alcoxy; R3 représente hydrogène, hydroxy, halogène, alkyle, halogénure d'alkyle, alcoxy, halogénure d'alcoxy, l'un des radicaux R2 et R3 représentant toujours hydrogène; Y représente oxygène ou soufre; R4 représente hydrogène l'un des radicaux suivants, éventuellement partiellement ou totalement halogénés: alkyle, cycloalkyle; R5 représente alkyle, cycloalkyle, aryle éventuellement substitués. L'invention concerne également des agents contenant lesdits composés ainsi que leur utilisation pour lutter contre les champignons nuisibles.
PCT/EP1997/002848 1996-06-03 1997-06-02 Amides d'acide pyrimidino-4-carboxylique WO1997046537A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP97927098A EP0912525A1 (fr) 1996-06-03 1997-06-02 Amides d'acide pyrimidino-4-carboxylique

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19622270.2 1996-06-03
DE1996122270 DE19622270A1 (de) 1996-06-03 1996-06-03 Pyrimidin-4-carbonsäureamide

Publications (1)

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WO1997046537A1 true WO1997046537A1 (fr) 1997-12-11

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EP (1) EP0912525A1 (fr)
AR (1) AR014610A1 (fr)
CA (1) CA2257080A1 (fr)
DE (1) DE19622270A1 (fr)
WO (1) WO1997046537A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11866426B2 (en) 2018-08-08 2024-01-09 Incyte Corporation Benzothiazole compounds and uses thereof
US11891388B2 (en) 2016-09-09 2024-02-06 Incyte Corporation Pyrazolopyridine compounds and uses thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0033195A1 (fr) * 1980-01-10 1981-08-05 NYEGAARD & CO. A/S Pyrimidine-2-thioéthers et leurs S-oxydes pour l'application thérapeutique, compositions pharmaceutiques les contenant, procédés pour leur préparation ainsi que composés en soi au cas où ils sont nouveaux
WO1995025723A1 (fr) * 1994-03-18 1995-09-28 Agrevo Uk Limited Derives d'anilide utilises comme fongicides

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0033195A1 (fr) * 1980-01-10 1981-08-05 NYEGAARD & CO. A/S Pyrimidine-2-thioéthers et leurs S-oxydes pour l'application thérapeutique, compositions pharmaceutiques les contenant, procédés pour leur préparation ainsi que composés en soi au cas où ils sont nouveaux
WO1995025723A1 (fr) * 1994-03-18 1995-09-28 Agrevo Uk Limited Derives d'anilide utilises comme fongicides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11891388B2 (en) 2016-09-09 2024-02-06 Incyte Corporation Pyrazolopyridine compounds and uses thereof
US11866426B2 (en) 2018-08-08 2024-01-09 Incyte Corporation Benzothiazole compounds and uses thereof

Also Published As

Publication number Publication date
DE19622270A1 (de) 1997-12-04
CA2257080A1 (fr) 1997-12-11
AR014610A1 (es) 2001-03-28
EP0912525A1 (fr) 1999-05-06

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