EP1732927A2 - 6-(2-fluorophenyl)-triazolopyrimidines, procede de production desdits composes, leur utilisation dans la lutte contre des champignons parasites et des agents contenant lesdits composes - Google Patents

6-(2-fluorophenyl)-triazolopyrimidines, procede de production desdits composes, leur utilisation dans la lutte contre des champignons parasites et des agents contenant lesdits composes

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Publication number
EP1732927A2
EP1732927A2 EP05716387A EP05716387A EP1732927A2 EP 1732927 A2 EP1732927 A2 EP 1732927A2 EP 05716387 A EP05716387 A EP 05716387A EP 05716387 A EP05716387 A EP 05716387A EP 1732927 A2 EP1732927 A2 EP 1732927A2
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EP
European Patent Office
Prior art keywords
formula
methyl
compounds
alkyl
triazolo
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.)
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Application number
EP05716387A
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German (de)
English (en)
Inventor
Carsten Blettner
Markus Gewehr
Wassilios Grammenos
Thomas Grote
Udo HÜNGER
Bernd Müller
Matthias NIEDENBRÜCK
Joachim Rheinheimer
Peter Schäfer
Frank Schieweck
Anja Schwögler
Oliver Wagner
Michael Rack
Barbara Nave
Maria Scherer
Siegfried Strathmann
Ulrich Schöfl
Reinhard Stierl
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BASF SE
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BASF SE
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Publication of EP1732927A2 publication Critical patent/EP1732927A2/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Withdrawn legal-status Critical Current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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Definitions

  • the present invention relates to 6- (2-fluorophenyl) triazolopyrimidines of the formula I.
  • RC 4 -C 8 -AIRyl C -C 8 -halogenoalkyl, C 3 -C 6 -cycloalkyl, substituted by at least one group R a , C 3 -C 8 -halo-cycloalkyl, C 3 -C 6 -cycloalkyl-C C 6 - alkyl, C 5 -C 8 alkenyl, C 2 -C 8 - .
  • Haloalkenyl C 3 -C 6 cycloalkenyl, C 3 -C 6 halocycloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl or phenyl, naphthyl, or a five- or six-membered saturated, partially unsaturated or aromatic Heterocycle containing one to four heteroatoms from the group O, N or S,
  • R 2 is hydrogen, CC 3 alkyl or one of the groups mentioned for R 1 ,
  • R 1 and R 2 also together with the nitrogen atom to which they are attached form a five- to eight-membered saturated or partially unsaturated heterocyclyl or five- or six-membered heteroaryl which is bonded via N and one to three further heteroatoms from the group O, N and S as ring member and / or one or more substituents from the group halogen, C ⁇ -C 6 -alkyl, C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 -alkoxy, d-Ce-haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -haloalkenyloxy, (exo) -CC 6 -alkylene and oxy-C 3 -C -alkyleneoxy can carry, where Piperidin-1-yl, which is unsubstituted or substituted by one or more methyl groups, remains excluded;
  • R 1 and / or R 2 can carry one to four identical or different groups R a :
  • R a halogen, cyano, nitro, hydroxy, Ci-Ce-alkyl, CC 6 -haloalkyl, dC 6 -AI- alkylcarbonyl, C 3 -C 6 -cycloalkyl, C ⁇ -C 6 -alkoxy, d-Ce-haloalkoxy, C r C 6 - alkoxycarbonyl, CC 6 -alkylthio, -C-C 6 -alkylamino, di-C C 6 -alkylamino, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 6 alkenyloxy, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C 3 -C 6 alkynyloxy, oxy-C C 3 alkyleneoxy, C 3 -C 8 cycloalkenyl, phenyl, naphthyl,
  • L 2 is hydrogen, if L 1 is fluorine, additionally fluorine;
  • the invention relates to a process for the preparation of these compounds, compositions containing them and their use for controlling phytopathogenic harmful fungi.
  • 5-alkyl-6-halophenyl-triazolopyrimidines are generally known from US Pat. No. 5,994,360.
  • Triazolopyrimidines with optically active amino substituents in the 7-position are generally proposed in WO 02/38565.
  • the present invention is based on the object of providing compounds with improved activity and / or broadened activity spectrum.
  • the compounds according to the invention differ from those described in the abovementioned publication by the specific combination of the substitution in the 5-position and the substitution of the 6-phenyl group with 7-amino groups of the triazolopyrimidine skeleton.
  • the compounds of the formula I have an increased activity or a broader spectrum of activity against harmful fungi than the known compounds.
  • the compounds according to the invention can be obtained in various ways.
  • Compounds of the formula I can advantageously be obtained by the following synthetic route:
  • the 5-alkyl-7-hydroxy-6-phenyltriazolopyrimidines IV are obtained.
  • X represents dC 4 alkyl.
  • the starting compounds III are advantageously prepared under the conditions described in EP-A 1002788.
  • the 5-alkyl-7-hydroxy-6-phenyltriazolopyrimidines IV are reacted with halogenating agents [HAL] under the conditions described above to give the 7-halotriazolopyrimidines of the formula V, in which Y represents a halogen atom.
  • Chlorination or bromination agents such as phosphorus oxybromide, phosphorus oxychloride, thionyl chloride, thionyl bromide or sulfuryl chloride are preferably used.
  • the reaction can be carried out in bulk or in the presence of a solvent. Usual reaction temperatures are from 0 to 150 ° C or preferably from 80 to 125 ° C.
  • reaction of V with amines VI is advantageously carried out at 0 ° C. to 70 ° C., preferably 10 ° C. to 35 ° C., preferably in the presence of an inert solvent, such as ether, e.g. B. dioxane, diethyl ether or in particular tetrahydrofuran, halogenated hydrocarbons such as dichloromethane and aromatic hydrocarbons such as toluene [cf. WO-A 98/46608].
  • ether e.g. B. dioxane, diethyl ether or in particular tetrahydrofuran
  • halogenated hydrocarbons such as dichloromethane
  • aromatic hydrocarbons such as toluene [cf. WO-A 98/46608].
  • a base such as tertiary amines, for example triethylamine or inorganic amines, such as potassium carbonate, is preferred; Excess amine of the formula VI can also serve as the base.
  • the subsequent saponification of the ester IX takes place under generally customary conditions, depending on the various structural elements, the alkaline or acid saponification of the compounds IX can be advantageous.
  • the decarboxylation to I can already take place in whole or in part.
  • the decarboxylation is usually carried out at from 20 ° C. to 180 ° C., preferably from 50 ° C. to 120 ° C., in an inert solvent, optionally in the presence of an acid, which can also serve as a solvent.
  • Suitable acids are hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, p-toluenesulfonic acid.
  • Suitable solvents are water, aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.
  • the reaction mixtures are usually worked up, for example by mixing with water, separating the phases and, if appropriate, purifying the crude products chromatographically.
  • the intermediate and end products are obtained in the form of colorless or slightly brownish, viscous oils, which are freed or purified from volatile components under reduced pressure and at a moderately elevated temperature. If the intermediate and end products are obtained as solids, they can also be purified by recrystallization or digesting. If individual compounds I are not accessible in the ways described above, they can be prepared by derivatizing other compounds I.
  • isomer mixtures occur during the synthesis, however, a separation is generally not absolutely necessary, since the individual isomers can partially convert into one another during preparation for use or during use (e.g. under the action of light, acid or base). Corresponding conversions can also take place after use, for example in the treatment of plants in the treated plant or in the harmful fungus to be controlled.
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkyl saturated, straight-chain or branched hydrocarbon radicals having 1 to 4, 6 or 8 carbon atoms, for example dC 6 -alkyl such as methyl, ethyl, propyl, 1-methyl, butyl, 1-methyl-propyl, 2-methyl-propyl, 1.1 -Dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethyl propyl, hexyl, 1,1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1, 2-dimethylIbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-eth
  • Haloalkyl straight-chain or branched alkyl groups with 1 to 2, 4, 6 or 8 carbon atoms (as mentioned above), it being possible for part or all of the hydrogen atoms in these groups to be replaced by halogen atoms as mentioned above: in particular C 1 -C 4 -haloalkyl such as chloromethyl, Bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2- Trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-t
  • Alkenyl unsaturated, straight-chain or branched hydrocarbon radicals with 2 to 4, 6, 8 or 10 carbon atoms and one or two double bonds 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-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2nd -Pentenyl, 3-pentenyl, 4-pentenyl, 1-Me- thyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl- 3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1
  • Haloalkenyl unsaturated, straight-chain or branched hydrocarbon radicals with
  • Alkynyl straight-chain or branched hydrocarbon groups with 2 to 4, 6 or 8 carbon atoms and one or two triple bonds in any position, for example C 2 -C 6 -alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl , 3-butynyl,
  • Cycloalkyl mono- or bicyclic, saturated hydrocarbon groups with 3 to 6 or 8 carbon ring members, for example C 3 -C 8 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl;
  • 5- or 6-membered heterocyclyl containing one to three nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, for example 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2 -Pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 4-oxazolidinyl , 5-oxazolidinyl, 2-thiazolidinyl, 4-thi
  • 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom
  • 5-ring heteroaryl groups which in addition to carbon atoms can contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members, eg 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4- Oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 1, 3,4-triazol-2-yl;
  • 6-membered heteroaryl containing one to three or one to four nitrogen atoms 6-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three or one to four nitrogen atoms as ring members, e.g. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl;
  • Oxyalkyleneoxy divalent unbranched chains of 1 to 3 CH 2 groups, both valences being bound to the skeleton via an oxygen atom, for example OCH 2 O, OCH 2 CH 2 O and OCH 2 CH 2 CH 2 O;
  • the scope of the present invention includes the (R) and (S) isomers and the racemates of compounds of the formula I which have chiral centers.
  • Z 1 is hydrogen, fluorine or dC 6 fluoroalkyl
  • Z 2 , Z 3 is hydrogen or fluorine, or Z 1 and Z 2 together form a double bond
  • q is 1, 2 or 3; and R 3 is hydrogen or methyl.
  • R 1 is C 4 -C 8 alkyl or C 4 -C 8 haloalkyl.
  • compounds I are preferred in which R 1 3 -C 6 cycloalkyl or C 3 -C 8 -halocycloalkyl or C 6 -C substituted by at least one group R a C - C cycloalkyl-C -alkyl.
  • R 1 is C 3 -C 6 cycloalkyl, which is substituted by CC alkyl, in particular methyl, are particularly preferred.
  • R 1 and / or R 2 contain haloalkyl or haloalkenyl groups with a chiral center, the (S) isomers are preferred for these groups.
  • the (R) -configured isomers are preferred.
  • a preferred embodiment of the invention relates to compounds of the formula 1.1:
  • GC 2 -C 6 alkyl especially ethyl, n- and i-propyl, n-, sec-, tert-butyl, and dC - alkoxymethyl, especially ethoxymethyl, or C 3 -C 6 cycloalkyl, especially cyclopropyl, cyclopentyl or cyclohexyl; and R 2 is hydrogen or methyl; mean.
  • Another preferred embodiment of the invention relates to compounds of the formula I.2.
  • Y is C 2 -C 4 alkyl, in particular ethyl and propyl.
  • a further preferred embodiment of the invention relates to compounds in which R 1 and R 2 together with the nitrogen atom to which they are attached form a five- or six-membered heterocyclyl or heteroaryl which is bonded via N and a further hetero atom from the group O , N and S contain as a ring member and / or one or more substituents from the group halogen, dC 6 -alkyl, d-Ce-haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, dC 6 -alkoxy , d-Ce-haloalkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 haloalkenyloxy, CC 6 alkylene and oxy-C C 3 - alkyleneoxy can wear.
  • These compounds correspond in particular to formula I.3,
  • D together with the nitrogen atom forms a five- or six-membered heterocyclyl or heteroaryl which is bonded via N and contains a further heteroatom from the group O, N and S as a ring member and / or one or more substituents from the group halogen, dC 6 - Alkyl, CC 6 -haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, dC 6 alkoxy, CC 6 haloalkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 haloalkenyloxy , (exo) -dC 6 -alkylene and oxy-C r C 3 - alkyleneoxy can carry; mean.
  • Compounds of the formula I are particularly preferred, in particular those of the formula I.3 in which the groups L and L 2 have the following meanings: L 1 and L 2 fluorine,
  • R 1 and R 2 together with the nitrogen atom to which they are attached form a morpholinyl or thiomorpholinyl ring, in particular a ring which may be halogenated by one to three groups, dC 4 -alkyl or dC 4 haloalkyl is substituted.
  • the compounds in which R 1 and R 2 together with the nitrogen atom to which they are attached form a morpholinyl or a pyrrolidinyl ring, in particular a pyrrolidinyl ring, are particularly preferred.
  • R 1 and R 2 together with the nitrogen atom to which they are attached form a pyrazole ring which may be halogen, CC 4 alkyl or dC through one or two groups - Haloalkyl, in particular substituted by 3,5-dimethyl or 3,5-di (trifluoromethyl).
  • R 2 is hydrogen or methyl; or
  • R 1 and R 2 together mean - (CH 2 ) 2 CH (CF 3 ) (CH 2 ) 2- or - (CH 2 ) 2 O (CH 2 ) 2 -.
  • the compounds I are suitable as fungicides. They are characterized by excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes. Some of them are systemically effective and can be used in plant protection as foliar, stain and soil fungicides.
  • the compounds I are also suitable for combating harmful fungi such as Pacilomyces variot in the protection of materials (for example wood, paper, dispersions for painting, fibers or fabrics) and in the protection of stored products.
  • the compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally active amount of the active compounds.
  • the application can take place both before and after the infection of the materials, plants or seeds by the fungi.
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.
  • the application rates in crop protection are between 0.01 and 2.0 kg of active ingredient per ha.
  • amounts of active compound of 1 to 1000 g / 100 kg, preferably 5 to 100 g, are generally required per 100 kg of seed.
  • the amount of active ingredient applied depends on the type of application and the desired effect. Usual application rates in material protection are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of treated material.
  • the compounds I can be converted into the usual formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the form of application depends on the respective purpose; in any case, it should ensure a fine and uniform distribution of the compound according to the invention.
  • the formulations are prepared in a known manner, for example by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants.
  • solvents / auxiliaries water, aromatic solvents (for example Solvesso products, xylene), paraffins (for example petroleum fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma -Butryolactone), pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters.
  • aromatic solvents for example Solvesso products, xylene
  • paraffins for example petroleum fractions
  • alcohols for example methanol, butanol, pentanol, benzyl alcohol
  • ketones for example cyclohexanone, gamma -But
  • solvent mixtures can also be used, - Carriers such as natural stone powder (eg kaolins, clays, talc, chalk) and synthetic stone powder (eg highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
  • natural stone powder eg kaolins, clays, talc, chalk
  • synthetic stone powder eg highly disperse silica, silicates
  • Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
  • mineral oil fractions from medium to high boiling points such as kerosene or diesel oil, furthermore coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, e.g. Dimethyl sulfoxide, N-methylpyrrolidone or water into consideration.
  • mineral oil fractions from medium to high boiling points such as kerosene or diesel oil
  • coal tar oils as well as oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coating, impregnation and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are e.g. Mineral earths, such as silica gels, silicates, talc, kaolin, attack clay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • Mineral earths such as silica gels, silicates, talc, kaolin, attack clay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics
  • the formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight, of the active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum). Examples of formulations are: 1. Products for dilution in water
  • a compound according to the invention 10 parts by weight of a compound according to the invention are dissolved in water or a water-soluble solvent. Alternatively, wetting agents or other aids are added. The active ingredient dissolves when diluted in water.
  • a compound according to the invention 20 parts by weight of a compound according to the invention are dissolved in cyclohexanone with the addition of a dispersant e.g. Dissolved polyvinyl pyrrolidone. When diluted in water, a dispersion results.
  • a dispersant e.g. Dissolved polyvinyl pyrrolidone.
  • a compound according to the invention 40 parts by weight of a compound according to the invention are dissolved in xylene with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (5% each).
  • This mixture is introduced into water using an emulsifying machine (Ultraturax) and brought to a homogeneous emulsion. Dilution in water results in an emulsion.
  • a compound according to the invention 20 parts by weight of a compound according to the invention are comminuted in a stirred ball mill to form a fine active ingredient suspension with the addition of dispersing and wetting agents and water or an organic solvent. Dilution in water results in a stable suspension of the active ingredient.
  • Water-dispersible and water-soluble granules 50 parts by weight of a compound according to the invention are finely ground with the addition of dispersants and wetting agents and are prepared as water-dispersible or water-soluble granules by means of technical equipment (e.g. extrusion, spray tower, fluidized bed). Dilution in water results in a stable dispersion or solution of the active ingredient.
  • Water-dispersible and water-soluble powders 75 parts by weight of a compound according to the invention are ground in a rotor-strator mill with the addition of dispersing and wetting agents and silica gel. at dilution in water results in a stable dispersion or solution of the active ingredient.
  • a compound according to the invention 0.5 part by weight is ground finely and combined with 95.5% carriers.
  • Common processes are extrusion, spray drying or fluidized bed. This gives granules for direct application.
  • the active ingredients as such in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, atomizing, dusting, scattering or pouring.
  • the application forms depend entirely on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
  • emulsions, pastes or oil dispersions the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates composed of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
  • the active ingredient concentrations in the ready-to-use preparations can be varied over a wide range. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be used with great success in the ultra-low-volume process (ULV), it being possible to apply formulations with more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume process
  • Oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides can be added to the active compounds, if appropriate also only immediately before use (tank mix). These agents can be added to the agents according to the invention in a weight ratio of 1:10 to 10: 1.
  • compositions according to the invention can also be present together with other active compounds which, e.g. with herbicides, insecticides, growth regulators, fungicides or also with fertilizers. Mixing the compounds I or the compositions containing them in the use form as fungicides with other fungicides results in an enlargement of the fungicidal spectrum of action in many cases.
  • Acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl,
  • Amine derivatives such as aldimorph, dodine, dodemorph, fenpropimorph, fenpropidine, guazatine, iminoctadine, spiroxamine, tridemorph • anilinopyrimidines such as pyrimethanil, mepanipyrim or cyprodinil,
  • Antibiotics such as cycloheximide, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin,
  • Azoles such as bitertanol, bromoconazole, cyproconazole, difenoconazole, dinitroconazole, enilconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole, flutriafol, hexaconazole, imazalil, ipconazole, metconazol, penocolazolol, myocazolol, myocazolol, myclazol, myclazol, myclazol, myocazolol, myclazol, myclazol, myclazol, myclazol, myclazol, myclazol, myclazol, myclazol, myclazol, myclazol , Tetraconazole, tri-dimefon, triadimenol, triflumizole, triticonazole,
  • Dicarboximides such as iprodione, myclozolin, procymidone, vinclozolin,
  • Dithiocarbamates such as Ferbam, Nabam, Maneb, Mancozeb, Metam, Metiram, Propineb, Polycarbamat, Thiram, Ziram, Zineb,
  • Heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim, carboxin, oxycarboxin, cyazofamid, dazomet, dithianon, famoxadone, fenamidon, fenarimol, fuberidazole, flutolanil, furametpyr, isoprothiolan, mepronazolifene, proquinolifene, proquinolifene, proquinolifene, proquinolifene, proquinolifene, proquinolifene, proquinolifene, proquinolifene, proquinolifene, proquinolifene, proquinolifene, nuquin Pyroquilon, quinoxyfen, silthofam, thiabendazole, thifluzamide, thiophanate-methyl, tiadinil, tricyclazole, triforins, Copper fungicides such as
  • Nitrophenyl derivatives such as binapacryl, dinocap, dinobuton, nitrophthal-isopropyl
  • Phenylpyrroles such as fenpiclonil or fludioxonil, sulfur,
  • fungicides such as acibenzolar-S-methyl, benthiavalicarb, carpropamide, chlorothalonil, cyflufenamide, cymoxanil, diclomezin, diclocymet, diethofencarb, edifenphos, ethaboxam, fenhexamide, fentin acetate, fenoxanil, namimzone, fluazi, fluazi, fluazi Fosetyl aluminum, phosphorous acid, iprovalicarb, hexachlorobenzene, metrafenone, pencycuron, penthiopyrad, propamocarb, phthalide, toloclofos-methyl, quintozene, zoxamide,
  • strobilurins such as azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, cresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin or trifloxystrobin, • sulfenoic acid derivatives such as captafol, captan, dichlofluanfluanid, folpet, tolpet, tolpet
  • Cinnamic acid amides and analogues such as dimethomorph, flumetover or flumorph.
  • Example 1a 5-chloro-6- (2,4,6-trifluorophenyl) -7- (2-methyl-pyrrolidin-1-yl) -1, 2,4-triazolo [1,5a] pyrimidine
  • Example 2a methyl 2- (2,4,6-trifluorophenyI) acetoacetate
  • reaction mixture was mixed with 450 ml of ammonium chloride solution. and conc. Acidified hydrochloric acid. After dilution with methyl t-butyl ether (MtBE), the organic phase was diluted with dil. acid and NaHCO 3 solution. washed, then dried and freed from solvent. The residue was fractionated. 34.5 g of the title compound were obtained as a light yellow liquid.
  • MtBE methyl t-butyl ether
  • Example 2d 5-methyl-6- (2,4,6-trifluorophenyl) -7- (R-1, 2-dimethylprop-1-yl) -1, 2,4-tri-azolo [1, 5a] pyrimidine
  • Phenyl substitution two diastereomers are present, which can differ in the physical data.
  • the active ingredients were prepared as a stock solution with 25 mg active ingredient, which was mixed with a mixture of acetone and / or DMSO and the emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) in a volume ratio of solvent emulsifier was filled from 99 to 1 ad 10 ml. Then ad 100 ml was made up with water. This stock solution was diluted with the solvent-emulsifier / water mixture described to the active ingredient concentration given below.
  • Pepper seedlings of the "Neusiedler Ideal Elite" variety after 2 to 3 leaves had developed well, were sprayed to runoff point with an aqueous suspension in the active compound concentration given below. The next day the treated plants were inoculated with a spore suspension of Botrytis cinerea containing 1.7 x 10 6 spores / ml in a 2% aqueous biomalt solution. The test plants were then placed in a climatic chamber with 22 to 24 ° C, darkness and high air humidity. After 5 days, the extent of the fungal attack on the leaves could be determined visually in%.
  • the plants treated with 250 ppm of the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7 or I-8 showed a maximum of 1% infection, while the untreated plants were 90% infected.
  • Leaves of cucumber seedlings grown in pots were sprayed in the cotyledon stage with an aqueous suspension in the active ingredient concentration given below to runoff. 3 days after the application, the plants were inoculated with an aqueous spore suspension of cucumber mehite (Sphaerotheca fuliginea). The plants were then cultivated in a greenhouse at temperatures between 20 and 24 ° C. and 60 to 80% relative atmospheric humidity for 7 days. The extent of mildew development was then determined visually in% of the cotyledon area.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pretreatment Of Seeds And Plants (AREA)
  • Catching Or Destruction (AREA)

Abstract

L'invention concerne des 6-(2-fluorophényl)-triazolopyrimidines de formule (I), dans laquelle les substituants ont la signification suivante : R1 = alkyle en C4-C8, halogénoalkyle en C4-C8, cycloalkyle en C3-C8 substitué, halogénocycloalkyle en C3-C8, alcényle en C5-C8, halogénoalcényle en C2-C8, cycloalcényle en C3-C6, halogénocycloalcényle en C3-C6, alcinyle en C2-C8, halogénoalcinyle en C2-C8 ou phényle, naphthyle ou un hétérocycle saturé, partiellement insaturé ou aromatique à cinq ou six chaînons, contenant un à quatre hétéroatomes du groupe O, N ou S ; R2 = hydrogène, alkyle en C1-C3 ou un des groupes mentionnés pour R1, R1 et R2 pouvant également former, conjointement avec l'atome d'azote auquel ces derniers sont liés, un hétéroaryle ou hétérocyclyle à cinq ou six chaînons, lié par l'intermédiaire de N et contenant un à trois autres hétéroatomes du groupe O, N et S comme chaînon cyclique, à l'exception de pipéridin-1-yle éventuellement substitué par des groupes méthyle, et R1 et/ou R2 pouvant être substitués selon la description ; L1 = chlore ou fluor ; L2 = hydrogène, si L1 signifie fluor, et fluor ; X = alkyle. Ladite invention concerne également un procédé pour produire ces composés, des agents contenant ces derniers ainsi que leur utilisation dans la lutte contre les champignons phytopathogènes.
EP05716387A 2004-03-30 2005-03-26 6-(2-fluorophenyl)-triazolopyrimidines, procede de production desdits composes, leur utilisation dans la lutte contre des champignons parasites et des agents contenant lesdits composes Withdrawn EP1732927A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004016082 2004-03-30
PCT/EP2005/003208 WO2005095404A2 (fr) 2004-03-30 2005-03-26 6-(2-fluorophenyl)-triazolopyrimidines, procede de production desdits composes, leur utilisation dans la lutte contre des champignons parasites et des agents contenant lesdits composes

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EP1732927A2 true EP1732927A2 (fr) 2006-12-20

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EP05716387A Withdrawn EP1732927A2 (fr) 2004-03-30 2005-03-26 6-(2-fluorophenyl)-triazolopyrimidines, procede de production desdits composes, leur utilisation dans la lutte contre des champignons parasites et des agents contenant lesdits composes
EP05736871A Withdrawn EP1735316A2 (fr) 2004-03-30 2005-03-29 6-(2,6-dichlorphenyl)-triazolopyrimidines, leur procede de production et leur utilisation pour lutter contre les champignons nuisibles et produits les contenant

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US (2) US20070208038A1 (fr)
EP (2) EP1732927A2 (fr)
JP (2) JP2007530618A (fr)
CN (2) CN1938313A (fr)
BR (2) BRPI0508717A (fr)
IL (2) IL177512A0 (fr)
WO (2) WO2005095404A2 (fr)

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WO2007113136A1 (fr) * 2006-03-30 2007-10-11 Basf Aktiengesellschaft Utilisation de triazolopyrimidines substituées dans la lutte contre des champignons phytopathogènes

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Publication number Priority date Publication date Assignee Title
US6117876A (en) * 1997-04-14 2000-09-12 American Cyanamid Company Fungicidal trifluorophenyl-triazolopyrimidines
US5994360A (en) * 1997-07-14 1999-11-30 American Cyanamid Company Fungicidal 5-alkyl-triazolopyrimidines
FR2765875B1 (fr) * 1997-07-14 1999-11-19 American Cyanamid Co 5-alkyl-triazolopyrimidines fongicides
EP1307200A2 (fr) * 2000-06-30 2003-05-07 Wyeth Triazolopyrimidines substitues comme agents anticancereux
AU2002221831A1 (en) * 2000-11-13 2002-05-21 Basf Aktiengesellschaft 7-(r)-amino-triazolopyrimidines, the production thereof and use of the same for combating phytopathogenic fungi
JP2004526767A (ja) * 2001-04-11 2004-09-02 ビーエーエスエフ アクチェンゲゼルシャフト ６−（２−クロロ−６−フルオロ−フェニル）−トリアゾロピリミジン類
JP2002308879A (ja) * 2001-04-13 2002-10-23 Nippon Soda Co Ltd ５−ハロアルキル−アゾロピリミジン化合物、製造方法及び有害生物防除剤
US20040162428A1 (en) * 2001-07-18 2004-08-19 Tormo I Blasco Jordi 6-(2,6-difluorophenyl)-triazolopyrimidines as fungicides
DE50304232D1 (de) * 2002-05-03 2006-08-24 Basf Ag Fungizide triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bek mpfung von schadpilzen sowie sie ent haltende mittel
UA80304C2 (en) * 2002-11-07 2007-09-10 Basf Ag Substituted 6-(2-halogenphenyl)triazolopyrimidines
AU2004226233A1 (en) * 2003-03-31 2004-10-14 Basf Aktiengesellschaft 7-alkenylamino-triazolopyrimidines, method for the production thereof and use thereof in controlling harmful fungi and substances containing said triazolopyrimidines
CA2520718A1 (fr) * 2003-04-02 2004-10-14 Basf Aktiengesellschaft 7-alkinylamino-triazolopyrimidines, leurs procedes de production et leur utilisation pour lutter contre les champignons nuisibles et les produits les contenant

Non-Patent Citations (1)

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Title
See references of WO2005095404A2 *

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WO2005095404A2 (fr) 2005-10-13
IL177661A0 (en) 2006-12-31
CN1938313A (zh) 2007-03-28
WO2005095405A2 (fr) 2005-10-13
WO2005095404A3 (fr) 2006-04-06
JP2007530618A (ja) 2007-11-01
CN1938312A (zh) 2007-03-28
BRPI0508717A (pt) 2007-08-07
WO2005095405A3 (fr) 2005-12-22
US20070208038A1 (en) 2007-09-06
EP1735316A2 (fr) 2006-12-27
JP2007530634A (ja) 2007-11-01
BRPI0508728A (pt) 2007-08-14
US20070142404A1 (en) 2007-06-21
IL177512A0 (en) 2006-12-10

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