WO2005058904A1 - 6-pentafluorophenyl-triazolopyrimidines, procede pour leur production et leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant - Google Patents

6-pentafluorophenyl-triazolopyrimidines, procede pour leur production et leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant Download PDF

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WO2005058904A1
WO2005058904A1 PCT/EP2004/014210 EP2004014210W WO2005058904A1 WO 2005058904 A1 WO2005058904 A1 WO 2005058904A1 EP 2004014210 W EP2004014210 W EP 2004014210W WO 2005058904 A1 WO2005058904 A1 WO 2005058904A1
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formula
compounds
alkyl
methyl
cyano
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PCT/EP2004/014210
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German (de)
English (en)
Inventor
Jordi Tormo I Blasco
Carsten Blettner
Bernd Müller
Markus Gewehr
Wassilios Grammenos
Thomas Grote
Joachim Rheinheimer
Peter Schäfer
Frank Schieweck
Anja Schwögler
Oliver Wagner
Maria Scherer
Siegfried Strathmann
Ulrich Schöfl
Reinhard Stierl
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Basf Aktiengesellschaft
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Priority to JP2006544309A priority Critical patent/JP2007514682A/ja
Priority to EP04803836A priority patent/EP1697364A1/fr
Priority to BRPI0417639-1A priority patent/BRPI0417639A/pt
Priority to US10/582,938 priority patent/US20070105928A1/en
Publication of WO2005058904A1 publication Critical patent/WO2005058904A1/fr
Priority to IL175895A priority patent/IL175895A0/en

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    • 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
    • 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

Definitions

  • 6-Pentafluorophenyl-triazolopyrimidines process for their preparation and their use for controlling harmful fungi, and agents containing them
  • the present invention relates to 6-pentafluorophenyl triazolopyrimidines of the formula I.
  • R 2 is hydrogen or one of the groups mentioned for R 1 ,
  • R 1 and R 2 together with the nitrogen atom to which they are attached can also form a five- or six-membered heterocyclyl or heteroaryl which is attached via N and contain one to three further heteroatoms from the group O, N and S as a ring member and / or one or more substituents from the group halogen, C r C 6 -alkyl, CC 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 1 -C 6 -alkoxy, dC 6 - Haloalkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 haloalkenyloxy, (exo) -C ⁇ -C 6 alkylene and oxy-dC 3 alkyleneoxy can wear;
  • R 1 and / or R 2 can carry one to four identical or different groups R a :
  • X is cyano, dd alkyl, CC 4 -alkoxy, C 3 -C 4 alkenyloxy, C ⁇ -C 2 -haloalkoxy or C 3 -C haloalkenyloxy.
  • the invention relates to a process for the preparation of these compounds, compositions containing them and their use for controlling plant pathogens
  • 5-Halogen-6-pentafluorotriazolopyrimidines are generally known from EP-A 834513.
  • 5-cyano- and 5-alkoxy-triazolopyrimidines are disclosed in WO 02/083677.
  • 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 document by the substitution in the 5-position 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. They are advantageously obtained starting from the 5-halogen-6-pentafluorophenyl-triazolopyrimidines of the formula II known from EP-A 834 513 by reaction with compounds MX (formula III). Depending on the meaning of the group X to be introduced, compounds III represent an inorganic cyanide or an alkoxylate. The reaction is advantageously carried out in the presence of an inert solvent.
  • the cation M in formula III is of little importance; for practical reasons, as ammonium, tetraalkylammonium or alkali or alkaline earth metal salts are preferred.
  • the reaction temperature is usually from 0 to 120 ° C., preferably from 10 to 40 ° C. [cf. J. Heterocycl. Chem., Vol. 12, pp. 861-863 (1975)].
  • R 2 is hydrogen
  • a removable protective group is advantageously introduced before reaction with III [cf. Greene, Protective Groups in Organic Chemistry, J. Willey & Sons, (1981)].
  • Suitable solvents include ethers such as dioxane, diethyl ether and, preferably tetrahydrofuran, alcohols such as methanol or ethanol, halogenated hydrocarbons such as dichloromethane and aromatic hydrocarbons such as toluene or acetonitrile.
  • halogenating agents [HAL] are converted with halogenating agents [HAL] under the conditions known from WO-A 94/20501 into the halogenopyrimidines of the formula VII, in which the shark represents a halogen atom , preferably a bromine or a chlorine atom, in particular a chlorine atom.
  • a halogenating agent [HAL] is advantageously a chlorinating or brominating agent such as phosphorus xybr ⁇ mid, phosphorus oxychloride, thionyl chloride, thionyl bromide or sulfuryl chloride used.
  • This reaction is usually carried out at 0 ° C. to 150 ° C., preferably at 80 ° C. to 125 ° C. [cf. EP-A 770 615].
  • a base such as tertiary amines, for example triethylamine or inorganic amines, such as potassium carbonate, is preferred; Excess amine of the formula VIII can also serve as the base.
  • the malonates IX are known in the literature [J. At the. Chem. Soc, Vol. 64, 2714 (1942); J. Org. Chem., Vol. 39, 2172 (1974); Helv. Chim. Acta, Vol. 61, 1565 (1978)] or can be prepared according to the literature cited.
  • the subsequent saponification of the ester X takes place under generally customary conditions, depending on the various structural elements, the alkaline or acid saponification of the compounds X can be advantageous. Under the conditions of ester saponification, 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, if appropriate in the presence of an acid.
  • 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.
  • reaction mixtures are worked up in a customary manner, for example by mixing with water, separating the phases and, if appropriate, purifying the crude products by chromatography.
  • the intermediate and end products sometimes fall in the form of colorless or weakly brownish, viscous oils, which are freed from volatile components or cleaned 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.
  • isomer mixtures are obtained in 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.
  • Alkyl saturated, straight-chain or branched hydrocarbon radicals with 1 to 4, 6 or 8 carbon atoms, for example dC 6 -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1- Dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyI, 2- Methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1- Ethyl butyl, 2-ethyl
  • Haloalkyl straight-chain or branched alkyl groups having 1 to 2, 4, 6 or 8 carbon atoms (as mentioned above), it being possible for some or all of the hydrogen atoms in these groups to be replaced by halogen atoms as mentioned above: in particular dC 2 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
  • Haloalkenyl unsaturated, straight-chain or branched hydrocarbon radicals with 2 to 8 carbon atoms and one or two double bonds in any position (as mentioned above), the hydrogen atoms in these groups being partially or completely replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine could be;
  • 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,
  • 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 e.g. 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isoliazolidinyl, 4-isolazolidinyl Pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyI, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl,
  • Nitrogen atoms and one sulfur or oxygen atom 5-ring heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members, e.g. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, and 1, 3,4-triazol-2-yI;
  • 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-pyrim ⁇ dinyI and 2-pyrazinyl;
  • Oxyalkyleneoxy divalent unbranched chains of 1 to 3 CH 2 groups, both valencies being bonded via an oxygen atom to the skeleton, such as OCH 2 0, OCH 2 CH 2 OCH 2 CH 2 0 and 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.
  • R is dd-alkyl, C 2 -C 6 -alkenyl or -C-C 8 haloalkyl.
  • Z 1 is hydrogen, fluorine or CrC 6 fluoroalkyl
  • Z 2 is hydrogen or fluorine, or Z 1 and Z 2 together form a double bond
  • q is 0 or 1
  • R 3 is hydrogen or methyl
  • R 1 is C 3 -C 6 cycloalkyl, which can be substituted by C 1 -C 4 alkyl.
  • 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-, partially butyl, and C1-C 4 - alkoxymethyl, especially ethoxymethyl, or C 3 -C 6 cycloalkyl, especially cyclopentyl or cyclohexyl;
  • R 2 is hydrogen or methyl;
  • X are as defined for formula I, in particular mean cyano, methoxy or ethoxy.
  • Another preferred embodiment of the invention relates to compounds of the formula I.2.
  • Y is hydrogen or dC 4 alkyl, in particular methyl and ethyl
  • X is as defined for formula I, in particular cyano, methoxy or ethoxy.
  • 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 as a ring member and / or contain one or more substituents from the group halogen, CC 6 alkyl, d-Ce-haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, dC 6 alkoxy , dd-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, Ci -Ce-alkyl, Ci-Ce-haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, dC 6 alkoxy, dC 6 haloalkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 -Halogenalkenyloxy, (exo) -dC 6 -alkylene and oxy-C ⁇ C 3 - alkyleneoxy can wear; and X are as defined for formula I, in particular mean cyano, methoxy or ethoxy.
  • R 1 and R 2 together with the nitrogen atom to which they are attached form a piperidinyl, morpholinyl or thimorpholinyl ring, in particular a piperidinyl ring which may be halogenated by one to three groups, dC 4 alkyl or dC haloalkyl is substituted.
  • the compounds in which R 1 and R 2 together with the nitrogen atom to which they are attached form a 4-methylpiperidine ring are particularly preferred.
  • the invention furthermore relates to compounds I in which R 1 and R 2 form, together with the nitrogen atom to which they are attached, a pyrazole ring which, if appropriate, is substituted by one or two groups halogen, C 1 -C 4 Alkyl or CC 4 - 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 - (CH 2 ) 2 CH (CH3) (CH 2 ) 2 -, - (CH 2 ) 2 CH (CF 3 ) (CH 2 ) 2 - or - (CH 2 ) 2 O ( CH 2 ) 2 - mean.
  • compounds I are particularly preferred in which X is cyano, methoxy or ethoxy, in particular cyano or methoxy.
  • X denotes methyl
  • Table 1 Compounds of the formula I in which X is cyano and the combination of R 1 and R 2 for each compound corresponds to one row of Table A.
  • 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 leaf and soil fungicides.
  • Botrytis cinerea (gray mold) on strawberries, vegetables, ornamental plants and vines
  • the compounds I are also suitable for combating harmful fungi such as Pacilomyces variotii in the protection of materials (e.g. wood, paper, dispersions for painting, fibers or fabrics) and in the protection of stored products.
  • harmful fungi such as Pacilomyces variotii in the protection of materials (e.g. 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 compound.
  • 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 amounts of 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 customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the arrival application form 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, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants.
  • solvents and auxiliaries The following are essentially considered as solvents / auxiliaries:
  • aromatic solvents e.g. Solvesso products, xylene
  • paraffins e.g. petroleum fractions
  • alcohols e.g. methanol, butanol, pentanol, benzyl alcohol
  • ketones e.g. cyclohexanone, gamma-butryolactone
  • pyrrolidones NMP, NOP
  • Acetates glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters.
  • solvent mixtures can also be used
  • Carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite liquors and methyl cellulose.
  • natural stone powder e.g. kaolins, clays, talc, chalk
  • synthetic stone powder e.g. highly disperse silica, silicates
  • Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite liquors and methyl cellulose.
  • Mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, also coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, are used to produce directly sprayable solutions, emulsions, pastes or oil dispersions.
  • 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).
  • 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. When diluted in water, an emulsion results.
  • E Suspensions (SC, OD) 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 dispersants 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.
  • 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. 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 substances as such in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, old-dispersions, pastes, dusts, Spreading agents, granules by spraying, atomizing, dusting, scattering or pouring can be used.
  • 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, old dispersions) by adding water.
  • 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.
  • 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, for example, with herbicides, insecticides,
  • Acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl, • Amine derivatives such as aldimorph, dodine, dodemorph, fenpropimorph, fenpropidin, guazatine, iminoctadine, spiroxamine, tridemorph
  • Anilinopyrimidines such as pyrimethanil, mepanipyrim or cyrodinyl,
  • Antibiotics such as cycloheximide, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin,
  • Azoles such as bitertanol, bromoconazole, cyproconazole, difenoconazole, dinitroconazole, enilconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole, hexaconazole, imazalil, metconazol, triazolazolone, triazolone, propiconone , 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, fenarimoi, fuberidazole, flutolanil, furametpyr, isoprothiolan, mepronazidolomolol, probolil, probolil, probolil, nuarolon, probolil Quinoxyfen, silthiofam, thiabenzazole, thifluzamide, thiophanate methyl, tiadinil, tricyclazole, triforins,
  • copper fungicides such as Bordeaux broth, copper acetate, copper oxychloride, basic copper sulfate, • nitrophenyl derivatives, such as binapacryl, dinocap, dinobutone, nitrophthaloisopropyl
  • Phenylpyrroles such as fenpiclonil or fludioxonil
  • fungicides such as acibenzolar-S-methyl, benthiavalicarb, carpropamide, chlorothalonil, cyflufenamid, cymoxanil, Dazomet, diclomezin, diclocymet, Diethofen-carb, edifenphos, ethaboxam, fenhexamide, fentin acetate, fennosetanyl, ferim Fosetyl aluminum, iprovalicarb, hexachlorobenzene, metrafenone, pencycuron, propamocarb, phthalide, toloclofos-methyl, quintozene, zoxamide
  • strobilurins such as azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin or trifloxystrobin, • sulfenoic acid derivatives such as captafol, captan, dichlofluanid, folpet, tolylfluanid
  • Cinnamic acid amides and analogues such as dimethomorph, flumetover or flumorph.
  • Step 2b 5-methyl-6- (pentafluorophenyI) -7-hydroxy-1, 2,4-triazolo [1,5a] pyrimidine (formula VI)
  • Step 2d 5-methyl-6- (pentafluorophenyl) -7- (4-methylpiperidinyl) -1, 2,4-triazolo [1,5a] pyrimidine (formula I)
  • the active ingredients were prepared as a stock solution with 0.25% by weight of active ingredient in acetone or DMSO. 1% by weight of emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) was added to this solution and diluted with water to the desired concentration.
  • emulsifier Uniperol® EL wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • 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 at 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%.
  • Example of use 3 Protective activity against the Septoria leaf spot disease of the wheat caused by Septoria tritici

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  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Catching Or Destruction (AREA)

Abstract

L'invention concerne des 6-pentafluorophényl-triazolopyrimidines de formule (I) dans laquelle les substituants ont la signification suivante : R1 représente alkyle, halogénure d'alkyle, cycloalkyle, halogénure de cycloalkyle, alcényle, halogénure d'alcényle, cycloalcényle, halogénure de cycloalcényle, alcynyle, halogénure d'alcynyle ou phényle, naphtyle ou un hétérocycle saturé, partiellement insaturé ou aromatique, à cinq ou six membres, contenant un à quatre hétéroatomes du groupe O, N ou S ; R2 représente hydrogène ou un des groupes cités pour R1 ; R1 et R2 peuvent également former avec l'atome d'azote auquel ils sont liés un hétérocyclyle ou un hétéroaryle à cinq ou six membres, qui est lié par l'intermédiaire de N et qui peut contenir un à trois autres hétéroatomes du groupe O, N et S comme terme cyclique ; R1 et/ou R2 peuvent être substitués conformément à la description ; X représente cyano, alkyle, alcoxy, alcényloxy, halogénure d'alcoxy ou halogénure d'alcényloxy. L'invention concerne également un procédé pour produire ces composés, des agents contenant ces composés, ainsi que leur utilisation pour lutter contre des champignons nuisibles phytopathogènes.
PCT/EP2004/014210 2003-12-17 2004-12-14 6-pentafluorophenyl-triazolopyrimidines, procede pour leur production et leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant WO2005058904A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2006544309A JP2007514682A (ja) 2003-12-17 2004-12-14 ６−ペンタフルオロフェニル−トリアゾロピリミジン、その製造方法、および病原真菌を防除するためのその使用、ならびに、これらの物質を含む薬剤
EP04803836A EP1697364A1 (fr) 2003-12-17 2004-12-14 6-pentafluorophenyl-triazolopyrimidines, procede pour leur production et leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant
BRPI0417639-1A BRPI0417639A (pt) 2003-12-17 2004-12-14 compostos, processo para preparar os mesmos, agente, semente, e, processo para combater fungos nocivos fitopatogênicos
US10/582,938 US20070105928A1 (en) 2003-12-17 2004-12-14 6-Pentafluorophenyl-triazolopyrimidines, method for their production and their use for combating pathogenic fungi, in addition to agents containing said substances
IL175895A IL175895A0 (en) 2003-12-17 2006-05-24 6-pentafluorophenyl-triazolopyrimidines, method for their production and their use for combating pathogenic fungi, in addition to agents containing said substances

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10359452 2003-12-17
DE10359452.3 2003-12-17

Publications (1)

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WO2005058904A1 true WO2005058904A1 (fr) 2005-06-30

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EP (1) EP1697364A1 (fr)
JP (1) JP2007514682A (fr)
CN (1) CN1894253A (fr)
AR (1) AR046906A1 (fr)
BR (1) BRPI0417639A (fr)
IL (1) IL175895A0 (fr)
WO (1) WO2005058904A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007012600A1 (fr) * 2005-07-27 2007-02-01 Basf Aktiengesellschaft Fongicide 5-alkyl-6-phenyl-pyrazolopyrimidine-7-ylamine
WO2007012603A1 (fr) * 2005-07-27 2007-02-01 Basf Aktiengesellschaft 6-phenyle-triazolopyrimidinylamines fongicides

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0071792A2 (fr) * 1981-08-01 1983-02-16 BASF Aktiengesellschaft 7-Amino-azolo (1,5-a) pyrimidines procédé pour leur production et fungicides les contenant
EP0834513A2 (fr) * 1996-10-07 1998-04-08 American Cyanamid Company Pentafluorophénylazolopyrimidines
US5994360A (en) * 1997-07-14 1999-11-30 American Cyanamid Company Fungicidal 5-alkyl-triazolopyrimidines
WO2002038565A2 (fr) * 2000-11-13 2002-05-16 Basf Aktiengesellschaft 7-(r)-amino-triazolopyrimidines, sa production et son utilisation dans la lutte contre les champignons pathogenes des plantes
WO2002083677A1 (fr) * 2001-04-11 2002-10-24 Basf Aktiengesellschaft 6-(2-chloro-6-fluoro-phenyl)-triazolopyrimidines
WO2003093271A1 (fr) * 2002-05-03 2003-11-13 Basf Aktiengesellschaft Triazolopyrimidines fongicides, leurs procedes de production et leur utilisation pour la lutte contre des champignons nuisibles, et agents contenant ces composes
WO2004058765A1 (fr) * 2002-12-20 2004-07-15 Basf Aktiengesellschaft Triazolopyrimidines, leurs procedes de production et leur utilisation pour lutter contre des champignons nuisibles et agents contenant lesdits composes
WO2004087705A1 (fr) * 2003-03-31 2004-10-14 Basf Aktiengesellschaft 7-alcenylamino-triazolopyrimidines, leurs procedes de production et leur utilisation pour lutter contre des champignons nuisibles, et agents contenant lesdits composes
WO2004087706A1 (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

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0071792A2 (fr) * 1981-08-01 1983-02-16 BASF Aktiengesellschaft 7-Amino-azolo (1,5-a) pyrimidines procédé pour leur production et fungicides les contenant
EP0834513A2 (fr) * 1996-10-07 1998-04-08 American Cyanamid Company Pentafluorophénylazolopyrimidines
US5965561A (en) * 1996-10-07 1999-10-12 American Cyanamid Company Pentafluorophenylazolopyrimidines
US5994360A (en) * 1997-07-14 1999-11-30 American Cyanamid Company Fungicidal 5-alkyl-triazolopyrimidines
WO2002038565A2 (fr) * 2000-11-13 2002-05-16 Basf Aktiengesellschaft 7-(r)-amino-triazolopyrimidines, sa production et son utilisation dans la lutte contre les champignons pathogenes des plantes
WO2002083677A1 (fr) * 2001-04-11 2002-10-24 Basf Aktiengesellschaft 6-(2-chloro-6-fluoro-phenyl)-triazolopyrimidines
WO2003093271A1 (fr) * 2002-05-03 2003-11-13 Basf Aktiengesellschaft Triazolopyrimidines fongicides, leurs procedes de production et leur utilisation pour la lutte contre des champignons nuisibles, et agents contenant ces composes
WO2004058765A1 (fr) * 2002-12-20 2004-07-15 Basf Aktiengesellschaft Triazolopyrimidines, leurs procedes de production et leur utilisation pour lutter contre des champignons nuisibles et agents contenant lesdits composes
WO2004087705A1 (fr) * 2003-03-31 2004-10-14 Basf Aktiengesellschaft 7-alcenylamino-triazolopyrimidines, leurs procedes de production et leur utilisation pour lutter contre des champignons nuisibles, et agents contenant lesdits composes
WO2004087706A1 (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

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007012600A1 (fr) * 2005-07-27 2007-02-01 Basf Aktiengesellschaft Fongicide 5-alkyl-6-phenyl-pyrazolopyrimidine-7-ylamine
WO2007012603A1 (fr) * 2005-07-27 2007-02-01 Basf Aktiengesellschaft 6-phenyle-triazolopyrimidinylamines fongicides

Also Published As

Publication number Publication date
AR046906A1 (es) 2005-12-28
EP1697364A1 (fr) 2006-09-06
IL175895A0 (en) 2006-10-05
CN1894253A (zh) 2007-01-10
BRPI0417639A (pt) 2007-03-27
JP2007514682A (ja) 2007-06-07

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