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WO2007023020A1 - Composes 7-amino-6-heteroaryl-1,2,4-triazolo[1,5-a]pyrimidine et utilisation dans la lutte contre des champignons parasites - Google Patents

Composes 7-amino-6-heteroaryl-1,2,4-triazolo[1,5-a]pyrimidine et utilisation dans la lutte contre des champignons parasites Download PDF

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Publication number
WO2007023020A1
WO2007023020A1 PCT/EP2006/063964 EP2006063964W WO2007023020A1 WO 2007023020 A1 WO2007023020 A1 WO 2007023020A1 EP 2006063964 W EP2006063964 W EP 2006063964W WO 2007023020 A1 WO2007023020 A1 WO 2007023020A1
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formula
alkyl
compounds
het
methyl
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PCT/EP2006/063964
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German (de)
English (en)
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Oliver Wagner
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Basf Aktiengeseelschaft
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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
    • A01N43/90—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 7-amino-6-heteroaryl-1, 2,4-triazolo [1, 5-a] pyrimidine compounds of the formula (I)
  • Het is a five-membered nitrogen-containing heteroaromatic ring selected from pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl and isothiazolyl, where Het is unsubstituted or substituted by one, two, three or four identical or different substituents L:
  • L is halogen, cyano, nitro, hydroxy, cyanato (OCN), (Ci-C 8) -alkyl, (Ci-C 8) -haloalkyl, (C 2 -Cs) -alkyl keny I, (C2-C8) - Haloalkenyl, (C 4 -C 10) -alkadienyl, (C 4 -C 10) -haloalkadienyl, (C 2 -C 8 ) -alkynyl, (C 2 -C 8 ) -halogeno-alkynyl, (C 1 -C 8 ) -alkoxy, (Ci-C8) -haloalkoxy, (C2-C8) alkenyloxy, (C 2 - C 8) haloalkenyloxy, (C2-C8) alkynyloxy, (C2-C8) haloalkynyloxy, (C2-C8) haloalkyny
  • n 0, 1 or 2;
  • a 1 is hydrogen, hydroxy, (Ci-C 8) -alkyl, (Ci-C 8) haloalkyl,
  • a 2 is one of the groups mentioned under A 1 or (C 2 -C 8 ) -alkenyl, (C 2 -
  • R 5 are independently hydrogen, (Ci-Cs) -alkyl, (Ci-C 8) - haloalkyl, (C 2 -Cs) -alkyl keny I, (C 2 -Cs) haloalkenyl, (C 2 - C 8) - alkynyl, (C 2 -C 8) -haloalkynyl, (C 3 -C 8) -cycloalkyl, (C 3 -C 8) -halocycloalkyl, (C3-C8) cycloalkenyl, or (C 3 -C 8 ) -halogeno-cycloalkenyl,
  • R 1 can carry one, two, three or four identical or different groups R a :
  • R a is halogen, cyano, nitro, hydroxy, carboxyl, amino (Ci-C 8) alkyl, (Ci C 8) haloalkyl, (C 2 -Cs) -alkyl keny I, (C 2 -C 8) - Haloalkenyl, (C 2 -C 8 ) -alkynyl, (C 2 -C 8 ) -haloalkynyl, (C 4 -C 10) -alkadienyl, (C 1 -C 8 ) -alkoxy,
  • R a may in turn carry one, two or three identical or different groups R b :
  • R b is halogen, cyano, nitro, hydroxy, carboxyl, mercapto, amino, formyl, aminocarbonyl, aminothiocarbonyl, (Ci-C 8) -alkyl, (d- C 8) haloalkyl, (C 2 -Cs) -alkyl keny I , (C2-C8) -haloalkenyl, (C 4 - Cio) alkadienyl, (C 2 -Cs) -alkyl kiny I, (C2-C8) haloalkynyl, (Ci-C 8) -
  • X is hydrogen, halogen, hydroxy, cyano, NR 3 R 4, (Ci-C 8) alkoxy, (Ci-C 8) - haloalkoxy, (Ci-C8) alkylthio, (Ci-C8) alkylsulfinyl, (C 1 -C 8 ) -alkylsulfonyl, where R 3 and R 4 independently of one another have the meanings given for R 1 ;
  • compositions which comprise at least one of the compounds according to the invention, processes for the preparation of these compounds, Intermediates for the preparation of the compounds and the agriculturally acceptable salts thereof, the preparation of the intermediates and the use of the compounds according to the invention for controlling phytopathogenic fungi.
  • the compounds of the formula (I) can have one or more centers of chirality and are then present as enantiomer or diastereomer mixtures.
  • the invention relates to both the pure enantiomers or diastereomers or rotamers and mixtures thereof.
  • Suitable compounds of formula (I) also include all possible stereoisomers (cis / trans isomers) and mixtures thereof.
  • the compounds of the invention and / or their agriculturally acceptable salts can be present in various crystal modifications, which may differ in their biological activity. They are also the subject of the present invention.
  • EP-A 613 900 is directed to 7-amino-1,2,4-triazolo [1,5-a] pyrimidine compounds and their use as fungicides. These compounds may have a secondary or tertiary amino group in the 7-position and an optionally substituted cycloalkyl ring or a heterocyclic group in the 6-position.
  • a heterocyclic group means a 3-6, preferably 5-6-membered ring system. Explicitly, a thien-3-yl residue is disclosed as the heterocyclyl residue at position 6.
  • WO 01/96341 discloses intermediates of the formula (II) which are used to prepare fungicidally active triazolopyrimidine-7-ylideneamines.
  • the intermediates have an amino group or a secondary amine in the 7-position; in position 6 in the compounds (II) according to WO 01/96341 there is a phenyl, cycloalkyl or a five- or six-membered heteroaryl group.
  • WO 01/96314 discloses intermediates of the formula (II) which are used to prepare fungicidally active 2- (cyanoamino) pyrimidines.
  • the substituent at position 7 may i.a. an amino group, a secondary or a tertiary amine, in position 6 is a phenyl, cycloalkyl or a 5- or 6-membered heteroaryl group.
  • WO 04/011467 is directed to 1, 2,4-triazolo [1, 5-a] pyrimidines, which can only carry a tertiary amino group in the 7-position, when an amino group is present at this position.
  • WO 04/108727 discloses 1, 2,4-triazolo [1, 5a] pyrimidines and their use for controlling unwanted microorganisms. In position 7, both secondary and tertiary amino groups may be present, the position 6 of the pyrimidine ring is substituted by either a pyridyl or a pyrimidyl group.
  • WO 04/113342 relates to 1, 2,4-triazolo [1, 5a] pyrimidines, which are necessarily substituted in the 2-position of the 1, 2,4-triazolo [1, 5-a] pyrimidine skeleton.
  • both secondary and tertiary amino groups may be present at position 6 of the pyrimidine ring is a 5- or 6-membered heterocyclyl group having 1 to 4 heteroatoms such as nitrogen, oxygen and / or sulfur, wherein pyridyl, pyrimidyl, thienyl and thiazolyl are preferred as Heterocyclylrest.
  • 1,2,4-triazolo [1,5-a] pyrimidines known from the prior art are in some cases unsatisfactory with regard to their fungicidal activity or have undesirable properties, such as low crop tolerance.
  • the present invention is therefore based on the object to provide new compounds with better fungicidal activity and / or better crop compatibility.
  • suitable agriculturally acceptable salts are, in particular, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the fungicidal action of the compounds according to the invention.
  • the ions of the alkali metals preferably sodium or potassium, the alkaline earth metals, preferably calcium, magnesium or barium, the transition metals, preferably manganese, copper, zinc or iron, or the ammonium ion, the desired one to four (Ci-C4 ) Alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably Tn- (C 1 -C 4) -alkylsulfonium and sulfoxonium ions, preferably tri (Ci -C4) -alkylsulfoxonium, into consideration.
  • the alkali metals preferably sodium or potassium
  • the alkaline earth metals preferably calcium, magnesium or barium
  • the transition metals preferably manganese,
  • Anions of advantageously usable acid addition salts are, for example, chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, Phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of (Ci-C4) -alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reaction of the compounds of the formula (I) according to the invention with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • the compounds of the formula (I) according to the invention can be obtained in various ways in analogy to prior art processes known per se.
  • the compounds according to the invention can be prepared as described below:
  • the method at temperatures ranging from 0 ° C to 7O 0 C, preferably 1O 0 C to 35 0 C.
  • the reaction is preferably carried out in an inert solvent, for example an ether, e.g. Dioxane, diethyl ether, diisopropyl ether, tert-butyl methyl ether or especially tetrahydrofuran, a halogenated hydrocarbon such as dichloromethane or dichloroethane or an aromatic hydrocarbon such as toluene or o-, m-, p-xylene or in a mixture of the aforementioned solvents.
  • an ether e.g. Dioxane, diethyl ether, diisopropyl ether, tert-butyl methyl ether or especially tetrahydrofuran
  • a halogenated hydrocarbon such as dichloromethane or dichloroethane or an aromatic hydrocarbon such as toluene or o-, m-, p-xylene or in a mixture of the aforementioned solvents.
  • a base such as, for example, tertiary amines, in particular triethylamine, biscyclohexylmethylamine, pyridine, picoline or inorganic bases, such as potassium carbonate.
  • a base such as, for example, tertiary amines, in particular triethylamine, biscyclohexylmethylamine, pyridine, picoline or inorganic bases, such as potassium carbonate.
  • Excess amine H2NR 1 can also serve as a base.
  • the amines H2NR 1 used in this process are generally commercially available or can be prepared by methods well known to those skilled in the art.
  • 5,7-Dihalogentriazolopyrimidines of the formula (II) can be obtained, for example, by reacting the corresponding 5,7-dihydroxytriazolopyrimidine of the formula (III)
  • the halogenating agent used is advantageously a phosphorus oxyhalide or a phosphorus (V) halide, such as phosphorus pentachloride, phosphorus oxybromide or phosphorus oxychloride or a mixture of phosphorus oxychloride and phosphorus pentachloride.
  • reaction of the compounds of the formula (III) with the halogenating agent is usually carried out at 0 ° C. to 150 ° C., preferably at 80 ° C. to 125 ° C. [cf. also EP-A 770 615].
  • the reaction may be carried out in bulk or in an inert solvent, e.g. a halogenated hydrocarbon, such as dichloromethane, dichloroethane or an aromatic hydrocarbon, such as toluene or o-, m-, p-xylene or in a mixture of said solvents.
  • a halogenated hydrocarbon such as dichloromethane, dichloroethane or an aromatic hydrocarbon, such as toluene or o-, m-, p-xylene or in a mixture of said solvents.
  • 5,7-Dihydroxytriazolopyrimidines of the formula (III) can be prepared in various ways, for example in analogy to those described in Adv. Het. Chem. Vol. 57, p. 81ff. (1993).
  • 5,7-dihydroxytriazolopyrimidines of the formula (III) can be prepared by reacting 3-amino-1,2,4-triazole with the corresponding heteroarylmalonate of
  • Het is defined as described for formula (I) and R is alkyl, preferably (C 1 -C 4 ) -alkyl, in particular methyl or ethyl.
  • the reaction of 3-amino-1, 2,4-triazole with a Heteroarylmalonat (IV) is usually carried out at temperatures of 80 0 C to 250 0 C, preferably from 120 0 C to 180 0 C.
  • the reaction is carried out without solvent, or an inert organic solvent is used.
  • a base may be preferred [cf. EP-A 770 615].
  • it may also be preferred to carry out the reaction in the presence of acetic acid under conditions well known to those skilled in the art.
  • Suitable solvents are, for example, aliphatic hydrocarbons, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, ethers, nitriles, ketones, alcohols, and N-methylpyrrolidone, dimethyl sulfoxide, dimethylformamide and dimethylacetamide.
  • the reaction is particularly preferably carried out without a solvent or in chlorobenzene, xylene, dimethyl sulfoxide or N-methylpyrrolidone. It is also possible to use mixtures of the solvents mentioned.
  • catalytic amounts of acids such as p-toluenesulfonic acid, acetic acid or propionic acid, may also be added.
  • Suitable bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides, alkali metal and alkaline earth metal oxides, alkali metal and alkaline earth metal hydrides, alkali metal amides, alkali metal and alkaline earth metal carbonates and alkali metal bicarbonates, such as potassium carbonate, organometallic compounds, in particular alkali metal alkyls, alkylmagnesium halides and alkali metal and alkaline earth metal alkoxides and dimethoxymagnesium , also organic bases, eg tertiary amines such as trimethylamine, triethylamine, triisopropylethylamine, tributylamine and N-methylpiperidine, N-methylmorpholine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic amines into consideration. Particular preference is given to using tertiary amines, such
  • the bases are generally used in catalytic amounts, but they can also be used equimolar, in excess or optionally as a solvent.
  • the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use the base and the heteroarylmalonate (IV) in excess, based on the 3-amino-1, 2,4-triazole.
  • Preferred compounds of the present invention can be obtained starting from heteroaryl malonates of formula (IV) wherein Het is selected from the Het. Particularly preferred compounds of the present invention are further accessible starting from heteroarylmalonates (IV) wherein Het has the meanings given in Tables 1 to 147.
  • Particularly preferred compounds can be prepared starting from 4-methylpyrazol-1-yl, 4-chloro-3,5-dimethylpyrazol-1-yl, 3,4-dimethylpyrazol-1-yl, 4,5-dimethylpyrazol-1-yl, 4- Chloropyrazol-1-yl, 3,4,5-tribromopyrazol-1-yl or 1, 3,5-trimethylpyrazol-4-yl.
  • Heteroarylmalonates of the formula (IV) can be prepared starting from heteroaryl compounds of the formula (V)
  • R z is hydrogen or a (Ci-C4) alkoxycarbonyl group, Het has the meanings given for formula (I), Q is halogen or (Ci-C4) alkoxy, in particular Methoxy or ethoxy, and R is (C 1 -C 4 ) alkyl.
  • the reaction described above is usually carried out in the presence of strong bases.
  • R z is hydrogen
  • alkali metal amides such as sodium amide or lithium diisopropylamide, or lithium organic compounds such as phenyl lithium or butyl lithium as base.
  • R z is hydrogen
  • the reaction of the compound (V) with compounds of the formula (VI) can be carried out in one stage or in two separate stages, in which latter case the intermediate (V) is obtained in which R z is an alkoxycarbonyl group.
  • the reaction of compound (V) with (VI) can be carried out in analogy to the method described in J.
  • R z is an alkoxycarbonyl group
  • an alkali metal alcoholate for example sodium or potassium ethanolate, sodium or potassium butoxide, sodium or potassium methoxide as the base.
  • malonates of the formula (IV) is also advantageously achieved by reaction of corresponding bromine heteroaryl compounds Br-Het with dialkyl malonates under Cu (I) catalysis [cf. Chemistry Letters, pp. 367-370, 1981; EP-A 10 02 788].
  • Z in the compounds ZY represents a cation
  • Y is a hydroxide, cyanide, (Ci-C 8) alkoxylate, (Ci-C 8) -Halogenalkoxylat or (Ci-C ⁇ J-alkylthiolate
  • ZY is dependent on the group to be introduced is thus a hydroxide, inorganic cyanide (for example KCN, NH 4 CN), a (halogen) alkoxylate or a thiolate
  • the cation Z is of little importance and many different types are suitable Ammonium, tetraalkylammonium salts such as tetramethylammonium or tetraethylammonium salts or alkali or alkaline earth metal salts are preferred.
  • the reaction with Z-Y is preferably carried out in an inert solvent.
  • suitable solvents include ethers such as dioxane, diethyl ether, methyl tert-butyl ether and preferably tetrahydrofuran, halogenated hydrocarbons such as dichloromethane or dichloroethane, aromatic hydrocarbons such as toluene, and mixtures thereof.
  • the reaction temperature is usually 0 to 120 ° C., preferably 10 to 40 ° C. [cf. J. Heterocycl. Chem., Vol. 12, pp. 861-863 (1975)].
  • Halogen fluorine, chlorine, bromine or iodine
  • Alkyl and the alkyl moieties in assembled groups saturated, straight-chain or branched hydrocarbon radicals.
  • the alkyl radicals are preferably (Ci-Cs) -AlkVl-, in particular (Ci-Ce) -alkyl radicals.
  • alkyl groups which are preferred according to the invention are 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-methylpentyl, 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-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1- Ethyl 1-methylpropyl
  • the alkyl groups are substituted at least once or completely by a particular halogen atom, preferably fluoro, chloro or bromo. In a further embodiment, the alkyl groups are partially or completely halogenated by various halogen atoms; for mixed halogen substitutions, the combination of chlorine and fluorine is preferred.
  • Examples of preferred mixed-substituted haloalkyl radicals are chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl.
  • Alkenyl and the alkenyl moieties in assembled groups monounsaturated, straight-chain or branched hydrocarbon radicals with a double bond in any position.
  • Preferred are (C 2 -C 8 ) -alkenyl radicals, more preferably (C 4 -C 6 ) -alkenyl radicals.
  • alkenyl groups are 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, 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, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-e
  • Haloalkenyl alkenyl as defined above, wherein in these groups at least one of the hydrogen atoms or all the hydrogen atoms are replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;
  • Alkadienyl diunsaturated, straight-chain or branched hydrocarbon radicals having two double bonds in any positions, but not adjacent. Preference is given to (C 4 -C 10) -alkadienyl radicals, more preferably (C 6 -C 8 ) -alkadienyl radicals.
  • alkadienyl radicals are 1, 3-butadienyl, 1-methyl-1, 3-butadienyl, 2-methyl-1,3-butadienyl, penta-1,3-dien-1-yl, hexa-1,4-diene 1-yl, hexa-1, 4-dien-3-yl, hexa-1, 4-dien-6-yl, hexa-1, 5-dien-1-yl, hexa-1, 5-diene-3 -yl, hexa-1, 5-dien-4-yl, hepta-1, 4-dien-i-yl, hepta-1, 4-dien-3-yl, hepta-1, 4-dien-6-yl , Hepta-1, 4-dien-7-yl, hepta-1, 5-dien-1-yl, hepta-1, 5-dien-3-yl, hepta-1, 5-dien-4-yl, hepta -1, 5-dien-7
  • Haloalkadienyl alkadienyl as defined above, wherein in these groups at least one of the hydrogen atoms or all the hydrogen atoms is replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;
  • Alkynyl and the alkynyl moieties in assembled groups straight-chain or branched hydrocarbon radicals of one or two triple bonds in any, but not adjacent position.
  • Preferred are (C 2 -C 8) -alkynyl radicals, more preferably (C 4 -C 6) -alkynyl radicals.
  • Preferred alkynyl radicals are: ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 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, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1 Methyl 2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pent
  • Haloalkynyl alkynyl, as defined above, wherein in these groups at least one of the hydrogen atoms or all are replaced by halogen atoms, as described above under haloalkyl, in particular fluorine, chlorine or bromine;
  • Cycloalkyl and the cycloalkyl parts in composite groups monocyclic, saturated hydrocarbon groups. Preferred are (C 3 -C 8 ) -cycloalkyl radicals, more preferred are (C 4 -C 6 ) -cycloalkyl radicals.
  • cycloalkyl radicals are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl;
  • Halogencycloalkyl cycloalkyl as defined above, wherein in these groups at least one of the hydrogen atoms or all hydrogen atoms are replaced by halogen atoms, as described above under haloalkyl, in particular fluorine, chlorine or bromine;
  • Cycloalkenyl and the cycloalkenyl moieties in assembled groups monocyclic monounsaturated hydrocarbon radicals with one double bond in any position. Preference is given to (C 3 -C 8 ) -cycloalkenyl, furthermore preferred are (C 5 -C 6 ) -cycloalkenyl.
  • Examples of preferred cycloalkenyl radicals are cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl, cyclohexen-4-yl;
  • Halocycloalkenyl cycloalkenyl as defined above, wherein in these groups at least one of the hydrogen atoms or all the hydrogen atoms are replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;
  • Bicycloalkyl bicyclic hydrocarbon radical, with (C5-Cio) -bicycloalkyl being preferred. Further preferred are (C7-C9) bicycloalkyl radicals.
  • bicycloalkyl radicals examples include bicyclo [2.2.1] hept-1-yl, bicyclo [2.2.1] -hept-2-yl, bicyclo [2.2.1] hept-7-yl, bicyclo [2.2.2] octyl 1-yl, bicyclo [2.2.2] oct-2-yl, bicyclo [3.3.0] octyl, bicyclo [4.4.0] decyl;
  • Halogenbicycloalkyl bicycloalkyl, as defined above, wherein in these groups at least one of the hydrogen atoms or all hydrogen atoms are replaced by halogen atoms, as described above under haloalkyl, in particular fluorine, chlorine or bromine;
  • Alkoxy for an alkyl group bonded via an oxygen atom as defined above.
  • (C 1 -C 6 -alkoxy radicals furthermore preferred are (C 2 -C 6) -alkoxy radicals.
  • alkoxy radicals are: methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1, 2, 2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;
  • Haloalkoxy Alkoxy, as defined above, wherein in these groups at least one of the hydrogen atoms or all hydrogen atoms are replaced by halogen atoms, as described above under haloalkyl, in particular fluorine, chlorine or bromine.
  • haloalkoxy groups such as (Ci- C4) -haloalkoxy to use
  • relatively long haloalkoxy groups such as (C 5 -C 8) -haloalkoxy use.
  • haloalkoxy radicals are short-chain OCH 2 F, OCHF 2, OCF 3, OCH 2 Cl, OCHCI 2, OCCI 3, chlorofluoromethoxy, dichlorofluoromethoxy, methoxy Chlordifluor-, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-lodethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC 2 Fs, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 2-bromopropoxy, 3-bro
  • Examples of preferred longer-chain haloalkoxy radicals are 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy;
  • Alkenyloxy Alkenyl as defined above, which is bonded via an oxygen atom. Preferred are (C 2 -C 8) alkenyloxy, more preferably (C 3 -C 6) alkenyloxy.
  • short-chain alkenyloxy radicals such as (C 2 -C 4) -alkenyloxy
  • longer-chain alkenyloxy groups such as (Cs-C ⁇ J-alkenyloxy
  • alkenyloxy radicals are 1-propenyloxy, 2-propenyloxy, 1-methyl-ethenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1-methyl-1-propenyloxy, 2-methyl-1-propenyloxy, 1-methyl 2-propenyloxy, 2-methyl-2-propenyloxy, 1-pentenyl-oxy, 2-pentenyloxy, 3-pentenyloxy, 4-pentenyloxy, 1-methyl-1-butenyloxy, 2-methyl-1-butenyloxy, 3-methyl 1-butenyloxy, 1-methyl-2-butenyloxy, 2-methyl-2-butenyloxy, 3-methyl-2-butenyloxy, 1-methyl-3-butenyloxy, 2-methyl-3-butenyloxy, 3-methyl-3 -butenyloxy, 1-ethenyl, 1-ethenyloxy, 2-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1-methyl-1-propeny
  • Haloalkenyloxy alkenyloxy as defined above, wherein in these groups at least one of the hydrogen atoms or all the hydrogen atoms is replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;
  • Alkynyloxy Alkynyl as mentioned above, which is bonded via an oxygen atom. Preference is given to (C 2 -C 8) -alkynyloxy radicals, furthermore preferably (C 3 -C 6) -alkynyloxy radicals. In the present invention, it may be preferable to use short-chain alkynyloxy groups such as (C 2 -C 4) -alkynyloxy, but on the other hand, it may also be preferable to use longer-chain alkynyloxy groups such as (C 5 -C 8 ) -alkynyloxy.
  • alkynyloxy radicals are 2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-propynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy, 1-methyl-2-butynyl oxy, 1-methyl-3-butynyloxy, 2-methyl-3-butynyloxy, 1-ethyl-2-propynyloxy, 2-hexynyloxy, 3-hexynyloxy, 4-hexynyloxy, 5-hexynyloxy, 1-methyl-2-pentynyloxy, 1-methyl-3-pentynyl-oxy;
  • Haloalkynyloxy alkynyloxy as defined above, wherein in these groups at least one of the hydrogen atoms or all the hydrogen atoms is replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;
  • Alkylene divalent linear chains of CH 2 groups. Preference is given to (C 1 -C 6 ) -
  • Alkylene more preferably (C 2 -C 4 ) -alkylene, furthermore it may be preferable to use (Ci-C 3 ) - alkylene groups.
  • preferred alkylene radicals are CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 (CH 2 J 2 CH 2 , CH 2 (CH 2 ) 3 CH 2 and CH 2 (CH 2 ) 4 CH 2 ;
  • Oxyalkylene Alkylene as defined above, wherein a valence is bonded to the skeleton via an oxygen atom.
  • Examples of preferred oxyalkylene radicals are OCH 2 , OCH 2 CH 2 , OCH 2 CH 2 CH 2 and OCH 2 (CH 2 ) 2 CH 2 ;
  • Oxyalkyleneoxy alkylene as defined above, wherein both valences are bonded to the skeleton via an oxygen atom.
  • Examples of preferred oxyalkyleneoxy radicals are OCH 2 O, OCH 2 CH 2 O and OCH 2 CH 2 CH 2 O.
  • Alkylthio Alkyl as defined above attached via an S atom.
  • Alkylsulfinyl alkyl as defined above bonded through an SO group.
  • Alkylsulfonyl Alkyl as defined above attached via an S (O) 2 group.
  • Aryl aromatic hydrocarbon radical, preference being given to (C 6 -C 4 ) -aryl radicals and (C 6 -C 10) -aryl radicals being particularly preferred.
  • Examples of preferred aryl radicals are phenyl, naphthyl and anthryl.
  • aryl radicals may be substituted by at least one halogen atom or completely by halogen atoms as defined above. According to the invention it may be advantageous to use haloaryl groups, wherein aryl is as defined above. Particularly preferred may be halophenyl and halonaphthyl.
  • Aryloxy Aryl as defined above, wherein the aryl radical is bonded to the skeleton via an oxygen atom.
  • Arylthio aryl, as defined above, wherein the aryl radical is linked to the skeleton via a sulfur atom.
  • the heterocycle is preferably a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S, as defined below.
  • the respective heterocycle may be attached via a carbon atom or via a nitrogen atom, if present. It may be preferred according to the invention that the respective heterocycle is bonded via carbon, on the other hand it may also be preferred that the heterocycle is bonded via nitrogen.
  • heterocycles containing one, two, three or four heteroatoms from the group oxygen, nitrogen and sulfur as ring members: for example, mono- and bicyclic heterocycles with 7
  • Ring members containing, in addition to carbon ring members one to three nitrogen atoms and / or an oxygen or sulfur atom or one or two oxygen and / or sulfur atoms for example tetra- and Hexahydroazepinyl such as 2,3,4,5-tetrahydro [1 H] azepine-1 -, -2-, -3-, -A-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro [2H] azepine-2-, -3-, -A-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro [1 H] azepine-1,
  • heterocyclyl Five- or six-membered saturated or partially unsaturated heterocycle (hereinafter also heterocyclyl) containing one, two, three or four heteroatoms from the group oxygen, nitrogen and sulfur as ring members: for example monocyclic saturated or partially unsaturated heterocycles containing, in addition to carbon ring members, 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-
  • aromatic heterocycle is attached via nitrogen. Examples are:
  • Nitrogen atoms and / or a sulfur or oxygen atom 5-membered ring heteroaryl groups, which in addition to carbon atoms one to four nitrogen atoms or may contain one to three nitrogen atoms and / or one sulfur or oxygen atom as ring members, eg furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (1,2,3-; 1,2,4-triazolyl), tetrazolyl, oxazolyl , Isoxazolyl, 1, 3,4-oxadiazolyl, thiazolyl, isothiazolyl and thiadiazolyl, especially 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4- isoxazolyl, 5-isoxazolyl,
  • carbon-bonded 5-membered heteroaryl groups may be preferred, containing one to three nitrogen atoms or one or two nitrogen atoms and one sulfur or oxygen atom as ring members.
  • Examples of these are: 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2- Oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4- Oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1, 2,4-triazol-3-yl, 5-tetrazolyl, 1,3,
  • carbon-bonded five-membered heteroaryl groups containing an oxygen atom or a sulfur atom such as 2-furyl, 3-furyl, 2-thienyl, 3-thienyl;
  • nitrogen-bonded 5-membered heteroaryl groups containing one to three nitrogen atoms as ring members, for example pyrrol-1-yl, pyrazol-1-yl, imidazol-1-yl, 1,2,3-triazole 1-yl and 1, 2,4-triazol-1-yl; 1-tetrazolyl;
  • 6-membered heteroaryl containing one to three or one to four nitrogen atoms 6-membered ring heteroaryl groups, which in addition to carbon atoms may contain one to three or one to four nitrogen atoms as ring members, e.g. Pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,2,3-triazinyl, 1, 2,4-triazinyl, 1, 3,5-triazinyl, especially 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4 Pyridazinyl, 2-
  • Heteroaryloxy Heteroaryl, as defined above, wherein the heteroaryl radical is bonded to the skeleton via an oxygen atom.
  • Heteroarylthio heteroaryl as defined above, wherein the heteroaryl radical is linked to the skeleton via a sulfur atom.
  • the (R) and (S) isomers or rotamers and racemates are comprised of compounds of formula (I) having chiral centers.
  • the compounds of the invention may be present in various crystal modifications, which may differ in biological activity, which are also included.
  • Formula (I) are the following meanings of the substituents, each alone or in combination, more preferably.
  • the preferred substituents or preferred combinations of substituents apply correspondingly to the precursors of the compounds of the formula (I):
  • the compounds of the present invention contain in the 6-position an optionally substituted five-membered nitrogen-containing heteroaryl radical selected from pyrrole, pyrazole, imidazole, oxazole, isoxazole, thiazole and isothiazole, wherein Het may be attached to the triazolopyrimidine skeleton via a ring carbon atom or via a ring nitrogen atom ,
  • Het may contain one to four or one to three or one or two identical or different substituents L, preferably identical substituents L. More preferably Het contains one or two substituents L, more preferably one or two identical substituents L. Furthermore, Het preferably has two identical substituents L.
  • Het may be preferred for Het to contain at least one substituent L, which is preferably present in the ortho position to the point of attachment to the pyrimidine skeleton.
  • Preferred compounds of the present invention are compounds of the formula (I) in which Het is optionally substituted pyrrolyl, preferably via a ring carbon bonded to the triazolopyrimidine pyrrolyl, ie 2-, or 3-pyrrolyl, more preferably 2-pyrrolyl.
  • the pyrrolyl radical has one, two, three or four substituents L.
  • Het is optionally substituted pyrazolyl, such as 1-, 3-, 4- or 5-pyrazolyl.
  • Het 1 pyrazolyl or 4-pyrazolyl is particularly preferred.
  • the pyrazolyl radical has one, two or three substituents L.
  • Further preferred compounds of the present invention are compounds of the formula (I) in which Het is optionally substituted imidazolyl, ie 1-, 2- or 4-imidazolyl, particularly preferably 1- or 2-imidazolyl.
  • the imidazolyl radical has one, two or three substituents L.
  • oxazolyl preferably oxazolyl bonded via a ring carbon to the triazolopyrimidine, ie 2-, A- or 5-thiazolyl, more preferably 4-oxazolyl.
  • the oxazolyl radical has one or two substituents L.
  • Preferred compounds of the present invention are also compounds of the formula (I) in which Het is optionally substituted isoxazolyl, preferably isoxazolyl bonded via a ring carbon to the triazolopyrimidine, ie 3-, 4- or 5-isoxazolyl, particularly preferably 4-isoxazolyl.
  • the isoxazolyl radical preferably has one or two substituents L.
  • thiazolyl radical has one or two substituents L, as defined above.
  • Preferred compounds of the present invention are also compounds of the formula (I) in which Het is optionally substituted isothiazolyl, preferably isothiazolyl bonded via a ring carbon to the triazolopyrimidine, ie 3-, A- or 5-isothiazolyl, more preferably 4-isothiazolyl.
  • the isothoazolyl radical has one or two substituents L, as defined above.
  • # means in each case the point of attachment of the respective het with the triazolopyrimidine skeleton of the compounds according to the invention or with the precursors thereof.
  • a substitution pattern is selected from A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29 and A-30. specifically selected from A-22, A-23, A-24, A-25 and A-27, A-28, and A-29.
  • L is particularly preferably each selected from halogen, cyano, nitro, (C 1 -C 4 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 1 -C 4 ) -cycloalkoxy, -COO (C 1 -C 4 ), CONH 2 or -CSNH 2 ;
  • L is particularly preferably methyl, ethyl, isopropyl, cyclopropyl, fluorine, chlorine, bromine, iodine, COOCH.sub.3 or CN.
  • Het has one, two or three identical or different substituents L, which are selected from halogen, cyano, nitro, amino, (C 1 -C 6 ) -alkylamino, di- (C 1 -C 6 ) -alkylamino, (C 1 -C 6 ) alkyl, (Ci-C 6) -haloalkyl, (Ci-C 6) alkoxy, (Ci-C 6) -haloalkoxy, NH (CO) - (Ci-C 6) alkyl, C (S) A 2 and C (O) A 2 , wherein A 2 has the abovementioned meanings and is preferably (C 1 -C 4 ) -alkoxy, NH 2 , (C 1 -C 4 ) -alkylamino or di- (C 1 -C 4 ) -alkylamino.
  • substituents L which are selected from halogen, cyano, nitro, amino, (C
  • L are selected from fluorine, chlorine, bromine, cyano, nitro, (d- C4) alkyl, (Ci-C 4) -haloalkyl, (Ci-C 4) alkoxy and (Ci-C 4) - Alkylcarbonyl, particularly preferably fluorine, chlorine, (Ci-C 2 ) alkyl such as methyl or ethyl, (Ci-C 2 ) fluoroalkyl such as trifluoroalkyl, (Ci-C2) alkoxy such as methoxy or (Ci-C2) alkoxycarbonyl such as methoxycarbonyl.
  • Het has at least one substituent which is in ortho-position to the point of attachment to the skeleton to which Het is bound.
  • L when L is bonded to a ring nitrogen of Het, it is particularly preferred that L each independently is
  • L is (Ci-C 6) alkyl or (Ci-C 6) -haloalkyl, more preferably (d-C4) -alkyl or (Ci-C 4) -haloalkyl, particularly methyl or ethyl, especially preferred for methyl.
  • L is independently:
  • Alkylamino means - A 1 is amino, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (Ci-C 6) alkylamino or di- (CrC 6);
  • n 0, 1 or 2;
  • a 2 is one of the groups mentioned under A 1 or (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -alkynyl, (C 2 -C 8 ) -haloalkynyl, (Ci-C 6) alkoxy, (Ci-C 6) -haloalkoxy, (C 2 - C 8) alkenyloxy, (C 2 -C 8) haloalkenyloxy, (C 2 -C 8) -alkynyloxy, (C 2 -C 8) alkynyloxy-halo, (C3-C8) cycloalkoxy or (C3-C means 8) -Halogencycloalkoxy;
  • R 5, R 6 are independently hydrogen or (Ci-C ⁇ J alkyl, (Ci-C ⁇ J haloalkyl, (C 2 -C 8) -haloalkenyl, (C 2 -C 8) -alkynyl, (C 2 -C 8) -haloalkynyl, (C 3 -C 8 -) - cycloalkyl, (C3-C 8 -) - halocycloalkyl, (C3-C8) cycloalkenyl, or (C3-C8) mean halocycloalkenyl.
  • L when it is bonded to a ring nitrogen of Het, in each case particularly preferably (C 1 -C 4 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, -COO (C 1 -C 4 ), -CONH 2 or -CSNH 2 , in particular methyl, ethyl, isopropyl, cyclopropyl or -COOCH 3 .
  • R 1 is hydrogen
  • R 1 is different from hydrogen.
  • R 1 is straight-chain or branched, unsubstituted or substituted (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -
  • Haloalkyl (C 2 -Cs) -Al keny I, (C 2 -Cs) -Al kiny I, (C3-Cs) -cycloalkyl, unsubstituted or substituted phenyl or naphthyl or a five- or six-membered saturated, partially unsaturated or aromatic Heterocycle containing one, two, three or four heteroatoms from the group O, N and S.
  • R 1 is, in particular (Ci-C 6) -alkyl, (C2 -Ce) -Al keny I, (C 2 -Ce) -Al kiny I, (C 3 -C 6) - cycloalkyl, where these radicals 1 , 2, 3, 4 or 5 times may be substituted by halogen, (C 1 -C 6) -alkyl or (C 1 -C 6) -haloalkyl.
  • a particularly preferred embodiment relates to compounds of the formula (I) in which R 1 is a group B:
  • Z 1 is hydrogen, fluorine or (C 1 -C 4 ) -fluoroalkyl
  • Z 2 is hydrogen or fluorine
  • R 7 is hydrogen or methyl.
  • R 1 is (C 3 -C 6) -cycloalkyl for which is obtained by (Ci-C 4) - may be substituted alkyl.
  • X has the meanings given above.
  • X is
  • Halogen in particular methoxy, halomethoxy or ethoxy, or
  • X is halogen, in particular fluorine, chlorine or bromine, preferably chlorine.
  • X is (Ci-Cs) -alkoxy or (C C ⁇ J haloalkoxy, preferably (Ci-C 4) alkoxy or (Ci-C4) - haloalkoxy, in particular methoxy or ethoxy.
  • X is cyano.
  • R 5 and R 6 independently of one another are preferably hydrogen or (C 1 -C 4 ) -alkyl.
  • a 1 is preferably hydrogen, (C 1 -C 6) -alkyl or amino.
  • the index n is preferably 0, 1 or 2.
  • a 2 is preferably (C 1 -C 4 ) -alkoxy, Nhfe, (C 1 -C 4 ) -alkylamine or di- (C 1 -C 4 ) -alkylamino.
  • Tables 1 to 147 compiled compounds (I).
  • the groups mentioned in Tables 1 to 147 for a substituent Het are also considered in isolation, regardless of the combination in which they are mentioned, a particularly preferred embodiment of the dar.
  • Table 2 Compounds of the formula (I) in which X corresponds to chlorine and Het 1, 4-dimethylpyrrol-2-yl and R 1 for a compound corresponds in each case to one row of Table B.
  • Table 8 Compounds of the formula (I) in which X is chlorine and Het is 3-ethyl-5-methylpyrazol-1-yl and R 1 for a compound corresponds in each case to one row of Table B.
  • Table 25 Compounds of the formula (I) in which X is chlorine and Het is 1,5-dimethylpyrazol-4-yl and R 1 for a compound corresponds in each case to one row of Table B.
  • Table 30 Compounds of the formula (I) in which X is chlorine and Het is 3,4,5-trichloropyrazol-1-yl and R 1 for each compound corresponds to one row of Table B.
  • Table 48 Compounds of the formula (I) in which X is chlorine and Het is 3-methylisothiazol-4-yl and R 1 for a compound corresponds in each case to one row of Table B.
  • R 1 for a compound corresponds in each case to one row of Table B.
  • Table 51 Compounds of the formula (I) in which X is CN and Het is 1, 4-dimethylpyrrol-2-yl and R 1 for each compound corresponds to one row of Table B.
  • R 1 for a compound corresponds in each case to one row of Table B.
  • R 1 for a compound corresponds in each case to one row of Table B.
  • R 1 for a compound corresponds in each case to one row of Table B.
  • R 1 for a compound of one row of Table B corresponds to Table 79
  • Table 82 Compounds of the formula (I) in which X is CN and Het is 1-methyl-3,5-dibromopyrazol-4-yl and R 1 for each compound corresponds to one row of Table B.
  • R 1 for a compound corresponds in each case to one row of Table B.
  • R 1 for a compound corresponds in each case to one row of Table B.
  • Table 105 Compounds of the formula (I) in which X is OCH3 and Het is 3-isopropyl-5-methylpyrazol-1-yl and R 1 for a compound corresponds in each case to one row of Table B.
  • Table 110 Compounds of the formula (I) in which X is OCH 3 and Het is 3-chloropyrazol-1-yl and R 1 for a compound corresponds in each case to one row of Table B.
  • Table 120 Compounds of the formula (I) in which X is OCH3 and Het is 1-methyl-3-trifluoromethylpyrazol-4-yl and R 1 for a compound corresponds in each case to one row of Table B.
  • Table B corresponds to Table 123
  • Table 126 Compounds of the formula (I) in which X is OCH3 and Het is 5-chloropyrazol-1-yl and R 1 for a compound corresponds in each case to one row of Table B.
  • Table 130 Compounds of the formula (I) in which X is OCH3 and Het is 1-methyl-3,5-dichloropyrazol-4-yl and R 1 for a compound corresponds in each case to one row of Table B.
  • Table 133 Compounds of the formula (I) in which X is OCH 3 and Het is 4,5-dimethylimidazol-1-yl and R 1 for a compound corresponds in each case to one row of Table B.
  • Table 138 Compounds of the formula (I) in which X is OCH 3 and Het is 3,5-dimethylisoxazol-4-yl and R 1 for a compound corresponds in each case to one row of Table B.
  • Table 143 Compounds of the formula (I) in which X is OCH 3 and Het is 2-methyl-5-chlorothiazol-4-yl and R 1 for each compound corresponds to one row of Table B.
  • Table 144 Compounds of the formula (I) in which X is OCH3 and Het is 2,5-dichlorothiazol-4-yl and R 1 for each compound corresponds to one row of Table B Table 145
  • the compounds I and / or their agriculturally acceptable salts are useful as fungicides. They are distinguished by outstanding activity against a broad spectrum of phytopathogenic fungi from the classes of the Ascomycetes, Deuteromycetes, Basidiomycetes and Peronosporomycetes (syn. Oomycetes). They are partially systemically effective and can be used in crop protection as foliar, pickling and soil fungicides.
  • Cochliobolus species on corn, cereals, rice e.g. Cochliobolus sativus on cereals, Cochliobolus miyabeanus on rice • Colletotricum species on soybeans and cotton
  • Drechslera species Pyrenophora species on maize, cereals, rice and turf, e.g. D.teres to barley or D. tritici-repentis to wheat
  • Fusarium and Verticillium species on various plants e.g. F. graminearum or F. culmorum on cereal or F. oxysporum on a variety of plants, e.g. Tomatoes • Gaeumanomyces graminis on cereals
  • Michrodochium nivale on cereals • Mycosphaerella species on cereals, bananas and peanuts, e.g. M. graminicola on wheat or M.fijiensis on bananas
  • Peronospora species on cabbage and bulbous plants such as P. brassicae on cabbage or P. destructor on onion
  • Phytophthora species on various plants e.g. P.capsici on paprika
  • Pseudoperonospora on various plants e.g. P. cubensis on cucumber or P. humili on hops
  • Puccinia species on various plants e.g. P. triticina, P. striformins, P. hordei or P. graminis on cereals, or P. asparagi on asparagus • Pyricularia oryzae, Corticium sasakii, Sarocladium oryzae, S.atumuatum,
  • Rhynchosporium secalis on barley, rye and triticale • Sclerotinia species on oilseed rape and sunflowers
  • Venturia species scab
  • apples and pears like. e.g. V. inaequalis to apple.
  • the compounds of formula (I) may also be used in cultures tolerant of insect or fungal growth by breeding, including genetic engineering methods.
  • Another object of the present invention is therefore the use of the inventive 7-amino-6-heteroaryl-1, 2-4-triazolo [1, 5-a] pyrimidines of the formula (I) and / or their agriculturally acceptable salts for controlling phytopathogenic fungi.
  • the compounds I and / or their agriculturally acceptable salts are also suitable for controlling harmful fungi in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
  • harmful fungi Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp.
  • Tyromyces spp. Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., moreover, in the protection of the following yeasts: Candida spp. and Saccharomyces cerevisae.
  • the compounds I and / or their agriculturally acceptable salts are used by treating the fungi or the plants, seeds, materials or soil to be protected against fungal attack with a fungicidally effective amount of the active compounds.
  • the application can be done 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 wt .-% of active ingredient.
  • the application rates in the application in crop protection depending on the nature of the desired effect between 0.01 and 2.0 kg of active ingredient per ha.
  • Seed treatment generally requires amounts of active substance of 1 to 1000 g / 100 kg, preferably 1 to 200 g / 100 kg, in particular 5 to 100 g / 100 kg of seed.
  • the application rate of active ingredient depends on the type of application and the desired effect. Usual application rates are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of material treated in the material protection.
  • a further subject of the present invention is therefore a process for controlling phytopathogenic fungi, which comprises treating the fungi or the materials, plants, the soil or seeds to be protected against fungal attack with an effective amount of at least one compound of the formula ( I) and / or an agriculturally acceptable salt thereof.
  • a further subject of the present invention is an agent for controlling phytopathogenic fungi comprising at least one compound of the formula (I) according to the invention and / or an agriculturally acceptable salt thereof and at least one solid or liquid carrier.
  • the compounds I and / or their agriculturally acceptable salts can be converted into the usual formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the application form depends on the respective purpose; It should in any case 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 compound with solvents and / or excipients, if desired under
  • Suitable solvents / auxiliaries are essentially:
  • Aromade e.g., Solvesso products, xylene
  • paraffins e.g., petroleum fractions
  • alcohols e.g., methanol, butanol, pentanol, benzyl alcohol
  • ketones e.g., cyclohexanone, gamma-butyrolactone
  • NMP pyrrolidones
  • glycol diacetate glycol diacetate
  • dimethyl fatty acid amides dimethyl fatty acids
  • Fatty acid ester Fatty acid ester
  • Carriers such as ground natural minerals (e.g., kaolins, clays, talc, chalk) and ground synthetic minerals (e.g., fumed silica, silicates); Emulsifiers such as non-ionic and anionic emulsifiers (e.g., polyoxyethylene
  • surface-active substances are alkali, alkaline earth, ammonium salts of ligninsulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid,
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, coal tar oils and 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, strong polar solvents, e.g. Dimethylsulfoxide, N-methylpyrrolidone or water into consideration.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or
  • Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
  • Granules for example coated, impregnated and homogeneous granules, can be prepared by binding the active compounds to solid carriers.
  • Solid carriers are, for example, mineral earths, such as silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as ammonium sulfate, ammonium phosphate , Ammonium nitrate, ureas and vegetable products such as cereal flour, bark, wood and nutshell flour, celiac powder and other solid carriers.
  • mineral earths such as silica gels, silicates, talc, kaolin, Attaclay, 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 wt .-%, preferably between 0.1 and 90 wt .-% of the active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • formulations are: 1. Products for dilution in water
  • a Water-soluble concentrates (SL, LS)
  • DC Dispersible Concentrates
  • 25 parts by weight of the active compounds are dissolved in 35 parts by weight of xylene with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate each 5 parts by weight).
  • This mixture is added to 30 parts by weight of water by means of an emulsifying machine (e.g., Ultraturax) and made into a homogeneous emulsion. Dilution in water results in an emulsion.
  • the formulation has an active ingredient content of 25% by weight.
  • E Suspensions 20 parts by weight of the active compounds are comminuted to a fine suspension of active substance in an agitated ball mill with the addition of 10 parts by weight of dispersing and wetting agents and 70 parts by weight of water or an organic solvent. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • the active ingredients are dispersed with the addition of 50 parts by weight dispersing and Wetting agents finely ground and produced by means of technical equipment (eg extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the formulation has an active ingredient content of 50% by weight.
  • Water-dispersible and water-soluble powders 75 parts by weight of the active compounds are ground in a rotor-stator mill with the addition of 25 parts by weight of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active ingredient content of the formulation is 75% by weight.
  • 0.5 parts by weight of the active ingredients are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for the direct application with 0.5 wt .-% active ingredient content.
  • LS water-soluble concentrates
  • FS suspensions
  • DS water-dispersible and water-soluble powders
  • WS water-dispersible and water-soluble powders
  • ES emulsifiable concentrates
  • GF gel formulations
  • the active compounds can be used 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, oil dispersions, pastes, dusts, scattering agents, granules by spraying, atomizing, dusting, scattering or Pouring be applied.
  • the forms of application depend entirely on the intended use; 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.
  • the substances as such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier. But it can also be made of effective substance wetting, adhesion, dispersing or emulsifying and possibly solvent or oil concentrates, which are suitable for dilution with water.
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. 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 (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume
  • wetting agents To the active ingredients oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides, optionally also just before use (tank mix), are added. These agents can be added to the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.
  • adjuvants in this sense are in particular: organically modified polysiloxanes, eg Break Thru S 240 ® ; Alcohol alkoxylates, eg. As Atplus 245 ®, Atplus MBA 1303 ®, Plurafac LF 300 ® and Lutensol ON 30 ®; EO-PO block polymers, eg. B.
  • Pluronic RPE 2035 ® and Genapol B ® Alcohol ethoxylates, eg. As Lutensol XP 80 ®; and sodium dioctylsulfosuccinate, e.g. B. Leophen RA ®.
  • the compounds of the invention may also be present in the application form as fungicides together with other active substances, e.g. with herbicides,
  • Insecticides growth regulators, fungicides or even with fertilizers.
  • the compounds (I) or the agents containing them with one or several other active ingredients, in particular fungicides, for example, in many cases, the spectrum of action can be broadened or resistance developments are prevented. In many cases, synergistic effects are obtained.
  • Another object of the present invention is therefore a combination of at least one compound of the formula (I) according to the invention and / or an agriculturally acceptable salt thereof and at least one further fungicidal, insecticidal, herbicidal and / or growth-regulating active ingredient.
  • Metominostrobin picoxystrobin, pyraclostrobin, trifloxystrobin, orysastrobin, (2-chloro-5- [1- (3-methyl-benzyloxyimino) -ethyl] -benzyl) -carbamic acid methyl ester, (2-chloro-5- [1- (6-methyl -pyridin-2-ylmethoxyimino) -ethyl] -benzyl) -carbamic acid methyl ester, 2- (ortho- (2,5-dimethylphenyl-oxymethylene) -phenyl) -3-methoxy-acrylic acid methyl ester;
  • Carboxylic acid anilides Benalaxyl, Benodanil, Boscalid, Carboxin, Mepronil, Fenfuram, Fenhexamid, Flutolanil, Furametpyr, Metalaxyl, Ofurace, Oxadixyl, Oxycarboxin, Penthiopyrad, Thifluzamide, Tiadinil, 4-Difluoromethyl-2-methyl-thiazole-5-carboxylic acid - (4 1 -bromo-biphenyl-2-yl) -amide, 4-difluoromethyl-2-methyl-thiazole-5-carboxylic acid
  • Benzoic acid amides flumetover, fluopicolide (picobenzamide), zoxamide;
  • bitertanol bitertanol
  • bromuconazoles cyproconazole
  • difenoconazole diniconazole
  • enilconazole epoxiconazole
  • fenbuconazole flusilazole, fluquinconazole
  • Flutriafol Flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, Penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimenol, triadimefon, triticonazole;
  • - imidazoles cyazofamide, imazalil, pefurazoate, prochloraz, triflumizole;
  • Benzimidazoles benomyl, carbendazim, fuberidazole, thiabendazole; - Other: Ethaboxam, Etridiazole, Hymexazole;
  • Pyridines fluazinam, pyrifenox, 3- [5- (4-chlorophenyl) -2,3-dimethylisoxazolidin-3-yl] pyridine; Pyrimidines: bupirimate, cyprodinil, ferimzone, fenarimol, mepanipyrim, nuarimol, pyrimethanil;
  • Morpholines aldimorph, dodemorph, fenpropimorph, tridemorph;
  • Dicarboximides iprodione, procymidone, vinclozolin;
  • acibenzolar-S-methyl anilazine, captan, captafol, dazomet, diclomethine, fenoxanil, folpet, fenpropidin, famoxadone, fenamidone, octhilinone, probenazole, proquinazide, pyroquilone, quinoxyfen, tricyclazole, 5-chloro-7- (4- methyl-piperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1, 2,4] triazolo [1,5-a] pyrimidine, 2-butoxy-6-iodo-3 propyl-chromen-4-one, 3- (3-bromo-6-fluoro-2-methyl-indole-1-sulfonyl) - [1, 2,4] triazole-1-sulfonic acid dimethylamide;
  • guanidines dodine, iminoctadine, guazatine
  • Organometallic compounds fentin salts
  • Sulfur-containing heterocyclyl compounds isoprothiolanes, dithianone
  • Organophosphorus compounds edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, pyrazophos, tolclofos-methyl, phosphorous acid and their salts;
  • Organochlorine compounds thiophanates methyl, chlorothalonil, dichlofluanid, tolylfluanid, flusulfamides, phthalides, hexachlorobenzene, pencycuron, quintozene; Nitrophenyl derivatives: binapacryl, dinocap, dinobuton;
  • Inorganic active substances Bordeaux broth, copper acetate, copper hydroxide, copper oxychloride, basic copper sulphate, sulfur; Other: Spiroxamine, Cyflufenamid, Cymoxanil, Metrafenone.
  • the present invention relates to the pharmaceutical use of the compounds of the formula (I) according to the invention and / or the pharmaceutically acceptable salts thereof, in particular their use for the treatment of tumors in mammals, such as in humans.
  • the active compounds were prepared separately as a stock solution with 25 mg of 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 the volume ratio solvent Emulsifier from 99 to 1 ad 10 ml was filled. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the active ingredient concentration given below.
  • Uniperol® EL wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • Paprika seedlings of the cultivar "Neusiedler Ideal Elite” were sprayed to drip point with an aqueous suspension in the concentration of active compound stated below, after 2-3 leaves had developed well.
  • 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 placed in a climatic chamber at 22 to 24 ° C, darkness and high humidity. After 5 days, the extent of fungal attack on the leaves could be determined visually in%.
  • the leaf areas treated with an application rate of 250 mg / l of the compounds C-1 or C-5 of Table C showed an infection of at most 30%, whereas the untreated leaf areas were 90% infected.
  • the active ingredients were formulated separately as stock solution with a concentration of 10,000 ppm in DMSO.
  • the stock solution is pipetted into a microtiter plate (MTP) and diluted with an aqueous malt-based mushroom nutrient medium to the stated active substance concentration. This was followed by the addition of an aqueous spore suspension of Pyricularia oryzae.
  • MTP microtiter plate
  • the plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. With an absorbance photometer, the MTP's were measured at 405 nm on the 7th day after inoculation.
  • compounds C-4, C-8, C-9, C-10, C-11, C-12, C-15 and C-16 resulted in maximum relative growth of 2%.
  • the stock solution is pipetted into a microtiter plate (MTP) and diluted with an aqueous malt-based mushroom nutrient medium to the stated active substance concentration. This was followed by the addition of an aqueous spore suspension of Septoria tritici.
  • MTP microtiter plate
  • the plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. With an absorbance photometer, the MTP's were measured at 405 nm on the 7th day after inoculation. The measured parameters were compared with the growth of the drug-free control variant (100%) and the fungus-free and drug-free blank to determine the relative growth in% of the pathogens in the individual drugs.
  • the stock solution is pipetted into a microtiter plate (MTP) and diluted with an aqueous malt-based mushroom nutrient medium to the stated active substance concentration. This was followed by the addition of an aqueous spore suspension of Botrytis cinerea.
  • MTP microtiter plate
  • the plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. With an absorbance photometer, the MTP's were measured at 405 nm on the 7th day after inoculation. The measured parameters were compared with the growth of the drug-free control variant and the fungus- and drug-free blank to determine the relative growth in% of the pathogens in the individual drugs.
  • compound C-15 resulted in a relative growth of 1%.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
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  • Nitrogen Condensed Heterocyclic Rings (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne des composés 7-amino-6-hétéroaryl-1,2,4-triazolo[1,5-a]pyrimidine représentés par la formule (I) dans laquelle les substituants Het, R1 et X ont les significations données dans le descriptif.
PCT/EP2006/063964 2005-07-13 2006-07-06 Composes 7-amino-6-heteroaryl-1,2,4-triazolo[1,5-a]pyrimidine et utilisation dans la lutte contre des champignons parasites WO2007023020A1 (fr)

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DE102005033145 2005-07-13

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WO (1) WO2007023020A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007101870A1 (fr) * 2006-03-08 2007-09-13 Basf Se Triazolopyrimidines substituées, procédés de production associés et leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant
WO2008151735A2 (fr) * 2007-06-13 2008-12-18 Bayer Cropscience Ag Dérivés d'acide hétérocyclyl-carboxylique à substitution hétérocyclique

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0613900A1 (fr) * 1993-03-04 1994-09-07 Shell Internationale Researchmaatschappij B.V. Dérivés de triazolopyrimidines ayant des activités fongicides
WO2004011467A1 (fr) * 2002-07-29 2004-02-05 Hokko Chemical Industry Co., Ltd. Derives de triazolopyrimidine et fongicides utilises dans l'agriculture et l'horticulture
WO2004113342A1 (fr) * 2003-06-25 2004-12-29 Bayer Cropscience Aktiengesellschaft Triazolopyrimidines

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0613900A1 (fr) * 1993-03-04 1994-09-07 Shell Internationale Researchmaatschappij B.V. Dérivés de triazolopyrimidines ayant des activités fongicides
WO2004011467A1 (fr) * 2002-07-29 2004-02-05 Hokko Chemical Industry Co., Ltd. Derives de triazolopyrimidine et fongicides utilises dans l'agriculture et l'horticulture
WO2004113342A1 (fr) * 2003-06-25 2004-12-29 Bayer Cropscience Aktiengesellschaft Triazolopyrimidines

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007101870A1 (fr) * 2006-03-08 2007-09-13 Basf Se Triazolopyrimidines substituées, procédés de production associés et leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant
WO2008151735A2 (fr) * 2007-06-13 2008-12-18 Bayer Cropscience Ag Dérivés d'acide hétérocyclyl-carboxylique à substitution hétérocyclique
EP2014661A1 (fr) * 2007-06-13 2009-01-14 Bayer CropScience AG Dérivés d'acides d'hétérocyclyle-carbonique substitués hétéroclites
WO2008151735A3 (fr) * 2007-06-13 2009-07-02 Bayer Cropscience Ag Dérivés d'acide hétérocyclyl-carboxylique à substitution hétérocyclique

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PE20070470A1 (es) 2007-06-08
AR057457A1 (es) 2007-12-05
UY29670A1 (es) 2007-02-28
TW200745115A (en) 2007-12-16
GT200600310A (es) 2006-12-13

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