EP1694682A1 - 7-amino-5-halopyrazolopyrimidine a action fongicide - Google Patents

7-amino-5-halopyrazolopyrimidine a action fongicide

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Publication number
EP1694682A1
EP1694682A1 EP04803616A EP04803616A EP1694682A1 EP 1694682 A1 EP1694682 A1 EP 1694682A1 EP 04803616 A EP04803616 A EP 04803616A EP 04803616 A EP04803616 A EP 04803616A EP 1694682 A1 EP1694682 A1 EP 1694682A1
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EP
European Patent Office
Prior art keywords
carbon atoms
formula
alkyl
chlorine
fluorine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP04803616A
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German (de)
English (en)
Inventor
Olaf Gebauer
Ulrich Heinemann
Stefan Herrmann
Herbert Gayer
Jörg Nico Greul
Stefan Hillebrand
Hans-Ludwig Elbe
Ronald Ebbert
Ulrike Wachendorff-Neumann
Peter Dahmen
Karl-Heinz Kuck
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Bayer CropScience AG
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Bayer CropScience AG
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Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1694682A1 publication Critical patent/EP1694682A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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 invention relates to pyrazolopyrimidines, several processes for their preparation and their use for controlling unwanted microorganisms.
  • Rl represents optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl or optionally substituted heterocyclyl,
  • R 2 represents hydrogen or alkyl
  • Rl and R 2 together with the nitrogen atom to which they are attached represent an optionally substituted heterocyclic ring
  • R 3 represents hydrogen, halogen, optionally substituted alkyl or optionally substituted cycloalkyl
  • R 4 represents halogen, cyano, nitro, alkyl, hydroxyalkyl, alkoxyalkyl, haloalkyl, cycloalkyl, formyl, thiocarbamoyl, alkoxycarbonyl, alkylcarbonyl, benzylcarbonyl, cycloalkylcarbonyl, hydroxyiminoalkyl, alkoximinoalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl or alkylaminocarbonyl, Hal stands for halogen and
  • R 5 represents alkyl, haloalkyl, alkenyl, haloalkenyl, cycloalkyl, cycloalkyl, cycloalkenyl substituted by halogen or alkyl or cycloalkenyl substituted by halogen or alkyl,
  • R 3 , R 5 and shark have the meanings given above,
  • R 6 represents halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, formyl, thiocarbamoyl, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl or alkylaminocarbonyl and Y * represents halogen, with amines of the formula
  • R * and R 2 have the meanings given above, if appropriate in the presence of a diluent, if appropriate in the presence of a catalyst and if appropriate in the presence of an acid acceptor,
  • Rl, R 2 , R 3 , R 5 and Hai have the meanings given above, either ⁇ ) with diisobutyl aluminum hydride in the presence of aqueous ammonium chloride solution and in the presence of an organic diluent, or ß) with Grignard compounds of the formula
  • R7 represents alkyl, benzyl or cycloalkyl
  • X represents chlorine, bromine or iodine, in the presence of a diluent and, if appropriate, in the presence of a catalyst,
  • Rl, R 2 , ⁇ ?, R 5 and Hai have the meanings given above and R ⁇ represents hydrogen, alkyl, benzyl or cycloalkyl,
  • R represents hydrogen or alkyl, in the presence of a diluent and, if appropriate, in the presence of a catalyst, the amino compounds of the formula (V) also being able to be used in the form of their acid addition salts,
  • R 1 , R 2 , R 3 , R 5 , R 8 and shark have the meanings given above, with alkylating agents of the formula R ⁇ - X 1 (VI) in which
  • R 10 represents alkyl
  • X 1 represents chlorine, bromine, iodine or the radical R 10 O-SO 2 -O-, if appropriate in the presence of a base and in the presence of a diluent, or
  • R1, R 2 , R 3 , R 5 and Hai have the meanings given above, with acid halides of the formula R 11 CX 2 (VHI) in which
  • R * * represents alkyl, benzyl or cycloalkyl
  • X 2 represents chlorine or bromine, or with acid anhydrides of the formula
  • R 12 represents alkyl
  • the pyrazolopyrimidines of the formula (I) are very suitable for controlling unwanted microorganisms. Above all, they show a strong fungicidal activity and can be used both in crop protection and in material protection. Surprisingly, the pyrazolopyrimidines of the formula (I) according to the invention have a significantly better microbicidal activity than the constitutionally most similar, previously known substances of the same activity.
  • the compounds according to the invention can optionally be present as mixtures of various possible isomeric forms, in particular of stereoisomers, such as E and Z, threo and erythro and optical isomers, but optionally also in the form of tautomers. If R 5 is unequally substituted on both atoms which are adjacent to the binding site, the compounds in question can exist in a special form of stereoisomerism, namely as atropisomers.
  • the pyrazolopyrimidines according to the invention are generally defined by the formula (I).
  • Preferred substances of the formula (I) are those in which
  • Rl stands for alkyl with 1 to 6 carbon atoms, which can be substituted one to five times, in the same way or differently, by halogen, cyano, hydroxy, alkoxy with 1 to 4 carbon atoms and / or cycloalkyl with 3 to 6 carbon atoms, or
  • Rl stands for alkenyl with 2 to 6 carbon atoms, which can be monosubstituted to triple, identical or differently substituted by halogen, cyano, hydroxy, alkoxy with 1 to 4 carbon atoms and / or cycloalkyl with 3 to 6 carbon atoms, or
  • Rl stands for alkynyl with 3 to 6 carbon atoms, which can be substituted once to three times, in the same way or differently, by halogen, cyano, alkoxy with 1 to 4 carbon atoms and / or cycloalkyl with 3 to 6 carbon atoms, or
  • Rl stands for cycloalkyl with 3 to 6 carbon atoms, which can be monosubstituted to trisubstituted, identical or different, by halogen and / or alkyl having 1 to 4 carbon atoms, or
  • R! represents saturated or unsaturated heterocyclyl with 5 or 6 ring members and 1 to 3 heteroatoms, such as nitrogen, oxygen and / or sulfur, where the heterocyclyl can be mono- or disubstituted by halogen, alkyl having 1 to 4 carbon atoms, cyano, nitro and / or cycloalkyl with 3 to 6 carbon atoms,
  • R 2 represents hydrogen or alkyl having 1 to 4 carbon atoms
  • Rl and R 2 together with the nitrogen atom to which they are attached represent a saturated or unsaturated heterocyclic ring with 3 to 6 ring members
  • the Heterocycle can contain a further nitrogen, oxygen or sulfur atom as a ring member and the heterocycle can be substituted up to three times by fluorine, chlorine, bromine, alkyl having 1 to 4 carbon atoms and / or haloalkyl having 1 to 4 carbon atoms and 1 to 9 Fluorine and / or chlorine atoms,
  • R 3 represents hydrogen, fluorine, chlorine, bromine, iodine, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 4 halogen atoms or cycloalkyl having 3 to 6 carbon atoms,
  • R 4 for cyano, fluorine, chlorine, bromine, iodine, nitro, formyl, haloalkyl with 1 to 4 carbon atoms and 1 to 9 fluorine, chlorine and / or bromine atoms, alkyl with 1 to 4 carbon atoms, hydroxyalkyl with 1 to 4 carbon atoms , Alkoxyalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl part, cycloalkyl with 3 to 6 carbon atoms, thiocarbamoyl, alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy part, alkylcarbonyl with 1 to 4 carbon atoms in the alkyl part, benzylcarbonyl, cycloalkylcarbonyl with 3 to 6 carbon atoms in the cycloalkyl part, hydroximinoalkyl with 1 to 4 carbon atoms in the alkyl part, alkoximino
  • R 5 is alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, cycloalkenyl with 3 to 8 carbon atoms, haloalkyl with 1 to 6 carbon atoms and 1 to 5 fluorine, chlorine and / or bromine atoms , Haloalkenyl with 2 to 6 carbon atoms and 1 to 5 fluorine, chlorine and / or bromine atoms, cycloalkyl with 3 to 8 carbon atoms substituted by 1 to 3 fluorine, chlorine and / or bromine atoms or methyl groups or for 1 to 3 fluorine , Chlorine and / or bromine atoms or methyl groups substituted cycloalkenyl having 3 to 8 carbon atoms.
  • R 2 represents hydrogen, methyl, ethyl or propyl, or
  • R * and R 2 together with the nitrogen atom to which they are attached represent pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, 3,6-dihydro-l (2H) -piperidmyl or tetrahydro-l (2H) -pyridazinyl, these radicals can be substituted by 1 to 3 fluorine atoms, 1 to 3 methyl groups and / or trifluoromethyl, or
  • R represents methyl, ethyl, fluorine, chlorine or trifluoromethyl
  • m stands for the numbers 0, 1, 2 or 3, where R "stands for identical or different radicals if m stands for 2 or 3,
  • R '" represents methyl, ethyl, fluorine, chlorine or trifluoromethyl
  • n stands for the numbers 0, 1, 2 or 3, where R '"stands for identical or different radicals if n stands for 2 or 3,
  • R 3 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, triflourmethyl, l-trifluoromethyl-2,2,2-trifluoroethyl or heptafluoroisopropyl,
  • R 4 for cyano, fluorine, chlorine, bromine, iodine, nitro, formyl, trifluoromethyl, difluoromethyl, chloromethyl, methyl, ethyl, cyclopropyl, thiocarbamoyl, methoxycarbonyl, methylcarbonyl, ethylcarbonyl, benzylcarbonyl, cyclopropylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, methoximino methyl , Methylthio, methylsulfinyl, methylsulfonyl, methylaminocarbonyl, hydroxymethyl, hydroxyeth-1-yl, methoxymethyl, ethoxymethyl or 1-methoxy-ethyl,
  • R 5 represents alkyl having 1 to 4 carbon atoms, alkenyl having 2 to 4 carbon atoms, cycloalkyl having 3 to 7 carbon atoms or cycloalkenyl having 3 to 7 carbon atoms, or
  • a very particularly preferred group of pyrazolopyrimidines according to the invention are those compounds of the formula (I) in which
  • R 1 , R 2 , R 4 and shark have the particularly preferred meanings given above, R 3 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, trifluoromethyl or cyclopropyl and
  • R 5 for methyl, ethyl, propyl, isopropyl, n-butyl, i-butyl, sec.-butyl, tert-butyl, alllyl, but-2-en-l-yl, cyclopropyl, cyclopentyl, 2-methylcyclopentyl, cyclohexyl, 2-methylcyclohexyl, cyclopentenyl, 2-methylcyclopentenyl, 2-chlorocyclopentenyl, cyclohexenyl, 2-methylcyclohexenyl, 2-chlorocyclohexenyl, chloromethyl, trifluoromethyl, trifluoroisopropyl, trichlorallyl, 2,2-dichlorocyclopropyl or dichlorocyclohexenyl.
  • radical definitions can be combined with one another in any way.
  • individual definitions can also be omitted.
  • Halogenpyrazolopyrimidine required for carrying out the inventive process (a) as starting materials are generally defined by the formula (D) '.
  • R 3 , R 5 and shark preferably have those meanings which have already been mentioned as preferred for these radicals in connection with the description of the compounds of the formula (I) according to the invention.
  • ⁇ l preferably represents fluorine, chlorine or bromine, particularly preferably fluorine or chlorine.
  • R 6 preferably represents cyano, fluorine, chlorine, bromine, iodine, nitro, haloalkyl with 1 to 4 carbon atoms and 1 to 9 fluorine, chlorine and / or bromine atoms, alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms , Formyl, thiocarbamoyl, alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy part, alkylthio with 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms or for alkylaminocarbonyl with 1 to 4 carbon atoms in the alkyl part.
  • R 6 particularly preferably represents cyano, fluorine, chlorine, bromine, iodine, nitro, trifluoromethyl, difluoromethyl, methyl, ethyl, cyclopropyl, formyl, thiocarbamoyl, methoxycarbonyl, methylthio, methylsulfinyl, methylsulfonyl or methylaminocarbonyl.
  • halopyrazolopyrimidines of the formula (H) can be prepared by e) hydroxy-pyrazolopyrimidines of the formula in which R 3 and R 5 have the meanings given above and
  • R represents halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, thiocarbamoyl, alkoxycarbomyl, alkylthio, alkylsulfinyl, alkylsulfonyl or alkylaminocarbonyl, with halogenating agents, if appropriate in the presence of a diluent, or
  • R 3 and R 5 have the meanings given above, reacted with phosphorus oxychloride in the presence of dimethylformamide and, if appropriate, allowed to after-react with the addition of phosphorus pentachloride.
  • Formula (X) provides a general definition of the hydroxypyrazolopyrimidines required as starting materials when carrying out process (e).
  • R 3 and R 5 preferably have those meanings which have already been mentioned as preferred for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • R preferably represents cyano, fluorine, chlorine, bromine, iodine, nitro, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 9 fluorine, chlorine and / or bromine atoms, cycloalkyl having 3 to 6 carbon atoms, Thiocarbamoyl, alkylcarbonyl with 1 to 4 carbon atoms in the alkoxy part, alkylthio with 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms Substance atoms, alkylsulfonyl with 1 to 4 carbon atoms or for alkylaminocarbonyl with 1 to 4 carbon atoms in the alkyl part.
  • R particularly preferably represents cyano, fluorine, chlorine, bromine, iodine, nitro, trifluoromethyl, difluoromethyl, chloromethyl, methyl, ethyl, cyclopropyl, thiocarbamoyl, methoxycarbonyl, methylthio, methylsulfmyl, methylsulfonyl or methylaminocarbonyl.
  • hydroxy-pyrazolopyrimidines of the formula (X) can be prepared by
  • R 13 represents alkyl having 1 to 4 carbon atoms, with aminopyrazoles of the formula
  • R 3 and R have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Formula (X ⁇ ) provides a general definition of the malonic ester derivatives required as starting materials when carrying out process (g).
  • R 5 preferably has those meanings which have already been mentioned as preferred for this radical in connection with the description of the substances of the formula (I) according to the invention.
  • R 13 preferably represents methyl or ethyl.
  • the malonic ester derivatives of the formula (XU) are known or can be prepared by known methods.
  • Formula (XIII) provides a general definition of the aminopyrazoles required as reaction components when carrying out process (g).
  • R 3 and R preferably have those meanings which have already been mentioned as preferred for these radicals in connection with the description of the substances of the formula (I) according to the invention, or of the hydroxy-pyrazolopyrimidines of the formula (X).
  • aminopyrazoles of the formula (XUI) are known or can be prepared by known methods.
  • Suitable diluents for carrying out process (g) are all inert organic solvents customary for such reactions.
  • Alcohols such as methanol, ethanol, n-propanol, i-propanol, n-butanol and tert-butanol can preferably be used.
  • Suitable acid binders for carrying out process (g) are all inorganic and organic bases customary for such reactions.
  • Tertiary amines such as tributylamine or pyridine can preferably be used. Amine used in excess can also act as a diluent.
  • the temperatures can be varied within a wide range when carrying out the process (g). In general, temperatures between 20 ° C and 200 ° C, preferably between 50 ° C and 180 ° C.
  • Process (f) is suitable for the preparation of halopyrazolopyrimidine of the formula
  • R 3 and R 5 have the meanings given above.
  • Formula (XI) provides a general definition of the hydroxypyrazolopyrimidines required as starting materials when carrying out process (f).
  • R 3 and R 5 have preferably those meanings which have already been mentioned as preferred for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • hydroxy-pyrazolopyrimidines of the formula (XI) can be prepared by process (g).
  • Process (f) is carried out under the conditions of Vilsmeier formylation using phosphorus oxychloride in the presence of dimethylformamide. Phosphorus pentachloride can also be added as a chlorinating agent.
  • reaction temperatures can be varied within a substantial range when carrying out process (f). In general, temperatures between -10 ° C and + 150 ° C, preferably between 0 ° C and 120 ° C.
  • Suitable halogenating agents for carrying out process (e) are all components which are customary for the replacement of hydroxyl groups by halogen.
  • Phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, phosphorus oxychloride, thionyl chloride, thionyl bromide or mixtures thereof are preferably usable.
  • the corresponding fluorine compounds of the formula (H) can be prepared from the chlorine or bromine compounds by reaction with potassium fluoride.
  • Suitable solvents for carrying out process (e) are all solvents customary for such halogenations.
  • Halogenated aliphatic or aromatic hydrocarbons such as chlorobenzene, can preferably be used.
  • the halogenating agent itself e.g. Phosphorus oxychloride or a mixture of halogenating agents act.
  • the temperatures can also be varied within a substantial range when carrying out process (e). In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
  • hydroxy-pyrazolopyrimidine of the formula (XI) is generally reacted with an excess of halogenating agent. The processing takes place according to usual methods.
  • Formula (TU) provides a general definition of the amines required as starting materials for carrying out process (a) according to the invention.
  • R 1 and R 2 preferably have those meanings which have already been given as preferred for R 1 and R 2 in connection with the description of the compounds of the formula (I) according to the invention.
  • the amines of the formula (HI) are known or can be prepared by known methods.
  • Suitable diluents for carrying out process (a) according to the invention are all customary inert organic solvents.
  • Halogenated hydrocarbons such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane, can preferably be used;
  • Ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole;
  • Nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile;
  • Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N
  • Suitable acid acceptors for carrying out process (a) according to the invention are all inorganic or organic bases customary for such reactions.
  • Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates such as, for example, sodium hydride, sodium amide, lithium diisopropylamide, sodium methylate, sodium ethylate, potassium tert-butoxide, are preferably usable , Sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate and sodium hydrogen carbonate, and also ammonium compounds such as ammonium hydroxide, ammonium acetate and ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N , N-dimethylbenzylamine, pyridine, N-methyl
  • Suitable catalysts for carrying out process (a) according to the invention are all reaction accelerators customary for such reactions. Fluorides such as sodium fluoride, potassium fluoride or ammonium fluoride can preferably be used.
  • the reaction temperatures can be varied within a substantial range when carrying out process (a) according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably at temperatures between 0 ° C and 80 ° C.
  • Formula (Ia) provides a general definition of the pyrazolopyrimidines required as starting materials when carrying out process (b) according to the invention.
  • R *, R 2 , R 3 , R 5 and shark preferably have those meanings which have already been mentioned as preferred for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • the pyrazolopyrimidines of the formula (Ia) are substances according to the invention which can be prepared by process (a) according to the invention.
  • Suitable diluents for carrying out the process (b, variant ⁇ ) are all customary inert, organic solvents.
  • Aliphatic or aromatic, optionally halogenated hydrocarbons, such as toluene, dichloromethane, chloroform or carbon tetrachloride, can preferably be used.
  • reaction temperatures can be varied within a certain range. In general, temperatures between -80 ° C and + 20 ° C, preferably between -60 ° C and + 10 ° C.
  • pyrazolopyrimidine of the formula (Ia) is generally employed in an equivalent amount or also in excess, preferably 1.1 to 1.2 mol, of di-isobutyl aluminum hydride and then add an excess of aqueous ammonium chloride solution.
  • the processing takes place according to usual methods. In general, the procedure is carried out by acidifying the reaction mixture, separating the organic phase, extracting the aqueous phase with a water-immiscible organic solvent, washing the combined organic phases, drying and concentrating under reduced pressure.
  • Formula (IV) provides a general definition of the Grignard compounds required as reaction components when carrying out process (b, variant ⁇ ) according to the invention.
  • R 7 preferably represents alkyl having 1 to 4 carbon atoms, benzyl or Cycloalkyl of 3 to 6 carbon atoms.
  • R 7 particularly preferably represents methyl, ethyl, cyclopropyl, cyclopentyl, cyclohexyl or benzyl.
  • X also preferably represents chlorine, bromine or iodine.
  • Suitable catalysts for carrying out the process according to the invention are all reaction accelerators customary for such Grignard reactions. Examples include potassium iodide and iodine.
  • Suitable diluents for carrying out the process (b, variant ⁇ ) according to the invention are all inert organic solvents which are customary for such reactions.
  • Ethers such as diethyl ether, dioxane or tetrahydrofuran, and also aromatic hydrocarbons, such as toluene, and also mixtures of ethers and aromatic hydrocarbons, such as toluene / tetrahydrofuran, can preferably be used.
  • reaction temperatures can be varied within a certain range when carrying out the process (b, variant ⁇ ). In general, temperatures between -20 ° C and + 100 ° C, preferably between 0 ° C and 80 ° C.
  • Formula (Ib) provides a general definition of the pyrazolopyrimidines required as starting materials when carrying out process (c) according to the invention.
  • R% RR ⁇ , R 5 and shark preferably have those meanings which have already been mentioned as preferred for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • R 8 preferably represents hydrogen or alkyl having 1 to 4 carbon atoms, benzyl or cycloalkyl having 3 to 6 carbon atoms.
  • R ° * is particularly preferably hydrogen, methyl, ethyl, benzyl, cyclopropyl, cyclopentyl or cyclohexyl.
  • the pyrazolopyrimidines of the formula (Ib) are substances according to the invention which can be prepared by process (b) according to the invention.
  • Formula (V) provides a general definition of the amino compounds required as reaction components when carrying out process (c, variant ⁇ ) according to the invention.
  • R 9 preferably represents hydrogen or alkyl having 1 to 4 carbon atoms, particularly preferably hydrogen, methyl or ethyl.
  • acid addition salts preferably hydrogen chloride addition salts of amino compounds of the formula (V).
  • Suitable diluents for carrying out the process (c, variant ⁇ ) are all customary inert, organic solvents. Alcohols such as methanol, ethanol, n-propanol or isopropanol can preferably be used.
  • Suitable catalysts for carrying out the process (c, variant ⁇ ) according to the invention are all reaction accelerators customary for such reactions.
  • Acidic or basic catalysts such as e.g. the weakly basic ion exchanger commercially available under the name Amberlyst A-21®.
  • reaction temperatures can be varied within a certain range when carrying out the process according to the invention (c, variant ⁇ ). In general, temperatures between 0 ° C and 80 ° C, preferably between 10 ° C and 60 ° C.
  • pyrazolopyrimidine of the formula (Ib) is generally employed in an equivalent amount or in excess, preferably between 1.1 and 1.5 mol, of the amino compound of the Formula (V) or an acid addition salt thereof.
  • the processing takes place according to usual methods. The general procedure is to filter the reaction mixture, if appropriate, then to concentrate and to purify it.
  • Formula (VI) provides a general definition of the alkylating agents required as reaction components when carrying out the process (c, variant ⁇ ).
  • R 10 preferably represents alkyl having 1 to 4 carbon atoms, particularly preferably methyl or ethyl
  • X 1 preferably represents chlorine, bromine, iodine or the radical R 10 -O-SO 2 -O, where R 10 is the same as above has given meanings.
  • the alkylating agents of the formula (VI) are known or can be prepared by known methods.
  • di-isobutylaluminum hydride is used as a reducing agent in the first stage when carrying out the process (c, variant ⁇ ) in the first stage, the procedure is expediently carried out under the conditions already described in connection with the description of the process (b, variant ⁇ ) were mentioned.
  • sodium borohydride is used as the reducing agent in carrying out the process (c, variant ⁇ ) in the first stage, alcohols, preferably methanol, ethanol or isopropanol, are generally used as diluents.
  • reaction temperatures can be varied within a certain range. In general, temperatures between 0 ° C and 70 ° C, preferably between 0 ° C and 50 ° C.
  • all customary acid binders are suitable as bases.
  • Alkali metal hydrides, alcoholates and carbonates such as sodium hydride, sodium methylate, potassium tert-butoxide, sodium carbonate, potassium carbonate or lithium carbonate, can preferably be used.
  • Suitable diluents for carrying out the second stage of the process (c, variant ⁇ ) are all customary inert organic solvents.
  • Ethers such as dioxane or tetrahydrofuran, and also nitriles, such as acetonitrile, are preferably usable.
  • the temperatures can be varied within a substantial range. In general, temperatures between 0 ° C and 100 ° C, preferably between 20 ° C and 80 ° C.
  • Formula (VII) provides a general definition of the pyrazolopyrimidines required as starting materials when carrying out process (d) according to the invention.
  • R *, R R3, R5 and shark preferably have those meanings which have already been mentioned as preferred for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • the pyrazolopyrimidines of the formula (VE) are known or can be prepared by known methods.
  • the formulas (NIH) and (IX) generally define the acid halides and acid anhydrides required as reaction components when carrying out process (d) according to the invention.
  • R ⁇ * is preferably alkyl having 1 to 4 carbon atoms, benzyl or cycloalkyl having 3 to 6 carbon atoms.
  • X ⁇ preferably represents chlorine or bromine.
  • R * 1 represents methyl, ethyl, propyl, benzyl, cyclopropyl, cyclopentyl or cyclohexyl and
  • X 2 represents chlorine or bromine.
  • R 2 preferably represents alkyl having 1 to 4 carbon atoms, particularly preferably methyl, ethyl or propyl.
  • Suitable catalysts for carrying out process (d) according to the invention are all reaction accelerators which can usually be used for Friedel-Crafts reactions.
  • Lewis acids such as aluminum trichloride, aluminum tribromide and iron (H [) chloride can preferably be used.
  • Suitable diluents for carrying out process (d) according to the invention are all inert organic solvents which are customary for such Friedel-Crafts reactions.
  • Ethers such as diethyl ether, methyl tert-butyl ether, dioxane and tetrahydrofuran, and also carbon disulphide can preferably be used.
  • reaction temperatures can be varied within a certain range when carrying out process (d) according to the invention. In general, temperatures between -10 ° C and + 100 ° C, preferably between 0 ° C and 80 ° C.
  • 1 to 5 mol, preferably 1 to 2 mol of acid halide of the formula (VIII) and 1.1 to 5 mol, preferably 1, are generally employed per mol of pyrazolopyrimidine of the formula (VII) , 1 to 3 mol of catalyst, or 1 to 5 mol, preferably 1 to 2 mol of acid anhydride of the formula (IX) and 2.1 to 6 mol, preferably 2.1 to 4 mol of catalyst.
  • the procedure is generally such that the reaction components are first combined at a low temperature and gradually heated to the reflux temperature after the initially violent reaction has subsided.
  • the substances according to the invention have a strong microbicidal action and can be used to control undesired microorganisms, such as fungi and bacteria, in crop protection and in material protection.
  • Fungicides can be used to protect plants against Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • Xanthomonas species such as, for example, Xanthomonas campestris pv. Oryzae;
  • Pseudomonas species such as, for example, Pseudomonas syringae pv. Lachrymans;
  • Erwinia species such as, for example, Erwinia amylovora
  • Pythium species such as, for example, Pythium ultimum
  • Phytophthora species such as, for example, Phytophthora infestans
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or
  • Plasmopara species such as, for example, Plasmopara viticola
  • Bremia species such as, for example, Bremia lactucae
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae;
  • Erysiphe species such as, for example, Erysiphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca fuliginea
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Venturia species such as, for example, Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Cochliobolus species such as, for example, Cochliobolus sativus
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium); Uromyces species, such as, for example, Uromyces appendiculatus;
  • Puccinia species such as, for example, Puccinia recondita
  • Sclerotinia species such as, for example, Sclerotinia sclerotiorum
  • Tilletia species such as, for example, Tilletia caries; Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae; Pellicularia species, such as, for example, Pellicularia sasakii; Pyricularia species, such as, for example, Pyricularia oryzae; Fusarium species, such as, for example, Fusarium culmorum; Botrytis species, such as, for example, Botrytis cinerea; Septoria species, such as, for example, Septoria nodorum; Leptosphaeria species, such as, for example, Leptosphaeria nodorum; Cercospora species, such as, for example, Cercospora canescens; Alternaria species, such as, for example, Alternaria brassicae; Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides.
  • the active compounds according to the invention also have a very good strengthening effect in plants. They are therefore suitable for mobilizing the plant's own defenses against attack by unwanted microorganisms.
  • Plant-strengthening (resistance-inducing) substances are to be understood in the present context as substances which are able to stimulate the defense system of plants in such a way that the treated plants develop extensive resistance to these microorganisms when subsequently inoculated with undesired microorganisms.
  • Undesired microorganisms are to be understood in the present case as phytopathogenic fungi, bacteria and viruses.
  • the substances according to the invention can thus be used to protect plants against attack by the pests mentioned within a certain period of time after the treatment.
  • the period within which protection is brought about generally extends from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the active compounds.
  • the active compounds according to the invention can be used with particularly good success for combating cereal diseases, for example against Erysiphe species, for diseases in wine, fruit and vegetable cultivation, for example against Botrytis, Venturia, Sphaerotheca and Podosphaera species ,
  • the active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance. If appropriate, the active compounds according to the invention can also be used in certain concentrations and application rates as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of further active compounds.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of the plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space using the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular in the case of seeds, furthermore by coating in one or more layers.
  • the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
  • technical materials are to be understood as non-living materials that have been prepared for use in technology.
  • technical materials which are to be protected against microbial change or destruction by active substances according to the invention can be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which can be attacked or decomposed by microorganisms .
  • parts of production systems for example cooling water circuits, are also mentioned which can be impaired by the multiplication of microorganisms.
  • adhesives, glues, papers and Cartons, leather, wood, paints, cooling lubricants and heat transfer liquids called, particularly preferably wood.
  • Bacteria, fungi, yeasts, algae and slime organisms may be mentioned as microorganisms which can cause degradation or change in the technical materials.
  • the active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • Microorganisms of the following genera may be mentioned, for example:
  • Alternaria such as Alternaria tenuis, Aspergillus, such as Aspergillus niger,
  • Chaetomium like Chaetomium globosum
  • Coniophora such as Coniophora puetana
  • Lentinus such as Lentinus tigrinus
  • Penicillium such as Penicillium glaucum
  • Polyporus such as Polyporus versicolor
  • Aureobasidium such as Aureobasidium pullulans
  • Sclerophoma such as Sclerophoma pityophila
  • Trichoderma like Trichoderma viride
  • Escherichia such as Escherichia coli
  • Pseudomonas such as Pseudomonas aeruginosa
  • Staphylococcus such as Staphylococcus aureus.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV -Cold and warm mist formulations.
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic carbons Hydrogen, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water.
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • Solid carrier materials come into question: for example natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates.
  • Solid carriers for granules are possible: e.g.
  • emulsifiers and / or foaming agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • Possible dispersants are: eg lignin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to to broaden the spectrum of activity or to prevent the development of resistance.
  • fungicides bactericides
  • acaricides nematicides or insecticides
  • synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • 2-phenylphenol 8-hydroxyquinoline sulfates; Acibenzolar-S-methyl; Aldimo h; amidoflumet; Ampropylfos; Ampropylfos-potassium; andoprim; anilazine; azaconazole; azoxystrobin; benalaxyl;
  • Benalaxyl-M Benodanil; benomyl; Benthiavalicarb-isopropyl; Benzamacril; Benzamacril-isobutyl; bilanafos; binapacryl; biphenyl; bitertanol; Blasticidin-S; boscalid; bromuconazole; Bupirimate;
  • Buthiobate butylamine; Calcium polysulfide; capsimycin; captafol; captan; carbendazim; carboxin;
  • cyprofuram Dagger G; debacarb; dichlofluanid; dichlone; dichlorophen; diclocymet; Diclomezine; dicloran; diethofencarb; Difenoconazole; diflumetorim; dimethirimol; Dimethomo ⁇ h; Dimoxystrobin; diniconazole; Diniconazole-M; dinocap; diphenylamines; Dipyrithione; Ditalimfos; dithianon;
  • fenamidone Fenapanil; fenarimol; Fenbuconazole; fenfuram; fenhexamid; Fenitropan; fenoxanil;
  • fenpiclonil fenpropidin; fenpropimorph; ferbam; fluazinam; Flubenzimine; fludioxonil; flumetover; Flumo ⁇ h; fluoromides; fluoxastrobin; fluquinconazole; Flu ⁇ rimidol; flusilazole; flusulfamide; Flutolanil; flutriafol; folpet; Fosetyl-Al; Fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; Furcarbanil;
  • iprovalicarb Irumamycin; isoprothiolane; Isovaledione; kasugamycin; Kresoxim-methyl; mancozeb; maneb; Meferimzone; mepanipyrim; mepronil; metalaxyl; Metalaxyl-M; metconazole; Methasulfocarb; Methfuroxam; metiram; metominostrobin; Metsulfovax; mildiomycin; myclobutanil;
  • propineb proquinazid; prothioconazole; pyraclostrobin; Pyrazohos; pyrifenox; pyrimethanil; Pyroquilon; Pyroxyfur; Pyrrolnitrine; Quinconazole; quinoxyfen; quintozene; Simeconazole; spiroxamine;
  • copper salts and preparations such as Bordeaux mixture; Copper hydroxide, copper naphthenate; copper oxychloride; Copper sulfate; Cufraneb; copper; mancopper; Kupferoxin.
  • Insecticides / acaricides / nematicides 1. Acetylcholinesterase (AChE) inhibitors
  • Carbamates e.g. Alanycarb, Aldicarb, Aldoxycarb, Allyxycarb, Aminocarb, Azamethiphos, Bendiocarb, Benfuracarb, Bufencarb, Butacarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Chloethocarb, Coumaphos, Cyanophosuco, Dimo Carbos, Cyanophosphos, Cyanophosphos, Cyanophosphos, Cyanophosphos, Cyanophospho Fenothiocarb, Formetanate, Furathiocarb, Isoprocarb, Metam-sodium, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Promecarb, Propoxur, LThiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC, X
  • organophosphates for example acephate, azamethiphos, azinphos (-methyl, -ethyl), Bromophos- ethyl, Bromfenvinfos (-methyl), Butathiofos, cadusafos, carbophenothion, chlorethoxyfos, chlorfenvinphos, chlormephos, Chlo ⁇ yrifos (-methyl ⁇ ethyl), coumaphos, Cyanofenphos, Cyanophos , Chlorfenvinphos, Demeton-S-methyl, Demeton-S-methylsulphone, Dialifos, Diazinon, Dichlofenthion, Dichlorvos / DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Dioxabenzofos, Disulfoton, EPN, Ethion, Ethoprophos, Etrimfothion, Fennophos, Fph ,
  • Pyrethroids e.g. acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, cis-chlorothrinet -Resmethrin, cis-permethrin, clocythrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, DDT, deltamethrin, empenthrin (lR-isomer), esfenxerate, fenpathrhrine, , Fenpyrithr
  • Chloronicotinyls / neonicotinoids e.g. acetamiprid, clothianidin, dinote Namean, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam
  • GABA-controlled chloride channel antagonists 5.1 Cyclodienes Organochlorine (e.g. Camphechlor, Chlordane, Endosulfan, Gamma-HCH, HCH, Heptachlor, Lindane, Methoxychlor
  • Fiprole e.g. Acetoprole, Ethiprole, Fipronil, Vaniliprole
  • Mectins e.g. abamectin, avermectin, emamectin, emamectin-benzoate, ivermectin, mitemectin, milbemycin
  • Diacylhydrazine e.g. chromafenozide, halofenozide, methoxyfenozide, tebufenozide
  • Benzoyl ureas e.g. bistrifluron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron,
  • organotins e.g. azocyclotin, cyhexatin, fenbutatin-oxide
  • METI's e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad
  • Microbial disruptors of the insect intestinal membrane strains of Bacillus thuringiensis 16. Inhibitors of fat synthesis
  • tetronic acids e.g. spirodiclofen, spiromesifen
  • 16.2 tetramic acids [e.g. 3- (2,5-Dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl carbonate (alias: Carbonic acid, 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl ester, CAS Reg.-No .: 382608-10-8) and Carbonic acid, cis-3- ( 2,5-dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl ester (CAS Reg.No .: 203313-25-1)]
  • Carboxamides e.g. flonicamide
  • Octopaminergic agonists e.g. Amitraz
  • Phthalamides e.g. N 2 - [l, l-dimethyl-2- (methylsulfonyl) ethyl] -3-iodo-N 1 - [2-methyl-4- [l, 2,2,2-tetrafluoro-l- (trifluoromethyl) ethyl] phenyl] -l, 2-benzenedicarboxamide (CAS-Reg.-No .: 272451-65-7), Fluben-diamide)
  • mite growth inhibitors e.g. clofentezine, etoxazole, hexythiazox
  • the compounds of the formula (I) according to the invention also have very good antimycotic effects. They have a very broad antimycotic activity spectrum in particular against dermatophytes and yeasts, molds and diphasic fungi (for example against Candida species such as Candida albicans, Candida glabrata), and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, microsporon species such as microsporon canis and audouinii.
  • Candida species such as Candida albicans, Candida glabrata
  • Epidermophyton floccosum Aspergillus species such as Aspergillus niger and Aspergillus fumigatus
  • Trichophyton species such as Trichophyton mentagrophytes
  • microsporon species such as microsporon canis and audouinii.
  • the list of these fungi is in no way
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient into the soil itself. The seeds of the plants can also be treated.
  • the application rates can be varied within a relatively wide range, depending on the type of application.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.
  • the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • all plants and their parts can be treated.
  • wild plant species or plant species and their parts obtained by conventional biological breeding methods are treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods if appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated.
  • the term “parts” or “parts of plants” or “parts of plants” was explained above.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with new properties (“traits”) which have been cultivated by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, breeds, bio- and genotypes.
  • the treatment according to the invention can also cause superadditive (“synergistic”) effects.
  • superadditive for example, reduced application rates and / or widening of the activity spectrum and / or one Strengthening the effect of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the effects that are actually to be expected.
  • the preferred transgenic plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous valuable properties (“traits”). Examples of such properties are better plant growth, Increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher storability and / or workability of the Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased tolerance of Plants against certain herbicidal agents.
  • transgenic plants are the important cultivated plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes , Cotton, tobacco and rapeseed are highlighted.
  • the traits are particularly emphasized as the increased defense of the plants against insects, arachnids, namatodes and snails by toxins that arise in the plants, especially those that are caused by the genetic material from Bacillus thuringiensis (eg by the genes Cry ⁇ A (a) , CryIA (b), Cry ⁇ A (c), CryHA, CryHIA, CryHIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
  • Bacillus thuringiensis eg by the genes Cry ⁇ A (a) , CryIA (b), Cry ⁇ A (c), CryHA, CryHIA, CryHIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations
  • Trans are also used the increased defense of plants against fungi, bacteria and viruses through systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins are particularly emphasized.
  • SAR systemic acquired resistance
  • the properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example hnidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example “PAT” gene).
  • the desired properties (“traits”) in each case. conferring genes can also occur in combinations with one another in the transgenic plants.
  • Bt plants are maize varieties, cotton varieties, soy varieties and potato varieties that are marketed under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucoton® (cotton) and NewLeaf® (potato).
  • herbicide-tolerant plants are maize varieties, cotton varieties and soy varieties that are marketed under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, e.g.
  • rapeseed rapeseed
  • IMI® tolerance to Imidazolinone
  • STS® tolerance to sulfonylureas such as maize
  • the herbicide-resistant plants include the varieties sold under the name Clearfield® (eg maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
  • the plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active compound mixtures according to the invention.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants.
  • Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants.
  • Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • the compounds of the formula (I) according to the invention are furthermore suitable for suppressing the growth of tumor cells in humans and mammals. This is based on an interaction of the compounds according to the invention with tubulin and microtubules and by promoting microtubule polymerization.
  • an effective amount of one or more compounds of formula (I) or pharmaceutically acceptable salts thereof can be administered.
  • a mixture of 15 g of 5,7-dihydroxy-6- (sec-butyl) pyrazolo [l, 5-a] pyrimidine and 35 ml of phosphorus oxychloride is heated under reflux for one hour and then cooled to 0 ° C.
  • the reaction mixture is then added dropwise with 10.6 g of dimethylformamide, with stirring, in such a way that the temperature of the mixture does not exceed 20 ° C.
  • the addition is complete, the mixture is first stirred at room temperature for 1 hour and then heated under reflux for 2 hours. The mixture is then concentrated under reduced pressure. The remaining residue is mixed with ice water stirred, and the resulting mixture is extracted with ethyl acetate.
  • Emulsifier 1.0 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in the greenhouse at approximately 21.degree. C. and a relative atmospheric humidity of approximately 90%.
  • Botrytis test (bean) / protective
  • Solvent 24.5 parts by weight of acetone, 24.5 parts by weight of dimethylacetamide
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Emulsifier 1.0 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Example 3 the compound according to the invention listed in Example 3 showed an efficiency of over 80% at a rate of 750 g / ha.

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Abstract

L'invention concerne de nouvelles pyrazolopyrimidines de formule (I), dans laquelle R1, R2, R3, R4, R5 et Hal ont les significations indiquées dans la description, plusieurs procédés pour réaliser ces substances et leur utilisation pour lutter contre des micro-organismes indésirables.
EP04803616A 2003-12-10 2004-12-08 7-amino-5-halopyrazolopyrimidine a action fongicide Withdrawn EP1694682A1 (fr)

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DE10357569A DE10357569A1 (de) 2003-12-10 2003-12-10 Pyrazolopyrimidine
PCT/EP2004/013939 WO2005056557A1 (fr) 2003-12-10 2004-12-08 7-amino-5-halopyrazolopyrimidine a action fongicide

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DE102005007534A1 (de) * 2005-02-17 2006-08-31 Bayer Cropscience Ag Pyrazolopyrimidine
WO2007101804A1 (fr) * 2006-03-07 2007-09-13 Basf Se Pyrazolopyrimidines substituées, procédés de production associés et leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant
SI2013280T1 (sl) * 2006-05-01 2010-02-26 Bnt Force Biodegradable Polyme Novi biorazgradljivi polimerni sestavek, uporaben za pripravo biorazgradljive umetne snovi in postopek za pripravo tega sestavka
DE102006039255A1 (de) * 2006-08-17 2008-02-21 Bayer Cropscience Ag Insektizide heterocyclische Carbonsäurederivate
BR112015022545A2 (pt) * 2013-03-13 2017-07-18 Constellation Pharmaceuticals Inc compostos de pirazolo e os usos disso
CN110016036B (zh) * 2019-05-16 2022-06-03 辽宁大学 吡唑并[1,5-a]嘧啶类化合物及其制备方法和应用

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3130633A1 (de) * 1981-08-01 1983-02-17 Basf Ag, 6700 Ludwigshafen 7-amino-azolo(1,5-a)pyrimidine und diese enthaltende fungizide
DE3338292A1 (de) * 1983-10-21 1985-05-02 Basf Ag, 6700 Ludwigshafen 7-amino-azolo(1,5-a)-pyrimidine und diese enthaltende fungizide
HUP9801135A2 (hu) * 1995-05-09 1998-08-28 Basf Aktiengesellschaft Pirazolo[1,5-a]pirimidinek, eljárás előállításukra és alkalmazásuk
US5817663A (en) * 1996-10-07 1998-10-06 American Cyanamid Company Pentafluorophenylazolopyrimidines
JP2001019693A (ja) * 1999-06-14 2001-01-23 American Cyanamid Co 殺菌・殺カビ性６−フェニル−ピラゾロピリミジン
EA200500719A1 (ru) * 2002-11-07 2005-10-27 Басф Акциенгезельшафт 5-алкил-7-аминотриазолопиримидины, способ и промежуточные продукты для их получения, содержащие их средства, а также их применение для борьбы с фитопатогенными грибами

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2005056557A1 *

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WO2005056557A1 (fr) 2005-06-23
US20080021045A1 (en) 2008-01-24
JP2007516249A (ja) 2007-06-21

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