WO2007116011A2 - Triazolopyrimidines substituées, procédé de fabrication, utilisation dans la lutte contre des champignons parasites et agent contenant ces composés - Google Patents

Triazolopyrimidines substituées, procédé de fabrication, utilisation dans la lutte contre des champignons parasites et agent contenant ces composés Download PDF

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WO2007116011A2
WO2007116011A2 PCT/EP2007/053355 EP2007053355W WO2007116011A2 WO 2007116011 A2 WO2007116011 A2 WO 2007116011A2 EP 2007053355 W EP2007053355 W EP 2007053355W WO 2007116011 A2 WO2007116011 A2 WO 2007116011A2
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alkyl
cio
compounds
formula
alkoxy
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PCT/EP2007/053355
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WO2007116011A3 (fr
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Jochen Dietz
Thomas Grote
Wassilios Grammenos
Bernd Müller
Jan Klaas Lohmann
Jens Renner
Sarah Ulmschneider
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Definitions

  • the present invention relates to compounds of the formula I.
  • X is hydrogen, halogen, hydroxy, cyano, N (A ') A, C 8 alkoxy, Ci-C8-halo-alkoxy, Ci -C8-Al alkylthio, Ci-C8-alkylsulfinyl, Ci-C 8- alkylsulfonyl, C 1 -C 8 -alkyl, d-
  • C 8 haloalkyl C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 kinyl -alkyl, C 2 -C 8 - haloalkynyl, cyano-Ci-C4-alkyl, Ci-C4- alkoxy-Ci-C4-alkyl;
  • Y is C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 3 -C 10 -cycloalkyl, C 3 -C 10 -cycloalkenyl or an imino group; these radicals being able to carry one, two, three or four identical or different groups R a and / or for two substituents bound to the same or adjacent atoms or ring atoms for C 1 -C 6 -alkylene, oxy-C 2 -C 4 -alkylene or oxy- Ci-C3-alkyleneoxy may be, where
  • R a is halogen, cyano, nitro, hydroxy, carboxyl, Ci-C 8 alkyl, Ci-C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 -alkyl kinyl , C 2 -C 8 haloalkynyl, C4-Cio-alkadienyl, C 8 alkoxy, Ci-C 8 haloalkoxy, C 2 -C 8 alkenyloxy, C 2 -C 8 haloalkenyloxy, C3-C 8 - alkynyloxy, C3-C8 haloalkynyloxy, C 3 C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 -CyCIo- alkoxy, C3-C 8 -Halogencyclo
  • R b is halogen, cyano, nitro, hydroxy, mercapto, Ci-C 8 alkyl, C 2 -C 8 alkene yl, C 2 -C 8 kinyl -alkyl, C 4 -Cio-alkadienyl, C 3 -C 8 cycloalkyl, C 3 -C 8 -CyCIo- alkenyl, Cs-Cio-bicycloalkyl, C 8 alkoxy, C 2 -C 8 alkenyloxy, C 2 -C 8 - alkynyloxy, C 3 -C 8 -alkoxy -CyClOaI, C 3 -C 8 -cycloalkenyloxy, Aminothiocar- carbonyl, d-Cs-alkyl-carbonyloxy, Ci-C ⁇ -alkylaminothiocarbonyl, di-Ci- C 8 -alkylaminothiocarbonyl, C 8
  • Ci-Cio-haloalkyl C 2 -Cio-alkenyl, C 2 -Cio-haloalkenyl, C 2 -C 0 - alkynyl, C 2 -C 0 haloalkynyl, C 3 -C 2 cycloalkyl , C 3 -C 2 halocycloalkyl, C 3 -
  • the invention relates to processes and intermediates for the preparation of these compounds, compositions containing them and their use for controlling phytopathogenic harmful fungi.
  • This reaction is usually carried out at temperatures of 8O 0 C to 25O 0 C, preferably 12O 0 C to 18O 0 C, without solvent or in an inert organic solvent in the presence of a base [see. EP-A 770 615] or in the presence of acetic acid under the conditions described in Adv. Het. Chem. Vol. 57, p. 81ff. (1993) known conditions.
  • Suitable solvents are 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, N-methylpyrrolidone. It is also possible to use mixtures of the solvents mentioned.
  • 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, organometallic compounds, especially alkali metal alkyls, alkylmagnesium halides and alkali metal and alkaline earth metal alkoxides and dimethoxymagnesium.
  • organic bases for example 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.
  • tertiary amines such as tri-isopropylethylamine, tributylamine, N-methylmorpholine or N-methylpiperidine.
  • 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 malonate IIb in an excess based on the triazole.
  • R is C 1 -C 6 -alkyl, preferably C 1 -C 4 -alkyl, in particular methyl or ethyl, from the reaction of corresponding alkyl, alkenyl or alkynyl halides, in particular of the bromides under Cu (I) catalysis [cf. , Chemistry Letters, pp. 367-370, 1981; EP-A 10 02 788], or under basic conditions [cf. Organikum, VEB German publishing house of the sciences, Berlin 1988, S. 517] to be obtained.
  • the reaction is preferably carried out at 0 ° C to 120 ° C.
  • the base there can be used, for example, alkali metal alcoholates (such as methanolates, ethanolates and isopropanolates of alkali metals such as sodium or potassium), alkali metal hydrides such as e.g. Sodium hydride, potassium hydride or lithium hydride, alkali metal amides, e.g. Lithium amide, sodium amide or lithium diisopropylamide (LDA) can be used.
  • alkali metal alcoholates such as methanolates, ethanolates and isopropanolates of alkali metals such as sodium or potassium
  • alkali metal hydrides such as e.g. Sodium hydride, potassium hydride or lithium hydride
  • alkali metal amides e.g. Lithium amide, sodium amide or lithium diisopropylamide (LDA)
  • LDA lithium diisopropylamide
  • Suitable solvents for this reaction are preferably alcohols, e.g. Methanol or ethanol, but also acetonitrile, DMSO, DMF, as will be apparent to those skilled in the art.
  • 5,7-Dihalogentriazolopyrimidines of the formula II can be obtained, for example, by reacting the corresponding 5,7-Dihydroxytriazolopyrimidin the formula Nc in analogy to the cited prior art or according to the methods described in WO-A 94/20501 methods with a halogenating agent , Y has the meanings or preferred meanings as given for the compounds of the formula I.
  • the halogenating agents used are preferably phosphorus oxyhalide or phosphorus (V) halide, for example phosphorus pentachloride, phosphorus oxybromide or phosphorus oxychloride or a mixture of phosphorus oxychloride with phosphorus pentachloride. It may be advantageous to use a hydrohalide of a tertiary amine, e.g. Triethylamine hydrochloride, as a cocatalyst add.
  • the halogenation reaction of compounds of formula Mc to compounds of formula II is usually carried out at temperatures of 0 ° C to 150 ° C, preferably from 8O 0 C to 125 ° C [cf. EP-A 770 615].
  • the dihalogentriazolopyrimidines of the formula II thus obtained can be reacted with organometallic compounds.
  • M w (-Z) w can be implemented, whereby the substituent Z can be introduced in the 7-position:
  • Y and Z here have the meanings or preferred meanings as given for the compounds of the formula I and Hal is halogen, preferably fluorine, chlorine or bromine.
  • M is a metal ion of valence w, for example B, Zn, Mg or Sn.
  • This reaction can be carried out, for example, by the following methods: J. Chem. Soc. Perkin Trans. 1, 1 187 (1994), ibid., 2345 (1996); WO-A 99/41255; Aust. J. Chem., Vol. 43, 733 (1990); J. Org. Chem., Vol. 43, 358 (1978); J. Chem. Soc. Chem. Commun. 866 (1979); Tetrahedron Lett, Vol. 34, 8267 (1993); ibid., Vol. 33, 413 (1992).
  • the reaction is carried out under transition metal catalysis, e.g. Ni or Pd catalysis.
  • a a in the compounds A a B b represents a cation
  • B b is hydroxide, cyanide, Ci-C 8 alkoxylate, C 8 - haloalkoxides or C 8 -Alkylthiolat.
  • the compounds A a B b are a hydroxide, inorganic cyanide (for example KCN, NH 4 CN), a (halogen) alkoxylate or a thiolate.
  • the cation A a has little significance and there are such different types into consideration. For practical reasons, ammonium, tetraalkylammonium salts such as tetramethylammonium or tetraethylammonium salts or alkali metal or alkaline earth metal salts are usually preferred.
  • the reaction with A a B b 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)].
  • compounds of the formula I in which X a is C 1 -C 6 -alkyl, C 2 -C 8 -alkenyl or C 2 -C 8 -alkynyl can be prepared in this way using the corresponding compounds MX a .
  • the reaction is preferably carried out in the presence of catalytic or in particular at least equimolar amounts of transition metal salts and / or compounds, in particular in the presence of Cu salts such as Cu (I) halides and especially Cu (I) - iodide.
  • the reaction is preferably carried out in an inert organic solvent, for example one of the abovementioned ethers, in particular tetrahydrofuran, an aliphatic or cycloaliphatic hydrocarbon such as hexane, cyclohexane and the like, an aromatic hydrocarbon such as toluene or in a mixture of these solvents.
  • an inert organic solvent for example one of the abovementioned ethers, in particular tetrahydrofuran, an aliphatic or cycloaliphatic hydrocarbon such as hexane, cyclohexane and the like, an aromatic hydrocarbon such as toluene or in a mixture of these solvents.
  • the preferred temperatures for the reaction are in the range of -100 to + 100 ° C, in particular in the range of -80 ° C to + 40 ° C. Methods for this are known, for. B. from the cited prior art (see, for example, WO 03/004465).
  • Suitable solvents are, for example, aliphatic hydrocarbons, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, ethers, nitriles, ketones, alcohols, and also N-methylpyrrolidone, dimethylsulfoxide, dimethylformamide and dimethylacetamide.
  • the reaction is particularly preferably carried out without solvents or in chlorobenzene, xylene, dimethyl sulfoxide or N-methylpyrrolidone. It is also possible to use mixtures of the solvents mentioned.
  • 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 Erdalkalimetallhydride, alkali metal amides, alkali metal and alkaline earth metal carbonates and alkali metal bicarbonates, such as potassium carbonate, organometallic
  • organic bases for example tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine, 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 as triethylamine, triisopropylamine, tributylamine, N-methylmorpholine or N-methylpiperidine.
  • 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 dicarbonyl compound IM in excess, based on the triazole of the formula IIa.
  • Dicarbonyl compounds of formula IM can be prepared, for example, by reacting a compound IMa
  • Hal-Y a> corresponding compound Hal-Y, wherein Hal is halogen, preferably chlorine, bromine or iodine, X is Ci-Cs-alkyl, Ci-C 8 - haloalkyl, C2-C8-alkenyl, C 2 -C 8 -haloalkenyl, C 2 -C 8 -alkynyl or C 2 -C 8 -halo-genalkinyl, Z is C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2- Cio-alkynyl, C 2 -C 10 -haloalkynyl, C 3 -C 12 -cycloalkyl, C 3 -C 12 -halocycloalkyl, C 3 -C 12 -cycloalkenyl or C 3 -C
  • R 1 and R 2 have the meanings given for compounds of the formula I.
  • 7-Halotriazolopyrimidines of the formula IV can be obtained by reacting the corresponding 7-hydroxytriazolopyrimidine of the formula IVa is reacted with a halogenating agent, wherein X and Y have the meanings as given for the compounds of formula IV.
  • halogenation is carried out in analogy to the cited prior art or according to the methods described in WO-A 94/20501 or as set forth above for the reaction of compounds of formula Mc with a halogenating agent.
  • 7-Hydroxytriazolopyrimidines of the formula IVa can be prepared analogously to known methods [cf.: Adv. Het. Chem. Vol. 57, p. 81 ff. (1993)].
  • Compounds of the formula IVa can be obtained by using a compound of the
  • reaction of the triazole of the formula IIa with a compound of the formula IIIb is carried out analogously to the above-described reaction of the compound IIa with Mb.
  • Compounds of the formula IIIb can be prepared analogously to standard processes in the form of a mixed ester condensation from the corresponding substituted acetic acid esters by reaction with the corresponding aliphatic C2-Cs-carboxylic acid alkyl esters such as ethyl acetate, ethyl propionate, ethyl butyrate or ethyl valerate or with a reactive derivative thereof, e.g. an acid chloride or an acid anhydride, in the presence of a strong base, e.g. an alkoxide, an alkali metal amide or an organolithium compound, for example in analogy to that described in J. Chem. Soc. Perkin Trans 1967, 767 or Eur. J. Org. Chem. 2002, p. 3986.
  • a strong base e.g. an alkoxide, an alkali metal amide or an organolithium compound
  • ester V The subsequent hydrolysis of the ester V is carried out under conditions well known to those skilled in the art. Depending on the various structural elements, the alkaline or acidic hydrolysis of the compounds V may be advantageous. Under the conditions of ester hydrolysis, the decarboxylation to the compounds of the formula I can already take place completely or partially.
  • the decarboxylation is usually carried out at temperatures from 2O 0 C to 18O 0 C, preferably 5O 0 C to 12O 0 C.
  • the decarboxylation is carried out in an inert solvent, optionally in the presence of an acid.
  • Suitable acids are hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, p-toluenesulfonic acid.
  • Suitable solvents are water, aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether , Dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, as well as Dimethyl sulfox
  • Another object of the present invention are compounds of formula V, wherein X "is hydrogen or C 1 -C 7 -alkyl and R is C 1 -C 4 -alkyl and Y and Z are as defined for compounds of formula I.
  • the reaction mixtures are worked up in the usual way, e.g. by mixing with water, separation of the phases and optionally chromatographic purification of the crude products.
  • the intermediate and end products are z.T. in the form of colorless or pale brownish, viscous oils, which are freed or purified under reduced pressure and at moderately elevated temperature from volatile constituents. If the intermediate and end products are obtained as solids, the purification can also be carried out by recrystallization or trituration.
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkyl saturated, straight-chain or branched hydrocarbon radicals having 1 to 4, 6 or 8 carbon atoms, e.g. C 1 -C 6 -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-d
  • Haloalkyl straight-chain or branched alkyl groups having 1 to 2, 4 or 6 carbon atoms (as mentioned above), in which groups the hydrogen atoms may be partially or completely replaced by halogen atoms as mentioned above: in particular C 1 -C 2 -haloalkyl, such as chloromethyl, Bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2- Trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroeth
  • C2-C6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1 Methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 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
  • Haloalkenyl unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 8 carbon atoms and having one or two double bonds in any position (as mentioned above), where in these groups the hydrogen atoms are partially hydrogenated. or completely replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine;
  • Alkynyl straight-chain or branched hydrocarbon groups having 2 to 4, 6 or 8 carbon atoms and one or two triple bonds in any position, for example C 2 -C 6 alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl , 3-butynyl, 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-pentyny
  • Cycloalkyl mono- or bicyclic saturated hydrocarbon groups having 3 to 6 or 8 carbon ring members, e.g. C 1 -C 8 cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl; A five- to ten-membered saturated, partially unsaturated or aromatic heterocycle containing one to four heteroatoms from the group O, N or S:
  • 5- or 6-membered heterocyclyl containing one to three nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms e.g. 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5- isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolindinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolid
  • 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. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl;
  • Alkylene divalent linear chains of 1 to 5 CH 2 groups, eg CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 and CH 2 CH 2 CH 2 CH 2 CH 2 ;
  • Oxyalkylene divalent unbranched chains of 2 to 4 Chb groups, wherein a valence is bonded to the skeleton via an oxygen atom, for example OCH 2 CH 2 , OCH 2 CH 2 CH 2 and OCH 2 CH 2 CH 2 CH 2 ;
  • Oxyalkylenoxy divalent unbranched chains of 1 to 3 Chb groups, wherein both valences are bonded to the skeleton via an oxygen atom, for example OCH 2 O, OCH 2 CH 2 O and OCH 2 CH 2 CH 2 O;
  • X is halogen, cyano, Ci-C8-alkoxy, Ci-C 8 - haloalkoxy, Ci-C 8 -alkyl or C 8 -haloalkyl, preferably halogen.
  • X is Ci-Cs-alkyl, d-Cs-haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 kinyl -alkyl, C 2 -C 8 Haloalkynyl, cyano-Ci-C4-alkyl or X is preferably C 1 -C 4 -alkyl, such as methyl or ethyl.
  • a further embodiment relates to compounds I in which X is C 1 -C 4 -haloalkyl, such as, for example, fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorofluoromethyl, dichlorofluoromethyl or chlorodifluoromethyl.
  • X is C 1 -C 4 -haloalkyl, such as, for example, fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorofluoromethyl, dichlorofluoromethyl or chlorodifluoromethyl.
  • Another embodiment relates to compounds I in which X is C 2 -C 6 -alkenyl or C 2 -C 6 -haloalkenyl, preferably C 2 -C 4 -alkenyl or C 2 -C 4 -haloalkenyl.
  • Another embodiment relates to compounds I in which X is halogen, in particular chlorine.
  • X is C 1 -C 8 -alkoxy, preferably C 1 -C 4 -alkoxy, in particular methoxy.
  • a further embodiment relates to compounds I in which X is C 1 -C 8 -haloalkoxy, preferably C 1 -C 4 -haloalkoxy. According to another embodiment of the present invention, X is cyano.
  • X is cyano-C 1 -C 4 -alkyl, preferably cyano-C 1 -C 2 -alkyl, in particular -CH 2 -N-CN.
  • X is C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, in particular C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl, such as methoxymethyl, or C 1 -C 4 -alkyl, in particular n-propyl, ethyl or Methyl.
  • One embodiment of the group Y relates to straight-chain or branched, unsubstituted or substituted C 1 -C 10 -alkyl. Another embodiment of the group Y relates to straight-chain or branched, unsubstituted or substituted C 2 -C 10 -alkenyl.
  • Another embodiment of the group Y relates to straight-chain or branched, unsubstituted or substituted C 2 -C 10 -alkynyl. Another embodiment of the group Y relates to unsubstituted or substituted C3-Cio-cycloalkyl.
  • the alkyl, alkenyl or alkynyl group is substituted by a five, six, seven, eight, nine or ten membered saturated, especially five- or six-membered, partially unsaturated or aromatic heterocycle containing , two, three or four heteroatoms from the group O, N and S, substituted.
  • Embodiments Groups Y.a and Y.b are identical to Embodiments Groups Y.a and Y.b:
  • W 1 , W 2 is hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -cycloalkyl, C 1 -C 4 -
  • W 3 , W 4 denote Cs-C ⁇ -alkyl or one of the groups mentioned for W 1 .
  • W 1 and W 2 independently represent, for example, hydrogen; Halogen, such as fluorine, chlorine, bromine; C 1 -C 4 -alkyl, such as CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH (CH 3 ) 2 ; C 1 -C 4 -haloalkyl, such as CH 2 Cl, CH 2 F, CH 2 Br, CHCH 2 , CHF 2 , CCI 3 , CF 3 , CH 2 CH 2 Cl,
  • W 3 and W 4 independently of one another are, for example, C 4 -C 6 -alkyl, such as CH 2 CH 2 CH 2 CH 3 , CH (CH 3 ) CH 2 CH 3 , CH 2 CH (CH) 2 , C (CH 3 ) 3 , CH 2 CH 2 CH 2 CH 2 CH 3 , CH (CH 3 ) CH 2 CH 2 CH 3 , CH 2 CH (CH 3 ) CH 2 CH 3 , CH 2 CH 2 CH (CHS) 2 , CH (CH 3 ) CH ( CHS) 2 , CH 2 CH 2 CH 2 CH 2 CHS, CH (CH 3 ) CH 2 CH 2 CHS, CH 2 CH (CH 3 ) CH 2 CH 2 CHS, CH 2 CH (CH 3 ) CH 2 CH 2 CHS, CH 2 CH 2 CH (CH 3 ) CH (CHS) CH 2 CH 3 , CH 2 CH (CH 2 CHS) 2 or one of the groups mentioned above for W 1 .
  • C 4 -C 6 -alkyl such as CH 2 CH 2 CH 2 CH 3
  • a preferred embodiment for alkynyl groups in position Y is the group Y.c:
  • W 1 and W 2 in the group Yc independently of one another denote, for example, hydrogen; Halogen, such as fluorine, chlorine, bromine; C 1 -C 4 -alkyl, such as CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH (CHa) 2 ; Halomethyl such as CH 2 Cl, CH 2 F, CH 2 Br, CHCH 2 , CHF 2 , CCI 3 , CF 3 ; C 1 -C 4 -alkoxy, such as OCH 3 ; hydroxy; cyano; substituted C 1 -C 2 -alkyl, such as CH 2 OH, CH 2 CN, CH 2 OCH 3 , CH (CN) 2 , CH 2 CH 2 OCH 3 , CH 2 CH 2 CN, CH 2 CH (CN) 2 , CH 2 CH 2 OH.
  • Halogen such as fluorine, chlorine, bromine
  • C 1 -C 4 -alkyl such as CH 3 , CH 2 CH 3 , CH 2 CH
  • W 1 and W 2 denote hydrogen or C 1 -C 4 -alkyl, such as CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH (CH 3 ) 2 .
  • W 3 in the group Yc is, for example, branched C 4 -C 6 -alkyl, such as
  • a preferred embodiment for alkyl groups in position Y is the group Yd: w! W 2
  • W 1 in the group Yd represents, for example, hydrogen; Halogen, such as fluorine, chlorine, bromine; C 1 -C 4 -alkyl, such as CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH (CH 3 ) 2 ; C 1 -C 4 -haloalkyl, such as CH 2 Cl, CH 2 F, CH 2 Br, CHCH 2 , CHF 2 , CCI 3 , CF 3 , CH 2 CH 2 Cl, CH 2 CH 2 F, CH 2 CH 2 Br, CH 2 CHCl 2 , CH 2 CHF 2 , CH 2 CCI 3 , CH 2 CF 3 , CCI 2 CCI 3 , CF 2 CF 3 , CH 2 CH 2 CH 2 Cl, CH 2 CH 2 CH 2 F, CH 2 CH 2 Br, CH 2 CCI 3 , CH 2 CF 3 , CCI 2 CCI 3 , CF 2 CF 3 , CH 2 CH 2 CH 2 Cl, CH 2 CH 2 CH 2 F, CH 2 CH 2 Br
  • W 3 in the group Yd is, for example, C 3 -C 6 -alkyl, such as CH (CH 3 ) 2 , CH 2 CH 2 CH 2 CH 3 , CH (CH 3 ) CH 2 CH 3 , CH 2 CH (CHa) 2 , C (CHa) 3, CH 2 CH 2 CH 2 CH 2 CH 3, CH (CH 3) CH 2 CH 2 CH 3, CH 2 CH (CH 3) CH 2 CH 3, CH 2 CH (CH 3) CH 2 CH 3, CH 2 CH 2 CH (CHa) 2 , CH (CH 3 ) CH (CH 3 ) 2 , CH 2 CH 2 CH 2 CH 2 CH 3 , CH (CH 3 ) CH 2 CH 2 CH 3 , CH 2 CH (CH 3 ) CH 2 CH 2 CH 3 , CH 2 CH (CH 3 ) CH 2 CH 2 CH 3 , CH 2 CH 2 CH (CH 3 ) CH (CH 3 ) CH 2 CH 3 , CH (CH 3 ) CH (CH 3 ) CH 2 CH 3 , CH 2 CH (CH 3 ) CH (CH 3
  • group Y relates to cycloalkyl groups in which the hydrogen atoms are partially or completely replaced by groups R a .
  • Preferred embodiments of cycloalkyl groups in position Y are the groups
  • W 1 in the group Ye is, for example, hydrogen or methyl
  • W 2 and W 3 in the group Ye independently of one another denote, for example, hydrogen; cyano; Halogen, such as chlorine or bromine; C 1 -C 3 -alkyl, such as CH 3, CH 2 CH 3; C 1 -C 8 alkoxy, such as OCH 3 ; Halomethyl such as CH 2 Cl, CH 2 F, CH 2 Br, CHCH 2 , CHF 2 , CCI 3 , CF 3 .
  • W 2 and W 3 are the same.
  • W 1 and W 2 in the groups Yf, Yg and Yh are preferably hydrogen.
  • Preferred embodiments of compounds of the formula I correspond to the formulas La to l.h, where the variables have the meanings given above.
  • Y is an unsubstituted or substituted by R a , as defined above, (C 3 -Cio) -Cycloalkenyl, preferably (C5-C7) -cycloalkenyl group.
  • the cycloalkenyl group preferably has one or two double bonds.
  • Examples of cycloalkenyl groups as substituent Y are cyclopent-1-en-1-yl, cyclohex-1-en-1-yl, which may be substituted according to the invention by R a , as defined above.
  • Y is an optionally substituted imino group, in particular a group (B)
  • R a1 and R a2 independently of one another have the meanings given for R a , in particular those given for R a .
  • R a1 and R a2 are preferably independently selected from hydrogen, Ci-C8-alkoxy, Ci-C 8 alkyl, Ci-C8-haloalkyl, Ci-C 8 alkoxy Ci-C8 alkyl, C2-C8 alkenyl, Ci-C6 Alkylamino and di (Ci-C6-alkyl) amino, in particular selected from Ci-C ⁇ -alkyl, in particular methyl, ethyl, n-propyl and iso-propyl; C 1 -C 6 haloalkyl, in particular trichloromethyl, trifluoromethyl, 1,1,1-trifluoroethyl; C 1 -C 6 -alkoxy, especially methoxy, ethoxy and propoxy; and Ci-C ⁇ -hal
  • Z is C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 2 -C 10 -haloalkynyl, C 3 -C 12 -cycloalkyl (in particular Ca-Cs-cycloalkyl and / or Cg-C 12 -cycloalkyl), C 3 -C 12 -halocycloalkyl, C 3 -C 12 -cycloalkenyl, C 3 -C 12 -halo-cycloalkenyl, phenyl, halophenyl, naphthyl, halonaphthyl or a five-, a six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic carbon-bonded heterocycle
  • Z is preferably C 1 -C 10 -alkyl, C 1 -C 10 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 -alkynyl, C 2 -C 10 -haloalkynyl, C 3 -C 12 -cycloalkyl, C 3 -C 12 -halocycloalkyl , C 3 -C 12 -cycloalkenyl, C 3 -C 12 -halocycloalkenyl, naphthyl or halonaphthyl or a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic carbon-bonded heterocycle containing one, two, three or four heteroatoms from the group oxygen, nitrogen and sulfur, more preferably Ci-Cio-alkyl, Ci-Cio-haloalkyl, C2-Cio
  • Z is C 3 -C 12 -cycloalkyl, more preferably C 6 -C 8 -cycloalkyl.
  • Z is Ci-Cio-alkyl, in particular Cs-Cs-alkyl, which is optionally substituted by one, two or three R a .
  • R a is preferably selected from halogen, cyano, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkoximino, C 2 -C 6 -alkenyloximino, C 2 -C 6 - Alkinyloximino, C3-C6-cycloalkyl or Cs-C ⁇ -cycloalkenyl, wherein the aliphatic and / or alicyclic groups may in turn be substituted by one, two or three groups R b .
  • R b is preferably independently of each halogen, cya no, d-Ce-alkyl, C 2 -C 6 alkenyl, C 2 -C 6 kinyl -alkyl, Ci-C 6 alkoxy, Ci-C 6 alkylcarbonyl or Ci-C6-haloalkylcarbonyl.
  • Z is Ci-Cio-haloalkyl, in particular Cs-C ⁇ -haloalkyl.
  • ZC 2 is - Cio-alkenyl, in particular C 3 -Cs-Al kenyl, which is optionally substituted by one, two or three R a , as defined herein.
  • ZC 2 represents - Cio-alkynyl, especially C 3 -Cs-Al kinyl, which if necessary by one, two or three R a is substituted, as defined herein.
  • ZC 3 -Ci2-cycloalkenyl in particular Cs-Cio-cycloalkenyl, especially C5- or C ⁇ -cycloalkenyl, which is optionally substituted by one, two or three R a , as defined herein.
  • the cycoalkenyl group is monosubstituted, disubstituted or trisubstituted by C 1 -C 4 -alkyl, such as, for example, methyl and / or ethyl.
  • Z is a saturated, partially unsaturated, unsaturated or aromatic heterocycle bonded via carbon to the triazolopyrimidine skeleton containing five, six, seven, eight, nine or ten membered heterocycles containing one, two, three or four heteroatoms from the group oxygen, nitrogen and sulfur, said heterocycle being unsubstituted or substituted with one, two, three or four identical or different substi- tuenten R a as defined herein.
  • Z is an optionally substituted five- or six-membered saturated or aromatic heterocycle bonded via carbon to the triazolopyrimidine skeleton.
  • One embodiment relates to compounds of Tables 1 to 2156, in which X is Cl and W 2 is H.
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is Cl and W 2 is CH 3 .
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is Cl and W 2 is CF 3 .
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is Cl and W 2 is CN.
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is Cl and W 2 is OCH 3 .
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is Cl and W 2 is F.
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is Cl and W 2 is Cl.
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is Cl and W 2 is Br. Another embodiment relates to compounds of Tables 1 to 2156, in which X is Cl and W 2 is CH 2 CH 3 .
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is Cl and W 2 is CH 2 CH 2 OH. Another embodiment relates to compounds of Tables 1 to 2156, in which X is Cl and W 2 is CH 2 CCI 3 .
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is Cl and W 2 is CH 2 CH 2 CH 3 .
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is Cl and W 2 is C (CH 3 ) 3 .
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is Cl and W 2 is CH 2 CH 2 CH 2 CN.
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is Cl and W 2 is CH (CH 2 ) 2 .
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is Cl and W 2 is CH (CH 3 ) CH 2 OCH 3 .
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is Cl and W 2 is CH 2 CH 2 CH 2 CH 3 .
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is Cl and W 2 is CH (CH 3 ) CH 2 CH 3 .
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is Cl and W 2 is CH 2 CH (CHs) 2 .
  • One embodiment relates to compounds of Tables 1 to 2156, in which X is CH 3 and W 2 is H.
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is CH 3 and W 2 is CH 3 .
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is CH 3 and W 2 is CF 3 .
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is CH 3 and W 2 is CN.
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is CH 3 and W 2 is OCH 3 .
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is CH 3 and W 2 is F.
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is CH 3 and W 2 is Cl.
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is CH 3 and W 2 is Br. Another embodiment relates to compounds of Tables 1 to 2156, in which X is CH 3 and W 2 is CH 2 CH 3 .
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is CH 3 and W 2 is CH 2 CH 2 OH.
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is CH 3 and W 2 is CH 2 CCI 3 .
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is CH 3 and W 2 is CH 2 CH 2 CH 3 .
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is CH 3 and W 2 is C (CH 3 ) 3 .
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is CH 3 and W 2 is CH 2 CH 2 CH 2 CN. Another embodiment relates to compounds of Tables 1 to 2156, in which X is CH 3 and W 2 is CH (CH 3 ) 2 .
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is CH 3 and W 2 is CH (CH 3 ) CH 2 OCH 3 .
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is CH 3 and W 2 is CH 2 CH 2 CH 2 CH 3 .
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is CH 3 and W 2 is CH (CH 3 ) CH 2 CH 3 .
  • Another embodiment relates to compounds of Tables 1 to 2156, in which X is CH 3 and W 2 is CH 2 CH (CHs) 2 .
  • the groups mentioned in the tables for a substituent also stand alone, irrespective of the combination in which they are mentioned represent a particularly preferred embodiment of the relevant substituent.
  • the compounds I are suitable as fungicides. They are distinguished by outstanding activity against a broad spectrum of phytopathogenic fungi from the classes of the Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes, in particular from the class of the Oomycetes. They are partially systemically effective and can be used in crop protection as foliar, pickling and soil fungicides.
  • fungi are particularly important for the control of a variety of fungi on various crops such as wheat, rye, barley, oats, rice, corn, grass, bananas, cotton, soy, coffee, sugar cane, wine, fruit and ornamental plants and vegetables such as cucumbers. Beans, tomatoes, potatoes and squashes, as well as the seeds of these plants. They may also be used in cultures tolerant of insect or fungal growth by breeding, including genetic engineering methods. In addition, they are suitable for combating Botryosphaeria species, Cylindrocarpon species, Eutypa lata, Neonectria liriodendri and Stereum hirsutum, which attack, among other things, the wood or roots of grapevines.
  • Ascochyta species on cereals and vegetables e.g. Ascochyta tritici (leaf drought) on wheat,
  • Blumeria graminis (powdery mildew) on cereals (such as wheat or barley), Botrytis cinerea (gray mold) on strawberries, vegetables, flowers, vines and wheat (cereal),
  • Bremia lactucae on lettuce Cercospora species on corn, rice, sugar beet and e.g. Cercospora sojina (leaf spot) or Cercospora kikuchii (leaf spot) on soybeans, Cladosporium herbarum (earwax) on wheat,
  • Corynespora cassiicola (leaf spots) on soybeans, Dematophora necatrix (root / stem rot) on soybeans, Diaporthe phaseolorum (stalk disease) on soybeans, Drechslera species, Pyrenophora species on maize, cereals, rice and turf
  • Barley e.g., D. teres
  • wheat e.g., D. tritici-repentis
  • Gaeumanomyces graminis root black on cereals (eg wheat or gers), Gibberella species on cereals and rice (eg Gibberella fujikuroi), Glomerella cingulata on grapevine and other plants, Grainstaining complex on rice, Guignardia budwelli on grapevine, Helminthosporium species on maize and rice, Isariopsis clavispora on grapevine,
  • Macrophomina phaseolina root / stem rot
  • Michrodochium nivale sichrodochium nivale
  • Microsphaera diffusa prowdery mildew
  • Mycosphaerella species on cereals, bananas, and peanuts, e.g. M. graminicola on wheat or M. fijiensis on bananas,
  • Peronospora species on cabbage e.g., P. brassicae
  • bulbous plants e.g., P. destructor
  • Peronospora manshurica downy mildew
  • Phakopsara pachyrhizi (soybean rust) and Phakopsara meibomiae (soybean rust) on soybeans
  • Phytophthora species on various plants e.g. P. capsici on sweet peppers, Phytophthora megasperma on soybeans, Phytophthora infestans on potatoes and tomatoes, Plasmopara viticola on vines, Podosphaera leucotricha on apples,
  • Puccinia species on various plants e.g. P. triticina, P. striformins, P. hordei or P. graminis on cereals (e.g., wheat or barley) or asparagus (e.g., P. asparagi),
  • Typhula incarnata (snow) on wheat or barley, Ustilago species on cereals, maize (e.g., U. maydis) and sugarcane, Venturia species (scab) on apples (e.g., V. inaequalis) and pears.
  • they are suitable for controlling harmful fungi from the class of Peronosporomycetes (syn.Oomyceten), such as Peronospora species, Phytophthora species, Plasmopara viticola, Pseudoperonospora species and Pythium species.
  • the compounds I 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. Deuterium fungi 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 are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally effective amount of the active ingredients.
  • 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.
  • amounts of active ingredient of 1 to 1000 g / 100 kg, preferably 5 to 100 g / 100 kg of seed are needed.
  • the application rate of active ingredient depends on the type of application and the desired effect. Typical application rates in the protection of materials 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.
  • the compounds of the formula I can be present in various crystal modifications, which may differ in their biological activity. They are also the subject of the present invention.
  • the compounds I can be converted into the usual formulations, e.g.
  • compositions are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants.
  • Suitable solvents / auxiliaries are essentially:
  • Ketones e.g., cyclohexanone, gamma-butyrolactone), pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols, dimethyl fatty acid amides, fatty acids, and fatty acid esters.
  • solvent mixtures can also be used
  • Excipients such as ground natural minerals (e.g., kaolins, clays, talc, calks) and ground synthetic minerals (e.g., fumed silica, silicates);
  • ground natural minerals e.g., kaolins, clays, talc, calks
  • ground synthetic minerals e.g., fumed silica, silicates
  • Emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.
  • nonionic and anionic emulsifiers for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates
  • dispersants such as lignin-sulphite liquors and methylcellulose.
  • the surface-active substances used are alkali metal, alkaline earth metal, ammonium salts of lithium sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers
  • emulsions, pastes or oil dispersions come 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, eg toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone or water into consideration.
  • Kerosene or diesel oil coal tar oils and oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons eg toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives
  • Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
  • Granules e.g. Coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers.
  • Solid carriers are e.g. Mineral earths, such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • Mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, 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)
  • the active compounds 20 parts by weight are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant, e.g. Polyvinylpyrrolidone dissolved. Dilution in water results in a dispersion.
  • the active ingredient content is 20% by weight
  • the formulation has an active ingredient content of 25% by weight.
  • the active ingredients 20 parts by weight of the active ingredients are comminuted with the addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine active substance suspension. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • F Water-dispersible and water-soluble granules (WG, SG) 50 parts by weight of the active compounds are finely ground with the addition of 50 parts by weight of dispersing and wetting agents and prepared by means of industrial equipment (for example 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.
  • 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.
  • the active compounds may be used as such, in the form of their formulations or the forms of use prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, litter, granules by spraying, misting, dusting, scattering or pouring.
  • 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.
  • wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides, possibly also just immediately 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.
  • As an adjuvant in this sense are in particular: organically modified polysiloxanes, eg Break Thru S 240 ® ; Alcohol alkoxylates, eg.
  • the agents according to the invention can also be present in the application form as fungicides together with other active substances, for example with herbicides, insecticides, growth regulators, fungicides or else with fertilizers.
  • the fungicides are preferably selected from the following groups: Strobilurins, carboxylic acid amides such as carboxylic acid anilides, carboxylic acid morpholides, benzoic acid amides, other carboxamides, azoles such as triazoles, imidazoles, benzimidazoles, others, nitrogen-containing heterocyclyl compounds such as pyridines, pyrimidines, pyrroles, morpholines, dicarboximides, other nitrogen-containing heterocyclyl compounds, thio- and dithiocarbamates, carbamates, guanidines , Antibiotics, nitrophenyl derivatives, organometallic compounds, sulfur-containing heterocyclyl compounds, organophosphorus compounds, organochlorine compounds
  • the present invention further relates to the compositions listed in Table B, wherein in each case one row of Table B corresponds to a fungicidal composition comprising a compound of the formula I (component 1), which is preferably one of the compounds described herein as preferred, and the in each case indicated in the relevant line further active ingredient (component 2).
  • component 1 in each row of table B is in each case one of the compounds of the formula I which are specifically individualized in tables 1 to 2172.
  • the active ingredients II mentioned above as component 2 their preparation and their action against harmful fungi are generally known (cf. they are commercially available.
  • the compounds named after IUPAC, their preparation and their fungicidal action are also known [cf. EP-A 226 917; EP-A 10 28 125; EP-A 10 35 122; EP-A 12 01 648; WO 98/46608; WO 99/24413; WO 03/14103; WO 03/053145; WO 03/066609; WO 04/049804].
  • Example 1 Preparation of 6-hexyl- [1,2,4] triazolo [1,5-a] pyrimidine-5,7-diol
  • a mixture of 6.67 g of 3-amino-1H-1, 2, 4- triazole and 20.0 g of hexyl diethylmalonate in 100 ml of n-tributylamine was heated at 180 ° C. for 3 hours under Dean-Stark conditions. After cooling to 60 ° C, the reaction mixture was washed with 30 ml of 25% aq. NaOH solution and stirred for a further 1 hr. After phase separation, the aqueous phase was extracted with methyl tert-butyl ether (MTBE).
  • MTBE methyl tert-butyl ether
  • Example 2 Preparation of 5,7-dichloro-6-hexyl- [1,2,4] triazolo [1,5-a] pyrimidine 12.00 g of the compound from Example 1 were slowly mixed with 50 ml of POCb, with stirring the mixture was refluxed for 10 hrs. After distilling off the excess POCb, the residue was taken up in 250 ml of CH 2 Cl 2, then admixed with 100 ml at a temperature of 25 to 30 ° C. After phase separation, the organic phase was extracted with water, then dried. After flash chromatography on silica gel (cyclohexane / ethyl acetate 100: 0 to 5: 1), 4.20 g of the title compound were obtained as a yellow crystalline mass.
  • Example 3 Preparation of 7-butyl-5-chloro-6-hexyl- [1,2,4] triazolo [1,5-a] pyrimidine. 300 mg of the compound from Example 2 were saturated with 5 ml. NaHCO3, then dried and freed from the solvent in vacuo.
  • Example 4b Preparation of 5,7,7-trimethyl-2-propionyl-octanoic acid 50 g of the compound from Example 4a dissolved in 100 ml of ethanol were hydrogenated with 400 mg of Pd / C in an autoclave for 10 hours (7O 0 C, 10 bar ). After filtration over Celite and distilling off the solvent, the crude product was obtained, which was washed after dissolving in 200 ml of MTBE with 100 ml of water. The MTBE solution was freed from the solvent after drying, leaving 43 g of the title compound behind.
  • Example 4d Preparation of 7-chloro-5-ethyl-6- (3,5,5-trimethyl-hexyl) - [1, 2,4] triazolo [1, 5-a] pyrimidine 4.2 g of the compound of Example 4c were refluxed in 20 ml POCb for 7 h. Then the excess POCb was distilled off, the residue was taken up in 100 ml of CH 2 Cl 2, then 50 ml was added with stirring. After phase separation, the organic phase with 50ml sat. NaHCO 3 solution, washed with water, then dried. After distilling off the solvent, 4.1 g of the title compound were obtained as an oil (purity about 90% by HPLC).
  • Example 4e Preparation of 5-ethyl-7-methyl-6- (3,5,5-trimethyl-hexyl) - [1,2,4] triazolo [1,5-a] pyrimidine A mixture of 1, 07g (3.5mmol) of the compound from Example 4d, 2mol%
  • Ni (acac) 2 in 10 mM THF (10 mL) at 20-25 ° C was slowly stirred with 1, 8 mL of a 3M solution of methylmagnesium chloride in THF and an additional 4 h. Then 5ml sat. NH4Cl solution and, after stirring for a further 5 minutes, 20 ml of MTBE are added and the phases are separated. The aqueous phase was extracted with MTBE, then the combined organic phases were washed with water, dried and freed from the solvent. After flash chromatography on silica gel (100% CH 2 Cl 2), 300 mg of the title compound were obtained.
  • HPLC retention times in the following table were calculated using the RP-18 column Chromolith Speed ROD (from Merck KgaA, Germany) with the eluent acetonitrile + 0.1% trifluoroacetic acid (TFA) / water + 0, 1% TFA in a 5:95 to 95: 5 gradient determined at 40 ° C for 5 min. Mass spectrometry was performed under Quadropol electrospray ionization, 80V (positive mode).
  • the active compounds were prepared as a stock solution with 25 mg of active ingredient, which with a mixture of acetone and / or DMSO and the emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkyl kylphenole) in the volume ratio solvent-emulsifier from 99 to 1 ad 10 ml. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the drug concentration given below.
  • Uniperol® EL wetting agent with emulsifying and dispersing action based on ethoxylated alkyl kylphenole
  • Leaves of potted tomato plants were sprayed to drip point with an aqueous suspension in the drug concentration below. The following day, the leaves were inoculated with an aqueous sporangia suspension of Phytophthora infestans. The plants were then placed in a water vapor-saturated chamber at temperatures between 18 and 20 ° C. After 6 days, the late blight on the untreated but infected control plants had developed so strongly that the infestation could be determined visually in%.
  • Capsicum seedlings were sprayed to dripping wetness after 2-3 sheets had developed well, with an aqueous suspension in the concentration of active compound given below.
  • the treated plants were inoculated with a spore suspension of Botrytis cinerea in 2% 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%. In this test, plants treated with 250 ppm of Compound I-9 showed
  • 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 Botrytis cinerea.
  • MTP microtiter plate
  • the plates were placed in a steam-saturated chamber at temperatures of 18 ° C. With an absorbance photometer, the MTPs 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.
  • the stock solution is pipetted into a microtiter plate (MTP) and diluted with an aqueous fungus nutrient medium based on pea juice to the stated active substance concentration. This was followed by the addition of an aqueous zoospore suspension of Phytophthora infestans.
  • MTP microtiter plate
  • the plates were placed in a water vapor-saturated chamber at temperatures of 18 ° C. Detection and evaluation were carried out analogously to application example 4. In this test, the samples treated with 125 ppm of compounds I-6, 1-6, 1-9, and 1-12 showed a maximum of 11% relative growth of the pathogens.
  • 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 steam-saturated chamber at temperatures of 18 ° C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne les composés représentés par la formule (I) dans laquelle X, Y et Z ont la signification donnée dans le descriptif, des procédés et des produits intermédiaires destinés à la fabrication desdits composés, des agents contenant ces composés et leur utilisation dans la lutte contre des champignons parasites phytopathogènes.
PCT/EP2007/053355 2006-04-10 2007-04-05 Triazolopyrimidines substituées, procédé de fabrication, utilisation dans la lutte contre des champignons parasites et agent contenant ces composés WO2007116011A2 (fr)

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Publication number Priority date Publication date Assignee Title
US10517849B2 (en) 2016-10-26 2019-12-31 Constellation Pharmaceuticals, Inc. LSD1 inhibitors and medical uses thereof
US10526287B2 (en) 2015-04-23 2020-01-07 Constellation Pharmaceuticals, Inc. LSD1 inhibitors and uses thereof
US11814734B2 (en) 2019-05-13 2023-11-14 Ecolab Usa Inc. 1,2,4-triazolo[1,5-a] pyrimidine derivative as copper corrosion inhibitor

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10526287B2 (en) 2015-04-23 2020-01-07 Constellation Pharmaceuticals, Inc. LSD1 inhibitors and uses thereof
US10517849B2 (en) 2016-10-26 2019-12-31 Constellation Pharmaceuticals, Inc. LSD1 inhibitors and medical uses thereof
US11013718B2 (en) 2016-10-26 2021-05-25 Constellation Pharmaceuticals, Inc. LSD1 inhibitors and medical uses thereof
US11547695B2 (en) 2016-10-26 2023-01-10 Constellation Pharmaceuticals, Inc. LSD1 inhibitors and medical uses thereof
US11814734B2 (en) 2019-05-13 2023-11-14 Ecolab Usa Inc. 1,2,4-triazolo[1,5-a] pyrimidine derivative as copper corrosion inhibitor

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AR060420A1 (es) 2008-06-18

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