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WO2007113136A1 - Utilisation de triazolopyrimidines substituées dans la lutte contre des champignons phytopathogènes - Google Patents

Utilisation de triazolopyrimidines substituées dans la lutte contre des champignons phytopathogènes Download PDF

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WO2007113136A1
WO2007113136A1 PCT/EP2007/052796 EP2007052796W WO2007113136A1 WO 2007113136 A1 WO2007113136 A1 WO 2007113136A1 EP 2007052796 W EP2007052796 W EP 2007052796W WO 2007113136 A1 WO2007113136 A1 WO 2007113136A1
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English (en)
Inventor
Jochen Dietz
Thomas Grotz
Wassilios Grammenos
Bernd Müller
Jan Klaas Lohmann
Jens Renner
Sarah Ulmschneider
Jordi Tormo I Blasco
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BASF SE
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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 the use of substituted triazolopyrimidine of the formula I,
  • R 5 can also form, with R 3 or R 7 together with the atoms to which these radicals are bonded, a five-, six-, seven-, eight-, nine- or ten-membered saturated or partially unsaturated ring which, in addition to carbon atoms one, two
  • R a is halogen, cyano, nitro, hydroxy, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl,
  • R b is halogen, cyano, nitro, hydroxyl, mercapto, amino, carboxyl, alkyl, haloalkyl, alkenyl, alkoxy, haloalkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylamino, dialkylamino, formyl, alkylcarbonyl, alkylsulfonyl, alkylsulfoxyl, alkoxycarbonyl, alkylcarbonyloxy, Alkoxycarbonyloxy, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, the alkyl groups in these radicals containing from 1 to 6 carbon atoms and said alkenyl or alkynyl groups in these radicals containing from 2 to 8 carbon atoms; Cycloalkyl, cycloalkoxy, hetero
  • Z is hydrogen, carboxyl, formyl, Ci -C 8 -alkyl, C 8 haloalkyl, C 2 -
  • R A , R B independently of one another are hydrogen, C 2 -alkenyl, C 2 -alkynyl or one of the groups mentioned for R ⁇ ;
  • R A and R B can also be taken together with the nitrogen atom to which they are attached, or R A and R ⁇ together with the carbon and hetero atoms through which they are attached, a five- or six-membered saturated, partially unsaturated or aromatic ring form, in addition to carbon atoms, one, two or three further heteroatoms from the group O, N and S contain as a ring member and / or can carry one or more substituents R a ; or
  • R 6 or R 8 a five- or six-membered saturated or partially unsaturated ring which, in addition to carbon atoms and Y, may contain one or two further heteroatoms from the group O, N and S as ring member and / or one or more can carry a plurality of substituents R a ; the group Z may be partially or completely halogenated and / or carry one, two or three groups R b ; Hydrogen or one of the groups mentioned for R 1 ; R 1 and R 2 , together with the nitrogen atom to which they are attached, may also form a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle containing, in addition to carbon atoms, one, two or three carbon atoms three further heteroatoms from the group O, N and S may contain as ring member and which contains at least one substituent selected from UO #, US # and UY- (CR 5 R 6 ) q -CR 3 R 4
  • Linkage site with the heterocycle and the heterocycle can also carry one, two or three groups R a ;
  • U is hydrogen, carboxyl, formyl, C 5 -C 8 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 8 -
  • W d-Cio-alkyl, Ci-Cio-haloalkyl, C 2 -Cio-alkenyl, C 2 -Cio-alkynyl, C 3 -C 8 -cycloalkyl, Ca-Cs-cycloalkenyl, phenyl-Ci-Cio-alkyl, wherein W may be unsubstituted or partially or completely halogenated and / or may carry one to three radicals from the group R a ;
  • X is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl or C 2 -C 6 -halo-genalkinyl; and agriculturally acceptable salts thereof, for controlling phytopathogenic fungi.
  • the invention relates to novel triazolopyrimidines, processes and intermediates for the preparation of these compounds, and agents containing them.
  • the compounds according to the invention differ from those described in the abovementioned publications essentially by the configuration of the group X or W.
  • the effect of the known compounds is in many cases unsatisfactory.
  • the object of the present invention is to provide compounds with improved activity and / or broadened spectrum of activity.
  • 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 [cf. 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.
  • tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine, tributylamine and N-methylpiperidine, N-methylmorpholine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethyl-aminopyridine and bicyclic amines into consideration.
  • tertiary amines such as diisopropylethylamine, 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.
  • Substituted malonates of the formula IIb are advantageously prepared from the reaction of corresponding alkyl, alkenyl or alkynyl halides, in particular the bromides, with dialkyl malonates 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] received.
  • This reaction is advantageously carried out at 0 0 C to 7O 0 C, preferably 1O 0 C to 35 0 C, preferably in the presence of an inert solvent such as ethers, eg. As dioxane, diethyl ether or especially tetrahydrofuran, halogenated hydrocarbons such as dichloromethane and aromatic hydrocarbons such as toluene [cp. WO 98/46608; WO 03/009687].
  • ethers eg. As dioxane, diethyl ether or especially tetrahydrofuran, halogenated hydrocarbons such as dichloromethane and aromatic hydrocarbons such as toluene [cp. WO 98/46608; WO 03/009687].
  • a base such as tertiary amines, for example triethylamine or inorganic bases, such as potassium carbonate is preferred; Excess amine of the formula IM can also serve as a base.
  • the subsequent saponification of the ester VI is carried out under generally customary conditions, depending on the various structural elements, the alkaline or the acidic saponification of the compounds VI may be advantageous.
  • the decarboxylation to 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, 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.
  • 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.
  • X is preferably C 1 -C 4 -alkyl.
  • the preparation of the compounds IMa takes place advantageously under known conditions [cf. Chemistry Letters, pp. 367-370, 1981; EP-A 10 02 788; Organikum, VEB German publishing house of the sciences, Berlin 1988, S. 517].
  • the 5-alkyl-7-hydroxy-6-alkyltriazolopyrimidines IVa thus obtained are reacted with halogenating agents [HAL] under the conditions described above to give the 7-halotriazolopyrimidines of the formula Va in which Hal is a halogen atom.
  • chlorinating or brominating agents such as phosphorus oxybromide, phosphorus oxychloride, thionyl chloride, thionyl bromide or sulfuryl chloride.
  • the reaction may be carried out neat or in the presence of a solvent. Typical reaction temperatures are from 0 to 15O 0 C or preferably from 80 to 125 0 C.
  • M is a metal ion of valence Y, such as Mg-HaI to form Grignard compounds, Li, B, Zn or Sn and X "is C 1 -C 3 -alkyl
  • valence Y such as Mg-HaI to form Grignard compounds, Li, B, Zn or Sn and X "is C 1 -C 3 -alkyl
  • the compounds of the formula I in which Z in R 1 is not hydrogen may also be prepared from hydroxy- or mercaptotriazolopyrimidines of the formula Ia.
  • the 7-hydroxy, or mercaptoaminotriazolopyrimidine of the formula Ia is reacted with an alkylating or acylating agent Z-L, where L is a nucleophilic cleavable group.
  • L is a nucleophilic cleavable group.
  • carboxylic anhydrides such as.
  • carboxylic acids used in conjunction with coupling reagents such as di-cyclohexylcarbodiimide or acids, such as HCl.
  • the reaction conditions suitable for the prevention or esterification are generally known to the person skilled in the art [cf .: Organikum, VEB Deutscher Verlag dermaschineen, Berlin (1981)].
  • the compounds of formula Ia are z. T. known from the documents cited above.
  • 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 slightly brownish, viscous oils which are freed from volatile constituents under reduced pressure and at moderately elevated temperature. 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 tion (as mentioned above), wherein in these groups, the hydrogen atoms may be partially 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
  • 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom 5-membered heteroaryl groups, which besides carbon atoms can contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members.
  • 6-membered heteroaryl containing one to three or one to four nitrogen atoms 6-membered heteroaryl containing one to three or one to four nitrogen atoms: 6- 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,
  • Alkylene divalent linear chains of 3 to 5 Chb 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, both valences being 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;
  • R 1 is C 1 -C 4 -alkyl, such as methyl or ethyl, in particular methyl.
  • R 1 is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl which is 1, 2, 3 or 4 times by halogen or C 1 -C 4 -AlkVl can be substituted, or d-Cs-haloalkyl.
  • a particularly preferred embodiment relates to compounds of
  • Z 1 is hydrogen, fluorine or C 1 -C 4 -fluoroalkyl
  • Z 2 is hydrogen or fluorine, or Z 1 and Z 2 together form a double bond
  • j is 0 or 1;
  • R 16 is hydrogen or methyl.
  • R 1 and / or R 2 contain haloalkyl or haloalkenyl groups with chiral centers, the (S) - isomers are preferred for these groups. In the case of halogen-free alkyl or alkenyl groups with chiral centers in R 1 or R 2 , the (R) -configured isomers are preferred.
  • a further embodiment relates to compounds I in which R 1 is C 3 -C 6 -cycloalkyl which may be substituted by C 1 -C 4 -alkyl.
  • a further embodiment relates to compounds I in which R 1 and R 2 together with the nitrogen atom to which they are bonded are saturated or simply unsaturated. saturated, in particular 5 or 6-membered heterocyclyl as defined above. Preferred among these are those compounds in which R 1 and R 2 together with the nitrogen atom to which they are attached form an optionally substituted piperidinyl, morpholinyl or thiomorpholinyl ring, especially a piperidinyl ring.
  • heterocyclyl is unsubstituted or substituted by 1, 2 or 3 substituents R a , with preferred substituents R a of heterocyclyl being selected from halogen, C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl.
  • R 1 and R 2 together with the nitrogen atom to which they are attached are a 4-methylpiperidine ring, a 4-trifluoromethylpiperidine ring, a morpholine ring or a 3,4-dimethylpiperidine ring and especially a 4-methyl - form piperidine ring or a 3,4-dimethylpiperidine ring.
  • R 1 and R 2 together with the nitrogen atom to which they are attached, are 5- or 6-membered heteroaryl as defined above, which may be unsubstituted or substituted, preferably by 1 , 2 or 3 groups R a . In particular, then forms the group
  • NR 1 R 2 is a pyrazole ring, which is optionally substituted in the manner described above, and especially by 1 or 2 of the following radicals: halogen, -C 4 -alkyl or -C 4 -haloalkyl, in particular by 2 methyl groups or 2 Trifluormethylgrup- pen 3, 5 position.
  • a further embodiment relates to compounds I in which the group NR 1 R 2 is ethylglycinol, leucinol, tert-leucinol, valinol, norvalinol, methioninol, phenylalaninol, lysinol, argininol, histidinol, asparaginol, glutaminol, serinol, isoleucinol, cysteinol, hydroxymethylpiperidine, cis-2-hydroxymethyl-4-methyl-piperidine, trans-2-hydroxymethyl-4-methyl-piperidine, cyclohexylgylcinol, cyclopentylglycinol, butylglycinol, pentylglycinol, cis-2-aminocyclohexanol, trans-2-aminocyclohexanol, cis 2-aminocyclopentanol, trans-2-aminocyclopentanol
  • Another object of the invention are compounds I, in which R 1 # -CR 3 R 4 - (CR 5 R 6 ) q - (CR 7 R 8 ) pYZ, where # is the point of attachment to the nitrogen atom.
  • R 2 is hydrogen or C 1 -C 6 -alkyl, such as hydrogen or methyl or ethyl.
  • R 2 is hydrogen.
  • R 3 is straight-chain or branched C 1 -C 8 -alkyl, C 3 -C -alkenyl or C 3 -C 6 -cycloalkyl, in particular Ci-C ⁇ -alkyl or C3-C6-cycloalkyl, preferably iso-propyl, iso-butyl, tert. Butyl, sec. Pen- tyl, cyclopropyl or cyclopentyl, in particular tert. Butyl.
  • Another embodiment relates to compounds I in which R 3 is not hydrogen or methyl.
  • the group R 3 has a branching on the ⁇ -carbon atom.
  • the group R 3 is substituted by heteroatom-bonded groups, such as halogen, alkoxy, alkylthio, amino, alkylamino, dialkylamino or formyl, carboxyl, alkoxycarbonyl, alkoxythiocarbonyl or alkenyl, alkynyl groups or C 2 -C 5 -alkylene, both valences the same carbon atom are bonded.
  • heteroatom-bonded groups such as halogen, alkoxy, alkylthio, amino, alkylamino, dialkylamino or formyl, carboxyl, alkoxycarbonyl, alkoxythiocarbonyl or alkenyl, alkynyl groups or C 2 -C 5 -alkylene, both valences the same carbon atom are bonded.
  • the group R 3 is substituted by C 3 -C 6 -cycloalkyl or C 3 -C 8 -cycloalkenyl.
  • the group R 3 is C (O) R A , C (O) OR A , C (S) OR A , C (O) NR A R B , C (S) NR A R B , C (NR A ) R B , C (O) SR ⁇ or C (S) SR ⁇ substituted.
  • R ⁇ is preferably d-Cs-alkyl or C3-C6-cycloalkyl, which groups may be partially or completely halogenated.
  • the group R 3 is represented by a five, six, seven, eight, nine or ten membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S, substituted.
  • a further embodiment relates to compounds I in which R 4 is hydrogen, straight-chain or branched C 1 -C 5 -alkyl or C 3 -C 6 -cycloalkyl, in particular hydrogen, C 1 -C 6 -alkyl or C 3 -C 6 -cycloalkyl, preferably hydrogen, iso -Propyl, tert. Butyl. If R 4 is an alkyl group, R 4 preferably has the same meaning as R 3 .
  • R 3 and R 4 together form a C 3 -C 6 -alkylene, in particular a C 3 -C 4 -alkylene group, where the carbon chains may be substituted by heteroatom-bonded groups, such as halogen, alkoxy, alkylthio , Amino, alkylamino, dialkylamino or alkoxycarbonyl.
  • R 3 and R 4 together form a C 3 -C 6 -alkylene, in particular a C 3 -C 4 -alkylene group, the carbon chains being interrupted by one or two heteroatoms from the group O, N and S. and may be substituted by heteroatom-bonded groups, such as halogen, alkoxy, alkylthio, amino, alkylamino, dialkylamino or alkoxycarbonyl.
  • R 4 , R 5 , R 6 , R 7 and R 8 are each hydrogen or C 1 -C 4 -alkyl, preferably hydrogen, methyl or ethyl, in particular hydrogen.
  • the substitution of the groups R 4 , R 5 , R 6 , R 7 and R 8 can be carried out according to the group R 3 .
  • R 3 and R 5 together form a C 3 -C 6 -alkylene, C 3 -C 6 -oxyalkylene or C 2 -C 5 -oxyalkyenoxy, in particular a C 3 -C 4 -alkylene group.
  • R 5 and R 6 form and / or R 7 and R 8 respectively together denote a C3-C6-Alkyen-, C3-C6-Oxyalkyen- or C2- Cs-Oxyalkyenoxy-, in particular a C3 C4-Alkyen distr.
  • the index q has the value zero.
  • Another embodiment relates to compounds I in which the index q is 1.
  • Another embodiment relates to compounds I in which the index p is zero or 1, in particular zero.
  • R 5 and R 6 are preferably hydrogen, provided that the index p has the value zero.
  • R 7 is not hydrogen and R 8 is hydrogen, provided that the index p is not equal to zero.
  • the index p has the value zero or 1 and the index q the value 1.
  • R 7 and R 8 are preferably hydrogen. In a further embodiment of the compounds of the formula I, R 7 is not hydrogen and R 8 is hydrogen.
  • Y is oxygen
  • Z represents a monovalent group.
  • a further embodiment relates to compounds I in which Z is C 1 -C 4 -alkylcarbonyl, in particular acetyl, n-propan-1-one, 2-methylpropan-1-one or butan-1-one.
  • Another embodiment relates to compounds I in which Z is hydrogen.
  • Another embodiment relates to compounds I in which Z is carboxyl. Another embodiment relates to compounds I in which Z is formyl.
  • Another embodiment relates to compounds I in which Z is C 1 -C 8 -alkyl.
  • Another embodiment relates to compounds I in which Z is C 1 -C 8 haloalkyl.
  • a further embodiment relates to compounds I in which Z is C 2 -C 8 -alkenyl.
  • Another embodiment relates to compounds I in which Z is C2-C8-haloalkenyl.
  • a further embodiment relates to compounds I in which Z is C2-Cs-alkynyl. Another embodiment relates to compounds I in which Z is C2-C8-haloalkynyl. Another embodiment relates to compounds I in which Z is C3-C6-cycloalkyl.
  • Another embodiment relates to compounds I in which Z is Ca-C ⁇ -cycloalkenyl.
  • a further embodiment relates to compounds I in which Z is C (O) R 1 "1 .
  • a further embodiment relates to compounds I in which Z is C (O) OR 1 "1 .
  • a further embodiment relates to compounds I in which Z is C (S) OR 1 "1 .
  • a further embodiment relates to compounds I in which Z is C (O) SR 1 "1 .
  • a further embodiment relates to compounds I in which ZC (S) SR is ⁇ .
  • a further embodiment relates to compounds I in which Z is C (NR A ) SR ⁇ .
  • a further embodiment relates to compounds I in which Z is C (S) R ⁇ .
  • a further embodiment relates to compounds I in which Z is C (NR ⁇ ) NR A R B.
  • a further embodiment relates to compounds I in which Z is C (NR ⁇ ) R A.
  • a further embodiment relates to compounds I in which Z is C (NR ⁇ ) OR A means.
  • Another embodiment relates to compounds I in which Z is C (O) NR A R B.
  • Another embodiment relates to compounds I in which Z is C (S) NR A R B.
  • Another embodiment relates to compounds I in which Z is C 1 -C 5 -alkylsulfinyl. Another embodiment relates to compounds I in which Z is C 1 -C 6 -alkylthio.
  • a further embodiment relates to compounds I in which Z is C 1 -C 5 -alkylsulfonyl.
  • a further embodiment relates to compounds I in which Z is C (O) -Ci-C 4 -alkylene-NR A C (NR ⁇ ) NR A R B.
  • a further embodiment relates to compounds I in which Z is C (S) -Ci-C 4 -alkylene-NR A C (NR ⁇ ) NR A R B.
  • a further embodiment relates to compounds I in which Z is C (NR ⁇ ) -Ci-C 4 -alkylene-NR A C (NR ⁇ ) NR A R B.
  • Another embodiment relates to compounds I in which Z is phenyl.
  • Another embodiment relates to compounds I in which Z is naphthyl.
  • a further embodiment relates to compounds I in which Z is a five-, six-, seven-, eight-, nine- or ten-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S which is bonded directly or via a carbonyl, thiocarbonyl, C 1 -C 4 -alkylcarbonyl or C 1 -C 4 -alkylthiocarbonyl group.
  • the abovementioned groups Z can be substituted by one or more groups R b .
  • the group Z is substituted by one, two, three or four groups R b , such as halogen, or basic or acidic groups, such as NR A R B , guanidyl, amidyl, hydroxy, carboxyl or sulfonic acids.
  • groups R b such as halogen, or basic or acidic groups, such as NR A R B , guanidyl, amidyl, hydroxy, carboxyl or sulfonic acids.
  • One embodiment relates to compounds I in which X is not methyl.
  • Another embodiment relates to compounds I in which X is alkyl, such as ethyl or n-propyl, in particular ethyl.
  • a further embodiment relates to compounds I in which X is C 3 -C 4 -alkynyl or C 3 -C 4 -haloalkynyl, such as CH 2 C ⁇ CH or CH 2 CH 2 C ⁇ CH.
  • groups R A and R B is hydrogen is Ci-C 4 alkyl or CrC 4 - haloalkyl, preferably hydrogen and methyl.
  • R ⁇ is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, preferably methyl.
  • One embodiment of the group W relates to straight-chain or branched CrCl 2 -alkyl.
  • the alkyl, alkenyl or alkynyl group is represented by a saturated, in particular five- or six-membered, partially unsaturated or aromatic heterocycle having a five, six, seven, eight, nine or ten membered, containing one, two, three or four heteroatoms from the group O, N and S, substituted.
  • Embodiments for alkenyl groups in the position W are the groups W.a and W.b:
  • W 1, W 2 is hydrogen, halogen, Ci -C4 -alkyl, Ci-C 4 haloalkyl, Ci-C4-cyanoalkyl, Ci-C 4 hydroxyalkyl;
  • 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, CH 2 CH 2 F, CH 2 CH 2 Br, CH 2 CHCl 2 , CH 2 CHF 2 , CH 2 CHBr 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 CH 2 CHF 2 , CH 2 CHBr 2 , CH
  • 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 (CHa) 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 (CH 3 ) CH 2 CH 3 , CH 2 CH 2 CH (CHa) 2 , CH (CH 3 ) CH (CHa) 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 (CH 3 ) CH 2 CH 3 , CH 2 CH (CH 3 ) CH (CH 3 ) CH 2 CH 3 , CH 2 CH (CH 3 ) CH (CH 3 ) CH 2 CH 3 , CH 2 CH
  • a preferred embodiment for alkynyl groups in the position W is the group W.c:
  • W 1 and W 2 in the group Wc independently of one another are, 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 ; 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 2 CH
  • W 3 in the group Wc is, for example, branched C 4 -C 6 -alkyl, such as CH (CH 3 ) CH 2 CH 3 , CH 2 CH (CH 2 ) 2 , C (CH 3 ) 3 , CH (CH 3 ) CH 2 CH 2 CHs, CH 2 CH (CH 3 ) CH 2 CH 3 , CH 2 CH 2 CH (CHs) 2 , CH (CH 3 ) CH (CHs) 2 , CH (CH 3 ) CH 2 CH 2 CH 2 CHS,
  • a preferred embodiment for alkyl groups in position W is the group W.d:
  • W 1 means, for example, hydrogen in the group Wd; 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 (CHs) 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,
  • W 2 means in the group Wd, for example, hydrogen or methyl, in particular hydrogen.
  • W 3 in the group Wd is, for example, C 3 -C 6 -alkyl, such as CH (CH 3 ) 2 ,
  • CH 2 CH 2 CH 2 CH 2 CH 3 CH (CH 3) CH 2 CH 3, CH 2 CH (CHs) 2, C (CHs) 3, CH 2 CH 2 CH 2 CH 3, CH (CH) CH 2 CH 2 CH 3 , CH 2 CH (CHs) 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 CH 2 CHS, CH 2 CH (CH 3 ) CH 2 CH 2 CHS, CH 2 CH (CH 3 ) CH 2 CHS, CH (CH 3 ) CH (CHS) CH 2 CH 3 , CH 2 CH (CH 2 CHS) 2 ; C 3 -C 4 halo genalkyl, such as CH (CH 3 ) CHCl 2 , CH (CH 3 ) CHF 2 , CH (CH 3 ) CHBr 2 , CH (CH 3 ) CCI 3 , CH (CH 3 ) CF 3 , CCI
  • group W relates to cycloalkyl groups in which the hydrogen atoms are partially or completely replaced by groups R a .
  • a further embodiment of the group W are cycloalkyl groups, where at least one group R a is ortho to the point of attachment to the triazolopyrimidine scaffold.
  • cycloalkyl groups in the position W are the groups W.e to W.h:
  • W 1 in the group We means, for example, hydrogen or methyl
  • W 2 and W 3 in the group We independently of one another represent, 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 6 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 Wf, Wg and Wh 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.
  • a further embodiment of the invention relates to compounds of the formula 1.1: in which the variables are as defined above.
  • a further embodiment of the invention relates to compounds of the formula I.2,
  • One embodiment relates to compounds of Tables 1 to 2340, in which X is CH 3 and W 2 is H. Another embodiment relates to compounds of Tables 1 to 2340, in which X is CH 3 and W 2 is CH 3 .
  • Another embodiment relates to compounds of Tables 1 to 2340, in which X is CH 3 and W 2 is CF 3 .
  • Another embodiment relates to compounds of Tables 1 to 2340, in which X is CH 3 and W 2 is CN.
  • Another embodiment relates to compounds of Tables 1 to 2340, in which X is CH 3 and W 2 is OH.
  • Another embodiment relates to compounds of Tables 1 to 2340, in which X is CH 3 and W 2 is OCH 3 .
  • Another embodiment relates to compounds of Tables 1 to 2340, in which X is CH 3 and W 2 is F.
  • Another embodiment relates to compounds of Tables 1 to 2340, in which X is CH 3 and W 2 is Cl.
  • Another embodiment relates to compounds of Tables 1 to 2340, in which X is CH 3 and W 2 is Br.
  • Another embodiment relates to compounds of Tables 1 to 2340, in which X is CH 3 and W 2 is CH 2 CH 3 .
  • Another embodiment relates to compounds of Tables 1 to 2340, in which X is CH 3 and W 2 is CH 2 CH 2 OH. Another embodiment relates to compounds of Tables 1 to 2340, in which X is CH 3 and W 2 is CH 2 CCI 3 .
  • Another embodiment relates to compounds of Tables 1 to 2340, 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 2340, in which X is CH 3 and W 2 is C (CH 3 ) 3 .
  • Another embodiment relates to compounds of Tables 1 to 2340 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 2340, in which X is CH 3 and W 2 is CH (CH 3 ) 2 .
  • Another embodiment relates to compounds of Tables 1 to 2340 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 2340, 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 2340 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 2340 in which X is CH 3 and W 2 is CH 2 CH (CHs) 2 .
  • R 1 and R 2 for a compound corresponds in each case to one row of Table A.
  • 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, Basidiomycetes and Peronospomycetes (Syn. 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 pumpkins, as well as the seeds of these plants. They may also be used in cultures tolerant by breeding, including genetic engineering, herbicidal or insect or fungal attack. In addition, they are suitable for the control of Botryosphaeria species, Cylindrocarpon species, Eutypa lata, Neonectria liriodendri and Stereum hirsutum, which attack, among other things, the wood or the roots of grapevines.
  • Ascochyta species on cereals and vegetables e.g. Ascochyta tritici (leaf drought) on wheat, bipolar and Drechslera species on maize (e.g., D. maydis), cereals, rice and turf,
  • Botrytis cinerea (gray mold) on strawberries, vegetables, flowers, vines and wheat (spike mold),
  • 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,
  • Drechslera species Pyrenophora species on maize, cereals, rice and turf, barley (eg D. teres) and wheat (eg D. tritici-repentis), Esca on grapevine caused by Phaeoacremonium chlamydosporium, Ph. Aleophilum, and Formitipora punctata (syn. Phellinus punctatus),
  • Fusarium and Verticillium species on different plants e.g. F. graminearum or F. culmorum (root rot) on cereals (e.g., wheat or barley) or e.g. F. oxysporum on tomatoes and Fusarium solani (stalk disease) on soybeans
  • Gaeumanomyces graminis root black on cereals (for example wheat or cereals),
  • Gibberella species on cereals and rice e.g., Gibberella fujikuroi
  • Michrodochium nivale (snow mold) on cereals (for example wheat or barley),
  • Microsphaera diffusa (powdery mildew) on soybeans, 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 peppers, Phytophthora megasperma (BladtwSgel rot) on soybeans, Phytophthora infestans on potatoes and tomatoes,
  • Puccinia species on various plants e.g. P. triticina, P. striformins, P. hordei or P. graminis on cereals (for example wheat or barley) or asparagus (for example P. asparagi), Pyricularia oryzae, Corticium sasakii, Sarocladium oryzae, S. attenuatum,
  • Pyrenophora tritici-repentis (leaf drought) on wheat or Pyrenophora teres (net spots) on barley, Entyloma oryzae on rice,
  • Pyricularia grisea on lawn and cereals Pythium spp. on turf, rice, corn, wheat, cotton, oilseed rape, sunflowers, sugar beets, vegetables and other plants (for example P. ultiumum or P. aphanidermatum),
  • Ramularia collo-cygni (Ramularia / sunburn complex / Physiological leaf spots) on barley
  • Rhizoctonia species on cotton, rice, potatoes, turf, corn, oilseed rape, potatoes, sugar beets, vegetables and various other plants e.g. Rhizoctonia solani (root / stem rot) on soybeans or Rhizoctonia cerealis (pointed eye spot) on wheat or barley,
  • Venturia species scab
  • apples e.g., V. inaequalis
  • Peronosporomycetes 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 (eg wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
  • 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.
  • Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp .; Basidiomycetes such as Coniophora
  • Tyromyces spp. Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., moreover, in the protection of the following yeasts: Candida spp. and Saccharomyces cerevisae.
  • the compounds I 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.
  • active ingredient in general, 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. Usual application rates are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of material treated in the material protection.
  • 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. Solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the application form depends on the respective purpose; It should in any case ensure a fine and uniform distribution of the compound according to the invention.
  • the formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants. Suitable solvents / auxiliaries are essentially:
  • aromatic solvents eg Solvesso products, xylene
  • paraffins eg petroleum fractions
  • alcohols eg methanol, butanol, pentanol, benzyl alcohol
  • ketones eg cyclohexanone, gamma-butyrolactone
  • pyrrolidones NMP, NOP
  • Acetates glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters.
  • solvent mixtures can also be used
  • - Carriers such as ground natural minerals (eg kaolins, clays, talc, chalk) and ground synthetic minerals (eg fumed silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene) Fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin liquors and methylcellulose.
  • ground natural minerals eg kaolins, clays, talc, chalk
  • ground synthetic minerals eg fumed silica, silicates
  • Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene) Fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin liquors and methylcellulose.
  • the surface-active substances used are alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, and 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
  • 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, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong polar solvents, e.g. Dimethylsulfoxide, N-methylpyrrolidone or water into consideration.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthal
  • 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 25 parts by weight of the active compounds are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
  • This mixture is added to water by means of an emulsifying machine (e.g., Ultraturax) in 30 parts by weight and made into a homogeneous emulsion. Dilution in water results in an emulsion.
  • 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.
  • Water-dispersible and water-soluble granules 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.
  • Water-dispersible and water-soluble powders 75 parts by weight of the active compounds are ground in a rotor-stator mill with the addition of 25 parts by weight of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active ingredient content of the formulation is 75% by weight.
  • 0.5 parts by weight of the active ingredients are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for direct application with 0.5 wt .-% active ingredient content.
  • LS water-soluble concentrates
  • FS suspensions
  • DS water-dispersible and water-soluble powders
  • WS water-dispersible and water-soluble powders
  • ES emulsions
  • EC emulsifiable concentrates
  • gel formulations GF
  • 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.
  • 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.
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume
  • wetting agents eg. Break Thru S 240 ®
  • Alcohol alkoxylates eg. As Atplus 245 ®, Atplus MBA 1303 ®, Plurafac LF 300 ® and Lutensol ON 30 ®
  • EO-PO block polymers eg. B.
  • Pluronic RPE 2035 ® and Genapol B ® Alcohol ethoxylates, eg. As Lutensol XP 80 ®; and sodium dioctylsulfosuccinate, e.g. B. Leophen RA ®.
  • the agents according to the invention in the form of application as fungicides, may also be present together with other active substances, e.g. with herbicides, insecticides, growth regulators, fungicides or with fertilizers.
  • other active substances e.g. with herbicides, insecticides, growth regulators, fungicides or with fertilizers.
  • the compounds (I) or the agents containing them with one or more further active compounds, in particular fungicides, for example, in many cases, the activity spectrum can be broadened or development of resistance can be prevented. In many cases, synergistic effects are obtained.
  • Azoxystrobin Dimoxystrobin, Enestroburin, Fluoxastrobin, Kresoxim-methyl, Methominostrobin, Orysastrobin, Picoxystrobin, Pyraclostrobin, Pyribencarb, Trifloxystrobin, 2- (2- (6- (3-chloro-2-methylphenoxy) -5-fluoropyrimidine 4-yloxy) -phenyl) -2-methoxyimino-N-methyl-acetamide, 2- (ortho - ((2,5-dimethylphenyl-oxymethylene) -phenyl) -3-methoxy-acrylic acid methyl ester, 3-methoxy-2- (2 - (N- (4-methoxy-phenyl) -cyclopropanecarbox-imidoylsulfanylmethyl) -phenyl) -acrylic acid methyl ester;
  • Carboxylic acid morpholides Dimethomorph, Flumorph; Benzoic acid amides: flumetover, fluopicolide, fluopyram, zoxamide, N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formylamino-2-hydroxybenzamide;
  • carboxamides carpropamide, diclocymet, mandipropamide, oxytetracycline, silthiofam, N- (6-methoxypyridin-3-yl) cyclopropanecarboxamide; azoles
  • Triazoles azaconazole, bitertanol, bromuconazoles, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothiocona - zole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, 1- (4-chloro-phenyl) -2 - ([1, 2,4] triazol-1-yl) -cycloheptanol;
  • - imidazoles cyazofamide, imazalil, imazalil sulfate, pefurazoate, prochloraz, triflumizole;
  • Benzimidazoles benomyl, carbendazim, fuberidazole, thiabendazole; Other: Ethaboxam, Etridiazole, Hymexazole, 1- (4-Chloro-phenyl) -1- (propyn-2-yl-oxy) -3- (4- (3,4-dimethoxyphenyl) -isoxazole-5- yl) -propan-2-one; Nitrogen-containing heterocyclyl compounds
  • - pyrimidines bupirimate, cyprodinil, diflumetorim, fenarimol, ferimzone, mepanipyrim, nitrapyrin, nuarimol, pyrimethanil;
  • - Pyrroles fludioxonil, fenpiclonil
  • - morpholines aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph
  • Dicarboximides fluoroimide, iprodione, procymidone, vinclozolin;
  • acibenzolar-S-methyl acibenzolar-S-methyl, amisulbrom, anilazine, blasticidin-S, captafol, captan, quinomethionate, dazomet, debacarb, diclomethine, difenzoquat, difenzoquat-methylsulphate, famoxadone, fenamidone, fenoxanil, fenpropidin,
  • Folpet octhilinone, oxolinic acid, piperaline, samplesazoles, proquinazide, pyroquilon, quinoxyfen, triazoxide, tricyclazoles, triforines, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluoro -phenyl) - [1,2,4] triazolo [1,5-a] pyimidine, 2-butoxy-6-iodo-3-propylgamate
  • A-ismi dithiocarbamate - thio- and dithiocarbamate Ferbam, Mancozeb, Maneb, Metam , Methasulphocarb, Metiram, Propineb, Thiram, Zineb, Ziram;
  • Guanidines dodine, dodine free base, guazatine, guazatine acetate, iminoctadine, iminoctadine triacetate, iminoctadine tris (albesilat); - antibiotics: kasugamycin, kasugamycin hydrochloride hydrate, polyoxins, streptomycin, validamycin A;
  • Organometallic compounds Fentin salts such as, for example, fentin acetate, fentin chloride, fentin hydroxide;
  • Sulfur-containing heterocyclyl compounds isoprothiolanes, dithianone;
  • Organophosphorus compounds edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, pyrazophos, tolclofos-methyl;
  • Organochlorine compounds chlorothalonil, dichlofluanid, dichlorophen, flusulfamides, hexachlorobenzene, pencycuron, pentachlorophenol and its salts, phtha-Nd, quintozene, thiophanate-methyl, tolylfluanid, N- (4-chloro-2-nitrophenyl) -N- ethyl-4-methyl-benzenesulfonamide;
  • Inorganic active substances Phosphorous acid and its salts, sulfur, Bordeaux broth, copper salts such as copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate;
  • Step A 2-Cyclopentyl-3-oxo-butyric acid ethyl ester
  • a solution of 5.75 g (0.25 mol) of sodium in 75 ml of ethanol was added dropwise within 15 min with 32.5 g (0.25 mol) of ethyl acetonate, Stirred 15 minutes further at 20 to 25 ° C, then added dropwise at 75 ° C 37.25 g (0.25 mol) of cyclopentyl bromide. After a further 15 hours of stirring at 75 ° C, the suspension was added to ice-water, extracted with methyl tert-butyl ether (MTBE), the combined MTBE phases with water and sat. NaCl solution. washed, dried and freed from the solvent. From the residue, 36 g of the title compound was fractionally distilled.
  • MTBE methyl tert-butyl ether
  • Step B 6-Cyclopentyl-5-methyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-ol 1 g (5 mmol) of the product from Step A was refluxed with 0.42 g (5 mmol) of amitrole and 10 ml of propionic acid for 15 hrs. The mixture was freed of solvent and poured into water. After neutralization with NaOH, the crystallized title compound was filtered off. 0.7 g of light brown crystals were obtained.
  • Step C / -chloro- ⁇ -cyclopentyl-S-methyl-fi ⁇ triazolo ⁇ .S-alpyrimidine
  • Step D (6-Cyclopentyl-5-methyl- [1,2,4] triazolo [1,5-a] pyrimidin-7-yl) - (S-2,2,2-trifluoro-1-methyl-ethyl ) amine
  • HPLC retention times (RT) in the following table were determined using the RP-18 column Chromolith Speed ROD (Merck KGaA, Germany) with the eluent acetonitrile + 0.1% trifluoroacetic acid (TFA) / water + 0, 1% TFA in one
  • the fungicidal activity of the compounds of the formula I was demonstrated by the following experiments:
  • the active compounds were prepared as a stock solution with 25 mg of active compound which was treated with a mixture of acetone and / or DMSO and the emulsifier Uniperol® EL (wetting agent with emulsifying and Dispersing effect based on ethoxylated alkylphenols) in the volume ratio solvent-emulsifier of 99 to 1 ad 10 ml was made up. 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 effect based on ethoxylated alkylphenols
  • Leaves of pot fry were sprayed to drip point with aqueous suspension in the concentration of active compound given below.
  • the undersurfaces of the leaves were inoculated with an aqueous sporangia suspension of Plasmopara viticola.
  • the vines were first set up for 24 hours in a water vapor-saturated chamber at 24 0 C and then for 5 days in a greenhouse at temperatures between 20 and 30 0 C. After this time, the plants were again placed in a humid chamber for 16 hours to accelerate the sporangiopathic outbreak. Then the extent of infestation on the undersides of the leaves was visually determined.
  • Leaves of potted wheat seedlings were sprayed to drip point with aqueous suspension in the concentration of active compound given below. Twenty-four hours after the spray coating had dried on, they were inoculated with an aqueous spore suspension of Septoria tritici. The test plants were then placed in the greenhouse for 3 days at temperatures between 16 and 22 ° C and a relative humidity near 100%, then at a relative humidity of about 70%. After 4 weeks, the extent of disease development was determined visually in% infestation of the total leaf area.
  • the active ingredients were formulated separately as stock solution with a concentration of
  • the stock solution is pipetted into a microtiter plate (MTP) and diluted with an aqueous malt-based mushroom nutrient medium to the stated active substance concentration. This was followed by the addition of an aqueous spore suspension of Botrytis cinerea.
  • MTP microtiter plate
  • the plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. With an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.
  • the measured parameters were compared with the growth of the active ingredient-free control variant and the fungus-free and active substance-free blank value in order to determine the relative growth in% of the pathogens in the individual active substances.
  • the stock solution is pipetted into a microtiter plate (MTP) and diluted to the indicated drug concentration with an aqueous, pea-based, mushroom nutrient medium. This was followed by the addition of an aqueous zoospore suspension of Phytophthora infestans.
  • 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 evaluation was carried out analogously to application example 4.
  • the stock solution is pipetted into a microtiter plate (MTP) and diluted with an aqueous malt-based fungal nutrient medium to the stated active substance concentration. This was followed by the addition of an aqueous spore suspension of Pyricularia oryzae.
  • MTP microtiter plate
  • the plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. With an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation. The evaluation was carried out analogously to application example 4.
  • the active compounds were formulated as described before Application Example 1.
  • Leaves of potted rice seedlings of the cultivar "Tai-Nong 67" were sprayed to drip point with aqueous suspension in the concentration of active compound stated below. The following day, the plants were inoculated with an aqueous spore suspension of Pyricularia oryzae. Subsequently, the test plants were placed in climatic chambers at 22 - 24 0 C and 95 - 99% relative humidity for 6 days. Then the extent of infestation on the leaves was visually determined. In this test, the plants treated with 63 ppm of Compound I-49 showed 5% infestation, while the plants treated with 63 ppm of Compound Compound H were 90% infested.
  • 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 infected with an aqueous sporangium suspension of Phytophthora infestans. Subsequently, the plants were 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%.

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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 l'utilisation de triazolopyrimidines substituées représentées par la formule (I), dans laquelle les substituants ont les significations données dans le descriptif, dans la lutte contre des champignons phytopathogènes, de nouvelles triazolopyrimidines, des procédés et des produits intermédiaires destinés à la fabrication des triazolopyrimidines, et des agents les contenant.
PCT/EP2007/052796 2006-03-30 2007-03-23 Utilisation de triazolopyrimidines substituées dans la lutte contre des champignons phytopathogènes Ceased WO2007113136A1 (fr)

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EP06112040.8 2006-03-30
EP06112040 2006-03-30
EP06115435.7 2006-06-14
EP06115435 2006-06-14

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WO2007113136A1 true WO2007113136A1 (fr) 2007-10-11

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108349979A (zh) * 2015-11-02 2018-07-31 詹森药业有限公司 [1,2,4]三唑并[1,5-a]嘧啶-7-基化合物
US10947242B2 (en) 2016-11-02 2021-03-16 Janssen Pharmaceutica, Nv [1,2,4]triazolo[1,5and#8208;A]pyrimidine compounds as PDE2 inhibitors
US11053248B2 (en) 2016-11-02 2021-07-06 Janssen Pharmaceutica Nv [1,2,4]triazolo[1,5-a]pyrimidine compounds as PDE2 inhibitors
US11319321B2 (en) 2016-11-02 2022-05-03 Janssen Pharmaceutica Nv [1,2,4]triazolo[1,5-a]pyrimidine compounds as PDE2 inhibitors

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US5387747A (en) * 1992-02-24 1995-02-07 Laboratoires Upsa Triazolopyrimidine derivatives which are angiotensin II receptor antagonists, their methods of preparation and pharmaceutical compositions in which they are present
WO2003009687A1 (fr) * 2001-07-26 2003-02-06 Basf Aktiengesellschaft 7-amino-triazolopyrimidines pour la lutte contre des champignons nuisibles
WO2005087771A2 (fr) * 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, procedes pour leur production, leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant
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EP0141317A2 (fr) * 1983-10-21 1985-05-15 BASF Aktiengesellschaft 7-Amino-azolo[1,5-a]pyrimidines et fongicides les contenant
US5387747A (en) * 1992-02-24 1995-02-07 Laboratoires Upsa Triazolopyrimidine derivatives which are angiotensin II receptor antagonists, their methods of preparation and pharmaceutical compositions in which they are present
WO2003009687A1 (fr) * 2001-07-26 2003-02-06 Basf Aktiengesellschaft 7-amino-triazolopyrimidines pour la lutte contre des champignons nuisibles
WO2005087771A2 (fr) * 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, procedes pour leur production, leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant
WO2005087770A2 (fr) * 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, procedes pour leur production, leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant
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WO2005120233A1 (fr) * 2004-06-09 2005-12-22 Basf Aktiengesellschaft Composes de triazolopyrimidine et leur utilisation pour lutter contre des champignons nocifs
WO2006000436A1 (fr) * 2004-06-25 2006-01-05 Basf Aktiengesellschaft Composes tirazolopyrimidine et leur utilisation pour lutter contre des champignons nuisibles
WO2006005492A1 (fr) * 2004-07-08 2006-01-19 Basf Aktiengesellschaft 6-phenyl-7-amino-triazolopyrimidines substituees, procedes permettant de les produire et leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant
WO2006027170A1 (fr) * 2004-09-08 2006-03-16 Basf Aktiengesellschaft 6-phenyl-7-amino-triazolopyrimidines, leurs procedes de production et leur utilisation pour lutter contre les champignons nuisibles, et agents les contenant

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108349979A (zh) * 2015-11-02 2018-07-31 詹森药业有限公司 [1,2,4]三唑并[1,5-a]嘧啶-7-基化合物
US10947239B2 (en) 2015-11-02 2021-03-16 Janssen Pharmaceutica Nv [1,2,4]triazolo[1,5-a]pyrimidin-7-yl compound
CN108349979B (zh) * 2015-11-02 2021-04-09 詹森药业有限公司 [1,2,4]三唑并[1,5-a]嘧啶-7-基化合物
US10947242B2 (en) 2016-11-02 2021-03-16 Janssen Pharmaceutica, Nv [1,2,4]triazolo[1,5and#8208;A]pyrimidine compounds as PDE2 inhibitors
US11053248B2 (en) 2016-11-02 2021-07-06 Janssen Pharmaceutica Nv [1,2,4]triazolo[1,5-a]pyrimidine compounds as PDE2 inhibitors
US11319321B2 (en) 2016-11-02 2022-05-03 Janssen Pharmaceutica Nv [1,2,4]triazolo[1,5-a]pyrimidine compounds as PDE2 inhibitors

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