EP1797095A1 - 6-phenyl-7-amino-triazolopyrimidines, leurs procedes de production et leur utilisation pour lutter contre les champignons nuisibles, et agents les contenant - Google Patents

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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Publication number
EP1797095A1
EP1797095A1 EP05784802A EP05784802A EP1797095A1 EP 1797095 A1 EP1797095 A1 EP 1797095A1 EP 05784802 A EP05784802 A EP 05784802A EP 05784802 A EP05784802 A EP 05784802A EP 1797095 A1 EP1797095 A1 EP 1797095A1
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European Patent Office
Prior art keywords
formula
hydrogen
alkyl
compounds
group
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EP05784802A
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German (de)
English (en)
Inventor
Carsten Blettner
Jordi Tormo I Blasco
Bernd Müller
Markus Gewehr
Wassilios Grammenos
Thomas Grote
Udo HÜNGER
Joachim Rheinheimer
Peter Schäfer
Frank Schieweck
Anja Schwögler
Jochen Dietz
John-Bryan Speakman
Thorsten Jabs
Siegfried Strathmann
Ulrich Schöfl
Maria Scherer
Reinhard Stierl
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BASF SE
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BASF SE
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Publication of EP1797095A1 publication Critical patent/EP1797095A1/fr
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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • 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

  • 6-phenyl-7-amino-triazolopyrimidines process for their preparation and their use for controlling harmful fungi and agents containing them
  • the present invention relates to 6-phenyl-7-amino-triazolopyrimidines of the formula I.
  • R 1 is hydrogen, C 1 -C 12 -alkyl, -C 12 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 8 -HaIo- gencycloalkyl, C 2 -C 2 -alkenyl, C 2 -C 12 haloalkenyl , C 3 -C 6 cycloalkenyl, C 3 -C 6 - halocycloalkenyl, C 2 -C 12 -AIkinyl, C 2 -C 12 -haloalkynyl or phenyl, naphthyl, or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one to four heteroatoms from the group O 1 N or S,
  • R 3 , R 4 , R 5 , R 6 , R 7 is hydrogen or one of the groups mentioned for R 2 ,
  • R 4 can also form with R 3 or R 6 a five- or six-membered saturated or unsaturated ring containing, in addition to carbon atoms, one to three further heteroatoms from the group O, N and S as ring member and / or one or more substituents R a can carry;
  • R 2 with R 3 , R 4 with R 5 , R 6 with R 7 may each also together to form
  • Carbonyl groups represent oxygen and to form spiro groups form a C 2 -C 5 alkylene or alkenylene, alkynylene, which may be interrupted by one to three heteroatoms from the group O, N and S;
  • R 1 to R 7 may each carry one to four identical or different groups R a :
  • R a is halogen, cyano, nitro, hydroxy, C r C 6 alkyl, CRCE haloalkyl, C 1 -C 6 kylcarbonyl -Al-, C 3 -C 6 cycloalkyl, C 1 -C 6 -alkoxy, d-Ce Haloalkoxy, C 1 -C 6 - Alkoxycarbonyl, C r C 6 alkylthio, C r C 6 -AlkyIamino, di-CrC 6 alkylamino, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 3 -C 8 cycloalkenyl, C 2 - C 6 -alkenyl-oxy, C 3 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -alkin
  • R b is halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, amino carbonyl, aminothiocarbonyl, alkyl, haloalkyl, alkenyl, alkenyloxy, alkynyloxy, alkoxy, haloalkoxy, alkylthio, alkylamino, dialkylamino,
  • Haloalkyl phenomenon can be substituted
  • p is zero or 1;
  • L is halo, C 1 -C 4 alkyl, dC 2 haloalkyl, C 1 -C 4 -alkoxy, cyano, nitro, amino, CrC 4 -AIkylamino, di- (Ci-C4) alkylamino, -C 4 alkylcarbonylamino , C (O) -R, S (O) n -R;
  • R is hydrogen, C - ⁇ - alkyl, d-Ca-haloalkyl, C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyl oxy, C 2 -C 4 alkynyloxy, amino, C r C 4 alkylamino, Di (C 1 -C 4 ) alkylamino; where the groups R can be substituted by one to three groups R b ; n is zero, 1 or 2;
  • n 1, 2, 3, 4 or 5;
  • X is halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyloxy, C 2 -C 4 -alkyl-oxyloxy or C 1 -C 4 -haloalkoxy,
  • Z can also form with R 5 or R 7 a five- or six-membered saturated or unsaturated ring which, in addition to carbon atoms and Y, contains one or two further heteroatoms from the group O, N and S as ring member and / or ei ⁇ may carry one or more substituents R a ;
  • the group Z may be partially or completely halogenated or carry one to three groups R b ;
  • R A, R B are independently hydrogen, C 1 -C 8 -alkyl C 2 -C 8 1 -AIKenyl, C 2 -C 8 - alkynyl, C 3 -C 6 -cycloalkyl or C 3 -C 6 cycloalkenyl;
  • R A and R B together with the nitrogen atom to which they are attached, form a five- or six-membered saturated, partially unsaturated or aromatic ring which, besides carbon atoms, contains one to three further heteroatoms from the group O, N and Contain S as Ring ⁇ member and / or can carry one or more substituents R a .
  • the invention relates to processes and intermediates for the preparation of these compounds, compounds containing them and their use for controlling phytopathogenic harmful fungi.
  • 6-phenyl-7-amino-triazolopyrimidines are well known. 6-phenyl-7-amino-triazolopyrimidines having 7-amino substituents containing hydroxy or ether groups are disclosed in EP-A 550,113, US 5,993,996, US 6,117,865, US 6,297,251 and WO 98/46607. These compounds are known for controlling harmful fungi.
  • the compounds according to the invention differ from the compounds disclosed in the abovementioned publications by the specific embodiment of the 7-amino group which has a branching on the ⁇ -carbon atom.
  • the object of the present invention is to provide compounds having an improved action and / or a broadened spectrum of activity.
  • the compounds of the invention can be obtained in various ways.
  • they are prepared by reacting 7-DihalogentriazoIopyrimidinen of formula II with amines of formula III, in which the variables are as defined for formula I.
  • This reaction is advantageously at 0 ° C to 7O 0 C, preferably 1O 0 C to 35 0 C Deutschenge leads, preferably in the presence of an inert solvent such as ether, z.
  • an inert solvent such as ether, z.
  • ether for example, dioxane, diethyl ether or, in particular, tetrahydrofuran, halogenated hydrocarbons, such as dichloromethane, and aromatic hydrocarbons, for example toluene [cf. WO-A 98/46608].
  • a base such as tertiary amines, for example triethylamine or inorganic amines, such as potassium carbonate is preferred; Excess amine of the formula III can also serve as a base.
  • 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.
  • the reaction conditions suitable for the etherification or esterification are generally known to the person skilled in the art [cf .: Organikum, VEB Deutscher Verlag dermaschineen, Berlin (1981)].
  • Amines of the formulas III and IIIa are known in the literature, can be prepared by known methods or are commercially available.
  • Compounds of the formula I in which X is cyano, C 1 -C 6 -alkoxy or C r C 2 -haloalkoxy can advantageously be prepared from the reaction of compounds I in which X is halogen, preferably chlorine, with compounds MX '(formula IV).
  • Compounds IV depending on the meaning of the group X 'to be introduced, are an inorganic cyanide, an alkoxylate or a haloalkoxylate.
  • the reaction is advantageously carried out in the presence of an inert solvent.
  • the cation M in formula IV has little significance; For practical reasons, ammonium, tetraalkylammonium or alkali or alkaline earth metal salts are usually preferred.
  • reaction temperature is usually 0 to 12O 0 C, preferably 10 to 40 0 C [see. J. Heterocycl. Chem., Vol. 12, pp. 861-863 (1975)].
  • Suitable solvents include ethers such as dioxane, diethyl ether and, preferably, tetrahydrofuran, halogenated hydrocarbons such as dichloromethane and aromatic hydrocarbons such as toluene.
  • the subsequent saponification of the ester VII takes place under generally customary conditions; depending on the various structural elements, the alkaline or acidic saponification of the compounds VII can be advantageous.
  • the decarboxylation to I can already take place completely or partially.
  • the decarboxylation is usually carried out at temperatures of from 2O 0 C to 18O 0 C 1 vor ⁇ preferably 5O 0 C to 12O 0 C, in an inert solvent, optionally in the presence of an acid presence.
  • 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.
  • M is a metal ion of valence Y, such as B, Zn or Sn and X "is C 1 -C 3 -alkyl.
  • This reaction can be carried out, for example, analogously to the following methods: J. Chem. Soc. Perkin Trans. 1, 1187 (1994), ibid. 1, 2345 (1996); WO 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 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 from volatile constituents under reduced pressure and at a moderately elevated temperature. If the intermediate and end products are obtained as solids, the purification can also be carried out by recrystallization or trituration.
  • individual compounds I are not accessible in the above-described ways, they can be prepared by derivatization of other compounds I. However, if isomer mixtures are obtained in the synthesis, a separation is generally not necessary, since the individual isomers can partly interconvert during preparation for use or during use (eg under the action of light, acid or base). Corresponding conversions can also take place after use, for example in the treatment of plants in the treated plant or in the harmful fungus to be controlled.
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkyl saturated, straight-chain or branched hydrocarbon radicals having from 1 to 4, 6 or 8 carbon atoms, for example C r 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-methyl pentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1, 2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylphenyl, 3,3- Dimethylbutyl, 1-ethylbutyl, 2-ethylbuty
  • 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-trichloroe
  • Alkenyl unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, 6 or 8 carbon atoms and one or two double bonds in any position, for example C 2 -C 6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethyl , 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-i-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-propen
  • Haloalkenyl unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 8 carbon atoms and one or two double bonds in any position (as mentioned above), wherein in these groups, the hydrogen atoms partially or completely replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine could be;
  • Alkynyl straight-chain or branched hydrocarbon groups 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, for example C 3 -C 8 -cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl;
  • 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 for example 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-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolid
  • 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 contain, in addition to carbon atoms, one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members can, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, and 1, 3,4-triazol-2-yl;
  • 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 unbranched chains of 3 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 J
  • Oxyalkylene divalent unbranched chains of 2 to 4 CH 2 groups, wherein a Va ⁇ lenz is bound via an oxygen atom to the skeleton, 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 CH 2 groups, both valences being bonded to the skeleton via an oxygen atom, eg OCH 2 O, OCH 2 CH 2 O and OCH 2 CH 2 CH 2 O;
  • R 1 is hydrogen or C 1 -C 4 -alkyl, such as hydrogen or methyl or ethyl, in particular hydrogen.
  • R 2 is C 1 -C 8 -alkyl or C 3 -C 6 -cycloalkyl, in particular C 1 -C 6 -alkyl or C 3 -C 6 -cycloalkyl, preferably methyl, ethyl , iso-propyl, iso-butyl, tert. Butyl, sec. Pentyl, cyclopropyl or cyclopentyl, in particular tert. Butyl.
  • R 3 is hydrogen, CrC ⁇ alkyl or C 3 -C 6 cycloalkyl, especially hydrogen, CrC 6 alkyl or C 3 -C 6 - cycloalkyl, preferably hydrogen, methyl, ethyl, n- Propyl or iso-propyl. If R 3 is an alkyl group, R 3 preferably has the same meaning as R 2 .
  • R 2 and R 3 together form a C 3 -C 6 -alkylene, in particular a C 3 -C 4 -alkylene group.
  • R 4 , R 5 , R 6 and R 7 are each hydrogen or C 1 -C 4 -alkyl, in particular hydrogen, methyl or ethyl, in particular hydrogen.
  • R 4 and R 5 and / or R 6 and R 7 in each case 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.
  • the index p has the value zero.
  • Y is oxygen
  • Z represents a monovalent group.
  • Alkyl, or -C 4 -alkylcarbonyl in particular methyl, ethyl, n-propyl, iso-propyl, acetyl tyl, propane-1-one or butane-1 -
  • X is halogen, C 1 -C 4 -alkyl, cyano or C 1 - C 4 alkoxy means such as chlorine, bromine, methyl, cyano, methoxy or ethoxy, especially chlorine.
  • At least one group L is ortho to the point of attachment to the triazolopyrimidine skeleton, in particular chlorine, fluorine or methyl.
  • # is the point of attachment to the triazolopyrimidine skeleton and L 1 is fluorine, chlorine, CH 3 or CF 3 ; L 2 , L 4 are independently hydrogen or fluorine;
  • L 3 is hydrogen, fluorine, chlorine, CN, CH 3 , OCH 3 , NH 2 , NHCH 3 , N (CH 3 ) 2 , C (O) NH 2 or C (O) CH 3 ; and L 5 is hydrogen, fluorine, chlorine or CH 3 .
  • L m is one of the following substituent combinations: 2-fluoro-6-chloro, 2,6-difluoro, 2,6-dichloro, 2-fluoro-6-methyl, 2,4 , 6-trifluoro, 2,6-difluoro-4-methoxy, 2-chloro-4-methoxy, pentafluoro, 2-methyl-4-fluoro, 2-trifluoromethyl, 2-methoxy-6-fluoro, 2-chloro, 2 Fluorine, 2,4-difluoro, 2-fluoro-4-chloro, 2-chloro-4-fluoro, 2-chloro-5-fluoro, 2,3-difluoro, 2,5-difluoro, 2,3,4 Trifluoro, 2-methyl, 2,4-dimethyl, 2-methyl-4-chloro, 2-methyl-5-fluoro, 2-fluoro-4-methyl, 2,6-dimethyl, 2,4,6-trimethyl , 2,6-Difluoro
  • a further preferred embodiment of the invention relates to compounds of the formula I.1:
  • a further embodiment of the invention relates to compounds of the formula I.2,
  • a further embodiment of the invention relates to compounds of the formulas I and 1.1 in which Z represents a group bonded via a carbonyl group.
  • Table 7 Compounds of the formula 1.1 in which X is chlorine, L m is pentafluoro and R 1 , R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound of one row of Table A corresponds to
  • Table 10 Compounds of the formula 1.1 in which X is chlorine, L m is 2-methoxy-6-fluoro and R 1 , R 4 and R 5 is hydrogen and the combination of R 2 , R 3 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 11 Compounds of the formula 1.1 in which X is chlorine, L m is 2-chloro and R 1 , R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound of one line in each case Table A corresponds
  • Table 12 Compounds of the formula 1.1 in which X is chlorine, L m is 2-fluoro and R 1 , R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound of one line in each case Table A corresponds
  • Table 14 Compounds of the formula 1.1, in which X is chlorine, L m is 2-fluoro-4-chloro, and R 1 , R 4 and R 5 are hydrogen, and the combination of R 2 , R 3 , Y and Z for each compound Line of Table A corresponds
  • Table 15 Compounds of the formula 1.1 in which X is chlorine, L n, 2-chloro-4-fluoro and R 1, R 4 and R 5 are hydrogen and the combination of R 2, R 3, Y and Z for each compound corresponds to one line of Table A.
  • Table 18 Compounds of the formula 1.1 in which X is chlorine, L m is 2,3,4-trifluoro and R 1 , R 4 and R 5 Represent hydrogen and the combination of R 2 , R 3 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 19 Compounds of the formula 1.1, in which X is chlorine, L m is 2-methyl and R 1 , R 4 and R 5 are hydrogen, and the combination of R 2 , R 3 , Y and Z is a compound of one line in each case Table A corresponds
  • Table 20 Compounds of the formula 1.1, in which X is chlorine, I_ m is 2,4-dimethyl and R 1 , R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound of one line in each case Table A corresponds
  • Table 23 Compounds of the formula 1.1, in which X is chlorine, L m is 2,6-dimethyl and R 1 , R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound of one row each of Table A corresponds
  • Table 25 Compounds of the formula 1.1, in which X is chlorine, L m is 2,6-difluoro-4-methyl and R 1 , R 4 and R 5 are hydrogen, and the combination of R 2 , R 3 , Y and Z is a compound corresponds to one row of Table A.
  • Table 27 Compounds of the formula 1.1 in which X is chlorine, L m is 2-trifluoromethyl-5-fluoro and R 1, R 4 and R 5 are hydrogen and the combination of R 2, R 3, Y and Z is a bond Ver ⁇ corresponds to one row of Table A.
  • Table 28 Compounds of the formula 1.1 in which X is chlorine, L m is 2-trifluoromethyl-5-chloro and R 1 , R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound corresponds to one row of Table A.
  • Table 32 Compounds of the formula 1.1, in which X is chlorine, L 01 is 2-chloro-4-methoxy and R 1 , R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound in each case Line of Table A corresponds
  • Table 33 Compounds of the formula 1.1, in which X is chlorine, L m is 2-fluoro-6-chloro and R 1 is methyl, R 4 and R 5 are hydrogen, and the combination of R 2 , R 3 , Y and Z is a Ver ⁇ corresponds in each case to one line of Table A.
  • Table 34 Compounds of the formula 1.1 in which X is chlorine, L m is 2,6-difluoro and R 1 is methyl, R 4 and R 5 is hydrogen and the combination of R 2 , R 3 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 36 Compounds of the formula 1.1, in which X is chlorine, 1- m 2-fluoro-6-methyl and R 1 is methyl, R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a Ver ⁇ corresponds in each case to one line of Table A.
  • Table 37 Compounds of the formula 1.1, in which X is chlorine, L m is 2,4,6-trifluoro and R 1 is methyl, R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound in each case corresponds to one line of Table A.
  • Table 38 Compounds of the formula 1.1 in which X is chlorine, m l_ 2,6-difluoro-4-methoxy and R 1 thyl Me ⁇ , R 4 and R 5 are hydrogen and the combination of R 2, R 3, Y and Z for a connection corresponds in each case to one row of Table A.
  • Table 39 Compounds of the formula 1.1, in which X is chlorine, L m is pentafluoro and R 1 is methyl, R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z for each compound corresponds to one row of table A.
  • Table 40 Compounds of the formula 1.1, in which X is chlorine, L m is 2-methyl-4-fluoro and R 1 is methyl, R 4 and R 5 are hydrogen, and the combination of R 2 , R 3 , Y and Z is a Ver ⁇ corresponds in each case to one line of Table A.
  • Table 41 Compounds of the formula 1.1, in which X is chlorine, L m is 2-trifluoromethyl and R 1 is methyl, R 4 and R 5 are hydrogen, and the combination of R 2 , R 3 , Y and Z for a compound in each case corresponds to one line Table A corresponds
  • Table 42 Compounds of the formula 1.1 in which X is chlorine, L m 2-methoxy-6-fluoro and R 1 is methyl, R 4 and R 5 is hydrogen and the combination of R 2 , R 3 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 43 Compounds of the formula 1.1, in which X is chlorine, L m is 2-chloro and R 1 is methyl, R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound of one row of the table A corresponds
  • Table 45 Compounds of the formula 1.1, in which X is chlorine, L m is 2,4-difluoro and R 1 is methyl, R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound of one line Table A corresponds
  • Table 46 Compounds of the formula 1.1, in which X is chlorine, L m is 2-fluoro-4-chloro and R 1 is methyl, R 4 and R 5 are hydrogen, and the combination of R 2 , R 3 , Y and Z is a Ver ⁇ corresponds in each case to one line of Table A.
  • Table 48 Compounds of the formula 1.1, in which X is chlorine, L m is 2,3-difluoro and R 1 is methyl, R 4 and R 5 are hydrogen, and the combination of R 2 , R 3 , Y and Z is a compound of one line Table A corresponds
  • Table 49 Compounds of the formula 1.1, in which X is chlorine, L m is 2,5-difluoro and R 1 is methyl, R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound of one line Table A corresponds
  • Table 50 Compounds of the formula 1.1, in which X is chlorine, L m is 2,3,4-trifluoro and R 1 is methyl, R 4 and R 5 is hydrogen and the combination of R 2 , R 3 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 51 Compounds of the formula 1.1, in which X is chlorine, L n , 2-methyl and R 1 is methyl, R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound of one line in each case Table A corresponds
  • Table 52 Compounds of the formula 1.1, in which X is chlorine, L m is 2,4-dimethyl and R 1 is methyl, R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound of one line Table A corresponds
  • Table 53 Compounds of the formula 1.1, in which X is chlorine, L m is 2-methyl-4-chloro and R 1 is methyl, R 4 and R 5 are hydrogen, and the combination of R 2 , R 3 , Y and Z is a Ver ⁇ corresponds in each case to one line of Table A.
  • Table 54 Compounds of the formula 1.1, in which X is chlorine, L n , 2-fluoro-4-methyl and R 1 is methyl, R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z for a Ver ⁇ binding corresponds to one row of Table A.
  • Table 55 Compounds of the formula 1.1 in which X is chlorine, L m is 2,6-dimethyl and R 1 is methyl, R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound of one line Table A corresponds
  • Table 56 Compounds of the formula 1.1 in which X is chlorine, L m is 2,4,6-trimethyl and R 1 is methyl, R 4 and R 5 are hydrogen, and the combination of R 2 , R 3 , Y and Z is a Ver ⁇ corresponds in each case to one line of Table A.
  • Table 57 Compounds of the formula 1.1, in which X is chlorine, I_ m is 2,6-difluoro-4-methyl and R 1 is methyl, R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a Compound corresponds to one line of Table A.
  • Table 58 Compounds of the formula 1.1 in which X is chlorine, L 01 is 2-trifluoromethyl-4-fluoro and R 1 is methyl- Thyl, R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z for a compound corresponds in each case to one row of Table A.
  • Table 59 Compounds of the formula 1.1, in which X is chlorine, L m is 2-trifluoromethyl-5-fluoro and R 1 is methyl, R 4 and R 5 are hydrogen, and the combination of R 2 , R 3 , Y and Z is a Compound corresponds to one line of Table A.
  • Table 60 Compounds of the formula 1.1, in which X is chlorine, 1- m 2-trifluoromethyl-5-chloro and R 1 is methyl, R 4 and R 5 are hydrogen, and the combination of R 2 , R 3 , Y and Z is a Compound corresponds to one line of Table A.
  • Table 61 Compounds of the formula 1.1 in which X is chlorine, L m is 2-chloro-4-fluoro and R 1 is methyl, R 4 and R 5 are hydrogen, and the combination of R 2 , R 3 , Y and Z is a Ver ⁇ corresponds in each case to one line of Table A.
  • Table 62 Compounds of the formula 1.1 in which X is chlorine, L m is 2-chloro-5-fluoro and R 1 is methyl, R 4 and R 5 are hydrogen, and the combination of R 2 , R 3 , Y and Z is a Ver ⁇ corresponds in each case to one line of Table A.
  • Table 63 Compounds of the formula 1.1, in which X is chlorine, L m is 2-methyl-5-fluoro and R 1 is methyl, R 4 and R 5 are hydrogen, and the combination of R 2 , R 3 , Y and Z is an ester corresponds in each case to one line of Table A.
  • Table 64 Compounds of the formula 1.1 in which X is chlorine, L m 2-chloro-4-methoxy and R 1 is methyl, R 4 and R 5 are hydrogen and the combination of R 2, R 3, Y and Z for each compound corresponds to one line of Table A.
  • Table 65 Compounds of the formula I.3 in which X is chlorine, L m is 2-fluoro-6-chloro and R 1 , R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound corresponds to one line of Table B.
  • Table 66 Compounds of the formula 1.3 in which X is chlorine, L m is 2,6-difluoro and R 1 , R 4 and R 5 are mean hydrogen and the combination of R 2 , R 3 , Y and Z for each compound corresponds to one row of Table B.
  • Table 70 Compounds of the formula I.3 in which X is chlorine, L m is 2,6-difluoro-4-methoxy and R 1 , R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound corresponds in each case to one row of Table B.
  • Table 71 Compounds of the formula I.3 in which X is chlorine, L m is pentafluoro and R 1 , R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound of one line in each case Table B corresponds
  • Table 72 Compounds of the formula I.3 in which X is chlorine, L m is 2-methyl-4-fluoro and R 1 , R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound corresponds to one line of Table B.
  • Table 73 Compounds of the formula I.3, in which X is chlorine, L m is 2-trifluoromethyl and R 1 , R 4 and R 5 are hydrogen, and the combination of R 2 , R 3 , Y and Z is a compound of one line in each case Table B corresponds
  • Table 74 Compounds of the formula I.3, in which X is chlorine, L m 2-methoxy-6-fluoro and R 1, R 4 and R 5 is hydrogen and the combination of R 2 , R 3 , Y and Z for a compound corresponds in each case to one row of Table B.
  • Table 75 Compounds of the formula 1.3 in which X is chlorine, 1- m 2-chloro and R 1 , R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound of one line in each case Table B corresponds
  • Table 76 Compounds of the formula 1.3 in which X is chlorine, L m is 2-fluoro and R 1 , R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound of one line in each case Table B corresponds
  • Table 77 Compounds of the formula 1.3 in which X is chlorine, I_ m is 2,4-difluoro and R 1 , R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound in each case one Line of Table B corresponds
  • Table 78 Compounds of the formula 1.3, in which X is chlorine, L m is 2-fluoro-4-chloro, and R 1 , R 4 and R 5 are hydrogen, and the combination of R 2 , R 3 , Y and Z for each compound Line of Table B corresponds
  • Table 79 Compounds of the formula 1.3 in which X is chlorine, L m is 2-chloro-4-fluoro and R 1 , R 4 and R 5 are hydrogen, and the combination of R 2 , R 3 , Y and Z for each compound is one Line of Table B corresponds
  • Table 80 Compounds of the formula 1.3 in which X is chlorine, L m is 2,3-difluoro and R 1 , R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound of one in each case Line of Table B corresponds
  • Table 81 Compounds of the formula 1.3 in which X is chlorine, L m is 2,5-difluoro and R 1 , R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound in each case one Line of Table B corresponds
  • Table 82 Compounds of the formula I.3 in which X is chlorine, L m is 2,3,4-trifluoro and R 1 , R 4 and R 5 Represent hydrogen and the combination of R 2 , R 3 , Y and Z for a compound corresponds in each case to one row of Table B.
  • Table 83 Compounds of the formula 1.3 in which X is chlorine, L n , 2-methyl and R 1 , R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound of one line in each case Table B corresponds
  • Table 84 Compounds of the formula I.3, in which X is chlorine, L m is 2,4-dimethyl and R 1 , R 4 and R 5 are hydrogen, and the combination of R 2 , R 3 , Y and Z is a compound in each case Line of Table B corresponds
  • Table 85 Compounds of the formula I.3 in which X is chlorine, 1- m 2-methyl-4-chloro and R 1 , R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound corresponds to one line of Table B.
  • Table 86 Compounds of the formula 1.3 in which X is chlorine, L n , 2-fluoro-4-methyl and R 1 , R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound in each case corresponds to one line of Table B.
  • Table 87 Compounds of the formula 1.3 in which X is chlorine, L m is 2,6-dimethyl and R 1 , R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a compound of one row each of Table B corresponds
  • Table 88 Compounds of the formula I.3, in which X is chlorine, L n , 2,4,6-trimethyl and R 1 , R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a Compound corresponds to one line of Table B.
  • Table 90 Compounds of the formula I.3 in which X is chlorine, L m is 2-trifluoromethyl-4-fluoro and R 1 , R 4 and R 5 is hydrogen and the combination of R 2 , R 3 , Y and Z for a compound corresponds in each case to one row of Table B.
  • Table 91 Compounds of the formula I.3, in which X is chlorine, L n , 2-trifluoromethyl-5-fluoro and R 1 , R 4 and R 5 are hydrogen and the combination of R 2 , R 3 , Y and Z is a Compound corresponds in each case to one row of Table B.
  • Table 92 Compounds of the formula I.3, in which X is chlorine, L m is 2-trifluoromethyl-5-chloro, and R 1 , R 4 and R 5 are hydrogen, and the combination of R 2 , R 3 , Y and Z for a Ver ⁇ binding corresponds to one line of Table B.
  • the compounds I are suitable as fungicides. They are distinguished by their excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Deuteromycetes, Oomycetes and Bassiomycetes. They are partially systemically effective and can be used in crop protection as foliar, pickling and soil fungicides. Furthermore, the present invention relates to the pharmaceutical use of the compounds of the formula I according to the invention and / or the pharmaceutically acceptable salts thereof, in particular their use for the treatment of tumors in mammals, for example in humans.
  • Botrytis cinerea (gray mold) on strawberries, vegetables, flowers and vines
  • Gibberella A anen on cereals and rice e.g., Gibberella fujikuroi on rice
  • the compounds I are also suitable for controlling harmful fungi such as Pecilomyces variotii in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
  • harmful fungi such as Pecilomyces variotii in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
  • the compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally 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.
  • seed treatment e.g. Pollination, coating or impregnation of seed good
  • amounts of active ingredient from 1 to 1000 g / 100 kg of seed, preferably 1 to 200 g / 100 kg, especially 5 to 100 g / 100 kg.
  • the application rate of active ingredient depends on the type of application and the desired effect.
  • Usual Wall quantities are in the material protection, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of treated material.
  • the compounds of the formula I can be present in various crystal modifications which are likewise the subject matter 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 form of application depends on the respective intended use; It should in each case ensure a fine and uniform distribution of the compound according to the invention.
  • Seed treatment formulations may additionally contain binders and / or gelling agents and optionally dyes.
  • Binders can be added to increase adhesion of the active ingredients to the seed after treatment.
  • suitable binders are EO / PO block copolymer surfactants, but also polyvinyl alcohols, polyvinylpyrrolidones, polyacrylates, polymethacrylates, polybutenes, polyisobutylenes, polystyrenes, polyethyleneamines, polyethylene amides, polyethyleneimines (Lupasol®, Polymin®), polyethers, polyurethanes, polyvinyl acetates, Tylose and Copolymers of these polymers.
  • a suitable gelling agent is, for example, carrageenan (Satiagel®).
  • the formulations are prepared in a known manner, e.g. by stretching the active compound with solvents and / or excipients, if desired using emulsifiers and dispersants.
  • Suitable solvents / auxiliaries are essentially:
  • Aromasoles e.g., Solvesso products, xylene
  • paraffins e.g., petroleum fractions
  • alcohols e.g., methanol, butanol, pentanol, benzyl alcohol
  • ketones e.g., cyclohexanone, gamma-butyrolactone
  • NMP pyrrolidones
  • NOP NOP
  • acetates glycol diacetate
  • glycols dimethyl fatty acid amides
  • fatty acids 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 finely divided silica, Silika ⁇ te); Emulsifiers such as nonionic and anionic emulsifiers (eg, polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.
  • ground natural minerals eg kaolins, clays, talc, chalk
  • ground synthetic minerals eg finely divided silica, Silika ⁇ te
  • Emulsifiers such as nonionic and anionic emulsifiers (eg, polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite 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
  • mineral oil fractions of medium to high boiling point such as kerosine 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, strongly polar solvents, e.g. Dimethylsulfoxide, N-methylpyrrolidone or water into consideration.
  • mineral oil fractions of medium to high boiling point such as kerosine 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 derivative
  • 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, such as 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,
  • 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).
  • the relevant formulations For seed treatment, the relevant formulations, diluted two to ten times, give active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations.
  • active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations.
  • Examples of formulations are: 1. Products for dilution in water
  • a Water-soluble Concentrates 10 parts by weight of a compound according to the invention are dissolved with 90 parts by weight of water or a water-soluble solvent. Alternatively, wetting agents or other adjuvants are added. When diluted in water, the active ingredient dissolves. This gives a formulation with 10 wt .-% active ingredient content.
  • a compound according to the invention 20 parts by weight of a compound according to the invention 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 gives a dispersion.
  • a dispersant e.g. Polyvinylpyrrolidone dissolved. Dilution in water gives a dispersion.
  • the active ingredient content is 20% by weight
  • a compound according to the invention 15 parts by weight of a compound according to the invention are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution in water results in an emulsion.
  • the formulation has 15% by weight active ingredient content.
  • a compound according to the invention 25 parts by weight of a compound according to the invention 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.
  • a compound according to the invention 20 parts by weight of a compound according to the invention 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 Wirkstoffsuspen ⁇ sion. 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 a compound according to the invention are finely ground with the addition of 50 parts by weight dispersing and wetting agents and by means of technical equipment (eg extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble Granules produced. 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.
  • 75 parts by weight of a compound according to the invention are ground with the addition of 25 parts by weight of dispersants and wetting agents and silica gel in a rotor-Strator mill. 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.
  • a ball mill 20 parts by weight of a compound of the invention, 10 parts by weight of dispersant, 1 part by weight of gelling agent and 70 parts by weight of water or an organic solvent are ground to a fine suspension. Dilution with water results in a stable suspension with 20% by weight of active substance content.
  • 0.5 parts by weight of a compound according to the invention 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
  • such formulations contain 1 to 800 g / l of active ingredient, 1 to 200 g / l of surfactants, 0 to 200 g / l of antifreeze, 0 to 400 g / l of binder, 0 to 200 g / l of dyes and solvents, preferably water.
  • the active compounds can be used as such, in the form of their formulations or the use forms 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 as far as possible the finest distribution of the active compounds according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders, oil dispersions) by addition of water.
  • emulsions, pastes or oil dispersions 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 To the active ingredients oils of various types, 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 inventive compositions in a weight ratio of 1:10 to 10: 1.
  • the agents according to the invention can also be present together with other active substances, for example with herbicides, insecticides, growth regulators, fungicides or else with fertilizers.
  • other active substances for example with herbicides, insecticides, growth regulators, fungicides or else with fertilizers.
  • Acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl,
  • Amine derivatives such as aldimorph, dodine, dodemorph, fenpropimorph, fenpropidin, guazatine, iminoctadine, spiroxamine, tridemorph,
  • Anilinopyrimidines such as pyrimethanil, mepanipyrim or cyrodinyl,
  • Antibiotics such as cycloheximide, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin,
  • Azoles such as bitertanol, bromoconazole, cyproconazole, difenoconazole, dinitroconazole, enilconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole, flutriafol, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, prochlorazole, prothioconazole, tebuconazole, triadimefon, triadimol, triflumizole , Triticonazole,
  • Dicarboximides such as iprodione, myclozoline, procymidone, vinclozolin,
  • Dithiocarbamates such as Ferbam, Nabam, Maneb, Mancozeb, Metam, Metiram, Propineb, Polycarbamate, Thiram, Ziram, Zineb,
  • Heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim, carboxaldine, oxycarboxine, cyazofamide, dazomet, dithianone, famoxadone, fenamidone,
  • Copper fungicides such as Bordeaux broth, copper acetate, copper oxychloride, basic copper sulfate,
  • Nitrophenyl derivatives such as binapacryl, dinocap, dinobutone, nitrophthalic-isopropyl, phenylpyrroles, such as fenpiclonil or fludioxonil, • sulfur,
  • fungicides such as acibenzolar-S-methyl, benthiavalicarb, carpropamide, chiorothalonil, cyflufenamid, cymoxanil, dazomet, diclomethine, didocymet, diethofen-carb, edifenphos, ethaboxam, fenhexamide, fentin-acetate, fenoxanil, ferimzone, fluazinam, fosetyl, Fosetyl-aluminum, phosphorous acid and its salts, iprovalacarb, hexachlorobenzene, mandipropamide, metrafenone, pencycuron, propamocarb, phthalide, toloclofos-methyl, quintozene, zoxamide, N- (2- [4- [3- (4-chloro) phenyl) - prop-2-ynyloxy] -3-methoxy-phen
  • strobilurins such as azoxystrobin, dimoxystrobin, enestroburine, fluoxastrobin, cresoxime-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin or
  • Sulfenic acid derivatives such as captafol, captan, dichlofluanid, folpet, tolylfluanid,
  • Cinnamic acid amides and analogues such as dimethomorph, flumetover or flumorph.
  • HPLC retention times in the following tables were determined 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 gradient from 5:95 to 95: 5 in 5 min at 40 ° C determined. Mass spectrometry was performed under Quadropol electrospray ionization, 80V (positive mode).
  • the active ingredients were formulated separately as stock solution with 0.25% by weight of active ingredient in acetone or DMSO. To this solution was added 1% by weight of Wettol EM 31 emulsifier (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenol). The stock solutions of the active ingredients were diluted with water according to the stated concentration.
  • Leaves of potted plants of the "golden queen" variety were sprayed to drip point with an aqueous suspension in the concentration of active compound stated below. The following day, the leaves were infected with an aqueous spore suspension of Alternaria solani in 2% biomalt solution with a density of 0.17 x 10 6 spores / ml. Subsequently, the plants were placed in a water vapor-saturated chamber at temperatures between 20 and 22 0 C. After 5 days, the disease on the untreated, but infected control plants had developed so strongly that the infestation could be determined visually in%.

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

Abstract

L'invention concerne des 6-phényl-7-amino-triazolopyrimidines de formule (I), dans laquelle les substituants ont la signification suivante: R<sup
EP05784802A 2004-09-08 2005-09-02 6-phenyl-7-amino-triazolopyrimidines, leurs procedes de production et leur utilisation pour lutter contre les champignons nuisibles, et agents les contenant Withdrawn EP1797095A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004043836 2004-09-08
PCT/EP2005/009456 WO2006027170A1 (fr) 2004-09-08 2005-09-02 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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EP1797095A1 true EP1797095A1 (fr) 2007-06-20

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US (1) US20070270311A1 (fr)
EP (1) EP1797095A1 (fr)
KR (1) KR20070104516A (fr)
CN (1) CN101014604A (fr)
AP (1) AP2007003927A0 (fr)
AR (1) AR050797A1 (fr)
AU (1) AU2005281882A1 (fr)
BR (1) BRPI0514955A (fr)
CA (1) CA2577041A1 (fr)
EA (1) EA200700554A1 (fr)
EC (1) ECSP077293A (fr)
IL (1) IL181313A0 (fr)
MA (1) MA28878B1 (fr)
MX (1) MX2007001869A (fr)
PE (1) PE20060445A1 (fr)
TW (1) TW200621782A (fr)
UY (1) UY29111A1 (fr)
WO (1) WO2006027170A1 (fr)
ZA (1) ZA200702822B (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007101810A1 (fr) * 2006-03-08 2007-09-13 Basf Se Triazolopyrimidines substituées, procédés de production associés et leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant
WO2007113136A1 (fr) * 2006-03-30 2007-10-11 Basf Aktiengesellschaft Utilisation de triazolopyrimidines substituées dans la lutte contre des champignons phytopathogènes

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Publication number Priority date Publication date Assignee Title
TW224044B (fr) * 1991-12-30 1994-05-21 Shell Internat Res Schappej B V
US6117876A (en) * 1997-04-14 2000-09-12 American Cyanamid Company Fungicidal trifluorophenyl-triazolopyrimidines
TWI252231B (en) * 1997-04-14 2006-04-01 American Cyanamid Co Fungicidal trifluorophenyl-triazolopyrimidines
TW460476B (en) * 1997-04-14 2001-10-21 American Cyanamid Co Fungicidal trifluoromethylalkylamino-triazolopyrimidines
US6117865A (en) * 1998-09-10 2000-09-12 American Cyanamid Company Fungicidal trifluorophenyl-triazolopyrimidines
JP2000103790A (ja) * 1998-09-25 2000-04-11 American Cyanamid Co 殺菌・殺カビ性のトリハロフェニル―トリアゾロピリミジン類
AU2002221831A1 (en) * 2000-11-13 2002-05-21 Basf Aktiengesellschaft 7-(r)-amino-triazolopyrimidines, the production thereof and use of the same for combating phytopathogenic fungi
DE10063115A1 (de) * 2000-12-18 2002-06-27 Bayer Ag Triazolopyrimidine

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2006027170A1 *

Also Published As

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MX2007001869A (es) 2007-04-24
US20070270311A1 (en) 2007-11-22
UY29111A1 (es) 2006-04-28
ECSP077293A (es) 2007-05-30
IL181313A0 (en) 2007-07-04
AU2005281882A1 (en) 2006-03-16
ZA200702822B (en) 2009-12-30
KR20070104516A (ko) 2007-10-26
WO2006027170A1 (fr) 2006-03-16
TW200621782A (en) 2006-07-01
PE20060445A1 (es) 2006-06-20
EA200700554A1 (ru) 2007-10-26
CN101014604A (zh) 2007-08-08
AR050797A1 (es) 2006-11-22
MA28878B1 (fr) 2007-09-03
AP2007003927A0 (en) 2007-02-28
CA2577041A1 (fr) 2006-03-16
BRPI0514955A (pt) 2008-07-01

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