EP2117312A1 - Utilisation d'azolopyrimidines pour la lutte contre des champignons parasites phytopathogenes - Google Patents

Utilisation d'azolopyrimidines pour la lutte contre des champignons parasites phytopathogenes

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Publication number
EP2117312A1
EP2117312A1 EP08701270A EP08701270A EP2117312A1 EP 2117312 A1 EP2117312 A1 EP 2117312A1 EP 08701270 A EP08701270 A EP 08701270A EP 08701270 A EP08701270 A EP 08701270A EP 2117312 A1 EP2117312 A1 EP 2117312A1
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European Patent Office
Prior art keywords
alkyl
formula
groups
compounds
group
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EP08701270A
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German (de)
English (en)
Inventor
Jochen Dietz
Wassilios Grammenos
Bernd Müller
Jan Klaas Lohmann
Jens Renner
Sarah Ulmschneider
Marianna Vrettou
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BASF SE
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BASF SE
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Priority to EP08701270A priority Critical patent/EP2117312A1/fr
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Definitions

  • the invention relates to the use of certain azolopyrimidines for the control of harmful fungi, a method for controlling phytopathogenic harmful fungi, novel fungicidal azolopyrimidine compounds, processes for their preparation and compositions containing these compounds.
  • 6-phenyl-7-amino-triazolopyrimidines are generally known.
  • WO 03/004465 discloses triazolopyrimidines which are substituted in positions 5 and 7 by groups bonded via carbon.
  • WO 02/002563 describes certain 6-phenyltriazolopyrimidines as fungicidal and pharmaceutically effective.
  • 5-halogen-7-amino-pyrazolopyrimidines are generally known, which are substituted in the 6-position by a heterocycle. These compounds are known for controlling harmful fungi.
  • Such compounds are known in part from WO 2002/002563 and WO 2005/030775 as anticancer agents.
  • the invention therefore relates to the use of azolopyrimidines of formula I.
  • G, E, Q a) G is N; E is CW 2 and Q is N or CW 3 ; b) G is CW 1 ; E is CW 2 and Q is N; or c) G is CW 1 ; E is N and Q is CW 3 ;
  • W 1 , W 2 , W 3 are each independently of one another hydrogen, halogen, cyano, nitro, C 1 -
  • C 4 -alkylcarbonyl C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkylaminocarbonyl, aminocarbonyl, di- (C 1 -C 4 -alkyl) aminocarbonyl, dC 1 -alkoximinoalkyl, hydroximinoalkyl,
  • R 10 R 11 OR 12 , C (R 13 ) NR 14 ;
  • R 10 , R 11 , R 12 independently of one another are hydrogen, C 1 -C 8 -alkyl, C 3 -C 3 -cycloalkyl,
  • R 11 and R 12 may together be oxy-C 1 -C 5 -alkyleneoxy, wherein the carbon chain may be substituted by one to three groups of methyl, ethyl, hydroxy, methoxy, ethoxy, hydroxymethyl, methoxymethyl, ethoxymethyl;
  • R 13 is hydrogen or C 1 -C 8 -alkyl
  • R 14 is C 1 -C 8 -alkyl, C 3 -C 6 -cycloalkyl, phenyl, phenylamino, where the phenyl groups may be substituted by one to five groups R b ;
  • R is NR 1 R 2 , C 3 -C 6 cycloalkyl or C 3 -C 12 halocycloalkyl; wherein R may contain one, two, three or four identical or different groups R a , which are independently selected from: R a R b , carboxyl, OC (O) OR ⁇ or C 1 -C 6 alkylthio; R b R c , hydroxy, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -
  • R c is hydrogen, cyano, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 5 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 8 -cycloalkenyl, C ( O) R ⁇ , C (O) OR ⁇ , C (S) OR ⁇ , C (O) SR ⁇ , C (S) SR ⁇ , amino, C 1 -C 6 -alkylamino, di-dC 6 -alkylamino, Aminocarbonyl, C (O) NHR ⁇ , C (O) NR ⁇ 2 , phenyl, naphthyl, 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
  • R a , R b , R c , R ⁇ R d and / or R dd form, together with the atom or atoms to which they are attached, a 3 to 12-membered saturated, partially unsaturated or aromatic ring which is carbocyclic or contains one to four heteroatoms from the group N, O and S and which is unsubstituted or substituted by 1 to 4, in the case of halogen also up to the maximum number, radicals R d ; R ⁇ C 1 -C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkylene, C 3 -C 6 cycloalkyl or
  • R d is halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, alkyl,
  • Haloalkyl alkenyl, alkynyl, alkoxy, haloalkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylamino, dialkylamino, formyl, alkylcarbonyl,
  • R dd is halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, alkyl, haloalkyl, alkenyl, alkoxy, haloalkoxy, alkenyloxy, alkynyloxy,
  • Alkoximino NOdC 8 alkyl
  • C 3 -C 8 alkenyloximino NOC 3 -C 8 alkenyl
  • C 3 -C 8 -Al kinyloximino NOC 3 -C 8 alkynyl
  • R 1 is C 1 -C 12 -haloalkyl, C 2 -C 12 -haloalkenyl, C 2 -C 12 -haloalkynyl;
  • R 2 is H, R 1 , C 1 -C 12 -alkyl, C 2 -C 12 -alkenyl, C 2 -C 12 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -HiIo- gencycloalkyl, C 3 -C 6 cycloalkenyl, C 3 -C 6 halocycloalkenyl, dC 8 alkoxy, C 2 - C 8 alkenyloxy, C 2 -C 8 alkynyloxy, C 3 -C 8 cycloalkoxy, NH 2, dC 8 - Alkylamino, di-
  • 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 or three heteroatoms from the group O, N and S can contain as ring member and / or can carry one or more substituents R a ;
  • R 3 with R 4, R 5 with R 6, R 7 with R 8 may each together denote carbonyl groups and the formation of oxygen and the formation of the spiro groups, a C 2 -C 5 alkylene or alkenylene, alkynylene form, by a , two or three heteroatoms from the group O, N and S may be interrupted;
  • R 1 to R 8 may each independently carry one, two, three or four identical or different groups R a ; Y oxygen or sulfur;
  • Z is hydrogen, carboxyl, formyl, C 1 -C 8 alkyl, dC 8 haloalkyl, C 2 -C 8 - alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 - Haloalkynyl, C 3 -C 5 -
  • Y 1 CR a R a ' C (O) O, C (O) NR b , O, NR b or S (O) r ; Y 2 C 3 -C 8 -alkylene, C 2 -C 8 -alkenylene, C 2 -C 8 -alkynylene, C 3 -C 8 -alkylene
  • L is halogen, hydroxy, cyanato (OCN), cyano, nitro, C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -haloalkenyl, C 2 -C 10 alkynyl, C 3 -C 6 - cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 cycloalkenyl, dC 8 alkoxy, d-
  • C 8 haloalkoxy C 2 -C 10 alkenyloxy, C 2 -C 10 alkynyloxy, C 3 -C 6 cycloalkyloxy, C 3 -C 6 cycloalkenyloxy, amino, C 1 -C 4 alkylamino, di - (C 1 -C 4 ) -alkylamino, C 1 -C 4 -alkylcarbonylamino, C (O) -R ⁇ , C (S) -R ⁇ S (O) n -R ⁇ ; C 1 -C 8 -alkyl-oxyimino (C 1 -C 8 ) -alkyl, C 2 -C 10 -alkenyloxyimino- (C 1 -C 8 ) -alkyl, C 2 -C 10 -alkynyl-oxyimino- (C C 1 -C 8 ) -alkyl, C 2 -C 1 -alky
  • alkylamino wherein the groups R ⁇ may be substituted by one, two or three identical or different groups R b as defined above; n is zero, 1 or 2; m is zero, 1, 2, 3, 4 or 5 and X is halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -Hio- genalkoxy.
  • R in formula I is NR 1 R 2
  • the compounds can be prepared by reacting an aminoazole of the formula II with correspondingly substituted phenylmalonates of the formula III where R "is alkyl, preferably C 1 -C 6 -alkyl, in particular represents methyl or ethyl.
  • This reaction is usually carried out at temperatures of from 80 ° C. to 250 ° C., preferably from 120 ° C. to 180 ° 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 from Adv. Het. Chem. Vol. 57, p. 81ff.
  • 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, dimethyl form - amide and dimethylacetamide.
  • the reaction is particularly preferably carried out without 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 hydrogencarbonates, organometallic compounds, in particular alkali metal alkyls, alkyl magnesium halides and alkali metal and alkaline earth metal alcohols.
  • organic bases for example tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine, tributylamine and N-methylpiperidine, N-methylmorpholine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethyl-aminopyridine and bicyclic amines into consideration. Particular preference is given to 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 III in an excess relative to the triazole.
  • the malonates of the formula III are advantageously obtained from the reaction of appropriately substituted bromoaromatics with dialkyl malonates under Cu (I) catalysis [cf. Chemistry Letters, pp. 367-370, 1981; EP-A 10 02 788].
  • malonates of Formula III may be synthesized according to the following scheme under well-known conditions [See: March, Advanced Organic Chemistry, 3rd ed., P.792ff, J. Wiley & Sons, New York (1985)]:
  • the dihydroxyazolopyrimidines of the formula IV are converted under the conditions known from WO-A 94/20501 into the dihaloazolopyrimidines of the formula V in which Y is a halogen atom, preferably a bromine or a chlorine atom, in particular a chlorine atom.
  • the halogenating agent [HAL] used is advantageously a chlorinating agent or a brominating agent, such as phosphorus oxybromide or phosphorus oxychloride, if appropriate in the presence of a solvent.
  • This reaction is usually carried out at 0 ° C to 150 ° C, preferably at 80 ° C to 125 ° C, performed [see. EP-A 770 615].
  • Dihalogenazolopyrimidines of the formula V are prepared with amines of the formula VI in which the variables are as defined for formula I.
  • This reaction is advantageously carried out at 0 ° C to 70 ° C, preferably 10 ° C to 35 ° C, preferably in the presence of an inert solvent such as ethers, eg. Eg oxane, diethyl ether or, in particular, tetrahydrofuran, halogenated hydrocarbons, such as dichloromethane and aromatic hydrocarbons, for example toluene [cf. WO 05/000851].
  • ethers eg. Eg oxane, diethyl ether or, in particular, tetrahydrofuran, halogenated hydrocarbons, such as dichloromethane and aromatic hydrocarbons, for example toluene [cf. WO 05/000851].
  • a base such as tertiary amines, for example triethylamine or inorganic amines, such as potassium carbonate is preferred; Excess amine of the formula VI can also serve as a base.
  • the 5-chloroazolopyrimidines of the formula I are thus accessible. They represent a preferred subject of the invention.
  • Other 5,7-Dihalogenazolo- pyrimidines are accessible analogously to the cited literature.
  • Amines of the formula VI are known in the literature, can be prepared by known methods or are commercially available.
  • the 5-alkyl-7-hydroxyazolopyrimidines IVa are obtained.
  • X 1 is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl.
  • the preparation of the starting compounds IIIa is advantageously carried out under the conditions described in EP-A 10 02 788 [cf. Chem. Pharm. Bull., 9, 801, (1961)].
  • the resulting 5-alkyl-7-hydroxyazolopyrimidines are reacted with halogenating agents [HAL] under the conditions described above to give the 7-haloazolopyrimidines 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 150 ° C, or preferably from 80 to 125 ° C.
  • compounds of the formula I in which X is C 1 -C 4 -alkyl may also be prepared from compounds I in which X is halogen, in particular chlorine, and malonates of the formula INb.
  • X is hydrogen or C 1 -C 3 -alkyl and R # is C 1 -C 4 -alkyl They are converted into compounds of formula VII and decarboxylated to compounds I [see US 5,994,360] VII are new.
  • the malonates INb are known in the literature [J. At the. Chem. Soc., Vol. 64, 2714 (1942); J. Org. Chem., Vol. 39, 2172 (1974); Helv. Chim. Acta, Vol. 61, 1565 (1978)] or can be prepared according to the cited literature.
  • 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 20 ° C to 180 ° C, preferably 50 ° C to 120 ° 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.
  • R in formula I is a group bonded via carbon (R 'in formula Ia) and X is alkyl or haloalkyl
  • the compounds are prepared by reacting an aminoazole of formula II with appropriately substituted 1,3-diketones of formula INc in which R is a group bonded via carbon according to formula I and X "is alkyl or haloalkyl, preferably C 1 -C 6 -alkyl, in particular methyl or ethyl.
  • This reaction is advantageously carried out under the conditions described above for the reaction of the compounds II with III.
  • Compounds of the formula I in which X is cyano, alkoxy or haloalkoxy can advantageously be obtained from the reaction of compounds I in which X denotes halogen, preferably chlorine, with compounds MX '(formula VIII).
  • compounds IV represent 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 VIII has little significance; For practical reasons, ammonium, tetraalkylammonium or alkali or alkaline earth metal salts are usually preferred.
  • the reaction temperature is usually 0 to 120.degree. C., preferably 10 to 40.degree. C. [cf. J. Heterocycl. Chem., Vol. 12, p. 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.
  • compounds of the formula I can be obtained from corresponding precursors which carry a nucleophilically exchangeable group on the group W instead of the group P 1 .
  • the introduction of the group P 1 is thus carried out by nucleophilic substitution [cf. WO 05/30775].
  • compounds of the formula I in which P 1 represents an oxygen-bonded group can be prepared from analogous hydroxy compounds (formula IX), which in turn can be prepared by ether cleavage from known compounds [cf. WO 99/48893] are accessible.
  • the introduction of the group P 1 is carried out by nucleophilic substitution of the hydroxy group under basic conditions.
  • These hydroxy compounds correspond to the formula I in which W is substituted by a hydroxyl group in addition to the group L m (formula IX).
  • 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, for example C 1 -C 6 -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 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-dimethylphenyl, 3,3- Dimethylbutyl, 1-ethylbutyl, 2-eth
  • 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; a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S: nonaromatic saturated or partially unsaturated 5- or 6-membered heterocyclyl containing one bis three nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, eg 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidiny
  • 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 2 to 8 CH 2 groups, eg CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 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 CH 2 CH 2 CH 2 CH 2 ;
  • Oxyalkylene divalent unbranched chains of 2 to 4 CH 2 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 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;
  • suitable agriculturally acceptable salts are, in particular, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the pesticidal activity of the pyrimidines according to the invention.
  • the ions of the alkali metals preferably sodium or potassium
  • the alkaline earth metals preferably calcium, magnesium or barium
  • the transition metals preferably manganese, copper, zinc or iron, or the ammonium ion
  • phosphonium ions, sulfonium ions preferably tri- (C 1 -C 4 ) -alkylsulfonium and sulfoxonium ions, preferably Tri (C 1 -C 4 ) alkylsulfoxonium, into consideration.
  • Anions of advantageously usable acid addition salts are, for example, chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of (C 1 -C 4 ) -alkanoic acids, preferably formate, acetate, Propionate and butyrate. They can be formed by reaction of the compounds according to the invention with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid. Included within the scope of the present invention are the (R) and (S) isomers and the racemates of compounds of Formula I which have chiral centers.
  • Hindered rotation of unsymmetrically substituted groups may give atropisomers of compounds of the formula I. They are also the subject of the invention.
  • One embodiment relates to compounds I in which R is NR 1 R 2 . These compounds correspond to the formula La.
  • R 1 is C- ⁇ -C 12 haloalkyl, C 2 -C 12 haloalkenyl, C 2 -C 12 haloalkynyl, and R 2 R 1 or H, more preferably represents H, are preferred.
  • R 1 is dC 16 -haloalkyl, C 2 -C 6 -haloalkenyl or C 2 -C 6 -haloalkynyl.
  • R 1 is C 2 haloalkyl, particularly preferably 2, 2, 2-trifluoroethyl.
  • R 1 is C 3 -haloalkyl, particularly preferably 1-methyl-2,2,2-trifluoroethyl.
  • R 2 is H, C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 2 -C 3 -haloalkyl or C 2 -C 4 - Haloalkenyl means.
  • R 2 is hydrogen. Also preferred are compounds in which R 2 is methyl.
  • R 2 is ethyl
  • R 1 is C 1 -C 6 -haloalkyl, C 2 -C 6 -haloalkenyl or C 2 -C 6 -haloalkynyl and R 2 is R 1 or H, very particularly preferably H.
  • Z 1 is hydrogen, fluorine or C 1 -C 6 -fluoroalkyl
  • Z 2 is hydrogen or fluorine, or Z 1 and Z 2 together form a double bond
  • w is 0 or 1
  • R 3A is hydrogen or methyl.
  • R 2 preferably denotes R 1 or H, particularly preferably H. methyl or ethyl, especially preferably H.
  • Z 1 and Z 2 independently of one another preferably represent fluorine or hydrogen or form a double bond.
  • 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 stands for a group bonded via carbon. These compounds correspond to the formula Lb, in which R 'is C 3 -C 6 -cycloalkyl or C 3 -C 12 -halocycloalkyl.
  • a further embodiment relates to compounds Ib in which R 'is C 3 -C 8 -halocycloalkyl or C 3 -C 6 -cycloalkyl.
  • a preferred embodiment relates to compounds Ib in which R 'is C 3 -cycloalkyl, C 5 - or C 6 -cycloalkyl, in particular C 6 -cycloalkyl.
  • a further preferred embodiment relates to compounds Ib in which R 'is C 3 -C 6 - cycloalkyl, more preferably C 6 cycloalkyl, or C 3- C 6 -Halogencylcoalkyl means.
  • R ' is C 3 - halogenocycloalkyl, C 4 -, C 5 - or C 6 -halocycloalkyl. If R 'carries at least one group R b , then R b is preferably selected from halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 - C 6 alkynyl,
  • One embodiment relates to compounds I in which VV stands for phenyl substituted by P 1 and L m .
  • L m the following groups are suitable for L m : halogen, such as fluorine or chlorine; cyano; nitro; alkoxycarbonyl; aminocarbonyl; C 1 -C 4 alkyl, such as methyl; C 1 -C 4 haloalkyl, such as trifluoromethyl; C 1 -C 4 -alkoxy, such as methoxy.
  • Embodiments of group W relate in particular to phenyl groups which, in addition to the group P 1 , may have the following substitution:
  • Position 2 fluorine, chlorine or methyl
  • Position 3 hydrogen, fluorine or methoxy
  • Position 4 hydrogen, fluorine, chlorine, methyl, methoxy, cyano, nitro, alkoxycarbonyl, aminocarbonyl or haloalkyl, particularly preferably fluorine, chlorine, methyl, methoxy or cyano
  • Position 5 hydrogen, fluorine, chlorine or methyl; particularly preferably hydrogen or fluorine
  • Position 6 hydrogen, fluorine, chlorine or methyl; especially preferably hydrogen or fluorine.
  • the group P 1 is preferably in the positions 3, 4 or 5.
  • the phenyl group substituted by the groups P 1 and L m represents the groups A or B.
  • L m is one of the following substituent combinations: 2-CI; 2-F; 2,6-Cl 2 ; 2,6-F 2 ; 2-CI-F.6; 2-Cl, 6-CH 3 , 2-F, 6-CH 3 ; 2,4,6-F 3 ; 2,6-F 2 -4-OCH 3 ; 2-CI, 4-OCH 3 ; 2-F, 4-OCH 3 , 2-CH 3 , 4-OCH 3 , 2-CH 3 -4-F; 2-CF 3 ;
  • L m is one of the following substituent combinations: 2-F; 2-CI; 2-CH 3 ; 2,6-F 2 ; 2-CI-F.6; 2-F, 6-CH 3 .
  • One embodiment relates to compounds I in which W is heteroaryl which is substituted by P 1 and L m and contains one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom.
  • the group W is substituted by P 1 and L m substituted heteroaryl, which is bonded via a nitrogen atom. In another embodiment, the group W is substituted by P 1 and L m substituted heteroaryl, which is bonded via a carbon atom.
  • One embodiment relates to compounds I in which W is a 5-membered heteroaryl substituted by P 1 and L m and containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom.
  • a further embodiment relates to compounds I in which W is pyrrole, furan, thiophene, pyrazole, isoxazole, isothiazole, imidazole, oxazole, thiazole, 1, 2,3-triazole or 1,2,4-triazole.
  • Another embodiment relates to compounds I in which W is thiophene, pyrazole or thiazole.
  • W is a 6-membered heteroaryl which is substituted by P 1 and L m and contains one to three or one to four nitrogen atoms.
  • a further embodiment relates to compounds I in which W is pyridine, pyrimidine, pyridazine or pyrazine.
  • W is pyridyl which is linked in the 2-, 3- or 4-position and may be monosubstituted, monosubstituted or differently substituted by L m , which preferably comprises fluorine, chlorine, bromine, Cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl, more preferably fluorine, chlorine, methyl, methoxy and / or cyano.
  • One embodiment of the compounds of the formula I relates to those of the formula I.
  • a further embodiment relates to compounds I in which W is pyrimidyl which is linked in the 2- or 4-position and may be monosubstituted, disubstituted, identical or differently substituted by L m , which preferably comprises fluorine, chlorine, bromine, Cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl, particularly preferably fluorine, chlorine, methyl, methoxy and / or cyano.
  • L m which preferably comprises fluorine, chlorine, bromine, Cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl, particularly preferably fluorine, chlorine,
  • One embodiment of the compounds of the formula I relates to those of the formula I. E and LF.
  • a further embodiment relates to compounds I in which W is thienyl which is linked in the 2- or 3-position and may be monosubstituted or disubstituted by identical or different substituents by L m , which preferably comprises fluorine, chlorine, bromine, cyano, Nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl, more preferably fluorine, chlorine, methyl, methoxy and / or cyano.
  • L m which preferably comprises fluorine, chlorine, bromine, cyano, Nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl, more preferably fluorine, chlorine, methyl
  • One embodiment of the compounds of the formula I relates to those of the formula LG and LH.
  • a further embodiment relates to compounds I 1 in which W is thiazolyl which is linked in the 2-, A- or 5-position and may be substituted by L m , which preferably comprises fluorine, chlorine, bromine, cyano, nitro, methyl, Ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl or trifluoromethyl, particularly preferably fluorine, chlorine, methyl, methoxy and / or cyano.
  • L m which preferably comprises fluorine, chlorine, bromine, cyano, nitro, methyl, Ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl or trifluoromethyl, particularly preferably fluorine, chlorine, methyl, methoxy and / or cyano.
  • One embodiment of the compounds of the formula I relates to those of the formula LI and LJ.
  • a further embodiment relates to compounds I in which W is imidazolyl which is linked in the 4- or 5-position and may be monosubstituted, disubstituted, identical or differently substituted by L m , which preferably comprises fluorine, chlorine, bromine, Cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl, particularly preferably fluorine, chlorine, methyl, methoxy and / or cyano.
  • L m which preferably comprises fluorine, chlorine, bromine, Cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl, particularly preferably fluorine, chlorine,
  • One embodiment of the compounds of the formula I relates to those of the formula I. K and I.L
  • a further embodiment relates to compounds I in which W is pyrazolyl which is linked in the 1-, 3-, 4- or 5-position and may be monosubstituted to trisubstituted, identically or differently substituted by L m , which is preferred Fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl, more preferably fluorine, chlorine, methyl, methoxy and / or cyano.
  • One embodiment of the compounds of the formula I relates to those of the formula I. M, LN and LO.
  • a further embodiment relates to compounds I in which W is oxazolyl which is linked in the 2-, 3- or 4-position and may be monosubstituted or disubstituted by identical or different substituents by L m , which preferably contains fluorine, chlorine , Bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl, more preferably fluorine, chlorine, methyl, methoxy and / or cyano.
  • L m which preferably contains fluorine, chlorine , Bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl, more preferably flu
  • At least one group L is ortho to the point of attachment of the group W with the azolopyrimidine scaffold, in particular chlorine, fluorine or methyl.
  • a heteroatom of the heteroaromatic is ortho to the junction.
  • the index m is preferably from 1 to 4, where the groups L may be the same or different.
  • the heteroaromatic groups W carry, in addition to a group P 1, further substituents, these are preferably selected from: fluorine, chlorine, methyl, methoxy, cyano, nitro, alkoxycarbonyl, aminocarbonyl and haloalkyl.
  • the optional substituents L m are selected from fluorine, chlorine, methyl and methoxy.
  • the optional substituents L m are selected from chlorine, methyl and methoxy.
  • a further embodiment relates to heteroaromatic groups W which are substituted by chlorine in addition to a group P 1 .
  • a further embodiment relates to heteroaromatic groups W, which are substituted by fluorine in addition to a group P 1 .
  • Y 1 is CR a R a ' .
  • Y 1 is C (O) O. In a further embodiment of the group P 1 , Y 1 is C (O) NR b .
  • Y 1 is oxygen
  • Y 1 denotes NR b .
  • Y 1 is sulfur
  • Y 2 is C 1 -C 8 -alkylene, preferably C 2 -C 8 -alkylene.
  • Y 2 is C 3 -C 8 -alkylene, preferably C 3 -C 4 -alkylene, more preferably C 3 -alkylene (propylene).
  • Y 2 is C 1 -alkylene (methylene).
  • Y 2 is C 2 -alkylene (ethylene). In a further embodiment of the group P 1 , Y 2 ##-CH (CH 3 ) -CH 2 - (## is the point of attachment to Y 1 ).
  • Y 2 denotes ## - CH 2 -CH (CH 3 ) - (## is the point of attachment to Y 1 ).
  • Y 2 is C 4 -alkylene (butylene). In a further embodiment of the group P 1 , Y 2 is C 2 -C 8 -alkenylene.
  • Y 2 is C 2 -C 8 -alkynylene.
  • Y 2 in particular C 1 -C 8 -alkylene, is interrupted by heteroatoms.
  • oxygen and NR b come as Heteroatoms in question, in which R b is preferably hydrogen, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or C 1 -C 4 -alkyl, preferably methyl.
  • One embodiment relates to compounds I in which T is OH.
  • a further embodiment relates to compounds I in which T is OR c , where R c is preferably
  • a further embodiment relates to compounds I in which T is OR c , where R c is preferably C 1 -C 4 -alkyl, particularly preferably methyl.
  • a further embodiment relates to compounds I in which T is OR c , in which R c is C 3 -C 6 -cycloalkyl; 5- or 6-membered heterocyclyl or 5- or 6-membered heteroaryl, preferably 6-membered hetaryl, such as pyridine, pyridazine, pyrimidine, pyrazine.
  • 1, 2,4-triazine and 1,3,5-triazine moreover preferably 5-membered heteroaryl such as pyrazole, isoxazole, isothiazole, imidazole, thiazole and oxazole, moreover preferably 6-membered heterocyclyl such as tetrahydropyran and piperidine, moreover preferred 5-membered heterocyclyl, such as tetrahydrofuran and pyrrolidine.
  • 5-membered heteroaryl such as pyrazole, isoxazole, isothiazole, imidazole, thiazole and oxazole
  • 6-membered heterocyclyl such as tetrahydropyran and piperidine
  • 5-membered heterocyclyl such as tetrahydrofuran and pyrrolidine.
  • R d has pre preferably the following meanings: halogen, cyano, nitro, hydroxy , Mercapto, amino, carboxyl, alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylamino, dialkylamino, formyl, alkylcarbonyl, alkylsulfonyl, alkylsulfoxyl, alkoxycarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, aminocarbo nyl, aminothiocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminothio
  • C 1 -C 8 -alkyl C 1 -C 8 -alkyl
  • C 1 -C 8 -alkoximino NOC 1 -C 8 -alkyl
  • C 3 -C 8 -alkenyloximino NOC 3 -C 8 -alkenyl
  • C 3 -C 8 -Alkinyloximino NOC 3 -C 8 alkynyl
  • a further embodiment relates to compounds I in which T is OC (O) R a , where R a has the following meanings: hydrogen, cyano, carboxyl, C 1 -C 6 -
  • R a is preferably hydrogen, C 1 - Ce-alkyl, C 1 -C 6 alkoxy, C (O) R ⁇ , C (O) oR ⁇ , amino, C 1 -C 6 -Alkylam ⁇ no, di-C 1 - C 6 alkylamino, aminocarbonyl, C (O) NHR ⁇ or C (O) NR ⁇
  • R d preferably has the following meanings: halogen, cyano, nitro, hydroxy , Mercapto, amino, carboxyl, alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylamino, dialkylamino, formyl, alkylcarbonyl, alkylsulfonyl, alkylsulfoxyl, alkoxycarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, aminocarbonyl , Aminothiocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylammothiocarbonyl, dialky
  • a further embodiment relates to compounds I in which T is NR b R b , where R b can assume the same meanings as R b and R b and R b independently of one another
  • R b, R b and R b are preferably hydrogen, cyano, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 8 - Cycloalkenyl, C (O) R ⁇ , C (O) OR ⁇ , C (S) OR ⁇ , C (O) SR ⁇ , C (S) SR ⁇ , amino, C 1 -C 6 -alkylamino, di-C 1 C 6 alkylamino, aminocarbonyl, C (O) NHR ⁇ or C (O) NR ⁇ 2
  • t NR b R b, R b and R b preferably serstoff water, 6 -alkyl, C (O) R ⁇ , C (O) OR ⁇ , aminocarbonyl, C (O) NHR or ⁇ C (O) NR ⁇ 2
  • T NR b R b , R b and R b together with the nitrogen to which they are attached form 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;
  • T NR b R b radicals mentioned R b, R b and R ⁇ unsubstituted or substituted by 1-3 substituents R d, wherein R d preferably has the following meanings: halogen, cyano, nitro, Hydroxyl, mercapto, amino, carboxyl, alkyl, halo
  • NR b R b are amino, methylamino, dimethylamino, pyrrolidinyl, piperidinyl, piperazinyl, N-methylpiperazinyl, morpholinyl, pyrazolyl, triazinyl and pyrrolidonyl particularly preferably methylamino, dimethylamino, piperazinyl and N-methylpiperazinyl.
  • the group N b R a is dimethylamino.
  • the group is methylamino.
  • the group stands for amino.
  • a further embodiment relates to compounds I in which T is C (O) NR b R b , where R b can assume the same meanings as R b and R b and R b independently of one another
  • R b, R b and R b are preferably hydrogen, cyano, C 1 -C 6 -alkyl, C 2 -C 3 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 8 cycloalkenyl, C (O) R ⁇ , C (O) OR ⁇ , C (S) OR ⁇ , C (O) SR ⁇ , C (S) SR ⁇ , Amino, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, aminocarbonyl, C (O) NHR ⁇ or C (O) NR ⁇ 2 ,
  • T C (O) NR b
  • R b, R b and R b are preferably hydrogen, C 1 -C 6 -alkyl, C (O) R ⁇ , C (O) OR ⁇ , aminocarbonyl, C ( O) NHR ⁇ or C (O) NR ⁇ 2 .
  • T C (O) NR b R b , R b and R b together with the nitrogen to which they are attached form a saturated, five-, six-, seven-, eight-, nine- or ten-membered one , partially unsaturated or aromatic heterocycles containing one, two, three or four heteroatoms from the group O, N and S.
  • R d preferably has the following meanings: halogen, cyano, hydroxy, mercapto, amino, carboxyl, alkyl, haloalkyl, alkenyl, alkynyl, alkoxy , Haloalkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylamino, dialkylamino, formyl, alkylcarbonyl, alkylsulfonyl, alkylsulfoxyl, alkoxycarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, aminocarbonyl, aminothiocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminocarbonyl, dialkylaminocarbonyl, dialkylaminocarbonyl, dialkylaminocarbonyl, dialkylaminocarbonyl, dialkylaminocarbonyl, dialkylaminocarbonyl,
  • C 1 -C 8 -alkyl C 1 -C 8 -alkyl
  • C 1 -C 8 -alkoximino NOC 1 -C 8 -alkyl
  • C 3 -C 8 -alkenyloximino NOC 3 -C 8 -alkenyl
  • C 3 -C 8 -Alkinyloximino NOC 3 -C 8 alkynyl
  • a further embodiment relates to compounds I in which T is C (NORNOR c ) R a , in which R a is hydrogen, cyano, hydroxyl, carboxyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 5 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 8 cycloalkenyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyloxy, C 3 -C 5 alkynyloxy, C 3 -C 5 -Cycloalkoxy, C 3 -C 6 -cycloalkenyloxy, C (O) R ⁇ , C (O) OR ⁇ , C (S) OR ⁇ , C (O) SR ⁇ , C (S) SR ⁇ , OC (O) OR ⁇ , C 1 -C 6 -alkylthio, amino, C 1 -C 6
  • T C (NORNOR c ) R a
  • R c is preferably hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 - C 6 -cycloalkyl, C 3 -C 8 -cycloalkenyl, C (O) R ⁇ , C (O) OR ⁇ , aminocarbonyl, C (O) NHR ⁇ or C (O) NR ⁇ 2 , more preferably hydrogen, dC 6 Alkyl, C 2 -C 6 alkenyl or C 2 -C 6 -Alk ⁇ nyl.
  • R a is preferably R a
  • R d preferably has the following meanings: Halogen, cyano, nitro, hydroxyl, mercapto, amino, carboxyl, alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, haloalkyl, alkenyloxy, alkynyloxy, alkylthio, alkylamino, dialkylamino, formyl, alkylcarbonyl, alkylsulfonyl, alkylsulfoxyl, alkoxycarbonyl, alkylcarbonyloxy, Alkoxycarbonyloxy, aminocarbonyl, ammothiocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylammothiocarbonyl, dialky
  • C 1 -C 8 -alkyl C 1 -C 8 -alkyl
  • C 1 -C 8 -alkoximino NOC 1 -C 8 -alkyl
  • C 3 -C 8 -alkenyloximino NOC 3 -C 8 -alkenyl
  • C 3 -C 8 -Alk ⁇ nylox ⁇ m ⁇ no NOC 3 -C 8 -Alk ⁇ nyl
  • T 1 means oxygen.
  • T 2 is oxygen.
  • T 2 is sulfur.
  • T 2 is NR b .
  • T 3 R a In a further embodiment, T 3 OR c .
  • T 3 SR c In another embodiment, T 3 is NR b R b .
  • R a preferably denotes hydrogen, cyano, hydroxyl, carboxyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkylene I, C 2 -C 6 -Al kiny I, C 3 -C 6 -cycloalkyl, C 3 -C 8 -cycloalkenyl, C 1 -C 5 -alkoxy, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkoxy, C 3 -C 6 -cycloalkenyloxy, C (O) R ⁇ , C (O) OR ⁇ , C (S) OR ⁇ , C (O) SR ⁇ , C (S) SR ⁇ , OC (O) OR ⁇ , C 1 -C 6 -alkylthio, amino
  • halogen hydroxyl, amino, carboxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkylamino, dialkylamino, alkylsulfonyl, alkylsulfoxyl, alkoxycarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, aminocarbonyl,
  • One embodiment relates to compounds I in which X is fluorine, chlorine or bromine, in particular chlorine.
  • a further embodiment relates to compounds I in which X is fluorine.
  • a further embodiment relates to compounds I 1 in which X is cyano.
  • a further embodiment relates to compounds I in which X is alkyl, in particular methyl.
  • a further embodiment relates to compounds I in which X is alkoxy, in particular methoxy.
  • One embodiment relates to compounds I in which G is N; E stands for CW 2 and Q stands for N. These compounds correspond to the formula 1.1.
  • Another embodiment relates to compounds I in which G is N; E stands for CW 2 and Q stands for CW 3 . These compounds correspond to the formula I.2.
  • Another embodiment relates to compounds I in which G is CW 1 ; E stands for CW 2 and Q stands for N. These compounds correspond to the formula 1.3.
  • Another embodiment relates to compounds I in which G is CW 1 ; E stands for N and Q stands for CW 3 . These compounds correspond to the formula 1.4.
  • W 1 is hydrogen, fluorine, chlorine or bromine, in particular hydrogen.
  • W 2 is hydrogen, cyano, fluorine
  • W 3 is hydrogen, cyano, fluorine, chlorine, bromine, iodine, nitro, formyl, haloalkyl having 1 to 4 carbon atoms and 1 to 9 fluorine, chlorine and / or bromine atoms, alkyl having 1 to 4 carbon atoms , Cycloalkyl having 3 to 6 carbon atoms, thiocarbamoyl, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy part, alkylcarbonyl having 1 to 4 carbon atoms in the alkyl part, hydroximinoalkyl having 1 to 4 carbon atoms in the alkyl part or alkoxyiminoalkyl having 1 to 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl moiety, aminocarbonyl, alkylaminocarbonyl having 1-4 carbon atoms in the alkyl moiety or dialkylaminocarbonyl each having 1-4 carbon atoms
  • W 3 is CR 10 R 11 OR 12 .
  • Tables 1 to 1254 - Compounds of the formula I.1A in which X is Cl, L m and P 1 each have the meaning identified and R is a compound which corresponds in each case to one row of Table A.
  • Y 1 is C (O) O, C (O) NR A , or S (O) t , t is 1 or 2 and the other symbols and indices have the meanings and preferences given for the formula I.
  • the invention further provides azolopyrimidines of the formula I in which T OR c (where R c ⁇ H), OC (O) R a , NR b R b ' , C (O) NR b R b' , C (NOR c ) R a ,
  • the invention furthermore relates to compounds of the formula I 1 in which W is five- or six-membered heteroaryl which, in addition to carbon atoms, contains one, two or three further heteroatoms from the group O, N and S as the ring member, the ring systems in addition to groups L m carry at least one substituent P 1 , and the other symbols and indices have the meanings and preferences given for the formula I.
  • G, E, Q a) G is N; E is CW 2 and Q is CW 3 ; b) G is CW 1 ; E is CW 2 and Q is N; or c) G is CW 1 ; E is N and Q is CW 3 ; and the remaining symbols and indices have the meanings and preferences given for the formula I.
  • the invention further relates to compounds of the formula I, wherein
  • Haloalkoxy and the other symbols and indices have the meanings and preferences given for the formula I.
  • the invention furthermore relates to compounds of the formula I 1 where R is C 3 -C 12 -halocycloalkyl and the other symbols and indices have the meanings and preferences given for the formula I.
  • the invention furthermore relates to compounds of the formula I 1 where T is OC (O) R a and the other symbols and indices have the meanings and preferences given for the formula I.
  • the compounds I are suitable as fungicides. They are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi from the class of the Ascomycetes, Deuteromycetes, Basidiomycetes and Peronospo- romyceten fsyn. Oomycetes). They are partially systemically effective and can be used in crop protection as foliar, pickling and soil fungicides.
  • Vegetables such as cucumbers, beans, tomatoes, potatoes and pumpkins, as well as the seeds of these plants.
  • the compounds I are suitable for controlling Alternaria species on vegetables, rapeseed, sugar beets and fruits and rice, such as. A. solani or A alternata on potatoes and tomatoes.
  • the compounds I are suitable for controlling Aphanomyces species on sugar beets and vegetables.
  • the compounds I are suitable for controlling Ascochyta species on cereals and vegetables.
  • the compounds I are suitable for controlling Bipolaris and Drechslera species on maize, cereals, rice and turf, such as e.g. D. maydis on corn.
  • the compounds I are suitable for controlling Blumeria graminis (powdery mildew) on cereals.
  • the compounds I are suitable for controlling Botrytis cinerea (gray shrimp) on strawberries, vegetables, flowers and grapevines.
  • the compounds I are suitable for controlling Bremia lactucae on lettuce.
  • the compounds I are suitable for controlling Cercospora species on maize, soybeans, rice and sugar beet.
  • the compounds I are suitable for controlling Cochliobolus species on maize, cereals, rice, such as e.g. Cochliobolus sativus on cereals, Cochliobolus miyabeanus on rice.
  • the compounds I are suitable for controlling Colletotricum species on soy beans and cotton.
  • the compounds I are suitable for controlling wood turner species, Pyrenophora species on corn, cereals, rice and turf, such as e.g. D. teres on barley or D. tritici- repentis on wheat.
  • the compounds I are suitable for controlling Esca on grapevine, caused by Phaeoacremonium chlamydosporium, Ph. Aleophilum, and Formitipora punctata (syn. Phellinus punctatus).
  • the compounds I are suitable for controlling Exserohilum species on maize.
  • the compounds I are suitable for controlling Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits.
  • the compounds I are useful for controlling Fusarium and Verticillium species on various plants, e.g. F. graminearum or F. culmorum on cereal or F. oxysporum on a variety of plants, e.g. Tomatoes.
  • the compounds I are suitable for controlling Gaeumanomyces graminis on cereals.
  • the compounds I are suitable for controlling Gibberella species on cereals and rice (eg Gibberella fujikuroi on rice).
  • the compounds I are suitable for controlling grainstaining complex in rice.
  • the compounds I are suitable for controlling Helminthosporium species on maize and rice.
  • the compounds I are suitable for controlling Michrodochium nivale on cereals.
  • the compounds I are suitable for controlling Mycosphaerella species on cereals, bananas and peanuts, such as e.g. M. graminicola on wheat or M. fijiensis on bananas.
  • the compounds I are suitable for controlling Peronospora species on cabbage and bulbous plants, such as e.g. P. brassicae on cabbage or P. destructor on onion.
  • the compounds I are suitable for controlling Phakopsara pachyrhizi and Phakopsara meibomiae on soybeans.
  • the compounds I are suitable for controlling Phomopsis species on soybeans and sunflowers.
  • the compounds I are suitable for controlling Phytophthora infestans on potatoes and tomatoes.
  • the compounds I are suitable for controlling Phytophthora species on various plants, such as e.g. P. capsici on paprika.
  • the compounds I are suitable for controlling Plasmopara viticola on grapevines.
  • the compounds I are suitable for controlling Podosphaera leucotricha on apple.
  • the compounds I are suitable for controlling Pseudocercosporella herpotriodides on cereals.
  • the compounds I are suitable for controlling Pseudoperonospora on various plants, such as e.g. P. cubensis on cucumber or P. humili on hops.
  • the compounds I are suitable for controlling Puccinia species on various plants, such as e.g. P. triticina, P. striformins, P. hordei or P. graminis on cereals, or P. asparagi on asparagus.
  • the compounds I are suitable for controlling Pyricularia oryzae, Corticium sasakii, Sarocladium oryzae, S. attenuatum, Entyloma oryzae, rice.
  • the compounds I are suitable for controlling Pyricularia grisea on lawns and cereals.
  • the compounds I are suitable for controlling Pythium spp. on turf, rice, corn, cotton, rape, sunflowers, sugar beet, vegetables and other plants, e.g. P.ultiumum on various plants, P. aphanidermatum on lawn.
  • the compounds I are suitable for controlling Rhizoctonia species on cotton, rice, potatoes, turf, maize, oilseed rape, potatoes, sugar beets, vegetables and various plants, such as e.g. R. solani on turnips and various plants.
  • the compounds I are suitable for controlling Rhynchosporium secalis on barley, rye and triticale.
  • the compounds I are suitable for controlling Sclerotinia species on rape and sunflowers.
  • the compounds I are suitable for controlling Septoria tritici and Stagonospora nodorum on wheat.
  • the compounds I are suitable for controlling Erysiphe (syn. Uncinula) necator on grapevine.
  • the compounds I are suitable for controlling Setospaeria species on maize and turf.
  • the compounds I are suitable for controlling Sphacelotheca reilinia on maize.
  • the compounds I are suitable for controlling Thievaliopsis species on soy beans and cotton.
  • the compounds I are suitable for controlling Tilletia species on cereals.
  • the compounds I are useful for controlling Ustilago species on cereals, maize and sugar cane, such as e.g. U. maydis on corn.
  • the compounds I are suitable for controlling Venturia species (scab) on apples and pears such as. e.g. V. inaequalis to apple.
  • the compounds according to the invention can also be used in cultures that are tolerant to insects or fungi by breeding, including genetic engineering methods.
  • the compounds I are also suitable for controlling harmful fungi in material protection (eg wood, paper, dispersions for painting, 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., Cololus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp.
  • Tyromyces spp. Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and zygomycetes such as Mucor spp., moreover, in the context of protection of materials, the following yeast fungi: Candida spp. and Saccharomyces cerevisae.
  • the compounds according to the invention and / or their agriculturally acceptable salts 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 compounds.
  • Another object of the invention is therefore a method for controlling phytopathogenic fungi, which is characterized in that the fungi or the fungal infection to be protected materials, plants, the soil or seeds with an effective amount of at least one compound I and / or of an agriculturally acceptable salt thereof.
  • Another object of the invention is an agent for controlling phytopathogenic fungi, comprising at least one compound of the formula (Ia) according to the invention and / or an agriculturally acceptable salt thereof and at least one solid or liquid carrier.
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90 wt .-% of active ingredient.
  • the application rates in crop protection range from 0.01 to 2.0 kg of active ingredient per ha.
  • amounts of active ingredient are from 1 to 1000 g / 100 kg, preferably from 5 to 100 g / 100 kg of seed 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; In any case, it should 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
  • glycol diacetate glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters.
  • solvent mixtures can also be used
  • Excipients such as ground natural minerals (e.g., kaolins, clays, talc, chalk) and ground synthetic minerals (e.g., fumed silica, silicates); Emulsifiers such as non-ionic and anionic emulsifiers (for example polyoxyethylene
  • 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, eg toluene, Xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, for example dimethylsulfoxide, N-methylpyrrolidone or water.
  • 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 eg toluene, Xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol,
  • Powders, litter and dusts may be prepared by mixing or co-mingling 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, lo
  • the formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight of the active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • formulations are: 1. Products for dilution in water
  • a Water-soluble concentrates (SL, LS)
  • the active compounds 20 parts by weight are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant, e.g. Polyvinylpyrrolidone dissolved. Dilution in water results in a dispersion.
  • the active ingredient content is 20% by weight
  • Dodecylbenzenesulfonate and castor oil ethoxylate (each 5 parts by weight) dissolved. 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.
  • E suspensions 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.
  • the active ingredients are finely ground with the addition of 50 parts by weight of dispersants 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.
  • the active ingredients 75 parts by weight of the active ingredients are ground with the addition of 25 parts by weight of dispersing 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.
  • 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 dusts
  • GF GF used.
  • These formulations may be applied to the seed undiluted or, preferably, diluted. The application can be done before sowing.
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, with grit, granules by spraying, atomising, dusting, sprinkling or pouring.
  • the forms of application depend entirely on the intended use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
  • the substances for the preparation of 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.
  • wetter tackifier
  • dispersant or emulsifier it is also possible to prepare from effective substance wetting agents, tackifiers, dispersants or emulsifiers and any solvents or oil concentrates which are suitable for diluting with water.
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
  • the active substances may be added to oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides, if appropriate also immediately before use (tank mix). These agents can be preferred to the agents according to the invention in a weight ratio of 1: 100 to 100: 1
  • Particularly suitable adjuvants in this sense are: organically modified polysiloxanes, for example Break Thru S 240® ; Alcohol alkoxylates, eg. B. Atplus 245 ®, Atplus
  • Pluronic RPE 2035 ® and Genapol B ® Alcohol ethoxylates, eg. As Lutensol XP 80 ®; and
  • the compounds of the invention may also be present in the application form as fungicides together with other active substances, e.g. with herbicides, insecticides, growth regulators, fungicides or with fertilizers.
  • active substances e.g. with herbicides, insecticides, growth regulators, fungicides or with fertilizers.
  • Another object of the invention is therefore a combination of at least one compound of the formula (I) according to the invention and / or an agriculturally acceptable salt thereof and at least one further fungicidal, insecticidal, herbicidal and / or growth-regulating active ingredient.
  • Azoxystrobin dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, orysastrobin, (2-chloro-5- [1 - (3-methyl-benzyloxyimino) -ethyl] -benzyl) -carbamic acid methyl ester, (2-Chloro-5- [1- (6-methyl-pyridin-2-ylmethoxyimino) -ethyl] -benzyl) -carbamic acid methyl ester, 2- (ortho- (2,5-dimethylphenyl-oxymethylene) -phenyl) -3- methoxy-methyl acrylate;
  • Benzoic acid amides flumetover, fluopicolide (picobenzamide), zoxamide;
  • carboxamides carpropamide, diclocymet, mandipropamide, N- (2- (4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-methanesulfonylamino
  • bitertanol bromuconazoles, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fenbuconazole, flusilazole, fluquinconazole, flutriol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazo - Ie, triadimenol, triadimefon, triticonazole;
  • - imidazoles cyazofamide, imazalil, pefurazoate, prochloraz, triflumizole; Benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole;
  • Pyridines fluazinam, pyrifenox, 3- [5- (4-chlorophenyl) -2,3-dimethylisoxazolidin-3-yl] pyridine; Pyrimidines: bupirimate, cyprodinil, ferimzone, fenarimol, mepanipyrim, nuarimol, pyrimethanil;
  • Morpholines aldimorph, dodemorph, fenpropimorph, tridemorph;
  • Dicarboximides iprodione, procymidone, vinclozolin;
  • guanidines dodine, iminoctadine, guazatine
  • Organometallic compounds fentin salts
  • Sulfur-containing heterocyclyl compounds isoprothiolanes, dithianone
  • Organophosphorus compounds edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, pyrazophos, tolclofos-methyl, phosphorous acid and their salts;
  • Organochlorine compounds thiophanates methyl, chlorothalonil, dichlofluanid, toiylfluanid, flusulfamides, phthalides, hexachlorobenzene, pencycuron, quintozene; Nitrophenyl derivatives: binapacryl, dinocap, dinobuton;
  • the present invention further relates to the compositions listed in Table B, wherein in each case one row of Table B corresponds to a fungicidal composition comprising a compound of Formula I (Component 1), which is preferably one of the compounds described herein as preferred and the further active ingredient (component 2) indicated in the respective line.
  • component 1 in each row of table B is in each case one of the compounds of the formula I which are specifically individualized in tables 1 to 1254.
  • the present invention furthermore relates to the pharmaceutical use of the azolopyrimidines of the formula II according to the invention, in particular the azolopyrimidines of the formula II described in the preceding description, and / or the pharmaceutically acceptable salts thereof, in particular their use for the treatment of Tumors in mammals such as humans.
  • the invention thus also provides a medicament, in particular for the treatment of tumors, containing a compound of the formula II, and the use of a compound of the formula II for the preparation of a medicament, in particular for the treatment of tumors.
  • HPLC column RP-18 column (Chromolit Speed ROD from Merck KgaA, Germany), 50 mm x 4.6 mm
  • Residue was purified by column chromatography with ethyl acetate / methanol mixtures.
  • the active compounds were prepared separately or together as a stock solution with 25 mg of active ingredient which was mixed with a mixture of acetone and / or DMSO and the emulsifier Wettol (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) in the volume ratio solvent Emulsifier from 99 to 1 ad 10 ml was filled. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the drug concentration given below.
  • Wettol wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • 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 spore suspension of Alternaria solani in 2% biomalt solution with a density of 0.17 ⁇ 10 6 spores / ml. Subsequently, the plants were placed in a water vapor-saturated chamber at temperatures between 20 and 22 ° 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%.
  • 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 sporangia 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 developed so strongly that the infestation could be determined visually in%.
  • the active ingredients were formulated separately as stock solution with a concentration of 10,000 ppm in DMSO.
  • the stock solution is pipetted into a microtiter plate (MTP) and diluted with an aqueous malt-based mushroom nutrient medium to the stated active substance concentration. This was followed by the addition of an aqueous spore suspension of Botrytis cinerea.
  • MTP microtiter plate
  • the plates were placed in a 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 drug-free control variant and the fungus- and drug-free blank to determine the relative growth in% of the pathogens in the individual drugs.
  • pathogens with a drug concentration of 125 ppm of Compounds 1-10, 1-12, 1-14, 1-18, 1-19, I-23, I-26, I-30, 1-31 , I-38 and II-6 were treated, a relative growth of less than 15%.
  • the stock solution is pipetted into a microtiter plate (MTP) and diluted with an aqueous fungus nutrient medium based on pea juice to the stated active substance concentration. This was followed by the addition of an aqueous zoospore suspension of Phytophthora infestans.
  • MTP microtiter plate
  • the plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. With an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.
  • the measured parameters were compared with the growth of the drug-free control variant and the fungus- and drug-free blank to determine the relative growth in% of the pathogens in the individual drugs.
  • pathogens treated with a drug concentration of 125 ppm of compounds 1-12, 1-18, 1-19, 1-31, I-38 and II-6 showed a relative growth of less than 10%.
  • the stock solution is pipetted into a microtiter plate (MTP) and diluted to the stated active substance concentration with an aqueous malt-based mushroom nutrient medium. This was followed by the addition of an aqueous spore suspension of Septoria tritici.
  • MTP microtiter plate
  • the plates were placed in a water vapor-saturated chamber at temperatures of 18 ° C. With an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.
  • the measured parameters were compared with the growth of the drug-free control variant (100%) and the fungus-free and drug-free blank to determine the relative growth in% of the pathogens in the individual drugs.
  • pathogens treated with a drug concentration of 125 ppm of compounds 1-10, 1-14 and I-26 showed a relative growth of less than 10%.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pretreatment Of Seeds And Plants (AREA)

Abstract

Des azolopyrimidines de formule (I), où les symboles ont les significations indiquées dans la description, conviennent pour la lutte contre des champignons parasites phytopathogènes.
EP08701270A 2007-01-08 2008-01-07 Utilisation d'azolopyrimidines pour la lutte contre des champignons parasites phytopathogenes Withdrawn EP2117312A1 (fr)

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EP07100233 2007-01-08
EP08701270A EP2117312A1 (fr) 2007-01-08 2008-01-07 Utilisation d'azolopyrimidines pour la lutte contre des champignons parasites phytopathogenes
PCT/EP2008/050093 WO2008084027A1 (fr) 2007-01-08 2008-01-07 Utilisation d'azolopyrimidines pour la lutte contre des champignons parasites phytopathogènes

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UA80304C2 (en) * 2002-11-07 2007-09-10 Basf Ag Substituted 6-(2-halogenphenyl)triazolopyrimidines
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WO2005030218A1 (fr) * 2003-09-24 2005-04-07 Wyeth Holdings Corporation 6-aryl-7-halo-imidazo[1,2-a]pyrimidines, agents anticancereux
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JP2010515669A (ja) 2010-05-13

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