EP1876899A2 - Utilisation de 5-alkyl-6-phenylalkyl-7-amino-azolopyrimidines, nouvelles azolopyrimidines, procede de fabrication et agents les contenant - Google Patents

Utilisation de 5-alkyl-6-phenylalkyl-7-amino-azolopyrimidines, nouvelles azolopyrimidines, procede de fabrication et agents les contenant

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Publication number
EP1876899A2
EP1876899A2 EP06754813A EP06754813A EP1876899A2 EP 1876899 A2 EP1876899 A2 EP 1876899A2 EP 06754813 A EP06754813 A EP 06754813A EP 06754813 A EP06754813 A EP 06754813A EP 1876899 A2 EP1876899 A2 EP 1876899A2
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EP
European Patent Office
Prior art keywords
formula
alkyl
sup
compounds
hydrogen
Prior art date
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EP06754813A
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German (de)
English (en)
Inventor
Jochen Dietz
Wassilios Grammenos
Thomas Grote
Udo HÜNGER
Jan Klaas Lohmann
Bernd Müller
Joachim Rheinheimer
Peter Schäfer
Frank Schieweck
Anja Schwögler
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BASF SE
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BASF SE
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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Definitions

  • the present invention relates to the use of 5-alkyl-6-phenylalkyl-7-amino-azolopyrimidinen of the formula I.
  • Y is d-Ce-alkylene, C ⁇ -C ⁇ -alkenylene or C ⁇ -C ⁇ -alkynylene, optionally substituted by 1 to 4 Ci-C 6 -alkyl groups;
  • R 1 is halogen, cyano, nitro, hydroxy, mercapto, CrC 6 alkyl, Ci-C 4 haloalkyl, C 2 - Ce alkenyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkenyl, C 6 alkoxy, Ci-6-halo-C alkoxy, C 2 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy Ci-C6 alkylthio, NR A R B, -C 6 - alkylcarbonyl, phenyl, naphthyl, or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one to four heteroatoms from the group O, N or S; R A , R B are hydrogen, C 1 -C 6 -alkyl and C 1 -C 6 -alkylcarbonyl;
  • n is zero, 1, 2, 3 or 4;
  • R 2 is C 2 -C 6 alkyl, C 2 -C 4 -alkyl keny I, C 3 -C 6 cycloalkyl, Ci-C 2 alkoxy-Ci-Ci 2 alkyl and Ci Ci Ci-2 alkylthio -Ci2-alkyl;
  • R 3 is hydrogen, halogen, cyano, NR A R B, hydroxyl, mercapto, C 2 -C 6 -A ⁇ yI, Ci-C 6 - haloalkyl, C 3 -C 8 cycloalkyl, Ci-C 6 alkoxy, C -C 6 alkylthio, C 3 -C 8 cycloalkoxy, C 3 -C 8 cycloalkylthio, carboxyl, formyl, Ci-Cio-alkylcarbonyl, Ci-Cio-AIkoxy- carbonyl, Ca-Cio-alkenyloxycarbonyl, C2-Cio Alkynyloxycarbonyl, phenyl, phenoxy, phenylthio, benzyloxy, benzylthio, Ci-C 6 -alkyl-S (O) m -; m is 0, 1 or 2;
  • R a is hydrogen and C 1 -C 6 -alkyl
  • R b is halogen, cyano, nitro, hydroxy, C 3 -C 6 cycloalkyl, Ci-C 6 alkoxy, -C 6 - alkylthio, and NR A R B;
  • the invention relates to novel 5-phenylalkyl-6-alkyl-7-amino-azolopyrimidines, processes for the preparation of these compounds and agents containing them.
  • the compounds of the formula I differ from the compounds known from EP-A 141 317 essentially by the specific embodiment of the substituent in the 5-position of the azolopyrimidine skeleton.
  • the compounds of the formula I have an over the known compounds increased activity against harmful fungi.
  • the compounds of the invention can be obtained in various ways.
  • the compounds according to the invention are obtained by reacting substituted ⁇ -ketoesters of the formula II with an aminoazole of the formula III to give 7-hydroxytriazolopyrimidines of the formula IV.
  • the groups R 1 and R 2 in formulas II and IV have the meanings as for formula I and the group R in formula II means C 1 -C 4 -alkyl, for practical reasons, methyl, ethyl or propyl is preferred therein.
  • reaction of the substituted ⁇ -keto esters of the formula II with the aminoazoles of the formula III can be carried out in the presence or absence of solvents. the. It is advantageous to use those solvents to which the starting materials are largely inert and in which they are completely or partially soluble.
  • Particularly suitable solvents are alcohols such as ethanol, propanols, butanols, glycols or glycol monoethers, diethylene glycols or their monoethers, aromatic hydrocarbons such as toluene, benzene or mesitylene, amides such as dimethylformamide, diethylformamide, dibutylformamide, N, N-dimethylacetamide, lower alkanoic acids such as formic acid, acetic acid, Propionic acid or bases, 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, especially alkali metal alkyls, alkyl magnesium halides and alkali metal and alkaline earth metal alkoxides and dimethoxy magnesium, and also organic Bases, for example
  • Suitable catalysts are bases, as mentioned above, or acids, such as sulfonic acids or mineral acids.
  • the reaction is particularly preferably carried out without a solvent or in chlorobenzene, xylene, dimethyl sulfoxide, N-methylpyrrolidone.
  • Particularly preferred bases are tertiary amines such as triisopropylethylamine, tributylamine, N-methylmorpholine or N-methylpiperidine.
  • the temperatures are between 50 and 300 ° C., preferably 50 to 180 ° C., when working in solution [cf. EP-A 770 615; Adv. Het. Chem. Vol. 57, p. 81 ff. (1993)].
  • the bases are generally used in catalytic amounts, but they can also be used equimolar, in excess or optionally as a solvent.
  • the condensation products of the formula IV thus obtained are usually precipitated from the reaction solutions in pure form and are, after washing with the same solvent or with water and subsequent drying with halogenating agents, in particular chlorinating or brominating agents, the compounds of the formula V 1 in the Hal is chlorine or bromine, in particular chlorine, reacted.
  • the reaction with chlorinating agents such as phosphorus oxychloride, thionyl onylchlorid or sulfuryl chloride is preferably carried out at 50 ° C to 15O 0 C, preferably in excess phosphorus oxytrichloride at reflux temperature. After evaporation of the excess Phosphoroxitrichlorids the residue is treated with ice water optionally with the addition of a water-immiscible solvent.
  • the isolated from the dried organic phase optionally after evaporation of the inert solvent chlorination product is usually very pure and is then with Ammonia in inert solvents at 100 0 C to 200 0 C to the 7-amino-triazolo [1, 5-a] -pyrimidines reacted.
  • the reaction is preferably carried out with 1 to 10 molar excess of ammonia under pressure of 1 to 100 bar.
  • the new 7-amino-azolo [1, 5-a] -pyrimidines are optionally isolated after evaporation of the solvent by trituration in water as crystalline compounds.
  • the ⁇ -keto esters of formula II can be prepared as in Organic Synthesis Coli. Vol. 1, p. 248, or are commercially available.
  • novel compounds of the formula I can be obtained by reacting substituted acyl cyanides of the formula VI, in which R 1 and R 2 have the meanings indicated above, with 3-amino-1, 2,4-triazole of the formula III.
  • the reaction can be carried out in the presence or absence of solvents. It is advantageous to use those solvents to which the starting materials are largely inert and in which they are completely or partially soluble.
  • the solvents used are, in particular, alcohols such as ethanol, propanols, butanols, glycols or glycol monoethers, diethylene glycols or their monoethers, aromatic hydrocarbons such as toluene, benzene or mesitylene, amides such as dimethylformamide, diethylformamide, dibutylformamide, N, N-dimethylacetamide, lower alkanoic acids such as formic acid, Acetic acid, propionic acid or bases, as mentioned above, and mixtures of these solvents with water in question.
  • the reaction temperatures are between 50 and 300 ° C, preferably at 50 to 150 ° C, when working in solution.
  • the new 7-amino-triazolo [1, 5-a] -pyrimidines are optionally isolated after evaporation of the solvent or dilution with water as crystalline compounds.
  • substituted alkyl cyanides of formula VI required for the preparation of the 7-amino-azolo [1,5-a] -pyrimidines are known in part or may be prepared by known methods from alkyl cyanides and carboxylic acid esters with strong bases, e.g. Alkali metal hydrides, alkali metal alcoholates, alkali diamides or metal alkyls [cf.: J. Amer. Chem. Soc. Vol. 73, (1951) p. 3766].
  • 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, separation is generally not necessary since the individual isomers may partially 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 mono- or di-branched hydrocarbon radicals having 1 to 4, 6, 8 or 12 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, n-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-dimethylphenyl methylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-e
  • Haloalkyl alkyl group as mentioned above, in which partially or completely the hydrogen atoms may be replaced by halogen atoms as mentioned above: in particular chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl;
  • Alkoxyalkyl saturated, straight-chain or mono-, di- or tri-branched hydrocarbon chain which is interrupted by an oxygen atom, for.
  • Cs-Ci 2 -Alkoxy- alkyl hydrocarbon chain as described above having 5 to 12 carbon atoms, which may be interrupted by an oxygen atom at any position, such as propoxy-ethyl, butoxy-ethyl, pentoxy-ethyl, hexyloxy-ethyl, heptyloxy ethyl, octyloxyethyl, nonyloxyethyl, 3- (3-ethyl-hexyloxy) -ethyl, 3- (2,4,4-trimethyl-pentyloxy) -ethyl, 3- (1-ethyl-3-methyl) butoxy) -ethyl, ethoxy-propyl, propoxy-propyl, butoxy-propyl, pentoxy-propyl, he
  • Alkynyl straight-chain or branched hydrocarbon groups having 2 to 4, 6, 8 or 10 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 e.g. 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5- isothiazolidinyl, 3-pyrazolidinyl, 4-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 besides carbon atoms may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members 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-thiazoline iyi 1 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
  • Alkylene divalent unbranched or branched chains of 1 to 6 CH 2 groups, which can carry up to four Ci-C 6 alkyl groups, eg CH 2 , CH 2 CH 2 , CH (CH 3 ) CH 2 , CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 , CH (CH 3 ) CH 2 CH 2 , CH (CH 2 CH 3 ) CH 2 CH 2 and CH 2 CH 2 CH 2 CH 2 CH 2 ;
  • the group Y has no or one branching, preferably Y represents unbranched C 1 -C 6 -cycles, in particular C 1 -C 4 -alkylene. Particularly preferred meanings for Y are methylene and ethylene.
  • one or two groups R 1 are present, which preferably has the following meaning: halogen, C 1 -C 6 -alkyl and halomethyl.
  • R 2 represents an ethyl or an n-propyl group.
  • R 3 is hydrogen, NH 2 or C 1 -C 6 -alkyl, preferably hydrogen or NH 2 , in particular hydrogen.
  • A is N or CH, in particular N.
  • Y is C 1 -C 6 -alkylene, optionally substituted by 1 to 4 C 1 -C 6 -alkyl groups;
  • R 1 is halogen, C 1 -C 6 -alkyl and halomethyl; n is zero, 1, 2 or 3;
  • R 2 is C 2 -C 6 -alkyl, C 3 -C 6 cycloalkyl and C r Ci2-alkoxy-Ci-Ci 2 alkyl;
  • R 3 is hydrogen, NH 2 and C r C 6 alkyl; AN and CR c ;
  • R c is hydrogen and C 1 -C 6 -alkyl.
  • Table 19 corresponds to those in compounds of formula I Y 1 CH 2, R 2 is n-propyl, AN, R 3 is hydrogen and R 1 ⁇ for each compound corresponds to one row of Table A
  • Table 25 Compounds of the formula I in which Y is CH 2 , R 2 is ethyl, A is CH, R 3 is amino and R 1 n for each compound corresponds to one row of Table A.
  • Table 26 Compounds of the formula I in which Y is CH 2 , R 2 is ethyl, A is CH, R 3 is amino and R 1 n for each compound corresponds to one row of Table A.
  • Table 48 Compounds of the formula I in which Y is CH (CH 3 ) CH 2 CH 2 , R 2 is n-propyl, AN, R 3 is amino and R 1 n for each compound corresponds to one row of Table A.
  • Table 58 Compounds of the formula I in which Y is CH (CH 3 ) CH 2 , R 2 is n-propyl, A is CH 1 R 3 is methyl and R 1 n for each compound corresponds to one row of Table A.
  • the compounds I are suitable as fungicides. They are distinguished by outstanding activity against a broad spectrum of phytopathogenic fungi from the classes of the Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes, in particular from the class of the Oomycetes. They are partially systemically effective and can be used in crop protection as foliar, pickling and soil fungicides.
  • Botrytis cinerea (gray mold) on strawberries, vegetables, flowers and vines;
  • Glbberella species on cereals and rice e.g., Gibberella fujikuroian rice, • Grainstaining complex of rice;
  • Mycosphaerella species on cereals, bananas and peanuts e.g. M. graminicola on wheat or M.fijiensis on bananas; Peronospora species on cabbage and bulbous plants, such as P. brassicae
  • Pseudoperonospora on various plants e.g. P. cubensfsan cucumber or P. humili on hops;
  • PucciniaA ⁇ en on various plants such. P. triticina, P. striformins, P. hordei or P. graminis on cereals, or P. asparagi on asparagus;
  • Rhizoctonia species on cotton, rice, potatoes, lawns, maize, rapeseed, potatoes, sugar beet, vegetables and various plants such as: R. solani on turnips and various plants;
  • Rhynchosporium secalis on barley, rye and triticale • Rhynchosporium secalis on barley, rye and triticale; • Sclerotinia species on oilseed rape and sunflowers;
  • Oomycetes such as Peronospora species, Phytophthora species, Plasmopara viticola and Pseudoperonospora species.
  • the compounds I are also suitable for controlling harmful fungi in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
  • harmful fungi ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sciophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., P / ei / -> spp., Por / a spp., Serpula spp.
  • Tyromyces spp. Deuteromycetes such as Aspergillus spp., Cladospori umspp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., moreover, in the protection of the following yeasts: Candida spp. and Saccharomyces cerevisae.
  • the compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally effective amount of the active ingredients.
  • the application can be done both before and after the infection of the materials, plants or seeds by the fungi.
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90 wt .-% of active ingredient.
  • the application rates in the application in crop protection depending on the nature of the desired effect between 0.01 and 2.0 kg of active ingredient per ha.
  • active ingredient in general, amounts of active ingredient of 1 to 1000 g / 100 kg, preferably 5 to 100 g / 100 kg of seed are needed.
  • the application rate of active ingredient depends on the type of application and the desired effect.
  • Usual 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 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 application; It should in any case ensure a fine and uniform distribution of the compound according to the invention.
  • the formulations are prepared in 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 1 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 or diesel oil, coal tar oils and oils of plant or animal origin
  • mineral oil fractions of medium to high boiling point such as or diesel oil, coal tar oils and oils of plant or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives
  • strongly polar solvents for example dimethyl sulfoxide, N-methylpyrrolidone or water into consideration.
  • Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
  • Granules e.g. Coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers.
  • Solid carriers are e.g. Mineral earths, such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell meal, cellulose powder and other solid carriers.
  • Mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics
  • the formulations generally contain between 0.01 and 95% 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
  • the active compounds 25 parts by weight of the active compounds are dissolved in 35 parts by weight of xylene with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
  • This mixture is added to water by means of an emulsifying machine (e.g., Ultraturax) in 30 parts by weight and made into a homogeneous emulsion. Dilution in water results in an emulsion.
  • the formulation has an active ingredient content of 25% by weight.
  • the active ingredients 20 parts by weight of the active ingredients are comminuted with the addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine active substance suspension. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • the active ingredients are finely ground with the addition of 50 parts by weight of dispersants and wetting agents and prepared by means of technical 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 substance.
  • the formulation has an active ingredient content of 50% by weight.
  • Water-dispersible and water-soluble powders 75 parts by weight of the active compounds are ground in a rotor-stator mill with the addition of 25 parts by weight of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active ingredient content of the formulation is 75% by weight.
  • 0.5 parts by weight of the active ingredients are finely ground and treated with 99.5 parts by weight of connected. 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
  • WS water-dispersible and water-soluble powders
  • ES emulsifiable concentrates
  • GF gel formulations
  • the active compounds may be used as such, in the form of their formulations or the forms of use prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, litter, granules by spraying, misting, dusting, scattering or pouring.
  • the forms of application depend entirely on the intended use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders, oil dispersions) by adding water.
  • the substances as such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier.
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume
  • the active substances may include oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides, if appropriate also only be added immediately before application (tank mix). These agents can be added to the Mittein invention in a weight ratio of 1: 100 to 100: 1, preferably 1: 10 to 10: 1.
  • organically modified polysiloxanes eg Break Thru S 240 ®
  • Alcohol alkoxylates eg. As Atplus 245 ®, Atplus MBA 1303 ®, Plurafac LF 300 ® and Lutensol ON 30 ®
  • EO-PO block polymers eg. B. Pluro- nic RPE 2035 ® and Genapol B ®
  • Alcohol ethoxylates eg. As Lutensol XP 80 ®
  • sodium dioctylsulfosuccinate e. B. Leophen RA ®.
  • the agents can also be present in the application form as fungicides together with other active ingredients, for example with herbicides, insecticides, • growth regulators, fungicides or else with fertilizers.
  • fungicides for example, in many cases the spectrum of activity can be widened or resistance developments can be prevented. In many cases, synergistic effects are obtained.
  • Azoxystrobin dimoxystrobin, enestroburine, 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-methylpyridin-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;
  • Other carboxamides carpropamide, diclocymet, mandipropamide, N- (2- (4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-methanesulfonylamino 3-methyl-butyramide, N- (2- (4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxy-phenyl) -ethyl) -2-ethanesulfonyl-amino-3-methyl- butyramide;
  • Azoles - triazoles bitertanol, bromuconazoles, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fenbuconazole, flusilazole, fluquinconazole, flutriol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, Tetraconazoles, triadimenol, triadimefon, triticonazole; - imidazoles: cyazofamide, imazalil, pefurazoate, prochloraz, triflumizole;
  • Benzimidazoles benomyl, carbendazim, fuberidazole, thiabendazole;
  • Nitrogen-containing heterocyclyl compounds - pyridines fluazinam, pyrifenox, 3- [5- (4-chloro-phenyl) -2,3-dimethyi-isoxazolidin-3-yl] -pyridine;
  • Pyrimidines bupirimate, cyprodinil, ferimzone, fenarimol, mepanipyrim, nuarimol, pyrimethanil;
  • - piperazines triforins
  • - Pyrroles fludioxonil, fenpiclonil
  • Dicarboximides iprodione, procymidone, vinclozolin;
  • acibenzolar-S-methyl anilazine, captan, captafol, dazomet, diclomethine, fenoxanil, folpet, fenpropidin, famoxadone, fenamidone, octhilinone, probenazole, proquinazide, pyroquilon, quinoxyfen, tricyclazole, 5-chloro-7- ( 4-methyl-piperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine, 2-butoxy-6- iodo-3-propyl-chromen-4-one, 3- (3-bromo-6-fluoro-2-methyl-indole-1-sulfonyl) - [1,2,4] triazole-1-sulfonic acid dimethylamide;
  • guanidines dodine, iminoctadine, guazatine
  • - Antibiotics Kasugamycin, Polyoxins, Streptomycin, Validamycin A
  • 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, toluylfluanid, flusulfamides, phthalides, hexachlorobenzene, pencycuron, quintozene; Nitrophenyl derivatives: binapacryl, dinocap, dinobuton;
  • Example 6 Preparation of 7-amino-6- (2-phenylethyl) -5-propyl- (1, 2,4) -triazolo- (1,5-a) -pyrimidine [I-2]
  • a solution of 1, 3 g of the chlorotriazolopyrimidine from Example 5 and 1, 1 ml of liquid ammonia in 50 ml of anhydrous 1,4-dioxane was stirred in an autoclave at 13O 0 C under autogenous pressure. Then, the solvent was distilled off and the residue was digested with dichloromethane / water. The organic phase was separated, washed with water, dried and freed from the solvent. Trituration with MTBE gave 0.52 g of the title compound, mp 190 -. 191 0 C.
  • the active compounds were prepared as a stock solution with 25 mg of active ingredient, which with a mixture of acetone and / or DMSO and the emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing based on ethoxylated alkylphenol Ie) in the volume ratio solvent-emulsifier made up from 99 to 1 ad 10 ml has been. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the drug concentration given below.
  • Uniperol® EL wetting agent with emulsifying and dispersing based on ethoxylated alkylphenol Ie
  • the comparative active substance used was the compound A known as Example No. 9 from EP-A 141 317:
  • Leaves of pot fry were sprayed to drip point with aqueous suspension in the concentration of active compound given below.
  • the undersurfaces of the leaves were inoculated with an aqueous sporangia suspension of Plasmopara viticola.
  • the vines were first placed for 48 hours in a water vapor-saturated chamber at 24 0 C and then for 5 days in a greenhouse at temperatures between 20 and 30 ° C. After this time, the plants were again placed in a humid chamber for 16 hours to accelerate the sporangiopathic outbreak. Then the extent of infestation on the undersides of the leaves was visually determined.
  • the plants treated with 250 ppm of the active ingredient I-5 showed 5% infestation, while the plants treated with 250 ppm of the comparative active substance A showed 90%, those with 63 ppm of the active ingredients 1-10, 1-11, 1-13 , 1-14, or 1-17 treated plants were up to 30% and the untreated plants 90% infected.
  • Leaves of pot fry were sprayed to drip point with aqueous suspension in the concentration of active compound given below.
  • the plants were placed in the greenhouse for 7 days after the spray coating had dried on. Only then were the leaves inoculated with an aqueous zoospore suspension of Plasmopara viticola. Thereafter, the vines were first set up for 48 hours in a water vapor-saturated chamber at 24 ° C and then for 5 days in the greenhouse at temperatures between 20 and 30 0 C. After this time, the plants were again placed in a humid chamber for 16 hours to accelerate the sporangiopathic outbreak. Then the extent of infestation on the undersides of the leaves was visually determined. In this test, the plants treated with 250 ppm of the active compounds 1-3, or 1-5 did not show more than 10% infestation, whereas the plants treated with 250 ppm of the comparative active substance A had 70% and the untreated plants 90%.
  • Leaves of pot fry were sprayed to drip point with aqueous suspension in the concentration of active compound given below.
  • the undersurfaces of the leaves were inoculated with an aqueous sporangia suspension of Plasmopara viticola.
  • the vines were first placed for 48 hours in a water vapor-saturated chamber at 24 ° C and then for 5 days in a greenhouse at temperatures between 20 and 30 ° C. After this time, the plants were again placed in a humid chamber for 16 hours to accelerate the sporangiopathic outbreak. Then the extent of infestation on the undersides of the leaves was visually determined.
  • Leaves of potted 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 0 C. After 6 days, the late blight on the untreated but infected control plants had developed so strongly that the infestation could be determined visually in%.
  • Leaves of potted tomato plants were sprayed to drip point with an aqueous suspension in the drug concentration below. After three days 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%.

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

Abstract

L'invention concerne l'utilisation de 5-alkyl-6-phénylalkyl-7-amino-azolopyrimidines représentées par la formule (I), dans laquelle Y est alkylène, alcénylène ou alkinylène éventuellement substitué par des groupes alkyl ; R<SUP>1</SUP> est halogène, cyano, nitro, hydroxy, mercapto, alkyl, halogénoalkyl, alcényl, cycloalkyl, cycloalcényl, alkoxy, halogénoalkoxy, alcényloxy, alkinyloxy, alkylthio, NR<SUP>A</SUP>R<SUP>B</SUP>, alkylcarbonyl, phényl, naphtyl ou un hétérocycle à cinq ou six membres, saturé, partiellement insaturé ou aromatique, contenant un à quatre hétéroatomes du groupe O, N ou S ; R<SUP>A</SUP> et R<SUP>B</SUP>sont hydrogène, alkyl ou alkylcarbonyl ; n est 0, 1, 2, 3 ou 4 ; R<SUP>2</SUP> est alkyl, alcényl, cycloalkyl, alkoxyalkyl et alkylthioalkyl ; R<SUP>3</SUP> est hydrogène, halogène, cyano, NR<SUP>A</SUP>R<SUP>B</SUP>, hydroxy, mercapto, alkyl, halogénoalkyl, cycloalkyl, alkoxy, alkylthio, cycloalkoxy, cycloalkylthio, carboxyl, formyl, alkylcarbonyl, alkoxycarbonyl, alcényloxycarbonyl, alkinyloxycarbonyl, phényl, phénoxy, phénylthio, benzyloxy, benzylthio, alkyl-S(O)<SUB>m</SUB>; m est 0, 1 ou 2 ; A est n et C-R<SUP>a </SUP>; R<SUP>a</SUP>est hydrogène et alkyl, les atomes de C de Y, R<SUP>1</SUP>, R<SUP>2</SUP>, R<SUP>3</SUP> et Ra pouvant être substitués comme indiqué dans le descriptif. Les composés selon l'invention peuvent être utilisés pour la lutte contre des champignons parasites phytopathogènes. L'invention concerne également de nouvelles 5-alkyl-6-phénylalkyl-7-amino-azolopyrimidines, des procédés de fabrication de ces composés et des agents les contenant.
EP06754813A 2005-04-25 2006-04-24 Utilisation de 5-alkyl-6-phenylalkyl-7-amino-azolopyrimidines, nouvelles azolopyrimidines, procede de fabrication et agents les contenant Withdrawn EP1876899A2 (fr)

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DE102005019399 2005-04-25
PCT/EP2006/061786 WO2006114405A2 (fr) 2005-04-25 2006-04-24 Utilisation de 5-alkyl-6-phenylalkyl-7-amino-azolopyrimidines, nouvelles azolopyrimidines, procede de fabrication et agents les contenant

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CN (1) CN101163404A (fr)
TW (1) TW200720276A (fr)
WO (1) WO2006114405A2 (fr)

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US8211828B2 (en) * 2007-01-19 2012-07-03 Basf Se Fungicidal mixtures of 1-methylpyrazol-4-ylcarboxanilides and azolopyrimidinylamines
BRPI0806766A2 (pt) * 2007-01-30 2011-09-13 Basf Se misturas pesticidas, métodos para melhorar a saúde de plantas, para controlar ou prevenir infestação fúngica em plantas, partes de planta, sementes, ou seu local de crescimento, para controlar ou prevenir nematódeos ou insetos nocivos em plantas, partes de planta, sementes, ou seu local de crescimento, e para proteger sementes, material de propagação de planta, semente, e, composição pesticida
EA020203B1 (ru) * 2007-09-20 2014-09-30 Басф Се Композиции и агенты, содержащие фунгицидный штамм и активное соединение
UY32099A (es) 2008-09-11 2010-04-30 Enanta Pharm Inc Inhibidores macrocíclicos de serina proteasas de hepatitis c
WO2011082269A2 (fr) 2009-12-30 2011-07-07 Arqule, Inc. Composés de benzo-pyrimido-tétrazolo-diazépine substituée
CA2822556A1 (fr) 2010-12-30 2012-07-05 Enanta Pharmaceuticals, Inc Inhibiteurs macrocycliques de serine protease d'hepatite c
EA201390988A1 (ru) 2010-12-30 2014-04-30 Энанта Фармасьютикалз, Инк. Фенантридиновые макроциклические ингибиторы сериновой протеазы вируса гепатита c
US10201584B1 (en) 2011-05-17 2019-02-12 Abbvie Inc. Compositions and methods for treating HCV
WO2015103490A1 (fr) 2014-01-03 2015-07-09 Abbvie, Inc. Formes galéniques antivirales solides
MX2020007994A (es) * 2018-02-02 2020-09-09 Boehringer Ingelheim Int Derivados de triazolopirimidina para usar como inhibidores de ghrelin o-aciltransferasa (goat).
CN115916789B (zh) 2020-05-22 2025-06-27 勃林格殷格翰国际有限公司 制备烷基7-氨基-5-甲基-[1,2,5]噁二唑并[3,4-b]吡啶羧酸酯的连续方法

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DE3338292A1 (de) * 1983-10-21 1985-05-02 Basf Ag, 6700 Ludwigshafen 7-amino-azolo(1,5-a)-pyrimidine und diese enthaltende fungizide
US5389632A (en) * 1992-02-24 1995-02-14 Laboratoires Upsa Pyrazolopyrimidine derivatives which are angiotensin II receptor antagonists
FR2687677B1 (fr) * 1992-02-24 1996-10-11 Union Pharma Scient Appl Nouveaux derives de polyazaindenes antagonistes des recepteurs a l'angiotensine ii ; leurs procedes de preparation, compositions pharmaceutiques les contenant.
WO2006092428A2 (fr) * 2005-03-02 2006-09-08 Basf Aktiengesellschaft 7-amino-azolopyrimidine 2-substituee, son procede de fabrication et son utilisation pour lutter contre les champignons nuisibles, et agents renfermant ce compose

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CN101163404A (zh) 2008-04-16
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JP2008538759A (ja) 2008-11-06
TW200720276A (en) 2007-06-01
US20080188494A1 (en) 2008-08-07

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