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EP1856122A2 - 7-amino-azolopyrimidine 2-substituee, son procede de fabrication et son utilisation pour lutter contre les champignons nuisibles, et agents renfermant ce compose - Google Patents

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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Publication number
EP1856122A2
EP1856122A2 EP06724913A EP06724913A EP1856122A2 EP 1856122 A2 EP1856122 A2 EP 1856122A2 EP 06724913 A EP06724913 A EP 06724913A EP 06724913 A EP06724913 A EP 06724913A EP 1856122 A2 EP1856122 A2 EP 1856122A2
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EP
European Patent Office
Prior art keywords
compounds
formula
alkyl
line
compound corresponds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP06724913A
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German (de)
English (en)
Inventor
Wassilios Grammenos
Thomas Grote
Udo HÜNGER
Jan Klaas Lohmann
Bernd Müller
Joachim Rheinheimer
Peter Schäfer
Anja Schwögler
Michael Rack
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BASF SE
Original Assignee
BASF SE
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Application filed by BASF SE filed Critical BASF SE
Publication of EP1856122A2 publication Critical patent/EP1856122A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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 2-substituted 7-amino-azolopyrimidines of the formula I.
  • R 1 is hydrogen, halogen, cyano, C r C 14 alkyl, Ci-C 4 haloalkyl, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, C 3 -C 8 cycloalkyl, C 1 -C 12 -alkoxy, Ci-C 12 alkoxy-C r C 12 alkyl, benzyl zyloxy-CrC ⁇ alkyl, C 1 -C 2 alkoxy-C 2 -C 12 -alkenyl or C 1 -C 12 -alkoxy -C 2 -C 12 alkynyl;
  • R 2 is hydrogen, halogen, cyano, C r C 12 alkyl, C 2 -C 12 -alkenyl, C 2 -C 12 -alkynyl, C 3 -C 8 -cycloalkyl, C 1 -C 12 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl and
  • R a is halogen, cyano, hydroxy, mercapto, CiC-io-alkyl, CrCio-haloalkyl, C 3 - C ⁇ cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C r C 6 alkoxy, C r C 6 alkylthio, CRCE-alkoxy-CRCE-alkyl, NR A R B, phenyl, C r C 6 alkyl-phenyl; R A, R B is hydrogen and Ci-C ⁇ alkyl; where the cyclic groups in R a can be substituted by one to four groups R b :
  • R b is halogen, cyano, hydroxy, mercapto, C 1 -C 10 -alkyl, halo-CrC 10 alkyl, C 2 -C 0 alkenyl, C 2 -C 10 alkynyl and C r C 6 alkoxy;
  • R x is hydrogen or one of the groups mentioned in R 3 .
  • the invention relates to processes for the preparation of these compounds, compositions containing them and their use for controlling phytopathogenic harmful fungi.
  • EP-A 141 317 discloses individual fungicidally active 5,6-dialkyl-7-aminoazolopyrimidine derivatives. However, their effect is in many cases unsatisfactory. On this basis, the object of the present invention is to provide compounds with improved activity and / or broadened spectrum of activity.
  • the compounds of the formula I differ from those mentioned above by the specific embodiment of the substituent in the 2-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-hydroxyazolopyrimidines of the formula IV.
  • the variables 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 .beta.-keto esters of the formula II with the aminoazoles of the formula III 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.
  • 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 and in particular organic bases, for example tertiary amines such as trimethylamine, triethylamine, triisopropylethylamine, tributylamine and N-methylpipe
  • 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 triisopropylamine, 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 in the US Pat Hal is chlorine or bromine, in particular chlorine, reacted.
  • the reaction is preferably with chlorinating agents such as phosphorus oxychloride, thionyl onylchlorid or sulfuryl chloride at 5O 0 C to 150 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 ° C to 200 ° C to the 7-amino-azolo [1, 5-a] - pyrimidines implemented.
  • 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 an aminoazole 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-azolo [1, 5-a] -pyrimidines are optionally isolated after evaporation of the solvent or dilution with water as crystalline compounds.
  • substituted alkyl cyanides of the formula VI required for the preparation of the 7-amino-azolo [1,5-a] -pyrimidines are known in some cases or can be prepared by known methods from alkyl cyanides and carboxylic acid esters with strong bases, e.g. Alkali hydrides, alkali metal alcoholates, alkali metal amides or metal alkyls, are prepared (see: J. Amer., Chem. Soc., Vol. 73, (1951) p. 3766).
  • Haloalkyl means are accessible by halogenation of corresponding halogen-free azo-lopyrimidine of the formula I, they are referred to as compounds I '.
  • R 1 * is a halogen-free group R 1 .
  • R 1 is a halogenated group R 1 :
  • the halogenation is usually carried out at temperatures of 0 0 C to 200 0 C, preferably 20 0 C to 110 0 C, in an inert organic solvent in the presence of a radical initiator (eg dibenzoyl peroxide or azobisisobutyronitrile or under UV irradiation, eg with a Hg vapor lamp ) or an acid [cf. Synthetic Reagents, Vol. 2, pp. 1-63, Wiley, New York (1974)].
  • a radical initiator eg dibenzoyl peroxide or azobisisobutyronitrile or under UV irradiation, eg with a Hg vapor lamp
  • an acid cf. Synthetic Reagents, Vol. 2, pp. 1-63, Wiley, New York (1974)
  • the reactants are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use the halogenating agent in an excess based on I '.
  • halogenating agents are, for example, elemental halogens (eg Cl 2 , Br 2 , J 2 ), N-bromo-succinimide, N-chloro-succinimide or Dibromdimethylhydrantoin.
  • the halogenating agents are generally used in equimolar amounts, in excess or, if appropriate, as solvents.
  • Halogen fluorine, chlorine, bromine and iodine, in particular fluorine or chlorine;
  • Alkyl saturated, straight-chain or branched hydrocarbon radicals having from 1 to 4, 6, 8 or 10 carbon atoms, for example C r C 6 alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1 Methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylpentyl butylbutyl, 3,3-dimethylbutyl, 1-ethylbuty
  • Haloalkyl straight-chain or branched alkyl groups having 1 to 2, 4 or 6 carbon atoms (as mentioned above), where in these groups some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above: in particular C 1 -C 4 -haloalkyl such as chloromethyl, Bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2- Trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroe
  • Alkenyl unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, 6, 8 or 10 carbon atoms and one or two double bonds in any position, for example C 2 -C 6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl 1-Butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2 Pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2 - Butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-benzenyl, 1, 1-dimethyl-2-propenyl, 1,
  • Alkoxyalkyl saturated, straight-chain or mono-, di- or tri-branched hydrocarbon chain which is interrupted by an oxygen atom
  • C 5 -C 12 alkoxyalkyl 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, Heptyloxyethyl, 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, hexyloxy-
  • Haloalkenyl unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 10 carbon atoms and one or two double bonds in any position (as mentioned above), wherein in these groups the hydrogen atoms partially or completely against halogen atoms as mentioned above, in particular fluorine, chlorine and bromine , can be replaced;
  • 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-pentynyl
  • Cycloalkyl mono- or bicyclic saturated hydrocarbon groups having 3 to 6 carbon ring members such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
  • R 1 and R 2 are independently halogen, cyano, Ci-C 12 alkyl, CrCl 2 -haloalkyl, C 2 -C 12 - alkenyl, C 2 -C 12 alkynyl, C 3 -C 8 cycloalkyl, C 1 -C 12 -alkoxy CRCE 1-alkoxy-CRCE-alkyl, WO- in which the carbon chains in R 1 and / or R 2 may be substituted by one to four identical or different of the following groups R a :
  • R 1 and R 2 are independently C 1 -C 12 -alkyl, CrC ⁇ -haloalkyl, C 2 -C 12 alkenyl, C 2 -C 2 alkynyl, C 3 -C 8 -cycloalkyl, C 1 -C 12 -alkoxy, Ci-Ce-alkoxy-CrCe-alkyl, wherein the carbon chains in R 1 and / or R 2 may be substituted as described above.
  • Haloalkyl C 2 -C 5 alkenyl, C 2 -C 5 alkynyl, C 3 -C 5 - - Particularly preferred are those compounds I in which R 2 is C 1 -C 5 -alkyl, C 1 -C 5 are cycloalkyl, C 1 -C 5 -alkoxy, C 1 -C 4 -AIk- oxy-CrC 4 alkyl, which groups are unsubstituted or substituted by halogen, cyano, methyl or ethyl substituted.
  • R 2 is C r C 5 alkyl, -C 5 haloalkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl, C 3 -C 5 -cycloalkyl C 1 -C 5 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, which groups are unsubstituted or substituted by halogen, cyano, methyl or ethyl.
  • R 1 is C 1 -C 12 -alkyl, C r C 2 -haloalkyl, C 2 -C 12 alkenyl, C 3 -C 2 alkynyl, C 1 -C 6 -
  • R 2 is C 5 alkyl, CRCS haloalkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl, C 1 -C 4 -AIkOXy-
  • R 2 stands for C 5 alkyl C r, C r C 5 haloalkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl, CrC ⁇ alkoxy-CrC ⁇ alkyl, wherein the carbon chains in R 1 and / or R 2 may be partially or fully halogenated.
  • R 2 is methyl, ethyl, isopropyl, n-propyl or n-butyl, in particular methyl.
  • Halogen atoms in the groups R 1 and / or R 2 are preferably on the ⁇ -carbon atom.
  • Cyano groups in R 1 and / or R 2 are preferably on the terminal carbon atom.
  • R 3 1 is halo, cyano, hydroxy, mercapto, amino, C 2 -C 6 -alkyl, halo-C 6 alkyl, C 3 -C 8 -cycloalkyl, C C 6 -Aikoxy or C 1 -C 6 -AlkVItIIiO, in particular for halogen or amines.
  • One embodiment of the compounds according to the invention relates to compounds I in which A is CR X , in particular CH. These compounds correspond to formula 1.1:
  • R x is halogen, cyano, hydroxyl, mercapto, amino, C 2 -C 6 -alkyl, C r C 6 -haloalkyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 - Alkoxy or C r C 6 alkylthio, in particular halogen, cyano and C-rdo-alkyl.
  • Another embodiment of the compounds according to the invention relates to compounds I in which A is N. These compounds correspond to formula 1.2:
  • Table 104 Compounds of the formula 1.1, in which R 1 for each compound corresponds to one line of Table A, R 2 denotes n-octyl and R 3 denotes ethyl
  • R 2 is n-nonyl and R 3 is n-propyl
  • Table 139 Compounds of the formula 1.1, in which R 1 for each compound corresponds to one line of Table A, R 2 is n-heptyl and R 3 is methylthio
  • Table 214 Compounds of the formula 1.2, in which R 1 for each compound corresponds to one row of Table A, R 2 denotes n-decyl and R 3 denotes mercapto
  • Table 249 Compounds of the formula 1.2, in which R 1 for each compound corresponds to one line of Table A, R 2 is n-nonyl and R 3 is ethyl
  • R 2 denotes n-decyl and R 3 denotes n-propyl
  • 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.
  • Bipolaris and Drechslera species on maize, cereals, rice and turf for example D. tars on barley, D. tritci-repentis on wheat), - Blumeria graminis (powdery mildew) on cereals,
  • Botrytis cinerea (gray mold) on strawberries, vegetables, flowers and vines
  • Cercospora species on maize, soybeans, rice and sugar beet for example C. beticula on sugar beets
  • Cochliobolus species on corn, cereals, rice e.g., Cochliobolus sativus on cereals, Cochliobolus miyabeanus on rice
  • Fusarium and Verticillium species e.g., V. dahliae
  • various plants e.g., F. graminearum on wheat
  • Gaeumanomyces graminis on cereals - Gibberella species on cereals and rice (e.g., Gibberella fujikuroi on rice),
  • Pseudoperonospora species on hops and cucurbits e.g., P. cubenis on cucumber
  • Rhizoctonia species e.g., R. solani
  • Sclerotinia species e.g., S. sclerotiorum
  • oilseed rape oilseed rape
  • sunflowers sunflowers and other plants
  • Septoria tritici and Stagonospora nodorum on wheat
  • Oomycetes such as Peronospora species, Phytophthora arias, Plasmopara viticola and Pseudoperonospora arias.
  • the compounds I are also suitable for controlling harmful fungi in the protection of materials (eg wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
  • harmful fungi ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sciophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp .; Basidi- omycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleu- rotus 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 protective material, the following yeasts: Candida spp. and Saccharomyces cerevisae.
  • the compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally effective amount of the active ingredients.
  • the application can be done both before and after the infection of the materials, plants or seeds by the fungi.
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90 wt .-% of active ingredient.
  • the application rates in the application in crop protection depending on the nature of the desired effect between 0.01 and 2.0 kg of active ingredient per ha.
  • active ingredient in general, amounts of active ingredient of 1 to 1000 g / 100 kg, preferably 5 to 100 g / 100 kg of seed are needed.
  • the application rate of active ingredient depends on the type of application and the desired effect. Usual application rates are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of material treated in the material protection.
  • the compounds of the formula I can be present in various crystal modifications, which may differ in their biological activity. They are also the subject of the present invention.
  • the compounds I can be converted into the usual formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the application form depends on the respective purpose; It should in any case ensure a fine and uniform distribution of the compound according to the invention.
  • the formulations are prepared in a known manner, for example by stretching the active ingredient with solvents and / or excipients, if desired using emulsifiers and dispersants.
  • Suitable solvents / auxiliaries are essentially: water, aromatic solvents (eg Solvesso products, xylene), paraffins (eg petroleum fractions), alcohols (eg methanol, butanol, pentanol, benzyl alcohol), ketones (eg cyclohexanone, gamma Butyrolactone), pyrrolidones (NMP, NOP), acetates (Glycol diacetate), glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters.
  • aromatic solvents eg Solvesso products, xylene
  • paraffins eg petroleum fractions
  • alcohols eg methanol, butanol, pentanol, benzyl alcohol
  • ketones eg cyclohe
  • solvent mixtures can also be used, - carriers such as ground natural minerals (eg kaolins, clays, talc, chalk) and ground synthetic minerals (eg finely divided silica, silicates); Emulsifiers such as non-ionic and anionic emulsifiers (eg polyoxyethylene)
  • ground natural minerals eg kaolins, clays, talc, chalk
  • ground synthetic minerals eg finely divided silica, silicates
  • Emulsifiers such as non-ionic and anionic emulsifiers (eg 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, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong polar solvents, e.g. Dimethylsulfoxide, N-methylpyrrolidone or water into consideration.
  • mineral oil fractions of medium to high boiling point such as kerosine or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivative
  • Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
  • Granules e.g. Coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers.
  • Solid carriers are e.g. Mineral earths, such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • Mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics
  • the formulations generally contain between 0.01 and 95 wt .-%, preferably between 0.1 and 90 wt .-% of the active ingredient.
  • the active ingredients are in a purity of 90% to 100%, preferably 95% to 100% (by NMR spectrum) used.
  • 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 each 5 parts by weight).
  • This mixture is added to water by means of an emulsifying machine (e.g., Ultraturax) in 30 parts by weight and made into a homogeneous emulsion. Dilution in water results in an emulsion.
  • the formulation has an active ingredient content of 25% by weight.
  • the active ingredients 20 parts by weight of the active ingredients are comminuted with the addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine active substance suspension. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • Water-dispersible and water-soluble granules 50 parts by weight of the active ingredients are finely ground with the addition of 50 parts by weight of dispersants and wetting agents and prepared by means of technical equipment (eg 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.
  • G Water-dispersible and water-soluble powders (WP, SP, SS, WS) 75 parts by weight of the active compounds are ground in a rotor-stator mill with the addition of 25 parts by weight of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active ingredient content of the formulation is 75% by weight.
  • 0.5 parts by weight of the active ingredients are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for direct application with 0.5 wt .-% active ingredient content.
  • LS water-soluble concentrates
  • FS suspensions
  • DS dusts
  • WS water-dispersible and water-soluble powders
  • ES emulsions
  • EC emulsifiable concentrates
  • gel formulations GF
  • 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, scattering agents, granules by spraying, atomizing, dusting, scattering or Pouring be applied.
  • the forms of application are based entirely on the application purposes; 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
  • wetting agents To the active ingredients oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides, possibly also just immediately before use (tank mix), are added. These agents can be added to the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.
  • adjuvants in this sense are in particular: 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- never RPE 2035 and Genapol ® B ®; Alcohol ethoxylates, eg. As Lutensol XP 80 ®; and sodium dioctylsulfosuccinate, e. B. Leophen RA ®.
  • 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-
  • the agents according to the invention in the form of application as fungicides, may also be present together with other active substances, e.g. with herbicides, insecticides, growth regulators, fungicides or with fertilizers.
  • other active substances e.g. with herbicides, insecticides, growth regulators, fungicides or with fertilizers.
  • 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;
  • Carboxylic acid anilides benalaxyl, benodanil, boscalid, carboxin, mepronil, fenfuram, fenhexamide, flutolanil, furametpyr, metalaxyl, ofurace, oxadixyl, oxycarboxin,
  • Penthiopyrad, thifluzamide, tiadinil 4-difluoromethyl-2-methyl-thiazole-5-carboxylic acid (4'-bromo-biphenyl-2-yl) -amide, 4-difluoromethyl-2-methyl-thiazole-5-carboxylic acid - (4'-trifluoromethyl-biphenyl-2-yl) -amide, 4-difluoro-methyl-2-methyl-thiazole-5-carboxylic acid (4'-chloro-3'-fluoro-biphenyl-2-yl) - amide, 3-Difluoromethyl-1-methyl-pyrazole-4-carboxylic acid (3 ', 4'-dichloro-4-fluoro-biphenyl-2-yl) -amide, 3,4-dichloro-isothiazole-5 carboxylic acid (2-cyano-phenyl) -amide;
  • 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
  • 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-dimethyl-isoxazolidin-3-yl] -pyridine;
  • Pyrimidines bupirimate, cyprodinil, ferimzone, fenarimol, mepanipyrim, nuarimol, pyrimethanil;
  • - piperazines triforins
  • - Pyrroles fludioxonil, fenpiclonil
  • Dicarboximides iprodione, procymidone, vinclozolin; - others: 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-sulfonyI) - [1, 2,4] triazole-1-
  • 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, toluylfluanid, flusulfamides, phthalides, hexachlorobenzene, pencycuron, quintozene; Nitrophenyl derivatives: binapacryl, dinocap, dinobuton;
  • the active compounds were prepared as a stock solution with 25 mg of active ingredient, with a mixture of acetone and / or DMSO and the emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) in the volume ratio solvent-emulsifier from 99 to 1 ad 10 ml. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the drug concentration given below.
  • Uniperol® EL wetting agent with emulsifying and dispersing action based on ethoxylated 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 sporangium 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%. In this test, the plants treated with 500 ppm of Compound 1-2 showed no attack, while the untreated plants were 90% infected.
  • 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 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.

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

Abstract

L'invention concerne une 7-amino-azolopyrimidine 2-substituée, de formule (I) dans laquelle les substituants ont les significations suivantes: R<SUP>1</SUP> : hydrogène, halogène, cyano, alkyle, halogénoalkyle, alcényle, alcynyle, cycloalkyle, alcoxy, alcoxyalkyle, benzyloxyalkyle, alcoxyalcényle ou alcoxyalcynyle; R<SUP>2</SUP> : hydrogène, halogène, cyano, alkyle, halogénoalkyle, alcényle, alcynyle, cycloalkyle, alcoxy, alcoxyalkyle et alkylthioalkyle, les chaînes carbonées dans R<SUP>1</SUP> et/ou dans R<SUP>2</SUP> pouvant être substituées conformément à la description ; R<SUP>3</SUP> : halogène, cyano, NR<SUP>A</SUP>R<SUP>B</SUP>, hydroxy, mercapto, alkyle, halogénoalkyle, cycloalkyle, alcoxy, alkylthio, cycloalcoxy, cycloalkylthio, carboxyle, formyle, alkylcarbonyle, alcoxycarbonyle, alcényloxycarbonyle, alcynyloxycarbonyle, phényle, phénoxy, phénylthio, benzyloxy, benzylthio, alkyl-S(O)<SUB>m-</SUB>; A N et CR<SUP>x</SUP>; R<SUP>x</SUP> : hydrogène ou l'un des groupes précités pour R<SUP>3</SUP>. L'invention concerne en outre un procédé et des produits intermédiaires pour la fabrication de ces composés, des agents renfermant ces composé, ainsi que leur utilisation pour lutter contre des champignons nuisibles pathogènes des végétaux
EP06724913A 2005-03-02 2006-03-02 7-amino-azolopyrimidine 2-substituee, son procede de fabrication et son utilisation pour lutter contre les champignons nuisibles, et agents renfermant ce compose Withdrawn EP1856122A2 (fr)

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DE102005010110 2005-03-02
DE102005023388 2005-05-17
PCT/EP2006/060399 WO2006092428A2 (fr) 2005-03-02 2006-03-02 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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EP1856122A2 true EP1856122A2 (fr) 2007-11-21

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US (1) US20080139581A1 (fr)
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WO (1) WO2006092428A2 (fr)

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US8063092B2 (en) 2006-11-10 2011-11-22 Basf Se Crystalline modification of fipronil
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WO2006092428A2 (fr) 2006-09-08
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TW200643022A (en) 2006-12-16
WO2006092428A3 (fr) 2006-11-30

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