EP1856119A1 - 5,6-dialkyl-7-amino-azolopyrimidines, leurs procedes de production, leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant - Google Patents

5,6-dialkyl-7-amino-azolopyrimidines, leurs procedes de production, leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant

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Publication number
EP1856119A1
EP1856119A1 EP06708583A EP06708583A EP1856119A1 EP 1856119 A1 EP1856119 A1 EP 1856119A1 EP 06708583 A EP06708583 A EP 06708583A EP 06708583 A EP06708583 A EP 06708583A EP 1856119 A1 EP1856119 A1 EP 1856119A1
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EP
European Patent Office
Prior art keywords
formula
compounds
methyl
propyl
ylamine
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.)
Withdrawn
Application number
EP06708583A
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German (de)
English (en)
Inventor
Peter Schäfer
Udo HÜNGER
Maria Scherer
Harald Köhle
Helmut Schiffer
Thomas Grote
Jochen Dietz
Wassilios Grammenos
Jan Klaas Lohmann
Bernd Müller
Joachim Rheinheimer
Frank Schieweck
Anja Schwögler
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BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1856119A1 publication Critical patent/EP1856119A1/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Withdrawn legal-status Critical Current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
    • 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

Definitions

  • R 1 is Ce-Cg-alkyl, C 4 -C 18 -alkoxymethylene or C 3 -Cio-alkoxyethylene, where the aliphatic groups may be substituted by one to three of the following groups:
  • R a , R b are hydrogen or C 1 -C 6 -alkyl;
  • R 2 is n-propyl or n-butyl
  • A is N or CH
  • R 3 CH 3 when A is CH additionally hydrogen.
  • the invention relates to processes for the preparation of these compounds, compositions containing them and their use for controlling phytopathogenic harmful fungi.
  • GB 1 148 629 generally suggests 5,6-dialkyl-7-amino-triazolo- and -pyrazolopyrimidines.
  • EP-A 141 317 discloses individual fungicidally active 5,6-dialkyl-7-amino-triazolo- and -pyrazolopyrimidines. 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 6-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.
  • 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, 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 alkoxides and dimethoxy magnesium, 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 triisopropylamine, tributylamine, N-methylmorpholine or N-methylpiperidine.
  • the temperatures are temperature between 50 and 300 0 C, preferably at 50 to 180 0 C, when working in solution [cp. 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 with chlorinating agents such as phosphorus oxychloride, thionyl onylchlorid or sulfuryl chloride is preferably carried out at 50 ° 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 organic from the overall dry phase is optionally isolated after evaporation of the inert solvent chlorination is generally very pure and is then reacted with ammonia in inert solvents at 100 0 C to 200 0 C to give the 7-aminoazolo [1, 5-a] - Implemented pyrimidines.
  • 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.
  • 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, Dibutylformaimid, 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-aminoazolo [1, 5-a] -pyrimidines of formula I 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 hydrides, alkali metal alcoholates, alkali metal amides or metal alkyls, are prepared (see: J. Amer., Chem. Soc., Vol. 73, (1951) p. 3766).
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkyl saturated, straight-chain or mono- or di-branched hydrocarbon radicals having 1 to 4 or 5 to 9 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-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethyl
  • hydrocarbon chain as described above having 3 to 11 carbon atoms such as propoxy-ethyl, butoxy-ethyl, pentoxy-ethyl, hexoxy-loxy-ethyl, heptyloxy-ethyl, octyloxy-ethyl, nonyloxy-ethyl, 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-propyl, heptyloxy-propyl, octyloxy-propyl, nonyloxy-propyl, 3- (3-ethyl-hexyloxy) -propyl, 3- (2,4,4,
  • the alkyl groups in R 1 in formula I are preferably unbranched or mono-, di- or trisubstituted alkyl groups, the alkyl groups preferably carrying no substituents.
  • R is C 3 -Cio-alkyl or C 5 -C 0 alkoxyalkyl and R 12 Ci-C 4 alkyl, especially methyl, 11 wherein R 11 and R 12 together do not have more than 12 carbon atoms and are unsubstituted or as R 1 may be substituted in formula I.
  • R 1 represents a cyano-substituted alkyl group
  • the cyano group is preferably on the terminal carbon atom.
  • R 1 is Ce-Cg-alkyl, C 4 -C 5 -alkoxy-methylene or C 3 -C -alko-oxyethylene.
  • R 1 is hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2.2 Dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl.
  • R 1 is n-heptyl, 1-methylhexyl, n-octyl, 1-methylheptyl, n-nonyl, 1-methyloctyl and 3,5,5-trimethyl-hexyl.
  • R 2 is n-propyl
  • R 2 is n-butyl
  • R 3 is methyl
  • One embodiment relates to compounds I in which A is CH. These compounds correspond to formula 1.1:
  • Another embodiment of the compounds according to the invention relates to compounds I in which A is 1:
  • 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 e.g., D. teres sn barley, D. tritci-repentis on wheat), - Blumeria graminis (powdery mildew) on cereals,
  • Botrytis cinerea (gray mold) on strawberries, vegetables, flowers and vines, Bremia lactucae on salad,
  • 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
  • Gibberella species on cereals and rice e.g., Gibberella fujikuroi on rice
  • - Grainstaining complex on rice e.g., Gibberella fujikuroi on rice
  • Helminthosporium species for example A. graminicola
  • Maize and rice Michrodochium nivale on cereals
  • Pseudoperonospora species on hops and cucurbits e.g., P. cubenis on cucumber
  • Puccinia species on cereals, maize and asparagus P. triticina and P. striformis on wheat, P. asparagi on asparagus
  • Rhizoctonia species e.g., P » so / anf
  • Sclerotinia species e.g., S. sclerotiorum
  • oilseed rape e.g., sunflowers and other plants
  • the compounds I are suitable for controlling harmful fungi from the class Oomycetes, such as Peronospora A ⁇ en, Phytophthora species, Plasmopara viticola and Pseudoperonospora species.
  • the compounds I are also suitable for controlling harmful fungi in the protection of materials (eg wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
  • ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sciophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., P / et / rotus spp., Porta spp., Serpula spp.
  • ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sciophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp .
  • Basidiomycetes such
  • Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as M / ccvspp., moreover, in the material contactor, 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 customary formulations, for example 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 cyclohexanone, gamma Butyrolactone
  • NMP pyrrolidones
  • acetates glycols
  • dimethyl fatty acid amides fatty acids and
  • 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 nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin liquors and methylcellulose.
  • ground natural minerals eg kaolins, clays, talc, chalk
  • ground synthetic minerals eg finely divided silica, silicates
  • Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin liquors and methylcellulose.
  • the surface-active substances used are alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, and condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde , Condensation products of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl
  • 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 for example coated, impregnated and homogeneous granules, can be prepared by binding the active compounds to solid carriers.
  • Solid carriers are, for example, mineral earths, such as silica gels, silicates, talc, kaolin, attaclay, limestone, Lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, milled plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, 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 sulfate, magnesium oxide, milled plastics
  • the formulations generally contain between 0.01 and 95 wt .-%, preferably between 0.1 and 90 wt .-% of the active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • formulations are: 1. Products for dilution in water
  • a Water Soluble Concentrates 10 parts by weight of the active ingredients are dissolved with 90 parts by weight of water or a water-soluble solvent. Alternatively, wetting agents or other adjuvants are added. When diluted in water, the active ingredient dissolves. This gives a formulation with 10 wt .-% active ingredient content.
  • 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 gives a dispersion.
  • a dispersant e.g. Polyvinylpyrrolidone dissolved. Dilution in water gives 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 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. In the Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • Water-dispersible and water-soluble granules 50 parts by weight of the active compounds are finely ground with the addition of 50 parts by weight of dispersing and wetting agents and prepared by means of industrial equipment (for example extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the formulation has an active ingredient content of 50% by weight.
  • Water-dispersible and water-soluble powders 75 parts by weight of the active compounds are ground in a rotor-stator mill with the addition of 25 parts by weight of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active ingredient content of the formulation is 75% by weight.
  • 0.5 parts by weight of the active ingredients are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for direct application with 0.5 wt .-% active ingredient content.
  • LS water-soluble concentrates
  • FS suspensions
  • DS dusts
  • WS water-dispersible and water-soluble powders
  • ES emulsions
  • EC 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 purposes of 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 addition of 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.
  • concentrates which are active substance, adhesion, dispersant or emulsifier and, if appropriate, solvent or oil, concentrates which are suitable for dilution 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.
  • UUV ultra-low-volume
  • wetting agents To the active ingredients oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides, optionally also just 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- nic 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 can also be present in the application form as fungicides together with other active substances, for example with herbicides, insecticides, growth regulators, fungicides or else with fertilizers.
  • fungicides for example, in many cases, the spectrum of activity 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;
  • Carboxylic acid morpholides Dimethomorph, Flumorph; Benzoic acid amides: flumetover, fluopicolide (picobenzamide), zoxamide;
  • - triazoles bitertanol, bromuconazoles, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fenbuconazole, flusilazole, fluquinconazole, flutriol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetracona - zole, 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; - piperazines: triforins;
  • 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-methylindol-1-sulfonyl) - [1, 2,4] triazole-1-sulfonic acid dimethylamide;
  • fungicides - 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, which with a mixture of acetone and / or DMSO and the emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing on the basis of ethoxylated alkylphenol Ie) 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 on the basis of ethoxylated alkylphenol Ie

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  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pretreatment Of Seeds And Plants (AREA)

Abstract

L'invention se rapporte à des 5,6-dialkyl-7-amino-azolopyrimidines de formule (I) dans laquelle les substituants sont définis comme suit : R1 représente alkyle, alcoxyméthylène ou alcoxyéthylène, les groupes aliphatiques pouvant être substitués conformément à la description ; R2 désigne n-propyle ou n-butyle ; A représente N ou CH ; R3 désigne méthyle, et lorsque A représente CH, R3 désigne méthyle ou hydrogène. La présente invention concerne en outre des procédés et des produits intermédiaires pour produire ces composés, des agents contenant ces composés, et l'utilisation desdits composés pour lutter contre des champignons nuisibles phytopathogènes.
EP06708583A 2005-03-01 2006-03-01 5,6-dialkyl-7-amino-azolopyrimidines, leurs procedes de production, leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant Withdrawn EP1856119A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005009888 2005-03-01
PCT/EP2006/060362 WO2006092412A1 (fr) 2005-03-01 2006-03-01 5,6-dialkyl-7-amino-azolopyrimidines, leurs procedes de production, leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant

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EP1856119A1 true EP1856119A1 (fr) 2007-11-21

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US (1) US20080171657A1 (fr)
EP (1) EP1856119A1 (fr)
JP (1) JP2008536805A (fr)
CN (1) CN101128466A (fr)
BR (1) BRPI0607502A2 (fr)
TW (1) TW200700419A (fr)
WO (1) WO2006092412A1 (fr)

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Publication number Priority date Publication date Assignee Title
TW200640927A (en) * 2005-03-01 2006-12-01 Basf Ag 5,6-Dialkyl-7-aminoazolopyrimidines, their preparation and their use for controlling harmful fungi, and compositions comprising these compounds
BRPI0806347A2 (pt) 2007-01-19 2011-09-06 Basf Se misturas fungicidas, agente fungicida, método para combater fungos nocivos fitopagênicos, semente, e, processo para preparar um agente
JP5351047B2 (ja) * 2007-01-30 2013-11-27 ビーエーエスエフ ソシエタス・ヨーロピア アゾロピリミジニルアミン誘導体及び殺虫剤を主成分とする殺虫性混合物
WO2008092836A2 (fr) * 2007-01-30 2008-08-07 Basf Se Procédé d'amélioration de la santé des plantes
DK2132167T3 (en) * 2007-03-02 2014-03-10 Basf Se PROCESS FOR THE PREPARATION OF beta-ketonitriles
BRPI0816948B1 (pt) 2007-09-20 2018-01-23 Basf Se Composição fungicida, seus usos, agente fungicida, método para controlar fungos nocivos fitopatogênicos, e semente resistente a fungos nocivos fitopatogênicos

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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
CN1046730C (zh) * 1994-06-21 1999-11-24 株式会社大塚制药工场 吡唑并[1,5-a]嘧啶衍生物
JP2007527885A (ja) * 2004-03-10 2007-10-04 ビーエーエスエフ　アクチェンゲゼルシャフト ５，６−ジアルキル−７−アミノトリアゾロピリミジン、その調製、および有害真菌類を防除するためのその使用、ならびにそれらの化合物を含む組成物
BRPI0508337A (pt) * 2004-03-10 2007-07-24 Basf Ag compostos, processos para a preparação dos mesmos, agente fungicida, semente, e, processo para o combate de fungos nocivos fitopatogênicos
CA2557781C (fr) * 2004-03-10 2012-01-10 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, procedes pour leur production, leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant

Non-Patent Citations (1)

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Title
See references of WO2006092412A1 *

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US20080171657A1 (en) 2008-07-17
WO2006092412A1 (fr) 2006-09-08
TW200700419A (en) 2007-01-01
JP2008536805A (ja) 2008-09-11
CN101128466A (zh) 2008-02-20
BRPI0607502A2 (pt) 2016-11-01

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