WO2007028434A1 - Nouveaux derives de pyrazolopyrimidine - Google Patents

Nouveaux derives de pyrazolopyrimidine Download PDF

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WO2007028434A1
WO2007028434A1 PCT/EP2006/005935 EP2006005935W WO2007028434A1 WO 2007028434 A1 WO2007028434 A1 WO 2007028434A1 EP 2006005935 W EP2006005935 W EP 2006005935W WO 2007028434 A1 WO2007028434 A1 WO 2007028434A1
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formula
compounds
ethyl
diseases caused
plants
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PCT/EP2006/005935
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English (en)
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Norio Sasaki
Mamoru Hatazawa
Yasuo Araki
Tetsuya Inuta
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Bayer Cropscience Ag
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Publication of WO2007028434A1 publication Critical patent/WO2007028434A1/fr

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    • 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 novel pyrazolopyrimidine derivatives, to their use as a microbicide, to a process for their preparation and novel intermediates.
  • certain pyrazolopyrimidine derivatives are known to function as an angiotensin II receptor antagonist [for example, see Japanese Patent Application Laid-open (KOHYO) No 7-504177], and it has been reported that certain pyrazolopyrimidine derivatives are utilized as photosensitive materials [for example, see Japanese Patent Application Laid-Open (KOKAI) No. 63-199347].
  • R 1 represents C 4-6 branched alkyl
  • R 2 represents halogen
  • R 3 represents C M alkyl
  • R 1 and R 2 have the same definition as aforementioned,
  • the pyrazolopyrimidines of the formula (I) are highly suitable for controlling unwanted microorganisms. Especially, they have strong fungicidal activity and can be used both in crop protection and in the protection of materials.
  • halogen indicates fluorine, chlorine, bromine or iodine, and, preferably, is fluorine or chlorine;
  • C 4-6 branched alkyl is, for example, sec-butyl, 1,2-dimethylpropyl, neopentyl, or 1,2,2- trimethylpropyl;
  • Ci -4 alkyl which may be linear or branched, is for example, methyl, ethyl, n-propyl, isopropyl, or n-, iso-, sec- or tert-butyl.
  • R 1 represents sec-butyl, 1,2-dimethylpropyl, neopentyl or 1,2,2-trimethylpropyl
  • R 2 is fluorine or chlorine.
  • R 1 represents . 1,2-dimethylpropyl or 1,2,2-trimethylpropyl
  • R 2 is fluorine or chlorine.
  • the radical definitions mentioned above can be combined with one another as desired. Moreover, individual definitions may not apply.
  • the compounds according to the invention of formula (I) can, if appropriate, be present as mixtures of different possible isomeric forms, in particular stereoisomers, such as E and Z, threo ⁇ nd erythro, and also optical isomers, such as R and S isomers or atrope isomers, and, if appropriate, also of tautomers.
  • R 2 and R 3 have the same definition as aforementioned,
  • R 1 is as defined above, in accordance with the method described, for example, in WO03/09798.
  • R 2 and R 3 have the same definitione as aforementioned
  • halogenating agent such as phosphorus oxychloride
  • R 2 and R 3 have the same definition as aforementioned,
  • R 3 have the same definition as aforementioned, in accordance with the method described, for example, in Japanese Patent Application Laid-Open (KOKAI) No. 2002-249492.
  • R 3 have the same definition as aforementioned
  • X represents halogen
  • R 2 have the same definition as aforementioned
  • the compounds of the above formula (VHJ) per se are conventionally known compounds, and typical examples thereof include diethyl malonate and dimethyl malonate.
  • the compounds of the above formula (IX) per se are conventionally known compounds, and typical examples thereof include 3-fluorobenzyl bromide and 3-chlorobenzyl bromide.
  • the compounds of the above formula (VIT), which are materials for the preparation of the compounds of the above formula (V), are conventionally known compounds, and examples thereof include ethyl 3-amino-4-pyrazolecarboxylate.
  • Specific examples of the compounds of the formula (II), which is used as the starting materials in the preparation method (a), include the followings:
  • the compounds of the formula (FV) per se, which are used as the starting materials in the preparation of the compounds of the formula (II), are known compounds, and specific examples thereof include the followings:
  • the compounds of the formula (HI) can be obtained starting from the compounds of the formula (VI) and (VII) in a continuous reaction without purification of the compounds of the formula (V).
  • R 2 and R 3 have the same definition as aforementioned,
  • R 4 represents hydroxy or a chlorine atom
  • Q represents hydroxy, a chlorine atom or a group -NH-R 1 , in which R 1 has the same definition as aforementioned, when R 4 represents hydroxyl, Q represents hydroxy, and when R 4 represents a chlorine atom, Q represents a chlorine atom or a group — NH- R 1 .
  • reaction of the preparation method (a) may be carried out in an appropriate diluent, and examples thereof to be used include:
  • ethers such as ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxy ethane (DME),
  • THF tetrahydrofuran
  • DGM diethylene glycol dimethyl ether
  • the preparation method (a) can be carried out in the presence of an acid binder, and examples thereof include inorganic bases, such as hydrides, hydroxides, carbonates and bicarbonates of alkali metals and alkali earth metals, and specific examples thereof include sodium hydride, lithium hydride, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide.
  • inorganic bases such as hydrides, hydroxides, carbonates and bicarbonates of alkali metals and alkali earth metals
  • specific examples thereof include sodium hydride, lithium hydride, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide.
  • the preparation method (a) can be carried out in a virtually wide temperature range.
  • the temperature range is generally set from about - 78°C to about 200 0 C, preferably, from about - 20 0 C to about 140 0 C.
  • the reaction may be carried out at high or reduced pressure, although it is preferably carried out under normal pressure.
  • the preparation method (a) may be carried out, for example, by allowing 1 mole of the compounds of the formula (II) to react in a diluent such as dioxane-water in the presence of 1.0 mole to 10.0 moles of potassium hydroxide thereby to obtain the aimed compounds of the formula (I).
  • the compounds according to the invention have potent microbicidal activity and can be employed for controlling unwanted microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.
  • Fungicides can be employed in crop protection for controlling Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be employed in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • Powdery Mildew Diseases such as
  • Blumeria diseases caused for example by Blumeria graminis Podosphaera diseases caused for example by Podosphaera leucotricha Sphaerotheca diseases caused for example by Sphaerotheca fuliginea Uncinula diseases caused for example by Uncinula necator
  • Rust Diseases such as Gymnosporangium diseases caused for example by Gymnosporangium sabinae Hemileia diseases caused for example by Hemileia vastatrix Phakopsora diseases caused for example by Phakopsora pachyrhizi and Phakopsora meibomiae Puccinia diseases caused for example by Puccinia recondita; Uromyces diseases caused for example by Uromyces appendiculatus
  • Leafspot, Leaf blotch and Leaf Blight Diseases such as Alternaria diseases caused for example by Alternaria solani
  • Cladiosporium diseases caused for example by Cladiosporium cucumerinum
  • Elsinoe diseases caused for example by Elsinoe fawcettii
  • Leptosphaeria diseases caused for example by Leptosphaeria maculans
  • Mycosphaerella diseases caused for example by Mycosphaerella graminicola and Mycosphaerella fijiensis
  • Phaeosphaeria diseases caused for example by Phaeosphaeria nodorum caused for example by Phaeosphaeria nodorum
  • Ramularia- diseases caused for example by Ramularia collo-cygni
  • Rhynchosporium diseases caused for example by Rhynchosporium secalis Septoria diseases caused for example by Septoria apii;
  • Root- and Stem Diseases such as
  • Corticium diseases caused for example by Corticium graminearum Fusarium diseases caused for example by Fusarium oxysporum caused for example by Corticium graminearum Fusarium diseases caused for example by Fusarium oxysporum
  • Gaeumannomyces diseases caused for example by Gaeumannomyces graminis caused for example by Gaeumannomyces graminis
  • Rhizoctonia diseases caused for example by Rhizoctonia solani
  • Thielaviopsis diseases caused for example by Thielaviopsis basicola
  • Fusarium diseases caused for example by Fusarium culmorum caused for example by Fusarium culmorum
  • Ustilago diseases caused for example by Ustilago nuda
  • Botrytis diseases caused for example by Botrytis cinerea
  • Penicillium diseases caused for example by Penicillium expansum and Penicillium purpurogenum Sclerotinia diseases caused for example by Sclerotinia sclerotiorum;
  • Verticillium diseases caused for example by Verticillium alboatrum
  • Nectria diseases caused for example by Nectria galligena
  • Leaf Blister or Leaf Curl Diseases including deformation of blooms and fruits such as Taphrina diseases caused for example by Taphrina deformans
  • Esca disease caused for example by Phaeomoniella clamydospora and Phaeoacremonium aleophilum and Fomitiporia mediterranea
  • Botrytis diseases caused for example by Botrytis cinerea
  • Rhizoctonia diseases caused for example by Rhizoctonia solani Helminthosporium diseases caused for example by Helminthosporium solani
  • Bacterial Organisms such as Xanthomanas species for example Xanthomonas campestris pv. Oryzae Pseudomonas species for example Pseudomonas syringae pv. Lachrymans Erwinia species for example Erwinia amylovora
  • the compounds releated to this invention are preferably used to control the following soybean diseases:
  • Alternaria leaf spot Alternaria spec, atrans tenuissima
  • Anthracnose Coldletotrichum gloeosporoides dematium var. truncatum
  • Brown spot Septoria glycines
  • Cercospora leaf spot and blight Cercospora kikuchii
  • Choanephora leaf blight Choanephora infundibulifera trispora
  • Dactuliophora leaf spot (Dactuliophora glycines), Downy Mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), Frogeye Leaf spot (Cercospora sojina), Leptosphaerulina Leaf Spot (Leptosphaerulina trifolii), Phyllostica Leaf Spot (Phyllosticta sojaecola), Pod and Stem Blight (Phomopsis sojae), Powdery Mildew (Microsphaera diffusa), Pyrenochaeta Leaf Spot (Pyrenochaeta glycines), Rhizoctonia Aerial, Foliage, and Web Blight (Rhizoctonia solani), Rust (Phakopsora pachyrhizi, Phakopsora meibomiae), Scab (Sphaceloma glycines), Stem
  • Roots and Lower Stems for example Black Root Rot (Calonectria crotalariae), Charcoal Rot (Macrophomina phaseolina), Fusarium Blight or Wilt, Root Rot, and Pod and Collar Rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus Root Rot (Mycoleptodiscus terrestris), Neocosmospora (Neocosmopspora vasinfecta), Pod and Stem Blight (Diaporthe phaseolorum), Stem Canker (Diaporthe phaseolorum var.
  • Black Root Rot Calonectria crotalariae
  • Charcoal Rot Macrophomina phaseolina
  • Fusarium Blight or Wilt Fusarium Blight or Wilt
  • Root Rot and Pod and Collar Rot
  • Fusarium oxysporum Fusarium orthoceras, Fusarium semitectum
  • unwanted microorganisms are to be understood as meaning phytopathogenic fungi, bacteria and viruses.
  • the compounds according to the invention can thus be used to protect plants within a certain period of time after treatment against attack by the pathogens mentioned.
  • the period of time for which this protection is achieved generally extends for 1 to 10 days, preferably 1 to 7 days, from the treatment of the plants with the active compounds.
  • the active compounds of the formula (I) include those that present superior controlling and/or eliminating effects particularly on pathogenic fungi against plants, such as Botiytis cinerea and Pyricularia or ⁇ zae. Moreover, the active compounds of the present invention also include those that present superior controlling and/or eliminating effects on Fusarium graminearum. According to the invention, it is possible to treat all plants and parts of plants. Plants are to be understood here as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including plant cultivars which can or cannot be protected by plant breeders' certificates.
  • Parts of plants are to be understood as meaning all above-ground and below-ground parts and organs of plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seeds and also roots, tubers and rhizomes.
  • Parts of plants also include harvested material and vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds.
  • the treatment of the plants and parts of plants according to the invention with the active compounds is carried out directly or by action on their environment, habitat or storage area according to customary treatment methods, for example by dipping, spraying, evaporating, atomizing, broadcasting, brushing-on and, in the case of propagation material, in particular in the case of seeds, furthermore by one- or multilayer coating.
  • the compounds according to the invention can be employed for protecting industrial materials against infection with, and destruction by, unwanted microorganisms.
  • Industrial materials in the present context are understood as meaning non-living materials which have been prepared for use in industry.
  • industrial materials which are intended to be protected by active compounds according to the invention from microbial change or destruction can be tackifiers, sizes, paper and board, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which can be infected with, or destroyed by, microorganisms.
  • Parts of production plants, for example cooling-water circuits which may be impaired by the proliferation of microorganisms may also be mentioned within the scope of the materials to be protected.
  • Industrial materials which may be mentioned within the scope of the present invention are preferably adhesives, sizes, paper and board, leather, wood, paints, cooling lubricants and heat- transfer liquids, particularly preferably wood.
  • Microorganisms capable of degrading or changing the industrial materials are, for example, bacteria, fungi, yeasts, algae and slime organisms.
  • the active compounds according to the invention preferably act against fungi, in particular molds, wood- discoloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • Microorganisms of the following genera may be mentioned as examples:
  • Altemaria such as Alternaria tenuis
  • Aspergillus such as Aspergillus niger
  • Chaetomium such as Chaetomium globosum
  • Coniophora such as Coniophora puetana
  • Lentinus such as Lentinus tigrinus
  • Penicillium such as Penicillium glaucum
  • Polyporus such as Polyporus versicolor
  • Aureobasidium such as Aureobasidium pullulans
  • Sclerophoma such as Sclerophoma pityophila
  • Trichoderma such as Trichoderma viride
  • Escherichia such as Escherichia coli
  • Pseudomonas such as Pseudomonas aeruginosa
  • Staphylococcus such as Staphylococcus aureus.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV cool and warm fogging formulations.
  • customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV cool and warm fogging formulations.
  • formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam formers.
  • extenders that is liquid solvents, liquefied gases under pressure, and/or solid carriers
  • surfactants that is emulsifiers and/or dispersants, and/or foam formers.
  • suitable liquid solvents are: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chloro- benzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide or dimethyl sulfoxide, or else water.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chloro- benzenes, chloroethylenes or methylene chloride
  • aliphatic hydrocarbons such as
  • Liquefied gaseous extenders or carriers are to be understood as meaning those liquids which are gaseous at standard temperature and under atmospheric pressure, for example aerosol propellants such as halogenated hydrocarbons, or else butane, propane, nitrogen and carbon dioxide.
  • Suitable solid carriers are: for example ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as finely divided silica, alumina and silicates.
  • Suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, pumice, marble, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks.
  • Suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, or else protein hydrolyzates.
  • Suitable dispersants are: for example lignosulfite waste liquors and methylcellulose.
  • Tackifiers such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other possible additives are mineral and vegetable oils.
  • colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments for example iron oxide, titanium oxide and Prussian Blue
  • organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs
  • trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can, as such or in their formulations, also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, to broaden, for example, the activity spectrum or to prevent development of resistance. In many cases, synergistic effects are obtained, i.e. the activity of the mixture is greater than the activity of the individual components.
  • Suitable mixing components are, for example, the following compounds:
  • Fungicides Bl) a compound capable to inhibit the nucleic acid synthesis like benalaxyl, benalaxyl-M, bupirimate, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazol, mefenoxam, metalaxyl, metalaxyl-M, ofurace, oxadixyl, oxolinic acid ;
  • B2 a compound capable to inhibit the mitosis and cell division like benomyl, carbendazim, diethofencarb, ethaboxam, fiiberidazole, pencycuron, thiabendazole, thiophanate-methyl, zoxamide
  • C ⁇ -respiration inhibitor like boscalid, carboxin, fenfuram, flutolanil, furametpyr, furmecyclox, mepronil, oxycarboxin, penthiopyrad, thifluzamide ;
  • CHI-respiration inhibitor like amisulbrom, azoxystrobin, cyazofamid, dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin ;
  • B5) a compound capable to inhibit ATP production like fentin acetate, fentin chloride, fentin hydroxide, silthiofam;
  • B8 a compound capable to inhibit lipid and membrane synthesis like biphenyl, chlozolinate, edifenphos, iodocarb, iprobenfos, iprodione, isoprothiolane, procymidone, propamocarb, propamocarb hydrochloride, pyrazophos, tolclofos-methyl, vinclozolin ;
  • a compound capable to inhibit ergosterol biosynthesis like aldimorph, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, dodemo ⁇ h, dodemo ⁇ h acetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole, fenhexamid, fenpropidin, fenpropimorph, fluquinconazole, flu ⁇ rimidol, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imazalil, imazalil sulfate, imibenconazole, ipconazole, metconazole, myclobutanil, naftifine, nuarimol, oxpoconazole,
  • BlO a compound capable to inhibit cell wall synthesis like benthiavalicarb, dimethomorph, flumorph, iprovalicarb, polyoxins, polyoxorim, validamycin A;
  • BI l a compound capable to inhibit melanine biosynthesis like carpropamid, diclocymet, fenoxanil, phthalide, pyroquilon, tricyclazole;
  • B 12 a compound capable to induce a host defence like acibenzolar-S-methyl, probenazole, tiadinil;
  • B 13) a compound capable to have a multisite action like Bordeaux mixture, captafol, captan, chlorothalonil, copper naphthenate, copper oxide, copper oxychloride, copper preparations such as copper hydroxide, copper sulphate, dichlofluanid, dithianon, dodine, dodine free base, ferbam, fluorofolpet, folpet, guazatine, guazatine acetate, iminoctadine, iminoctadine albesilate, iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, metiram zinc, oxine-copper, propineb, sulphur and sulphur preparations including calcium polysulphide, thiram, tolylfluanid, zineb, ziram ;
  • B 14 a compound selected in the following list: (2E)-2-(2- ⁇ [6-(3-chloro-2-methylphenoxy)-5- fluoropyrimidin-4-yl]oxy ⁇ phenyl)-2-(methoxyimino)-N-methylacetamide, (2E)-2- ⁇ 2-[( ⁇ [(lE)-l-(3- ⁇ [(E)-l-fluoro-2-phenylvinyl]oxy ⁇ phenyl)ethylidene]amino ⁇ oxy)methyl]phenyl ⁇ -2- (methoxyimino)-N-methylacetamide, l-(4-chlorophenyl)-2-(lH-l,2,4-triazol-l-yl)cycloheptanol, 1- [(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl lH-imidazole-1-carboxylate, 2-(4-chlorophenyl)- N- ⁇ 2-[3-me
  • bronopol dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.
  • carbamates for example alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, azamethi- phos, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, chloethocarb, coumaphos, cyanofenphos, cyanophos, dimetilan, ethiofencarb, fenobucarb, fenothiocarb, formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb)
  • organophosphates for example acephate, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos (-methyl/-ethyl), coumaphos, cyanofenphos, cyanophos, chlorofenvinphos, demeton-S-methyl, demeton-S-methylsulfone, dialifos, diazinon, dichlofenthion, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, dioxabenzofos, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fe
  • pyrethroids for example acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentyl-isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrin, cycloprothrin, cyflu- thrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, DDT, deltamethrin, empenthrin (lR-isomer), esfenvalerate, etofenprox, fen
  • chloronicotinyls/neonicotinoids for example acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam
  • Antagonists of GABA-gated chloride channels 5.1 cyclodiene organochlorines (for example camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor
  • fiproles for example acetoprole, ethiprole, fipronil, vaniliprole
  • mectins for example abamectin, avermectin, emamectin, emamectin-benzoate, ivermectin, milbemectin, milbemycin
  • diacylhydrazines for example chromafenozide, halofenozide, methoxyfenozide, tebufenozide
  • benzoylureas for example bistrifluron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron
  • organotins for example azocyclotin, cyhexatin, fenbutatin-oxide
  • dinitrophenols for example binapacryl, dinobuton, dinocap, DNOC
  • Site-I electron transport inhibitors 12.1 METIs (for example fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad)
  • Phthalamides for example N2-[ 1 , 1 -dimethyl-2-(methylsulfonyl)ethyl]-3-iodo-Nl -[2-methyl-4-[l , 2,2,2- tetrafluoro-l-(trifluoromethyl)ethyl]phenyl]-l,2-benzenedicarboxamide (CAS Reg. No.: 272451- 65-7), flubendiamide)
  • fumigants for example aluminum phosphide, methyl bromide, sulfuryl fluoride
  • a mixture with other known active compounds, such as herbicides, or with fertilizers and growth regulators, safeners and/or semiochemicals is also possible.
  • the compounds of the formula (T) according to the invention also have very good antimycotic activity. They have a very broad antimycotic activity spectrum in particular against dermatophytes and yeasts, molds and diphasic fungi (for example against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii.
  • Candida species such as Candida albicans, Candida glabrata
  • Epidermophyton floccosum for example against Candida species such as Candida albicans, Candida glabrata
  • Epidermophyton floccosum for example against Candida species such as Candida albicans, Candida glabrata
  • Epidermophyton floccosum for example against Candida species such as Candida albicans, Candida glabrata
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules.
  • Application is carried out in a customary manner, for example by watering, spraying, atomizing, broadcasting, dusting, foaming, spreading, etc. It is furthermore possible to apply the active compounds by the ultra-low-volume method, or to inject the active compound preparation or the active compound itself into the soil. It is also possible to treat the seeds of the plants.
  • the application rates can be varied within a relatively wide range, depending on the kind of application.
  • the active compound application rates are generally between 0.1 and 10 000 g/ha, preferably between 10 and 1000 g/ha.
  • the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the active compound application rates are generally between 0.1 and 10 000 g/ha, preferably between 1 and 5 000 g/ha.
  • plants of the plant cultivars which are in each case commercially available or in use are treated according to the invention.
  • Plant cultivars are to be understood as meaning plants having new properties ("traits") and which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, varieties, bio- or genotypes.
  • the treatment according to the invention may also result in superadditive (“synergistic") effects.
  • superadditive for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the substances and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products are possible which exceed the effects which were actually to be expected.
  • transgenic plants or plant cultivars which are preferably to be treated according to the invention include all plants which, in the genetic modification, received genetic material which imparted particularly advantageous useful properties ("traits") to these plants.
  • traits particularly advantageous useful properties
  • Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products.
  • transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), corn, soy beans, potatoes, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), and particular emphasis is given to corn, soy beans, potatoes, cotton, tobacco and oilseed rape.
  • Traits that are particularly emphasized are increased defense of the plants against insects, arachnids, nematodes and slugs and snails by toxins formed in the plants, in particular those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A(a), CryIA(b), Cry ⁇ A(c), CryllA, CrylDLA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (hereinbelow referred to as "Bt plants”).
  • Traits that are also particularly emphasized are the increased defense of the plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Traits that are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example the "PAT" gene).
  • the genes which impart the desired traits in question can also be present in combination with one another in the transgenic plants.
  • Bt plants are com varieties, cotton varieties, soy bean varieties and potato varieties which are sold under the trade names YIELD GARD® (for example corn, cotton, soy beans), KnockOut® (for example corn), StarLink® (for example corn), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato).
  • YIELD GARD® for example corn, cotton, soy beans
  • KnockOut® for example corn
  • StarLink® for example corn
  • Bollgard® cotton
  • Nucoton® cotton
  • NewLeaf® potato
  • herbicide-tolerant plants examples include corn varieties, cotton varieties and soy bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example corn, cotton, soy bean), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulfonylureas, for example corn).
  • Herbicide-resistant plants plants bred in a conventional manner for herbicide tolerance
  • Clearf ⁇ eld® for example corn.
  • these statements also apply to plant cultivars which have these genetic traits or genetic traits still to be developed, and which will be developed and/or marketed in the future.
  • the plants listed can be treated according to the invention in a particularly advantageous manner with the compounds of the general formula (I) or the active compound mixtures according to the invention.
  • the preferred ranges stated above for the active compounds or mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compounds or mixtures specifically mentioned in the present text.
  • the resulting compound was used in the next step without purification.
  • Emulsif ⁇ er Polyoxyethylene alkylphenyl ether 7.5 parts by weight
  • the above active compound, acetone and emulsifier were mixed, and diluted with water to a predetermined concentration to prepare a sample.
  • Cucumber (cultivar: Sagamihanpaku) was grown in a plastic pot of 4 cm in diameter, and to the small seedling that had grown to cotyledons was sprayed a diluent of the active compound having a predetermined concentration preliminarily prepared at an amount of 6 ml per 3 pots.
  • an inoculation source prepared by mixing a suspension of spores of Botrytis cinerea that had been artificially cultivated with agar gel (2 x 10 4 spores/ml gel), was put on the cotyledons so as to be inoculated, and the resulting cotyledons were transferred into a wet box and kept at 20 0 C to allow the infection so that the symptoms were made to appear.
  • the morbidity per cotyledon was classified and evaluated based on the basis of the following criteria, and the preventive value (%) was further determined.
  • the phyto- toxicity was simultaneously examined. The present tests were carried out based upon the average of the results of two sections with four leaves.
  • Preventive value (%) [1 - (Morbidity of treated section / Morbidity of non-treated section)] x 100
  • Paddy-field rice (cultivar: Koshihikari) was grown in a plastic pot of 4 cm in diameter, and to the small seedling that had grown to have 1.5 to 2 leaves was sprayed a diluent of the active compound having a predetermined concentration prepared in accordance with the manner as in Test Example 1 above, at an amount of 6 ml per 3 pots.
  • a suspension of spores of Pyricularia oryzae that had been artificially cultivated was atomized over the plants so as to be inoculated (once), and the resulting plants were maintained at 25°C and a relative humidity of 100 % so as to allow the infection.
  • the morbidity per pot was classified and evaluated, and the preventive value (%) was further determined.
  • the phytotoxicity was simultaneously examined. The present tests were carried out based upon the average of the results of one section including three pots.
  • Clay mineral grains (95 parts) having a grain-size distribution of 0.2 to 2 mm was charged into a rotary mixer, and Compound No. 13 (5 parts) of the present invention mixed in a liquid diluent was atomized under rotation so as to be uniformly moistened, and the resulting grains were dried at a temperature in a range of 40 to 50 0 C to prepare granules.
  • Compound No. 14 (15 parts) of the present invention, a mixture of white carbon (hydrous non- crystallized silicon oxide fine powder) and powdered clay (l:5)(80 parts), alkylbenzene sodium sulfonate (2 parts) and polymer sodium alkylnaphthalene-sulfonate-formalin (3 parts) were powder-mixed to prepare wettable powders.
  • Compound No. 11 (20 parts) of the present invention, sodium lignosulfonate (30 parts), bentonite (15 parts) and calcined diatomaceous earth powder (35 parts) were mixed sufficiently, and water was added thereto, and the resulting mixture was extruded through a screen of 0.3 mm and dried to prepare water-dispersible granules.

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

Abstract

La présente invention propose de nouveaux dérivés de pyrazolopyrimidine de formule (I) dans lesquels R1 représente un alkyle ramifié en C4-6, et R2 représente un halogène, un procédé pour leur préparation, de nouveaux intermédiaires et l'utilisation des nouveaux composés de formule (I) en tant que microbicides.
PCT/EP2006/005935 2005-06-30 2006-06-21 Nouveaux derives de pyrazolopyrimidine WO2007028434A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2005191675A JP2007008864A (ja) 2005-06-30 2005-06-30 ピラゾロピリミジン誘導体及び農園芸用殺菌剤
JP2005-191675 2005-06-30

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WO2007028434A1 true WO2007028434A1 (fr) 2007-03-15

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008019723A1 (fr) * 2006-08-17 2008-02-21 Bayer Cropscience Ag Dérivés hétérocycliques insecticides d'acide carboxylique
WO2011134867A1 (fr) * 2010-04-26 2011-11-03 Basf Se Azolopyrimidines herbicides

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0071792A2 (fr) * 1981-08-01 1983-02-16 BASF Aktiengesellschaft 7-Amino-azolo (1,5-a) pyrimidines procédé pour leur production et fungicides les contenant
FR2794745A1 (fr) * 1999-06-14 2000-12-15 American Cyanamid Co 6-phenylpyrazolopyrimidines fongicides
WO2002048151A1 (fr) * 2000-12-11 2002-06-20 Basf Aktiengesellschaft 6-phenyl-pyrazolopyrimidines
WO2004000844A1 (fr) * 2002-05-29 2003-12-31 Bayer Cropscience Aktiengesellschaft Pyrazolopyrimidines
WO2005000851A1 (fr) * 2003-06-27 2005-01-06 Bayer Cropscience Aktiengesellschaft Pyrazolopyrimidines

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0071792A2 (fr) * 1981-08-01 1983-02-16 BASF Aktiengesellschaft 7-Amino-azolo (1,5-a) pyrimidines procédé pour leur production et fungicides les contenant
FR2794745A1 (fr) * 1999-06-14 2000-12-15 American Cyanamid Co 6-phenylpyrazolopyrimidines fongicides
WO2002048151A1 (fr) * 2000-12-11 2002-06-20 Basf Aktiengesellschaft 6-phenyl-pyrazolopyrimidines
WO2004000844A1 (fr) * 2002-05-29 2003-12-31 Bayer Cropscience Aktiengesellschaft Pyrazolopyrimidines
WO2005000851A1 (fr) * 2003-06-27 2005-01-06 Bayer Cropscience Aktiengesellschaft Pyrazolopyrimidines

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008019723A1 (fr) * 2006-08-17 2008-02-21 Bayer Cropscience Ag Dérivés hétérocycliques insecticides d'acide carboxylique
WO2011134867A1 (fr) * 2010-04-26 2011-11-03 Basf Se Azolopyrimidines herbicides

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