EP1194417A1 - Phenoxyfluoropyrimidines - Google Patents

Phenoxyfluoropyrimidines

Info

Publication number
EP1194417A1
EP1194417A1 EP00954416A EP00954416A EP1194417A1 EP 1194417 A1 EP1194417 A1 EP 1194417A1 EP 00954416 A EP00954416 A EP 00954416A EP 00954416 A EP00954416 A EP 00954416A EP 1194417 A1 EP1194417 A1 EP 1194417A1
Authority
EP
European Patent Office
Prior art keywords
chloro
phenyl
methyl
methylphenyl
methoxyphenyl
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Withdrawn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
EP00954416A
Other languages
German (de)
English (en)
Inventor
Herbert Gayer
Ralf Dunkel
Peter Gerdes
Ulrich Heinemann
Bernd-Wieland Krüger
Martin Vaupel
Astrid Mauler-Machnik
Ulrike Wachendorff-Neumann
Gerd Hänssler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from DE10006210A external-priority patent/DE10006210A1/de
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP1194417A1 publication Critical patent/EP1194417A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the invention relates to new phenoxyfluoropyrimidines, several processes for their preparation and their use as pesticides.
  • Z represents substituted monocyclic aryl, substituted or unsubstituted polycyclic aryl or substituted or unsubstituted heterocyclyl and
  • L 1 , L 2 , L 3 and L 4 are the same or different and each independently represents hydrogen, halogen, cyano, nitro, each optionally substituted by halogen, alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl.
  • the hydrocarbon chains such as alkyl or alkenyl, are also in combination with heteroatoms, such as, for example, in alkoxy, alkylthio, alkoxyalkyl, alkylthioalkyl, hydroximinoalkylphenyl, alkoxyiminoalkyl or alkoxyiminoalkyl, straight-chain or branched. Unless otherwise stated, preference is given to hydrocarbon chains having 1 to 6 carbon atoms.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • Heterocyclyl stands for saturated or unsaturated, as well as aromatic, ring-shaped
  • At least one ring member has a heteroatom, i.e. is an atom other than carbon. If the ring contains several heteroatoms, these can be the same or different. Heteroatoms are preferably oxygen, nitrogen or sulfur. If the ring contains several oxygen atoms, these are not adjacent. If appropriate, the ring-shaped compounds together with other carbocyclic or heterocyclic, fused or bridged rings together form a polycyclic ring system.
  • a polycyclic ring system can be linked to the heterocyclic ring or a fused-on carbocyclic ring.
  • the heterocyclyl described in this way can also be mono- or polysubstituted, preferably by methyl, ethyl, halogen or oxo.
  • Mono- or bicyclic ring systems are preferred, in particular mono- or bicyclic ring systems.
  • Haloalkoxy stands for partially or completely halogenated alkoxy.
  • the halogen atoms can be the same or different.
  • Preferred halogen atoms are fluorine and especially chlorine. If the haloalkyl carries further substituents, the maximum possible number of halogen atoms is reduced to the remaining free valences. Unless otherwise stated, preference is given to hydrocarbon chains having 1 to 6 carbon atoms.
  • Haloalkyl stands for partially or completely halogenated alkyl. In the case of polyhalogenated haloalkyl, the halogen atoms can be the same or different.
  • Preferred halogen atoms are fluorine and chlorine, especially fluorine. If the haloalkyl carries further substituents, the maximum possible number of halogen atoms is reduced to the remaining free valences. Unless otherwise stated, preference is given to hydrocarbon chains having 1 to 6 carbon atoms.
  • Aryl stands for aromatic, mono or polycyclic hydrocarbon rings, e.g. Phenyl, naphthyl, anthranyl, phenanthryl, which may optionally also be condensed with further aliphatic or heterocyclic rings.
  • aryl also stands for tetralinyl, indolyl, or benzofuranyl, but the linkage occurs at the phenyl part.
  • L 1 , L 2 , L 3 and L 4 have the meanings given above,
  • Y 1 represents halogen
  • L 1 , L 2 , L 3 and L 4 have the meanings given above and
  • Y 2 represents halogen
  • active substances may also have an effect against plant or animal pests.
  • Harmful organisms are understood to mean in particular microorganisms and animal pests.
  • the compounds of the invention can optionally be used as mixtures of various possible isomeric forms, especially stereoisomers, such as e.g. E- and Z-. Both the E and the Z isomers, as well as any mixtures of these isomers, are claimed.
  • the invention relates to compounds of formula (I) in which
  • Z represents substituted monocyclic aryl, substituted or unsubstituted polycyclic aryl
  • L 1 , L 2 , L 3 and L 4 are the same or different and each independently represent hydrogen, halogen, cyano, nitro, each optionally substituted by halogen substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl.
  • the invention preferably relates to compounds of the formula (I) in which
  • L 1 , L 2 , L 3 and L 4 are the same or different and are each independently of one another hydrogen, halogen, cyano, nitro, in each case alkyl, alkoxy, alkylthio, alkylsulfmyl or alkylsulfonyl each optionally substituted by 1 to 5 halogen atoms, each having 1 to 6 Carbon atoms, especially hydrogen.
  • the invention relates in particular to compounds of the formula (I) in which
  • Acetylamino-3-hydroxyphenyl 2-acetylamino-3-methoxyphenyl, 2-ethoxycarbonyl-3-hydroxyphenyl, 2-ethoxycarbonyl-3-methoxyphenyl, 2-oxo-l, 3-benzoxioxol-4-yl, 2- Hydroxy-3-formylphenyl, 2-n-propoxy-3-formylphenyl, 2-chloro-3-trifluoromethylphenyl, 2-methoxycarbonyl-3-hydroxyphenyl, 2-methoxycarbonyl-3-methoxyphenyl, 2-aminosulfonyl-3-hydroxyphenyl, 2-
  • L 1 , L 2 , L 3 and L 4 are the same or different and are each independently of one another hydrogen, halogen, cyano, nitro, in each case alkyl, alkoxy, alkylthio, alkylsulfmyl or alkylsulfonyl each optionally substituted by 1 to 5 halogen atoms, each having 1 to 6 Carbon atoms, especially hydrogen.
  • Compounds in which L 1 , L 2 , L 3 and L 4 are hydrogen are preferred.
  • radical definitions given for these radicals in the respective combinations or preferred combinations of radicals are independently replaced by radical definitions of other preferred ranges independently of the respectively specified combination of the radicals.
  • Formula (II) provides a general definition of the 2- (2-hydroxyphenyl) -2-methoxyiminoacetamides required as starting materials for carrying out process a) according to the invention.
  • L 1 , L 2 , L 3 and L 4 preferably or in particular have those meanings which have already been associated with the
  • the starting materials of the formula (II) are known and can be prepared by known processes (compare, for example, WO-A 95-24396).
  • Formula (III) provides a general definition of the fluo ⁇ yrimidines required as starting materials for carrying out process a) according to the invention.
  • Z preferably or in particular has the meaning which has already been stated as preferred or as particularly preferred for Z in connection with the description of the compounds of the formula (I) according to the invention.
  • Y 1 represents halogen, preferably fluorine or chlorine.
  • the starting materials of the formula (III) are known and / or can be prepared by known methods (compare, for example, DE-A 4340181; Chem. Ber., 90
  • Formula (IV) provides a general definition of the phenoxypyrimidines required as starting materials for carrying out process b) according to the invention.
  • L 1 , L 2 , L 3 and L 4 preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or particularly preferred for L 1 , L 2 , L 3 and L 4 were given.
  • Y 2 represents halogen, preferably fluorine or chlorine.
  • Formula (V) provides a general definition of the ring compounds which are further required as starting materials for carrying out process b) according to the invention.
  • Z preferably or in particular has the meaning which has already been stated as preferred or as particularly preferred for Z in connection with the description of the compounds of the formula (I) according to the invention.
  • the ring compounds of the formula (V) are known synthetic chemicals or can be prepared by simple methods.
  • Suitable diluents for carrying out processes a) and b) according to the invention are all inert organic solvents.
  • examples include and preferably ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; Sulfoxides such as dimethyl sulfoxide; or sulfones, such as sulfolane.
  • ethers such as diethyl ether
  • Processes a) and b) according to the invention are optionally carried out in the presence of a suitable acid acceptor.
  • a suitable acid acceptor All conventional inorganic or organic bases are suitable as such. These include, by way of example and by way of preference, alkaline earth metal or alkali metal hydrides, hydroxides, alcoholates, carbonates or hydrogen carbonates, such as, for example, sodium hydride, sodium amide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, potassium hydrogen carbonate or sodium hydrogen carbonate.
  • Suitable catalysts for processes a) and b) according to the invention are all copper (I) salts, such as, for example and preferably, copper (I) chloride, copper (I) bromide or copper (I) iodide.
  • reaction temperatures can be varied within a substantial range when carrying out processes a) and b) according to the invention. In general, temperatures from -20 ° C to 100 ° C, preferably at temperatures from -10 ° C to 80 ° C.
  • All of the processes according to the invention are generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar.
  • the reaction products are worked up, worked up and isolated using generally customary processes (see also the preparation examples).
  • the substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and
  • Bacteria can be used in crop protection and material protection.
  • Fungicides can be used to protect plants against Plasmodiophoromycetes. Use Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • Xanthomonas species such as, for example, Xanthomonas campestris pv. Oryzae;
  • Pseudomonas species such as, for example, Pseudomonas syringae pv. Lachrymans;
  • Erwinia species such as, for example, Erwinia amylovora;
  • Pythium species such as, for example, Pythium ultimum
  • Phytophthora species such as, for example, Phytophthora infestans
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or
  • Plasmopara species such as, for example, Plasmopara viticola
  • Bremia species such as, for example, Bremia lactucae
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae
  • Erysiphe species such as, for example, Erysiphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca fuliginea
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Venturia species such as, for example, Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
  • Cochliobolus species such as, for example, Cochliobolus
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Puccinia species such as, for example, Puccinia recondita
  • Sclerotinia species such as, for example, Sclerotinia sclerotiorum
  • Tilletia species such as, for example, Tilletia caries
  • Ustilago species such as, for example, Ustilago nuda or Ustilago avenae;
  • Pellicularia species such as, for example, Pellicularia sasakii;
  • Pyricularia species such as, for example, Pyricularia oryzae
  • Fusarium species such as, for example, Fusarium culmorum
  • Botrytis species such as, for example, Botrytis cinerea
  • Septoria species such as, for example, Septoria nodorum
  • Leptosphaeria species such as, for example, Leptosphaeria nodorum;
  • Cercospora species such as, for example, Cercospora canescens
  • Alternaria species such as, for example, Alternaria brassicae
  • Pseudocercosporella species such as, for example, Pseudocercosporella he ⁇ otrichoides.
  • the active compounds according to the invention can be used with particularly good success in combating cereal diseases, such as, for example, against Erysiphe species, Puccinia species and Fusarium species, and diseases in wine, fruit and vegetable cultivation, such as, for example, against Venturia and Plasmopara species , or rice diseases such as those against Pyricularia species.
  • cereal diseases such as, for example, against Erysiphe species, Puccinia species and Fusarium species
  • diseases in wine, fruit and vegetable cultivation such as, for example, against Venturia and Plasmopara species
  • rice diseases such as those against Pyricularia species.
  • the active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance.
  • the active compounds according to the invention can also be used in certain concentrations and application amounts as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates and products for the synthesis of further active ingredients.
  • the active substances are suitable for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the pests mentioned above include:
  • Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Thysanura e.g. Lepisma saccharina.
  • Phthiraptera e.g. Pediculus humanus co ⁇ oris, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp ..
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.
  • Trialeurodes vaporariorum Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phoropalisumum , Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.
  • Conoderus spp. Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Siphonaptera for example Xenopsylla cheopis, Ceratophyllus spp ..
  • From the class of the Arachnida for example Sco ⁇ io maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyommomma spp., ., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.,
  • Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp.,
  • insects which damage plants, for example against the caterpillars of the cockroach (Plutella maculipennis) or the green peach aphid (Mycus persicae).
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or cultivated plants (including naturally occurring cultivated plants), cultivated plants can be plants which are obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods can, including transgenic plants and including plant varieties that can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, as well as roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds. - 25 -
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space using the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by single- or multilayer coating.
  • the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
  • technical materials are to be understood as non-living materials that have been prepared for use in technology.
  • technical materials that are to be protected against microbial change or destruction by active substances according to the invention can be used.
  • parts of production plants, for example cooling water circuits may also be mentioned which can be impaired by the multiplication of microorganisms.
  • technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer liquids, particularly preferably wood.
  • Bacteria, fungi, yeasts, algae and mucilaginous organisms may be mentioned as microorganisms which can break down or change the technical materials.
  • the active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • microorganisms of the following genera may be mentioned:
  • Alternaria 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 like Trichoderma viride
  • Escherichia such as Escherichia coli
  • Pseudomonas such as Pseudomonas aeruginosa
  • Staphylococcus such as Staphylococcus aureus.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV -Cold and warm mist formulations.
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, ie liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents Means. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or Methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions
  • alcohols such as butanol or glycol
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • Solid carrier materials are suitable: for example natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates.
  • Possible solid carriers for granules are: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules made from inorganic and organic flours as well as granules made from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks.
  • Possible emulsifiers and / or foaming agents are: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Further,
  • Additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt,
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt,
  • Molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the spectrum of activity or to prevent the development of resistance.
  • fungicides bactericides
  • acaricides nematicides or insecticides
  • synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Fungicides Aldimo ⁇ h, Ampropylfos, Ampropylfos Potassium, Andoprim, Anilazine, Azaconazole,
  • Buthiobate calcium polysulfide, capsimycin, captafol, captan, carbendazim, carboxin, carvon,
  • Ferimzon Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Flu ⁇ rimidol, Flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminum, fosetyl
  • Iodocarb Ipconazole, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan,
  • copper preparations such as: copper hydroxide, copper phthalate, copper oxychloride, copper sulfate, copper oxide, oxy-copper and
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl,
  • Metconazole methasulfocarb, methfuroxam, metiram, metomeclam, metsulfovax,
  • Oxadixyl Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
  • Paclobutrazole pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin
  • Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetcyclacis, tetraconazole, thiabendazole,
  • Thicyofen Thifluzamide, Thiophanate-methyl, Thiram, Tioxymid, Tolclofos-methyl, Tolylfluanid, Triadimefon, Triadimenol, Triazbutil, Triazoxid, Trichlamid,
  • Tricyclazole tridemo ⁇ h, triflumizole, triforin, triticonazole,
  • OK-8705, OK-8801 ⁇ - (1, 1-dimethylethyl) -ß- (2-phenoxyethyl) - 1 H-1, 2,4-triazole-1-ethanol, ⁇ - (2,4-dichlo ⁇ henyl) -ß-fluorine -b-propyl-1 H-1, 2,4-triazole-1-ethanol, ⁇ - (2,4-dichloro phhenyl) -ß-methoxy-a-methyl-lH-l, 2,4-triazole-l - ethanol, ⁇ - (5-methyl-l, 3-dioxan-5-yl) -ß - [[4- (trifluoromethyl) phenyl] methylene] -lH-l, 2,4-triazol-1-ethanol,
  • Ethiofencarb Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimfos, Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxoxinon, Flutoxinoxuron, Fluutinoxuron, Fluutinoxuron, Fluutinoxuron, , Furathiocarb,
  • Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene, Imidacloprid, Isazofos, Isofenphos, Isoxathion, Ivermectin, Kernpolyederviruses Lambda-cyhalothrin, Lufenuron
  • Paecilomyces fumosoroseus Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propoxur, Prothiofos, Prothoat, Pyromhrhridosine, Pymmethrofinos, Pymmethrofinos , Pyridathione, pyrimidifen, pyriproxyfen,
  • the compounds of formula (I) according to the invention also have very good antifungal effects. They have a very broad spectrum of antimycotic effects, especially against dermatophytes and shoot fungi, mold and diphasic fungi (e.g. against Candida species such as Candida albicans, Candida glabrata)
  • Trichophyton species such as Trichophyton mentagrophytes
  • Microsporon species such as Microsporon canis and audouinii.
  • the list of these fungi is in no way a limitation of the detectable mycotic spectrum, but is only of an explanatory nature.
  • 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 takes place in the usual way, e.g. by watering, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients using the ultra-low-volume process or to inject the active ingredient preparation or the active ingredient into the soil itself.
  • the seeds of the plants can also be treated.
  • the application rates can be varied within a relatively wide range, depending on the type of application.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and
  • the active compound application rates are in the generally between 0.001 and 50 g per kg of seed, preferably between 0.01 and 10 g per kg of seed. In the treatment of the soil, the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • Active ingredient characterized by an excellent residual effect on wood and clay as well as a good alkali stability on limed substrates.
  • Emulsifier 0.6 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80% in order to promote the development of mildew pustules.
  • Emulsifier 0.6 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in a greenhouse at a temperature of approximately 20.degree. C. and a relative atmospheric humidity of 80% in order to promote the development of rust pustules.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Emulsifier 0.6 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are placed in a greenhouse under translucent incubation hoods at a temperature of approx. 15 ° C and a relative humidity of approx. 100%.
  • Evaluation is carried out 4 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • dimethylacetamide emulsifier 1.0 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • dimethylacetamide emulsifier 1.0 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in a greenhouse at approx. 21 ° C and a relative humidity of approx. 90%.
  • Evaluation is carried out 12 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Emulsifier 0.6 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Example G the substances according to the invention listed in Examples (3, 9, 10, 11, 12, 14 and 16) show an efficiency of 80% or more at an application rate of 125 g / ha.
  • Example G the substances according to the invention listed in Examples (3, 9, 10, 11, 12, 14 and 16) show an efficiency of 80% or more at an application rate of 125 g / ha.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with larvae of the horseradish beetle (Phaedon cochleariae) while the leaves are still moist.
  • the kill is determined in%>. 100% means that all beetle larvae have been killed; 0% means that none of the beetle larvae have been killed.
  • the compounds of the preparation examples at an exemplary active ingredient concentration of 0.01% had a kill of 100% after 7 days, while the known compound (A) showed no kill.
  • Example H the substances according to the invention listed in Examples (3 and 7) show a degree of killing of 95% or more after 7 days at an active ingredient concentration of 0.01%>.
  • Emulsifier 1900 parts by weight of methanol
  • a specified amount of active compound preparation of the desired concentration is pipetted onto a standardized amount of synthetic feed. After the methanol has evaporated, a film can lid with about 100 plutella eggs is placed on each cavity. The newly hatched larvae migrate to the treated synthetic food.
  • the kill is determined in%. 100% means that all animals have been killed; 0% means that no animals have been killed.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)

Abstract

L'invention concerne de nouvelles phénoxyfluoropyrimidines, plusieurs procédés permettant de les préparer et leur utilisation comme agents de lutte contre les parasites.
EP00954416A 1999-06-18 2000-06-06 Phenoxyfluoropyrimidines Withdrawn EP1194417A1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE19927913 1999-06-18
DE19927913 1999-06-18
DE10006210 2000-02-11
DE10006210A DE10006210A1 (de) 1999-06-18 2000-02-11 Phenoxyfluorpyrimidine
PCT/EP2000/005161 WO2000078733A1 (fr) 1999-06-18 2000-06-06 Phenoxyfluoropyrimidines

Publications (1)

Publication Number Publication Date
EP1194417A1 true EP1194417A1 (fr) 2002-04-10

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EP00954416A Withdrawn EP1194417A1 (fr) 1999-06-18 2000-06-06 Phenoxyfluoropyrimidines

Country Status (7)

Country Link
EP (1) EP1194417A1 (fr)
JP (1) JP2003502408A (fr)
CN (1) CN1356988A (fr)
AU (1) AU6687900A (fr)
BR (1) BR0012291A (fr)
PL (1) PL352285A1 (fr)
WO (1) WO2000078733A1 (fr)

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DE19955130A1 (de) 1999-11-17 2001-05-23 Bayer Ag Hydroxamsäurederivate
DE10211428A1 (de) * 2002-03-15 2003-10-23 Bayer Ag Bekämpfung von Parasiten an Tieren durch Halogenpyrimidine
ATE405840T1 (de) 2002-12-19 2008-09-15 Scripps Research Inst Zusammensetzungen und verfahren zur stabilisierung von transthyretin und zur hemmung von transthyretin-fehlfaltung
EP1768968A1 (fr) 2004-05-20 2007-04-04 Foldrx Pharmaceuticals, Inc. Composes 2-(heteroaryl)benzoxazoles et derives, compositions et procedes servant a stabiliser la transthyretine et a inhiber le mauvais repliement de la transthyretine
CN100443463C (zh) * 2005-06-28 2008-12-17 沈阳化工研究院 取代的对三氟甲基苯醚类化合物及其制备与应用
EP3208272B1 (fr) 2005-11-08 2020-01-08 Vertex Pharmaceuticals Incorporated Modulateurs hétérocycliques de transporteurs de cassette à liaison atp
EP2164840A2 (fr) 2007-05-09 2010-03-24 Vertex Pharmaceuticals Incorporated Modulateurs de cftr
EA201070700A1 (ru) 2007-12-07 2011-06-30 Вертекс Фармасьютикалз Инкорпорейтед Способы получения циклоалкилкарбоксамидопиридинбензойных кислот
RS55559B1 (sr) 2007-12-07 2017-05-31 Vertex Pharma Čvrste forme 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioksol-5-il)ciklopropankarboksamido)-3-metilpiridin-2-il) benzoeve kiseline
JP5523352B2 (ja) 2008-02-28 2014-06-18 バーテックス ファーマシューティカルズ インコーポレイテッド Ｃｆｔｒ修飾因子としてのへテロアリール誘導体
NZ602838A (en) 2010-04-07 2015-06-26 Vertex Pharma Pharmaceutical compositions of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid and administration thereof
CN102933206A (zh) * 2010-04-07 2013-02-13 弗特克斯药品有限公司 3-(6-(1-(2，2-二氟苯并[d][1，3]二氧杂环戊烯-5-基)环丙烷甲酰胺基)-3-甲基吡啶-2-基)苯甲酸的固体形式
CA2847293C (fr) 2011-09-16 2017-03-28 Richard Frederic Labaudiniere Formes solides d'un inhibiteur de la dissociation de derives de transthyretine
JP6963896B2 (ja) 2013-11-12 2021-11-10 バーテックス ファーマシューティカルズ インコーポレイテッドVertex Pharmaceuticals Incorporated Ｃｆｔｒ媒介性疾患の処置のための医薬組成物を調製する方法
RU2691136C2 (ru) 2014-11-18 2019-06-11 Вертекс Фармасьютикалз Инкорпорейтед Способ проведения высокопроизводительной тестовой высокоэффективной жидкостной хроматографии

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GB9404375D0 (en) * 1994-03-07 1994-04-20 Zeneca Ltd Fungicides
DE19646407A1 (de) * 1996-11-11 1998-05-14 Bayer Ag Halogenpyrimidine
DE19739982A1 (de) * 1996-12-10 1998-06-18 Bayer Ag Fungizide Wirkstoffkombinationen
DE19723195A1 (de) * 1997-06-03 1998-12-10 Bayer Ag Fluormethoximinoverbindungen
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Also Published As

Publication number Publication date
WO2000078733A1 (fr) 2000-12-28
JP2003502408A (ja) 2003-01-21
CN1356988A (zh) 2002-07-03
BR0012291A (pt) 2002-03-26
PL352285A1 (en) 2003-08-11
AU6687900A (en) 2001-01-09

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