WO1997028133A1 - 4-amino- et 4-hydrazinopyrimidines acylees et leur utilisation comme agents pour lutter contre les parasites - Google Patents

4-amino- et 4-hydrazinopyrimidines acylees et leur utilisation comme agents pour lutter contre les parasites Download PDF

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Publication number
WO1997028133A1
WO1997028133A1 PCT/EP1997/000240 EP9700240W WO9728133A1 WO 1997028133 A1 WO1997028133 A1 WO 1997028133A1 EP 9700240 W EP9700240 W EP 9700240W WO 9728133 A1 WO9728133 A1 WO 9728133A1
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Prior art keywords
alkyl
spp
cyano
nitro
formula
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PCT/EP1997/000240
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German (de)
English (en)
Inventor
Thomas Bretschneider
Gerd Kleefeld
Konrad Wernthaler
Christoph Erdelen
Klaus Stenzel
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Bayer Aktiengesellschaft
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Priority to JP9527274A priority Critical patent/JP2000503998A/ja
Priority to EP97902189A priority patent/EP0880505A1/fr
Priority to AU15932/97A priority patent/AU1593297A/en
Publication of WO1997028133A1 publication Critical patent/WO1997028133A1/fr

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    • 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
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • 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
    • 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

  • the invention relates to new 4-amino and 4-hydrazinopyrimidines, processes for their preparation and their use for controlling animal pests and as fungicides.
  • R 1 and R 2 are independently hydrogen, halogen, nitro, cyano alkyl
  • A represents -NR 3 - or -NR 3 -NR 4 -, where R 3 and R 4 independently of one another represent hydrogen, alkyl, alkoxyalkyl,
  • alkylcarbonyl or in each case optionally substituted aryl or arylcarbonyl,
  • X represents oxygen or sulfur
  • Y stands for a direct bond, in each case optionally substituted alkylidene, alkylideneoxy and alkylidethio or for alkenylidene and
  • Ar represents optionally substituted aryl or optionally substituted hetaryl.
  • R 1 and R 2 have the meaning given above, with acid halides of the formula (III) Hal-CO-Y-Ar (III) in which Y and Ar have the meaning given above and
  • Hai represents halogen, in the presence of a base and in the presence of a diluent, and optionally b) the 4-amino- and 4-hydrazinopyrimidines of the formula (Ia) thus obtained
  • R 1 , R 2 , Y and Ar have the meaning given above, with a sulfurizing agent, if appropriate in the presence of a diluent
  • the new acylated 4-amino- and 4-hydrazinopyrimidines of the formula (I) are very good as fungicides and for controlling animal pests, in particular insects, arachnids and nematodes, which are used in agriculture, in forests and in stock - and material protection as well as on the
  • the acylated 4-amino- and 4-hydrazinopyrimidines of the formula (I) according to the invention show a considerably better activity against animal pests than the constitutionally similar known compounds.
  • the compounds according to the invention are generally defined by the formula (I) Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below.
  • R 1 and R 2 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C 1 -C 6 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 - C 4 -haloalkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 - C 4 -alkyl, C 1 -C 4 -alkylthio, C 1 -C 4 - Alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 - C 2 haloalkylthio, C 1 -C 2 haloalkylsulfinyl, C 1 -C 2 haloalkylsulfonyl, amino, C 1 -C 4 alkylamino, di (C 1 -C
  • Haloalkylthio come into question, wherein at least one of the substituents R 1 and R 2 is different from hydrogen or
  • R 1 and R 2 together with the carbon atoms to which they are attached, preferably represent an optionally single to triple, identical or different, halogen, nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy , C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or C 1 -C 4 haloalkylthio substituted, saturated or unsaturated 5- or 6-membered ring, which has 1 or 2 heteroatoms , such as N, O or S atoms
  • A preferably represents -NR 3 - or -NR 3 -NR 4 -, wherein
  • R 3 and R 4 independently of one another for hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl or for in each case optionally up to three times the same or different halogen, nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, C 1 -C 4 -haloalkoxy or C 1 -C 4 haloalkylthio substituted phenyl or phenylcarbonyl X preferably represents oxygen or sulfur.
  • Y preferably stands for a direct bond, in each case optionally through
  • Ar preferably represents phenyl which is monosubstituted to trisubstituted by identical or different substituents, the following being suitable as substituents: halogen, nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 - Alkylthio, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio and each optionally mono- to trisubstituted, identically or differently substituted, phenyl, phenoxy, phenylthio, benzyl, pyridinyloxy, pyrimidinyloxy, thiazolyloxy or Thiadiazolyloxy, where the following are suitable as substituents:
  • Halogen nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 - C 4 haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio;
  • a condensed bi- or tricyclic radical which is optionally monosubstituted to fivefold, identical or different, substituted by halogen, nitro, cyano or C 1 -C 4 -alkyl and also contains one or more heteroatoms, such as O, S or N atoms can or for optionally mono- to trisubstituted, identically or differently substituted 5- or 6-membered hetaryl with 1 to 3 heteroatoms.
  • N, S and O atoms the following being suitable as substituents:
  • Halogen nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 - C 4 haloalkyl, C 1 -C 4 -haloalkoxy and C 1 -C 4 haloalkylthio.
  • R 1 and R 2 independently of one another particularly preferably represent hydrogen, chlorine, bromine, nitro, cyano, methyl, ethyl, chloromethyl, trifluoromethyl,
  • phenyl which is monosubstituted to trisubstituted identically or differently, where fluorine, chlorine, bromine, nitro, Cyano, methyl, ethyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy and trifluoromethylthio come into question, where at least one of the substituents R 1 and R 2 is different from hydrogen or R 1 and R 2 are together with the carbon atoms to which they are attached are particularly preferred for phenyl, pyrazolyl, imidazolyl or thiazolyl which are each substituted once or twice, identically or differently, by fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio.
  • R 3 and R 4 independently of one another represent hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, ethoxyethyl, acetyl or optionally phenylcarbonyl which is substituted once or twice, identically or differently, by fluorine, chlorine, nitro, cyano, methyl or trifluoromethyl.
  • X particularly preferably represents oxygen or sulfur.
  • Ar particularly preferably represents phenyl which is monosubstituted to trisubstituted identically or differently, the following being suitable as substituents:
  • hydrocarbon radicals mentioned above in the definition of the compounds according to the invention can also be used in connection with heteroatoms such as
  • Alkoxy - if possible, be straight-chain or branched
  • Y and Ar represent the general, preferred and particularly preferred meanings mentioned above.
  • Formula (II) provides a general definition of the pyrimidine derivatives required as starting materials for carrying out process (a) according to the invention.
  • A, R and R preferably or particularly preferably have those meanings which are preferred or particularly preferred for these in connection with the description of the compounds of formula (I)
  • pyrimidine derivatives of the formula (II) are known (cf., for example, Rasmussen, van der Pias, Recl. Trav. Chim. Pays-Bas 97, 288 (1978); J. Heterocycl. Chem. 28 (5), 1357 (1991)) or they can be obtained in a known manner (cf. also the following information on the preparation of new pyrimidine derivatives of the formula (Ha)).
  • the new pyrimidine derivatives of the formula (IIa) are obtained, for example, by the 4,5-dichloro-6-ethylpyrimidine of the formula (IV)
  • HAH (V) in which A has the meaning given above, in the presence of a base and optionally in the presence of a diluent.
  • Halogenated aliphatic or aromatic hydrocarbons, ethers or nitriles such as e.g. Cyclohexane, toluene, chlorobenzene, chloroform, dichloromethane, dichloroethane, dioxane, tetrahydrofuran, diethyl ether or acetonitrile.
  • Alkali or alkaline earth metal hydroxides, alkali or alkaline earth metal carbonates or hydrogen carbonates or nitrogen bases are preferably usable.
  • Examples include sodium hydroxide, calcium hydroxide, potassium carbonate, sodium hydrogen carbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoiin, diazabicyclooctane (DABCO), diazabicyclonones (DBN) and diazabicycloundecene (DBU).
  • a corresponding excess of amine or hydrazine of the formula (V) can preferably also be used.
  • reaction temperatures can be varied over a wide range. In general, temperatures between -40 ° C and + 200 ° C, preferably between 0 ° C and 150 ° C.
  • 4,5-dichloro-6-ethyl is generally employed per mole pyrimidine of the formula (IV) 1 to 3 mol, preferably 1 to 2 mol of amine or hydrazine of the formula (V).
  • the amines or hydrazines of the formula (V) are generally known compounds of organic chemistry
  • Formula (III) provides a general definition of the acid halides required as starting materials for carrying out process (a) according to the invention.
  • Y and Ar preferably or particularly preferably have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) or particularly preferably for these substituents.
  • Shark is preferably chlorine or bromine.
  • the acid halides of the formula (III) are generally known compounds of organic chemistry.
  • the starting materials of the formula (Ia) used in the production process (b) are compounds according to the invention and can be obtained in accordance with the information from the production process (a).
  • Suitable diluents for carrying out process (a) according to the invention are all customary solvents.
  • Halogenated aliphatic or aromatic hydrocarbons, ethers or nitriles such as, for example, cyclohexane, toluene, chlorobenzene, chloroform, dichloromethane, dichloroethane, dioxane, tetrahydrofuran, diethyl ether or acetonitrile are preferably usable
  • Process (a) described above for the preparation of the compounds of the formula (I) is carried out in the presence of a base
  • All conventional proton acceptors can be used as bases in process (a).
  • Alkali or alkaline earth metal hydroxides, alkali or alkaline earth metal carbonates or hydrogen carbonates or nitrogen bases are preferably usable. Examples include sodium hydroxide, calcium hydroxide, potassium carbonate, sodium hydrogen carbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine,
  • DBU diazabicyclooctane
  • DBN diazabicyclonones
  • DBU diazabicycloundecene
  • reaction temperatures can be varied within a wide range in process (a) described above. In general, temperatures between -40 ° C and + 200 ° C, preferably between 0 ° C and 100 ° C.
  • the end products are worked up and isolated in a generally known manner.
  • Possible sulfurizing agents in carrying out process (b) according to the invention are: phosphorus pentasulfide or Lawesson's reagent [2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetane-2,4-dithione] ( see also Tetrahedron Vol. 41, No. 22, 5061 ff (1985))
  • Suitable diluents for carrying out process (b) according to the invention are preferably hydrocarbons, such as toluene, xylene, tetralin, hexane or cyclohexane.
  • reaction temperatures can be varied within a substantial range in carrying out process (b) according to the invention. In general, temperatures between 0 ° C. and 200 ° C., preferably between 20 ° C. and 150 ° C.
  • temperatures between 0 ° C. and 200 ° C., preferably between 20 ° C. and 150 ° C.
  • sulfurizing agent When carrying out process (b) according to the invention, generally between 1 and 3 mol, preferably between 1 and 2 mol, of sulfurizing agent are used per mol of compound of the formula (Ia).
  • the processing takes place according to usual methods. In some cases it may prove advantageous to directly combine the pyrimidine derivatives of the formula (II) with halides of the formula (purple)
  • the active ingredients are suitable for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stocks 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, Porcelli o scaber. From the order of the Diplopoda e.g. Blaniulus guttulatus.
  • Thysanura e.g. Lepisma saccharina
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.
  • Heteroptera e.g. Eurygaster spp., Dysdercus intermedius
  • Aleurodes brassicae Bemisia tabaci
  • Trialeurodes vaporariorum Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigususpp.
  • Sitophilus spp. Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Niptus holium ps spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.
  • Hymenoptera e.g. Diprion spp, Hoplocampa spp, Lasius spp, Monom orium pharaonis, Vespa spp
  • Diptera From the order of Diptera, for example Aedes spp, Anopheles spp, Culex spp, Drosophila melanogaster, Musca spp, Fannia spp, Calliphora erythrocephala, Lucilia spp, Chrysomyia spp, Cuterebra spp, Gastrophilus spp., Hyppobosca spp,
  • Siphonaptera for example Xenopsylla cheopis
  • Ceratophyllus spp From the order of the Arachnida for example Scorpio maurus, Latrodectus mactans
  • Acarina for example Acarus siro, Argas spp, Ornithodoros spp, Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp, Rhipicephalus spp., Amblyomma spp, Hyalomma spp, Ixodes spp., Psoroptes spp., Psoroptes spp , Tarsonemus spp, Bryobia praetiosa, Panonychus spp, Tetranychus spp
  • Plant parasitic nematodes include, for example, Pratylenchus spp, Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp, Globodera spp., Meloidogyne spp, Aphelenchoides spp, Longidorus spp, Xiphinema spp, Trichodor
  • the compounds of the formula (I) according to the invention are notable in particular for outstanding insecticidal activity. They can be used with particularly good success in combating plant-damaging insects.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents
  • Agents ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • Liquid solvents are essentially suitable.
  • Aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, 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 and dimethyl sulfoxide, and water.
  • 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 and dimethyl sulfoxide, and water.
  • Eg ammonium salts and natural rock flour such as kaolins, clays.
  • Talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks;
  • Suitable emulsifying and / or foam-generating agents are: for example 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 dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phosphophides.
  • Other additives can be mineral and vegetable oils
  • Dyes such as inorganic pigments, for example 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% by weight of active compound, preferably between 0.5 and 90%.
  • the active compound according to the invention can be used in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides and attractants , Sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides are present.
  • Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons,
  • Phenylureas substances produced by microorganisms u. a.
  • Fenpropimorph Fentin Acetate, Fentin Hydroxyd, Ferbam, Ferimzone, Fluazinam, Fludioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanil, Flutriafol, Folpet, Fosetyl-Aluminum, Fthalide, Fuberidazol, Furalaxyl, Guazecatine
  • Tebuconazole Tecloftalam, Tecnazen, Tetraconazole, Thiabendazole, Thicyofen, Thiophanat-methyl, Thiram, Tolclophos-methyl, Tolylfluanid, Triadimefon, Triadimenol, Triazoxid, Trichlamid, Tricyclazol, Tridemorph, Trifluminol, Trifluminol
  • Bactericides bronopol, dichlorophene, nitrapyrin, nickel-dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox,
  • Imidacloprid Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Lambda-cyhalothrin, Lufenuron, Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos,
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophos,
  • the active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds through which the action of the active ingredients is increased 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.
  • the active ingredient When used against hygiene pests and pests of stored products, the active ingredient is distinguished by an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates.
  • the active compounds according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas.
  • animal parasites ectoparasites
  • tick ticks leather ticks
  • mites running mites
  • flies stinging and licking
  • parasitic fly larvae lice, hair lice, Featherlings and fleas.
  • Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
  • Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota ., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Glossina spp., Calliphora spp., Glossina spp.,
  • Hyalomma spp. Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp ..
  • Actinedida Prostigmata
  • Acaridida Acaridida
  • Acarapis spp. Cheyletiella spp., Omithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectolich spp., Pod ., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp ..
  • the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used in agricultural animals, e.g. Cattle, sheep,
  • the active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, of feed-through
  • suppositories by parenteral administration, such as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), Pouring on (pour-on and spot-on), washing, powdering and with the help of active ingredients
  • the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or apply after 100 to 10,000-fold dilution or use it as a chemical bath.
  • insects may be mentioned by way of example and preferably, but without limitation:
  • Kalotermes flavicollis Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
  • Bristle tails such as Lepisma saccarina.
  • technical materials include non-living ones
  • the material to be protected against insect infestation is very particularly preferably wood and wood processing products.
  • Wood and wood processing products which can be protected by the agent according to the invention or mixtures containing it are to be understood as examples: timber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone masts, wooden cladding, wooden windows and doors , Plywood, chipboard, carpentry or wood products that are used in general in house construction or joinery.
  • the active substances can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
  • the formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments and further processing aids.
  • the insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active ingredient according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
  • the amount of the agents or concentrates used depends on the type and occurrence of the insects and on the medium. The optimum amount to be used can be determined in each case by use of test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected
  • the organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
  • Water-insoluble, oily and oil-like solvents are used corresponding mineralols or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene.
  • Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, turpentine oil and Like the use.
  • liquid aliphatic hydrocarbons with a boiling range from 180 to 210 ° C or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range from 180 to 220 ° C and / or locker oil and / or monochloronaphthalene, preferably monochloronaphthalene, are used.
  • the organic non-volatile oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number above 35 and has a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.
  • a part of the organic chemical solvent or solvent mixture is replaced by an ahphatic polar organic chemical solvent or solvent mixture.
  • Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups, such as, for example, glycol ether esters or the like, are preferably used.
  • the known organic-chemical binders are the water-dilutable synthetic resins and / or synthetic resins which are soluble or dispersible or emulsifiable in the organic chemical solvents used and / or binding drying oils, in particular binders consisting of or containing an acrylate resin, a vinyl resin, e.g. Polyvinyl acetate,
  • Polyester resin polycondensation or poly addition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene Coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or synthetic resin are used.
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellent agents, odor-correcting agents and inhibitors or anticorrosive agents and the like. be used.
  • At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder.
  • binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer (mixture).
  • a fixing agent mixture
  • a plasticizer mixture
  • additives are intended to prevent the active ingredients from cursing and from crystallizing or precipitating. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).
  • the plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, higher glycated glycol ether or glycated ether and p-toluenesulfonic acid ester.
  • phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate
  • phosphoric acid esters such as tributyl phosphate
  • adipic acid esters such as di- (2-ethylhexyl) adipate
  • stearates such as butyl stearate or amy
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvmylmethylether or ketones such as benzophenone, ethylene benzophenone.
  • Water is also particularly suitable as a solvent or diluent, optionally in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
  • a particularly effective wood protection is achieved by industrial impregnation processes, e.g. vacuum, double vacuum or pressure processes.
  • the ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides.
  • the insecticides and fungicides mentioned in WO 94/29 268 are preferably suitable as additional admixing partners.
  • the compounds mentioned in this document are an integral part of the present application.
  • Insecticides such as chlorpyriphos, phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, decamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron, triflumurone, and epizazole, as well as fungizazone, such as epizazole, such as epizazole, as well as fungizazone, such as epizazole, such as epizazole, such as epizazole, as well as fungizazone, such as epizazole, as Cyproconazole, metconazole, imazalil, dichlorfluanid, tolylfluanid, 3-iodo-2-propynyl-butylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-
  • Fungicidal agents in crop protection are used to combat Piasmodi ophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.
  • Bactericidal agents are used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • Some pathogens of fungal and bacterial diseases that fall under the generic names listed above may be mentioned as examples, but not by way of limitation:
  • 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 Pseudoperonospora cubensis;
  • 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
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Cochliobolus species such as, for example, Cochliobolus sativus
  • 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 herpotrichoides.
  • the active compounds are well tolerated by plants in the concentrations required to combat plant diseases permits treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil. They can be used, for example, with particularly good success against the pathogen of apple mildew (Podosphaera leucotricha) and apple scab (Venturia inaequalis).
  • the active compounds according to the invention can be used as such, in the form of their commercially available formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusting agents and granules.
  • the application is carried out in the customary manner, e.g. by pouring, spraying, atomizing, scattering, 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 itself into the soil. It can also be
  • Seeds of the plants are treated.
  • the active compound concentrations in the use forms can be varied within a substantial range: they are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001% by weight.
  • amounts of active ingredient of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.
  • active ingredient concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, are required at the site of action.
  • the solid is filtered off with suction, the filtrate is concentrated and the residue is partitioned between dichloromethane and water, the org. Phase dried and concentrated.
  • the crude product is triturated with a little ether, the product is obtained in the form of a solid.
  • reaction mixture is washed with dilute hydrochloric acid, water, dried and evaporated.
  • the mixture is concentrated, the residue is partitioned between warm sodium bicarbonate solution and chloroform, the product is filtered off and recrystallized from ethanol.
  • Phaedon larval test solvent 7 parts by weight of dimethylformamide
  • 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 at the desired concentration and with horseradish leaf beetle larvae (Phaedon cochleariae) occupied while the leaves are still moist
  • the death rate is determined in%. 100% means that all beetle larvae have been killed, 0% means that no beetle larvae have been killed
  • the compounds according to Preparation Examples 8, 10, 13, 23, 24, 30, 35, 43, 52, 62, 71 and 74 caused a death rate of 100% according to FIG. 7 at an exemplary active ingredient concentration of 0.1% Days
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of 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 dipping into the active ingredient preparation of the desired concentration and with caterpillars of the cabbage cockroach
  • the death rate is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed. In this test, e.g. the compounds according to the preparation examples
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, mix 1
  • Cabbage leaves (Brassica oleracea) are treated by dipping into the active ingredient preparation of the desired concentration and with caterpillars of the owl butterfly
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of 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.
  • Broad bean seedlings (Vicia faba), which are infested with green peach aphids (Myzus persicae), are immersed in the active compound preparation of the desired concentration and placed in a plastic can.
  • the death rate is determined in percent. 100% means that all aphids have been killed, 0% means that no aphids have been killed. In this test, for example, the compound according to Preparation Example 13 caused a death rate of 90% after 6 days at an exemplary active ingredient concentration of 0.1%.
  • Nephotettix test solvent 7 parts by weight of dimethylformamide
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, mix 1
  • Rice seedlings (Oryza sativa) are treated by immersing them in the active ingredient preparation of the desired concentration and with larvae of the green rice leafhopper
  • the kill is determined in%. 100% means that all cicadas have been killed, 0% means that no cicadas have been killed. In this test, at an exemplary active ingredient concentration of 0.1
  • Emulsifier 0.3 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of 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 23 ° C. and a relative humidity of approx. 70%.
  • Evaluation is carried out 10 days after the inoculation. This test showed, for example. the compound according to preparation example 52 has an efficiency of 98% at an exemplary active ingredient concentration of 100 ppm.
  • Emulsifier 0.3 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, mix 1
  • the plants are then placed in a greenhouse at 20 ° C. and a relative humidity of approx. 70%. Evaluation is carried out 12 days after the inoculation.
  • the compound according to preparation example 52 has an efficiency of 99% at an active ingredient concentration of 100 ppm.

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

Abstract

L'invention concerne de nouveaux composés de la formule (I) dans laquelle R1, R2, Ar, A et X ont la notation mentionnée dans la description, des procédés permettant de les préparer et leur utilisation pour lutter contre des parasites animaux et comme fongicides.
PCT/EP1997/000240 1996-02-01 1997-01-20 4-amino- et 4-hydrazinopyrimidines acylees et leur utilisation comme agents pour lutter contre les parasites WO1997028133A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP9527274A JP2000503998A (ja) 1996-02-01 1997-01-20 アシル化された４―アミノ―及び４―ヒドラジノピリミジン及びその有害生物防除剤としての使用
EP97902189A EP0880505A1 (fr) 1996-02-01 1997-01-20 4-amino- et 4-hydrazinopyrimidines acylees et leur utilisation comme agents pour lutter contre les parasites
AU15932/97A AU1593297A (en) 1996-02-01 1997-01-20 Acylated 4-amino- and 4-hydrazinopyrimidines and their use as pesticides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1996103576 DE19603576A1 (de) 1996-02-01 1996-02-01 Acylierte 4-Amino und 4-Hydrazinopyrimidine
DE19603576.7 1996-02-01

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WO1997028133A1 true WO1997028133A1 (fr) 1997-08-07

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JP (1) JP2000503998A (fr)
AU (1) AU1593297A (fr)
DE (1) DE19603576A1 (fr)
WO (1) WO1997028133A1 (fr)

Cited By (57)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009506125A (ja) * 2005-08-29 2009-02-12 ジェラルド・エム・ハウシー セラミューテイン・モジュレーター
US7560564B2 (en) 2001-03-05 2009-07-14 E.I. Du Pont De Nemours And Company Heterocyclic diamide invertebrate pest control agents
US7989462B2 (en) 2003-07-03 2011-08-02 Myrexis, Inc. 4-arylamin-or-4-heteroarylamino-quinazolines and analogs as activators of caspases and inducers of apoptosis and the use thereof
US8071606B2 (en) 2009-01-20 2011-12-06 Pfizer Inc. Substituted pyrazinone amides useful for activation of glucokinase
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US8604032B2 (en) 2010-05-21 2013-12-10 Infinity Pharmaceuticals, Inc. Chemical compounds, compositions and methods for kinase modulation
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Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19727162A1 (de) * 1997-06-26 1999-01-07 Bayer Ag Substituierte Aminoheterocyclylamide
WO2002070483A1 (fr) * 2001-03-05 2002-09-12 E. I. Du Pont De Nemours And Company Agents heterocycliques diamide de lutte contre des parasites invertebres
JPWO2016175017A1 (ja) * 2015-04-28 2018-02-22 アグロカネショウ株式会社 新規な４−ピリジンカルボキサマイド誘導体及びこれを有効成分として含む農園芸用薬剤

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2956998A (en) * 1960-10-18 Adenine derivatives and process
GB963924A (en) * 1961-07-25 1964-07-15 Takeda Chemical Industries Ltd Fungicidal compositions for agricultural use
EP0313512A2 (fr) * 1987-08-21 1989-04-26 Ciba-Geigy Ag Benzothiadiazoles et leur utilisation dans des procédés et des compositions contre les maladies végétales
EP0370704A2 (fr) * 1988-11-21 1990-05-30 Ube Industries, Ltd. Dérivés d'aralkylamine, leur préparation et fungicides les contenant
EP0467760A1 (fr) * 1990-07-18 1992-01-22 Sumitomo Chemical Company, Limited Derivés de pyrimidine, procédés pour leur préparation et fongicides, insecticides et/ou acaricides les contenant comme ingrédient actif
EP0606011A1 (fr) * 1992-12-28 1994-07-13 SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD. Dérivés d'aminopyriden, procédé pour leur préparation et leur utilisation
EP0649855A1 (fr) * 1993-10-20 1995-04-26 Roche Diagnostics GmbH Utilisation de nucléosides et dérivés nucléosides avec groupes protégeants qui sont coupables avec enzymes dans la synthèse des oligonucléotides
WO1995018795A1 (fr) * 1994-01-07 1995-07-13 Dowelanco N-(4-pyrimidinyle)amide en tant que pesticides
DE4417163A1 (de) * 1994-05-17 1995-11-23 Hoechst Schering Agrevo Gmbh Heterocyclylamino- und Heterocyclyloxy-cycloalkyl-Derivate, ihre Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel und Fungizide

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2956998A (en) * 1960-10-18 Adenine derivatives and process
GB963924A (en) * 1961-07-25 1964-07-15 Takeda Chemical Industries Ltd Fungicidal compositions for agricultural use
EP0313512A2 (fr) * 1987-08-21 1989-04-26 Ciba-Geigy Ag Benzothiadiazoles et leur utilisation dans des procédés et des compositions contre les maladies végétales
EP0370704A2 (fr) * 1988-11-21 1990-05-30 Ube Industries, Ltd. Dérivés d'aralkylamine, leur préparation et fungicides les contenant
EP0467760A1 (fr) * 1990-07-18 1992-01-22 Sumitomo Chemical Company, Limited Derivés de pyrimidine, procédés pour leur préparation et fongicides, insecticides et/ou acaricides les contenant comme ingrédient actif
EP0606011A1 (fr) * 1992-12-28 1994-07-13 SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD. Dérivés d'aminopyriden, procédé pour leur préparation et leur utilisation
EP0649855A1 (fr) * 1993-10-20 1995-04-26 Roche Diagnostics GmbH Utilisation de nucléosides et dérivés nucléosides avec groupes protégeants qui sont coupables avec enzymes dans la synthèse des oligonucléotides
WO1995018795A1 (fr) * 1994-01-07 1995-07-13 Dowelanco N-(4-pyrimidinyle)amide en tant que pesticides
DE4417163A1 (de) * 1994-05-17 1995-11-23 Hoechst Schering Agrevo Gmbh Heterocyclylamino- und Heterocyclyloxy-cycloalkyl-Derivate, ihre Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel und Fungizide

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
J. B. POLYA ET. AL.: "Polyazanaphthalenes. Part I. Synthesis of Pyrimido-[5,4-e] as-triazines.", JOURNAL OF THE CHEMICAL SOCIETY, vol. 1964, OXFORD,GB, pages 4986 - 92, XP000654084 *
J. J. TRAVERSO ET. AL.: "The Synthesis and Pharmacological Activities of Amide, Sulfamide and Urea Derivatives of 4,6-Diaminopyrimidine.", JOURNAL OF MEDICINAL AND PHARMACEUTICAL CHEMISTRY, vol. 5, 1962, pages 808 - 15, XP000653960 *

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