WO2003059903A2 - Derives substitues de 4-aminopyridine - Google Patents

Derives substitues de 4-aminopyridine Download PDF

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Publication number
WO2003059903A2
WO2003059903A2 PCT/EP2003/000051 EP0300051W WO03059903A2 WO 2003059903 A2 WO2003059903 A2 WO 2003059903A2 EP 0300051 W EP0300051 W EP 0300051W WO 03059903 A2 WO03059903 A2 WO 03059903A2
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spp
formula
substituted
chlorine
alkyl
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PCT/EP2003/000051
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German (de)
English (en)
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WO2003059903A3 (fr
Inventor
Fritz Maurer
Christoph Erdelen
Karl-Heinz Kuck
Astrid Mauler-Machnik
Ulrike Wachendorff-Neumann
Andreas Turberg
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Bayer Cropscience Aktiengesellschaft
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Priority to AU2003235696A priority Critical patent/AU2003235696A1/en
Publication of WO2003059903A2 publication Critical patent/WO2003059903A2/fr
Publication of WO2003059903A3 publication Critical patent/WO2003059903A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to new substituted 4-aminopyridine derivatives, processes for their preparation and their use as pesticides and for controlling unwanted microorganisms.
  • R 1 represents alkyl
  • R 2 represents halogen
  • Het represents an optionally substituted heterocycle
  • n 1 or 2
  • Y stands for halogen, alkyl or haloalkyl and p stands for 0, 1 or 2.
  • R 1 and R 2 have the meanings given above,
  • Het, Y, n and p have the meanings given above,
  • halogenating agent preferably thionyl chloride, optionally in the presence of an acid binding agent and optionally in the presence of a diluent;
  • Het, Y and p have the meanings given above and m represents 0 or 1,
  • the 4-aminopyridine derivatives according to the invention are generally defined by the formula (I).
  • R 1 is preferably C ⁇ -C 4 - alkyl.
  • R 2 preferably represents fluorine, chlorine, bromine or iodine.
  • Het preferably represents an optionally mono- or polysubstituted, identically or differently substituted 5- or 6-membered heterocycle having 1 to 4 heteroatoms, such as N, O or S, examples of which may be mentioned as substituents:
  • n is preferably 1 or 2.
  • Y preferably represents fluorine, chlorine, bromine; C 1 -C 4 alkyl or dC 4 - haloalkyl, p preferably represents 0, 1 or 2.
  • R 1 is particularly preferably C 1 -C 2 -alkyl.
  • R 2 particularly preferably represents fluorine, chlorine or bromine.
  • Het particularly preferably represents 5- or 6-membered heterocycles from the series of thienyl, oxazolyl, isoxazolyl, pyrazolyl; 1,2,4-oxadiazolyl; 1,2,4-thia-diazolyl; 1,3,4-thiadiazolyl; Tetrazolyl, pyridinyl, pyrimidinyl or pyridonyl, each of which can be substituted one to three times (depending on the respective substitution options), identically or differently, examples of such substituents being: fluorine, chlorine, bromine, iodine; Gi alkyl; C ⁇ -C 4 alkoxy, C 1 -C 4 alkylthio; each one to five times, the same or different, substituted by fluorine or chlorine substituted Ci- -alkyl, Cr -alkoxy and CrC -alkylthio; Cyano, nitro, formyl, hydroxyimino, C 1 -C alkyl: oxy
  • n particularly preferably represents 1 or 2.
  • Y particularly preferably represents fluorine, chlorine, methyl or trifluoromethyl.
  • p particularly preferably represents 0, 1 or 2.
  • R 1 very particularly preferably represents ethyl.
  • R 2 very particularly preferably represents chlorine.
  • Het very particularly preferably represents 5- or 6-membered heterocycles from the
  • Pyridonyl each one to three times (depending on the respective substitution options), may be substituted identically or differently, examples of which may be mentioned as substituents: fluorine, chlorine, bromine; Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; Methoxy, ethoxy, n- or i-propoxy; Methylthio, ethylthio, n- or i-propylthio; Trifluoromethyl, difluoromethyl, fluoromethyl; Trifluoromethoxy, difluoromethoxy; trifluoromethylthio; Cyano, formyl, hydroximino, methoxyimino, ethoxyimino; Methylcarbonyl, ethylcarbonyl; Methoxycarbonyl, ethoxycarbonyl; Methoxycarbonyl-methyl, 1-methoxycarbonyl-1-
  • n very particularly preferably represents 1 or 2.
  • p very particularly preferably represents 0.
  • radical definitions can be combined with one another in any way.
  • individual definitions can also be omitted.
  • radical definitions listed in the above and below are carbon residues, such as alkyl - also in combination with heteroatoms, such as alkoxy - as far as possible, in each case straight-chain or branched.
  • the starting materials for carrying out process (a) according to the invention are generally defined by the formula (E).
  • R and R are preferably, particularly preferably or very particularly preferably, those meanings which have already been mentioned as preferred, particularly preferred or very particularly preferred for these radicals in connection with the description of the compounds of the formula (I) according to the invention ,
  • the 4-aminopyridines of the formula (E) are generally known compounds of organic chemistry.
  • Formula (ET) provides a general definition of the phenylacetic acids to be used as starting materials in process (a) according to the invention.
  • Het, n, Y and p are preferred, particularly preferred or very particularly preferred for those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred, particularly preferred or entirely for these radicals were particularly preferred.
  • the phenylacetic acids of the formula (ET) are new and also the subject of this application. They are obtained by building up the heterocyclic radical on the correspondingly substituted phenyl in a known manner.
  • the 4-tetrazolylphenylacetic acids are obtained by mixing 4-cyanophenylacetic acid with sodium azide in the presence of an amine hydrochloride (for example ammonium chloride or trialkylammonium chloride) and in the presence of an inert organic solvent (for example toluene) at temperatures between 50 ° C. and 150 ° C., preferably between 80 ° C and 120 ° C (see also the manufacturing examples).
  • the tetrazolyl radical can then be alkylated in a conventional manner (see also the preparation examples).
  • the 4-pyrazolylphenylacetic acids are e.g. obtained by using 4-hydrazino-phenylacetic acid hydrochloride with sodium salts of 2-substituted 1-hydroxy-
  • the formula (TV) generalizes the substituted 4-aminopyridines to be used as starting materials for carrying out process (b) according to the invention
  • R and R are preferably, particularly preferably or very particularly preferably, those meanings which have already been mentioned for these radicals in connection with the description of the compounds of the formula (I) according to the invention.
  • Q is preferably B (OH); 4,4,5,5-tetramethyl-l, 3,2-dioxoborolan-2-yl; 5,5-dimethyl-3,2-dioxo-borinan-2-yl; 4,4,6-trimethyl-l, 3,2-di-oxo-borinan-2-yl or l, 3,2-benzodioxoborolan-2-yl.
  • the substituted 4-aminopyridines of the formula (TV) are new and also the subject of this application. They are obtained by first of all 4-aminopyridines of the formula (E) in which
  • R 1 and R 2 have the meanings given above,
  • R 1 and R 2 have the meanings given above,
  • Formula (V) provides a general definition of the bromides to be used as starting materials in process (b) according to the invention.
  • Het, Y and p are preferred, particularly preferred or very particularly preferred for those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred, particularly preferred or very particularly preferred for these radicals were mentioned, m preferably represents 0 or 1.
  • the bromides of the formula (V) are known or can be obtained in a known manner.
  • R and R are preferably, particularly preferably or very particularly preferably, those meanings which have already been mentioned as preferred, particularly preferred or very particularly preferred for these radicals in connection with the description of the compounds of the formula (I) according to the invention ,
  • the substituted 4-aminopyridines of Foremi (VI) are obtained by reacting 4-ammopyridines of the formula (E) with 4-bromophenylacetic acid in accordance with the conditions of process (a).
  • Formula (VE) provides a general definition of the compounds to be used as starting materials in process (c) according to the invention.
  • Het, Y and p are preferred, particularly preferred or very particularly preferred for those meanings which have been mentioned as preferred, particularly preferred or very particularly preferred for these radicals in connection with the description of the compounds of the formula (I) according to the invention
  • m preferably represents 0 or 1.
  • Q preferably represents those meanings which have already been mentioned as preferred for these radicals in connection with the description of the 4-aminopyridines of the formula (TV).
  • the compounds of formula (VE) are obtained by reacting bromides of formula (V) with boron derivatives of formula (TX) in accordance with the conditions of process (c).
  • DABCO diazabicyclooctane
  • DBU Diazabicyclonones
  • DBU diazabicycloundecen
  • Suitable diluents for carrying out process (a, variant 1) are all inert, organic solvents.
  • Aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin can preferably be used; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; 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,
  • reaction temperatures can be varied within a relatively wide range. In general, temperatures between 0 ° C and + 120 ° C, preferably between 20 ° C and 80 ° C.
  • Suitable catalysts for carrying out process are all customary reaction accelerators which are suitable for activating the carboxyl group of the phenylacetic acid derivative of the formula (ET).
  • Carbonyldiimidazole and dicyclohexylcarbodiimide can preferably be used.
  • the reaction can also be carried out in the presence of water-binding agents.
  • Suitable diluents for carrying out the process are all inert organic solvents which are customary for such reactions.
  • Aliphatic, alicyclic or aromatic can preferably be used
  • Hydrocarbons such as dioxane, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane.
  • halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane.
  • reaction temperatures can be varied within a certain range. In general, temperatures between 0 ° C and 120 ° C, preferably between 20 ° C and 80 ° C.
  • the procedure (a, variant 2) is generally carried out using equimolar amounts. However, it is also possible to use one or the other component in excess.
  • the processing takes place according to usual methods. In general, the procedure is such that the solid which has precipitated is filtered off with suction, the filtrate is concentrated under reduced pressure and the residue which remains is chromatographed.
  • the diluents used in the process are those of the invention
  • Hydrocarbons such as are preferably used PT / EP03 / 00051
  • halogenated hydrocarbons such as methylene chloride, chloroform, chlorobenzene, o-dichlorobenzene
  • ethers such as diethyl ether, diisopropyl ether, dimethoxyethane, tetiahydrofuran, dioxane
  • nitriles such as acetonitrile
  • Suitable bases for carrying out processes (b) and (c) according to the invention are all customary acid acceptors.
  • Tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicyclo- undecene (DBU), diazabicyclonones (DBN), N, N-dimethylaniline, also alkaline earth metal oxides such as magnesium or calcium oxide, and also alkali metal and alkaline earth metal carbonates are preferably usable such as sodium carbonate, potassium carbonate and calcium carbonate, alkali metal hydroxides such as sodium or potassium hydroxide, and also alcoholates such as sodium ethanolate or potassium tert-butoxide.
  • reaction temperatures can be when carrying out the inventive reaction temperatures
  • Processes (b) and (c) can be varied over a wide range. In general, temperatures between 0 ° C and 120 ° C, preferably between 20 ° C and 80 ° C or at the boiling point of the solvent used.
  • the reaction is generally carried out in equimolar amounts, with 0.01 to 0.1 mol being optionally added
  • Catalyst and 1 to 5 mol of base can be used.
  • the end products are worked up and isolated in a generally customary manner.
  • the active ingredients are suitable with good plant tolerance and inexpensive warm Blood toxicity to control animal pests, especially insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stocks and materials as well as 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. From the order of the Diplopoda e.g. Blaniulus guttulatus.
  • Chüopoda e.g. Geophilus carpophagus, Scutigera spp ..
  • Thysanura e.g. Lepisma saccharina.
  • Phthiraptera e.g. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp ..
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci
  • Thrips palmi, Frankliniella accidentalis From the order of the Heteroptera e.g. Eurygaster spp., Dysdercus intermedius,
  • Trialeurodes vaporariorum Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabäe, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phoroponosum , Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.
  • Conoderus spp. Melolontha melolontha, Amphimallon s ⁇ lstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Diptera e.g. Aedes spp., Anopheles spp., Culex spp.
  • Drosophila melanogaster Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tabanus spp.
  • Tannia spp. Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp ..
  • Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetians, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaph.
  • the substances according to the invention can be used with particularly good success for combating plant-damaging insects, such as e.g. against the larvae of the cucumber beetle (Diabrotica balteata), the caterpillars of the cotton capsule worm (Heliothis virescens), the larvae of the horseradish beetle (Phaedon cochleariae), the
  • Cabbage caterpillars Panlla xylostella
  • army worm caterpillars Spodoptera exigua and Spodoptera frugiperda
  • cotton aphid Aphis gossypii
  • peach aphid Mycus persicae
  • plant-damaging mites such as against bean spanym mite (tica spica mite)
  • the substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.
  • Fungicides can be used to control Plasmodiophoromycetes
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • Some pathogens of fungal and bacterial are exemplary but not limiting
  • 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 grarninis;
  • 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. grarninea
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • CochHobolus species such as, for example, Cocbliobolus sativus (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 sclerotiorurn
  • 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.
  • Plants on. They are therefore suitable for mobilizing the plant's own defenses against attack by unwanted microorganisms.
  • Plant-strengthening (resistance-inducing) substances are to be understood in the present context as those substances that are able to
  • undesirable microorganisms include phytopathogenic
  • the substances according to the invention can therefore be used to protect plants against attack by the named pathogens within a certain period of time after the treatment.
  • the period within which protection is brought about generally extends from 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active compounds.
  • the active compounds according to the invention can be used with particularly good success to combat cereal diseases, such as mildew and rust, and against diseases in wine, fruit and vegetable cultivation, such as Venturia, Podosphaera and Sphaerothera 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 rates as herbicides, for influencing plant growth, and for controlling animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of further active compounds.
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants).
  • Cultivated 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 the plant cultivars which 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.
  • 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 according to the customary treatment methods, for example by dipping, spraying, evaporating, atomizing, scattering, spreading and in the case of propagation material, in particular seeds single or multi-layer wrapping.
  • the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
  • technical materials that are to be protected against microbial change or destruction by active substances according to the invention can be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials that can be attacked or decomposed by microorganisms .
  • parts of production plants for example cooling water circuits, are also mentioned which can be impaired by the multiplication of microorganisms.
  • the preferred technical materials are adhesives, glues, papers and cartons, leather, wood,
  • Bacteria, fungi, yeasts, algae and slime organisms may be mentioned as microorganisms which can cause degradation or a change in the technical materials.
  • the active compounds according to the invention preferably act against fungi, in particular scummel fungi, 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 like 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 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 also ULV cold and warm fog formulations.
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • 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 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.
  • Liquefied gaseous triangular agents 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.
  • Possible solid carriers are: for example natural stone powders such as kaolins, alumina, 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 as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems.
  • Suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • Possible dispersants are: e.g. Lignin sulfite liquors and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as Giimmiarabicum, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Other 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, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight
  • Active ingredient preferably between 0.5 and 90%.
  • the active compounds according to the invention can be used as such or in their formulations, also in a mixture " with known fungicides, bactericides, acaricides, nematicides or insecticides, in order to broaden the spectrum of action or to prevent development of resistance, for example. In many cases, one obtains synergistic effects, ie the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Debacafb dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dodipoxazolone, dodipoxazolone, dithipoxazol Ethirimol, etridiazole,
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepampyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax,
  • Thicyofen Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, uniconazole, validamycin A, vinclozolin, Viniconazol, Zarilamid , Zineb, ziram as well
  • Dagger G OK-8705, OK-8801, ⁇ - (1, 1-dimethylethyl) -ß- (2-phenoxyethyl) - 1 H-1, 2,4-triazole-1-ethanol, ⁇ - (2,4 -Dichlorophenyl) -ß-fluoro-ß-propyl-1 H-1, 2,4- ⁇ riazole-1-ethanol, ⁇ - (2,4-dichlorophenyl) -ß-methoxy- ⁇ -methyl-1H-1, 2 , 4-triazol-1-ethanol, ⁇ - (5-methyl-l, 3-dioxan-5-yl) -ß - [[4- (trifluoromethyl) phenyl] methylene] -lH-l, 2.4 triazole-1-ethanol,
  • Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene, Imidacloprid, Indoxacarb, Isazofos, Isofenphos, Isoxathion, Ivermectin, Kernpolyederviruses, Lambda-cyhalothrin, Lufenuron
  • Pirimiphos M Profenofos, Promecarb, Propargite, Propoxur, Prothiofos, Prothoat,
  • Triarathenes triazamates, triazophos, triazuron, trichlophenidines, trichlorfon,
  • the compounds of formula (I) according to the invention also have very good antifungal effects. They have a very broad antimycotic activity spectrum, especially against dermatophytes and fungi, mold and diphasic fungi (eg against Candida species such as Candida albicans, Candida glabrata) as well as Epidermophyton floccosum, Aspergillus species such as Aspergillus nigerumigatus and Aspergillus -Species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audoüinii.
  • Candida species such as Candida albicans, Candida glabrata
  • Epidermophyton floccosum Aspergillus species such as Aspergillus nigerumigatus and Aspergillus -Species such as Trichophyton mentagrophytes
  • Microsporon species such as Microsporon canis and audoüinii.
  • the list of these fungi does not in any way limit the my
  • 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. They are used in the usual way, e.g. by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by 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 1,000 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
  • 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 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 ingredient concentration of Application forms can be from 0.0000001 to 95% by weight of active compound, 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.
  • plants and their parts can be treated according to the invention.
  • transgenes are also preferred.
  • Plants and plant varieties that have been obtained by genetic engineering methods, possibly in combination with conventional methods (Genetic Modified Organisms) and their parts treated.
  • Genetic Modified Organisms Geneous Modified Organisms
  • the term “parts” or “parts of plants” or “plant parts” was explained above.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with new properties (“traits”) which have been grown both by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, breeds, bio and genotypes.
  • the treatment according to the invention can also give rise to superadditive ("synergistic") effects.
  • superadditive for example, reduced application rates and / or extensions of the
  • W kimgsspektrum and / or an enhancement of the effect of the substances and agents usable according to the invention better plant growth, increased tolerance against high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher harvest yields, higher quality and or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, that go beyond the expected effects.
  • the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which, by virtue of the genetic engineering modification, have received genetic material which gives these plants particularly advantageous, valuable properties (“traits”). 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 ripening, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products.
  • transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes and cotton and rapeseed are highlighted.
  • the traits are particularly emphasized as the increased defense of the plants against insects by toxins which arise in the plants, in particular those which are caused by the genetic material from BaciUus thuringiensis (for example by the genes CryIA (a), CryIA (b), CryIA (c), CryEA, CryEIA, CryEIB2 5 Cry9c Cry2Ab, Cry3Bb and CryTF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
  • Bt plants The increased resistance of plants against fungi, bacteria and viruses are also particularly emphasized as traits through systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • herbicidal active compounds for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example “P P-
  • genes imparting the desired properties can also occur in combinations with one another in the transgenic plants.
  • “Bt plants” are corn varieties, cotton varieties, soy varieties and potato varieties that are marketed under the trade names YTELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard®
  • herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties which are sold under the trade names Roundup Ready® (tolerance against glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance against phosphinotricin, e.g. rape), TMI® (tolerance against Imidazolinone) and STS®
  • the herbicide-resistant plants include the varieties sold under the name Clearfield® (e.g. maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
  • plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active compound mixtures according to the invention.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • the active compounds according to the invention act not only against plants, hygiene and
  • Pests, but also against the veterinary sector animal parasites such as tortoise ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, featherlings and fleas.
  • ectoparasites such as tortoise ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, featherlings and fleas.
  • Ischnocerina e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp.,
  • 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 spp., Philipomyia spp.,
  • Braula spp. Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,
  • Xenopsylla spp. Ceratophyllus spp .. From the order of the Heteropterida e.g. Cimex spp., Triatoma spp., Rhodnius spp.,
  • Hyalomma spp. Rhipicephalus spp., Dermanyssus spp., Raillietia spp.,
  • Actinedida Prostigmata
  • Acaridida Acaridida
  • Acarapis spp. Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp.
  • Tyfophagus spp. Caloglyphus spp., Hypodectes spp., Pterolichus spp., 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, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice. By fighting these arthropods, deaths and
  • 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, the feed-through method, suppositories, by parenteral administration, for example 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 shaped articles containing active ingredients, such as necklaces, ear tags, tail tags, limb tapes, holsters, marking devices, etc.
  • the active compounds of the formula (T) 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.
  • formulations for example powders, emulsions, flowable agents
  • 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 saccharina.
  • 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:
  • Lumber wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles,
  • 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.
  • formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active ingredients with at least one solution or
  • insecticides used to protect wood and wood-based materials or
  • Concentrates contain the 'active ingredient according to the invention in a concentration of 0.0001 to 95 wt .-%, in particular 0.001 to 60 wt .-%.
  • the amount of the agents or concentrates used depends on the type and occurrence of the insects and on the medium. The optimal amount can be determined in each case by 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.
  • An organic chemical solvent or solvent mixture and / or an oily or oily heavy serves as the solvent and / or diluent volatile organic chemical solvent or solvent mixture and / or a polar organic chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agent.
  • the organic chemical solvents used are preferably oily or oily ones
  • Solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, are used.
  • Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.
  • 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. Used.
  • 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 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.
  • part of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced.
  • Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups such as, for example, glycol ethers, esters or the like, are preferably used.
  • the known organic-chemical binders are water-thinnable and / or soluble or dispersible or emulsifiable in the organic-chemical solvents used
  • Synthetic resins 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 polyaddition 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 used.
  • binders consisting of or containing an acrylate resin, a vinyl resin, e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition 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 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-repellants, odor correctors and inhibitors or anticorrosive agents and the like can 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.
  • Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
  • All or part of the binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. 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 glycerol glycerol or glycerol ether - Kolether, glycerol ester 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
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
  • Water is also particularly suitable as a solvent or diluent, if appropriate 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 through industrial impregnation processes, e.g. Vacuum, double vacuum or pressure process.
  • the ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides.
  • 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, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermetiirin, deltämethrin, Permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthrin, thiacloprid, methoxyphenoxide and triflumuron,
  • fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorfluanide, tolylfluanid,
  • the compounds according to the invention can be used to protect objects, in particular hulls, sieves, nets, structures,
  • Scalpellum species or by species from the group Balanomorpha (barnacles), such as Baianus or Pollicipes species, increases the frictional resistance of ships and consequently leads to a significant increase in operating costs due to increased energy consumption and, moreover, frequent dry dock stays.
  • (trialkyltin) sulfides tri-n-butyltin laurate, tri-n-butyltin chloride, copper (I) oxide, triethyltin chloride, tri-w-butyl (2-phenyl-4-chlorophenoxy) tin, tributyltin oxide, molybdenum disulfide, antimony oxide, polymeric butyl titanate, phenyl (bispyridine) bismuth chloride, tri - «- butyltin fluoride, manganese ethylene bisthiocarbamate, zinc dimethyl dithiocarbamate, zinc ethylene bisthiocarbamate, zinc and copper salts of 2-pyridine-thiol-1-oxy-oxychloride, bis (bisdimide) oxydimethylamide, bisdimide (bisdimide), bis (bisdimide), bis (bisdimide), bis (bisdimide) amide, bisdimide (bis) amdiboxamide, bis
  • the ready-to-use antifouling paints may also contain other active ingredients, preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.
  • Suitable combination partners for the anti-fouling agents according to the invention are preferably:
  • Benzo [&] thiophenecarboxylic acid cyclohexylamide-S, S-dioxide, dichlofluanide, fluorofolpet, 3-iodo-2-propynyl butyl carbamate, tolyl fluanide and azoles such as
  • Molluscicides such as fentin acetate, metaldehyde, methiocarb, niclosamide, thiodicarb and trimethacarb; or conventional antifouling agents such as
  • the antifouling agents used contain the active compound according to the invention of the compounds according to the invention in a concentration of 0.001 to 50% by weight, in particular of 0.01 to 20% by weight.
  • the antifouling agents according to the invention furthermore contain the usual constituents, e.g. in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.
  • antifouling paints contain in particular binders.
  • Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in one
  • Solvent system in particular in an aqueous system, vinyl chloride / vinyl acetate copolymer systems.
  • aqueous dispersions or in the form of organic solvent systems, butadene / styrene acrylonitrile rubbers, drying oils, such as linseed oil, resin esters or modified hard resins in combination with tar or bitumen , Asphalt and epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.
  • Paints may also contain inorganic pigments, organic
  • Pigments or dyes which are preferably insoluble in sea water. Paints may also contain materials such as rosin in order to be controlled
  • the paints can also Plasticizers containing modifiers affecting theological properties and other conventional ingredients.
  • the compounds according to the invention or the abovementioned mixtures can also be incorporated into self-polishing antifouling systems. -
  • the active ingredients are also suitable for controlling animal pests, in particular insects, arachnids and mites, which live in closed spaces such as apartments, factory halls, offices, vehicle cabins, etc. occurrence. To control these pests, they can be used alone or in combination with other active ingredients and auxiliaries in household insecticide products.
  • Scorpionidea e.g. Buthus occitanus.
  • Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp.
  • Diplopoda e.g. Blaniulus guttulatus, Polydesmus spp ..
  • Saltatoria for example Acheta domesticus.
  • Dermaptera for example, Forficula auricularia.
  • Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
  • Ctenocephalides canis Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • Rhodinus prolixus Triatoma infestans.
  • reaction mixture is poured onto water and extracted with ethyl acetate.
  • organic phase is dried over sodium sulfate and evaporated in vacuo.
  • residue is triturated with disiopropyl ether and the precipitated product is filtered off with suction.
  • the determination is carried out in the acidic range at pH 2.3 with 0.1% aqueous phosphoric acid and acetonitrile as eluents; linear gradient from 10% acetonitrile to 90% acetonitrile.
  • the calibration is carried out with unbranched alkan-4-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention time by linear interpolation between two successive alkanones).
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • Cotton leaves which are heavily infested with the cotton aphid (Aphis gossypii), are treated by immersing them in the active ingredient preparation of the desired concentration.
  • the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • Pots filled with soil are poured into the active ingredient preparation. Immediately after the preparation, 5 corn kernels are laid out per pot and after 3 days the Diabrotica balteata larvae are placed on the treated soil. The concentration given relates to the amount of active ingredient per unit volume of soil (mg / 1).
  • the accumulated maize plants are counted and the efficiency is calculated. 100% means that all maize plants have emerged; 0% means that no maize plants have emerged.
  • Emulsifier 2. Parts by weight of alkylaryl polyglycol ether
  • Soybean shoots (Glycine max) are treated by dipping into the active ingredient preparation of the desired concentration and populated with Heliothis virescens caterpillars while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • compound 7 of the preparation examples shows a kill of 100% after 7 days.
  • Emulsifier 2 parts 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.
  • Vessels are filled with sand, active ingredient solution, Meloidogyne incognita egg larva suspension and lettuce seeds.
  • the lettuce seeds germinate and the plantlets develop.
  • the galls develop at the roots.
  • the nematicidal effect is determined in% using the formation of bile. 100% means that no galls were found; 0% means that the number of galls on the treated plants corresponds to that of the untreated control.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • Savoy cabbage plants (Brassica oleracea), which are heavily infested with the green peach aphid (Myzus persicae), are watered with 10 ml active ingredient preparation of the desired concentration, so that the active ingredient preparation in the
  • the active ingredient is absorbed by the roots and passed on to the shoot.
  • the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • Example F % and compound 34 of the preparation examples killed 99%, in each case after 6 days.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • 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 leaf 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 no beetle larvae have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the cockroach (Plutella xylostella) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • compound 7 of the preparation examples shows a kill of 100% after 7 days.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active ingredient of the desired concentration and populated with caterpillars of the army worm (Spodoptera exigua) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • compound 7 of the preparation examples shows a kill of 100% after 7 days.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the army worm (Spodoptera frugiperda) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
  • compound 19 of the preparation examples shows 95% kill and compound 34 of the preparation examples shows 100% kill, in each case after 7 days.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Soybean shoots (Glycine max) of the Roundup Ready variety (trademark of Monsanto Comp. USA) are treated by dipping into the preparation of active compound of the desired concentration and are populated with the tobacco bud caterpillar Heliothis virescens while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • Amount of emulsifier and dilute the concentrate with water to the desired concentration is required.
  • the active ingredient preparation is poured onto the floor.
  • the concentration of the active ingredient in the preparation is practically irrelevant, the only decisive factor is the amount of active ingredient per unit volume of soil, which is given in ppm (mg / 1). You fill the bottom in 0.25 1 pots and let them stand at 20 ° C.
  • 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.
  • 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.
  • 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 the greenhouse at approx. 21 ° C. and a relative humidity of approx. 90%.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Emulsifier 1 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.
  • 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.

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

Abstract

Nouveaux dérivés substitués de 4-aminopyridine de formule (I) dans laquelle R1, R2, Het, n, Y et p possèdent les significations figurant dans le descriptif. La présente invention concerne également plusieurs procédés de production de ces substances et leur utilisation dans la lutte contre les parasites, ainsi que de nouveaux intermédiaires et des procédés de production desdits intermédiaires.
PCT/EP2003/000051 2002-01-18 2003-01-07 Derives substitues de 4-aminopyridine WO2003059903A2 (fr)

Priority Applications (1)

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AU2003235696A AU2003235696A1 (en) 2002-01-18 2003-01-07 Substituted 4-aminopyridine derivatives used as pest control agents

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Application Number Priority Date Filing Date Title
DE2002101764 DE10201764A1 (de) 2002-01-18 2002-01-18 Substituierte 4-Aminopyridin-Derivate
DE10201764.6 2002-01-18

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WO2006071960A3 (fr) * 2004-12-28 2007-05-24 Kinex Pharmaceuticals Llc Compositions et procedes de traitement de troubles de la proliferation cellulaire
US7691882B2 (en) 2005-10-31 2010-04-06 Eisai R&D Management Co., Ltd. Heterocycles substituted pyridine derivatives and antifungal agent containing thereof
US7851470B2 (en) 2006-12-28 2010-12-14 Kinex Pharmaceuticals, Llc Composition and methods for modulating a kinase cascade
WO2011022473A1 (fr) * 2009-08-19 2011-02-24 Ambit Biosciences Corporation Composés biaryles et procédés d’utilisation de ceux-ci
US7935697B2 (en) 2006-12-28 2011-05-03 Kinex Pharmaceuticals, Llc Compositions for modulating a kinase cascade and methods of use thereof
US7939529B2 (en) 2007-05-17 2011-05-10 Kinex Pharmaceuticals, Llc Process for the preparation of compositions for modulating a kinase cascade and methods of use thereof
US7968574B2 (en) 2004-12-28 2011-06-28 Kinex Pharmaceuticals, Llc Biaryl compositions and methods for modulating a kinase cascade
US8124605B2 (en) 2007-07-06 2012-02-28 Kinex Pharmaceuticals, Llc Compositions and methods for modulating a kinase cascade
US8513287B2 (en) 2007-12-27 2013-08-20 Eisai R&D Management Co., Ltd. Heterocyclic ring and phosphonoxymethyl group substituted pyridine derivatives and antifungal agent containing same
US8748423B2 (en) 2010-04-16 2014-06-10 Kinex Pharmaceuticals, Llc Compositions and methods for the prevention and treatment of cancer
US8937071B2 (en) 2013-03-15 2015-01-20 Glaxosmithkline Intellectual Property Development Limited Compounds as rearranged during transfection (RET) inhibitors
US9382238B2 (en) 2013-03-15 2016-07-05 Glaxosmithkline Intellectual Property Development Limited Pyridine derivatives as rearranged during transfection (RET) kinase inhibitors
US9879021B2 (en) 2014-09-10 2018-01-30 Glaxosmithkline Intellectual Property Development Limited Compounds as rearranged during transfection (RET) inhibitors
US9918974B2 (en) 2014-09-10 2018-03-20 Glaxosmithkline Intellectual Property Development Limited Pyridone derivatives as rearranged during transfection (RET) kinase inhibitors
US9926273B2 (en) 2012-08-30 2018-03-27 Athenex, Inc. Composition and methods for modulating a kinase cascade
US9951089B2 (en) 2010-02-03 2018-04-24 Infinity Pharmaceuticals, Inc. Methods of treating a fatty acid amide hydrolase-mediated condition
US10196357B2 (en) 2007-04-13 2019-02-05 Athenex, Inc. Biaryl compositions and methods for modulating a kinase cascade
JP2019512505A (ja) * 2016-03-16 2019-05-16 プレキシコン インコーポレーテッドＰｌｅｘｘｉｋｏｎ Ｉｎｃ． キナーゼ調節およびその適応症のための化合物および方法
US10492494B2 (en) 2015-11-13 2019-12-03 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
US10499644B2 (en) 2015-11-19 2019-12-10 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
US10555526B2 (en) 2015-11-05 2020-02-11 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
US10674727B2 (en) 2015-11-19 2020-06-09 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
US10687532B2 (en) 2015-11-13 2020-06-23 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
US10785980B2 (en) 2016-06-09 2020-09-29 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
US10986839B2 (en) 2016-04-11 2021-04-27 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi

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EP2282742A1 (fr) 2008-04-09 2011-02-16 Infinity Pharmaceuticals, Inc. Inhibiteurs d'hydrolase d'amide d'acide gras

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US7968574B2 (en) 2004-12-28 2011-06-28 Kinex Pharmaceuticals, Llc Biaryl compositions and methods for modulating a kinase cascade
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US7691882B2 (en) 2005-10-31 2010-04-06 Eisai R&D Management Co., Ltd. Heterocycles substituted pyridine derivatives and antifungal agent containing thereof
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US10323001B2 (en) 2006-12-28 2019-06-18 Athenex, Inc. Compositions for modulating a kinase cascade and methods of use thereof
US8293739B2 (en) 2006-12-28 2012-10-23 Kinex Pharmaceuticals, Llc Process for the preparation of compositions for modulating a kinase cascade and methods of use thereof
US8309549B2 (en) 2006-12-28 2012-11-13 Kinex Pharmaceuticals, Llc Compositions for modulating a kinase cascade and methods of use thereof
US9556120B2 (en) 2006-12-28 2017-01-31 Athenex, Inc. Compositions for modulating a kinase cascade and methods of use thereof
US7935697B2 (en) 2006-12-28 2011-05-03 Kinex Pharmaceuticals, Llc Compositions for modulating a kinase cascade and methods of use thereof
US8901297B2 (en) 2006-12-28 2014-12-02 Kinex Pharmaceuticals, Llc Compositions for modulating a kinase cascade and methods of use thereof
US7851470B2 (en) 2006-12-28 2010-12-14 Kinex Pharmaceuticals, Llc Composition and methods for modulating a kinase cascade
US10196357B2 (en) 2007-04-13 2019-02-05 Athenex, Inc. Biaryl compositions and methods for modulating a kinase cascade
US7939529B2 (en) 2007-05-17 2011-05-10 Kinex Pharmaceuticals, Llc Process for the preparation of compositions for modulating a kinase cascade and methods of use thereof
US8124605B2 (en) 2007-07-06 2012-02-28 Kinex Pharmaceuticals, Llc Compositions and methods for modulating a kinase cascade
US8513287B2 (en) 2007-12-27 2013-08-20 Eisai R&D Management Co., Ltd. Heterocyclic ring and phosphonoxymethyl group substituted pyridine derivatives and antifungal agent containing same
WO2011022473A1 (fr) * 2009-08-19 2011-02-24 Ambit Biosciences Corporation Composés biaryles et procédés d’utilisation de ceux-ci
CN102470127A (zh) * 2009-08-19 2012-05-23 埃姆比特生物科学公司 联芳基化合物和其使用方法
US9951089B2 (en) 2010-02-03 2018-04-24 Infinity Pharmaceuticals, Inc. Methods of treating a fatty acid amide hydrolase-mediated condition
US8748423B2 (en) 2010-04-16 2014-06-10 Kinex Pharmaceuticals, Llc Compositions and methods for the prevention and treatment of cancer
US9926273B2 (en) 2012-08-30 2018-03-27 Athenex, Inc. Composition and methods for modulating a kinase cascade
US10106505B2 (en) 2012-08-30 2018-10-23 Athenex, Inc. Composition and methods for modulating a kinase cascade
US9035063B2 (en) 2013-03-15 2015-05-19 Glaxosmithkline Intellectual Property Development Limited Compounds as rearranged during transfection (RET) inhibitors
US9789100B2 (en) 2013-03-15 2017-10-17 Glaxosmithkline Intellectual Property Development Limited Compounds as rearranged during transfection (RET) inhibitors
US8937071B2 (en) 2013-03-15 2015-01-20 Glaxosmithkline Intellectual Property Development Limited Compounds as rearranged during transfection (RET) inhibitors
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US10709695B2 (en) 2014-09-10 2020-07-14 Glaxosmithkline Intellectual Property Development Limited Compounds as rearranged during transfection (RET) inhibitors
US10292975B2 (en) 2014-09-10 2019-05-21 Glaxosmithkline Intellectual Property Development Limited Compounds as rearranged during transfection (RET) inhibitors
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US10555526B2 (en) 2015-11-05 2020-02-11 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
US10687532B2 (en) 2015-11-13 2020-06-23 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
US10492494B2 (en) 2015-11-13 2019-12-03 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
US10499644B2 (en) 2015-11-19 2019-12-10 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
US10674727B2 (en) 2015-11-19 2020-06-09 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
JP2019512505A (ja) * 2016-03-16 2019-05-16 プレキシコン インコーポレーテッドＰｌｅｘｘｉｋｏｎ Ｉｎｃ． キナーゼ調節およびその適応症のための化合物および方法
US10986839B2 (en) 2016-04-11 2021-04-27 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
US10785980B2 (en) 2016-06-09 2020-09-29 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi

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AU2003235696A1 (en) 2003-07-30
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WO2003059903A3 (fr) 2003-12-11

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