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WO1995006033A1 - Derives d'acide 2-oximino-2-pyridylacetique utilises comme agents de lutte contre les parasites (fongicides) - Google Patents

Derives d'acide 2-oximino-2-pyridylacetique utilises comme agents de lutte contre les parasites (fongicides) Download PDF

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Publication number
WO1995006033A1
WO1995006033A1 PCT/EP1994/002689 EP9402689W WO9506033A1 WO 1995006033 A1 WO1995006033 A1 WO 1995006033A1 EP 9402689 W EP9402689 W EP 9402689W WO 9506033 A1 WO9506033 A1 WO 9506033A1
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Prior art keywords
carbon atoms
chain
straight
formula
branched
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PCT/EP1994/002689
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German (de)
English (en)
Inventor
Dietmar Kuhnt
Herbert Gayer
Peter Gerdes
Stefan Dutzmann
Heinz-Wilhelm Dehne
Gerd Hänssler
Original Assignee
Bayer Aktiengesellschaft
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Priority to JP7507317A priority Critical patent/JPH09501685A/ja
Priority to AU76530/94A priority patent/AU7653094A/en
Priority to EP94926831A priority patent/EP0715621A1/fr
Publication of WO1995006033A1 publication Critical patent/WO1995006033A1/fr

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Classifications

    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C07D213/643—2-Phenoxypyridines; Derivatives thereof
    • 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
    • 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
    • C07D213/61—Halogen atoms or nitro radicals

Definitions

  • the invention relates to new 2-oximino-2-pyridyl-acetic acid derivatives, several processes for their preparation and their use as pesticides, in particular as fungicides.
  • Ar represents optionally substituted aryl or heteroaryl
  • R represents alkyl or haloalkyl
  • R 2 and R 3 independently of one another each represent hydrogen, halogen, cyano, nitro, alkyl, alkoxy, alkylthio, alkenyl, alkenyloxy, alkynyl, alkynyloxy, haloalkyl, haloalkoxy, haloalkylthio, haloalkenyl, haloalkenyloxy, haloalkynyl, haloalkynyloxy, alkoxycarbonyl,
  • Hydroximinoalkyl alkoximinoalkyl or optionally substituted phenyl, phenoxy, benzyl, benzyloxy, phenylethyl or phenylethyloxy,
  • Z represents a radical of the formula -OR 5 or -NR 6 R 7 , where
  • R 4 represents alkyl, haloalkyl, cycloalkyl or cyano
  • R 5 represents alkyl or haloalkyl
  • R and R 7 each independently represent hydrogen, alkyl, haloalkyl, alkoxy or haloalkoxy and
  • n 0, 1 or 2
  • the compounds of the formula (I) can optionally be present as geometric and / or optical isomers or isomer mixtures of different compositions. Both the pure isomers and the isomer mixtures are claimed according to the invention.
  • Ar represents optionally substituted aryl or heteroaryl
  • R 1 represents alkyl or haloalkyl
  • R 2 and R 3 independently of one another each represent hydrogen, halogen, cyano, nitro, alkyl, alkoxy, alkylthio, alkenyl, alkenyloxy, alkynyl, alkynyloxy, haloalkyl, haloalkoxy, haloalkylthio, haloalkenyl, haloalkenyloxy, haloalkynyl, haloalkynyloxy, alkoxycarbonyl, Hydroximinoalkyl, alkoximinoalkyl or optionally substituted phenyl, phenoxy, benzyl, benzyloxy, phenylethyl or phenylethyloxy,
  • Z represents a radical of the formula -OR 5 or -NR 6 R 7 , where
  • 'R 4 represents alkyl, haloalkyl, cycloalkyl or cyano
  • R 5 represents alkyl or haloalkyl
  • R 6 and R 7 each independently represent hydrogen, alkyl, halogen alkyl, alkoxy or haloalkoxy and
  • n 0. 1 or 2 get when one
  • R 2 , R 3 , Ar, A and Z have the meaning given above,
  • R 2 , R 3 , Ar, A and Z have the meaning given above and
  • R 8 represents alkyl
  • R 1 , R 2 , R 3 and Z have the meaning given above and
  • R 4 has the meaning given above, if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary,
  • R 1 , R 2 , R 3 , R 5 , Ar and A have the meaning given above,
  • R 6 and R 7 have the meaning given above
  • R 2 , R 3 , Ar, A and Z have the meaning given above, with oximation agents and then with alkylating agents of the formula (VIII)
  • R 1 has the meaning given above and
  • X represents halogen or the grouping -O-SO 2 -OR 1 ,
  • the 2-oximino-2-pyridyl-acetic acid derivatives of the general formula (I) according to the invention show a considerably better activity against microorganisms which damage the plants in comparison to the 2-methoxy-acrylic acid esters known from the prior art, such as, for example, the compound 3- Methyl methoxy-2- (6-phenyl-2-pyridylthio) acrylic acid or the compound 3- methoxy-2- [N- (6-phenyl-2-pyridyl) -N-methylamino] acrylic acid methyl ester or the compound 3- Methyl methoxy-2- [5- (4-chlorophenyl) -3-pyridyloxy] acrylic acid. which are chemically and functionally obvious compounds.
  • the 2-oximino-2-pyridyl-acetic acid derivatives according to the invention are generally defined by the formula (I). Compounds of formula (I) are preferred. in which
  • Ar for optionally single or multiple, identical or different substituted aryl with 6 to 10 carbon atoms or for optionally single or multiple, identical or different substituted and / or benzo-fused heteroaryl with 2 to 9 carbon atoms and 1 to 5 identical or different heteroatoms stands, with the following being suitable as substituents: halogen, cyano, nitro, hydroxy, amino, formyl, carbamoyl, thiocarbamoyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio,
  • Alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms, each straight-chain or branched halogenoalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched haloalkenyl or haloalkenyloxy each with 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or
  • Alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts, in each case optionally one or more times, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 same or different
  • R 1 represents straight-chain or branched alkyl having 1 to 8 carbon atoms or straight-chain or branched haloalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms,
  • R 2 and R 3 independently of one another each represent hydrogen, halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy, alkylthio
  • 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms and / or straight-chain or branched alkoxy having 1 to 4 carbon atoms and / or straight-chain or branched haloalkoxy having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms are substituted phenyl, phenoxy, benzyl, benzyloxy, phenylethyl or phenylethyloxy
  • A represents oxygen, ethene-1,2-diyl, ethyne-1,2-diyl or one of the following
  • Z represents a radical of the formula -OR 5 or -NR 6 R 7 , where
  • R 4 represents straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched haloalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, cycloalkyl having 3 to 8 carbon atoms or cyano,
  • R 5 represents straight-chain or branched alkyl having 1 to 8 carbon atoms or straight-chain or branched haloalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms,
  • R 6 and R 7 each independently represent hydrogen, straight-chain or branched alkyl having 1 to 8 carbon atoms, straight-chain or branched haloalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, or straight-chain or branched alkoxy 1 to 8 carbon atoms stand and
  • n 0, 1 or 2
  • Ar for optionally single to five times, identical or differently substituted aryl having 6 or 10 carbon atoms or for optionally single to four times, identical or differently substituted and / or benzo-fused Heteroaryl with 2 to 9 carbon atoms and 1 to 3 identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur - is available, the following being suitable in each case: halogen, cyano, nitro, hydroxy, amino, formyl, carbamoyl, thiocarbamoyl , in each case straight-chain or branched alkyl, alkoxy, alkylthio,
  • Alkylsulfinyl or alkylsulfonyl each having 1 to 4 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each
  • R 1 represents straight-chain or branched alkyl having 1 to 6 carbon atoms or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms
  • R 2 and R 3 independently of one another each represent hydrogen, halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy, alkylthio, each with
  • each straight-chain or branched alkenyl or alkenyloxy each having 2 to 4 carbon atoms
  • each straight-chain or branched haloalkyl each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each straight-chain or branched haloalkenyl or
  • Haloalkenyloxy each having 2 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each straight-chain or branched alkoxycarbonyl, hydroximinoalkyl or alkoximinoalkyl each having 1 to 4 carbon atoms in the individual alkyl parts and, moreover, in each case optionally in the phenyl part, simply to five times, identical or different from halogen and / or straight-chain or branched alkyl having 1 to 3 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms and / or straight-chain the branched alkoxy having 1 to 3 carbon atoms and / or straight chain or branched
  • Z represents a radical of the formula -OR 5 or -NR 6 R 7 , where
  • R 4 for straight-chain or branched alkyl having 1 to 4 carbon atoms, straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, represents cycloalkyl having 3 to 7 carbon atoms or cyano
  • R 5 for straight-chain or branched alkyl having 1 to 6 carbon atoms or for straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different
  • R 6 and R 7 each independently represent hydrogen, straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, or straight-chain or branched alkoxy 1 to 6 carbon atoms are and
  • n 0, 1 or 2
  • Ar for phenyl or naphthyl which is optionally monosubstituted to trisubstituted identically or differently or for each optionally monosubstituted to trisubstituted and / or substituted in the same or different ways and / or benzo-annelated
  • Thiocarbamoyl Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, Methylthio, ethylthio, methylsulfinyl, methylsulfonyl, allyl, butenyl, allyloxy, butenyloxy, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulfinyl, Trifluoromethylsulfonyl, dimethylamino, diethylamino, acetyl, acetoxy, methylsulfonyloxy, ethylsulfonyloxy, methoxycarbonyl, ethoxycarbonyl, hydroximinomethyl, hydro
  • R 1 represents straight-chain or branched alkyl having 1 to 4 carbon atoms or haloalkyl having 1 to 2 carbon atoms and 1 to 5 identical or different halogen atoms,
  • R 2 and R 3 independently of one another each represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
  • Z represents a radical of the formula -OR 5 or -NR 6 R 7 , where
  • R 4 represents methyl, ethyl, trifluoromethyl, cyclopropyl or cyano
  • R represents straight-chain or branched alkyl having 1 to 4 carbon atoms or haloalkyl having 1 to 2 carbon atoms and 1 to 5 identical or different halogen atoms and
  • R 6 and R 7 each independently represent hydrogen, straight-chain or branched alkyl having 1 to 4 carbon atoms, halogeno alkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms or straight-chain or branched alkoxy have 1 to 4 carbon atoms and
  • n 0, 1 or 2
  • a very particularly preferred group of compounds of the formula (I) are the compounds of the formula (IA)
  • A, Ar, R 1 , R 2 , R 3 and Z are those specified above as being particularly preferred
  • Particularly preferred groups of compounds of the formula (I) are the compounds of the formulas (IA) to (ID):
  • A, Ar, R, R 2, D R3 and Z have the meanings given particularly preferably above.
  • Very particularly preferred groups of compounds of the formula (I) are compounds of the formulas (IA-1) to (IA-17):
  • Rl l 1, R 2, R 3, R 4, R 6 and Z have the meanings given above as being very particularly preferred.
  • Very particularly preferred groups of compounds of the formula (I) are also compounds of the formulas (IB-1) to (IB-17):
  • Ar, R, R, R, R, R, R and Z have the meanings given above as being particularly preferred.
  • Very particularly preferred groups of compounds of the formula (I) are furthermore compounds of the formulas (IC-1) to (IC 1-17):
  • Ar, R 1 , R 2 , R 3 , R 4 , R 6 and Z have the meanings given above as being particularly preferred.
  • Very particularly preferred groups of compounds of the formula (I) are also compounds of the formulas (ID-1) to (ID-17):
  • R 1 , R 2 , R 3 , R 4 , R 6 and Z have the meanings given above as being particularly preferred.
  • Examples of the possible combinations of the compounds of the formulas (IA1) to (ID-17) defined above are listed below, with Z for each of the compounds of the formulas (IA1) to (ID-17) for -OCH 3 and -NHCH 3 where R 4 and R 6 in the examples of formulas (IA, B, C, D-15, 16, 17) is methyl, and R 1 , R 2 , R 3 and Ar are each indicated as follows.
  • reaction sequence in process (b) according to the invention can be represented by the following formula:
  • reaction sequence in process (d) according to the invention can be represented by the following formula ⁇ make:
  • the a-oxopyridyl acetic acid derivatives required as starting compounds for carrying out process (a) according to the invention are generally defined by the formula (IIa) and the corresponding ketals by the formula (IIb).
  • R 2 , R 3 , Ar, A and Z preferably or in particular have those meanings which are preferred or particularly preferred in connection with the description of the compounds of the formula (I) according to the invention were preferably given for R 2 , R 3 , Ar, A and Z;
  • R 8 preferably represents alkyl having 1 to 4 carbon atoms, in particular methyl or ethyl.
  • R 2 , R 3 , R 8 and Z have the meaning given above and
  • R 4 has the meaning given above
  • reaction auxiliary e.g. Copper (I) chloride
  • diluent e.g. Dioxane
  • halogenated oxopyridyl acetic acid derivatives of the general formulas (IXa) and (IXb) are not yet known from the literature; as new substances, they are the subject of the present application.
  • R 2 and R 3 have the meaning given above and
  • hydrolyzed with aqueous acids for example with hydrochloric acid at temperatures between 10 ° C and 100 ° C, then by reaction with alcohols, for example with methanol, optionally in the presence of a reaction auxiliary, such as e.g. Sulfuric acid and optionally in the presence of a diluent, e.g.
  • orthoesters for example with trimethyl orthoformate or triethyl ester
  • amines for example with methylamine
  • halogenated pyridine-carboxylic acid cyanides of the formula (X) are not yet known from the literature; as new substances, they are the subject of the present application.
  • metal cyanides for example with copper (I) cyanide, optionally in the presence of a diluent, such as e.g. Acetonitrile, at temperatures between 10 ° C and 100 ° C.
  • a diluent such as e.g. Acetonitrile
  • halogenated pyridine-carboxylic acid chlorides of the formula (XI) are known and / or can be prepared by processes known per se (cf. DE-OS 2713316, J. Heterocycl. Chem. 25 (1988), 1367-1371).
  • Formula (III) provides a general definition of the hydroxylamines further required as starting materials in process (a) according to the invention.
  • R 1 preferably or in particular has the meaning which has already been stated as preferred or as particularly preferred for R 1 in connection with the description of the compounds of the formula (I) according to the invention.
  • Particularly suitable hydrogen halide adducts are the hydrogen chloride and hydrogen bromide adducts.
  • the starting materials of formula (III) are known organic synthetic chemicals.
  • Formula (IV) provides a general definition of the 2-oximino-2- (halogenopyridyl) acetic acid derivatives to be used as starting compounds for carrying out process (b) according to the invention.
  • R 1 , R 2 , R 3 and Z preferably or in particular have the meaning which, in connection with the description of the compounds of the formula (I) according to the invention, is preferred or particularly preferred for R 1 , R 2 , R 3 and Z was specified.
  • R 2 , R, R and Z have the meaning given above and
  • R 1 has the meaning given above
  • reaction auxiliary e.g. Acetic acid
  • diluent e.g. Methanol
  • Formula (V) generally defines the nucleophiles to be used further as starting compounds for carrying out process (b) according to the invention.
  • Ar in formula (V) preferably or in particular has the meaning which has already been stated as preferred or as particularly preferred for Ar in connection with the description of the compounds of the formula (I) according to the invention;
  • the starting materials of formula (V) are known organic synthetic chemicals.
  • Formula (Ia) provides a general definition of the 2-oximino-2-pyridyl-acetic acid derivatives to be used as starting compounds for carrying out process (c) according to the invention.
  • R 1 , R 2 , R 3 , R 5 , Ar and A preferably or in particular have the meaning which, in connection with the description of the compounds of the formula (I) according to the invention, is preferred or was given as being particularly preferred for R 1 , R 2 , R 3 , R 5 , Ar and A.
  • the starting materials of the formula (Ia) for process (c) are new compounds according to the invention; they can be prepared by processes (a) and (b) according to the invention.
  • Formula (VI) provides a general definition of the amines to be used as starting compounds for carrying out process (c) according to the invention.
  • R 6 and R 7 preferably or in particular have the meaning which has already been stated as preferred or as particularly preferred for R 6 and R 7 in connection with the description of the compounds of the formula (I) according to the invention has been.
  • the starting materials of formula (VI) are known organic synthetic chemicals.
  • Formula (VII) provides a general definition of the halogenated 2-pyridyl-acetic acid derivatives to be used as starting compounds for carrying out process (d) according to the invention.
  • R 2 , R 3 , Ar, A and Z preferably or in particular have the meaning which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or as particularly preferred for R 2 , R 3 , Ar, A and Z was specified.
  • the starting materials of the formula (VII) are known and / or can be prepared by processes known per se (cf. EP-A 243012, EP-A 312243).
  • Formula (VIII) provides a general definition of the alkylating agents which are further used as starting compounds for carrying out process (d) according to the invention.
  • R 1 preferably or in particular the meaning which has already been given in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for R 1 ;
  • X preferably represents chlorine, bromine, iodine or the grouping -O-SO 2 -OR 1 .
  • the alkylating agents of formula (VIII) are known organic synthesis chemicals.
  • Process (a) according to the invention for the preparation of the new 2-oximino-2-pyridylacetic acid derivatives of the formula (I) is preferably carried out using diluents.
  • Inert organic solvents are particularly suitable as diluents for carrying out process (a) according to the invention.
  • aliphatic, alicyclic or aromatic optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as N N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Alcohols, such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl
  • Process (a) according to the invention is preferably carried out in the presence of a suitable reaction auxiliary.
  • a suitable reaction auxiliary All customary inorganic or organic acids are suitable as such. These preferably include protonic acids, for example hydrochloric acid, sulfuric acid, methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid.
  • reaction temperatures can be varied within a substantial range when carrying out process (a) according to the invention. In general, temperatures between 0 ° C and + 150 ° C, preferably at temperatures between 20 ° C and + 120 ° C.
  • Process (a) according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
  • 1.0 to 3.0 mol, preferably 1.0 to 2.0 mol, of hydroxylamine are generally employed per mol of a-oxopyridyl acetic acid derivative of the formula (II) Formula (III) or a corresponding hydrogen halide and optionally 1.0 to 6.0 mol, preferably 1.0 to 3.0 mol, of reaction auxiliaries.
  • the reaction is carried out, worked up and isolated by known methods.
  • Inert organic solvents are particularly suitable as diluents for carrying out process (b) according to the invention.
  • These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as NJM-dimethylformamide, N, N-dimethylacetamide, N-
  • the process according to the invention can (b) also be carried out in a two-phase system, such as water / toluene or water / dichloromethane, if appropriate in the presence of a suitable phase transfer catalyst.
  • suitable phase transfer catalysts are: tetrabutylammonium iodide, tetrabutylammonium bromide, tetrabutylammonium chloride, tributyl-methylphosphonium bromide, trimethyl-C ⁇ / C ⁇ -alkylammonium chloride, trimethyl-C ⁇ / C j s-alkylammonium bromide, dibenzyl-methyl- 12 -dimethyl-ammonium-dimethyl- 14 -methyl-ammonium-ammonium alkylbenzylammonium chloride, dimethyl-C 12 / C 14 -alkyl-benzylammonium bromide, tetrabutylammonium hydroxide, tri
  • Process (b) according to the invention is preferably carried out in the presence of a suitable reaction auxiliary.
  • All customary inorganic or organic bases are suitable as such. These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium ⁇ hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate and tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N -Dimethylaminopyridine, diazabicyclooctane (
  • reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. In general, temperatures between 0 ° C and + 150 ° C, preferably at temperatures between 20 ° C and + 120 ° C.
  • Process (b) according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
  • organic solvents include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Alcohols, such as methanol, ethanol, n- or i-propanol; Ether like Diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanil
  • Process (c) according to the invention is optionally carried out in the presence of a suitable reaction auxiliary.
  • All customary inorganic or organic bases are suitable as such. These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium ⁇ hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N -Dimethylaminopyridine, diazabicyclooctan
  • reaction temperatures can be varied within a substantial range when carrying out process (c) according to the invention. In general, temperatures between -30 ° C and + 150 ° C, preferably at temperatures between -20 ° C and + 120 ° C.
  • Process (c) according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
  • Oximino-2-pyridyl-acetic acid derivative of the formula (Ia) in general 1.0 to 3.0 mol, preferably 1.0 to 1.5 mol of amine of the formula (VI) and optionally 0.1 to 3.0 mol, preferably 0.5 to 1.5 mol of base used as reaction auxiliary on.
  • oximizing agents are the reagents suitable for converting methylene compounds into hydroximino compounds.
  • suitable oximation agents are: nitrous acid, nitrosyl chloride, alkyl nitrites such as e.g. Methyl, ethyl, n or i propyl, n, i, s and t-butyl nitrite
  • Inert organic solvents are particularly suitable as diluents for carrying out process (d) according to the invention.
  • These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as N, N-dimethylformamide, NJNf-dimethylacetamide, N
  • Process (d) according to the invention is optionally carried out in the presence of a suitable reaction auxiliary.
  • All conventional inorganic or organic bases are suitable as such. These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as sodium hydride, sodium amide, sodium methylate, Sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate.
  • Ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate and tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO) , Diazabicyclonones (DBN) or diazabicycloun- decene (DBU).
  • reaction temperatures can be varied within a substantial range when carrying out process (d) according to the invention. In general, temperatures between -20 ° C and + 120 ° C, preferably at temperatures between 0 ° C and + 100 ° C.
  • the process according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
  • the active compounds according to the invention have a strong microbicidal action and can be used practically to combat unwanted microorganisms.
  • the active ingredients are suitable for use as crop protection agents, in particular as fungicides.
  • Fungicidal agents in crop protection are used to combat plasmidiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes. Deuteromycetes.
  • 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 Pseu ⁇ doperonospora cubense;
  • Plasmopara species such as, for example, Plasmopara viticola
  • Peronospora species such as, for example, Peronospora pisi or Peronospora 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 Pyrenophora graminea (conidial form: Drechslera, synonym: Helminthosporium);
  • Cochliobolus species such as, for example, Cochliobolus sativus (conidial form: Drechs ⁇ lera, synonym: Helminthosporium);
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Puccinia species such as, for example, Puccinia recondita
  • 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 according to the invention can be used with particularly good success for combating diseases in fruit and vegetable cultivation, such as, for example, against Venturia, Uncinula or Podosphaera species, or for controlling cereal diseases, for example against Erysiphe species.
  • the active compounds according to the invention have good in vitro activity.
  • the active compounds can be converted into customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV Cold and warm mist formulations.
  • These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, under pressure the liquefied gases and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • aromas such as xylene, toluene, 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 or dimethyl sulfoxide, and water
  • liquefied gaseous extenders or carriers mean those liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide
  • Solid carrier materials are suitable: for example natural flour, such as ka
  • Alkylaryl polyglycol ethers alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • the following may be used as dispersants: 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 phospholipids.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments can be used.
  • iron oxide eg iron oxide, titanium oxide, ferrocy blue and organic dyes such as alizarin.
  • Azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can be present in the formulations in a mixture with other known active compounds, such as fungicides, insecticides, acaricides and herbicides, and also in mixtures with fertilizers and growth regulators.
  • 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, spraying, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume method 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 active compound concentrations in the use forms can be varied within a substantial range: in general they are 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 are from 0.00001 to 0.1% by weight. preferably from 0.0001 to 0.02% by weight required at the site of action.
  • Solvent 10 parts by weight of N-methyl-pyrrolidone emulsifier: 0.6 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • the plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80% in order to promote the development of mildew pustules.
  • Evaluation is carried out 7 days after the inoculation.
  • Emulsifier 0.3 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 23 ° C. and a relative atmospheric humidity of approx. 70%.
  • Evaluation is carried out 10 days after the inoculation.
  • the compounds of Preparation Examples 1, 2, 3, 5, 11, 13 and 14 show an efficiency of at least 95% at an active ingredient concentration of 25 ppm.
  • Emulsifier 0.3 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 the greenhouse at 23.degree. C. to 24.degree. C. and a relative atmospheric humidity of approx. 75%.
  • Evaluation is carried out 14 days after the inoculation.
  • the compound according to Preparation Example 4 shows an efficiency of at least at an active ingredient concentration of 25 ppm
  • Emulsifier 0.3 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 20 ° C. and a relative atmospheric humidity of approx. 70%.
  • Evaluation is carried out 12 days after the inoculation.
  • the compounds according to Preparation Examples 2, 3, 4, 5, 6, 7, 8, 10, 11, 12, 13 and 14 show an efficiency of up to 100% at an active ingredient concentration of 10 ppm.
  • Emulsifier 0.3 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 disease infestation is evaluated 4 days after the inoculation.
  • the compounds according to Preparation Examples 8, 9 and 11 show efficiencies of 90 to 100% at an active ingredient concentration of 0.025%.
  • Emulsifier 0.3 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 23 to 24 ° C and at a relative humidity of approx. 75%.
  • Evaluation is carried out 10 days after the inoculation.
  • the compounds of preparation examples 8, 14, 17 and 18 have an efficacy of up to 100% at an active ingredient concentration of 10 ppm.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (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)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne de nouveaux dérivés d'acide 2-oximino-2-pyridylacétique de la formule (I), dans laquelle R?1, R2, R3¿, Z, Ar et A ont la notation mentionnée dans la description. L'invention concerne par ailleurs leurs procédés de préparation et leur utilisation comme agents de lutte contre les parasites.
PCT/EP1994/002689 1993-08-24 1994-08-11 Derives d'acide 2-oximino-2-pyridylacetique utilises comme agents de lutte contre les parasites (fongicides) WO1995006033A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP7507317A JPH09501685A (ja) 1993-08-24 1994-08-11 抗有害生物剤（殺菌・殺カビ剤）としての２−オキシイミノ−２−ピリジル−酢酸誘導体
AU76530/94A AU7653094A (en) 1993-08-24 1994-08-11 2-oximino-2-pyridyl acetic acid derivatives as anti-parasitic agents (fungicides)
EP94926831A EP0715621A1 (fr) 1993-08-24 1994-08-11 Derives d'acide 2-oximino-2-pyridylacetique utilises comme agents de lutte contre les parasites (fongicides)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4328385.3 1993-08-24
DE19934328385 DE4328385A1 (de) 1993-08-24 1993-08-24 2-Oximino-2-pyridyl-essigsäurederivate

Publications (1)

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WO1995006033A1 true WO1995006033A1 (fr) 1995-03-02

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PCT/EP1994/002689 WO1995006033A1 (fr) 1993-08-24 1994-08-11 Derives d'acide 2-oximino-2-pyridylacetique utilises comme agents de lutte contre les parasites (fongicides)

Country Status (6)

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EP (1) EP0715621A1 (fr)
JP (1) JPH09501685A (fr)
CN (1) CN1133036A (fr)
AU (1) AU7653094A (fr)
DE (1) DE4328385A1 (fr)
WO (1) WO1995006033A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998012179A1 (fr) * 1996-09-18 1998-03-26 Basf Aktiengesellschaft Derives de pyridine, leur procede de preparation et leur utilisation pour lutter contre les parasites animaux et les champignons nuisibles
WO1999040082A3 (fr) * 1998-02-05 1999-10-21 Basf Ag Derives de 2-(pyrazolyloxy)-pyridine-3-yle-acide acetique, agents les contenant et leur utilisation pour lutter contre des champignons nuisibles et des parasites animaux
EP0766673B1 (fr) * 1994-06-23 2002-01-30 Celltech Chiroscience Limited Derives d'oximes substitues efficaces en tant qu'inhibiteurs de phosphodiesterases de type iv

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0383117A2 (fr) * 1989-02-17 1990-08-22 Bayer Ag Esters de l'acide acrylique substitués par une pyridine
EP0472300A2 (fr) * 1990-08-22 1992-02-26 Zeneca Limited Fongicides
EP0477631A1 (fr) * 1990-09-22 1992-04-01 BASF Aktiengesellschaft Amides d'acides phénylacétiques ortho-substitués
WO1992013830A1 (fr) * 1991-01-30 1992-08-20 Zeneca Limited Fongicides
JPH05201980A (ja) * 1992-01-30 1993-08-10 Mitsubishi Kasei Corp メトキシイミノ酢酸誘導体およびこれを有効成分とする農園芸用殺菌剤

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0383117A2 (fr) * 1989-02-17 1990-08-22 Bayer Ag Esters de l'acide acrylique substitués par une pyridine
EP0472300A2 (fr) * 1990-08-22 1992-02-26 Zeneca Limited Fongicides
EP0477631A1 (fr) * 1990-09-22 1992-04-01 BASF Aktiengesellschaft Amides d'acides phénylacétiques ortho-substitués
WO1992013830A1 (fr) * 1991-01-30 1992-08-20 Zeneca Limited Fongicides
JPH05201980A (ja) * 1992-01-30 1993-08-10 Mitsubishi Kasei Corp メトキシイミノ酢酸誘導体およびこれを有効成分とする農園芸用殺菌剤

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 120, no. 11, 14 March 1994, Columbus, Ohio, US; abstract no. 134461f, M. ODA ET AL.: "Preparation of 2-(5-pyrazolyl or 2-pyridyl)-2-(methoxyimino)acetic acid derivatives as agricultural and horticultural fungicides." page 1041; *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0766673B1 (fr) * 1994-06-23 2002-01-30 Celltech Chiroscience Limited Derives d'oximes substitues efficaces en tant qu'inhibiteurs de phosphodiesterases de type iv
WO1998012179A1 (fr) * 1996-09-18 1998-03-26 Basf Aktiengesellschaft Derives de pyridine, leur procede de preparation et leur utilisation pour lutter contre les parasites animaux et les champignons nuisibles
US6228810B1 (en) 1996-09-18 2001-05-08 Basf Ag Pyridine derivatives, process for preparing the same and their use for controlling animal pests and harmful fungi
WO1999040082A3 (fr) * 1998-02-05 1999-10-21 Basf Ag Derives de 2-(pyrazolyloxy)-pyridine-3-yle-acide acetique, agents les contenant et leur utilisation pour lutter contre des champignons nuisibles et des parasites animaux
US6362192B1 (en) 1998-02-05 2002-03-26 Basf Aktiengesellschaft 2-(Pyrazolyloxy) -pyridin-3-ylacetic acid derivatives, agents containing the same and use thereof against noxious fungi and animal parasites

Also Published As

Publication number Publication date
EP0715621A1 (fr) 1996-06-12
DE4328385A1 (de) 1995-03-02
AU7653094A (en) 1995-03-21
CN1133036A (zh) 1996-10-09
JPH09501685A (ja) 1997-02-18

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