EP0796242A1 - Amides d'acide carboxylique substitues et leur utilisation sous forme de fongicides - Google Patents

Amides d'acide carboxylique substitues et leur utilisation sous forme de fongicides

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Publication number
EP0796242A1
EP0796242A1 EP95941029A EP95941029A EP0796242A1 EP 0796242 A1 EP0796242 A1 EP 0796242A1 EP 95941029 A EP95941029 A EP 95941029A EP 95941029 A EP95941029 A EP 95941029A EP 0796242 A1 EP0796242 A1 EP 0796242A1
Authority
EP
European Patent Office
Prior art keywords
cyano
methyl
ethyl
carbon atoms
fluorine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
EP95941029A
Other languages
German (de)
English (en)
Inventor
Thomas Seitz
Ulrich Heinemann
Klaus Stenzel
Stefan Dutzmann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0796242A1 publication Critical patent/EP0796242A1/fr
Ceased legal-status Critical Current

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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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40—Acylated substituent nitrogen atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • 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
    • A01N43/72—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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
    • C07C255/29—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton containing cyano groups and acylated amino groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
    • 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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond

Definitions

  • the invention relates to new substituted carboxamides, a process for their preparation and their use as fungicides.
  • a 1 represents hydrogen or alkyl.
  • A represents hydrogen or alkyl.
  • a J represents hydrogen, alkyl or cyano.
  • Ar 1 represents optionally substituted arylene or heteroarylene
  • Ar stands for optionally substituted aryl or heteroaryl
  • E stands for a 1-alkene-1,1-diyl grouping, in the 2-position a residue
  • R 1 contains, or represents a 2-aza-l-alkene-l, l-diyl grouping which contains a radical R 2 in the 2-position, or an optionally substituted one
  • Imino grouping ("Azamethylene", NR 3 ), or a 3-aza-l-propene-2,3-diyl grouping which has a radical R 4 in the 1 position and a radical R in the 3 position 5 contains, or stands for a 3-aza-l-propene-2,3-diyl group which contains a radical R 4 in the 1-position, or for a 3-thia-l-propene-2,3-diyl -Group, which contains a radical R 4 in the 1-position, or stands for an l-aza-l-propene-2,3-diyl group, which has a radical R 6 in the 1-position and one in the 3-position Contains radical R 3 , or represents an l-aza-l-propene-2,3-diyl grouping which contains a radical R 4 in the 1 position and a radical R 5 in the 3 position, or for a 1, 3-Diaza-l-propen-2,3-d ⁇ yl grouping, in the 1 position a radical
  • 3-position contains a radical R 5 , or stands for an l-aza-3-oxa-l-propene-2,3-diyl grouping which contains a radical R 6 in the 1-position, or for an l-aza -3-th ⁇ a-l-propen-2,3-diyl grouping which contains a radical R 6 in the 1 position, where
  • R 1 represents hydrogen, halogen, cyano or optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino,
  • R stands for hydrogen, amino, cyano or for optionally substituted alkyl, alkoxy, alkylamino or dialkylamino, and
  • R 3 represents hydrogen, cyano or optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl,
  • R 4 represents hydrogen, halogen, cyano or any optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, R, 5 D represents alkyl,
  • R 6 represents hydrogen, amino, cyano or optionally substituted alkyl, alkoxy, alkylamino or dialkylamino.
  • G for a single bond, for oxygen, sulfur or for each optionally by halogen, hydroxy, alkyl, haloalkyl or
  • n the numbers 0, 1 or 2
  • Q oxygen or sulfur
  • R 7 represents hydrogen, cyano or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and
  • R 8 represents hydrogen, hydroxy, cyano or in each case optionally substituted alkyl, alkoxy or cycloalkyl,
  • n 0, 1 or 2
  • Cycloalkyl aryl or heterocyclyl.
  • Ar 1 , E, G and Z have the meaning given above and
  • R represents hydroxy, halogen or alkoxy
  • the compounds according to the invention can optionally be in the form of mixtures of various possible isomeric forms, in particular stereoisomers, such as, for. B. E- and Z-, threo- and erythro-, and optical isomers, but optionally also of tautomers are present. Both the E and the Z isomers, as well as the threo- and erythro- as well as the optical isomers, any mixtures of these isomers and the possible tautomeric forms are claimed
  • the invention preferably relates to compounds of the formula (I) in which
  • a 1 represents hydrogen or alkyl having 1 to 6 carbon atoms
  • a 2 represents hydrogen or alkyl having 1 to 6 carbon atoms
  • a 3 represents hydrogen, alkyl having 1 to 6 carbon atoms or cyano
  • Ar 1 stands for optionally substituted phenylene or naphthylene or for heteroarylene with 5 or 6 ring members, at least one of which is oxygen, sulfur or nitrogen and optionally one or two more are nitrogen, the possible substituents preferably being derived from the the following list is selected:
  • 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; in each case straight-chain or branched haloalkyl, 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 having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy
  • Heterocyclyl or heterocyclyl-methyl each with 3 to 7 ring members, of which 1 to 3 are identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur -; and in each case optionally in the phenyl moiety one or more times, identically or differently
  • R 1 represents hydrogen, halogen, cyano or alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, each of which has from 1 to 6 carbon atoms in the alkyl radicals, optionally substituted by halogen, cyano or C 1 -C 4 alkoxy,
  • R 2 for hydrogen, amino, cyano or for each optionally by
  • R 3 for hydrogen, cyano or for alkyl, alkenyl or alkynyl each optionally substituted by halogen, cyano or C j - -alkoxy, each having up to 6 carbon atoms or for each optionally by
  • R 4 represents hydrogen, halogen, cyano or alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, each of which has 1 to 6 carbon atoms in the alkyl radicals, optionally substituted by halogen, cyano or C, -C 4 -alkoxy,
  • R 5 represents alkyl having 1 to 6 carbon atoms
  • R 6 for hydrogen, amino, cyano or for alkyl, alkoxy, alkylamino or dialkylamino, each optionally substituted by halogen, cyano or C 1 -C 4 -alkoxy, each having 1 to 6 carbon atoms in the
  • G for a single bond, for oxygen, sulfur or for alkane diyl, alkenediyl, alkynediyl each optionally substituted by halogen, hydroxy, C, -C 4 alkyl, C ] -C haloalkyl or C 3 -C 6 cycloalkyl, each with up to 4 carbon atoms or one of the following
  • n the numbers 0, 1 or 2
  • Q oxygen or sulfur
  • R 7 represents hydrogen, cyano, alkyl, alkoxy, alkylthio, alkylamino or dialkylamino optionally substituted by halogen, cyano or C, -C 4 -alkoxy, each having 1 to 6 carbon atoms in the alkyl groups or each optionally substituted by halogen, cyano , Carboxy, C, -C 4 alkyl or C, -C 4 alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms, and R ° for hydrogen, hydroxy, cyano or for optionally by
  • n 0, 1 or 2 and
  • Z for optionally single or multiple, identical or different, by halogen, cyano, hydroxy, amino, C, -C 4 -alkoxy, C, -C 4 -alkylthio, C, -C 4 -alkylsulfonyl or C, -C 4 -alkylsulfonyl (which can in each case optionally be substituted by halogen) substituted alkyl with 1 to 8 carbon atoms; for alkenyl or alkynyl, each optionally substituted by halogen, each having up to 8 carbon atoms; for each optionally one or more times, identically or differently, by halogen, cyano, carboxy, phenyl (which may be by halogen, cyano, C ] -C 4 -alkyl, C ] -C 4 -haloalkyl, C, -C 4 -alkoxy or C 1 -C 4 -haloalkoxy is substituted), C, - C
  • Heterocyclyl or heterocyclyl-methyl each with 3 to 7 ring members, of which 1 to 3 are identical or different heteroatoms - in particular nitrogen, oxygen and / or
  • the saturated or unsaturated hydrocarbon chains such as alkyl, alkanediyl, alkenyl or alkynyl, are in each case straight-chain or branched, also in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • the invention relates in particular to compounds of the formula (I) in which
  • a 1 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
  • a 2 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
  • a 3 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or cyano
  • R 1 represents hydrogen, fluorine, chlorine, bromine, cyano or methyl, ethyl, propyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino, each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy,
  • R 2 represents hydrogen, amino, cyano or methyl, ethyl, methoxy, ethoxy, methylamino, ethylamino or dimethylamino, each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy,
  • R 3 represents hydrogen, cyano or, in each case optionally by fluorine,
  • R 4 represents hydrogen, fluorine, chlorine, bromine, cyano or methyl, ethyl, propyl, methoxy, ethoxy, methylthio, each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy,
  • R 5 represents methyl, ethyl n- or i-propyl, n-, i- or s-butyl,
  • R 6 represents hydrogen, amino, cyano or methyl, ethyl, methoxy, ethoxy, methylamino, ethylamino or dimethylamino which is optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, and
  • G for a single bond, for oxygen, sulfur or for each optionally substituted by fluorine, chlorine, bromine, hydroxy, methyl, ethyl, n- or i-propyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, methylene, dimethylene (Ethane-1,2-diyl), ethene-1,2-diyl, ethyne-1,2-diyl or one of the groups below
  • n the numbers 0, 1 or 2
  • Q oxygen or sulfur
  • R 7 for hydrogen, cyano, for methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, propoxy, butoxy, methylthio optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy , Ethylthio, propylthio, butylthio, methylamino, ethylamino, propylamino, dimethylamino or diethylamino or for each optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and
  • R 8 represents hydrogen, hydroxyl, cyano or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl substituted by fluorine, chlorine, cyano, methoxy or ethoxy or for optionally by fluorine, chlorine, cyano,
  • n 0, 1 or 2 and
  • Cyano hydroxy, amino, methoxy, ethoxy, methylthio, ethylthio, Methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl (which are each optionally substituted by fluorine and / or chlorine) substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; for allyl, crotonyl, 1-methyl-allyl, propargyl or 1-methyl-propargyl which are optionally monosubstituted to trisubstituted by fluorine, chlorine or bromine; for each one optionally up to six times by fluorine, chlorine,
  • Difluoromethoxy or trifluoromethoxy is substituted), methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; for in each case monosubstituted to trisubstituted phenyl, naphthyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1, 2,4-thiadiazolyl, 1 , 3,4-thiadiazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl,
  • a particularly preferred group of compounds according to the invention are those compounds of the formula (I) in which
  • a 1 represents hydrogen or methyl
  • a 2 represents hydrogen, methyl or ethyl
  • a J represents hydrogen, methyl, ethyl or cyano
  • Ar 1 represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,
  • R and R each represent methoxy
  • n represents the numbers 0, 1 or 2, - 18 -
  • Q oxygen or sulfur
  • R 7 represents hydrogen, cyano, methyl, ethyl or cyclopropyl
  • R 8 represents hydrogen, methyl, ethyl or cyclopropyl
  • n 0, 1 or 2 and,
  • a 1 represents hydrogen or methyl
  • a 2 represents hydrogen, methyl or ethyl
  • a 3 represents hydrogen, methyl, ethyl or cyano
  • Ar 1 represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,
  • n 0, 1 or 2 and,
  • Z 1 represents phenyl which is optionally monosubstituted to trisubstituted identically or differently, the possible substituents preferably being selected from the following list: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n -, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfony l, trifluoromethyl l , Difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoro
  • a 1 represents hydrogen or methyl
  • a 2 represents hydrogen, methyl or ethyl
  • a 3 represents hydrogen, methyl, ethyl or cyano
  • Ar 1 represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,
  • n 0, 1 or 2 and,
  • 2r stands for phenyl, pyridyl or pyrimidyl which is optionally monosubstituted to trisubstituted identically or differently, the possible ones Substituents are preferably selected from the list below
  • a 1 represents hydrogen or methyl
  • a 2 represents hydrogen, methyl or ethyl
  • a J represents hydrogen, methyl, ethyl or cyano
  • R and R ⁇ each represent methoxy
  • n 0, 1 or 2 and,
  • Substituents are preferably selected from the following list Fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i- propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, Difluorchlormethyl ⁇ thio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, and each optionally substituted in the phenyl,
  • Formula (II) provides a general definition of the carboxylic acid derivatives required as starting materials for carrying out the process according to the invention.
  • Ar 1 , E, G and Z preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or particularly preferred for Ar 1 , E, G and Z have been specified,
  • R preferably represents alkoxy having 1 to 4 carbon atoms, in particular methoxy or ethoxy, hydroxyl or chlorine.
  • the starting materials of the formula (II) are known and / or can be prepared by processes known per se (cf. EP-A 178826, EP-A 242081, EP-A 382375, EP-A 49371 1, EP-A 432503 , DE-A 3938054) - 25 -
  • Formula (III) provides a general definition of the amines to be used further as starting materials.
  • a 1 , A 2 , A 3 , Ar and m preferably or in particular have the meaning which have been preferred or particularly preferred in connection with the description of the compounds of the formula (I) according to the invention for A 1 , A 2 , A 3 , Ar and m was specified.
  • the starting materials of the formula (III) are known organic synthesis chemicals and / or can be prepared by processes known per se.
  • the process according to the invention is optionally carried out in the presence of a suitable acid acceptor.
  • a suitable acid acceptor All conventional inorganic or organic bases are suitable as such. These include, 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, N, N- Dimethyl-benzylamine, pyridine, N-methylpiperidine, N, N-di
  • the process according to the invention is optionally carried out in the presence of a suitable condensing agent.
  • a suitable condensing agent all condensation agents which can usually be used for such amidation reactions are suitable.
  • acid halide formers such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride;
  • Anhydride formers such as ethyl chloroformate, methyl chloroformate or methanesulfonyl chloride;
  • Carbodiimides such as N, N'-dicyclohexylcarbodiimide (DCC) or other customary condensing agents, such as phosphorus pentoxide, polyphosphoric acid, N, N'-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-l, 2-dihydroquinoline (EEDQ ) or triphenylphosphin
  • the process according to the invention is optionally carried out in the presence of a diluent.
  • Water and organic solvents are suitable as diluents for carrying out the process according to the invention Consideration. 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
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between -20 ° C and + 200 ° C, preferably at temperatures between 0 ° C and 150 ° C.
  • 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 plasmodiophoromycetes, 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 Pseudoperonospora 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: Drechslera, 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 Pseudocercosporella herpotrichoides.
  • the active compounds according to the invention can be used with particularly good results in combating cereal diseases, for example against Erysiphe species, - 28 -
  • the active compounds according to the invention have a particularly good in vitro effect.
  • 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.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate 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.
  • water is used as an extender, e.g. also organic solvents as
  • Auxiliary solvents can be used.
  • aromatics 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, e.g. 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 liquids which are gaseous at normal temperature and under normal pressure, e.g.
  • Aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide
  • Solid carrier materials are suitable: for example natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates;
  • Solid carriers for granules are possible: for example broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks;
  • Possible emulsifying 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, alky
  • Adhesives such as carboxymethyl cellulose, natural and synthetic, powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
  • 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 are used.
  • the formulations generally contain between 0, 1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the activity spectrum or to prevent the development of resistance. In many cases, synergistic effects occur.
  • Difenoconazole Dimethirimol, Dimethomorph, Diniconazol, Dinocap, Diphenylamin, Dipyrithion, Ditalimfos, Dithianon, Dodin, Drazoxolon, Edifenphos, Epoxyconazole, Ethirimol, Etridiazol,
  • Fenarimol Fenbuconazole, Fenfuram, Fenitropan, Fenpicionil, Fenpropidin, Fenpropi-morph, Fentinacetate, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam,
  • Fludioxonil fluoromide, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl aluminum, fthalide, fuberidazole, furalaxyl, furmecyclox, guazatine, hexachlorobenzene, hexaconazole, hymexazole,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetraconazole, thiabendazole, thicyofen, thiophanate-methyl, thiram, tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, trichlamide, tricyclazole, tridemo ⁇ ol, triflumine, triflumine
  • Bactericides bronopol, dichlorophene, nitrapyrin, nickel dimethyl dithiocarbamate,
  • Methamidophos methidathione, methiocarb, methomyl, metolcarb, milbemectin,
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet,
  • 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.
  • the active compound concentrations in the use forms can be varied within a substantial range: they are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001% by weight.
  • amounts of active ingredient of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.
  • active ingredient concentrations are from 0.00001 to
  • 0.1% by weight preferably from 0.0001 to 0.02% by weight, is required at the site of action.
  • Emulsifier 0.6 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.
  • the plants are placed in a greenhouse at a temperature of approx. 20 ° C and at a relative humidity of approx. 80% in order to
  • Evaluation is carried out 7 days after the inoculation.
  • Example B the compound according to Preparation Example (6) shows an efficiency of 100% with an exemplary amount of active ingredient applied of 250 g / ha.
  • 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 0.6 parts by weight of alkylaryl polyglycol ether
  • the plants are placed in a greenhouse at a temperature of approx. 20 ° C and at a relative humidity of approx. 80% in order to promote the development of mildew pustules
  • Example D the compound according to preparation example (6) shows an efficiency of 100% with an exemplary active compound application rate of 250 g / ha.
  • Emulsifier 0.6 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.
  • 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 parts by weight of alkylaryl polyglycol ether
  • the plants are placed in a greenhouse at 23 ° C and at a relative humidity of approx. 70%.
  • Evaluation is carried out 10 days after the inoculation.

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

Abstract

L'invention concerne des amides d'acide carboxylique de formule (I) et leur utilisation sous forme de pesticides. Dans la formule (I), A1 représente hydrogène ou alkyle; A2 représente hydrogène ou alkyle; A3 représente hydrogène, alkyle, ou cyano; Ar1 représente arylène ou hétéroarylène, chacun étant éventuellement substitué; Ar2 représente aryle ou hétéroaryle, chacun étant éventuellement substitué; E représente l'un des groupes (a); G représente une liaison simple, oxygène, soufre ou l'un des composants suivants: alcanediyle, alcènediyle, alcynediyle, chacun étant éventuellement substitué par halogène, hydroxy, alkyle, halogénure d'alkyle ou cycloalkyle, ou un des groupes suivants -Q-CQ-, -CQ-Q-, -CH¿2?-Q-; -Q-CH2-, -CQ-Q-CH2-, -CH2-Q-CQ-, -Q-CQ-CH2-, -Q-CQ-Q-CH2-, -N=N-, -S(O)n-, -CH2-S(O)n-, -CQ-, -S(O)n-CH2, -C(R?7¿)=N-O-, -C(R7)=N-O-CH¿2?-, -N(R?8¿)-, -CQ-N(R8)-, -N(R8)-CQ-, -Q-CQ-N(R8)-, -N=C(R7)-Q-CH2-, -CH¿2?-O-N=C(R?7¿)-, -N(R8)-CQ-Q-, -CQ-N(R8)-CQ-Q-, -N(R8)-CQ-Q-CH¿2?-, -Q-C(R?7¿)=N-O-CH¿2?- ou -N(R?8)-C(R7¿)=N-O-CH¿2?- où n vaut 0, 1 ou 2; Q représente oxygène ou soufre; R?7¿ représente hydrogène, cyano ou l'un des composants suivants éventuellement substitués: alkyle, alcoxy, alkylthio, alkylamino, dialkylamino ou cycloalkyle; et R8 représente hydrogène, hydroxy, cyano ou l'un des composants suivants éventuellement substitués: alkyle, alcoxy ou cycloalkyle; m est égal à 0, 1, ou 2; et z représente alkyle, alcényle, alcynyle, cycloalkyle, aryle ou hétérocyclyle, chacun étant éventuellement substitué.
EP95941029A 1994-12-08 1995-11-27 Amides d'acide carboxylique substitues et leur utilisation sous forme de fongicides Ceased EP0796242A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4443641 1994-12-08
DE19944443641 DE4443641A1 (de) 1994-12-08 1994-12-08 Substituierte Carbonsäureamide
PCT/EP1995/004668 WO1996017825A1 (fr) 1994-12-08 1995-11-27 Amides d'acide carboxylique substitues et leur utilisation sous forme de fongicides

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EP0796242A1 true EP0796242A1 (fr) 1997-09-24

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JP (1) JPH11500103A (fr)
AU (1) AU4257096A (fr)
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WO (1) WO1996017825A1 (fr)

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DE19646407A1 (de) * 1996-11-11 1998-05-14 Bayer Ag Halogenpyrimidine
DE19648009A1 (de) 1996-11-20 1998-05-28 Bayer Ag Glyoxylsäureamide
CN100475034C (zh) 2000-06-14 2009-04-08 巴斯福股份公司 苯乙基丙烯酰胺的用途,新的苯乙基丙烯酰胺,其制备及包含它们的组合物
EP1295868A4 (fr) 2000-06-29 2004-03-17 Sumitomo Chemical Co Composes d'amides et utilisation associee
AU2003214116A1 (en) 2002-03-14 2003-09-22 Basf Aktiengesellschaft Z-substituted acrylamides, methods for production thereof and agents comprising the same
AR047894A1 (es) 2004-02-25 2006-03-01 Wyeth Corp Derivados de tiofeno como inhibidores de la proteina tirosina fosfatasa 1b (ptpasa 1b); metodos para su preparacion, composiciones farmaceuticas que los contienen y su uso en el tratamiento de enfermedades mediadas por ptpasa 1b
US7550499B2 (en) 2004-05-12 2009-06-23 Bristol-Myers Squibb Company Urea antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions
KR20070032648A (ko) 2004-05-12 2007-03-22 브리스톨-마이어스 스큅 컴퍼니 혈전 상태의 치료에 유용한 ｐ２ｙ１ 수용체의 우레아길항제
MX2007008434A (es) 2005-01-19 2007-07-25 Squibb Bristol Myers Co Derivados de 2-fenoxi-n-(1,3,4-tiadizol-2il)piridin-3-amina y compuestos relacionados como inhibidores del receptor p2y1 para el tratamiento de trastornos tromboembolicos.
EP1899299B1 (fr) 2005-06-27 2010-10-20 Bristol-Myers Squibb Company Antagonistes cycliques a liaison c du recepteur p2y1, utiles pour traiter des etats pathologiques thrombotiques
WO2007002634A1 (fr) 2005-06-27 2007-01-04 Bristol-Myers Squibb Company Antagonistes carbocycliques et heherocycliques du recepteur p2y1, utiles pour traiter des etats pathologiques thrombotiques
EP1896466B1 (fr) 2005-06-27 2011-04-13 Bristol-Myers Squibb Company Antagonistes heterocycliques a liaison n du recepteur p2y1, utiles pour traiter des etats pathologiques thrombotiques
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DE4443641A1 (de) 1996-06-13
AU4257096A (en) 1996-06-26
WO1996017825A1 (fr) 1996-06-13
JPH11500103A (ja) 1999-01-06

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