WO2001012587A1 - Amides d'acide aminosalicylique et leur utilisation pour lutter contre les organismes nuisibles pour les plantes - Google Patents

Amides d'acide aminosalicylique et leur utilisation pour lutter contre les organismes nuisibles pour les plantes Download PDF

Info

Publication number
WO2001012587A1
WO2001012587A1 PCT/EP2000/007523 EP0007523W WO0112587A1 WO 2001012587 A1 WO2001012587 A1 WO 2001012587A1 EP 0007523 W EP0007523 W EP 0007523W WO 0112587 A1 WO0112587 A1 WO 0112587A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
optionally substituted
represents hydrogen
methyl
ethyl
Prior art date
Application number
PCT/EP2000/007523
Other languages
German (de)
English (en)
Inventor
Christiane Boie
Dirk Backhaus
Herbert Gayer
Stephan Jordan
Martin Vaupel
Ulrike Wachendorff-Neumann
Karl-Heinz Kuck
Original Assignee
Bayer Aktiengesellschaft
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 Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to EP00958374A priority Critical patent/EP1210321A1/fr
Priority to AU69920/00A priority patent/AU6992000A/en
Priority to JP2001516888A priority patent/JP2003507360A/ja
Publication of WO2001012587A1 publication Critical patent/WO2001012587A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • C07C323/59—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton with acylated amino groups 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
    • 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
    • A01N37/46—N-acyl derivatives
    • 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
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/52—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • the invention relates to known and new acylaminosalicyl acid amides, several processes for their preparation and their use for controlling plant-damaging organisms, and new intermediates and processes for their production.
  • R.1 represents hydrogen or alkyl
  • R.2 represents hydrogen or alkyl, or for a grouping stands in what
  • A represents oxygen, sulfur or - (N-R ⁇ ) -, in which
  • R9 represents hydrogen or alkyl or, together with R "and the nitrogen atom to which they are attached, forms an optionally substituted heterocyclic ring,
  • R ⁇ represents hydrogen, optionally substituted alkyl or optionally substituted aryl or
  • R5 represents hydrogen or alkyl
  • R6 represents hydrogen or in each case optionally substituted alkyl, cycloalkyl, aryl or heterocyclyl,
  • R ⁇ represents hydrogen or alkyl
  • R8 represents hydrogen or alkyl and Z represents hydrogen or in each case optionally substituted alkyl, alkylcarbonyl, cycloalkyl, cycloalkylcarbonyl, aryl, arylcarbonyl, heterocyclyl or heterocyclylcarbonyl,
  • This organism is understood to mean in particular microorganisms.
  • hydrocarbon chains such as alkyl, alkylene, alkenyl or alkynyl
  • heteroatoms such as in alkoxy, alkylthio or
  • Alkylamino each straight-chain or branched. Unless otherwise stated, preference is given to hydrocarbon chains having 1 to 6 carbon atoms.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • Aryl stands for aromatic, mono or polycyclic hydrocarbon rings, e.g. Phenyl, naphthyl, anthranyl, phenanthryl, preferably for phenyl or naphthyl, in particular for phenyl.
  • Heterocyclyl stands for saturated or unsaturated, as well as aromatic, ring-shaped compounds with up to eight ring members, in which at least one ring member is a hetero atom, ie an atom other than carbon. If the ring contains several heteroatoms, these can be the same or different. Heteroatoms are preferably oxygen, nitrogen or sulfur. If the ring contains several oxygen atoms, these are not directly adjacent. If appropriate, the ring-shaped compounds together with other carbocyclic or heterocyclic, fused or bridged rings together form a polycyclic ring system. Mono- or bicyclic ring systems are preferred, in particular mono- or bicyclic aromatic ring systems. Cycloalkyl stands for saturated, carbocyclic, ring-shaped compounds which optionally form a polycyclic ring system with other carbocyclic, fused or bridged rings.
  • Cycloalkenyl stands for carbocyclic, ring-shaped compounds which contain at least one double bond and optionally form a polycyclic ring system with further carbocyclic, fused or bridged rings.
  • Haloalkoxy stands for partially or completely halogenated alkyl.
  • the halogen atoms can be the same or different.
  • Preferred halogen atoms are fluorine or chlorine, especially fluorine. If the haloalkoxy carries further substituents, the maximum possible number of halogen atoms is reduced to the different free valences. Unless otherwise stated, preference is given to hydrocarbon chains having 1 to 6 carbon atoms.
  • Haloalkyl stands for partially or completely halogenated alkyl.
  • the halogen atoms can be the same or different.
  • Preferred halogen atoms are fluorine, or chlorine, especially fluorine. If the haloalkyl carries other substituents, the maximum possible number of halogen atoms is reduced to the different free valences. Unless otherwise stated, preference is given to hydrocarbon chains having 1 to 6 carbon atoms.
  • the compounds of formula (I) are optionally 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 before. Both the
  • Rl represents hydrogen or methyl
  • R ⁇ represents hydrogen or C 1 -C 4 alkyl
  • A represents oxygen, sulfur or - (N-R ⁇ ) -, in which
  • R represents hydrogen or alkyl having 1 to 4 carbon atoms or, together with R" and the nitrogen atom to which they are attached, forms a heterocyclic ring with 3 to 7 ring members which is optionally substituted by C1-C4-alkyl,
  • R ⁇ represents hydrogen or optionally substituted by hydroxyl, formyloxy, arylcarbonyloxy or alkoxy optionally substituted in the aryl part,
  • R2 and R ⁇ together with the atoms to which they are attached form a heterocyclic ring with 3 to 6 ring members
  • R5 represents hydrogen or -CC-alkyl or R ⁇ and R5 together with the carbon atom to which they are attached form a carbocyclic ring with 3 to 6 ring members,
  • R6 for hydrogen or Ci-C 12-alkyl, optionally substituted by C1-C4-alkyl substituted Cß-C cycloalkyl, each optionally in the aryl or
  • Heterocyclyl part substituted aryl, arylalkyl with 1 to 6 carbon atoms in the alkyl part, heterocyclyl or heterocyclylalkyl with 1 to 6 carbon atoms in the alkyl part,
  • R 7 represents hydrogen or C 1 -C 4 alkyl
  • R8 represents hydrogen or C1-C4-alkyl
  • each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
  • Rl represents hydrogen or methyl
  • R-2 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl and
  • A represents oxygen, sulfur or - (N-R ⁇ ) -, in which
  • R9 stands for hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or together with R ⁇ and the nitrogen atom to which they are attached, optionally substituted by methyl or ethyl Pyrrolidinyl, morpholinyl, piperidinyl, piperazinyl or hexahydroazepinyl,
  • R4 is hydrogen or phenylcarbonyloxy, methoxy, ethoxy, methylthio, ethylthio, methoxycarbonyl, ethoxycarbonyl, methylcarbonyloxy, ethylcarbonyloxy, propylcarbonyloxy, pentylcarbonyloxy or hexylcarbonyloxy substituted methyl, ethyl, n- or i-propyl, which is optionally substituted in the phenyl part by phenylcarbonyloxy, methoxy, ethoxy , n-, i-, s- or t-butyl or in each case optionally in
  • Phenyl part or heterocyclyl part substituted phenyl, benzyl, 1-phenethyl, 2-phenethyl or indolylmethyl or R ⁇ and R4 together with the atoms to which they are attached represent a pyrrolidine or piperidine ring,
  • R5 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or
  • R ⁇ and R * together with the carbon atom to which they are attached represent a cyclopropane ring, cyclopentane or cyclohexane ring,
  • R 7 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
  • R8 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl and
  • Z represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
  • Halogen amino, hydroxy, oxo, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propyl-thio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino.
  • the present application further relates to new substituted acylaminosalicyl acid amides of the general formula (I-a),
  • R 1 1 represents hydrogen or alkyl
  • R 12 represents hydrogen or alkyl, or
  • A represents oxygen, sulfur or - (N-R19) -, in which
  • Rl9 represents hydrogen or alkyl or, together with R 1 "and the nitrogen atom to which they are attached, forms an optionally substituted heterocyclic ring,
  • R 1 ⁇ represents hydrogen, optionally substituted alkyl or optionally substituted aryl or
  • Rl 5 represents hydrogen or alkyl
  • Rl4 and Rl5 together with the carbon atom to which they are attached form a carbocyclic ring
  • R'6 represents hydrogen or in each case optionally substituted alkyl, cycloalkyl, aryl or heterocyclyl,
  • R 7 f is hydrogen or alkyl and R - • 8 represents hydrogen or alkyl
  • Z 1 represents hydrogen or in each case optionally substituted alkyl, alkylcarbonyl, cycloalkyl, cycloalkylcarbonyl, aryl, arylcarbonyl, heterocyclyl or heterocyclylcarbonyl,
  • R ⁇ O represents hydrogen, optionally substituted alkyl or optionally substituted aryl or hetaryl or
  • R2 represents hydrogen or alkyl
  • R20 and R21 together with the carbon atom to which they are attached form a carbocyclic ring.
  • R '2 and Rl3 have the meanings given above, with an acylating agent of the general formula (III),
  • ⁇ represents halogen, hydroxy, alkoxy or alkylcarbonyloxy
  • R 2 and R 3 have the meanings given above,
  • the new acylaminosalicyl acid amides of the general formula (Ia) show a strong action against organisms which damage plants and materials, in particular a very strong fungicidal action.
  • the active compounds according to the invention may also have an action against plant and animal pests.
  • Harmful organisms are understood in particular to be microorganisms.
  • the compounds according to the invention are optionally in the form of mixtures of various possible isomeric forms, in particular stereoisomers, such as e.g. E and Z, threo and erythro and optical isomers before. Both the E and the Z isomers, as well as the threo and erythro and optical isomers and any mixtures of these isomers are claimed.
  • R represents hydrogen or methyl
  • R 2 represents hydrogen or C 1 -C 4 alkyl
  • A represents oxygen, sulfur or - (NR ") _, wherein R 9 represents hydrogen or alkyl having 1 to 4 carbon atoms or, together with R "and the nitrogen atom to which they are attached, forms a heterocyclic ring with 3 to 7 ring members which is optionally substituted by C1-C4-alkyl,
  • R 4 represents hydrogen or optionally substituted by hydroxyl, formyloxy, optionally substituted arylcarbonyloxy or alkoxy, alkylthio, alkoxycarbonyl or alkylcarbonyloxy each having 1 to 6 carbon atoms in the alkyl part substituted alkyl or optionally substituted aryl in the aryl part or heterocyclyl part,
  • Heterocyclyl, arylalkyl or heterocyclylalkyl each having 1 to 6 carbon atoms in the alkyl part or
  • R 2 and R 4 together with the atoms to which they are attached form a heterocyclic ring with 3 to 6 ring members
  • Rl ⁇ represents hydrogen or C1 -C4 alkyl
  • Rl6 for hydrogen or Cf-C ⁇ alkyl, optionally substituted by C1-C4-alkyl C3-C7-cycloalkyl, each optionally in the aryl or
  • Heterocyclyl part substituted aryl, arylalkyl with 1 to 6 carbon atoms in the alkyl part, heterocyclyl, heterocyclylalkyl with 1 to 6
  • Rl 7 represents hydrogen or Cf-C4-alkyl
  • R 18 represents hydrogen or C1-C4-alkyl, Z 1 for hydrogen or C 1 -C 2 -alkyl or alkylcarbonyl, optionally substituted by C 1 -C 4 -alkyl, C3-cy-cycloalkyl or cycloalkylcarbonyl, in each case optionally substituted aryl, arylcarbonyl, arylalkyl, arylalkylcarbonyl in the aryl or heterocyclyl part with 1 to 6
  • R20 represents hydrogen or optionally arylcarbonyloxy or alkoxy, alkylthio, alkoxycarbonyl or alkylcarbonyloxy each substituted by formyloxy, optionally substituted in the aryl part, each having 1 to 6 carbon atoms in the alkyl part substituted C1-C4-alkyl or in each case optionally substituted in the aryl part or heterocyclyl part aryl, heterocyclyl, arylalkyl with 2 to 6 carbon atoms in the alkyl part or heterocyclylalkyl with 1 to 6 carbon atoms in the alkyl part or substituted benzyl or
  • R 2 and R20 together with the atoms to which they are attached form a heterocyclic ring with 3 to 6 ring members
  • R21 represents hydrogen or C 4 -C 4 alkyl
  • each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
  • the invention particularly relates to the new compounds of formula (J) in which
  • Rl represents hydrogen or methyl
  • Rl 2 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl and
  • A represents oxygen, sulfur or - (N-RI9) -, in which
  • R 9 represents hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or together with R ° "U nd the nitrogen atom to which they are attached represent optionally methyl- or ethyl-substituted pyrrolidinyl, Mo ⁇ holinyl, piperidinyl, piperazinyl or hexahydroazepinyl, R 4 for hydrogen or phenylcarbonyloxy, methoxy, ethoxy, methylthio, ethylthio, methoxycarbonyl, ethoxycarbonyl, methylcarbonyloxy, ethylcarbonyloxy, propylcarbonyloxy, pentylcarbonyloxy or hexylcarbonyloxy substituted methyl, ethyl, n- or i- Propyl, n-, i-, s- or t-butyl
  • Rl2 and Rl4 together with the atoms to which they are attached represent a pyrrolidine or piperidine ring
  • Rl5 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or
  • Rl ⁇ and RlS together with the carbon atom to which they are attached represent a cyclopropane, cyclopentane or cyclohexane ring,
  • Rl6 for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
  • R 7 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl and R 8 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
  • R20 for hydrogen or phenylcarbonyloxy, methoxy, ethoxy, methylthio, ethylthio, methoxycarbonyl, ethoxycarbonyl, methylcarbonyloxy, ethylcarbonyloxy, propylcarbonyloxy, pentylcarbonyloxy or hexylcarbonyloxy substituted methyl, ethyl, n- or i-propyl, n -, i-, s- or t-butyl or in each case optionally in the phenyl part or
  • R and R 0 together with the atoms to which they are attached represent a pyrrolidine or piperidine ring
  • R21 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or
  • R20 nd R are together with the carbon atom to which they are attached represent a cyclopropane ring, cyclopentane or cyclohexane ring.
  • heterocyclyl or heterocyclylalkyl are listed in the list below: Halogen, amino, hydroxy, oxo, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propyl-thio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino.
  • Formula (II) provides a general definition of the aminosalicylic acid amides required as starting materials for carrying out process a) according to the invention.
  • R and Rl3 preferably or in particular have those meanings which have already been given as preferred or as particularly preferred for R 2 and Rl3 in connection with the description of the compounds of the formula (I) according to the invention.
  • R 2 has the meaning given above, and
  • Rl3 for a grouping or or
  • R 14 , R 15 , R 16 , R 17 , R 18 , Z 1 and R 2 1 have the meanings given above,
  • R22 nd R 1 together with the carbon atom to which they are attached form a carbocyclic ring.
  • Aminosalicylic acid amides of the formula (II-a) are preferred, in which
  • R 14 , R 15 , R 16 , R 17 , R 8 , Z 1 and R 21 have the meanings given above,
  • R U and R21 together with the carbon atom to which they are attached represent a cyclopentane or cyclohexane ring.
  • R 2 has the meaning given above, and
  • R 14 , R 15 , R 16 , R 17 , R 18 , Z 1 and R 2 1 have the meanings given above,
  • R and R together with the atoms to which they are attached represent a pyrrolidine or piperidine ring or
  • R22 and R2I together with the carbon atom to which they are attached represent a cyclopentane or cyclohexane ring.
  • R and R 3 have the meanings given above,
  • a diluent preferably an ester such as methyl acetate or ethyl acetate; an alcohol, such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, ethanediol, propan-l, 2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene; Water, a salt solution, such as ammonium chloride solution, an acid, such as hydrochloric acid or acetic acid, and any mixtures of the diluents mentioned and optionally in the presence of a catalyst, such as Raney nickel, palladium or
  • Formula (IV-a) provides a general definition of the nitrosalicylic acid amides required as starting materials for carrying out process c) according to the invention.
  • R and Rl3 preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (II-a) according to the invention, have been indicated as preferred or as particularly preferred for Rl U d R 3 were.
  • nitrosalicylic acid amides of the formula (IV-a) are new and are also the subject of the present application.
  • R 2 and R 3 have the meanings given above,
  • a diluent for example and preferably an aliphatic, alicyclic or aromatic hydrocarbon, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; a halogenated hydrocarbon such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; an ether, such as, for example, diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; a ketone such as acetone, butanone, methyl isobutyl hydrocarbon, such as petroleum
  • the 2-hydroxy-3-nitrobenzoic acid or 2-hydroxy-3-nitrobenzoic acid chloride required as starting materials for carrying out process d) according to the invention are known (compare, for example, JJ Het. Chem., 1971, 8 (6), 889-891, J Chem.Soc, 1953 2049, 2050 or U.S. Patent 03527865).
  • Formula (V) provides a general definition of the amines required as starting materials for carrying out process d) according to the invention.
  • R 2 and R 3 have examples and preferably or in particular 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 R 2 and R 3 were specified.
  • the amines of the formula (VII) are known reagents in organic chemistry.
  • the compounds of the formula (I) are known in some cases and can be prepared by processes which are known in some cases (cf. Biochim. Biophys. Acta 1993, 262-268).
  • Formula (III) provides a general definition of the acylating agents which are furthermore required as starting materials for carrying out process a) according to the invention.
  • R preferably or in particular has the meaning which has already been stated as preferred or as particularly preferred for R1 in connection with the description of the compounds of the formula (I) according to the invention.
  • ⁇ stands for halogen, hydroxy, alkoxy or alkylcarbonyloxy, preferably for chlorine, hydroxy, methoxy, ethoxy or acetoxy.
  • acylating agents of the general formula (III) are known reagents in organic chemistry.
  • Formula (IV) provides a general definition of the nitrosalicylic acid amides required as starting materials for carrying out process b) according to the invention.
  • R and Rl3 preferably or in particular have those meanings which have already been given as preferred or as particularly preferred for R and Rl3 in connection with the description of the compounds of the formula (I) according to the invention.
  • Some of the starting materials of the formula (IV) are known (cf., for example, Heterocycl. Chem. (1971), 8 (6), 989-991).
  • nitrosalicylic acid amides of the formula (IV-a) are new and have already been described above in connection with the description of the process c) according to the invention.
  • Suitable diluents for carrying out process a) according to the invention are all inert organic solvents. These include, for example and preferably, aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as, for example, diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole;
  • Process a) 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 preferably include alkaline earth metal or alkali metal hydroxides, acetates, carbonates or hydrogen carbonates, such as, for example, sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate or sodium hydrogen carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, tributylamine .
  • DABCO diazabicyclooctane
  • DBN diaza-bicyclonones
  • DBU diazabicycloundecene
  • Process b) according to the invention is optionally carried out in the presence of a catalyst.
  • a catalyst As such, all catalysts come into question that are also suitable for
  • Hydrogenations are commonly used. Examples include: Raney nickel, palladium or platinum, optionally on a support material, such as activated carbon.
  • reaction temperatures can be carried out when the inventive compounds
  • Processes a) and b) can be varied over a wide range. In general, temperatures from 0 ° C to 180 ° C, preferably at temperatures from 0 ° C to 130 ° C.
  • acylating agent of the formula (III) are generally employed per mole of the aminosalicylic acid amide of the formula (II).
  • the processes according to the invention are generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar.
  • the substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and
  • Bacteria can be used in crop protection and material protection.
  • Fungicides can be used to protect plants against Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • pathogens of fungal and bacterial are exemplary but not limiting
  • Xanthomonas species such as, for example, Xanthomonas campestris pv. Oryzae;
  • Pseudomonas species such as, for example, Pseudomonas syringae pv. Lachrymans; Erwinia species, such as, for example, Erwinia amylovora;
  • Pythium species such as, for example, Pythium ultimum
  • Phytophthora species such as, for example, Phytophthora infestans
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or
  • Plasmopara species such as, for example, Plasmopara viticola
  • Bremia species such as, for example, Bremia lactucae
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae;
  • Erysiphe species such as, for example, Erysiphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca Faniginea
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Venturia species such as, for example, Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Cochliobolus species such as, for example, Cochliobolus sativus (conidial form: Drechslera, Syn: Helminthosporium);
  • Uromyces species such as, for example, Uromyces appendiculatus; Puccinia species, such as, for example, Puccinia recondita; Sclerotinia species, such as, for example, Sclerotinia sclerotiorum; Tilletia species, such as, for example, Tilletia caries; Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae; Pellicularia species, such as, for example, Pellicularia sasakii;
  • Pyricularia species such as, for example, Pyricularia oryzae; Fusarium species, such as, for example, Fusarium culmorum; Botrytis species, such as, for example, Botrytis cinerea; Septoria species, such as, for example, Septoria nodorum; Leptosphaeria species, such as, for example, Leptosphaeria nodorum;
  • Cercospora species such as, for example, Cercospora canescens; Alternaria species, such as, for example, Alternaria brassicae; Pseudocercosporella species, such as, for example, Pseudocercosporella he ⁇ otrichoides.
  • the active compounds according to the invention can be used with particularly good success to combat diseases in wine, fruit and vegetable cultivation, such as, for example, against Botrytis, Phytophtora and Plasmopara species, or rice diseases, such as, for example, against Pyricularia species.
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or cultivated plants (including naturally occurring cultivated plants).
  • Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological good genetic engineering methods or combinations of these methods, including the transgenic plants and including those which can or cannot be protected by plant breeders' rights Plant varieties.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as sprout, leaf, flower and root, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space according to the customary treatment methods, e.g. by dipping, spraying,
  • Grain diseases are also combated with good success.
  • the active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV -Cold and warm mist formulations.
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, 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. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and or solid carriers, 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.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • aromatics such as Xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions
  • alcohols such as butanol or glycol
  • ketones such as acetone, methyl ethyl ketone, Methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • solid carriers for example, natural rock powder, such as
  • the following are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems.
  • Possible emulsifiers and / or foaming agents are: e.g.
  • non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • polyoxyethylene fatty acid esters polyoxyethylene fatty alcohol ethers
  • e.g. Alkylaryl polyglycol ethers alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • dispersants come in
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum mariabicum, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the spectrum of activity or to prevent the development of resistance.
  • fungicides bactericides
  • acaricides nematicides or insecticides
  • synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Fenpropidine fenpropimoiph, fentin acetate, fentin hydroxide, ferbam, ferimzon, Fluazinam, flumetover, fluoromide, fluquinconazole, flu ⁇ rimidol, flusilazole,
  • Imazalil Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan,
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl,
  • Metconazole methasulfocarb, meth hyporoxam, metiram, metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,
  • Oxadixyl Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
  • Tebuconazole Tecloftalam, Tecnazen, Tetcyclacis, Tetraconazole, Thiabendazole, Thicyofen, Thifluzamide, Thiophanate-methyl, Thiram, Tioxymid, Tolclofos-methyl,
  • Ethiofcncarb Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimfos, Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxoxinon, Flutoxinoxuron, Fluutinoxuron, Fluutinoxuron, Fluutinoxuron, , Furathiocarb,
  • Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene, Imidacloprid, Isazofos, Isofenphos, Isoxathion, Ivermectin, Kempo lyedervi ren Lambda-cyhalothrin, Lufenuron
  • Paecilomyces fumosoroseus Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propoxur, Prothiofos, Prothoat, Pyromhrhridosine, Pymmethrofinos, Pymmethrofinos , Pyridathione, pyrimidifen, pyriproxyfen,
  • the compounds of formula (I) according to the invention also have very good antifungal effects. They have a very broad spectrum of antimycotic effects, in particular against dermatophytes and shoots, mold and diphasic fungi (for example against Candida species such as Candida albicans, Candida glabrata) such as Epidermophyton floecosum, Aspergillus species such as Aspergillus niger and Aspergillusiesumumumum such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii.
  • Candida species such as Candida albicans, Candida glabrata
  • fungi for example against Candida species such as Candida albicans, Candida glabrata
  • fungi for example against Candida species such as Candida albicans, Candida glabrata
  • Epidermophyton floecosum such as Epidermophyton floecosum
  • Aspergillus species such as Aspergillus niger and Aspergillusiesum
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume 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 application rates can be varied within a relatively wide range, depending on the type of application.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the case of seed treatment, the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the Wall amounts of active ingredient in general between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • logP values were determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC (gradient method, acetonitrile 1 / 0.1% aqueous phosphoric acid)
  • dimethylacetamide emulsifier 1.0 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Evaluation is carried out 3 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Example B the substances according to the invention listed in Examples (2), (4), (8) and (12) show an efficiency of 92% or more at an application rate of 100 g / ha.
  • Example B the substances according to the invention listed in Examples (2), (4), (8) and (12) show an efficiency of 92% or more at an application rate of 100 g / ha.
  • dimethylacetamide emulsifier 1.0 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 for 5 days at approx. 21 ° C and approx. 90% humidity.
  • the plants are then moistened and placed in an incubation cabin for 1 day.
  • Botrytis test (bean) / protective
  • dimethylacetamide emulsifier 1.0 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 inoculated plants are placed in a darkened chamber at approx. 20 ° C and 100% relative humidity.
  • Example D the substances according to the invention listed in Examples (2), (4), (6), (8) and (12) show an efficiency of 90% or more at an application rate of 500 g / ha.
  • Emulsifier 1.2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in a greenhouse at 80% relative atmospheric humidity and a temperature of 26 ° C.
  • Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)
  • Indole Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pyrrole Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des amides d'acide aminosalicylique connus et nouveaux, plusieurs procédés de production correspondants et leur utilisation pour lutter contre les organismes nuisibles pour les plantes, ainsi que de nouveaux produits intermédiaires et leurs procédés de production.
PCT/EP2000/007523 1999-08-16 2000-08-03 Amides d'acide aminosalicylique et leur utilisation pour lutter contre les organismes nuisibles pour les plantes WO2001012587A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP00958374A EP1210321A1 (fr) 1999-08-16 2000-08-03 Amides d'acide aminosalicylique et leur utilisation pour lutter contre les organismes nuisibles pour les plantes
AU69920/00A AU6992000A (en) 1999-08-16 2000-08-03 Aminosalicylclic acid amides and their use for combating organisms that are harmful to plants
JP2001516888A JP2003507360A (ja) 1999-08-16 2000-08-03 アミノサリチル酸アミド類及び植物に有害な生物を防除するためのそれらの使用

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19938737A DE19938737A1 (de) 1999-08-16 1999-08-16 Aminosalicylsäureamide
DE19938737.0 1999-08-16

Publications (1)

Publication Number Publication Date
WO2001012587A1 true WO2001012587A1 (fr) 2001-02-22

Family

ID=7918514

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2000/007523 WO2001012587A1 (fr) 1999-08-16 2000-08-03 Amides d'acide aminosalicylique et leur utilisation pour lutter contre les organismes nuisibles pour les plantes

Country Status (5)

Country Link
EP (1) EP1210321A1 (fr)
JP (1) JP2003507360A (fr)
AU (1) AU6992000A (fr)
DE (1) DE19938737A1 (fr)
WO (1) WO2001012587A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT201900006543A1 (it) 2019-05-06 2020-11-06 Isagro Spa Composti ad attività fungicida, relative composizioni agronomiche e uso per il controllo di funghi fitopatogeni
IT201900011127A1 (it) * 2019-07-08 2021-01-08 Isagro Spa Composti ad attività fungicida, relative composizioni agronomiche e uso per il controllo di funghi fitopatogeni
IT201900021960A1 (it) 2019-11-22 2021-05-22 Isagro Spa Composti ad attività fungicida, loro composizioni agronomiche e relativo metodo di preparazione
US11365175B2 (en) 2017-11-03 2022-06-21 Isagro S.P.A. Aromatic amides having a fungicidal activity, their agronomic compositions and relative preparation method

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103562158B (zh) * 2010-12-31 2018-04-27 拜耳知识产权股份有限公司 提高植物质量的方法
WO2012088645A1 (fr) * 2010-12-31 2012-07-05 Bayer Cropscience Ag Procédé d'amélioration de la qualité d'une plante

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3527865A (en) * 1966-04-04 1970-09-08 Ben Venue Lab Inc Method of controlling sea lamprey
WO1997008135A1 (fr) * 1995-08-30 1997-03-06 Bayer Aktiengesellschaft Amides d'acide acylaminosalicylique et leur utilisation comme pesticides
DE19710609A1 (de) * 1997-03-14 1998-09-17 Bayer Ag Substituierte Aminosalicylsäureamide
WO1999027783A1 (fr) * 1997-12-04 1999-06-10 Dow Agrosciences Llc Compositions fongicides, procedes correspondants, composes et procedes concourant a leur elaboration

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3527865A (en) * 1966-04-04 1970-09-08 Ben Venue Lab Inc Method of controlling sea lamprey
WO1997008135A1 (fr) * 1995-08-30 1997-03-06 Bayer Aktiengesellschaft Amides d'acide acylaminosalicylique et leur utilisation comme pesticides
DE19710609A1 (de) * 1997-03-14 1998-09-17 Bayer Ag Substituierte Aminosalicylsäureamide
WO1999027783A1 (fr) * 1997-12-04 1999-06-10 Dow Agrosciences Llc Compositions fongicides, procedes correspondants, composes et procedes concourant a leur elaboration

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 86, no. 3, 17 January 1977, Columbus, Ohio, US; abstract no. 15140v, ISHIYAMA, TADAYUKI ET AL: "Deisovalerylblastmycin produced by Streptomyces species." page 304; column 1; XP002155387 *
E. E. VAN TAMELEN ET AL: "The Chemistry of antimycin A. X. Structure of the antimycins.", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 83, 1961, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC., US, pages 1639 - 46, XP002155384, ISSN: 0002-7863 *
F. SHIGEO OKUMURA ET AL: "The chemistry of antimycin A. V. Synthesis of antimycic acid methyl ester methyl ether and its analogues.", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 81, 1959, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC., US, pages 3753 - 56, XP002155385, ISSN: 0002-7863 *
J. ANTIBIOT., vol. 29, no. 8, 1976, pages 804 - 8 *
M T WU AND R E LYLE: "Synthesis of some simple actinomycin analogs", JOURNAL OF HETEROCYCLIC CHEMISTRY., vol. 8, 1971, HETEROCORPORATION. PROVO., US, pages 989 - 91, XP002155386, ISSN: 0022-152X *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11365175B2 (en) 2017-11-03 2022-06-21 Isagro S.P.A. Aromatic amides having a fungicidal activity, their agronomic compositions and relative preparation method
IT201900006543A1 (it) 2019-05-06 2020-11-06 Isagro Spa Composti ad attività fungicida, relative composizioni agronomiche e uso per il controllo di funghi fitopatogeni
WO2020225700A1 (fr) * 2019-05-06 2020-11-12 Isagro S.P.A. Composés ayant une activité fongicide, leurs compositions agronomiques et leur utilisation pour lutter contre des champignons phytopathogènes
IT201900011127A1 (it) * 2019-07-08 2021-01-08 Isagro Spa Composti ad attività fungicida, relative composizioni agronomiche e uso per il controllo di funghi fitopatogeni
WO2021005512A1 (fr) * 2019-07-08 2021-01-14 Isagro S.P.A. Composés ayant une activité fongicide, leurs compositions agronomiques et leur utilisation pour lutter contre des champignons phytopathogènes
EP4162799A1 (fr) 2019-07-08 2023-04-12 ISAGRO S.p.A. Composés à activité fongicide, leurs compositions agronomiques et leur utilisation pour lutter contre les champignons phytopathogènes
IT201900021960A1 (it) 2019-11-22 2021-05-22 Isagro Spa Composti ad attività fungicida, loro composizioni agronomiche e relativo metodo di preparazione

Also Published As

Publication number Publication date
AU6992000A (en) 2001-03-13
JP2003507360A (ja) 2003-02-25
EP1210321A1 (fr) 2002-06-05
DE19938737A1 (de) 2001-02-22

Similar Documents

Publication Publication Date Title
EP1161420A2 (fr) Carboxanilides de pyrazole fongicides
WO2002008197A1 (fr) Biphenylcarboxamides
EP1474407A1 (fr) Difluoromethyl thiazolyl carboxanilides
EP1474406A1 (fr) Thiazolylcarboxanilides disubstitues et leur utilisation comme microbicides
WO2000076979A1 (fr) Pyridinecarboxamides et leur utilisation en tant que produits phytosanitaires
EP1501832A1 (fr) Triazolopyrimidines
EP1509513A1 (fr) Oxathiine-carboxamides
EP1210321A1 (fr) Amides d'acide aminosalicylique et leur utilisation pour lutter contre les organismes nuisibles pour les plantes
EP1173425A1 (fr) Enantiomere(-) de la 2- 2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro 1,2,4]triazol-3-thione
EP1105372A1 (fr) Amides d'acide methoximinophenylacetique
DE19958166A1 (de) Pyridincarbamide
EP1235813B1 (fr) Derives d'acide hydroxamique
EP1237850B1 (fr) Amides d'acide glyoxylique
DE10145771A1 (de) Phthalazinone
WO2002050059A1 (fr) Azinylsulfonylimidazoles servant d'agents microbicides
DE10122447A1 (de) Biphenylcarboxamide
EP1114036A1 (fr) Sulfonyloxazolones et leur utilisation pour lutter contre des micro-organismes indesirables
EP1117654A1 (fr) Derives de sulfonyltriazol et leur utilisation pour lutter contre des micro-organismes
EP1345904A1 (fr) Dichlorpyridyl methyl cyanamidines
WO2000008003A2 (fr) Thiophene-dioximethers
WO2000032563A1 (fr) Oximes substituees
EP1345934A2 (fr) Sulfonylpyrroles
WO2002050038A1 (fr) Dichloropyridylmethylimines utilisees comme produit phytosanitaire

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CR CU CZ DE DK DM DZ EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG US UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
WWE Wipo information: entry into national phase

Ref document number: 2000958374

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 10069197

Country of ref document: US

WWP Wipo information: published in national office

Ref document number: 2000958374

Country of ref document: EP

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

WWW Wipo information: withdrawn in national office

Ref document number: 2000958374

Country of ref document: EP