EP0730592A1 - Derives d'acide 2,3,5,6-tetrafluorobenzoique et leur utilisation pour lutter contre les parasites - Google Patents

Derives d'acide 2,3,5,6-tetrafluorobenzoique et leur utilisation pour lutter contre les parasites

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Publication number
EP0730592A1
EP0730592A1 EP95901380A EP95901380A EP0730592A1 EP 0730592 A1 EP0730592 A1 EP 0730592A1 EP 95901380 A EP95901380 A EP 95901380A EP 95901380 A EP95901380 A EP 95901380A EP 0730592 A1 EP0730592 A1 EP 0730592A1
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EP
European Patent Office
Prior art keywords
substituted
carbon atoms
alkyl
unsubstituted
ethyl
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.)
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Application number
EP95901380A
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German (de)
English (en)
Inventor
Udo Kraatz
Gerd Hänssler
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
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Bayer AG
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Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0730592A1 publication Critical patent/EP0730592A1/fr
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
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    • 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
    • A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
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    • 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
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    • 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
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    • 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
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    • A01N37/24—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides containing at least one oxygen or sulfur atom being directly attached to the same aromatic ring system
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    • 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
    • A01N37/36—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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    • 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
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    • 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
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
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    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
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    • C07C233/66—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
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    • C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/78—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
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    • C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/83—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of an acyclic saturated carbon skeleton
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    • C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/87—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
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    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Definitions

  • the invention relates to new derivatives of 2,3,5,6-tetrafluorobenzoic acid, a process for their preparation and their use for controlling pests.
  • Y stands for oxygen or sulfur
  • R 1 and R 2 independently of one another are optionally substituted alkyl, cycloalkyl and aryl, R 3 is alkyl with at least 2 carbon atoms, substituted alkyl and optionally substituted cycloalkyl, aryl and aralkyl,
  • R 4 , R 5 and R 6 independently of one another are hydrogen and optionally substituted alkyl, aryl and aralkyl, or
  • R 5 and R 6 together with the nitrogen atom to which they are attached form an optionally substituted ring, or
  • R 7 and R 8 independently of one another are hydrogen and optionally substituted alkyl, cycloalkyl, aryl, aralkyl, alkylheteroaryl and heteroaryl, or represent the groups -CHR 4 -COOH and -CHR 4 -COOCH 3 , where R 7 and R 8 are not simultaneously stand for hydrogen, or
  • R 7 and R 8 together with the nitrogen atom to which they are attached form an optionally substituted ring
  • the new derivatives of 2,3,5,6-tetrafluorobenzoic acid of the general formula (I) have an excellent microbicidal activity, in particular against microorganisms which are pathogenic to plants.
  • the active compounds according to the invention have an excellent resistance-inducing activity in plants against attack by undesired microorganisms.
  • Alkyl individually or in composite radicals, straight-chain or branched alkyl having 1 to 8, in particular 1 to 4, carbon atoms. Examples include methyl, ethyl, n.- and i.-propyl, n-, i-, s- and t-butyl.
  • Cycloalkyl - a 3- to 7-membered ring, in particular a ring with 3, 5 or 6 carbon atoms. Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl may be mentioned by way of example and preferably.
  • Aryl unsubstituted or substituted aryl having 6 to 10 carbon atoms examples are unsubstituted or substituted
  • Aralkyl unsubstituted or substituted aralkyl having 1 to 4, in particular 1 or 2, carbon atoms in the straight-chain or branched alkyl part and 6 to
  • Preferred heteroatoms are oxygen, sulfur and nitrogen.
  • heteroarylalkyl the heteroaryl part corresponds to the definitions and preferred ranges given above.
  • the alkyl part is straight-chain or branched and contains 1 to
  • 4 especially 1 or 2 carbon atoms.
  • exemplary and preferred are heteroarylmethyl, 1,1- and 1,2-heteroarylethyl and 1,1-, 1,2-, 1,3- and 2,2-heteroarylpropyl.
  • the optionally substituted radicals of the general formulas can carry one or more, preferably 1 to 3, in particular 1 or 2, identical or different substituents.
  • substituents are: alkyl having preferably 1 to 4, in particular 1 or 2, carbon atoms, such as methyl, ethyl, n.- and i.-propyl and n.-, i.-, sea and t.
  • Alkoxy preferably having 1 to 4, in particular 1 or 2, carbon atoms, such as methoxy, ethoxy, n.- and i.-propyloxy and n.-, L-, see- and t.-butyloxy
  • Alkylthio with preferably 1 to 4, in particular 1 or 2 carbon atoms, such as methylthio, ethylthio, n.- and i.-propylthio and n.-, i.-, see- and t.-butylthio
  • Haloalkyl, haloalkoxy and haloalkylthio with preferably 1 to 4, in particular 1 or 2 carbon atoms and preferably 1 to 9, in particular 1 to 5 halogen atoms, where the halogen atoms are identical or different and are halogen atoms, preferably fluorine, chlorine or bromine, in particular fluorine, such as trifluoromethyl, difluoromethyl, pentafluoroe
  • R 1 and R 2 are the same or different and each represents unsubstituted or substituted alkyl having 1 to 4 carbon atoms, cycloalkyl having 3 to 7 carbon atoms or phenyl,
  • R 3 represents alkyl with 2 to 8 carbon atoms, substituted alkyl with 1 to 8 carbon atoms, each unsubstituted or substituted cycloalkyl with 3 to 7 carbon atoms, phenyl or phenylalkyl with 1 to 4 carbon atoms in the alkyl part,
  • R 4 , R 5 , R 6 , R 7 and R 8 are the same or different and represent hydrogen, in each case unsubstituted or substituted alkyl having 1 to 8 carbon atoms, phenyl or phenylalkyl having 1 to 4 carbon atoms in the alkyl part, where R and R 8 does not simultaneously represent hydrogen,
  • R 7 and R 8 independently of one another, in addition, each for unsubstituted or substituted cycloalkyl having 3 to 7 carbon atoms, 5- to 9-membered heteroaryl which contains 1 to 4 identical or different heteroatoms such as oxygen, nitrogen and sulfur, or corresponding heteroarylalkyl having 1 to 4 carbon atoms in the alkyl part, or
  • R 8 represents the groups -CHR 4 -COOH and -CHR 4 -COOCH 3 or
  • R 5 and R 6 together with the nitrogen atom to which they are attached form an unsubstituted or substituted 5- to 7-membered ring which can additionally contain 1 or 2 identical or different heteroatoms such as oxygen, nitrogen and sulfur, or
  • R 7 and R 8 together with the nitrogen atom to which they are attached form an unsubstituted or substituted 5- to 7-membered ring which can additionally contain 1 or 2 identical or different heteroatoms such as oxygen, nitrogen and sulfur.
  • R 1 and R 2 are the same or different and each represents unsubstituted branched alkyl having 4 to 6 carbon atoms or substituted alkyl having 1 to 6 carbon atoms, each unsubstituted or substituted cyclopropyl, cyclobutyl, cyclopropyl, cyclohexyl or phenyl,
  • R 3 represents alkyl having 2 to 6 carbon atoms, substituted alkyl having 1 to 6 carbon atoms, in each case unsubstituted or substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl or
  • R 4 represents hydrogen or alkyl having 1 to 4 carbon atoms or optionally substituted phenyl or benzyl,
  • R 5 and R 6 are the same or different and represent hydrogen, alkyl having 1 to 8 carbon atoms and unsubstituted or substituted phenyl, the preferred substituents being halogen, alkyl, alkoxy, Alkylthio, haloalkyl, haloalkoxy and haloalkylthio may be mentioned,
  • R 7 and R 8 are identical or different and represent hydrogen, in each case unsubstituted or substituted alkyl having 1 to 6 carbon atoms, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl and benzyl, the substituents preferably being halogen, alkyl, alkoxy, alkylthio, Haloalkyl, haloalkoxy, haloalkylthio and dialkylamino may be mentioned, but R 7 and R 8 do not simultaneously represent hydrogen, and
  • R 8 additionally stands for the groups -CHR 4 -COOH and -CHR 4 -COOCH 3 or
  • R 3 and R 6 together with the nitrogen atom to which they are attached represent an unsubstituted or substituted piperidine
  • R 7 and R 8 together with the nitrogen atom to which they are attached are in each case an unsubstituted or substituted piperidine,
  • R 1 represents methyltriazolyl
  • R 2 represents butyl, pentyl, hexyl and heptyl which is optionally substituted by unsubstituted or halogen-substituted phenoxy, or in each case optionally one to three times by fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy,
  • R 3 stands for ethyl, n- and i-propyl, n-, i-, s- and t-butyl, or for methyl, ethyl, n- and i-propyl substituted by dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl , n.-, i.-, s.- and t.-butyl, or for each optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy or phenyl, benzyl or
  • R 5 represents hydrogen, methyl, ethyl, n.-, i.-propyl, n.-, i.-, s.- and t.-butyl,
  • R 6 represents hydrogen, methyl, ethyl, n.-, i.-propyl, n.-, i.-, s.- and t.-butyl, or
  • R 5 and R 6 together with the nitrogen atom to which they are attached form a piperidine, morpholine, hexahydroazepine or piperazine ring,
  • R 7 represents hydrogen, methyl, ethyl, n.-, i.-propyl, n.-, i.-, s.- and t.-butyl,
  • R 8 represents methyl, ethyl, n.- and i.-propyl, n.-, i.-, s.- and t.-butyl, optionally substituted by dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, or each in each case optionally monosubstituted to trisubstituted by fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl and / or trifluoromethoxy
  • R 4 represents hydrogen, methyl, ethyl, n.-, i.-propyl, n.-, i.-, s.- and t.-butyl, phenyl, biphenyl and hydroxybiphenyl and benzyl, or R 7 and R 8 together with the nitrogen atom to which they are bonded form a piperidine, pyrrolidine, morpholine or piperazine ring, which are optionally mono- or disubstituted by methyl, ethyl, hydroxymethyl and hydroxyethyl
  • Preferred compounds are also addition products of acids and those derivatives of the formula (I) in which the substituents R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 have the meanings which are already preferred for these substituents
  • the acids which can be added preferably include hydrohalic acids, such as, for example, hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, furthermore phosphoric acid, nitric acid, sulfuric acid, mono-, bi- and trifunctional carboxylic acids and hydroxycarboxylic acids, such as, for example, acetic acid, maleic acid, succinic acid, Fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid and lactic acid, sulfonic acids such as p-toluenesulfonic acid and 1,5-naphthalenedisulfonic acid as well as saccharin or thiosaccharin
  • hydrohalic acids such as, for example, hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, furthermore phosphoric acid, nitric acid, sulfuric acid, mono-, bi- and trifunctional carboxylic acids and hydroxycarboxylic acids, such as, for example, acetic acid, maleic
  • preferred compounds are addition products of salts and metals of main groups II to IV and groups I and II as well as groups IV to VIII and those derivatives of formula (I) in which the substituents R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 have the meanings which have already been mentioned preferably for these substituents
  • Salts of copper, zinc, manganese, magnesium, tin, iron and nickel are particularly preferred.
  • Anions of these salts are those which are derived from acids which lead to environmentally compatible addition products.
  • Particularly preferred acids in this context are Hydrogen halide acids, such as, for example, hydrochloric acid and hydrobromic acid, nitric acid and sulfuric acid
  • the new derivatives of tetrafluorobenzoic acid of the formula (I) can be prepared in an analogous manner by known processes.
  • the starting compounds required for the preparation of the compounds of the formula (I) are known or can be prepared by generally known methods
  • the starting compounds are preferably reacted in an inert water-immiscible diluent, such as aromatic, non-aromatic or halogenated hydrocarbons such as: esters, such as ethyl acetate; Chlorinated hydrocarbons, such as dichloromethane, trichloroethane; Aromatics such as toluene; Hydrocarbons such as cyclohexane or their mixtures and / or in the presence of an acid binder such as potassium carbonate, triethylamine, pyridine, N-methylpiperidine or potassium or sodium hydroxide, at temperatures from 0 ° C to 100 ° C, preferably 20 ° C to 40 ° C and under normal pressure.
  • the invention encompasses both the pure isomers and the mixtures. These mixtures can be prepared using common methods, e.g. selective crystallization from suitable solvents or chromatography on silica gel or aluminum oxide are separated into the components. Racemates can be separated into the individual enantiomers by conventional methods, e.g. by salt formation with optically active acids such as champhersulfonic acid or dibenzoyl acid and selective crystallization or by derivatization with suitable, optically active reagents, separation of the diastereomeric derivatives and cleavage or separation on optically active column material.
  • optically active acids such as champhersulfonic acid or dibenzoyl acid
  • suitable, optically active reagents separation of the diastereomeric derivatives and cleavage or separation on optically active column material.
  • the active compounds of the formula (I) according to the invention have a strong action against pests and can be used practically to combat unwanted harmful organisms.
  • the active ingredients are suitable for use as crop protection agents, in particular as fungicides.
  • Fungicidal agents in crop protection are used to control 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
  • Plasmopara species such as, for example, Plasmopara viticola
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae
  • Erysiphe species such as, for example, Erysiphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca fuliginea
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Venturia species such as, for example, Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or P. graminea (conidia form: Drechslera, Syn: Helminthosporium);
  • Cochliobolus species such as, for example, Cochliobolus sativus
  • Drechslera (Coni form: Drechslera, Syn: Helminthosporium);
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Puccinia species such as, for example, Puccinia recondita
  • Tilletia species such as, for example, Tilletia caries
  • Ustilago species such as, for example, Ustilago nuda or Ustilago avenae;
  • Pellicularia species such as, for example, Pellicularia sasakii;
  • Pyricularia species such as, for example, Pyricularia oryzae
  • Fusarium species such as, for example, Fusarium culmorum
  • Botrytis species such as, for example, Botrytis cinerea
  • Septoria species such as, for example, Septoria nodorum
  • Leptosphaeria species such as, for example, Leptosphaeria nodorum;
  • Cercospora species such as, for example, Cercospora canescens
  • Alternaria species such as, for example, Alternaria brassicae
  • Pseudocercosporella species such as, for example, Pseudocercosporella herpotrichoides.
  • the active compounds according to the invention can be used with particular good protection for controlling Pyricularia species on rice.
  • the active compounds according to the invention furthermore have a strong resistance-inducing action in plants. They are therefore suitable for generating resistance in plants against attack by undesired microorganisms
  • resistance-inducing substances are to be understood as those substances which, on the one hand, show only a low activity when directly affected by the undesired microorganisms, but on the other hand are able to stimulate the immune system of plants in such a way that the affected If the plants are subsequently inoculated with undesirable microorganisms, they will develop extensive resistance to these microorganisms
  • Undesired microorganisms are to be understood in the present case as phytopathogenic fungi, bacteria and viruses.
  • the substances according to the invention can therefore be used to produce resistance to the attack by the named pathogens in plants within a certain period of time after the treatment.
  • the period within which resistance is brought about is generally from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the active compounds
  • Unwanted microorganisms in crop protection include fungi from the classes of the Plasmodiophoromycetes, Oomycetes and Chytridiomycetes. Zygomycetes. Ascomycetes. Basidiomycetes and Deuteromycetes
  • 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 shapes
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents If water is used as an extender, organic solvents can also be used, for example Auxiliary solvents are used.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-generating agents
  • organic solvents can also be used, for example Auxiliary solvents are used.
  • Liquid solvents are essentially aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions Alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide and water; Liquefied gaseous extenders or carriers are liquids that are gaseous at normal temperature and pressure, e.g.
  • aerosol propellants such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide
  • solid rock materials can be considered, for example, natural rock powder , such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flours, such as highly disperse silicic acid, aluminum oxide and silicates, as solid carriers for granules are, 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, as emulsifiers and / or foam-generating agents, for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters , Poly oxyethylene fatty alcohol ethers, for example alkylaryl polygly
  • adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phosphophides, such as wafers and lecithins, and synthetic phospholipids, and 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 Aliza ⁇ n, azo and metal phthalocyanine substances and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can be present in the formulations in a mixture with other known active compounds, such as fungicides, insecticides, acaricides and herbicides, and in mixtures with fertilizers and growth regulators.
  • 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.
  • the following compounds are particularly favorable mixing partners.
  • Difenoconazole dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodine, drazoxolone,
  • Fludioxonil fluoromide, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl aluminum, fthalides, fuberidazole, furalaxyl, furmecyclox,
  • copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture,
  • Mancopper Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol,
  • Oxadixyl Oxamocarb, Oxycarboxin, Pefurazoat, Penconazol, Pencycuron, Phosdiphen, Pimaricin, Piperalin, Polyoxin,
  • Amitraz Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M,
  • Bacillus thuringiensis Bendiocarb, Benfuracarb, Bensultap, Betacyluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin,
  • Cadusafos Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap,
  • Chlorfenvinphos Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis- Resmethrin, Clocythrin, Clofentezin, Cyanophos, Cycloprothrin, Cyfluthrin,
  • Fenamiphos fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb,
  • Fenoxycarb fenpropathrin, fenpyrad, fenpyroximate, fenthion, fenvalerate, fipronil,
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyraclhrhos, Pyrraclofhion, Pyrraclofhion, Pyrraclofhion, Pyrraclofhion, Pyrraclofhion, Pyrraclofhion, Pyrraclofhion, Pyrraclofhion, Pyrraclofhion, Pyrraclofhion, Pyrraclofhion, Pyrraclofhion, Pyrraclofhion, Pyrraclofhion, Pyrraclofhion, Pyrraclofhion, Pyrraclof
  • Tebufenozid Tebufenpyrad, Tebupirimiphos, Teflubenuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiomethon, Thionazin, Thuringiensin, Tralometonium, Triaromenoriazonium, Triaromenoriazonium YI 5301/5302, zetamethrin.
  • the active ingredients 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 plants can also be treated.
  • the active compound concentrations in the use forms can be varied within a substantial range. They are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001%. In the seed treatment, amounts of active ingredient of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.
  • active ingredient concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02%, are required at the site of action.
  • the active substance concentrations for the treatment of parts of plants in the use forms can be varied within a substantial range. They are generally between 1 and 0.0001 percent by weight, preferably between 0.5 and 0.001%.
  • Solvent 12.5 parts by weight of acetone emulsifier: 0.3 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and the concentrate is diluted to the desired concentration with water and the stated amount of emulsifier.
  • the disease infestation is evaluated 4 days after the inoculation.
  • the compounds according to the manufacturing examples 1, 2, 3 and 37 show 100% efficiency at an application rate of 100 mg of active ingredient per 100 cm 3 .

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

Abstract

L'invention concerne des dérivés d'acide 2,3,5,6-tétrafluorobenzoïque de la formule (I) dans laquelle Y désigne oxygène ou soufre et X désigne les groupes -O-N=CR?1R2, -OR3, -OCHR4-CO-NR5R6 ou -NR7R8¿. L'invention concerne également un procédé permettant de les préparer, ainsi que leur utilisation pour lutter contre les parasites.
EP95901380A 1993-11-25 1994-11-14 Derives d'acide 2,3,5,6-tetrafluorobenzoique et leur utilisation pour lutter contre les parasites Withdrawn EP0730592A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4340180 1993-11-25
DE4340180A DE4340180A1 (de) 1993-11-25 1993-11-25 Derivate der 2,3,5,6-Tetrafluorbenzoesäure
PCT/EP1994/003775 WO1995014688A1 (fr) 1993-11-25 1994-11-14 Derives d'acide 2,3,5,6-tetrafluorobenzoique et leur utilisation pour lutter contre les parasites

Publications (1)

Publication Number Publication Date
EP0730592A1 true EP0730592A1 (fr) 1996-09-11

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EP95901380A Withdrawn EP0730592A1 (fr) 1993-11-25 1994-11-14 Derives d'acide 2,3,5,6-tetrafluorobenzoique et leur utilisation pour lutter contre les parasites

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Country Link
EP (1) EP0730592A1 (fr)
JP (1) JPH09511221A (fr)
CN (1) CN1141037A (fr)
AU (1) AU1064995A (fr)
BR (1) BR9408162A (fr)
CZ (1) CZ147396A3 (fr)
DE (1) DE4340180A1 (fr)
HU (1) HUT74715A (fr)
PL (1) PL314587A1 (fr)
SK (1) SK65896A3 (fr)
TW (1) TW258646B (fr)
WO (1) WO1995014688A1 (fr)

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Publication number Priority date Publication date Assignee Title
DE19615452A1 (de) * 1996-04-19 1997-10-23 Bayer Ag 2,3,5,6-Tetrafluorbenzoesäureamide
KR100587198B1 (ko) * 1997-08-28 2006-10-19 신젠타 파티서페이션즈 아게 곤충 또는 대표적 진드기 목의 방제용 물질
CN103819408B (zh) * 2014-03-13 2015-08-05 山东理工大学 硝基咪唑衍生物及其制备方法和用途
CN105254577B (zh) * 2015-08-07 2017-08-01 常州大学 一种双三氮唑取代苯二甲酸酯类化合物、制备方法和用途

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DE1642224B2 (de) * 1967-04-28 1976-04-29 Basf Ag, 6700 Ludwigshafen Verwendung von substituierten benzoesaeureaniliden zur bekaempfung von pilzen aus der klasse der basidiomyceten
US4055663A (en) * 1974-06-27 1977-10-25 National Patent Development Corporation Halogenated acylamino acids as fungicides
DE2944446A1 (de) * 1979-11-03 1981-06-11 Bayer Ag, 5090 Leverkusen Trisubstituierte benzyl-oximether, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide

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Title
See references of WO9514688A1 *

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Publication number Publication date
HU9601420D0 (en) 1996-07-29
TW258646B (fr) 1995-10-01
HUT74715A (en) 1997-02-28
AU1064995A (en) 1995-06-13
CZ147396A3 (en) 1996-08-14
SK65896A3 (en) 1996-11-06
JPH09511221A (ja) 1997-11-11
DE4340180A1 (de) 1995-06-01
PL314587A1 (en) 1996-09-16
CN1141037A (zh) 1997-01-22
BR9408162A (pt) 1997-08-05
WO1995014688A1 (fr) 1995-06-01

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