EP1119569A1 - Heterocyclylamides d'acide phenylacetique ayant un effet insecticide - Google Patents

Heterocyclylamides d'acide phenylacetique ayant un effet insecticide

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Publication number
EP1119569A1
EP1119569A1 EP99948849A EP99948849A EP1119569A1 EP 1119569 A1 EP1119569 A1 EP 1119569A1 EP 99948849 A EP99948849 A EP 99948849A EP 99948849 A EP99948849 A EP 99948849A EP 1119569 A1 EP1119569 A1 EP 1119569A1
Authority
EP
European Patent Office
Prior art keywords
formula
spp
optionally substituted
phenylacetic acid
alkyl
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.)
Withdrawn
Application number
EP99948849A
Other languages
German (de)
English (en)
Inventor
Markus Heil
Hans-Christian Militzer
Thomas Bretschneider
Bernd Alig
Astrid Mauler-Machnik
Klaus Stenzel
Ulrike Wachendorff-Neumann
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 CropScience AG
Original Assignee
Bayer AG
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Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP1119569A1 publication Critical patent/EP1119569A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to novel phenylacetic acid heterocyclylamides, a process for their preparation and their use for controlling unwanted microorganisms and animal pests.
  • N- (5-isothiazolyl) amides or N- (5-thiadiazolyl) amides have insecticidal and fungicidal properties (cf. WO 97-188, WO 97-26 251 and WO 95 -31 448). The effectiveness of these substances is good, but leaves something to be desired in some cases at low application rates.
  • R 1 represents alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio or optionally substituted cycloalkyl,
  • R 2 represents hydrogen, alkylcarbonyl, alkoxy carbonyl or optionally substituted arylcarbonyl, aryloxycarbonyl or aralkyloxycarbonyl,
  • R 3 represents hydrogen or alkyl
  • R 4 stands for optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted aralkyloxy or for optionally substituted aralkyloxyalkyl, or two geminal or vicinal R 4 radicals together with the hydrogen atom (s) to which they are bound form a saturated or unsaturated, optionally substituted, five- or six-membered ring which may contain one or two heteroatoms,
  • n stands for integers from 1 to 4,
  • X represents a nitrogen atom or a group of the formula CH, C-Cl, C-Br,
  • A represents a direct bond or a CH 2 group
  • R 1 , R 3 , R 4 , A, X and n have the meanings given above,
  • R 5 represents alkyl, alkoxy or optionally substituted aryl, aryloxy or aralkyloxy
  • phenylacetic acid heterocyclylamides of the formula (I) are very suitable for controlling unwanted microorganisms and animal pests.
  • the substances according to the invention have a significantly better fungicidal and insecticidal activity than the constitutionally most similar, previously known substances with the same direction of action.
  • the phenylacetic acid heterocyclylamides according to the invention are generally defined by the formula (I).
  • R 1 preferably represents C 1 -C 4 alkyl, C 1 -C 4 haloalkyl with 1 to 5 fluoro,
  • Chlorine and / or bromine atoms for C r C alkyl thio-C j -C ⁇ alkyl, CC 4 - alkoxy, C ] -C 4 alkylthio or for optionally single to triple, identical or different by C j -C 4 alkyl or
  • R 2 preferably represents hydrogen, C] -C -alkylcarbonyl, C ] -C 4 -alkoxy-carbonyl or phenyl-carbonyl, phenyloxy-carbonyl or phenyl-C ] -C 4 -alkyloxy-carbonyl, the three the latter radicals in the phenyl part can be substituted once to three times, in the same way or differently by Halogen, nitro, cyano, C r C 4 alkyl, C r C 4 alkoxy, C r C 4 alkylthio, haloalkyl with 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, haloalkoxy with 1 or 2 carbon atoms and 1 up to 5 identical or different halogen atoms and / or halogeno alkylthio with 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms.
  • R 3 preferably represents hydrogen or C j -C 4 alkyl.
  • R 4 preferably represents C 1 -C 12 -alkyl, C Cg-haloalkyl having 1 to 8 identical or different halogen atoms, CC 4 -hydroxyalkyl, C 2 -C 8 -halogenated alkenyl having 1 to 8 identical or different halogen atoms, C 2 -C 8 - alkynyl, C 2 -C 8 haloalkynyl with 1 to 8 halogen atoms, C j -C 8 alkoxy- C j -C 4 alkyl, C 2 -C 8 - alkenoxy-C j -C 4 alkyl , C 2 -C 8 - Alkinoxy-C -C 4 -alkyl 1, C j -C -haloalkoxy-C j -C 4 -alkyl with 1 to 8 identical or different
  • Halogen atoms C 2 -C 8 haloalkenyloxy -CC 4 -alkyl having 1 to 8 identical or different halogen atoms, C 2 -C 8 -halogenalkynyloxy-C ] -C 4 -alkyl having 1 to 8 identical or different halogen atoms, C j -C 8 -alkoxycarbonyl-C j -C 4 -alkyl, C j -C 8 -alkylcarbonyloxy-C j -C -alkyl, C j -C 8 -haloalkyl-carbonyloxy-Cj-C 4 -alkyl with 1 to 8 identical or different
  • Carbon atoms and 1 to 5 identical or different halogen atoms Alkylsulfmyl having 1 to 4 carbon atoms, alkylsulfonyl having 1 to 4 carbon atoms, alkylcarbonyl having 1 to 4 carbon atoms in the alkyl part and / or alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy part.
  • two geminal or vicinal R radicals together with the carbon atom (s) to which they are attached can preferably represent a saturated or unsaturated, five- or six-membered ring
  • the one or two oxygen - Can contain sulfur and / or nitrogen atoms and can be mono- or disubstituted by halogen, alkyl having 1 to 4 carbon atoms and / or alkoxy having 1 to 4
  • n is preferably 1, 2 or 3.
  • X preferably represents a nitrogen atom or a grouping of the formula
  • A also preferably represents a direct bond or a CH 2 group.
  • R 1 particularly preferably represents methyl, ethyl, propyl, isopropyl, n-butyl, i-
  • R 2 particularly preferably represents hydrogen, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, Butoxycarbonyl, i-butoxycarbonyl, sec.-butoxycarbonyl, tert.-butoxycarbonyl, phenylcarbonyl, phenyloxycarbonyl or phenylalkoxycarbonyl with 1 or 2 carbon atoms in the alkoxy part, where the last three radicals in the phenyl part can be substituted once or twice, in the same way or differently, by fluorine , Chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, chloromethyl, dichloromethyl, difluoromethyl, trifluoromethyl, trifluoromethoxy and / or trifluoromethylthio.
  • R 3 particularly preferably represents hydrogen, methyl or ethyl.
  • R 4 particularly preferably represents C 1 -C 8 -alkyl, haloalkyl with 1 to 8 carbon atoms and 1 to 8 fluorine, chlorine and / or bromine atoms, hydroxyalkyl with 1 or 2 carbon atoms, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl with 1 to 8 fluorine, chlorine and / or bromine atoms, C 2 -C 8 alkynyl, C 2 - C 8 haloalkynyl with 1 to 8 fluorine, chlorine and / or bromine atoms, C j -C 8 -
  • two geminal or vicinal R 4 radicals together with the carbon atom (s) to which they are attached can particularly preferably stand for a saturated or monounsaturated, six-membered ring
  • the one or two oxygen - can contain sulfur and / or nitrogen atoms and can be mono- or disubstituted by fluorine, chlorine, methyl, ethyl and / or methoxy.
  • n particularly preferably represents 1 or 2.
  • X particularly preferably represents a nitrogen atom or a grouping of the formula CH, CC1, CBr, C-CN, CC ⁇ CH or CC-NH 2 .
  • A also particularly preferably represents a direct bond or a CH 2 -
  • R 1 very particularly preferably represents methyl, ethyl, chloromethyl, difluoromethyl, trifluoromethyl, methoxymethyl, ethoxymethyl, methylthiomethyl,
  • R 2 very particularly preferably represents hydrogen, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, phenylcarbonyl, phenyloxycarbonyl or phenylmethoxycarbonyl, it being possible for the three latter radicals in the phenyl part to be mono- or disubstituted, identical or different, by fluorine, chlorine, bromine, nitro, cyano , Methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, chloromethyl, dichloromethyl, difluoromethyl, trifluoromethyl, trifluoromethoxy and / or trifluoromethylthio.
  • R 3 very particularly preferably represents hydrogen or methyl.
  • R 4 very particularly preferably represents C 1 -C 6 -alkyl, haloalkyl having 1 to 4 carbon atoms and 1 to 5 fluorine, chlorine and / or bromine atoms, hydroxymethyl, hydroxyethyl, C 2 -C 6 alkenyl, C 2 -C 6 -Halogenalkenyl with 1 to 5 fluorine, chlorine and / or bromine atoms, C 2 -C 6 alkynyl, C 2 -Cg-haloalkynyl with 1 to 5 fluorine, chlorine and / or bromine atoms, C j -Cg -Alkoxy-methyl, C 2 -C5 -alkenoxy-methyl, C 2 -C 6 -alkinoxy-methyl, C j -C 4 -halogenalkoxy-methyl with 1 to 3 fluorine, chlorine and / or bromine atoms, C 2 -C 4 - haloalkenyloxy-methyl with 1 to 3
  • C 2 -C 4 haloalkynyloxy-methyl with 1 to 3 fluorine, chlorine and / or bromine atoms C j -C 4 - alkoxy-carbonyl 1-methyl, C j -C - alkyl-carbonyloxy-methyl, C 1 -C -haloalkyl-carbonyloxy-methyl with 1 to 3 fluorine, chlorine and / or bromine atoms, C j -C 4 -alkylthio-methyl, or for phenyl, phenylalkyl with 1 or 2 carbon atoms in the alkyl part, phenylalkoxy with 1 or 2 Carbon atoms in the alkoxy part or for phenylmethyloxymethyl, where the four last-mentioned radicals in the phenyl part can be substituted once or twice, in the same way or differently, by fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy, eth
  • two geminal or vicinal R 4 radicals together with the carbon atom (s) to which they are attached can very particularly preferably stand for a saturated or mono-unsaturated, six-membered ring, the one or can contain two non-adjacent oxygen atoms and can be mono- or disubstituted by fluorine, chlorine, methyl, ethyl and / or methoxy.
  • X very particularly preferably represents 1 or 2.
  • X very particularly preferably represents a nitrogen atom or one
  • A also very particularly preferably represents a direct bond or a CH 2 group.
  • radical definitions can be combined with one another in any way.
  • individual definitions can also be omitted.
  • phenylacetic acid heterocyclylamides of the formula (I) according to the invention are the substances listed in the tables below.
  • Formula (II) provides a general definition of the amino derivatives required as starting materials when carrying out process (a) according to the invention.
  • R 1 , R 3 and X preferably have those meanings which have already been mentioned as preferred for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • the amino derivatives of the formula (II) have hitherto not been known. They can be made by Heterocyclyl amines of the formula
  • R 1 and X have the meanings given above,
  • R 3 has the meaning given above and
  • R 3 has the meaning given above
  • Formula (V) provides a general definition of the heterocyclic amines required as starting materials in carrying out process (c). Have in this formula
  • R 1 and X preferably have the meanings which have already been mentioned as preferred for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • heterocyclyl amines of the formula (V) are known or can be prepared by known methods (cf. DE-A 4 328 425, DE-A 2 249 162, WO 93-19 054, WO 94-21 617, J. Het Chem. 26, 1575 (1989), Gazz. Chim. Ital. 107, 1 (1977), Chem. Ber. 195, 57 and EP-A 0 455 356).
  • Formula (VI) provides a general definition of the acid halides required as reaction components when carrying out process (c, variant ⁇ ).
  • R 3 preferably has those meanings which have already been mentioned as preferred for this radical in connection with the description of the substances of the formula (I) according to the invention.
  • Hai ' preferably represents chlorine.
  • the acid halides of the formula (VI) are known or can be prepared by known methods (cf. Monthly Chem. 85, 80 (1954) and J. Chem. Soc. 1956, 404).
  • Formula (VII) provides a general definition of the phenylacetic acid derivatives required as reaction components when carrying out process (c, variant ⁇ ).
  • R 3 preferably has those meanings which have already been mentioned as preferred for this radical in connection with the description of the substances of the formula (I) according to the invention.
  • phenylacetic acid derivatives of the formula (VII) are also known or can be prepared by known methods (cf. the publications cited above).
  • Suitable acid binders for carrying out the process (c, variant ⁇ ) are all customary inorganic and organic bases.
  • Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, are preferably usable.
  • Diazabicyclooctane (DABCO), Diazabicyclononen (DBN) or Diazabicycloundecen (DBU).
  • Suitable diluents for carrying out process (c, variant ⁇ ) are all inert organic solvents.
  • Aliphatic, alicyclic or aromatic hydrocarbons such as 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 diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, 1, 2-diethoxyethane or anisole; Nitriles, such as acetoni- tril, propion
  • reaction temperatures can be varied within a substantial range when carrying out the process (c, variant ⁇ ). In general, temperatures between -10 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C.
  • process (c, variant ⁇ ) When carrying out process (c, variant ⁇ ), the process is carried out in the same way as when carrying out process (c, variant ⁇ ) and processes (a) and (b) in general under atmospheric pressure. However, it is also possible to work under increased or reduced pressure.
  • an equimolar amount of acid halide and an equivalent amount or an excess of acid binder are generally employed per mole of heterocyclic amine of the formula (V).
  • the processing takes place according to usual methods. In general, the procedure is such that the reaction mixture is concentrated after the reaction has ended, water and a water-immiscible organic solvent are added to the remaining residue, and the organic phase is separated off, washed, dried and concentrated. The remaining product can be freed of any impurities that may be present using customary methods.
  • Suitable catalysts for carrying out the process (c, variant ⁇ ) are all customary reaction accelerators which are suitable for activating the carboxyl group of the phenylacetic acid derivative of the formula (VII). Carbonyldiimidazole and dicyclohexylcarbodiimide can preferably be used. Furthermore, the reaction can also be carried out in the presence of water-binding agents. WO 00/20415 "., PCT / EP99 / 07105
  • Suitable diluents for carrying out the process (c, variant ⁇ ) are all inert organic solvents which are customary for such reactions.
  • Ahphatic, ahcyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane.
  • reaction temperatures can be varied within a certain range when carrying out the process (c, variant ⁇ ). In general, temperatures between 0 ° C and 80 ° C, preferably between 10 ° C and 70 ° C.
  • Formula (III) provides a general definition of the diols required as reaction components when carrying out process (a) according to the invention.
  • A, R 4 and n preferably have those meanings which have already been mentioned as preferred for these radicals or for this index in connection with the description of the substances of the formula (I) according to the invention.
  • the diols of the formula (III) are known or can be prepared by known methods.
  • Suitable diluents for carrying out process (a) according to the invention are all inert organic solvents which are customary for such reactions.
  • Aromatic hydrocarbons such as benzene, toluene or xylene can preferably be used.
  • Suitable water-releasing agents for carrying out process (a) according to the invention are all customary reagents which are capable of dehydration. Acids, such as sulfuric acid or p-toluenesulfonic acid, and also drying agents, such as anhydrous silica gel or molecular sieves, and furthermore formic acid orthoesters, can preferably be used.
  • reaction temperatures can also be varied within a substantial range when carrying out process (a) according to the invention. Generally one works at temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 130 ° C.
  • the phenylacetic acid heterocyclyl amides of the formula (Ia) required as starting materials when carrying out process (b) according to the invention are compounds according to the invention which can be prepared by process (a).
  • Formula (IV) provides a general definition of the acid halides required as reaction components when carrying out process (b) according to the invention. In this formula it says
  • R 5 preferably for C j -C 4 alkyl, Cj-C alkoxy, for phenyl, phenyloxy or
  • Phenyl-C j -C -alkyloxy where the last three radicals in the phenyl part can be monosubstituted to triple, identical or differently substituted by halogen, nitro, cyano, C r C 4 alkyl, C r C 4 alkoxy, C r C 4 - alkylthio, haloalkyl with 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, haloalkoxy with 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms and / or haloalkylthio with 1 or 2 carbon atoms and 1 to 5 same or different halogen atoms.
  • R 5 particularly preferably represents methyl, ethyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, i-butoxy, sec-butoxy, tert-butoxy, phenyl, phenyloxy or phenylalkoxy with 1 or 2 carbon atoms in the alkoxy part, where the three last-mentioned radicals in the phenyl part can be substituted once or twice, in the same way or differently, by fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, chloromethyl,
  • R 5 very particularly preferably represents methyl, ethyl, methoxy, ethoxy, phenyl, phenyloxy or phenylmethoxy, the three last-mentioned radicals in
  • Phenyl moiety can be substituted once or twice, in the same way or differently, by fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, chloromethyl, dichloromethyl, difluoromethyl, trifluoromethyl, trifluoromethoxy and / or trifluoromethylthio.
  • the acid halides of the formula (IV) are known or can be prepared by known methods.
  • Suitable acid binders for carrying out process (b) according to the invention are all customary inorganic and organic bases.
  • Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium acetate, are preferably usable.
  • DABCO diazabicyclooctane
  • DBN diazabicyclonones
  • DBU diazabicycloundecene
  • Suitable diluents for carrying out process (b) according to the invention are all inert organic solvents.
  • Ahphatic, ahcyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or are preferably usable
  • halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane
  • Ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, 1, 2-diethoxyethane or anisole
  • Nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile
  • Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide
  • Esters such as methyl acetate or ethyl acetate
  • Sulfoxides such
  • reaction temperatures can be carried out when carrying out the process according to the invention.
  • Process (b) can be varied within a wide range. In general one works at temperatures between -10 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C.
  • Acid halide of formula (IV) and an equivalent amount or an excess of acid binder takes place according to usual methods. In general, the reaction mixture is concentrated after the reaction has ended, water and a water-immiscible organic solvent are added to the remaining residue, and the organic phase is separated off, washed, dried and concentrated. The remaining product can be freed of any impurities that may be present using customary methods.
  • the active compounds according to the invention are suitable for controlling unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.
  • Fungicides can be used in crop protection to combat Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.
  • Bactericides can be used in crop protection to control Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • Xanthomonas species such as Xanthomonas campestris pv. Oryzae
  • Pseudomonas species such as Pseudomonas syringae pv. Lachrymans
  • Erwinia species such as Erwinia amylovora
  • Pythium species such as Pythium ultimum
  • Phytophthora species such as Phytophthora infestans
  • Pseudoperonospora species such as Pseudoperonospora humuli or Pseudoperonospora cubensis
  • Plasmopara species such as Plasmopara viticola
  • Bremia species such as Bremia lactucae
  • Peronospora species such as Peronospora pisi or P. brassicae
  • Erysiphe species such as Erysiphe graminis
  • Sphaerotheca species such as Sphaerotheca fuliginea
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Venturia species such as Venturia inaequalis
  • Pyrenophora species such as Pyrenophora teres or P.
  • graminea dial form: Drechslera, Syn: Helminthosporium
  • Cochliobolus species such as Cochliobolus sativus (conidial form: Drechslera, Syn: Helminthosporium);
  • Uromyces species such as Uromyces appendiculatus
  • Puccinia species such as Puccinia recondita
  • Sclerotinia species such as Sclerotinia sclerotiorum
  • Tilletia species such as Tilletia caries
  • Ustilago species such as Ustilago nuda or Ustilago avenae
  • Pellicularia species such as Pellicularia sasakii
  • Pyricularia species such as Pyricularia oryzae
  • Fusarium species such as Fusarium culmorum
  • Botrytis species such as Botrytis cinerea
  • Septoria species such as Septoria nodorum
  • Leptosphaeria species such as Leptosphaeria nodorum
  • Cercospora species such as Cercospora canescens
  • Alternaria species such as, for example, Alternaria brassicae;
  • Pseudocercosporella species such as Pseudocercosporella herpotrichoides.
  • the fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases permits treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.
  • the active compounds according to the invention can be used with particularly good success for combating cereal diseases, such as mildew, and against diseases in wine, fruit and vegetable cultivation, such as Venturia, Podosphaera and Plasmo-para species. They also have good in vitro activity against oomycetes.
  • the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
  • technical materials which are to be protected against microbial change or destruction by active substances according to the invention can be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which can be attacked or decomposed by microorganisms .
  • parts of production plants, for example cooling water circuits are also mentioned which can be impaired by the multiplication of microorganisms.
  • the preferred technical materials are adhesives, glues, papers and cartons, leather, wood,
  • microorganisms of the following genera may be mentioned:
  • Altemaria such as Alternaria tenuis, Aspergillus, such as Aspergillus niger, Chaetomium, such as Chaetomium globosum, Coniophora, such as Coniophora puetana, Lentinus, such as Lentinus tigrinus, Penicillium, such as Penicillium versicolor,
  • Aureobasidium such as Aureobasidium pullulans
  • Sclerophoma such as Sclerophoma pityophila
  • Trichoderma such as Trichoderma viride
  • Escherichia such as Escherichia coli
  • Pseudomonas such as Pseudomonas aeruginosa
  • Staphylococcus such as Staphylococcus aureus.
  • the active compounds according to the invention are also suitable for combating animal pests, in particular insects, arachnids and nematodes which are used in agriculture, in good plant tolerance and favorable warm-blood toxicity
  • Thysanura for example Lepisma saccharina.
  • Collembola for example Onychiurus armatus.
  • Orthoptera e.g. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.
  • Homoptera
  • Cacoecia podana Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.
  • Leptinotarsa decemlineata Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatordimidhmpphppm, spp.
  • Anthrenus spp. Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha., Amphimalltra solitus
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp.
  • Siphonaptera for example Xenopsylla cheopis, Ceratophyllus spp.
  • Arachnida for example Scorpio maurus, Latrodectus mactans.
  • Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,
  • Chorioptes spp. Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.
  • Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp.
  • Pratylenchus spp. Radopholus similis
  • Ditylenchus dipsaci Ditylenchus dipsaci
  • Tylenchulus semipenetrans Heterodera spp.
  • Globodera spp. Meloidogyne spp.
  • Aphelenchoides spp. Longidorus spp.
  • Xiphinema spp. Trichodorus spp.
  • the substances which can be used according to the invention can be used with particularly good success for combating mites which damage plants, such as bean spider mite (Tetranychus urticae), or for controlling insects which damage plants, such as the caterpillar caterpillars (Plutella maculipennis), the larvae of the horseradish beetle ( Phaedon cochleariae) and green rice leafhopper (Nephotettix cincticeps).
  • mites which damage plants such as bean spider mite (Tetranychus urticae)
  • insects which damage plants such as the caterpillar caterpillars (Plutella maculipennis), the larvae of the horseradish beetle ( Phaedon cochleariae) and green rice leafhopper (Nephotettix cincticeps).
  • the substances which can be used according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice and hair lice , Featherlings and fleas.
  • animal parasites ectoparasites
  • tick ticks such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice and hair lice , Featherlings and fleas.
  • Anoplurida for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp ..
  • Mallophagida and the subordinates Amblycerina and Ischnocerina for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.
  • Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota ., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Glossina spp., Calliphora spp., Glossina spp., Calliphora spp
  • Siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
  • Hyalomma spp. Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp.
  • Actinedida Prostigmata
  • Acaridida Acaridida
  • Acarapis spp. Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp.
  • Tyrophagus spp. Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
  • the active compounds according to the invention are also suitable for increasing the crop yield.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols,
  • formulations are made in a known manner, e.g. 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.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • water e.g. organic solvents can also be used as auxiliary solvents.
  • aromatics such as
  • chlorinated aromatics or chlorinated ahphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • ahphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions
  • alcohols such as butanol or glycol
  • 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 flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diato- sea earth and synthetic rock powder, such as highly disperse silica, aluminum oxide and silicates.
  • Possible solid carriers for granules are: e.g.
  • emulsifiers and / or foaming agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • Possible dispersants are, for example, lignin sulfite liquor and methyl cellulose.
  • 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, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt,
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt,
  • Molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • 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.
  • the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the activity spectrum or to prevent the development of resistance. In many cases, synergistic effects are obtained, ie the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Debacarb dichlorophene, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomo h, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrifhione, ditalimfos, dorphianon, dithianon
  • copper preparations such as: copper hydroxide, 5 copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxyne copper and
  • Paclobutrazole pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidon, propamocarb, propanosine sodium, propiconazole, propineb, pyrazophos, pyrifen, pyifenox, pyrroyilonil
  • Tebuconazole Tecloftalam, Tecnazen, Tetcyclacis, Tetraconazole, Thiabendazole, Thicyofen, Thifluzamide, Thiophanate-methyl, Thiram, Tioxymid, Tolclofos-methyl,
  • Tolylfluanid Triadimefon, Triadimenol, Triazbutil, Triazoxid, Trichlamid, Tricyclazol, Tridemorph, Triflumizol, Triforin, Triticonazol,
  • Bactericides bronopol, dichlorophene, nitrapyrin, nickel-dimethyldithiocarbamate, kasugamycin,
  • Fenamiphos fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb, fenoxacrim
  • Fenoxycarb Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxuron, Flucythrinate, Flufenoxuron, Flutenzine, Fluvalinate, Fonophos, Fosmethilan, Fathhocproxate, Fosthiazproate,
  • Granulosis viruses Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene, Imidacloprid, Isazofos, Isofenphos, Isoxathion, Ivermectin,
  • Metolcarb Metoxadiazone, Mevinphos, Milbemectin, Monocrotophos,
  • 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,
  • Bacillus thuringiensis strain EG-2348 Bacillus thuringiensis strain EG-2348,
  • 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.
  • Application takes place in the usual way, e.g. by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients using the ultra-low-volume process or to inject the active ingredient preparation or the active ingredient into the soil itself.
  • the seeds of the plants can also be treated.
  • the application rates can be varied within a relatively wide range, depending on the type of application.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.
  • the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • the agents used to protect industrial materials generally contain the active ingredients in an amount of 1 to 95%, preferably 10 to 75%.
  • the application concentrations of the active compounds according to the invention depend on the type and the occurrence of the microorganisms to be controlled and on the composition of the material to be protected.
  • the optimal amount can be determined by test series.
  • the application concentrations are in the range from 0.001 to 5% by weight, preferably from 0.05 to 1.0% by weight, based on the material to be protected.
  • the effectiveness and the spectrum of activity of the active substances to be used according to the invention in the protection of materials or of the agents, concentrates or very generally formulations which can be produced therefrom can be increased if further antimicrobial compounds, fungicides, bactericides, herbicides, insecticides or other active substances are used to enlarge the spectrum of activity or
  • the substances according to the invention can also be present in commercially available formulations and in the use forms prepared from these formulations as a mixture with synergists.
  • Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • Solessc e present in all cases. Specified higher log p-value. Manufacture of starting substances
  • reaction mixture is stirred for 16 hours at room temperature, then washed with 1N HCl, dried over sodium sulfate and concentrated in vacuo, by stirring the residue thus obtained with diethyl ether, 16.9 g (69% of theory) 5- [3- (Acetylphenyl) - acetaminol] -4-chloro-3-methyl-isothiazole isolated in the form of a solid.
  • Emulsifier 3 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are sprayed with an aqueous spore suspension of Plasmopara viticola and then remain in an incubation cabin at about 20 ° C. and 100% relative atmospheric humidity for 1 day.
  • the plants are then placed in a greenhouse for 5 days at approx. 21 ° C and approx. 90% relative humidity.
  • the plants are then moistened and placed in an incubation cabin for 1 day.
  • Emulsifier 3 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Emulsifier 0.6 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80% in order to promote the development of mildew pustules.
  • Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Rice seedlings (Oryza sativa) are treated by dipping into the active ingredient preparation of the desired concentration and populated with larvae of the green rice leafhopper (Nephotettix cincticeps) while the seedlings are still moist.
  • the kill is determined in%. 100% means that all cicadas have been killed; 0% means that no cicadas have been killed.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with horseradish leaf beetle larvae (Phaedon cochleariae) while the leaves are still moist.
  • the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active ingredient of the desired concentration and populated with caterpillars of the army worm Spodoptera frugiperda while the leaves are still moist.
  • the effect is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted to the desired concentrations with water containing emulsifier.
  • Bean plants Phaseolus vulgaris which are heavily infested with all stages of the common spider mite (Tetranychus urticae) are immersed in a preparation of active compound of the desired concentration.
  • the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

L'invention concerne de nouveaux hétérocyclylamides d'acide phénylacétique de formule (I) dans laquelle R<1>, R<2>, R<3>, R<4>, A, X et n ont les significations données dans la description. L'invention concerne également un procédé pour produire ces nouvelles substances et leur utilisation pour lutter contre des micro-organismes indésirables et des parasites animaux (insecticides). L'invention concerne également de nouveaux produits intermédiaires de la formule (II) et plusieurs procédés pour leur production.
EP99948849A 1998-10-06 1999-09-23 Heterocyclylamides d'acide phenylacetique ayant un effet insecticide Withdrawn EP1119569A1 (fr)

Applications Claiming Priority (3)

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DE19846008A DE19846008A1 (de) 1998-10-06 1998-10-06 Phenylessigsäure-heterocyclylamide
DE19846008 1998-10-06
PCT/EP1999/007105 WO2000020415A1 (fr) 1998-10-06 1999-09-23 Heterocyclylamides d'acide phenylacetique ayant un effet insecticide

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US6777217B1 (en) 1996-03-26 2004-08-17 President And Fellows Of Harvard College Histone deacetylases, and uses related thereto
US20030129724A1 (en) 2000-03-03 2003-07-10 Grozinger Christina M. Class II human histone deacetylases, and uses related thereto
US7244853B2 (en) 2001-05-09 2007-07-17 President And Fellows Of Harvard College Dioxanes and uses thereof
WO2005040143A1 (fr) * 2003-10-27 2005-05-06 Basf Aktiengesellschaft Composes 5-(2-arylacetamido)isothiazole ii
AU2006226861B2 (en) 2005-03-22 2012-08-16 Dana-Farber Cancer Institute, Inc. Treatment of protein degradation disorders
BRPI0707826B1 (pt) 2006-02-14 2022-04-19 Dana-Farber Cancer Institute, Inc. Compostos inibidores de histona desacetilase, composição farmacêutica e uso dos referidos compostos
AU2007345292B2 (en) 2006-02-14 2013-10-31 Dana-Farber Cancer Institute, Inc. Bifunctional histone deacetylase inhibitors
AU2007248656B2 (en) 2006-05-03 2013-04-04 Dana-Farber Cancer Institute, Inc. Histone deacetylase and tubulin deacetylase inhibitors
US8440716B2 (en) 2008-07-23 2013-05-14 President And Fellows Of Harvard College Deacetylase inhibitors and uses thereof
US8716344B2 (en) 2009-08-11 2014-05-06 President And Fellows Of Harvard College Class- and isoform-specific HDAC inhibitors and uses thereof
WO2014002106A1 (fr) * 2012-06-25 2014-01-03 Cadila Healthcare Limited Nouveaux composés pour le traitement de la dyslipidémie et de maladies associées

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE790010A (fr) 1971-10-15 1973-04-12 Fmc Corp Herbicides nouveaux
US4895849A (en) * 1986-10-08 1990-01-23 Ube Industries, Ltd. Aralkylaminopyrimidine compounds which are useful as for producing thereof and insecticides
DE3864839D1 (de) * 1987-01-19 1991-10-24 Ciba Geigy Ag Substituierte dioxolanderivate.
GB9008123D0 (en) 1990-04-10 1990-06-06 Lilly Industries Ltd Pharmaceutical compounds
TW231257B (fr) * 1992-03-02 1994-10-01 Ciba Geigy
EP0586686A1 (fr) 1992-03-26 1994-03-16 Dowelanco Nitro-anilines n-heterocycliques utilisees comme fongicides
WO1994021617A1 (fr) 1993-03-19 1994-09-29 Dowelanco Procede de preparation d'isothiazoles halogenes
EP0623282A1 (fr) * 1993-05-05 1994-11-09 Shell Internationale Researchmaatschappij B.V. Procédés et composés pesticides
DE4328425A1 (de) 1993-08-24 1995-03-02 Basf Ag Acylamino-substituierte Isoxazol- bzw. Isothiazolderivate, Verfahren zu deren Herstellung und ihre Verwendung
ES2138653T3 (es) * 1993-12-30 2000-01-16 Novartis Ag Eteres fenilicos substituidos.
AU2641295A (en) * 1994-05-17 1995-12-05 Dowelanco N-(5-isothiazolyl)amide pesticides
DE19542372A1 (de) 1995-11-14 1997-05-15 Bayer Ag Acylierte 5-Aminoisothiazole
DE19601139A1 (de) * 1996-01-15 1997-07-17 Bayer Ag Acylierte 5-Amino-1,2,4-thiadiazole
DE19628569A1 (de) 1996-07-16 1998-01-22 Bayer Ag Substituierte N-(5-Isothiazolyl)-thioamide
DE19630814A1 (de) * 1996-07-31 1998-02-05 Bayer Ag Substituierte N-Isothiazolyl-(thio)amide
DE19715017A1 (de) * 1997-04-11 1998-10-15 Bayer Ag Substituierte Aryluracile

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0020415A1 *

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DE19846008A1 (de) 2000-04-13
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WO2000020415A1 (fr) 2000-04-13
AU6195899A (en) 2000-04-26
JP2002526541A (ja) 2002-08-20
US6403622B1 (en) 2002-06-11

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