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WO1996005170A1 - 4-trifluoromethylbenzamides et leur utilisation sous forme de pesticides dans la protection phytosanitaire et la protection des materiaux - Google Patents

4-trifluoromethylbenzamides et leur utilisation sous forme de pesticides dans la protection phytosanitaire et la protection des materiaux Download PDF

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Publication number
WO1996005170A1
WO1996005170A1 PCT/EP1995/003026 EP9503026W WO9605170A1 WO 1996005170 A1 WO1996005170 A1 WO 1996005170A1 EP 9503026 W EP9503026 W EP 9503026W WO 9605170 A1 WO9605170 A1 WO 9605170A1
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Prior art keywords
methyl
chain
carbon atoms
straight
compounds
Prior art date
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PCT/EP1995/003026
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German (de)
English (en)
Inventor
Dietmar Kuhnt
Michael Haug
Klaus Jelich
Klaus Stenzel
Heinz-Wilhelm Dehne
Gerd Hänssler
Ulrike Wachendorff-Neumann
Christoph Erdelen
Martin Kugler
Heinrich Schrage
Original Assignee
Bayer Aktiengesellschaft
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Publication date
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU33822/95A priority Critical patent/AU3382295A/en
Publication of WO1996005170A1 publication Critical patent/WO1996005170A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—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
    • A01N37/38—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 having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—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 having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/64—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/68—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom and to a carbon atom of a six-membered aromatic ring wherein at least one ortho-hydrogen atom has been replaced
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C07C255/60—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton at least one of the singly-bound nitrogen atoms being acylated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/40—Y being a hydrogen or a carbon atom
    • C07C323/42—Y being a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/415—Amides of aromatic carboxylic acids; Acylated aromatic amines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic

Definitions

  • Amino, aminocarbonyl in each case straight-chain or branched alkylamino, alkylaminocarbonyl, dialkylamino or dialkylaminocarbonyl each having 1 to 4 carbon atoms in the individual alkyl parts; each straight-chain or branched alkenyl, alkenyloxy or alkenylthio each having 2 to 4 carbon atoms; and optionally phenyl which is monosubstituted to trisubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms.
  • Aklylthio each with 1 to 6 carbon atoms; each straight-chain or branched haloalkyl; Halogenalkoxy or haloalkylthio with each 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms; each straight-chain or branched alkoxycarbonyl or alkoximino-alkyl each having 1 to 4 carbon atoms in the individual alkyl parts; Amino, aminocarbonyl; in each case straight-chain or branched alkylamino, alkylaminocarbonyl, dialkylamino or dialkylaminocarbonyl each having 1 to 4 carbon atoms in the individual alkyl parts; each straight-chain or branched alkenyl, alkenyloxy or alkenylthio each having 2 to 4 carbon atoms; and optionally phenyl which is monosubstituted to trisubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl
  • Alkoxy or aklylthio each having 1 to 6 carbon atoms; each straight-chain or branched haloalkyl; Haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms; each straight-chain or branched alkoxycarbonyl or alkoximino-alkyl each having 1 to 4 carbon atoms in the individual alkyl parts; Amino, aminocarbonyl; in each case straight-chain or branched alkylamino, alkylaminocarbonyl, dialkylamino or dialkylaminocarbonyl each having 1 to 4 carbon atoms in the individual alkyl parts; each straight-chain or branched alkenyl, alkenyloxy or alkenylthio each having 2 to 4 carbon atoms; and optionally phenyl which is monosubstituted to trisubstituted, identically or differently, by halogen and / or straight-chain or
  • Cyano nitro; each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 6 carbon atoms; each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms; each straight-chain or branched alkoxycarbonyl or alkoximino-alkyl each having 1 to 4 carbon atoms in the individual alkyl parts; Amino, aminocarbonyl; in each case straight-chain or branched alkylamino, alkylaminocarbonyl, dialkylamino or dialkylaminocarbonyl each having 1 to 4 carbon atoms in the individual alkyl parts; each straight-chain or branched alkenyl, alkenyloxy or alkenylthio each having 2 to 4 carbon atoms; and optionally phenyl which is monosubstituted to trisubstituted,
  • Methoxycarbonyl ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl;
  • aminocarbonyl methylamino, ethylamino, n- or i-propylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, Dimethylaminocarbonyl, ethylmethylaminocarbonyl, methyl-n-propylaminocarbonyl, methyl-i-propylaminocarbonyl, diethylaminocarbonyl, propenyl, butenyl, isobutyl, propenyloxy, butenyloxy, isobutenyloxy, propenylthio, butenylthio, isobutenylthio; or phenyl which is optionally mono- to trisubstituted,
  • aminocarbonyl methylamino, ethylamino, n- or i-propylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, ethylmethylamino, methyl-n-propylamino, methyl-i-propylamino, diethylamino, Dimethylaminocarbonyl, ethylmethylaminocarbonyl, methyl-n-propyl-aminocarbonyl, methyl-i-
  • R- for fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl; n-, i-, s- or t-pentyl; Methoxy, ethoxy, n- or i-propoxy; n-, i-, s- or t-butoxy; Methylthio, ethylthio, n- or i- Propylthio; n-, i-, s- or t-butylthio; Trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, e
  • R 4 represents methyl
  • R ⁇ and R 2 or R- and R 4 or R 3 and R 4 together represent methylenedioxo, ethylenedioxo, difluoromethylenedioxo or tetrafluoroethylenedioxo. If, for example, 2-hydroxy-4-trifluoromethylbenzoic acid and 3-chloro-4-fluoroaniline are used as starting materials, the course of the reaction of the process according to the invention can be represented by the following formula:
  • Formula (IT) provides a general definition of the 2-hydroxy-4-trifluoromethylbenzoic acid required as the starting material for carrying out the process according to the invention, or the esters thereof.
  • R preferably represents hydrogen or straight-chain or branched alkyl having 1 to 4 carbon atoms.
  • the 2-hydroxy-4-trifluoromethylbenzoic acid or its esters are known (cf. e.g. WO-A 92/17066).
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between -60 ° C and 220 ° C, preferably at temperatures between 20 ° C and 180 ° C.
  • Pythium species such as, for example, Pythium ultimum
  • Phytophthora species such as, for example, Pseudoperonospora humuli or Pseudopero- nospora cubensis;
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae;
  • Erysiphe species such as, for example, Erysiphe graminis
  • Tilletia species such as, for example, Tilletia caries
  • the active compounds according to the invention can be used with particularly good results to combat diseases in fruit and vegetable production, such as, for example, against the pathogen causing tomato brown rot (Phytophthora infestans) or against the pathogen causing downy mildew on vines (Plasmopara viticola) or for combating cereal diseases, such as For example, against the pathogen causing brown furs in wheat (Septoria nodorum) or against the pathogen causing brown spot disease on barley or wheat (Cochliobolus sativus) or against the pathogen causing net spot disease on barley (Pyrenophora teres) or for combating rice diseases, such as against Rice stain pathogen (Pyricularia oryzae) or against the rice stem disease (Pellicularia sasakii).
  • diseases in fruit and vegetable production such as, for example, against the pathogen causing tomato brown rot (Phytophthora infestans) or against the pathogen causing downy mildew on
  • Diplopoda e.g. Blaniulus guttulatus.
  • Chilopoda e.g. Geophilus carpophagus
  • S cutiger a spec.
  • Symphyla e.g. S cutiger ella immaculata.
  • Thysanura e.g. Lepisma saccharina.
  • Collembola e.g. Onychiurus armatus.
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.
  • Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodoniphascei, spp.
  • Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodoniphasce
  • Coniophora such as Coniophora souna
  • Lentinus such as Lentinus tigrinus
  • Penicillium such as Penicillium glaucum
  • Polyporus such as Polyporus versicolor
  • Pseudomonas such as Pseudomonas aeruginosa
  • Adhesives such as carboxymethyl cellulose, natural and synthetic, powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • 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 do this Spectrum of effects to spread or prevent 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.
  • Difenoconazole dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine
  • Etrimphos Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb,
  • HCH Heptenophos, Hexaflumuron, Hexythiazox, Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivemectin,
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet,
  • seed treatment when used as fungicides, amounts of active ingredient of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.
  • the active compounds according to the invention can be present in their commercially available formulations and in the use forms prepared from the formulations in a mixture with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms and others The following connections are mentioned:
  • the agents used to protect technical materials generally contain the active ingredients in an amount of 1 to 95%, preferably 10 to 75%.
  • Iodine derivatives such as diiodomethyl-p-arylsulfones e.g. Diiodomethyl p-tolyl sulfone;
  • Organic tin compounds such as tributyltin naphtenate and tributyltin oxide;
  • Phosphoric acid esters such as azinphos-ethyl, azinphos-methyl, l- (4-chl ⁇ henyl) -4- (O-ethyl, S-propyl) phosphoryloxypyrazole (TIA-230), Chlo ⁇ yrifos, Coumaphos, Demetone, Demeton-S-methyl, Diazinon, Dichlorfos, Dimethoate, Ethoprophos, Etrimfos, Fenitrothion, Fention, Heptenophos, Parathion, Parathion-methyl, Phosalone, Phoxim, Pirimiphos-ethyl, Pirimiphos-methyl, Profenofos, Prothiofos, Sulprofos, Triazophon and Trichlo ⁇ .
  • Chlo ⁇ yrifos Coumaphos, Demetone, Demeton-S-methyl, Diazinon, Dichlorfos, Dimethoate, Ethoprophos, Etrim
  • Solvent 4.7 parts by weight of acetone emulsifier 0.3 parts by weight of alkyl aryl 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 an incubation cabin with 100% relative humidity and approx. 20 ° C.
  • Evaluation is carried out 3 days after the inoculation.
  • Example B the compounds of Examples 1, 2, 5, 6, 7, 12, 13, 14, 15, 17, 19, 20, 21, 22, 25, 26, 27, 28, 29, 34, 38, 39, 41, 42, 48, 64, 66, 87, 94, 96, 97, 104 and 105 at an active ingredient concentration of 10 ppm an efficiency of 70% to 100%, while the comparison substance (C) has an efficiency of 15% .
  • Example B the compounds of Examples 1, 2, 5, 6, 7, 12, 13, 14, 15, 17, 19, 20, 21, 22, 25, 26, 27, 28, 29, 34, 38, 39, 41, 42, 48, 64, 66, 87, 94, 96, 97, 104 and 105 at an active ingredient concentration of 10 ppm an efficiency of 70% to 100%, while the comparison substance (C) has an efficiency of 15% .
  • Example B the comparison substance (C) has an efficiency of 15% .
  • 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.
  • young plants are sprayed with the active ingredient preparation to drip-hate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Plasmopara viticola and then remain in a moist chamber at 20-22 ° C. and 100% relative atmospheric humidity for 1 day. The plants are then placed in a greenhouse at 21 ° C. and 90% humidity for 5 days. The plants are then moistened and placed in a moisture chamber for 1 day.
  • Solvent 12.5 parts by weight of acetone emulsifier 0.3 parts by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and the concentrate is diluted with water and the stated amount of emulsifier to the desired concentration.
  • Solvent 31 parts by weight of acetone emulsifier, 1 part by weight of alkyl aryl 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.
  • Cabbage leaves (Brassica oleracea) are treated with the active ingredient preparation of the desired concentration. A treated leaf is placed in the plastic can and filled with larvae (L2) of the cockroach (PluteUa xylosteüa). After 3 days, an untreated sheet is used for refilling.
  • the kill is determined in%. 100% means that all animals have been killed; 0% means that no animals have been killed.
  • Tatranychus test (OP-resistant / diving treatment)
  • Solvent 7 parts by weight of acetone emulsifier, 1 part by weight of alkyl aryl 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.
  • the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
  • Solvent 7 parts by weight of dimethylformamide emulsifier, 1 part by weight of alkyl aryl 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 concentrations.
  • Cabbage leaves (Brassica oleracea) are treated by dipping into the active ingredient preparation 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.
  • Cabbage leaves (Brassica oleracea) are treated by dipping into the active ingredient preparation of the desired concentration and populated with caterpillars of the cockroach (Plutella maculipennis) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Colonies of Gloeophyüum trabeum, Coniophora tenuina, Poria placenta, Lentinus tigrinus, Coriolus versicolor and Stereum sanguinolentum were excised and mycelium pieces were incubated at 26 ° C on an agar medium containing malt extract peptone.
  • the inhibition of hyphal growth on active nutrient media was compared with the lengthy growth on nutrient media without the addition of an active ingredient and rated as a percentage inhibition.
  • the compounds of Examples 1, 3, 17, 34, 38 and 92 according to the invention show an inhibition of growth of 50 to 100% at an active substance concentration of 20 ppm.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Pest Control & Pesticides (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Agronomy & Crop Science (AREA)
  • Biochemistry (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Microbiology (AREA)
  • Wood Science & Technology (AREA)
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  • Environmental Sciences (AREA)
  • Hydrology & Water Resources (AREA)
  • Environmental & Geological Engineering (AREA)
  • Water Supply & Treatment (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne de nouveaux 4-trifluorométhylbenzamides de formule (I), leur procédé de fabrication et leur utilisation sous forme de pesticides dans la protection phytosanitaire et la protection des matériaux.
PCT/EP1995/003026 1994-08-11 1995-07-31 4-trifluoromethylbenzamides et leur utilisation sous forme de pesticides dans la protection phytosanitaire et la protection des materiaux WO1996005170A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU33822/95A AU3382295A (en) 1994-08-11 1995-07-31 4-trifluoromethylbenzamides and their use as pesticides in plant and materials protection

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4428380.6 1994-08-11
DE19944428380 DE4428380A1 (de) 1994-08-11 1994-08-11 4-Trifluormethylbenzamide

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WO2003016300A1 (fr) * 2001-08-15 2003-02-27 E. I. Du Pont De Nemours And Company Amides d'aryle a substitution ortho utilises dans le controle des depredateurs invertebres
WO2005072681A3 (fr) * 2004-01-23 2005-09-22 Amgen Inc Ligands des recepteurs vanilloides et utilisation de ceux-ci dans divers traitements
RU2278852C2 (ru) * 2000-03-22 2006-06-27 Е.И.Дюпон Де Немур Энд Компани Инсектицидные антраниламиды
CN100347162C (zh) * 2002-02-07 2007-11-07 诺瓦提斯公司 N－苯基－2－嘧啶胺衍生物
EP1542699A4 (fr) * 2002-07-15 2009-03-25 Myriad Genetics Inc Composes, compositions et methodes d'utilisation de ces derniers
US20170332635A1 (en) * 2013-11-12 2017-11-23 Nihon Nohyaku Co., Ltd. Amide compound or salt thereof, agricultural and horticultural insecticide and microbicide comprising the compound, and method for using the insecticide and microbicide

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US7319112B2 (en) 2000-07-14 2008-01-15 The Procter & Gamble Co. Non-halogenated antibacterial agents and processes for making same
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AR036872A1 (es) 2001-08-13 2004-10-13 Du Pont Compuesto de antranilamida, composicion que lo comprende y metodo para controlar una plaga de invertebrados
RU2004107485A (ru) 2001-08-15 2005-03-27 Е.И.Дюпон де Немур энд Компани (US) Орто-гетероциклические замещенные ариламиды для борьбы с беспозвоночными вредителями
KR100869002B1 (ko) 2001-08-16 2008-11-17 이 아이 듀폰 디 네모아 앤드 캄파니 무척추 해충 방제를 위한 치환된 안트라닐아미드
ES2271371T3 (es) 2001-09-21 2007-04-16 E. I. Du Pont De Nemours And Company Antranilamidas artropodicidas.
TW200724033A (en) 2001-09-21 2007-07-01 Du Pont Anthranilamide arthropodicide treatment
JP4317752B2 (ja) 2001-10-15 2009-08-19 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 無脊椎害虫を防除するためのイミノベンゾオキサジン、イミノベンズチアジンおよびイミノキナゾリン
AU2007203463B2 (en) * 2002-02-07 2010-12-23 Novartis Pharma Ag N-phenyl-2-pyrimidine-amine derivatives
US10640457B2 (en) 2009-12-10 2020-05-05 The Trustees Of Columbia University In The City Of New York Histone acetyltransferase activators and uses thereof
CN106432137B (zh) 2010-12-22 2020-11-06 纽约市哥伦比亚大学理事会 组蛋白乙酰转移酶调节剂和其用途
CA2838844A1 (fr) 2011-06-10 2012-12-13 The Trustees Of Columbia University In The City Of New York Utilisations d'activateurs d'histone acetyl tansferase

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FR2234274A1 (fr) * 1973-06-25 1975-01-17 Yoshitomi Pharmaceutical
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Cited By (12)

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RU2278852C2 (ru) * 2000-03-22 2006-06-27 Е.И.Дюпон Де Немур Энд Компани Инсектицидные антраниламиды
WO2003016300A1 (fr) * 2001-08-15 2003-02-27 E. I. Du Pont De Nemours And Company Amides d'aryle a substitution ortho utilises dans le controle des depredateurs invertebres
RU2283839C2 (ru) * 2001-08-15 2006-09-20 Е.И.Дюпон Де Немур Энд Компани Ортозамещенные ариламиды, способ борьбы с насекомыми, композиция для борьбы с насекомыми, промежуточное соединение
US7288554B2 (en) 2001-08-15 2007-10-30 E.I. Du Pont De Nemours And Company Ortho-substituted aryl amides for controlling invertebrate pests
AU2002331706B2 (en) * 2001-08-15 2009-01-22 E.I. Du Pont De Nemours And Company Ortho-substituted aryl amides for controlling invertebrate pests
CN100528862C (zh) * 2001-08-15 2009-08-19 纳幕尔杜邦公司 用于控制无脊椎害虫的邻位取代的芳基酰胺化合物
CN100347162C (zh) * 2002-02-07 2007-11-07 诺瓦提斯公司 N－苯基－2－嘧啶胺衍生物
EP1542699A4 (fr) * 2002-07-15 2009-03-25 Myriad Genetics Inc Composes, compositions et methodes d'utilisation de ces derniers
US7547804B2 (en) 2002-07-15 2009-06-16 Myriad Genetics, Inc. Compounds, compositions, and methods employing same
WO2005072681A3 (fr) * 2004-01-23 2005-09-22 Amgen Inc Ligands des recepteurs vanilloides et utilisation de ceux-ci dans divers traitements
US20170332635A1 (en) * 2013-11-12 2017-11-23 Nihon Nohyaku Co., Ltd. Amide compound or salt thereof, agricultural and horticultural insecticide and microbicide comprising the compound, and method for using the insecticide and microbicide
US10123537B2 (en) * 2013-11-12 2018-11-13 Nihon Nohyaku Co., Ltd. Amide compound or salt thereof, agricultural and horticultural insecticide and microbicide comprising the compound, and method for using the insecticide and microbicide

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DE4428380A1 (de) 1996-02-15
AU3382295A (en) 1996-03-07

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