EP0863867A2 - Fluorobutenylesters d'acide aminocarboxylique - Google Patents

Fluorobutenylesters d'acide aminocarboxylique

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Publication number
EP0863867A2
EP0863867A2 EP96939836A EP96939836A EP0863867A2 EP 0863867 A2 EP0863867 A2 EP 0863867A2 EP 96939836 A EP96939836 A EP 96939836A EP 96939836 A EP96939836 A EP 96939836A EP 0863867 A2 EP0863867 A2 EP 0863867A2
Authority
EP
European Patent Office
Prior art keywords
spp
formula
compounds
iii
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.)
Ceased
Application number
EP96939836A
Other languages
German (de)
English (en)
Inventor
Udo Kraatz
Wolfram Andersch
Andreas Turberg
Norbert Mencke
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
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Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0863867A2 publication Critical patent/EP0863867A2/fr
Ceased 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic 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
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—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
    • A01N43/04—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 one hetero atom
    • A01N43/06—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 one hetero atom five-membered rings
    • A01N43/10—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 one hetero atom five-membered rings with sulfur as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms 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
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms 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
    • C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms 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 having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • 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
    • C07C233/81—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • 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
    • C07C233/81—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—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
    • 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
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
    • C07D263/36—One oxygen atom
    • C07D263/40—One oxygen atom attached in position 4

Definitions

  • the present invention relates to new aminocarboxylic acid fluorobutenyl esters, processes for their preparation and their use for combating animal
  • Pests in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector.
  • X represents hydrogen or halogen
  • R 1 -CH C- (a) I
  • R 1 represents in each case optionally substituted alkyl, aryl or hetaryl
  • R 2 represents hydrogen, alkyl, haloalkyl or optionally substituted aryl
  • R 3 represents hydrogen, alkyl, haloalkyl, alkenyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio or in each case optionally substituted aralkyloxy or aryl,
  • R 4 , R 5 and R 6 independently of one another represent hydrogen, alkyl or in each case optionally substituted aralkyl or aryl or
  • R s and R 6 together represent optionally substituted alkanediyl and
  • A stands for a direct bond or for NH
  • R 1 , R 2 , R 3 , R 4 , R s , R 6 , A and X have the meaning given above
  • the compounds of the formula (I) can exist as geometric and / or optical isomers or isomer mixtures of different compositions.
  • the invention relates to both the pure isomers and the isomer mixtures
  • R 1 and R 2 have the meaning given above
  • R 3 , R 4 , R 5 and R 6 have the meaning given above,
  • R 3 , R 5 and R 6 have the meaning given above,
  • Formula (I) generally defines the ammocarboxylic acid fluorobutenyl esters according to the invention
  • X preferably represents hydrogen, fluorine or chlorine
  • R preferably represents one of the groups
  • R 1 preferably represents C, -C 6 -alkyl or optionally single to triple, identical or different by halogen, C j -C ⁇ alkyl, C, -C 4 -haloalkyl, C r C 6 -alkoxy, C r C 4 -Halogenalkoxy, C r C 6 alkylthio, C r C 4 -Halogenalkylthio, cyano, nitro or SCN substituted phenyl or for each optionally substituted once or twice, identically or differently by halogen or C, -C 4 alkyl Thienyl, furanyl or pyridyl
  • R 2 preferably represents hydrogen, C, -C 6 -alkyl, C r C 6 -haloalkyl or optionally single to triple, identical or different by halogen, C, -C 6 -alkyl, C r C 4 -haloalkyl, C , -C 6 alkoxy, C, -C 4 haloalkoxy,
  • R 3 preferably represents hydrogen, C, -C 6 alkyl, C, -C 4 haloalkyl, C 2 -C 6 alkenyl, C, -C 6 alkoxy, C r C 4 haloalkoxy, C, -C 6 -Alkylth ⁇ o, C r C 4 -Halogenalkylthio, optionally in the phenyl part single to triple, identical or different by halogen or C, -C 6 alkyl substituted benzyloxy or optionally single to triple, identical or different by halogen, C j - C 6 - alkyl, C ] -C 4 haloalkyl, C, -C 6 alkoxy, C r C 4 haloalkoxy, C, -C 6 alkylthio, CpC ⁇ haloalkylthio, cyano, nitro or SCN substituted phenyl
  • R 4 , R 5 and R 6 independently of one another preferably represent hydrogen, C, -C 6 -alkyl, optionally in the phenyl part monosubstituted to triple, identical or differently substituted by halogen, C j -C 6 -alkyl or CC 6 -alkoxy or for optionally single to triple, identical or different by halogen, C, -C 6 alkyl, C, -C 4 haloalkyl, C r C 6 alkoxy,
  • R b and R 6 together represent C, -C 7 -alkanedyl optionally substituted by C ] -C 6 -alkyl or phenyl (which is optionally substituted by halogen or CC 6 -alkyl)
  • A preferably represents a direct bond or NH
  • X particularly preferably represents hydrogen or fluorine
  • R particularly preferably represents one of the groups
  • R 1 -CH C-
  • R 1 particularly preferably represents C r C 4 alkyl or optionally single to triple, identical or different by fluorine, chlorine, bromine, C ] -C 4 alkyl, C, -C 3 haloalkyl with one to seven fluorine and / or chlorine atoms, C r C 4 alkoxy, C j -C ⁇ haloalkoxy with one to seven fluorine and / or chlorine atoms, C ] -C 4 alkylthio, C ] -C 2 haloalkylthio with one to five Fluorine and / or chlorine atoms, cyano or nitro substituted phenyl or thienyl, furanyl or pyridyl substituted in each case optionally once or twice, identically or differently by fluorine, chlorine, bromine, methyl or ethyl
  • R ⁇ particularly preferably represents C 1 -C 4 -alkyl, C r C 2 -haloalkyl having one to five fluorine and / or chlorine atoms, or optionally single to triple, identical or different, by fluorine, chlorine, C r C 4- alkyl, C, -C, - haloalkyl with one to five fluorine and / or chlorine atoms, C 1 -C 4 alkoxy, C j -G j -haloalkoxy with one to five fluorine and / or chlorine atoms, cyano or Nitro substituted phenyl
  • R J particularly preferably represents hydrogen, C 1 -C 4 alkyl, C, -C -, - haloalkyl with one to five fluorine and / or chlorine atoms, C 2 -C 4 alkenyl, C, -C 4 -
  • R 4, R 5 and R independently of one another particularly preferably represent hydrogen, C] -C 4 alkyl, optionally monosubstituted in the phenyl or disubstituted by identical or different fluorine, chlorine, bromine, C r C 4 alkyl or
  • R and R together represent C, -C 5 -alkanediyl which is optionally substituted by C, -C 4 -alkyl or phenyl
  • X very particularly preferably represents hydrogen or fluorine
  • R very particularly preferably represents one of the groups
  • R 1 -CH C- (a) I,
  • R very particularly preferably represents C 1 -C 4 -alkyl or, if appropriate, once or twice, identically or differently, by fluorine, chlorine, C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl with one to seven fluorine and / or chlorine atoms, C, -C -alkoxy or C j -C ⁇ -haloalkoxy with one to seven fluorine and / or chlorine atoms substituted phenyl or for thienyl or furanyl optionally optionally substituted by chlorine or methyl.
  • R 2 very particularly preferably represents C ] -C 3 -alkyl, trifluoromethyl or phenyl which is substituted once or twice, identically or differently, by fluorine, chlorine or methyl.
  • R 3 is very particularly preferably represents hydrogen, C ⁇ G j alkyl, C 2 -C 4 -
  • R 4 , R 5 and R 6 independently of one another very particularly preferably represent hydrogen, C, -C 3 alkyl or in the phenyl part in each case optionally mono- or disubstituted, identically or differently, by fluorine, chlorine or C j -C 3 alkyl substituted phenyl or benzyl or
  • R and R 6 together represent C 2 -C 5 alkanediyl.
  • hydrocarbon radicals such as alkyl or alkenyl
  • heteroatoms such as
  • Alkoxy or alkylthio - as far as possible, straight-chain or branched.
  • Process A) described above for the preparation of compounds of the formula (Ia) is characterized in that azlactones of the formula (II) are reacted with alcohols of the formula (III), if appropriate in the presence of a diluent and if appropriate in the presence of a base.
  • Process A) according to the invention is preferably carried out in the presence of a diluent.
  • Suitable diluents are in particular organic solvents, for example chlorinated aliphatic or aromatic hydrocarbons such as cyclohexane, toluene, xylene, dichloromethane, dichloroethane, chloroform, chlorobenzene or dichlorobenzene, ethers such as dioxane or tetrahydrofuran, nitrites such as acetonitrile, sulfoxides such as dimethyl , Amides such as dimethylformamide, dimethylacetamide or N-methylpyrrolidone and also sulfolane.
  • organic solvents for example chlorinated aliphatic or aromatic hydrocarbons such as cyclohexane, toluene, xylene, dichloromethane, dichloroethane, chloroform, chlorobenzene or dichlorobenzene, ethers such as dioxane or tetrahydrofuran, nitrites such as
  • Organic and inorganic bases are suitable as bases.
  • Amines are preferably used, in particular tertiary amines such as triethylamine, diazabicycloundecene (DBU), diazabicyclonones (DBN), diazabicyclooctane (DABCO) or pyridine or alkali metal or alkaline earth metal carbonates, hydrogen carbonates or hydroxides. Examples include sodium carbonate, potassium carbonate, sodium bicarbonate, sodium hydroxide, potassium hydroxide and calcium hydroxide.
  • the reaction temperature can be varied within a wide range in process A). In general, temperatures between 10 ° C and 200 ° C, preferably between 20 ° C and 160 ° C.
  • the molar ratio of the compound of formula (II) to the compound of formula (III) is generally 3 1 to 1 3, preferably 1.5 1 to 1 1.5
  • the reaction is generally carried out under normal pressure
  • the reaction mixture is hydrolyzed and the product is extracted with an organic solvent such as ethyl acetate, dichloromethane or toluene or the crude product is chromatographed.
  • organic solvent such as ethyl acetate, dichloromethane or toluene
  • the compounds of the formulas (Ib) and (Ic) can also be prepared, for example, if salts (for example alkali metal salts such as sodium or potassium salts) of the acylated amino acids of the formulas (IV) and (VI) with a fluorobutenyl bromide of the formula (VII)
  • salts for example alkali metal salts such as sodium or potassium salts
  • X has the meaning given above, in the presence of a diluent (for example dimethylformamide, dimethyl sulfoxide, sulfolane, dioxane or acetonitrile) (see the preparation examples)
  • a diluent for example dimethylformamide, dimethyl sulfoxide, sulfolane, dioxane or acetonitrile
  • azlactones of the formulas (II) and (V) required as starting materials in processes A) and Bß) are known and / or can be prepared in a simple manner by known methods (cf. the preparation examples)
  • acylated amino acids of the formulas (IV) and (VI) required as starting materials in processes B ⁇ ) and C) are known and / or can be prepared in a simple manner, for example by acylation of the corresponding amino acids (cf. Houben-Weyl , Methods of Organic Chemistry, Georg
  • the fluorobutenyl bromides of the formula (VII) are known and / or can be prepared in a simple manner by known processes (cf. C.A 1 19, 94 942)
  • the active ingredients are suitable for controlling animal pests, in particular insects, arachnids and nematodes, which protect in agriculture, in forests, in the supply and material and in the hygiene sector. They can preferably be used as crop protection agents. They are sensitive to normal and resistant species and also effective against all or individual stages of development.
  • the pests mentioned above include insects, arachnids and nematodes, which protect in agriculture, in forests, in the supply and material and in the hygiene sector. They can preferably be used as crop protection agents. They are sensitive to normal and resistant species and also effective against all or individual stages of development.
  • the pests mentioned above include
  • Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber
  • Thysanura for example Lepisma saccha ⁇ na
  • Collembola for example Onychiurus armatus
  • Anoplura e.g. Pediculus humanus corporis, Haematopinus spp, Linognathus spp
  • Thysanoptera for example Hercinoth ⁇ ps femoralis, Th ⁇ ps tabaci
  • From the order of Homoptera for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis,
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Drosophila melanogaster Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tabanus spp.
  • Tannia spp. Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.
  • 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.,. Chori ., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..
  • Plant-parasitic nematodes include, for example, Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp ..
  • the compounds of the formula (I) according to the invention are notable in particular for an outstanding nematicidal action, for example against Meloidogyne incognita.
  • Some of the active compounds according to the invention also have a systemic action and can, if appropriate, be used in foliar application.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as very fine encapsulation in polymeric substances.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents and / or solid carriers
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, 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.
  • ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic Table stone flours, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g.
  • Possible 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 dispersing agents are, for example, lignin sulfite waste 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 natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • the formulations generally contain between 0.1 and 95% by weight
  • Active ingredient preferably between 0.5 and 90%.
  • the active ingredient according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active ingredients, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • the insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
  • Fungicides are particularly favorable mixed partners:
  • Cadusafos Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157
  • Fenamiphos fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb,
  • Fenoxycarb Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb,
  • Imidacloprid Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Lambda-cyhalothrin, Lufenuron, Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathione, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin, Naled, NC 184, NI 25, Nitenpyram, Omethoat, Oxofonon, Oxamyl, Oxamyl, Oxydos
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophhine, Pyrachlophhion, Pyrachlophion, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin
  • Tebufenozid Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thio-methon, Thionazin, Thuringiensin, Tralomenhronidonium, Tronomethononium, Tronomethononium, Tronomoshroniazonium, Triaromenhroniazonium, Triaromenhroniazonium, Triaromenhroniazonium, Triaromenhroniazonium, Triaromenhronium, Tri , XMC, xylylcarb, YI 5301/5302, zetamethrin
  • the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in 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
  • the active ingredient is characterized by an excellent residual effect on wood and clay as well as a good stability to alkali on limed substrates
  • the active substances according to the invention act not only against plant, hygiene and stored pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, rough mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas
  • animal parasites ectoparasites
  • tick ticks leather ticks, rough mites, running mites, flies (stinging and licking)
  • parasitic fly larvae lice, hair lice, Featherlings and fleas
  • Anoplurida e.g. Haematopinus spp., Linognathus spp, Pediculus spp, Phtirus spp, Solenopotes spp
  • Brachycerina eg Aedes spp, Anopheles spp, Culex spp, Simulium spp, Eusimuhum spp., Phlebotomus spp, Lutzomyia spp, Cuhcoides spp, Chrysops spp., Hybomitra spp, Atylotus spp, Tabanus spp, Haematiaota spp, Philipoma spp, Philipoma spp, Philip Musca spp., Hydrotaea spp, Stomoxys spp, Haematobia spp, Morellia spp, Fannia spp, Glossina spp, Cal phora spp, Lucilia spp,
  • Argas spp Omithodorus spp, Otobius spp, Ixodes spp, Amblyomma spp, Boophilus spp, Dermacentor spp, Haemophysahs spp, Hyalomma spp, Rhipicephalusus spp, D , Railhetia spp, Pneumonyssus spp, Sternostoma spp, Varroa spp
  • Acarapis spp for example Acarapis spp, Cheyletiella spp, Ornitrocheyletia spp, Myobia spp, Psorergates spp, Demodex spp, Trombicula spp, Listrophorus spp, Acarus spp, Calrophagusph spp, Tyrophagus spp, Tyrophagus spp , Pterolichus spp, Psoroptes spp, Chonoptes spp, Otodectes spp, Sarcoptes spp, Notoedres spp, Knemidocoptes spp, Cytodites spp, Lammosioptes spp,
  • the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used in agricultural animals, such as, for example, cattle,
  • Wool, skin, eggs, honey, etc. can be reduced, so that the use of the active compounds according to the invention enables more economical and simple animal husbandry
  • the active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinks, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, such as Example by injections (intramuscular, subcutaneous, intravenous, intrape ⁇ tonal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring
  • enteral administration in the form of, for example, tablets, capsules, drinks, drenches, granules, pastes, boluses, the feed-through method, suppositories
  • parenteral administration such as Example by injections (intramuscular, subcutaneous, intravenous, intrape ⁇ tonal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray
  • the active compounds of the formula (I) can be formulated (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or after 100 Apply up to 10,000-fold dilution or use it as a chemical bath
  • Test nematode Meloidogyne incognita solvent: 4 parts by weight acetone
  • 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, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • the active ingredient preparation is mixed intimately with soil that is heavily contaminated with the test nematodes.
  • the treated soil is filled into pots, lettuce is sown and the pots are kept at a greenhouse temperature of 25 ° C.
  • the lettuce roots are examined for nematode infestation (root galls) and the effectiveness of the active ingredient is determined in%.
  • the degree of efficiency is 100% if the infestation is completely avoided, it is 0% if the infestation is just as high as that of the control plants in untreated but contaminated soil in the same way.
  • the test is carried out in 5-fold determination. 1 ⁇ l of the solutions is injected into the abdomen, the animals are transferred into dishes and stored in an air-conditioned room. The effect is determined by the inhibition of egg laying. 100% means that no tick has laid
  • the compound according to preparation example Ia-4 had an activity of 100% at an exemplary active ingredient concentration of 20 ⁇ g / animal

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pyrrole Compounds (AREA)

Abstract

L'invention concerne de nouveaux fluorobuténylesters d'acide aminocarboxylique de la formule (I) R-CO-O-CH2-CH2-CX=CF2, où X représente hydrogène ou halogène et R représente un des groupes (a), (b) R3-A-CO-NR4-CR5R6- ou (c), où A, R?1, R2, R3, R4, R5 et R6¿ ont la signification donnée dans la description. L'invention concerne également un procédé de production de ces esters et leur utilisation dans la lutte contre les animaux nuisibles.
EP96939836A 1995-11-30 1996-11-18 Fluorobutenylesters d'acide aminocarboxylique Ceased EP0863867A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19544674 1995-11-30
DE19544674A DE19544674A1 (de) 1995-11-30 1995-11-30 Aminocarbonsäurefluorbutenylester
PCT/EP1996/005076 WO1997019599A1 (fr) 1995-11-30 1996-11-18 Fluorobutenylesters d'acide aminocarboxylique

Publications (1)

Publication Number Publication Date
EP0863867A2 true EP0863867A2 (fr) 1998-09-16

Family

ID=7778830

Family Applications (1)

Application Number Title Priority Date Filing Date
EP96939836A Ceased EP0863867A2 (fr) 1995-11-30 1996-11-18 Fluorobutenylesters d'acide aminocarboxylique

Country Status (7)

Country Link
US (1) US6004992A (fr)
EP (1) EP0863867A2 (fr)
JP (1) JP2000501088A (fr)
AU (1) AU7693096A (fr)
BR (1) BR9611835A (fr)
DE (1) DE19544674A1 (fr)
WO (1) WO1997019599A1 (fr)

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Publication number Priority date Publication date Assignee Title
CN111362933A (zh) * 2017-05-16 2020-07-03 南开大学 一种α-氨基丙烯酸类杀微生物剂及其制备方法和用途
WO2020222118A1 (fr) * 2019-04-30 2020-11-05 Isagro S.P.A. Esters de composés hétérocycliques non aromatiques ayant une activité nématicide, leurs compositions agronomiques et leur utilisation

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Publication number Priority date Publication date Assignee Title
US4950666A (en) * 1989-03-30 1990-08-21 Fmc Corporation Difluoroalkane and difluoroalkenylalkane pesticides
US5081287A (en) * 1989-06-30 1992-01-14 Fmc Corporation Pesticidal polyhalo alkenoic acid esters
DE3941966A1 (de) * 1989-12-15 1991-06-20 Schering Ag Halogenierte olefine, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel
DK0640069T3 (da) * 1991-03-01 1999-07-19 Monsanto Co Fluoralkenylforbindelser og deres anvendelse som midler til bekæmpelse af skadelige organismer

Non-Patent Citations (1)

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Title
See references of WO9719599A1 *

Also Published As

Publication number Publication date
AU7693096A (en) 1997-06-19
US6004992A (en) 1999-12-21
JP2000501088A (ja) 2000-02-02
WO1997019599A1 (fr) 1997-06-05
DE19544674A1 (de) 1997-06-05
BR9611835A (pt) 1999-08-24

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