WO1995021156A1 - Phenylthio acetic acid derivatives, process and intermediate products for their production and agents containing them - Google Patents

Phenylthio acetic acid derivatives, process and intermediate products for their production and agents containing them Download PDF

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Publication number
WO1995021156A1
WO1995021156A1 PCT/EP1995/000014 EP9500014W WO9521156A1 WO 1995021156 A1 WO1995021156 A1 WO 1995021156A1 EP 9500014 W EP9500014 W EP 9500014W WO 9521156 A1 WO9521156 A1 WO 9521156A1
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WIPO (PCT)
Prior art keywords
alkylamino
alkyl
aryl
halogen
hetaryl
Prior art date
Application number
PCT/EP1995/000014
Other languages
German (de)
French (fr)
Inventor
Herbert Bayer
Hubert Sauter
Ruth Müller
Wassilios Grammenos
Albrecht Harreus
Reinhard Kirstgen
Franz Röhl
Eberhard Ammermann
Gisela Lorenz
Original Assignee
Basf Aktiengesellschaft
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Filing date
Publication date
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to BR9506718A priority Critical patent/BR9506718A/en
Priority to JP7520336A priority patent/JPH09508396A/en
Priority to MX9603175A priority patent/MX9603175A/en
Priority to SK1022-96A priority patent/SK102296A3/en
Priority to AU14547/95A priority patent/AU686304B2/en
Priority to EP95906289A priority patent/EP0741698A1/en
Publication of WO1995021156A1 publication Critical patent/WO1995021156A1/en

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    • 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
    • A01N37/50—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 the nitrogen atom being doubly bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/20—Esters of monothiocarboxylic acids
    • C07C327/22—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms

Definitions

  • the present invention relates to phenylacetic acid derivatives of the formula I.
  • R 1 is hydrogen and -CC alkyl
  • n 0, 1 or 2, where the radicals R 2 can be different if represents 2;
  • R 3 is hydrogen, cyano, nitro, hydroxy, amino, halogen,
  • R 4 is hydrogen, cyano, nitro, hydroxy, amino, halogen,
  • N-C ⁇ -C 6 -alkylamino where the hydrocarbon radicals of these groups can be partially or completely halogenated or can carry one to three of the following radicals: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, amino hiocarbonyl, halogen, C ⁇ -C 6 alkylaminocarbonyl,
  • A represents oxygen, sulfur or nitrogen and the nitrogen carries hydrogen or Ci-C ⁇ -alkyl
  • n 0 or 1
  • R 6 is hydrogen or Ci-Ce-alkyl
  • R 7 is hydrogen or -CC 6 alkyl, as well as their salts.
  • the invention also relates to processes and intermediates for the preparation of these compounds and compositions containing them for controlling animal pests and harmful fungi.
  • Phenylacetic acid derivatives for pest control are known from the literature (EP-A 432 503, EP-A 463 488).
  • the present invention was based on new compounds with improved activity as an object.
  • the compounds I can be obtained in various ways by processes known per se in the literature.
  • the structure of the grouping -C (NOCH 3 ) -COSR 1 is known, for example, from the literature cited at the beginning.
  • L 1 in formula II stands for a nucleophilically exchangeable leaving group, for example halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.
  • the reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, e.g. Sodium hydride, potassium hydroxide, potassium carbonate and triethylamine according to the methods described in Houben-Weyl, vol. E 14b, p. 370 f and Houben-Weyl, vol. 10/1, p. 1189 f.
  • a base e.g. Sodium hydride, potassium hydroxide, potassium carbonate and triethylamine according to the methods described in Houben-Weyl, vol. E 14b, p. 370 f and Houben-Weyl, vol. 10/1, p. 1189 f.
  • the required hydroxyimine III is obtained by reacting a corresponding dihydroxyimine IV with a nucleophilically substituted reagent VI
  • L 2 in formula VI stands for a nucleophilically exchangeable leaving group, for example halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.
  • reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, e.g. Potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine according to the in Houben-Weyl, Vol. E 14b,
  • a base e.g. Potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine according to the in Houben-Weyl, Vol. E 14b,
  • the compounds I can also be obtained by first reacting the benzyl derivative II with the dihydroxyimino derivative IV into a corresponding benzyloxime of the formula V, V then being converted to I with the nucleophilically substituted reagent VI.
  • the reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, e.g. Potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine according to the in Houben-Weyl, Vol. 10/1, p. 1189 f; Houben-Weyl, Vol. E 14b, p. 307 f, p. 370 f and p. 385 f; Houben-Weyl, Vol. 10/4, p. 55 f, p. 180 f and p. 217 f; Houben-Weyl, vol. E5, p. 780 f.
  • a base e.g. Potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine according to the in Houben-Weyl, Vol. 10/1, p. 1189 f; Houben-Weyl, Vol. E 14b, p. 307 f,
  • Q ⁇ in formula IXb stands for the anion of an acid, in particular an inorganic acid, e.g. Halide such as chloride.
  • reaction is carried out in a manner known per se in an inert organic solvent according to that described in EP-A 513 580; Houben-Weyl, Vol. 10/4, pp. 73 f; Houben-Weyl, Vol. E14b, p. 369 f and p. 385 f.
  • the compounds I can also be obtained by first reacting the benzyl derivative II with the carbonylhydroxyimino derivative VIIa into a corresponding benzyloxyimine of the formula VIII, VIII subsequently being converted to I with the hydroxylamine IXa or its salt IXb.
  • the reaction is carried out in a manner known per se in an inert organic solvent according to that in Houben-Weyl, vol. E14b, p. 369 f; Houben-Weyl, vol. 10/1, p. 1189 f and Hou ⁇ ben-Weyl, vol. 10/4, p. 73 f or EP-A 513 580.
  • reaction is carried out in a manner known per se in an inert orange solvent in accordance with the methods described in EP-A 463 488 and DE application. No. 42 28 867.3 methods described.
  • the required carbonyl compound X is obtained e.g. by reacting a corresponding hydroxyiminocarbonyl Vllb with a nucleophilically substituted reagent VI
  • the compounds I can also be obtained by first reacting the benzylhydroxylamine Ha with the hydroxyiminocarbonyl Vllb in the corresponding benzyloxyimine of the formula V, V then being converted to I with the nucleophilically substituted reagent VI as described above .
  • the compounds I can also be prepared by first converting the benzylhydroxylamine Ha with the dicarbonyl of the formula XI into the benzyloxyimine of the formula VIII and then VIII with the hydroxylamine IXa or its salt IXb as described above for I is implemented.
  • R 3 is not halogen
  • Compounds in which R 3 is not halogen are preferably obtained by first converting a compound X according to the methods described in EP-A 493 711 with a lactone XII into the corresponding benzoic acid XIII and XIII via the corresponding ones Halides are converted into the cyanocarboxylic acids XIV, which are then converted into the ⁇ -keto esters XV by the Pinner reaction (Angew. Chem. 94, 1 (1982)). The corresponding thioesters are obtained from the derivatives XV by "transesterification" and are subsequently converted into the compounds I.
  • the compounds II can according to the in EP-A 432 503,
  • the compounds I can be produced as E / Z isomer mixtures which, for example, can be separated into the individual compounds by crystallization or chromatography in the usual way.
  • isomer mixtures occur during the synthesis, however, a separation is generally not absolutely necessary since the individual isomers can partially convert into one another during preparation for use or during use (e.g. under the influence of light, acid or base). Corresponding conversions can also take place after use, for example in the treatment of plants in the treated plant or in the harmful fungus or animal pest to be controlled.
  • the E isomers of the compounds I are preferred in terms of their activity (configuration based on the -0CH 3 group in relation to the -COSR 1 group).
  • the cis isomers of the compounds I are preferred in terms of their activity (configuration based on the radical R 3 in relation to the -OCH group).
  • Alkyl straight or branched alkyl groups with 1 to 4, 6 or 10 carbon atoms, e.g. Ci-C ⁇ -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1, 2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl
  • Alkylcarbonyl straight-chain or branched alkyl groups with 1 to 10 carbon atoms, which are bonded to the skeleton via a carbonyl group (-CO-);
  • Alkylaminothiocarbonyl Alkylamino groups with 1 to 6 carbon atoms as mentioned above, which are bonded to the skeleton via a thiocarbonyl group (-CS-);
  • Dialkylamino groups each having 1 to 6 carbon atoms per alkyl radical as mentioned above, which are bonded to the skeleton via a thiocarbonyl group (-CS-);
  • Halo ⁇ enalkyl straight-chain or branched alkyl groups with 1 to 6 carbon atoms, in which groups the hydrogen atoms in these groups can be partially or completely replaced by halogen atoms as mentioned above, for example C 1 -C 2 -haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, Difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2- difluoro-ethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;
  • Haloalkoxy straight-chain or branched alkyl groups with 1 to 6 carbon atoms, the hydrogen atoms in these groups being partially or completely replaced by halogen atoms as above hend called may be replaced, and wherein these groups are bonded to the structure via an oxygen atom;
  • Alkylthio straight-chain or branched alkyl groups with 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the skeleton via a sulfur atom (-S-), for example C 1 -C 6 -alkyl thio such as methylthio, ethylthio, propylthio, 1-methylethylthio, Butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1- Dimethylpropylthio, 1,2-Dirnethylpropylthio, 1-Methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio,
  • Cvcloalkyl monocyclic alkyl groups with 3 to 6 carbon ring members, e.g. Cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
  • Alk ⁇ nyloxy straight-chain or branched alkenyl groups with 2 to 6 carbon atoms and a double bond in any position, which are bonded to the skeleton via an oxygen atom (-0-);
  • Alk ⁇ nylcarbonyl straight-chain or branched alkenyl groups with 2 to 10 carbon atoms and a double bond in any position which are bonded to the skeleton via a carbonyl group (-CO-);
  • Alkenvlthio or Alkenvlamino straight-chain or branched alkenyl groups with 2 to 6 carbon atoms and a double bond in any position which (alkenylthio) are bonded to the skeleton via a sulfur atom or (alkenylamino) a nitrogen atom;
  • Alkynyl straight-chain or branched alkynyl groups with 2 to 10 carbon atoms and a triple bond in any position, for example C -C 6 -alkynyl such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl , 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 1, l-dimethyl-2-propynyl, l-ethyl-2-propynyl , 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, l-methyl-2-pentynyl, l-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-p
  • Alkynylcarbonyl straight-chain or branched alkynyl groups with 3 to 10 carbon atoms and a triple bond in any position, which are bonded to the skeleton via a carbonyl group (-CO-);
  • Alkinvloxv or Alkinvlthio and Alkinvlamino straight-chain or branched alkynyl groups with 2 to 6 carbon atoms and a triple bond in any position, which (alkynyloxy) via an acid atom or (alkynylthio) via a sulfur atom or (alkynylamino) via a nitrogen atom are bonded to the skeleton; Pvcloalkoxy or Cycloalkylthio and Cvcloalkyl «minn; monocyclic alkenyl groups with 3 to 6 carbon ring members which (cycloalkyloxy) are bonded to the skeleton via an oxygen atom or (cycloalkylthio) a sulfur atom or (cycloalkylamino) via a nitrogen atom, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl ;
  • Cvcloalkanvl or Cvcloalkenvloxy Cycloalkenylthio and Cvclo- monocyclic alkenyl groups with 3 to 6 carbon ring members, which directly or (cycloalkenyloxy) via one
  • Oxygen atom or (cycloalkenylthio) a sulfur atom or (cycloalkenylamino) are bonded to the skeleton via a nitrogen atom, e.g. Cyclopropenyl, cyclobutenyl, cyclopentenyl or cyclohexenyl;
  • Aromatic mono- or polycyclic hydrocarbon residues which are bonded to the skeleton via a nitrogen atom;
  • Hetarylcarbonyl and hetarylaulfonyl aromatic mono- or polycyclic radicals which, in addition to carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom and which or (hetaryloxy ) via an oxygen atom (-0-) or (hetarylthio) a sulfur atom (-S-), (hetarylcarbonyl) via a carbonyl group (-C0-) or (hetaryl-sulfonyl) via a sulfonyl group (-S0 2 -) to the skeleton are bound, e.g.
  • 5- ⁇ liedri ⁇ es heteroarvl. containing one to three nitrogen atoms 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three nitrogen atoms as ring members, for example 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2- Imidazolyl, 4-imidazolyl, 1,2,4-triazol-3-yl and 1,3,4-triazol-2-yl;
  • heteroarvl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or one
  • Sulfur atom 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or sulfur atom as ring members, e.g. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3- Pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-0xazolyl, 4-0xazolyl, 5-0xazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4- Oxadiazol-3-yl, l, 2,4-oxadiazol-5-yl, 1,2,4-thiadiazol -3-y
  • 6-membered heteroaryl containing one to three or one to four nitrogen atoms 6-ring heteroaryl groups which, in addition to carbon atoms, may contain one to three or one to four nitrogen atoms as ring members, e.g. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, l, 3,5-triazin-2-yl, 1, 2,4-triazin-3-yl and 1,2,4,5-tetrazinyl;
  • Buta-1,3-diene-1,4-diyl group may be bridged, e.g. Quinoline, isoquinoline, quinazoline and quinoxaline,
  • Hetarylffi ⁇ 'iiin '? I aromatic mono- or polycyclic radicals which, in addition to carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom, and which have one Nitrogen atom are bound to the scaffold.
  • R 3 represents hydrogen, hydroxyl, cyclopropyl, chlorine, methyl, ethyl, 1-methylethyl, methoxy, methylthio or phenyl.
  • R 4 represents hydrogen, hydroxyl, cyclopropyl, chlorine, methyl, ethyl, isopropyl, methoxy or methylthio.
  • R 4 represents aryl or hetaryl.
  • R 5 represents arylalkyl or hetarylalkyl.
  • R 5 represents aryloxyalkyl or hetaryloxyalkyl.
  • R 4 for optionally subst. Aryl or hetaryl is.
  • R 4 for optionally subst.
  • R 4 for optionally subst. Furyl, thienyl or pyrrolyl.
  • R 4 for optionally subst.
  • R 4 for optionally subst. Oxdiazolyl, thiadiazolyl or triazolyl.
  • R 4 is phenyl which is unsubstituted or carries one or two of the following groups: nitro, cyano, hydroxy, amino, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 4 alkyl, C 1 -C -Halogenalkyl, C ⁇ -C -alkoxy, C ⁇ -C -halalkalkoxy, C ⁇ -C -alkylamino, di-C 1 -C 4 -alkylamino, C 1 -C 4 -alkylsulfonyl, C ⁇ -C -alkoxycarbonyl, C ⁇ -C 4 -Alkylaminocarbonyl or Di-C ⁇ -C 4 -Alkylaminocarbonyl.
  • R 5 represents aryl or hetaryl.
  • the compounds I are suitable as fungicides.
  • the compounds I are notable for excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes and Basidio ycetes. Some of them are systemically effective and can be used as foliar and soil fungicides.
  • Erysiphe graminis in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin plants, Podosphaera leucotricha on apples, Uncinula necator on vines, Puc- cinia species on cereals Species on cotton and grass, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species on cereals, Seporia nodoru on wheat, Botrytis cinerea (gray mold) on strawberries, vines , Cercospora arachidicola on peanuts, Pseudocercosporella herpotrichoides on wheat, barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Fusa7rium and Verticillium species on various plants, Plasmopara viticola on vine
  • the compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally active amount of the active compounds. It is used before or after the infection of the materials, plants or seeds by the fungi.
  • the formulations can be converted into the usual formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the form of application depends on the respective purpose; in any case, it should ensure a fine and uniform distribution of the ortho-substituted benzyl ester of a cyclopropanecarboxylic acid.
  • the formulations are prepared in a known manner, for example by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, and in the case of water as diluent other organic solvents can also be used as auxiliary solvents - nen.
  • auxiliaries solvents such as aromatics (e.g.
  • chlorinated aromatics e.g. chlorobenzenes
  • paraffins e.g. petroleum fractions
  • alcohols e.g. methanol, butanol
  • ketones e.g. cyclohexanone
  • amines e.g.
  • Carriers such as natural stone powder (eg kaolins, clays, talc, chalk) and synthetic stone powder (eg highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
  • Carriers such as natural stone powder (eg kaolins, clays, talc, chalk) and synthetic stone powder (eg highly disperse silica, silicates)
  • Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.
  • the application rates are between 0.01 and 2.0 kg of active ingredient per ha.
  • active ingredient 0.001 to 0.1 g, preferably 0.01 to 0.05 g, per kg of seed are generally required.
  • agents according to the invention can also be present in the use form as fungicides together with other active ingredients, which e.g. with herbicides, insecticides, growth regulators, fungicides or also with fertilizers.
  • Sulfur, dithiocarbamates and their derivatives such as ferridi ethyl dithiocarbamate, zinc dimethyl dithiocarbamate, zinc ethylene bisdithiocarbamate, manganese ethylene bisdithiocarbamate, manganese-zinc ethylene diamine bis-dithiocarbamate, tetra ethyl thiuram disulfide zinc (ammonium n-bisulfide, ethylenedisulfide, (ammonia -dithiocarbamate), ammonia complex of zinc (N, N'-propylene-bis-dithiocarbamate), zinc (N, N'-propylene-bis-dithiocarbamate), N, N'-polypropylene-bis- ( thiocarbamoyD disulfide; Nitroderivatives such as dinitro- (1-methylheptyl) phenyl crotonate, 2-sec-butyl-4, 6-dini
  • heterocyclic substances such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6- (o-chloroanilino) -s-triazine, 0.0-diethyl-phthalimidophosphonothioate, 5-amino-l- [bis - (dimethylamino) phosphinyl] -3-phenyl-l, 2,4-triazole, 2,3-dicyano-l, 4-dithioanthraquinone, 2-thio-l, 3-dithiolo [4,5-b] quinoxaline, 1- (butylcarbamoy1) -2-benzimidazole-carbamic acid methyl ester, 2-methoxycarbonylamino-benzimidazole, 2- (furyl- (2)) -benzimidazole, 2- (thiazolyl- (4)) -benzimidazole, N- (1,1,2,2-tetrachloroethyl
  • the compounds of the formula I are also suitable for effectively controlling pests from the class of the insects, arachnids and nematodes. They can be used as pesticides in crop protection and in the hygiene, stored product protection and veterinary sectors.
  • the harmful insects include, for example, Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulobura, chumumobella, Cheumatobella - ferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia po- monella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandio- sella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia am- biguella, Evetria bouliana, Fella diella, granella Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis
  • Diptera From the order of the two-winged species (Diptera), for example, Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropuce phumacuceaculaceacucia, pita Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glos ⁇ sina morsitans, Haematobia irritans, Haplodiplosis equestris, Hy- lemyia platura, Hypoderma lineata, Lirio yza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia seriaalalisata, Lucilia seriola rata,
  • Thysanoptera From the order of the thrips (Thysanoptera), for example, Franklini fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci.
  • hymenoptera From the order of the hymenoptera (Hymenoptera), for example, Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta.
  • Heteroptera From the order of the bugs (Heteroptera), for example, Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Eu- schistus impictiventris, Leptoglossus phyllopus, Lygus lineola- ris, Lygus parsatidis, Lygus parsatidis, Lygus prairisensis , Solubea insularis, Thyanta perditor.
  • suckers from the order of the plant suckers (Ho optera), for example, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Bre- vicoryne brassicae, Cerosipha gossypyususiusi, Dreiafusiai, Dreiafusolia, Dreiafusiaia, Dreiafusiaia, Dreiafusiaia, Dreiafusiaia, Dreyfusiaia, Dreiafusiaia , Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus
  • Orthoptera From the order of the straight-winged wing (Orthoptera), for example Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanusus, Melanoplus sanguinisusptipisipei, Melanoplasci, melanoplasmic , Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus, Tachycines asynamorus.
  • Orthoptera for example Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus fe
  • arachnids such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus micro-croplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentoretronichumum, Eri Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus mou- bata, Otobius megnini, Paratetranychus pilosus, Dermanyssus gal- linae, Phyllocoptruta oleivora, Polyphagotarsonemususus, Ticendiphodinusiabi, Ticipinusiabi, Ticipinusiabusi, Ticinociabusi - wai, Tetranychus pacificus, Tetranychus
  • root gall nematodes e.g. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, e.g. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schach- tii, Heterodera trifolii, stick and leaf wholes, e.g.
  • root gall nematodes e.g. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, e.g. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schach- tii, Heterodera trifolii, stick and leaf wholes, e.g.
  • the active ingredients as such in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, spreading agents, granules by spraying, atomizing, dusting, scattering or pouring.
  • the application forms depend entirely on the intended use; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • the active substance concentrations in the ready-to-use preparations can be varied over a wide range.
  • they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be used with great success in the ultra-low-volume process (ULV), it being possible to apply formulations with more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume process
  • the amount of active ingredient used to control pests is 0.1 to 2.0, preferably 0.2 to 1.0 kg / ha under field conditions.
  • mineral oil fractions from medium to high boiling points such as kerosene or diesel oil, also coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example benzene, toluene, xylene, Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, Butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, for example dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, into consideration.
  • solvents for example dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, into consideration.
  • Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
  • emulsion concentrates pastes or wettable powders (wettable powders, oil dispersions)
  • wettable powders oil dispersions
  • water water
  • emulsions, pastes or oil dispersions the substances as such or dissolved in an oil or solvent, by means of wetting, adhesive,
  • Dispersants or emulsifiers can be homogenized in water. However, it is also possible to prepare concentrates composed of an active substance, wetting agents, adhesives, dispersants or emulsifiers and possibly solvents or oil, which are suitable for dilution with water.
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • the formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight, of the active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum). Examples of formulations are:
  • V. 80 parts by weight of an active ingredient are mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 10 parts by weight of the sodium salt of a lignin sulfonic acid from a sulfite waste liquor and 7 parts by weight in powder form Mix the silica gel well and grind it in a hammer mill (active ingredient content 80% by weight).
  • Parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil consists. By pouring and Distributing the solution in 100,000 parts by weight of water gives an aqueous dispersion which contains 0.02% by weight of the active ingredient.
  • Granules e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are e.g. Mineral soils, such as silica gel, silicas, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as e.g. Ammonium sulfate,
  • Ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • Oils of various types, herbicides, fungicides, other pesticides, bactericides can be added to the active compounds, if appropriate also only immediately before use (tank mix). These agents can be added to the agents according to the invention in a weight ratio of 1:10 to 10: 1.
  • the active ingredients were administered as a 20% emulsion in a mixture of 70% by weight cyclohexanone, 20% by weight Nekanil ® IN (Lutensol ® AP6, detergent with emulsifying and dispersing action based on ethoxylated alkylphenols) and 10% by weight.
  • % Emulphor ® EL Emulphor ® EL (Emulan ® EL, emulsifier based on ethoxylated fatty alcohols) prepared and diluted with water according to the desired concentration.
  • Leaves of wheat seedlings ("Chancellor" variety) were first treated with the aqueous preparation of the active ingredients (containing 63 ppm). After about 24 hours, the plants were dusted with spores of wheat powdery mildew (Erysiphe graminis var. Tritici). The plants treated in this way were then incubated for 7 days at 20-22 ° C. and a relative atmospheric humidity of 75-80%. The extent of the fungal development was then determined.
  • the active ingredients were:
  • Emulphor ® EL Emulphor ® EL, emulsifiers tor based on ethoxylated fatty alcohols

Abstract

Phenylthio acetic acid derivatives of formula (I) in which the components and index have the following meanings: R1 is hydrogen and alkyl; R2 is cyano, nitro, trifluoro methyl, halogen, alkyl and alkoxy; m is 0, 1 or 2, in which the radicals R2 may be different if m is 2; R3 is hydrogen, cyano, nitro, hydroxy, amino, halogen, alkyl, halogen alkyl, alkoxy, halogen alkoxy, alkylthio, alkylamino or dialkylamino; R4 is hydrogen, cyano, nitro, hydroxy, amino, halogen, possibly substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, alkenyl, alkenyloxy, alkenylthio, alkenylamino, N-alkenyl-N-alkylamino, alkinyl, alkinyloxy, alkinylthio, alkinylamino, N-alkinyl-N-alkylamino, possibly substituted cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, N-cycloalkyl-N-alkylamino, cycloalkenyl, cycloalkenyloxy, cycloalkenylthio, cycloalkenylamino, N-cycloalkenyl-N-alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-heterocyclyl-N-alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N-alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino, N-hetaryl-N-alkylamino; R5 is hydrogen, possibly substituted alkyl, cycloalkyl, alkenyl, alkinyl, alkyl carbonyl, alkenyl carbonyl, alkinyl carbonyl or alkyl sulphonyl, possibly substituted aryl, aryl carbonyl, aryl sulphonyl, hetaryl, hetaryl carbonyl or hetaryl sulphonyl. The invention also concern their salts, the process and intermediate products for their production and their use.

Description

PHENYLTHIOESSIGSAUREDEÄIVATE, VERFAHREN UND ZWISCHENPRODUKTE ZU IHRER i HERSTELLUNG UND SIE ENTHALTENDE MITTEL PHENYLTHIO ACID ACID DERIVATIVES, METHODS AND INTERMEDIATE PRODUCTS FOR THEIR PREPARATION AND MEANS CONTAINING IT
Beschreibungdescription
Die vorliegende Erfindung betrifft Phenylessigsäurederivate der Formel IThe present invention relates to phenylacetic acid derivatives of the formula I.
Figure imgf000003_0001
Figure imgf000003_0001
O-C-SR1 OC-SR 1
in der die Substituenten und der Index die folgende Bedeutung haben:in which the substituents and the index have the following meaning:
R1 Wasserstoff und Cι-C -Alkyl;R 1 is hydrogen and -CC alkyl;
R2 Cyano, Nitro, Trifluormethyl, Halogen, Cι-C4-Al yl und Cι-C4-Al oxy;R 2 cyano, nitro, trifluoromethyl, halogen, -C-C4-Al yl and Cι-C 4 -Al oxy;
m 0, 1 oder 2, wobei die Reste R2 verschieden sein können, wenn
Figure imgf000003_0002
für 2 steht;m is 0, 1 or 2, where the radicals R 2 can be different if
Figure imgf000003_0002
represents 2;
R3 Wasserstoff, Cyano, Nitro, Hydroxy, Amino, Halogen,R 3 is hydrogen, cyano, nitro, hydroxy, amino, halogen,
C_.-C -Alkyl, Cι-C4-Halogenalkyl, Cι-C4-Alkoxy, Cι-C4-Halogen- alkoxy, Cι-C4-Alkylthio, C1-C4-Alkylanu.no oder Di-Cι-C4-alkyl- a ino;C _.- C -alkyl, -C-C 4 -haloalkyl, Cι-C 4 -alkoxy, Cι-C 4 -haloalkoxy, Cι-C 4 -alkylthio, C 1 -C4- alkylanu.no or di-Cι- C 4 alkyl a ino;
R4 Wasserstoff, Cyano, Nitro, Hydroxy, Amino, Halogen,R 4 is hydrogen, cyano, nitro, hydroxy, amino, halogen,
Cι-C6-Alkyl, Ci-Cε-Alkoxy, Ci-Ce-Alkylthio, Cι-C6-Alkylamino, Di-Ci-Cβ-alkylamino, C2-C6-Alkenyl, C2-C6-Alkenyloxy, C -C6-Alkenylthio, C2-C6-Alkenylamino, N-C2-C6-Alkenyl- N-Ci-Cδ-alkylamino, C2-C6-Alkinyl, C2-C6-Alkinyloxy, C2-C6-Alkinylthio, C2-C6-Alkinylamino, N-C2-C6-Alkinyl-C 1 -C 6 -alkyl, Ci-Cε-alkoxy, Ci-Ce-alkylthio, Cι-C 6 -alkylamino, di-Ci-Cβ-alkylamino, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, C -C 6 alkenylthio, C 2 -C 6 alkenylamino, NC 2 -C 6 alkenyl- N-Ci-C δ -alkylamino, C 2 -C 6 alkynyl, C 2 -C 6 alkynyloxy, C 2 -C 6 alkynylthio, C 2 -C 6 alkynylamino, NC 2 -C 6 alkynyl-
N-Cι-C6-alkylamino, wobei die Kohlenwasserstoffreste dieser Gruppen partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Reste tragen können: Cyano, Nitro, Hydroxy, Merkapto,Amino, Carboxyl, Aminocarbonyl, Amino hiocarbonyl, Halogen, Cι-C6-Alkylaminocarbonyl,N-Cι-C 6 -alkylamino, where the hydrocarbon radicals of these groups can be partially or completely halogenated or can carry one to three of the following radicals: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, amino hiocarbonyl, halogen, Cι -C 6 alkylaminocarbonyl,
Di-Ci-Ce-alkylaminocarbony1, Ci-Cδ-Alkylaminothiocarbonyl, Di-Ci-Cδ-alkylaminothiocarbonyl, Ci-Cβ-Alkylsulfonyl, Cι-C6-Alkylsulfoxyl, Cι-C6-Alkoxy, Ci-Cβ-Halogenalkoxy, Cι-C6-Alkoxycarbonyl, Cι-C6-Alkylthio, Cι-C6-Alkylamino, Di-Ci-Cε-alkylamino, C -C6-Alkenyloxy, C3-C6-Cycloalkyl, Cs-Cg-Cycloalkyloxy, Heterocyclyl, Heterocyclylox , Aryl, Aryloxy, Aryl-Cι-C4-alkoxy, Arylthio, Aryl-Cι-C4-alkylthio,Di-Ci-Ce-alkylaminocarbony1, Ci-C δ- alkylaminothiocarbonyl, di-Ci-C δ -alkylaminothiocarbonyl, Ci-Cβ-alkylsulfonyl, C 1 -C 6 alkyl sulfoxyl, C 1 -C 6 alkoxy, C 1 -C 6 halogenoalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylamino, di-C 1 -C 6 alkylamino, C -C 6 -alkenyloxy, C 3 -C6 -cycloalkyl, Cs-Cg-cycloalkyloxy, heterocyclyl, heterocyclylox, aryl, aryloxy, aryl-Cι-C 4 -alkoxy, arylthio, aryl-Cι-C 4 -alkylthio,
Hetaryl, Hetaryloxy, Hetaryl-Cι-C -alkox , Hetarylthio, Heta- ryl-Cι-C4-alkylthio, wobei die cyclischen Reste ihrerseitspar¬ tiell oder vollständig halogeniert sein können und/oder ein bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothio- carbonyl, Ci-Cδ-Alkyl, Cι-C6-Halogenalkyl, Cι-C6-Alkyl- sulfonyl, Ci-Cδ-Alkylsulfoxyl, C3C6-Cycloalkyl, Ci-Cε-Alkoxy, Ci-Cς-Halogenalkoxy, Cι-C6-Alkoxycarbonyl, Cι-C6-Alkylthio, Cι-C6-Alkylamino, Di-Ci-Cε-alkylamino, Cι-C6-Alkylamino- carbonyl, Di-Cι-C6-alkylaminocarbonyl, Cι-C6-Alkylaminothio- carbonyl, Di-Ci-Cδ-alkylaminothiocarbonyl, C2-C6-Alkenyl, C -C6~Alkenyloxy, Benzyl, Benzyloxy, Airyl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy, Hetarylthio und C(=NOR6)-An-R7;Hetaryl, hetaryloxy, hetaryl-Cι-C -alkox, hetarylthio, hetaryl-Cι-C 4 -alkylthio, where the cyclic radicals may be ihrerseitspar¬ tially or fully halogenated and / or may carry one to three of the following groups: cyano , Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothio-carbonyl, Ci-C δ- Alkyl, Cι-C 6 -Halogenalkyl, Cι-C 6 -Alkyl-sulfonyl, Ci-C δ -Alkylsulfoxyl, C 3 C 6- cycloalkyl, Ci-Cε-alkoxy, Ci-Cς-haloalkoxy, Cι-C 6 -alkoxycarbonyl, Cι-C 6 -alkylthio, Cι-C 6 -alkylamino, di-Ci-Cε-alkylamino, Cι-C 6 - Alkylamino-carbonyl, di-C 6 -alkylaminocarbonyl, C-C 6 -alkylaminothio-carbonyl, di-Ci-C δ -alkylaminothiocarbonyl, C 2 -C 6 -alkenyl, C -C 6 ~ alkenyloxy, benzyl, benzyloxy, Airyl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C (= NOR 6 ) -A n -R 7 ;
C -C6-Cycloalkyl, C3-C6-Cycloalkyloxy, C3-C6-Cycloalkylthio, C -C6-Cycloalkylamino, N-C3-C6-Cycloalkyl-N-Cι-C6-alkylamino, C3-C6~Cycloalkenyl, C3-C6-Cycloalkenyloxy, C3-Cg-Cycloalke- nylthio, C3-C6-Cycloalkenylamino, N-C -C6-Cycloalkenyl- N-Ci-Cδ-alkylamino, Heterocyclyl, Heterocyclyloxy, Heterocy- clylthio, Heterocyclylamino, N-Heterocyclyl-N-Ci-Cδ-alkyl- amino, Aryl, Aryloxy, Arylthio, Arylamino, N-Aryl- N-Ci-Cε-alkylamino, Hetaryl, Hetaryloxy, Hetarylthio, Hetary¬ lamino, N-Hetaryl-N-Cι-C6-alkylamino, wobei die cyclischen Re¬ ste partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Halogen, Cι-C6-Alkyl, Cι-C6-Halogenalkyl, Cι-C6-Alkylsulfonyl, Cι-C6-Alkylsulfoxyl, C3-C6-Cycloalkyl, Ci-Cδ-Alkoxy, Ci-Cε-Halogenalkoxy, Cι-C6-Alkoxycarbonyl, Ci-Cε-Alkylthio, Cι-C6-Alkylamino, Di-Ci-Cδ-alkylamino, Cι-C6-Alkylaminocarbonyl, Di-Cι-C6-alkylaminocarbonyl, Ci-Cβ-Alkylaminothiocarbonyl, Di-Ci-Cε-alkylaminothiocarbonyl, C -C6-Alkenyl, C -C6-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Hetaryl und Hetaryloxy;C -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, C 3 -C 6 -cycloalkylthio, C -C 6 -cycloalkylamino, NC 3 -C 6 -cycloalkyl-N-Cι-C 6 -alkylamino, C 3 - C 6 ~ Cycloalkenyl, C 3 -C 6 cycloalkenyloxy, C 3 -Cg cycloalkenylthio, C 3 -C 6 cycloalkenylamino, NC -C 6 cycloalkenyl- N-Ci-Cδ-alkylamino, heterocyclyl, heterocyclyloxy, heterocy clylthio, heterocyclylamino, N-heterocyclyl-N-Ci-C δ -alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N-Ci-Cε-alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino, N-hetaryl-N -CC-C6-alkylamino, where the cyclic radicals can be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Cι-C 6 -alkyl, C 6 haloalkyl, Cι-C 6 alkylsulfonyl, Cι-C 6 alkylsulfoxyl, C 3 -C 6 cycloalkyl, Ci-Cδ-alkoxy, Ci-Cε-haloalkoxy, -C-C 6 alkoxycarbonyl, Ci-Cε-alkylthio, Cι-C 6 alkylamino, di-Ci-C δ -alkylamino, -C-C6-alkylaminocarbonyl, di-Cι-C 6 -alkylaminocarbonyl, Ci-Cβ-alkylaminothiocarbonyl, di-Ci-Cε-alkylaminothiocarbonyl, C -C 6 alkenyl, C -C 6 alkenyloxy, benzyl, benzyloxy , Aryl, aryloxy, hetaryl and hetaryloxy;
Wasserstoff,Hydrogen,
Cι-Cιo-Alkyl, C3-C6-Cycloalkyl, C2-Cι0-Alkenyl, C2-Cι0-Alkinyl, Cι-Cιo-Alkylcarbonyl, C -Cιo-Alkenylcarbonyl, C3-Cιo-Alkinyl- carbonyl oder Ci-Cio-Alkylsulfonyl, wobei diese Reste partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Halogen, Ci-Cβ-Alkyl, Ci-Cε-Halogenalkyl, Ci-Cε-Alkylsulfonyl, Ci-Cε-Alkylsulfoxyl, Ci-Cδ-Alkoxy, Ci-Cβ-Halogenalkoxy, Ci-Cδ-Alkoxycarbonyl, Ci-Cβ-Alkylthio, Ci-Ce-Alkylamino, Di-Ci-Cδ-alkylamino, Ci-Cβ-Alkylaminocarbonyl, Di-Ci-Cδ-alkyl- aminocarbonyl, Cι-C6-Alkylaminothiocarbonyl, Di-Ci-Cε-alkyl- aminothiocarbonyl, C2-Ce-Alkenyl, C -C6-Alkenyloxy, C -C6-Cycloalkyl, C3-C6-Cycloalkyloxy, Heterocyclyl, Hetero¬ cyclyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy und Hetarylthio, wobei die cyclischen Gruppen ihrerseits partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen kön¬ nen: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Amino¬ carbonyl, Aminothiocarbonyl, Halogen, Ci-Cß-Alkyl, Ci-Cδ-Halogenalkyl, Ci-Cε-Alkylsulfonyl, Ci-Cδ-Alkylsulfoxyl, C3-C6-Cycloalkyl, Ci-Cε-Alkoxy, Ci-Cß-Halogenalkoxy,Cι-Cιo-alkyl, C 3 -C 6 cycloalkyl, C 2 -Cι 0 -alkenyl, C 2 -Cι 0 -alkynyl, Cι-Cιo-alkylcarbonyl, C -Cιo-alkenylcarbonyl, C 3 -Cιo-alkynylcarbonyl or Ci-Cio-alkylsulfonyl, where these radicals can be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, Halogen, Ci-Cβ-alkyl, Ci-Cε-haloalkyl, Ci-Cε-alkylsulfonyl, Ci-Cε-alkylsulfoxyl, Ci-C δ -alkoxy, Ci-Cβ-haloalkoxy, Ci-C δ -alkoxycarbonyl, Ci-Cβ- Alkylthio, Ci-Ce-alkylamino, Di-Ci-C δ -alkylamino, Ci-Cβ-alkylaminocarbonyl, Di-Ci-C δ -alkyl-aminocarbonyl, Cι-C 6 -alkylaminothiocarbonyl, Di-Ci-Cε-alkyl aminothiocarbonyl , C 2 -Ce alkenyl, C -C 6 alkenyloxy, C -C 6 cycloalkyl, C 3 -C 6 cycloalkyloxy, heterocyclyl, heterocyclicoxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and Hetarylthio, where the cyclic groups can in turn be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Ci-C ß - Alkyl, Ci-C δ -haloalkyl, Ci-Cε-alkylsulfonyl, Ci-C δ -alkylsulfoxyl, C 3 -C 6 -cycloalkyl, Ci-Cε-alkoxy, Ci-C ß -haloalkoxy,
Ci-Cδ-Alkyloxycarbonyl, Ci-Cδ-Alkylthio, Ci-Cg-Alkylamino, Di-Ci-Cδ-Alkylamino, Ci-Cδ-Alkylaminocarbonyl, Di-Cι-C6-Al_cyl- aminocarbonyl, Ci-Cö-Alkylaminothiocarbonyl, Di-Ci-Cε-Alkyl- . aminothiocarbonyl, C -C6-Alkenyl, C -C6-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy, He¬ tarylthio oder C(=NOR6)-An-R7;Ci-C δ- alkyloxycarbonyl, Ci-C δ- alkylthio, Ci-Cg-alkylamino, di-Ci-C δ -alkylamino, Ci-C δ -alkylaminocarbonyl, di-Cι-C 6 -Al_cyl- aminocarbonyl, Ci-C ö -alkylaminothiocarbonyl, di-Ci-Cε-alkyl-. aminothiocarbonyl, C -C 6 alkenyl, C -C 6 alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hearylthio or C (= NOR 6 ) -A n -R 7 ;
Aryl, Arylcarbonyl, Arylsulfonyl, Hetaryl, Hetarylcarbonyl oder Hetarylsulfonyl, wobei diese Reste partiell oder voll- ständig halogeniert sein können oder einen bis drei der fol¬ genden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Halogen, Ci-Cε-Alkyl, Ci-Cε-Halogenalkyl, Cι-C6-Alkylcarbonyl, Ci-Cδ-Alkylsulfonyl, Ci-Ce-Alkylsulfoxyl, C3-C6-Cycloalkyl, Ci-Cß-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cδ-Alkyloxycarbonyl, Ci-Cε-Alkylthio, Ci-Cε-Alkylamino, Di-Ci-Cβ-Alkylamino, Ci-Cg-Alkylaminocarbonyl, Di-Ci-Ce-Alkylaminocarbonyl, Cι-C6-Alkylaminothiocarbonyl, Di-Ci-Ce-Alkylaminothiocarbonyl, C -C6-Alkenyl, C2-C6-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Hetaryl, Hetaryloxy oder C(=NOR6)-An-R7;Aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, where these radicals can be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl , Halogen, Ci-Cε-alkyl, Ci-Cε-haloalkyl, Cι-C6-alkylcarbonyl, Ci-C δ -alkylsulfonyl, Ci-Ce-alkylsulfoxyl, C 3 -C 6 cycloalkyl, Ci-C ß -alkoxy, Ci -Cg-haloalkoxy, Ci-C δ -alkyloxycarbonyl, Ci-Cε-alkylthio, Ci-Cε-alkylamino, di-Ci-Cβ-alkylamino, Ci-Cg-alkylaminocarbonyl, di-Ci-Ce-alkylaminocarbonyl, Cι-C 6 -Alkylaminothiocarbonyl, Di-Ci-Ce-Alkylaminothiocarbonyl, C -C 6 alkenyl, C 2 -C 6 alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C (= NOR 6 ) -A n -R 7 ;
wobeiin which
A für Sauerstoff, Schwefel oder Stickstoff steht und wobei der Stickstoff Wasserstoff oder Ci-Cβ-Alkyl trägt;A represents oxygen, sulfur or nitrogen and the nitrogen carries hydrogen or Ci-Cβ-alkyl;
n 0 oder 1 bedeutet;n represents 0 or 1;
R6 Wasserstoff oder Ci-Ce-Alkyl bedeutet undR 6 is hydrogen or Ci-Ce-alkyl and
R7 Wasserstoff oder Cι-C6-Alkyl bedeutet, sowie deren Salze.R 7 is hydrogen or -CC 6 alkyl, as well as their salts.
Außerdem betrifft die Erfindung Verfahren und Zwischenprodukte zur Herstellung dieser Verbindungen sowie sie enthaltende Mittel zur Bekämpfung tierischer Schädlinge und Schadpilze.The invention also relates to processes and intermediates for the preparation of these compounds and compositions containing them for controlling animal pests and harmful fungi.
Aus der Literatur sind Phenylessigsäurederivate zur Schädlingsbe¬ kämpfung bekannt (EP-A 432 503, EP-A 463 488).Phenylacetic acid derivatives for pest control are known from the literature (EP-A 432 503, EP-A 463 488).
Der vorliegenden Erfindung lagen neue Verbindungen mit verbesser¬ ter Wirkung als Aufgabe zugrunde.The present invention was based on new compounds with improved activity as an object.
Demgemäß wurden die eingangs definierten Phenylessigsäurederivate I gefunden. Außerdem wurden Verfahren und Zwischenprodukte zu ih- rer Herstellung sowie sie enthaltende Mittel zur Bekämpfung von tierischen Schädlingen und Schadpilzen und ihre Verwendung in diesem Sinne gefunden.We have found that this object is achieved by the phenylacetic acid derivatives I defined at the outset. In addition, processes and intermediates for their production and compositions containing them for controlling animal pests and harmful fungi and their use were found in this sense.
Die Verbindungen I sind auf verschiedenen Wegen nach an sich in der Literatur bekannten Verfahren erhältlich.The compounds I can be obtained in various ways by processes known per se in the literature.
Grundsätzlich ist es bei der Synthese der Verbindungen I unerheb¬ lich, ob zunächst die Gruppierung -C(NOCH3)-COSR1 oder die Grup¬ pierung -CH2ON=C(R3)-C(R )=NOR5 aufgebaut wird.Basically, it is irrelevant in the synthesis of the compounds I whether the group -C (NOCH 3 ) -COSR 1 or the grouping -CH 2 ON = C (R 3 ) -C (R) = NOR 5 is initially set up becomes.
Der Aufbau der Gruppierung -C(NOCH3)-COSR1 ist beispielsweise aus der eingangs zitierten Literatur bekannt.The structure of the grouping -C (NOCH 3 ) -COSR 1 is known, for example, from the literature cited at the beginning.
Die Art der Synthese der -CH2ON=C(R3)-C(R4)=NOR5 Seitenkette rich- tet sich im wesentlichen nach der Art der Substituenten R3 und R4.The type of synthesis of the -CH 2 ON = C (R 3 ) -C (R 4 ) = NOR 5 side chain depends essentially on the type of substituents R 3 and R 4 .
1. Für den Fall, daß R3 und R4 nicht Halogen bedeuen, geht man beim Aufbau der Gruppierung -CH2ON=C(R3)-C(R4)=NOR5 im allge¬ meinen so vor, daß man ein Benzylderivat der Formel II mit einem Hydroxyimin der Formel III umsetzt. 1. In the event that R 3 and R 4 do not mean halogen, the grouping -CH 2 ON = C (R 3 ) -C (R 4 ) = NOR 5 is generally carried out in such a way that reacting a benzyl derivative of the formula II with a hydroxyimine of the formula III.
Figure imgf000007_0001
Figure imgf000007_0001
L1 in der Formel II steht für eine nukleophil austauschbare Abgangsgruppe, z.B. Halogen oder Sulfonatgruppen, vorzugs¬ weise Chlor, Brom, lod, Mesylat, Tosylat oder Triflat.L 1 in formula II stands for a nucleophilically exchangeable leaving group, for example halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.
Die Umsetzung erfolgt in an sich bekannter Weise in einem inerten organischen Lösungsmittel in Gegenwart einer Base, z.B. Natriumhydrid, Kaliumhydroxid, Kaliumcarbonat und Tri- ethylamin gemäß den in Houben-Weyl, Bd. E 14b, S. 370 f und Houben-Weyl, Bd. 10/1, S. 1189 f beschriebenen Methoden.The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, e.g. Sodium hydride, potassium hydroxide, potassium carbonate and triethylamine according to the methods described in Houben-Weyl, vol. E 14b, p. 370 f and Houben-Weyl, vol. 10/1, p. 1189 f.
Das benötigte Hydroxyimin III erhält man durch Umsetzung eines entsprechenden Dihydroxyimins IV mit einem nukleophil substituierten Reagens VIThe required hydroxyimine III is obtained by reacting a corresponding dihydroxyimine IV with a nucleophilically substituted reagent VI
Figure imgf000007_0002
Figure imgf000007_0002
L2 in der Formel VI steht für eine nukleophil austauschbare Abgangsgruppe, z.B. Halogen oder Sulfonatgruppen, vorzugs- weise Chlor, Brom, lod, Mesylat, Tosylat oder Triflat.L 2 in formula VI stands for a nucleophilically exchangeable leaving group, for example halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.
Die Umsetzung erfolgt in an sich bekannter weise in einem inerten organischen Lösungsmittel in Gegenwart einer Base, z.B. Kaliumcarbonat, Kaliumhydroxid, Natriumhydrid, Pyridin und Triethylamin gemäß den in Houben-Weyl, Bd. E 14b,The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, e.g. Potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine according to the in Houben-Weyl, Vol. E 14b,
S. 307 f, S. 370 f und S. 385 f; Houben-Weyl, Bd. 10/4, S. 55 f, S. 180 f und S. 217 f; Houben-Weyl, Bd. E5, S. 780 f, beschriebenen Methoden.P. 307 f, p. 370 f and p. 385 f; Houben-Weyl, Vol. 10/4, P. 55 f, p. 180 f and p. 217 f; Houben-Weyl, vol. E5, p. 780 f.
1.1 Alternativ können die Verbindungen I auch dadurch erhalten werden, daß das Benzylderivat II zunächst mit dem Dihydroxy- iminoderivat IV in ein entsprechendes Benzyloxim der Formel V umgesetzt wird, wobei V anschließend mit dem nukleophil sub¬ stituierten Reagens VI zu I umgesetzt wird.1.1 Alternatively, the compounds I can also be obtained by first reacting the benzyl derivative II with the dihydroxyimino derivative IV into a corresponding benzyloxime of the formula V, V then being converted to I with the nucleophilically substituted reagent VI.
Figure imgf000008_0001
Figure imgf000008_0001
C=NOCH3 C = STILL 3
V C^C-SR1 VC ^ C-SR 1
Figure imgf000008_0002
Figure imgf000008_0002
Die Umsetzung erfolgt in an sich bekannter Weise in einem in¬ erten organischen Lösungsmittel in Gegenwart einer Base, z.B. Kaliumcarbonat, Kaliumhydroxid, Natriumhydrid, Pyridin und Triethylamin gemäß den in Houben-Weyl, Bd. 10/1, S. 1189 f; Houben-Weyl, Bd. E 14b, S. 307 f, S. 370 f und S. 385 f; Houben-Weyl, Bd. 10/4, S. 55 f, S. 180 f und S. 217 f; Houben-Weyl, Bd. E5, S. 780 f, beschriebenen Methoden.The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, e.g. Potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine according to the in Houben-Weyl, Vol. 10/1, p. 1189 f; Houben-Weyl, Vol. E 14b, p. 307 f, p. 370 f and p. 385 f; Houben-Weyl, Vol. 10/4, p. 55 f, p. 180 f and p. 217 f; Houben-Weyl, vol. E5, p. 780 f.
1.2 Analog ist es ebenfalls möglich, das benötigte Hydroxyimin der Formel III aus einem Carbonylhydroxyi in Vlla durch Um¬ setzung mit einem Hydroxylamin IXa oder seinem Salz IXb her¬ zustellen.
Figure imgf000009_0001
1.2 Analogously, it is also possible to prepare the required hydroxyimine of the formula III from a carbonylhydroxyi in VIIIa by reaction with a hydroxylamine IXa or its salt IXb.
Figure imgf000009_0001
R5-ON=C(R4)-C(R3)=NOH IIIR 5 -ON = C (R 4 ) -C (R 3 ) = NOH III
QΘ in der Formel IXb steht für das Anion einer Säure, ins¬ besondere einer anorganischen Säure, z.B. Halogenid wie Chlorid.QΘ in formula IXb stands for the anion of an acid, in particular an inorganic acid, e.g. Halide such as chloride.
Die Umsetzung erfolgt in an sich bekannter Weise in einem inerten organischen Lösungsmittel gemäß den in EP-A 513 580; Houben-Weyl, Bd. 10/4, S. 73 f; Houben-Weyl, Bd. E14b, S. 369 f und S. 385 f beschriebenen Methoden.The reaction is carried out in a manner known per se in an inert organic solvent according to that described in EP-A 513 580; Houben-Weyl, Vol. 10/4, pp. 73 f; Houben-Weyl, Vol. E14b, p. 369 f and p. 385 f.
1.3 Alternativ können die Verbindungen I auch dadurch erhalten werden, daß das Benzylderivat II zunächst mit dem Carbonylhy- droxyiminoderivat VIIa in ein entsprechendes Benzyloxyimin der Formel VIII umgesetzt wird, wobei VIII anschließend mit dem Hydroxylamin IXa bzw. dessen Salz IXb zu I umgesetzt wird.1.3 Alternatively, the compounds I can also be obtained by first reacting the benzyl derivative II with the carbonylhydroxyimino derivative VIIa into a corresponding benzyloxyimine of the formula VIII, VIII subsequently being converted to I with the hydroxylamine IXa or its salt IXb.
Figure imgf000009_0002
Figure imgf000009_0002
Figure imgf000009_0003
Die Umsetzung erfolgt in an sich bekannter Weise in einem in¬ erten organischen Lösungsmittel gemäß den in Houben-Weyl, Bd. E14b, S. 369 f; Houben-Weyl, Bd. 10/1, S. 1189 f und Hou¬ ben-Weyl, Bd. 10/4, S. 73 f oder EP-A 513 580 beschriebenen Methoden.
Figure imgf000009_0003
The reaction is carried out in a manner known per se in an inert organic solvent according to that in Houben-Weyl, vol. E14b, p. 369 f; Houben-Weyl, vol. 10/1, p. 1189 f and Hou¬ ben-Weyl, vol. 10/4, p. 73 f or EP-A 513 580.
1.4 Eine weitere Möglichkeit zur Herstellung der Verbindungen I ist die Umsetzung des Benzylderivats II mit N-Hydroxyphthali- mid und nachfolgender Hydrazinolyse zum Benzylhydroxylamin Ha und die weitere Umsetzung von Ha mit einer Carbonyl- verbindung X.1.4 A further possibility for the preparation of the compounds I is the reaction of the benzyl derivative II with N-hydroxyphthalimide and subsequent hydrazinolysis to give the benzylhydroxylamine Ha and the further reaction of Ha with a carbonyl compound X.
Figure imgf000010_0001
Figure imgf000010_0001
HaHa
R5-ON=C(R4)-C(R3)=0 Ha IR 5 -ON = C (R 4 ) -C (R 3 ) = 0 Ha I
Die Umsetzung erfolgt in an sich bekannter Weise in einem in¬ erten oranischen Lösungsmittel gemäß den in EP-A 463 488 und DE-Anm. Nr. 42 28 867.3 beschriebenen Methoden.The reaction is carried out in a manner known per se in an inert orange solvent in accordance with the methods described in EP-A 463 488 and DE application. No. 42 28 867.3 methods described.
Die benötigte Carbonylverbindung X erhält man z.B. durch Um¬ setzung eines entsprechenden Hydroxyiminocarbonyls Vllb mit einem nukleophil substituierten Reagens VIThe required carbonyl compound X is obtained e.g. by reacting a corresponding hydroxyiminocarbonyl Vllb with a nucleophilically substituted reagent VI
R5-L2 + HON=C(R )-C(R3)=0 ► R5-ON=C(R4) -C(R3)=0R5-L 2 + HON = C (R) -C (R 3 ) = 0 ► R 5 -ON = C (R 4 ) -C (R 3 ) = 0
VI VIIb XVI VIIb X
oder durch Umsetzung einer entsprechenden Dicarbonyl- verbindung XI mit einem Hydrox lamin IXa oder dessen Salz IXb
Figure imgf000011_0001
or by reacting a corresponding dicarbonyl compound XI with a hydrox lamin IXa or its salt IXb
Figure imgf000011_0001
► R5-ON=C(R )-C(R3)=0► R 5 -ON = C (R) -C (R 3 ) = 0
XX
Die Umsetzungen erfolgen in an sich bekannter Weise in einem inerten organischen Lösungsmittel gemäß den in EP-A 513 580, Houben-Weyl, Bd. 10/4, S. 55 f, S. 73 f, S. 180 f und S. 217 f, Houben-Weyl, Bd. E14b, S. 307 f und 369 f, Houben- Weyl, Bd. E5, S. 780 f, beschriebenen Methoden.The reactions are carried out in a manner known per se in an inert organic solvent in accordance with the methods described in EP-A 513 580, Houben-Weyl, Vol. 10/4, p. 55 f, p. 73 f, p. 180 f and p. 217 f, Houben-Weyl, vol. E14b, p. 307 f and 369 f, Houben-Weyl, vol. E5, p. 780 f.
1.5 Entsprechend können die Verbindungen I auch dadurch erhalten werden, daß das Benzylhydroxylamin Ha zunächst mit dem Hy- droxyiminocarbonyl Vllb in das entsprechende Benzyloxyimin der Formel V umgesetzt wird, wobei V anschließend mit dem nu¬ kleophil substituierten Reagens VI wie vorstehend beschrieben zu I umgesetzt wird.1.5 Correspondingly, the compounds I can also be obtained by first reacting the benzylhydroxylamine Ha with the hydroxyiminocarbonyl Vllb in the corresponding benzyloxyimine of the formula V, V then being converted to I with the nucleophilically substituted reagent VI as described above .
Figure imgf000011_0002
Figure imgf000011_0002
Figure imgf000011_0003
1.6 Analog können die Verbindungen I ebenfalls dadurch herge¬ stellt werden, daß das Benzylhydroxylamin Ha zunächst mit dem Dicarbonyl der Formel XI in das Benzyloxyimin der Formel VIII überführt wird und VIII anschließend mit dem Hydroxyl- amin IXa oder dessen Salz IXb wie vorstehdend beschrieben zu I umgesetzt wird.
Figure imgf000011_0003
1.6 Analogously, the compounds I can also be prepared by first converting the benzylhydroxylamine Ha with the dicarbonyl of the formula XI into the benzyloxyimine of the formula VIII and then VIII with the hydroxylamine IXa or its salt IXb as described above for I is implemented.
Figure imgf000012_0001
Figure imgf000012_0001
Figure imgf000012_0002
Figure imgf000012_0002
Figure imgf000012_0003
Figure imgf000012_0003
2 . Verbindungen, in denen R3 und/oder R4 für ein Halogenatom ste¬ hen, erhält man aus den entsprechenden Vorstufen, in denen der betreffende Rest für eine Hydroxygruppe steht nach an sich bekannten Methoden (vgl. Houben-Weyl, Vol. E5, S. 631;2nd Compounds in which R 3 and / or R 4 represent a halogen atom are obtained from the corresponding precursors in which the radical in question represents a hydroxyl group by methods known per se (cf. Houben-Weyl, vol. E5, P. 631;
J. Org. Chem. 36, 233 (1971); J. Org. Chem. 57, 3245 (1992)). Vorzugsweise werden die entsprechenden Umsetzungen zum Halogenderivat auf den Stufen I und VIII vorgenommen.J. Org. Chem. 36, 233 (1971); J. Org. Chem. 57, 3245 (1992)). The corresponding reactions to the halogen derivative are preferably carried out at stages I and VIII.
3. Verbindungen, in denen R3 und/oder R4 über ein 0-, S- oder N- Atom an das Gerüst gebunden sind, erhält man aus den entspre¬ chenden Vorstufen, in denen der betreffende Rest für ein Halogenatom steht nach an sich bekannten Methoden (vgl. Hou¬ ben-Weyl, Bd. E5, S. 826 f und 1280 f, J. Org. Chem. 36, 233 (1971), J. Org. Chem. 46, 3623 (1981)). Vorzugsweise werden die entsprechenden Umsetzungen der Halogenderivat auf den Stufen I und VIII vorgenommen.3. Compounds in which R 3 and / or R 4 are bonded to the skeleton via a 0, S or N atom are obtained from the corresponding precursors in which the radical in question is a halogen atom known methods (cf. Hou¬ ben-Weyl, vol. E5, pp. 826 f and 1280 f, J. Org. Chem. 36, 233 (1971), J. Org. Chem. 46, 3623 (1981)) . Preferably be the corresponding implementations of the halogen derivative were carried out at stages I and VIII.
4. Verbindungen, in denen R3 und/oder R4 über ein Säuerstoffatom an das Gerüst gebunden sind, erhält man z.T. auch aus den entsprechenden Vorstufen, in denen der betreffende Rest für eine Hydroxygruppe steht nach an sich bekannten Methoden (vgl. Houben-Weyl, Bd. E5, S. 826-829, Aust. J. Chem. 21, 1341-9 (1974)). Vorzugsweise werden die entsprechenden Umsetzungen zu den Alkoxyderivaten auf den Stufen I und VIII vorgenommen.4. Compounds in which R 3 and / or R 4 are bonded to the skeleton via an oxygen atom are in some cases also obtained from the corresponding precursors in which the radical in question represents a hydroxyl group by methods known per se (cf. Houben- Weyl, Vol. E5, pp. 826-829, Aust. J. Chem. 21, 1341-9 (1974)). The corresponding reactions to the alkoxy derivatives are preferably carried out at stages I and VIII.
5. Verbindungen, in denen R3 nicht Halogen bedeutet, erhält man bevorzugt dadurch, daß man eine Verbindung X gemäß den in EP-A 493 711 beschriebenen Methoden mit einem Lacton XII zu¬ nächst in die entsprechende Benzoesäure XIII überführt und XIII über die entsprechenden Halogenide in die Cyanocarbon- säuren XIV überführt, welche dann im Wege der Pinner-Reaktion (Angew. Chem. 94, 1 (1982)) in die α-Ketoester XV überführt werden. Aus den Derivaten XV erhält man durch "Umesterung" die entsprechenden Thioester, die anschließend in die Verbindungen I überführt werden.5. Compounds in which R 3 is not halogen are preferably obtained by first converting a compound X according to the methods described in EP-A 493 711 with a lactone XII into the corresponding benzoic acid XIII and XIII via the corresponding ones Halides are converted into the cyanocarboxylic acids XIV, which are then converted into the α-keto esters XV by the Pinner reaction (Angew. Chem. 94, 1 (1982)). The corresponding thioesters are obtained from the derivatives XV by "transesterification" and are subsequently converted into the compounds I.
R5-ON=C(R ) -C(R3) =NOHR 5 -ON = C (R) -C (R 3 ) = NOH
Figure imgf000013_0001
Figure imgf000013_0001
Figure imgf000013_0002
Figure imgf000013_0002
XIIIXIII
Figure imgf000013_0003
XIII.a
Figure imgf000014_0001
Figure imgf000013_0003
XIII.a
Figure imgf000014_0001
Figure imgf000014_0002
Figure imgf000014_0002
Figure imgf000014_0003
Figure imgf000014_0003
,.
Figure imgf000014_0004
Figure imgf000014_0004
6. In einem anderen Verfahrensablauf erhält man die Verbindungen I beispielsweise auch ausgehend von den6. In another process sequence, the compounds I are also obtained, for example, from the
Verbindungen XV, indem man zunächst die Ketogruppe in den Oximether überführt und anschließend die Esterfunktion über die Carbonsäure entweder direkt oder nach Aktivierung (Bil¬ dung beispielsweise der Carbonsäurechloride) in die entspre- chenden Thioester überführt [Organikum, 16. Aufl., S. 415, 423 und 622 (1985)] .
Figure imgf000015_0001
Compounds XV by first converting the keto group into the oxime ether and then converting the ester function via the carboxylic acid either directly or after activation (formation of, for example, the carboxylic acid chlorides) into the corresponding thioesters [Organikum, 16th ed., P. 415 , 423 and 622 (1985)].
Figure imgf000015_0001
Die Verbindungen II können nach den in EP-A 432 503,The compounds II can according to the in EP-A 432 503,
EP-A 463 488, EP-A 386 561 beschriebenen Methoden hergestellt werden.Methods described in EP-A 463 488, EP-A 386 561 can be produced.
Die Verbindungen I können bei der Herstellung aufgrund ihrer C=C und C=N Doppelbindungen als E/Z-Isomerengemische anfallen, die z.B. durch Kristallisation oder Chromatographie in üblicher Weise in die EinzelVerbindungen getrennt werden können.Due to their C = C and C = N double bonds, the compounds I can be produced as E / Z isomer mixtures which, for example, can be separated into the individual compounds by crystallization or chromatography in the usual way.
Sofern bei der Synthese Isomerengemische anfallen, ist im allge- meinen jedoch eine Trennung nicht unbedingt erforderlich, da sich die einzelnen Isomere teilweise während der Aufbereitung für die Anwendung oder bei der Anwendung (z.B. unter Licht-, Säure- oder Baseneinwirkung) ineinander umwandeln können. Entsprechende Um¬ wandlungen können auch nach der Anwendung, beispielsweise bei der Behandlung von Pflanzen in der behandelten Pflanze oder im zu be¬ kämpfenden Schadpilz oder tierischen Schädling erfolgen.If isomer mixtures occur during the synthesis, however, a separation is generally not absolutely necessary since the individual isomers can partially convert into one another during preparation for use or during use (e.g. under the influence of light, acid or base). Corresponding conversions can also take place after use, for example in the treatment of plants in the treated plant or in the harmful fungus or animal pest to be controlled.
In Bezug auf die C=N0CH3 Doppelbindung werden hinsichtlich ihrer Wirksamkeit die E-Isomere der Verbindungen I bevorzugt (Konfigu- ration bezogen auf die -0CH3 Gruppe im Verhältnis zur -COSR1 Gruppe) . In Bezug auf die -C(R3)=NOCH - Doppelbindung werden hinsichtlich ihrer Wirksamkeit die cis-lsomere der Verbindungen I bevorzugt (Konfiguration bezogen auf den Rest R3 im Verhältnis zur -OCH - Gruppe) .With regard to the C = N0CH 3 double bond, the E isomers of the compounds I are preferred in terms of their activity (configuration based on the -0CH 3 group in relation to the -COSR 1 group). With regard to the -C (R 3 ) = NOCH double bond, the cis isomers of the compounds I are preferred in terms of their activity (configuration based on the radical R 3 in relation to the -OCH group).
Bei der eingangs angegebenen Definitionen der Verbindungen I wur¬ den Sammelbegriffe verwendet, die allgemein repräsentativ für die folgenden Gruppen stehen:In the definitions of the compounds I given at the outset, collective terms were used which are generally representative of the following groups:
Haloσen; Fluor, Chlor, Brom und Jod;Halos; Fluorine, chlorine, bromine and iodine;
Alkyl; geradkettige oder verzweigte Alkylgruppen mit 1 bis 4, 6 oder 10 Kohlenstoffatomen, z.B. Ci-Cε-Alkyl wie Methyl, Ethyl, Propyl, 1-Methylethyl, Butyl, 1-Methyl-propyl, 2-Methylpropyl, 1,1-Dimethylethyl, Pentyl, 1-Methylbutyl, 2-Methylbutyl, 3-Methylbutyl, 2,2-Di-methylpropyl, 1-Ethylpropyl, Hexyl, 1, 1-Dimethylpropyl, 1,2-Dimethylpropyl, 1-Methylpentyl, 2-Methyl- pentyl, 3-Methylpentyl, 4-Methylpentyl, 1,1-Dimethylbutyl, 1,2-Dimethylbutyl, 1,3-Dimethylbutyl, 2,2-Dimethylbutyl, 2,3-Dimethylbutyl, 3,3-Dimethylbutyl, 1-Ethylbutyl, 2-Ethylbutyl, 1,1,2-Trimethylpropyl, 1,2,2-Trimethylpropyl, 1-Ethyl-l-methyl- propyl und 1- Ethyl-2-methylpropyl;Alkyl; straight or branched alkyl groups with 1 to 4, 6 or 10 carbon atoms, e.g. Ci-Cε-alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1, 2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2- Trimethylpropyl, 1-ethyl-l-methylpropyl and 1-ethyl-2-methylpropyl;
-MkYlflm nO- eine Aminogruppe, welche eine geradkettige oder ver- zweigte Alkylgruppe mit 1 bis 6 Kohlenstoffatomen wie vorstehend genannt trägt;-MkYlflm nO- an amino group which carries a straight-chain or branched alkyl group with 1 to 6 carbon atoms as mentioned above;
Diallylaπι-1nn» eine Aminogruppe, welche zwei voneinander unabhän¬ gige, geradkettige oder verzweigte Alkylgruppen mit jeweils 1 bis 6 Kohlenstoffatomen wie vorstehend genannt, trägt;Diallylaπι-1nn » an amino group which carries two independent, straight-chain or branched alkyl groups each having 1 to 6 carbon atoms as mentioned above;
Alkylcarbonyl; geradkettige oder verzweigte Alkylgruppen mit 1 bis 10 Kohlenstoffatomen, welche über eine Carbonylgruppe (-CO-) an das Gerüst gebunden sind;Alkylcarbonyl; straight-chain or branched alkyl groups with 1 to 10 carbon atoms, which are bonded to the skeleton via a carbonyl group (-CO-);
Alkylsulfonyl; geradkettige oder verzweigte Alkylgruppen mit 1 bis 6 oder 10 Kohlenstoffatomen, welche über eine Sulfonylgruppe (-S(=0) -) an das Gerüst gebunden sind;Alkylsulfonyl; straight-chain or branched alkyl groups with 1 to 6 or 10 carbon atoms, which are bonded to the skeleton via a sulfonyl group (-S (= 0) -);
AUcylsulfoxyl; geradkettige oder verzweigte Alkylgruppen mit 1 bis 6 Kohlenstoffatomen, welche über eine Sulfoxylgruppe ( -S(=0)-) an das Gerüst gebunden sind;Acylsulfoxyl; straight-chain or branched alkyl groups with 1 to 6 carbon atoms, which are bonded to the skeleton via a sulfoxyl group (-S (= 0) -);
AIVyi«Tninocarbonyl; Alkylaminogruppen mit 1 bis 6 Kohlenstoff- atomen wie vorstehend genannt, welche über eine Carbonylgruppe (-CO-) an das Gerüst gebunden sind; Pialkvlaminocarbonyl; Dialkylaminogruppen mit jeweils 1 bis 6 Kohlenstoffatomen pro Alkylrest wie vorstehend genannt, welche über eine Carbonylgruppe (-C0-) an das Gerüst gebunden sind;AIVyi «Tninocarbonyl; Alkylamino groups with 1 to 6 carbon atoms as mentioned above, which are bonded to the skeleton via a carbonyl group (-CO-); Pialkvlaminocarbonyl; Dialkylamino groups each having 1 to 6 carbon atoms per alkyl radical as mentioned above, which are bonded to the skeleton via a carbonyl group (-C0-);
Alkylaminothiocarbonyl; Alkylaminogruppen mit 1 bis 6 Kohlen¬ stoffatomen wie vorstehend genannt, welche über eine Thiocarbo- nylgruppe (-CS-) an das Gerüst gebunden sind;Alkylaminothiocarbonyl; Alkylamino groups with 1 to 6 carbon atoms as mentioned above, which are bonded to the skeleton via a thiocarbonyl group (-CS-);
*-**■?7fcy1p™inothiocarbonyl; Dialkylaminogruppen mit jeweils 1 bis 6 Kohlenstoffatomen pro Alkylrest wie vorstehend genannt, welche über eine Thiocarbonylgruppe (-CS-) an das Gerüst gebunden sind;* - ** ■? 7fcy 1 p ™ inothiocarbonyl; Dialkylamino groups each having 1 to 6 carbon atoms per alkyl radical as mentioned above, which are bonded to the skeleton via a thiocarbonyl group (-CS-);
Haloσenalkyl: geradkettige oder verzweigte Alkylgruppen mit 1 bis 6 Kohlenstoffatomen, wobei in diesen Gruppen teilweise oder voll- ständig die Wasserstoffatome durch Halogenatome wie vorstehend genannt ersetzt sein können, z.B. Cι-C2-Halogenalkyl wie Chlor¬ methyl, Dichlormethyl, Trichlormethyl, Fluormethyl, Difluor- methyl, Trifluormethyl, Chlorfluormethyl, Dichlorfluormethyl, Chlordifluormethyl, 1-Fluorethyl, 2-Fluorethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, 2-Chlor-2-fluorethyl, 2-Chlor-2,2-difluor¬ ethyl, 2,2-Dichlor-2-fluorethyl, 2,2,2-Trichlorethyl und Penta- fluorethyl;Haloσenalkyl: straight-chain or branched alkyl groups with 1 to 6 carbon atoms, in which groups the hydrogen atoms in these groups can be partially or completely replaced by halogen atoms as mentioned above, for example C 1 -C 2 -haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, Difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2- difluoro-ethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;
Alko.κγi geradkettige oder verzweigte Alkylgruppen mit 1 bis 4 oder 6 Kohlenstoffatomen wie vorstehend genannt, welche über ein Säuerstoffatom (-0-) an das Gerüst gebunden sind, z.B. Ci-C6-Alkoxy wie Methyloxy, Ethyloxy, Propyloxy, 1-Methylethyloxy, Butyloxy, 1-Methyl-propyloxy, 2-Methylpropyloxy, 1,1-Dimethyl- ethyloxy, Pentyloxy, 1-Methylbutyloxy, 2-Methylbutyloxy, 3-Methylbutyloxy, 2,2-Di-methylpropyloxy, 1-Ethylpropyloxy,Alko.κγi straight-chain or branched alkyl groups with 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the structure via an oxygen atom (-0-), for example Ci-C 6 -alkoxy such as methyloxy, ethyloxy, propyloxy, 1-methylethyloxy , Butyloxy, 1-methyl-propyloxy, 2-methylpropyloxy, 1,1-dimethylethyloxy, pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 2,2-dimethylpropyloxy, 1-ethylpropyloxy,
Hexyloxy, 1,1-Dimethylpropyloxy, 1,2-Dimethylpropyloxy, 1-Methyl- pentyloxy, 2-Methylpentyloxy, 3-Methylpentyloxy, 4-Methylpentyl- oxy, 1,1-Dimethylbutyloxy, 1,2-Dimethylbutyloxy, 1,3-Dimethyl- butyloxy, 2,2-Dimethylbutyloxy, 2,3-Dimethylbutyloxy, 3,3-Dimethylbutyloxy, 1-Ethyl-butyloxy, 2-Ethylbutyloxy, 1,1,2-Trimethylpropyloxy, 1,2,2-Trimethylpropyloxy, 1-Ethyl-l-methylpropyloxy und l-Ethyl-2-methylpropyloxy;Hexyloxy, 1,1-dimethylpropyloxy, 1,2-dimethylpropyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutyloxy, 1,2-dimethylbutyloxy, 1,3- Dimethylbutyloxy, 2,2-dimethylbutyloxy, 2,3-dimethylbutyloxy, 3,3-dimethylbutyloxy, 1-ethylbutyloxy, 2-ethylbutyloxy, 1,1,2-trimethylpropyloxy, 1,2,2-trimethylpropyloxy, 1- Ethyl-l-methylpropyloxy and l-ethyl-2-methylpropyloxy;
Alkoxycarbonyl; geradkettige oder verzweigte Alkylgruppen mit 1 bis 6 Kohlenstoffatomen, welche über eine Oxycarbonylgruppe (-0C(=0)-) an das Gerüst gebunden sind;Alkoxycarbonyl; straight-chain or branched alkyl groups with 1 to 6 carbon atoms, which are bonded to the skeleton via an oxycarbonyl group (-0C (= 0) -);
Halogenalkoxy; geradkettige oder verzweigte Alkylgruppen mit 1 bis 6 Kohlenstoffatomen, wobei in diesen Gruppen teilweise oder vollständig die Wasserstoffatome durch Halogenatome wie vorste- hend genannt ersetzt sein können, und wobei diese Gruppen über ein Sauerstoffatom an das Gerüst gebunden sind;Haloalkoxy; straight-chain or branched alkyl groups with 1 to 6 carbon atoms, the hydrogen atoms in these groups being partially or completely replaced by halogen atoms as above hend called may be replaced, and wherein these groups are bonded to the structure via an oxygen atom;
Alkylthio; geradkettige oder verzweigte Alkylgruppen mit 1 bis 4 oder 6 Kohlenstoffatomen wie vorstehend genannt, welche über ein Schwefelatom (-S-) an das Gerüst gebunden sind, z.B. Cι-C6-Alkyl- thio wie Methylthio, Ethylthio, Propylthio, 1-Methylethylthio, Butylthio, 1-Methylpropylthio, 2-Methylpropylthio, 1,1-Dimethyl- ethylthio, Pentylthio, 1-Methylbutylthio, 2-Methylbutylthio, 3-Methylbutylthio, 2,2-Di-methylpropylthio, 1-Ethylpropylthio, Hexylthio, 1,1-Dimethylpropylthio, 1,2-Dirnethylpropylthio, 1-Methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methylpentylthio, 1,1-Dimethylbutylthio, 1,2-Dimethylbutylthio, 1,3-Dimethylbutylthio, 2,2-Dimethylbutylthio, 2,3-Dimethylbutyl- thio, 3,3-Dimethylbutylthio, 1-Ethylbutylthio, 2-Ethylbutylthio, 1,1,2-Trimethylpropylthio, 1,2,2-Trimethylpropylthio, 1-Ethyl-l-methylpropylthio und l-Ethyl-2-methylpropylthio;Alkylthio; straight-chain or branched alkyl groups with 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the skeleton via a sulfur atom (-S-), for example C 1 -C 6 -alkyl thio such as methylthio, ethylthio, propylthio, 1-methylethylthio, Butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1- Dimethylpropylthio, 1,2-Dirnethylpropylthio, 1-Methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methylpentylthio, 1,1-Dimethylbutylthio, 1,2-Dimethylbutylthio, 1,3-Dimethylbutylthio, 2,2-Dimethylbutylthio, 2, 3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-l-methylpropylthio and l-ethyl-2- methylpropylthio;
Cvcloalkyl; monocyclische Alkylgruppen mit 3 bis 6 Kohenstof- fringgliedern, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl und Cyclohexyl;Cvcloalkyl; monocyclic alkyl groups with 3 to 6 carbon ring members, e.g. Cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
Alkenyl; geradkettige oder verzweigte Alkenylgruppen mit 2 bis 6 oder 10 Kohlenstoffatomen und einer Doppelbindung in einer belie- bigen Position, z.B. C2-C6-Alkenyl wie Ethenyl, 1-Propenyl, 2-Propenyl, 1-Methylethenyl, 1-Butenyl, 2-Butenyl, 3-Butenyl, 1-Methyl-l-propenyl, 2-Methyl-l-propenyl, l-Methyl-2-propenyl, 2-Methyl-2-propenyl, 1-Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1-Methyl-l-butenyl, 2-Methyl-l-butenyl, 3-Methyl-l-butenyl, l-Methyl-2-butenyl, 2-Methyl-2-butenyl, 3-Methyl-2-butenyl, l-Methyl-3-butenyl, 2-Methyl-3-butenyl, 3-Methyl-3-butenyl, 1,l-Dimethyl-2-propenyl, 1,2-Dimethyl-l-propenyl, 1,2-Dimethyl-2-propenyl, 1-Ethyl-l-propenyl, l-Ethyl-2-propenyl, 1-Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5-Hexenyl, 1-Methyl-l-pentenyl,Alkenyl; straight-chain or branched alkenyl groups with 2 to 6 or 10 carbon atoms and a double bond in any position, for example C 2 -C 6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2- Butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2- butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, l-dimethyl-2-propenyl, 1,2-dimethyl-l-propenyl, 1,2- Dimethyl-2-propenyl, 1-ethyl-l-propenyl, l-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-l-pentenyl,
2-Methyl-l-pentenyl, 3-Methyl-l-pentenyl, 4-Methyl-l-pentenyl, l-Methyl-2-pentenyl, 2-Methyl-2-pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl, l-Methyl-3-pentenyl, 2-Methyl-3-pentenyl, 3-Methyl-3-pentenyl, 4-Methyl-3-pentenyl, l-Methyl-4-pentenyl, 2-Methyl-4-pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1,l-Dimethyl-2-butenyl, 1,l-Di-methyl-3-butenyl, 1,2-Dimethyl-l-butenyl, 1,2-Dimethyl-2-butenyl, l,2-Dimethyl-3-butenyl, 1,3-Dimethyl-l-butenyl, 1,3-Dimethyl-2-butenyl, 1,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3-Dimethyl-l-butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3-Dimethyl-l-butenyl, 3,3-Dimethyl-2-butenyl, 1-Ethyl-l-butenyl, l-Ethyl-2-butenyl, l-Ethyl-3-butenyl, 2-Ethyl-l-butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, 1,1,2-Trimethyl-2-propenyl, 1- Ethyl-l-methyl-2-propenyl, l-Ethyl-2-methyl-l-propenyl und l-Ethyl-2-methyl-2-propenyl;2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4- Methyl-2-pentenyl, l-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, l-methyl-4-pentenyl, 2-methyl- 4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, l-dimethyl-2-butenyl, 1, l-dimethyl-3-butenyl, 1,2-dimethyl-l- butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3- butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-l-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-l- butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1, 1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;
Alkβnyloxy; geradkettige oder verzweigte Alkenylgruppen mit 2 bis 6 Kohlenstoffatomen und einer Doppelbindung in einer beliebigen Position, welche über ein Sauerstoffatom (-0-) an das Gerüst ge¬ bunden sind;Alkβnyloxy; straight-chain or branched alkenyl groups with 2 to 6 carbon atoms and a double bond in any position, which are bonded to the skeleton via an oxygen atom (-0-);
Alkβnylcarbonyl; geradkettige oder verzweigte Alkenylgruppen mit 2 bis 10 Kohlenstoffatomen und einer Doppelbindung in einer be¬ liebigen Position, welche über eine Carbonylgruppe (-CO-) an das Gerüst gebunden sind;Alkβnylcarbonyl; straight-chain or branched alkenyl groups with 2 to 10 carbon atoms and a double bond in any position which are bonded to the skeleton via a carbonyl group (-CO-);
Alkenvlthio bzw. Alkenvlamino; geradkettige oder verzweigte Alkenylgruppen mit 2 bis 6 Kohlenstoffatomen und einer Doppelbin¬ dung in einer beliebigen Position, welche (Alkenylthio) über ein Schwefelatom bzw. (Alkenylamino) ein Stickstoffatom an das Gerüst gebunden sind;Alkenvlthio or Alkenvlamino; straight-chain or branched alkenyl groups with 2 to 6 carbon atoms and a double bond in any position which (alkenylthio) are bonded to the skeleton via a sulfur atom or (alkenylamino) a nitrogen atom;
Alkinyl; geradkettige oder verzweigte Alkinylgruppen mit 2 bis 10 Kohlenstoffatomen und einer Dreifachbindung in einer beliebigen Position, z.B. C -C6-Alkinyl wie Ethinyl, 2-Propinyl, 2-Butinyl, 3-Butinyl, l-Methyl-2-propinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, l-Methyl-2-butinyl, l-Methyl-3-butinyl, 2-Methyl-3-butinyl, 1,l-Dimethyl-2-propinyl, l-Ethyl-2-propinyl, 2-Hexinyl, 3-Hexinyl, 4-Hexinyl, 5-Hexinyl, l-Methyl-2-pentinyl, l-Methyl-3-pentinyl, 1-Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl-4-pentinyl, 3-Methyl-4-pentinyl, 4-Methyl-2-pentinyl, 1, l-Dimethyl-2-butinyl, l,l-Dimethyl-3-butinyl, 1,2-Dimethyl-3-butinyl, 2,2-Dimethyl-3-butinyl, l-Ethyl-2-butinyl, l-Ethyl-3-butinyl, 2-Ethyl-3-butinyl und l-Ethyl-l-methyl-2-propinyl;Alkynyl; straight-chain or branched alkynyl groups with 2 to 10 carbon atoms and a triple bond in any position, for example C -C 6 -alkynyl such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl , 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 1, l-dimethyl-2-propynyl, l-ethyl-2-propynyl , 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, l-methyl-2-pentynyl, l-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2nd -Methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1, l-dimethyl-2-butynyl, l, l-dimethyl-3-butynyl, 1,2-dimethyl-3 -butinyl, 2,2-dimethyl-3-butynyl, l-ethyl-2-butynyl, l-ethyl-3-butynyl, 2-ethyl-3-butynyl and l-ethyl-l-methyl-2-propynyl;
Alkinylcarbonyl; geradkettige oder verzweigte Alkinylgruppen mit 3 bis 10 Kohlenstof atomen und einer Dreifachbindung in einer be¬ liebigen Position, welche über eine Carbonylgruppe (-CO-) an das Gerüst gebunden sind;Alkynylcarbonyl; straight-chain or branched alkynyl groups with 3 to 10 carbon atoms and a triple bond in any position, which are bonded to the skeleton via a carbonyl group (-CO-);
Alkinvloxv bzw. Alkinvlthio und Alkinvlamino; geradkettige oder verzweigte Alkinylgruppen mit 2 bis 6 Kohlenstoffatomen und einer Dreifachbindung in einer beliebigen Position, welche (Alkinyloxy) über ein Sauers offatom bzw. (Alkinylthio) über ein Schwefelatom oder (Alkinylamino) über ein Stickstoffatom an das Gerüst gebun¬ den sind; Pvcloalkoxy bzw. Cycloalkylthio und Cvcloalkyl«minn; mono- cyclische Alkenylgruppen mit 3 bis 6 Kohlenstoffringgliedern, welche (Cycloalkyloxy) über ein Sauerstoffatom oder (Cycloalkyl¬ thio) ein Schwefelatom oder (Cycloalkylamino) über ein Stick- stoffatom an das Gerüst gebunden sind, z.B. Cyclopropyl, Cyclo- butyl, Cyclopentyl oder Cyclohexyl;Alkinvloxv or Alkinvlthio and Alkinvlamino; straight-chain or branched alkynyl groups with 2 to 6 carbon atoms and a triple bond in any position, which (alkynyloxy) via an acid atom or (alkynylthio) via a sulfur atom or (alkynylamino) via a nitrogen atom are bonded to the skeleton; Pvcloalkoxy or Cycloalkylthio and Cvcloalkyl «minn; monocyclic alkenyl groups with 3 to 6 carbon ring members which (cycloalkyloxy) are bonded to the skeleton via an oxygen atom or (cycloalkylthio) a sulfur atom or (cycloalkylamino) via a nitrogen atom, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl ;
Cvcloalkanvl bzw. Cvcloalkenvloxy. Cycloalkenylthio und Cvclo-
Figure imgf000020_0001
monocyclische Alkenylgruppen mit 3 bis 6 Kohlenstoff- ringgliedern, welche direkt bzw. (cycloalkenyloxy) über einCvcloalkanvl or Cvcloalkenvloxy. Cycloalkenylthio and Cvclo-
Figure imgf000020_0001
monocyclic alkenyl groups with 3 to 6 carbon ring members, which directly or (cycloalkenyloxy) via one
Sauerstoffatom oder (Cycloalkenylthio) ein Schwefelatom oder (Cy¬ cloalkenylamino) über ein Stickstoffatom an das Gerüst gebunden sind, z.B. Cyclopropenyl, Cyclobutenyl, Cyclopentenyl oder Cyclo- hexenyl;Oxygen atom or (cycloalkenylthio) a sulfur atom or (cycloalkenylamino) are bonded to the skeleton via a nitrogen atom, e.g. Cyclopropenyl, cyclobutenyl, cyclopentenyl or cyclohexenyl;
Heterocvclvl bzw. Heterocvclvloacv. Heterocvclylthio und Hetβrocv- CλYJ.-Pr.irgi drei- bis sechsgliedrige, gesättigte oder partiell un- • gesättigte mono- oder polycyclische Heterocyclen, die ein bis drei Hereroatome ausgewählt aus einer Gruppe bestehend aus Sauer- stoff, Stickstoff und Schwefel enthalten, und welche direkt bzw. (Heterocyclyloxy) über ein Sauerstoffatom oder (Heterocyclylthio) über ein Schwefelatom oder (Heterocyclylamino) über ein Stick- stoffatom an das Gerüst gebunden sind, wie z.B. 2-Tetrahydro- furanyl, Oxiranyl, 3-Tetrahydrofuranyl, 2-Tetrahydrothienyl, 3-Tetrahydrothienyl, 2-Pyrrolidinyl, 3-Pyrrolidinyl, 3-lsoxazol- dinyl, 4-Isoxazolidinyl, 5-Isoxazolidinyl, 3-Isothiazolidinyl, 4-Isothiazolidinyl, 5-Isothiazolidinyl, 3-Pyrazolidinyl, 4-Pyrazolidinyl, 5-Pyrazolidinyl, 2-Oxazolidinyl, 4-Oxazolidinyl, 5-Oxazolidinyl, 2-Thiazolidinyl, 4-Thiazolidinyl, 5-Thia- zolidinyl, 2-lmidazolidinyl, 4-Imidazolidinyl, 1,2,4-Oxadia- zolidin-3-yl, 1,2,4-Oxadiazolidin-5-yl, 1,2,4-Thiadia- zolidin-3-yl, 1,2,4-Thiadiazolidin-5-yl, 1,2,4-Triazolidin-3-yl, l,3,4-Oxadiazolidin-2-yl, 1,3,4-Thiadiazolidin-2-yl, 1,3,4-Tri- azolidin-2-yl, 2,3-Dihydrofur-2-yl, 2,3-Dihydrofur-3-yl, 2,3-Di- hydro-fur-4-yl, 2,3-Dihydro-fur-5-yl, 2,5-Dihydro-fur-2-yl, 2,5-Dihydro-fur-3-yl, 2,3-Dihydrothien-2-yl, 2,3-Dihydro- thien-3-yl, 2,3-Dihydrothien-4-yl, 2,3-Dihydrothien-5-yl, 2,5-Dihydrothien-2-yl, 2,5-Dihydrothien-3-yl, 2,3-Dihydropyr- rol-2-yl, 2,3-Dihydropyrrol-3-yl, 2,3-Dihydropyrrol-4-yl, 2,3-Di- hydropyrrol-5-yl, 2, 5-Dihydropyrrol-2-yl, 2,5-Dihydropyrrol-3-yl, 2,3-Dihydroisoxazol-3-yl, 2,3-Dihydroisoxazol-4-yl, 2,3-Dihydroi- soxazol-5-yl, 4,5-Dihydroisoxazol-3-yl, 4,5-Dihydroisoxazol-4-yl, 4,5-Dihydroisoxazol-5-yl, 2,5-Dihydroisothiazol-3-yl, 2,5-Dihy- droisothiazol-4-yl, 2,5-Dihydroisothiazol-5-yl, 2,3-Dihydroisopy- razol-3-yl, 2,3-Dihydroisopyrazol-4-yl, 2,3-Dihydroisopyra- zol-5-yl, 4,5-Dihydroisopyrazol-3-yl, 4,5-Dihydroisopyrazol-4-yl, 4,5-Dihydroisopyrazol-5-yl, 2,5-Dihydroisopyrazol-3-yl, 2,5-Dihy- droisopyrazol-4-yl, 2, 5-Dihydroisopyrazol-5-yl, 2,3-Dihydrooxa- zol-3-yl, 2,3-Dihydrooxazol-4-yl, 2,3-Dihydrooxazol-5-yl, 4,5-Di- hydrooxazol-3-yl, 4, 5-Dihydrooxazol-4-yl, 4,5-Dihydrooxazol-5-yl, 2,5-Dihydrooxazol-3-yl, 2, 5-Dihydrooxazol-4-yl, 2, 5-Dihydrooxa- zol-5-yl, 2,3-Dihydrothiazol-2-yl, 2,3-Dihydrothiazol-4-yl, 2,3-Dihydrothiazol-5-yl, 4,5-Dihydrothiazol-2-yl, 4,5-Dihydro- thiazol-4-yl, 4,5-Dihydrothiazol-5-yl, 2,5-Dihydrothiazol-2-yl, 2, 5-Dihydrothiazol-4-yl, 2,5-Dihydrothiazol-5-yl, 2,3-Dihydroimi- dazol-2-yl, 2,3-Dihydroimidazol-4-yl, 2,3-Dihydroimidazol-5-yl, 4,5-Dihydroimidazol-2-yl, 4,5-Dihydroimidazol-4-yl, 4,5-Dihydroi- midazol-5-yl, 2,5-Dihydroimidazol-2-yl, 2,5-Dihydroimidazol-4-yl, 2,5-Dihydroimidazol-5-yl, 2-Morpholinyl, 3-Morpholinyl, 2-Piperidinyl, 3-Piperidinyl, 4-Piperidinyl, 3-Tetrahydropyrida- zinyl, 4-Tetrahydropyridazinyl, 2-Tetrahydropyrimidinyl, 4-Tetra- hydropyrimidinyl, 5-Tetrahydropyrimidinyl, 2-Tetrahydropyrazinyl, 1,3,5-Tetrahydrotriazin-2-yl, 1,2,4-Tetrahydrotriazin-3-yl, l,3-Dihydrooxazin-2-yl, 1,3-Dithian-2-yl, 2-Tetrahydropyranyl, 1,3-Dioxolan-2-yl, 3,4,5,6-Tetrahydropyridin-2-yl, 4H-1,3-Thiazin-2-yl, 4H-3,l-Benzothiazin-2-yl, 1,l-Dioxo-2,3,4,5-tetrahydrothien-2-yl, 2H-1,4-Benzothiazin-3-yl, 2H-l,4-Benzoxazin-3-yl, 1,3-Dihydrooxazin-2-yl, 1,3-Dithian-2-yl,Heterocvclvl or Heterocvclvloacv. Heterocvclylthio and Hetβrocv- CλYJ.-Pr.irgi three- to six-membered, saturated or partially unsaturated • mono- or polycyclic heterocycles containing one to three hereroatoms selected from a group consisting of oxygen, nitrogen and sulfur, and which directly or (heterocyclyloxy) via an oxygen atom or (heterocyclylthio) via a sulfur atom or (heterocyclylamino) via a nitrogen atom are bound to the structure, such as 2-tetrahydrofuranyl, oxiranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3 -Tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazole-dinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2 -Oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2 , 4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4 -Thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, l, 3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-tri azolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,3-dihydro-fur-4-yl, 2,3-dihydro-fur-5 -yl, 2,5-dihydro-fur-2-yl, 2,5-dihydro-fur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydro-thien-3-yl, 2 , 3-dihydrothien-4-yl, 2,3-dihydrothien-5-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 2,3-dihydropyrrol-2-yl , 2,3-dihydropyrrol-3-yl, 2,3-dihydropyrrol-4-yl, 2,3-dihydropyrrol-5-yl, 2,5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3 -yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazole -4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl, 2,3 -Dihydroisopyrazol-3-yl, 2,3-dihydroisopyrazol-4-yl, 2,3-dihydroisopyrazol-5-yl, 4,5-dihydroisopyrazol-3-yl, 4,5-dihydroisopyrazol-4-yl , 4,5-dihydroisopyrazol-5-yl, 2,5-dihydroisopyrazol-3-yl, 2,5-dihy- droisopyrazol-4-yl, 2, 5-dihydroisopyrazol-5-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4, 5-dihydrooxazol-3-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-3-yl, 2,5-dihydrooxazol-4-yl, 2, 5-dihydrooxazol-5-yl, 2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 4,5-dihydrothiazol-2- yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2, 5-dihydrothiazol-4-yl, 2,5-dihydrothiazol- 5-yl, 2,3-dihydroimidazol-2-yl, 2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl, 4,5- Dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl, 2- Morpholinyl, 3-morpholinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-tetra-hydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetraz 5-tetrahydrotriazin-2-yl, 1,2 , 4-tetrahydrotriazin-3-yl, 1,3-dihydrooxazin-2-yl, 1,3-dithian-2-yl, 2-tetrahydropyranyl, 1,3-dioxolan-2-yl, 3,4,5,6 -Tetrahydropyridin-2-yl, 4H-1,3-thiazin-2-yl, 4H-3, l-benzothiazin-2-yl, 1, l-dioxo-2,3,4,5-tetrahydrothien-2-yl , 2H-1,4-benzothiazin-3-yl, 2H-l, 4-benzoxazin-3-yl, 1,3-dihydrooxazin-2-yl, 1,3-dithian-2-yl,
Aryl feajw, Arylgyy, J TYlthiP, A*CrJ,c rt>PPYl φnfl ArylSttlfoBYl i aro¬ matische mono- oder polycyclische Kohenwasserstoffreste welche direkt bzw. (Aryloxy) über ein Sauerstoffatom (-0-) oder (Aryl¬ thio) ein Schwefelatom (-S-), (Arylcarbonyl) über eine Carbonyl¬ gruppe (-CO-) oder (Arylsulfonyl) über eine Sulfonylgruppe (-S02-) an das Gerüst gebunden sind, z.B. Phenyl, Naphthyl und Phenant- hrenyl bzw. Phenyloxy, Naphthyloxy und Phenanthrenyloxy und die entsprechenden Carbonyl- und Sulfonylreste;Aryl feajw, Arylgyy, J TYlthiP, A * CrJ, c rt> PPYl φnfl ArylSttlfoBYl i aromatic mono- or polycyclic hydrocarbon residues which are directly or (aryloxy) via an oxygen atom (-0-) or (aryl¬ thio) a sulfur atom (-S-), (arylcarbonyl) via a carbonyl group (-CO-) or (arylsulfonyl) via a sulfonyl group (-S0 2 -) are bound to the skeleton, for example phenyl, naphthyl and phenanthrenyl or phenyloxy, Naphthyloxy and phenanthrenyloxy and the corresponding carbonyl and sulfonyl radicals;
Λτ"ylftιπ.infl. aromatische mono- oder polycyclische Kohlenwasser- stoffreste, welche über ein Stickstoffatom an das Gerüst gebunden sind;Λ τ "ylftιπ.infl. Aromatic mono- or polycyclic hydrocarbon residues which are bonded to the skeleton via a nitrogen atom;
Hetarvl bzw. He rvloxv. Hetarylthio. Hetarylcarbonyl und Hetarylaulfonyl: aromatische mono- oder polycyclische Reste wel¬ che neben Kohlenstoffringgliedern zusätzlich ein bis vier Stick¬ stoffatome oder ein bis drei Stickstoffatome und ein Sauerstoff- oder ein Schwefelatom oder ein Sauerstoff- oder ein Schwefelatom enthalten können und welche direkt bzw. (Hetaryloxy) über ein Sauerstoffatom (-0-) oder (Hetarylthio) ein Schwefelatom (-S-) , (Hetarylcarbonyl) über eine Carbonylgruppe (-C0-) oder (Hetaryl- sulfonyl) über eine Sulfonylgruppe (-S02-) an das Gerüst gebunden sind, z.B. 5-σliedriσes Heteroarvl. enthaltend ein bis drei Stickstoff¬ atome: 5-Ring Heteroarylgruppen, welche neben Kohlenstoff- atomen ein bis drei Stickstoffatome als Ringglieder enthalten können, z.B. 2-Pyrrolyl, 3-Pyrrolyl, 3-Pyrazolyl, 4-Pyrazolyl, 5-Pyrazolyl, 2-Imidazolyl, 4-Imidazolyl, 1,2,4- Triazol-3-yl und 1,3,4-Triazol-2-yl;Hetarvl or He rvloxv. Hetarylthio. Hetarylcarbonyl and hetarylaulfonyl: aromatic mono- or polycyclic radicals which, in addition to carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom and which or (hetaryloxy ) via an oxygen atom (-0-) or (hetarylthio) a sulfur atom (-S-), (hetarylcarbonyl) via a carbonyl group (-C0-) or (hetaryl-sulfonyl) via a sulfonyl group (-S0 2 -) to the skeleton are bound, e.g. 5-σliedriσes heteroarvl. containing one to three nitrogen atoms: 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three nitrogen atoms as ring members, for example 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2- Imidazolyl, 4-imidazolyl, 1,2,4-triazol-3-yl and 1,3,4-triazol-2-yl;
5-σliedriσes Heteroarvl. enthaltend ein bis vier S ickstoff- atome oder ein bis drei Stickstoffatome und ein Schwefel- oder Sauerstoffatom oder ein Sauerstoff oder ein5-σliedriσes heteroarvl. containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or one
Schwefelatom: 5-Ring Heteroarylgruppen, welche neben Kohlen¬ stoffatomen ein bis vier Stickstoffatome oder ein bis drei Stickstoffatome und ein Schwefel- oder Sauerstoffatom oder ein Sauerstoff- oder Schwefelatom als Ringglieder enthalten können, z.B. 2-Furyl, 3-Furyl, 2-Thienyl, 3-Thienyl, 2-Pyrrolyl, 3-Pyrrolyl, 3-Isoxazolyl, 4-Isoxazolyl, 5-Isoxazolyl, 3-Isothiazolyl, 4-Isothiazolyl, 5-Isothiazolyl, 3-Pyrazolyl, 4-Pyrazolyl, 5-Pyrazolyl, 2-0xazolyl, 4-0xa- zolyl, 5-0xazolyl, 2-Thiazolyl, 4-Thiazolyl, 5-Thiazolyl, 2-Imidazolyl, 4-Imidazolyl, 1,2,4-Oxadiazol-3-yl, l,2,4-Oxadiazol-5-yl, 1,2,4- Thiadiazol -3-yl, 1,2,4-Thiadiazol-5-yl, 1,2,4-Triazol-3-yl, l,3,4-Oxadiazol-2-yl, 1,3,4-Thiadiazol-2-yl und 1,3,4- Tri- azol-2-yl;Sulfur atom: 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or sulfur atom as ring members, e.g. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3- Pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-0xazolyl, 4-0xazolyl, 5-0xazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4- Oxadiazol-3-yl, l, 2,4-oxadiazol-5-yl, 1,2,4-thiadiazol -3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol- 3-yl, l, 3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl and 1,3,4-triazol-2-yl;
b hgpkond nsie tes S-gi edriges Heteroaryl. enthaltend ein bis drei Stickstoffatome oder ein Stickstoffatom und/oder ein Sauerstoff- oder Schwefelatom: 5-Ring Heteroarylgruppen, wel¬ che neben Kohlenstoffatomen ein bis vier Stickstoffatome oder ein bis drei Stickstoffatome und ein Schwefel- oder Sauer¬ stoffatom oder ein Sauerstoff- oder ein Schwefelatom als Ringglieder enthalten können, und in welchen zwei benachbarte Kohlenstoffringglieder oder ein Stickstoff- und ein benach¬ bartes Kohlenstoffringglied durch eine Buta-1,3-dien- 1,4-diylgruppe verbrückt sein können;b hgpkond nsie tes S-gi noble heteroaryl. containing one to three nitrogen atoms or one nitrogen atom and / or one oxygen or sulfur atom: 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or one Can contain sulfur atom as ring members, and in which two adjacent carbon ring members or a nitrogen and a neighboring carbon ring member can be bridged by a buta-1,3-diene-1,4-diyl group;
über Stickstoff gebundenes 5-σliedriσes Heteroarvl. enthal¬ tend ein bis vier Stickstoffatome. oder über Stickstoff ge¬ bundenes benzokondensiertes 5-σliedriσes Heteroarvl, enthal- tend ein bis drei Stickstoffatome: 5-Ring Heteroarylgruppen, welche neben Kohlenstoffatomen ein bis vier Stickstoffatome bzw. ein bis drei Stickstoffatome als Ringglieder enthalten können, und in welchen zwei benachbarte Kohlenstoffringglie¬ der oder ein Stickstoff- und ein benachbartes Kohlenstof- fringglied durch eine Buta-l,3-dien- 1,4-diylgruppe verbrückt sein können, wobei diese Ringe über eines der Stickstoffring¬ glieder an das Gerüst gebunden sind;5-σliedriσes heteroarvl bound via nitrogen. containing one to four nitrogen atoms. or nitrogen-bonded benzo-fused 5-membered heteroaryl containing one to three nitrogen atoms: 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to four nitrogen atoms or one to three nitrogen atoms as ring members, and in which two adjacent carbon ring members the or a nitrogen and an adjacent carbon ring member are bridged by a buta-1,3-diene-1,4-diyl group can be, wherein these rings are bound to the frame via one of the nitrogen ring members;
6-σliedriσes Heteroarvl, enthaltend ein bis drei bzw. ein bis vier Stickstoffatome: 6-Ring Heteroarylgruppen, welche neben Kohlenstoffatomen ein bis drei bzw. ein bis vier Stickstoff¬ atome als Ringglieder enthalten können, z.B. 2-Pyridinyl, 3-Pyridinyl, 4-Pyridinyl, 3-Pyridazinyl, 4-Pyridazinyl, 2-Pyrimidinyl, 4-Pyrimidinyl, 5-Pyrimidinyl, 2-Pyrazinyl, l,3,5-Triazin-2-yl, 1,2,4-Triazin-3-yl und 1,2,4,5-Tetra- zinyl;6-membered heteroaryl containing one to three or one to four nitrogen atoms: 6-ring heteroaryl groups which, in addition to carbon atoms, may contain one to three or one to four nitrogen atoms as ring members, e.g. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, l, 3,5-triazin-2-yl, 1, 2,4-triazin-3-yl and 1,2,4,5-tetrazinyl;
benzokondensiertes 6-σliedriσes Heteroarvl. enthaltend ein bis vier S ickstoffatome: 6-Ring Heteroarylgruppen in welchen zwei benachbarte Kohlenstoffringglieder durch einebenzo-fused 6-σliedriσes heteroarvl. containing one to four nitrogen atoms: 6-ring heteroaryl groups in which two adjacent carbon ring members by one
Buta-1,3-dien-l,4-diylgruppe verbrückt sein können, z.B. Chinolin, Isochinolin, Chinazolin und Chinoxalin,Buta-1,3-diene-1,4-diyl group may be bridged, e.g. Quinoline, isoquinoline, quinazoline and quinoxaline,
bzw. die entsprechenden Oxy-, Thio-, Carbonyl- oder Sulfonyl- gruppen.or the corresponding oxy, thio, carbonyl or sulfonyl groups.
Hetarylffiπ'iiin'?i aromatische mono- oder polycyclische Reste, welche neben Kohlenstoffringgliedern zusätzlich ein bis vier Stickstoff¬ atome oder ein bis drei Stickstoffatome und ein Sauerstoff- oder ein Schwefelatom oder ein Sauerstoff- oder ein Schwefelatom ent¬ halten können und welche über ein Stickstoffatom an das Gerüst gebunden sind.Hetarylffiπ'iiin '? I aromatic mono- or polycyclic radicals which, in addition to carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom, and which have one Nitrogen atom are bound to the scaffold.
Die Angabe "partiell oder vollständig halogeniert" soll zum Aus- druck bringen, daß in den derart charakterisierten Gruppen die Wasserstoffatome zum Teil oder vollständig durch gleiche oder verschiedene Halogenatome wie vorstehend genannt ersetzt sein können.The expression “partially or fully halogenated” is intended to express that the hydrogen atoms in the groups characterized in this way can be replaced in part or in full by the same or different halogen atoms as mentioned above.
Im Hinblick auf ihre biologische Wirkung sind Verbindungen der Formel I bevorzugt, in denen m für 0 steht.With regard to their biological action, preference is given to compounds of the formula I in which m is 0.
Gleichermaßen bevorzugt sind Verbindungen der Formel I, in denen R1 für Methyl steht.Likewise preferred are compounds of formula I in which R 1 is methyl.
Daneben werden Verbindungen I bevorzugt, in denen R3 für Wasser¬ stoff, Hydroxy, Cyclopropyl, Chlor, Methyl, Ethyl, 1-Methylethyl, Methoxy, Methylthio oder Phenyl steht.In addition, compounds I are preferred in which R 3 represents hydrogen, hydroxyl, cyclopropyl, chlorine, methyl, ethyl, 1-methylethyl, methoxy, methylthio or phenyl.
Außerdem werden Verbindungen I bevorzugt, in denen R3 für Methyl steht. Des weiteren werden Verbindungen I bevorzugt, in denen R3 für Methoxy steht.In addition, compounds I are preferred in which R 3 is methyl. Furthermore, compounds I are preferred in which R 3 is methoxy.
Außerdem werden Verbindungen I bevorzugt, in denen R3 für Hydroxy steht.In addition, compounds I are preferred in which R 3 is hydroxy.
Des weiteren werden Verbindungen I bevorzugt, in denen R3 für Chlor steht.Furthermore, compounds I are preferred in which R 3 represents chlorine.
Des weiteren werden Verbindungen I bevorzugt, in denen R4 für Was¬ serstoff, Hydroxy, Cyclopropyl, Chlor, Methyl, Ethyl, iso-Propyl, Methoxy oder Methylthio steht.Furthermore, compounds I are preferred in which R 4 represents hydrogen, hydroxyl, cyclopropyl, chlorine, methyl, ethyl, isopropyl, methoxy or methylthio.
Außerdem werden Verbindungen I bevorzugt, in denen R4 für Methyl steht.In addition, compounds I are preferred in which R 4 is methyl.
Des weiteren werden Verbindungen I bevorzugt, in denen R4 für Methoxy steht.Furthermore, compounds I are preferred in which R 4 is methoxy.
Außerdem werden Verbindungen I bevorzugt, in denen R4 für Hydroxy steht.In addition, compounds I are preferred in which R 4 is hydroxy.
Des weiteren werden Verbindungen I bevorzugt, in denen R4 für Ethyl steht.Furthermore, compounds I are preferred in which R 4 is ethyl.
Außerdem werden Verbindungen I bevorzugt, in denen R4 für iso-Pro¬ pyl steht.In addition, compounds I are preferred in which R 4 is isopropyl.
Außerdem werden Verbindungen I bevorzugt, in denen R4 für Cyclo- propyl steht.In addition, compounds I are preferred in which R 4 is cyclopropyl.
Des weiteren werden Verbindungen I bevorzugt, in denen R4 für Aryl oder Hetaryl steht.Furthermore, compounds I are preferred in which R 4 represents aryl or hetaryl.
Außerdem werden Verbindungen I bevorzugt, in denen R4 für Phenyl steh .In addition, compounds I are preferred in which R 4 is phenyl.
Außerdem werden Verbindungen I bevorzugt, in denen R5 für Methyl oder Ethyl steht.In addition, compounds I are preferred in which R 5 is methyl or ethyl.
Des weiteren werden Verbindungen I bevorzugt, in denen R5 für Arylalkyl oder Hetarylalkyl steht.Furthermore, compounds I are preferred in which R 5 represents arylalkyl or hetarylalkyl.
Außerdem werden Verbindungen I bevorzugt, in denen R5 für Aryloxy- alkyl oder Hetaryloxyalkyl steht. Des weiteren werden Verbindungen I bevorzugt, in denen R4 für ggf. subst. Aryl oder Hetaryl steht.In addition, compounds I are preferred in which R 5 represents aryloxyalkyl or hetaryloxyalkyl. Furthermore, compounds I are preferred in which R 4 for optionally subst. Aryl or hetaryl is.
Des weiteren werden Verbindungen I bevorzugt, in denen R4 für ggf. subst. Pyridyl, Pyrimidyl, Pyrazinyl, Pyridazinyl oder Triazinyl steht.Furthermore, compounds I are preferred in which R 4 for optionally subst. Pyridyl, pyrimidyl, pyrazinyl, pyridazinyl or triazinyl.
Des weiteren werden Verbindungen I bevorzugt, in denen R4 für ggf. subst. Furyl, Thienyl oder Pyrrolyl steht.Furthermore, compounds I are preferred in which R 4 for optionally subst. Furyl, thienyl or pyrrolyl.
Des weiteren werden Verbindungen I bevorzugt, in denen R4 für ggf. subst. Oxazolyl, Thiazolyl, Isoxazolyl, Isothiazolyl, Pyrazolyl oder Imidazolyl steht.Furthermore, compounds I are preferred in which R 4 for optionally subst. Oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyrazolyl or imidazolyl.
Des weiteren werden Verbindungen I bevorzugt, in denen R4 für ggf. subst. Oxdiazolyl, Thiadiazolyl oder Triazolyl steht.Furthermore, compounds I are preferred in which R 4 for optionally subst. Oxdiazolyl, thiadiazolyl or triazolyl.
Außerdem werden Verbindungen I bevorzugt, in denen R4 für Phenyl _ steht, welches unsubstituiert ist oder ein oder zwei der folgen- den Gruppen trägt: Nitro, Cyano, Hydroxy, Amino, Aminocarbonyl, Aminothiocarbonyl, Halogen, Cι-C -Alkyl, Cι-C -Halogenalkyl, Cχ-C -Alkoxy, Cι-C -Halogenalkoxy, Cι-C -Alkylamino, Di-C1-C4-Alkylamino, C1-C4-Alkylsulfonyl, Cι-C -Alkoxycarbonyl, Cι-C4-Alkylaminocarbonyl or Di-Cι-C4-Alkylaminocarbonyl.In addition, compounds I are preferred in which R 4 is phenyl which is unsubstituted or carries one or two of the following groups: nitro, cyano, hydroxy, amino, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 4 alkyl, C 1 -C -Halogenalkyl, Cχ-C -alkoxy, Cι-C -halalkalkoxy, Cι-C -alkylamino, di-C 1 -C 4 -alkylamino, C 1 -C 4 -alkylsulfonyl, Cι-C -alkoxycarbonyl, Cι-C 4 -Alkylaminocarbonyl or Di-Cι-C 4 -Alkylaminocarbonyl.
Außerdem werden Verbindungen I bevorzugt, in denen R5 für Aryl oder Hetaryl steht.In addition, compounds I are preferred in which R 5 represents aryl or hetaryl.
Insbesondere sind im Hinblick auf ihre Verwendung die in den fol- genden Tabellen zusammengestellten Verbindungen I bevorzugt.In view of their use, particular preference is given to the compounds I compiled in the tables below.
Tabelle 1Table 1
Verbindungen der allgemeinen Formel 1.1, in denen (R2)m für Was- serstoff steht und die Kombination der Substituenten R3, R4 und R5 für eine Verbindung jeweils einer Zeile der Tabelle A entsprichtCompounds of the general formula 1.1, in which (R 2 ) m represents hydrogen and the combination of the substituents R 3 , R 4 and R 5 for each compound corresponds to one row of Table A.
Figure imgf000025_0001
Tabelle 2
Figure imgf000025_0001
Table 2
Verbindungen der allgemeinen Formel I.l in denen (R2)m für Chlor steht und die Kombination der Substituenten R3, R4 und R5 für eine Verbindung jeweils einer Zeile der Tabelle A entspricht.Compounds of the general formula II in which (R 2 ) m represents chlorine and the combination of the substituents R 3 , R 4 and R 5 for each compound corresponds to one row of Table A.
Tabelle ATable A
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Die Verbindungen I eignen sich als Fungizide.The compounds I are suitable as fungicides.
Die Verbindungen I zeichnen sich durch eine hervorragende Wirk- samkeit gegen ein breites Spektrum von pflanzenpathogenen Pilzen, insbesondere aus der Klasse der Ascomyceten und Basidio yceten, aus. Sie sind zum Teil systemisch wirksam und können als Blatt- und Bodenfungizide eingesetzt werden.The compounds I are notable for excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes and Basidio ycetes. Some of them are systemically effective and can be used as foliar and soil fungicides.
Besondere Bedeutung haben sie für die Bekämpfung einer Vielzahl von Pilzen an verschiedenen Kulturpflanzen wie Weizen, Roggen, Gerste, Hafer, Reis, Mais, Gras, Baumwolle, Soja, Kaffee, Zucker¬ rohr, Wein, Obst- und Zierpflanzen und Gemüsepflanzen wie Gurken, Bohnen und Kürbisgewächsen, sowie an den Samen dieser Pflanzen.They are of particular importance for combating a large number of fungi on various crops such as wheat, rye, barley, oats, rice, corn, grass, cotton, soybeans, coffee, sugar cane, wine, fruit and ornamental plants and vegetable plants such as cucumbers, Beans and pumpkin plants, as well as on the seeds of these plants.
Speziell eignen sie sich zur Bekämpfung folgender Pflanzenkrank¬ heiten: Erysiphe graminis (echter Mehltau) in Getreide, Erysiphe cichoracearum und Sphaerotheca fuliginea an Kürbisgewächsen, Po- dosphaera leucotricha an Äpfeln, Uncinula necator an Reben, Puc- cinia-Arten an Getreide, Rhizoctonia-Arten an Baumwolle und Ra¬ sen, Ustilago-Arten an Getreide und Zuckerrohr, Venturia inaequa- lis (Schorf) an Äpfeln, Helminthosporium-Arten an Getreide, Sep- toria nodoru an Weizen, Botrytis cinerea (Grauschimmel) an Erd¬ beeren, Reben, Cercospora arachidicola an Erdnüssen, Pseudocer- cosporella herpotrichoides an Weizen, Gerste, Pyricularia oryzae an Reis, Phytophthora infestans an Kartoffeln und Tomaten, Fusa7rium- und Verticillium-Arten an verschiedenen Pflanzen, Plasmopara viticola an Reben, Alternaria-Arten an Gemüse und Obst.They are particularly suitable for combating the following plant diseases: Erysiphe graminis (powdery mildew) in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin plants, Podosphaera leucotricha on apples, Uncinula necator on vines, Puc- cinia species on cereals Species on cotton and grass, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species on cereals, Seporia nodoru on wheat, Botrytis cinerea (gray mold) on strawberries, vines , Cercospora arachidicola on peanuts, Pseudocercosporella herpotrichoides on wheat, barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Fusa7rium and Verticillium species on various plants, Plasmopara viticola on vines, Alternaria species on vegetables and fruit.
Die Verbindungen I werden angewendet, indem man die Pilze oder die vor Pilzbefall zu schützenden Pflanzen, Saatgüter, Materia¬ lien oder den Erdboden mit einer fungizid wirksamen Menge der Wirkstoffe behandelt. Die Anwendung erfolgt vor oder nach der In- fektion der Materialien, Pflanzen oder Samen durch die Pilze.The compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally active amount of the active compounds. It is used before or after the infection of the materials, plants or seeds by the fungi.
Sie können in die üblichen Formulierungen überführt werden, wie Lösungen, Emulsionen, Suspensionen, Stäube, Pulver, Pasten und Granulate. Die Anwendungsform richtet sich nach dem jeweiligen Verwendungszweck; sie soll in jedem Fall eine feine und gleichmä¬ ßige Verteilung des ortho-substituierten Benzylesters einer Cy- clopropancarbonsäure gewährleisten. Die Formulierungen werden in bekannter Weise hergestellt, z.B. durch Verstrecken des Wirk¬ stoffs mit Lösungsmitteln und/oder Trägerstoffen, gewünschten- falls unter Verwendung von Emulgiermitteln und Dispergiermitteln, wobei im Falle von Wasser als Verdünnungsmittel auch andere orga¬ nische Lösungsmittel als Hilfslösungsmittel verwendet werden kön- nen. Als Hilfsstoffe kommen dafür im wesentlichen in Betracht: Lösungsmittel wie Aromaten (z.B. Xylol), chlorierte Aromaten (z.B. Chlorbenzole), Paraffine (z.B. Erdölfraktionen) , Alkohole (z.B. Methanol, Butanol) , Ketone (z.B. Cyclohexanon) , Amine (z.B. Ethanolamin, Dimethylformamid) und Wasser; Trägerstoffe wie na¬ türliche Gesteinsmehle (z.B. Kaoline, Tonerden, Talkum, Kreide) und synthetische Gesteinsmehle (z.B. hochdisperse Kieselsäure, Silikate) ; Emulgiermittel wie nichtionogene und anionische Emul- gatoren (z.B. Polyoxyethylen-Fettalkohol-Ether, Alkylsulfonate und Arylsulfonate) und Dispergiermittel wie Lignin-Sulfitablaugen und Methylcellulose.They can be converted into the usual formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The form of application depends on the respective purpose; in any case, it should ensure a fine and uniform distribution of the ortho-substituted benzyl ester of a cyclopropanecarboxylic acid. The formulations are prepared in a known manner, for example by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, and in the case of water as diluent other organic solvents can also be used as auxiliary solvents - nen. The following are essentially considered as auxiliaries: solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g. ethanolamine, dimethylformamide) ) and water; Carriers such as natural stone powder (eg kaolins, clays, talc, chalk) and synthetic stone powder (eg highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
Die fungiziden Mittel enthalten im allgemeinen zwischen 0,1 und 95, vorzugsweise zwischen 0,5 und 90 Gew.% Wirkstoff.The fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.
Die Aufwandmengen liegen je nach Art des gewünschten Effektes zwischen 0,01 und 2,0 kg Wirkstoff pro ha.Depending on the type of effect desired, the application rates are between 0.01 and 2.0 kg of active ingredient per ha.
Bei der Saatgutbehandlung werden im allgemeinen Wirkstoffmengen von 0,001 bis 0,1 g, vorzugsweise 0,01 bis 0,05 g je Kilogramm Saatgut benötigt.In the case of seed treatment, amounts of active ingredient of 0.001 to 0.1 g, preferably 0.01 to 0.05 g, per kg of seed are generally required.
Die erfindungsgemäßen Mittel können in der Anwendungsform als Fungizide auch zusammen mit anderen Wirkstoffen vorliegen, der z.B. mit Herbiziden, Insektiziden, Wachstumsregulatoren, Fungizi¬ den oder auch mit Düngemitteln.The agents according to the invention can also be present in the use form as fungicides together with other active ingredients, which e.g. with herbicides, insecticides, growth regulators, fungicides or also with fertilizers.
Beim Vermischen mit Fungiziden erhält man dabei in vielen Fällen eine Vergrößerung des fungiziden Wirkungsspektrums.When mixed with fungicides, the fungicidal activity spectrum is enlarged in many cases.
Die folgende Liste von Fungiziden, mit denen die erfindungs¬ gemäßen Verbindungen gemeinsam angewendet werden können, soll die Kombinationsmöglichkeiten erläutern, nicht aber einschränken:The following list of fungicides with which the compounds according to the invention can be used together is intended to explain, but not to limit, the possible combinations:
Schwefel, Dithiocarbamate und deren Derivate, wie Ferridi ethyl- dithiocarbamat, Zinkdimethyldithiocarbamat, Zinkethylenbisdithio- carbamat, Manganethylenbisdithiocarbamat, Mangan-Zink-ethylen- diamin-bis-dithiocarbamat, Tetra ethylthiuramdisulfide, Ammoniak- Komplex von Zink-(N,N-ethylen-bis-dithiocarbamat) , Ammoniak-Kom- plex von Zink-(N,N'-propylen-bis-dithiocarbamat) , Zink-(N,N'-pro- pylenbis-dithiocarbamat) , N,N'-Polypropylen-bis-(thiocarba- moyDdisulfid; Nitroderivate, wie Dinitro-(1-methylheptyl)-phenylcrotonat, 2-sec-Butyl-4, 6-dinitrophenyl-3,3-dimethylacrylat, 2-sec-Bu- tyl-4,6-dinitrophenyl-isopropylcarbonat, 5-Nitro-isophthalsäure- di-isopropylester;Sulfur, dithiocarbamates and their derivatives, such as ferridi ethyl dithiocarbamate, zinc dimethyl dithiocarbamate, zinc ethylene bisdithiocarbamate, manganese ethylene bisdithiocarbamate, manganese-zinc ethylene diamine bis-dithiocarbamate, tetra ethyl thiuram disulfide zinc (ammonium n-bisulfide, ethylenedisulfide, (ammonia -dithiocarbamate), ammonia complex of zinc (N, N'-propylene-bis-dithiocarbamate), zinc (N, N'-propylene-bis-dithiocarbamate), N, N'-polypropylene-bis- ( thiocarbamoyD disulfide; Nitroderivatives such as dinitro- (1-methylheptyl) phenyl crotonate, 2-sec-butyl-4, 6-dinitrophenyl-3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenyl-isopropyl carbonate, 5-nitro -isophthalic acid - di-isopropyl ester;
heterocyclische Substanzen, wie 2-Heptadecyl-2-imidazolin-acetat, 2,4-Dichlor-6-(o-chloranilino)-s-triazin, 0,0-Diethyl-phthal- imidophosphonothioat, 5-Amino-l-[bis-(dimethy1amino)-phosphi- nyl]-3-phenyl-l,2,4- triazol, 2,3-Dicyano-l,4-dithioanthrachinon, 2-Thio-l,3-dithiolo[4,5-b]chinoxalin, 1-(Butylcarbamoy1)-2-benz- imidazol-carbaminsäuremethylester, 2-Methoxycarbonylamino-benz- imidazol, 2-(Furyl-(2) )-benzimidazol, 2-(Thiazolyl-(4) )-benz- imidazol, N- (1,1,2,2-Tetrachlorethylthio)-tetrahydrophthalimid, N-Trichlormethylthio-tetrahydrophthalimid, N-Trichlormethylthio- phthalimid,heterocyclic substances such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6- (o-chloroanilino) -s-triazine, 0.0-diethyl-phthalimidophosphonothioate, 5-amino-l- [bis - (dimethylamino) phosphinyl] -3-phenyl-l, 2,4-triazole, 2,3-dicyano-l, 4-dithioanthraquinone, 2-thio-l, 3-dithiolo [4,5-b] quinoxaline, 1- (butylcarbamoy1) -2-benzimidazole-carbamic acid methyl ester, 2-methoxycarbonylamino-benzimidazole, 2- (furyl- (2)) -benzimidazole, 2- (thiazolyl- (4)) -benzimidazole, N- (1,1,2,2-tetrachloroethylthio) tetrahydrophthalimide, N-trichloromethylthio-tetrahydrophthalimide, N-trichloromethylthiophthalimide,
N-Dichlorfluormethylthio-N' ,N'-dimethy1-N-phenyl-schwefelsäure- dia id, 5-Ethoxy-3-trichlormethyl-l,2,3-thiadiazol, 2-Rhodan- methylthiobenzthiazol, 1,4-Dichlor-2, 5-dimethoxybenzol, 4- (2-Chlorphenylhydrazono)-3-methyl-5-isoxazolon,N-dichlorofluoromethylthio-N ', N'-dimethyl-N-phenylsulfuric acid dia id, 5-ethoxy-3-trichloromethyl-l, 2,3-thiadiazole, 2-rhodanomethylthiobenzothiazole, 1,4-dichloro-2 , 5-dimethoxybenzene, 4- (2-chlorophenylhydrazono) -3-methyl-5-isoxazolone,
Pyridin-2-thio-l-oxid, 8-Hydroxychinolin bzw. dessen Kupfersalz, 2,3-Dihydro-5-carboxanilido-6-methyl-l,4-oxathiin, 2,3-Di- hydro-5-carboxanilido-6-methyl-l,4-oxathiin-4,4-dioxid, 2-Methyl-5,6-dihydro-4H-pyran-3-carbonsäure-anilid, 2-Methyl-fu- ran-3-carbonsäureanilid, 2,5-Dimethyl-furan-3-carbonsäureanilid, 2,4, 5-Trimethyl-furan-3-carbonsäureanilid, 2,5-Dimethyl-fu- ran-3-carbonsäurecyclohexylamid, N-Cyclohexyl-N-methoxy- 2,5-dimethyl-furan-3-carbonsäureamid, 2-Methyl-benzoesäure- anilid, 2-Iod-benzoesäure-anilid, N-Formyl-N-morpho- lin-2,2,2-trichlorethylacetal, Piperazin-1,4-diyl- bis- (l-(2,2,2-trichlor-ethyl)-formamid, l-(3,4-Dichlorani- lino)-l-formylamino-2,2,2-trichlorethan , 2, 6-Dimethyl-N-tride- cyl-morpholin bzw. dessen Salze, 2,6-Dimethyl-N-cyclododecyl- morpholin bzw. dessen Salze, N-[3-(p-tert.-Butylphenyl)-2-methyl- propyl]-cis-2, 6-dimethyl- orpholin, N-[3-(p-tert.-Butylphe¬ nyl)-2-methylpropyl]-piperidin, 1-[2-(2,4-Dichlor- phenyl)-4-ethyl-l,3-dioxolan-2-yl-ethyl]-1H- 1,2,4-triazol, 1-[2-(2,4-Dichlorphenyl)-4-n-propyl-l,3-dioxolan-2-yl-ethyl]-1H- 1,2,4-triazol, N-(n-Propyl)-N-(2,4,6-trichlorphenoxyethyl)-N'- imidazol-yl- harnstoff, l-(4-Chlorphenoxy)-3,3-dimethyl-l- (lH-l,2,4-triazol-l-yl)-2- butanon, 1- (4-Chlorphen¬ oxy)-3,3-dimethy1-1-(1H-1,2,4-triazol-l-yl)-2- butanol, α-(2-Chlorphenyl)-α-(4-chlorphenyl)-5-pyrimidin-methanol, 5-Butyl-2-dimethylamino-4-hydroxy-6-methyl-pyrimidin, Bis-(p- chlorphenyl)-3-pyridinmethanol, 1,2-Bis-(3-ethoxycarbonyl-2- thioureido)-benzol, 1,2-Bis-(3-methoxycarbonyl-2-thiou- reido)-benzol,Pyridine-2-thio-l-oxide, 8-hydroxyquinoline or its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-l, 4-oxathiine, 2,3-di-hydro-5-carboxanilido 6-methyl-l, 4-oxathiin-4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxylic acid anilide, 2-methyl-furan-3-carboxylic acid anilide, 2, 5-dimethyl-furan-3-carboxylic acid anilide, 2,4, 5-trimethyl-furan-3-carboxylic acid anilide, 2,5-dimethyl-furan-3-carboxylic acid cyclohexylamide, N-cyclohexyl-N-methoxy-2,5- dimethyl-furan-3-carboxamide, 2-methyl-benzoic acid anilide, 2-iodo-benzoic acid anilide, N-formyl-N-morpholine-2,2,2-trichloroethyl acetal, piperazine-1,4-diyl- bis- (l- (2,2,2-trichloroethyl) formamide, l- (3,4-dichloroanilino) -l-formylamino-2,2,2-trichloroethane, 2,6-dimethyl-N -tride-cyl-morpholine or its salts, 2,6-dimethyl-N-cyclododecyl-morpholine or its salts, N- [3- (p-tert-butylphenyl) -2-methyl-propyl] -cis- 2,6-dimethyl-orpholine, N- [3- (p-tert-butylphenyl) -2-methylpropyl] piperidine, 1- [2- (2,4-dichlorophenyl) -4-ethyl- l, 3-dioxolan-2-yl- ethyl] -1H- 1,2,4-triazole, 1- [2- (2,4-dichlorophenyl) -4-n-propyl-l, 3-dioxolan-2-yl-ethyl] -1H- 1,2 , 4-triazole, N- (n-propyl) -N- (2,4,6-trichlorophenoxyethyl) -N'- imidazol-yl urea, l- (4-chlorophenoxy) -3,3-dimethyl-l- (lH-l, 2,4-triazol-l-yl) -2-butanone, 1- (4-chlorophenoxy) -3,3-dimethy1-1- (1H-1,2,4-triazol-l -yl) -2-butanol, α- (2-chlorophenyl) -α- (4-chlorophenyl) -5-pyrimidine-methanol, 5-butyl-2-dimethylamino-4-hydroxy-6-methyl-pyrimidine, bis- (p-chlorophenyl) -3-pyridinemethanol, 1,2-bis (3-ethoxycarbonyl-2- thioureido) -benzene, 1,2-bis- (3-methoxycarbonyl-2-thiou-reido) -benzene,
sowie verschiedene Fungizide, wie Dodecylguanidinacetat, 3-[3-(3, 5-Dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]-glutarimid, Hexachlorbenzol, DL-Methyl-N- (2,6-dimethyl-phenyl)-N-fu- roy1 (2)-alanina , DL-N-(2,6-Dimethy1-pheny1)-N-(2'-methoxyace- tyl)-alanin-methyl- ester, N-(2, 6-Dimethylphenyl)-N-chloracetyl- D,L-2-aminobutyrolacton, DL-N-(2,6-Dimethylphenyl)-N-(phenylace- tyl)-alaninmethylester, 5-Methyl-5-vinyl-3- (3,5-dichlor- phenyl)-2,4-dioxo-l,3-oxazolidin, 3-[3,5-Dichlorphe- nyl (-5-methyl-5-methoxymethyl]-l,3-oxazolidin- 2,4-dion, 3-(3,5-Dichlorphenyl)-1-isopropylcarbamoylhydantoin, N-(3,5-Dich- lorphenyl)-1,2-dimethylcyclopropan-1,2-dicarbonsäureimid, 2-Cyano-[N-(ethylaminocarbonyl)-2-methoximino]-acetamid,as well as various fungicides, such as dodecylguanidine acetate, 3- [3- (3, 5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl] glutarimide, hexachlorobenzene, DL-methyl-N- (2,6-dimethyl-phenyl) -N -foroy1 (2) -alanina, DL-N- (2,6-dimethy1-pheny1) -N- (2'-methoxyacetyl) -alanine-methyl ester, N- (2, 6-dimethylphenyl) -N-chloroacetyl- D, L-2-aminobutyrolactone, DL-N- (2,6-dimethylphenyl) -N- (phenylacetyl) -alanine methyl ester, 5-methyl-5-vinyl-3- (3,5- dichlorophenyl) -2,4-dioxo-l, 3-oxazolidine, 3- [3,5-dichlorophenyl (-5-methyl-5-methoxymethyl] -l, 3-oxazolidine-2,4-dione, 3- (3,5-dichlorophenyl) -1-isopropylcarbamoylhydantoin, N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cyano- [N- (ethylaminocarbonyl) -2 -methoximino] -acetamide,
1-[2-(2,4-Dichlorphenyl)-pentyl]-1H-1,2,4-triazol, 2,4-Difluor- α-(1H-1,2,4-triazolyl-l-methyl)-benzhydrylalkohol, N- (3-Chlor- 2-, 6-dinitro-4-trifluormethyl-phenyl)-5-trifluormethyl-3- chlor-2-aminopyridin, 1-( (bis-(4-Fluorphenyl)-methylsilyl)- methyl)-lH-l,2,4-triazol.1- [2- (2,4-dichlorophenyl) pentyl] -1H-1,2,4-triazole, 2,4-difluoro-α- (1H-1,2,4-triazolyl-l-methyl) - benzhydryl alcohol, N- (3-chloro-2-, 6-dinitro-4-trifluoromethyl-phenyl) -5-trifluoromethyl-3-chloro-2-aminopyridine, 1- ((bis- (4-fluorophenyl) methylsilyl) - methyl) -IH-l, 2,4-triazole.
Die Verbindungen der Formel I sind außerdem geeignet, Schädlinge aus der Klasse der Insekten, Spinnentiere und Nematoden wirksam zu bekämpfen. Sie können im Pflanzenschutz sowie auf dem Hygiene-, Vorratsschutz- und Veterinärsektor als Schädlings¬ bekämpfungsmittel eingesetzt werden.The compounds of the formula I are also suitable for effectively controlling pests from the class of the insects, arachnids and nematodes. They can be used as pesticides in crop protection and in the hygiene, stored product protection and veterinary sectors.
Zu den schädlichen Insekten gehören aus der Ordnung der Schmet¬ terlinge (Lepidoptera) beispielsweise Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia muri- nana, Capua reticulana, Cheimatobia brumata, Choristoneura fumi- ferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia po- monella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandio- sella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia am- biguella, Evetria bouliana, Feltia subterranea, Galleria mello- nella, Grapholitha funebrana, Grapholitha molesta, Heliothis ar- migera, Heliothis virescens, Heliothis zea, Hellula undalis, Hi- bernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Kei- feria lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leu- coptera coffeella, Leucoptera scitella, Lithocolletis blancar- della, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Ma- mestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Pano- lis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pie- ris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplu- sia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Si- totroga cerealella, Sparganothis pilleriana, Spodoptera frugi- perda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pi- tyocampa, Tortrix viridana, Trichoplusia ni, Zeiraphera canaden- sis.From the order of the butterflies (Lepidoptera), the harmful insects include, for example, Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulobura, chumumobella, Cheumatobella - ferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia po- monella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandio- sella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia am- biguella, Evetria bouliana, Fella diella, granella Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Kei- feria lycopersicella, Lambdina fiscellaria, Laphygma exigua scella, Leucella leucella arteria, Leucopaula della, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Ma- mestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panellis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnathis plicaellaellaella, Plella risella- Plella risella, Pie- risella Pella sia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Si- totroga cerealella, Sparganothis pilleriana, Spodoptera frugi- perda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia niaden, Zeirap.
Aus der Ordnung der Käfer (Coleoptera) beispielsweise Agrilus si- nuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solsti- tialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomo- rum, Atomaria linearis, Blastophagus piniperda, Blitophaga un- data, Bruchus rufimanus, Bruchus pisoru , Bruchus lentis, Bycti- scus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhyn- chus assimilis, Ceuthorrynchus napi, Chaetocnema tibialis, Cono- derus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varive- stis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limo- nius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melo- lontha, Onlema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllo- phaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllo¬ treta striolata, Popillia japonica, Sitona lineatus, Sitophilus granaria.From the order of the beetles (Coleoptera), for example Agrilus si- nuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisoru, Bruchus lentis, Bycti- scus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhyn- chus assimilis, Ceuthorrynchus napi, Chaetocnema tibialis, Conodusus vespertinus, Crioceris asparagi, Punctica viratailicaica diabroticaica- nica longica stis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilesonololamololonolamololinolanololinololonolus, Melanotolusola melolotinus, Melanotolusola melolotolus, Melanotolusola melolotolus, Melanotolusola, Melanotolusola, Melanotolasola, Melanotolusola, Melanotolus, Melanot , Onlema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllo treta chrysocephala, Phyllo-phaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllo-treta striolata, Popillia japonica, Sitona lineatus, Sitophilus granaria.
Aus der Ordnung der Zweiflügler (Diptera) beispielsweise Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropo- phaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glos¬ sina morsitans, Haematobia irritans, Haplodiplosis equestris, Hy- lemyia platura, Hypoderma lineata, Lirio yza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Ly- coria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phor- bia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis ce- rasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea, Ti- pula paludosa.From the order of the two-winged species (Diptera), for example, Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropuce phumacuceaculaceacucia, pita Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glos¬ sina morsitans, Haematobia irritans, Haplodiplosis equestris, Hy- lemyia platura, Hypoderma lineata, Lirio yza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia seriaalalisata, Lucilia seriola rata, Lucilia seriolataa destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phor- bia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula olula paludosa, Ti-.
Aus der Ordnung der Thripse (Thysanoptera) beispielsweise Fran¬ kliniella fusca, Frankliniella occidentalis, Frankliniella tri- tici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips ta- baci. Aus der Ordnung der Hautflügler (Hymenoptera) beispielsweise Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplo- campa minuta, Hoplocampa testudinea, Monomorium pharaonis, Sole- nopsis geminata, Solenopsis invicta.From the order of the thrips (Thysanoptera), for example, Franklini fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci. From the order of the hymenoptera (Hymenoptera), for example, Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta.
Aus der Ordnung der Wanzen (Heteroptera) beispielsweise Acroster- num hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Eu- schistus impictiventris, Leptoglossus phyllopus, Lygus lineola- ris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyanta perditor.From the order of the bugs (Heteroptera), for example, Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Eu- schistus impictiventris, Leptoglossus phyllopus, Lygus lineola- ris, Lygus parsatidis, Lygus parsatidis, Lygus prairisensis , Solubea insularis, Thyanta perditor.
Aus der Ordnung der Pflanzensauger (Ho optera) beispielsweise Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Bre- vicoryne brassicae, Cerosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Ma- crosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanugi- nosa, Trialeurodes vaporariorum, Viteus vitifolii.From the order of the plant suckers (Ho optera), for example, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Bre- vicoryne brassicae, Cerosipha gossypyususiusi, Dreiafusiaii, Dreiafusolia, Dreiafusiaia, Dreiafusiaia, Dreiafusiaia, Dreiafusiaia, Dreyfusiaia, Dreiafusiaia , Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella sacchariculii, Psylodalidiumi, Psylodalidiumi, Psylodaloniumi, Psorodaloniumi, Psorodaloniumi, Psorodalonidi, Psorodaloniumi, Psorodaloniumi, Psorodaloniumi, Psorodalonium, Psorodalonium, Psorodalonium, Psorodalonid, Psorodalonium, Psorodalidium, Psorodalonium, Psorodalidium, , Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Trialeurodes vaporariorum, Viteus vitifolii.
Aus der Ordnung der Termiten (Isoptera) beispielsweise Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus, Ter- mes natalensis.From the order of the termites (Isoptera), for example, Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus, and Termes natalensis.
Aus der Ordnung der Geradflügler (Orthoptera) beispielsweise Acheta domestica, Blatta orientalis, Blattella germanica, Forfi- cula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexi- canus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus, Tachycines asyna- morus.From the order of the straight-winged wing (Orthoptera), for example Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanusus, Melanoplus sanguinisusptipisipei, Melanoplasci, melanoplasmic , Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus, Tachycines asynamorus.
Aus der Klasse der Arachnoidea beispielsweise Spinnentiere (Aca- rina) wie Amblyomma americanum, Amblyomma variegatum, Argas per- sicus, Boophilus annulatus, Boophilus decoloratus, Boophilus mi- croplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus mou- bata, Otobius megnini, Paratetranychus pilosus, Dermanyssus gal- linae, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Pso- roptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanza- wai, Tetranychus pacificus, Tetranychus* telarius, Tetranychus ur- ticae.From the class of the arachnoid, for example arachnids (Arina) such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus micro-croplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentoretronichumum, Eri Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus mou- bata, Otobius megnini, Paratetranychus pilosus, Dermanyssus gal- linae, Phyllocoptruta oleivora, Polyphagotarsonemususus, Ticendiphodinusiabi, Ticipinusiabi, Ticipinusiabusi, Ticinociabusi - wai, Tetranychus pacificus, Tetranychus * telarius, Tetranychus ur- ticae.
Aus der Klasse der Nematoden beispielsweise Wurzelgallennemato- den, z.B. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Zysten bildende Nematoden, z.B. Globodera rostochien- sis, Heterodera avenae, Heterodera glycines, Heterodera schach- tii, Heterodera trifolii, Stock- und Blattälchen, z.B. Belonolai- mus longicaudatus, Ditylenchus destructor, Ditylenchus dipsac^, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchor- hynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglec- tus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylen¬ chus goodeyi.From the class of nematodes, for example, root gall nematodes, e.g. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, e.g. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schach- tii, Heterodera trifolii, stick and leaf wholes, e.g. Belonolai- mus longicaudatus, Ditylenchus destructor, Ditylenchus dipsac ^, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchor- hynchus claytoni, Tylenchorhynchus tubus negchatatylenes Prubus, Prychatatusus tyus negate, Prylenchitatusus, Prychatatususus, Prychatatususus, Prychatatususus, Prychatatususus, Prychatatus, .
Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder den daraus bereiteten Anwendungsformen, z.B. in Form von di¬ rekt versprühbaren Lösungen, Pulvern, Suspensionen oder Disper¬ sionen, Emulsionen, Öldispersionen, Pasten, Stäubemitteln, Streu- mitteln, Granulaten durch versprühen, Vernebeln, Verstäuben, Ver¬ streuen oder Gießen angewendet werden. Die Anwendungsformen rich¬ ten sich ganz nach den Verwendungszwecken; sie sollten in jedem Fall möglichst die feinste Verteilung der erfindungsgemäßen Wirk¬ stoffe gewährleisten.The active ingredients as such, in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, spreading agents, granules by spraying, atomizing, dusting, scattering or pouring. The application forms depend entirely on the intended use; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
Die Wirkstoffkonzentrationen in den anwendungsfertigen Zu¬ bereitungen können in größeren Bereichen variiert werden.The active substance concentrations in the ready-to-use preparations can be varied over a wide range.
Im allgemeinen liegen sie zwischen 0,0001 und 10 %, vorzugsweise zwischen 0,01 und 1 %.In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
Die Wirkstoffe können auch mit gutem Erfolg im Ultra-Low- Volume-Verfahren (ULV) verwendet werden, wobei es möglich ist, Formulierungen mit mehr als 95 Gew.% Wirkstoff oder sogar den Wirkstoff ohne Zusätze auszubringen.The active ingredients can also be used with great success in the ultra-low-volume process (ULV), it being possible to apply formulations with more than 95% by weight of active ingredient or even the active ingredient without additives.
Die Aufwandmenge an Wirkstoff zur Bekämpfung von Schädlingen be¬ trägt unter Freilandbedingungen 0,1 bis 2,0, vorzugsweise 0,2 bis 1,0 kg/ha.The amount of active ingredient used to control pests is 0.1 to 2.0, preferably 0.2 to 1.0 kg / ha under field conditions.
Zur Herstellung von direkt versprühbaren Lösungen, Emulsionen, Pasten oder Öldispersionen kommen Mineralölfraktionen von mittle¬ rem bis hohem Siedepunkt, wie Kerosin oder Dieselöl, ferner Kohlenteeröle sowie Öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyclische und aromatische Kohlenwasserstoffe, z.B. Benzol, Toluol, Xylol, Paraffin, Tetrahydronaphthalin, alkylierte Naphthaline oder deren Derivate, Methanol, Ethanol, Propanol, Butanol, Chloroform, Tetrachlorkohlenstoff, Cyclohexanol, Cyclo- hexanon, Chlorbenzol, Isophoron, stark polare Lösungsmittel, z.B. Dimethylformamid, Dimethylsulfoxid, N-Methylpyrrolidon, Wasser, in Betracht.For the production of directly sprayable solutions, emulsions, pastes or oil dispersions, mineral oil fractions from medium to high boiling points, such as kerosene or diesel oil, also coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example benzene, toluene, xylene, Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, Butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, for example dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, into consideration.
Wäßrige Anwendungsformen können aus Emulsionskonzentraten, Pasten oder netzbaren Pulvern (Spritzpulver, Öldispersionen) durch Zu¬ satz von Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Öldispersionen können die Substanzen als solche oder in einem Öl oder Lösungsmittel gelöst, mittels Netz-, Haft-,Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water. For the production of emulsions, pastes or oil dispersions, the substances as such or dissolved in an oil or solvent, by means of wetting, adhesive,
Dispergier- oder Emulgiermitttel in Wasser homogenisiert werden. Es können aber auch aus wirksamer Substanz Netz-, Haft-, Dispergier- oder Emulgiermittel und eventuell Lösungsmittel oder Öl bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind.Dispersants or emulsifiers can be homogenized in water. However, it is also possible to prepare concentrates composed of an active substance, wetting agents, adhesives, dispersants or emulsifiers and possibly solvents or oil, which are suitable for dilution with water.
Als oberflächenaktive Stoffe kommen Alkali-, Erdalkali-, Ammoniumsalze von Ligninsulfonsäure, Naphthalinsulfonsäure, Phenolsulfonsäure, Dibutylnaphthalinsulfonsäure, Alkylarylsulfo- nate, Alkylsulfate, Alkylsulfonate, Fettalkoholsulfate und Fett¬ säuren sowie deren Alkali- und Erdalkalisalze, Salze von sulfa- tiertem Fettalkoholglykolether, Kondensationsprodukte von sulfo- niertem Naphthalin und Naphthalinderivaten mit Formaldehyd, Kon¬ densationsprodukte des Naphthalins bzw. der Naphtalinsulfonsäure mit Phenol und Formaldehyd, Polyoxyethylenoctylphenolether, ethoxyliertes Isooctylphenol, Octylphenol, Nonylphenol, Alkylphe- nolpolyglykolether, Tributylphenylpolyglykolether, Alkylarylpoly- etheralkohole, Isotridecylalkohol, Fettalkoholethylenoxid-Konden- sate, ethoxyliertes Rizinusöl, Polyoxyethylenalkylether, ethoxy- liertes Polyoxypropylen, Laurylalkoholpolyglykoletheracetal, Sorbitester, Ligninsulfitablaugen und Methylcellulose in Be¬ tracht.Alkali, alkaline earth, ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates and fatty acids as well as their alkali and alkaline earth metal salts, fatty alcohol sulfonates, salts of sulfonated alcohol sulfates - Nated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether, tributylphenyl ether alcohol, fatty alcohol, fatty alcohol, fatty alcohol, fatty alcohol, fatty alcohol, fatty alcohol, fatty alcohol, fatty alcohol, fatty alcohol Castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin sulfite waste liquors and methyl cellulose are considered.
Pulver-, Streu- und Stäubemittel können durch Mischen oder ge- meinsames Vermählen der wirksamen Substanzen mit einem festen Trägerstoff hergestellt werden.Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
Die Formulierungen enthalten im allgemeinen zwischen 0,01 und 95 Gew.%, vorzugsweise zwischen 0,1 und 90 Gew.% des Wirkstoffs. Die Wirkstoffe werden dabei in einer Reinheit von 90 % bis 100 %, vorzugsweise 95 % bis 100 % (nach NMR-Spektrum) eingesetzt. Beispiele für Formulierungen sind:The formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight, of the active ingredient. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum). Examples of formulations are:
I. 5 Gew.-Teile eines Wirkstoffs werden mit 95 Gew.-Teilen feinteiligem Kaolin innig vermischt. Man erhält auf diese Weise ein Stäubemittel, das 5 Gew.% des Wirkstoffs ent¬ hält.I. 5 parts by weight of an active ingredient are intimately mixed with 95 parts by weight of finely divided kaolin. In this way, a dusting agent is obtained which contains 5% by weight of the active ingredient.
II. 30 Gew.-Teile eines Wirkstoffs werden mit einer Mischung aus 92 Gew.-Teilen pulverförmigem Kieselsäuregel und 8 Gew.-Teilen Paraffinöl, das auf die Oberfläche diesesII. 30 parts by weight of an active ingredient are mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil on the surface of this
Kieselsäuregels gesprüht wurde, innig vermischt. Man er¬ hält auf diese Weise eine Aufbereitung des Wirkstoffs mit guter Haftfähigkeit (Wirkstoffgehalt 23 Gew.%).Silica gel was sprayed, mixed intimately. In this way, a preparation of the active ingredient with good adhesiveness is obtained (active ingredient content 23% by weight).
III. 10 Gew.-Teile eines Wirkstoffs werden in einer Mischung gelöst, die aus 90 Gew.-Teilen Xylol, 6 Gew.-Teilen des Anlagerungsproduktes von 8 bis 10 Mol Ethylenoxid an 1 Mol Ölsäure-N-monoethanolamid, 2 Gew.-Teilen Calciumsalz der Dodecylbenzolsulfonsäure und 2 Gew.-Teilen des Anla- gerungsproduk es von 40 Mol Ethylenoxid an 1 Mol Ricinusöl besteht (Wirkstoffgehalt 9 Gew.%).III. 10 parts by weight of an active ingredient are dissolved in a mixture consisting of 90 parts by weight of xylene, 6 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 2 parts by weight of calcium salt of the dodecylbenzenesulfonic acid and 2 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil (active ingredient content 9% by weight).
IV. 20 Gew.-Teile eines Wirkstoffs werden in einer Mischung gelöst, die aus 60 Gew.-Teilen Cyclohexanon, 30 Gew.-Tei- len Isobutanol, 5 Gew.-Teilen des Anlagerungsproduktes von 7 Mol Ethylenoxid an 1 Mol Isooctylphenol und 5 Gew.- Teilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl besteht (Wirkstoffgehalt 16 Gew.%).IV. 20 parts by weight of an active ingredient are dissolved in a mixture consisting of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 5 Parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil (active ingredient content 16% by weight).
V. 80 Gew.-Teile eines Wirkstoffs werden mit 3 Gew.-Teilen des Natriumsalzes der Diisobutylnaphthalin-alpha-sulfon- säure, 10 Gew.-Teilen des Natriumsalzes einer Lignin- sulfonsäure aus einer Sulfit-Ablauge und 7 Gew.-Teilen pulverförmigem Kieselsäuregel gut vermischt und in einer Hammermühle vermählen (Wirkstoffgehalt 80 Gew.%).V. 80 parts by weight of an active ingredient are mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 10 parts by weight of the sodium salt of a lignin sulfonic acid from a sulfite waste liquor and 7 parts by weight in powder form Mix the silica gel well and grind it in a hammer mill (active ingredient content 80% by weight).
VI. Man vermischt 90 Gew.-Teile eines Wirkstoffs mit 10 Gew.- Teilen N-Methyl-α-pyrrolidon und erhält eine Lösung, die zur Anwendung in Form kleinster Tropfen geeignet ist (Wirkstoffgehalt 90 Gew.%).VI. 90 parts by weight of an active ingredient are mixed with 10 parts by weight of N-methyl-α-pyrrolidone, and a solution is obtained which is suitable for use in the form of tiny drops (active ingredient content 90% by weight).
VII. 20 Gew.-Teile eines Wirkstoffs werden in einer Mischung gelöst, die aus 40 Gew.-Teilen Cyclohexanon, 30 Gew.-Tei¬ len Isobutanol, 20 Gew.-Teilen des Anlagerungsproduktes von 7 Mol Ethylenoxid an 1 Mol Isooctylphenol und 10VII. 20 parts by weight of an active ingredient are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide and 1 mole of isooctylphenol and 10
Gew.-Teilen des Anlagerungsproduktes von 40 Mol Ethylen¬ oxid an 1 Mol Ricinusöl besteht. Durch Eingießen und fei- nes Verteilen der Lösung in 100 000 Gew.-Teilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew.% des Wirkstoffs enthält.Parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil consists. By pouring and Distributing the solution in 100,000 parts by weight of water gives an aqueous dispersion which contains 0.02% by weight of the active ingredient.
VIII. 20 Gew.-Teile eines Wirkstoffs werden mit 3 Gew.-Teilen des Natriumsalzes der Diisobutylnaphthalin-α-sulfonsäure, 17 Gew.-Teilen des Natriumsalzes einer Ligninsulfonsäure aus einer Sulfit-Ablauge und 60 Gew.-Teilen pulver¬ förmigem Kieselsäuregel gut vermischt und in einer Ham- mermühle vermählen. Durch feines Verteilen der Mischung in 20 000 Gew.-Teilen Wasser erhält man eine Spritzbrühe, die 0,1 Gew.% des Wirkstoffs enthält.VIII. 20 parts by weight of an active ingredient are combined with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel mixed and ground in a hammer mill. By finely distributing the mixture in 20,000 parts by weight of water, a spray liquor is obtained which contains 0.1% by weight of the active ingredient.
Granulate, z.B. Umhüllungs-, Imprägnierungs- und Homogen- granulate, können durch Bindung der Wirkstoffe an feste Träger¬ stoffe hergestellt werden. Feste Trägerstoffe sind z.B. Mineral¬ erden, wie Silicagel, Kieselsäuren, Kieselgele, Silikate, Talkum, Kaolin, Attaclay, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolo¬ mit, Diatomeenerde, Calcium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, Düngemittel, wie z.B. Ammoniumsulfat,Granules, e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers. Solid carriers are e.g. Mineral soils, such as silica gel, silicas, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as e.g. Ammonium sulfate,
Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Pro¬ dukte, wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver und andere feste Trägerstoffe.Ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
Zu den Wirkstoffen können Öle verschiedenen Typs, Herbizide, Fun¬ gizide, andere Schädlingsbekämpfungsmittel, Bakterizide, gegebe¬ nenfalls auch erst unmittelbar vor der Anwendung (Tankmix) , zuge¬ setzt werden. Diese Mittel können zu den erfindungsgemäßen Mit¬ teln im Gewichtsverhältnis 1:10 bis 10:1 zugemischt werden.Oils of various types, herbicides, fungicides, other pesticides, bactericides can be added to the active compounds, if appropriate also only immediately before use (tank mix). These agents can be added to the agents according to the invention in a weight ratio of 1:10 to 10: 1.
SynthesebeispieleSynthesis examples
Die in den nachstehenden Synthesebeispielen wiedergegebenen Vor¬ schriften wurden unter entsprechender Abwandlung der Ausgangs- Verbindungen zur Gewinnung weiterer Verbindungen I benutzt. Die so erhaltenen Verbindungen sind in den anschließenden Tabellen mit physikalischen Angaben aufgeführt.The instructions given in the synthesis examples below were used to obtain further compounds I, with a corresponding modification of the starting compounds. The compounds thus obtained are listed in the tables below with physical details.
SynthesebeispieleSynthesis examples
Beispiel 1example 1
Darstellung von (E,E) -2-Methoxyimino-2-[2'- (l"-methyl, 1' '-acetyl)-iminooxymethyl]phenylessigsäuremethylester Zu 6,4 g (0,21 mol) Natriumhydrid (80 %) in 150 ml trockenem Dimethylformamid gibt man unter Schutzgas und leichtem Kühlen bei Raumtemperatur 21 g (0,21 mol) Diacetylmonoxim und rührt den An¬ satz 30 min bei Raumtemperatur. Anschließend wird eine Lösung von 60 g (0,21 mol) 2-Methoxyimino-2- (2'brommethyDphenylessigsäure- methylester in 360 ml Dimethylformamid zugetropft und 16 h bei Raumtemperatur gerührt. Nach Zugabe von 10 %iger Salzsäure wird mit Methyl-tert.-butyl-ether extrahiert. Die vereinigten organi¬ schen Phasen werden mit Wasser gewaschen, über Na2S04 getrocknet und eingeengt. Der Rückstand wird in wenig kaltem Methanol sus¬ pendiert. Nach Absaugen erhält man 38 g (59 %) der Titel¬ verbindung als hellbraune Kristalle mit einem Schmelzpunkt von 69 - 71°C. iH-NMR (CDCl3):δ= l,87(s,3H); 2,30(s,3H); 3,85(s,3H); 4,05(s,3H); 5,15(s,2H); 7,17-7,48 (m,4H) ppm.Preparation of (E, E) -2-methoxyimino-2- [2'- (1 "-methyl, 1" -acetyl) -iminooxymethyl] phenylacetic acid, methyl ester 21 g (0.21 mol) of diacetyl monoxime are added to 6.4 g (0.21 mol) of sodium hydride (80%) in 150 ml of dry dimethylformamide under protective gas and gentle cooling at room temperature and the mixture is stirred for 30 minutes at room temperature. A solution of 60 g (0.21 mol) of methyl 2-methoxyimino-2- (2'-bromomethylphenylacetate in 360 ml of dimethylformamide is then added dropwise and the mixture is stirred at room temperature for 16 h. After the addition of 10% hydrochloric acid, methyl tert. The combined organic phases are washed with water, dried over Na 2 SO 4 and concentrated. The residue is suspended in a little cold methanol. After suctioning off, 38 g (59%) of the title are obtained compound as light brown crystals with a melting point of 69-71 ° C. i H-NMR (CDCl 3 ): δ = 1.87 (s, 3H); 2.30 (s, 3H); 3.85 (s, 3H) ); 4.05 (s, 3H); 5.15 (s, 2H); 7.17-7.48 (m, 4H) ppm.
Beispiel 2Example 2
Darstellung von (E,E,E) -2-Methoxyimino-2- [2'- (1' '-methyl, 1' '- (1' ' '-ethoxyiminoethyl) )iminooxymethyl]phenylessigsäure- methylesterPreparation of (E, E, E) -2-methoxyimino-2- [2'- (1 '' -methyl, 1 '' - (1 '' '-ethoxyiminoethyl)) iminooxymethyl] phenylacetic acid, methyl ester
Zur Lösung von 2,5 g (8,2 mmol) (E,E) -2-Methoxyi- mino-2-[2'- (1' '-methyl, 1' '-acetyl)iminooxymethyl]phenylessig- säuremethylester in 60 ml warmen Methanol gibt man nach Abkühlen auf Raumtemperatur 0,96 g (9,8 mmol) O-Ethylhydroxylamin-Hydro- chlorid sowie 0,6 g trockene Molekularsiebperlen (3 A) und läßt 5 Tage bei Raumtemperatur stehen. Nach Abfiltrieren des Moleku¬ larsiebes wird die Lösung eingeengt, der Rückstand zwischen Me- thyl-tert.-butyl-ether und Wasser verteilt, die organische Phase mit Wasser gewaschen, über Na2Sθ4 getrocknet und eingeengt. Nach Verreiben des Rückstandes mit n-Hexan und Absaugen erhält man 1,8 g (63 %) der Titelverbindung als hellgelbe Kristalle mit einem Schmelzpunkt von 69 - 72°C.For the solution of 2.5 g (8.2 mmol) of (E, E) -2-methoxyimino-2- [2'- (1 '' methyl, 1 '' acetyl) iminooxymethyl] phenylacetic acid, methyl ester in After cooling to room temperature, 60 ml of warm methanol are added to 0.96 g (9.8 mmol) of O-ethylhydroxylamine hydrochloride and 0.6 g of dry molecular sieve beads (3A) and left to stand for 5 days at room temperature. After filtering off the molecular sieve, the solution is concentrated, the residue is partitioned between methyl tert-butyl ether and water, the organic phase is washed with water, dried over Na 2 SO 4 and concentrated. After triturating the residue with n-hexane and suction, 1.8 g (63%) of the title compound are obtained as light yellow crystals with a melting point of 69-72 ° C.
iH-NMR (CDCl3):δ= l,27(t,3H); 1,96(S,3H); 1,99(S,3H); 3,84(S,3H); 4,04(s,3H); 4,17(q,2H); 5,06(s,2H); 7,17-7,49(m,4H) ppm i H NMR (CDCl 3 ): δ = 1.27 (t, 3H); 1.96 (S, 3H); 1.99 (S, 3H); 3.84 (S, 3H); 4.04 (s, 3H); 4.17 (q, 2H); 5.06 (s. 2H); 7.17-7.49 (m, 4H) ppm
Beispiel 3Example 3
Darstellung von (E,E,E) -2-Methoxyimino-2- [2'- (l'-methyl,Preparation of (E, E, E) -2-methoxyimino-2- [2'- (l'-methyl,
1"- (1" '-ethoxyiminoethyl) ) iminooxymethyllphenylthioessigsäure-1 "- (1" '-ethoxyiminoethyl)) iminooxymethyllphenylthioacetic acid -
S-methylesterS-methyl ester
7,0 g (20 mmol) (E,E,e) -2-Methox imino-2-[2'- (l"-methyl,7.0 g (20 mmol) (E, E, e) -2-methoximino-2- [2'- (l "-methyl,
1"- (1" '-ethoxyiminoethyl) ) iinooxymethyl]phenylessigsäuremethyl- ester werden in 60 ml 1 M wäßriger KOH-Lösung 4 Stunden auf 80°C erhitzt. Nach dem Abkühlen wird mit Methyl-tert.-butyl-ether ex¬ trahiert, die wäßrige Phase mit •halbkonz. Salzsäure angesäuert und mit Methyl-tert.-butyl-ether extrahiert. Nach Waschen der or¬ ganischen Phase mit Wasser, Trocknen (Na2S04) und Einengen erhält man 6,0 g (E,E,E) -2-Methoxyimino-2- [2 '- (l"-methyl, 1"- (1" '-etho¬ xyiminoethyl) ) iminooxymethyl]phenylessigsäure als farblosen Fest¬ stoff, der anschließend in 100 ml trockenem DMF gelöst wird. Nach Zugabe von 2,9 g (18 mmol Carbonyldiimidazol rührt man 1 Stunde, gibt anschließend 2,5 g (36 mmol) Natriummethanthiolat zu und läßt 16 Stunden weiterrühren. Der Ansatz wird eingeengt, der Rückstand in Methyl-tert.-butyl-ether und Wasser aufgenommen, die organische Phase mit 1 M wäßriger NaOH-Lösung extrahiert, mit Wasser gewaschen, über a2S04 getrocknet und eingeengt. Man erhält so 4,1 g (57 %) der TitelVerbindung als hellgelbes öl.1 "- (1"'-ethoxyiminoethyl)) iinooxymethyl] phenylacetic acid methyl ester are in 60 ml of 1 M aqueous KOH solution at 80 ° C for 4 hours heated. After cooling, the mixture is extracted with methyl tert-butyl ether, the aqueous phase with • half-conc. Acidified hydrochloric acid and extracted with methyl tert-butyl ether. After washing the organic phase with water, drying (Na 2 S0 4 ) and concentrating, 6.0 g of (E, E, E) -2-methoxyimino-2- [2 '- (l "-methyl, 1 "- (1"'-ethoxyiminoethyl)) iminooxymethyl] phenylacetic acid as a colorless solid which is then dissolved in 100 ml of dry DMF. After adding 2.9 g (18 mmol of carbonyldiimidazole, stirring is carried out for 1 hour, followed by 2 5 g (36 mmol) of sodium methanethiolate and stirring is continued for 16. The mixture is concentrated, the residue is taken up in methyl tert-butyl ether and water, the organic phase is extracted with 1 M aqueous NaOH solution and washed with water , dried over a2SO 4 and concentrated to give 4.1 g (57%) of the title compound as a light yellow oil.
iH-NMR (CDC13): δ = 1,27 (t,3H); 1,95 (s,3H); 1,98 (s,3H); 2,33 (s,3H); 4,05 (s,3H); 4,17 (q,2H) ; 5,03 (s,2H); 7,12-7,48 (m,4H) ppm. i H NMR (CDC1 3 ): δ = 1.27 (t, 3H); 1.95 (s, 3H); 1.98 (s, 3H); 2.33 (s, 3H); 4.05 (s, 3H); 4.17 (q, 2H); 5.03 (s. 2H); 7.12-7.48 (m, 4H) ppm.
Tabelle:Table:
Figure imgf000103_0001
Figure imgf000103_0001
Figure imgf000103_0002
Figure imgf000103_0002
Beispiele zur Wirkung gegen SchadpilzeExamples of the action against harmful fungi
Die fungizide Wirkung der Verbindungen der allgemeinen Formel I ließ sich durch folgende Versuche zeigen:The fungicidal activity of the compounds of the general formula I was demonstrated by the following tests:
Die Wirkstoffe wurden als 20 %-ige Emulsion in einem Gemisch aus 70 Gew.-% Cyclohexanon, 20 Gew.-% Nekanil® IN (Lutensol® AP6, Νetzmittel mit Emulgier- und Dispergierwirkung auf der Basis ethoxylierter Alkylphenole) und 10 Gew.-% Emulphor® EL (Emulan® EL, Emulgator auf der Basis ethoxylierter Fettalkohole) aufbereitet und entsprechend der gewünschten Konzentration mit Wasser verdünnt.The active ingredients were administered as a 20% emulsion in a mixture of 70% by weight cyclohexanone, 20% by weight Nekanil ® IN (Lutensol ® AP6, detergent with emulsifying and dispersing action based on ethoxylated alkylphenols) and 10% by weight. % Emulphor ® EL (Emulan ® EL, emulsifier based on ethoxylated fatty alcohols) prepared and diluted with water according to the desired concentration.
1. Erysiphe graminis var. tritici1. Erysiphe graminis var. Tritici
Blätter von Weizenkeimlingen (Sorte "Kanzler") wurden zunächst mit der wäßrigen Aufbereitung der Wirkstoffe (63 ppm-haltig) be- • handelt. Nach ca. 24 h wurden die Pflanzen mit Sporen des Weizen¬ mehltaus (Erysiphe graminis var. tritici) bestäubt. Die so behan- delten Pflanzen wurden anschließend für 7 Tage bei 20-22°C und einer relativen Luftfeuchtigkeit von 75-80% inkubiert. Anschlie¬ ßend wurde das Ausmaß der Pilz.entwicklung ermittlelt.Leaves of wheat seedlings ("Chancellor" variety) were first treated with the aqueous preparation of the active ingredients (containing 63 ppm). After about 24 hours, the plants were dusted with spores of wheat powdery mildew (Erysiphe graminis var. Tritici). The plants treated in this way were then incubated for 7 days at 20-22 ° C. and a relative atmospheric humidity of 75-80%. The extent of the fungal development was then determined.
In diesem Text zeigten die mit den erfindungsgemäßen Verbindungen behandelten Pflanzen keinen Befall, die mit einem bekannten Wirk¬ stoff (Verbindung Nr. 497, Tabelle 2, EP-A 463 488) behandelten Pflanzen 40 % Befall und die unbehandelten Pflanzen 70 % Befall.In this text, the plants treated with the compounds according to the invention showed no infection, the plants treated with a known active ingredient (compound No. 497, Table 2, EP-A 463 488) showed 40% attack and the untreated plants 70% attack.
Beispiele zur Wirkung gegen tierische SchädlingeExamples of action against animal pests
Die insektizide Wirkung der Verbindungen der allgemeinen Formel I ließ sich durch folgende Versuche zeigen:The insecticidal activity of the compounds of the general formula I was demonstrated by the following tests:
Die Wirkstoffe wurdenThe active ingredients were
a) als 0,1 %-ige Lösung in Aceton odera) as a 0.1% solution in acetone or
b) als 10 %-ige Emulsion in einem Gemisch aus 70 Gew.-% Cyclo- hexanol, 20 Gew.-% Nekanil® LN (Lutensol® AP6, Netzmittel mit Emulgier- und Dispergierwirkung auf der Basis ethoxylierterb) as a 10% emulsion in a mixture of 70 wt .-% cyclohexanol, 20 wt .-% Nekanil ® LN (Lutensol ® AP6, wetting agent having emulsifying and dispersing action based on ethoxylated
Alkylphenole) und 10 Gew.-% Emulphor® EL (Emulan® EL, Emulga¬ tor auf der Basis ethoxylierter Fettalkohole)Alkylphenols) and 10 wt .-% Emulphor ® EL (Emulan ® EL, emulsifiers tor based on ethoxylated fatty alcohols)
aufbereitet und entsprechend der gewünschten Konzentration mit Aceton im Fall von a) bzw. mit Wasser im Fall von b) ver¬ dünnt. Nach Abschluß der Versuche wurde die jeweils niedrigste Konzentration ermittelt, bei der die Verbindungen im Ver¬ gleich zu unbehandelten Kontrollversuchen noch eine 80 bis 100 %-ige Hemmung bzw. Mortalität hervorriefen (Wirkschwelle bzw. Minimal- konzentration) . processed and diluted according to the desired concentration with acetone in the case of a) or with water in the case of b). At the end of the tests, the lowest concentration was determined at which the compounds still caused an 80 to 100% inhibition or mortality compared to untreated control tests (threshold of action or minimum concentration).

Claims

Patentansprüche claims
1. Phenylessigsäurederivate der Formel I1. Phenylacetic acid derivatives of the formula I.
Figure imgf000106_0001
Figure imgf000106_0001
0=C-SR1 0 = C-SR 1
in der die Substituenten und der Index die folgende Bedeutung haben:in which the substituents and the index have the following meaning:
R1 Wasserstoff und Cι-C4-Alkyl;R 1 is hydrogen and -CC 4 alkyl;
R2 Cyano, Nitro, Trifluormethyl, Halogen, Cι~C4-Alkyl und Cι-C4-Alkoxy;R 2 cyano, nitro, trifluoromethyl, halogen, C 1 -C 4 alkyl and C 1 -C 4 alkoxy;
m 0, 1 oder 2, wobei die Reste R2 verschieden sein können, wenn m für 2 steht;m is 0, 1 or 2, it being possible for the radicals R 2 to be different if m is 2;
R3 Wasserstoff, Cyano, Nitro, Hydroxy, Amino, Halogen, Cι-C4-Alkyl, Cι-C4-Halogenalkyl, Cι-C4-Alkoxy, Cι-C -Halogenalkoxy, Cι-C -Alkylthio, Cι-C -Alkylamino oder Di-Cι-C4-alkylamino;R 3 is hydrogen, cyano, nitro, hydroxy, amino, halogen, -CC 4 -alkyl, -C-C 4 -haloalkyl, -C-C 4 -alkoxy, -C-C -haloalkoxy, -C-C-alkylthio, -C-C -Alkylamino or Di-Cι-C 4 alkylamino;
R4 Wasserstoff, Cyano, Nitro, Hydroxy, Amino, Halogen,R 4 is hydrogen, cyano, nitro, hydroxy, amino, halogen,
Ci-Cε-Alkyl, Ci-Cε-Alkoxy, Ci-Cδ-Alkylthio, Ci-Cε-Alkyl- amino, Di-Ci-Cε-alkylamino, C -C6-Alkenyl, C2-C6-Alkenyl- oxy, C2~C6-Alkenylthio, C2-C6-Alkenylamino, N-C2-C6-Alke- nyl-N-Ci-Cδ-alkylamino, C2-C6-Alkinyl, C2-C6-Alkinyloxy, C2-C6-Alkinylthio, C2-C6-Alkinylamino, N-C2-C6~Alkinyl- N-Cι-C6-alkylamino, wobei die KohlenwasserStoffreste die¬ ser Gruppen partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Reste tragen können: Cyano, Nitro, Hydroxy, Merkapto,Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Halogen, Cι-C6-Alkyl- aminocarbonyl, Di-Ci-Cε-alkylaminocarbonyl, Ci-Cδ-Alkyl- aminothiocarbonyl, Di-Cι-C6-alkylaminothiocarbonyl, Ci-Cε-Alkylsulfonyl, Ci-Cε-Alkylsulfoxyl, Ci-Cβ-Alkoxy, Ci-Ce-Halogenalkoxy, Cι-C6-Alkoxycarbonyl, Ci-Ce-Alkyl- thio, Cι-C6-Alkylamino, Di-Ci-Ce-alkylamino, C2-Ce-Alkenyloxy, C3-C6-Cycloalkyl, C3-C6-Cycloalkyloxy, Heterocyclyl, Heterocyclyloxy, Aryl, Aryloxy, Aryl-Cι-C4-alkoxy, Arylthio, Aryl-Cι-C4-alkylthio, Hetaryl, Hetaryloxy, Hetaryl-Cι-C -alkoxy, Hetarylthio, Hetaryl-Cι-C4-alkylthio, wobei die cyclischen Reste ih- rerseitspartiell oder vollständig halogeniert sein können und/oder ein bis drei der folgenden Gruppen tragen kön¬ nen: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Ci-Cε-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkylsulfonyl, Ci-Cε-Alkyl- ■ sulfoxyl, C3C6-Cycloalkyl, Cι-C6-Alkoxy, Ci-Cδ-Halogen- alkoxy, Cι-C6-Alkoxycarbonyl, Ci-Cβ-Alkylthio, Ci-Cδ-Alkylamino, Di-Cι-C6-alkylamino, Ci-Cδ-Alkylamino- carbonyl, Di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-Alkylamino- thiocarbonyl, Di-Ci-Cε-alkylaminothiocarbonyl, C2~C6-Alkenyl, C2-C6-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy, Hetarylthio und C(=NOR6)-An-R7;Ci-Cε-alkyl, Ci-Cε-alkoxy, Ci-C δ- alkylthio, Ci-Cε-alkylamino, di-Ci-Cε-alkylamino, C -C 6 -alkenyl, C 2 -C 6 -alkenyl- oxy, C 2 ~ C 6 alkenylthio, C 2 -C 6 alkenylamino, NC 2 -C 6 alkenyl-N-Ci-C δ -alkylamino, C 2 -C 6 alkynyl, C 2 -C 6 Alkynyloxy, C 2 -C 6 -alkynylthio, C 2 -C 6 -alkynylamino, NC 2 -C 6 ~ alkynyl-N--C-C6-alkylamino, where the hydrocarbon radicals of these groups can be partially or completely halogenated or one can carry up to three of the following radicals: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkyl aminocarbonyl, di-Ci-Cε-alkylaminocarbonyl, Ci-C δ- alkyl- aminothiocarbonyl, di-Cι-C 6 -alkylaminothiocarbonyl, Ci-Cε-alkylsulfonyl, Ci-Cε-alkylsulfoxyl, Ci-Cβ-alkoxy, Ci-Ce-haloalkoxy, Cι-C 6 -alkoxycarbonyl, Ci-Ce-alkylthio, Cι-C 6 alkylamino, di-Ci-Ce-alkylamino, C 2 -Ce-alkenyloxy, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyloxy, Heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl -CC 4 alkoxy, arylthio, aryl -CC 4 -alkylthio, hetaryl, hetaryloxy, hetaryl -CC-alkoxy, hetarylthio, hetaryl -CC 4 -alkylthio , where the cyclic radicals on their side can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, Ci-Cε-alkyl, Ci -Cg-haloalkyl, Ci-Cg-alkylsulfonyl, Ci-Cε-alkyl- ■ sulfoxyl, C 3 C 6 -cycloalkyl, Cι-C 6 -alkoxy, Ci-C δ -halogenalkoxy, Cι-C 6 -alkoxycarbonyl, Ci-Cβ-alkylthio, Ci-C δ- alkylamino, di-Cι-C 6 -alkylamino, Ci-C δ -alkylamino-carbonyl, di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkylamino-thiocarbonyl, di-Ci -Cε-alkylaminothiocarbonyl, C 2 ~ C 6 alkenyl, C 2 -C 6 alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C (= NOR 6 ) -A n -R 7 ;
C3-C6-Cycloalkyl, C3-C6-Cycloalkyloxy, C3-C6-Cycloalkyl- thio, C3-C6-Cycloalkylamino, N-C3-C6-Cycloalkyl-C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyloxy, C 3 -C 6 cycloalkylthio, C 3 -C 6 cycloalkylamino, NC 3 -C 6 cycloalkyl-
N-Cι-C6-alkylamino, C -C6-Cycloalkenyl, C3-C6~Cycloalkeny- loxy, C3-C6-Cycloalkenylthio, C3-C6-Cycloalkenylamino, N-C3-C6~Cycloalkenyl-N-Cι-C6-alkylamino, Heterocyclyl, Heterocyclyloxy, Heterocyclylthio, Heterocyclylamino, N- Heterocyclyl-N-Cι-C6-alkylamino, Aryl, Aryloxy, Arylthio, Arylamino, N-Aryl-N-Ci-Cg-alkylamino, Hetaryl, Hetaryl¬ oxy, Hetarylthio, Hetarylamino, N-Hetaryl-N-Ci-Ce-alkyl- amino, wobei die cyclischen Reste partiell oder vollstän¬ dig halogeniert sein können oder einen bis drei der fol- genden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothio¬ carbonyl, Halogen, Ci-Ce-Alkyl, Ci-Cε-Halogenalkyl, Ci-Cβ-Alkylsulfonyl, Cι-C6-Alkylsulfoxyl, C3-C6-Cyclo- alkyl, Ci-Cβ-Alkoxy, Ci-Cε-Halogenalkoxy, Ci-Ce-Alkoxy- carbonyl, Ci-Cε-Alkylthio, Ci-Cδ-Alkylamino,N-Cι-C 6 alkylamino, C -C 6 cycloalkenyl, C 3 -C 6 ~ cycloalkenyloxy, C 3 -C 6 cycloalkenylthio, C 3 -C 6 cycloalkenylamino, NC 3 -C 6 ~ cycloalkenyl N-Cι-C 6 -alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N- heterocyclyl-N-Cι-C 6 -alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N-Ci-Cg-alkylamino Hetaryl, hetaryloxy, hetarylthio, hetarylamino, N-hetaryl-N-Ci-Ce-alkylamino, where the cyclic radicals can be partially or completely halogenated or can carry one to three of the following groups: cyano, Nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Ci-Ce-alkyl, Ci-Cε-haloalkyl, Ci-Cβ-alkylsulfonyl, Cι-C 6 alkylsulfoxyl, C 3 -C 6 cyclo alkyl, Ci-Cβ-alkoxy, Ci-Cε-haloalkoxy, Ci-Ce-alkoxycarbonyl, Ci-Cε-alkylthio, Ci-C δ -alkylamino,
Di-Ci-Cg-alkylamino, Cι-C6-Alkylaminocarbonyl, Di-Ci-Cβ-alkylaminocarbonyl, Cι-C6-Alkylaminothiocarbonyl, Di-Ci-Cö-alkylaminothiocarbonyl, C2~C6-Alkenyl, C2~C6-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Hetaryl und Hetaryloxy;Di-Ci-Cg-alkylamino, Cι-C 6 -alkylaminocarbonyl, Di-Ci-Cβ-alkylaminocarbonyl, Cι-C 6 -alkylaminothiocarbonyl, Di-Ci-C ö -alkylaminothiocarbonyl, C 2 ~ C 6 -alkenyl, C 2 ~ C 6 alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy;
Wasserstoff,Hydrogen,
Cι-Cιo-Alkyl, C3-C6-Cycloalkyl, C2-Cιo~Alkenyl, C2-Cιo-Alkinyl, Cι-Cιo-Alkylcarbonyl, C2-Cιo-Alkenyl- carbonyl, C3-Cιo-Alkinylcarbonyl oder Cι-Cιo-Alkyl- sulfonyl, wobei diese Reste partiell oder vollständig ha¬ logeniert sein können oder einen bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Halo- . gen, Ci-Cε-AlJcyl, Ci-Ce-Halogenalkyl, Ci-Cß-Alkylsulfonyl, Cι-C6-Alkylsulfoxyl, Ci-Cε-Alkoxy, Ci-Cδ-Halogenalkoxy, Ci-Cε-Alkoxycarbonyl, Ci-Cε-Alkylthio, Cι-C6-Alkylamino, Di-Ci-Cβ-alkylamino, Cι-C6-Alkylaminocarbonyl, Di-Cι-C6-alkylaminocarbonyl, Ci-Cδ-Alkylaminothiocarbonyl, Di-Ci-Cδ-alkylaminothiocarbonyl, C2-C6-Alkenyl, C2 _C6-Alkenyloxy, C3-C6-Cycloalkyl, C3-C6-Cycloalkyloxy, Heterocyclyl, Heterocyclyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy und Hetarylthio, wobei die cyclischen Gruppen ihrerseits partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Amino¬ thiocarbonyl, Halogen, Cι-C6-Alkyl, Ci-Ce-Halogenalkyl, Ci-Cδ-Alkylsulfonyl, Cι-C6-Alkylsulfoxyl, C3-C6-Cyclo- alkyl, Ci-Cε-Alkoxy, Ci-Cδ-Halogenalkoxy, Ci-Cδ-Alkyloxy- carbonyl, Ci-Cß-Alkylthio, Cι-C6-Alkylamino, Di-Ci-Cδ-Alkylamino, Cι-C6-Alkylaminocarbonyl,-C-Cιo-alkyl, C 3 -C 6 -cycloalkyl, C 2 -Cιo ~ alkenyl, C 2 -Cιo-alkynyl, Cι-Cιo-alkylcarbonyl, C 2 -Cιo-alkenylcarbonyl, C 3 -Cιo-alkynylcarbonyl or -C-Cιo-alkyl sulfonyl, where these residues can be partially or completely halogenated or one to three of the following Groups can wear: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halo. gene, Ci-Cε-AlJcyl, Ci-Ce-haloalkyl, Ci-C ß -Alkylsulfonyl, Cι-C6-alkylsulfoxyl, Ci-Cε-alkoxy, Ci-C δ -haloalkoxy, Ci-Cε-alkoxycarbonyl, Ci-Cε- Alkylthio, -C-C 6 alkylamino, di-Ci-Cβ-alkylamino, Cι-C 6 -alkylaminocarbonyl, di-Cι-C 6 -alkylaminocarbonyl, Ci-C δ -alkylaminothiocarbonyl, di-Ci-C δ -alkylaminothiocarbonyl, C 2 -C 6 alkenyl, C 2 _ C 6 alkenyloxy, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyloxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio , wherein the cyclic groups in turn can be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, amino thiocarbonyl, halogen, C 1 -C 6 alkyl, Ci -Ce-haloalkyl, Ci-C δ -alkylsulfonyl, Cι-C 6 -alkylsulfoxyl, C 3 -C 6 -cycloalkyl, Ci-Cε-alkoxy, Ci-C δ -haloalkoxy, Ci-Cδ-alkyloxycarbonyl, Ci-C ß- alkylthio, -C-C 6 alkylamino, Di-Ci-C δ alkylamino, -C-C 6 alkylaminocarbonyl,
Di-Cι-C6-Alkylaminocarbonyl, Ci-Cß-Alkylaminothiocarbonyl, Di-Cι-C6-Alkylaminothiocarbonyl, C2~C6-Alkenyl, C2~C6-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Aryl¬ thio, Hetaryl, Hetaryloxy, Hetarylthio oder C(=NOR6)-An-R7;Di-Cι-C 6 -alkylaminocarbonyl, Ci-C ß -alkylaminothiocarbonyl, Di-Cι-C 6 -alkylaminothiocarbonyl, C 2 ~ C 6 -alkenyl, C 2 ~ C 6 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, aryl ¬ thio, hetaryl, hetaryloxy, hetarylthio or C (= NOR 6 ) -A n -R 7 ;
Aryl, Arylcarbonyl, Arylsulfonyl, Hetaryl, Hetaryl¬ carbonyl oder Hetarylsulfonyl, wobei diese Reste partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können: Cyano, Nitro,Aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, where these radicals can be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro,
Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Amino¬ thiocarbonyl, Halogen, Ci-Cß-Alkyl, Ci-Cβ-Halogenalkyl, Ci-Cß-Alkylcarbonyl, Ci-Cg-Alkylsulfonyl, Ci-Cδ-Alkyl- sulfoxyl, C3-C6-Cycloalkyl, Ci-Cε-Alkoxy, Ci-Cε-Halogen- alkoxy, Ci-Cδ-Alkyloxycarbonyl, Ci-Cε-Alkylthio,Hydroxy, mercapto, amino, carboxyl, aminocarbonyl, amino thiocarbonyl, halogen, Ci-C ß- alkyl, Ci-Cβ-haloalkyl, Ci-C ß- alkylcarbonyl, Ci-Cg-alkylsulfonyl, Ci-C δ -alkylsulfoxyl , C 3 -C 6 cycloalkyl, Ci-Cε-alkoxy, Ci-Cε-haloalkoxy, Ci-C δ- alkyloxycarbonyl, Ci-Cε-alkylthio,
Ci-Cδ-Alkylamino, Di-Ci-Ce-Alkylamino, Ci-Cε-Alkylamino- carbonyl, Di-Cι-C6-Alkylaminocarbonyl, Ci-Cδ-Alkylamino- thiocarbony1, Di-Ci-Cδ-Alkylaminothiocarbonyl, C2-Cg-Alkenyl, C2-C6-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Hetaryl, Hetaryloxy oder C(=NOR6)-An-R7;Ci-C δ- alkylamino, di-Ci-Ce-alkylamino, Ci-Cε-alkylamino-carbonyl, di-Cι-C6-alkylaminocarbonyl, Ci-C δ -alkylamino-thiocarbony1, di-Ci-C δ- alkylaminothiocarbonyl, C 2 -Cg alkenyl, C 2 -C 6 alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C (= NOR 6 ) -A n -R 7 ;
wobeiin which
für Sauerstoff, Schwefel oder Stickstoff steht und wobei der Stickstoff Wasserstoff oder Ci-Cg-Alkyl trägt; 107 n 0 oder 1 bedeutet;represents oxygen, sulfur or nitrogen and the nitrogen carries hydrogen or Ci-Cg-alkyl; 107 n represents 0 or 1;
R6 Wasserstoff oder Cι-C6~Alkyl bedeutet undR 6 is hydrogen or -CC 6 ~ alkyl and
R7 Wasserstoff oder Ci-Cβ-Al yl bedeutet,R 7 denotes hydrogen or Ci-Cβ-Al yl,
sowie deren Salze.as well as their salts.
2. Verbindungen der Formel I gemäß Anspruch 1, in denen R3, R4 und R5 die folgende Bedeutung haben:2. Compounds of formula I according to claim 1, in which R 3 , R 4 and R 5 have the following meaning:
R3 Wasserstoff, Hydroxy, Cyclopropyl, Halogen, Cι-C -Alkyl, Cι-C -Alkoxy oder C -C4-Alkylthio;R 3 is hydrogen, hydroxy, cyclopropyl, halogen, -CC alkyl, -CC alkoxy or C -C 4 alkylthio;
R4 Wasserstoff, Hydroxy, Halogen, Cyclopropyl, Cyclohexyl, Cι-C4-Alkyl, Cι-C4-Alkoxy, Cι-C4-Alkylthio, Aryl oder Hetary, wobei diese Gruppen partiell oder voll¬ ständig halogeniert sein können oder ein bis 3 der fol¬ genden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mer- kapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Halogen, Cι-C6-Alkyl, Ci-Cε-Halogenalkyl, Ci-Cδ-Alkyl- sulfonyl, Ci-Cε-Alkylsulfoxyl, C3-C6-Cycloalkyl, Cι~ Cß-Alkoxy, Ci-Cß-Halogenalkoxy, Ci-Cg-Alkoxycarbonyl, Ci-Cß-Alkylthio, Ci-Cδ-Alkylamino, Di-Ci-Cö-alkylamino, Ci-Cß-Alkylaminocarbonyl, Di-Ci-Cg-alkylaminocarbonyl,R 4 is hydrogen, hydroxyl, halogen, cyclopropyl, cyclohexyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, aryl or hetary, where these groups can be partially or completely halogenated or a may carry one to 3 of the folic constricting groups: cyano, nitro, hydroxy, mer- kapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Cι-C6 alkyl, Ci-Cε-haloalkyl, Ci-C alkyl δ sulfonyl, Ci-Cε-alkylsulfoxyl, C 3 -C 6 cycloalkyl, Cι ~ C ß -alkoxy, Ci-C ß -haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cß-alkylthio, Ci-C δ -alkylamino, Di -Ci-C ö alkylamino, Ci-C ß alkylaminocarbonyl, di-Ci-Cg-alkylaminocarbonyl,
C -Cg-Alkylaminothiocarbonyl, Di-Cι-C6 _alkylaminothiocar- bonyl, C2-C6-Alkenyl, C2-C6-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Hetaryl und Hetaryloxy;C -Cg-Alkylaminothiocarbonyl, Di-Cι-C 6 _ alkylaminothiocarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy;
R5 Wasserstoff,R 5 is hydrogen,
Cι-Cιo-Alkyl, C3-C6-Cycloalkyl, C2-Cι0-Alkenyl, C2-Cι0- Alkinyl, Cι-Cιo-Alkylcarbonyl, C2-Cιo-Alkenylcarbonyl, C3-Cιo-Alkinylcarbonyl oder Ci-Cio-Alkylsulfonyl, wobei diese Gruppen partiell oder vollständig halogeniert sein können oder ein bis 3 der folgenden Gruppen tragen kön¬ nen: Cyano, Nitro, Hydroxy, Merkapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Halogen, Ci-Cβ-Alkyl, Ci-Cß-Halogenalkyl, Ci-Cε-Alkylsulfonyl, Ci-Cε-Alkylsulfo- xyl, C3-C6-Cycloalkyl, Ci-Cß-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cδ-Alkoxycarbonyl, Ci-Cß-Alkylthio, Ci-Cβ-Alkylamino,Cι-Cιo-alkyl, C 3 -C 6 cycloalkyl, C 2 -Cι 0 -alkenyl, C2-Cι 0 - alkynyl, Cι-Cιo-alkylcarbonyl, C 2 -Cιo-alkenylcarbonyl, C 3 -Cιo-alkynylcarbonyl or Ci -Cio-alkylsulfonyl, where these groups can be partially or completely halogenated or can carry one to 3 of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Ci-Cβ-alkyl, Ci-C ß -haloalkyl, Ci-Cε-alkylsulfonyl, Ci-Cε-alkylsulfoxyl, C 3 -C 6 -cycloalkyl, Ci-C ß- alkoxy, Ci-Cg-haloalkoxy, Ci-C δ- alkoxycarbonyl, Ci -C ß- alkylthio, Ci-Cβ-alkylamino,
Di-Ci-Cg-alkylamino, Ci-Cg-Alkylaminocarbonyl, Di- Ci-Cg-alkylaminocarbonyl, Ci-Ce-Alkylaminothiocarbonyl, Di-Ci-Cg-alkylaminothiocarbonyl, C2-C6-Alkenyl, C2-C6-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Aryl- thio, Hetaryl, Hetaryloxy und Hetarylthio, wobei die aro¬ matischen und heteroaromatischen Reste ihrerseits parti¬ ell oder vollständig halogeniert sein können und/oder ein bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Halogen, Cι-C6-Alkyl, Ci-Cg-Halogen- alkyl, Cι-C6-Alkylsulfonyl, Ci-Cε-Alkylsulfoxyl, C3-C6-Cycloalkyl, Ci-Ce-Alkoxy, Ci-Cε-Halogenalkoxy,Di-Ci-Cg-alkylamino, Ci-Cg-alkylaminocarbonyl, di-Ci-Cg-alkylaminocarbonyl, Ci-Ce-alkylaminothiocarbonyl, di-Ci-Cg-alkylaminothiocarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 - Alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, where the aromatic and heteroaromatic radicals can in turn be partially or completely halogenated and / or can carry up to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylsulfonyl, Ci-Cε Alkyl sulfoxyl, C 3 -C 6 cycloalkyl, Ci-Ce alkoxy, Ci-Cε-haloalkoxy,
Ci-Cε-Alkyloxycarbonyl, Ci-Ce-Alkylthio, Ci-Cß-Alkylamino, Di-Ci-Cδ-Alkylamino, Cι-C6-Alkylaminocarbonyl, Di-Ci-Cö-Alkylaminocarbonyl, Cι-C6-Alkylaminothiocarbonyl, Di-C -C6-Alkylaminothiocarbonyl, C2-C6-Alkenyl, C2-C6-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Aryl¬ thio, Hetaryl, Hetaryloxy, Hetarylthio oder C(=NOR6)-An-R7;Ci-Cε-alkyloxycarbonyl, Ci-Ce-alkylthio, Ci-C ß -alkylamino, di-Ci-C δ -alkylamino, Cι-C 6 -alkylaminocarbonyl, di-Ci-C ö -alkylaminocarbonyl, Cι-C 6 -alkylaminothiocarbonyl , Di-C -C 6 alkylaminothiocarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, aryl thio, hetaryl, hetaryloxy, hetarylthio or C (= NOR 6 ) -A n -R 7 ;
Aryl, Hetaryl, Arylcarbonyl, Hetarylcarbonyl, Arylsulfo- nyl oder Hetarylsulfonyl, wobei diese Gruppen partiell oder vollständig halogeniert sein können oder ein bis 3 der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Merkapto, Amino, Carboxyl, Aminocarbonyl, Amino¬ thiocarbonyl, Halogen, Cι-C6-Alkyl, Ci-Ce-Halogenalkyl, Cι-C6-Alkylcarbonyl Cι-C6-Alkylsulfonyl, Cι-C6-Alkylsulfo- xyl, C3-Ce-Cycloalkyl, Ci-Cg-Alkoxy, Ci-Cε-Halogenalkoxy, Cι-C6~Alkoxycarbonyl, Ci-Cε-Alkylthio, Ci-Cε-Alkylamino, Di-Ci-Cε-alkylamino, Ci-Cg-Alkylaminocarbonyl, Di-Cι-C6-alkylaminocarbonyl, Cι-C6-Alkylaminothiocarbonyl, Di-C -C6-alkylaminothiocarbonyl, C2~C6-Alkenyl,Aryl, hetaryl, arylcarbonyl, hetarylcarbonyl, arylsulfonyl or hetarylsulfonyl, where these groups can be partially or completely halogenated or can carry one to 3 of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, amino thiocarbonyl , Halogen, -C-C 6 alkyl, Ci-Ce-haloalkyl, -C-C 6 alkylcarbonyl Cι-C 6 alkylsulfonyl, Cι-C 6 alkylsulfoxyl, C 3 -Ce cycloalkyl, Ci-Cg-alkoxy , Ci-Cε-haloalkoxy, -C-C 6 ~ alkoxycarbonyl, Ci-Cε-alkylthio, Ci-Cε-alkylamino, di-Ci-Cε-alkylamino, Ci-Cg-alkylaminocarbonyl, di-Cι-C 6 -alkylaminocarbonyl, Cι -C 6 alkylaminothiocarbonyl, di-C -C 6 alkylaminothiocarbonyl, C 2 ~ C 6 alkenyl,
C2-C6-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Hetaryl, Hetaryloxy oder C(=NOR6)-An-R7;C 2 -C 6 alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C (= NOR 6 ) -A n -R 7 ;
wobeiin which
A für Sauerstoff, Schwefel oder Stickstoff steht und wobei der Stickstoff Wasserstoff oder Ci-Ce-Alkyl trägt;A represents oxygen, sulfur or nitrogen and the nitrogen carries hydrogen or Ci-Ce-alkyl;
n 0 oder 1;n 0 or 1;
R6 Wasserstoff oder Ci-Ce-Alkyl bedeutet undR 6 is hydrogen or Ci-Ce-alkyl and
R7 Wasserstoff oder Ci-Cε-Alkyl bedeutet,R 7 denotes hydrogen or Ci-Cε-alkyl,
sowie deren Salze.as well as their salts.
3. Verbindungen der Formel I gemäß Anspruch 1, in denen m für 0 steht. 3. Compounds of formula I according to claim 1, in which m is 0.
4. Verbindungen der Formel I gemäß Anspruch 1, in denen R1 für Mehtyl steht.4. Compounds of formula I according to claim 1, in which R 1 is methyl.
5. Verfahren zur Herstellung der Verbindungen der Formel I gemäß Anspruch 1, in denen R3 nicht Halogen bedeutet, dadurch ge¬ kennzeichnet, daß man ein Benzylderivat der Formel II5. A process for the preparation of the compounds of the formula I according to claim 1, in which R 3 is not halogen, characterized in that a benzyl derivative of the formula II
Figure imgf000111_0001
Figure imgf000111_0001
in der L1 für eine nucleophil austauschbare Abgangsgruppe steht, in an sich bekannter Weise mit einem Hydroxyimin der Formel IIIin which L 1 represents a nucleophilically exchangeable leaving group, in a manner known per se, with a hydroxyimine of the formula III
R5ON=C (R4) -C(R3)=NOH IIIR 5 ON = C (R 4 ) -C (R 3 ) = NOH III
umsetzt.implements.
6. Verfahren zur Herstellung der Verbindungen der Formel I gemäß Anspruch 1, in denen R3 und R4 nicht Halogen bedeutet, dadurch gekennzeichnet, daß man ein Benzylderivat der Formel II gemäß Anspruch 5 in an sich bekannter Weise mit einem Dihydroxyi- min der Formel IV6. A process for the preparation of the compounds of formula I according to claim 1, in which R 3 and R 4 is not halogen, characterized in that a benzyl derivative of formula II according to claim 5 in a manner known per se with a dihydroxyimine of the formula IV
HON=C(R ) -C(R3)=NOH IVHON = C (R) -C (R 3 ) = NOH IV
zu einer Verbindung der Formel Vto a compound of formula V
Figure imgf000111_0002
umsetzt und V anschließend mit einer Verbindung der Formel VI
Figure imgf000111_0002
reacted and V then with a compound of formula VI
R5-L2 VI in der L2 für eine nucleophil austauschbare Abgangsgruppe steht, zu I umsetzt.R 5 -L 2 VI in which L 2 represents a nucleophilically exchangeable leaving group, converts to I.
7. Verfahren zur Herstellung der Verbindungen der Formel I gemäß Anspruch 1, in denen R3 nicht Halogen bedeutet, dadurch ge¬ kennzeichnet, daß man ein Benzylderivat der Formel II gemäß Anspruch 5 in an sich bekannter Weise mit einem Carbonylhy- droxyimin der Formel Vlla7. A process for the preparation of the compounds of the formula I according to claim 1, in which R 3 is not halogen, characterized in that a benzyl derivative of the formula II according to claim 5 is known in a manner known per se using a carbonylhydroxyimine of the formula VIIa
0=C(R4)-C(R3)=NOH VIIa0 = C (R 4 ) -C (R 3 ) = NOH VIIa
zu einer Verbindung der Formel VIIIto a compound of formula VIII
Figure imgf000112_0001
Figure imgf000112_0001
umsetzt, VIII anschließend entwederimplements VIII then either
a) zunächst mit Hydroxylamin oder dessen Salz und danach mit einer Verbindung der Formel VI (R5-L2) gemäß Anspruch 6 odera) first with hydroxylamine or its salt and then with a compound of formula VI (R 5 -L 2 ) according to claim 6 or
b) mit einem Hydroxylamin oder einem Hydroxylammoniumsalz der Formel IXa bzw. IXbb) with a hydroxylamine or a hydroxylammonium salt of the formula IXa or IXb
R5-0NH R5-ONH3® IXa IXbR 5 -0NH R 5 -ONH 3 ® IXa IXb
in der Q~ für das Anion einer Säure steht,in which Q ~ represents the anion of an acid,
zu I umsetzt.converts to I.
8. Mittel gegen tierischer Schädlinge oder Schadpilze, erhal- tend übliche Zusatzstoffe und eine wirksame Menge einer Ver¬ bindung der Formel I gemäß Anspruch 1.8. Agents against animal pests or harmful fungi, containing conventional additives and an effective amount of a compound of the formula I according to claim 1.
9. Verfahren zur Bekämpfung von tierischen Schädlingen oder Schadpilzen, dadurch gekennzeichnet, daß man die Schädlinge oder Schadpilze, deren Lebensraum oder die von ihnen freizu¬ haltenden Pflanzen, Flächen, Materialien oder Räume mit einer wirksamen Menge einer Verbindung der Formel I gemäß Anspruch' 1 behandelt.9. A method for controlling animal pests or harmful fungi, characterized in that the pests or harmful fungi, their habitat or the plants, surfaces, materials or spaces to be kept free by them with a effective amount of a compound of formula I according to claim '1 treated.
10. Verwendung der Verbindungen I gemäß Anspruch 1 zur Herstel- 5 lung von Mitteln gegen tierische Schädlinge oder Schadpilze.10. Use of the compounds I according to claim 1 for the production of agents 5 against animal pests or harmful fungi.
11. Verwendung der Verbindungen I gemäß Anspruch 1 zur Bekämpfung von tierischen Schädlingen oder Schadpilzen.11. Use of the compounds I according to claim 1 for combating animal pests or harmful fungi.
10 12. Verbindungen der Formel VIII gemäß Anspruch 7.10 12. Compounds of formula VIII according to claim 7.
13. Verwendung der Verbindungen der Formel VIII gemäß Anspruch 7 als Zwischenprokukte.13. Use of the compounds of formula VIII according to claim 7 as intermediate products.
1515
2020th
2525
3030
3535
4040
45 45
PCT/EP1995/000014 1994-02-04 1995-01-03 Phenylthio acetic acid derivatives, process and intermediate products for their production and agents containing them WO1995021156A1 (en)

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SK1022-96A SK102296A3 (en) 1994-02-04 1995-01-03 Phenylthio acetic acid derivatives, process and intermediate products for their production and agent containing them
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WO1997037968A1 (en) * 1996-04-11 1997-10-16 Shionogi & Co., Ltd. α-ALKOXYIMINOBENZYL DERIVATIVES AND AGRICULTURAL CHEMICALS CONTAINING THEM AS ACTIVE INGREDIENTS
US5929279A (en) * 1995-04-08 1999-07-27 Basf Aktiengesellschaft Preparation of Bisoximes
US5935908A (en) * 1995-08-15 1999-08-10 Novartis Crop Protection, Inc. Pesticidal indazole derivatives
US5985921A (en) * 1995-12-07 1999-11-16 Novartis Corporation 2-Phenyl-2-methoxyimino acetic acid esters
US6043197A (en) * 1995-11-02 2000-03-28 Basf Aktiengesellschaft Pyridylacetic acid derivatives, process and intermediate products for their preparation and their use
US6156923A (en) * 1995-12-07 2000-12-05 Novartis Corporation Process for the preparation of pesticides
US6255352B1 (en) 1997-05-28 2001-07-03 Basf Aktiengesellschaft Method for combating harmful fungi
US6265613B1 (en) 1995-10-10 2001-07-24 Basf Aktiengesellschaft Phenylacetic acid derivatives, process for their preparation and their use as pesticides and fungicides
US6313344B1 (en) 1998-05-27 2001-11-06 Bayer Aktiengesellschaft Organic compounds

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EP0432503A1 (en) * 1989-11-16 1991-06-19 BASF Aktiengesellschaft Thiocarboxylic acid esters and fungicides containing them
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US5929279A (en) * 1995-04-08 1999-07-27 Basf Aktiengesellschaft Preparation of Bisoximes
US5935908A (en) * 1995-08-15 1999-08-10 Novartis Crop Protection, Inc. Pesticidal indazole derivatives
US6265613B1 (en) 1995-10-10 2001-07-24 Basf Aktiengesellschaft Phenylacetic acid derivatives, process for their preparation and their use as pesticides and fungicides
US6043197A (en) * 1995-11-02 2000-03-28 Basf Aktiengesellschaft Pyridylacetic acid derivatives, process and intermediate products for their preparation and their use
US5985921A (en) * 1995-12-07 1999-11-16 Novartis Corporation 2-Phenyl-2-methoxyimino acetic acid esters
US6156923A (en) * 1995-12-07 2000-12-05 Novartis Corporation Process for the preparation of pesticides
US6420423B1 (en) 1995-12-07 2002-07-16 Bayer Aktiengesellschaft Pesticides
US6646151B1 (en) 1995-12-07 2003-11-11 Bayer Aktiengesellschaft Process for the preparation of pesticides
WO1997037968A1 (en) * 1996-04-11 1997-10-16 Shionogi & Co., Ltd. α-ALKOXYIMINOBENZYL DERIVATIVES AND AGRICULTURAL CHEMICALS CONTAINING THEM AS ACTIVE INGREDIENTS
US6255352B1 (en) 1997-05-28 2001-07-03 Basf Aktiengesellschaft Method for combating harmful fungi
US6313344B1 (en) 1998-05-27 2001-11-06 Bayer Aktiengesellschaft Organic compounds

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NZ278588A (en) 1997-04-24
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AU1454795A (en) 1995-08-21
HUT76523A (en) 1997-09-29
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