EP1212307A1 - Ether oximes insatures et leur utilisation dans la lutte contre la peste fongique et les parasites d'animaux - Google Patents

Ether oximes insatures et leur utilisation dans la lutte contre la peste fongique et les parasites d'animaux

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Publication number
EP1212307A1
EP1212307A1 EP00966014A EP00966014A EP1212307A1 EP 1212307 A1 EP1212307 A1 EP 1212307A1 EP 00966014 A EP00966014 A EP 00966014A EP 00966014 A EP00966014 A EP 00966014A EP 1212307 A1 EP1212307 A1 EP 1212307A1
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European Patent Office
Prior art keywords
alkyl
halogen
compounds
formula
phenyl
Prior art date
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EP00966014A
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German (de)
English (en)
Inventor
Markus Gewehr
Hubert Sauter
Bernd Müller
Andreas Gypser
Wassilios Grammenos
Jordi Tormo I Blasco
Arne Ptock
Oliver Cullmann
Thomas Grote
Eberhard Ammermann
Siegfried Strathmann
Gisela Lorenz
Volker Harries
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BASF SE
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BASF SE
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Publication of EP1212307A1 publication Critical patent/EP1212307A1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to unsaturated oxime ethers, intermediates for their preparation and their use for controlling harmful fungi and animal pests.
  • Fungicidal oxime ether compounds are already known.
  • WO 95/14009, WO 96/17851, WO 96/36229, WO 96/36615, WO 96/36616, WO 96/36633, WO 97/0612, WO 98/05652 and WO 98/23155 are strobilurins with triazolone -Pharmacophores of the
  • Rj 7 and Ris are H, -CC 3 -alkyl or phenyl.
  • the present invention is based on the object of providing compounds with improved activity and / or broadened activity spectrum. Surprisingly, it has now been found that this object is achieved with compounds which have a triazolone pharmacophore and an unsaturated oxime ether side chain.
  • the present invention therefore relates to unsaturated oxime ether 4Q compounds of the formula 1
  • W -OCH 2 -, -C (R ⁇ o) N-0-CH 2 - (the CH 2 end is in each case bound to the phenyl group which carries the triazolone radical);
  • R 3 H, -CC-alkyl
  • R 5 H, -CC 4 alkyl, C 2 -C alkenyl
  • R 6 H, -C -C alkyl, -C -C haloalkyl, C 2 -C alkenyl, aryl;
  • R 7 H halogen, -C-C 6 alkyl, -C-C 6 haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 cycloalkyl, C 3 -C 6- halocycloalkyl, optionally substituted aryl;
  • R 8 H halogen, -CC 6 alkyl, C ! -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, optionally substituted aryl, or
  • R 7 and Rs together with the carbon atoms to which they are attached, form an unsaturated heterocycle with 5 or 6 ring atoms, which has one or two heteroatoms which are selected independently of one another from a nitrogen, oxygen and sulfur atom and which may optionally be substituted by one or two radicals which are selected independently of one another and ter C ! -C 4 alkyl, halogen, nitro, CN, halo -CC 4 alkyl, OH, -C -alkoxy, optionally substituted aryl, C 2 -C alkenyl, halo-C 2 -C alkenyl, C 2 -C alkynyl, haloC 2 -C alkynyl;
  • R 9 is H, halogen, C ⁇ -C 6 -alkyl, C 6 haloalkyl, C 2 -C 6 -Alke- nyl, C 2 -C 6 haloalkenyl, C 3 -C 6 cycloalkyl, C 3 -C 6 -Halogenocycloalkyl, optionally substituted aryl;
  • Halogen fluorine, chlorine, bromine, iodine, preferably fluorine or chlorine;
  • C x -C 4 alkyl methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, preferably methyl;
  • C ! -C 6 alkyl C ⁇ -C alkyl as mentioned above, and n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-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, l-ethyl- 2-methylpropyl, preferably methyl, ethyl, n-prop
  • C 2 -C 6 alkenyl ethenyl, prop-1-en-l-yl, prop-2-en-l-yl, 1-methylethenyl, n-buten-1-yl, n-buten-2-yl, n-buten-3-yl, 1-methylprop-l-en-l-yl, 2-methylprop-l-en-l-yl, 1-methylprop-2-en-l-yl, 2-methylprop- 2-en-l-yl, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1-methylbut-1-en- l-yl, 2-methylbut-l-en-l-yl, 3-methylbut-l-en-l-yl, l-methylbut-2-en-l-yl, 2-methylbut-2-en-l- yl, 3-methylbut-2-en-l-yl, l-methylbut-2-en-l-
  • C 2 -C alkynyl ethynyl, prop-1-yn-l-yl, prop-2-yl-3-in, n-but-1-yn-l-yl, n-but-l-yn-4 -yl, n-but-2-yn-l-yl, preferably prop-2-yn-yl-yl;
  • -C-C 2 haloalkyl z. B. 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-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, preferably difluoromethyl or trifluoromethyl;
  • Ci L -Cö-haloalkyl -C-C 6 alkyl as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, that is, for.
  • CC 6 haloalkenyl C 2 -C 6 alkenyl as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, that is, for.
  • C 2 -C haloalkynyl C 2 -C alkynyl as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, e.g. B. chloroethynyl, 3-chloropropynyl;
  • cycloalkyl cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, preferably cyclopropyl, cyclopentyl or cyclohexyl;
  • Halogen-C 3 -C 6 cycloalkyl C 3 -C 6 as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, that is, for. B. 2-, 3- or 4-chlorocyclopentyl, 2-, 3- or 4-chlorocyclohexyl, 2, 3,4-trichlorocyclopentyl or 2,3,4,5, 6-pentachlorocyclohexyl;
  • Aryl is preferably phenyl and naphthyl, especially phenyl.
  • the unsaturated heterocycle with 5 or 6 ring atoms can be aromatic or non-aromatic.
  • An aromatic heterocycle is in particular 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, l, 2,4-0xadiazol-3-yl, l, 2,4-0xadiazol-5-yl, l, 2,4-thiadiazol-3-yl,
  • the aryl radical is substituted, it preferably has one or two substituents which are selected independently of one another from halogen, in particular fluorine or chlorine, C 1 -C alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 alkoxy, nitro , OH and CN. Halogen and / or -CC 4 alkyl is preferred.
  • R 2 is H, -CC alkyl, halogen, halogen-C ⁇ -alkyl, especially H or -CC alkyl;
  • R 5 is H or Cx-d-alkyl
  • R 6 H, -CC-alkyl or halogen -CC-C-alkyl, especially H or C ⁇ -C alkyl;
  • R 7 is H, halogen, C ⁇ -C6 alkyl, halo-C ⁇ -C 6 alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 halocycloalkyl or phenyl, especially H, halogen, C ⁇ -C 6 alkyl and particularly preferably H or halogen;
  • R 8 is H, halogen, C ⁇ -C6 alkyl, halo-C ⁇ -C 6 alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 halocycloalkyl, C 2 -C 6 alkenyl or phenyl, in particular H, halogen, -CC 6 alkyl; or
  • R 7 and R ⁇ together with the carbon atoms to which they are attached represent thienyl, furyl, oxazolyl or thiazolyl f, where these groups are optionally substituted by C ⁇ -C-alkyl, halogen or phenyl, which is optionally substituted by one or two halogen can be substituted and in particular for thienyl or oxazolyl, these groups optionally being substituted by one or two halogen or phenyl and the phenyl substituent in turn being substituted by one or two halogen;
  • Rg is H, halogen, C ⁇ -C6 alkyl, halo-C ⁇ -C 6 alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 halocycloalkyl or phenyl, especially H, halogen, C ⁇ -C 6 Alkyl and particularly preferably H or halogen;
  • the oxime side chain can be attached to the phenyl ring in the o, m or p position to W.
  • the p position is preferred.
  • the radical R is preferably in the 6 position. If the oxime side chain is bonded to W in the p-position, the radical R 2 is preferably in the 2- and / or 5-position.
  • Preferred embodiments are the compounds of formula 1, in which the substituents have the following meanings:
  • R 5 H or -CC 4 alkyl
  • R 6 H -CC 4 alkyl, halo -CC 4 alkyl
  • R 7 H halogen, -CC 6 alkyl, halogen -CC 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, phenyl;
  • R 8 is H, halogen, C ⁇ -C6 alkyl, halo-C ⁇ -C 6 alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 halocycloalkyl, C 2 -C 6 alkenyl, phenyl; or
  • R and R 8 together with the carbon atoms to which they are attached form an unsaturated heterocycle with 5 or 6 ring atoms, which has one or two heteroatoms which are selected independently of one another from a nitrogen, oxygen and sulfur atom and that can optionally be substituted with one or two radicals which are selected independently of one another from C -C -alkyl, halogen, halogen -CC-C -alkyl, C ⁇ -C -alkoxy and phenyl, which is optionally substituted by one or two halogen or C ⁇ - C alkyl is substituted;
  • Rg H, halogen, -CC 6 alkyl, halogen-C ! -C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, phenyl;
  • R 5 H, -CC alkyl
  • R 7 H halogen, -CC 6 alkyl
  • R 8 H, halogen, -CC 6 alkyl
  • R 7 and Rg together with the carbon atoms to which they are attached form thienyl, furanyl, oxazolyl, thiazolyl, where these groups may have one or two substituents which are selected independently of one another from C 1 -C 4 -alkyl, halogen and Phenyl which is optionally substituted by one or two halogen;
  • R 9 H halogen, -CC 6 alkyl
  • R 3 -CC 4 alkyl R 5 H, -CC alkyl;
  • R 8 H, -CC alkyl, halogen
  • R and Rg together with the carbon atoms to which they are attached form thiophenyl or oxazolyl, these groups optionally being substituted by one or two halogen or phenyl and the phenyl optionally being substituted by one or two halogen;
  • R 2 chlorine, methyl
  • R 7 H methyl, chlorine
  • R 8 H methyl, ethyl, chlorine, phenyl, ethenyl, prop-1-en-1-yl
  • Rg H, methyl, chlorine
  • Rg H methyl, chlorine.
  • the oxime side chain is preferably bound in the p-position.
  • R means:
  • radicals X, R 2 and R 5 have the meanings given above or preferably the following meanings:
  • R 2 2-methyl, 2-chloro, 2,5-dimethyl
  • R means:
  • radicals X and R 5 have the meanings given above or preferably the following meanings:
  • the compounds of the invention can be prepared by several methods. The preparation is preferably carried out according to one of the synthesis routes A or B, which are explained in the formula scheme below.
  • the starting point for the synthesis is a compound of the formula 2 in which Xi in the case of route A is CH 3 or SGOCH 2 -, where SG is a protective group for benzyl ether. After the triazolone ring has been built up, the protective group is split off and the benzyl alcohol obtained is converted into X 2 CH 2 - using methods known from the literature, where X 2 is a nucleophilically cleavable group (cf. TW Greene: "Protective Groups in Organic Synthesis", 2. Edition 1991, John Wiley, New York).
  • Xi X 2 CH 2 -
  • X 2 denotes a nucleophilically cleavable group, such as chlorine, fluorine, bromine, nitro, alkyl or aryl sulfonate, such as mesylate, tosylate or triflate.
  • a nucleophilically cleavable group such as chlorine, fluorine, bromine, nitro, alkyl or aryl sulfonate, such as mesylate, tosylate or triflate.
  • the amino function of the compounds 2 is first converted into a thiazolone group, the compounds 3 being obtained.
  • the reaction sequence leading to this conversion is described in detail in WO 95/14009 (compounds No. 21 ⁇ 19 ⁇ 17 ⁇ 1) and in WO 96/26191 and DE 198 09 995.
  • the group Xi is then converted into a reactive group which can react with the radical V in the compound 7 or the radical x in the compound of the formula 8 by linking the two phenyl rings and forming the group W.
  • a leaving group is introduced into group Xi, which is split off with the hydrogen atom of the phenolic or oximic OH group in the presence of a base.
  • Examples of such leaving groups are chloride, bromide, p-toluenesulfonate, methanesulfonate or trifluoromethanesulfonate.
  • the reaction of compound 3 with compound 7 or 8 takes place, for example, in an inert solvent or diluent, such as acetone, acetonitrile, dimethyl sulfoxide, dimethylformamide, N-methylpyrrolidone etc., using a base (for example sodium carbonate, potassium carbonate) , Sodium hydroxide, potassium hydroxide, sodium hydride, potassium hydride etc.).
  • a base for example sodium carbonate, potassium carbonate
  • the bases are generally used in equimolar amounts or in excess. It may also be advantageous to add a catalytic amount of a crown ether (e.g. 18-crown-6 or 15-crown-5).
  • the reaction temperature is generally in the range from 0 to 80 ° C., preferably 20 to 60 ° C.
  • Compound 4 obtained by reacting 3 with 7 is then oximated with an O-alkenylhydroxylamine or a salt thereof.
  • the preparation of the O-alkenylhydroxylamine is known to the person skilled in the art and is described, for example, in Chem. Pharm. Bull. 1983, 91, 2601 and J. Am. Chem. Soc. 1949, 71, 3423.
  • a compound 2 is reacted with a compound 7 under the etherification conditions mentioned above to give a compound 5.
  • This is, in the same way as in route A, oximized with O-alkenylhydroxylamine or a salt thereof, giving compound 6, into which, as already described, the thiazolone ring is subsequently introduced.
  • the invention encompasses both the individual isomer compounds and their mixtures and all enantiomers, racemates and diastereomers.
  • the new compounds 1 are notable for excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes and Basidio mycetes, and can be used as leaf and soil fungicides. Some of them have remarkably high systemic mobility and effectiveness after soil application and especially after leaf application.
  • Erysiphe graminis (powdery mildew) in cereals, Erysiphe cichoracearum and Shaerotheca fuliginea on pumpkin plants, Podosphaera leucotricha on apples, Uncinula necator on vines,
  • Botrytis cinerea (gray mold) on strawberries, vines,
  • the compounds 1 are applied 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 application forms depend on the purposes; in any case, they should ensure a fine and uniform distribution of the connections 1.
  • the formulations are prepared in a known manner, e.g. B. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, and in the case of water as a diluent other organic solvents can also be used as auxiliary solvents.
  • auxiliaries solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g.
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient. Depending on the type of effect desired, the application rates are between 0.01 and 3 kg of active ingredient per ha.
  • active ingredient 0.001 to 50 g, preferably 0.01 to 10 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, for. B. with herbicides, insecticides, growth regulators, fungicides or with fertilizers.
  • the compounds of the formula Ia 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 as well as in the hygiene, storage 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 reticulana data, Cheimatobone bria , Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea gran-diosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterraneaella, Graphitaolitaolitaolitaolitaolitaolitaolitaolitaolitaolitaolitaolitaolitaolitaolita
  • 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 anthulucuceaphacaceacita phacaceacia phacaceacia phacaceacia phacaceacia phacaceacia phacaceacia phacaceacia phacaceacia phacaceacia phacaceacia phacaceacia phacaceacia phacaceacia phacaceacia phacaceacia phaceaceaceaceapeaceacophaceaceaceaceaceacophaceaceaceacophaceapeaceaceacophaceacophaceacophaceae Dasineura brassicae, Fannia
  • 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 For example Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Eus- chistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyanta perditor.
  • suckers for example, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Bemisia tabaci, Brachy- caudus cardui, Brevicoryne brassicae, Dreosiafiaiaiaiaia, Dreosusphiaiaiausiaia, Cerosiphayiaypia radicola, Dysau- lacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae,
  • Macrosiphum euphorbiae Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nephotettix cincticeps, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psyllaopalsi waiver, Psyllaumidi asi mali, Schizaphis graminum, Schizoneura lanuginosa, Trialeurodes vaporariorum, Viteus vitifolii.
  • 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 microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, shedelodi, iodine eroniophus, Iotetroniiuncus, Iotetranyius, Iotetronii Ixodes rubicundus, Metatetranychus (Phanonychus) ulmi, Ornithodorus moubata, Otobins megnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllocoptruta oleivora, Polyphagotarsonemusususus Tar, Tice, Rhipicephultsiabi
  • root gall nematodes e.g. B. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, for example Globodera rosto- chiensis, Heterodera avenae, Heterodera glycinae, Heterodera schachtii, Heterodera trifolii, stick and leaf whale, e.g. B.
  • Belonolaimus longicaudatus Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchusus Prubus neglechatatylusus, Prenate, prenovate, Prid.
  • the application forms depend entirely on the purposes; 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.
  • 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 application rate of active ingredient for controlling pests is 0.1 to 2.0, preferably 0.2 to 1.0 kg / ha under field conditions.
  • emulsions, pastes or oil dispersions come mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, distant coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. B.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
  • the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • wetting agents adhesives, dispersants or emulsifiers
  • concentrates composed of an active substance, wetting agents, adhesives, dispersants or emulsifiers and possibly solvents or oil, which are suitable for dilution with water.
  • Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ethers tiertem, condensation products of sulfonated 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,
  • 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).
  • Granules e.g. B. coating, impregnation and homogeneous granules; they can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are e.g. B. 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. B. 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 agents according to the invention can also be present in these use forms together with other active ingredients, such as, for. B. herbicides, insecticides, growth regulators and fungicides, or mixed with fertilizers and applied. When mixed with fungicides, the fungicidal activity spectrum is enlarged in many cases.
  • the crude product is taken up in 100 ml MTBE, mixed with 150 ml hexane and cooled to 0 ° C.
  • the precipitate is separated off and dried in vacuo at 40 ° C. for 1 h. 37.6 g (78%) of the product are obtained as a light beige powder.
  • aqueous active ingredient preparation which was prepared from a stock solution consisting of 10% active ingredient, 63% cyclohexanone and 27% emulsifier, and 24 hours after the spray coating had dried on dusted with spores of powdery mildew (Erysiphe graminis forma specialis tritici).
  • the test plants were then placed in a greenhouse at temperatures between 20 and 24 ° C and 60 to 90% relative humidity. After 7 days, the extent of mildew development was determined visually in% infestation of the entire leaf area.
  • Leaves of pot vines of the "Müller-Thurgau" variety were sprayed to runoff point with aqueous preparation of active compound, which was prepared with a stock solution of 10% active compound, 63% cyclohexanone and 27% emulsifier.
  • the following day the leaves were inoculated with an aqueous suspension of zoospores from Plasmopara viticola.
  • the vines were then placed for 48 hours in a steam-saturated chamber at 24 ° C and then for 5 days in a greenhouse at temperatures between 20 and 30 ° C. After this time, the plants were again placed in a humid chamber for 16 hours to accelerate the sporangium carrier outbreak. The extent of the development of the infestation on the undersides of the leaves was then determined visually.
  • Leaves of "Tai-Nong 67" rice seedlings grown in pots were sprayed to runoff point with aqueous active compound preparation which was prepared with a stock solution of 10% active compound, 63% cyclohexanone and 27% emulsifier. The following day, the plants were inoculated with an aqueous spore suspension of Pyricularia oryzae. The test plants were then placed in climatic chambers at 22 to 24 ° C and 95 to 99% relative humidity for 6 days. The extent of the development of the infestation on the leaves was then determined visually.

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

Abstract

La présente invention concerne des composés éther oximes insaturés de formule (1), dans laquelle les substituants sont tels que définis dans la description. Ces composés sont utilisés dans la lutte contre la peste fongique et les parasites d'animaux.
EP00966014A 1999-09-15 2000-09-14 Ether oximes insatures et leur utilisation dans la lutte contre la peste fongique et les parasites d'animaux Withdrawn EP1212307A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19944258 1999-09-15
DE19944258 1999-09-15
PCT/EP2000/009000 WO2001019803A1 (fr) 1999-09-15 2000-09-14 Ether oximes insatures et leur utilisation dans la lutte contre la peste fongique et les parasites d'animaux

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EP1212307A1 true EP1212307A1 (fr) 2002-06-12

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JP6269504B2 (ja) * 2012-11-29 2018-01-31 住友化学株式会社 テトラゾリノン化合物及びその用途
WO2014104268A1 (fr) * 2012-12-27 2014-07-03 住友化学株式会社 Composé de tétrazolinone et ses applications
WO2014104384A1 (fr) * 2012-12-27 2014-07-03 住友化学株式会社 Composé de tétrazolinone et ses applications
WO2014104382A1 (fr) * 2012-12-27 2014-07-03 住友化学株式会社 Composé tétrazolinone et ses applications

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ATE172597T1 (de) * 1992-07-15 1998-11-15 Basf Ag Substituierte oximether und ihre verwendung zur bekämpfung von schädlingen
ATE186909T1 (de) * 1993-11-19 1999-12-15 Du Pont Cyclische fungizide amide
JP2771334B2 (ja) * 1995-05-16 1998-07-02 イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー 殺菌・殺カビ性環状アミド類
CZ394097A3 (cs) * 1995-06-20 1998-09-16 E. I. Du Pont De Nemours And Company Artropodicidní a fungicidní amidy
JP2000516583A (ja) * 1996-08-01 2000-12-12 イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー 殺節足動物性および殺菌・殺カビ性の環状アミド類

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Title
See references of WO0119803A1 *

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JP2003509415A (ja) 2003-03-11

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