EP0879232A1 - Derives 3-aryl-5-halogeno-pyrone utilises comme pesticides - Google Patents

Derives 3-aryl-5-halogeno-pyrone utilises comme pesticides

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Publication number
EP0879232A1
EP0879232A1 EP96934687A EP96934687A EP0879232A1 EP 0879232 A1 EP0879232 A1 EP 0879232A1 EP 96934687 A EP96934687 A EP 96934687A EP 96934687 A EP96934687 A EP 96934687A EP 0879232 A1 EP0879232 A1 EP 0879232A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkoxy
chlorine
fluorine
optionally substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP96934687A
Other languages
German (de)
English (en)
Inventor
Reiner Fischer
Folker Lieb
Michael Ruther
Jörg Stetter
Markus Dollinger
Christoph Erdelen
Norbert Mencke
Hans-Joachim Santel
Andreas Turberg
Ulrike Wachendorff-Neumann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
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Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0879232A1 publication Critical patent/EP0879232A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/6552—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom

Definitions

  • the invention relates to new 3-aryl-5-halogen-pyrone derivatives, several processes and intermediates for their preparation and their use as pesticides and herbicides.
  • Phenyl-pyrone derivatives substituted in the phenyl ring with herbicidal, acaricidal and insecticidal properties are described in EP-A-588 137.
  • X represents halogen, nitro, cyano, alkyl, alkenyl, alkoxy, alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkyl, haloalkenyl, haloalkoxy, haloalkenyloxy or in each case optionally substituted phenyl, phenoxy, phenylthio, benzyloxy or benzylthio
  • Y represents hydrogen, halogen, nitro, cyano, alkyl, alkenyl, alkoxy, alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkyl, haloalkenyl, haloalkoxy or haloalkenyloxy,
  • Z represents halogen, nitro, cyano, alkyl, alkenyl, alkoxy, alkenyloxy, haloalkyl, haloalkenyl, haloalkoxy or haloalkenyloxy,
  • n one of the numbers 0, 1, 2 or 3
  • A represents halogen
  • D represents hydrogen or an optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated cycloalkyl, saturated or unsaturated heterocyclyl, arylalkyl, aryl, hetarylalkyl or hetaryl and
  • G is hydrogen (a) or for one of the groups
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulfur
  • M oxygen or sulfur
  • R 1 for each optionally substituted by halogen, alkyl, alkenyl, alkoxyalkyl, alkyl thioalkyl or polyalkoxyalkyl or for each cycloalkyl or heterocyclyl optionally substituted by halogen, alkyl or alkoxy or for each optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,
  • R 2 represents alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl optionally substituted by halogen, or cycloalkyl, phenyl or benzyl optionally substituted,
  • R 3 , R 4 and R 5 independently of one another each represent optionally substituted by halogen alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio or each optionally substituted phenyl, benzyl, phenoxy or phenylthio,
  • R and R independently of one another represent hydrogen, in each case optionally substituted by halogen, alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, in each case optionally substituted phenyl or benzyl, or together with the N atom to which they are attached , form an optionally oxygen or sulfur-containing cycle.
  • the compounds of the formula (I) can be present in different compositions as geometric and / or optical isomers or isomer mixtures, which can optionally be separated in a customary manner. Both the pure isomers and the isomer mixtures, their preparation and use, and agents containing them are the subject of the present invention. For the sake of simplicity, however, the following always refers to compounds of the formula (I), although both the pure compounds and, if appropriate, mixtures with different proportions of isomeric compounds are meant.
  • the compounds of the formula (I) can exist in the two isomeric forms of the formulas (I) a and (I) b , which is to be expressed by the dashed line in formula (I).
  • the compounds of the formulas (I) a and (I) b can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulas (I) a and (I) b can, if appropriate, be separated in a manner known per se by physical methods, for example by chromatographic methods.
  • A, D, E, L, M, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and n have the meanings given above.
  • A, D, X, Y, Z and n have the meanings given above,
  • X, Y, Z and n have the meanings given above and
  • R 1 has the meaning given above and
  • R 1 has the meaning given above
  • Me for a mono- or divalent metal preferably an alkali or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium
  • an alkali or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium
  • R 9 , R 10 , R 11 , R 12 independently of one another represent hydrogen or alkyl (preferably C ] -C 8 -alkyl),
  • X, Y, Z and n have the meanings given above, in each case
  • R 6 and L have the meanings given above,
  • the new compounds of the formula (I) have very good activity as pesticides, preferably as insecticides and acaricides, with good plant tolerance. Herbicidal effects were found preferably at higher application rates.
  • X preferably represents fluorine, chlorine, bromine, iodine, nitro, cyano, C j -C 8 alkyl, C 2 -C 6 alkenyl, C r C 6 alkoxy, C 2 -C 6 alkenyloxy, C r C 6 - alkylthio, C r C 6 -
  • Y preferably represents hydrogen, fluorine, chlorine, bromine, iodine, nitro, cyano, C, -
  • Z preferably represents fluorine, chlorine, bromine, iodine, nitro, cyano, C j -C 8 alkyl,
  • n preferably represents one of the numbers 0, 1, 2 or 3.
  • A preferably represents fluorine, chlorine, bromine or iodine.
  • D preferably represents hydrogen, in each case optionally substituted by halogen C, -C 12 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C, -C ] 0 alkoxy-
  • C 2 -C 8 alkyl poly-C r C 8 alkoxy-C 2 -C 8 alkyl or C r C 10 alkylthio-C 2 -C 8 alkyl, for by cyano, C j -C 8 - alkyloxycarbonyl or C, -C 8 -Alkylcarbo- nyloxy substituted C, -C 12 alkyl, optionally substituted by halogen, C, - C 4 alkyl, C j -C 4 alkoxy or C r C 4 -haloalkyl-substituted C 3 -C 8 -Cyc- loalkyl, in which optionally one or two not directly adjacent
  • Methyl groups are replaced by oxygen and / or sulfur or represents in each case optionally substituted by halogen, C ⁇ -C6 alkyl, C j -C 6 haloalkyl, C r C 6 - alkoxy, C, -C 6 haloalkoxy, cyano or nitro Phenyl, hetaryl with 5 to 6 ring atoms and one or two heteroatoms from the series oxygen, sulfur and nitrogen, phenyl-C r C 6 -alkyl or
  • Hetaryl-C j -C 8 alkyl with 5 to 6 ring atoms and one or two hetero atoms from the series oxygen, sulfur and nitrogen.
  • G preferably represents hydrogen (a) or one of the groups
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulfur
  • M stands for oxygen or sulfur.
  • R 1 preferably represents in each case optionally substi ⁇ tutechnischs by halogen C r C 20 alkyl, C 2 -C 20 - alkenyl, C r C 8 -alkoxy-C r C 8 alkyl, C r C 8 alkylthio-C, -C 8 alkyl or poly-CpC 8 alkoxy-C j -C 8 alkyl or for C 3 -C 8 cycloalkyl optionally substituted by halogen, -C-C 6 alkyl or C r C 6 - alkoxy, in which optionally one or two not directly adjacent methylene groups are replaced by oxygen and / or sulfur,
  • R 2 preferably represents in each case optionally substituted by halogen C, -C 20 alkyl, C 2 -C 20 alkenyl, C r C 8 alkoxy-C 2 -C 8 alkyl or poly-C ] -C 8 -alkoxy-C 2 -C 8 -alkyl,
  • C 3 -C 8 cycloalkyl optionally substituted by halogen, C, -C 6 alkyl or C, -C 6 alkoxy or
  • phenyl or benzyl optionally substituted by halogen, cyano, nitro, C ] -C 6 -alkyl, C r C 6 -alkoxy, C r C 6 -haloalkyl or C r C 6 -haloalkoxy.
  • R 3 preferably represents C which is optionally substituted by halogen
  • R 4 and R 5 independently of one another preferably represent respectively optionally halogen-substituted C, -C 8 alkyl, C j -C 8 alkoxy, C, - C 8 - alkyl amino, C j -C 8 alkylthio or C 2 - C 8 -alkenylthio or represent in each case optionally halogen-,
  • R 6 and R 7 independently of one another preferably represent hydrogen, in each case optionally substituted by halogen C ] -C 8 -alkyl,
  • X particularly preferably represents fluorine, chlorine, bromine, nitro, cyano, C j -C 6 alkyl, C 2 -C 4 alkenyl, C r C 4 alkoxy, C 2 -C 4 alkenyloxy, C r C 4 -Alkylthio, C ] -C 4 - alkylsulfinyl, C ] -C 4 -alkylsulfonyl, for C r C 4 -alkyl, C 2 -C 4 -alkenyl, C, -C 4 -alkoxy or C each substituted by fluorine or chlorine 2 - C 4 -alkenyloxy or optionally by fluorine, chlorine, bromine, nitro,
  • Y particularly preferably represents hydrogen, fluorine, chlorine, bromine, nitro, cyano, C, -C 6 -alkyl, C 2 -C 4 -alkenyl, C r C 4 -alkoxy, C 2 -C 4 -alkenyloxy, C, -
  • Z particularly preferably represents fluorine, chlorine, bromine, nitro, cyano, C j -C 6 -
  • n particularly preferably represents one of the numbers 0, 1 or 2.
  • D particularly preferably represents hydrogen, represents in each case optionally substituted by fluorine or chlorine, C j ⁇ -C alkyl, C 3 -C 6 - alkenyl, C 3 -C 6 - alkynyl, C r C 8 -alkoxy-C 2 -C 6- alkyl, poly-C r C 6 alkoxy-C 2 -C 6 alkyl or
  • C ] -C 8 alkylthio-C 2 -C 6 alkyl for C, -C 8 alkyl substituted by cyano, C, -C 6 alkoxy carbonyl or C j -C 6 alkylcarbonyloxy, optionally substituted by fluorine, Chlorine, C j -C 4 alkyl, C, -C 4 alkoxy or C r C 2 haloalkyl substituted C 3 -C 7 cycloalkyl, in which one or two not directly adjacent methylene groups by oxygen and / or
  • Sulfur are replaced or for phenyl optionally substituted by fluorine, chlorine, bromine, C r C 4 alkyl, C r C 4 haloalkyl, C r C 4 alkoxy, C r C 4 haloalkoxy, cyano or nitro, Furanyl, imidazolyl, pyridyl, thiazolyl, pyrazolyl, pyrimidyl, pyridazyl, pyrazinyl, pyrrolyl, thienyl, triazolyl or phenyl-C r C 4 alkyl.
  • G particularly preferably represents hydrogen (a) or one of the groups 5 (e) ,
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulfur
  • M stands for oxygen or sulfur.
  • R 1 particularly preferably represents in each case optionally substituted by fluorine or chlorine, C r C] 6 alkyl, C 2 -C 16 - alkenyl, C, -C 6 -alk- oxy-C j -CG alkyl, C r C 6 -Alkylthio-C r C 6 -alkyl or poly-C r C 6 -alk-oxy-C j -C 6 -alkyl or for optionally substituted by fluorine, chlorine, C ⁇ Cs- alkyl or C ] -C 5 -alkoxy C 3 -C 7 cycloalkyl, in which one or two non-directly adjacent methylene groups are optionally replaced by oxygen and / or sulfur,
  • pyrazolyl for pyrazolyl, thiazolyl, pyridyl, pyrimidyl which are optionally substituted by fluorine, chlorine, bromine or C 1 -C 4 -alkyl,
  • R 2 particularly preferably represents in each case optionally substituted by fluorine or chlorine C ] -C ] 6 alkyl, C 2 -C 16 alkenyl. C, -C 6 -
  • C 3 -C 7 cycloalkyl optionally substituted by fluorine, chlorine, C, -C 4 alkyl or C r C 4 alkoxy or
  • R 3 particularly preferably represents optionally substituted by fluorine or chlorine, C r C 6 -alkyl or represents in each case optionally
  • R 4 and R 5 independently of one another particularly preferably each represent C, -C 6 -alkyl optionally substituted by fluorine or chlorine,
  • R 6 and R 7 independently of one another particularly preferably represent hydrogen, in each case optionally substituted by fluorine or chlorine, C, -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C, -C 6 -alkoxy, C 3 -C 6 -alkenyl or C r C 6 -alkoxy-C 2 -C 6 -alkyl, for each optionally by fluorine, chlorine, bromine, C r C 5 -haloalkyl, C, -C 5 -alkyl or C , -C 5 alkoxy substituted phenyl or benzyl, or together for a C 3 -C 6 alkylene radical in which a methylene group is optionally replaced by oxygen or sulfur
  • X very particularly preferably represents fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, n- or i-propyl, n-, s-, i- or t-butyl, vinyl, allyl, methallyl, methoxy, ethoxy, n- or i-propoxy, allyloxy, methallyloxy,
  • Y very particularly preferably represents hydrogen, fluorine, chlorine, bromine, nitro, cyano, methyl, ethyl, n- or i-propyl, n-, s-, I- or t-butyl, methoxy, ethoxy, n- or i Propoxy, allyloxy, methallyloxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, trifluoroethoxy, methylthio, methylsulfinyl or methylsulfonyl
  • Z very particularly preferably represents fluorine, chlorine, bromine, nitro, cyano,
  • n very particularly preferably represents one of the numbers 0 or 1
  • a very particularly preferably represents fluorine, chlorine or bromine
  • D very particularly preferably represents hydrogen, represents in each case optionally fluorine or chlorine-substituted C j -C 8 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 -
  • G very particularly preferably represents hydrogen (a) or one of the groups
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulfur
  • M stands for oxygen or sulfur.
  • R 1 very particularly preferably represents in each case optionally
  • benzyl optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy,
  • furanyl, thienyl or pyridyl each optionally substituted by fluorine, chlorine, bromine, methyl or ethyl, for optionally substituted by fluorine, chlorine, methyl or ethyl phenoxy-C ] -C 4 -alkyl or
  • R very particularly preferably represents C, -C 14 -alkyl, C 2 -C ] 4- alkenyl, C, - C 4 -alkoxy-C 2 -C 6 -alkyl or poly-C r, each optionally substituted by fluorine or chlorine C 4 alkoxy-C 2 -C 6 alkyl,
  • C 3 -C 6 cycloalkyl optionally substituted by fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl or methoxy,
  • phenyl or benzyl optionally substituted by fluorine, chlorine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy.
  • R 3 very particularly preferably represents methyl, ethyl, propyl, isopropyl optionally substituted by fluorine or chlorine or in each case optionally by fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy , tert-butoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro substituted phenyl or benzyl.
  • R 4 and R 5 independently of one another very particularly preferably represents in each case optionally substituted by fluorine or chlorine, C j -C, - alkyl, C r C 4 alkoxy, C r C 4 alkylamino, di- (C r C 4 -alkyl) amino or C j -C 4 alkylthio or for phenyl, phenoxy or phenylthio which are each optionally substituted by fluorine, chlorine, bromine, nitro, cyano, methyl, methoxy, trifluoromethyl or trifluoromethoxy.
  • R 6 and R 7 independently of one another very particularly preferably represent
  • Hydrogen for in each case optionally substituted by fluorine or chlorine, C 4 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C r C 4 -alkoxy, C 3 -C 4 -
  • Alkenyl or C j -C 4 alkoxy-C 2 -C 4 alkyl each optionally with fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl substituted phenyl or benzyl, or together for a C 5 -C 6 alkylene radical in which a methylene group is optionally replaced by oxygen or sulfur.
  • Saturated or unsaturated hydrocarbon residues such as alkyl or alkenyl can also be used in connection with heteroatoms, e.g. in alkoxy, where possible, be straight-chain or branched.
  • Optionally substituted radicals can be mono- or polysubstituted, whereby in the case of multiple substitutions the substituents can be the same or different.
  • Variant ( ⁇ ) can be represented by the following reaction scheme:
  • halocarbonylketenes of the formula (III) required as starting materials in process (A) are partly new and are the subject of a prior, not yet published application by the applicant (German patent application 195 04 621.8). They can be prepared in a simple manner by methods known in principle (cf. for example Org. Prep. Proced. Int., 7, (4), 155-158, 1975, DE-1 945 703 and EP-508 126).
  • X, Y, Z and n have the meanings given above and
  • acid halides such as thionyl chloride, phosphorus (V) chloride, phosphorus (III) chloride, oxalyl chloride, phosgene or thionyl bromide, if appropriate in the presence of catalysts, such as, for example, diethylformamide, methyl sterylformamide or triphenylphosphine and, if appropriate, in the presence of bases such as e.g. Pyridine or triethylamine, at a temperature between -20 ° C and 200 ° C, preferably between 0 ° C and 150 ° C.
  • acid halides such as thionyl chloride, phosphorus (V) chloride, phosphorus (III) chloride, oxalyl chloride, phosgene or thionyl bromide
  • catalysts such as, for example, diethylformamide, methyl sterylformamide or triphenylphosphine
  • bases such as e.g.
  • a and D have the meanings given above, are commercially available compounds which are known or which can be obtained by known processes.
  • the acid halides of the formula (TV), carboxylic anhydrides of the formula (V) required as starting materials for carrying out processes (B), (C), (D), (E), (F), (G) and (H) as starting materials, Chloroformic acid esters or chloroformic acid thioesters of the formula (VI), chloronothio formic acid esters or chlorodithio formic acid esters of the formula (VII), alkyl halides of the formula (VIII), sulfonic acid chlorides of the formula (IX), phosphorus compounds of the formula (X) and metal hydroxides, metal alkoxides or amines of the formula (XI) and (XII), isocyanates of the formula (XTII) and carbamic acid chlorides of the formula (XIV) are generally known compounds of organic or inorganic chemistry.
  • Process (A) according to the invention is characterized in that carbonyl compounds of the formula (II) are reacted with ketene acid halides of the formula (III), if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.
  • Diluents which can be used in process (A) according to the invention are all organic solvents which are inert to the reactants.
  • Hydrocarbons such as o-dichlorobenzene, tetralin, toluene and xylene, preferably ethers such as dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents such as dimethyl sulfoxide, are preferably usable.
  • All customary acid acceptors can be used as acid acceptors when carrying out process (A) according to the invention.
  • Tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecane (DBU), diazabicyclonones (DBN),
  • reaction temperature can be varied within a substantial range when carrying out process (A) according to the invention. Expediently one works at temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 220 ° C.
  • Process (A) according to the invention is preferably carried out under normal pressure.
  • reaction components of the formulas (II) and (III) and, if appropriate, the acid acceptor are generally employed in approximately equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 5 mol).
  • Process (B ⁇ ) is characterized in that compounds of the formula (I-a) are reacted with carboxylic acid halides of the formula (TV), if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid binder.
  • Diluents which can be used in process (B ⁇ ) according to the invention are all solvents which are inert to the acid halides.
  • Hydrocarbons such as gasoline, benzene, toluene, xylene and tetralin, and furthermore halogenated hydrocarbons, such as methylene chloride, chloroform, can preferably be used.
  • Suitable acid binders for the reaction according to process (B ⁇ ) according to the invention are all customary acid acceptors.
  • Tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclonones (DBN), Hunig base and N, N-dimethylaniline, and also alkaline earth metal oxides, such as magnesium oxide and calcium oxide, are preferably usable , also alkali and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate, and alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
  • the reaction temperature can be varied within a substantial range in the process (B ⁇ ) according to the invention. Generally you work at temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C.
  • the starting material of the formula (I-a) and the carboxylic acid halide of the formula (TV) are generally in each case used in approximately equivalent amounts. However, it is also possible to use the carboxylic acid halide in a larger excess (up to 5 mol).
  • the processing takes place according to usual methods
  • Process (Bß) is characterized in that compounds of the formula (I-a) are reacted with carboxylic anhydrides of the formula (V), if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid binder.
  • the diluents which can be used in the process (Bß) according to the invention are preferably those diluents which are also preferred when using acid halides. Otherwise, an excess of carboxylic acid anhydride can also act as a diluent.
  • Suitable acid binders which may be added in the process (Bß) are preferably those acid binders which are also preferred when using acid halides
  • reaction temperature in the process (Bß) according to the invention can be varied within a substantial range. In general, temperatures between -20 ° C. and + 150 ° C., preferably between 0 ° C. and 100 ° C.
  • the starting material of the formula (Ia) and the carboxylic acid anhydride of the formula (V) are generally used in approximately equivalent amounts in each case.
  • the carboxylic acid anhydride in a larger excess (up to 5 mol ) use
  • the processing takes place according to usual methods
  • the process (C) is characterized in that compounds of the formula (I-a) with chloroformates or chloroformates of the formula (VI), if appropriate in the presence of a diluent and if appropriate in
  • Suitable acid binders in process (C) according to the invention are all customary acid acceptors.
  • Tertiary amines such as triethylamine, pyridine, DABCO, DBU, DBA, Hunig base and N, N-dimethylaniline, furthermore alkaline earth metal oxides, such as magnesium and calcium oxide, and also alkali and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate, are preferably usable and calcium carbonate and alkali hydroxides such as sodium hydroxide and potassium hydroxide.
  • Diluents which can be used in process (C) according to the invention are all inert towards the chloroformates or chloroformates
  • Hydrocarbons such as gasoline, benzene, toluene, xylene and tetralin are preferably usable, furthermore halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, and also ketones such as acetone and methyl isopropyl ketone, furthermore ethers such as diethyl ether and tetrahydrofuran Dioxane, nitriles such as acetonitrile, moreover carboxylic acid esters, such as ethyl acetate, and also strongly polar solvents, such as dimethylformamide, dimethyl sulfoxide and sulfolane.
  • halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene
  • ketones such as acetone and methyl iso
  • reaction temperature can be varied within a relatively wide range.
  • the reaction temperature is generally between -20 ° C and + 100 ° C, preferably between
  • Process (C) according to the invention is generally carried out under normal pressure.
  • Chloroformic acid thioesters of the formula (VI) are generally approximated in each case equivalent amounts used. However, it is also possible to use one or the other component in a larger excess (up to 2 mol).
  • the processing takes place according to customary methods. The general procedure is to remove precipitated salts and to concentrate the remaining reaction mixture by stripping off the diluent.
  • Process (D) is characterized in that compounds of the formula (Ia) with (Da) compounds of the formula (VII) in the presence of a diluent and, if appropriate, in the presence of an acid binder or (Dß) carbon disulfide and then with Alkyl halides of the formula (VIII), if appropriate in the presence of a diluent and, if appropriate, in the presence of a base.
  • Possible diluents added are all inert polar organic solvents, such as ethers, amides, carboxylic esters, nitriles, sulfones, sulfoxides, but also haloalkanes.
  • Dimethyl sulfoxide, ethyl acetate, acetonitrile, tetrahydrofuran, dimethylformamide or methylene chloride are preferably used.
  • the addition of strong deprotonating agents such as e.g. Sodium hydride or potassium tert-butylate is the enolate salt of the compound (I-a), the further addition of acid binders can be dispensed with.
  • customary inorganic or organic bases are suitable, for example sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.
  • the reaction can be carried out at atmospheric pressure or under elevated pressure, preferably at atmospheric pressure.
  • the processing takes place according to usual methods.
  • the equimolar amount or an excess of carbon disulfide is added per mole of starting compound of the formula (Ia).
  • the process is preferably carried out at temperatures from 0 to 50 ° C. and in particular at 20 to 30 ° C.
  • Alkali metal hydrides, alkali metal alcoholates, alkali metal or alkaline earth metal carbonates or hydrogen carbonates or nitrogen bases are preferably usable.
  • Examples include sodium hydride, sodium methoxide, sodium hydroxide, calcium hydroxide, potassium carbonate, sodium hydrogen carbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline, diazabicycloctane (DABCO), diazabicyclonones (DBN) and diazabicycloundecene (DBU).
  • Aromatic hydrocarbons such as benzene or toluene, alcohols such as methanol, ethanol, isopropanol or ethylene glycol, nitriles such as acetonitrile, ethers such as tetrahydrofuran or dioxane, amides such as dimethylformamide or other polar solvents such as dimethyl sulfoxide or sulfolane can preferably be used.
  • the further reaction with the alkyl halide of the formula (VIII) is preferably carried out at 0 to 70 ° C. and in particular at 20 to 50 ° C.
  • at least the equimolar amount of alkyl halide is used.
  • Process (E) according to the invention is characterized in that compounds of the formula (Ia) are reacted with sulfonic acid chlorides of the formula (TX), if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid binder.
  • Formula (I-a) about 1 mol of sulfonic acid chloride of formula (IX) at -20 to 150 ° C, preferably at 20 to 70 ° C.
  • Process (E) is preferably carried out in the presence of a diluent.
  • Dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride are preferably used.
  • the enolate salt of the compound (I-a) is prepared by adding strong deprotonating agents (such as sodium hydride or potassium tert-butbutylate), the further addition of acid binders can be dispensed with.
  • strong deprotonating agents such as sodium hydride or potassium tert-butbutylate
  • customary inorganic or organic bases are suitable, examples being sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.
  • the reaction can be carried out at atmospheric pressure or under elevated pressure, preferably at atmospheric pressure.
  • the workup takes place according to customary methods.
  • Process (F) is characterized in that compounds of the formula (Ia) are reacted with phosphorus compounds of the formula (X) if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid binder.
  • 1 mol of the compound (Ia), 1 to 2, preferably 1 to 1.3 mol of the phosphorus compound of the formula (X) are used at temperatures between -40 ° C. to obtain compounds of the formula (Ie) and 150 ° C, preferably between -10 and 110 ° C.
  • Process (F) is preferably carried out in the presence of a diluent.
  • Suitable diluents are all inert, polar organic solvents such as halogenated hydrocarbons, carboxylic acid esters, ethers, amides, nitriles, sulfones, sulfoxides etc.
  • Acetonitrile, dimethyl sulfoxide, tetrahydrofuran, dimethyl formamide and methylene chloride are preferably used.
  • Possible inorganic binders which may be added are conventional inorganic or organic bases, such as hydroxides, carbonates or amines. Examples include sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.
  • the reaction can be carried out under normal pressure or under elevated pressure, preferably under normal pressure.
  • Working up takes place according to the usual methods of organic chemistry.
  • the end products are preferably obtained by crystallization, chromatographic purification or by so-called “distillation", i.e. Removal of the volatile constituents cleaned in a vacuum.
  • Process (G) is characterized in that compounds of the formula (I-a) are reacted with metal hydroxides or metal alkoxides of the formula (XI) or amines of the formula (XII), if appropriate in the presence of a diluent.
  • Diluents which can be used in process (G) according to the invention are preferably ethers such as tetrahydrofuran, dioxane, diethyl ether or alcohols such as methanol, ethanol, isopropanol, but also water.
  • Process (G) according to the invention is generally carried out under normal pressure.
  • the reaction temperature is generally between -20 ° C and 100 ° C, preferably between 0 ° C and 50 ° C.
  • the process (H) according to the invention is characterized in that compounds of the formula (Ia) with (H ⁇ ) compounds of the formula (Xül) optionally in the presence of a diluent and, if appropriate, in the presence of a catalyst or (H ⁇ ) with compounds of Formula (XTV) if appropriate in the presence of a diluent and optionally in the presence of an acid binder.
  • Process (H ⁇ ) is preferably carried out in the presence of a diluent.
  • Suitable diluents are all inert organic solvents, such as ethers, amides, nitriles, sulfones or sulfoxides.
  • catalysts can be added to accelerate the reaction.
  • Organic tin compounds such as e.g. Dibutyltin dilaurate can be used.
  • any inert polar organic solvents such as ethers, carboxylic acid esters, nitriles, amides, sulfones, sulfoxides or halogenated hydrocarbons are suitable as diluents which may be added.
  • Dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride are preferably used.
  • the enolate is prepared by adding strong deprotonating agents (such as sodium hydride or potassium tertiary butoxide). salt of the compound (Ia), the further addition of acid binders can be dispensed with.
  • strong deprotonating agents such as sodium hydride or potassium tertiary butoxide
  • customary inorganic or organic bases are suitable, for example sodium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine.
  • the reaction can be carried out at atmospheric pressure or under elevated pressure, preferably at atmospheric pressure.
  • the workup takes place according to customary methods.
  • the compounds according to the invention are suitable, with good plant tolerance and favorable toxicity to warm-blooded animals, for combating animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which are used in agriculture, in forests, in the protection of stored products and materials and in the hygiene sector occurrence. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • animal pests preferably arthropods and nematodes, in particular insects and arachnids, which are used in agriculture, in forests, in the protection of stored products and materials and in the hygiene sector occurrence. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the pests mentioned above include:
  • Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Diplopoda e.g. Blaniulus guttulatus
  • Chilopoda e.g. Geophilus carpophagus
  • Scutigera spec.
  • Symphyla e.g. Scutigerella immaculata.
  • Thysanura e.g. Lepisma saccharina.
  • Collembola e.g. Onychiurus armatus.
  • Anoplura for example Phylloxera vastatrix, Pemphigus spp, Pediculus humanus corporis, Haematopinus spp., Linognathus spp ..
  • Mallophaga for example Trichodectes spp., Damalinea spp.
  • Thysanoptera for example Hercinothrips femoralis, Thrips tabaci.
  • Heteroptera for example Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
  • Trialeurodes vaporariorum Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus sp. Sais- setia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii,
  • Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp.
  • Antho nomus spp. Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Ptigusususole , Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Cono derus spp., Melolontha melolontha, Amphimallon solsti tialis,
  • Hymenoptera From the order of the Hymenoptera, for example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp. From the order of the Diptera, for example Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca ., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitat
  • Dacus oleae Tipula paludosa.
  • Siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp .. From the order of the Arachnida e.g. Scorpio maurus, Latrodectus mactans.
  • Acarina e.g. Acarus siro, Argas spp., Omithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp.,
  • Rhipicephalus spp. Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..
  • the active compounds according to the invention are notable for high insecticidal and acaricidal activity.
  • insects which damage plants, such as, for example, against the larvae of the horseradish leaf beetle (Phaedon cochleariae), against the caterpillars of the cockroach (Plutella maculipennis), against the caterpillars of the owl butterfly (Spodoptera frugiperda), against the larvae of the green leafhopper (Nephotettix cincticeps) or against peach aphids (Myzus persicae) and for combating plant-damaging arachnids (Acari) such as, for example, against the common spider mite (Tetrany ⁇ chus urticae).
  • the active compounds according to the invention can furthermore be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • the dosages of the active compounds according to the invention required for weed control are between 0.001 and 10 kg / ha, preferably between 0.005 and 5 kg / ha.
  • the active compounds according to the invention can e.g. can be used for the following plants:
  • the compounds are suitable depending on the concentration
  • Total weed control for example on industrial and track systems and on paths and squares with and without tree cover.
  • the compounds for weed control in permanent crops for example forest, ornamental trees, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa and berry fruit and hop plants, on ornamental and sports turf and pastures and for selective weed control in annual crops.
  • the active compounds according to the invention are very suitable for the selective control of weeds in the pre-emergence process. They can be used, for example, in barley or soybeans with very good success to control harmful grasses.
  • the compounds according to the invention When used in appropriate amounts, the compounds according to the invention also have a fungicidal action, in particular against Pyricularia oryzae on rice.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as very fine encapsulation in polymeric substances.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents and / or solid carriers
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters
  • Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Possible solid carriers are: e.g. Ammonium salts and natural rock flours, such as kaolins, clays,
  • Talc chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and Synthetic rock flour, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g.
  • suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
  • the active ingredient according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active ingredients, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
  • Fungicides are particularly favorable mixed partners:
  • Fenarimol, Fenbuconazole, Fen Inenarimol, Fenbuconazole, Fen Nameam, Fenitropan, Fenpiclonil, Fenpropidin, Fen ⁇ propimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam, Flu-dioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolafosil, Fol- Fthalides, Fuberidazole, Furalaxyl, Beaumecyclox, Guazatine,
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenproothat, Fufionfox, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufone HCH, heptenophos, hexaflumuron, hexythiazox,
  • Imidacloprid Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivemectin, Lamda-cyhalothrin, Lufenuron, Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathione, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin, Naled, NC 184, NI 25, Nitenpyram, Omethoat, Oxofonon, Oxamyl, Oxamyl, Oxydos
  • Parathion A parathion M, permethrin, phenthoate, phorate, phosalone, phosmet, Phosphamdon, phoxim, pirimicarb, pirimiphos M, Primiphos A, profenofos, promecarb, propaphos, propoxur, prothiofos, prothoate, pymetrozine, Pyrachlophos, Pyradaphenthion, Pyresmethrin, pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen, Quinalphos,
  • Herbicides for example anilides, e.g. Diflufenican and Propanil; Aryl carboxylic acids, e.g. Dichloropicolinic acid, dicamba and picloram; Aryloxyalkanoic acids, e.g. 2.4 D, 2.4 DB, 2.4 DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, e.g. Diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, shark oxyfop-m ethyl and quizalofop-ethyl; Azinones, e.g.
  • Chloridazon and norflurazon Carbamates, e.g. Chlorpropham, desmedipham, phenmedipham and propham; Chloroacetanilides, e.g. Alachlor, acetochlor, butachlor,
  • Metazachlor metolachlor, pretilachlor and propachlor
  • Dinitroanilines such as oryzalin, pendimethalin and trifluralin
  • Diphenyl ethers such as acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen
  • Ureas such as, for example, chlorotoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron
  • Hydroxylamines such as, for example, alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim
  • Imidazolinones such as imazethapyr, imazamethabenz, imazapyr and imazaquin
  • Nitriles such as bromoxynil, dichlobenil and ioxynil
  • Oxyacetamides such as mefen
  • Fluorochloridones Glufosinate, Glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and Tridiphane.
  • the active ingredient according to the invention can furthermore be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • the active compound When used against hygiene pests and pests of stored products, the active compound is distinguished by an outstanding residual action on wood and clay and by a good stability to alkali on limed substrates.
  • the active compounds according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice,
  • animal parasites ectoparasites
  • tick ticks leather ticks
  • mites running mites
  • flies stinging and licking
  • parasitic fly larvae lice
  • Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp ..
  • Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota ., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Glossina spp., Calliphora spp., Glossina spp.,
  • Siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp ..
  • Actinedida Prostigmata
  • Acaridida e.g. Acarapis spp., Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypppectoles spp ., Psoroptes spp.,
  • Chorioptes spp. Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp ..
  • the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used for agricultural purposes, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, Turkeys, ducks, geese, bees, other domestic animals such as dogs, cats, house birds, aquarium fish and so-called experimental animals such as hamsters, guinea pigs, rats and mice are attacked.
  • arthropods which are used for agricultural purposes, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, Turkeys, ducks, geese, bees, other domestic animals such as dogs, cats, house birds, aquarium fish and so-called experimental animals such as hamsters, guinea pigs, rats and mice are attacked.
  • arthropods which are used for agricultural purposes, such as, for example, cattle, sheep, goats, horses, pig
  • the active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, such as Example by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on) ), washing, powdering and with the help of active ingredients
  • Shaped bodies such as collars, ear tags, tail tags, limb tapes, holsters, marking devices, etc.
  • the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or after Apply 100 to 10,000-fold dilution or use it as a chemical bath.
  • formulations for example powders, emulsions, flowable agents
  • insects may be mentioned by way of example and preferably, but without limitation:
  • Lyctus pubescens Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus.
  • Kalotermes flavicollis Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwinisis, Zootermopsis nevadensis, Coptotermes formosanus.
  • Bristle tails such as Lepisma saccharina.
  • materials such as preferably plastics, adhesives, glues, papers and cartons, leather, wood and wood processing products and paints.
  • the material to be protected against insect infestation is very particularly preferably wood and wood processing products.
  • Means or mixtures containing them can be protected is to be understood as examples: construction timber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone poles, wooden cladding, wooden windows and doors, plywood, chipboard, carpentry or woodworking. Products that are used in general in house construction or in joinery.
  • the active compounds can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
  • the formulations mentioned can be prepared in a manner known per se, for example by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellants, optionally desiccants and UV stabilizers and where appropriate dyes and pigments and further processing aids.
  • the insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active ingredient according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
  • the amount of the agents or concentrates used depends on the type and occurrence of the insects and on the medium. The optimal amount can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active ingredient, based on the material to be protected.
  • the organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
  • Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.
  • Mineral oils with a boiling range of 170 to 220 ° C, test gasoline with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° are advantageous C, turpentine oil and the like.
  • the organic low-volatility oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, can be partially replaced by slightly or medium-volatile organic chemical cal solvents are replaced, with the proviso that the solvent mixture also has an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C., and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.
  • Solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture replaced.
  • the known organic-chemical binders are the water-dilutable synthetic resins and / or synthetic resins which are soluble or dispersible or emulsifiable in the organic-chemical solvents used and / or binding drying oils, in particular binders consisting of or containing an acrylic resin, a vinyl resin, e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / / or synthetic resin used.
  • binders consisting of or containing an acrylic resin, a vinyl resin, e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as in
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellants, odor correctors and inhibitors or anticorrosive agents and the like can be used.
  • At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder.
  • Alkyd resins having an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
  • binder mentioned can be replaced by a fixative (mixture) or a plasticizer (mixture). These additions should volatilize the active ingredients and crystallize or precipitate! prevent. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).
  • the plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, higher glycerol glycerol or glycerol ether ⁇ kol ether, glycerol ester and p-toluenesulfonic acid ester.
  • phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate
  • phosphoric acid esters such as tributyl phosphate
  • adipic acid esters such as di- (2-ethylhexyl) adipate
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
  • Water is also particularly suitable as a solvent or diluent, if appropriate in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
  • a particularly effective wood protection is achieved through industrial impregnation processes, e.g. Vacuum, double vacuum or pressure process.
  • the ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides.
  • insecticides and fungicides mentioned in WO 94/29 268 are preferably suitable as additional admixing partners.
  • the ones mentioned in this document are preferably suitable as additional admixing partners.
  • Insecticides such as chloropyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, delta-methrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and triflumuron, as well as fungazazole, such as fungazizides, such as epizazole, as well as fungazizides such as Azaconazole, Pro piconazole, Tebuconazole, Cyproconazole e, Metconazole, Imazalil, Dichlorfluanid, Tolylfluanid, 3-Iodo-2-propynylbutylcarbamate, N-Octyl-isothiazolin-3-one and 4,5-Dichloro-N-octylisothiazolin-3 -on called.
  • the preparation and use of the active compounds according to the invention can be seen
  • Solvent 7 parts by weight of acetone emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with horseradish leaf beetle larvae (Phaedon cochleariae) while the leaves are still moist.
  • the plants are populated with horseradish leaf beetle larvae (Phaedon cochleariae).
  • the death rate is determined in% after every 3 days. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
  • the compounds according to Preparation Examples Ia-1, Ia-2, Ia-4, Ib-1, Ib-2, Ib-7, Ib-8, Ic-1 and Ic-6 showed at an exemplary active ingredient concentration of 0.01% after 7 days a degree of killing of 100%.
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage leaves (Brassica oleracea) are treated by dipping into the active ingredient preparation of the desired concentration and with caterpillars of the cabbage cockroach
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the owl butterfly (Spodoptera frugiperda) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Ib-1, 1-c-2, Ic-5 with an exemplary active ingredient concentration of 0.1% after 7 days a degree of killing of 85 to 100%.
  • Solvent 7 parts by weight of dimethylforamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Rice seedlings (Oryzae sativa) are treated by immersing them in the active ingredient preparation of the desired concentration and with larvae of the green rice leafhopper
  • the detachment is determined in%. 100% means that all cicadas have been killed; 0% means that no cicadas have been killed.
  • Solvent 3 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage leaves (Brassica oleracea), which are heavily infested with peach aphids (Myzus persicae), are treated by being dipped into the preparation of active compound of the desired concentration.
  • the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • the compounds according to the preparation examples Ia-1, Ia-4, Ia-5, Ia-9, Ia-1 1, Ib-4 and Ib-7 demonstrated at an exemplary active ingredient concentration of 0.1% 6 days a kill rate of 80 to 100%.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Bean plants Phaseolus vulgaris
  • Bean plants which are severely affected by all stages of development of the common spider mite or bean spider mite (Tetranychus urticae)
  • the kill is determined in%. 100% means that all spider mites have been killed; 0% means that none of the spider mites have been killed.
  • the compounds according to the preparation examples Ia-3, Ia-4, Ia-11, Ib-1, Ic-2 and Ic-3 showed a degree of kill of 13% after 13 days with an exemplary active ingredient concentration of 0.01% at least 95%.
  • Solvent 5 parts by weight of acetone emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Test animals adult Musca domestica, trunk Reichswald (OP, SP,
  • the effectiveness of the active substance preparation is determined. 100% means that all flies have been killed; 0% means that no flies have been killed.
  • the compound according to preparation example Ic-4 had an effectiveness of 100% at an exemplary active ingredient concentration of 1000 ppm.
  • Test animals All larval stages of Lucilia cuprina (OP-resistant)
  • 30 to 50 larvae per concentration are placed on horse meat (1 cm 3 ) in glass tubes, onto which 500 ⁇ l of the dilution to be tested are pipetted.
  • the glass tubes are placed in plastic beakers, the bottom of which is covered with sea sand, and stored in an air-conditioned room (26 ° C ⁇ 1.5 ° C, 70% relative humidity ⁇ 10%). The effects are checked after 24 hours and 48 hours (larvicidal action). After the larvae have emigrated (approx. 72 h), the glass tubes are removed and perforated plastic lids are placed on the beakers. After l ' ⁇ times the development period (hatching of the control flies), the hatched flies and the dolls / doll covers are counted.
  • Larvae after 48 h (larvicidal effect), or the inhibition of adult hatching from the pupa or the inhibition of pupa formation.
  • the criterion for the in vitro effect of a substance is the inhibition of flea development or a development standstill before the adult stage. 100% larvicidal activity means that all larvae have died after 48 hours. 100% development-inhibitory effect means that no adult flies have hatched.
  • Test animals adult sucked females
  • the test is carried out in 5-fold determination. 1 ⁇ l of the solutions is injected into the abdomen, the animals are transferred to dishes and stored in an air-conditioned room. The effect is determined by the inhibition of egg laying. 100% means that no tick has laid.
  • Example I-a-9 has an activity of 100% at an exemplary active ingredient concentration of 20 ⁇ g / animal.

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

Abstract

L'invention concerne de nouveaux dérivés 3-aryl-5-halogéno-pyrone de formule (I), dans laquelle A, D, G, X, Y, Z et n ont les significations données dans la description, plusieurs procédés de fabrication et produits intermédiaires pour la fabrication de ces composés, ainsi que leur utilisation comme pesticides et herbicides.
EP96934687A 1995-10-27 1996-10-15 Derives 3-aryl-5-halogeno-pyrone utilises comme pesticides Withdrawn EP0879232A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19540080A DE19540080A1 (de) 1995-10-27 1995-10-27 3-Aryl-5-halogen-pyron-Derivate
DE19540080 1995-10-27
PCT/EP1996/004475 WO1997016436A1 (fr) 1995-10-27 1996-10-15 Derives 3-aryl-5-halogeno-pyrone utilises comme pesticides

Publications (1)

Publication Number Publication Date
EP0879232A1 true EP0879232A1 (fr) 1998-11-25

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP96934687A Withdrawn EP0879232A1 (fr) 1995-10-27 1996-10-15 Derives 3-aryl-5-halogeno-pyrone utilises comme pesticides

Country Status (7)

Country Link
US (1) US5977029A (fr)
EP (1) EP0879232A1 (fr)
JP (1) JPH11514630A (fr)
AU (1) AU7292896A (fr)
BR (1) BR9611130A (fr)
DE (1) DE19540080A1 (fr)
WO (1) WO1997016436A1 (fr)

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JP3227424B2 (ja) * 1998-02-13 2001-11-12 大日精化工業株式会社 育成効果を有する芝生着色剤組成物
DE19808261A1 (de) * 1998-02-27 1999-10-28 Bayer Ag Arylphenylsubstituierte cyclische Ketoenole
DE19813354A1 (de) 1998-03-26 1999-09-30 Bayer Ag Arylphenylsubstituierte cyclische Ketoenole
DE19818732A1 (de) * 1998-04-27 1999-10-28 Bayer Ag Arylphenylsubstituierte cyclische Ketoenole
AU5745099A (en) * 1998-09-11 2000-04-03 Bayer Aktiengesellschaft Thiopyron-derivative and their use as pesticides
DE19848895A1 (de) * 1998-10-23 2000-04-27 Bayer Ag 3-Halogen-3-phenyl-pyrone
US6486128B1 (en) 1999-04-08 2002-11-26 Schering-Plough Veterinary Corporation Method of using emamectin to treat fish parasites
DE19935963A1 (de) 1999-07-30 2001-02-01 Bayer Ag Biphenylsubstituierte cyclische Ketoenole
US6432877B2 (en) * 2000-01-21 2002-08-13 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Lawn colorant composition having rearing effects
DE10016544A1 (de) 2000-04-03 2001-10-11 Bayer Ag C2-phenylsubstituierte Ketoenole
DE10062422A1 (de) * 2000-12-14 2002-06-20 Bayer Ag Verwendung von Acetyl-CoA Carboxylase zum Identifizieren von insektizid wirksamen Verwendung
DE10139465A1 (de) 2001-08-10 2003-02-20 Bayer Cropscience Ag Selektive Herbizide auf Basis von substituierten, cayclischen Ketoenolen und Safenern
DE10311300A1 (de) 2003-03-14 2004-09-23 Bayer Cropscience Ag 2,4,6-Phenylsubstituierte cyclische Ketoenole
US6958146B2 (en) * 2003-05-28 2005-10-25 Bug Buster Ltd. Compounds to affect insect behavior and to enhance insecticides
US7867479B2 (en) * 2003-11-14 2011-01-11 Bug Buster, Ltd. Compounds to affect insect behavior and/or bird behavior
DE10326386A1 (de) 2003-06-12 2004-12-30 Bayer Cropscience Ag N-Heterocyclyl-phenylsubstituierte cyclische Ketoenole
DE102004014620A1 (de) * 2004-03-25 2005-10-06 Bayer Cropscience Ag 2,4,6-phenylsubstituierte cyclische Ketoenole
DE102004035133A1 (de) * 2004-07-20 2006-02-16 Bayer Cropscience Ag Selektive Insektizide auf Basis von substituierten, cyclischen Ketoenolen und Safenern
DE102004044827A1 (de) 2004-09-16 2006-03-23 Bayer Cropscience Ag Jod-phenylsubstituierte cyclische Ketoenole
DE102005059469A1 (de) 2005-12-13 2007-06-14 Bayer Cropscience Ag Insektizide Zusammensetzungen mit verbesserter Wirkung
DE102006007882A1 (de) 2006-02-21 2007-08-30 Bayer Cropscience Ag Cycloalkyl-phenylsubstituierte cyclische Ketoenole
WO2010102758A2 (fr) 2009-03-11 2010-09-16 Bayer Cropscience Ag Cétoénols à substitution halogénoalkylméthylèneoxy-phényle
DE102010008644A1 (de) 2010-02-15 2011-08-18 Bayer Schering Pharma Aktiengesellschaft, 13353 Zyklische Ketoenole zur Therapie
DE102010008643A1 (de) 2010-02-15 2011-08-18 Bayer Schering Pharma Aktiengesellschaft, 13353 Zyklische Ketoenole zur Therapie
DE102010008642A1 (de) 2010-02-15 2011-08-18 Bayer Schering Pharma Aktiengesellschaft, 13353 Zyklische Ketoenole zur Therapie
DE102011011040A1 (de) 2011-02-08 2012-08-09 Bayer Pharma Aktiengesellschaft (5s,8s)-3-(4'-Chlor-3'-fluor-4-methylbiphenyl-3-yl)-4-hydroxy-8-methoxy-1-azaspiro[4.5]dec-3-en-2-on (Verbindung A) zur Therapie
DK2806741T3 (da) 2012-01-26 2020-05-18 Bayer Ip Gmbh Phenylsubstituerede ketoenoler til bekæmpelse af fiskeparasitter
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Also Published As

Publication number Publication date
DE19540080A1 (de) 1997-04-30
JPH11514630A (ja) 1999-12-14
WO1997016436A1 (fr) 1997-05-09
BR9611130A (pt) 1999-03-30
AU7292896A (en) 1997-05-22
US5977029A (en) 1999-11-02

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