EP1687272A1 - Derives d'acide tetramique spirocycliques a substitution 2-ethyl-4,6-dimethyl-phenyle - Google Patents

Derives d'acide tetramique spirocycliques a substitution 2-ethyl-4,6-dimethyl-phenyle

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Publication number
EP1687272A1
EP1687272A1 EP04803114A EP04803114A EP1687272A1 EP 1687272 A1 EP1687272 A1 EP 1687272A1 EP 04803114 A EP04803114 A EP 04803114A EP 04803114 A EP04803114 A EP 04803114A EP 1687272 A1 EP1687272 A1 EP 1687272A1
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EP
European Patent Office
Prior art keywords
alkyl
alkoxy
optionally
formula
compounds
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Withdrawn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
EP04803114A
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German (de)
English (en)
Inventor
Reiner Fischer
Stefan Lehr
Mark Wilhelm Drewes
Dieter Feucht
Jörg KONZE
Peter Lösel
Olga Malsam
Guido Bojack
Christian Arnold
Thomas Auler
Martin Jeffrey Hills
Heinz Kehne
Christopher Hugh Rosinger
Christoph Di Erdelen
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Bayer CropScience AG
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Bayer CropScience AG
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Publication of EP1687272A1 publication Critical patent/EP1687272A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/54—Spiro-condensed
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/10—Spiro-condensed systems

Definitions

  • the invention relates to new 2-ethyl-4,6-dimethyl-phenyl-substituted spirocyclic tetramic acid derivatives, several processes and intermediates for their preparation and their use as pesticides and / or herbicides.
  • the invention also relates to new selectively herbicidal active compound combinations which contain 2-ethyl-4,6-dimethyl-phenyl-substituted spirocyclic tetramic acid derivatives on the one hand and at least one compound which improves the tolerance to crop plants on the other hand and can be used with particularly good success for selective weed control with various crop plants ,
  • EP-A-0 262 399 and GB-A-2 266 888 disclose similarly structured compounds (3-arylpyrrolidine-2,4-diones), of which no herbicidal, insecticidal or acaricidal activity has been disclosed.
  • Unsubstituted, bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives EP-A-355 599 and EP-A-415 211) and substituted monocyclic 3-aryl-pyrrolidine-2 are known with herbicidal, insecticidal or acaricidal activity , 4-dione derivatives (EP-A-377 893 and EP-A-442 077).
  • a and B together with the carbon atom to which they are attached represent a saturated or unsaturated C -Cg ring which may contain at least one heteroatom and which is optionally substituted,
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulfur
  • M oxygen or sulfur
  • R 1 represents optionally substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl or represents cycloalkyl or heterocyclyl optionally substituted by halogen, alkyl or alkoxy or represents optionally substituted phenyl or hetaryl,
  • R 2 represents in each case optionally substituted by halogen alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl or for in each case optionally substituted cycloalkyl, phenyl or benzyl, ⁇ 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 represent optionally substituted phenyl, benzyl, phenoxy or phenylthio,
  • R 6 and R 7 independently of one another represent hydrogen, each optionally substituted by halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, each optionally substituted phenyl or benzyl, or together with the N atom to which they are attached, one optionally form oxygen or sulfur-containing, optionally substituted 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. However, for the sake of simplicity, 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.
  • A, B, E, L, M, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given above.
  • R 1 has the meaning given above and
  • R 1 has the meaning given above
  • R 2 and M have the meanings given above,
  • R 2 has the meaning given above and
  • R 4 and R 5 have the meanings given above and
  • Me for a mono- or divalent metal preferably an alkali or alkaline earth metal like
  • R 10 , R 11 , R 12 independently of one another represent hydrogen or alkyl (preferably C 1 -C 6 -alkyl),
  • 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 / or acaricides and / or as herbicides.
  • n a number 0, 1, 2, 3, 4 or 5
  • a 1 represents one of the divalent heteroeyclic groups outlined below,
  • n stands for a number 0, 1, 2, 3, 4 or 5
  • a 2 represents alkanediyl with 1 or 2 carbon atoms which is optionally substituted by Ci-GrAlkyl and / or C 1 -C 4 alkoxy-carbonyl and / or C] -C - alkenyloxy-carbonyl,
  • R 14 represents hydroxyl, mercapto, amino, C ⁇ -C 6 -alkoxy, C 6 alkylthio, -C 6 alkylamino or di- (C ⁇ -C4 alkyl) amino group,
  • R 15 for hydroxy, mercapto, amino, CC 7 -alkoxy, CC 6 -alkenyloxy, CC 6 -alkenoxy-C ⁇ -C, 6 "alkoxy, CC 6 -alkylthio, -C-C 6 -alkylamino or di- (CC 4 - alkyl) amino
  • R 16 represents CrC 4 alkyl optionally substituted by fluorine, chlorine and or bromine
  • R 17 for hydrogen, each optionally substituted by fluorine, chlorine and / or bromine - C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, C, -C 4 alkoxy-C, -C 4- alkyl, dioxolanyl-C r C 4 -alkyl, furyl, furyl-C 1 -C 4 -alkyl, thienyl, thiazolyl, piperidinyl, or optionally by fluorine, chlorine and / or bromine - C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, C, -C 4 alkoxy-C, -C 4- alkyl, dioxolanyl-C r C 4 -alkyl, furyl, furyl-C 1 -C 4 -alkyl, thienyl, thiazolyl, piperidinyl, or optionally by
  • R 18 for hydrogen, in each case optionally substituted by fluorine, chlorine and / or bromine, C-alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl, CC 4 -alkoxy-C 1 -C 4 -alkyl, dioxolanyl- C, -C 4 alkyl, furyl, furyl-C C 4 alkyl, thienyl, thiazolyl, piperidinyl, or phenyl optionally substituted by fluorine, chlorine and / or bromine or CC 4 alkyl, or R 17 and R 18 also together for each C 3 - substituted by CC 4 alkyl, phenyl, furyl, a fused benzene ring or by two substituents which together with the C atom to which they are attached form a 5- or 6-membered carboxy cycle C 6 - alkanediyl or C 2 -C 5 -oxaalkan
  • R 19 represents hydrogen, cyano, halogen, or C] -C 4 -alkyl, C 3 -C 6 -cycloalkyl or phenyl which are each optionally substituted by fluorine, chlorine and or bromine,
  • R 20 represents hydrogen, optionally substituted by hydroxy, cyano, halogen or -CC alkoxy C, -C 6 alkyl, C 3 -C 6 cycloalkyl or tri- (C, -C 4 alkyl) silyl,
  • R 21 represents hydrogen, cyano, halogen, or CC 4 -alkyl, C 3 -C 6 -cycloalkyl or phenyl which are optionally substituted by fluorine, chlorine and / or bromine,
  • X 1 for nitro, cyano, halogen, CC 4 -alkyl, CC 4 -haloalkyl, -C 4 -alkoxy or CC 4 -
  • X 2 represents hydrogen, cyano, nitro, halogen, C ⁇ -C 4 -alkyl, C 4 haloalkyl, CC 4 -alkoxy or C] -C 4 haloalkoxy,
  • X 3 represents hydrogen, cyano, nitro, halogen, C, -C 4 -alkyl, C, -C 4 -haloalkyl, C r C 4 -alkoxy or C] -C -haloalkoxy,
  • t represents a number, 0, 1, 2, 3, 4 or 5
  • v represents a number 0, 1, 2, 3, 4 or 5
  • R 22 represents hydrogen or -Q-alkyl
  • R 23 represents hydrogen or C, -C 4 alkyl
  • R 24 for hydrogen, in each case optionally substituted by cyano, halogen or CC 4 -alkoxy-substituted C, -C 6 -alkyl, C, -C 6 -alkoxy, d- -alkylthio, CC 6 -alkylamino or di- (CC 4 -alkyl) - a ino, or in each case optionally substituted by cyano, halogen or -CC 4 alkyl
  • R 25 represents hydrogen, optionally cyano-, hydroxyl-, halogen or - - alkoxy substituted C ⁇ -C 6 -alkyl, in each case optionally cyano- or halogen-substituted C 3 -C 6 -
  • R 2 ⁇ for hydrogen, optionally substituted by cyano, hydroxy, halogen or CC 4 alkoxy C] -C 6 alkyl, in each case optionally substituted by cyano or halogen, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl, optionally cyano-, halogen- or C 4 -alkyl-substituted C 3 - cycloalkyl, or optionally substituted by nitro, cyano, halogen, CC alkyl, CC 4 haloalkyl, -CC 4 alkoxy or CC 4 -haloalkoxy substituted phenyl, or together with R 25 for C 2 -C 6 -alkanediyl or C 2 -C 5 - optionally substituted by -C-C 4 alkyl Oxaalkanediyl stands,
  • X 4 represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halogen, CC-alkyl, Q- -haloalkyl, CC 4 -alkoxy or CC 4 -haloalkoxy, and
  • X 5 represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halo, C] - C ⁇ -C 4 alkoxy or C, -C 4 -haloalkoxy CrAlkyl, C ⁇ -C 4 haloalkyl.
  • A, B and the carbon atom to which they are attached are preferably saturated C 3 -C 8 -cycloalkyl or unsaturated C5-Cg-cycloalkyl, in which a methylene group is optionally replaced by oxygen or sulfur and which is optionally replaced by C ⁇ -C 6 - Alkyl, C 1 -C 4 -haloalkyl or C 1 -C 6 -alkoxy is substituted,
  • G preferably represents 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 13 CON ⁇ , 3 . substituted C, -C 20 alkyl, C 2 -C 20 alkenyl, d-C ⁇ -alkoxy-Ci-C ⁇ -alkyl, CC 6 - R
  • R 2 preferably represents in each case optionally mono- to trisubstituted by halogen
  • CC 20 -alkyl C 2 -C 20 -alkenyl, -C-C 6 -alkoxy-C 2 -C 6 -alkyl or poly-C ⁇ -C 6 -alkoxy-C 2 -C 6 - alkyl,
  • C 3 -C 8 cycloalkyl which is optionally mono- to disubstituted by halogen, Ci-C ⁇ -alkyl or -CC 6 alkoxy or
  • halogen optionally monosubstituted in each case up to three times by halogen, cyano, nitro, CC ß -alkyl, C 6 -alkoxy, C 6 haloalkyl or C ⁇ -C 6 haloalkoxy-substituted phenyl or benzyl,
  • R 3 preferably represents CC 8 -alkyl which is optionally mono- to polysubstituted by halogen or represents in each case optionally mono- or disubstituted by halogen, CC 6 -alkyl,
  • R 4 and R 5 independently of one another preferably represent in each case optionally mono- to trisubstituted by halogen-substituted C Cg-alkyl, C ⁇ -C 8 -alkoxy, C 8 alkylamino, di- (C 1 -C 8 ⁇ alkyl) amino, Cj-Cg-alkylthio or C 2 -C 8 -alkenylthio or for each optionally optionally up to triple by halogen, nitro, cyano, CC 4 -alkoxy, CC 4 -haloalkoxy, CC -alkylthio, CC 4 -haloalkylthio, CC 4 -alkyl or C 1 -C 4 haloalkyl-substituted phenyl, phenoxy or phenylthio,
  • R 6 and R 7 independently of one another preferably represent hydrogen, represent in each case optionally mono- to trisubstituted by halogen CC 8 alkyl, C 3 -C 8 cycloalkyl, C ⁇ -C 8 -
  • R ⁇ 3 preferably represents in each case mono- to trisubstituted or substituted by halogen Ci-Cg-alkyl, C3-Cg-alkenyl, C3-Cg-Alkt.nyl or C ⁇ -C4-alkoxy-C2-C4- alkyl or optionally optionally up to disubstituted by halo, C ⁇ ⁇ -C2-alkyl or Ci-C2-alkoxy-substituted C3-C5-cycloalkyl, in which optionally one or two not directly adjacent methylene groups are replaced by oxygen or represents in each case optionally mono- to disubstituted by fluorine, chlorine, bromine , C ⁇ x -C4 alkyl, C1 -C4-
  • R 13 ' preferably represents hydrogen, C1-Cg-alkyl or C3-Cg-alkenyl.
  • halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
  • A, B and the carbon atom to which they are attached are particularly preferred for saturated C3-C7-cycloalkyl, in which a methylene group may have been replaced by oxygen and which may be monosubstituted or disubstituted by C 1 -C 4 -alkyl, C -C 2 -haloalkyl or C j -C4 ⁇ alkoxy is substituted,
  • G particularly preferably represents one of the groups
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulfur
  • M represents oxygen or sulfur
  • R 1 particularly preferably represents in each case optionally up to five times by fluorine or
  • Chlorine, simply by cyano, simply by CO-R 13 , C N-OR 13 or C0 2 R 13 substituted C-Cio-alkyl, C 2 -C ⁇ o-alkenyl, C, -C 4 -alkoxy-C, -C 2 -alkyl, CrC 4 -alkylthio-C, -C 2 -alkyl or poly-C ] -C3-alkoxy-C ⁇ -C2-alkyl or for optionally single to double by fluorine, chlorine, CC 2 -alkyl or CC 2 - Alkoxy substituted C 3 -C 6 cycloalkyl, in which one or two not directly adjacent methylene groups are optionally replaced by oxygen,
  • pyrazolyl for pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine or CC 2 alkyl,
  • R 2 particularly preferably represents in each case one to three times by fluorine or
  • C 3 -C 7 cycloalkyl which is optionally substituted by C 1 -C 4 -alkyl or CC 2 -alkoxy or
  • phenyl or benzyl optionally substituted once or twice by fluorine, chlorine, bromine, cyano, nitro, CC 4 -alkyl, methoxy, trifluoromethyl or trifluoromethoxy,
  • R 3 particularly preferably represents CC 4 alkyl which is optionally monosubstituted to trisubstituted by fluorine or chlorine or represents in each case optionally monosubstituted by fluorine, chlorine, bromine, C 1 -C 4 alkyl, CC 4 alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro substituted phenyl or benzyl,
  • R 4 and R 5 are, independently of one another, particularly preferably each of C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, CC 6 -alkylamino, di- (C 1 -C 6 -alkyl) which is optionally mono- to trisubstituted by fluorine or chlorine.
  • R 6 and R independently of one another are particularly preferably hydrogen, for each optionally mono- to trisubstituted by fluorine or chlorine substituted C r C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 3 -C 6 -Alkenyl or -CC 6 -alkoxy-C 2 -C 6 -alkyl, for optionally optionally mono- to disubstituted by fluorine, chlorine, bromine, trifluoromethyl, -CC alkyl or
  • R i3 particularly preferably represents -C4-alkyl, C3-C4-alkenyl, C3-C4-alkynyl, or C1-C4-alkoxy-C2-C3-alkyl or for C3-C6-cycloalkyl, in which a methylene group is optionally through Oxygen is replaced.
  • halogen represents fluorine, chlorine and bromine, in particular fluorine and chlorine.
  • A, B and the carbon atom to which they are attached very particularly preferably represent saturated Cg-cycloalkyl, in which a methylene group is optionally replaced by oxygen and which is optionally simply replaced by methyl, ethyl, trifluoromethyl,
  • G very particularly preferably represents one of the groups
  • M oxygen or sulfur
  • R 1 very particularly preferably represents in each case mono- to trisubstituted by fluorine or chlorine-substituted C, -C 6 -alkyl, C 2 -C 6 -alkenyl, CrC 2 -alkoxy-CrC 2 -alkyl, CC 2 -
  • Cyclopentyl or cyclohexyl for phenyl optionally substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethyl or trifluoromethoxy, for in each case optionally furanyl, thienyl or pyridyl which is simply substituted by chlorine, bromine or methyl,
  • R 2 very particularly preferably represents C 1 -C 6 -alkyl, C 2 -C 6 alkenyl or C 1 -C 4 alkoxy-C 2 -C 3 -a] lcyl, cyclopentyl or cyclohexyl,
  • R 3 very particularly preferably represents —Gralkyl optionally monosubstituted to trisubstituted by fluorine or chlorine, or represents phenyl or phenyl substituted by fluorine, chlorine, bromine, Q- alkyl, Ci- -alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro benzyl,
  • R 6 very particularly preferably represents hydrogen, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl or AUyl, or phenyl optionally substituted by fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl,
  • R 7 very particularly preferably represents methyl, ethyl, n-propyl, isopropyl or allyl,
  • R and R together very particularly preferably represent a Cs-C ö alkylene radical in which a methylene group is optionally replaced by oxygen.
  • A, B and the carbon atom to which they are attached are highlighted for saturated Cg-cycloalkyl, which is optionally simply substituted by methyl, methoxy or n-propoxy,
  • M stands for oxygen
  • R 1 stands for CC 6 -alkyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl or cyclopropyl
  • R 2 stands for C 1 -C 8 -alkyl or C 2 -C 6 -alkenyl
  • R 3 stands for C 1 -C 4 -alkyl.
  • Saturated or unsaturated hydrocarbon radicals such as alkyl, alkanediyl 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, and in the case of multiple substitutions the substituents can be the same or different.
  • G preferably represents hydrogen
  • A, B and the carbon atom to which they are attached are preferably saturated C3 ⁇ Cg-cycloalkyl or unsaturated C5-Cg-cycloalkyl, in which a methylene group is optionally replaced by oxygen or sulfur and which is optionally replaced by Ci-Cg-alkyl, C ⁇ - C4-haloalkyl or C1-Cg-alkoxy is substituted,
  • G particularly preferably represents hydrogen
  • A, B and the carbon atom to which they are attached are particularly preferred for saturated C3-C7-cycloalkyl, in which a methylene group may have been replaced by oxygen and which may be simply C 1 -C 4 -alkyl, C 1 -C 2 -haloalkyl or C 1 -C 4 alkoxy is substituted,
  • G very particularly preferably represents hydrogen
  • A, B and the carbon atom to which they are attached very particularly preferably represent saturated C0-cycloalkyl, in which, if appropriate, a methylene group by oxygen is replaced and which is optionally simply substituted by methyl, ethyl, trifluoromethyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy or iso-butoxy.
  • herbicide safeners of the formulas (Da), (üb), (He), (Ild) and (He) which improve crop plant tolerance are defined below.
  • m preferably represents the numbers 0, 1, 2, 3 or 4.
  • a 1 preferably represents one of the divalent heteroeyclic groups outlined below
  • n preferably represents the numbers 0, 1, 2, 3 or 4.
  • a 2 preferably represents in each case methylene or ethylene which is optionally substituted by methyl, ethyl, methoxycarbonyl or ethoxycarbonyl or allyloxycarbonyl.
  • 14 preferably represents hydroxy, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i- , s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino.
  • R 1S preferably represents hydroxy, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, 1-methyl-hexyloxy, allyloxy, 1-allyloxymethyl-ethoxy, methyl thio, ethyl-thio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, Dimethylamino or Diethyla ino.
  • R 16 preferably represents methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine, chlorine and or bromine.
  • R 17 preferably represents hydrogen, in each case optionally substituted by fluorine and / or chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl, methoxymethyl, Ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl, or optionally by fluorine, chlorine,
  • R 18 preferably represents hydrogen, in each case optionally substituted by fluorine and / or chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl, methoxymethyl, Ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl, or optionally by fluorine, chlorine,
  • R 19 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl, each optionally substituted by fluorine, chlorine and or bromine.
  • R 20 preferably represents hydrogen, optionally substituted by hydroxy, cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy methyl, ethyl, n- or i-propyl, n-, i-, s- or t- butyl.
  • R 21 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, n-, i-, s- or t- which is optionally substituted by fluorine, chlorine and / or bromine. Butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl.
  • X 1 preferably represents nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoro- methyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
  • X 2 preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl , Fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
  • X 3 preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl , Fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
  • t preferably represents the numbers 0, 1, 2, 3 or 4.
  • v preferably represents the numbers 0, 1, 2, 3 or 4.
  • R 22 preferably represents hydrogen, methyl, ethyl, n- or i-propyl.
  • R 23 preferably represents hydrogen, methyl, ethyl, n- or i-propyl.
  • R 24 preferably represents hydrogen, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino , Ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, or in each case optionally substituted by cyano, fluorine, chlorine, bro
  • Cyclobutyl Cyclopentyl, Cyclohexyl, Cyclopropyloxy, Cyclobutyloxy, Cyclopentyloxy, Cyclohexyloxy, Cyclopropylthio, Cyclobutylthio, Cyclopentylthio, Cyclohexylthio, Cyclopropylamino, Cyclobutylamino, Cyclopentylamino or Cyclohexylamino.
  • R 25 preferably represents hydrogen, in each case optionally methyl, ethyl, n- or i-propyl, n-, i- or s-butyl substituted by cyano, hydroxyl, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, propenyl, butenyl, propynyl or butynyl, optionally substituted by cyano, fluorine, chlorine or bromine, or cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl.
  • R 26 preferably represents hydrogen, in each case optionally methyl, ethyl, n- or i-propyl, n-, i- or substituted by cyano, hydroxy, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy s-butyl, in each case optionally substituted by cyano, fluorine, chlorine or bromine, propenyl, butenyl, propynyl or butinyl, in each case optionally by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl
  • X 4 preferably represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Trifluoromethyl,
  • X 5 preferably represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
  • the compounds of the general formula (Ha) to be used as safeners according to the invention are known and or can be prepared by processes known per se (cf. WO-A-91/07874, WO-A-95/07897).
  • the compounds of the general formula (He) to be used as safeners according to the invention are known and / or can be prepared by processes known per se (cf. DE-A-2218097, DE-A-2350547).
  • the compounds of the general formula (Hd) to be used according to the invention as safeners are known and / or can be prepared by processes known per se (cf. DE-A-19621522 / US-A-6235680).
  • the compounds of the general formula (He) to be used as safeners according to the invention are known and / or can be prepared by processes known per se (cf. WO-A-99/66795 / US-A-6251827).
  • component (c ') in particular with regard to the protection of cereal plants, such as, for example, Wheat, barley and rye, but also maize and rice, as crops.
  • Process (A ⁇ ) is characterized in that compounds of the formula (I-a) are each reacted with carboxylic acid halides of the formula (II), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • All solvents which are inert towards the acid halides can be used as diluents in process (A ⁇ ) according to the invention.
  • 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, also ketones such as acetone and methylisopropyl ketone, and furthermore ethers such as diethyl ether, Tetrahydrofuran and dioxane, in addition carboxylic acid esters, such as ethyl acetate, and also strongly polar solvents, such as dimethyl sulfoxide and sulfolane. If the hydrolysis stability of the acid halide permits, the reaction can also be carried out in the presence of water.
  • Suitable acid binders for the reaction according to process (A ⁇ ) according to the invention are all customary acid acceptors.
  • Tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN), Hunig base and N, N-dimethylaniline, and also alkaline earth metal oxides, such as magnesium oxide and calcium oxide, are also preferably used
  • reaction temperature in process (A ⁇ ) 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 materials of the formula (Ia) and the carboxylic acid halide of the formula (H) 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.
  • the process (Aß) is characterized in that compounds of the formula (Ia) are reacted with carboxylic anhydrides of the formula (in), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Diluents which can be used in the process (Aß) according to the invention are preferably those diluents which are also preferred when using acid halides.
  • an excess of carboxylic acid anhydride can also act as a diluent.
  • the acid binders which are optionally added in the process (Aß) are preferably those acid binders which are also preferred when using acid halides.
  • the reaction temperature can be varied within a substantial range in the process (A ⁇ ) according to the invention. In general, temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C.
  • the starting materials of the formula (I-a) and the carboxylic anhydride of the formula (JE) are generally used in approximately equivalent amounts in each case. However, it is also possible to use the carboxylic anhydride in a larger excess (up to 5 mol). The processing takes place according to usual methods.
  • the general procedure is to remove diluent and excess carboxylic acid anhydride and the carboxylic acid formed by distillation or by washing with an organic solvent or with water.
  • Process (B) is characterized in that compounds of the formula (I-a) are in each case reacted with chloroformic acid esters or chloroformic acid thiolesters of the formula (IV), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Suitable acid binders in process (B) 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 (B) according to the invention are all solvents which are inert to the chloroformic acid esters or chloroformic acid thiol esters.
  • Hydrocarbons such as gasoline, benzene, toluene, xylene and tetralin are preferably usable, furthermore halogenated hydrocarbons such as methylene chloride, chloroform, hydrocarbon tetrachloride, chlorobenzene and o-dichlorobenzene, also ketones such as acetone and methylisopropyl ketone, furthermore ethers such as diethyl ether, tetrahydrofuran and dioxane in addition carboxylic acid esters, such as ethyl acetate, and also strongly polar solvents, such as dimethyl sulfoxide and sulfolane.
  • halogenated hydrocarbons such as methylene chloride, chloroform, hydrocarbon tetrachloride, chlorobenzene and o-dichlorobenzene
  • ketones such as acetone and methylisopropyl ketone
  • furthermore ethers such as diethy
  • the reaction temperature can be varied within a substantial range when carrying out process (B) according to the invention.
  • the reaction temperature is generally between -20 ° C and + 100 ° C, preferably between 0 ° C and 50 ° C.
  • Process (B) according to the invention is generally carried out under normal pressure.
  • the starting materials of the formula (I-a) and the corresponding chloroformate or chloroformate thiol ester of the formula (IV) are generally in each case used in approximately equivalent amounts. 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 usual methods. The general procedure is to remove precipitated salts and to concentrate the remaining reaction mixture by stripping off the diluent.
  • Process (C) is characterized in that compounds of the formula (Ia) in each case with (C ⁇ ) compounds of the formula (V) in the presence of a diluent and optionally in the presence of an acid binder or (C ⁇ ) carbon disulfide and then with alkyl halides of the formula (VI) 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, esters, amides, sulfones, sulfoxides, but also haloalkanes.
  • Dimethyl sulfoxide, ethyl acetate, tetrahydrofuran, dimethylformamide or methylene chloride are preferably used. If, in a preferred embodiment, the enolate salt of the compound (Ia) is prepared by adding strong deprotonating agents, such as, for example, sodium hydride or potassium tert-butylate, the further addition of acid binders can be dispensed with.
  • strong deprotonating agents such as, for example, sodium hydride or potassium tert-butylate
  • customary inorganic or organic bases are suitable, examples being 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.
  • the processing takes place according to usual methods.
  • the equimolar amount or an excess of carbon disulfide is added per mole of starting compounds of the formula (I-a).
  • 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 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, diisopropylethylamine, pyridine, quinoline, diazabicyclooctane (DABCO), diazabicyclonones (DBN) and diazabicycloundecen (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 (VT) 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.
  • the processing is again carried out using customary methods.
  • Process (D) according to the invention is characterized in that compounds of the formula (I-a) are each reacted with sulfonic acid chlorides of the formula (VH), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Process (D) is preferably carried out in the presence of a diluent.
  • Suitable diluents are all inert polar organic solvents, such as ethers, esters, amides, nitriles, sulfones, sulfoxides or halogenated hydrocarbons such as methylene chloride.
  • Dimethyl sulfoxide, tetrahydrofuran, ethyl acetate, dimethylformamide, 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 tertiary butoxide), 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, examples being 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.
  • the processing takes place according to usual methods.
  • Process (E) according to the invention is characterized in that compounds of the formula (I-a) are each reacted with phosphorus compounds of the formula (VHS), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Process (E) is preferably carried out in the presence of a diluent.
  • Suitable diluents are all inert, polar organic solvents such as ethers, esters, amides, nitriles, sulfides, sulfones, sulfoxides etc.
  • Acetonitrile, ethyl acetate, dimethyl sulfoxide, tetrahydrofuran, dimethylformamide, 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.
  • the processing 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 volatile components cleaned in vacuo.
  • Process (F) is characterized in that compounds of the formula (I-a) are each reacted with metal hydroxides or metal alkoxides of the formula (IX) or amines of the formula (X), if appropriate in the presence of a diluent.
  • Diluents which can be used in process (F) according to the invention are preferably ethers such as tetrahydrofuran, dioxane, diethyl ether or alcohols such as methanol, ethanol, isopropanol, but also water.
  • Process (F) 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.
  • Process (G) according to the invention is characterized in that compounds of the formula (Ia) are each treated with (G ⁇ ) compounds of the formula (XI) optionally in the presence of a diluent and optionally in the presence of a catalyst or (Gß) with compounds of the formula (X ⁇ ) if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid binder.
  • Process (G ⁇ ) is preferably carried out in the presence of a diluent.
  • Suitable diluents are all inert organic solvents, such as ethers, esters, amides, nitriles, sulfones or sulfoxides. If necessary, catalysts can be added to accelerate the reaction. Organotin compounds such as dibutylzirmdilaurate can be used very advantageously as catalysts.
  • inert polar organic solvents such as ethers, esters, amides, sulfones, sulfoxides or halogenated hydrocarbons, are suitable as diluents which may be added.
  • Dimethyl sulfoxide, ethyl acetate, 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 tertiary butoxide), 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 under normal pressure or under elevated pressure, preferably under normal pressure.
  • the processing takes place according to usual methods.
  • the active substances are suitable for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They can preferably be used as pesticides. 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.
  • Symphyla for example, Scutigerella immaculata.
  • Thysanura for example Lepisma saccharina.
  • Orthoptera e.g. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
  • Phthiraptera e.g. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella occidentalis.
  • Homoptera e.g.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Chorioptes spp. Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp.
  • Plant parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaph.
  • the compounds or active compound combinations according to the invention can, if appropriate, also be used as herbicides in certain concentrations or application rates. If appropriate, the compounds can also be used as intermediates or precursors for the synthesis of further active compounds.
  • Plants are understood to mean all plants and plant populations, such as desired and unwanted wild plants or crops (including naturally occurring crops).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and plant parts according to the invention with the active substances or combinations of active substances takes place directly or by acting on their surroundings, living space or storage space according to the usual treatment methods, e.g. by dipping, spraying, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular in the case of seeds, furthermore by coating in one or more layers.
  • the active ingredients or combinations of 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 and very fine encapsulations polymeric fabrics.
  • 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, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and or foam-forming 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 as well as 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.
  • solid carriers e.g. ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, as solid carriers for granulates are possible: e.g.
  • emulsifiers and / or foam-generating agents are: for example non-ionogenic 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; The following may be used as dispersants: for example lignin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to to broaden the spectrum of activity or to prevent the development of resistance.
  • fungicides bactericides
  • acaricides nematicides or insecticides
  • synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Aldimorph ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin, Benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos, binapacrylic, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,
  • Debacarb dichlorophene, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dirnethomorph, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dorphianzodone, dithianonodone, dithianonodone
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Meth tartroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
  • Oxadixyl Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole,
  • Methane tetrathiol sodium salt methyl l- (2,3-dihydro-2,2-dimethyl-lH-inden-l-yl) -lH-imidazole-5-carboxylate,
  • Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
  • Mecarbam Metaldehyde, Methamidophos, Metharhician anisopliae, Metharhician flavoviride, Methidathione, Methiocarb, Methoprene, Methomyl, Methoxyfenozide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Milbemycin, Monocrotophos,
  • Paecilomyces fumosoroseus Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propargite, Propoxur, Prothiofos, Prothrohrinos, Pothrohrinos, Pothrohrinos, Pothrohrinos, Pothrohrinos , Pyridaben, pyridathione, pyrimidifen, pyriproxyfen,
  • the active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself being active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • the active ingredient or combination of active ingredients When used against hygiene pests and pests of stored products, the active ingredient or combination of active ingredients is distinguished by an excellent residual action on wood and clay and by a good stability to alkali on limed substrates.
  • plants and their parts can be treated.
  • wild plant species or plant species and their parts obtained by conventional biological breeding methods such as crossing or protoplast fusion
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods if appropriate in combination with conventional methods (genetic modified organisms) and their parts are treated.
  • the term "parts” or “parts of plants” or “plant parts” was explained above. Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention. Plant cultivars are understood to mean plants with new properties (“traits”) which have been grown both by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, bio and genotypes.
  • the treatment according to the invention can also cause superadditive (“synergistic") effects.
  • superadditive for example, reduced application rates and / or widening of the activity spectrum and / or an increase in the action of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance , easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvest products, higher storability and / or workability of the harvest products possible, which go beyond the expected effects.
  • the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which, through the genetic engineering modification, have received genetic material which gives these plants particularly advantageous, valuable properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher harvest yields, higher quality and or higher nutritional value of the crop products, higher shelf life and / or workability of the crop products. Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicidal active ingredients.
  • transgenic plants include the important cultivated plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed, beets, sugar cane and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with maize , Soy, potato, cotton and rapeseed are particularly highlighted.
  • the traits are particularly emphasized as the increased defense of the plants against insects by toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), CryIA (b), Cry ⁇ A (c), CryllA, CrylllA, CryIHB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
  • Bt plants As Properties (“traits”) are also particularly emphasized the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • SAR systemic acquired resistance
  • the properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example “PAT” gene).
  • the genes conferring the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
  • Examples of "Bt plants” are maize varieties, cotton varieties, soy varieties and potato varieties that are marketed under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato).
  • herbicide-tolerant plants are maize varieties, cotton varieties and soy varieties that are marketed under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, e.g. rapeseed), IMI® (tolerance to Imidazolinone) and STS® (tolerance to sulfonylureas such as maize).
  • the herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (eg maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
  • the plants listed can be treated particularly advantageously with the compounds according to the invention or the active compound mixtures according to the invention.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • the active substances or combinations of active substances 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, space mites, running mites, flies (stinging and licking), parasitic fly larvae and lice , Hair lice, featherlings and fleas.
  • animal parasites ectoparasites
  • tick ticks such as tick ticks, leather ticks, space mites, running mites, flies (stinging and licking), parasitic fly larvae and lice , Hair lice, featherlings and fleas.
  • parasites include:
  • Anoplurida for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp ..
  • Mallophagida and the subordinates Amblycerina and Ischnocerina for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Wemeckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp ..
  • Nematocerina and Brachycerina From 3 of the order Diptera and the subordinates Nematocerina and Brachycerina, for example Aedes sp r p r ., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp.
  • Hybomitra spp. Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus 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., Hypodterol spp ., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp ..
  • the active substances or combinations of active substances according to the invention are also suitable for combating arthropods, agricultural animals such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees and other domestic animals such as dogs, cats, house birds, aquarium fish and so-called experimental animals such as hamsters, guinea pigs, rats and mice. Fighting these arthropods is said to result in deaths and reduced performance Wool, skins, eggs, honey, etc.) can be reduced, so that more economical and simple animal husbandry is possible through the use of the active compounds according to the invention.
  • arthropods agricultural animals such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees and other domestic animals such as dogs, cats, house birds, aquarium fish and so-called experimental animals such as hamsters, guinea
  • the active substances or combinations of active substances according to the invention are used 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 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 ingredient-containing shaped bodies, such as collars, ear tags, tail tags, limb straps, holsters, marking devices, etc.
  • enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories
  • parenteral administration such as by
  • the active ingredients or combinations of active ingredients can be used as formulations (for example powders, emulsions, flowable agents) which contain the active ingredients in an amount of 1 to 80% by weight, directly or after 100 Apply up to 10,000-fold dilution or use it as a chemical bath.
  • formulations for example powders, emulsions, flowable agents
  • insects may be mentioned by way of example and preferably, but without limitation:
  • Termites like Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
  • Bristle tails such as Lepisma saccharina.
  • non-living materials such as preferably plastics, adhesives, glues, papers and cartons, leather, wood, wood processing products and paints.
  • the material to be protected from insect infestation is very particularly preferably wood and wood processing products.
  • Wood and wood processing products that can be protected by the agent according to the invention or mixtures containing it are to be understood as examples:
  • the active substances or active substance combinations 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, e.g. by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellants, optionally siccatives and UV stabilizers and optionally 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 optimum amount of use 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, white spirit 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 ° C, Te ⁇ entinöl and Like. Used.
  • liquid aliphatic hydrocarbons with a boiling range from 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range from 180 to 220 ° C. and or lock oil and / or monochloronaphthalene, preferably ⁇ -monochloronaphthalene, are used.
  • 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 solvents, with the proviso that the solvent mixture also has an evaporation number 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.
  • part of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced.
  • Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups, such as, for example, glycol ethers, esters or the like, are preferably used.
  • the known organic-chemical binders are the water-thinnable and / or soluble or dispersible or emulsifiable synthetic resins and / or binders which are soluble or dispersible in the organic-chemical solvents used drying oils, in particular binders consisting of or containing an acrylate resin, a vinyl resin, for example 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 are used.
  • binders consisting of or containing an acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such
  • 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 with 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 fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. 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 glycol or glycerol ether 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
  • stearates such as butyl stearate or amyl
  • 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, optionally 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 may optionally contain further insecticides and, if appropriate, one or more fungicides.
  • the insecticides and fungicides mentioned in WO 94/29 268 are preferably suitable as additional mixing partners.
  • the compounds mentioned in this document are an integral part of the present application.
  • Insecticides such as Chlo ⁇ yriphos, Phoxim, Silafluofin, Alphamethrin, Cyfluthrin, Cypermethrin, Deltamethrin, Permethrin, Imidacloprid, NI-25, Flufenoxuron, Hexaflumuron, Transfluthrin, Methoxyphenuronoprid, Thiacloxiduron
  • fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluoride, tolylfluanid, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro octylisothiazolin-3-one.
  • the compounds or active substance combinations according to the invention can be used to protect objects, in particular ship hulls, sieves, nets, structures, quay systems and signaling systems which come into contact with sea or brackish water.
  • heavy metals such as in bis (trialkyltin) sulfides, tri-butyltin laurate, tri-butyltin chloride, copper (I) oxide, triethyltin chloride, Tri - «- butyl (2-phenyl-4-chloro-phenoxy) tin, tributyltin oxide, molybdenum disulfide, antimony oxide, polymeric butyl titanate, phenyl (bispyridine) bismuth chloride, tri - « - butyltin fluoride, manganese ethylenebisfhio carbamate, zinc dimethyldithamate, zinc dimethyldithamate, zinc carbamate, zinc carbamate, zinc carbamate, zinc carbamate, zinc carbamate, zinc carbamate and copper salts of 2-pyridinthiol-1-oxide, bisdimethyldithiocarbamoylzin
  • the ready-to-use antifouling paints can optionally contain other active ingredients, preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.
  • Suitable combination partners for the antifouling agents according to the invention are preferably:
  • Benzo [b] thiophenecarboxylic acid cyclohexylamide-S, S-dioxide, dichlofluanid, fluorfolpet, 3-iodo-2-propynyl-butylcarbamate, tolylfluanid and azoles such as
  • the antifouling agents used contain the active compound according to the invention of the compounds according to the invention in a concentration of 0.001 to 50% by weight, in particular 0.01 to 20% by weight.
  • the antifouling agents according to the invention furthermore contain the usual constituents such as, for example, in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, described in 1973.
  • antifouling paints contain in particular binders.
  • Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system, in particular in an aqueous system, vinyl chloride / vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene / styrene / acrylonitrile Rubbers, drying oils, such as linseed oil, resin esters or modified hard resins in combination with tar or bitumen, asphalt and epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.
  • Paints may also contain inorganic pigments, organic pigments or dyes, which are preferably insoluble in seawater. Paints may also contain materials, such as rosin, to enable controlled release of the active ingredients. The paints may also contain plasticizers, modifiers affecting theological properties, and other conventional ingredients. The compounds according to the invention or the abovementioned mixtures can also be incorporated into self-polishing antifouling systems.
  • the active substances or combinations of active substances are also suitable for controlling animal pests, in particular insects, arachnids and mites, which live in closed rooms, such as, for example, apartments, factory halls, offices, vehicle cabins and the like. occurrence. To combat these pests, they can be used alone or in combination with other active ingredients and auxiliaries in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:
  • Sco ⁇ ionidea e.g. Buthus occitanus.
  • Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
  • Opiliones for example Pseudosco ⁇ iones chelifer, Pseudosco ⁇ iones cheiridium, Opiliones phalangium.
  • Isopoda for example Oniscus asellus, Porcellio scaber.
  • Diplopoda e.g. Blaniulus guttulatus, Polydesmus spp ..
  • Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia inte ⁇ unctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
  • Ctenocephalides canis Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • Pediculus humanus capitis for example Pediculus humanus capitis, Pediculus humanus co ⁇ oris, Phthirus pubis.
  • Heteroptera for example Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
  • the active substances or active substance combinations according to the invention can also be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow up 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 active substances or active substance combinations according to the invention can e.g. can be used in the following plants:
  • Echinochloa Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, hnperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Sci ⁇ us, Setaria, Sorghum.
  • the active substances or active substance combinations according to the invention are suitable for combating total weeds, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the active compounds according to the invention for combating weeds in permanent crops e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land and for selective purposes Weed control can be used in annual crops.
  • the compounds or active ingredient combinations according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocot and dicot weeds in monocot and dicot crops, both in the pre-emergence and in the post-emergence process.
  • the active substances or active substance combinations according to the invention can also be used in certain concentrations or application rates for controlling animal pests and fungal or bacterial plant diseases. If appropriate, they can also be used as intermediates or products for the synthesis of further active ingredients.
  • the active substances or active substance combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations polymeric fabrics.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and or dispersants and or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorefhylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, for example 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 powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known herbicides and / or with substances which improve crop tolerance (“safeners”) for weed control, ready-to-use formulations or tank mixes being possible are also mixtures with weed Pesticides possible, which contain one or more known herbicides and a safener.
  • safeners substances which improve crop tolerance
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
  • the active substances or active substance combinations can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules.
  • the change is made in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
  • the active substances or active substance combinations according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
  • 1 part by weight of active compound of the formula (I) salts comprises 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight, particularly preferably 0.05 to 20 parts by weight of one of the compounds mentioned above under (c ') which improve the tolerance to crop plants ( antidotes / safeners).
  • the active compound combinations according to the invention are generally used in the form of finished formulations.
  • the contained in the drug combinations Active ingredients can also be mixed in the form of individual emulsions during use, ie they can be used in the form of tank mixtures.
  • mineral or vegetable oils compatible with plants e.g. the commercial preparation "Rako Binol”
  • ammonium salts such as e.g. Include ammonium sulfate or ammonium rhodanide.
  • the new active compound combinations can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. by pouring, spraying, spraying, dusting or scattering.
  • the application rates of the active compound combinations according to the invention can be varied within a certain range; depending on the weather and soil factors. In general, the application rates are between 0.001 and 5 kg per ha, preferably between 0.005 and 2 kg per ha, particularly preferably between 0.01 and 0.5 kg per ha.
  • the active substance combinations according to the invention can be applied before and after emergence of the plants, that is to say in the pre-emergence and post-emergence process.
  • the safeners to be used according to the invention can be used for pretreating the seed of the cult pot plant (dressing the seeds) or introduced into the seed furrows before sowing or used separately before the herbicide or together with the herbicide before or after the plants have run off become.
  • Seeds of monocotyledonous or dicotyledonous weed or cultivated plants are laid out in wood fiber pots in sandy loam soil and covered with soil and grown in the greenhouse under good growing conditions. After 2 to 3 weeks after sowing, the test plants are treated at the single-leaf stage.
  • Formulation code g a.i./ha Avena sativa Lolium Setaria
  • Test plants are laid out in wood fiber pots or in plastic pots in sandy loam soil, covered with soil and grown in the greenhouse, during the growing season also outdoors outside the greenhouse, under good growing conditions.
  • the test plants are treated in the one- to three-leaf stage.
  • the test compounds formulated as wettable powder (WP) or liquid (EC) are sprayed onto the plants and the soil surface in various dosages with a water application rate of the equivalent of 300 l / ha with the addition of wetting agent (0.2 to 0.3%).
  • WP wettable powder
  • EC liquid
  • cultivated plants are sprayed with the safener at a certain hectare rate (usually 1 day before using the test substances
  • the safener is applied together with the test substance as a tank mixture
  • the effect of the safener can be assessed by comparing the effect of test substances on cultivated plants which have been treated with and without safener. Mefenpyr 1 day before herbicide application
  • Emulsifier 0.5 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 emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Chinese cabbage leaf slices (Brassica pekinensis) are sprayed with an active ingredient preparation of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochlea ⁇ ae).
  • the effect is determined in%. 100% means that all beetle larvae have been killed; 0% means that none of the beetle larvae have been killed.
  • Emulsifier 0.5 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 emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Chinese cabbage leaf slices (Brassica pekinensis), which are affected by all stages of the green peach aphid (Myzus persicae), are sprayed with an active ingredient preparation of the desired concentration.
  • the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • Emulsifier 0.5 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 emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Bean leaf slices Phaseolus vulgaris
  • Triticae Tricholine dexase
  • Bean leaf slices Phaseolus vulgaris
  • which are affected by all stages of the common spider mite Tetranychus urticae
  • an active ingredient preparation of the desired concentration is sprayed with an active ingredient preparation of the desired concentration.
  • the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
  • Test insect Diabrotica balteata - larvae in the soil
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • the active ingredient preparation is poured onto the floor.
  • the concentration of the active ingredient in the preparation is practically irrelevant, the only decisive factor is the amount of active ingredient per unit volume of soil, which is given in ppm (mg / 1). You fill the bottom in 0.25 1 pots and let them stand at 20 ° C.
  • 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.
  • Soybean shoots (Glycine max) of the Roundup Ready variety (trademark of Monsanto Comp. USA) are treated by dipping into the preparation of active compound of the desired concentration and populated with the tobacco bud caterpillar Heliothis virescens while the leaves are still moist.
  • the killing of the insects is determined.

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Abstract

La présente invention concerne des dérivés d'acide tétramique spirocycliques à substitution 2-éthyl-4,6-diméthyl-phényle de formule (I) dans laquelle A, B et G possèdent la signification définie dans le descriptif, plusieurs procédés et produits intermédiaires de fabrication desdits dérivés et leur utilisation en tant que produits de lutte contre les parasites et / ou herbicides, ainsi que des agents sélectivement herbicides qui contiennent les dérivés d'acide tétramique spirocycliques à substitution 2-éthyl-4,6-diméthyl-phényle de formule (I) d'une part (G pouvant également représenter hydrogène) et au moins un composé améliorant la compatibilité avec les plantes cultivées d'autre part.
EP04803114A 2003-11-22 2004-11-09 Derives d'acide tetramique spirocycliques a substitution 2-ethyl-4,6-dimethyl-phenyle Withdrawn EP1687272A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10354629A DE10354629A1 (de) 2003-11-22 2003-11-22 2-Ethyl-4,6-dimethyl-phenyl substituierte spirocyclische Tetramsäure-Derivate
PCT/EP2004/012644 WO2005049569A1 (fr) 2003-11-22 2004-11-09 Derives d'acide tetramique spirocycliques a substitution 2-ethyl-4,6-dimethyl-phenyle

Publications (1)

Publication Number Publication Date
EP1687272A1 true EP1687272A1 (fr) 2006-08-09

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US20070298969A1 (en) 2007-12-27
DE10354629A1 (de) 2005-06-30
WO2005049569A1 (fr) 2005-06-02
BRPI0416209A (pt) 2006-12-26
AR046780A1 (es) 2005-12-21
US7727933B2 (en) 2010-06-01
CA2546815A1 (fr) 2005-06-02
CN1914172A (zh) 2007-02-14
JP2007513882A (ja) 2007-05-31

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