EP1686856A1 - Derives d'acide tetramique susbtitues par 2-ethyl-4,6-dimethyl-phenyle comme antiparasitaires et/ou herbicides - Google Patents

Derives d'acide tetramique susbtitues par 2-ethyl-4,6-dimethyl-phenyle comme antiparasitaires et/ou herbicides

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Publication number
EP1686856A1
EP1686856A1 EP04797725A EP04797725A EP1686856A1 EP 1686856 A1 EP1686856 A1 EP 1686856A1 EP 04797725 A EP04797725 A EP 04797725A EP 04797725 A EP04797725 A EP 04797725A EP 1686856 A1 EP1686856 A1 EP 1686856A1
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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.)
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Application number
EP04797725A
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German (de)
English (en)
Inventor
Reiner Fischer
Stefan Lehr
Dieter Feucht
Peter Lösel
Olga Malsam
Guido Bojack
Thomas Auler
Martin Jeffrey Hills
Heinz Kehne
Christopher Hugh Rosinger
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Bayer CropScience AG
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Bayer CropScience AG
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Priority to EP10159199A priority Critical patent/EP2218330A1/fr
Publication of EP1686856A1 publication Critical patent/EP1686856A1/fr
Withdrawn legal-status Critical Current

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    • 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
    • C07D495/04—Ortho-condensed systems
    • 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
    • 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
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/38—2-Pyrrolones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Definitions

  • the invention relates to new 2-ethyl-4,6-dimethyl- ⁇ henyl-substituted tetramic acid derivatives, several processes and intermediates for their preparation and their use as pesticides and / or herbicides.
  • the invention also relates to new selective herbicidal active substance 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 crop tolerance on the other hand and with particularly good success for selective weed control with various crop plants can be used.
  • 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).
  • EP-A-442 073 polycyclic 3-arylpyrrolidine-2,4-dione derivatives
  • EP-A-613 884 polycyclic 3-arylpyrrolidine-2,4-dione derivatives
  • EP-A-613 884 polycyclic 3-arylpyrrolidine-dione derivatives
  • EP-A-613 885 EP-A 94/01 997, WO 93/26954, WO 95/20 572, EP-A 0 668 267, WO 96/25 395, WO 96 35 664, WO 97/01 535, WO 97/02243, WO 97/36 868, WO 97/43275, WO / 98/05638, WO 98/06721, WO 98/25928, WO 99/16748, WO 99/24437, WO 99 / 43649, WO 99/48869, WO 99/55673, WO 01/09092, WO 01/17972, WO 01/23354
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulfur
  • M stands for oxygen or sulfur
  • R 1 stands for optionally substituted alkyl, alkenyl, alkoxyalkyl, al ylthioalkyl or polyalkoxyalkyl or for each cycloalkyl or heterocyclyl optionally substituted by halogen, alkyl or alkoxy or for optionally substituted phenyl, phenylalkyl, phenylalkenyl or hetaryl .
  • R 2 represents in each case optionally substituted by halogen alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl or represents 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 substituted 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,
  • A represents hydrogen, represents in each case optionally substituted by halogen, alkyl, alkenyl, alkoxyalkyl or alkylthioalkyl or represents optionally substituted cycloalkyl,
  • B represents hydrogen, alkyl or alkoxyalkyl
  • D represents hydrogen or an optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, or optionally substituted cycloalkyl or
  • a and D together with the atoms to which they are attached represent a saturated or unsaturated and optionally at least one heteroatom-containing cycle which is unsubstituted or substituted in the A, D part, and if
  • B for hydrogen or alkyl
  • D for an optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl or optionally substituted cycloalkyl
  • a and D together with the atoms to which they are attached for a saturated or unsaturated and optionally at least one heteroatom contained in the A, D part of the unsubstituted or 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. In the following the However, for the sake of simplicity, compounds of the formula (I) are always used, although both the pure compounds and, if appropriate, mixtures with different proportions of isomeric compounds are meant.
  • A, B, D, E, L, M, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given above.
  • R 8 stands for alkyl (preferably CC 6 alkyl), intramolecularly condensed in the presence of a diluent and in the presence of a base.
  • R 1 has the meaning given above and
  • R 1 has the meaning given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • R 2 and M have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • M and R 2 have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder or
  • R 2 has the meaning given above and
  • Shark represents chlorine, bromine or iodine, if appropriate in the presence of a diluent and if appropriate in the presence of a base.
  • Hai represents halogen (especially chlorine or bromine), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Me for a mono- or divalent metal (preferably an alkali or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium), t for the number 1 or 2 and
  • R 10 , R 11 , R 12 independently of one another represent hydrogen or alkyl (preferably C 8 -C 8 alkyl), optionally reacted in the presence of a diluent.
  • R 6 and L have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst or
  • L, R 6 and R 7 have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • the new compounds of the formula (I) have very good activity as pesticides, preferably as insecticides and / or acaricides and / or as herbicides.
  • A represents hydrogen, represents in each case optionally substituted by halogen alkyl, alkenyl, alkoxyalkyl or alkylthioalkyl or represents optionally substituted cycloalkyl
  • B represents hydrogen, alkyl or alkoxyalkyl
  • EP-A-582198 4-carboxy-chroman-4-yl-acetic acid (AC-304415, cf. EP-A-613618), 4-chlorophenoxy-acetic acid, 3,3'-dimethyl -4-methoxy-benzophenone, l-bromo-4-chloromethylsulfonylbenzene, l- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea (aka N- (2-methoxybenzoyl) - 4 - [(methylaminocarbonyl) amino] benzenesulfonamide), 1 - [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3,3-dimethylurea, l- [4- (N-4 , 5-dimethylbenzoylsulfamoyl) phenyl] -3-methylurea, l-
  • n a number 0, 1, 2, 3, 4 or 5
  • a 1 represents one of the divalent heterocyclic groupings outlined below,
  • n stands for a number between 0 and 5
  • a 2 represents alkanediyl with 1 or 2 carbon atoms which is optionally substituted by C 1 -C 4 -alkyl and / or Ci- -alkoxy-carbonyl and / or CC-alkenyloxy-carbonyl,
  • R 14 represents hydroxyl, mercapto, amino, -C 6 -alkoxy, -C 6 -alkylthio, -C-C 6 -alkylamino or di- (-C 4 -alkyl) -amino,
  • R 16 represents CC 4 alkyl which is optionally substituted by fluorine, chlorine and / or bromine,
  • R 17 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 -Al nyl, C r C 4 -alkoxy-C r C 4 - alkyl, dioxolanyl-C C 4 -alkyl, furyl, furyl-C r C -alkyl, thienyl, thiazolyl, piperidinyl, or phenyl optionally substituted by fluorine, chlorine and / or bromine or CC-alkyl,
  • R 18 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 r C 4 alkoxy-C r C 4 - alkyl, dioxolanyl-C r C 4 -alkyl, furyl, furyl -CC-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 together for each optionally by -C 4 alkyl, phenyl, furyl, one fused benzene ring or C 3 -C 6 alkanediyl or C 2 -C 5 oxaalkanediyl which are substituted by two substituents which together with the carbon atom to which they are attached form a 5- or 6-membered carb
  • R 19 represents hydrogen, cyano, halogen, or C r C -alkyl, C 3 -C 6 -cycloalkyl or phenyl which are each optionally substituted by fluorine, chlorine and or bromine,
  • R 20 represents hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl or tri- (C, -C 4 -alkyl) -silyl optionally substituted by hydroxyl, cyano, halogen or CC 4 -alkoxy, C 3 -C 6 -cycloalkyl,
  • R 21 represents hydrogen, cyano, halogen, or C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl or phenyl which is optionally substituted by fluorine, chlorine and / or bromine,
  • X 1 represents nitro, cyano, halogen, C r C 4 alkyl, CC 4 haloalkyl, CC 4 alkoxy or -C 4 haloalkoxy,
  • X 2 represents hydrogen, cyano, nitro, halogen, CC 4 alkyl, CC haloalkyl, CC alkoxy or CC 4 haloalkoxy, represents hydrogen, cyano, nitro, halogen, -GrAlkyl, C r C 4 haloalkyl, C ⁇ -C 4 alkoxy or CC 4 haloalkoxy,
  • t stands for 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 CC 4 alkyl
  • R 23 represents hydrogen or C r C 4 alkyl
  • R 25 for hydrogen, optionally substituted by cyano, hydroxy, halogen or -C 4 alkoxy -CC 6 alkyl, in each case optionally substituted by cyano or halogen, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl, or C -C-cycloalkyl optionally substituted by cyano, halogen or CC 4 alkyl,
  • R 26 represents hydrogen, optionally cyano-, hydroxyl-, halogen or -G t -alkoxy-substituted Ci-C ⁇ -alkyl, in each case optionally cyano- or halogen-substituted C 3 -C ⁇ - alkenyl or C 3 -C 6 -alkynyl, optionally cyano- , Halogen or -CC alkyl substituted C 3 -C 6 cycloalkyl, or optionally substituted by nitro, cyano, halogen, C] -C 4 alkyl, -C-C 4 haloalkyl, CC 4 alkoxy or CC haloalkoxy Is phenyl, or together with R 25 stands for C 2 -C 6 -alkanediyl or C 2 -C 5 -oxaalkanediyl which is optionally substituted by C 1 -C 4 -alkyl,
  • X 4 represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halogen, CC 4 -alkyl, C 4 haloalkyl, CC 4 -alkoxy or C ⁇ -C is 4 haloalkoxy, and
  • X 5 represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halogen, - C 4 -alkyl, C 4 haloalkyl, CC 4 -alkoxy or CC is 4 -haloalkoxy.
  • G preferably represents hydrogen (a)
  • A preferably represents hydrogen or C j -CG alkyl
  • B preferably represents hydrogen or C j -CG alkyl
  • D preferably represents in each case optionally monosubstituted to pentasubstituted by halogen CC 8 - alkyl, CC 8 alkenyl, C ⁇ -C 6 -alkoxy-C 2 -C 4 -alkyl or C 6 alkylthio-C 2 -C 4 -alkyl, optionally C 3 -C 8 cycloalkyl which is monosubstituted to trisubstituted by halogen, -CC 4 -alkyl, CC -alkoxy or CC 2 -halogenoalkyl,
  • a and D together preferably for a C 3 -C 6 -alkanediyl or C 3 -C 6 -alkenediyl group, in which a methylene group is optionally replaced by oxygen or sulfur and which are each optionally mono- to disubstituted by halogen, hydroxy, -GrAlkyl or -C ⁇ alkoxy, or by a further, a fused ring forming C 3 -Cg-alkanediyl, C 3 -C 6 -alkenediyl or C 4 -C 6 -alkanedienediyl group
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulfur
  • M oxygen or sulfur
  • R 2 preferably represents in each case optionally mono- to trisubstituted by halogen-substituted CC 20 -alkyl, QrQzo-alkenyl, CrC 6 -alkoxy-C 2 -C6-alkyl or poly-C r C 6 -alkoxy-C 2 -C 6 - alkyl , for C 3 -C 8 -cycloalkyl which is optionally mono- to disubstituted by halogen, Cj-C ⁇ -alkyl or Ci-C ⁇ -alkoxy or for in each case optionally monosubstituted to triple by halogen, cyano, nitro, Ci-C ö alkyl, C r C 6 alkoxy, Ci-C ö haloalkyl or -C ⁇ -haloalkoxy substituted phenyl or benzyl,
  • R 3 preferably represents optionally mono- to polysubstituted by halogen, C ⁇ -C 8 - alkyl, or represents in each case optionally mono- to disubstituted by halogen, C ⁇ -C6 alkyl, -C 6 alkoxy, CC 4 haloalkyl, CC 4 -haloalkoxy , Cyano or nitro substituted phenyl or benzyl,
  • R 4 and R 5 independently of one another preferably represent in each case optionally monosubstituted to trisubstituted by halogen C ⁇ -C 8 alkyl, CC 8 alkoxy, CC 8 alkylamino, di- (C ⁇ -C 8 - alkyl) amino, - -Allcylthio or C 2 -C 8 alkenylthio or for each optionally single to triple by halogen, nitro, cyano, -C 4 alkoxy, -C-C 4 -haloalkoxy, CC 4 - alkylthio, -C-C 4 -haloalkylthio, C] - C 4 alkyl or C) -C 4 haloalkyl substituted phenyl, phenoxy or phenylthio,
  • R 6 and R 7 independently of one another preferably represent hydrogen, for each optionally mono- to trisubstituted by halogen -CC 8 alkyl, C 3 -C 8 cycloalkyl, CC 8 alkoxy, C 3 -C 8 alkenyl or CC 8 -alkoxy-C 2 -C 8 -alkyl, each optionally optionally up to three times by halogen, C] -C 8 -alkyl, CC 8 -haloalkyl or CC 8 -alkoxy substituted phenyl or benzyl or together represent an optionally mono- or disubstituted by C ⁇ -C 4 alkyl-substituted C 3 -C 6 -alkylene radical in which optionally one methylene group is replaced by oxygen or sulfur,
  • R * 3 preferably represents in each case optionally up to three times by halogen, substituted Ci-Cg-alkyl, C3-Cg-alkenyl, C3-Cg-alkynyl or C 1 -C 4 -alkoxy-C2-C 4 -alkyl or for optionally simply to C3-C6-cycloalkyl substituted twice by halogen, C 1 -C 2 -alkyl or Ci - C2-alkoxy, in which one or two not directly adjacent methylene groups are optionally replaced by oxygen,
  • R 13 ' preferably represents hydrogen, C] -C 6 alkyl or C 3 -C 6 alkenyl, then stands
  • a preferred for hydrogen for in each case optionally mono- to trisubstituted by halogen CC 8 -alkyl, C 2 -C 8 -alkenyl, QC ö -alkoxy- ⁇ -alkyl or -Ce-alkylthio-- CC -alkyl, for optionally single to C 3 -C 8 cycloalkyl substituted three times by halogen, CC 6 alkyl or CC 6 alkoxy,
  • B is preferred for hydrogen, -CC 6 alkyl or -CC 4 alkoxy -CC 2 -alkyl or
  • D is preferred for hydrogen, for in each case optionally mono- to trisubstituted by halogen -Cs-alkyl, CC 8 -alkenyl, CC 6 -alkoxy-C 2 -C 4 -alkyl or CC 6 -alkylthio-C 2 -C 4 -alkyl, for C 3 -C 8 cycloalkyl which is optionally monosubstituted to trisubstituted by halogen, C 1 -C 6 -alkyl, CC 4 -alkoxy or C 1 -C 2 -haloalkyl,
  • a and D together preferably for a C 3 -C 6 -alkanediyl or C 3 -C 6 -alkenediyl group, in which a methylene group is optionally replaced by oxygen or sulfur and which are each optionally mono- to disubstituted by halogen, hydroxy, -C-C 4 alkyl or C] -C4 alkoxy, or by a further, a fused ring forming -Cg-alkanediyl, C 3 -C 6 -alkenediyl or C -C 6 -alkanediene diyl group.
  • halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
  • G particularly preferably represents hydrogen (a), then stands
  • B particularly preferably represents hydrogen or C j -C 4 alkyl
  • D is particularly preferred for CC 6 -alkyl, C3-Cö-alkenyl, -C 4 -alkoxy-C 2 -C 3 -alkyl or -C 4 -Akylthio- C 2 -C 3, each optionally mono- to trisubstituted by fluorine or chlorine alkyl, for C 3 -C 6 cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine, CC 2 alkyl, CC 2 alkoxy or trifluoromethyl,
  • a and D together are particularly preferred for a C 3 -C 5 -alkanediyl group, in which a methylene group is optionally replaced by oxygen or sulfur and which is optionally monosubstituted or disubstituted by C 1 -C 2 -alkyl or C] -C 2 -alkoxy,
  • a and D together with the atoms to which they are attached represent one of the groups AD-1 to AD-10
  • E represents a metal ion equivalent or an ammonium ion
  • L stands for oxygen or sulfur and M stands for oxygen or sulfur
  • R 2 particularly preferably represents in each case optionally mono- to trisubstituted by fluorine or chlorine-substituted alkyl, C 2 -C ] 0 -alkenyl, -C-C 4 -alkoxy-C 2 -C 4 -alkyl or poly-Cr C 4 -alkoxy-C 2 -C 4 -alkyl, for C 3 -C 7 -cycloalkyl which is optionally monosubstituted or substituted by C 1 -C 2 -alkyl or C 1 -C 2 -alkoxy or for each optionally optionally up to twice by fluorine, chlorine, bromine , Cyano, nitro, CC 4 alkyl, methoxy, trifluoromethyl or trifluoromethoxy substituted phenyl or benzyl, R 3 particularly preferably represents CC 4 alkyl which is optionally monosubstituted to trisubstituted by fluorine or chlorine or represents in each case
  • R 4 and R 5 independently of one another are particularly preferably each QQ ⁇ alkyl, QQ-alkoxy, QQ-alkylamino, di- (C 1 -C 6 -alkyl) amino, CC 6 -alkylthio or optionally substituted up to three times by fluorine or chlorine QQ-alkenylthio or phenyl, phenoxy or phenylthio, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, nitro, cyano, QQ-alkoxy, trifluoromethoxy, C 1 -C 3 -alkylthio, QQ-alkyl or trifluoromethyl,
  • R 6 and R 7 independently of one another particularly preferably represent hydrogen, in each case QQ-alkyl, QQ-cycloalkyl, C r C -alkoxy, C 3 -C 6 -alkenyl or QQ-alkoxy- which is optionally mono- to trisubstituted by fluorine or chlorine.
  • QQ-alkyl for phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, trifluoromethyl, C 1 -C 4 -alkyl or QQ-alkoxy, or together for a QQ-alkylene radical which is optionally monosubstituted or disubstituted by methyl, in which optionally one Methylene group is replaced by oxygen,
  • R 13 stands particularly preferably for C 1 -C 4 -alkyl, C3-C ⁇ .-alkenyl, C3-C4-alkynyl or C1-C4-alkoxy-C2-C3 -alkyl or for C3-Cg-cycloalkyl, in which, if appropriate, a methylene group is formed by Oxygen is replaced, then stands
  • A is particularly preferred for hydrogen, for QQ-alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 3 -alkyl or C 1 -C 4 -alkylthio-C 1 -substituted or disubstituted by fluorine or chlorine -C 3 -alkyl or for QQ-cycloalkyl which is optionally monosubstituted or disubstituted by fluorine, chlorine, C 1 -C 2 -alkyl or QQ-alkoxy,
  • B particularly preferably for hydrogen, Q-C-alkyl or Q-Q-alkoxy-Q-Q-alkyl
  • D also particularly preferably for QQ-alkyl, C3-Cg-alkenyl, QQ-alkoxy-QQ-alkyl or QQ-alkylthio-QQ-alkyl, which are optionally monosubstituted to trisubstituted by fluorine or chlorine, for optionally monosubstituted to twice by fluorine, chlorine , QQ-alkyl, QQ-alkoxy or trifluoromethyl substituted QQ-cycloalkyl, with the proviso that then A only represents hydrogen or C 1 -C 3 alkyl,
  • a and D together are particularly preferred for a Q-Q-alkanediyl group in which a methylene group is optionally replaced by oxygen or sulfur and which is optionally mono- to disubstituted by Q-Q-alkyl or Q-Q-alkoxy,
  • a and D together with the atoms to which they are attached represent one of the groups AD-1 to AD-10
  • halogen represents fluorine, chlorine and bromine, in particular fluorine and chlorine.
  • G very particularly preferably represents hydrogen (a), then stands
  • D very particularly preferably for methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, cyclopropyl, cyclopentyl or cyclohexyl,
  • a and D together very particularly preferably for a Q-Q-alkanediyl group, in which in each case one methylene group is replaced by oxygen or sulfur and which is optionally mono- to disubstituted by methyl
  • M oxygen or sulfur
  • R 1 very particularly preferably represents in each case mono- to trisubstituted by fluorine or chlorine-substituted QQ-alkyl, QQ-alkenyl, QQ-alkoxy-QQ-alkyl, QQ-AJkyltWo-QQ-alkyl or poly-C 1 -C 2 -alkoxy-C 1 -C2-alkyl or for each optionally cyclopropyl, cyclopentyl or cyclohexyl substituted simply by fluorine, chlorine, methyl, ethyl or methoxy, for optionally simply by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, methoxy, ethoxy, methylthio, Ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfony
  • R 2 very particularly preferably represents QQ-alkyl, QQ-alkenyl or QQ-alkoxy-QQ-alkyl, cyclopentyl or cyclohexyl, or each in each case simply by fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy substituted phenyl or benzyl,
  • R 3 very particularly preferably represents QQ-alkyl which is monosubstituted to trisubstituted by fluorine or chlorine or phenyl or benzyl which is optionally monosubstituted by fluorine, chlorine, bromine, QQ-alkyl, QQ-alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro .
  • R 6 very particularly preferably represents hydrogen, QQ-alkyl, QQ-cycloalkyl or allyl, each phenyl optionally substituted by fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl,
  • R7 very particularly preferably represents methyl, ethyl, n-propyl, isopropyl or allyl,
  • R and R ⁇ together very particularly preferably represent a Q-Q-alkylene radical in which a methylene group is optionally replaced by oxygen, then stands
  • B very particularly preferably for hydrogen, methyl or ethyl
  • D also very particularly preferably for methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, cyclopropyl, cyclopentyl or cyclohexyl, with the proviso that then
  • R 1 stands for QQ-alkyl or QQ-alkoxy-QQ-alkyl
  • R 2 stands for QQ-alkyl
  • R 3 stands for QQ-alkyl, then stands for QQ-alkyl
  • Saturated or unsaturated hydrocarbon radicals such as alkyl, alkanediyl or alkenyl, can also be straight-chain or branched as far as possible, also in conjunction with heteroatoms, such as, for example, in alkoxy.
  • 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 preferably represents hydrogen, C j -CG alkyl or C 1 -CG-alkoxy-C ⁇ is -Qj-alkyl.
  • G particularly preferably represents hydrogen (a),
  • A is particularly preferred for hydrogen, C 1 -C 6 -alkyl, C 1 -C 2 haloalkyl having one to three fluorine atoms or C 1 -C 4 alkoxy C 1 -C 4 alkyl or for optionally one to two times by fluorine, chlorine, C 1 -C 2 Alkyl or -C 2 -C alkoxy substituted C3 ⁇ C - cycloalkyl,
  • B particularly preferably represents hydrogen, C 1 -C 2 -alkyl or C 1 -C 8 -alkoxy-C 1 -C 2 -alkyl.
  • G very particularly preferably represents hydrogen (a),
  • B very particularly preferably represents hydrogen, methyl or ethyl.
  • herbicide safeners of the formulas (Ha), (üb), (Hc), (Ild) and (He) which improve crop plant tolerance are defined below.
  • n preferably represents the numbers 0, 1, 2, 3 or 4,
  • a 1 preferably represents one of the divalent heterocyclic groups outlined below
  • a 2 preferably represents in each case methylene or ethylene which is optionally substituted by methyl, ethyl, methoxycarbonyl or ethoxycarbonyl or allyloxycarbonyl,
  • R 1 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, Me ylarnino, E ylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino,
  • R 1 15 preferably represents hydroxy, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, 1-methyl-hexyloxy, allyloxy, 1-allyloxymethyl-ethoxy, 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 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 phenyl substituted by fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl .
  • 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 phenyl substituted by fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , or together with R 17 for one of the radicals -CH 2 -O-CH 2 -CH2- and -CH2-CH 2 -O-CH 2 -CH2-, which are optionally substituted by methyl,
  • 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, chlorodifluoromethyl , 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, dime ylamino or diethylamino, or in each case optionally by cyano, fluorine, chlorine, bro
  • 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 qvano, 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 s-butyl substituted by cyano, hydroxy, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, propenyl, butenyl, propynyl or butynyl optionally substituted by cyano, fluorine, chlorine or bromine, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, or optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy
  • 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, methoxy, ethoxy, n- or i-propoxy, difluoimethoxy or trifluoromethoxy,
  • 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,
  • Table 7 Examples of the selectively herbicidal combinations according to the invention, each of an active ingredient of the formula (I) and in each case one of the safeners defined above, are listed in Table 7 below. Table 7 Examples of the combinations according to the invention
  • the compounds of the general formula (Ha) to be used according to the invention as safeners 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 (ex) to be used as safeners according to the invention are known and / or can be prepared by processes known per se (cf. EP-A-191736).
  • the compounds of the general formula Rc) 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 ⁇ TJd) 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).
  • component c The particularly advantageous effect of the particularly and most preferred combination partners from component c 'should be emphasized, in particular with regard to the protection of cereal plants, such as Wheat, barley and rye, but also maize and rice, as crops.
  • carboxylic acid activation reagents such as carbonyldiimidazole, carbonyldiimides (such as dicyclohexylcarbodiimide), phosphorylation reagents (such as POCI3, BOP-Cl), halogenating agents such as e.g. Thionyl chloride, oxalyl chloride, phosgene or chloroformate ester introduced leaving group,
  • D, A and B have the meanings given above, and D ⁇ H,
  • halogenating agents e.g. thionyl chloride, thionyl bromide, oxalyl chloride, phosgene, phosphorus trichloride, phosphorus tribromide or phosphorus pentachloride
  • phosphonylation reagents such as (e.g. POCI3, BOP-Cl), carbonyldiimidazole, carbonyldiimides (e.g.
  • dicyclohexyl carbonate optionally in the presence of a (eg aromatic hydrocarbons such as toluene or methylene chloride or ethers, for example tetrahydrofuran, dioxane, methyl tert-butyl ether) at temperatures of from -20 ° C. to 150 ° C., preferably from -10 ° C. to 100 ° C.
  • a aromatic hydrocarbons such as toluene or methylene chloride or ethers, for example tetrahydrofuran, dioxane, methyl tert-butyl ether
  • the compound of the formula (XV ⁇ i) is in principle analogous to G.C. Lloyd-Jones, Angew. Chem. Int. Ed. 2002, 41, 953-956; S.L. Buchwald, W.A. Moradi, JACS 2001, L23, 7996-8002 and S. Lee, N.A. Beare, J.F. Hartwig, JACS 2001, 123, 8410-8411 can be produced:
  • the process is characterized in that 2-ethyl-4,6-dimethylbromobenzene is reacted with tert-butyl acetate, if appropriate in the presence of a diluent, if appropriate in the presence of a base, if appropriate in the presence of a phosphine ligand and if appropriate in the presence of palladium-O compounds and then reacted with an acid.
  • All solvents which are inert to the reagents can be used as diluents in the process according to the invention.
  • Hydrocarbons such as gasoline, benzene, toluene, xylene and tetralin, and furthermore ethers, such as diethyl ether, dimethoxyethane, tetrahydrofuran and dioxane, can preferably be used.
  • Suitable bases for the reaction according to the process of the invention are lithium amide bases, preferably lithium hexyl disilazide, lithium diisopropyl amide, lithium dicyclohexyl amide.
  • Suitable phosphine ligands are tri-tert-butylphosphine and 2-
  • Bis- (dibenzylidene acetone) -palladium may be mentioned as the palladium-0 compound.
  • Organic acids may be mentioned as acids, e.g. For example, formic acid or inorganic acids such as, for example, hydrochloric acid or sulfuric acid.
  • the reaction temperature can be varied within a substantial range in the process according to the invention. In general, temperatures between -80 ° C and + 150 ° C, preferably between 0 ° C and 100 ° Q
  • the starting materials are generally used in approximately equivalent amounts.
  • the acid halides of the formula (DT), carboxylic anhydrides of the formula (IV) which are also required as starting materials for carrying out processes (B), (C), (D), (E), (F), (G) and (H) , Chloroformate or chloroformate thioester of the formula (V), chloromothio formate or chlorodithio formate ester of the formula (VI), alkyl halides of the formula (VII), sulfonic acid chlorides of the formula (VTJJ), phosphorus compounds of the formula (DO.
  • metal hydroxides, metal alkoxides or amines of the formula ( X) and (XI) and isocyanates of the formula (XH) and carbamic acid chlorides of the formula (XQT) are generally known compounds of organic or inorganic chemistry.
  • Process (A) is characterized in that compounds of the formula (II) in which A, B and R 8 have the meanings given above and D ⁇ H are in the presence of a diluent and in the presence of a base of an intramolecular condensation subjects.
  • 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 toluene and xylene are preferably usable, furthermore ethers such as dibutyl ether, tetrahydrofuran, Dioxane, glycol dimethyl ether and diglycol dimethyl ether, as well as polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone, and alcohols such as methanol, ethanol, propanol, iso-propanol, butanol, iso-butanol and tert-butanol.
  • All the usual proton acceptors can be used as the base (deprotonating agent) when carrying out process (A) according to the invention.
  • Alkali metals such as sodium or potassium can also be used.
  • alkali metal and alkaline earth metal amides and hydrides such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates, such as sodium methylate, sodium ethylate and potassium tert-butoxide, can also be used.
  • reaction temperature can be varied within a substantial range when carrying out process (A) according to the invention. In general, temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C.
  • Process (A) according to the invention is generally carried out under normal pressure.
  • reaction component of the formula (II) and the deprotonating base are generally employed in equimolar to approximately double-equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles).
  • Process (B ⁇ ) is characterized in that compounds of the formulas (I-a) or (I-a ') are each reacted with carboxylic acid halides of the formula (HI), 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 the process (B ⁇ ) 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, 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.
  • 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.
  • alkali and alkaline earth metal carbonates such as sodium carbonate, potassium carbonate and calcium carbonate
  • alkali hydroxides such as sodium hydroxide and potassium hydroxide.
  • reaction temperature in process (B ⁇ ) 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 formulas (I-a) or (I-a ') and the carboxylic acid halide of the formula (TU) 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 formulas (I-a) or (I-a ') are each reacted with carboxylic anhydrides of the formula (IV), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Suitable diluents for the process (Bß) 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.
  • Suitable acid binders which may be added in process (Bß) 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 (Bß) according to the invention. In general, temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° Q
  • Formulas (Ia) or (Ia 1 ) and the carboxylic anhydride of the formula (TV) are generally used in approximately equivalent amounts. However, it is also possible to use the carboxylic anhydride in use a larger excess (up to 5 moles). 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 (C) is characterized in that compounds of the formulas (I-a) or (I-a ') are in each case reacted with chloroformic acid esters or chloroformic acid thiolesters of the formula (V), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • 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 metal and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate, can preferably be used 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 solvents which are inert to chloroformic acid esters or chloroformic acid thioliol esters.
  • 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, 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.
  • the reaction temperature can be varied within a substantial range when carrying out process (C) according to the invention.
  • the reaction temperature is generally between -20 ° C and + 100 ° C, preferably between 0 ° C and 50 ° C.
  • Process (C) according to the invention is generally carried out under normal pressure.
  • the starting materials of the formulas (Ia) or (I-a ') and the corresponding chloroformic acid ester or chloroformic acid thiol ester of the formula (V) 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. in the 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 formulas (Ia) or (I-a ') are each reacted with (Da) compounds of the formula (VI) 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 (VII), 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.
  • the addition of strong deprotonating agents such as e.g. Sodium hydride or potassium tert-butylate, the enolate salt of the compounds (I-a) or (I-a '), can be dispensed with the further addition of acid binders.
  • 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 to each mole of starting compounds of the formulas (Ia) or (Ia 1 ).
  • the process is preferably carried out at temperatures from 0 to 50 ° C. and in particular at 20 to 30 ° C.
  • 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 diazabicycloundecene (DBU).
  • DABCO diazabicyclooctane
  • DBN diazabicyclonones
  • DBU diazabicycloundecene
  • 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 (VII) 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 (E) is characterized in that compounds of the formulas (I-a) or (I-a ') are each reacted with sulfonyl chlorides of the formula (VIII), 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, sulfones, sulfoxides or halogenated hydrocarbons such as methylene chloride.
  • Dimethyl sulfoxide, tetrahydrofuran, ethyl acetate, dimethylformamide, methylene chloride are preferably used. If, in a preferred embodiment, the enolate salt of the compounds (Ia) or (I-a ') 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.
  • Process (F) is characterized in that compounds of the formulas (I-a) or (I-a ') are each reacted with phosphorus compounds of the formula (TX), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Process (F) 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.
  • Process (G) is characterized in that compounds of the formulas (Ia) or fj-a ') are each reacted with metal hydroxides or metal alkoxides of the formula (X) or amines of the formula (XI), 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.
  • Process (H) is characterized in that compounds of the formulas (Ia) or (Ia ") are each treated with (H ⁇ ) compounds of the formula (XH), if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst or (Hß) Compounds of formula (XuT) optionally 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, esters, amides, nitriles, sulfones or sulfoxides.
  • catalysts can be added to accelerate the reaction.
  • Organotin compounds such as e.g. Dibutyltin dilaurate can be used.
  • 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 compounds (I-a) or (I-a ') is represented by the addition of strong deprotonating agents (such as sodium hydride or potassium tertiary butylate), the further addition of acid binders can be dispensed with.
  • strong deprotonating agents such as sodium hydride or potassium tertiary butylate
  • 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.
  • Thysanura e.g. Lepisma saccharina.
  • Orthoptera e.g. Acheta domesticus, Gryllotalpa spp., Locustä 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 accidentalis.
  • Homoptera e.
  • Otiorrhynchus sulcatus Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Giptusibbium psol. Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.
  • 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
  • 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 here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • 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 the plants, such as sprout, leaf, flower and root, examples being leaves, needles, stems, stems, flowers, cargo 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, for example by dipping, spraying, spraying, vaporising, atomizing, spreading, spreading and, in the case of propagation material, in particular in the case of seeds, still by single or multi-layer coating.
  • 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, 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 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.
  • 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 nonionogenic 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, widen the spectrum of activity or prevent the development of resistance. In many cases, synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Debacarb dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalirnfos, dithorphoxinodonine, dithorphononodine
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
  • Oxadixyl Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
  • Paclobutrazole pefurazoate, penconazole, pencycuron, Phosdiphen, picoxystrobin, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidon, propamocarb, propanosine sodium,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, tridemorph, trifloxystrobin, Triflurnizol, triforine, triticonazole,
  • Fenamiphos Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxuron, Fluthrinoxin, Fluutinoxin, Fluutinoxin , Fubfenprox, Furathiocarb,
  • 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 having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • the active ingredient 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.
  • all 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 cultivars 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 effort quantities and / or extensions of the spectrum of action 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, Accelerated ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products, which go beyond the effects that are actually to be expected.
  • the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, 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 crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products.
  • transgenic plants are the important crop 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 corn , Soy, potato, cotton and rapeseed are 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), Cry ⁇ A (b), Cry ⁇ A (c), CryllA, CrylllA, Cry] JIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
  • the properties (“traits”) also particularly emphasize 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 imparting the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
  • Examples of "Bt plants” are maize, cotton, soybean and Potato varieties named under the trade names YTELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato) to be expelled.
  • herbicide-tolerant plants are maize varieties, cotton varieties and soy varieties that are sold under the trade names Roundup Ready® (tolerance to glyphosate, e.g. maize, cotton, soy), Liberty Link® (tolerance to phosphinotricin, e.g. rape), IMI® ( Tolerance to imidazolinones) 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 shield ticks, leather ticks, space mites, running mites, flies (stinging and licking), parasitic fly larvae , Lice, hair lice, featherlings and fleas.
  • animal parasites ectoparasites
  • shield ticks such as shield ticks, leather ticks, space mites, running mites, flies (stinging and licking), parasitic fly larvae , Lice, hair lice, featherlings and fleas.
  • parasites include:
  • Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
  • Nematocerina and Brachycerina for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia s cw pp>., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota s ⁇ p r ⁇ p)., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp
  • Actinedida Prostigmata
  • Acaridida Acaridida
  • 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 which are used in agricultural animals, e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice.
  • arthropods e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice.
  • 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 for 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, pumping in and with the help of active ingredient-containing shaped bodies such as necklaces, ear tags, tail tags, limb tapes, 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 for example
  • the active ingredients or combinations of active ingredients can be formulated (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.
  • insects may be mentioned by way of example and preferably, but without limitation:
  • 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 which can be protected by the agent according to the invention or mixtures containing it are to be understood as examples: Lumber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone poles, wooden cladding, wooden windows and doors, plywood, chipboard, carpentry or wooden products that are generally used in house construction or joinery.
  • the active substances or combinations of active substances 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.
  • 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 locker 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 is replaced by an aliphatic polar organic chemical solvent or solvent mixture.
  • 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 organic-chemical binders used are the water-thinnable synthetic resins which are known per se and / or 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 acrylate 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 acrylate resin, a vinyl resin, e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydro
  • 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-repellent agents, odor correctors and inhibitors or anticorrosive agents and the like can be used. According to the invention, 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.
  • 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
  • the compounds or active substance combinations according to the invention can be used to protect objects, in particular hulls, sieves, nets, structures, quay systems and signaling systems which come into contact with sea or brackish water.
  • heavy metals such as e.g. in bis (trialkyltin) sulfide, tri-M-butyltin laurate, tri-butyltin chloride, copper (I) oxide, triethyltin chloride, tri-n-butyl (2-phenyl-4-chl ⁇ henoxy) tin, tributyltin oxide, molybdenum disulfide, Antimony oxide, polymeric butyl titanate, phenyl (bispyridine) bismuth chloride, tri- / z-butyltin fluoride, manganese ethylene bisthiocarbamate, zinc dimethyldithiocarbamate, zinc ethylene bisthiocarbamate, zinc and copper salts of 2-pyridinethiol-1-oxide, bisdimethyldihamide, bisdimethyldihamidoxydihamidoxydiamide, bisdimethyldimidiumd
  • the ready-to-use antifouling paints may also contain other active ingredients, preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.
  • 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 further contain the usual ingredients such as in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 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 / acrylic - Nitrile 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 that affect the rheological 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 e.g. Pseudosco ⁇ iones chelifer, Pseudosco ⁇ iones cheiridium, Opiliones phalangium.
  • 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.
  • the active substances or combinations of active substances 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 understood to mean 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 combinations of active substances according to the invention can e.g. can be used in the following plants:
  • the active compounds or combinations of active compounds according to the invention are suitable for combating total weeds, for example on industrial and track systems and on Because of and places with and without tree cover.
  • the active compounds according to the invention for weed control in permanent crops for example forests, ornamental trees, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants can also be used , on ornamental and sports turf and pasture land as well as for selective weed control 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 monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in the pre-emergence and in the post-emergence process.
  • the active substances or combinations of active substances 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 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 manufactured in a known manner, e.g. B. by mixing the active ingredients with extenders, that is liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie 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 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.
  • Possible solid carriers are: for example ammonium salts and natural rock powders 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 dispersants are: eg lignin sulfate leachate 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 formulation 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, finished formulations or tank mixes being possible. Mixtures are therefore also possible possible with weed control agents 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 combinations of active substances 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. They are used in the customary manner, for example by watering, spraying, spraying or scattering.
  • the active substances or combinations of active substances 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 improves the tolerance of the crop plants ( antidotes / safeners).
  • the active compound combinations according to the invention are generally used in the form of finished formulations.
  • the active ingredients contained in the active ingredient combinations can also be mixed in individual formulations during use, i.e. be used in the form of tank mixes.
  • mineral or vegetable oils which are compatible with plants (e.g. the commercial preparation "Rako Binol") or ammonium salts such as e.g. Include ammonium sulfate or ammonium rhodanide.
  • the new active substance combinations can be used as such, in the form of their formulation or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. 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; they depend, among other things, 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 compound 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 cultivated plant (dressing the seeds) or introduced into the seed furrows prior to sowing or used separately before the herbicide or together with the herbicide before or after the plants have run off become.
  • Example Id-2 Analogous to Example Id-1, Example Id-2 with a melting point of 102 ° C. is obtained.
  • component K 5.7 g are stirred in 100 ml of formic acid for 2 hours at room temperature. It is then poured onto 500 ml of ice water, allowed to stir at room temperature for 30 min and the solid formed is filtered off with suction. To dry, the residue is taken up in dichloromethane and this solution is dried with sodium sulfate. After concentration, 3.67 g of 2-ethyl-4,6-dimethyl-phenylacetic acid are obtained, which corresponds to an overall yield of 81% over all stages. Mp 128-129 ° C.
  • Seeds of monocotyledonous or dicotyledonous weed or cultivated plants are laid out in wood fiber pots in sandy loam soil, covered with earth and grown in the greenhouse under good growth conditions.
  • the test plants are treated at the single-leaf stage 2-3 weeks after sowing.
  • the test compounds formulated as wettable powder (WP) are sprayed onto the green parts of the plant in various metering rods with a water application rate of the equivalent of 600 l / ha with the addition of 0.2% wetting agent.
  • WP wettable powder
  • 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 1 ha with the addition of wetting agents (0.2 to 0.3%).
  • WP wettable powder
  • EC liquid
  • Seeds of the cultivated plants are stained with the safener substance before sowing (indication of the safener quantity in percent based on the seed weight)
  • cultivated plants are sprayed with the safener using a certain amount of hectare (usually 1 day after using the test substances).
  • the safener is applied together with the test substance as a tank mix (indication of the safener quantity in g / ha or as a ratio to the herbicide).
  • 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. Vascular experiments with grain in the greenhouse
  • 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 cochleariae).
  • 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.
  • 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 substance in the preparation is practically irrelevant, the only decisive factor is the weight of the active substance 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

L'invention concerne de nouveaux dérivés d'acide tétramique substitués par 2-éthyl-4,6-diméthyl-phényle de formule (I), dans laquelle A, B, D et G ont les significations indiquées dans les revendications, plusieurs procédés et produits intermédiaires pour la production desdits dérivés et leur utilisation comme antiparasitaires et/ou herbicides ainsi que des agents herbicides sélectifs contenant, d'une part, des dérivés d'acide tétramique substitués par 2-éthyl-4,6-diméthyl-phényle de formule (I) et, d'autre part, au moins un composé améliorant la tolérance des plantes cultivées.
EP04797725A 2003-11-22 2004-11-09 Derives d'acide tetramique susbtitues par 2-ethyl-4,6-dimethyl-phenyle comme antiparasitaires et/ou herbicides Withdrawn EP1686856A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP10159199A EP2218330A1 (fr) 2003-11-22 2004-11-09 Procedé pour la préparation de acide acétique 2-éthyl-4,6-diméthylphényl par réaction de 2-éthyl-4,6-diméthylbromobenzene avec tert.-butylacetate

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10354628A DE10354628A1 (de) 2003-11-22 2003-11-22 2-Ethyl-4,6-dimethyl-phenyl-substituierte Tetramsäure-Derivate
PCT/EP2004/012646 WO2005048710A1 (fr) 2003-11-22 2004-11-09 Derives d'acide tetramique susbtitues par 2-ethyl-4,6-dimethyl-phenyle comme antiparasitaires et/ou herbicides

Publications (1)

Publication Number Publication Date
EP1686856A1 true EP1686856A1 (fr) 2006-08-09

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EP10159199A Withdrawn EP2218330A1 (fr) 2003-11-22 2004-11-09 Procedé pour la préparation de acide acétique 2-éthyl-4,6-diméthylphényl par réaction de 2-éthyl-4,6-diméthylbromobenzene avec tert.-butylacetate
EP04797725A Withdrawn EP1686856A1 (fr) 2003-11-22 2004-11-09 Derives d'acide tetramique susbtitues par 2-ethyl-4,6-dimethyl-phenyle comme antiparasitaires et/ou herbicides

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EP10159199A Withdrawn EP2218330A1 (fr) 2003-11-22 2004-11-09 Procedé pour la préparation de acide acétique 2-éthyl-4,6-diméthylphényl par réaction de 2-éthyl-4,6-diméthylbromobenzene avec tert.-butylacetate

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US (2) US20070225167A1 (fr)
EP (2) EP2218330A1 (fr)
JP (1) JP2007511557A (fr)
KR (1) KR20060097136A (fr)
CN (2) CN101823951A (fr)
AR (1) AR047251A1 (fr)
AU (2) AU2004290516B2 (fr)
BR (1) BRPI0416207A (fr)
CA (1) CA2546817A1 (fr)
DE (1) DE10354628A1 (fr)
RU (1) RU2386615C2 (fr)
WO (1) WO2005048710A1 (fr)

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CN101823951A (zh) 2010-09-08
CA2546817A1 (fr) 2005-06-02
KR20060097136A (ko) 2006-09-13
CN1905793A (zh) 2007-01-31
JP2007511557A (ja) 2007-05-10
US20100240924A1 (en) 2010-09-23
AR047251A1 (es) 2006-01-11
BRPI0416207A (pt) 2006-12-26
EP2218330A1 (fr) 2010-08-18
AU2004290516A1 (en) 2005-06-02
DE10354628A1 (de) 2005-06-16
WO2005048710A1 (fr) 2005-06-02
RU2386615C2 (ru) 2010-04-20
US20070225167A1 (en) 2007-09-27
RU2006121917A (ru) 2007-12-27
AU2004290516B2 (en) 2010-03-04
AU2010202042A1 (en) 2010-06-10

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