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WO2003067986A1 - $g(d)1-pyrrolines et leur utilisation dans la lutte antiparasitaire - Google Patents

$g(d)1-pyrrolines et leur utilisation dans la lutte antiparasitaire Download PDF

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WO2003067986A1
WO2003067986A1 PCT/EP2003/001024 EP0301024W WO03067986A1 WO 2003067986 A1 WO2003067986 A1 WO 2003067986A1 EP 0301024 W EP0301024 W EP 0301024W WO 03067986 A1 WO03067986 A1 WO 03067986A1
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alkyl
chlorine
fluorine
alkoxy
bromine
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PCT/EP2003/001024
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German (de)
English (en)
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Udo Kraatz
Martin FÜSSLEIN
Johannes Rudolf Jansen
Thomas Seitz
Christoph Erdelen
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Bayer Cropscience Ag
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Priority to AU2003206816A priority Critical patent/AU2003206816A1/en
Publication of WO2003067986A1 publication Critical patent/WO2003067986A1/fr

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    • 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
    • C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/18—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by doubly-bound oxygen atoms
    • 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
    • C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D207/20—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • 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
    • C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings

Definitions

  • the present invention relates to new ⁇ ⁇ pyrrolines, several processes for their preparation and their use as pesticides.
  • R 1 represents alkyl or optionally substituted aryl
  • R represents halogen, cyano, nitro, amino, alkyl or alkoxy
  • R represents hydrogen, halogen, alkyl or alkoxy
  • R 4 stands for the grouping -XYZE, with the proviso that Y does not stand for a direct bond if X does not stand for a direct bond
  • R 5 represents halogen, in each case optionally substituted alkyl, alkoxy or alkylthio,
  • n 0, 1, 2, 3 or 4, where the radicals R 5 can be the same or different if m represents 2, 3 or 4, X for a direct bond, oxygen, -S (O) w -, -NR 6 -, carbonyl, carbonyloxy, oxycarbonyl, oxysulfonyl (OSO 2 ), alkylene, haloalkylene, alkenylene, haloalkenylene, alkynylene, alkyleneoxy, oxyalkylene, oxyalkyleneoxy , -S (O) w - alkylene, cyclopropylene or oxiranylene,
  • Y stands for a direct bond or for optionally substituted phenylene, naphthylene, tetrahydronaphthylene or heterocyclylene,
  • Z represents a direct bond or - (CH 2 ) n -
  • Pentafluorthio, -S (O) w R 7 , -OSO 2 R 7 , -NR 8 R 9 , -COR 7 , -CO 2 R 7 , -OC (O) R 7 , -CONR 10 R ⁇ , -N ( R 12 ) COR 13 , -C (R 14 ) N-OR 15 , -SO 2 NR 16 R 17 ,
  • R 6 represents optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
  • R represents in each case optionally substituted alkyl, cycloalkyl, aryl or arylalkyl,
  • R 8 and R 9 independently of one another represent hydrogen, -SO R 7 , each optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or saturated or unsaturated heterocyclyl or heterocyclylalkyl,
  • R 8 and R 9 also together represent optionally substituted alkenylene or alkylene, where the alkylene chain can in each case be interrupted by -O-, -S- or -NR -, R 10 and R n independently of one another represent hydrogen, -SO 2 R 7 , each optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or saturated or unsaturated heterocyclyl or heterocyclylalkyl,
  • R, 10 and R also together represent optionally substituted alkylene, where the alkylene chain can be interrupted by -O-, -S- or -NR 21 -,
  • R 12 and R 13 independently of one another represent hydrogen, in each case optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
  • R 12 and R 13 also together represent optionally substituted alkylene or alkenylene,
  • R 14 and R 15 independently of one another represent hydrogen, in each case optionally substituted alkyl or alkenyl,
  • R 16 and R 17 independently of one another represent hydrogen, in each case optionally substituted alkyl or cycloalkyl
  • R 16 and R 17 together also represent optionally substituted alkylene, alkoxyalkylene or alkylthioalkylene,
  • R 18 represents hydrogen or alkyl
  • R 19 and R 20 independently of one another represent hydrogen, in each case optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, saturated or unsaturated heterocyclyl or heterocyclylalkyl,
  • R 18 and R 19 also together represent optionally substituted alkylene, or R 19 and R 20 together with the nitrogen atom to which they are attached also represent a saturated or unsaturated heterocycle which can optionally contain a further hetero atom group from the series -O-, -S- or -NR 22 - and which optionally can be substituted
  • R 21 is hydrogen, -SO 2 R 7 , -COR 7 or -CO 2 R 7 ; represents in each case optionally substituted alkyl, alkenyl, cycloalkyl, aryl, or saturated or unsaturated heterocyclyl,
  • , 22 represents hydrogen, alkyl or alkenyl
  • w 0, 1 or 2
  • n stands for 1, 2, 3 or 4.
  • the compounds of the formula (I) can optionally be present as geometric and / or optical isomers or regioisomers or their isomer mixtures in different compositions. Both the pure isomers and the isomer mixtures are claimed according to the invention.
  • R ⁇ R 2 R 3 , R 4 , R 5 and m have the meanings given above,
  • R 41 stands for the grouping -Y ⁇ E
  • Y 1 represents in each case optionally substituted phenylene or heterocyclylene
  • ⁇ > 42 Z represents chlorine, bromine, iodine, -OSO 2 CF 3 or -OSO 2 (CF 2 ) 3 CF 3 ,
  • R 1 , R 2 , R 3 , R 5 and m have the meanings given above,
  • a 1 represents chlorine, bromine, iodine, -OSO 2 CF 3 or -OSO 2 (CF 2 ) 3 CF 3 ,
  • a 2 for -B (OH) 2 (4,4,5,5-tetramethyl-l, 3,2-dioxaborolane) -2-yl, (5,5-dimethyl-1, 3,2-dioxaborinane ) -2-yl, (4,4,6-trimethyl-1,3, 2-dioxaborinan) -2-yl or l, 3,2-benzodioxaborol-2-yl,
  • R 1 , R 2 , R 3 , R 5 and m have the meanings given above,
  • R, R, R, R, R, m and R, 42 have the meanings given above, with boronic acid derivatives of the formula (VI) A - YE (VI) in which
  • R »43 represents bromine or iodine
  • R 1 , R 2 , R 3 , R 5 and m have the meanings given above,
  • organometallic compounds of the formula (Vif) -Y— E (v ⁇ ) in which
  • M represents ZnCl, Sn (Me) 3 or Sn (n-Bu) 3 ,
  • Y 1 and E have the meanings given above, in the presence of a catalyst, optionally in the presence of an acid binder and optionally in the presence of a diluent.
  • the compounds of the formula (I) according to the invention have very good insecticidal properties and can be used both in crop protection and in material protection to control unwanted pests, such as insects.
  • ⁇ ⁇ pyrrolines according to the invention are generally defined by the formula (I).
  • R 1 is C 1 -C 8 -alkyl or optionally mono- or polysubstituted, identical or differently substituted aryl, the substituents being selected from the group consisting of halogen, cyano, nitro, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy and haloalkylthio .
  • R 2 represents halogen, cyano, nitro, amino, C 1 -C 4 alkyl or Ci-C 4 alkoxy,
  • R 3 represents hydrogen, halogen, -CC 6 -alkyl or -CC 6 alkoxy
  • R 4 stands for the grouping -XYZE, with the proviso that Y does not stand for a direct bond if X does not stand for a direct bond
  • R 5 represents halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or haloalkylthio,
  • n 0, 1, 2, 3 or 4, where the radicals R 5 can be the same or different if m represents 2, 3 or 4, X for a direct bond, oxygen, -S (O) w -, -NR 6 -, carbonyl, carbonyloxy, oxycarbonyl, oxysulfonyl (OSO 2 ), alkylene, haloalkylene, alkenylene, haloalkenylene, alkynylene, alkyleneoxy, oxyalkylene, oxyalkyleneoxy , -S (O) w - alkylene, cyclopropylene or oxiranylene,
  • Y for a direct bond or for in each case optionally up to four times, identical or different, substituted by radicals from the list W 1, phenylene, naphthylene, tetrahydronaphthylene or 5- to 10-membered, saturated or unsaturated heterocyclylene with one or more heteroatoms from the nitrogen series , Oxygen and sulfur stands,
  • Z represents a direct bond or - (CH) n -
  • Pentafluorthio, -S (O) w R 7 , -OSO 2 R 7 , -NR 8 R 9 , -COR 7 , -CO 2 R 7 , -OC (O) R 7 , -CONR 10 R ⁇ , -N ( R 12 ) COR 13 , -C (R 14 ) N-OR 15 , -SO 2 NR 16 R 17 ,
  • alkyl alkenyl, alkynyl, alkoxy, alkenyloxy optionally substituted once or several times, identically or differently by halogen, cyano, alkoxy and / or -NR 8 R 9 ; or for cycloalkyl, cycloalkylalkyl, cycloalkyloxy, aryl, arylalkyl, aryloxy which are optionally mono- or polysubstituted, identically or differently, by halogen, cyano, nitro, alkyl, haloalkyl, alkenyl, haloalkenyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio.
  • W 1 for halogen, cyano, formyl, nitro, trialkylsilyl, alkyl, haloalkyl, alkoxy, haloalkoxy, alkenyl, haloalkenyl, alkenyloxy, haloalkenyloxy, alkylcarbonyl, alkoxycarbonyl, -S (O) w R 7 , -C (R 14 ) N-OR 15 , -SO 2 NR 16 R 17 , - (CH 2 ) P NR 16 R 17 , - (CH 2 ) p N (R 16 ) COR 17 , - (CH 2 ) p N (R 16 ) SO 2 R 17 , -OSO 2 R 16 , -OSO 2 NR 16 R 17 , R 6 stands for alkyl, haloalkyl, or for cycloalkyl, cycloalkylalkyl, aryl or arylalkyl which is optionally mono- or
  • R 7 for optionally mono- or polysubstituted, identically or differently, by halogen and / or -NR 8 R 9 substituted alkyl, in each case optionally mono- or polysubstituted, identically or differently by halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio substituted cycloalkyl, aryl or arylalkyl,
  • R 8 and R 9 independently of one another for hydrogen, -SO 2 R 7 , for in each case optionally singly or multiply, identically or differently, alkyl or alkenyl substituted by halogen, alkylcarbonyl, alkylcarbonyloxy, alkylamino, dialkylamino, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio ; for cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, saturated or unsaturated, 5- to 10-membered heterocyclyl or heterocyclylalkyl, each optionally mono- or polysubstituted, identically or differently, by halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio with one or more heteroatoms from the series nitrogen, oxygen and sulfur,
  • R 8 and R 9 furthermore together for optionally substituted one or more times, identically or differently by halogen, cyano, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio, or for optionally once or more times, identically or differently, by halogen, cyano, alkyl, haloalkyl , Alkoxy, haloalkoxy, alkylthio and / or haloalkylthio substituted alkylene, where the alkylene chain can be interrupted by -O-, -S- or -NR 21 -,
  • R 10 and R 11 independently of one another for hydrogen, -SO 2 R 7 , for each in each case optionally singly or multiply, identically or differently by halogen, Alkylamino, dialkylamino, alkoxy and / or alkylthio substituted alkyl or alkenyl; for cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, saturated or unsaturated, 5- to 10-membered heterocyclyl or heterocyclylalkyl, each optionally mono- or polysubstituted, identically or differently, by halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio with one or more heteroatoms from the series nitrogen, oxygen and sulfur,
  • R 10 and R 11 also jointly represent alkylene which is optionally mono- or polysubstituted, identically or differently, by halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio, the alkylene chain being represented by -O-, -S- or -NR 21 - may be interrupted
  • R 12 and R 13 independently of one another for hydrogen, for alkyl which is optionally mono- or polysubstituted identically or differently by halogen, cyano, alkoxy and / or alkylthio, for in each case optionally mono- or polysubstituted, identically or differently by halogen, cyano, alkyl, haloalkyl , Alkoxy, haloalkoxy, alkylthio and / or haloalkylthio substituted cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
  • R 12 and R 13 furthermore each stand for alkylene or alkenylene which is optionally mono- or polysubstituted, identically or differently, by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio,
  • R 14 and R 15 independently of one another represent hydrogen, alkyl, alkenyl, haloalkyl or haloalkenyl
  • R 16 and R 17 independently of one another represent hydrogen, alkyl, haloalkyl or cycloalkyl which is optionally mono- or polysubstituted identically or differently by halogen or alkyl, R 16 and R 17 furthermore together represent alkylene, alkoxyalkylene or alkylthioalkylene which may be mono- or polysubstituted identically or differently by halogen or alkyl,
  • R 18 represents hydrogen or alkyl
  • R 19 and R 20 independently of one another for hydrogen, each optionally mono- or polysubstituted, identically or differently, by halogen, alkylcarbonyloxy, alkylcarbonyloxy, alkylamino, dialkylamino, alkoxy, alkylthio, alkoxyalkoxy, haloalkoxy, haloalkylthio and / or haloalkoxyalkoxy-substituted alkyl or alkenyl;
  • R 18 and R 19 also together represent alkylene which is mono- or polysubstituted by alkyl, or
  • R 19 and R 20 together with the nitrogen atom to which they are attached also represent a saturated or unsaturated 5- to 10-membered heterocycle which may optionally be a further hetero atom group from the series -O-, -S- or -NR 22 - May contain and which may optionally be substituted one or more times, identically or differently, by halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy and / or haloalkylthio, and
  • R 21 is hydrogen, -SO 2 R 7 , -COR 7 or -CO 2 R 7 ; for in each case optionally one or more times, identically or differently, by halogen, cyano, alkylamino, dialkylamino, alkoxy, haloalkoxy, alkylthio and / or Ha- logenalkylthio substituted alkyl or alkenyl; for cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, saturated or unsaturated, 5- to 10-membered heterocyclyl or heterocyclylalkyl, each optionally mono- or polysubstituted, identically or differently, by halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio with one or more heteroatoms from the series nitrogen, oxygen and sulfur,
  • R 22 represents hydrogen, alkyl or alkenyl
  • w 0, 1 or 2
  • n 1, 2, 3 or 4
  • p stands for 0, 1 or 2.
  • R 1 represents C 1 -C 4 -alkyl or aryl (in particular phenyl) which is optionally monosubstituted to tetrasubstituted by identical or different substituents, the substituents from the series fluorine, chlorine, bromine, iodine, cyano, nitro, -Q alkyl, Ci- C 4 - alkoxy, C ⁇ -C 4 - alkylthio, -C 4 haloalkyl, -C 4 -haloalkoxy and - haloalkylthio thereof with in each case 1 to 9 fluorine, chlorine and / or bromine atoms,
  • R 2 represents fluorine, chlorine, bromine, cyano, nitro, amino, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy,
  • R 3 represents hydrogen, fluorine, chlorine, bromine, - -alkyl or Ci- -alkoxy
  • R 4 stands for the grouping -XYZE with the proviso that Y does not stand for a direct bond if X does not stand for a direct bond
  • R 5 for fluorine, chlorine, bromine, -C 6 alkyl, -C 6 alkoxy, -C 6 alkylthio.
  • C ⁇ -C 6 - haloalkyl, C ⁇ -C 6 haloalkoxy or C ! -C 6 haloalkylthio each having 1 to 13 fluorine, chlorine and / or bromine atoms,
  • n 0, 1, 2 or 3, where the radicals R 5 can be identical or different if m represents 2 or 3,
  • X for a direct bond, oxygen, -S (O) w -, -NR 6 -, carbonyl, carbonyloxy, oxycarbonyl, oxysulfonyl (OSO 2 ), -C ⁇ - alkylene, dC 6 -haloalkylene, C 2 -C 6 - Alkenylene, C 2 -C 6 haloalkenylene, C -C 6 alkynylene, CrC ⁇ alkylene oxy, Ci-C ⁇ -oxyalkylene, oxy-CrC 6 alkyleneoxy or -S (O) w -C ⁇ -C 6 alkylene stands,
  • Y for a direct bond or for in each case optionally up to four times, identical or different, 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 2,6-naphthylene substituted by radicals from the list W 1 , 7-naphthylene, 1,4-naphthylene, 2,6- (l, 2,3,4-tetrahydro) naphthylene, 2,7- (l, 2,3,4-tetrahydro) -naphthylene, 1,4- ( 1, 2,3,4-tetrahydro) naphthylene, 5,8- (l, 2,3,4-tetrahydro) naphthylene; or for in each case optionally up to four times, identically or differently, 5- or 6-membered, saturated or unsaturated heterocyclylene substituted by radicals from the list W 1 with 1 to 3 heteroatoms, which has 0 to 3 nitrogen atoms, 0 to 2 non-adjacent oxygen atoms and
  • Z represents a direct bond or - (CH 2 ) n -
  • W 1 for fluorine, chlorine, bromine, cyano, formyl, nitro, tri- (dC 6 -alkyl) silyl, dC 6 - alkyl, C ⁇ -C 6 -haloalkyl, dC 6 -alkoxy, dC 6 -haloalkoxy, C 2 - C 6 -alkenyl, C 2 -C 6 -halogenalkenyl, C 2 -C 6 -alkenyloxy, C -C 6 -halogenalkenyloxy, dC 6 -alkylcarbonyl, dC 6 -alkoxycarbonyl, -S (O) w R 7 , - C (R 14 ) N-OR 15 , -SO 2 NO.
  • R 6 is C 6 - alkyl, dC ö haloalkyl, or represents in each case optionally mono- to tetrasubstituted by identical or different substituents from halogen, C ⁇ -C6 alkyl, dC logenalkyl 6 -Ha-, dC 6 alkoxy, C ⁇ - C 6 -haloalkoxy, dC 6 -alkylthio and / or dC 6 -haloalkylthio substituted C 3 -C 7 -cycloalkyl, C 3 -C 6 -cycloalkyl- C 1 -C 4 -alkyl, aryl or aryl -CC-C 4 - alkyl stands, R 7 for dC 2 -alkyl which is optionally mono- or polysubstituted, identically or differently, by halogen and / or -NR R, in each case optionally up to eight times, identically or differently, by halogen,
  • R 8 and R 9 independently of one another for hydrogen, -SO 2 R 7 , for each optionally one or more times, identically or differently by halogen, dC 6 - alkylcarbonyl, -C-C 6 -alkylcarbonyloxy, C ⁇ -C 6 -alkylamino, di- (C 1 -C 6 -Alkyl) amino, dC 6 -alkoxy, dC 6 -haloalkoxy, -C-C 6 - alkylthio and / or C ⁇ -C 6 -haloalkylthio-substituted C ⁇ -C 0 alkyl or C 2 -C 20 alkenyl; in each case optionally mono- to tetrasubstituted by identical or different halogen, cyano, dC 6 -alkyl, C 6 haloalkyl, dC 6 alkoxy, dC logenalkoxy 6 -Ha-, dC 6
  • R 8 and R 9 furthermore together for C - C which are optionally mono- or polysubstituted, identically or differently, by halogen, cyano, dC 6 -alkoxy, dC ö -haloalkoxy, dC 6 - alkylthio and / or Ci-C ⁇ -haloalkylthio 12 alkenylene or optionally monosubstituted in the alkylene or polysubstituted by identical or different halogen, cyano, dC 6 -alkyl, halo-C 6 alkyl, C ⁇ -C6 alkoxy, dC 6 haloalkoxy, C ⁇ -C 6 -Alkylthio and / or dC 6 - Haloalkylthio substituted C 3 -C 12 alkylene, the alkylene chain by
  • -O-, -S- or -NR - can be interrupted
  • R 10 and R 11 independently of one another for hydrogen, -SO R 7 , for each in each case optionally up to thirteen times, identically or differently by halogen, dC 6 - alkylamino, di- (C 1 -C 6 -alkyl) amino, C 1 -C 6 - alkoxy, C ⁇ -C 6 haloalkoxy, dC ö -alkylthio and / or C 6 haloalkylthio substituted dC 6 alkyl or C 2 -C 6 alkenyl; in each case optionally mono- to tetrasubstituted by identical or different halogen, cyano, dC 6 -alkyl, C 6 haloalkyl, dC 6 -alkoxy, C 6 haloalkoxy, Ci-C 6 - alkylthio and / or C ⁇ - C 6 haloalkylthio substituted C 3 -C 7 cycloalkyl, C 3 -
  • R 10 and R 11 furthermore together represent optionally in the alkylene mono- to tetrasubstituted by identical or different halogen, cyano, C 6 alkyl, dC 6 - haloalkyl, dC 6 - alkoxy, C ⁇ -C 6 haloalkoxy, dC 6 - Alkylfhio and / or dC 6 haloalkylthio substituted C 3 -C 6 alkylene, - (CH 2 ) 2 -O- (CH 2 ) 2 -, - (CH 2 ) 2 -S- (CH 2 ) 2 - or - (CH 2 ) 2 -N (R 21 ) - (CH 2 ) 2 - stand,
  • R 12 and R 13 are independently hydrogen, optionally monosubstituted to thirteen times by identical or different halogen, cyano, C 6 - alkoxy, C ⁇ -C 6 - alkylthio substituted dC ö -alkyl, represents in each case optionally substituted once to eight times, the same or different halogen, cyano, alkyl dC 6 -Al-, dC 6 haloalkyl, dC 6 alkoxy, dC 6 haloalkoxy, dC 6 alkyl thio and / or dC 6 haloalkylthio substituted C 3 -C 7 cycloalkyl, C 3 -C - cycloalkyl -CC 4 -alkyl, aryl or aryl-dC 4 -alkyl,
  • R 12 and R 13 furthermore together represent in each case optionally substituted once to eight times in an identical or different manner by halogen, C 6 - alkyl, dC ⁇ haloalkyl, dC 6 alkoxy, dC o - ⁇ alogenalkoxy, C J -C ⁇ - alkylthio and / or C ⁇ -C 6 -Halo- halogenoalkylthio substituted C 3 -C ⁇ o alkylene or C 3 -C 10 alkenylene stand,
  • R 14 and R 15 independently of one another are hydrogen, C 6 alkyl, C 2 -C 6 alkenyl, C ⁇ -C 6 haloalkyl or C 2 -C 6 haloalkenyl,
  • R 16 and R 17 independently of one another are hydrogen, C 6 -alkyl, halo-C 6 alkyl or optionally substituted once to eight times by identical or different fluorine, chlorine, bromine and / or C ⁇ -C 6 alkyl are substituted C 3 -C cycloalkyl,
  • R and R also together for each optionally single to nine-fold, identical or different by fluorine, chlorine, bromine and / or dC 6 - alkyl substituted C 3 -C 6 alkylene, dd-AUtoxy-dd-alkylene or C ⁇ -C 3 - Are alkylthio-dC 3 -alkylene,
  • R 18 represents hydrogen or dC 6 alkyl
  • R 19 and R 20 independently of one another for hydrogen, for each optionally one or more times, identically or differently, by fluorine, chlorine, bromine, Ci-C 6 -alkylcarbonyl, dC 6 -alkylcarbonyloxy, CrC ö -alkylamino, di- (-C-C 6 -Alkyl) amino, dd ö -alkoxy, -C-C 10 -alkylfhio, d-do-alkoxy-d-do-alkoxy, d-do-haloalkoxy, d-do-haloalkylthio and / or Ci-do- Halogen alkoxy-C do-alkoxy substituted dC 2 o-alkyl or C -C 2 o-alkenyl;
  • R and R furthermore together represent C 2 -C 4 alkylene which is optionally mono- to tetrasubstituted by d-C 4 -alkyl, or
  • R 19 and R 20 together with the nitrogen atom to which they are attached also represent a saturated or unsaturated 5- to 10-membered heterocycle which, if appropriate, is a further heteroatom group from the series -O-, -S- or -NR - can contain and optionally up to four times, identical or different by fluorine, chlorine, bromine, dC 6 -alkyl, dC 6 - alkoxy, dC 6 - alkylthio, dC 6 -haloalkyl, dC 6 -haloalkoxy and / or C ⁇ -C 6 -Halogenalkylthio can be substituted, and
  • R 21 is hydrogen, -SO 2 R 7 , -COR 7 or -CO 2 R 7 ; for each optionally one or more times, identically or differently, by halogen, cyano, d-C 6 -alkylamino, di- (-C-C 6 -alkyl) amino, -C-C 6 -alkoxy, d-C ⁇ -haloalkoxy, dC 6- alkylthio and / or dC 6 -haloalkylthio substituted dC 0 -alkyl or C 2 -C 2 o-alkenyl; for each optionally one to four times, the same or different, by halogen, cyano, dC 6 alkyl, dC 6 halo alkyl, C 1 -C 6 alkoxy, dC 6 haloalkoxy, dC 6 alkylthio and / or dC 6 - haloalkylthio substituted C 3 -C 12
  • R, 22 represents hydrogen, dC 6 -alkyl or C 2 -C 6 -alkenyl
  • w 0, 1 or 2
  • n 1, 2 or 3
  • R 1 represents methyl, ethyl, n- or i-propyl, or aryl which is optionally mono- or disubstituted, identically or differently, the substituents from the series fluorine, chlorine, bromine, iodine, cyano, nitro, dC 4 - Alkyl, dC 4 -alkoxy, C 1 -C 4 -alkylthio, dC -haloalkyl, dC 4 -haloalkoxy and -C-C 4 -haloalkylfhio, each with 1 to 9 fluorine, chlorine and / or bromine atoms,
  • R 2 represents fluorine, chlorine, bromine, cyano, nitro, amino, C 1 -C 4 -alkyl or dC 4 - alkoxy
  • R 3 represents hydrogen, fluorine, chlorine, bromine, cyano, nitro, amino, C 1 -C 4 -alkyl or dC 4 - alkoxy
  • R 4 stands for the grouping -XYZE with the proviso that Y does not stand for a direct bond if X does not stand for a direct bond
  • R 5 is fluorine, chlorine, dC 4 alkyl, dC 4 alkoxy, C 1 -C 4 alkylthio; genalkyl dC 4 -Halo-, dC 4 haloalkoxy, C ⁇ -C is 4 -haloalkylthio having in each case 1 to 9 fluorine, chlorine and / or bromine atoms,
  • n 0, 1 or 2
  • R 5 can be identical or different if m represents 2
  • X for a direct bond, oxygen, -S (O) w -, -NR 6 -, carbonyl, carbonyloxy, oxycarbonyl, oxysulfonyl (OSO 2 ), -C-C 4 alkylene, dC 4 haloalkylene with 1 to 8 fluorine , Chlorine and / or bromine atoms, C 2 -C 4 alkenylene, C -C haloalkenylene with 1 to 6 fluorine, chlorine and / or bromine atoms, C 2 -C 4 alkynylene, d-Gi -Alkyleneoxy, oxy -CC 4 -alkylene, oxy-C 1 -C 4 -alkyleneoxy or -S (O) w -dC 4 -alkylene,
  • Y for a direct bond or for 1 to 3 times in each case optionally 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 2,6-naphthylene substituted by radicals from the list W 1 , 2,7-naphthylene, 1,4-naphthylene, 2,6- (l, 2,3,4-tetrahydro) naphthylene, 2,7- (l, 2,3,4-tetrahydro) naphthylene, 1,4 - (l, 2,3,4-tetrahydro) naphthylene, 5,8- (l, 2,3,4-tetrahydro) - naphthylene, 2,4-furylene, 2,4-thienylene, 2,4-pyrrolylene, 2,5-oxazolylene, 2,5-thiazolylene, 2,5-pyridinylene, 2,6-pyridinylene, 2,5-pyrimidinylene or 3,6-pyridazinylene or 2,5-
  • Z represents a direct bond or - (CH 2 ) n -, E for hydrogen, fluorine, chlorine, bromine, hydroxy, cyano, formyl, nitro,
  • R 6 for methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl, trifluoroethyl, or for each optionally one to four times, identical or different by fluorine, chlorine , Bromine, dC 4 -alkyl, d- C 4 -alkoxy, -CC alkylthio, dC 4 -haloalkyl, dC 4 -haloalkoxy and / or C -C -haloalkylthio, each with 1 to 9 fluorine, chlorine and / or bromine atoms, substituted cyclopropyl, cyclopropylmethyl, cyclopentyl, cyclopentylmethyl , Cyclohexyl, cyclohexylmethyl, phenyl, benzyl or phenylethyl,
  • R 7 for optionally single or multiple, identical or different by fluorine, chlorine, bromine and / or -NR 8 R 9 substituted -CC-alkyl, for each optionally single to four times, identical or different by fluorine, chlorine, bromine, cyano , CC 4 -alkyl, -C-C 4 -alkoxy, C ⁇ -C 4 -alkylthio, C ⁇ -C 4 - haloalkyl, C ⁇ -C 4 -haloalkoxy and / or dC 4 -haloalkylthio, each with 1 to 9 fluorine, chlorine and / or bromine atoms substituted cyclopropyl, cyclopentyl, cyclohexyl, phenyl or benzyl,
  • R 8 and R 9 independently of one another represent hydrogen, -SO 2 R 7, in each case optionally monosubstituted or polysubstituted by identical or different fluorine, chlorine, bromine, dQ-alkylcarbonyl, C ⁇ -C 4 alkylcarbonyloxy, C 1 -C 4 - alkylamino, di- (dd-alky amino, C 1 -C 4 -alkoxy, C 4 - alkylthio, C ⁇ -C -haloalkoxy and / or C -C haloalkylthio having in each case 1 to 9 fluorine, chlorine and!
  • R 8 and R 9 also together for optionally single or multiple, identical or different by fluorine, chlorine, bromine, -CC 4 alkoxy, -C -C alkylthio, dC 4 -haloalkoxy and / or C 1 -C -haloalkylthio with in each case 1 to 9 fluorine, chlorine and / or bromine atoms substituted C 2 -C 10 -alkenylene or, optionally or in the alkylene part, one or more times, identically or differently, by fluorine, chlorine, cyano, dC 4 -alkyl, dC 4 -alkoxy, C 1 -C 4 alkylthio, d- C 4 haloalkyl, dC 4 haloalkoxy and or C !
  • -C 4 -haloalkylthio each with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C 3 -C 10 alkylene, where the alkylene chain can be interrupted by -O-, -S- or -NR 21 -,
  • R 10 and R 11 independently of one another for hydrogen, -SO R 7 , each in each case optionally up to nine times, identically or differently by fluorine, chlorine, bromine, dd-alkylamino, di- (dC 4 -alkyl) amino, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, dC -haloalkoxy and / or dC 4 -haloalkylthio, each with 1 to 9 fluorine, chlorine and / or bromine atoms, substituted dC 6 -alkyl or C 2 -C 6 -alkenyl; in each case optionally mono- to trisubstituted by identical or different fluorine, chlorine, bromine, cyano, C 1 -C 4 alkyl, dC 4 -alkoxy, C 4 - alkylthio, C ⁇ -C haloalkyl, haloalkoxy, and dC 4 / or
  • R 10 and R 11 also together, in each case optionally in the alkylene part, one to four times, identically or differently, by fluorine, chlorine, cyano, QC-alkyl, dC 4 -alkoxy, C 1 -C 4 -alkylthio, dC 4 -haloalkyl, dC 4 -Halogenalkoxy and / or -CC 4 -Halogenalkylthio each with 1 to 9 fluorine, chlorine and / or Bromine substituted C 4 -C 5 alkylene, - (CH 2 ) 2 -O- (CH 2 ) 2 -,
  • R and R independently of one another for hydrogen, optionally optionally up to nine times, identically or differently by fluorine, chlorine, bromine, dC 4 - alkoxy and / or C 1 -C 6 -alkylthio substituted C 1 -C 6 -alkyl, for each optionally optionally up to four times , identical or different by fluorine, chlorine, bromine, dC 4 alkyl, dC 4 alkoxy, dC 4 alkylthio, dC 4 haloalkyl, dC 4 haloalkoxy and / or dC 4 haloalkylthio, each with 1 to 9 fluorine - C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-dC 4 alkyl, phenyl, benzyl or phenylethyl are substituted by chlorine and / or bromine atoms,
  • R 12 and R 13 also together, in each case optionally for one to four times, in the same way or differently, by fluorine, chlorine, bromine, C -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, dC 4 -haloalkyl, C ⁇ -C 4 -haloalkoxy and / or C ⁇ -C4-haloalkylthio having in each case 1 to 9 fluorine, chlorine and / or bromine-substituted C 3 -C 8 - alkylene or C -C 8 - are alkenylene,
  • R 16 and R 17 are independently hydrogen, dC 4 -alkyl, halo-C 4 alkyl group having 1 to 9 fluorine, chlorine and / or bromine atoms or represents optionally monosubstituted to tetrasubstituted by identical or different fluorine, chlorine , Bromine and / or C 1 -C 4 alkyl-substituted C 3 -C 6 cycloalkyl,
  • R 16 and R 17 also together for - (CH 2 ) 3 -, - (CH 2 ) 4 -, - (CH 2 ) 5 -, - (CH 2 ) 2 -O- (CH 2 ) 2 - or - ( CH 2 ) 2 -S- (CH 2 ) 2 - stand,
  • R 18 represents hydrogen or dC 4 alkyl
  • R 19 and R 20 independently of one another for hydrogen, for each optionally one or more times, identically or differently, by fluorine, chlorine, bromine, d- C 4 -alkylcarbonyl, C 1 -C 4 -alkylcarbonyloxy, dC 4 - alkylamino, di- (C ⁇ - C - alkyl) amino, d-do-alkoxy, d-dQ-alkylfhio, d-C ⁇ 0 -alkoxy-C ⁇ -C 6 -alkoxy, Cj-Cio-haloalkoxy, d-do-haloalkylthio and / or d-Cio-haloalkoxy-C ⁇ -C 6 -alkoxy each with 1 to 21 fluorine, chlorine and / or bromine atoms substituted -CC 16 -alkyl or C -C 16 alkenyl;
  • R 18 and R 19 also together represent C 2 -C 3 alkylene which is optionally monosubstituted to trisubstituted by d-C 4 alkyl, or
  • R 19 and R 20 together with the nitrogen atom to which they are attached also represent a saturated or unsaturated 5- to 7-membered heterocycle which may optionally be a further hetero atom group from the series -O-, -S- or -NR 22 - May contain (in particular from the series Piperidino, Mo ⁇ holino, Thiomo ⁇ holino, Piperazino, Pyrrolidino, Oxazolidino, Thiazolidino, 4H-1-Oxazinyl, 4H-1-Thiazinyl) and the optionally single to fourfold, identical or different by fluorine, chlorine , dC 4 -alkyl, dC 4 -alkoxy, dC 4 -A] kylthio, -C-C 4 -haloalkyl, dC 4 -haloalkoxy and or C 1 -C 4 -haloalkylthio, each with 1 to 9 fluorine, chlorine and or or Bromine atoms
  • R 21 for hydrogen, -SO 2 R 7 , for -COR 7 or -CO 2 R 7 ; for in each case optionally single or multiple, identical or different by fluorine, chlorine, bromine, Cyano, methylamino, ethylamino, di- (dC 6 -alkyl) amino, dC -alkoxy, d- C 4 -haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms, dC 4 - alkylthio and / or C 1 - C 4 haloalkylthio with 1 to 9 fluorine, chlorine and / or bromine atoms substituted dC ⁇ alkyl or C 2 -C 6 alkenyl; for each optionally single to triple, identical or different, by fluorine, chlorine, bromine, cyano, C 1 -C 4 -alkyl, dC -alkoxy, C 1 -C 4 -alkylthio,
  • R 22 represents hydrogen, -CC 4 - alkyl or C 2 -C 4 alkenyl
  • w 0, 1 or 2
  • n 1 or 2
  • p stands for 0 or 1.
  • R 1 represents methyl, ethyl, or optionally monosubstituted aryl, where the substituents from the series fluorine, methyl, ethyl, n-, i-propyl, n-, i-, s-, t-butyl, methoxy, ethoxy , n-, i-propoxy, n-, i-, s-, t-butoxy, methylthio, ethylthio, n-, i-propylthio, n-, i-, s-, t-butylthio, trifluoromethyl, and trifluoro- methoxy are selected, R 2 represents fluorine, chlorine, bromine, cyano or methyl,
  • R 3 represents hydrogen or fluorine
  • R 4 stands for the grouping -XYZE with the proviso that Y does not stand for a direct bond if X does not stand for a direct bond
  • R 5 for fluorine, chlorine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl, trifluoroethyl, methoxy, ethoxy, n-propoxy, i-prop - oxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, trifluoromethoxy, trifluoroethoxy, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio , t-butylthio, trifluoromethylthio or trifluoroethylthio,
  • n 0 or 1
  • Y for a direct bond or for in each case optionally single or double, identical or different, 1,4-phenylene, 1,3-phenylene, 2,6-naphthylene, 2,7-naphthylene, 2, substituted by radicals from the list W 1 , 4-furylene, 2,4-thienylene, 2,5-pyridinylene, 2,5-pyrimidinylene, 3,6-pyridazinylene or 2,5-pyrazinylene,
  • Z is a direct bond, methylene or ethylene
  • R 7 for methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, pentyl, hexyl, -CF 3 , -CHF 2 , -CC1 3 , - CC1 2 F, dimethylaminomethyl, dimethylaminoethyl, diethylaminomethyl, diethylaminoethyl, cyclopropyl, cyclopentyl, cyclohexyl, phenyl or benzyl,
  • R 8 and R 9 independently of one another for hydrogen, -SO 2 R 7 , for each optionally one or more times, identical or different, by fluorine, chlorine, bromine, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkylcarbonyloxy, C ⁇ -C 4 alkylamino, di- (C ⁇ -C4 alkyl) amino, C 1 -C 4 -alkoxy, C 4 -haloalkoxy having 1 to 9 fluorine, chlorine and / or bromine atoms, C 1 -C 4 - alkylthio and / or C 1 -C 4 haloalkylthio with 1 to 9 fluorine, chlorine and / or bromine atoms substituted Ci-C 16 alkyl, C 2 -C 16 alkenyl; for each optionally single to triple, identical or different by fluorine, chlorine, bromine, cyano, dC 4 - alkyl, d- C 4 haloalkyl with 1
  • R 8 and R 9 also together for optionally single or multiple, the same or different by fluorine, chlorine, bromine, -C-C 4 alkoxy, C 1 -C 4 halogen- alkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms, -CC alkylthio and / or C 1 -C 4 haloalkylthio with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C 2 -C 8 - Alkenylene or for single or multiple, optionally in the alkylene part, the same or different by fluorine, chlorine, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, C ⁇ - C 4 -haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, methoxy, ethoxy, n-propoxy
  • R 10 and R 11 independently of one another are hydrogen, -SO 2 CF, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, pentyl, hexyl, -CF 3 , -CH 2 CF 3 , - (CF 2 ) 3 CF 3 , cyclopropyl, cyclopentyl, cyclohexyl, methoxymethyl, methoxyethyl, or for each optionally single to triple, identical or different by fluorine, chlorine, bromine, methyl, trifluoromethyl, Methoxy, trifluoromethoxy substituted phenyl or benzyl,
  • R 10 and R 11 also together for - (CH 2 ) 4 -, - (CH 2 ) 5 -, - (CH 2 ) 6 -, -CH 2 -CH (CH 3 ) -CH 2 -CH (CH 3 ) -CH 2 -, - (CH 2 ) 2 -O- (CH 2 ) 2 -, - (CH 2 ) 2 -S- (CH 2 ) 2 - or - (CH 2 ) 2 -N (R 21 ) - (CH 2 ) 2 - stand,
  • R 12 and R 13 independently of one another are methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-hexyl, trifluoromethyl, trifluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl or represent phenyl or benzyl which are each mono- to tetrasubstituted, identically or differently, by fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, trifluoromethoxy
  • R 12 and R 13 also together, in each case optionally in each case up to four times, identically or differently by fluorine, chlorine, bromine, methyl, ethyl, methoxy Ethoxy, methylthio, ethylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio substituted - (CH 2 ) 3 -, - (CH 2 ) 4 -, - (CH 2 ) 5-, - (CH 2 ) 6 -,
  • R 16 and R 17 independently of one another are hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-hexyl, trifluoromethyl, trifluoroethyl, cyclopropyl, cyclopentyl or Cyclohexyl,
  • R 16 and R 17 also together for - (CH 2 ) 3 -, - (CH 2 ) 4 -, - (CH 2 ) 5 -, - (CH 2 ) 2 -O- (CH 2 ) 2 - or - ( CH 2 ) 2 -S- (CH 2 ) 2 - stand,
  • R 18 represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl or t-butyl,
  • R 19 and R 20 independently of one another for hydrogen, for each optionally one or more times, the same or different, by fluorine, chlorine, bromine, dd-alkylcarbonyl, C 1 -C 4 -alkylcarbonyloxy, dC 4 - alkylamino, di- (C 1 - C 4 -alkyl) amino, d-do-alkoxy, dC 8 -alkoxy-C 6 -C 6 -alkoxy, C-C 10 -alkyl thio, d-Cjo-haloalkoxy, -C-C ⁇ o-haloalkylthio, each with 1 to 21 fluorine -, Chlorine and / or bromine atoms, d-Cs-haloalkoxy-dd-alkoxy with 1 to 17 fluorine, chlorine and / or bromine atoms substituted d-do-alkyl or C 2 -C ⁇ o alkenyl (especially methyl,
  • R 18 and R 19 also together represent in each case optionally single or double, identical or different, methylene or ethylene substituted by methyl, ethyl, n-propyl or i-propyl, or
  • R 19 and R 20 also together with the nitrogen atom to which they are attached, for a 5- or 6-membered heterocycle from the series Piperidino, Morpholino, Thiomo ⁇ holino, Piperazino, Pyrrolidino, Oxazolidino, Thiazolidino, 4H-l-oxazinyl , 4H-1-Tl ⁇ iazinyl stand, which is optionally up to four times, identical or different by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t- Butyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, methylthio, ethylthio, n-propylthio, i-propylthio, n
  • R 21 for hydrogen, -SO 2 R 7 , for -COR 7 or -CO 2 R 7 ; for each optionally one or more times, the same or different, by fluorine, chlorine, bromine, cyano, methylamino, ethylamino, di- (C 1 -C 6 -alkyl) amino, -C-C 4 alkoxy, Ci- C 4 -haloalkoxy 1 to 9 fluorine, chlorine and / or bromine atoms, C 1 -C 4 -alkylthio and / or dC -haloalkylthio with 1 to 9 fluorine, chlorine and / or bromine atoms substituted dC 16 -alkyl, C 2 -C ⁇ 6 alkenyl; for each optionally single to triple, identical or different, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl,
  • R 22 represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, vinyl or allyl.
  • ⁇ 1 -pyrrolines of the formula (I) in which R 1 represents methyl are also preferred.
  • ⁇ ⁇ pyrrolines of the formula (I) in which R 1 represents phenyl are also preferred.
  • ⁇ 1 -pyrrolines of the formula (I) in which R 2 and R 3 are fluorine are also preferred.
  • ⁇ ⁇ pyrrolines of the formula (I) in which R 2 represents fluorine, chlorine, bromine, cyano or methyl and R 3 represents hydrogen.
  • ⁇ ⁇ pyrrolines of the formula (I) in which R 4 represents the grouping -YE, Y is 1,4-phenylene and E is the general, preferred, particularly preferred, very particularly preferred or in particular entirely given above has particularly preferred meanings. Also preferred are ⁇ ⁇ pyrrolines of the formula (Id) (group 1)
  • R la stands for C 1 -C 6 -alkyl (preferably for C 1 -C 4 -alkyl),
  • R 2a represents fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 alkyl or dC 4 alkoxy,
  • R 3a represents hydrogen, fluorine, chlorine, bromine, dC 4 alkyl or dC 4 alkoxy
  • R 4a for hydrogen, fluorine, chlorine, bromine, iodine, Ci-Cg-alkyl, dC 8 -haloalkyl, -OSO 2 CF 3 or for optionally single or double, identical or different by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C alkylthio, Ci- C haloalkyl, C ⁇ -C4 haloalkoxy, and Ci-C4-haloalkylthio having in each case 1 to 9 fluorine, chlorine and / or bromine-substituted phenyl or in each case optionally monosubstituted by halogen, C ⁇ -C alkyl, C 1 -C 4 - alkoxy, C ⁇ -C 4 - alkylthio, dC 4 -Halogenaikyl, dQ-haloalkoxy and dC 4 -haloalkylthio having 1 to 9 fluorine
  • R la represents methyl, ethyl, n-, i-propyl, n-, i-, s-, t-butyl,
  • R 2a represents fluorine, chlorine, bromine, cyano or methyl
  • R 3a represents hydrogen or fluorine
  • R represents hydrogen, fluorine, chlorine, bromine, iodine, -OSO 2 CF 3 or simply phenyl substituted in the 4-position by chlorine, methoxy, i-propoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio,
  • R 4a also stands for pyridinyl which is simply substituted in the 4-position by chlorine, methoxy, i-propoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio.
  • R la for unsubstituted phenyl or for single or double, identical or different by fluorine, chlorine, bromine, iodine, cyano, nitro, dd-alkyl, C 1 -C 4 -alkoxy, dC 4 -alkylfhio, dd-haloalkyl, dC 4 -Halogenalkoxy and d- C 4 -Halogenalkylthio each with 1 to 9 fluorine, chlorine and / or bromine atoms substituted phenyl,
  • R 2 ⁇ b D represents fluorine, chlorine, bromine, cyano, nitro, dC 4 -alkyl or dC 4 -alkoxy,
  • R, 3 J b D represents hydrogen, fluorine, chlorine, bromine, CC 4 alkyl or dC 4 alkoxy
  • R 4b for hydrogen, fluorine, chlorine, bromine, iodine, dC 8 alkyl, dC 8 haloalkyl, -OSO 2 CF 3 or for optionally single or double, identical or different, by halogen, C 1 -C 4 -alkyl, dd-alkoxy , C 1 -C 4 - alkylthio, cid-haloalkyl, dd-haloalkoxy and dd-haloalkylfhio, each with 1 to 9 fluorine, chlorine and / or bromine atoms, substituted phenyl or for each optionally optionally by halogen, C 1 -C 4 -alkyl, C1-C4- Alkoxy, dq alkylthio, C ⁇ -C4 haloalkyl, C ⁇ -C 4 haloalkoxy and CC 4 -haloalkylthio having in each case 1 to 9 fluorine, chlorine and / or
  • R 1b represents unsubstituted phenyl or phenyl which is simply substituted in the 4-position by fluorine, trifluoromethyl, trifluoromethoxy or trifluoromethylthio,
  • R 2b represents fluorine, chlorine, bromine, cyano or methyl
  • R 3b represents hydrogen or fluorine
  • R 4 represents hydrogen, fluorine, chlorine, bromine, iodine, -OSO 2 CF 3 or simply phenyl which is substituted in the 4-position by chlorine, methoxy, i-propoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio,
  • R 4b also stands for pyridinyl substituted in the 4-position by chlorine, methoxy, i-propoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio.
  • Saturated hydrocarbon residues such as alkyl can be straight-chain or branched as far as possible.
  • Formula (U) provides a general definition of the aroylpyrrolidinones required as starting materials when carrying out process (A) according to the invention.
  • R 1, R 2, R 3, R 4, R 5 and m being preferred, particularly preferred, very particularly preferred or especially preferably has those meanings which have already been in connection with the description of the substances according to the invention of the formula (I) were mentioned as preferred, particularly preferred etc. for these radicals.
  • Aroylpyrrolidinones of the formula (J ⁇ ) are new. They can be made by
  • R ! , R 4 R 5 and m have the meanings given above,
  • G represents chlorine, -CC 6 alkoxycarbonyl or -N (OCH 3 ) CH 3 ,
  • a base e.g. Lithium bis (trimethylsilyl) amide
  • a diluent e.g tefrahydrofuran
  • Formula (VIII) provides a general definition of the lactams required as starting materials when carrying out process (a) according to the invention.
  • R 1, R 4, R 5 and m being preferred, particularly preferred, very particularly preferred or especially preferably has those meanings already in connection with the description of the inventive compounds of formula (I) for these radicals as preferred, particularly preferred, etc. were mentioned.
  • Lactams of the formula (Vfll) are new. They can be made by
  • R 1 , R 4 , R 5 and m have the meanings given above,
  • di-tert-butyl dicarbonate in the presence of a base (e.g. dimethylaminopyridine) and optionally in the presence of a diluent (e.g. dimethylformamide), (see Tetrahedron Letters, 1998, 39, 2705-2706).
  • a base e.g. dimethylaminopyridine
  • a diluent e.g. dimethylformamide
  • Formula (IX) provides a general definition of the compounds required as starting materials when carrying out process (a) according to the invention. In this
  • Formula R and R are preferred, particularly preferred, very particularly preferred or in particular very particularly preferred for those meanings which have already been mentioned as preferred, particularly preferred etc. for these radicals in connection with the description of the compounds of the formula (I) according to the invention.
  • G preferably represents chlorine, methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, t-butoxycarbonyl or -N (OCH 3 ) CH3, particularly preferably chlorine.
  • Formula (X) provides a general definition of the pyrrolidinones required as starting materials when carrying out process (b) according to the invention.
  • R, R, R 5 and m are preferably, particularly preferably, very particularly preferably or particularly very particularly preferably those meanings which have already been mentioned as preferred, particularly preferred etc. in connection with the description of the compounds of the formula (I) according to the invention for these radicals.
  • R 1 , R 4 , R 5 and m have the meanings given above,
  • a diluent e.g. xylene
  • a base e.g. aqueous ammonia solution
  • R, ⁇ , R, R and m have the meanings given above,
  • Formula (XI) provides a general definition of the amino acids required as starting materials when carrying out process (c) according to the invention.
  • R 1, R 4, R 5 and m being preferred, particularly preferred, very particularly preferred or especially preferably has those meanings already in connection with the description of the inventive compounds of formula (I) for these radicals as preferred, particularly preferred, etc. were mentioned.
  • Amino acids of the formula (XI) are new. They can be made by
  • a diluent e.g. toluene
  • an acid e.g. p-toluenesulfonic acid
  • R> 4 R and m have the meanings given above, with an ⁇ , ⁇ -unsaturated ester or nitrile of the formula (XV)
  • R 19 represents C 1 -C 4 alkoxycarbonyl or cyano
  • R 1 has the meanings given above,
  • Formula (XEi) provides a general definition of the benzylammes required as starting materials when carrying out process (e) according to the invention.
  • R 4 , R 5 and m are preferred, particularly preferred, very particularly preferred or in particular very particularly preferred for those meanings which are particularly preferred for these radicals already in connection with the description of the compounds of the formula (I) according to the invention preferred etc. were mentioned.
  • Benzylamines of the formula (XHI) are known and / or can be prepared by known processes.
  • Formula (XV) provides a general definition of the ⁇ , ⁇ -unsaturated esters or nitriles required as starting materials when carrying out process (e) according to the invention.
  • R 1 is preferably, particularly preferably, very particularly preferably or in particular very particularly preferably for those meanings which have already been mentioned as preferred, particularly preferred etc.
  • R 19 preferably represents methoxycarbonyl, ethoxycarbonyl, n-, i-Propoxycarbonyl, n-, i-, s-, t-butoxycarbonyl or cyano, particularly preferably for methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, t-butoxycarbonyl or cyano, very particularly preferably for methoxycarbonyl or cyano.
  • ⁇ -unsaturated esters or nitriles of the formula (XV) are known and / or can be prepared by known processes.
  • Formula (XII) provides a general definition of the ketocarboxylic acids required as starting materials when carrying out process (d) according to the invention.
  • R 1, R 4, R 5 and m being preferred, particularly preferred, very particularly preferred or especially preferably has those meanings already in connection with the description of the inventive compounds of formula (I) for these radicals as preferred, particularly preferred, etc. were mentioned.
  • ketocarboxylic acids of the formula (XII) are known and / or can be prepared by known processes (cf., for example, Eur. J. Med. Chem. 1993, 28, 129; J. Chin. Pharm. Sei. 1992. 1, 27) ,
  • Process (A) according to the invention is carried out in the presence of an acid.
  • Acids which can be used in carrying out the process according to the invention are all of the protonic acids which are customary for such reactions or strong organic acids (such as sulfonic acids) or halocarboxylic acids.
  • Hydrochloric acid, sulfuric acid, hydrofluoric acid, phosphoric acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoroacetic acid or trichloroacetic acid can preferably be used.
  • Hydrochloric acid, sulfuric acid, p-toluenesulfonic acid or trifluoroacetic acid are particularly preferably used, very particularly preferably sulfuric acid.
  • the acid used can optionally be used in a mixture with water.
  • the process according to the invention can optionally be carried out in the presence of a diluent.
  • Organic acids are suitable as diluents when carrying out the process according to the invention.
  • preferential propionic acid, acetic acid or formic acid are usable.
  • Acetic acid is particularly preferably used.
  • any mixture of sulfuric acid (as acid) and acetic acid (as diluent) and optionally water when carrying out the process according to the invention.
  • other mixing ratios can also be set and used.
  • reaction temperatures can be varied within a substantial range when carrying out process (A) according to the invention. In general, temperatures between 20 ° C and 200 ° C, preferably at temperatures between 60 ° C and 150 ° C.
  • reaction time is between 0.5 h and 6 h.
  • Formula (m) provides a general definition of the compounds required as starting materials when carrying out process (B) according to the invention.
  • R 1 , R 2 , R 3 , R 4 , R and m are preferably, particularly preferably, very particularly preferably or particularly very particularly preferably those meanings which have already been associated with the description of the substances of the formula ( I) were mentioned as preferred, particularly preferred etc. for these radicals.
  • R 1 , R 4 , R 5 and m have the meanings given above,
  • R> 2 and 3 ⁇ R> 3 have the meanings given above
  • Formula (XVI) provides a general definition of the lithium compounds required as starting materials when carrying out process (f) according to the invention.
  • R 2 and R 3 are preferred, particularly preferred, very particularly preferred or in particular very particularly preferred for those meanings which are already preferred, particularly preferred, etc. in connection with the description of the compounds of the formula (I) according to the invention for these radicals . were called.
  • Lithium compounds of the formula (XVI) are known and / or can be prepared from the corresponding 1,3-disubstituted phenyl derivatives by known processes.
  • Process (B) according to the invention is carried out in the presence of an acid.
  • Acids which can be used in carrying out the process according to the invention are all of the protonic acids which are customary for such reactions or strong organic acids (such as sulfonic acids) or halocarboxylic acids.
  • Hydrochloric acid, sulfuric acid, hydrofluoric acid, phosphoric acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoroacetic acid or trichloroacetic acid can preferably be used.
  • Trifluoroacetic acid is particularly preferably used.
  • the acid used can optionally be used in a mixture with water.
  • Suitable diluents for carrying out process (B) according to the invention are all customary inert, organic solvents.
  • Halogenated aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; Chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, Tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole.
  • Dichloromethane is particularly preferably used.
  • reaction temperatures can be varied within a substantial range when carrying out process (B) according to the invention. In general, temperatures between -20 ° C and + 60 ° C, preferably at temperatures between -10 ° C and 40 ° C.
  • an excess of acid (between 1 mol and 50 mol) is generally employed per mol of a compound of the formula (HI).
  • other ratios of the reaction components can also be selected.
  • the processing takes place according to usual methods. The general procedure is to neutralize the reaction mixture with sodium hydrogen carbonate, extract the product, wash the organic phase, dry and concentrate under reduced pressure. The raw product is then freed of any residues that may still be present using customary methods (e.g. chromatography or recrystallization).
  • a ⁇ ⁇ pyrroline of the formula (I-b) is coupled with a diboronic acid ester in the presence of a palladium catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a solvent.
  • a compound of the formula (IV) is coupled in the same reaction vessel in a second reaction step in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a solvent (cf., for example, Tefraedron Lett. 1997. 38 , 3841).
  • Process (C) can be carried out in two variants. It can either be a compound of formula (Ib) or a compound of Formula (TV) can be submitted. Process (C) is to be regarded as a tandem reaction of processes (D) and (E) described below.
  • Formula (Ib) provides a general definition of the ⁇ 1 -pyrrolines required as starting materials when carrying out process (C) according to the invention.
  • R 1 , R 2 , R 3 , R 5 and m preferably, particularly preferably, very particularly preferably or in particular very particularly preferably represent those meanings which have already been associated with the description of the substances of the formula (I) according to the invention were mentioned as preferred, particularly preferred etc. for these radicals.
  • R 42 preferably represents chlorine, bromine, iodine, -OSO 2 CF 3 or -SO 2 (CF 2 ) 3 CF 3 , particularly preferably chlorine, bromine, -OSO 2 CF 3 or -OSO 2 (CF 2 ) CF 3 , very particularly preferably for chlorine, bromine or -OSO 2 CF 3 .
  • ⁇ 1 -pyrrolines of the formula (Ib) are the subject of this invention and can be prepared by one of the processes (A) or (B).
  • Formula (IV) provides a general definition of the cyclic compounds required as starting materials when carrying out process (C) according to the invention.
  • E preferably, particularly preferably, very particularly preferably or in particular very particularly preferably represents those meanings which have already been mentioned as preferred, particularly preferred etc. for these radicals in connection with the description of the substances of the formula (I) according to the invention
  • Y 1 preferably represents in each case optionally up to four times, the same or different phenylene substituted by radicals from the list W 1 or 5- to 10-membered, saturated or unsaturated heterocyclylene with one or more heteroatoms from the series nitrogen, oxygen and sulfur.
  • Y 1 particularly preferably represents 1,4-phenylene, 1,3-phenylene, 1,2-phenylene which may be mono- to tetrasubstituted, identically or differently, by radicals from the list W 1 ; or represents in each case optionally mono- to tetrasubstituted by identical or different radicals from the list W 1 is substituted 5- to 6-membered saturated or unsaturated heterocyclylene having 1 to 3 heteroatoms, containing 0 to 3 nitrogen atoms, 0 to 2 nonadjacent oxygen atoms and / or 0 to 2 non-adjacent sulfur atoms contains (especially furylen, thienylene, pyrrolylene, oxazolylene, thiazolylene, pyridinylene, pyrimidinylene, pyridazinylene or pyrazinylene).
  • Y 1 very particularly preferably represents 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 2,4-furylene, which may be monosubstituted to trisubstituted, identically or differently, by radicals from the list W 1 , 2,4-thienylene, 2,4-pyrrolylene, 2,5-oxazolylene, 2,5-thiazolylene, 2,5-pyridinylene, 2,6-pyridinylene, 2,5-pyrimidinylene, 3,6-pyridazinylene or 2, 5-pyrazylylene.
  • Y 1 particularly particularly preferably represents 1,4-phenylene, 1,3-phenylene, 2,4-furylene, 2,4-thienylene, 2, which may be mono- or disubstituted, identically or differently, by radicals from the list W 1 , 5-pyridinylene, 2,5-pyrimidinylene, 3,6-pyridazinylene or 2,5-pyrazinylene.
  • W 1 preferably, particularly preferably, very particularly preferably or in particular very particularly preferably represents those meanings which have already been mentioned as preferred, particularly preferred etc. in connection with the description of the compounds of the formula (I) according to the invention for these radicals.
  • a 1 preferably represents bromine, chlorine, iodine or - SO 2 CF 3 , particularly preferably bromine, chlorine or iodine, very particularly preferably bromine or chlorine.
  • the cyclic compounds of the formula (IV) are known or can be prepared by known processes (cf. Aust. J. Chem. 1964, 17, 794; Chem. Ber. 1992, 125, 1169; Chem. Pharm. Bull. 1995. 43, 247; Eur. I. Med. Chem. 1989. 24, 249; J. Chem. Soc. C 1971. 1889; J. Chem. Soc. Perkin Trans. 1 1995. 2497; J. Med. Chem. JJ21 , 34, 315; J. Org. Chem. J, 49, 2240; J. Org. Chem. J 2Q, 55, 69; Org. Prep. Proced. Int. 1998. 30, 433; Synthesis 1999. 1163; Tefrahedron 1999. 40, 7975; Tefrahedron Lett. 19Jä, 37, 4447; Tefrahedron Lett. 2QQQ, 41, 4335).
  • Diboronic acid esters used in carrying out process (C) 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi-l, 3,2-dioxaborolane, 5 , 5,5 ⁇ 5'-tetramethyl-2,2'-bi-l, 3,2-dioxaborinane, 4,4,4 ', 4', 6,6'-hexamethyl-2,2'-bi-l , 3,2-di-oxaborinan or 2,2'-Bi-l, 3,2-benzodioxaborol in question.
  • Formula (V) provides a general definition of the ⁇ 1 -pyrrolines required as starting materials when carrying out process (D) according to the invention.
  • R, R, R, R and m are preferably, particularly preferably, very particularly preferably or particularly very particularly preferably those meanings which have already been given in connection with the description of the substances of the formula (I) according to the invention Residues were mentioned as preferred, particularly preferred, etc.
  • a 2 preferably represents -B (OH) 2 , (4,4,5,5-teframethyl-l, 3,2-dioxaborolane) -2-yl, (5,5-dimethyl-l, 3,2-dioxaborinane ) -2-yl, (4,4,6-trimethyl-l, 3,2-dioxaborinan) -2-yl or l, 3,2-benzodioxaborol-2-yl, particularly preferred for -B (OH) 2 , (4,4,5,5-tetramethyl-l, 3,2-dioxaborolane) -2-yl, (5,5-dimethyl-l, 3,2-dioxaborinane) -2-yl or (4,4 , 6- Trimethyl-l, 3,2-dioxaborinan) -2-yl, very particularly preferred for -B (OH) 2 , (4,4,5,5-tetramethyl-l, 3,2-dioxaborolan) -2
  • R, ⁇ , R, R, R, m and R .42 have the meanings given above,
  • Suitable diboronic acid esters for carrying out process (g) have already been mentioned in the description of process (C) according to the invention.
  • Formula (VI) provides a general definition of the boronic acid derivatives required as starting materials when carrying out process (E) according to the invention.
  • E is preferably, particularly preferably, very particularly preferably or in particular very particularly preferably those meanings which have already been mentioned as preferred, particularly preferred etc. for these radicals in connection with the description of the substances of the formula (I) according to the invention
  • Y 1 preferably, particularly preferably, very particularly preferably or in particular very particularly preferably represents those meanings which have already been mentioned as preferred, particularly preferred etc. in connection with the description of the substances of the formula (IV) for these radicals.
  • a 2 preferably, particularly preferably, very particularly preferably or in particular very particularly preferably represents those meanings which have already been mentioned as preferred, particularly preferred etc. for these radicals in connection with the description of the substances of the formula (V).
  • the compounds of the formula (VI) are known or can be prepared by known processes (cf. J. Org. Chem. 1995. 60, 7508, Tefrahedron Lett. 1997. 38, 3447).
  • Formula (Ic) provides a general definition of the ⁇ 1 -pyrrolines required as starting materials when carrying out process (F) according to the invention.
  • R 1 , R 2 , R 3 , R 5 and m preferably, particularly preferably, very particularly preferably or in particular very particularly preferably represent those meanings which have already been associated with the description of the substances of the formula (I) according to the invention were mentioned as preferred, particularly preferred etc. for these radicals.
  • R 43 preferably represents bromine or iodine.
  • ⁇ 1 -pyrrolines of the formula (Ic) are the subject of this invention and can be prepared by one of processes (A) or (B).
  • Formula (VH) provides a general definition of the organometallic compounds required as starting materials when carrying out process (F) according to the invention.
  • E is preferably, particularly preferably, very particularly preferably or in particular very particularly preferably those meanings which have already been mentioned as preferred, particularly preferred etc. for these radicals in connection with the description of the substances of the formula (I) according to the invention
  • Y 1 preferably, particularly preferably, very particularly preferably or in particular very particularly preferably denotes those meanings which, in connection with the description of the substances of the formula (IV) according to the invention, are preferred, particularly preferred, etc. for these radicals were.
  • M preferably represents ZnCl, Sn (Me) 3 or Sn (n-Bu) 3 .
  • Organometallic compounds of the formula (VII) are known in some cases and / or can be prepared by known methods. For example, it is possible to prepare compounds of the formula (VII) in situ from the corresponding compounds of the formula (IV) in which A 1 is -OSO 2 CF 3 (cf. Tefrahedron Lett. 1995, 36, 9085).
  • a palladium catalyst is used in each case, which in turn can be used with or without the addition of further ligands.
  • Triarylphosphines, trialkylphosphines or arsines are suitable as ligands.
  • Dppf, PPh 3 , P (t-Bu) 3 , Pcy 3 or AsPh 3 are preferably used, particularly preferably dppf.
  • Suitable diluents for carrying out processes (C), (D) and (E) according to the invention are all customary inert, organic solvents.
  • Halogenated aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, Cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; Chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tefrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Nitriles, such as acetonit
  • Acetone, dimethoxyethane, dioxane, tefrahydrofuran, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, ethanol, toluene or, if appropriate, mixtures of these diluents with water are particularly preferably used.
  • Suitable diluents for carrying out process (F) according to the invention are all customary inert, organic solvents.
  • Halogenated ahphatic, ahcyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; Chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tefrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole. Dioxane, tefrahydrofur
  • Suitable acid binders for carrying out processes (C), (D), (E) and (F) are all inorganic and organic bases customary for such reactions.
  • Preferably usable alkaline earth or alkali metal hydroxides such as sodium hydroxide, calcium hydroxide, potassium hydroxide, or also A are moniumhydroxid, alkali metal carbonates as Natriumcar- carbonate, potassium carbonate, Kaliirmhydrogencarbonat, sodium hydrogencarbonate, alkali or alkaline earth metal acetates such as sodium acetate, calcium acetate, metal fluorides Kaliurnacetat alkali metal, and tertiary amines such as trimethylamine , Triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, Diazabicyclooctane (DABCO), Diazabicyclononen (DBN) or Diazabicyclounde
  • reaction temperatures can in each case be varied within a substantial range.
  • temperatures between 0 ° C and 140 ° C, preferably between 20 ° C and 120 ° C, particularly preferably between 60 ° C and 100 ° C.
  • reaction temperatures can be varied over a wide range when carrying out process (F) according to the invention. In general, temperatures between 0 ° C and 140 ° C, preferably between 20 ° C and 120 ° C.
  • R, R, R, R, m and R, 42 have the meanings given above, or the pyrrolidinones of the formula (X)
  • R »1, ⁇ R> 4, R and m have the meanings given above,
  • a resolution For example, preparative chromatography, preferably high performance liquid chromatography (HPLC), is used.
  • HPLC high performance liquid chromatography
  • a chiral stationary silica gel phase is used.
  • a silica gel modified with tris (3,5-dimethylphenyl carbamate) cellulose has proven to be particularly suitable for the separation of the compounds of the formula (I-b) into the two enantiomers.
  • This trerm material is commercially available.
  • Halogenated ahphatic, ahcyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane; Dichloromethane, chloroform; Alcohols such as methanol, ethanol, propanol; Nitriles such as acetonitrile; Esters such as methyl acetate or ethyl acetate.
  • Ahphatic hydrocarbons, such as hexane or heptane, and alcohols, such as methanol or propanol, are particularly preferably used, and n-heptane and isopropanol or mixtures of these are very particularly preferred.
  • temperatures between 10 ° C and 60 ° C, preferably between 10 ° C and 40 ° C, particularly preferably at room temperature.
  • the (R) -configured enantiomers obtained in this way are then used as starting materials for processes (C) or (E).
  • the active ingredients are suitable for the protection of plants and plant organisms with good plant tolerance, favorable toxicity to warm-blooded animals and good environmental compatibility.
  • ganen to increase crop yields, improve the quality of the crop and to combat animal pests, especially insects, arachnids and nematodes, which occur in agriculture, in forests, in gardens and leisure facilities, in the protection of stocks and materials and in the hygiene sector.
  • insects especially insects, arachnids and nematodes, which occur in agriculture, in forests, in gardens and leisure facilities, in the protection of stocks 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., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
  • Phthiraptera e.g. Pediculus humanus co ⁇ oris, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci
  • Trialeurodes vaporariorum Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis,
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa 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 of the formula (I) according to the invention are distinguished in particular by an excellent action against caterpillars, beetle larvae, spider mites, aphids and leaf miners.
  • the substances according to the invention also show a very good duration of action, e.g. against the caterpillars of the cotton capsule worm (Heliothis virescens) or the caterpillars of the army worm (Spodoptera frugiperda).
  • the compounds according to the invention can also be used in certain concentrations or application rates as herbicides and microbicides, for example as fungicides, antifungals and bactericides. If appropriate, they can also be used as intermediates or products for the synthesis of further active ingredients.
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring cultivated plants).
  • Cultivated plants can be plants 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 plant varieties that can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space according to the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading, injecting and, in the case of propagation material, in particular in the case of seeds, furthermore by single- or multi-layer coating.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrations, natural and synthetic substances impregnated with active substances, and very fine encapsulations in polymeric substances.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents and / or solid carriers
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • auxiliary solvents include aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated ahphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable Oils, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methylsobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water.
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated ahphatic hydrocarbons such
  • Possible solid carriers are: e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95% 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, for example in order to broaden the spectrum of activity or to prevent the development of resistance; in many cases synergistic effects, ie the activity, are obtained the mixture is greater than the effectiveness of the individual components.
  • Calcium polysulfide Ca ⁇ ropamid, Capsimycin, Captafol, Captan, Carbendazim, Carboxin, Carvon, Quinomethionate (Quinomethionat), Chlobenthiazon, Chlorfenazol, Chloroneb, Chloropicrin, Chlorothalonil, Chlozolinat, Clozylaconox, Cufranil, Cufranil, Cufranil, Cufranil
  • Debacarb dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomo ⁇ h, diniconazole, diniconazole-M,
  • Ferbam Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Fhuprimidol, Flusilazol, Flusulfamid, Flutolanil, Flutriafol, Folpet, Fosetyl-Alminium,
  • Imazalil imibenconazole, iminoctadine, iminoctadineal besilate, iminoctadine triacetate, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Iprovalicarb, Irumamycin, Isoprothiolan, Isovaledione,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, Tefraconazol, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, Tridemo ⁇ h, trifloxystrobin, Triflurnizol, triforine, Triticonazole, Uniconazole, Validamycin A, Vinclozolin, Viniconazol, Zarilamid, Zineb, Ziram as well as Dagger G, OK-8705, OK-8801, ⁇ - (l, 1-dimethylethyl) -ß- (2-phenoxyethyl) - 1 H-1 , 2,4-triazole-1-ethanol, - (2,4-dich
  • Cadusafos Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloetho- carb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos,
  • Chlo ⁇ yrifos Chlo ⁇ yrifos M, Chlovaporthrin, Chromafenozide, Cis-Resmethrin,
  • Fenamiphos fenazaqum, fenbutatin oxide, fenitrothion, fenothiocarb, fenoxacrim
  • Fenoxycarb Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenthion, Fenvalerate, Fipronil, Fluazuron, Flubrocythrinate, Flucycloxuron, Flucythrinate, Flufen- oxuron, Flumethrin, Flupyrazofos, Flutenzophone, Fluvalinine, Fluvalinine
  • Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
  • Metharhilic flavoviride methidathione, methiocarb, methoprene, methomyl,
  • Methoxyfenozide Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Milbe mycin, Monocrotophos,
  • Pirimiphos M Profenofos, Promecarb, Propargite, Propoxur, Prothiofos, Prothoat, Pymetrozine, Pyraclofos, Pyresmethrin, Pyrethrum, Pyridaben, Pyridathion,
  • Tefluthrin Tefluthrin, temephos, temivinphos, terbufos, tetrachlorvinphos, tetradifon, theta-cypermethrin, thiacloprid, thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox, thuringinhrine, tri
  • Triarathenes triazamates, triazophos, triazuron, trichlophenidines, trichlorfon,
  • 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 compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in mixtures with inhibitors which reduce degradation of the active compound after use in the environment of the plant, on the surface of parts of plants or in plant tissues ,
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the drug concentration of the Application forms can be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • the active ingredient When used against hygiene pests and pests of stored products, the active ingredient is distinguished by an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates.
  • plants and their parts can be treated according to the invention.
  • plant species and plant cultivars and their parts occurring wildly or obtained by conventional organic breeding methods, such as crossbreeding or protoplast fusion are treated.
  • 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 “parts of plants” was explained above.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with new properties (“traits”) which have been grown by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, bio- and genotypes.
  • the treatment according to the invention can also result in superadditive (“synergistic”) effects.
  • superadditive for example, reduced application rates and or widening the spectrum of action and / or strengthening the effect 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 against water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest 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 expected effects.
  • the preferred transgenic 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, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher storage life and / or Processability of the crop products Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased tolerance of the plants to certain herbicidal active ingredients.
  • the important cultivated plants such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes) are mentioned as examples of fransgenic plants, with corn, soybeans , Potato, cotton, tobacco, and rapeseed are particularly highlighted.
  • the traits are particularly emphasized as the increased defense of the plants against insects, arachnids, nematodes and snails by toxins that arise in the plants, especially those that are caused by the genetic material from Bacillus thuringiensis (eg by the genes Cry ⁇ A (a) , CryIA (b), Cry ⁇ A (c), CryllA, CrylTIA, CryIHB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter referred to as “Bt plants”).
  • Bacillus thuringiensis eg by the genes Cry ⁇ A (a) , CryIA (b), Cry ⁇ A (c), CryllA, CrylTIA, CryIHB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations
  • the properties (“traits”) also particularly emphasize the increased defense of plants against fungi, bacteria and viruses through systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and ent speaking proteins and toxins.
  • the properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example “PAT” gene).
  • the genes conferring the desired properties (“traits”) can also be found in combinations with one another in the transgenic plants.
  • Bt plants are maize varieties, cotton varieties, soy varieties and potato varieties that are marketed under the trade names YIELD GARD® (eg maize , Cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato).
  • herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties that are sold under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, e.g.
  • rapeseed rapeseed
  • UVII® tolerance to Imidazolinone
  • STS® tolerance to sulfonylureas such as maize
  • the herbicide-resistant plants 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”).
  • plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula (I) 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 compounds according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, and mite mites, Running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, featherlings and fleas.
  • animal parasites ectoparasites
  • tick ticks such as tick ticks, leather ticks, and mite mites, Running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, featherlings and fleas.
  • Ischnocerina e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp.,
  • Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota ., Philipomyia spp., Braula spp.,
  • Musca spp. Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp.,
  • Sarcophaga spp. Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.
  • Mesostigmata e.g. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp.,
  • Hyalomma spp. Rhipicephalus spp., Dermanyssus spp., Raillietia spp.,
  • Acarapis spp. Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Lisfrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypppectterol spp ., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
  • the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used 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 compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitonal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing , powdering and with the help of active substance-containing shaped bodies, such as collars, ear tags, tail tags, limb straps, holsters, marking devices, etc.
  • enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories
  • parenteral administration for example by
  • the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or apply after 100 to 10,000-fold dilution or use it as a chemical bath.
  • formulations for example powders, emulsions, flowable agents
  • insects which destroy industrial materials.
  • insects may be mentioned by way of example and preferably, but without limitation:
  • Kalotermes flavicolhs 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 against 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 compounds can be used as such, in the form of concentrate fractions 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 repellent, 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 compound according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
  • the amount of the agents or concentrates used depends on the type and occurrence of the insects and on the medium. The optimal amount can be determined 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 compound, based on the material to be protected.
  • organic-chemical solvent or solvent mixture and / or an oily or oily or low-volatility organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agents.
  • the organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
  • Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.
  • Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, Te ⁇ entinöl and Like. Used.
  • liquid aliphatic hydrocarbons with a boiling range from 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range from 180 to 220 ° C. and / or locker oil and / or monochloronaphthalene, preferably ⁇ -monochloromaphthalene, are used.
  • the organic semi-volatile 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 above 35 and has a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.
  • part of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced.
  • Aliphatic hydroxyl and / or ester and / or ether groups are preferably used organic chemical solvents such as glycol ether, ester or the like. For use.
  • the organic-chemical binders which are known are water-dilutable and / or synthetic resins which are soluble or dispersible or emulsifiable in the organic-chemical solvents used and / or binding drying oils, in particular binders consisting of or containing an 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, hydrocarbon resin such
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellants, odor correctors and inhibitors or anticorrosive agents and the like can be used.
  • At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder.
  • Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
  • binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).
  • the plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, higher glycerol glycerol or glycerol ether - Kolether, glycerol ester and p-toluenesulfonic acid ester.
  • phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate
  • phosphoric acid esters such as tributyl phosphate
  • adipic acid esters such as di- (2-ethylhexyl) adipate
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
  • Water is also particularly suitable as a solvent or diluent, if appropriate in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
  • a particularly effective wood protection is achieved through industrial impregnation processes, e.g. Vacuum, double vacuum or pressure process.
  • the ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides.
  • insecticides and fungicides mentioned in WO 94/29 268 are preferably suitable as additional admixing partners.
  • the compounds mentioned in this document are an integral part of the present application.
  • Especially preferred mixing partners which may insecticides such Chlo ⁇ yri-, phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, Permefhrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthrin, thia cloprid, methoxyfenozide, triflumuron, clothianidin, spinosad and tefluthrin,
  • fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorfluanid, tolylfluanid, 3-iodo-2-propynyl butyl carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octyl-isothiazolin-3-one.
  • the compounds according to the invention can be used to protect objects, in particular ship hulls, sieves, nets, structures, quay systems and signaling systems which come into contact with sea or brackish water.
  • barnacles such as various Lepas and Scalpellum species
  • Balanomo ⁇ ha (barnacles) such as Baianus or Pollicipes species
  • heavy metals such as in bis (frialkyltin) sulfides, tri-n-butyltin laurate, tri - «- butyltin chloride, copper ( ⁇ ) 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-n-butyltin fluoride, manganethylene bisistocarboxy Zinc dimethyldithiocarbamate, zinc ethylene bishiocarbamate, zinc and copper salts of 2-pyridinthiol-l-oxide, bisdimethyldithiocarbamoylzinc ethylene bisthiocarbamate, zinc oxide, copper (I) - ethylene bisdithi
  • the ready-to-use antifouling paints can optionally contain other active ingredients, preferably algicides, fungicides, herbicides, muusicicides or other antifouling active ingredients.
  • Suitable combination partners for the antifouling agents according to the invention are preferably:
  • 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 of 0.01 to 20% by weight.
  • the antifouling agents according to the invention further contain the usual ingredients such as e.g. 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 / acrylonitrile Rubbers, drying oils, such as linseed oil, resin esters or modified hard resins in combination with tar or bitumen, asphalt and epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.
  • Paints may also contain inorganic pigments, organic pigments or dyes, which are preferably insoluble in sea water. Paints may also contain materials such as rosin to enable controlled release of the active ingredients. The paints may also contain plasticizers, modifiers affecting theological properties, and other conventional ingredients. The compounds according to the invention or the abovementioned mixtures can also be incorporated into self-polishing antifouling systems.
  • the active ingredients are also suitable for controlling animal pests, in particular insects, arachnids and mites, which live in closed rooms, such as For example, apartments, factories, offices, vehicle cabins, etc. occur.
  • animal pests in particular insects, arachnids and mites, which live in closed rooms, such as For example, apartments, factories, offices, vehicle cabins, etc. occur.
  • insects in particular insects, arachnids and mites
  • closed rooms such as For example, apartments, factories, offices, vehicle cabins, etc. occur.
  • insects in particular insects, arachnids and mites
  • closed rooms such as For example, apartments, factories, offices, vehicle cabins, etc. occur.
  • active ingredients and auxiliaries in household insecticide products. They are effective against sensitive and resistant species and against all stages of development.
  • Sco ⁇ ionidea e.g. Buthus occitanus.
  • Dermanyssus gallinae Glyciphagus domesticus, Ornithodorus moubat, Rhipi- cephalus 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.
  • Aedes aegypti Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis,
  • Musca domestica Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa.
  • 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.
  • Rhodinus prolixus Triatoma infestans.
  • the mixture is allowed to slowly rise to room temperature and, after stirring, is diluted with water for 16 h. After acidification with dilute hydrochloric acid, the product is extracted with dichloromethane. The organic phase is separated off, dried over magnesium sulfate and concentrated.
  • logP values specified in the tables and manufacturing examples above are determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 43 ° C.
  • the determination is carried out in the acidic range at pH 2.3 with 0.1% aqueous phosphoric acid and acetonitrile as eluents; linear gradient from 10% acetonitrile to 90% acetonitrile.
  • the values are marked in the tables with a).
  • the determination is carried out in the neutral range at pH 7.5 with 0.01 molar aqueous phosphate buffer solution and acetonitrile as eluent; linear gradient from 10% acetonitrile to 90% acetonitrile.
  • the values are marked in the tables with b).
  • the calibration is carried out using unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive alkanones).
  • the lambda max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals. applications
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Soybean shoots (Glycine max) are treated by being dipped into the preparation of active ingredient of the desired concentration and populated with caterpillars of the cotton capsule worm (Heliothis armigera) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with larvae of the horseradish leaf beetle (Phaedon cochleariae) while the leaves are still moist.
  • the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the cockroach (Plutella xylostella) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the army worm (Spodoptera exigua) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the army worm (Spodoptera frugiperda) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Bean plants Phaseolus vulgaris
  • Tetranychus urticae which are heavily infested with all stages of the common spider mite (Tetranychus urticae), are immersed in 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.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Cabbage leaves (Brassica oleracea), which are heavily infested with peach aphids (Myzus persicae), are treated by being dipped into the preparation of active compound of the desired concentration.
  • the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Amount of emulsifier and dilute the concentrate with water to the desired concentration is required.
  • the active ingredient preparation is poured onto the floor.
  • the concentration of the active ingredient in the preparation is practically irrelevant, the only decisive factor is the amount of active ingredient per unit volume of soil, which is given in ppm (mg / 1). You fill the bottom in 0.25 1 pots and let them stand at 20 ° C.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Soybean shoots (Glycine max) of the Roundup Ready variety (trademark of Monsanto Comp. USA) are treated by dipping into the preparation of active compound of the desired concentration and are populated with the tobacco bud caterpillar Heliothis virescens while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne de nouvelles Δ1-pyrrolines correspondant à la formule (I), dans laquelle R1, R2, R3, R4, R5 et m ont la signification donnée dans la description. L'invention concerne également plusieurs procédés de production de ces substances et leur utilisation dans la lutte antiparasitaire.
PCT/EP2003/001024 2002-02-13 2003-02-03 $g(d)1-pyrrolines et leur utilisation dans la lutte antiparasitaire WO2003067986A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003206816A AU2003206816A1 (en) 2002-02-13 2003-02-03 Delta1 PYRROLINES AND THE USE THEREOF IN PEST CONTROL

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10205862.8 2002-02-13
DE2002105862 DE10205862A1 (de) 2002-02-13 2002-02-13 DELTA1-Pyrroline

Publications (1)

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WO2003067986A1 true WO2003067986A1 (fr) 2003-08-21

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AU (1) AU2003206816A1 (fr)
DE (1) DE10205862A1 (fr)
WO (1) WO2003067986A1 (fr)

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WO2004031176A3 (fr) * 2002-09-24 2004-06-17 Bayer Cropscience Ag Pyrrolines
WO2008128711A1 (fr) * 2007-04-23 2008-10-30 Bayer Cropscience Ag Insecticides d'aryle pyrrolidines
WO2010124845A1 (fr) * 2009-04-30 2010-11-04 Bayer Cropscience Ag Arylpyrrolidines à activité pesticide
US9266830B2 (en) 2007-04-23 2016-02-23 Bayer Intellectual Property Gmbh Pesticidal arylpyrrolidines
EP3095780A1 (fr) * 2008-10-17 2016-11-23 Bayer Intellectual Property GmbH Arylpyrrolidines pesticides

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SU1298204A1 (ru) * 1985-11-21 1987-03-23 МГУ им.М.В.Ломоносова Способ получени 3,4-диарил-гамма-аминомасл ных кислот или их циклических амидов
WO1995029150A1 (fr) * 1994-04-21 1995-11-02 Ciba-Geigy Ag Synthese des prototypes des inhibiteurs de la renine
WO1999059967A1 (fr) * 1998-05-18 1999-11-25 Bayer Aktiengesellschaft Derives de 2-(2-methylphenyl)-3,4-dihydro-2h-pyrrol
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YEE, NATHAN K.: "A practical one-pot synthesis of trans-4,5-disubstituted 2-pyrrolidinones and the related pyrrolidines", TETRAHEDRON LETTERS (1997), 38(29), 5091-5094, XP004082953 *

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004031176A3 (fr) * 2002-09-24 2004-06-17 Bayer Cropscience Ag Pyrrolines
JP2006511480A (ja) * 2002-09-24 2006-04-06 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト ピロリン類
US7297797B2 (en) 2002-09-24 2007-11-20 Bayer Cropscience Ag Pyrrolines
AU2008240984B2 (en) * 2007-04-23 2014-03-20 Bayer Intellectual Property Gmbh Insecticidal aryl pyrrolidines
JP2010526035A (ja) * 2007-04-23 2010-07-29 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト 殺虫性アリールピロリジン
US8188122B2 (en) 2007-04-23 2012-05-29 Bayer Cropscience Ag Insecticidal aryl pyrrolidines
EP2463265A3 (fr) * 2007-04-23 2012-11-21 Bayer CropScience AG Procédé pour la préparation d'insecticides d'aryle pyrrolidines
WO2008128711A1 (fr) * 2007-04-23 2008-10-30 Bayer Cropscience Ag Insecticides d'aryle pyrrolidines
JP2014208670A (ja) * 2007-04-23 2014-11-06 バイエル・クロップサイエンス・アーゲーＢａｙｅｒ Ｃｒｏｐｓｃｉｅｎｃｅ Ａｇ 殺虫性アリールピロリジン
US8980937B2 (en) 2007-04-23 2015-03-17 Bayer Cropscience Ag Insecticidal aryl pyrrolidines
CN103483235B (zh) * 2007-04-23 2015-09-09 拜尔农作物科学股份公司 杀虫的芳基吡咯烷类化合物
US9266830B2 (en) 2007-04-23 2016-02-23 Bayer Intellectual Property Gmbh Pesticidal arylpyrrolidines
EP3095780A1 (fr) * 2008-10-17 2016-11-23 Bayer Intellectual Property GmbH Arylpyrrolidines pesticides
WO2010124845A1 (fr) * 2009-04-30 2010-11-04 Bayer Cropscience Ag Arylpyrrolidines à activité pesticide
CN102414175A (zh) * 2009-04-30 2012-04-11 拜耳作物科学公司 杀虫的芳基吡咯烷

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AU2003206816A1 (en) 2003-09-04

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