Classifications

• • 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
• • 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
• • 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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
  • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
  • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
  • C07D207/333—Radicals substituted by oxygen or sulfur atoms

Definitions

• the present invention relates to novel, 3-substituted ⁇ '-pyrrolines, several processes for their preparation and their use as pesticides.
• R 1 represents halogen, in each case optionally substituted alkyl, alkoxy or represents -S (O) w R 7 ,
• R and R independently of one another represent hydrogen, halogen or each optionally substituted alkyl or alkoxy,
• R represents halogen, optionally substituted alkyl or represents -SO 3 R,
• R 5 represents hydrogen, halogen, optionally substituted alkyl or represents -SO 3 R, R 4 and R s also together for grouping stand,
• R 6 represents halogen, in each case optionally substituted alkyl, alkoxy or alkylthio,
• n 0, 1, 2, 3 or 4
• Q represents the grouping -X-Y-Z-E, with the proviso that if X is not a direct bond, Y is not a direct bond,
• R 7 represents optionally substituted alkyl
• R 8 represents hydrogen or optionally substituted alkyl
• R 9 represents hydrogen or in each case optionally substituted alkyl, aryl or
• X for a direct bond, oxygen, -S (O) w -, -NR 10 -, carbonyl, carbonyloxy, oxycarbonyl, oxysulfonyl (OSO 2 ), alkylene, haloalkylene, alkenylene, haloalkenylene, alkynylene, alkyleneoxy, oxyalkylene, oxyalkyleneoxy,
• 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 ⁇ , -OSO 2 R ⁇ , -NR 12 R 13 , -COR 11 , -CO 2 R ⁇ , -OC (O) R ⁇ , -CONR 14 R 15 , -N ( R 16 ) COR 17 , -C (R 18 ) N-OR 19 , -SO 2 NR 20 R 21 ; or for each optionally substituted alkyl, alkenyl, alkynyl, Alkoxy, alkenyloxy, cycloalkyl, cycloalkylalkyl, cycloalkyloxy, aryl, arylalkyl, aryloxy, aryloxyalkyl, saturated or unsaturated heterocyclyl or heterocyclylalkyl,
• R 10 for optionally substituted alkyl, cycloalkyl, cycloalkylalkyl,
• R n stands for optionally substituted alkyl, cycloalkyl, aryl or arylalkyl,
• R 12 and R 13 independently of one another represent hydrogen, -SO R ⁇ , in each case optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or saturated or unsaturated heterocyclyl or heterocyclylalkyl,
• R 12 and R 13 also together represent optionally substituted alkenylene or alkylene, where the alkylene chain can in each case be interrupted by -O-, -S- or -NR -,
• R 14 and R 15 independently of one another represent hydrogen, -SO 2 R n , in each case optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or saturated or unsaturated heterocyclyl or heterocyclylalkyl,
• R 14 and R 15 also together represent optionally substituted alkylene, where the alkylene chain can be interrupted by -O-, -S- or -NR 22 -,
• R and R independently of one another represent hydrogen, in each case optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
• R 16 and R 17 also together represent optionally substituted alkylene or alkenylene
• R 18 and R 19 independently of one another represent hydrogen, in each case optionally substituted alkyl or alkenyl
• R 20 and R 21 independently of one another represent hydrogen, each optionally substituted alkyl or cycloalkyl,
• R 20 and R 21 also together represent optionally substituted alkylene, alkoxyalkylene or alkylthioalkylene,
• R 22 is hydrogen, -SO 2 R ⁇ , -COR 11 or -CO 2 R n ; represents in each case optionally substituted alkyl, alkenyl, cycloalkyl, aryl, or saturated or unsaturated heterocyclyl,
• w 0, 1 or 2
• n stands for 1, 2, 3 or 4.
• the compounds of the formula (I) can optionally be present in different compositions as geometric and / or optical isomers, regioisomers or configuration isomers or their isomer mixtures. Both the pure isomers and the isomer mixtures are claimed according to the invention.
• R, 4 "- " 1 1 represents chlorine or bromine
• R> 5 3 - " l 1 represents hydrogen, chlorine or bromine
• R 1 , R 2 , R 3 , R 6 , m and Q have the meanings given above,
• R> 2 "3 represents alkyl or haloalkyl, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
• R 1 , R 2 , R 3 , R 6 , m and Q have the meanings given above,
• R 4 "2 represents alkyl or haloalkyl
• R 5 "2 represents hydrogen, alkyl or haloalkyl
• R 1 , R 2 , R 3 , R 6 , m and Q have the meanings given above,
• R 4 "3 represents -SO 3 R 8 , where R 8 has the meanings given above,
• R 5 "3 represents hydrogen
• R 8 has the meanings given above
• R, R, R, R, m, Q and R have the meanings given above,
• R 9 has the meanings given above,
• 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 preferably represents halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or -S (O) w R 7 .
• R 2 and R 3 independently of one another preferably represent hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkoxyalkyl.
• R 4 preferably represents halogen, alkyl, haloalkyl or -SO 3 R 8 .
• R 5 preferably represents hydrogen, halogen, alkyl, haloalkyl or -SO 3 R 8 .
• R 4 and R 5 also together preferably represent the grouping R 6 preferably represents halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or haloalkylthio.
• m preferably represents 0, 1, 2, 3 or 4.
• Q preferably stands for the grouping -X-Y-Z-E with the proviso that Y does not stand for a direct bond if X does not stand for a direct bond.
• R 7 preferably represents alkyl or haloalkyl.
• R 8 preferably represents hydrogen, alkyl or haloalkyl.
• R 9 preferably represents hydrogen, alkyl, haloalkyl or, in each case, optionally up to four times, identical or different from the list W 1 substituted aryl or 5- to 10-membered heteroaryl with one or more heteroatoms from the series nitrogen, oxygen and sulfur.
• X preferably represents a direct bond, oxygen, -S (O) w -, -NR 10 -, carbonyl, carbonyloxy, oxycarbonyl, oxysulfonyl (OSO 2 ), alkylene, halogenoalkylene, alkenylene, haloalkenylene, alkynylene, alkyleneoxy, oxy - alkylene, oxyalkyleneoxy, -S (O) w -alkylene, cyclopropylene or oxiranylene.
• Y preferably represents a direct bond or in each case optionally up to four times, identically or differently, 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 Range of nitrogen, oxygen and sulfur.
• Z preferably represents a direct bond or - (CH) possibly-.
• W 1 preferably represents halogen, cyano, formyl, nitro, trialkylsilyl, alkyl,
• Haloalkyl, alkoxy, haloalkoxy, alkenyl, haloalkenyl, alkenyloxy, haloalkenyloxy, alkylcarbonyl, alkoxycarbonyl, -S (O) w R ⁇ , -C (R 18 ) N-
• R 10 preferably represents alkyl, haloalkyl, or in each case optionally one or more times, identically or differently by halogen, alkyl,
• R 11 preferably represents alkyl which is optionally mono- or polysubstituted, identical or different, by halogen and / or -NR 12 R 13 , and in each case optionally mono- or polysubstituted, identically or differently by
• R 12 and R 13 independently of one another preferably represent hydrogen, -SO 2 R ⁇ , each optionally singly or multiply, identically or differently by halogen, alkylcarbonyl, alkylcarbonyloxy, alkylamino, dialkylamino, Alkoxy, haloalkoxy, alkylthio and / or haloalkylthio 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 12 and R 13 also preferably together represent optionally substituted one or more times, identically or differently by halogen, cyano, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio, or optionally substituted 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 22 -.
• R 14 and R 15 independently of one another preferably represent hydrogen, -SO 2 R u , each optionally mono- or polysubstituted, 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 14 and R 15 together preferably 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 22 - can be interrupted.
• R 16 and R 17 independently of one another preferably represent hydrogen, optionally optionally mono- or polysubstituted, identically or differently, substituted by halogen, cyano, alkoxy and / or alkylthio, each 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 16 and R 17 together preferably represent alkylene or alkenylene which is optionally mono- or polysubstituted, identically or differently, by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio.
• R 18 and R 19 independently of one another preferably represent hydrogen, alkyl, alkenyl, haloalkyl or haloalkenyl.
• R 20 and R 21 independently of one another, preferably represent hydrogen, alkyl, haloalkyl or optionally cycloalkyl which is mono- or polysubstituted, identically or differently, by halogen or alkyl.
• R 20 and R 21 preferably together represent alkylene, alkoxyalkylene or alkylthioalkylene which may be mono- or polysubstituted, identically or differently, by halogen or alkyl.
• R 22 preferably represents hydrogen, -SO 2 R ⁇ , -COR 11 or -CO 2 R n ; for alkyl or alkenyl which is optionally mono- or polysubstituted, identically or differently, by halogen, cyano, alkylamino, dialkylamino, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio; for cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, saturated or unsaturated, 5- to 10-membered heterocyclyl, each optionally mono- or polysubstituted, identically or differently, by halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and / or haloalkylthio or heterocyclylalkyl with one or more heteroatoms from the series nitrogen, oxygen and sulfur.
• w is preferably 0, 1 or 2.
• n is preferably 1, 2, 3 or 4.
• p is preferably 0, 1 or 2.
• R 1 particularly preferably represents halogen, d- -alkyl, dC 6 -haloalkyl,
• R and R independently of one another are particularly preferably hydrogen, halogen, -CC 6 -alkyl, -C-C 6 -haloalkyl, -C-C 6 -alkoxy, CC 6 -haloalkoxy or C-C 6 -alkoxy-C ⁇ -C 6 alkyl.
• R 4 particularly preferably represents halogen, Ci-Cio-alkyl, dC ⁇ -haloalkyl or -SO 3 R 8 .
• R and R 5 also together are particularly preferred for the grouping
• R 5 particularly preferably represents hydrogen, halogen, Ci-Cio-alkyl, Q-Cio-haloalkyl or -SO 3 R 8 .
• R 6 particularly preferably represents fluorine, chlorine, bromine, Ci-C ⁇ -alkyl, C 6 oxy -Alk-, C I -C ⁇ - alkylthio, Ci-COE-haloalkyl, C ⁇ -C 6 haloalkoxy or Cj -C 6 - haloalkylthio.
• m particularly preferably represents 0, 1, 2 or 3.
• Q particularly preferably 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 7 particularly preferably represents C i -C 6 alkyl or C j -C 6 haloalkyl.
• R 8 particularly preferably represents hydrogen, -CC 6 - alkyl or dC 6 - haloalkyl.
• R 9 particularly preferably represents hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, or each optionally monosubstituted to tetrasubstituted, identically or differently, by radicals from the list W substituted aryl or 5- or 6-membered heteroaryl With 1 to 3 heteroatoms, which contains 0 to 3 nitrogen atoms, 0 to 2 non-adjacent oxygen atoms and 0 to 2 non-adjacent sulfur atoms (especially furyl, thienyl, pyrrolyl, oxazolyl, thiazolyl or pyridinyl).
• X particularly preferably represents a direct bond, oxygen, -S (O) w -,
• Y particularly preferably stands for a direct bond or for in each case optionally up to four times, identically or differently by residues from the
• List W 1 substituted 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 2,6-naphthylene, 2,7-naphthylene, 1,4-naphthylene, 2,6- (1,2 , 3,4-tetrahydro) naphthylene, 2,7- (l, 2,3,4-tetrahydro) naphthylene, 1,4- (l, 2,3,4-tetrahydro) naphylene, 5,8- (l, 2,3,4-tetrahydro) naphthylene; or for each optionally monosubstituted to tetrasubstituted, identically or differently, by radicals from list W 1
• Z particularly preferably represents a direct bond or - (CH 2 ) n -.
• E particularly preferably represents hydrogen, fluorine, chlorine, bromine, hydroxy
• Cyano, formyl, nitro, tri- (-C 6 alkyl) silyl, pentafluorothio, -S (O) w R ⁇ , -OSO 2 R H , -NR 12 R 13 , -COR 11 , -CO2R 11 , - OC (O) R u , -CONR 14 R 15 , -N (R 16 ) COR 17 , -C (R 18 ) N-OR 19 , -SO 2 NR 20 R 21 ; for each optionally singly or multiply, identically or differently, by halogen, cyano, Ci-Cio-alkoxy and / or -NR 12 R 13 substituted dC 20 alkyl, C 2 -C 20 alkenyl, C 2 -C ⁇ o alkynyl, C ⁇ -C 2 o-alkoxy, C2-C 20 alkenyloxy; or in each case optionally mono- to tetrasubstitute
• W 1 particularly preferably represents fluorine, chlorine, bromine, cyano, formyl, nitro, tri-
• (-C 6 -alkyl) silyl, dC 6 -alkyl, C ⁇ -C 6 -haloalkyl, C ⁇ -C 6 -alkoxy, C ⁇ -C 6 - haloalkoxy, C 2 -Cö-alkenyl, C -C 6 -haloalkenyl, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C i -C 6 alkylcarbonyl, C i -C 6 alkoxycarbonyl, -S (O) w R ⁇ , -C (R 18 ) N-OR 19 , -SO 2 NR 20 R 21 , - (CH 2 ) P NR 20 R 21 ,
• R 10 particularly preferably represents dC 6 -alkyl, Ci-C ⁇ -haloalkyl, or each in each case optionally up to four times, identically or differently by halogen, dC 6 -alkyl, dC 6 -haloalkyl, C 1 -C 6 -alkoxy, C ⁇ -C 6 -haloalkoxy, -C-C 6 - alkylthio and / or -C-C 6 -haloalkylthio substituted C 3 - C 7 -cycloalkyl, C 3 -C 6 -cycloalkyl-dC 4 -alkyl, aryl or aryl-Cj -C 4 alkyl.
• R 11 particularly preferably represents C 1 -C 20 -alkyl which is optionally mono- or polysubstituted, identically or differently, by halogen and / or -NR 12 R 13 , in each case optionally by up to eight times, identically or differently, by halogen, cyano, C ⁇ - C 6 alkyl, Cj-C6 haloalkyl, Cj-C ö -alkoxy, C 6 haloalkoxy, C ⁇ -C 6 alkylthio and / or C ⁇ -C6 haloalkylthio substituted C 3 -C 6 cycloalkyl, Aryl or aryl -CC-alkyl.
• R and R independently of one another particularly preferably represent hydrogen, —SO 2 R 11 , each optionally optionally singly or multiply, identically or differently by halogen, dC 6 -alkylcarbonyl, dC 6 -alkylcarbonyloxy, d-
• R 12 and R 13 also together are particularly preferably optionally single or multiple, identical or different by halogen, cyano, Ci-C ⁇ -alkoxy, Ci-C ö -haloalkoxy, C I -C ⁇ - alkylthio and / or C ⁇ - C 6 - haloalkylthio substituted C 2 -d - alkenylene or for one or more, optionally in the alkylene part, identical or different by halogen,
• R 14 and R 15 independently of one another particularly preferably represent hydrogen, -SO 2 R ⁇ , each optionally up to thirteen times, identically or differently by halogen, Ci-C ⁇ -alkylamino, di- (C ⁇ -C ⁇ - alkyl) amino, C ⁇ -C 6 - alkoxy, Ci-C ö haloalkoxy, C J -C ⁇ - alkylthio and / or halo-Ci-C ö alkylthio substituted C ö alkyl or C 2 -C 6 alkenyl; in each case optionally mono- to tetrasubstituted by identical or different halogen, cyano, Ci-C ö -alkyl, C 6 haloalkyl, Ci-C ö alkoxy, Ci-C ö haloalkoxy, d-C ⁇ - alkylthio, and / or Ci-C ö haloalkylthio substituted C 3 -C 7
• -C 4 -alkyl aryl, aryl -CC-alkyl, saturated or unsaturated, 5- to 10-membered heterocyclyl or heterocyclyl -CC 4 -alkyl having 1 to 4 heteroatoms, which have 0 to 4 nitrogen atoms, 0 to Contain 2 non-adjacent oxygen atoms and / or 0 to 2 non-adjacent sulfur atoms (in particular tetrazolyl, furyl, furfuryl, benzofuryl, tetrahydrofuryl, thienyl, thenyl, benzothienyl, thiolanyl, pyrrolyl, indolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, benzoxazolyl, benzoxazolyl, benzoxazolyl, imidazolyl,
• R 14 and R 15 also together, particularly preferably, represent, if appropriate, one to four times in the alkylene part, identical or different by halogen,
• R 16 and R 17 independently of one another particularly preferably represent hydrogen, optionally monosubstituted to thirteen times by identical or different halogen, cyano, Ci-C ö alkoxy, CI-COE alkylthio substituted C I -C ⁇ - alkyl, in each case optionally single to eightfold, identical or different by halogen, cyano, C1-C0-alkyl, Ci-Cö-haloalkyl, Ci-Cö-alkoxy, C1-C0- haloalkoxy, C J -C ⁇ - alkylthio and / or dC ö - Haloalkylthio substituted C 3 -C cycloalkyl, C 3 -C 7 cycloalkyl -CC 4 -alkyl, aryl or aryl -CC 4 -alkyl.
• R 16 and R 17 together also particularly preferably represent in each case optionally up to eight times, identical or different from halogen, C1-C0-
• R 18 and R 19 independently of one another particularly preferably represent hydrogen, dd- alkyl, C 2 -C 6 - alkenyl, C ⁇ -C 6 haloalkyl or C 2 -C 6 haloalkenyl.
• R 20 and R 21 independently of one another particularly preferably represent hydrogen, Ci-C ö -alkyl, Coe haloalkyl or optionally substituted once to eight times by identical or different fluorine, chlorine, bromine and / or C1-C0
• R 20 and R 21 furthermore together particularly preferably represent in each case optionally substituted once to nine times in an identical or different manner by fluorine, chlorine, bromine and / or C I -C ⁇ - alkyl substituted C 3 -C ⁇ alkylene, C] -C3 - Alkoxy -CC 3 alkylene or -C 3 alkylthio -C -C 3 alkylene.
• R 22 particularly preferably represents hydrogen, -SO 2 R u , -COR 11 or -CO 2 R ⁇ ; for each optionally single or multiple, identical or different by halogen, cyano, CpC ⁇ -alkylamino, di- (C] -C ö alkyl) amino, -C-C 6 alkoxy, Ci-C ö haloalkoxy, C
• w particularly preferably represents 0, 1 or 2.
• n particularly preferably represents 1, 2 or 3.
• p particularly preferably represents 0, 1 or 2.
• R 1 very particularly preferably represents fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 - haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, C 1 -C 4 - Alkoxy, dC 4 -haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms or -S (O) w R 7 .
• R 2 and R 3 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine, bromine, C ⁇ -C 4 -alkyl, C 4 -haloalkyl having 1 to 9 fluorine,
• Chlorine and / or bromine atoms Cj-C - alkoxy or C ⁇ -C 4 haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms.
• R 4 very particularly preferably represents fluorine, chlorine, bromine, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl having 1 to 13 fluorine, chlorine and / or bromine atoms, or
• R 5 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, C 1 -C 0 -alkyl, Cj-C ⁇ -haloalkyl having 1 to 13 fluorine, chlorine and / or bromine atoms, or -SO 3 R 8 ,
• R 4 and R 5 also together are particularly preferred for the group
• R 6 very particularly preferably represents fluorine, chlorine, C ⁇ -C 4 - alkyl, C ⁇ -C 4 alkoxy,
• n very particularly preferably represents 0, 1 or 2.
• Q very particularly preferably stands for the grouping -X-Y-Z-E with the
• Y is not a direct bond if X is not a direct bond.
• R 7 very particularly preferably represents -CC alkyl or methyl or ethyl substituted in each case by fluorine or chlorine.
• R 8 very particularly preferably represents hydrogen, -CC alkyl or -CC 4 haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms.
• R 9 very particularly preferably represents hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, or each optionally substituted up to three times by radicals from the list W 1 Phenyl, furyl, thienyl, pyrrolyl, oxazolyl, thiazolyl or pyridinyl.
• X very particularly preferably represents a direct bond, oxygen, -S (O) w -, -NR 10 -, carbonyl, carbonyloxy, oxycarbonyl, oxysulfonyl (OSO 2 ), Cj-C 4 -alkylene, -C-C -haloalkylene 1 to 8 fluorine, chlorine and / or bromine atoms, dd-alkenylene, dd-haloalkenylene with 1 to 6 fluorine, chlorine and / or bromine atoms, dd-alkynylene, CC 4 -alkyleneoxy, oxy-C ⁇ -C 4 - alkylene, oxy -CC 4 alkyleneoxy or -S (O) w -C 4 -alkylene.
• Y very particularly preferably stands for a direct bond or for 1, 4-phenylene, 1,3-phenylene, 1, 2-phenylene, 1, 2-phenylene, 1, 4-phenylene, substituted by radicals from the list W 1, which are optionally mono- to triple, identical or different.
• Z very particularly preferably represents a direct bond or - (CH 2 ) n -
• E very particularly preferably represents hydrogen, fluorine, chlorine, bromine, hydroxy, cyano, formyl, nitro, trimethylsilyl, dimethyl-tert-butylsilyl,
• W is very particularly preferably represents fluorine, chlorine, bromine, cyano, formyl, trimethylsilyl, dimethyl-tert-butylsilyl, C ⁇ -C 4 alkyl, CC 4 -alkoxy, C 2 -C 4 -
• R 10 very particularly preferably represents methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl, trifluoroethyl, or in each case optionally up to four times, the same or different through fluorine,
• R 11 very particularly preferably represents optionally mono- or polysubstituted, identically or differently, by fluorine, chlorine, bromine and / or -NR 12 R 13 substituted d-C 1 -alkyl, in each case optionally up to four times, identically or differently by fluorine, chlorine and / or bromine, cyano, C 4 alkyl, Ci- C 4 - alkoxy, C ⁇ -C 4 alkylthio, C ⁇ -C haloalkyl, haloalkoxy dC and / or C ⁇ -C haloalkylthio having in each case 1 to 9 fluorine, chlorine and / or
• R 12 and R 13 independently of one another very particularly preferably represent hydrogen, -SO2R 11 , each optionally singly or multiply, identically or differently by fluorine, chlorine and / or bromine, C 1 -C 4 -alkyl carbonyl, C 1 -C 4 -Alkylcarbonyloxy, -C-C -alkylamino, di- (-C-C -alkyl) - amino, C ⁇ -C 4 - alkoxy, C ⁇ -C 4 -haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms, Cj- C - alkylthio and / or -CC haloalkylthio with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C 1 -C 1 alkyl or
• C 2 -C 1 alkenyl for each optionally single to triple, identical or different, by fluorine, chlorine and or bromine, cyano, C 1 -C 4 -alkyl, C 1 -C 4 - haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms, C 1 -C 4 - alkoxy, C ⁇ -C atoms 4 -haloalkoxy having 1 to 9 fluorine, chlorine and / or bromine, C ⁇ -C 4 - alkylthio and / or C ⁇ -C4-haloalkylthio having 1 to 9 fluorine,
• R 12 and R 13 also together very particularly preferably represent optionally one or more, identical or different by fluorine, chlorine and / or bromine, -C-C 4 alkoxy, Cj-C 4 haloalkoxy with 1 to 9 fluorine, chlorine - And / or bromine atoms, C 1 -C 4 alkylthio and / or C 1 -C 4 halogen alkylthio with 1 to 9 fluorine, chlorine and / or bromine atoms substituted C 2 -C 0 -alkenylene or for enteil optionally in the alkyl single or multiple, identical or different, by fluorine, chlorine, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, C 1 -C 4 alkoxy, Ci-C 4 -haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms, -C-
• R 14 and R 15 are, independently of one another, very particularly preferably hydrogen, —SO 2 R 11 , each in each case optionally up to nine times, identically or differently by fluorine, chlorine and / or bromine, —CC 4 -alkylamino, di- (C ⁇ - C 4 alkyl) amino, -C -C alkoxy, -C -C haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms, -C 4 - alkylthio and / or -C -C halogen alkylthio 1 to 9 fluorine, chlorine and / or bromine atoms substituted Ci
• C ⁇ alkyl or C 2 -C 0 alkenyl in each case optionally mono- to trisubstituted by identical or different fluorine, chlorine and / or bromine, C ⁇ -C4 alkyl, cyano, C 4 -haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, C ⁇ - C - alkoxy, -C-C 4 haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms, dC - alkylthio and / or C 1 -C 4 haloalkylthio with 1 to 9
• R 14 and R 15 furthermore together very particularly preferably represents in each case optionally mono- to tetrasubstituted in the alkylene moiety by identical or different fluorine, chlorine, cyano, C 4 -alkyl, C 4 -haloalkyl having 1 to 9 fluorine, Chlorine and / or bromine atoms, -C-C 4 - alkoxy, -C-C -haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms, dC - alkylthio and / or C ⁇ -C -haloalkylthio with 1 to 9 fluorine , Chlorine and / or bromine atoms substituted C 4 -C 5 alkylene, - (CH 2 ) 2 -O- (CH 2 ) 2 -, - (CH 2 ) 2 -S- (CH 2 ) 2-, - ( CH 2 ) 2 - N (R 22 ) - (CH 2
• R 16 and R 17 independently of one another very particularly preferably represent hydrogen, optionally optionally up to nine times, identically or differently, by fluorine, chlorine, bromine, C 1 -C 4 -alkoxy and / or C 1 -C 4 alkylthio substituted Cj-C ⁇ -Alkyl, for each optionally up to fourfold, the same or different by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl
• R 16 and R 17 furthermore together very particularly preferably represents in each case optionally mono- to tetrasubstituted by identical or different fluorine, chlorine, bromine, C ⁇ -C 4 -alkyl, C 4 -haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy with 1 to 9
• R 20 and R 21 independently of one another very particularly preferably are hydrogen, C 4 - alkyl, C ⁇ -C 4 -haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms or represents optionally monosubstituted to tetrasubstituted by identical or ver - separated by fluorine, chlorine, bromine and / or -CC 4 alkyl substituted C 3 - C ö cycloalkyl.
• R 20 and R 21 together also very particularly preferably represent - (CH 2 ) 3 -, - (CH 2 ) 4 -, - (CH 2 ) 5 -, - (CH 2 ) 2-O- (CH 2 ) 2 - or - (CH 2 ) 2-S- (CH 2 ) 2 -.
• R 22 very particularly preferably represents hydrogen, -SO 2 R n , -COR 11 or -CO 2 R 11 ; in each case optionally monosubstituted or polysubstituted by identical or different fluorine, chlorine, bromine, cyano, methylamino, ethylamino, di- (C ⁇ -C ö alkyl) amino, C ⁇ -C 4 - alkoxy, C ⁇ -C 4 -haloalkoxy having 1 up to 9 fluorine,
• w very particularly preferably represents 0, 1 or 2.
• n very particularly preferably represents 1 or 2.
• R 1 is particularly particularly preferably fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, trifluoromethoxy, methylthio or trifluoromethylthio.
• R 2 and R 3 independently of one another are particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy or trifluoromethoxy.
• R 4 particularly preferably represents chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl,
• Trifluoroethyl or for -SO 3 R 8 Trifluoroethyl or for -SO 3 R 8 .
• R 5 particularly preferably represents hydrogen, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl, trifluoroethyl or -SO 3 R 8 .
• R 4 and R 5 also together are particularly preferred for
• R 6 particularly preferably represents fluorine, chlorine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl, trifluoroethyl, methoxy, ethoxy, n- Propoxy, i-propoxy, 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 is particularly preferably 0 or 1.
• Q particularly particularly preferably 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 8 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, i-propyl, trifluoromethyl or trifluoroethyl.
• R 9 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, i-propyl, trifluoromethyl, trifluoroethyl, or in each case optionally monosubstituted to trisubstituted, identically or differently, by radicals from the list W 1, phenyl, furyl, thienyl , Pyrrolyl or pyridinyl.
• X particularly preferably represents a direct bond
• Oxygen, sulfur, -SO 2 -, -NR 10 -, -CO-, -C (O) -O-, -OC (O) -, -CH 2 -, - (CH 2 ) 2 -, -C C- (E or Z), -C ⁇ C-, -CH 2 O-, - (CH 2 ) 2 O-, -OCH 2 -, -O (CH 2 ) 2 -, -O-CH 2 -O -, -SCH 2 -, -S (CH 2 ) 2 -, -CH 2 S- or - (CH 2 ) 2 S-.
• Y very particularly preferably stands for a direct bond or for 1, 4-phenylene, 1, 3-phenylene, 2,6-naphthylene, 2,7, which is optionally substituted once or twice, identically or differently by radicals from the list W 1 -Naphthylene, 2,4-furylene, 2,4-thienylene, 2,5-pyridinylene, 2,5-pyrimidinylene, 3,6-pyridazinylene or 2,5-pyrazinylene.
• Z is particularly preferably a direct bond, methylene or ethylene.
• E particularly particularly preferably represents hydrogen, fluorine, chlorine, bromine, hydroxy, cyano, formyl, -S (O) w R ⁇ , -OSO 2 R u , -NR 12 R 13 , -COR 11 ,
• W 1 particularly preferably represents fluorine, chlorine, bromine, cyano, formyl, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl,
• R 10 particularly preferably represents methyl, ethyl, n-propyl, i-
• R 11 particularly preferably represents methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, pentyl, hexyl, -CF 3 , -CHF 2 , -CC1 3 ,
• R 12 and R 13 independently of one another are particularly preferably hydrogen, -SO 2 R ⁇ , each optionally one or more times, identically or differently, by fluorine, chlorine and / or bromine, —CC 4 -alkylcarbonyl, —CC -C 4 alkylcarbonyloxy, C ⁇ -C alkylamino, di (dC 4 alkyl) amino, C ⁇ -C 4 - alkoxy, C ⁇ -C 4 -haloalkoxy having 1 to 9 fluorine, chlorine and / or bromine atoms, C ⁇ -C 4 - Alkylthio and / or -C-C 4 haloalkylthio with 1 to 9
• R 12 and R 13 also together, in particular, very particularly preferably represent, if appropriate, single or multiple, identical or different from fluorine, Chlorine and / or bromine, C 1 -C alkoxy, C 1 -C 4 haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms, C 1 -C 4 alkylthio and / or C r C 4 haloalkylthio with 1 up to 9 fluorine, chlorine and / or bromine atoms substituted C 2 -C 8 alkenylene or for one or more, optionally in the alkylene part, identical or different by fluorine, chlorine, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, C 1 -C 4 -haloalkyl with 1 to 9 fluorine, chlorine and / or bromine atoms,
• R 14 and R 15 independently of one another are particularly preferably hydrogen, -SO 2 CF 3 , 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 14 and R 15 together also particularly particularly preferably represent - (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 22 ) - (CH 2 ) 2-.
• R 16 and R 17 independently of one another are particularly preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-hexyl, trifluoromethyl, trifluoroethyl, cyclopropyl , Cyclopentyl, cyclohexyl or for phenyl or benzyl substituted in each case optionally up to four times, identically or differently by fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, trifluoromethoxy.
• R 16 and R 17 also together, in particular, very particularly preferably, each have a single to four-fold structure, the same or different
• R 20 and R 21 independently of one another are particularly preferably hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-hexyl, trifluoromethyl, trifluoroethyl , Cyclopropyl, cyclopentyl or
• R 20 and R 21 together also particularly particularly preferably represent - (CH 2 ) 3 -, - (CH 2 ) 4 -, - (CH 2 ) 5 -, - (CH 2 ) 2 -O- (CH 2 ) 2 - or - (CH 2 ) 2 -S- (CH 2 ) 2 -.
• R particularly preferably represents hydrogen, -SO 2 R, -COR 11 or -CO 2 R n ; in each case optionally monosubstituted or polysubstituted by identical or different fluorine, chlorine, bromine, cyano, methylamino, ethylamino, di- (C ⁇ -C ⁇ alkyl) amino, C ⁇ -C 4 -alkoxy, C 4 -haloalkoxy having 1 up to 9 fluorine, chlorine and / or bromine atoms, -C-C - alkylthio and / or Ci
• R, ⁇ , R, R, R, R, m and Q have the meanings given above.
• R 1 represents fluorine or chlorine
• R 2 represents hydrogen or fluorine and R 4 , R s , R 6 , m and Q have the meanings given above.
• Saturated hydrocarbon radicals such as alkyl
• heteroatoms e.g. in alkoxy, where possible, be straight-chain or branched.
• ⁇ 1 -pyrrolines required as starting materials when carrying out process (A) according to the invention are generally defined by the formulas (II) and (II-a).
• R 1 , R 2 , R 3 , R, m and Q are preferably, particularly preferably, very particularly preferably or particularly very particularly preferably those meanings which are already in connection with the description of the compounds of the formula according to the invention (I) were mentioned as preferred, particularly preferred etc. for these radicals.
• Pyrrolines of the formulas (II) and (II-a) are known and / or can be prepared by known processes (cf. e.g. WO 98/22438, WO 99/59967 and WO 99/59968).
• Formula (III) provides a general definition of the succinimides required as starting materials when carrying out process (A) according to the invention.
• shark 1 preferably represents chlorine or bromine.
• Formula (IV) provides a general definition of the sulfonyl chlorides required as starting materials when carrying out process (A) according to the invention.
• shark 2 preferably represents chlorine or bromine, particularly preferably chlorine.
• R 23 preferably represents C 1 -C 4 alkyl or C 1 -C 4 haloalkyl, particularly preferably methyl or trifluoromethyl.
• Suitable diluents for carrying out process (A) according to the invention are all customary inert, organic solvents.
• preferential 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,
• Suitable acid binders for carrying out process (A) according to the invention are, if appropriate, in each case all of the inorganic and organic bases customary for such reactions.
• Alkaline earth metal or alkali metal hydroxides such as sodium hydroxide, calcium hydroxide, potassium hydroxide, or also ammonium hydroxide
• alkali metal carbonates such as sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate, and also alkali metal or alkaline earth metal acetates such as sodium acetate, potassium acetate, calcium acetate, alkali metal alkali metal, are preferably usable.
• Sodium hydroxide or potassium hydroxide is particularly preferably used.
• reaction temperatures can in each case be varied within a substantial range. In general, temperatures between 20 ° C and 140 ° C, preferably between 50 ° C and 100 ° C.
• reaction components in other ratios.
• the Refurbishment is carried out using customary methods. In general, the procedure is such that a precipitate is optionally obtained after addition of a diluent and this is filtered off. The filtrate is washed, dried, filtered and concentrated. If appropriate, the residue is freed of any impurities that may still be present using customary methods, such as chromatography or recrystallization.
• Formula (V) provides a general definition of the amino ketones required as starting materials when carrying out process (B) according to the invention.
• R 1, R 2, R 3, R 6, m and Q preferred, particularly preferred, very particularly preferred or especially preferably has those meanings which have already been in connection with the description of the inventive compounds of formula ( I) were mentioned as preferred, particularly preferred etc. for these radicals.
• R 4 "2 preferably represents Cj-Cio-alkyl, Ci-CIO haloalkyl, more preferably Ci-COE-alkyl, Ci-C ö haloalkyl having 1 to 13 fluorine, chlorine and bromine atoms or, especially for Methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl or trifluoroethyl.
• R 5 "2 preferably represents hydrogen, -CC-alkyl, C ⁇ -C ⁇ o -Halogenalkyl, particularly preferably for hydrogen, -CC 6 alkyl, Ci-C ö -haloalkyl with 1 to 13 fluorine, chlorine and / or bromine atoms, very particularly preferably for hydrogen, methyl, ethyl, n-propyl, i Propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl or trifluoroethyl.
• Aminoketones of the formula (V) are new. They can be made by
• R 4 "2 , R 5" 2 , R 6 , m and Q have the meanings given above,
• R 1 , R 2 and R 3 have the meanings given above and
• M 1 represents Li, MgCl, MgBr, Mgl or ZnCl,
• a diluent e.g. tetrahydrofuran
• the lactams required as starting materials when carrying out process (a) are generally defined by the formula (IX).
• R 6 , m and Q are preferably, particularly preferably, very particularly preferably or in particular very particularly preferably 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.
• R 4'2 and R 5 "2 are preferably, particularly preferably or very particularly preferably for those meanings which are already in connection with the description of the compounds of the formula (V) for these radicals have been mentioned as preferred, particularly preferred etc.
• Lactams of the formula (IX) are new. They can be made by
• R 6 , m and Q have the meanings given above,
• R 4 "2 has the meanings given above and
• G represents a leaving group
• a diluent e.g. tetrahydrofuran
• a diluent e.g. tetrahydrofuran
• Formula (X) provides a general definition of the metallated aromatics required as starting materials when carrying out process (a).
• R 1 , R 2 and R 3 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. in connection with the description of the compounds of the formula (I) according to the invention for these radicals.
• M 1 preferably represents Li, MgCl, MgBr, Mgl or ZnCl, particularly preferably Li, MgCl, MgBr or Mgl, very particularly preferably Li, MgCl or MgBr.
• Metallized aromatics of the formula (X) are known or can be prepared from the corresponding aromatics or halogen aromatics by known methods (e.g. lithiation or Grignard reaction).
• Formula (XI) provides a general definition of the pyrrolidones required as starting materials when carrying out process (b).
• R 6 , m and Q are preferably, particularly preferably, very particularly preferably or in particular very particularly preferably 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.
• Pyrrolidones of the formula (XI) are known and / or can be prepared by known processes (cf. WO 98/22438).
• Formula (XII) provides a general definition of the electrophiles required as starting materials when carrying out process (b).
• R 4 is preferably, particularly preferably or very particularly preferably, those radicals which have already been mentioned as preferred, particularly preferred, etc. in connection with the description of the amino ketones of the formula (V).
• G is preferred for halogen, methanesulfonyl, trifluoromethylsulfonyl or toluenesulfonyl.
• Electrophiles of the formula (XII) are known.
• 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; Nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide or sulfones such as sulfolane. Methylene chloride, chloroform, toluene, methanol or ethanol are 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 + 120 ° C, preferably between -10 ° C and + 60 ° C.
• 100 moles of a protonic acid are generally employed per mole of compound of the formula (V).
• the reaction components in other ratios.
• the processing takes place according to usual methods. In general, the reaction mixture is concentrated in a suitable manner
• Formula (VI) provides a general definition of the cyclopropanes required as starting materials when carrying out process (C) according to the invention.
• R 1, R 2, R 3, R 6, m and Q preferred, particularly preferred, very particularly preferred or especially preferably has those meanings which have already been in connection with the description of the inventive compounds of formula ( I) were mentioned as preferred, particularly preferred etc. for these radicals.
• R 1 , R 2 , R 3 , R 6 , m and Q have the meanings given above,
• a trialkylsulfoxonium halide e.g. trimethylsulfoxonium iodide
• a base e.g. sodium hydride
• a diluent e.g. dimethylsulfoxide
• Formula (VII) provides a general definition of the alcohols required as starting materials when carrying out process (C) according to the invention.
• R 8 preferably, particularly preferably, very particularly preferably or in particular very particularly preferably denotes 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 were.
• Formula (XIII) provides a general definition of the ⁇ , ⁇ -unsaturated ketones required as starting materials when carrying out process (c). In this
• Formula R 1 , R 2 , R 3 , R 6 , m and Q are preferably, particularly preferably, very particularly preferably or particularly very particularly preferably those meanings which have already been associated with the description of the compounds of the formula (I) according to the invention were mentioned as preferred, particularly preferred etc. for these radicals.
• ⁇ , ⁇ -Unsaturated ketones of the formula (XIII) are known and / or can be prepared by known methods.
• reaction temperatures when carrying out process (C) according to the invention can be varied within a substantial range. In general, temperatures between 40 ° C. and 200 ° C., preferably between 40 ° C. and 140 ° C., particularly preferably between 60 ° C and 120 ° C. If one works at temperatures below 40 ° C., predominantly ⁇ -ketosulfonic acid derivatives of the formula (XIV)
• R, R, R, R, m and Q have the meanings given above.
• ß-Ketosulfonic acid derivatives can be deacylated in the presence of an acid (e.g. 6N hydrochloric acid), optionally in the presence of a diluent (e.g. ethanol) and then cyclize in situ to ⁇ '-pyrrolines of the formula (I-g)
• an acid e.g. 6N hydrochloric acid
• a diluent e.g. ethanol
• R 1 , R 2 , R 3 , R 6 , m and Q have the meanings given above.
• ⁇ 1 -pyrrolines of the formula (Ig) can be prepared by conventional methods to give compounds of the formula (Ih)
• R represents optionally substituted alkyl
• Formula (VIII) provides a general definition of the aldehydes required as starting materials when carrying out process (D) according to the invention.
• Formula R 9 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 this radical in connection with the description of the compounds of the formula (I) according to the invention.
• Suitable diluents for carrying out process (D) according to the invention are mixtures of glacial acetic acid and alcohols, such as methanol, ethanol or propanol. Mixtures of glacial acetic acid and methanol are preferably used.
• Suitable acid binders for carrying out process (D) according to the invention are all inorganic and organic bases customary for such reactions.
• Alkaline earth metal or alkali metal hydroxides such as sodium hydroxide, calcium hydroxide, potassium hydroxide, or also ammonium hydroxide
• alkali metal carbonates such as sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate, alkali metal or alkaline earth metal acetates, such as sodium acetate, potassium acetate, calcium acetate, and tertiary, are preferably usable Trimethylamine, triethylamine, tributylamine, diethylisopropylamine, N, N-dimethylaniline,
• reaction temperatures can in each case be varied within a substantial range. In general, temperatures between 0 ° C and 180 ° C, preferably between 20 ° C and 160 ° C, particularly preferably between 60 ° C and 120 ° C.
• Halogenated aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane; Dichloromethane, chloroform; Alcohols, such as methanol, ethanol, propanol; Nitriles such as acetonitrile; Esters like Methyl acetate or ethyl acetate. It is particularly preferred to use aliphatic hydrocarbons, such as hexane or heptane, and alcohols, such as methanol or propanol, very particularly preferably n-heptane and isopropanol or mixtures of these.
• 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 example in one of the processes (A) or (D) according to the invention.
• the procedure is generally carried out under atmospheric pressure. However, it is also possible to work under increased or reduced pressure.
• the active compounds according to the invention are suitable, with good plant tolerance and favorable warm-blood toxicity, for combating animal pests, in particular insects, arachnids and nematodes which occur in agriculture, in forests, in the protection of stored products 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.
• Diplopoda e.g. Blaniulus guttulatus.
• Chilopoda e.g. Geophilus ca ⁇ ophagus, Scutigera spp.
• Thysanura e.g. Lepisma saccharina.
• Orthoptera e.g. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
• Leucophaea maderae, Blattella germanica From the order of the Dermaptera, for example, Forficula auricularia. From the order of the Isoptera, for example Reticulitermes spp ..
• Phthiraptera e.g. Pediculus humanus co ⁇ oris, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp ..
• Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci
• Heteroptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp. From the order of the Homoptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp. From the order of the Homoptera e.g.
• Empoasca spp. Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.
• Ceuthorrhynchus assimilis Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.
• Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
• Dacus oleae Tipula paludosa, Hylemyia spp., Liriomyza spp .. From the order of the Siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp .. From the Arachnida class e.g.
• Hyalomma spp. Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp ..
• Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaph.
• the compounds 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 compounds according to the invention can also be used in certain concentrations or application rates as herbicides and microbicides, for example as fungicides, antifungal agents and bactericides. You leave may also be used as intermediates or products for the synthesis of other 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 cultivated plants (including naturally occurring cultivated plants).
• Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including those by
• Plant variety rights of protectable or non-protectable plant varieties 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.
• Storage room according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by single- or multi-layer coating.
• the active compounds according to the invention can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances ,
• formulations are prepared in a known manner, for example by mixing the active compounds according to the invention with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
• extenders that is to say liquid solvents and / or solid carriers
• surface-active agents ie emulsifiers and / or dispersants and / or foam-generating agents.
• water is used as an extender, e.g. also organic
• Solvents are used as auxiliary solvents.
• the following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable
• Oils Oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
• ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
• strongly polar solvents such as dimethylformamide and dimethyl sulfoxide
• 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 as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems;
• natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth
• 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
• non-ionic 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 dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.
• Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
• Other additives can be mineral and vegetable oils.
• Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
• the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
• the active compounds according to the invention can be present in commercially available formulations and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
• Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
• Debacarb dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomo ⁇ h, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon,
• Famoxadone Fenapanil, Fenarimol, Fenbuconazol, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimo ⁇ h, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Flu ⁇ rimidol, Flusilimidol
• Metconazole Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin, Nickel-dimethyldithiocarbamate, Nitrothal-isopropyl, Nuarimol, Ofurace, Oxadixyl, Oxamocarb, Oxoliniciminol, Oxyoboxicoxinolimid, Oxyobenzolimidolacid, Oxyobenzolimidolacid, Oxyobenzolimidolacid, Oxyacidoximidolacid, Oxyacidoximidolacid, Oxyacidoximidolacid, Oxyacid Oximicolin, Oxyacid Oximidolacin, Oxyacid Oximidolacid, Oxyacid Oximidolacid, Oxyacidoximidolacid, Oxyacid Oximidolacid, Oxyacid Oximidolacid, Oxyacidoximidolacid
• Tebuconazole Tecloftalam, Tecnazen, Tetcyclacis, Tetraconazole, Thiabendazole, Thicyofen, Thifluzamide, Thiophanate-methyl, Thiram, Tioxymid, Tolclofos-methyl, Tolylfluanid, Triadimefon, Triadimenol, Triazbutil, Triazoxid, Trichlamid, Tricyclazol,
• Dagger G OK-8705, OK-8801, ⁇ - (1, 1-dimethylethyl) -ß- (2-phenoxyethyl) - 1 H-1, 2,4-triazole-1-ethanol, ⁇ - (2,4 -Dichl ⁇ henyl) -ß-fluoro-ß-propyl-1 H-1, 2,4-triazole-1-ethanol, ⁇ - (2,4-dichlo ⁇ henyl) -ß-methoxy- ⁇ -methyl-1 H-1, 2,4-triazol-1-ethanol, ⁇ - (5-methyl-l, 3-dioxan-5-yl) -ß - [[4- (trifluoromethyl) phenyl] methylene] -lH-l, 2, 4-triazole-1-ethanol,
• Bactericides bronopol, dichlorophene, nitrapyrin, nickel-dimethyldithiocarbamate, kasugamycin,
• Insecticides / acaricides / nematicides Abamectin, Acephate, Acetamiprid, Acrinathrin, Alanycarb, Aldicarb, Aldoxycarb,
• Cadusafos Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlo ⁇ yrifos, Chlo ⁇ yrifos M, Chlovaporthrin, Cis-Resmethrin,
• Fenamiphos Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate,
• Fipronil fluazuron, flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,
• Granuloseviruses Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
• Metolcarb Metoxadiazone, Mevinphos, Milbemectin, Monocrotophos,
• Paecilomyces fumosoroseus Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A,
• Pirimiphos M Profenofos, Promecarb, Propoxur, Prothiofos, Prothoat, Pymetrozine,
• Tefluthrin Temephos, Temivinphos, Terbufos, Tetrachlorvinphos, Thetacypermethrin, Thiamethoxam, Thiapronil, Thiatriphos, Thiocyclam hydrogen oxalate, Thiodicarb, Thiofanox, Thuringiensin, Tralocythrin, Tralomethrin
• Triarathenes triazamates, triazophos, triazuron, trichlophenidines, trichlorfon,
• 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 a mixture with synergists.
• Synergists are compounds through which the action of the active compounds according to the invention is increased without the added synergist itself having to be active.
• the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
• the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
• the application takes place in a customary manner adapted to the application forms.
• the active 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.
• transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods are treated.
• Organisms and their parts treated.
• the treatment according to the invention can also give rise to additive (“synergistic”) effects.
• additive for example, reduced application rates and / or widening of the activity spectrum and / or an increase in the action of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting,
• 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 shelf life and / or Machinability of crop products Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial
• Pests such as insects, mites, phytopathogenic fungi, bacteria and / or viruses and an increased tolerance of the plants to certain herbicides Active ingredients
• transgenic plants are the important cultivated plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits of apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes and cotton and rapeseed are highlighted.
• the properties (“traits”) which are particularly emphasized are the plants' increased defense against insects by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), Cry ⁇ A (b), Cry ⁇ A (c), CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
• the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins are also particularly emphasized as properties (“traits”).
• properties (“traits”) are also particularly emphasized the increased tolerance of the plants to certain herbicidal active ingredients, for example
• Imidazolinones sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene).
• the genes which impart the desired properties can also occur in combinations with one another in the transgenic plants.
• Examples of “Bt plants” are corn varieties, cotton varieties, soy varieties and potato varieties that are sold under the trade names YIELD GARD ® (e.g.
• herbicide-tolerant plants are maize varieties, cotton varieties and soy varieties which are sold under the trade names Roundup Ready ® (tolerance against glyphosate, for example corn, cotton, soybeans), Liberty Link ® (tolerance against
• Phosphinotricin for example rape
• IMI ® tolerance to imidazolinones
• STS tolerance to sulfonylureas, for example corn
• Herbicide-resistant plants (bred conventionally for herbicide tolerance) plants also sold under the name Clearfield ® varieties (eg maize) are mentioned. It goes without saying that these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties (“traits”).
• the plants listed can be treated particularly advantageously 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 ingredients 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, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas.
• animal parasites ectoparasites
• tick ticks leather ticks
• 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., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola 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.,
• Siphonaptrida for example Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp ..
• the Heteropterida for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp ..
• Actinedida Prostigmata
• Acaridida e.g. Acarapis spp., Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypppectoles spp ., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp ..
• ticks such as Amblyomma hebraeum
• parasitic flies such as against Lucilia cuprina
• fleas such as Ctenocephalides felis.
• 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. By fighting these arthropods, death traps and
• 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,
• the active compounds of the formula (I) according to the invention can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds according to the invention in an amount of 1 to 80% by weight, apply directly or after 100 to 10,000-fold dilution or use it as a chemical bath.
• formulations for example powders, emulsions, flowable agents
• insects may be mentioned by way of example and preferably, but without limitation:
• Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.
• Kalotermes flavicollis Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
• Bristle tails such as Lepisma saccharina.
• non-living materials such as preferably plastics, adhesives, glues, papers and cartons, leather, wood, wood processing products and paints.
• the material to be protected 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,
• the active compounds according to the invention can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
• the formulations mentioned can be prepared in a manner known per se, for example by mixing the active compounds according to the invention with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellants, optionally desiccants and UV stabilizers and optionally dyes and pigments and other processing aids.
• insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active ingredient according to the invention in a concentration of
• the amount of the agents or concentrates used depends on the type and occurrence of the insects and on the medium. The optimal amount can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.
• the organic chemical solvents used are preferably oily or oily ones
• Solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, are used.
• Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.
• liquid aliphatic hydrocarbons with a boiling range from 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range from 180 to 220 ° C. and / or spindle oil and / or monochloronaphthalene, preferably ⁇ -monochloronaphthalene, are used.
• organic non-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 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.
• Solvent or solvent mixture replaced by an aliphatic polar organic chemical solvent or solvent mixture.
• the known organic-chemical binders are the water-thinnable 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 as inden
• the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellants, odor correctors and inhibitors or anticorrosive agents and the like can be used.
• At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder.
• Alkyd resins having an oil content of more than 45% by weight, preferably 50 to, are preferred according to the invention
• binder All or part of the 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 originate 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 ether or higher molecular glycol glycerol ether , Glycerol ester and p-toluenesulfonic acid ester.
• phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate
• phosphoric acid esters such as tributyl phosphate
• adipic acid esters such as di- (2-ethylhexyl) adipate
• stearates such as butyl stearate or am
• Fixing agents are chemically based on polyvinyl alkyl ethers such as polyvinyl methyl ether or ketones such as benzophenone and 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.
• Insecticides such as chlo ⁇ yriphos, phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthronid, as well as thifloxiduron, and methifluorideuron, fifluorideuron, and methifluorideuron, as well as thifluorideuron, as well as fungloxidonuron, as well as fungloxidonuron, as well as fungloxidonuron, as well as fungloxidonuron, as well as fungalidium clonid, as well as Funglumidopuron, as well Epoxyconazole, Hexaconazole, Azaconazole, Propiconazole, Tebuconazole, Cyproconazole, Metconazole, Imaz
• 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.
• Baianus or Pollicipes species increases the frictional resistance of ships and subsequently leads to a significant increase in operating costs due to increased energy consumption and, moreover, frequent dry dock stays.
• Antifouling (anti-fouling) - have effect.
• heavy metals such as e.g. in bis (trialkyltin) sulfides, tri-M-butyltin laurate, tri-w-butyltin chloride, copper (I) oxide,
• Triethyltin chloride tri - «- butyl (2-phenyl-4-chl ⁇ henoxy) tin, tributyltin oxide, molybdenum disulfide, antimony oxide, polymeric butyl titanate, phenyl- (bispyridine) - bismuth chloride, tri-tt-butyltin fluoride, manganethylene-zincdihodi-carbamate-diblami-carbamate-dibi-thiobi-carbamate-dibi-carbamate-dibi-carbamate-dibi-carbamate-dibi-carbamate, Zinc and copper salts of 2-pyridinthiol-1-oxide, bisdimethyldithiocarbamoylzincethylene bisthiocarbamate, zinc oxide, copper (I) ethylene bisdithiocarbamate, copper thiocyanate, copper naphthenate and tributyltin halides can be dispensed with
• the ready-to-use antifouling paints can also be used if necessary
• active ingredients preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.
• Suitable combination partners for the antifouling agents according to the invention are preferably: Algicides like
• 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.
• 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 r 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
• Paints may also contain materials such as rosin to enable controlled release of the active ingredients.
• the paints may also contain plasticizers, modifiers that affect the rheological properties, and other conventional ingredients. Also in self-polishing antifouling
• the active compounds according to the invention are also suitable for controlling animal pests, in particular insects, arachnids and mites, which live in closed spaces, such as, for example, apartments, factory halls, offices, vehicle cabins and the like. occurrence. To combat these pests, they can be used alone or in combination with other active ingredients and auxiliaries in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:
• Sco ⁇ ionidea e.g. Buthus occitanus.
• Acarina e.g. Argas persicus, Argas reflexus, Bryobia spp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis,
• Dermatophagoides pteronissimus Dermatophagoides forinae.
• Dermatophagoides forinae From the order of the Araneae, for example Aviculariidae, Araneidae.
• From the order of the Opiliones for example Pseudosco ⁇ iones chelifer, Pseudosco ⁇ iones cheiridium, Opiliones phalangium.
• Diplopoda e.g. Blaniulus guttulatus, Polydesmus spp ..
• Chilopoda e.g. Geophilus spp ..
• Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia inte ⁇ unctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
• Ctenocephalides canis Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
• Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
• Pediculus humanus capitis for example Pediculus humanus capitis, Pediculus humanus co ⁇ oris, Phthirus pubis.
• Heteroptera for example Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
• the filtrate is washed in succession with 1N sodium hydroxide solution, saturated sodium bicarbonate solution and saturated ammonia. Washed sodium chloride solution.
• the organic phase is dried over sodium sulfate, filtered and concentrated.
• the crude product is purified by chromatography on silica gel (mobile phase: n-hexane / ethyl acetate 9: 1).
• the precipitate is filtered off and discarded.
• the filtrate is concentrated.
• the crude product is purified by chromatography on silica gel (mobile phase: n-hexane / ethyl acetate 4: 1).
• the mixture is stirred at this temperature for two hours and then allowed to warm to room temperature within 16 hours.
• the mixture is poured into an aqueous ammonium chloride solution and extracted with ethyl acetate.
• the organic phase is washed with water, dried over magnesium sulfate, filtered and concentrated.
• the crude product is purified by chromatography on silica gel (mobile phase: cyclohexane / ethyl acetate 8: 1).
• 1,3-difluorobenzene (0.48 g, 4.18 mmol) is placed in tetrahydrofuran (25 ml).
• n-butyllithium (2.61 ml, 1.6 M in hexane, 4.18 mmol) is added dropwise and the mixture is stirred at this temperature for one hour.
• a solution of tert-butyl-3,3-dimethyl-2-oxo-5- [4 , - (trifluoromethoxy) -l, r-biphenyl-4-yl] -l-pyr ⁇ olidine carboxylate (1.70 g, 3.8 mmol) in tetrahydrofuran (50 ml) is added dropwise at -78 ° C. The mixture is stirred for two hours at this temperature and then left
• the reaction mixture is subsequently stirred at 80 ° C. for 16 hours.
• the mixture is cooled to room temperature, diluted with water (50 ml) and the precipitate is filtered off with suction.
• the product is obtained as a mixture of diastereomers.
• 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 calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values using the
• the lambda max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
• Solvent 30 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the stated amount of solvent and emulsifier and the concentrate is diluted to the desired concentration with water containing emulsifier.
• Soybean shoots (Glycine max) are treated by dipping into the active ingredient preparation of the desired concentration and are populated with the Heliothis virescens caterpillars 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 1 part 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.
• the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
• Solvent 30 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the stated 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.
• Solvent 30 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the stated 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 1 part 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 1 part 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 1 part 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.
• Test animals Lucilia cuprina larvae
• test tube containing approx. 1 cm horse meat and 0.5 ml of the active ingredient preparation to be tested. The effectiveness of the active substance preparation is determined after 24 and 48 hours.
• the test tubes are transferred to beakers with a sand-covered bottom. After a further 2 days, the test tubes are removed and the dolls are counted.
• the effect of the active substance preparation is assessed according to the number of flies hatched after 1.5 times the development time of an untreated control. 100% means that no flies have hatched; 0% means that all flies hatched normally.
• Test animals Amblyomma variegatum or A. hebraeum, fully soaked
• Active ingredients Active ingredient effect on the concentration in ppm molting in%
• 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
• Soybean shoots (Glycine max) of the Roundup Ready variety (trademark of Monsanto Comp. USA) are treated by dipping into the preparation of active compound of the desired concentration and populated with the tobacco bud caterpillar Heliothis virescens while the leaves are still moist.
• the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.

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

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• 2001
  • 2001-02-13 DE DE10106455A patent/DE10106455A1/de not_active Withdrawn
• 2002
  • 2002-01-31 JP JP2002564494A patent/JP2004527485A/ja not_active Withdrawn
  • 2002-01-31 BR BR0207171-1A patent/BR0207171A/pt not_active Application Discontinuation
  • 2002-01-31 EP EP02710823A patent/EP1368311A1/de not_active Withdrawn
  • 2002-01-31 MX MXPA03007242A patent/MXPA03007242A/es unknown
  • 2002-01-31 CN CNA028049039A patent/CN1491211A/zh active Pending
  • 2002-01-31 IL IL15713302A patent/IL157133A0/xx unknown
  • 2002-01-31 WO PCT/EP2002/000990 patent/WO2002064561A1/de not_active Application Discontinuation
  • 2002-01-31 KR KR10-2003-7009779A patent/KR20030074730A/ko not_active Application Discontinuation
  • 2002-01-31 US US10/467,992 patent/US20040077881A1/en not_active Abandoned

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