Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
  • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
  • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
  • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
  • C07D279/12—1,4-Thiazines; Hydrogenated 1,4-thiazines not condensed with other rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
  • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
  • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
  • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
  • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

• the invention relates to new aryl-substituted heterocyclic enaminones, several processes for their preparation, intermediates and their use as crop protection agents, in particular as herbicides, acaricides, nematicides and insecticides.
• K oxygen or sulfur
• Ar represents substituted phenyl, naphthyl or optionally substituted mono- or bicyclic hetaryl with 5 to 10 ring atoms
• V represents oxygen or the groups -S (O) n - or ⁇ NW
• W represents hydrogen, optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxy, phenylalkyloxy, phenyl, phenylalkyl, hetaryl, hetarylalkyl or for the groups -COR 1 , -CO2R 1 ,
• Y 1 and Y 3 independently of one another for hydrogen, halogen or in each case optionally substituted alkyl, alkoxy, alkoxyalkyl, phenyl, phenylalkyl, hetaryl, hetarylalkyl or for the groups
• R 1 - CO 2 R 1 or - CO ⁇ stand, and R2
• Y 2 , Y 4 , Y 6 independently of one another represent hydrogen, halogen or optionally substituted alkyl
• Y 5 represents hydrogen or in each case optionally substituted alkyl or phenyl, or
• Y 4 and Y 5 together with the carbon atoms to which they are attached represent an optionally substituted saturated or unsaturated cycle which is optionally interrupted by heteroatoms, or Y 1 and Y 2 together with the carbon atom to which they are attached represent an optionally substituted saturated or unsaturated cycle which is optionally interrupted by heteroatoms,
• R 1 for hydrogen, for optionally substituted, saturated or unsaturated, each optionally interrupted by heteroatoms
• Hetaryl represents in each case optionally substituted phenylalkyl or hetarylalkyl
• R represents hydrogen, in each case optionally substituted, saturated or unsaturated alkyl or alkoxy, for in each case optionally substituted phenyl, phenylalkyl or phenylalkyloxy, or R 1 , R 2 , together with the nitrogen atom to which they are attached, can furthermore represent an optionally substituted and optionally interrupted by heteroatoms,
• R 3 represents hydrogen, each optionally substituted alkyl or alkoxy, each optionally substituted phenyl or phenylalkyl,
• R 4 represents hydrogen or optionally substituted alkyl
• R 5 , R 6 independently of one another represent hydrogen or optionally substituted alkyl.
• Ar preferably represents Ar 1 , where Ar 1 is in each case optionally one to five times by halogen, d-Cg-alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, dC 8 -alkoxy, C 2 -C 8 alkenyloxy, C 3 -C 8 alkynyloxy, dC 8 alkylthio, dC 6 - alkylsulfinyl, alkylsulfonyl 6 dC, dC 6 haloalkyl, halo-dC 6 alkoxy, C 2 -C 8 haloalkenyloxy, dC -Alkylidendiyl -dioxy, dC 2 -haloalkylidendiyl-dioxy, halogen -CC-C 4 -alkylthio, halogen-C 1 -C 4 -alkylsulfinyl,
• Ar 2 is Ar 1 , which is additionally substituted by phenyl, naphthyl, five- or six-membered hetaryl, phenyl-C 1 -C 4 -alkyl, phenyl-d-
• Haloalkyl, -C-C4-haloalkoxy, nitro or cyano are substituted.
• K preferably represents oxygen or sulfur.
• L preferably represents oxygen or sulfur.
• V preferably represents oxygen or the groups -S (O) n - or ⁇ NW •
• W preferably represents hydrogen, represents optionally fluorine and / or chlorine-substituted C r C 8 - alkyl, C 3 -C 8 - alkenyl, C 3 -C 8 - alkynyl,
• Y 1 and Y 3 are preferably independently of one another hydrogen, halogen, C.
• Y 2 , Y 4 , Y 6 preferably independently of one another represent hydrogen, halogen or C 1 -C 6 -alkyl substituted by fluorine and / or chlorine.
• Y 5 preferably represents hydrogen, dC 6 alkyl optionally substituted by fluorine or optionally optionally up to four times by halogen, d C 6 alkyl, dC 6 alkoxy, dC 4 haloalkyl, dC 4 haloalkoxy, cyano or nitro substituted phenyl, or
• Y 4 and Y 5 are preferably together with the carbon atoms to which they are attached a 5- to 8-membered, saturated or unsaturated Cycle which may be interrupted by from 1 to 3 heteroatoms from the series N, O, S and which is optionally monosubstituted to trisubstituted by halogen, C1-C4 - alkyl, C1-C4 alkoxy, C drHalogenalkyl, Ci-dpHalogenalkoxy, cyano or nitro can be substituted.
• Y 1 and Y 2 preferably together with the carbon atom to which they are attached represent a cycloalkyl ring ö dC.
• Z preferably represents hydrogen, in each case optionally substituted by fluorine and / or chlorine -CC 8 alkyl, cyano-C Cg-alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl- C r C 2 -alkyl, C r C4-alkoxy-C ⁇ -C4-alkyl, Ci-dt-haloalkoxy-Ci-di-alkyl, for each optionally simple to phenoxy-Ci-dj-alkyl, phenyl-Ci-di-alkyloxy-Ci substituted four times by halogen, C Cg-alkyl, C j -Cg-alkoxy, Ci-d j -haloalkyl, C ⁇ -C4-haloalkoxy, nitro or cyano -di-alky
• p is preferably 0 to 2.
• 1 preferably represents 0 to 2.
• R 1 preferably represents hydrogen (but not the residues -CO2R 1 and -SO 2 R 1 ), each optionally substituted by fluorine and / or chlorine.
• Cj-Cio-alkyl, C 2 -C 10 alkenyl, C 3 -Cg-alkynyl for each optionally substituted by fluorine, chlorine, C1-C4-alkyl, Ci-dj-alkoxy C 3 - C cycloalkyl or C5 -C 8 cycloalkenyl, in which a methylene group can optionally be interrupted by oxygen or sulfur, or for each optionally by up to four times by halogen, C j -Cg-
• R 2 preferably represents hydrogen, in each case optionally substituted by fluorine and / or chlorine Cj-Cg-alkyl, C 3 -Cg-alkenyl, C 3 -Cg-alkynyl, C Cg-alkoxy, C 3 -Cg-alkenyloxy or for phenyl, phenyl-C 1- dj-alkyl or phenyl, each optionally monosubstituted to tetrasubstituted by halogen, C j -Cg alkyl, C j -Cg alkoxy, C 1 -C haloalkyl, C 1 -C 4 haloalkoxy, cyano or nitro -C j -dralkoxy.
• R 1 , R 2 may preferably, together with the nitrogen atom to which they are attached, represent a five- to eight-membered cycle which is optionally substituted by C d j -alkyl and in which a methylene group may optionally be replaced by oxygen or sulfur ,
• R 3 preferably represents hydrogen, Cj-Cg-alkyl optionally substituted by halogen or in each case optionally up to four times by halogen, C Cg-alkyl, C Cg-alkoxy, C 1 -C -haloalkyl, C j -dt-halogen- alkoxy, cyano or nitro substituted phenyl or phenyl-C-C2-alkyl.
• R 4 preferably represents hydrogen or C j -Cg alkyl.
• R 5 , R 6 are preferably independently of one another hydrogen or optionally substituted by fluorine and / or chlorine
• R 7 preferably represents in each case optionally substituted by fluorine and / or chlorine CJ-CJ Q -alkyl, C 2 -C IQ-alkenyl, C 3 -C 10 -alkynyl, CC ⁇ - alkoxy, -C-C 4 -alkoxy-C 1 -C 4 alkyl, C d alkyl thio-C r C alkyl, each optionally substituted by fluorine, chlorine, C dp alkyl and / or C dp alkoxy C 3 -C 8 cycloalkyl or C 3 -C 8 -Cycloalkoxy, in which a methylene group can optionally be replaced by oxygen or sulfur, for each optionally up to four times by halogen, CpCg-alkyl, C j -Cg-alkoxy, C 1 -
• R 8 preferably represents hydrogen or Cj -dp alkyl.
• R 9 preferably represents hydrogen, in each case optionally substituted by fluorine and / or chlorine, C r C 10 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C r C 10 alkoxy, C -Cg- Alkenyloxy, optionally substituted by fluorine, chlorine, Cpd alkyl or CC 4 - alkoxy-substituted C 3 -C 8 cycloalkyl, in which a methylene group can optionally be replaced by oxygen or sulfur, each optionally up to four times by halogen, Cj- Cg-alkyl, CpCg-alkoxy, Cpdp-haloalkyl, CpC 4 -haloalkoxy, cyano or nitro substituted phenyl, phenyl-C pdpalkyl or phenyl-C C2-alkoxy.
• R 1 ° preferably represents hydrogen, C -Cg alkyl or C 3 -C 6 alkenyl.
• R 9 , R 10 may preferably, together with the nitrogen atom to which they are attached, represent a five- to eight-membered cycle optionally substituted by C4-alkyl, in which a methylene group may optionally be replaced by oxygen or sulfur.
• m preferably represents 0 to 2.
• n preferably represents 0 to 2.
• K particularly preferably represents oxygen or sulfur.
• Ar particularly preferably represents Ar 1 , where Ar 1 is in each case optionally one to three times by fluorine, chlorine, bromine, CpCg-alkyl, C -C 6 -alkenyl, C2-Cg-alkynyl, CpCg-alkoxy, C 3 -Cg- Alkenyloxy, C 3 -Cg-alkynyloxy, CpCg-alkylthio, C r C 4 -alkylsulfionyl, C dp -alkylsulfonyl, Cpdp-haloalkyl,
• CpC -haloalkoxy C 2 -C -haloalkenyloxy, CpC 2 -alkylidendiyl-dioxy, CpC 2 -haloalkylidendiyl-dioxy, halo -CC 2 -alkylthio, halo-CpC2-alkylsulfinyl, halo-CpC 2 -alkylsulfonyl , Hydroxy, mercapto, nitro, cyano, amino or by one of the following groups
• Ar 2 is Ar 1 , which is additionally substituted by phenyl, pyridyl, pyrimidyl, thienyl, furanyl, thiazolyl, tetrazolyl, triazolyl, benzyl, phenyl-dC 2 -alkoxy, phenyl-C 1 -C 2 -alkyl -S (O) p -, thienyl-dC 2 -alkoxy, thiazolyl-C ⁇ -C 2 -alkoxy, pyridyl-C 1 -C 2 -alkoxy, pyrimidyl-dC 2 -alkoxy, thiazolyl-C ⁇ -C 2 -alkyl- S (O) p -, pyridyl-dC 2 -alkyl-S (O) p , phenoxy, phenyl- S (O) p -, pyridyl-dC 2 -
• S (O) p - or thiazolyl-S (O) p - is substituted, these substituents in turn optionally being mono- to triple by fluorine, chlorine, bromine, Cp dpAlkyl, C 2 -C 4 alkenyl, CpC 4 alkoxy, C r C 2 -haloalkyl, C r C 2 - haloalkoxy, nitro or cyano.
• L particularly preferably represents oxygen or sulfur.
• V particularly preferably represents oxygen or the groups -S (O) n - or
• W particularly preferably represents hydrogen, in each case optionally substituted by fluorine and / or chlorine, CpCg-alkyl, C 3 -Cg-alkenyl, C 3 -Cg-
• X particularly preferably represents CN
• Y 1 and Y 3 independently of one another particularly preferably represent hydrogen, optionally fluorine, CpC4-alkyl, CpC 2 haloalkyl, C C4-alkoxy, Cpd ⁇ alkoxy-CpC-alkyl, each optionally up to three times by fluorine, chlorine, bromine, CpdpAlkyl, CpC4-alkoxy, -CC 2 haloalkyl,
• Y 2 , Y 4 , Y 6 are particularly preferably independently of one another hydrogen or C r dp alkyl.
• Y 5 particularly preferably represents hydrogen, represents optionally substituted by fluorine dC 4 - alkyl or optionally mono- to trisubstituted by fluorine, chlorine, bromine, C ⁇ -C 4 alkyl, dC 4 alkoxy, dC 2 haloalkyl, dC 2 - Halogenalkoxy, nitro or cyano substituted phenyl.
• Y 4 and Y 5 furthermore particularly preferably, with the carbon atoms to which they are attached, represent a 5- or 6-membered, saturated or unsaturated cycle which can be interrupted by a hetero atom from the series N, O, S and, if appropriate single or double by fluorine, chlorine, bromine, methyl, tert-butyl, methoxy, trif iormethyl, trifluoromethoxy,
• Y and Y furthermore particularly preferably together with the carbon atom to which they are attached represent a C 4 -C 6 cycloalkyl ring.
• Z particularly preferably represents hydrogen, in each case optionally substituted by fluorine and / or chlorine, dC 6 -alkyl, cyano-dC-alkyl, C 3 -C 6 -alkenyl, C 3 -C 8 -alkynyl, C 3 -C 6 - Cycloalkyl, C 3 -C 6 -cycloalkyl-dC 2 -alkyl, -C-C 4 -alkoxy-dC 2 -alkyl, C ⁇ -C 4 -halo-C 1 -C 2 -alkyl, for each in each case optionally up to three times by fluorine, chlorine, bromine, -C 4 alkyl, -C 4 -
• p particularly preferably represents 0 to 2.
• R 1 particularly preferably stands for hydrogen (but not for the radicals -CO2R 1 and -SO2R 1 ), for dC 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C - in each case optionally substituted by fluorine and / or chlorine.
• alkynyl which is optionally substituted in each case by fluorine, chlorine, dC 2 -alkyl, C 2 alkoxy C 3 -C 6 -Cy- cloalkyl or in each case optionally mono- or disubstituted by fluorine,
• R 2 particularly preferably represents hydrogen, in each case optionally substituted by fluorine and / or chlorine, dC 4 -alkyl, C -C 4 -alkenyl, C 3 -C 4 -
• R 1 , R 2 can particularly preferably, together with the nitrogen atom to which they are attached, represent a five- or six-membered cycle which may be substituted by C 1 -C 2 -alkyl and in which a methylene group may optionally be replaced by oxygen.
• R 5 particularly preferably represents hydrogen, methyl or ethyl.
• R 7 particularly preferably represents in each case optionally by fluorine and / or
• R 9 particularly preferably represents hydrogen, in each case optionally substituted by fluorine and / or chlorine, dC 6 -alkyl, C 3 -C 6 -alkenyl, dQ-alkynyl, d-C o -alkoxy, C 3 -C 6 -cycloalkyl, in which may optionally replace a methylene group with oxygen, for phenyl or phenyl-C substituted in each case optionally mono- or disubstituted by fluorine, chlorine, bromine, dC 4 -alkyl, dC 4 -alkoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, cyano or nitro ] -C 2 alkyl.
• R 10 particularly preferably represents hydrogen or -CC 4 - alkyl.
• R 9 , R 10 may furthermore particularly preferably, together with the nitrogen atom to which they are attached, represent a five- or six-membered cycle which may be substituted by dC 2 -alkyl and in which a methylene group may optionally be replaced by oxygen.
• n particularly preferably represents 0 or 1. n particularly preferably represents 0 to 2.
• Ar very particularly preferably stands for oxygen and sulfur.
• Ar very particularly preferably represents Ar 1 , where Ar 1 is in each case optionally one to three times by fluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl, s-, n-, i- or t-butyl, Methoxy, ethoxy, propoxy, i-propoxy, s-, n-, i- or t-butoxy, allyloxy, methallyloxy, 2-butenyloxy, propargyloxy, 2-butynyloxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl , Trifluoromethyl, difluoromethoxy, trifluoromethoxy, methylene dioxy, difluoromethylene dioxy, tetrafluoroethylene dioxy,
• Ar 2 is Ar 1 , which is additionally substituted by phenyl, pyridyl, thienyl, tetrazolyl, triazolyl, benzyloxy, benzylthio, thiazolylmethyloxy, pyridylmethyloxy, pyrimidylmethyloxy, thiazolylmethylthio, pyridylmethylthio, phenoxy or phenylthio is, these substituents in turn, if necessary, once or twice by fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, s-, n-, i- or t-butyl, methoxy, ethoxy, i-propoxy, s -, n- or t-butoxy, trifluoromethyl, trifluoromethoxy,
• Nitro or cyano are substituted.
• L very particularly preferably represents oxygen or sulfur.
• V very particularly preferably represents oxygen or sulfur.
• X very particularly preferably stands for - C, - CO-NH 2 , - C •
• Y 1 and Y 3 very particularly preferably independently of one another represent hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, in each case, if appropriate, in one to three times by fluorine, chlorine, Bromine, methyl, methoxy, trifluoromethyl, difluoromethoxy or trifluoromethoxy substituted phenyl or benzyl.
• Y 2 , Y 4 , Y 6 are very particularly preferably independently of one another hydrogen, methyl, ethyl.
• Y 5 very particularly preferably represents hydrogen, methyl, ethyl, propyl, i-propyl or optionally, once or twice, by fluorine, chlorine, bromine, methyl, ethyl, i-propyl, tert-butyl, methoxy, ethoxy, i- Propoxy, tert-butoxy, trifluoromethyl or trifluoromethoxy, substituted phenyl.
• Y 4 and Y 5 also very particularly preferably, together with the carbon atoms to which they are attached, represent a six-membered, unsaturated cycle which is optionally simply substituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro can be.
• Y 1 and Y 2 furthermore very particularly preferably together with the carbon atom to which they are attached represent a cyclobutyl radical.
• Z very particularly preferably represents hydrogen, methyl, ethyl, allyl, propargyl, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, methoxymethyl, ethoxymethyl, each in each case optionally one to two times by fluorine, chlorine, bromine, methyl , Methoxy, trifluoromethyl or trifluoromethoxy, cyano or nitro-substituted phenyl, benzyl, pyridylmethyl, thiazolylmethyl or for the groups R 1
• R 1 very particularly preferably represents hydrogen (but not the residues - CO 2 R! And -SO2R 1 ), methyl, ethyl, propyl, isopropyl, n-, s-, i- or t-butyl, allyl, propargyl, Cyclopropyl, cyclopentyl, cyclohexyl for phenyl or benzyl optionally substituted once or twice by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro.
• R 2 very particularly preferably represents hydrogen, methyl, ethyl, propyl, isopropyl, allyl, propargyl, methoxy, ethoxy, allyloxy or optionally optionally one to two times by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro substituted benzyloxy.
• R 1 , R 2 together with the nitrogen atom to which they are attached can very particularly preferably furthermore represent a pyrrolidine, thiazine, piperidine or morpholine residue.
• R 5 very particularly preferably represents hydrogen, methyl or ethyl.
• R 7 very particularly preferably represents methyl, ethyl, propyl, isopropyl, n-, s-, i- or t-butyl, vinyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, n-, s-, i- or t -Butyloxy, cyclopropyl, cyclopentyl, cyclohexyl, cyclopentyloxy, cyclohexyloxy, for each optionally single or double by fluorine, chlorine, bromine, methyl, n-, s-, i- or t-butyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro-substituted phenyl, pyridyl or benzyl or, in the case of the radicals a) and c) mentioned under Ar, also for a group R a
• R 9 very particularly preferably represents hydrogen, methyl, ethyl, propyl, isopropyl, n-, s-, i- or t-butyl, cyclopropyl, cyclopentyl, cyclohexyl, for optionally single or double by fluorine, chlorine, bromine, Methyl,
• R 10 very particularly preferably represents hydrogen, methyl or ethyl.
• R 9 , R 10 together with the nitrogen atom to which they are attached very particularly preferably represent a pyrrolidine, piperidine or morpholine radical.
• n very particularly preferably stands for 1.
• Ar particularly preferably represents Ar 1 , where Ar 1 is in each case optionally one to three times by fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, n-, s-, i- or t-butyl, methoxy, ethoxy, propoxy , Isopropoxy, n-, s-, i- or t-butoxy, allyloxy, methallyloxy, 2-butenyloxy, propargyloxy, 2-butynyloxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl,
• Ethylsulfonyl trifluoromethyl, difluoromethoxy, trifluoromethoxy, methylenedioxy, difluoromethylenedioxy, tetrafluoroethylenedioxy, difluoromethylthio, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, hydroxyl, nitro, phenyl, phenyl, pyrylto pyryl, pyryl, pyryl, pyryl, pyridyl, pyryl, pyridyl, pyryl, pyryl, pyridyl, pyryl, pyryl, pyridyl, pyryl, pyridyl, pyryl, pyridyl, pyryl, pyridyl, pyryl, pyridyl, pyryl, pyridyl, pyr
• Ar 2 is Ar 1 , which is additionally substituted by phenyl, benzyloxy or phenoxy, these substituents in turn optionally being mono- or disubstituted by fluorine, chlorine, bromine, methyl, Ethyl, isopropyl, n-, s-, i- or t-butyl, methoxy, ethoxy, isopropoxy, n-, s-, i- or t-butoxy, trifluoromethyl, trifluoromethoxy, nitro or cyano are substituted.
• K particularly preferably represents oxygen or sulfur.
• V particularly preferably represents oxygen or sulfur.
• X particularly preferably represents CN.
• Y 1 and Y 3 are particularly preferably independently of one another hydrogen, methyl, ethyl or propyl.
• Z particularly preferably represents hydrogen or methyl.
• n particularly preferably represents 1.
• Y 2 , Y 4 , Y 5 , Y 6 are particularly preferably independently of one another hydrogen, methyl and ethyl.
• Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl can also be used in connection with heteroatoms, e.g. in alkoxy, where possible, be straight-chain or branched.
• optionally substituted radicals can be mono- or polysubstituted, and in the case of multiple substitutions the substituents can be the same or different.
• Ar, V, X, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and m have the meanings given above, and
• V, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and m have the meanings given above, and
• A is O or S (O) q , where q is 0 or 2, and
• R 1 ' represents alkyl, in particular dC 6 alkyl, or benzyl,
• Me stands for a divalent transition metal atom, in particular nickel, and
• V, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and m have the meanings given above,
• V, Ar, X, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and m have the meanings given above,
• a base optionally in the presence of a base and optionally in the presence of a trivalent phosphorus compound (e.g. triphenylphosphine, triethylphosphite)
• a trivalent phosphorus compound e.g. triphenylphosphine, triethylphosphite
• Ar, V, X, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and m have the meanings given above and K for oxygen as well
• Ar, V, Z, X, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and m and n have one of the meanings given above, and
• V, Z, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and m have one of the meanings given above,
• halogenating agents such as phosgene, diphosgene and triphosgene, optionally in the presence of a diluent, to give compounds of the formula (VIII),
• V, Z, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and m have one of the meanings given above,
• Ar, V, Z, XjY 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and m have one of the meanings given above and
• K represents oxygen, with alkylating agents, acylating agents, sulfonylating agents or condensing agents of the formula (IX)
• G represents a leaving group such as halogen (in particular iodine, bromine, chlorine), sulfonate (such as mesylate, triflate or toluenesulfonate) or alkoxy,
• Ar 2 , V, X, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , Z and m have the meaning given above, and
• Ar 2 represents the substituents mentioned above under Ar 2 as additional substituents for Ar 1 ,
• a solvent optionally in the presence of a base and a noble metal complex, preferably a palladium complex.
• Ar, Z, V, X, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and m have the meaning given above, and
• Ar, Z, V, X, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and m have the meaning given above, and
• a sulfurization reagent such as phosphorus pentasulfide or 2,4-bis- (4-methoxyphenyl) -l, 2,3,4-dithiaphosphetane-2,4-disulfide (Lawesson-
• Ar, K, X, Z, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and m have the meaning given above, and
• n stands for the numbers 1 and 2
• Ar, K, Z, X, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and m have the meaning given above, and
• V represents sulfur atom
• reaction scheme e.g. 4-methyl-benzoylacetonitrile and 2-methoxy-2-dihydro-morpholine as starting materials
• T has the meaning given in the following table:
• R 12 represents alkyl, in particular dC 6 -alkyl, or benzyl, which may optionally be substituted, in the presence of an acid (e.g. an inorganic acid, such as hydrochloric acid) or a base (e.g. an alkali hydroxide such as sodium or potassium hydroxide) and optionally a diluent (e.g. an aqueous alcohol such as methanol or ethanol) at temperatures between an acid and a base (e.g. an alkali hydroxide such as sodium or potassium hydroxide) and optionally a diluent (e.g. an aqueous alcohol such as methanol or ethanol) at temperatures between
• an acid e.g. an inorganic acid, such as hydrochloric acid
• a base e.g. an alkali hydroxide such as sodium or potassium hydroxide
• a diluent e.g. an aqueous alcohol such as methanol or ethanol
• 0 ° C and 200 ° C preferably between 20 ° C and 150 ° C hydrolyzed and then decarboxylated.
• the compounds of the formula (XI) can be prepared by known processes (Organikum, 16th edition, p. 480, VEB Deutscher Verlag dermaschineen, Berlin 1986).
• R 12 represents alkyl, in particular dC 6 alkyl
• a base for example a metal alcoholate, such as sodium methylate or sodium ethylate
• a diluent for example ether or the alcohol derived from the alcoholate
• halogenating agents e.g. thionyl chloride, phosgene, phosphorus trichloride
• a diluent e.g. optionally chlorinated aliphatic or aromatic hydrocarbons, such as
• Toluene or methylene chloride at temperatures from 0 ° C to 150 ° C, preferably between 20 ° C and 100 ° C.
• Cyanoacetic acid esters of the formula (XTII) are known compounds of organic chemistry.
• V, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , R 11 and m have the meanings given above
• A stands for oxygen
• V, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and m have the meanings given above
• alkylating agents e.g. dimethyl sulfate, triethyloxonium tetrafluoroborate (Meerwein salt)
• alkylating agents e.g. dimethyl sulfate, triethyloxonium tetrafluoroborate (Meerwein salt)
• V, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , R 11 and m have the meanings given above
• A stands for sulfur
• V, Z, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and m have the meanings given above
• a sulfurization reagent e.g. Lawesson's reagent
• V, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and m have the meanings given above
• R 11 has the meaning given above, and
• Process (A) is characterized in that compounds of the formula
• R 11 , V, W, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and m have the meanings given above,
• Chlorinated aliphatic or aromatic hydrocarbons such as toluene, xylene, 1,2-dichlorobenzene, chloroform or methylene chloride, and polar solvents such as dimethyl sulfoxide, dimethylformamide, dimethyl acetamide or N-methylpyrrolidone are preferably usable.
• Solvents which can also be used are ethers such as, for example, diethyl ether,
• Methyl tert-butyl ether, tetrahydrofiiran or dioxane, and nitriles such as, for example, acetonitrile and also esters such as, for example, ethyl acetate, and also ketones such as acetone or isopropyl methyl ketone.
• Tertiary amines such as diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclonones (DBN), triethylamine, pyridine or are preferably usable
• Alcoholates such as sodium methylate, sodium ethylate, magnesium ethylate, potassium tert-butoxide and metal hydrides such as sodium hydride, calcium hydride and also alkali metal or alkaline earth metal carbonates or hydrogen carbonates such as sodium hydrogen carbonate, potassium carbonate or sodium carbonate can also be used.
• Acids which can be used in carrying out process (A) are all acids which do not hydrolyze towards the reactants.
• Organic acids such as p-toluenesulfonic acid and trifluoroacetic acid can preferably be used.
• the reaction temperature can be varied within a substantial range when carrying out process (A). It is expedient to work at temperatures between -20 ° C and 160 ° C, preferably between 0 ° C and 120 ° C.
• Process (A) is preferably carried out under normal pressure.
• reaction component of the formula (III) is used in an equimolar amount or in a larger excess (up to 5 mol), preferably in a 1.5 to 2 molar amount, in relation to the reaction component of the formula (II).
• the base if used, is preferably used in an equimolar amount to the reaction component of the formula (II).
• the acid optionally used is preferably used in catalytic amounts.
• Process (B) is characterized in that compounds of the formula (IV) are each reacted with thioamides of the formula (V), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
• the starting compounds of the formula (IV) can be prepared by known processes (Sequin, Dies, BSCFAS, Bull. Soc. Chim. Fr. (1956) 1210, 1211; Bushey, Hoover, J. Org. Chem. 45, 4198, ( 1980)).
• the compounds of the formula (V) can be prepared from the corresponding keto compound in inert solvents, such as, for example, toluene, by using thionylating agents, in particular P2S5 and the Lawesson reagent (see Preparation Example 4).
• Diluents which can be used in process (B) according to the invention are all solvents which are inert to the compounds of the formula (IV).
• Hydrocarbons such as gasoline, benzene, toluene, xylene and tetralin are preferably usable, furthermore halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, also ketones such as acetone and methylisopropyl ketone, furthermore ethers such as diethyl ether, tetrahydrofuran and Dioxane, in addition carboxylic acid esters, such as ethyl acetate, and also strongly polar solvents, such as dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide and sulfolane.
• halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene
• ketones such as acetone and methylisopropyl ket
• Suitable acid binders for the reaction according to process (B) according to the invention are all customary acid acceptors.
• Tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclonones (DBN), Hunig base and N, N-dimethylaniline, polymeric bases such as diisopropylaminopolystyrene, and also alkaline earth metal oxide, are preferably usable - And calcium oxide, also alkali and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate, and alkali metal hydroxides, such as sodium hydroxide and potassium hydroxide.
• Alkyl phosphites such as triethyl phosphite, tributyl phosphite or triphenylphosphines, such as triphenylphosphine, can be used as phosphorus reagents in process (B) according to the invention.
• reaction temperature in process (B) according to the invention can be varied within a substantial range. In general, temperatures between 0 ° C and 200 ° C, preferably between -20 ° C and 150 ° C.
• the starting materials of the formula (IV) and thioamide of the formula (V) are generally in each case used in approximately equivalent amounts. However, it is also possible to use one or the other use other components in a larger excess. The processing takes place according to the usual methods.
• Process (C) is characterized in that compounds of the formula (VII) with halogenating agents, such as e.g. Phosgene, diphosgene, triphosgene, if appropriate in the presence of a diluent, to give compounds of the formula (VIII), which are then reacted with compounds of the formula (II), if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
• halogenating agents such as e.g. Phosgene, diphosgene, triphosgene
• Suitable acid binders for the reaction according to process (C) according to the invention are all customary acid acceptors.
• Tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclonones (DBN), Hunig base and N, N-dimethylaniline, polymeric bases such as, for example, diisopropylaminopolystyrene, and also alkaline earth metal oxides, and also alkaline earth metal oxides, are preferably used. and calcium oxide, also alkali and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate, and alkali metal hydroxides, such as sodium hydroxide and potassium hydroxide.
• Diluents which can be used in process (C) according to the invention are all solvents which are inert to the halogenating reagents.
• Hydrocarbons such as gasoline, benzene, toluene, xylene and tetralin, and furthermore halogenated hydrocarbons, such as methylene chloride, chloroform, are preferably usable.
• reaction temperature in process (C) according to the invention can be varied within a substantial range. In general, temperatures between -20 ° C and 100 ° C, preferably between 0 ° C and 80 ° C.
• Process (C) according to the invention is generally carried out under normal pressure.
• the starting materials of the formula (VII) and the corresponding halogenating agent are generally in each case used in approximately equivalent amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 mol).
• the processing takes place according to the usual methods. The general procedure is to remove the precipitated salts and to concentrate the remaining reaction mixture by stripping off the diluent.
• Process (D) is characterized in that compounds of the formula (I) in which Ar, V, X, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and m have the meaning given above, K represents oxygen and Z represents hydrogen, in each case with alkylating agent, acylating agent, sulfonating agent or condensing agent of the formula (IX), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
• alkylating agents, acylating agents, sulfonating agents or condensing agents of the formula (LX) to be used are known synthetic chemicals of organic chemistry.
• Diluents which can be used in process (D) according to the invention are all solvents which are inert to the above-mentioned reagents.
• Hydrocarbons such as gasoline, benzene, toluene, xylene and tetraline
• Hydrocarbons such as gasoline, benzene, toluene, xylene and tetraline
• halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene
• ketones such as acetone and methyl isopropyl ketone
• furthermore ethers such as diethyl ether, tetrahydrofuran and dioxane
• carboxylic acid esters such as ethyl acetate
• strongly polar solvents such as, for example, dimethyl sulfoxide, dimethylformamide, N-methylpyrrolidone and sulfo
• Suitable acid binders for the reaction according to process (D) according to the invention are all customary acid acceptors.
• Tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclonones (DBN), Hunig base and N, N-dimethylaniline, furthermore alkaline earth metal oxides, such as magnesium and calcium oxide, and also alkali metal oxides, are preferably usable.
• alkaline earth metal carbonates such as sodium carbonate, potassium carbonate and calcium carbonate
• alkali metal hydroxides such as sodium hydroxide and potassium hydroxide
• alkali metal hydrides such as sodium hydride, potassium hydride or alkali metal alcoholates, such as potassium tert-butoxide.
• reaction temperatures can be varied within a substantial range in process (D) according to the invention. In general, temperatures between -70 ° C and + 150 ° C, preferably between -20 ° C and
• Palladium (0) complexes are preferably suitable as catalysts for carrying out process (E) according to the invention.
• tetrakis is preferred.
• arylboronic acids required for carrying out process (E) are in some cases commercially available, such as 4-chlorophenylboronic acid, or can be prepared by known processes.
• Inorganic or organic bases are suitable as acid acceptors for carrying out process (E) according to the invention.
• These preferably include alkaline earth metal or alkali metal hydroxides, acetates, carbonates or hydrogen carbonates, such as, for example, sodium, potassium, barium or ammonium hydroxide, sodium, potassium, calcium or ammonium acetate, sodium, potassium or ammonium carbonate , Sodium bicarbonate or potassium bicarbonate, alkali fluorides, such as cesium fluoride, and tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N -Dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclonones
• DABCO di
• Suitable diluents for carrying out process (E) according to the invention are water, organic solvents and any mixtures thereof.
• Examples include: aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, methylene chloride, chloroform, carbon tetrachloride, dichloro, trichloroethane or carbon tetrachloride; Ethers such as diethyl, diisopropyl, methyl tert-butyl, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, diethylene glycol dimethyl ether or anisole;
• the boronic acid of the formula (X) in which Ar 2 has the meaning given above and compounds of the formula (I 1 ) in which Ar 1 , K, V, X, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , Z, m and shark have the meaning given above, in a molar ratio of 1: 1 to 3: 1, preferably 1: 1 to 2: 1.
• the catalyst is generally used from 0.005 to 0.5 mol, preferably from 0.01 to 0.1 mol, per mol of the compound of the formula (I 1 ).
• Base is generally used in an excess.
• the process (F) is characterized in that compounds of the formula (I) in which Ar, V, X, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , Z and m have the meaning given above - Tung and K stands for oxygen, optionally reacted with sulfurization reagents in the presence of a diluent.
• the sulfurization reagents to be used are known synthetic chemicals such as, for example, phosphorus pentasulfide or 2,4-bis- (4-methoxyphenyl) -l, 2,3,4-dithiaphosphetane-2,4-disulfide (Lawesson's reagent).
• diluents in process (F) all of the above-mentioned.
• Reagents inert solvents are used.
• Hydrocarbons such as, for example, gasoline, benzene, toluene, xylene and tetralin, preferably halogen hydrocarbons such as methylene chloride, chloroform, chlorobenzene and o-dichlorobenzene, ethers such as tetrahydrofuran, dioxane, diisopropyl ether or methyl tert-butyl ether can preferably be used.
• reaction temperatures in process (F) according to the invention can be varied within a relatively wide range. In general, temperatures between 0 ° C and 250 ° C, preferably between 40 ° C and 200 ° C.
• the starting materials of the formula (I) and the abovementioned reagents are generally in each case used in approximately equivalent amounts. However, it is also possible to use a large excess of the above-mentioned reagents up to 5 mol.
• the processing takes place according to the usual methods.
• Process (G) is characterized in that compounds of the formula (I) in which Ar, K, X, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 and m have the meaning given above tion and V stands for a sulfur atom, with an oxidizing agent such as
• halogenated hydrocarbons such as methylene chloride, chloroform, chlorobenzene, o-dichlorobenzene, carboxylic acid esters such as ethyl acetate or strongly polar solvents such as dimethyl sulfoxide and sulfolane can be used.
• reaction temperature in process (G) according to the invention can be varied within a substantial range. In general, temperatures between -30 ° C and 100 ° C, preferably between -10 ° C and 80 ° C.
• the starting materials of the formula (I) and the oxidizing agent are generally used in a molar ratio of 1: 1 or 1: 2. However, it is also possible to use one or the other component in a larger excess (up to 5 mol). The processing takes place according to the usual methods.
• Process (G) according to the invention is generally carried out under normal pressure.
• the active compounds according to the invention are particularly well suited as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are understood to mean all plants that grow up in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
• the dosages of the active compounds according to the invention required for weed control are between 0.001 and 10 kg / ha, preferably between 0.005 and 5 kg / ha.
• the active compounds according to the invention can e.g. can be used in the following plants:
• Apera Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa,
• 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 the plant cultivars which can or cannot be protected by plant breeders' rights.
• Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as sprout, leaf, flower and root, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
• the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
• the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space according to the customary treatment methods, for example by dipping, spraying, evaporating, atomizing, scattering, spreading and using propagation material, in particular seeds. continue by wrapping one or more layers.
• the compounds are suitable for total weed control, for example on industrial and rail tracks and on paths and squares with and without tree cover.
• the compounds for weed control in permanent crops for example forest, ornamental trees, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, can also be used
• the active compounds according to the invention are very well suited for the selective control of monocotyledon weeds in dicotyledon crops in the pre- and post-process.
• they can be used in cotton or sugar beet with very good results to control harmful grasses.
• the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers substances.
• formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
• extenders that is to say liquid solvents and / or solid carriers
• surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
• organic solvents can, for example, also be used as auxiliary solvents.
• auxiliary solvents include aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils , Alcohols such as butanol or glycol and their ethers and esters, ketones such as Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
• aromatics such as xylene, toluene, or alkylnaphthalenes
• chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes
• Possible solid carriers are: e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g.
• nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
• Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
• Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
• Other additives can be mineral and vegetable oils.
• Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
• the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90% and, in addition, preferably extenders and / or surface-active agents.
• the active substance according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active substances, such as insecticides, attractants, sterilants, acaricides, nematocides, 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.
• safeners can also be mixed with the compounds according to the invention in order to increase the tolerance to cultivated plants.
• Debacarb dichlorophene, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomo ⁇ h, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianonodol, dithianonodol, dithianonodol, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dit
• Famoxadone Fenapanil, Fenarimol, Fenbuconazol, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimo ⁇ h, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Flu ⁇ rimidol, Flusilimidol
• Imazalil Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan,
• Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
• Oxadixyl Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
• Paclobutrazole pefurazoate, penconazole, pencycuron, phosdiphene, pimaricin, piperalin,
• Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetcyclacis, tetraconazole, thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram, dioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazbutichl, triazoxid, triazoxid, triazoxid, triazoxide
• Cadusafos Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlo ⁇ yrifos, Chlo ⁇ yrifos M, Chlovaporthrin, Cis-Resmethrin, Clispethythrine, Cispermethrin, Cispermethrin, Cispermethrin, Cispermethrin, Cispermethrin, Cispermethrin, Cispermethrin, Cispermethrin, Cispermethrin, Cispermethrin, Cispermethrin, Cispermethrin, Cispermethrin, Cispermethrin, Cispermethrin, Cispermethrin, Cispermethrin, Cispermethrin
• Fenamiphos fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb, fenoxacrim
• Fenoxycarb fenpropathrin, fenpyrad, fenpyrithrin, fenpyroximate, fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxuron, Flucythrinate, Flufenoxuron, Flutenzine, Fluvalinate, Fonophos, Fosmethilan, Fosthiazate, Fubfenprox, Furathiocarb,
• Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
• Metharhilicium flavoviride methidathione, methiocarb, methomyl, methoxyfenozide, metolcarb, metoxadiazone, mevinphos, milbemectin, monocrotophos,
• Imazamethapyr Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Iodosulfuron (-methyl, -sodium), Ioxynil, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Loxapofenif, LCP, Mox , Mefenacet, Mesotrione, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metolachlor, Metosulam, Metoxuron,
• the active ingredient according to the invention can also be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
• Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.
• the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
• the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
• the application takes place in a customary manner adapted to the application forms.
• the active compounds are furthermore suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which are used in agriculture, in forests, in the protection of stored goods and materials, and on occur in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
• animal pests preferably arthropods and nematodes, in particular insects and arachnids, which are used in agriculture, in forests, in the protection of stored goods and materials, and on occur in the hygiene sector. 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 spec.
• Symphyla e.g. Scutigerella immaculata.
• Thysanura e.g. Lepisma saccharina.
• Thysanoptera e.g. Frankliniella occidentalis, Hercinothrips femoralis, Thrips palmi, Thrips tabaci.
• From the order of the Homoptera for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vasturix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphoca stratataonidium, Aspyonidium sap ., Psylla spp.
• Hymenoptera From the order of the Hymenoptera, for example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp. From the order of the Diptera, for example Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca ., Liriomyza spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyo
• Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,.
• Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,.
• Chori . Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipulpus spp ..
• Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semi penetrans, Heteroderma spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelench
• the active compounds according to the invention are notable for high insecticidal and acaricidal activity after leaf and soil use.
• Compounds according to the invention also have a fimgicidal action in certain concentrations or application rates. They can also be used as microbicides or antifungals.
• 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 and by a good stability to alkali on limed substrates.
• the active compounds according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mite mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, Hairlooms, featherlings and fleas.
• animal parasites ectoparasites
• tick ticks such as tick ticks, leather ticks, mite mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, Hairlooms, featherlings and fleas.
• parasites include:
• Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp ..
• Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota ., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Glossina spp., Calliphora spp., Glossina spp., Calliphora spp
• Siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp ..
• Actinedida Prostigmata
• Acaridida e.g. Acarapis spp., Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypppectoles spp ., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp ..
• the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used 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, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or
• Bathing (dipping), spraying (spray), pouring (pour-on and spot-on), des Washing, powdering and with the help of shaped bodies containing active ingredients, such as collars, ear tags, tail tags, limb tapes, holsters, marking devices, etc.
• active ingredients such as collars, ear tags, tail tags, limb tapes, holsters, marking devices, etc.
• the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or apply after 100 to 10,000-fold dilution or use it as a chemical bath.
• formulations for example powders, emulsions, flowable agents
• Termites like Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwinisis, Zootermopsis nevadensis, Coptotermes formosanus.
• non-living materials such as preferably plastics, adhesives, glues, papers and cartons, leather, wood and wood processing products and paints.
• the material to be protected against insect infestation is very particularly preferably wood and wood processing products.
• Agents or mixtures containing them can be protected is to be understood as examples: timber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone poles, wooden cladding, wooden windows and doors, plywood, chipboard, carpentry or wood products, which are generally used in house construction or in carpentry.
• the active substances can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
• the formulations mentioned can be prepared in a manner known per se, for example by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellants, optionally siccatives and UV stabilizers and other - if dyes and pigments and other processing aids.
• the insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active compound according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
• the amount of the agents or concentrates used depends on the type and occurrence of the insects and on the medium. The optimal amount can be determined 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.
• organic-chemical solvent or solvent mixture and / or an oily or oily or low-volatile organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agents.
• the organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
• Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.
• Mineral oils with a boiling range of 170 to 220 ° C, test gasoline with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C are advantageous. Te ⁇ entinöl and the like. For use.
• the organic low-volatility oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C. can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture is also a Evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.
• part of the organic chemical solvent or solvent mixture is replaced by an aliphatic polar organic chemical solvent or solvent mixture.
• Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups, such as, for example, glycol ethers, esters or the like, are preferably used.
• the known water-thinnable synthetic resins and / or synthetic resins which are soluble or dispersible or emulsifiable in the organic chemical solvents used and / or binding drying oils, in particular binders consisting of or containing, are used as organic chemical binders 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.
• 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
• the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous nous substances up to 10 wt .-% can be used. In addition, known dyes, pigments, water-repellants, odor correctors and inhibitors or anticorrosive agents and the like can be used.
• At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder.
• Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
• binder mentioned can be replaced by a fixative (mixture) or a plasticizer (mixture).
• fixative mixture
• plasticizer mixture
• additives are intended to volatilize the active ingredients and crystallize or precipitate! prevent. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).
• the plasticizers 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 oleate or higher-molecular glycerol ether, glycerol glycerol glycerol ether, glycerol ether - 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-
• Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
• Water is also particularly suitable as a solvent or diluent, if appropriate in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
• a particularly effective wood protection is achieved by industrial impregnation processes, e.g. vacuum, double vacuum or pressure processes.
• 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, Imidacloprid, NI-25, Flufenoxuron, Hexaflumuron, as well as Fazonazole, as well as Tebuconazole, cyproconazole, metconazole, imazalil, dichlorfluanid, tolylfluanid, 3-iodo-2-propynyl butyl carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octyl-isothiazolin-3-one ,
• the active compounds according to the invention can be used particularly well to control insects which damage plants, for example against the larvae of the horseradish leaf beetle (Phaedon cochleariae), against the larvae of the green rice leafhopper (Nephotettix cincticeps) and against the larvae of the green peach aphid
• a fimgicidal activity of the active compounds according to the invention can also be determined.
• a broad antifungal effect can be observed in both “in vitro” and “in vivo” studies.
• the active compounds are particularly suitable for combating mildew, leaf spots and fusariums in the plants infested with them.
• the preparation and use of the active compounds according to the invention can be seen from the examples below.
• 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 beetle (Phaedon cochleariae) while the leaves are still moist.
• the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
• Emulsifier 1 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted to the desired concentration with water containing emulsifier.
• a specified quantity of active compound preparation of the desired concentration is pipetted onto a standardized quantity of artificial filter.
• one larva (L3) of the army worm (Spodoptera frugiperda) is placed on the feed.
• the kill is determined in%. 100% means that all animals have been killed; 0% means that no animals 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.
• Soybean shoots (Glycine max) are treated by immersing them in the active ingredient preparation of the desired concentration and populating them with 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.
• 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 kill is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
• Emulsifier 1 part by weight of alkylaryl polyglycol ether
• Test plants which have a height of 5 to 15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area. After 3 weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
• Emulsifier 1 part by weight of alkylaryl polyglycol ether
• Seeds of the test plants are sown in normal soil and watered with the active compound preparation after 24 hours.
• the amount of water per unit area is expediently kept constant.
• the concentration of active substance in the preparation is irrelevant, the only decisive factor is the amount of active substance applied per unit area.
• the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Dentistry (AREA)
• Wood Science & Technology (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Agronomy & Crop Science (AREA)
• General Health & Medical Sciences (AREA)
• Pest Control & Pesticides (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Plural Heterocyclic Compounds (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

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• 1999
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• 2000
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