EP1537080A1 - Ketoenoles spirocycliques substitues - Google Patents

Ketoenoles spirocycliques substitues

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Publication number
EP1537080A1
EP1537080A1 EP03794887A EP03794887A EP1537080A1 EP 1537080 A1 EP1537080 A1 EP 1537080A1 EP 03794887 A EP03794887 A EP 03794887A EP 03794887 A EP03794887 A EP 03794887A EP 1537080 A1 EP1537080 A1 EP 1537080A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
chlorine
alkoxy
methyl
optionally
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP03794887A
Other languages
German (de)
English (en)
Inventor
Reiner Fischer
Thomas Bretschneider
Christoph Erdelen (Deceased) Di
Jörg KONZE
Peter Lösel
Mark Wilhelm Drewes
Dieter Feucht
Karl-Heinz Kuck
Ulrike Wachendorff-Neumann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
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Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to EP10160913.9A priority Critical patent/EP2233466B1/fr
Publication of EP1537080A1 publication Critical patent/EP1537080A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/54—Spiro-condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C229/48—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms of the same non-condensed ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/52—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/96—Spiro-condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • the present invention relates to new substituted spirocyclic ketoenols, several processes for their preparation and their use as pesticides, microbicides and herbicides.
  • 1-H-arylpyrrolidinediene derivatives with herbicidal, insecticidal or acaricidal activity are known: EP-A-456 063, EP-A-521 334, EP-A-613 884, EP-A-613 885, WO 95/01 358, WO 98/06 721, WO 98/25 928, WO 99/16 748, WO 99/24437 or
  • Alkoxy-substituted spirocyclic 1H-arylpyrrolidinedione derivatives are also known: EP-A-596298, WO 95/26 954, WO 95/20 572, EP-A-0 668 267, WO 96/25 395, WO 96/35 664 , WO 97/01 535, WO 97/02 243, WO 97/36 868, WO
  • the herbicidal and / or acaricidal and / or insecticidal activity and / or breadth of activity and / or the plant tolerance of the known compounds, in particular with respect to crop plants, is not always sufficient.
  • W represents alkyl or alkoxy
  • X represents halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano
  • Y in the 4-position represents hydrogen, halogen, cyano or haloalkyl
  • W also represents hydrogen, halogen or alkyl
  • X also represents halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano
  • Y in the 4-position also represents optionally substituted phenyl
  • Z also stands for hydrogen.
  • W also represents hydrogen or alkyl
  • X also for halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or
  • Cyano stands, Y in the 5-position also represents optionally substituted phenyl
  • Z in the 4-position also represents hydrogen, alkyl or halogen.
  • W also represents hydrogen, methyl, propyl, isopropyl or halogen
  • X also represents halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano
  • Y in the 3 or 5 position also represents hydrogen, halogen or alkyl
  • Z in the 4-position also represents hydrogen, halogen, alkyl, haloalkyl, cyano or haloalkoxy.
  • A represents an optionally substituted alkanediyl group or for optionally substituted and / or optionally interrupted by a heteroatom cycloalkyl
  • Heteroatoms and / or C interrupted cycloalkyl
  • D represents NH or oxygen
  • E represents a metal ion or an ammonium ion
  • L represents oxygen or sulfur
  • M oxygen or sulfur
  • R2 stands for alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl, each optionally substituted by halogen or cyano, or for optionally substituted cycloalkyl, phenyl or benzyl,
  • R3, R4 and R5 independently of one another each for alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio optionally substituted by halogen, or for optionally optionally substituted phenyl,
  • R6 and R 7 independently of one another represent hydrogen, each represent optionally substituted by halogen or cyano alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, represent optionally substituted phenyl or benzyl, or together with the N atom to which they are attached, form an optionally substituted or optionally substituted cycle containing oxygen or sulfur.
  • the compounds of the formula (I) can be present as optical isomers or isomer mixtures, in different compositions, which can, if appropriate, be separated in a customary manner. Both the pure isomers and the isomer mixtures, their preparation and use, and agents containing them are the subject of the present invention. For the sake of simplicity, however, the following always refers to compounds of the formula (I), although both the pure compounds and, if appropriate, also mixtures with different proportions of isomeric compounds are meant.
  • A, B, G, W, X, Y and Z have the meaning given above.
  • A, B, E, L, M, W, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R? have the meanings given above.
  • A, B, E, L, M, W, X, Y, Z, Rl, R 2 , R3, R4 R5, R6 and R 7 have the meaning given above.
  • A, B, W, X, Y and Z have the meanings given above, if
  • R 8 represents alkyl (preferably C i -C alkyl)
  • A, B, W, X, Y, Z and R 8 have the meanings given above,
  • R has the meaning given above and Shark represents halogen (especially chlorine or bromine)
  • Rl has the meaning given above
  • R 2 and M have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder;
  • R 3 has the meaning given above
  • Me for a mono- or divalent metal preferably an alkali or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium
  • an alkali or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium
  • RIO, II, R12 independently of one another represent hydrogen or alkyl (preferably Cj-Cg-alkyl),
  • R6 and L have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst or
  • the new compounds of the formula (I) have good activity as pesticides, preferably as insecticides, acaricides and / or fungicides and / or herbicides and, moreover, are frequently very well tolerated by plants, in particular by crop plants.
  • W preferably represents Ci-Cg-alkyl or Ci-Cg-alkoxy
  • X preferably represents halogen, Ci-Cg-alkyl, Ci-Cö-alkoxy, C ⁇ -C4-halo-alkyl, Cj-C4-haloalkoxy or cyano
  • Y preferably stands in the 4-position for hydrogen, halogen, cyano or C ⁇ -Q- j -haloalkyl
  • Z preferably represents hydrogen.
  • W also preferably represents hydrogen, halogen or C 1 -C 6 -alkyl
  • X also preferably represents halogen, Cj-Cg-alkyl, Ci-Cg-alkoxy, C1-C4-haloalkyl, Cj-C4-haloalkoxy or cyano,
  • Y is also preferably in the 4-position for the rest
  • Z also preferably represents hydrogen
  • V 1 also preferably represents halogen, dr alkyl, C 1 -C 6 alkoxy, C 1 -C haloalkyl or C 1 -C 4 haloalkoxy,
  • V 2 also preferably represents hydrogen, halogen, -C ö alkyl, -C -C 6 alkoxy or -GrHalogenalkyl,
  • V 1 and V 2 together preferably also represent C3-C4-alkanediyl, which can optionally be substituted by halogen and / or C 1 -C 2 -alkyl and which can optionally be interrupted by one or two oxygen atoms.
  • W also preferably represents hydrogen or C 1 -C 6 -alkyl
  • X also preferably represents halogen, Ci-Cö-alkyl, Cj-C 6 -Ajlkoxy, C r C - haloalkyl, C ⁇ -C haloalkoxy or Cyan ⁇ Y is also preferably in the 5-position for the rest
  • Z is also preferably in the 4-position for hydrogen, Ci-Cg-alkyl or halogen,
  • V 1 also preferably represents halogen, C 1 -Ct 2 alkyl, -Cö-alkoxy, dC 4 - haloalkyl or dQ-haloalkoxy,
  • V 2 also preferably represents hydrogen, halogen, -CC 6 -alkyl, dC 6 -alkoxy or C 1 -C -haloalkyl,
  • V 1 and V 2 together also preferably represent C3 ⁇ C4-alkanediyl, which can optionally be substituted by halogen and or -CC-C 2 alkyl and which can optionally be interrupted by one or two oxygen atoms.
  • W also preferably represents hydrogen, methyl, propyl, isopropyl or halogen
  • X also preferably represents halogen, Ci-Cg-alkyl, C r C 6 alkoxy, C r C -
  • Haloalkyl C 1 -C 4 -haloalkoxy or cyano
  • Y is also preferably in the 3 or 5 position for hydrogen, halogen or C r C 6 alkyl
  • Z is also preferably in the 4-position for hydrogen, halogen, C r C 6 alkyl, C r C 4 haloalkyl, cyano or C r C haloalkoxy.
  • A is preferably an optionally by C 1 -C 4 - alkyl-substituted C 1 -C4- or alkanediyl optionally substituted by C 1 -C 4 alkyl-substituted d-Cs-cycloalkyl, in which optionally one methylene group is replaced by oxygen,
  • B preferably represents C 2 -C 8 -alkylene, dC 6 -alkoxy, d-C ⁇ -alkoxy-dQ-alkyloxy optionally substituted by halogen, optionally halogen, dC 6 -alkyl, dC ö -alkoxy, C ⁇ - C 4 haloalkyl, dC 4 haloalkoxy, cyano or nitro substituted phenyl, for optionally substituted by halogen, dC 4 alkyl or C 1 -C 2 haloalkyl substituted pyridyl, pyrimidyl, thiazolyl or thienyl or for optionally substituted by halogen , dC 4 - alkyl, dC 4 alkoxy or dC 2 haloalkyl substituted C 3 -C 8 cycloalkyl, in which one or two not directly adjacent methylene groups are replaced by oxygen or three methylene groups by the radical -
  • D preferably represents JNH or oxygen
  • G preferably represents hydrogen (a) or one of the groups
  • E represents a metal ion or an ammonium ion
  • L represents oxygen or sulfur and M represents oxygen or sulfur
  • phenyl optionally substituted by halogen, cyano, nitro, C 1-6 -alkyl, C 1 -C -alkoxy, C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio or C 1 -C 6 -alkylsulfonyl,
  • Ci-Cß-alkyl for optionally substituted by halogen, nitro, cyano, Ci-Cß-alkyl, Cj-Cg-alkoxy, Ci-Cö-haloalkyl or Ci-Cg-haloalkoxy substituted phenyl -CC 6 -alkyl,
  • phenoxy-Ci-Cg-alkyl optionally substituted by halogen or Ci-Cg-alkyl or
  • R 2 preferably represents in each case optionally substituted by halogen or cyano -CC20-alkyl, C2-C20 "alkenyl, -C-Cg-alkoxy-C2-Cg-alkyl or poly-C ⁇ -Cg-alkoxy-C2-Cg-alkyl,
  • C3-Cg-cycloalkyl which is optionally substituted by halogen, Ci-C ⁇ -alkyl or Ci-Cg-alkoxy or
  • R 3 preferably represents Ci-Cg-alkyl optionally substituted by halogen or in each case optionally substituted by halogen, Ci-Cg-alkyl, Ci-Cg-alkoxy, -C-C4-haloalkyl, -C-C4-haloalkoxy, cyano or nitro benzyl,
  • R 4 and R5 independently of one another preferably each represent C 1 -C 6 -alkyl optionally substituted by halogen, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino, di- (C 1 -C 6 -alkyl) amino, Ci-Cg-alkylthio or C3-Cg-alkenylthio or for each optionally by halogen, nitro, cyano, C1-C4-alkoxy,
  • ⁇ and R? independently of one another preferably represent hydrogen, in each case optionally substituted by halogen or cyano C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -alkenyl or C 1 -C 6 -alkoxy-C 2 -Cg alkyl, for phenyl or benzyl which are each optionally substituted by halogen, Cj-Cg-alkyl, Cj-Cg-halogenoalkyl or Ci-Cg-alkoxy or together for a C3-C6- which is optionally substituted by Ci-Cg-alkyl AI kylene radical, in which a methylene group is optionally replaced by oxygen or sulfur.
  • halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
  • W particularly preferably represents C j -C4-alkyl or C -Q ⁇ -alkoxy
  • X particularly preferably represents chlorine, bromine, C1-C4-alkyl, C1-C4-alkoxy, C ⁇ -C2-haloalkyl, C ⁇ -C2-haloalkoxy or cyano,
  • Y is particularly preferably in the 4-position for hydrogen, chlorine, bromine, cyano or trifluoromethyl.
  • Z particularly preferably represents hydrogen.
  • W also particularly preferably represents hydrogen, chlorine, bromine or C 1 -C 4 -alkyl
  • X also particularly preferably represents chlorine, bromine, C 1 -C -alkyl, C 1 -C -
  • Y is also particularly preferably in the 4-position for the rest
  • V 1 also particularly preferably represents fluorine, chlorine, C1-C4 - alkyl, dC 4 -alkoxy, C 2 haloalkyl or C ⁇ -C -haloalkoxy
  • V 2 also particularly preferably represents hydrogen, fluorine, chlorine, C 1 -C alkyl, dC 4 alkoxy or dC 2 haloalkyl
  • V 1 and V 2 together also particularly preferably represent -O-CH2-O- and
  • W also particularly preferably represents hydrogen or C 1 -d alkyl
  • X also particularly preferably represents chlorine, C1-C4-alkyl or C1-C2-
  • Y is also particularly preferably in the 5-position for the rest
  • Z is also particularly preferably in the 4-position for hydrogen, C1-C4-alkyl or chlorine.
  • V 1 also particularly preferably represents fluorine, chlorine, dC -alkyl, dC -
  • V 2 also particularly preferably represents hydrogen, fluorine, chlorine, dC 4 -
  • V 1 and V 2 together also particularly preferably represent -O-CH2-O- or
  • W also particularly preferably represents hydrogen, methyl, chlorine or bromine
  • X also particularly preferably represents chlorine, bromine, d - alkyl, C 1 -C alkoxy, C 1 -C 2 haloalkyl, C 1 -C 2 haloalkoxy or cyano
  • Y is also particularly preferably in the 3 or 5 position for hydrogen
  • Z is also particularly preferably in the 4-position for hydrogen, chlorine, bromine, C1-C4-alkyl, -C-C2-haloalkyl, cyano or ⁇ -haloalkoxy.
  • B particularly preferably represents C 2 -C 6 -alkenyl, dC 4 -alkoxy, C 1 -C 4 -alkoxy-dd-alkyloxy which is optionally monosubstituted to trisubstituted by fluorine or chlorine, optionally monosubstituted to trisubstituted by fluorine, chlorine, bromine , dC 4 -alkyl, dC 4 -alkoxy, dC 2 -haloalkyl, dC 2 - haloalkoxy, cyano or nitro-substituted phenyl, for each pyridyl, pyrimidyl which is monosubstituted or disubstituted by fluorine, chlorine, bromine, methyl, ethyl or trifluoromethyl, Thiazolyl or thienyl or for C 3 -C 6 -cycloalkyl which is optionally mono- to disubstituted by flu
  • G particularly preferably represents hydrogen (a) or one of the groups in which
  • E represents a metal ion or an ammonium ion
  • L represents oxygen or sulfur
  • M oxygen or sulfur
  • Ci-Cig-alkyl particularly preferably represents in each case optionally mono- to trisubstituted by fluorine or chlorine-substituted Ci-Cig-alkyl, C2-Ci6-Alk en yl> C ⁇ ⁇ C6-alkoxy-C ⁇ -C4-alkyl, C ⁇ -C6-alkylthio-C ⁇ -C4- alkyl or poly-C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl or for C 3 -C 7 -cycloalkyl which is optionally monosubstituted or disubstituted by fluorine, chlorine, C 1 -C 5 -alkyl or C 1 -C 8 -alkoxy, in which optionally one or two methylene groups which are not directly adjacent are replaced by oxygen and / or sulfur,
  • phenyl-C4-C4-alkyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, C1-C4-alkyl, C-C4-alkoxy, C ⁇ -C3-haloalkyl or C ⁇ -C3-haloalkoxy, for pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine or C1-C4-alkyl,
  • pyridyloxy-C5-C5-alkyl pyrimidyl-oxy-C5-C5-alkyl or thiazolyloxy-C5-C5-alkyl which is optionally substituted once or twice by fluorine, chlorine, bromine, A ino or C1-C4-alkyl,
  • R 2 particularly preferably represents in each case monosubstituted to trisubstituted by fluorine or chlorine, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 1 -C 6 -alkoxy-C 2 -co-alk 1 or poly-C 1 -C 6 -alkoxy ⁇ -cg alkyl,
  • C3 to C7 ⁇ cycloalkyl which is optionally monosubstituted or disubstituted by fluorine, chlorine, C1-C4-alkyl or -CC4-alkoxy or
  • R 3 particularly preferably represents Ci-Cg-alkyl which is optionally monosubstituted to trisubstituted by fluorine or chlorine or in each case optionally monosubstituted or disubstituted by fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-alkoxy, C1-C2-
  • R 4 and R5 independently of one another particularly preferably each represent C 1 -C 6 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 8 -alkylamino, di- (C 1 -C 6 -alkyl) which is optionally mono- to trisubstituted by fluorine or chlorine ) amino, Cj-Cg-Al- Jkylthio or C3-C4-alkenylthio or for each optionally single to double by fluorine, chlorine, bromine, nitro, cyano, -C -C3 alkoxy, C1-C3- haloalkoxy, C - [- C3-alkylthio, C ⁇ -C3-haloalkylthio , C1-C3 alkyl or C1 -C3 haloalkyl substituted phenyl, phenoxy or phenylthio,
  • R "and RJ independently of one another particularly preferably represent hydrogen, for each Ci-Cg-alkyl, C3-C6-cycloalkyl, Ci-Cg-alkoxy, C3-Cö-alkenyl or C ⁇ -C6 which is optionally mono- to trisubstituted by fluorine or chlorine -Alko y-C2-C6-alkyl, for each optionally single to triple by fluorine, chlorine, bromine, Ci-Cs-haloalkyl, Ci-Cs-alkyl or C1-C5-
  • halogen represents fluorine, chlorine and bromine, in particular fluorine and chlorine.
  • W very particularly preferably represents ethyl or methoxy
  • X very particularly preferably represents chlorine, bromine, methyl, ethyl, propyl, methoxy, trifluoromethyl, difluoromethoxy, trifluoroethoxy or cyano,
  • Y very particularly preferably in the 4-position represents hydrogen, chlorine or bromine
  • Z very particularly preferably represents hydrogen.
  • W also very particularly preferably represents hydrogen, chlorine, bromine or methyl
  • X also very particularly preferably represents chlorine, bromine, methyl, ethyl, propyl, methoxy, trifluoromethyl, difluoromethoxy or cyano
  • Y also very particularly preferably stands in the 4-position for the rest
  • Z also very particularly preferably represents hydrogen
  • V 1 also very particularly preferably represents fluorine, chlorine, methyl, methoxy,
  • V 2 also very particularly preferably represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl.
  • W also very particularly preferably represents hydrogen or methyl
  • X also very particularly preferably represents chlorine, methyl or trifluoromethyl
  • Y is also very particularly preferably in the 5-position for the rest
  • Z is also very particularly preferably in the 4-position for hydrogen or methyl
  • V 1 also very particularly preferably represents fluorine, chlorine, methyl, methoxy, trifluoromethyl or trifluoromethoxy
  • V 2 also very particularly preferably represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl.
  • W also very particularly preferably represents hydrogen, methyl, chlorine or
  • X also very particularly preferably represents chlorine, bromine, methyl, ethyl, propyl, methoxy, trifluoromethyl, difluoromethoxy, trifluoroethoxy or cyano,
  • Y is also very particularly preferably in the 3 or 5 position for hydrogen, chlorine, bromine or methyl
  • Z is also very particularly preferably in the 4-position for hydrogen
  • B very particularly preferably represents C 2 -C 4 -alkenyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, optionally optionally one to two times by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or Nitro substituted phenyl, for cyclopropyl, for cyclopentyl or cyclohexyl, in which a methylene group is optionally replaced by oxygen,
  • D very particularly preferably represents NH
  • G very particularly preferably represents hydrogen (a) or one of the groups ( g ), in which
  • E represents a metal ion or an ammonium ion
  • L represents oxygen or sulfur
  • M oxygen or sulfur
  • R very particularly preferably represents in each case mono- to trisubstituted by fluorine or chlorine-substituted C 1 -C 4 -alkyl, C 2 -C 10 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 4 -alkyltMo-C ⁇ - C 2 is substituted alkyl or optionally monosubstituted by fluorine, chlorine, methyl, ethyl or methoxy, C3-C (5 cycloalkyl,
  • phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy,
  • furanyl, thienyl or pyridyl each optionally substituted by chlorine, bromine or methyl
  • R 2 very particularly preferably represents in each case mono- to trisubstituted by fluorine or chlorine substituted C ⁇ -C ⁇ Q-alkyl, C2-C10-alkenyl or -CC-C4-alkoxy-C2-C4-al yl, for cyclopentyl or cyclohexyl or for phenyl or benzyl which is optionally mono- to disubstituted by fluorine, chlorine, cyano, nitro, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy,
  • R 3 very particularly preferably represents methyl, ethyl, propyl or isopropyl which is optionally mono- to trisubstituted by fluorine or chlorine, or optionally monosubstituted by fluorine, chlorine, bromine, methyl, ethyl, isopropyl or tert-butyl, Methoxy, ethoxy, iso-propoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro substituted phenyl,
  • R 4 and R5 independently of one another very particularly preferably represent C1-C4-alkoxy or Ci-C4-alkylthio or each in each case optionally substituted by fluorine, chlorine, bromine, nitro, cyano, methyl, methoxy, trifluoromethyl or trifluoromethoxy or phenyl, phenoxy or phenylthio,
  • R 0 " and R? Independently of one another very particularly preferably represent hydrogen, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, dd ⁇ -alkoxy, C 3 -C -alkenyl or C 1 -C 4 -alkoxy-C2 -C4-alkyl, for phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl, or together for a C5-Cg'-alkylene radical in which a methylene group is optionally replaced by oxygen or sulfur.
  • W particularly preferably represents ethyl or methoxy
  • X particularly preferably represents chlorine, bromine, methyl, ethyl, propyl, methoxy, trifluoromethyl, difluoromethoxy or cyano,
  • Y particularly preferably in the 4-position represents hydrogen, chlorine or bromine
  • Z particularly preferably in the 5-position represents hydrogen
  • B particularly preferably represents C 2 -C 4 alkenyl, methoxy, ethoxy, propoxy,
  • D particularly preferably represents NH
  • G particularly preferably represents hydrogen (a) or one of the groups
  • M oxygen or sulfur
  • Rl particularly preferably represents C 1 -C 6 -alkyl which is optionally mono- to trisubstituted by fluorine or chlorine, C 2 -C 12 -alkenyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 2 -alkylthio-C 1 -C 2 -C alkyl or for cyclopropyl,
  • phenyl optionally substituted simply by fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy, for furanyl, thienyl or pyridyl, each optionally substituted by chlorine or methyl,
  • R 2 particularly preferably represents Ci-Cg-alkyl, d ⁇ -Cg-alkenyl or C1-C2-
  • W also particularly preferably represents hydrogen, chlorine, bromine or methyl
  • X also particularly preferably represents chlorine, bromine, methyl, ethyl, propyl,
  • Y is also particularly preferably in the 4 position for the rest
  • V also particularly preferably represents fluorine, chlorine, methyl, methoxy, trifluoromethyl or trifluoromethoxy,
  • V 2 also particularly preferably represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl,
  • A also particularly preferably stands for -CH 2 -, -CHCH 3 - or -CH 2 -CH 2 -
  • B also particularly preferably represents C 2 -C 4 -alkenyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, optionally optionally one to two times by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, Cyano or nitro substituted phenyl,
  • D also particularly preferably stands for NH
  • G also particularly preferably represents hydrogen (a) or one of the groups
  • M oxygen or sulfur
  • Rl also particularly preferably represents in each case C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -substituted or substituted by fluorine or chlorine,
  • phenyl optionally substituted simply by fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy,
  • R 2 also particularly preferably represents Ci-Cg-alkyl, C2-C6-alkenyl or C ⁇ - C2-alkoxy-C2-C3-alkyl, cyclopentyl or cyclohexyl, or each optionally simply by fluorine, chlorine, cyano, nitro , Methyl, methoxy, trifluoromethyl or trifluoromethoxy substituted phenyl or benzyl.
  • W also particularly preferably represents hydrogen or methyl
  • X also particularly preferably represents chlorine or methyl
  • Y is also particularly preferably in the 5 position for the rest
  • Z is also particularly preferably in the 4-position for hydrogen or methyl
  • V 1 also particularly preferably represents fluorine, chlorine, methyl, methoxy, trifluoromethyl or trifluoromethoxy,
  • V 2 also particularly preferably represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl,
  • A also particularly preferably represents -CH 2 -, -CHCH 3 - or -CH2-CH2-,
  • B also particularly preferably represents C 2 -C 4 -alkenyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, optionally optionally one to two times by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or Nitro substituted phenyl, D also particularly preferably stands for JNH,
  • G also particularly preferably represents hydrogen (a) or one of the groups
  • M oxygen or sulfur
  • R also particularly preferably represents in each case C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl which is optionally mono- to trisubstituted by fluorine or chlorine,
  • phenyl optionally substituted simply by fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy,
  • furanyl, thienyl or pyridyl each optionally substituted by chlorine or methyl
  • R 2 also particularly preferably represents C 1 -C 6 -alkyl, QJ-C ⁇ -alkenyl or
  • Ci -C2-alkoxy-C 2 -C 3 -alkyl for cyclopentyl or cyclohexyl, or for each optionally simply by fluorine, chlorine, cyano, nitro,
  • W also particularly preferably represents hydrogen, methyl, chlorine or bromine,
  • X also particularly preferably represents chlorine, bromine, methyl, ethyl,
  • Y is also particularly preferably in the 3 or 5 position for hydrogen, chlorine, bromine or methyl
  • Z is also particularly preferably in the 4-position for hydrogen, chlorine, bromine, methyl, trifluoromethyl or trifluoromethoxy,
  • A also particularly preferably stands for -CH 2 -, -CHCH 3 - or -CH 2 -CH 2 -,
  • B also particularly preferably stands for C -C 4 -alkenyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, for phenyl optionally substituted once or twice by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro for cyclopropyl, for cyclopentyl or cyclohexyl, in which a methylene group is optionally replaced by oxygen,
  • D also particularly preferably stands for JNH
  • G also particularly preferably represents hydrogen (a) or one of the
  • M oxygen or sulfur
  • R also particularly preferably represents in each case mono- to trisubstituted or substituted by fluorine or chlorine-C 1-6 alkyl, C 2 -C 6 -alkenyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl, d ⁇ -alkylthio-Ci ⁇ - alk l or for cyclopropyl, cyclopentyl or cyclohexyl,
  • R 2 also particularly preferably represents C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl or C 1 -C 2 -alkoxy-C 2 -C 4 -alkyl, cyclopentyl or cyclohexyl, or each optionally simply by fluorine, chlorine, cyano, nitro, Methyl, methoxy, trifluoromethyl or trifluoromethoxy substituted phenyl or benzyl.
  • W stands for hydrogen
  • X stands for methyl or chlorine
  • Y stands in the 5-position for chlorine-substituted phenyl
  • A stands for -CH2-
  • B stands for chlorine-substituted phenyl
  • G stands for hydrogen.
  • W also stands for hydrogen or methyl
  • X also stands for methyl or chlorine
  • Y is also highlighted in the 3- or 5-position for hydrogen or methyl
  • Z is also highlighted in the 4-position for hydrogen, methyl or
  • A also stands out for -CH 2 - or -CH 2 -CH 2 -,
  • B also stands out for methoxy, ethoxy, isopropyl, cyclopentyl, in which a methylene group is optionally replaced by oxygen, cyclohexyl, ethenyl or for phenyl which is optionally substituted by chlorine,
  • G also stands for hydrogen (a) or for one of the groups
  • R 1 also stands for C i -Cg-alkyl
  • R 2 also stands for d-Cg-alkyl
  • Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl
  • alkyl or alkenyl can also be straight-chain or branched as far as possible, also in conjunction with heteroatoms, such as, for example, in alkoxy.
  • Optionally substituted radicals can be mono- or polysubstituted, and in the case of multiple substitutions the substituents can be the same or different.
  • reaction process can be represented by the following reaction scheme:
  • A, B, W, X, Y, Z and R 8 have the meanings given above,
  • acylamino acid esters of the formula (IT) are obtained, for example, if amino acid derivatives of the formula (JXIV)
  • A, B and R 8 have the meaning given above,
  • W, X, Y and Z have the meanings given above and
  • W, X, Y and Z have the meanings given above and
  • the compounds of the formulas (XIV) and (JXVJD) are new and can be prepared by known processes (see, for example, Compagnon, Ann. Chim. (Paris) [14] 5, pp. 11-22, 23-27 (1970), L. Munday, J. Chem. Soc. 4372 (1961); JT Eward, C. Jitrangeri, Can. J. Chem. 53, 3339 (1975).
  • the 1-amino-cyclohexane-carboxylic acids (JXVII) are new and generally available after the Bucherer-Bergs synthesis or after the Strecker synthesis and are obtained in different forms of isomers.
  • the isomer (hereinafter referred to as ⁇ for the sake of simplicity) is predominantly obtained, in which the 4-substituent and the carboxyl group are in equatorial fashion, while under the conditions of the Strecker synthesis this is predominantly Isomer (hereinafter referred to as ⁇ for the sake of simplicity) occurs in which the amino group and the 4-substituent are equatorial.
  • W, X, Y, Z and shark have the meanings given above,
  • the compounds of the formula (XDQ are also new.
  • the compounds of the formula (JXVHI) are also new.
  • A, B, W, X, Y, Z and R 8 have the meanings given above,
  • A, B and R 8 have the meanings given above,
  • W, X, Y, Z and shark have the meanings given above,
  • the 1-hydroxy-cyclohexyl-carboxylic acid esters of the formula (XX) are partly new. They are obtained, for example, by substituting substituted 1-hydroxy-cyclohexane-carboxylic acid nitriles in the presence of acids, e.g. according to Pinner with alcohols.
  • the cyanohydrin is obtained, for example, by reacting substituted cyclohexan-1-ones with hydrocyanic acid.
  • Process (A) is characterized in that compounds of the formula (H), in which A, B, W, X, Y, Z and R 8 have the meanings given above, in the presence of a diluent and in the presence of a base subject to intramolecular condensation.
  • Diluents which can be used in process (A) according to the invention are all organic solvents which are inert to the reactants. Hydrocarbons such as toluene and xylene are also preferably usable
  • Ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone, and alcohols such as methanol, ethanol, propanol, isopropanol, butanol and iso -Butanol and tert-butanol.
  • polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone
  • alcohols such as methanol, ethanol, propanol, isopropanol, butanol and iso -Butanol and tert-butanol.
  • All the usual proton acceptors can be used as the base (deprotonating agent) when carrying out process (A) according to the invention.
  • Alkali metal and alkaline earth metal oxides, hydroxides and carbonates such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, which can also be used in the presence of
  • Alkali metals such as sodium or potassium can also be used.
  • alkali metal and alkaline earth metal amides and hydrides, such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alcoholates such as sodium methylate, sodium ethylate and potassium tert-butoxide can be used.
  • reaction temperature can be varied within a substantial range. In general, temperatures between -75 ° C and 200 ° C, preferably between -50 ° C and 150 ° C.
  • Process (A) according to the invention is generally carried out under normal pressure.
  • reaction component of the formula (II) and the deprotonating base are generally employed in equimolar to approximately double-equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles).
  • the process (B) is characterized in that compounds of the formula (III), in which A, B, W, X, Y, Z and R 8 have the meanings given above, are intramolecularly in the presence of a diluent xmd in the presence of a base condensed.
  • Diluents which can be used in process (B) according to the invention are all organic solvents which are inert to the reactants. Hydrocarbons such as toluene and xylene are also preferably usable
  • Ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone.
  • Alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol and tert-butanol can also be used. All conventional proton acceptors can be used as the base (deprotonating agent) when carrying out process (B) according to the invention.
  • Alkali metal and alkaline earth metal oxides, hydroxides and carbonates such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, which can also be used in the presence of
  • Alkali metals such as sodium or potassium can also be used.
  • alkali metal and alkaline earth metal amides and hydrides such as sodium amide, sodium hydride and calcium hydride, xmd and also alkali metal alcoholates, such as sodium methylate, sodium ethylate and potassium tert.-butylate, can also be used.
  • reaction temperature can be varied within a relatively wide range. In general, temperatures between -75 ° C and 200 ° C, preferably between -50 ° C and 150 ° C.
  • Process (B) according to the invention is generally carried out under normal pressure.
  • reaction components of the formula (HU) xmd and the deprotonating bases are generally employed in approximately equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles).
  • the process (C ⁇ ) is characterized in that compounds of the formulas (Ila) to (I-2-a) are each reacted with carboxylic acid halides of the formula (IV), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Diluents which can be used in process (C ⁇ ) according to the invention are all solvents which are inert to the acid halides.
  • Hydrocarbons such as gasoline, benzene, toluene, xylene and tetralin
  • Hydrocarbons are preferably usable, furthermore halogenated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene xmd o-dichlorobenzene, and also ketones, such as acetone and methylisopropyl ketone, and furthermore ethers, such as diethyl ether, Tetrahydrofxiran and dioxane, in addition carboxylic acid esters, such as ethyl acetate, and also strongly polar solvents, such as dimethylformamide, dimethyl sulfoxide and sulfolane. If the hydrolysis stability of the acid halide permits, the reaction can also be carried out in the presence of water.
  • Suitable acid binders for the reaction according to the 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 xmd N, N-dimethylaniline, and also alkaline earth metal oxides, such as magnesium and calcium oxide, are preferably usable.
  • alkali and alkaline earth metal carbonates such as sodium carbonate, potassium carbonate and calcium carbonate
  • alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
  • the reaction temperature can be varied within a substantial range in the process (C ⁇ ) according to the invention. In general, temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C.
  • Suitable diluents diluents for use in the inventive process is preferably be used those which preferably come from the use of acid halides into consideration. Otherwise, an excess of carboxylic acid anhydride can also act as a diluent.
  • acid-binding agents for process (C p) are preferably those acid-binding agents in question, which are preferably even with the use of acid halides into consideration.
  • the reaction temperature can be varied within a substantial range in the process ( C ⁇ ) according to the invention. In general, temperatures between -20 ° C xmd + 150 ° C, preferably between 0 ° C and 100 ° C.
  • the starting materials of the formulas (Ila) to (I-2-a) and the carboxylic anhydride of the formula (V) are generally used in approximately equivalent amounts. However, it is also possible to use the carboxylic anhydride in a larger excess (up to 5 mol). The processing takes place according to usual methods.
  • the general procedure is to remove diluent and excess carboxylic acid anhydride and the carboxylic acid formed by distillation or by washing with an organic solvent or with water.
  • Process (D) is characterized in that compounds of the formulas (Ila) to (I-2-a) are each treated with chloroformates or chloroformates esters of the formula (VI), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Suitable acid binders in process (D) according to the invention are all customary acid acceptors.
  • Tertiary amines such as triethylamine, pyridine, DABCO, DBU, DBN, Hunig base and N, N-dimethylaniline, furthermore alkaline earth metal oxides such as magnesium and calcium oxide, and also alkali metal and alkaline earth metal carbonates such as sodium carbonate, potassium carbonate and calcium carbonate are preferably usable and alkali hydroxides such as sodium hydroxide and potassium hydroxide.
  • Diluents which can be used in process (D) according to the invention are all solvents which are inert to the chloroformates or chloroformates.
  • Hydrocarbons such as gasoline, benzene, toluene, xylene and tetralin, and furthermore halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-
  • Dichlorobenzene also ketones, such as acetone and methyl isopropyl ketone, further ethers, such as diethyl ether, tetrahydrofuran xmd dioxane, in addition carboxylic acid esters, such as ethyl acetate, and also nitriles such as acetonitrile xmd, and also strongly polar solvents, such as dimethylformamide, dimethyl sulfoxide and sulfolane.
  • ketones such as acetone and methyl isopropyl ketone
  • further ethers such as diethyl ether, tetrahydrofuran xmd dioxane
  • carboxylic acid esters such as ethyl acetate
  • nitriles such as acetonitrile xmd
  • strongly polar solvents such as dimethylformamide, dimethyl sulfoxide and sulfolane.
  • reaction temperature can be varied within a substantial range.
  • the reaction temperature is generally between -20 ° C and + 100 ° C, preferably between 0 ° C and 50 ° C.
  • Process (D) according to the invention is generally carried out under normal pressure.
  • the starting materials of the formulas (Ila) to (I-2-a) and the corresponding chloroformic acid ester or chloroformic acid thiolester of the formula (VI) are generally in each case indicated in approaches equivalent amounts used. However, it is also possible to use one or the other component in a larger excess (up to 2 mol).
  • the processing takes place according to usual methods. The general procedure is to remove precipitated salts and to concentrate the remaining reaction mixture by stripping off the diluent.
  • Process (E) according to the invention is characterized in that compounds of the formulas (I-l-a) to (I-2-a) are each reacted with compounds of the formula (V ⁇ ) in the presence of a diluent and, if appropriate, in the presence of an acid binder.
  • chloromothio formate or chlorodithio formate of formula (VD) is set at 0 to 120 ° C., preferably at 20 to 60, per mole of starting compound of the formulas (Ila) to (I-2-a) ° C around.
  • Possible diluents added are all inert polar organic solvents, such as ethers, amides, sulfones, sulfoxides, but also haloalkanes.
  • Dimethyl sulfoxide, tetrahydrofuran, dimethylformamide, ethyl acetate or methylene chloride are preferably used.
  • the addition of strong deprotonating agents such as e.g. Sodium hydride or potassium tert-butylate is the enolate salt of
  • Alkali or alkaline earth metal carbonates or hydrogen carbonates or nitrogen bases examples include sodium hydride, sodium methoxide, sodium hydroxide, calcium hydroxide, potassium carbonate, matrix hydrogen carbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline, diazabicyclooctane (DABCO), diazabicyclonones (DBJN) xmd diazabicycloundecen (DBU).
  • the reaction can be carried out under normal pressure or under elevated pressure, preferably under normal pressure.
  • the processing takes place according to usual methods.
  • Process (F) is characterized in that compounds of the formulas (I-l-a) to (I-2-a) are each reacted with sulfonyl chlorides of the formula (VTD), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Production process (F) uses per mole of starting compound of the formula
  • Process (F) is preferably carried out in the presence of a diluent.
  • Suitable diluents are all inert polar organic solvents such as ethers, amides, ketones, carboxylic acid esters, nitriles, sulfones, sulfoxides or halogenated hydrocarbons such as methylene chloride.
  • Dimethyl sulfoxide, tetrahydrofuran, dimethylformamide, ethyl acetate and methylene chloride are preferably used.
  • the enolate salt is made by adding strong deprotonating agents (such as sodium hydride or potassium tertiary butoxide) of the compounds (Ila) to (I-2-a), the further addition of acid binders can be dispensed with.
  • strong deprotonating agents such as sodium hydride or potassium tertiary butoxide
  • customary inorganic or organic bases are suitable, for example sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.
  • the reaction can be carried out at atmospheric pressure or at elevated pressure, preferably at atmospheric pressure.
  • the processing takes place according to usual methods.
  • Process (G) according to the invention is characterized in that compounds of the formulas (I-l-a) to (I-2-a) are each reacted with phosphorus compounds of the formula (IX), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • Process (G) is preferably carried out in the presence of a diluent.
  • Acetonitrile, dimethyl sulfoxide, tetrahydrofuran, dimethylformamide, methylene chloride are preferably used.
  • Possible inorganic binders which may be added are conventional inorganic or organic bases, such as hydroxides, carbonates or amines. Examples include sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.
  • the reaction can be carried out under normal pressure or under elevated pressure, preferably under normal pressure.
  • the processing takes place according to the usual methods of organic chemistry.
  • the end products are preferably obtained by crystallization, chromatographic purification or by so-called “distillation", i.e. Removal of volatile components cleaned in vacuo.
  • the process (H) is characterized in that compounds of the formulas (Ila) to (I-2-a) each with metal hydroxides or metal alkoxides of the formula (X) or amines of the formula (XI), optionally in the presence of a diluent means.
  • Diluents which can be used in process (H) according to the invention are preferably ethers such as tetrahydrofuran, dioxane, diethyl ether or alcohols such as methanol, ethanol, isopropanol, but also water.
  • Process (H) according to the invention is generally carried out under normal pressure.
  • the reaction temperature is generally between -20 ° C and 100 ° C, preferably between 0 ° C xmd 50 ° C.
  • Process (I) is characterized in that compounds of the formulas (Ila) to (I-2-a) are each treated with (I) compounds of the formula (XII), if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst or ( Iß) with compounds of the formula (JJXIII), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • manufacturing processes (I ⁇ ) about 1 mol of isocyanate of the formula (XE) is reacted per mole of starting compound of the formulas (Ila) to (I-2-a) at 0 to 100 ° C., preferably at 20 to 50 ° C.
  • Process (I ⁇ ) is preferably carried out in the presence of a diluent.
  • Suitable diluents are all inert organic solvents, such as aromatic hydrocarbons, halogenated hydrocarbons, ethers, amides, nitriles, sulfones or sulfoxides.
  • catalysts can be added to accelerate the reaction.
  • Organotin compounds such as e.g. Dibutyltin dilaurate can be used.
  • any inert polar organic solvents such as ethers, carboxylic acid esters, nitriles, ketones, amides, sulfones, sulfoxides or halogenated hydrocarbons come into consideration as optionally added diluents.
  • Dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride are preferably used.
  • the enolate salt is prepared by adding strong deprotonating agents (such as sodium hydride or potassium tertiary butoxide) of the compounds (Ila) to (I-2-a), the further addition of acid binders can be dispensed with.
  • strong deprotonating agents such as sodium hydride or potassium tertiary butoxide
  • customary inorganic or organic bases are suitable, for example sodium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine.
  • the reaction can be carried out under normal pressure or under elevated pressure, preferably under normal pressure.
  • the processing takes place according to usual methods.
  • the active substances are suitable for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in stockpiling and material protection as well as in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species and against all or individual stages of development.
  • the pests mentioned above include:
  • Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Thysanura e.g. Lepisma saccharina.
  • Phthiraptera e.g. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp ..
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci
  • Empoasca spp. Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.
  • Choristoneura ftimiferana Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae.
  • Leptinotarsa decemlineata Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sultusorrimushmpphppm, 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, Amphimalltra solitus Lissorhoptrus oryzophilus.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp.
  • Siphonaptera for example Xenopsylla cheopis, Ceratophyllus spp ..
  • From the class of the Arachnida for example Scorpio mauras, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyommomma spp., ., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus 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.,
  • the compounds according to the invention can optionally also be used in certain concentrations or application rates as herbicides and microbicides, for example as fungicides, antifungals and bactericides. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Cultivated plants can be plants which can be obtained by conventional breeding xmd optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
  • Plant parts also include crops and vegetative xmd generative sales propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space according to the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular in the case of seeds, furthermore by coating in one or more layers.
  • the active compounds 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 made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents and / or solid carriers
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol 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
  • 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 silicic acid, 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;
  • dispersants e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations. Further,
  • 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 xmd metal phthalocyanine dyes xmd trace nutrients such as salts of iron, manganese, boron, copper, cobalt,
  • Molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to widen the spectrum of action or to prevent development of resistance. In many cases, synergistic effects are obtained, ie the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Aldimo ⁇ h Ampropylfos, Ampropylfos-Kahum, Andoprim, Anilazin, Azaconazol, Azoxystrobin,
  • Famoxadon Fenapanil, Fenarimol, Fenbuconazol, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimo ⁇ h, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Flu ⁇ rimidol, Flusrimidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax,
  • Oxadixyl Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, Tridemo ⁇ h, trifloxystrobin, triflumizole, triforine, triticonazole,
  • Cyanophos Cycloprene, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazine,
  • Fenamiphos Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxuron, Fluthrinoxin, Fluutinoxin, Fluutinoxin , Fubfenprox, Furathiocarb,
  • Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
  • Mecarbam Metaldehyde, Methamidophos, Metharhician anisopliae, Metharhician flavoviride, Methidathione, Methiocarb, Methoprene, Methomyl, Methoxyfenozide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectm, Milbemycin, Monocrotophos,
  • Tefluthrin Tefluthrin, temephos, temivinphos, terbufos, tetrachlorvinphos, tetradifon, theta-cypermethrin, thiacloprid, thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox, thuringinhrine, tri Triarathenes, triazamates, triazophos, triazuron, trichlophenidines, trichlorfon, triflumuron, trimethacarb,
  • Bacillus thuringiensis strain EG-2348 benzoic acid [2-benzoyl-l- (l, l-dimethylethyl) hydrazide Butanoic acid 2,2-dimethyl-3- (2,4-dichlorophenyl) -2-oxo-l-oxaspiro [4.5] dec-3-en-4-yl ester
  • the active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds by 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 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 cleaned substrates.
  • Protoplast fusion obtained plant species and plant varieties and their parts treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetic modified organisms) and their parts are treated.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with new properties (“traits”) which have been grown both by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, bio and genotypes.
  • the treatment according to the invention can also cause superadditive (“synergistic") effects.
  • superadditive for example, reduced application rates and / or widening of the activity spectrum and / or an enhancement of the action of the substances which can be used according to the invention are xmd agents, better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to water or soil salt content, increased flowering performance easier harvest Accelerated ripeness, higher crop yields, higher quality and / or higher nutritional value of the crop products, higher storability and / or workability of the crop products possible, which go beyond the effects that are actually to be expected.
  • the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which, by virtue of the genetic engineering modification, have received genetic material which gives these plants particularly advantageous properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher crop yields, higher quality and / or higher nutritional value of the crop products , higher shelf life and / or workability of the harvest products. Further and particularly highlighted examples of such
  • Properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants against certain herbicidal active ingredients.
  • the important cultivated plants such as cereals (wheat, rice), corn, soybeans, potatoes, cotton,
  • Oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and grapes) are mentioned, whereby maize, soybeans, potatoes, cotton and oilseed rape are particularly emphasized.
  • the properties (“traits”) are particularly emphasized of the plants' increased defense against insects by toxins which arise in the plants, in particular those which are caused by the genetic material
  • Bacillus thuringiensis e.g. by the genes CryIA (a), CryIA (b), Cry ⁇ A (c), CryllA, CryUlA, C ⁇ yi ⁇ B2, Cry9c, Cry2Ab, Cry3Bb and CrylF and their combinations
  • Bt plants The properties (“traits") also particularly emphasize the increased defense of plants against fungi, bacteria and viruses through systemic acquired resistance (SAR),
  • SAR systemic acquired resistance
  • Plant plants are corn varieties, cotton varieties, soy varieties and potato varieties which are marketed under the trade names YIELD GARD ® (e.g. corn, cotton, soy), KnockOut ® (e.g. corn), StarLink ® (e.g. corn), Bollgard ® ( Cotton), Nucotn ® (cotton) and NewLeaf ® (potato).
  • YIELD GARD ® e.g. corn, cotton, soy
  • KnockOut ® e.g. corn
  • StarLink ® e.g. corn
  • Bollgard ® Cotton
  • Nucotn ® cotton
  • NewLeaf ® potato
  • Herbicide-tolerant plants are maize varieties, cotton varieties and soy varieties that are marketed under the trade names Roundup Ready ® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link ® (tolerance to phosphinotricin, e.g. rapeseed), EMI ® (tolerance to imidazolinones) and STS ® (tolerance to sulfonylureas such as corn) are sold.
  • Herbicide-resistant plants (bred conventionally for herbicide tolerance) plants also sold under the name Clearfield ® varieties (eg maize) are mentioned. Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
  • the plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active compound mixtures according to the invention.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants.
  • the active compounds according to the invention act not only against pests from plants, hygiene and stored products, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, and mite mites, Laufinilben, flies (stinging and licking), parasitic fly larvae, lice, hair lice, featherlings and fleas.
  • animal parasites ectoparasites
  • tick ticks such as tick ticks, leather ticks, and mite mites, Laufinilben, flies (stinging and licking), parasitic fly larvae, lice, hair lice, featherlings and fleas.
  • Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
  • Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota ., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Glossina spp., Calliphora spp., Glossina spp.,
  • Amblyomma spp. Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Stemostoma spp., Varroa spp.
  • Actinedida Prostigmata
  • Acaridida Acaridida
  • Acarapis spp. Cheyletiella spp., Omithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophoras spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectolich spp., Pod ., 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 combating arthropods which are used in agricultural animals, such as 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 Hamsters, guinea pigs, rats and
  • Infest mice By fighting these arthropods, deaths and reduced performance (for meat, milk, wool, skins, eggs, honey, etc.) are to be reduced, so that the use of the active compounds according to the invention enables more economical and simple animal husbandry.
  • 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, through nasal
  • 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.
  • Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticuliter es flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
  • Bristle tails such as Lepisma saccharina.
  • technical materials are to be understood as non-living materials, such as preferably plastics, adhesives, glues, papers and cardboard boxes, leather, wood, wood processing products and paints.
  • the one to be protected against insect attack is very particularly preferably
  • Wood and wood processing products that can be protected by the agent according to the invention or mixtures containing it are to be understood as examples:
  • the active compounds can be used as such, in the form of concentrates or generally customary formulations, such as powders, granules, solutions, suspensions, emulsions or pastes.
  • the formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellent, optionally siccatives and UV stabilizers and, where appropriate, dyes and pigments and other processing aids.
  • the insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active ingredient according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
  • the amount of the agents or concentrates used depends on the type and occurrence of the insects and on the medium. The optimum amount to be used can be determined in each case by test series, but in general 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 oil-like low-volatility organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agents.
  • the organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
  • Suitable mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.
  • Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, turpentine oil and Like. Used.
  • liquid aliphatic hydrocarbons with a boiling range from 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range from 180 to 220 ° C. and / or locker oil and / or monochloronaphthalene, preferably ⁇ -monochloromaphthalene are used.
  • the organic low-volatility oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and a flash point above
  • insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.
  • part of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced.
  • Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups, such as, for example, glycol ethers, esters or the like, are preferably used.
  • the known organic-chemical binders are the water-dilutable 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 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.
  • 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
  • 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 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 failure. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).
  • the plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, higher glycerol glycerol or glycerol ether - Kolether, glycerol ester and p-toluenesulfonic acid ester.
  • phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate
  • phosphoric acid esters such as tributyl phosphate
  • adipic acid esters such as di- (2-ethylhexyl) adipate
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
  • Water is also particularly suitable as a solvent or diluent, optionally in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
  • a particularly effective wood protection is achieved through industrial impregnation processes, e.g. Vacuum, double vacuum or pressure process.
  • the ready-to-use compositions may optionally contain further insecticides and, if appropriate, one or more fungicides.
  • the insecticides and fungicides mentioned in WO 94/29268 are preferably suitable as additional admixing partners.
  • the compounds mentioned in this document are an integral part of the present application.
  • Insecticides such as chlorpyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, JNI-25, flufenoxuron, hexaflumuron, transflutoxuron, trifluorophenurin, trifluorophenol, trifluorophenol, methifluorophenol,
  • fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluoride, tolylfluanid, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5- - octylisothiazolin-3-one.
  • the compounds according to the invention can be used to protect objects, in particular ship hulls, sieves, nets, structures, quay systems and signaling systems which come into contact with sea or brackish water.
  • heavy metals such as e.g. in bis- (trialkyltin) sulfides, tri-n-butyltin laurate, tri-n-butyltin chloride, copper (JT) oxide, triethyltin chloride, tri-butyl (2-phenyl-4-chlorophenoxy) tin, tributyltin oxide, molybdenum disulfide , Antimony oxide, polymeric butyl titanate, phenyl- (bispyridine) bismuth chloride, tri-R-butyltin fluoride, manganese ethylene bisthiocarbamate, zinc dimethyldithiocarbamate, zinc ethylene bisthiocarbamate, zinc and copper salts of 2-pyridinethiol-1-oxide, bisdimethyldihamidoxydiamidoxydiamidoxydiaminodiaminodiaminodiimide, bis
  • the ready-to-use antifouling paints may also contain other active ingredients, preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.
  • Suitable combination partners for the antifouling agents according to the invention are preferably:
  • Fungicides like Benzo [b] thio ⁇ hencarboxylic acid cyclohexylamide-S, S-dioxide, dichlofluanid, fluoropolpet, 3-iodo-2-propynyl butyl carbamate, tolyl fluanide and azoles such as
  • Fentin acetate, metaldehyde, methiocarb, niclosamide, thiodicarb xmd trimethacarb; or conventional antifouling agents such as
  • the antifouling agents used contain the active compound according to the invention of the compounds according to the invention in a concentration of 0.001 to 50% by weight, in particular of 0.01 to 20% by weight.
  • the antifouling agents according to the invention further contain the usual ingredients such as in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.
  • antifouling paints contain in particular binders.
  • Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in one 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 polystyrene acrylonitrile rubbers, drying oils, such as linseed oil, resin esters or modified hard resins in combination with tar or bitumen, asphalt and epoxy compounds , small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.
  • Paints may also contain inorganic pigments, organic pigments or dyes, which are preferably insoluble in seawater. Paints may also contain materials such as rosin in order to be controlled
  • the paints may also contain plasticizers, modifiers affecting theological properties, and other conventional ingredients.
  • the compounds according to the invention or the abovementioned mixtures can also be incorporated into self-polishing antifouling systems.
  • the active ingredients are also suitable for controlling animal pests, in particular insects, arachnids and mites, which live in closed spaces such as apartments, factory halls, offices, vehicle cabins, etc. occurrence.
  • animal pests in particular insects, arachnids and mites, which live in closed spaces such as apartments, factory halls, offices, vehicle cabins, etc. occurrence.
  • insects in particular insects, arachnids and mites
  • they can be used alone or in combination with other active ingredients 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 for example Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, JRhipi- cephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forteratississus.
  • Araneae for example Aviculariidae, Araneidae.
  • Opiliones e.g. Pseudosco ⁇ iones chelifer, Pseudosco ⁇ iones cheiridium, Opiliones phalangium.
  • Diplopoda e.g. Blaniulus guttulatus, Polydesmus spp.
  • Anthrenus spp. From the order of the Coleptera, for example Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.
  • Aedes aegypti Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora eiythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila sppica, Musannotiapppp , Simulium spp., Stomoxys calcitrans, Tipula paludosa.
  • Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia inte ⁇ unctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
  • Ctenocephalides canis Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula sp. , Tetramorium caespitum.
  • Rhodinus prolixus Triatoma infestans.
  • Atomizer sprays automatic fog machines, foggers, foams, gels, vaporizer products with vaporizer plates made of cellulose or plastic, liquid vaporizers,
  • the active compounds according to the invention can also be used as defoliants, desiccants, haulm killers and in particular as weed killers.
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • Sci ⁇ us, Setaria, Sorghum Monocot cultures of the genera: Allium, pineapple, asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea.
  • the active compounds according to the invention are suitable for combating total weeds, e.g. on industrial and track systems and on
  • the active compounds for weed control in permanent crops e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry freight and hop systems, on ornamental and sports turf and pasture areas as well for selective weed control in annual crops.
  • the compounds of the formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for selective use
  • the active compounds according to the invention can also be used to control animal pests and fungal or bacterial plant diseases. If appropriate, they can also be used as intermediates or products for the synthesis of further active ingredients.
  • the active ingredients can be converted into the usual formulations, such as
  • Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as fine encapsulation in polymeric substances.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is liquid solvents and or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Possible solid carriers are: e.g. Ammonium salts and natural rock powders such as kaolins, alumina, talc, JE reide, 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,
  • Alkylaryl polyglycol ethers alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates;
  • the following may be used as dispersants: for example lignin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxyethyl 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 are used.
  • 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 are used.
  • the formulations generally contain between 0.1 and 95 percent by weight
  • Active ingredient preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known herbicides and / or with substances which improve crop tolerance ("safenein") for weed control, ready-to-use formulations or tank mixes being possible. Mixtures are therefore also possible possible with weed control agents which contain one or more known herbicides and a safener.
  • safenein crop tolerance
  • Acetochlor Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amicarbazone, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Beflubutamide, Benazolin (-ethyl), Benulfureson -methyl), bentazone, benzfendizone, benzobicyclone, benzofenap, benzoylprop
  • Known safeners are also suitable for the mixtures, for example: AD-67, BAS-145138, Benoxacor, Cloquintocet (-mexyl), Cyomeüinil, 2,4-D, DJ A-24, dichlormid, Dymron, Fenclorim, Fenchlorazol (- ethyl), flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), MCPA, mecoprop (-P), mefenpyr (-diethyl), MG-191, oxabetrinil, PPG-1292, R-29148.
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil pollution is also possible.
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
  • the substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.
  • Fungicides can be used in crop protection to combat Plasmodiophoromyces, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae xmd Streptomycetaceae.
  • Xanthomonas species such as, for example, Xanthomonas campestris pv. Oryzae;
  • Pseudomonas species such as, for example, Pseudomonas syringae pv. Lachrymans;
  • Erwinia species such as, for example, Erwinia amylovora;
  • Pythium species such as, for example, Pythium ultimum
  • Phytophthora species such as, for example, Phytophthora infestans
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;
  • Plasmopara species such as, for example, Plasmopara viticola
  • Bremia species such as, for example, Bremia lactucae
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae;
  • Erysiphe species such as, for example, Erysiphe grarninis;
  • Sphaerotheca species such as, for example, Sphaerotheca ftxliginea
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Venturia species such as, for example, Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
  • Cochliobolus species such as, for example, Cochliobolus sativus
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Puccinia species such as, for example, Puccinia recondita
  • Sclerotinia species such as, for example, Sclerotinia sclerotiorum
  • Tilletia species such as, for example, Tilletia caries
  • Ustilago species such as, for example, Ustilago nuda or Ustilago avenae;
  • Pellicularia species such as, for example, Pellicularia sasakii;
  • Pyricularia species such as, for example, Pyricularia oryzae
  • Fusarium species such as, for example, Fusarium culmorum
  • Botrytis species such as, for example, Botrytis cinerea
  • Septoria species such as, for example, Septoria nodorum
  • Leptosphaeria species such as, for example, Leptosphaeria nodorum;
  • Cercospora species such as, for example, Cercospora canescens
  • Altemaria species such as, for example, Altemaria brassicae;
  • Pseudocercosporella species such as, for example, Pseudocercosporella he ⁇ otrichoides.
  • the active compounds according to the invention also have a strong strengthening effect in plants. They are therefore suitable for mobilizing the plant's own defenses against attack by unwanted microorganisms.
  • Plant-strengthening (resistance-inducing) substances are to be understood in the present context as those substances which are able to stimulate the defense system of plants in such a way that the treated plants largely react to subsequent inocolation with undesired microorganisms
  • undesired microorganisms are understood to mean phytopathogenic fungi, bacteria and viruses.
  • the substances according to the invention can thus be used to protect plants against attack by the pests mentioned within a certain period of time after the treatment.
  • the period within which protection is brought about generally ranges from 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active compounds.
  • the active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance.
  • the active compounds according to the invention can also be used in certain concentrations and application rates as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates and products for the synthesis of further active ingredients.
  • the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
  • technical materials are understood to mean non-living materials that have been prepared for use in technology.
  • technical materials which are to be protected against microbial change or destruction by active substances according to the invention can be used.
  • parts of production systems, for example cooling water circuits are also mentioned that can be impaired by the multiplication of microorganisms.
  • technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer liquids, particularly preferably wood.
  • Bacteria, fungi, yeasts, algae and slime organisms can be mentioned as materials.
  • the active compounds according to the invention preferably act against fungi, in particular molds, wood-coloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • Microorganisms of the following genera may be mentioned, for example:
  • Altemaria such as Alternaria tenuis
  • Aspergillus such as Aspergillus niger
  • Chaetomium like Chaetomium globosum
  • Coniophora such as Coniophora puetana
  • Lentinus such as Lentinus tigrinus
  • Penicillium such as Penicillium glaucum
  • Polyporus such as Polyporus versicolor
  • Aureobasidium such as Aureobasidium pullulans
  • Sclerophoma such as Sclerophoma pityophila
  • Trichoderma like Trichoderma viride
  • Pseudomonas such as Pseudomonas aeruginosa
  • Staphylococcus such as Staphylococcus aureus.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols,
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • water e.g. organic solvents can also be used as auxiliary solvents.
  • aromatics such as
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions
  • alcohols such as butanol or glycol
  • ketones such as
  • Gaseous extenders or carriers are those liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • solid carriers for example, 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.
  • Possible solid carriers for granules are: e.g.
  • emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyemylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example 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 also 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 xmd trace nutrients, such as salts of iron, manganese, boron, copper, cobalt,
  • Molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order to broaden the spectrum of action, for example, or to prevent the development of resistance. In many cases, synergistic effects are obtained, ie the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • bromuconazole Bupirimate; Buthiobate; butylamine;
  • Dagger G debacarb; dichlofluanid; dichlone; dichlorophen; diclocymet;
  • dimethirimol Dimethomo ⁇ h; dimoxystrobin; diniconazole; Diniconazole-M; dinocap; diphenylamines; Dipyrithione; Ditalimfos; dithianon; dodine; Drazoxolon;
  • edifenphos epoxiconazole; ethaboxam; ethirimol; etridiazole; famoxadone;
  • fluazinam Flubenzimine; fludioxonil; flumetover; Flumo ⁇ h; fluoromides; fluoxastrobin; fluquinconazole; Flu ⁇ rimidol; flusilazole; flusulfamide; flutolanil; flutriafol; folpet; Fosetyl-Al; Fosetyl-sodium; fuberidazole; furalaxyl; furametpyr;
  • Furcarbanil Furmecyclox
  • mancozeb maneb; Meferimzone; mepanipyrim; mepronil; metalaxyl; Metalaxyl-M; metconazole; methasulfocarb; Methfuroxam; metiram; metominostrobin;
  • natamycin natamycin
  • nicobifen Nitro Thal-isopropyl
  • Noviflumuron nuarimol
  • procymidone propamocarb; Propanosine-sodium; propiconazole; propineb;
  • proquinazid prothioconazole; pyraclostrobin; Pyrazohos; pyrifenox; pyrimethanil;
  • Thicyofen Thifluzamide; Thiophanate-methyl; thiram; Tioxymid; Tolclofos-methyl;
  • Bacillus popilliae Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Baculoviruses, Beauveria bassiana, Beauveria tenella, Bendiocarb, Benfuracarb,
  • Cadusafos Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron,
  • Chlormephos Chlo ⁇ yrifos, Chlo ⁇ yrifos M, Chlovaporthrin, Chromafenozide, Cis- Resmethrin, cispermethrin, clocythrin, cloethocarb, clofentezine, clothianidine,
  • Fenamiphos Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate,
  • Fipronil fluazuron, flubrocytlirinate, flucycloxuron, flucythrinate, flufenoxuron,
  • Granuloseviruses Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
  • Methoxyfenozide metolcarb, metoxadiazone, mevinphos, milbemectin,
  • Pirimiphos M Profenofos, Promecarb, Propargite, Propoxur, Prothiofos, Prothoat,
  • Tefluthrin Temephos, Temivinphos, Terbufos, Tetrachlorvinphos, Tetradifon Thetacypermethrin, Thiacloprid, Thiamethoxam, Thiapronil, Thiatriphos, Thiocyclam hydrogen oxalate, Thiodicarb, TJhiofanox, Thuringythrin, Truringin
  • Triarathenes triazamates, triazophos, triazuron, trichlophenidines, trichlorfon,
  • the compounds of the formula (I) according to the invention also have very good antifungal effects. They have a very broad anti-mycotic spectrum of activity, in particular against dermatophytes xmd sprout fungi, mold xmd diphasic fungi (e.g. against Candida species such as Candida albicans, Candida glabrata) and Epider ophyton floccosum, Aspergilfus species such as
  • Trichophyton species such as Trichophyton mentagrophytes
  • Microsporon species such as Microsporon canis and audouimi.
  • the list of these fungi is in no way a limitation of the detectable mycotic spectrum, but is only of an explanatory nature.
  • the active ingredients can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules.
  • Application takes place in the usual way, for example by pouring, spraying, spraying, Scattering, dusting, foaming, brushing etc. It is also possible to apply the active ingredients using the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient into the soil itself.
  • the seeds of the plants can also be treated.
  • the application rates can be varied within a relatively wide range, depending on the type of application.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.
  • the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • the solvent is then distilled off and the residue is taken up in 50 ml of water and brought to pH 2 with hydrochloric acid.
  • the precipitate is suctioned off.
  • the mixture is stirred under reflux and the reaction is monitored by thin layer chromatography.
  • reaction solution is spun in, the precipitate is taken up in dichloromethane and washed twice with 50 ml of 0.5N sodium hydroxide solution x g. The mixture is then dried, the solvent is distilled off and recrystallized from MTB ether / n-hexane.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Furan Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Indole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne des kétoénoles spirocycliques substitués de formule (I), dans laquelle W, X, Y, Z, A, B, D et G ont la signification susmentionnée. La présente invention porte également sur plusieurs procédés pour produire ces substances et sur leur utilisation comme agents phytosanitaires, microbicides et herbicides.
EP03794887A 2002-08-28 2003-08-18 Ketoenoles spirocycliques substitues Withdrawn EP1537080A1 (fr)

Priority Applications (1)

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EP10160913.9A EP2233466B1 (fr) 2002-08-28 2003-08-18 Dérivés de l'acide 4-alkoxy-1-amino-cyclohexane-1-carboxylique et leur utilisation comme intermédiaires

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10239479 2002-08-28
DE10239479A DE10239479A1 (de) 2002-08-28 2002-08-28 Substituierte spirocyclische Ketoenole
PCT/EP2003/009103 WO2004024688A1 (fr) 2002-08-28 2003-08-18 Kétoénoles spirocycliques substitués

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KR101236399B1 (ko) 2013-02-22
US20100234229A1 (en) 2010-09-16
AU2003264061B2 (en) 2008-11-13
KR20110091820A (ko) 2011-08-12
JP2006503027A (ja) 2006-01-26
US7754654B2 (en) 2010-07-13
EP2233466A1 (fr) 2010-09-29
CN100575342C (zh) 2009-12-30
CN1694869A (zh) 2005-11-09
US20070275858A1 (en) 2007-11-29
WO2004024688A1 (fr) 2004-03-25
MXPA05002118A (es) 2005-05-23
EP2233466B1 (fr) 2015-06-10
BR0314087A (pt) 2005-07-19
DE10239479A1 (de) 2004-03-04
US8314254B2 (en) 2012-11-20
BR0314087B1 (pt) 2014-07-22
KR20050036961A (ko) 2005-04-20
AU2003264061A1 (en) 2004-04-30
CA2497074C (fr) 2009-11-03
KR101160572B1 (ko) 2012-06-28
CA2497074A1 (fr) 2004-03-25

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