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WO2019081485A1 - Pyrazoles substitués, leurs sels et leur utilisation comme agents herbicides - Google Patents

Pyrazoles substitués, leurs sels et leur utilisation comme agents herbicides

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Publication number
WO2019081485A1
WO2019081485A1 PCT/EP2018/078994 EP2018078994W WO2019081485A1 WO 2019081485 A1 WO2019081485 A1 WO 2019081485A1 EP 2018078994 W EP2018078994 W EP 2018078994W WO 2019081485 A1 WO2019081485 A1 WO 2019081485A1
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WIPO (PCT)
Prior art keywords
alkyl
cycloalkyl
compounds
aryl
alkoxy
Prior art date
Application number
PCT/EP2018/078994
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German (de)
English (en)
Inventor
Thomas Müller
Christopher Robert GARDNER
Uwe Döller
Birgit Kuhn
Andreas Van Almsick
David Michael BARBER
Hansjörg Dietrich
Anu Bheemaiah MACHETTIRA
Elmar Gatzweiler
Christopher Hugh Rosinger
Dirk Schmutzler
Original Assignee
Bayer Cropscience Aktiengesellschaft
Bayer Aktiengesellschaft
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Publication date
Application filed by Bayer Cropscience Aktiengesellschaft, Bayer Aktiengesellschaft filed Critical Bayer Cropscience Aktiengesellschaft
Publication of WO2019081485A1 publication Critical patent/WO2019081485A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • 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
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
    • C07D419/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D419/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
    • C07D419/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems

Definitions

  • the invention relates to the technical field of crop protection agents, in particular that of herbicides for the selective control of weeds and grass weeds in crops. Specifically, this invention relates to substituted pyrazoles and their salts, to processes for their
  • substituted pyrazoles or their salts as herbicidal active substances which carry one of the defined substituted radicals, however, has not yet been described. Surprisingly, it has now been found that substituted pyrazoles or their salts are particularly suitable as herbicidal active compounds which carry one of the defined substituted radicals as herbicides.
  • the present invention thus provides substituted pyrazoles of the general formula (I) or salts thereof
  • each ring or each ring system may optionally be substituted with up to 5 substituents from the group R 3 , is an optionally substituted aryl, heteroaryl, or heterocyclyl, wherein each ring or ring system may be optionally substituted with up to 5 substituents from the group R 4 , is hydrogen, halogen, cyano, (Ci-Cg) alkyl, (Ci-C8) -haloalkyl, (Ci-Cg) cyanoalkyl, (Ci-C8) hydroxyalkyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, (C 3 -Cio) cycloalkyl, (C 3 -Cio) cycloalkyl- (C -C 8) alkyl, (C 3 -C 8) halocycloalkyl, (Ci-C 8) alkoxy, (Ci-C 8)
  • Heteroarylcarbonylamino, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkylcarbonylamino, (C 1 -C 8 ) -hydroxyalkylcarbonylamino, (C 1 -C 8 ) -trialkylsilyl represents hydrogen, hydroxyl, amino, halogen, C 1) -alkyl, (C 1 -C 10) -haloalkyl, (C 2 -C 10) -alkenyl, (C 3 -C 10) -alkynyl, (C 1 -C 10) -cyanoalkyl, (C 1 -C 10) -hydroxyalkyl, (C 3 - Cio) cycloalkyl, (C3-Cio) halocycloalkyl, (C3-Cio) -Cyanocycloalkyl, (C3-Cio) -cycloalkenyl, (
  • the compounds of general formula (I) can be prepared by addition of a suitable organic compound.
  • inorganic or organic acid such as mineral acids such as HCl, HBr, H2SO4, ftPO.sub.i or HNO.sub.3, or organic acids, e.g. Carboxylic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid, or sulfonic acids, such as p-toluenesulfonic acid, to a basic group, e.g. Amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts. These salts then contain the conjugate base of the acid as an anion. Suitable substituents which are in deprotonated form, e.g. Sulfonic acids, certain
  • Sulfonklareamide or carboxylic acids may form internal salts with their turn protonatable groups, such as amino groups. Salt formation can also be due to the action of a base
  • Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine and ammonium, alkali or
  • Potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate are compounds in which the azide hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or
  • Alkaline earth metal salts in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula
  • R a to R d are each independently an organic radical, in particular alkyl, aryl, arylalkyl or alkylaryl. Also suitable are alkylsulfonium and
  • Alkylsulfoxoniumsalze such as (Ci-C4) -trialkylsulfonium and (Ci-C4) -Trialkylsulfoxoniumsalze.
  • substituted pyrazoles of the general formula (I) according to the invention may be present in various tautomeric structures, all of which are intended to be encompassed by the general formula (I).
  • the compounds of the formula (I) used according to the invention and their salts are referred to below as "compounds of the general formula (I)".
  • Preferred subject of the invention are compounds of the general formula (I) wherein
  • each ring or each ring system may optionally be substituted with up to 5 substituents from the group R 3 , is an optionally substituted aryl, heteroaryl, or heterocyclyl, wherein each ring or ring system may optionally be substituted with up to 5 substituents from the group R 4 , is hydrogen, halogen, cyano, (C 1 -C 6) -alkyl, (C 1 -C 6) -haloalkyl, (C 1 -C 6) cyanoalkyl, (Ci-C 6) hydroxyalkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (C 3 -C 8) cycloalkyl, (C 3 -C 8) cycloalkyl (Ci-C 6) alkyl, (C 3 -C 8) halocycloalkyl, (Ci-C 6) alkoxy,
  • R 1 is (C 1 -C 6 ) -alkyl and (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -alkyl and (C 1 -C 8 ) -haloalkyl, or where R 1 and R 2 are together with the C-atom to which they are each bonded, a fully saturated, or partially saturated, optionally interrupted by one to three heteroatoms from the group N, O and S and optionally further substituted, form a total 3-7-membered ring is , hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci-C 8) -alkyl, (C 3 -C 8) cycloalkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) alkynyl, aryl, aryl (Ci-C 8) alkyl, aryl (C 2 -C 8) -
  • Heteroarylcarbonylamino (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkylcarbonylamino, (C 1 -C 8 ) -hydroxyalkylcarbonylamino, (C 1 -C 8 ) -trialkylsilyl, for hydrogen, hydroxyl, amino, halogen, (C 1 -C 8 ) alkyl, (Ci-C 8) haloalkyl, (C 2 -C 8) -
  • Particularly preferred subject matter of the invention are compounds of the general formula (I) in which Q is an optionally substituted aryl, heteroaryl or heterocyclyl, where each ring or each ring system may optionally be substituted by up to 5 substituents from the group R 5
  • Z is an optionally substituted aryl, heteroaryl, or heterocyclyl, where each ring or each ring system may optionally be substituted with up to 5 substituents from the group R 4 ,
  • Y is hydrogen, fluorine, chlorine, bromine, iodine, cyano , (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C 3 -C 6) - cycloalkyl, (C 3 -C 6) halocycloalkyl, (Ci-C 4) -alkoxy, (C -C 4) haloalkoxy, (Ci-C 4) alkylthio, (Ci-C4) haloalkylthio, (Ci-C 4) -Alkylsulfmyl, (Ci-C 4) -Haloalkylsulfmyl, (Ci-C 4) - Alkylsulfonyl, (C 1
  • R 2 is (C 1 -C 6 ) -alkyl and (C 1 -C 6 ) -haloalkyl, or where R 1 and R 2, together with the C-atom to which they are each bonded, are a completely saturated or partially saturated, form optionally interrupted by one to three heteroatoms from the group N, O and S interrupted and optionally further substituted, total 3-7-membered ring is,
  • R 3 is hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6) alkynyl, aryl, aryl (Ci-C 6) alkyl, aryl (C 2 -C 6) - alkenyl, aryl- (C2-C6) alkynyl, aryl (Ci-C6) alkoxy, heteroaryl, (Ci-C6) alkoxy (Ci-C8) alkyl, (Ci-C 6) hydroxyalkyl, (Ci-C 6) -haloalkyl, (C 3 -C 6) halocycloalkyl, (Ci-C 6 ) -alkoxy, (C 1 -C 6 ) -halo
  • Heteroarylcarbonylamino, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkylcarbonylamino, (C 1 -C 6) -hydroxyalkylcarbonylamino, (C 1 -C 6) -trialkylsilyl represents hydrogen, hydroxyl, amino, fluorine, chlorine, bromine, iodine, (Ci-C6) alkyl, (Ci-C6) -haloalkyl, (C 2 -C 6) -alkenyl, (C 3 -C 6) alkynyl, (Ci-C 6) cyanoalkyl, (Ci-C 6 ) hydroxyalkyl, (C 3 -C 6) - cycloalkyl, (C3-C6) halocycloalkyl, (C3-C6) -Cyanocycloalkyl, (C3-C6) cycloalkenyl, (CI-C
  • Q is an optionally substituted aryl, heteroaryl, or heterocyclyl, where each ring or each ring system may optionally be substituted by up to 5 substituents from the group R 5 ,
  • Z is an optionally substituted aryl, heteroaryl, or heterocyclyl, where each ring or each ring system may optionally be substituted by up to 5 substituents from the group R 4 ,
  • Y represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, (Ci-C 3) alkyl, (Ci-C 3) -haloalkyl, (C 3 -C 6) - cycloalkyl, (C 3 -C 6) - Halocycloalkyl, (C 1 -C 3 ) -alkoxy, (C 1 -C 3 ) -haloalkoxy, (C 1 -C 3 ) -alkylthio, (C 1 -C 3 ) -haloalkylthio, (C 1 -C 3 ) -alkylsulfmyl, ( C 3 ) -haloalkylsulfmyl, (C 1 -C 3 ) -alkylsulfonyl, (C 1 -C 3 ) -haloalkylsulfonyl,
  • R 1 is (C 1 -C 4 ) -alkyl and (C 1 -C 4 ) -haloalkyl
  • R 2 is (C 1 -C 4 ) -alkyl and (C 1 -C 4 ) -haloalkyl, or where R 1 and R 2, together with the carbon atom to which they are respectively bonded, are a completely saturated or partially saturated, form optionally interrupted by one to three heteroatoms from the group N, O and S interrupted and optionally further substituted, total 3-7-membered ring is,
  • R 3 is hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (C 1 -C 4 ) -alkyl,
  • (C 3 -C 4) cycloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, aryl, aryl (Ci-C 4) alkyl, aryl (C 2 -C 4 ) -alkenyl, aryl- (C 2 -C 4 ) -alkynyl, aryl- (C 1 -C 4 ) -alkoxy, heteroaryl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, C 4) hydroxyalkyl, (Ci-C 4) -haloalkyl, (C 3 -C 4) halocycloalkyl, (Ci-C 4) alkoxy, (Ci-C6) - haloalkoxy, aryloxy, heteroaryloxy, (C 3 -C 4) cycloalkyloxy, hydroxy, (C 3 -
  • R 4 represents hydrogen, hydroxyl, amino, fluorine, chlorine, bromine, iodine, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 2 -C 4 ) -alkenyl, (C 3 -C 4 ) Alkynyl, (C 1 -C 4 ) cyanoalkyl, (C 1 -C 4 ) -hydroxyalkyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -halocycloalkyl, (C 3 -C 6 ) -cyclo-cycloalkyl, (C 3 -C 6 ) -cycloalkyl, C6) -cycloalkenyl, (C 1 -C 4) - alkyl (C 3 -C 6) cycloalkyl, (Ci-C 4) alkoxy (C3-C6) cycloalky
  • each Ring or any ring system may optionally be substituted with up to 5 substituents from the group R 4 , is hydrogen, fluorine, chlorine, bromine, iodine, cyano, (Ci-C 2 ) alkyl, (Ci-C 2 ) haloalkyl , (C 3 -C 4) - cycloalkyl, (Ci-C 2) alkoxy, (Ci-C2) haloalkoxy, (Ci-C2) alkylthio, (Ci-C 2) haloalkylthio, (Ci- C 2 ) -alkylsulfmyl, (C 1 -C
  • R 4 is hydrogen, hydroxy, amino, fluorine, chlorine, bromine, iodine, (Ci-C i) alkyl, (Ci-C 4 ) -haloalkyl, (C 2 -C 4 ) -alkenyl, (C 3 -C 4 ) -alkynyl, (C 1 -C 4 ) -cyanoalkyl, (C 1 -C 4 ) -hydroxyalkyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -halocycloalkyl, (C 3 -C 6 ) -cyclo-cycloalkyl, ( C3-C6) cycloalkenyl, (C 1 -C 4) alkyl- (C 3 -C 6) cycloalkyl, (Ci-C 4) alkoxy (C 3 -C 6) cycloalkyl, (Ci-C 4 ) -Halo
  • Y represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, (Ci-C 2) alkyl, (Ci-C 2) -haloalkyl, (C 3 -C 4) - cycloalkyl, (Ci-C 2) alkoxy , (C 1 -C 2 ) -haloalkoxy, (C 1 -C 2 ) -alkylthio, (C 1 -C 2 ) -haloalkylthio, (C 1 -C 2 ) -alkylsulfmyl, (C 1 -C 2 ) -haloalkylsulfmyl, (C 1 -C 4) -alkyl 2 ) -alkylsulfonyl, (C1-C2) - haloalkylsulfonyl,
  • R 1 is CH 3 ,
  • R 2 is CH 3 ,
  • R 6 , R 7 , R 8 and R 9 are hydrogen, hydroxyl, amino, fluorine, chlorine, bromine, iodine, cyano, (C 1 -C 12) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 2 - C 4) alkenyl, (C 3 -C 4) alkynyl, (Ci-C 4) cyanoalkyl, (C1-C4) - hydroxyalkyl, (C3-C6) cycloalkyl, (C 3 -C 6) halocycloalkyl , (C 3 -C 6) -Cyanocycloalkyl, (C 1 -C 4) - alkylthio, (Ci-C 4) alkyl, (Ci-C 4) -Alkylsulfmyl- (Ci-C 4) alkyl, (Ci-C 4) alkylsulfonyl (Ci
  • R 16 and R 17 represents hydrogen, fluorine, chlorine, bromine, iodine, (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C 2 -C 4) -alkenyl, (C 3 -C 4 ) -alkynyl, (C 1 -C 4 ) -cyanoalkyl, (C 1 -C 4 ) -hydroxyalkyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -halocycloalkyl, (C 3 -C 6 ) -cyclo-cycloalkyl, ( C3-C6) cycloalkenyl, (C 1 -C 4) - alkoxycarbonyl (C3-C6) cycloalkyl, Hydroxcarbonyl- (C3-C6) cycloalkyl, (C3-C6) cycloalkyl- (Ci-C 4) -
  • R 18 is hydrogen, amino, fluorine, chlorine, bromine, iodine, (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C2-C4) - alkenyl, (C 3 -C 4) alkynyl , (Ci-C 4) cyanoalkyl, (Ci-C 4) hydroxyalkyl, (C 3 -C 6) -cycloalkyl, (C3-C6) halocycloalkyl, (C3-C6) -Cyanocycloalkyl stands,
  • Y represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, (Ci-C 2) alkyl, (Ci-C 2) -haloalkyl, (C 3 -C 4) - cycloalkyl, (Ci-C 2) alkoxy , (C 1 -C 2 ) -haloalkoxy, (C 1 -C 2 ) -alkylthio, (C 1 -C 2 ) -haloalkylthio, (C 1 -C 2 ) -alkylsulfmyl, (C 1 -C 2 ) -haloalkylsulfmyl, (C 1 -C 4) -alkyl 2 ) -alkylsulfonyl, (C 1 -C 2 ) -haloalkylsulfonyl,
  • R 1 is CH 3 ,
  • R is CH 3 .
  • Q stands for one of the groupings Q-1.1 to Q-1.30 specifically mentioned in the table above. for the groups Zl. l to Z-21.60. for hydrogen, fluorine, chlorine, bromine, iodine, cyano, CH 3, (Ci) haloalkyl, (C 3 -C 3) -cycloalkyl, (Ci-C 2 ) -alkoxy, (Ci) -haloalkoxy, (Ci-C 2 ) Alkylthio, (C 1 -C 2 ) -alkylsulphinyl, (C 1 -C 2 ) -alkylsulphonyl,
  • R 1 is CH 3
  • R 2 is CH 3 ,.
  • the designation of chemical groups generally means that the attachment to the skeleton or the rest of the molecule takes place via the last-mentioned structural element of the relevant chemical group that is, for example, in the case of (C 2 -C 6) -alkenyloxy via the oxygen atom, and in the case of heterocyclyl (Ci-Cg) -alkyl or R 12 0 (0) C (Ci-Cg) -alkyl in each case via the C Atom of the alkyl group.
  • alkylsulfonyl alone or as part of a chemical group - is straight-chain or branched alkylsulfonyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms e.g. (but not limited to) (C 1 -C 6) alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methyl-propylsulfonyl, 1, 1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1, 1-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentyl
  • heteroarylsulfonyl is optionally substituted pyridylsulfonyl
  • Heteroarylsulfonyl here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups.
  • alkylthio alone or as part of a chemical group - is straight-chain or branched S-alkyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms such as (Ci-Cio) -, (CI-C ⁇ ) - or (Ci-C4) -alkylthio, e.g. (but not limited to) (ce-Ce) -alkylthio, such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1, 1-dimethylpropylthio, 1, 2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1, 1 Dimethylbut
  • Cycloalkylthio means according to the invention a bonded via a sulfur atom
  • Alkoxy means an alkyl radical attached via an oxygen atom, for example (but not limited to) (C 1 -C 6) -alkoxy, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-alkoxy.
  • Methylpropoxy 1, 1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 - ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1, 2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy.
  • Alkenyloxy means a bonded via an oxygen atom
  • alkynyloxy means an alkynyl radical bonded via an oxygen atom, such as (C 2 -C 10) -, (C 2 -C 6 ) - or (C 2 -C 4 ) -alkenoxy or (C 3 -C 10) -, (C 3 -C 6 ) - or (C 3 -C 4 ) -alkoxy.
  • Cycloalkyloxy means a cycloalkyl group bonded via an oxygen atom.
  • the number of C atoms here refers to the alkyl radical in the
  • the number of C atoms here refers to the alkyl radical in the alkoxycarbonyl group, analogously “alkenyloxycarbonyl” and “alkynyloxycarbonyl”, unless otherwise defined elsewhere, according to the invention for alkenyl or alkynyl radicals which are bonded to the skeleton via -O-C ( O), such as (C 2 -C 10) -, (C 2 -C 6 ) - or (C 2 -C 4 ) - alkenyloxycarbonyl or (C3-C10) -, (C 3 -C 6) - or (C3-C4) -
  • the number of carbon atoms refers to the alkyl radical in the alkylcarbonyloxy group.
  • aryl means an optionally substituted mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl and the like, preferably phenyl
  • optionally substituted aryl are also Vectorcyclische systems, such as
  • Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkylthio, haloalkyl, alkoxy, haloalkoxy, Cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bis-alkylaminoalkoxy, tris [alkyl] silyl, Bis- [alkyl] arylsilyl, bis [alkyl] alkylsilyl, tris [alkyl] silylalkyn
  • heterocyclic radical contains at least one heterocyclic ring
  • heterocyclic ring in which at least one C atom is replaced by a heteroatom, preferably by a heteroatom from the group N, O, S, P
  • N, O, S, P saturated, unsaturated, partially saturated or heteroaromatic and may be unsubstituted or substituted, wherein the binding site is located on a ring atom.
  • heterocyclyl or heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings.
  • polycyclic systems are also included, for example 8-azabicyclo [3.2.1] octanyl, 8-azabicyclo [2.2.2] octanyl or 1-azabicyclo [2.2.1] heptyl.
  • optionally substituted heterocyclyl also become
  • the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but not two
  • Oxygen atoms are to be directly adjacent, such as with a heteroatom from the group N, O and S 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2 or 3-yl, 2,3- dihydro-lH-pyrrole
  • 3-membered and 4-membered heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3 -Dioxetan-2-yl.
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical having two heteroatoms from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazole-3 or 4 or 5-yl; 4,5-dihydro-1H-pyrazole-1 - or 3 or 4 or 5-yl; 2,3-dihydro-1H-pyrazole-1 - or 2 - or
  • 6-yl 1,4,5,6-tetrahydropyridazine-1- or 3- or 4- or 5- or 6-yl; 3,4,5,6-tetrahydropyridazine-3- or 4- or 5-yl; 4,5-dihydropyridazine-3 or 4-yl; 3,4-dihydropyridazine-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazine-3 or 4-yl; 1,6-dihydropyriazine-1- or 3- or 4- or 5- or 6-yl;
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group N, O and S, such as, for example, l, 4,2-dioxazolidin-2 or 3 or 5-yl; l, 4,2-dioxazol-3 or 5-yl; 1,2,2-dioxazinane-2- or -3- or 5- or 6-yl; 5,6-dihydro-l, 4,2-dioxazine-3 or 5 or 6-yl; l, 4,2-dioxazine-3- or 5- or 6-yl; l, 4,2-dioxazepan-2 or 3 or 5 or 6 or 7-yl; 6,7-dihydro-5H-l, 4,2-dioxazepine-3 or 5 or 6 or 7-yl; 2,3-dihydro-7H-l, 4,2-dioxazepin-2 or 3 or 5 or 6 or 7-yl; 2,3-dihydro-5H-1,
  • heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl,
  • Alkylaminocarbonyl bis-alkylaminocarbonyl, cycloalkylaminocarbonyl,
  • Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below, in addition to oxo and thioxo.
  • the oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring.
  • lactones and lactams are preferably also included.
  • the oxo group may also be attached to the hetero ring atoms, which may exist in different oxidation states, e.g. For example, at N and S, the divalent groups N (O), S (O) (also SO for short) and S (O) 2 (also SO2 for short) occur and form in the heterocyclic ring.
  • N (O) and -S (0) groups both enantiomers are included.
  • heteroaryl stands for heteroaromatic compounds, ie.
  • heteroaryls are, for example, 1H-pyrrol-1-yl; lH-pyrrol-2-yl; lH-pyrrole
  • Carbon atoms part of another aromatic ring they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatic.
  • quinolines e.g., quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • Isoquinolines e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl
  • quinoxaline quinazoline
  • cinnoline 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyrazine
  • heteroaryl are also 5- or 6-membered benzo-fused rings from the group 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indol-4-yl, 1H- Indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran 5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophene-2-yl, 1-benzothiophen-3-yl, 1-benzothiophene-4-yl, 1-benzothiophene-5 yl, 1-benzothiophene-6-yl, 1-benzothiophene-7-yl, 1H-indazol-1-yl, 1H-indazol-3-y
  • halogen means, for example, fluorine, chlorine, bromine or iodine.
  • halogen means, for example, a fluorine, chlorine, bromine or iodine atom.
  • alkyl means a straight-chain or branched, open-chain, saturated
  • Hydrocarbon radical which is optionally monosubstituted or polysubstituted and which is referred to in the latter case as "substituted alkyl.”
  • Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, particular preference is given to methoxy , Methyl, fluoroalkyl, cyano, nitro, fluoro, chloro, bromo or iodo.
  • the prefix "bis” also includes the combination of different alkyl radicals, e.g. For example, methyl (ethyl) or ethyl (methyl).
  • Haloalkyl denote by identical or different halogen atoms, partially or completely substituted alkyl, alkenyl or alkynyl, for example monohaloalkyl
  • ( Monohaloalkyl) such.
  • B. CH 2 CH 2 C1, CH 2 CH 2 Br, CHCICH3, CH 2 C1, CH 2 F; Perhaloalkyl such.
  • Polyhaloalkyl such. CH 2 CHFC1, CF 2 CC1FH, CF 2 CBrFH, CH 2 CF 3;
  • perhaloalkyl also encompasses the term perfluoroalkyl.
  • Partially fluorinated alkyl means a straight-chain or branched, saturated hydrocarbon which is monosubstituted or polysubstituted by fluorine, it being possible for the corresponding fluorine atoms to be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain, for example CHFCH3, CH 2 CH 2 F, CH 2 CH 2 CF 3, CHF 2, CH 2 F, CF 3 CHFCF 2
  • Partially fluorinated haloalkyl means a straight-chain or branched, saturated one
  • Hydrocarbon which is substituted by various halogen atoms having at least one fluorine atom, wherein all other optional halogen atoms are selected from the group fluorine, chlorine or bromine, iodine.
  • the corresponding halogen atoms may be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain.
  • Partially fluorinated haloalkyl also includes the complete substitution of halogen with the participation of at least one fluorine atom of the straight-chain or branched chain.
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl; the same applies to haloalkenyl and other radicals substituted by halogen -C4) -Alkyl "means a short notation for straight or branched alkyl having one to four carbon atoms according to the
  • Range indication for C atoms, d. H. includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl.
  • General alkyl radicals having a larger specified range of carbon atoms eg. As "(Ci-C6) alkyl", accordingly also include straight-chain or branched alkyl radicals having a larger number of C atoms, d. H. according to example, the alkyl radicals with 5 and 6 carbon atoms.
  • the lower carbon skeletons for example having 1 to 6 carbon atoms or in unsaturated groups having 2 to 6 carbon atoms, are preferred.
  • Alkyl radicals including in the assembled radicals such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i Hexyl and 1, 3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1, 4-dimethylpentyl;
  • Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, wherein at least one double bond or triple bond is contained. Preference is given to radicals having a double bond or
  • alkenyl in particular also includes straight-chain or branched open-chain
  • Hydrocarbon radicals having more than one double bond such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulated double bonds, such as allenyl (1,2-propadienyl), 1, 2-butadienyl and 1,2,3-pentatrienyl.
  • Alkenyl is, for example, vinyl, which may optionally be substituted by further alkyl radicals, for example (but not limited to) (C 2 -C 6) alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl , 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3 Pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl -2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl
  • alkynyl in particular also includes straight-chain or branched open-chain
  • C 2 -C 6) -alkynyl is, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3 Pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1 Ethyl 2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl,
  • cycloalkyl means a carbocyclic, saturated ring system preferably having 3-8 ring C atoms, eg cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio , Haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, alkocycarbonyl,
  • Cycloalkylaminocarbonyl In the case of optionally substituted cycloalkyl cyclic systems are included with substituents, wherein substituents having a double bond on
  • alkylidene group such as methylidene
  • polycyclic aliphatic systems are also included, such as, for example, bicyclo [1,1.0] butan-1-yl, bicyclo [1,1-0] butan-2-yl, bicyclo [2.1.0] pentan-1-yl , Bicyclo [1,11] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1 ] hept-2-yl, bicyclo [2.2.2] octan-2-yl, bicyclo [3.2.1] octan-2-yl, bicyclo [3.2.2] nonan-2-yl, adamantane-1-yl and
  • spirocyclic aliphatic systems are also included, such as spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl, spiro [3.3] hept-1-yl, spiro [3.3] hept-2-yl.
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 C atoms, eg 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2- Cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl, wherein substituents having a double bond on the cycloalkenyl radical, for example an alkylidene group such as methylidene, are also included in the case of optionally substituted cycloalkenyl the explanations for substituted Corresponding to cycloalkyl.
  • substituents having a double bond on the cycloalkenyl radical for example an alkylidene group such as methylidene
  • alkoxyalkyl means an alkoxy group attached via an alkyl group and "alkoxyalkoxy” means an alkoxyalkyl group bonded through an oxygen atom, for example (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy.
  • Alkylthioalkyl means an alkylthio radical bonded via an alkyl group
  • Alkylthioalkylthio means an alkylthioalkyl radical bonded via an oxygen atom.
  • Arylalkoxyalkyl stands for an aryloxy radical bound via an alkyl group
  • Heteroaryloxyalkyl means a heteroaryloxy group bonded via an alkyl group.
  • Haloalkoxyalkyl means a haloalkoxy radical attached and "haloalkylthioalkyl” means a haloalkylthio radical attached via an alkyl group.
  • Arylalkyl means an aryl group attached via an alkyl group
  • heteroarylalkyl means a heteroaryl group bonded via an alkyl group
  • heterocyclylalkyl means a heterocyclyl group bonded through an alkyl group.
  • Cycloalkylalkyl means a cycloalkyl radical attached via an alkyl group, for example (but not limited to) cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropyleth-1-yl, 2-cyclopropyleth-1-yl, 1-cyclopropylpropyl l -yl, 3-cyclopropylprop-1-yl.
  • haloalkylthio alone or as part of a chemical group - represents straight-chain or branched S-haloalkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as (C 1 -C 5) -, (C 1 -C 5) - or (C 1 -C 4) -haloalkylthio, for example (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio, 3,3,3-prop-1-ylthio.
  • Halocycloalkyl and “Halocycloalkenyl” mean by the same or different halogen atoms, such as. B. F, Cl and Br, or by haloalkyl, such as. Trifluoromethyl or difluoromethyl, partially or fully substituted cycloalkyl or cycloalkenyl, e.g.
  • “trialkylsilyl” - alone or as part of a chemical group - is straight-chain or branched Si-alkyl, preferably with 1 to 8, or with 1 to 6 Carbon atoms, such as tri - [(Ci-Cs) -, (CI-C ⁇ ) - or (Ci-C4) -alkyl] silyl, for example (but not limited to) trimethylsilyl, triethylsilyl, tri (n-propyl) silyl, Tri (iso-propyl) silyl, tri (n-butyl) silyl, tri (1-methylprop-1-yl) silyl, tri (2-methylprop-1-yl) silyl, tri (1, l) Dimethyleth-1-yl) silyl, tri (2,2-dimethyl-1-yl) silyl.
  • the compounds of the general formula (I) can exist as stereoisomers.
  • the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the general formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur.
  • Stereoisomers can be distinguished from those in the
  • stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants.
  • the invention thus also relates to all stereoisomers which comprises the general formula (I) but are not specified with their specific stereoform, and mixtures thereof.
  • the purification can also by
  • Suitable isolation, purification and stereoisomer separation methods of compounds of the general formula (I) are methods which are generally known to the person skilled in the art from analogous cases, for example by physical methods such as crystallization, chromatography methods, especially column chromatography and HPLC (high pressure liquid chromatography), distillation optionally under reduced pressure, extraction and other methods may, if appropriate remaining mixtures are usually separated by chromatographic separation, for example on chiral solid phases.
  • Suitable for preparative amounts or on an industrial scale are processes such as crystallization, for example diastereomeric salts, which can be obtained from the diastereomer mixtures with optically active acids and optionally in the presence of acidic groups having optically active bases.
  • the substituted pyrazoles of the general formula (I) according to the invention can be prepared starting from known processes.
  • the synthetic routes used and investigated are based on commercially available or easily prepared amines, on appropriately substituted aldehydes and on commercially available chemicals such as malonic acid derivatives and nitromethane.
  • the groupings Q, Y, W, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 of the general formula (I) have the previously defined meanings in the following schemes, unless exemplary but non-limiting definitions take place.
  • the synthesis of the compounds of general formula (Ia) according to the invention is carried out via a
  • reaction of the compound of general formula (II) in the presence of a fluorinating reagent, such as deoxofluor preferably takes place in the temperature range between -50 ° C and 80 ° C, in an adequate solvent such as dichloromethane or toluene (see Scheme 1).
  • the synthesis of the compounds of the general formula (II) takes place via an amide coupling of an acid of the general formula (III) with an amine of the general formula (IV) in the presence of an amide coupling reagent such as T3P, dicyclohexylcarbodiimide, N- (3-dimethylaminopropyl) -N '-ethylcarbodiimid, N, N' -Cabonyldiimidazol, 2-chloro-l, 3-dimethyl-imidazolium chloride or 2-chloro-l-methylpyridinium iodide (see Chemistry of peptide Synthesis, Ed. ⁇ .
  • Polymer-bound reagents such as polymer-bound dicyclohexylcarbodiimide are also suitable for this coupling reaction.
  • the reaction preferably takes place in the temperature range between 0 ° C and 80 ° C, in an adequate solvent such as dichloromethane, acetonitrile, N, N-dimethylformamide or ethyl acetate and in the presence of a base such as triethylamine, N, N-diisopropylethylamine or l, 8-diazabicyclo [5.4.0] undec-7-cene (see Scheme 2).
  • an adequate solvent such as dichloromethane, acetonitrile, N, N-dimethylformamide or ethyl acetate
  • a base such as triethylamine, N, N-diisopropylethylamine or l, 8-diazabicyclo [5.4.0] undec-7-cene
  • the saponification can be carried out in the presence of a base or a Lewis acid.
  • the base may be a hydroxide salt of an alkali metal (such as lithium, sodium or potassium, Scheme 3), and the saponification reaction preferably occurs in the temperature range
  • the Lewis acid may be boron tribromide, and the reaction may be carried out in a temperature range between -20 ° C and 100 ° C, preferably -5 ° C and 50 ° C.
  • R ' (C 1 -C 4 ) -alkyl.
  • the synthesis of the compound of the general formula (V) can be prepared by alkylating the compound of the general formula (VI) with a halide of the general formula (VII) in the presence of a base according to methods known to those skilled in the art (see Scheme 4).
  • the base may be a carbonate salt of an alkali metal (such as lithium, sodium, potassium or cesium) and the reaction preferably takes place in the temperature range between room temperature and 150 ° C in an adequate solvent such as dichloromethane, acetonitrile , N, N-dimethylformamide or ethyl acetate. See J. Med. Chem. 2011, 54 (16), 5820-5835 and
  • R ' (C 1 -C 4 ) -alkyl.
  • Scheme 5 describes the synthesis of the compound of general formula (VI) by reaction of an enamine of general formula (VIII) with a hydrazine of general formula (IX) in an adequate solvent such as methanol or ethanol. Alternatively, one can carry out reaction in a solvent such as tetrahydrofuran. Please refer to Scheme 4.
  • the compounds of the general formula (VIII) can be prepared by condensation of a ketone of the general formula (X) and dimethylformamide dimethyl acetal of the general formula (XI) (see Scheme 6, Tetrahedron 1998, 54 (20), 5075-5088).
  • Scheme 11 describes the synthesis of the compound of general formula (XVIII) by reaction of an enamine of general formula (XVI) with a hydrazine of general formula (IX) in an adequate solvent such as, for example, methanol or ethanol. Alternatively, the reaction may be carried out in a solvent such as tetrahydrofuran. Please refer to an adequate solvent such as, for example, methanol or ethanol. Alternatively, the reaction may be carried out in a solvent such as tetrahydrofuran.
  • Scheme 12 describes the synthesis of the compound of general formula (XX) by reaction of a pyrazole of general formula (XVIII) with a halosuccinimide of general formula (XIX) in an appropriate solvent such as DMF.
  • the base may be a carbonate salt of an alkali metal (such as lithium, sodium, potassium or cesium) and the reaction preferably takes place in the temperature range between room temperature and 150 ° C in an adequate solvent such as dichloromethane, acetonitrile , N, N-dimethylformamide or ethyl acetate.
  • an alkali metal such as lithium, sodium, potassium or cesium
  • R ' (C 1 -C 4 ) -alkyl.
  • the synthesis of the acid of general formula (XXII) can be prepared by saponification of the compound of general formula (XXI) or analogously to methods known in the art.
  • the saponification can be carried out in the presence of a base or a Lewis acid.
  • the base may be a hydroxide salt of an alkali metal (such as lithium, sodium or potassium, Scheme 14), and the saponification reaction preferably occurs in the temperature range
  • the Lewis acid may be boron tribromide, and the reaction may be carried out in a temperature range between -20 ° C and 100 ° C, preferably -5 ° C and 50 ° C.
  • R ' (C 1 -C 4 ) -alkyl.
  • X " chlorine, bromine and iodine.
  • Dicyclohexylcarbodiimide N- (3-dimethylaminopropyl) -N '-ethylcarbodiimid, N, N' -Cabonyldiimidazol, 2-chloro-l, 3-dimethyl-imidazolium chloride or 2-chloro-l-methylpyridinium iodide (see Chemistry of Peptide Synthesis, Ed., N. Leo Benoiton, Taylor & Francis, 2006, ISBN 10: 1-57444-454-9).
  • Polymer-bound reagents such as polymer-bound dicyclohexylcarbodiimide are also suitable for this coupling reaction.
  • the reaction preferably takes place in the temperature range between 0 ° C and 80 ° C, in an adequate solvent such as dichloromethane, acetonitrile, N, N-dimethylformamide or ethyl acetate and in the presence of a base such as triethylamine, N, N-diisopropylethylamine or l, 8-diazabicyclo [5.4.0] undec-7-cene (see Scheme 15).
  • an adequate solvent such as dichloromethane, acetonitrile, N, N-dimethylformamide or ethyl acetate
  • a base such as triethylamine, N, N-diisopropylethylamine or l, 8-diazabicyclo [5.4.0] undec-7-cene
  • Fluorinating reagent such as deoxofluor ().
  • the reaction preferably takes place in the
  • the synthesis of the compounds of the general formula (XXV) is carried out via a condensation of the acid of the general formula (III) with an amidoxime of the general formula (XXIV) in the presence of an amide coupling reagent such as dicyclohexylcarbodiimide and a phenol such as 2,4- Dinitrophenol (see Scheme 17).
  • an amide coupling reagent such as dicyclohexylcarbodiimide and a phenol such as 2,4- Dinitrophenol
  • the synthesis of the compounds of general formula (XXVII) according to the invention is carried out via a condensation of the acid of general formula (III) with a compound of general formula (XXVI) in the presence of an amide coupling reagent such as TBTU and a
  • Sulfonic acid chlorides such as p-toluenesulfonyl chloride (see Scheme 18).
  • the reaction preferably takes place in the temperature range between -10 ° C and 120 ° C, in an adequate
  • Solvent such as acetonitrile and in the presence of a base such as N, N-diisopropylethylamine instead.
  • the synthesis of the acid of general formula (XXVIII) can be prepared by saponification of the compound of general formula (XXX) according to or analogous to those skilled in the known methods.
  • the saponification can be carried out in the presence of a base or a Lewis acid.
  • the base may be a hydroxide salt of an alkali metal (such as lithium, sodium or potassium, Scheme 20), and the saponification reaction preferably occurs in the temperature range
  • the Lewis acid may be boron tribromide, and the reaction may be carried out in a temperature range between -20 ° C and 100 ° C, preferably -5 ° C and 50 ° C.
  • Amidkupplungsreagenzes such as T3P, dicyclohexylcarbodiimide, N- (3-dimethylaminopropyl) -N '-ethylcarbodiimid, N, N' -Cabonyldiimidazol, 2-chloro-l, 3-dimethyl-imidazolium chloride or 2-chloro-l-methylpyridinium iodide (see Chemistry of Peptide Synthesis, Ed., Leo Benoiton, Taylor & Francis, 2006, ISBN 10: 1-57444-454-9).
  • Polymer-bound reagents such as polymer-bound dicyclohexylcarbodiimide are also suitable for this coupling reaction.
  • the reaction preferably takes place in the temperature range between 0 ° C and 80 ° C, in an adequate solvent such as dichloromethane, acetonitrile, N, N-dimethylformamide or
  • R ' (C 1 -C 4 ) -alkyl.
  • the compounds of general formula (XXXIII) are prepared by reacting the compound of general formula (XXXII) in the presence of a fluorinating reagent such as DAST.
  • a fluorinating reagent such as DAST.
  • the reaction preferably takes place in the temperature range between -100 ° C and 100 ° C, in an adequate solvent such as THF and in the presence of a base such as potassium carbonate (see Scheme 22).
  • R ' (C 1 -C 4 ) -alkyl.
  • the compounds of general formula (XXXIX) are prepared by condensing a thioamide of general formula (XXXVII) with compounds of general formula (XXXVIII) in the presence of a Broensted acid such as p-toluenesulfonic acid in an adequate solvent such as acetic acid (Scheme 25 ).
  • R ' (C 1 -C 4 ) -alkyl.
  • the compounds of general formula (XXXXII) are prepared by reaction of a compound of general formula (XXXXI) with hydroxylamine-O-sulfonic acid in the presence of a base such as pyridine in an adequate solvent such as methanol or ethanol (Scheme 27).
  • the compounds of the general formula (XXXXI) are prepared by condensation of a thioamide of the general formula (XXXVII) with compounds of the general formula (XXXXIII) (Scheme 28).
  • the synthesis of the compounds of the general formula (XXXXVI) is carried out by condensation of amidoximes of the general formula (XXXXIV) with carboxylic acid of the general formula (XXXXV) in the presence of carbonyldiimidazole.
  • the reaction preferably takes place in the temperature range between 0 ° C and 150 ° C, in an adequate solvent such as N, N-dimethylformamide (see Scheme 29).
  • the synthesis of the compound of the general formula (XXXXVIII) can be prepared by alkylating the compound of the general formula (VI) with a nitrile of the general formula (XXXXX) in the presence of a base according to methods known to those skilled in the art (see Scheme 4).
  • the base may be a carbonate salt of an alkali metal (such as lithium, sodium, potassium or cesium) and the reaction preferably takes place in the temperature range between room temperature and 150 ° C in an adequate solvent such as dichloromethane, acetonitrile , N, N-dimethylformamide or ethyl acetate (Scheme 32).
  • the synthesis of the compounds of the general formulas (XXXXXIIIa and XXXXIIIb) can be known by alkylating the compound of the general formula (XXXXXI) with a compound of the general formula (XXXXII) in the presence of a base after or analogously to the person skilled in the art Establish methods.
  • the base may be a carbonate salt of an alkali metal (such as lithium, sodium, potassium or cesium), and the reaction preferably takes place in the
  • the synthesis of the compounds of general formula (XXXXXVII) is carried out by cycloaddition of compounds of general formula (XXXXXV) with compounds of general formula (XXXXXVI) in the presence of sodium hypochlorite.
  • the reaction preferably takes place in the Temperature range between -40 ° C and 100 ° C, in an adequate solvent such as THF instead (see Scheme 35).
  • the oximes of the general formula (XXXXXV) are synthesized by reaction of aldehydes of the general formula (XXXXXVIII) with hydroxylamine hydrochloride of the general formula (XXXXVII) in the presence of sodium hypochlorite.
  • the reaction preferably takes place in the
  • Diisobutylaluminum hydride preferably takes place in the temperature range between -100 ° C and 100 ° C, in an adequate solvent such as THF (see Scheme 37).
  • the synthesis of the compounds of general formula (XXXXXIX) is carried out via an amide coupling of an acid of general formula (III) with an amine of general formula (XXXXX) in the presence of an amide coupling reagent such as T3P, dicyclohexylcarbodiimide, N- (3-dimethylaminopropyl) -N '-ethylcarbodiimid, N, N' -Cabonyldiimidazol, 2-chloro-l, 3-dimethyl-imidazolium chloride or 2-chloro-l-methylpyridinium iodide (see Chemistry of peptide Synthesis, Ed. ⁇ .
  • Polymer-bound reagents such as polymer-bound dicyclohexylcarbodiimide are also suitable for this coupling reaction.
  • the reaction preferably takes place in the temperature range between 0 ° C and 80 ° C, in an adequate solvent such as dichloromethane, acetonitrile, N, N-dimethylformamide or
  • the compounds of general formula (XXXXXXV) are made by reacting a compound of general formula (XXXXXXIII) with compounds of general formula (XXXXXIII) in an adequate solvent such as methanol or ethanol (Scheme 40).
  • the compounds of general formula (XXXXXXVIII) are prepared by reacting a compound of general formula (XXXXXXVI) with compounds of general formula (XXXXXII) in the presence of a base such as potassium carbonate or sodium hydride in an adequate solvent such as THF or ⁇ , ⁇ - Dimethylformamide (Scheme 42).
  • the compounds of general formula (XXXXXXVI) are prepared by reaction of a compound of general formula (XXXXXXVI) with a compound of general formula (XXVI) (Scheme 43).
  • the compounds of general formula (XXXXXXXIa and XXXXXXIb) are prepared by reaction of a compound of general formula (XXXXXXIX) with a compound of general formula (XXXXXX (Scheme 44).
  • the compounds of the general formula (XXXXXXIX) are prepared by reaction of a compound of the general formula (XXXXXXII) with a compound of the general formula (XXXXIII)
  • Tetrahydrofuran The reaction preferably takes place in the temperature range between -100 ° C and 100 ° C.
  • the synthesis of the compounds of the general formula (XXXXXXXV) is carried out by oxidation of the compound of the general formula (XXXXXXIV) in the presence of an oxidizing agent such as m-chloroperbenzoic acid in a suitable solvent such as, for example
  • the synthesis of the compounds of general formula (XXXXXXXVI) is carried out by reacting the compound of general formula (XXXXXXXVII) with a compound of general formula (XXXXXXXVIII) in the presence of a base such as potassium carbonate in a suitable solvent such as ⁇ , ⁇ -dimethylformamide (see Scheme 49).
  • R ' (C 1 -C 4 ) -alkyl.
  • the synthesis of the compounds of general formula (XXXXXXXXI) is carried out by reacting the compound of general formula (XXXXXXXII) with a compound of general formula (XXXXXXX) in the presence of a base such as triethylamine in a suitable solvent such as ⁇ , ⁇ -dimethylformamide ( see Scheme 53).
  • a base such as triethylamine
  • a suitable solvent such as ⁇ , ⁇ -dimethylformamide
  • R ' (C 1 -C 4 ) -alkyl.
  • Dicyclohexylcarbodiimide N- (3-dimethylaminopropyl) -N '-ethylcarbodiimid, N, N' -Cabonyldiimidazol, 2-chloro-1,3-dimethylimidazolium chloride or 2-chloro-1-methylpyridinium iodide (see Chemistry of Peptide Synthesis, Ed. N. Leo Benoiton, Taylor & Francis, 2006, ISBN 10: 1-57444-454 -9).
  • Polymer-bound reagents such as polymer-bound dicyclohexylcarbodiimide are also suitable for this coupling reaction.
  • the reaction preferably takes place in the temperature range between 0 ° C and 80 ° C, in an adequate solvent such as dichloromethane, acetonitrile, N, N-dimethylformamide or ethyl acetate and in the presence of a base such as triethylamine, N, N-diisopropylethylamine or I, 8-diazabicyclo [5.4.0] undec-7-cene (see Scheme 55).
  • an adequate solvent such as dichloromethane, acetonitrile, N, N-dimethylformamide or ethyl acetate
  • a base such as triethylamine, N, N-diisopropylethylamine or I, 8-diazabicyclo [5.4.0] undec-7-cene (see Scheme 55).
  • a base
  • Ammonium chloride (1.91 g, 35.68 mmol, 10.00 equiv.) was dissolved in DMF (20 mL) and stirred at room temperature overnight. After cooling, the reaction mixture was diluted with ethyl acetate (100 ml), the mixture was washed twice with saturated ammonium chloride solution (50 ml) and with saturated sodium chloride solution. The organic phase was dried over magnesium sulfate and the solvent removed in vacuo.
  • Synthesis Example No. 1.96-578 Synthesis step 1: 2- ⁇ 2- [3- (2,6-difluorophenyl) -4-methyl-1H-pyrazol-1-yl] propan-2-yl ⁇ -1,3-thiazole (1.96- 578)
  • Preferred compounds of the formula (L I) are the compounds 1.1-1 to 1.1-718, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.1-1 to 1.1-718 of Table LI are thus characterized by the meaning of the respective entries no. 1 to 718 defined for Z of Table 1.

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Abstract

La présente invention concerne des pyrazoles substitués de formule générale (I) ou leurs sels, les fractions de la formule générale (I) ayant les définitions figurant dans le descriptif, ainsi que leur utilisation comme herbicides, en particulier pour lutter contre les plantes adventices et/ou les mauvaises herbes dans les cultures de plantes utiles et/ou comme régulateurs de croissance des plantes pour influencer la croissance des cultures de plantes utiles.
PCT/EP2018/078994 2017-10-26 2018-10-23 Pyrazoles substitués, leurs sels et leur utilisation comme agents herbicides WO2019081485A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114957234A (zh) * 2022-05-31 2022-08-30 浙江工业大学 一种含三唑的苯基连噁二唑类衍生物及其制备方法和应用

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114957234A (zh) * 2022-05-31 2022-08-30 浙江工业大学 一种含三唑的苯基连噁二唑类衍生物及其制备方法和应用

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