WO2019081477A1 - 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
WO2019081477A1
WO2019081477A1 PCT/EP2018/078983 EP2018078983W WO2019081477A1 WO 2019081477 A1 WO2019081477 A1 WO 2019081477A1 EP 2018078983 W EP2018078983 W EP 2018078983W WO 2019081477 A1 WO2019081477 A1 WO 2019081477A1
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Prior art keywords
alkyl
cycloalkyl
compounds
nmr
cio
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PCT/EP2018/078983
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German (de)
English (en)
Inventor
Thomas Müller
Birgit Kuhn
Uwe Döller
Christopher Robert GARDNER
Andreas Van Almsick
David Michael BARBER
Hansjörg Dietrich
Elmar Gatzweiler
Anu Bheemaiah MACHETTIRA
Christopher Hugh Rosinger
Dirk Schmutzler
Original Assignee
Bayer Cropscience Aktiengesellschaft
Bayer Aktiengesellschaft
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Publication of WO2019081477A1 publication Critical patent/WO2019081477A1/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
    • 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
    • C07D231/14—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/16—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 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
    • C07D409/02—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
    • C07D409/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • C07D498/08—Bridged 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 ingredients which carry one of the defined substituted phenyl, thiophene, thiazole or pyrimidine radicals on the pyrazole is, however, not yet described.
  • substituted pyrazoles or their salts as herbicidal active compounds which carry one of the defined substituted phenyl, thiophene, thiazole or pyrimidine radicals on pyrazole are particularly suitable as herbicides.
  • 10 is hydrogen, halogen, cyano, (Ci-Cg) -alkyl, (Ci-Cg) -haloalkyl, (Ci-Cg) -cyanoalkyl, (Ci-Cg) -hydroxyalkyl, (Ci-Cg) -alkoxy- ( Ci-Cg) -alkyl, (C 3 -Cio) -cycloalkyl, (C 3 -Cio) -cycloalkyl (Ci-Cg) -alkyl, (C 3 -Cg) -Halocycloalkyl, (Ci-Cg) -alkoxy, (Ci-Cg) -haloalkoxy, (Ci-Cg) -alkylthio, (Ci-Cg) -haloalkylthio, (C 3 -Cg) -cycloalkylthio, (Ci-Cg) -alkylsulfmyl
  • R is hydrogen, (C 1 -C 10) -alkyl, (C 1 -C 10) -haloalkyl, (C 2 -C 10) -alkenyl, (C 3 -C 10) -alkynyl,
  • 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 [NR a R b R c R d ] + wherein 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.
  • the 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).
  • Preferred subject of the invention are compounds of general formula (I), wherein Q is the groups Q-l. l to Q-7.1
  • Z for the group is hydrogen, halogen, cyano, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -cyanoalkyl, (C 1 -C 6 ) -hydroxyalkyl, (C 1 -C 6 ) -alkoxy (C 1 -C 6 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 3 -C 8 ) -halocycloalkyl, ( Ci-C 6) alkoxy, (Ci-C 6) -haloalkoxy, (Ci-C 6) alkylthio, (Ci-C 6) haloalkylthio, (C 3 -C 6) -cycloalkylthio, (Ci-C
  • R is hydrogen, (Ci-C 8) -alkyl, (Ci-C8) -haloalkyl, (C 2 -C 8) alkenyl, (C3-C8) alkynyl, (Ci-C8) - alkoxy (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkylthio - (Ci-C 8) alkyl, (C 3 -C 8) cycloalkyl, hydroxy (Ci-C 8) alkylcarbonyl, amino (Ci-C8) alkyl, (Ci-C8) alkoxycarbonyl ( Ci-C 8) alkyl, (Ci-C 8) cyanoalkyl,
  • a particularly preferred subject of the invention are compounds of the general formula (I) in which Q represents the groups Q-1. l to Q-7.1
  • Q-4.2 Q-5.1 Q-6.1 Q-7.1 stands for the group represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C 3 -C 6) - cycloalkyl, (C 3 -C 6) -Halocycloalkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -haloalkylthio, (C 1 -C 4 ) -alkylsulfmyl, (Ci -C 4) -Haloalkylsulfmyl, (Ci-C 4) alkylsulfonyl, (Ci-C4) haloalkylsulfonyl, represents oxygen or sulfur, is (C
  • R 4 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) -alkenyl, (C 3 -C 6) alkynyl, (Ci-C 6) - Alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, C 6) -Haloalkylthio- (Ci-C 6) alkyl, (C 3 -C 6) cycloalkyl, hydroxy (Ci-C 6) alkylcarbonyl, amino (Ci-C 6) alkyl, (Ci- C 6) alkoxycarbonyl (Ci-C 6) alkyl, (Ci-C 6) cyan
  • a very particularly preferred subject matter of the invention are compounds of the general formula (I) in which Q denotes the groups Q1. l to Q-7.1
  • Z for the group 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, (Ci -C 3) -Haloalkylsulfmyl, (Ci-C 3) alkylsulfonyl, (Ci-C 3) haloalkylsulfonyl, represents oxygen or sulfur,
  • R 1 is (C 1 -C 4 ) -alkyl and (C 1 -C 4 ) -haloalkyl
  • R is (C 1 -C 4 ) -alkyl and (C 1 -C 4 ) -haloalkyl, or wherein R 1 and R 2 together with the C-atom to which they are each bonded, a completely saturated or partially saturated, optionally interrupted by one to three heteroatoms from the group N, O and S and optionally further substituted, in total 3 Form -7- membered ring stands,
  • R 3 is hydroxy, amino, (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C 2 -C 4) alkenyl, (C 3 -C 4) alkynyl, (Ci-C 4 ) -Cyanoalkyl, (C 1 -C 4 ) -hydroxyalkyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -halocycloalkyl, (C 3 -C 6 ) -cyanocycloalkyl, (C 3 -C 6 ) cycloalkenyl, (Ci-C 4) -alkyl- (C 3 -C 6) cycloalkyl, (Ci-C4) - alkoxy- (C 3 -C 6) cycloalkyl, (Ci-C 4) haloalkoxy (C 3 -C 6) cycloalkyl, (Ci-
  • R 4 is hydrogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, hydroxycarbonyl- (C 1 -C 6 ) -alkyl, amino- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxycarbonyl - (Ci-C 6 ) -alkyl, or R 3 and R 4 with the N-atom to which they are attached, a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring is formed, except the following compound:
  • 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, represents oxygen or sulfur, represents (C 1 -C 2 ) -alkyl, is (C 1 -C 2 )
  • Y represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, (C 1 -C 2 ) -alkyl, (C 1 -C 2 ) -haloalkyl, (C 3 -C 4) -cycloalkyl, (C 1 -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 2 ) Alkylsulfonyl, (C 1 -C 2) - haloalkylsulfonyl,
  • W is oxygen or sulfur
  • R 1 is CH 3 ,
  • R 2 is CH 3 , with the exception of the following compound:
  • Q stands for one of the groupings Q-1.1 to Q-7.1 mentioned specifically in the table above.
  • Z stands for the groups Z-1.1 to Z-1,400.
  • Y is 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 ) -alkylsulfinyl, (C 1 -C 2 ) -alkylsulfonyl,
  • W is oxygen or sulfur; R 1 is CH 3 ,
  • R is CH 3 , with the exception of the following compound:
  • 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 for example (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-methylpent
  • 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 bonded through 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-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-
  • Alkenyloxy means an alkenyl radical bonded through an oxygen atom
  • alkynyloxy means an above an oxygen atom bonded alkynyl group such as (C 2 -C 1 0) -, (C 2 -C 6) - or (C 2 -C 4) alkenoxy, and (C3-C10) -, (C 3 -C 6) - or (C 3 -C 4 ) -alkoxy.
  • Cycloalkyloxy means a cycloalkyl group bonded via an oxygen atom.
  • the number of carbon atoms 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 C atoms here 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 also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, the binding site being on the aromatic system.
  • Aryl is also generally known from the term “optionally 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,
  • 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-1H-pyrrole 1- or 2- or 3- or 4- or 5-yl; 2,5-dihydro-1H-pyrrol-1 - or 2- or 3-yl, 1- or 2- or 3- or 4-piperidinyl; 2,3,4,5-tetrahydropyridine-2- or 3- or 4- or 5-yl or 6-yl; 1,2,3,6-tetrahydropyridine-1 or 2 or 3 or 4 or 5 or 6-yl; 1,2,3,4-tetrahydropyridine-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4-dihydropyridine-I - or 2- or 3- or 4-yl; 2,3-dihydropyridine-2 or 3 or 4 or 5 or 6-yl; 2,5-dihydropyridine-2- or 3- or 4- or
  • Preferred 3-membered ring and 4-membered ring heterocycles
  • 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- or 7-yl 2,5-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-1,3-oxazepine 2- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; l, 3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 1,4-oxazepan-2- or 3- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-l,
  • 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, Halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl,
  • Alkylaminocarbonyl bis-alkylaminocarbonyl, cycloalkylaminocarbonyl,
  • 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) S (O)
  • S (O) 2 also SO2 for short
  • 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-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1
  • 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.
  • bis also includes the combination of different alkyl radicals, e.g. For example, methyl (ethyl) or ethyl (methyl).
  • Haloalkyl means by the same or different halogen atoms, partially or fully substituted alkyl, alkenyl and alkynyl, for example monohaloalkyl
  • ( Monohaloalkyl) such. CH 2 CH 2 Cl, CH 2 CH 2 Br, CHClCH 3 , CH 2 Cl, CH 2 F; Perhaloalkyl such. B. CCl 3, CC1F 2, CFC1 2 CF 2 CC1F 2, CF 2 CC1FCF 3; Polyhaloalkyl such. CH 2 CHFC1, CF 2 CC1FH, CF 2 CBrFH, CH 2 CF 3; The term 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, and the same applies to haloalkenyl and other radicals substituted by halogen.
  • (C 1 -C 4) -alkyl denotes a short notation for straight-chain or branched alkyl having one to four carbon atoms corresponding to the formula
  • Range for C atoms 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. B. "(Ci-C6) -alkyl”, accordingly also include straight-chain or branched alkyl radicals having a larger number of carbon atoms, ie according to Example, the alkyl radicals having 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 denotes, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2 Butinyl, 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-butinyl, 1, 1-dimethyl-2-propynyl, 1-ethyl
  • 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, for example 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 also substituents having a double bond on the cycloalkenyl radical, for.
  • substituents having a double bond on the cycloalkenyl radical for.
  • an alkylidene group such as methylidene
  • substituted cycloalkyl the explanations for substituted cycloalkyl apply correspondingly.
  • alkylidene for example also in the form (C 1 -C 10) -alkylidene, means the radical of a straight-chain or branched open-chain hydrocarbon radical which has a double bond is bound.
  • Cycloalkylidene means a
  • Alkoxyalkyl means an alkoxy group attached via an alkyl group
  • alkoxyalkoxy means an alkoxyalkyl group bonded via an oxygen atom, e.g. (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. B. trifluoromethyl or difluoromethyl partially or fully substituted cycloalkyl or cycloalkenyl, for example 1-fluorocycloprop-l -yl, 2-fluorocycloprop-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocyclobutyl-1, Trifluoromethylcycloprop-1-yl, 2 Trifluoromethylcycloprop-1-yl, 1-chlorocycloprop-1-yl, 2-chlorocycloprop-1-yl, 2,2-dichlorocycloprop-1-yl, 3,3-difluorocyclobutyl,
  • 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-Cg) -, (Ci-Ce) - or (Ci-C4) -alkyl] silyl, e.g. (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 (1,1-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
  • 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, R 1 , R 2 , R 3 , R 4 and R 5 of the general formula (I) have the meanings defined above in the following schemes, unless exemplary but non-limiting definitions take place.
  • the synthesis of the compounds of the general formula (Ia) according to the invention is carried out via an amide coupling of an acid of the general formula (II) with an amine of the general formula (III) 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 Synthsis, Ed. N.
  • 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 1).
  • 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 (see Scheme 1).
  • the synthesis of the acid of the general formula (II) can be prepared by saponification of the compound of the general formula (IV) according to or analogously to methods known to those skilled 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), and the saponification reaction preferably takes place in the temperature range between room temperature and 100 ° C.
  • the Lewis acid may be boron tribromide and the reaction 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 (IV) can be prepared by alkylating the compound of the general formula (V) with a halide of the general formula (VI) in the presence of a base or by methods analogous to those skilled in the art (see Scheme 3).
  • the base can be Carbonate salt of an alkali metal (such as lithium, sodium, potassium or cesium), and the saponification reaction preferably occurs in the temperature range
  • R ' (C 1 -C 4 ) -alkyl.
  • Scheme 4 describes the synthesis of the compound of general formula (V) by reaction of an enamine of general formula (VII) with a hydrazine of general formula (VIII) in an adequate solvent such as methanol or ethanol. Alternatively, the reaction may be carried out in a solvent such as tetrahydrofuran.
  • the compounds of the general formula (VII) can be prepared by condensation of a ketone of the general formula (IX) and dimethylformamide dimethyl acetal of the general formula (X) (see Scheme 5, Tetrahedron 1998, 54 (20), 5075-5088).
  • the compounds of the general formula (XVI) can be prepared by condensation of a ketone of the general formula (XV) and dimethylformamide dimethyl acetal of the general formula (X) (see Scheme 9, Tetrahedron 1998, 54 (20), 5075-5088).
  • Scheme 10 describes the synthesis of the compound of general formula (XVII) by reaction of an enamine of general formula (XVI) with a hydrazine of general formula (VIII) in an adequate solvent such as methanol or ethanol. Alternatively, the reaction may be carried out in a solvent such as tetrahydrofuran.
  • the base may be a carbonate salt of an alkali metal (such as lithium, sodium, potassium or cesium), and the saponification reaction preferably takes place in the temperature range between room temperature and 150 ° C in an adequate solvent such as, for example
  • R ' (C 1 -C 4 ) -alkyl.
  • the synthesis of the acid of general formula (XXI) can be prepared by saponification of the compound of general formula (XX) or analogously to methods known to those skilled 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), and the saponification reaction preferably takes place in the temperature range between room temperature and 100 ° C.
  • 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.
  • 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 1).
  • 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 (see Scheme 1).
  • 3-Fluoropyridine-2-carbonitrile (8.0 g, 65.52 mmol, 1.0 equiv) was dissolved in diethyl ether (150 ml) under a nitrogen atmosphere and cooled to 0 ° C with an ice-bath. To the solution was added dropwise within 30 min. add a 3M methylmagnesium bromide solution in diethyl ether (24.02mL, 72.07mmol). The resulting reaction mixture was stirred at room temperature overnight.
  • the suspension was cooled to 0 to 4 ° C. with an ice bath, mixed with 2M hydrochloric acid and stirred for 2 hours at room temperature. Thereafter, the pH was reduced by adding conc. Ammonia adjusted to pH 8. The reaction mixture was washed three times with 100 ml each time
  • reaction mixture was poured into water (50 ml) and extracted three times with 20 ml of ethyl acetate each time. Then the solvent was removed in vacuo and the residue was purified
  • Synthesis step 7 2- [4-bromo-3- (3-fluoropyridin-2-yl) -1H-pyrazol-1-yl] -N, N, 2-trimethylpropanamide (1.46-167)
  • reaction mixture was diluted with saturated sodium bicarbonate solution (10 ml) and then extracted with ethyl acetate (10 ml).
  • ethyl acetate 10 ml
  • the aqueous phase was extracted three times with ethyl acetate (10 ml) and the combined organic phases were dried over magnesium sulfate.
  • Cyclopropylacetic acid (23.00 g, 230 mmol, 1.0 equiv) was dissolved in dichloromethane (800 ml) and then treated with cabonyldiimidazole (CDI, 40.27 g, 248 mmol, 1.08 equiv.) Under nitrogen atmosphere. The reaction mixture was stirred for 2 h at room temperature and then admixed with N-methoxymethanamine hydrochloride (1: 1) (22.88 g, 234 mmol, 1.02 equiv.).
  • CDI cabonyldiimidazole
  • reaction mixture was stirred for 16 h at room temperature and then with ice water and
  • Synthesis step 2 2-Cyclopropyl-1- (2,6-difluorophenyl) ethanone 1,3-Difluorobenzene (7.50 g, 65.78 mmol, 1.0 equiv) was dissolved in THF (75 mL) and cooled to -78 ° C with a cold bath (nitrogen atmosphere). A 2M LDA solution (2M in THF, 65.5 mL, 98.67 mmol, 1.50 equiv.) was added dropwise.
  • reaction mixture was poured into water (100 ml) and extracted three times with 100 ml of ethyl acetate each time.
  • Table L I Preferred compounds of the formula (L I) are the compounds 1.1-1 to 1.1-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.1-1 to 1.1-400 of Table LI are thus characterized by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.2 Preferred compounds of the formula (1.2) are the compounds 1.2-1 to 1.2-400, wherein Z has the meanings indicated in the respective line of Table 1.
  • the compounds 1.2-1 to 1.2- 400 of Table 1.2 are thus by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.3 Preferred compounds of the formula (1.3) are the compounds 1.3-1 to 1.3-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.3-1 to 1.3-400 of Table 1.3 are thus characterized by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.4 Preferred compounds of the formula (1.4) are the compounds 1.4-1 to 1.4-400, wherein Z has the meanings indicated in the respective line of Table 1.
  • the compounds 1.4-1 to 1.4-400 of Table 1.4 are thus characterized by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.5 Preferred compounds of the formula (1.5) are the compounds 1.5-1 to 1.5-400, wherein Z has the meanings indicated in the respective line of Table 1.
  • the compounds 1.5-1 to 1.5-346 of Table 1.5 are thus by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.6 Preferred compounds of the formula (1.6) are the compounds 1.6-1 to 1.6-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.6-1 to 1.6-400 of Table 1.6 are thus characterized by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.7 Preferred compounds of the formula (1.7) are the compounds 1.7-1 to 1.7-400, wherein Z has the meanings indicated in the respective line of Table 1.
  • the compounds 1.7-1 to 1.7-400 of Table 1.7 are thus characterized by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.8 Preferred compounds of the formula (1.8) are the compounds 1.8-1 to 1.8-400, wherein Z has the meanings indicated in the respective line of Table 1.
  • the compounds 1.8-1 to 1.8-400 of Table 1.8 are thus characterized by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.9 Preferred compounds of the formula (1.9) are the compounds 1.9-1 to 1.9-400, wherein Z has the meaning given in the respective line of Table 1.
  • the compounds 1.9-1 to 1.9-400 of Table 1.9 are thus characterized by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.10 Preferred compounds of the formula (1.10) are the compounds 1.10-1 to 1.10-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.10-1 to 1.10-400 of Table 1.10 are therefore distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.11 Preferred compounds of the formula (1.11) are the compounds 1.11 - 1 to 1.11 -400, in which Z has the meanings of Table 1 given in the respective line.
  • the compounds LI 1-1 to LI 1-400 of Table LI 1 are thus characterized by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.12 Preferred compounds of the formula (1.12) are the compounds 1.12-1 to 1.12-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.12-1 to 1.12-400 of Table 1.12 are thus characterized by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.13 Preferred compounds of the formula (1.13) are the compounds 1.13-1 to 1.13-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.13-1 to 1.13-400 of Table 1.13 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.14 Preferred compounds of the formula (1.14) are the compounds 1.14-1 to 1.14-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.14-1 to 1.14-400 of Table 1.14 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.15 Preferred compounds of the formula (1.15) are the compounds 1.15-1 to 1.15-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.15-1 to 1.15-400 of Table 1.15 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.16 Preferred compounds of the formula (1.16) are the compounds 1.16-1 to 1.16-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.16-1 to 1.16-400 of Table 1.16 are therefore distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.17 Preferred compounds of the formula (1.17) are the compounds 1.17-1 to 1.17-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.17-1 to 1.17-400 of Table 1.17 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.18 Preferred compounds of the formula (1.18) are the compounds 1.18-1 to 1.18-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.18-1 to 1.18-400 of Table 1.18 are thus characterized by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.19 Preferred compounds of the formula (1.19) are the compounds 1.19-1 to 1.19-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.19-1 to 1.19-400 of Table 1.19 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.20 Preferred compounds of the formula (1.20) are the compounds 1.20-1 to 1.20-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.20-1 to 1.20-400 of Table 1.20 are therefore distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.21 Preferred compounds of the formula (1.21) are the compounds 1.21-1 to 1.21 -400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.21-1 to 1.21-400 of Table 1.21 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.22 Preferred compounds of the formula (1.22) are the compounds 1.22-1 to 1.22-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.22-1 to 1.22-400 of Table 1.22 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.23 Preferred compounds of the formula (1.23) are the compounds 1.23-1 to 1.23-400, in which Z has the meanings given in Table 1 in the respective line.
  • the compounds 1.23-1 to 1.23-400 of Table 1.23 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.24 Preferred compounds of the formula (1.24) are the compounds 1.24-1 to 1.24-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.24-1 to 1.24-400 of Table 1.24 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.25 Preferred compounds of the formula (1.25) are the compounds 1.25-1 to 1.25-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.25-1 to 1.25-400 of Table 1.25 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.26 Preferred compounds of the formula (1.26) are the compounds 1.26-1 to 1.26-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.26-1 to 1.26-400 of Table 1.26 are thus characterized by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.27 Preferred compounds of the formula (1.27) are the compounds 1.27-1 to 1.27-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.27-1 to 1.27-400 of Table 1.27 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.28 Preferred compounds of the formula (1.28) are the compounds 1.28-1 to 1.28-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.28-1 to 1.28-400 of Table 1.28 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.29 Preferred compounds of the formula (1.29) are the compounds 1.29-1 to 1.29-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.29-1 to 1.29-400 of Table 1.29 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.30 Preferred compounds of the formula (1.30) are the compounds 1.30-1 to 1.30-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.30-1 to 1.30-400 of Table 1.30 are therefore distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.31 Preferred compounds of the formula (1.31) are the compounds 1.31-1 to 1.31-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.31-1 to 1.31-400 of Table 1.31 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.32 Preferred compounds of the formula (1.32) are the compounds 1.32-1 to 1.32-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.32-1 to 1.32-400 of Table 1.32 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.33 Preferred compounds of the formula (1.33) are the compounds 1.33-1 to 1.33-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.33-1 to 1.33-400 of Table 1.33 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.34 Preferred compounds of the formula (1.34) are the compounds 1.34-1 to 1.34-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.34-1 to 1.34-400 of Table 1.34 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.35 Preferred compounds of the formula (1.35) are the compounds 1.35-1 to 1.35-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.35-1 to 1.35-400 of Table 1.35 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.36 Preferred compounds of the formula (1.36) are the compounds 1.36-1 to 1.36-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.36-1 to 1.36-400 of Table 1.36 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.37 Preferred compounds of the formula (1.37) are the compounds 1.37-1 to 1.37-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.37-1 to 1.37-400 of Table 1.37 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.38 Preferred compounds of the formula (1.38) are the compounds 1.38-1 to 1.38-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.38-1 to 1.38-400 of Table 1.38 are therefore distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.39 Preferred compounds of the formula (1.39) are the compounds 1.39-1 to 1.39-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.39-1 to 1.39-400 of Table 1.39 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.40 Preferred compounds of the formula (1.40) are the compounds 1.40-1 to 1.40-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.40-1 to 1.40-400 of Table 1.40 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.41 Preferred compounds of the formula (1.41) are the compounds 1.41-1 to 1.41-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.41-1 to 1.41-400 of Table 1.41 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.42 Preferred compounds of the formula (1.42) are the compounds 1.42-1 to 1.42-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.42-1 to 1.42-400 of Table 1.42 are therefore distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.43 Preferred compounds of the formula (1.43) are the compounds 1.43-1 to 1.43-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.43-1 to 1.43-400 of Table 1.43 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.44 Preferred compounds of the formula (1.44) are the compounds 1.44-1 to 1.44-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.44-1 to 1.44-400 of Table 1.44 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.45 Preferred compounds of the formula (1.45) are the compounds 1.45-1 to 1.45-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.45-1 to 1.45-400 of Table 1.45 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.46 Preferred compounds of the formula (1.46) are the compounds 1.46-1 to 1.46-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.46-1 to 1.46-400 of Table 1.46 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.47 Preferred compounds of the formula (1.47) are the compounds 1.47-1 to 1.47-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.47-1 to 1.47-400 of Table 1.47 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.48 Preferred compounds of the formula (1.48) are the compounds 1.48-1 to 1.48-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.48-1 to 1.48-400 of Table 1.48 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.49 Preferred compounds of the formula (1.49) are the compounds 1.49-1 to 1.49-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.49-1 to 1.49-400 of Table 1.49 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.50 Preferred compounds of the formula (1.50) are the compounds 1.50-1 to 1.50-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.50-1 to 1.50-400 of Table 1.50 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.51 Preferred compounds of the formula (1.51) are the compounds 1.51-1 to 1.51-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.51-1 to 1.51-400 of Table 1.51 are thus characterized by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.52 Preferred compounds of the formula (1.52) are the compounds 1.52-1 to 1.52-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.52-1 to 1.52-400 of Table 1.52 are thus characterized by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.53 Preferred compounds of the formula (1.53) are the compounds 1.53-1 to 1.53-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.53-1 to 1.53-400 of Table 1.53 are thus characterized by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.54 Preferred compounds of the formula (1.54) are the compounds 1.54-1 to 1.54-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.54-1 to 1.54-400 of Table 1.54 are thus characterized by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.55 Preferred compounds of the formula (1.55) are the compounds 1.1-55 to I. 55-400, wherein Z has the meanings indicated in the respective line of Table 1.
  • the compounds 1.55-1 to 1.55-400 of Table 1.55 are thus characterized by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.56 Preferred compounds of the formula (1.56) are the compounds 1.56-1 to 1.56-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.56-1 to 1.56-400 of Table 1.56 are thus characterized by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.57 Preferred compounds of the formula (1.57) are the compounds 1.57-1 to 1.57-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.57-1 to 1.57-400 of Table 1.57 are thus characterized by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.58 Preferred compounds of the formula (1.58) are the compounds 1.58-1 to 1.58-400, wherein Z has the meanings indicated in the respective line of Table 1.
  • the compounds 1.58-1 to 1.58-400 of Table 1.58 are thus characterized by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.59 Preferred compounds of the formula (1.59) are the compounds 1.59-1 to 1.59-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.59-1 to 1.59-346 of Table 1.59 are thus characterized by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.60 Preferred compounds of the formula (1.60) are the compounds 1.60-1 to 1.60-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.60-1 to 1.60-400 of Table 1.60 are thus characterized by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.61 Preferred compounds of the formula (1.61) are the compounds 1.61-1 to 1.61-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.61-1 to 1.61-400 of Table 1.61 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.62 Preferred compounds of the formula (1.62) are the compounds 1.62-1 to 1.62-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.62-1 to 1.62-400 of Table 1.62 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.63 Preferred compounds of the formula (1.63) are the compounds 1.63-1 to 1.63-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.63-1 to 1.63-400 of Table 1.63 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.64 Preferred compounds of the formula (1.64) are the compounds 1.64-1 to 1.64-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.64-1 to 1.64-400 of Table 1.64 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.65 Preferred compounds of the formula (1.65) are the compounds 1.1-65 to I 65-400, wherein Z has the meanings indicated in the respective line of Table 1. The compounds 1.65-1 to 1.65-400 of Table 1.65 are thus affected by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.66 Preferred compounds of the formula (1.66) are the compounds 1.66-1 to 1.66-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.66-1 to 1.66-400 of Table 1.66 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.67 Preferred compounds of the formula (1.67) are the compounds 1.67-1 to 1.67-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.67-1 to 1.67-400 of Table 1.67 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.68 Preferred compounds of the formula (1.68) are the compounds 1.68-1 to 1.68-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.68-1 to 1.68-400 of Table 1.68 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.69 Preferred compounds of the formula (1.69) are the compounds 1.69-1 to 1.69-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.69-1 to 1.69-346 of Table 1.69 are thus characterized by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.70 Preferred compounds of the formula (1.70) are the compounds 1.70-1 to 1.70-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.70-1 to 1.70-400 of Table 1.70 are thus characterized by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.71 Preferred compounds of the formula (1.71) are the compounds 1.71-1 to 1.71-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.71-1 to 1.71-400 of Table 1.71 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.72 Preferred compounds of the formula (1.72) are the compounds 1.72-1 to 1.72-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.72-1 to 1.72-400 of Table 1.72 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above,
  • Table 1.73 Preferred compounds of the formula (1.73) are the compounds 1.73-1 to 1.73-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.73-1 to 1.73-400 of Table 1.73 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.74 Preferred compounds of the formula (1.74) are the compounds 1.74-1 to 1.74-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.74-1 to 1.74-400 of Table 1.74 are thus characterized by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.75 Preferred compounds of the formula (1.75) are the compounds 1.1-75 to I 75-400, wherein Z has the meanings indicated in the respective line of Table 1.
  • the compounds 1.75-1 to 1.75-400 of Table 1.75 are thus characterized by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.76 Preferred compounds of the formula (1.76) are the compounds 1.76-1 to 1.76-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.76-1 to 1.76-400 of Table 1.76 are therefore distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.77 Preferred compounds of the formula (1.77) are the compounds 1.77-1 to 1.77-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.77-1 to 1.77-400 of Table 1.77 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.78 Preferred compounds of the formula (1.78) are the compounds 1.78-1 to 1.78-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.78-1 to 1.78-400 of Table 1.78 are thus characterized by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.79 Preferred compounds of the formula (1.79) are the compounds 1.79-1 to 1.79-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.79-1 to 1.79-346 of Table 1.79 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.80 Preferred compounds of the formula (1.80) are the compounds 1.80-1 to 1.80-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.80-1 to 1.80-400 of Table 1.80 are therefore distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.81 Preferred compounds of the formula (1.81) are the compounds 1.81-1 to 1.81-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.81-1 to 1.81-400 of Table 1.81 are thus characterized by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.82 Preferred compounds of the formula (1.82) are the compounds 1.82-1 to 1.82-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.82-1 to 1.82-400 of Table 1.82 are therefore distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.83 Preferred compounds of the formula (1.83) are the compounds 1.83-1 to 1.83-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.83-1 to 1.83-400 of Table 1.83 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.84 Preferred compounds of the formula (1.84) are the compounds 1.84-1 to 1.84-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.84-1 to 1.84-400 of Table 1.84 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.85 Preferred compounds of the formula (1.85) are the compounds 1.1-85 to I 85-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.85-1 to 1.85-400 of Table 1.85 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.86 Preferred compounds of the formula (1.86) are the compounds 1.86-1 to 1.86-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.86-1 to 1.86-400 of Table 1.86 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.87 Preferred compounds of the formula (1.87) are the compounds 1.87-1 to 1.87-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.87-1 to 1.87-400 of Table 1.87 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.88 Preferred compounds of the formula (1.88) are the compounds 1.88-1 to 1.88-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.88-1 to 1.88-400 of Table 1.88 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.89 Preferred compounds of the formula (1.89) are the compounds 1.89-1 to 1.89-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.89-1 to 1.89-346 of Table 1.89 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.90 Preferred compounds of the formula (1.90) are the compounds 1.90-1 to 1.90-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.90-1 to 1.90-400 of Table 1.90 are therefore distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.91 Preferred compounds of the formula (1.91) are the compounds 1.91-1 to 1.91-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.91-1 to 1.91-400 of Table 1.91 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.92 Preferred compounds of the formula (1.92) are the compounds 1.92-1 to 1.92-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.92-1 to 1.92-400 of Table 1.92 are therefore distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.93 Preferred compounds of the formula (1.93) are the compounds 1.93-1 to 1.93-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.93-1 to 1.93-400 of Table 1.93 are thus characterized by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.94 Preferred compounds of the formula (1.94) are the compounds 1.94-1 to 1.94-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.94-1 to 1.94-400 of Table 1.94 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.95 Preferred compounds of the formula (1.95) are the compounds 1.95-1 to 1.95-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.95-1 to 1.95-400 of Table 1.95 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.96 Preferred compounds of the formula (1.96) are the compounds 1.96-1 to 1.96-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.96-1 to 1.96-400 of Table 1.96 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.97 Preferred compounds of the formula (1.97) are the compounds 1.97-1 to 1.97-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.97-1 to 1.97-400 of Table 1.97 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.98 Preferred compounds of the formula (1.98) are the compounds 1.98-1 to 1.98-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.98-1 to 1.98-400 of Table 1.98 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.99 Preferred compounds of the formula (1.99) are the compounds 1.99-1 to 1.99-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.99-1 to 1.99-346 of Table 1.99 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Preferred compounds of the formula (I00) are the compounds 11006-1 to 1100-400, in which Z has the meanings given in Table 1 in the respective line.
  • the compounds 1.100-1 to 1.100-400 of Table 1.100 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.101 Preferred compounds of the formula (1.101) are the compounds 1.101-1 to 1.101-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.101-1 to 1.101-400 of Table 1.101 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.102 Preferred compounds of the formula (1.102) are the compounds 1.102-1 to 1.102-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the connection 1.102-1 to 1.102-400 of Table 1.102 are thus defined by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.103 Preferred compounds of the formula (1.103) are the compounds 1.103-1 to 1.103-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.103-1 to 1.1039-400 of Table 1.103 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.104 Preferred compounds of the formula (1.104) are the compounds 1.104-1 to 1.104-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.104-1 to 1.104-400 of Table 1.104 are therefore distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.105 Preferred compounds of the formula (1.105) are the compounds 1.105-1 to 1.105-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.105-1 to 1.105-400 of Table 1.105 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.106 Preferred compounds of the formula (1.106) are the compounds 1.106-1 to 1.106-400, wherein Z has the meaning given in the respective line of Table 1.
  • the connection 1.106-1 to 1.106-400 of Table 1.106 are thus by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.107 Preferred compounds of the formula (1.107) are the compounds 1.107-1 to 1.107-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.107-1 to 1.107-400 of Table 1.107 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.108 Preferred compounds of the formula (1.108) are the compounds 1.108-1 to 1.108-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.108-1 to 1.108-400 of Table 1.108 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.109 Preferred compounds of the formula (1.109) are the compounds 1.109-1 to 1.109-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.109-1 to 1.109-400 of Table 1.109 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.110 Preferred compounds of the formula (1.110) are the compounds L I 10-1 to L I 10-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compound L I 10-1 to L I 10-400 of the table LI 10 are thus characterized by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.111 Preferred compounds of the formula (1.111) are the compounds I. ll ll to 1.111-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the compound I. ll ll to 1.111-400 of Table 1.111 are thus characterized by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.112 Preferred compounds of the formula (1.112) are the compounds L I 12-1 to L I 12-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the connection L I 12-1 to L I 12-400 of the table LI 12 are thus characterized by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table LI 13 Preferred compounds of the formula (LI 13) are the compounds LI 13-1 to LI 13-400, wherein Z has the meaning given in the respective line of Table 1.
  • the connection LI 13-1 to LI 13-400 of the table LI 13 are thus by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.114 Preferred compounds of the formula (1.114) are the compounds 1.114-1 to 1.114-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compound L I 14-1 to L I 14-400 of the table L I 14 are thus by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.115 Preferred compounds of the formula (1.115) are the compounds 1.115-1 to 1.115-400, wherein Z has the meanings indicated in the respective line of Table 1.
  • the connection LI 15-1 to LI 15-400 of the table LI 15 are thus characterized by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Preferred compounds of the formula (L I 16) are the compounds L I 16-1 to L I 16-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compound L I 16-1 to L I 16-400 of Table L I 16 are thus by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Preferred compounds of the formula (LI 17) are the compounds 1.117-1 to 1.117-400, wherein Z has the meaning given in the respective line of Table 1.
  • the connection LI 17-1 to LI 17-400 of Table LI 17 are thus by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.118 Preferred compounds of the formula (1.118) are the compounds 1.118-1 to 1.118-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compound L I 18-1 to L I 18-400 of the table L I 18 are thus characterized by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table LI 19 Preferred compounds of the formula (LI 19) are the compounds LI 19-1 to LI 19-400, wherein Z has the meaning given in the respective line of Table 1.
  • the connection LI 19-1 to LI 19-400 of the table LI 19 are thus characterized by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.120 Preferred compounds of the formula (1.120) are the compounds 1,120-1 to 1,120-400, in which Z has the meanings given in Table 1 of each line.
  • the connection 1.120-1 to 1.120-400 of Table 1.120 are thus determined by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.121 Preferred compounds of the formula (1.121) are the compounds 1.121-1 to 1.121-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.121-1 to 1.121-400 of Table 1.121 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.122 Preferred compounds of the formula (1.122) are the compounds 1.122-1 to 1.122-400, wherein Z has the meanings given in Table 1 of each line.
  • the connection 1.122-1 to 1.122-400 of Table 1.122 are thus by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.123 Preferred compounds of the formula (1.123) are the compounds 1.123-1 to 1.123-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.123-1 to 1.123-400 of Table 1.123 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.124 Preferred compounds of the formula (1.124) are the compounds 1.124-1 to 1.124-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.124-1 to 1.124-400 of Table 1.124 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.125 Preferred compounds of the formula (1.125) are the compounds 1.125-1 to 1.125-400, wherein Z has the meaning given in the respective line of Table 1.
  • the connection 1.125-1 to 1.125-400 of Table 1.125 are thus by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.126 Preferred compounds of the formula (1.126) are the compounds 1.126-1 to 1.126-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.126-1 to 1.126-400 of Table 1.126 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.127 Preferred compounds of the formula (1.127) are the compounds 1.127-1 to 1.127-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.127-1 to 1.127-400 of Table 1.127 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.128 Preferred compounds of the formula (1.128) are the compounds 1.128-1 to 1.128-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.128-1 to 1.128-400 of Table 1.128 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.129 Preferred compounds of the formula (1.129) are the compounds 1.129-1 to 1.129-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.129-1 to 1.129-400 of Table 1.129 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.130 Preferred compounds of the formula (1.130) are the compounds 1.130-1 to 1.130-400, in which Z has the meanings given in Table 1 of each line.
  • the compounds 1.130-1 to 1.130-400 of Table 1.130 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.131 Preferred compounds of the formula (1.131) are the compounds 1.131-1 to 1.131-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.131-1 to 1.131-400 of Table 1.131 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.132 Preferred compounds of the formula (1.132) are the compounds 1.132-1 to 1.132-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.132-1 to 1.132-400 of Table 1.132 are therefore distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.133 Preferred compounds of the formula (1.133) are the compounds 1.133-1 to 1.133-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.133-1 to 1.133-400 of Table 1.133 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.134 Preferred compounds of the formula (1.134) are the compounds 1.134-1 to 1.134-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.134-1 to 1.134-400 of Table 1.134 are thus characterized by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.135 Preferred compounds of the formula (1.135) are the compounds 1.135-1 to 1.135-400, wherein Z has the meanings indicated in the respective line of Table 1.
  • the compounds 1.135-1 to 1.135-400 of Table 1.135 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.136 Preferred compounds of the formula (1.136) are the compounds 1.136-1 to 1.136-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.136-1 to 1.136-400 of Table 1.136 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.137 Preferred compounds of the formula (1.137) are the compounds 1.137-1 to 1.137-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.137-1 to 1.137-400 of Table 1.137 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.138 Preferred compounds of the formula (1.138) are the compounds 1.138-1 to 1.138-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.138-1 to 1.138-400 of Table 1.138 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.139 Preferred compounds of the formula (1.139) are the compounds 1.139-1 to 1.139-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.139-1 to 1.139-400 of Table 1.139 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.140 Preferred compounds of the formula (1.140) are the compounds 1.140-1 to 1.140-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the connection 1.140-1 to 1.140-400 of Table 1.140 are thus by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.141 Preferred compounds of the formula (1.141) are the compounds 1.141-1 to 1.141-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.141-1 to 1.141-400 of Table 1.141 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.142 Preferred compounds of the formula (1.142) are the compounds 1.142-1 to 1.142-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.142-1 to 1.142-400 of Table 1.142 are therefore distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.143 Preferred compounds of the formula (1.143) are the compounds 1.143-1 to 1.143-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.143-1 to 1.143-400 of Table 1.143 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.144 Preferred compounds of the formula (1.144) are the compounds 1.144-1 to 1.144-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.144-1 to 1.144-400 of Table 1.144 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.145 Preferred compounds of the formula (1.145) are the compounds 1.145-1 to 1.145-400, wherein Z has the meanings given in Table 1 of each Table.
  • the connection 1.145-1 to 1.145-400 of Table 1.145 are thus by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.146 Preferred compounds of the formula (1.146) are the compounds 1.146-1 to 1.146-400, wherein Z has the meaning given in the respective line of Table 1.
  • the compounds 1.146-1 to 1.146-400 of Table 1.146 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.147 Preferred compounds of the formula (1.147) are the compounds 1.147-1 to 1.147-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.147-1 to 1.147-400 of Table 1.147 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.148 Preferred compounds of the formula (1.148) are the compounds 1.48-1 to 1.148-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.148-1 to 1.148-400 of Table 1.148 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.149 Preferred compounds of the formula (1.149) are the compounds 1.149-1 to 1.149-400, wherein Z has the meaning given in the respective line of Table 1.
  • the compounds 1.149-1 to 1.149-400 of Table 1.85 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.150 Preferred compounds of the formula (1.150) are the compounds 1.150-1 to 1.150-400, in which Z has the meanings of Table 1 indicated in the respective line.
  • the connection 1.150-1 to 1.150-400 of Table 1.150 are thus determined by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.151 Preferred compounds of the formula (1.151) are the compounds 1.151-1 to 1.151-400, wherein Z has the meanings given in Table 1 of each line.
  • the compounds 1.151-1 to 1.151-400 of Table 1.151 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.152 Preferred compounds of the formula (1.152) are the compounds 1.152-1 to 1.152-400, wherein Z has the meanings given in Table 1 of each line.
  • the connection 1.152-1 to 1.152-400 of Table 1.152 are thus determined by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.153 Preferred compounds of the formula (1.153) are the compounds 1.153-1 to 1.153-400, wherein Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.153-1 to 1.153-400 of Table 1.153 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.154 Preferred compounds of the formula (1.154) are the compounds 1.154-1 to 1.154-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.154-1 to 1.154-400 of Table 1.154 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.155 Preferred compounds of the formula (1.155) are the compounds 1.155-1 to 1.155-400, wherein Z has the meaning given in the respective line of Table 1.
  • the connection 1.155-1 to 1.155-400 of Table 1.155 are thus determined by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.156 Preferred compounds of the formula (1.156) are the compounds 1.156-1 to 1.156-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.156-1 to 1.156-400 of Table 1.156 are thus distinguished by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.157 Preferred compounds of the formula (1.157) are the compounds 1.157-1 to 1.157-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.157-1 to 1.157-400 of Table 1.157 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.158 Preferred compounds of the formula (1.158) are the compounds 1.158-1 to 1.158-400, wherein Z has the meanings of Table 1 given in the respective line.
  • the compounds 1.158-1 to 1.158-400 of Table 1.158 are thus distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.159 Preferred compounds of the formula (1.159) are the compounds 1.159-1 to 1.159-400, wherein Z has the meanings given in Table 1 of each Table.
  • the compounds 1.159-1 to 1.159-400 of Table 1.159 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.
  • Table 1.160 Preferred compounds of the formula (1.160) are the compounds 1.160-1 to 1.160-400, wherein Z has the meaning given in the respective line of Table 1.
  • the connection 1.160-1 to 1.160-400 of Table 1.160 are thus determined by the meaning of the respective entries no. 1 to 400 for Z of Table 1 above.
  • Table 1.161 Preferred compounds of the formula (1.161) are the compounds 1.161-1 to 1.161-400, wherein Z has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.161-1 to 1.161-400 of Table 1.161 are therefore distinguished by the meaning of the respective entries no. 1 to 400 defined for Z of Table 1.

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  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
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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/EP2018/078983 2017-10-26 2018-10-23 Pyrazoles substitués, leurs sels et leur utilisation comme agents herbicides WO2019081477A1 (fr)

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EP0346620A1 (fr) 1988-05-20 1989-12-20 Hoechst Aktiengesellschaft Agents phytoprotecteurs contenant des dérivés du 1,2,4-triazole ainsi que dérivés du 1,2,4-triazole
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US11046660B2 (en) * 2016-09-28 2021-06-29 Mironid Limited Compounds and their use as PDE4 activators
US20210214311A1 (en) * 2018-09-28 2021-07-15 Shenzhen Edk Pharmaceutical Technology Co., Ltd. N-aromatic amide compunds, preparation methods and uses thereof
EP3858811A4 (fr) * 2018-09-28 2022-05-11 Shenzhen EDK Pharmaceutical Technology Co., Ltd. Composé amide n-aromatique et son procédé de préparation et utilisation associée
US11760727B2 (en) 2018-09-28 2023-09-19 Shenzhen Edk Pharmaceutical Technology Co., Ltd. N-aromatic amide compounds, preparation methods and uses thereof

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