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WO2018177837A1 - Dérivés de 4-cyclopentyl-2-oxopyrrolidin-3-carboxamide et de 4-cyclopropyl-2-oxopyrrolidin-3-carboxamide et composés apparentés utilisés comme produits phytosanitaires herbicides - Google Patents

Dérivés de 4-cyclopentyl-2-oxopyrrolidin-3-carboxamide et de 4-cyclopropyl-2-oxopyrrolidin-3-carboxamide et composés apparentés utilisés comme produits phytosanitaires herbicides Download PDF

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Publication number
WO2018177837A1
WO2018177837A1 PCT/EP2018/057156 EP2018057156W WO2018177837A1 WO 2018177837 A1 WO2018177837 A1 WO 2018177837A1 EP 2018057156 W EP2018057156 W EP 2018057156W WO 2018177837 A1 WO2018177837 A1 WO 2018177837A1
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alkyl
compounds
alkoxy
aryl
cycloalkyl
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PCT/EP2018/057156
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German (de)
English (en)
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Thomas Müller
Hendrik Helmke
Olaf Peters
Michael Charles MCLEOD
Uwe Döller
Stefan Lehr
Hansjörg Dietrich
Anu Bheemaiah MACHETTIRA
Christoph Hugh Rosinger
Elmar Gatzweiler
Dirk Schmutzler
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Bayer Aktiengesellschaft
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Publication of WO2018177837A1 publication Critical patent/WO2018177837A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones

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.
  • this invention relates to substituted pyrrolidinones and their salts, to processes for their use
  • Crop crops or agents for controlling undesirable plant growth are contributing to
  • Plant growth regulators may be used in some crops, in others
  • WO2016 / 094117 The process for the synthesis of substituted pyrrolidinones is described in WO2016 / 094117.
  • WO2016 / 182780 describes substituted bicyclic compounds having herbicidal properties which carry aryls or substituted heteroaryls substituted on the amide bond.
  • substituted pyrrolidinones or their salts are particularly well suited as herbicides as herbicidal active ingredients which carry a substituted cycloalkylalkyl radical on the amide bond.
  • the present invention thus provides substituted pyrrolidinones of the general formula (I) or salts thereof
  • Q is an optionally substituted aryl, heteroaryl, (C3-Cio) -cycloalkyl or (C3-C10) -
  • Cycloalkenyl each ring or ring system optionally being substituted with up to 5 substituents from the group R 6 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or an optionally substituted 8-10-membered bicyclic
  • Ring system is optionally substituted with up to 5 substituents from the group R 6 , or
  • Q is (C 2 -C 10) -alkenyl, (C 2 -C 10) -alkynyl, (C 2 -C 10) -haloalkenyl, (C 2 -C 10) -haloalkynyl, (C 3 -C 10) -halocycloalkenyl, (Ci-Cio ) -Alkylcarbonyl or (C 1 -C 10) -alkoxy- (C 1 -C 10) -alkyl, (C 1 -C 10) -haloalkoxy- (C 1 -C 10) -alkyl, Z for the group stands,
  • Y is -C (R 7 ) (R 8 ) -, oxygen, or NR 1 ,
  • W 1 and W 2 are independently oxygen or sulfur
  • R 1 represents hydrogen, amino, hydroxyl, cyano, formyl, (C 1 -C 6) -alkyl, (C 1 -C 6) -haloalkyl, (C 1 -C 6) -cyanoalkyl, (C 1 -C 6) -hydroxyalkyl, (C 1 -C -g) Alkoxy- (Ci-Cg) -alkyl, aryl- (Ci-Cg) -alkyl, heteroaryl- (Ci-Cg) -alkyl, heterocyclyl- (Ci-Cg) -alkyl, (C 3 -Cio) -cycloalkyl, (C 3 -Cio) -Cycloalkyl- (Ci-Cg) -alkyl, (C 3 -Cg) -Halocycloalkyl, (C 3 -Cg) -Halocycloalkyl- (Ci-Cg) -
  • R 2 is hydrogen, halogen, hydroxy, (Ci-Cg) alkyl, (Ci-Cg) -haloalkyl, (Ci-Cg) -Hydroxyalkyl, (Ci-Cg) -alkoxy- (Ci-Cg) -alkyl,
  • R 3 is hydrogen, halogen, hydroxy, (Ci-Cg) alkyl, (Ci-Cg) -haloalkyl, (Ci-Cg) -Hydroxyalkyl, (Ci-Cg) -alkoxy, (Ci-Cg) -alkoxy- Ci-Cg) -alkyl,
  • R 4 is optionally substituted (C 1 -C 10) -haloalkyl, (C 3 -C 10) -cycloalkyl- (C 1 -C 10) -alkyl,
  • R 5 is hydrogen, hydroxy, amino, (Ci-Cg) alkyl, (Ci-Cg) -haloalkyl, (C 2 -Cg) -alkenyl, (C 3 -Cg) -alkynyl, (Ci-Cg) -alkoxyalkyl , (Ci-Cg) -haloalkoxyalkyl, (Ci-Cg) -alkylthio (Ci-Cg) -alkyl, (Ci-Cg) -alkylsulfmyl (Ci-Cg) -alkyl, (Ci-Cg) -alkylsulfonyl- ( Ci-Cg) -alkyl, (Ci-Cg) -alkylcarbonyl, (Ci-Cg) -haloalkylcarbonyl, (C 3 -Cg) -cycloalkylcarbonyl, (Ci-Cg) -alk
  • R 6 represents hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (C 1 -C 8) -alkyl,
  • R 7 and R 8 independently of one another represent hydrogen, hydroxyl, halogen, (C 1 -C 8 ) -alkyl, (C 1 -C 5) -
  • Haloalkyl (C 2 -C 8) alkenyl, (C 2 -C 8) alkynyl, (Ci-C 8) alkoxyalkyl, (Ci-C 8) -Haloalkoxyalkyl, (Ci-C8) alkylthio ( C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfmyl (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfonyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) alkylcarbonyl, (Ci-C 8) haloalkylcarbonyl, (C3-C8) cycloalkylcarbonyl, (Ci-C8) alkoxycarbonyl, (C 2 -C 8) - haloalkoxycarbonyl, (C4-C8) -cycloal
  • the compounds of general formula (I) may be prepared by addition of a suitable inorganic or organic acid such as, for example, mineral acids such as HCl, HBr, H 2 SO 4, H 2 PO or HNO 3, or organic acids, e.g.
  • a suitable inorganic or organic acid such as, for example, mineral acids such as HCl, HBr, H 2 SO 4, H 2 PO or HNO 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 form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts.
  • These salts then contain the conjugate base of the acid as an anion.
  • Sulfonklareamide or carboxylic acids may form internal salts with their turn protonatable groups, such as amino groups. Salt formation can also be due to the action of a base
  • Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine and ammonium, alkali or
  • Potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate are compounds in which the azide hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or
  • Alkaline earth metal salts in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula
  • R a to R d are each independently an organic radical, in particular alkyl, aryl, arylalkyl or alkylaryl. Also suitable are alkylsulfonium and
  • Alkylsulfoxoniumsalze such as (Ci-C4) -trialkylsulfonium and (Ci-C4) -Trialkylsulfoxoniumsalze.
  • the substituted pyrrolidinones 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 the general formula (I) wherein
  • Q is an optionally substituted aryl or heteroaryl, (C3-Cio) -cycloalkyl or (C3-C10) -
  • Cycloalkenyl each ring or ring system optionally being substituted with up to 5 substituents from the group R 6 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or an optionally substituted 8-10 membered bicyclic ring system in which each ring or ring system is selected from carbon atoms and 1-5
  • Y is -C (R 7 ) (R 8 ) -, oxygen, or NR 1 ,
  • W 1 and W 2 are independently oxygen or sulfur; is hydrogen, amino, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (Ci-C 6) hydroxyalkyl, (Ci-C6) - alkoxy- (Ci-C 6) alkyl, aryl (Ci-C 6) alkyl, heteroaryl (Ci-C 6) alkyl, heterocyclyl (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, (C3-C6) - Cycloalkyl- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -halocycloalkyl, (C 3 -C 6 ) -halocycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylcarbonyl, C6) alkoxycarbonyl, (C 2 -C
  • R 5 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) -alkenyl, (C 3 -C 6) alkynyl, (Ci-C 6) - Alkoxyalkyl, (C 1 -C 6 ) -haloalkoxyalkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfmyl (C 1 -C 6 ) -alkyl, C 6 ) -alkylsulfonyl- (C 1 -C 6 ) -alkyl, (C 2 -C 8 ) -dialkylaminosulfonyl or (C 3 -C 8 ) -trialkylsilyl,
  • R 6 is hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (C 1 -C 7 ) -alkyl,
  • R 7 and R 8 independently of one another represent hydrogen, hydroxyl, halogen, (C 1 -C 6) -alkyl, (C 1 -C 6) -
  • Haloalkyl (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, (Ci-C 6) alkoxyalkyl, (Ci-C 6) -Haloalkoxyalkyl, (Ci-C 6) alkylthio ( Ci-C 6 ) -alkyl.
  • Particularly preferred subject of the invention are compounds of general formula (I), wherein Q is an optionally substituted aryl or heteroaryl, (C 3 -C 8 ) -cycloalkyl or (C 3 -C 8 ) -
  • Cycloalkenyl each ring or ring system optionally being substituted with up to 5 substituents from the group R 6 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or an optionally substituted 8-10 membered bicyclic ring system in which each ring or ring system is selected from carbon atoms and 1-5
  • Q is (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl,, (C 3 -C 8 ) Haloalkloalkenyl, (C 1 -C 8 ) -alkylcarbonyl or (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl,
  • Y is -C (R 7 ) (R 8 ) -
  • W 1 and W 2 are independently oxygen or sulfur
  • R 1 is hydrogen, amino, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -hydroxyalkyl, (C 1 -C 6 ) -
  • R 4 when Q is 3,4-dimethoxyphenyl, R 4 is not 3,4-dimethoxyphenyl) ethyl and when Q is phenyl R 4 is not 1 - (naphthalenyl) ethyl is hydrogen, (C 1 -C 6 ) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) -alkenyl, (C 3 -C 6) alkynyl, (Ci-C6) - alkoxy- (Ci-C 6) alkyl, (Ci- C 6 ) haloalkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfmyl (C 1 -C 6 ) -alkyl, (Ci-C 6) alkyl
  • R 7 and R 8 independently of one another represent hydrogen, hydroxyl, halogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 2 -C 6 ) -alkenyl, (C 3 -C 6 ) -alkynyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C6) - haloalkoxy (Ci-C 6) alkyl, (Ci-C 6) alkylthio (Ci-C 6 ) alkyl.
  • Very particularly preferred subject of the invention are compounds of the general formula (I) wherein
  • Q is an optionally substituted aryl or heteroaryl, (C3-C 7) -cycloalkyl or (C3-C7) -
  • Cycloalkenyl each ring or ring system optionally being substituted with up to 5 substituents from the group R 6 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or an optionally substituted 8-10-membered bicyclic
  • Ring system is optionally substituted with up to 5 substituents from the group R 6 , or
  • Q is (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 7 ) -halocycloalkenyl, (C 1 -C 7 ) -alkylcarbonyl or (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, Z represents the group stands, Y stands for -CH (R 7 ) -,
  • W 1 and W 2 are independently oxygen or sulfur; preferably oxygen are;
  • R 1 is hydrogen, amino, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 4 ) -alkyl, C 6) alkyl, heterocyclyl (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) cycloalkyl
  • R 4 when Q is 3,4-dimethoxyphenyl, R 4 is not 3,4-dimethoxyphenyl) ethyl and when Q is phenyl R 4 is not 1 - (naphthalenyl) ethyl is hydrogen, (C 1 -C 6 ) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) -alkenyl, (C 3 -C 6) alkynyl, (Ci-C6) - alkoxy- (Ci-C 6) alkyl, (Ci- C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, represents hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (C 1 -C 4 ) -alkyl, (C 3 -C 5 ) -cycloalkyl, (C 2 -C 4) alkeny
  • R 7 is hydrogen, hydroxy, halogen, (Ci-C 3) alkyl, (Ci-C 3) -haloalkyl, (C 2 -C 3) alkenyl, (C2-C3) - alkynyl, (Ci-C 3 ) Alkoxy- (C 1 -C 3 ) -alkyl, (C 1 -C 3 ) -haloalkoxy- (C 1 -C 3 ) -alkyl, (C 1 -C 3 ) -alkylthio (C 1 -C 3 ) -alkyl ,
  • Q is an optionally substituted aryl or heteroaryl, (C 3 -C 7 ) -cycloalkyl or (C 3 -C 7 ) -
  • Cycloalkenyl each ring or ring system optionally being substituted with up to 5 substituents from the group R 6 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or an optionally substituted 8-10 membered bicyclic ring system in which each ring or ring system is selected from carbon atoms and 1-5
  • Q is (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 7 ) -halocycloalkenyl, (C 1 -C 6) -alkylcarbonyl or (C 1 -C 6) -alkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 6) -haloalkoxy- (C 1 -C 6) -alkyl,
  • Y is -CH 2 -
  • W 1 and W 2 are independently oxygen or sulfur; preferably oxygen are;
  • R 1 represents hydrogen, amino, (Ci-C 3) alkyl, aryl (Ci-C 3) alkyl, heteroaryl (Ci-C 3) alkyl, (C 3 -C 6) - cycloalkyl, (C 3 -C 5) cycloalkyl (Ci-C 3) alkyl, (Ci-C 6) alkylcarbonyl, (Ci-C 6) -alkoxycarbonyl, (C 2 -C 6) alkenyl, (C 2 -C 6 ) alkynyl, is hydrogen, is hydrogen, fluorine or chlorine.
  • R 4 when Q is 3,4-dimethoxyphenyl, R 4 is not 3,4-dimethoxyphenyl) ethyl and when Q is phenyl R 4 is not 1 - (naphthalenyl) ethyl is hydrogen, (C 1 -C 6 ) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) -alkenyl, (C 3 -C 6) alkynyl, (Ci-C6) - alkoxy- (Ci-C 6) alkyl, (Ci- C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl,
  • Y is -CH 2 -
  • W 1 and W 2 are oxygen
  • R 1 is hydrogen, amino, methyl, cyclopropyl, benzyl, p-methoxy-benzyl, allyl, propargyl
  • R 2 is hydrogen
  • R 3 is hydrogen, fluorine or chlorine.
  • Q is one of the groupings Q-1.1 to Q-13.16 specifically mentioned in the table above,
  • Z represents the groups Z-1 .1 to Z-3.60.
  • Y is -CH 2 -
  • W 1 and W 2 are oxygen
  • R 1 is hydrogen, methyl, cyclopropyl, benzyl, p-methoxy-benzyl, allyl, propargyl
  • R 2 is hydrogen
  • R is hydrogen
  • the designation of chemical groups generally means that the attachment to the skeleton or the rest of the molecule takes place via the last-mentioned structural element of the relevant chemical group that is, for example, in the case of (C 2 -C 6) -alkenyloxy via the oxygen atom, and in the case of heterocyclyl (Ci-Cg) -alkyl or R 12 0 (0) C (Ci-Cg) -alkyl in each case via the C Atom of the alkyl group.
  • alkylsulfonyl alone or as part of a chemical group - is straight-chain or branched alkylsulfonyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms 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 is optionally substituted pyridylsulfonyl, pyrimidinylsulfonyl, pyrazinylsulfonyl or optionally substituted polycyclic
  • 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) (ci-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- Dimethylbuty
  • Cycloalkylthio means according to the invention a bonded via a sulfur atom
  • Alkoxy means an alkyl radical attached via an oxygen atom, for example (but not limited to) (C 1 -C 6) -alkoxy, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-alkoxy.
  • Alkenyloxy is an alkenyl radical bound via an oxygen atom
  • alkynyloxy is an alkynyl radical bonded via an oxygen atom, such as (C 2 -C 10) -, (C 2 -C 6 ) - or (C 2 -C 4 ) -alkenoxy or (C 3 -C 10) -, (C 3 -C 6 ) - or (C 3 -C 4 ) -Alkmoxy.
  • Cycloalkyloxy means a cycloalkyl radical bonded via an oxygen atom.
  • the number of C 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) -
  • alkyl radicals attached to the skeleton via a carbonyloxy group such as (C1-C10) -, (CI-C ⁇ ) - or (Ci-C i) alkylcarbonyloxy.
  • the number of C atoms refers to the alkyl radical in the alkylcarbonyloxy group.
  • aryl means an optionally substituted mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl and the like, preferably phenyl
  • optionally substituted aryl are also Vectorcyclische systems, such as
  • aryl is usually also of the term 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,
  • heterocyclic radical contains at least one heterocyclic ring
  • heterocyclic ring in which at least one C atom is replaced by a heteroatom, preferably by a heteroatom from the group N, O, S, P
  • N, O, S, P saturated, unsaturated, partially saturated or heteroaromatic and may be unsubstituted or substituted, wherein the binding site is located on a ring atom.
  • heterocyclyl or heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings.
  • polycyclic systems are also included, for example 8-azabicyclo [3.2.1] octanyl, 8-azabicyclo [2.2.2] octanyl or 1-azabicyclo [2.2.1] heptyl.
  • optionally substituted heterocyclyl also become
  • the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but not two
  • Oxygen atoms are to be directly adjacent, such as with a heteroatom from the group N, O and S 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2 or 3-yl, 2,3- dihydro-lH-pyrrole
  • 3-membered and 4-membered heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3 -Dioxetan-2-yl.
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical having two heteroatoms from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazole-3 or 4 or 5-yl; 4,5-dihydro-1H-pyrazole-1 - or 3 or 4 or 5-yl; 2,3-dihydro-1H-pyrazole-1 - or 2 - or
  • 6-yl 1,4,5,6-tetrahydropyridazine-1- or 3- or 4- or 5- or 6-yl; 3,4,5,6-tetrahydropyridazine-3- or 4- or 5-yl; 4,5-dihydropyridazine-3 or 4-yl; 3,4-dihydropyridazine-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazine-3 or 4-yl; 1,6-dihydropyriazine-1- or 3- or 4- or 5- or 6-yl;
  • 1,2-dithiin-3 or 4-yl 1,2-dithiin-3 or 4-yl; l, 2-dithiin-3 or 4-yl; l, 3-dithian-2 or 4 or 5-yl; 4H-l, 3-dithiin-2 or 4 or 5 or 6-yl; Isoxazolidine-2 or 3 or 4 or 5-yl; 2,3-dihydroisoxazole-2- or 3- or
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group N, O and S, such as, for example, l, 4,2-dioxazolidin-2 or 3 or 5-yl; l, 4,2-dioxazol-3 or 5-yl; 1,2,2-dioxazinane-2- or -3- or 5- or 6-yl; 5,6-dihydro-l, 4,2-dioxazine-3 or 5 or 6-yl; l, 4,2-dioxazine-3- or 5- or 6-yl; l, 4,2-dioxazepan-2 or 3 or 5 or 6 or 7-yl; 6,7-dihydro-5H-l, 4,2-dioxazepine-3 or 5 or 6 or 7-yl; 2,3-dihydro-7H-l, 4,2-dioxazepin-2 or 3 or 5 or 6 or 7-yl; 2,3-dihydro-5H-1,
  • heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl,
  • Alkylaminocarbonyl bis-alkylaminocarbonyl, cycloalkylaminocarbonyl,
  • Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below, in addition to oxo and thioxo.
  • the oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring.
  • lactones and lactams are preferably also included.
  • the oxo group may also be attached to the hetero ring atoms, which may exist in different oxidation states, e.g. For example, at N and S, the divalent groups N (O), S (O) (also SO for short) and S (O) 2 (also SO2 for short) occur and form in the heterocyclic ring.
  • N (O) and -S (0) groups both enantiomers are included.
  • heteroaryl stands for heteroaromatic compounds, ie.
  • Heteroaryls according to the invention are, for example, 1H-pyrrol-1-yl; lH-pyrrol-2-yl; 1H-pyrrol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, 1H-imidazol-1-yl; lH-imidazol-2-yl; 1H-imidazol-4-yl; lH-imidazol-5-yl; lH-pyrazol-l-yl; lH-pyrazol-3-yl; lH-pyrazol-4-yl; lH-pyrazol-5-yl, 1H-1,2,3-triazol-1-yl, 1H-l, 2,3-triazol-4-yl, 1H-l, 2,
  • Carbon atoms part of another aromatic ring they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatic.
  • quinolines e.g., quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • Isoquinolines e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl
  • quinoxaline quinazoline
  • cinnoline 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyrazine
  • heteroaryl are also 5- or 6-membered benzo-fused rings from the group 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indol-4-yl, 1H- Indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran 5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophene-2-yl, 1-benzothiophen-3-yl, 1-benzothiophene-4-yl, 1-benzothiophene-5 yl, 1-benzothiophene-6-yl, 1-benzothiophene-7-yl, 1H-indazol-1-yl, 1H-indazol-3-y
  • halogen means, for example, 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 is referred to in the latter case as “substituted alkyl".
  • Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, particularly preferred Methoxy, methyl, fluoroalkyl, cyano, nitro, fluoro, chloro, bromo or iodo.
  • the prefix "bis” also includes the combination of different alkyl radicals, 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 indication for C atoms, d. H. includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl.
  • General alkyl radicals having a larger specified range of carbon atoms eg. As "(Ci-C6) alkyl", accordingly also include straight-chain or branched alkyl radicals having a larger number of C atoms, d. H. according to example, the alkyl radicals with 5 and 6 carbon atoms.
  • the lower carbon skeletons are, for example, 1 to 6 C atoms or in unsaturated groups having 2 to 6 carbon atoms, preferably.
  • Alkyl radicals including in the assembled radicals such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i Hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1, 4-dimethylpentyl;
  • Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, wherein at least one double bond or triple bond is contained. Preference is given to radicals having a double bond or
  • alkenyl in particular also includes straight-chain or branched open-chain
  • Hydrocarbon radicals having more than one double bond such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulated double bonds, such as allenyl (1,2-propadienyl), 1, 2-butadienyl and 1,2,3-pentatrienyl.
  • Alkenyl is, for example, vinyl, which may optionally be substituted by further alkyl radicals, for example (but not limited to) (C 2 -C 6) -alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3 Pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl 2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl
  • alkynyl in particular also includes straight-chain or branched open-chain
  • C 2 -C 6) -alkynyl is, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3 Pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1 Ethyl 2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl,
  • cycloalkyl means a carbocyclic, saturated ring system preferably having 3-8 ring C atoms, eg cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio , Haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, alkocycarbonyl,
  • Cycloalkylaminocarbonyl In the case of optionally substituted cycloalkyl cyclic systems are included with substituents, wherein substituents having a double bond on
  • 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 [1.1.1] 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 adamantane -2-yl, but also systems such.
  • spirocyclic aliphatic systems are also included, such as spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl, spiro [3.3] hept-1-yl, spiro [3.3] hept-2-yl.
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 C atoms, eg 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2- Cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl, wherein substituents having a double bond on the cycloalkenyl radical, for example an alkylidene group such as methylidene, are also included in the case of optionally substituted cycloalkenyl the explanations for substituted Corresponding to cycloalkyl.
  • substituents having a double bond on the cycloalkenyl radical for example an alkylidene group such as methylidene
  • Cycloalkylidene means carbocyclic radical bonded via a double bond.
  • 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 denotes an aryloxy radical bonded via an alkyl group and
  • 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 attached via an alkyl group
  • heterocyclylalkyl means a heterocyclyl group bonded through an alkyl group.
  • Cycloalkylalkyl means a cycloalkyl group attached through an alkyl group, e.g. B.
  • cyclopropylmethyl (but not limited to) cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropyleth-1-yl, 2-cyclopropyleth-1-yl, 1-cyclopropylprop-1-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, According to the invention "trialkylsilyl" - alone or as part of a chemical group - is straight-chain or
  • Carbon atoms such as tri - [(Ci-Cs) -, (CI-C ⁇ ) - 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-dimethyl-1-yl) silyl, tri (2,2-dimethyl-1-yl) silyl.
  • stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants.
  • the invention thus also relates to all stereoisomers which comprises the general formula (I) but are not specified with their specific stereoform, and mixtures thereof.
  • the purification can also by
  • Suitable isolation, purification and stereoisomer separation methods of compounds of the general formula (I) are methods which are generally known to the person skilled in the art from analogous cases, for example by physical methods such as crystallization, chromatography methods, especially column chromatography and HPLC (high pressure liquid chromatography), distillation . optionally under reduced pressure, extraction and other methods, any remaining mixtures can usually be separated by chromatographic separation, for example on chiral solid phases.
  • Suitable for preparative amounts or on an industrial scale are processes such as crystallization, for example diastereomeric salts, which can be obtained from the diastereomer mixtures with optically active acids and optionally in the presence of acidic groups having optically active bases.
  • the substituted pyrrolidinones of the general formula (I) 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 1 , W 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 of the general formula (I) have the meanings defined above in the following schemes unless definitions are given by way of example but not by way of limitation.
  • 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. ⁇ .
  • 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 may be carried out in a temperature range between -20 ° C and 100 ° C, preferably -5 ° C and 50 ° C.
  • R ' (C 1 -C 4 ) -alkyl.
  • the synthesis of the compound of general formula (IV) can be effected by reduction of the compound of general formula (V) and subsequent in situ cyclization of the amine formed.
  • R ' (C 1 -C 4 ) -alkyl.
  • Scheme 4 describes the synthesis of the compound of the general formula (V) by reacting a diester of the general formula (VI) with a nitroalkane of the general formula (VII) in the presence of a base.
  • the base may be an alkoxide salt of an alkali metal (such as sodium methylate or sodium ethylate) in an adequate solvent such as methanol or ethanol.
  • the reaction may be carried out with bases such as lithium hexa-methyldisilazane, sodium hexamethyldisilazane or lithium diisopropylamide in an adequate solvent such as tetrahydrofuran.
  • R ' (C 1 -C 4 ) -alkyl.
  • the compounds of general formula (VI) can be prepared by Knoevenagel condensation of an aldehyde of general formula (VIII) and malonic esters of general formula (IX) (see Scheme 5, G. Jones, Organic Reactions Volume 15, John Wiley and Sons, 1967 ).
  • the base may be an alkanolate salt or hydroxide of an alkali metal (such as sodium methylate or sodium ethylate), in an adequate solvent such as methanol or ethanol, or bases such as lithium hexamethyldisilazane,
  • the compounds of general formula (X) can be prepared by condensation of an aldehyde of general formula (VIII) and compounds of general formula (XI) in the presence of a base such as sodium hydride in an adequate solvent such as tetrahydrofuran (see Scheme 7) ).
  • the compounds of the general formula (Ia) can be obtained by reduction of the compound of the general formula (XII) and subsequent in situ cyclization of the amine formed.
  • Nickel (II) chloride
  • R ' (C 1 -C 4 ) -alkyl.
  • Scheme 9 describes the synthesis of the compound of general formula (XII) by reaction of a malonic ester of general formula (XIII) with a nitro olefin of general formula (X) in the presence of a base.
  • the base may be an alkanolate salt or hydroxide of an alkali metal (such as sodium methylate or sodium ethylate) in an adequate solvent such as methanol or ethanol.
  • an alkanolate salt or hydroxide of an alkali metal such as sodium methylate or sodium ethylate
  • an adequate solvent such as methanol or ethanol.
  • Lithiumhexamethyldisilazan, Natriumhexamethyldisilazan or lithium diisopropylamide perform in an adequate solvent such as tetrahydrofuran.
  • R ' (C 1 -C 4 ) -alkyl.
  • Monomalonic acid chlorides of the general formula (XIV) with an amine of the general formula (XV) in the presence of a base see Scheme 10).
  • the base can be triethylamine or
  • Diisopropylethylamine and the reaction can be carried out in an adequate solvent such as dichloromethane or tetrahydrofuran.
  • R ' (C 1 -C 4 ) -alkyl.
  • reaction mixture was again stirred under reflux on a water separator overnight and then cooled to room temperature and washed with 2M aqueous HCl and subsequently with sat. Washed sodium chloride solution, dried over magnesium sulfate, filtered and concentrated.
  • the reaction mixture was stirred overnight at room temperature and then sat.
  • Table 1.1 Preferred compounds of the formula (1.1) are the compounds 1.1-1 to 1.1-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.1-1 to 1.1-270 of Table LI are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1 Preferred compounds of the formula (1.1) are the compounds 1.1-1 to 1.1-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.1-1 to 1.1-270 of Table LI are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1 Preferred compounds of the formula (1.1) are the compounds 1.1-1 to 1.1-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.1-1 to 1.1-270 of Table LI are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1 Preferred compounds of the formula (1.1) are the
  • Table 1.2 Preferred compounds of the formula (1.2) are the compounds 1.2-1 to 1.2-270, wherein Q has the meanings indicated in the respective line of Table 1.
  • the compounds 1.2-1 to 1.2-270 of Table 1.2 are thus characterized by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.3 Preferred compounds of the formula (1.3) are the compounds 1.3-1 to 1.3-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.3-1 to 1.3-270 of Table 1.3 are thus determined by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.4 Preferred compounds of the formula (1.4) are the compounds 1.4-1 to 1.4-270, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.4-1 to 1.4-270 of Table 1.4 are thus characterized by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.5 Preferred compounds of the formula (1.5) are the compounds 1.5-1 to 1.5-270, wherein Q 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 270 defined for Q of Table A.
  • Table 1.6 Preferred compounds of the formula (1.6) are the compounds 1.6-1 to 1.6-270, in which Q has the meanings given in Table 1 of each Table.
  • the compounds 1.6-1 to 1.6-270 of Table 1.6 are thus characterized by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.7 Preferred compounds of the formula (1.7) are the compounds 1.7-1 to 1.7-270, wherein Q has the meanings indicated in the respective line of Table 1.
  • the compounds 1.7-1 to 1.7-270 of Table 1.7 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.8 Preferred compounds of the formula (1.8) are the compounds 1.8-1 to 1.8-270, in which Q has the meanings indicated in the respective line of Table 1.
  • the compounds 1.8-1 to 1.8-270 of Table 1.8 are thus characterized by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.9 Preferred compounds of the formula (1.9) are the compounds 1.9-1 to 1.9-270, wherein Q has the meanings indicated in the respective line of Table 1.
  • the compounds 1.9-1 to 1.9-270 of Table 1.9 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.10 Preferred compounds of the formula (1.10) are the compounds 1.10-1 to 1.10-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.10-1 to 1.10-270 of Table 1.10 are therefore distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.11 Preferred compounds of the formula (1.11) are the compounds 1.11 - 1 to 1.11 -270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds LI 1-1 to LI 1-270 of Table LI 1 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.12 Preferred compounds of the formula (1.12) are the compounds 1.12-1 to 1.12-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.12-1 to 1.12-270 of Table 1.12 are thus distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.13 Preferred compounds of the formula (1.13) are the compounds 1.13-1 to 1.13-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.13-1 to 1.13-270 of Table 1.13 are thus distinguished by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.14 Preferred compounds of the formula (1.14) are the compounds 1.14-1 to 1.14-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.14-1 to 1.14-270 of Table 1.14 are thus distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.15 Preferred compounds of the formula (1.15) are the compounds 1.15-1 to 1.15-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.15-1 to 1.15-270 of Table 1.15 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.16 Preferred compounds of the formula (1.16) are the compounds 1.16-1 to 1.16-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.16-1 to 1.16-270 of Table 1.16 are therefore distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.17 Preferred compounds of the formula (1.17) are the compounds 1.17-1 to 1.17-270, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.17-1 to 1.17-270 of Table 1.17 are thus distinguished by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.18 Preferred compounds of the formula (1.18) are the compounds 1.18-1 to 1.18-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.18-1 to 1.18-270 of Table 1.18 are thus distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.19 Preferred compounds of the formula (1.19) are the compounds 1.19-1 to 1.19-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.19-1 to 1.19-270 of Table 1.19 are therefore distinguished by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.20 Preferred compounds of the formula (1.20) are the compounds 1.20-1 to 1.20-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.20-1 to 1.20-270 of Table 1.20 are thus distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.21 Preferred compounds of the formula (1.21) are the compounds 1.21-1 to 1.21-270, wherein Q has the meanings given in Table 1 of each line.
  • the compounds 1.21-1 to 1.21-270 of Table 1.21 are thus distinguished by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.22 Preferred compounds of the formula (1.22) are the compounds 1.22-1 to 1.22-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.22-1 to 1.22-270 of Table 1.22 are thus distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.23 Preferred compounds of the formula (1.23) are the compounds 1.23-1 to 1.23-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the connections 1.23-1 to 1.23-270 of Table 1.23 are therefore distinguished by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.24 Preferred compounds of the formula (1.24) are the compounds 1.24-1 to 1.24-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.24-1 to 1.24-270 of Table 1.24 are thus distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.25 Preferred compounds of the formula (1.25) are the compounds 1.25-1 to 1.25-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.25-1 to 1.25-270 of Table 1.25 are thus distinguished by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.26 Preferred compounds of the formula (1.26) are the compounds 1.26-1 to 1.26-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.26-1 to 1.26-270 of Table 1.26 are thus distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.27 Preferred compounds of the formula (1.27) are the compounds 1.27-1 to 1.27-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.27-1 to 1.27-270 of Table 1.27 are thus distinguished by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.28 Preferred compounds of the formula (1.28) are the compounds 1.28-1 to 1.28-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the connections 1.28-1 to 1.28-270 of Table 1.28 are therefore distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.29 Preferred compounds of the formula (1.29) are the compounds 1.29-1 to 1.29-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.29-1 to 1.29-270 of Table 1.29 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.30 Preferred compounds of the formula (1.30) are the compounds 1.30-1 to 1.30-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.30-1 to 1.30-270 of Table 1.30 are thus distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.31 Preferred compounds of the formula (1.31) are the compounds 1.31-1 to 1.31-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.31-1 to 1.31-270 of Table 1.31 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.32 Preferred compounds of the formula (1.32) are the compounds 1.32-1 to 1.32-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.32-1 to 1.32-270 of Table 1.32 are therefore distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.33 Preferred compounds of the formula (1.33) are the compounds 1.33-1 to 1.33-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.33-1 to 1.33-270 of Table 1.33 are thus distinguished by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.34 Preferred compounds of the formula (1.34) are the compounds 1.34-1 to 1.34-270, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.34-1 to 1.34-270 of Table 1.34 are therefore distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.35 Preferred compounds of the formula (1.35) are the compounds 1.35-1 to 1.35-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.35-1 to 1.35-270 of Table 1.35 are thus distinguished by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.36 Preferred compounds of the formula (1.36) are the compounds 1.36-1 to 1.36-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the connections 1.36-1 to 1.36-270 of Table 1.36 are therefore distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.37 Preferred compounds of the formula (1.37) are the compounds 1.37-1 to 1.37-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.37-1 to 1.37-270 of Table 1.37 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.38 Preferred compounds of the formula (1.38) are the compounds 1.38-1 to 1.38-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.38-1 to 1.38-270 of Table 1.38 are thus distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.39 Preferred compounds of the formula (1.39) are the compounds 1.39-1 to 1.39-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.39-1 to 1.39-270 of Table 1.39 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.40 Preferred compounds of the formula (1.40) are the compounds 1.40-1 to 1.40-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.40-1 to 1.40-270 of Table 1.40 are therefore distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.41 Preferred compounds of the formula (1.41) are the compounds 1.41-1 to 1.41-270, in which Q has the meanings given in Table 1 in each line.
  • the compounds 1.41-1 to 1.41-270 of Table 1.41 are thus distinguished by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.42 Preferred compounds of the formula (1.42) are the compounds 1.42-1 to 1.42-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.42-1 to 1.42-270 of Table 1.42 are thus distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.43 Preferred compounds of the formula (1.43) are the compounds 1.43-1 to 1.43-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.43-1 to 1.43-270 of Table 1.43 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.44 Preferred compounds of the formula (1.44) are the compounds 1.44-1 to 1.44-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.44-1 to 1.44-270 of Table 1.44 are thus distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.45 Preferred compounds of the formula (1.45) are the compounds 1.45-1 to 1.45-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.45-1 to 1.45-270 of Table 1.45 are therefore distinguished by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.46 Preferred compounds of the formula (1.46) are the compounds 1.46-1 to 1.46-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.46-1 to 1.46-270 of Table 1.46 are thus characterized by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.47 Preferred compounds of the formula (1.47) are the compounds 1.47-1 to 1.47-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.47-1 to 1.47-270 of Table 1.47 are therefore distinguished by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.48 Preferred compounds of the formula (1.48) are the compounds 1.48-1 to 1.48-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.48-1 to 1.48-270 of Table 1.48 are thus characterized by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.49 Preferred compounds of the formula (1.49) are the compounds 1.49-1 to 1.49-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.49-1 to 1.49-270 of Table 1.49 are thus distinguished by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.50 Preferred compounds of the formula (1.50) are the compounds 1.50-1 to 1.50-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.50-1 to 1.50-270 of Table 1.50 are therefore distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.51 Preferred compounds of the formula (1.51) are the compounds 1.51-1 to 1.51-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.51-1 to 1.51-270 of Table 1.51 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Preferred compounds of the formula (I. 52) are the compounds I. 52-1 to I. 52-270, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds I. 52-1 to I. 52-270 of Table I. 52 are thus characterized by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.53 Preferred compounds of the formula (1.53) are the compounds 1.53-1 to 1.53-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.53-1 to 1.53-270 of Table 1.53 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.54 Preferred compounds of the formula (1.54) are the compounds 1.54-1 to 1.54-270, in which Q has the meanings given in Table 1 of each Table.
  • the compounds 1.54-1 to 1.54-270 of Table 1.54 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.55 Preferred compounds of the formula (I. 55) are the compounds I. 55-1 to I. 55-270, wherein Q has the meanings indicated in the respective line of Table 1.
  • the compounds I. 55-1 to I. 55-270 of Table I. 55 are thus by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.56 Preferred compounds of the formula (1.56) are the compounds 1.56-1 to 1.56-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.56-1 to 1.56-270 of Table 1.56 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.57 Preferred compounds of the formula (I. 57) are the compounds I. 57-1 to I. 57-270, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds I. 57-1 to I. 57-270 of Table I. 57 are thus characterized by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.58 Preferred compounds of the formula (1.58) are the compounds 1.58-1 to 1.58-270, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.58-1 to 1.58-270 of Table 1.58 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.59 Preferred compounds of the formula (I. 59) are the compounds I. 59-1 to I. 59-270, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds I. 59-1 to I. 59-270 of Table I. 59 are thus characterized by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.60 Preferred compounds of the formula (1.60) are the compounds 1.60-1 to 1.60-270, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.60-1 to 1.60-270 of Table 1.60 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.61 Preferred compounds of the formula (1.61) are the compounds 1.61-1 to 1.61-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.61-1 to 1.61-270 of Table 1.61 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.62 Preferred compounds of the formula (1.62) are the compounds 1.62-1 to 1.62-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.62-1 to 1.62-270 of Table 1.62 are therefore distinguished by the meaning of the respective entries no. 1 to 270 for Q of Table A above.
  • Table 1.63 Preferred compounds of the formula (1.63) are the compounds 1.63-1 to 1.63-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.63-1 to 1.63-270 of Table 1.63 are thus distinguished by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.64 Preferred compounds of the formula (I.64) are the compounds I. 64-1 to I. 64-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds I. 64-1 to I. 64-270 of Table I. 64 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.65 Preferred compounds of the formula (I. 65) are the compounds I. 65-1 to I. 65-270, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds I. 65-1 to I. 65-270 of Table I. 65 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.66 Preferred compounds of the formula (I. 66) are the compounds I. 66-1 to I. 66-270, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds I. 66-1 to I. 66-270 of Table I. 66 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.67 Preferred compounds of the formula (I. 67) are the compounds I. 67-1 to I. 67-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds I. 67-1 to I. 67-270 of Table I. 67 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.68 Preferred compounds of the formula (I. 68) are the compounds I. 68-1 to I. 68-270, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds I. 68-1 to I. 68-270 of Table I. 68 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.69 Preferred compounds of the formula (I. 69) are the compounds I. 69-1 to I. 69-270, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds I. 69-1 to I. 69-270 of Table I. 69 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.70 Preferred compounds of the formula (I. 70) are the compounds I. 70-1 to I. 70-270, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds I. 70-1 to I. 70-270 of Table I. 70 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.71 Preferred compounds of the formula (I.71) are the compounds I. 71-1 to I. 71-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds I. 71-1 to I. 71-270 of Table I. 71 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.72 Preferred compounds of the formula (I. 72) are the compounds I. 72-1 to I. 72-270, wherein Q has the meanings indicated in the respective line of Table 1.
  • the compounds I. 72-1 to I. 72-270 of Table I. 72 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.73 Preferred compounds of the formula (I. 73) are the compounds I. 73-1 to I. 73-270, wherein Q has the meanings indicated in Table 1 of each Table.
  • the compounds I. 73-1 to I. 73-270 of Table I. 73 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.74 Preferred compounds of the formula (I.74) are the compounds I.74-1 to I.74-270, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds I. 74-1 to I. 74-270 of Table I. 74 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Preferred compounds of the formula (I. 75) are the compounds I. 75-1 to I. 75-270, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds I. 75-1 to I. 75-270 of Table I. 75 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.76 Preferred compounds of the formula (I. 76) are the compounds I. 76-1 to I. 76-270, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds I. 76-1 to I. 76-270 of Table I. 76 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.77 Preferred compounds of the formula (I.77) are the compounds I. 77-1 to I. 77-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds I. 77-1 to I. 77-270 of Table I. 77 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.78 Preferred compounds of the formula (I. 78) are the compounds I. 78-1 to I. 78-270, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds I. 78-1 to I. 78-270 of Table I. 78 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.79 Preferred compounds of the formula (I.79) are the compounds I. 79-1 to I. 79-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds I. 79-1 to I. 79-270 of Table I. 739 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • Table 1.80 Preferred compounds of the formula (I.80) are the compounds I. 80-1 to I. 80-270, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds I. 80-1 to I. 80-270 of Table I. 80 are thus characterized by the meaning of the respective entries no. 1 to 270 defined for Q of Table A.
  • the 1H NMR data of selected examples are noted in terms of 1H NMR peak lists. For each signal peak, first the ⁇ value in ppm and then the signal intensity in round brackets are listed. The ⁇ -value signal intensity number pairs of different signal peaks are listed separated by semicolons.
  • the peak list of an example therefore has the form: ⁇ (intensity ⁇ ; 82 (intensity 2);; ⁇ ; (intensity ⁇ ;; ⁇ ⁇ (intensity n )
  • the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum.
  • the peaks of stereoisomers of the target compounds and / or peaks of impurities usually have on average a lower intensity than the peaks of the target compounds (for example with a purity of> 90%).
  • stereoisomers and / or impurities may be typical of each
  • An expert calculating the peaks of the target compounds by known methods can isolate the peaks of the target compounds as needed, using additional intensity filters if necessary. This isolation would be similar to peak picking in classical 1H NMR interpretation.
  • ⁇ 7.5180 (1.2); 7.3091 (6.2); 7.2903 (10.4); 7.2830 (9.1); 7.2695 (15.3); 7.2592 (170.5); 7.2510 (12.8); 7.2374 (7.3); 7.2056 (3.1); 7.1154 (4.9); 7.0991 (6.8); 7.0966 (7.5); 7.0749 (5.3); 7.0500 (5.2); 7.0286 (3.6); 6.9951 (1.4); 6.2269 (1.1); 4.5159 (12.9); 4.5013 (13.0); 3.7498 (0.7); 3.7386 (0.9); 3.7267 (0.9); 3.7085 (0.6); 3.5525 (1.0); 3.5405 (1.0); 3.5297 (0.8); 3.5031 (0.9); 3.4866 (1.3); 3.4698 (0.9); 3.2748 (16.0); 2.2834 (0.8); 2.2604 (0.9); 2.2456 (2.2); 2.2252 (0.6); 2.1941 (3.0); 2.1298 (0.6); 2.0978 (0.7); 1.5788 (0.6); 1.5591 (0.6); 1.3890 (0.6); 1.3703 (0.6);
  • ⁇ 7.5186 (4.5); 7,5009 (2.8); 7.3095 (0.8); 7.2598 (521.0); 7.2259 (0.6); 7.1333 (0.6); 7.1083 (3.5); 7.0909 (7.0); 7.0858 (8.1); 7.0777 (6.0); 7.0692 (6.5); 7.0627 (5.9); 7.0549 (7.6); 7.0466 (6.8); 7.0410 (11.4); 7.0310 (2.4); 7.0248 (3.8); 7.0220 (3.7); 7.0136 (1.6); 7.0013 (1.4); 6.9957 (3.0); 5.9019 (2.9); 4.5589 (16.0); 4.5442 (15.8); 3.7453 (0.6); 3.7339 (0.6); 3.7221 (0.7); 3.5602 (5.2); 3.5495 (1.0); 3.5380 (11.1); 3.5263 (0.9); 3.5143 (6.2); 3.5009 (0.8); 3.4844 (1.3); 3.4684 (0.6); 3.3608 (0.6); 3.1892 (6.5); 3.1731 (6.9); 3.1652 (6.0); 3.1487 (6.0); 3.1241 (11.4
  • ⁇ 7.5190 (0.7); 7.2601 (78.8); 7.2108 (0.6); 7.1308 (0.7); 7.1207 (1.3); 7.1126 (1.4); 7.1048 (2.0); 7.0865 (2.3); 7.0805 (2.2); 7.0678 (2.4); 7.0633 (2.5); 7.0543 (3.2); 7.0493 (1.9); 7.0470 (2.0); 7.0445 (1.7); 7.0405 (1.4); 7.0347 (2.2); 7.0253 (1.0); 7.0163 (0.8); 6.9961 (0.7); 4.5481 (1.9); 4.5333 (3.5); 4.5167 (3.3); 4.5002 (2.6); 3.4721 (1.1); 3.4519 (0.5); 3.2393 (2.9); 3.0482 (1.0); 3.0400 (0.7); 3.0267 (0.8); 2.8238 (1.1); 2.8077 (1.0); 2.5074 (0.5); 2.0439 (0.6); 2.0213 (16.0); 2.0083 (0.9); 1.8732 (0.6); 1.8534 (0.6); 1.8452 (0.9); 1.8323 (1.0); 1.8244 (1.1); 1.8119 (
  • herbicide and / or plant growth regulator preferably in crops of useful and / or ornamental plants.
  • the present invention furthermore relates to a method for controlling harmful plants and / or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one which is characterized as being preferred or particularly preferred
  • Embodiment in particular one or more compounds of the formulas (LI) to (1.80) and / or salts thereof, each as defined above, or an agent according to the invention, as defined below, on the (harmful) plants, (harmful) plant seeds, the soil , in which or on which the (harmful) plants grow, or the cultivated area is applied.
  • the present invention also provides a process for controlling undesirable plants, preferably in crops, characterized in that an effective amount of one or more compounds of the general formula (I) and / or salts thereof, as defined above, preferably in one of preferred or particularly preferred marked
  • Embodiment in particular one or more compounds of the formulas (LI) to (1.80) and / or salts thereof, each as defined above, or an agent according to the invention, as defined below, on undesirable plants (eg harmful plants such as mono- or dicotyledonous weeds or unwanted Crops), the seed of the undesirable plants (ie, plant seeds, eg, grains, seeds or vegetative propagules such as tubers or sprouts with buds), the soil in which or on which the undesirable plants grow (eg, the soil of cultivated land or non-cultivated land ) or the area under cultivation (ie area on which the unwanted plants will grow) is applied.
  • undesirable plants eg harmful plants such as mono- or dicotyledonous weeds or unwanted Crops
  • the seed of the undesirable plants ie, plant seeds, eg, grains, seeds or vegetative propagules such as tubers or sprouts with buds
  • the soil in which or on which the undesirable plants grow eg, the soil of cultivated land or non-cultivated land
  • the present invention further provides methods for controlling the growth of plants, preferably of useful plants, characterized in that an effective amount - one or more compounds of general formula (I) and / or their salts, as defined above, preferably in a which is characterized as being preferred or particularly preferred
  • Embodiment in particular one or more compounds of the formulas (LI) to (1.80) and / or salts thereof, each as defined above, or - an agent according to the invention, as defined below, the plant, the seed of the plant (ie plant seeds, eg grains , Seeds or vegetative
  • Propagating organs such as tubers or sprouts with buds
  • the soil in which or on which the plants grow e.g., the soil of cultivated land or non-cultivated land
  • the cultivated area i.e., area on which the plants will grow
  • the compounds according to the invention or the agents according to the invention may e.g. in Vorsaat- (possibly also by incorporation into the soil), pre-emergence and / or
  • one or more compounds of the general formula (I) and / or their salts are employed for controlling harmful plants or regulating growth in crops of crops or ornamental plants, the crops or ornamentals in a preferred embodiment are transgenic plants.
  • the compounds of general formula (I) and / or their salts according to the invention are suitable for controlling the following genera of monocotyledonous and dicotyledonous harmful plants:
  • the compounds according to the invention are applied to the surface of the earth (weeds and / or weeds) prior to germination (pre-emergence method), either the emergence of the weed seedlings or weed seedlings is completely prevented or they grow up to the cotyledon stage, but then grow and eventually die off after three to four weeks.
  • the compounds of the invention have excellent herbicidal activity against mono- and dicotyledonous weeds, crops of economically important crops, e.g. dicotyledonous cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous cultures of the genera Allium, Pineapple , Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea, depending on the structure of the respective compound of the invention and their application rate only insignificantly or not at all damaged.
  • the present compounds are very well suited for the selective control of undesired plant growth in crops such as
  • the compounds according to the invention (depending on their respective structure and the applied application rate) have excellent growth-regulatory properties in crop plants. They regulate the plant's metabolism and can thus be used to specifically influence plant ingredients and facilitate harvesting, eg by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth, without killing the plants.
  • An inhibition of vegetative growth plays in many mono- and dicots Cultures play an important role because, for example, the storage can be reduced or completely prevented.
  • the active compounds can also be used to control harmful plants in crops of genetically engineered or conventional mutagenized plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties concern e.g. the crop in terms of quantity, quality, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or altered quality of starch or those with others
  • Preferred for transgenic cultures is the use of the compounds of the invention and / or their salts in economically important transgenic crops of useful and ornamental plants, e.g. of cereals such as wheat, barley, rye, oats, millet, rice and maize or also crops of sugar beet, cotton, soya, rapeseed, potato, tomato, pea and other vegetables.
  • the compounds of the invention may also be used as herbicides in
  • Crop plants are used, which are resistant to the phytotoxic effects of herbicides or have been made genetically resistant.
  • the active compounds can also be used for controlling harmful plants in crops of known or yet to be developed genetically modified plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties concern e.g. the crop in terms of quantity, quality, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or altered quality of starch or those with others
  • Other particular properties may include tolerance or resistance to abiotic stressors, e.g. Heat, cold, drought, salt and ultraviolet radiation are present.
  • Crop plants are used, which are resistant to the phytotoxic effects of herbicides or have been made genetically resistant.
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences.
  • Base exchanges are made, partial sequences removed or natural or synthetic sequences added.
  • adapters or linkers can be attached to the fragments.
  • RNA for example, be achieved by the expression of at least one corresponding antisense RNA, a sense RNA to achieve a Cosuppressions freees or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product.
  • DNA molecules can be used which comprise the entire coding sequence of a gene product including any flanking sequences, as well as DNA molecules which comprise only parts of the coding sequence, which parts have to be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
  • the synthesized protein may be located in any compartment of the plant cell.
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment.
  • Sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227).
  • the expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
  • the transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants can in principle be plants of any one
  • Plant species i. both monocotyledonous and dicotyledonous plants.
  • the compounds (I) according to the invention can be used in transgenic cultures which are resistant to growth factors, such as e.g. Dicamba or against herbicides, the essential
  • Plant enzymes e.g. Acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or
  • Hydoxyphenylpyruvate dioxygenases are resistant to herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues.
  • effects which are specific for the application in the respective transgenic crop often occur, for example a modified or specially extended weed spectrum which can be controlled Application rates that can be used for the application, preferably good combinability with the herbicides to which the transgenic culture is resistant, and influencing growth and yield of the transgenic crops.
  • the invention therefore also relates to the use of the compounds of the general formula (I) according to the invention and / or salts thereof as herbicides for controlling harmful plants in crops of useful or ornamental plants, optionally in transgenic crop plants.
  • cereals preferably corn, wheat, barley, rye, oats, millet, or rice, in the pre- or post-emergence.
  • Preference is also the use in soy in the pre or postemergence.
  • Growth regulation of plants also includes the case where the active ingredient of general formula (I) or its salt is formed from a precursor substance ("prodrug”) only after plant, plant or soil application.
  • the invention also provides the use of one or more compounds of the general formula (I) or salts thereof or an agent according to the invention (as defined below) (in a process) for controlling harmful plants or regulating the growth of plants, characterized in that an effective amount of one or more compounds of general formula (I) or their salts on the plants (weeds, optionally together with the crops) plant seeds, the soil in which or on which the plants grow, or applied to the acreage.
  • the invention also provides a herbicidal and / or plant growth-regulating agent, characterized in that the agent
  • Embodiment in particular one or more compounds of the formulas (LI) to (1.80) and / or salts thereof, in each case as defined above,
  • one or more further agrochemically active substances preferably selected from the group consisting of insecticides, acaricides, nematicides, other herbicides (ie those which do not correspond to formula (I) as defined above), fungicides, safeners, fertilizers and / or other growth regulators,
  • a herbicidal or plant growth-regulating agent according to the invention preferably comprises one, two, three or more formulation aids customary in crop protection (ii) selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusts, at 25 ° C and 1013 mbar solid carriers, preferably adsorptive, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoams, water, organic solvents, preferably at 25 ° C and 1013 mbar with water in any ratio miscible organic solvents.
  • the compounds of the general formula (I) according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations.
  • the invention therefore also relates to herbicidal and plant growth-regulating agents which contain compounds of the general formula (I) and / or salts thereof.
  • the compounds of the general formula (I) and / or their salts can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions .
  • WP wettable powder
  • SP water-soluble powders
  • EC emulsifiable concentrates
  • EW emulsions
  • sprayable solutions such as oil-in-water and water-in-oil emulsions, sprayable solutions .
  • SC Suspension concentrates
  • granules in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations,
  • Microcapsules and waxes are Microcapsules and waxes.
  • formulation and formulation aids such as inert materials, surfactants, solvents and other additives are known to those skilled in the art and are described, for example, in Watkins, Handbook of Insecticides Dust Diluents and Carriers, 2nd Ed., Darland
  • Injectable powders are preparations which are uniformly dispersible in water and, in addition to the active substance, also contain surfactants of an ionic and / or nonionic type (wetting agent,
  • Dispersants for example polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, dibutylnaphthalene-sulfonic acid sodium or also contain oleoylmethyltaurine acid sodium.
  • the herbicidal active compounds are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air-jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents
  • surfactants of ionic and / or nonionic type emulsifiers
  • emulsifiers can be used for example: Alkylarylsulfonsaure calcium salts such as
  • Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol ester
  • Alkylaryl polyglycol ethers fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as e.g. Sorbitan fatty acid esters or
  • Polyoxethylenesorbitanester such. Polyoxyethylene.
  • Dusts are obtained by milling the active ingredient with finely divided solids, e.g.
  • Talc natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates may be water or oil based. They can be prepared, for example, by wet grinding using commercially available bead mills and, if appropriate, addition of surfactants, as described, for example, in US Pat. are already listed above for the other formulation types.
  • Emulsions e.g. Oil-in-water emulsions (EW), for example, by means of stirrers,
  • Solvents and optionally surfactants such as e.g. listed above for the other formulation types.
  • Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • spray drying for the preparation of plate, fluidized bed, extruder and spray granules, see, for example, the procedure in "Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London; JE Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff .; Perry's Chemical Engineer's Handbook, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne des dérivés de 4-cyclopentyl-2-oxopyrrolidin-3-carboxamide et de 4-cyclopropyl-2-oxopyrrolidin-3-carboxamide et des composés apparentés de formule générale (I) utilisés comme produits phytosanitaires 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. La présente invention concerne en outre des agents herbicides et/ou régulateurs de croissance des plantes comprenant un ou plusieurs composés de formule (I).
PCT/EP2018/057156 2017-03-30 2018-03-21 Dérivés de 4-cyclopentyl-2-oxopyrrolidin-3-carboxamide et de 4-cyclopropyl-2-oxopyrrolidin-3-carboxamide et composés apparentés utilisés comme produits phytosanitaires herbicides WO2018177837A1 (fr)

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Cited By (3)

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CN110128419A (zh) * 2019-05-17 2019-08-16 南开大学 一类二氟吡唑杂环甲酰胺类衍生物及其制备方法和用途
WO2020161148A3 (fr) * 2019-02-05 2020-09-17 Syngenta Crop Protection Ag Dérivés de pyrazole
RU2836442C2 (ru) * 2019-02-05 2025-03-17 Сингента Кроп Протекшн Аг Производные пиразола

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WO2016182780A1 (fr) 2015-05-12 2016-11-17 E I Du Pont De Nemours And Company Composés bicycliques substitués par un aryle à titre d'herbicides
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