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WO2019179928A1 - Succinimide-3-carboxamides substitués, leurs sels et leur utilisation comme agents herbicides - Google Patents

Succinimide-3-carboxamides substitués, leurs sels et leur utilisation comme agents herbicides Download PDF

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Publication number
WO2019179928A1
WO2019179928A1 PCT/EP2019/056681 EP2019056681W WO2019179928A1 WO 2019179928 A1 WO2019179928 A1 WO 2019179928A1 EP 2019056681 W EP2019056681 W EP 2019056681W WO 2019179928 A1 WO2019179928 A1 WO 2019179928A1
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alkyl
compounds
cycloalkyl
amino
cas
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English (en)
Inventor
Michael Charles MCLEOD
Thomas Müller
Hendrik Helmke
Olaf Peters
Stefan Lehr
Uwe Döller
Hansjörg Dietrich
Anu Bheemaiah MACHETTIRA
Dirk Schmutzler
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Bayer AG
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Bayer AG
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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
    • C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—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 two 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/416—2,5-Pyrrolidine-diones 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 other ring carbon atoms

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 succinimide-3-carboxamides and their salts, processes for their preparation and their use as herbicides.
  • succinimide-3-carboxamides are named which are unsubstituted in the 4-position of the succinimide and claimed as aldose reductase inhibitors with pharmaceutical benefits.
  • substituted succinimide-3-carboxamides or their salts as herbicidal active ingredients, however, has not yet been described.
  • certain substituted succinimide-3-carboxamides or their salts are particularly suitable as herbicides.
  • the present invention thus provides substituted succinimide-3-carboxamides of the general formula (I) or salts thereof
  • Q is an optionally substituted aryl, heteroaryl, (C 3 -C 10 ) -cycloalkyl or (C 3 -C 10 ) -
  • Ring or each ring system is optionally substituted with up to 5 substituents from the group R 5 , or for (C 2 -C 10) -alkenyl, (C 2 -C 10) -alkynyl, (C 2 -C 10) -haloalkenyl, (C 2 - Cio) -haloalkynyl, (C 3 -C 10 ) -halocycloalkenyl, or (C 1 -C 10 ) -alkoxy- (C 1 -C 10 ) -alkyl, (C 1 -C 10 ) -haloalkoxy- (C 1 -C 10 ) -alkyl,
  • W is oxygen or sulfur
  • R 1 represents hydrogen, formyl, hydroxy, amino, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -haloalkoxy, (C 3 -C 10 ) -
  • R 2 is hydrogen, halogen, hydroxy, (Ci-Cg) -alkyl, (Ci-Cg) -haloalkyl, (Ci-Cg) -Hydroxyalkyl, (Ci-Cg) -alkoxy, (Ci-Cg) -alkoxy- Ci-Cg) -alkyl,
  • R 3 is an optionally substituted aryl and heteroaryl, where each ring or each ring system may optionally be substituted with up to 5 substituents from the group R 5 , or, for a (C 3 -Cio) -cycloalkyl, (C 3 -) Cio) halocycloalkyl, (C 3 -Cio) -Cyanocycloalkyl, (Ci-Cio) alkyl- (C 3 -Cio) cycloalkyl, (Ci-Cio) alkoxy (C 3 -Cio) cycloalkyl, (C -Cio) -haloalkoxy- (C 3 -Cio) -cycloalkyl, (Ci-Cio) -alkylthio (C 3 -Cio) -cycloalkyl, aryl- (C 3 -Cio) -cycloalkyl, heteroaryl- (C 3
  • R 4 is hydrogen, hydroxy, amino, (Ci-Cg) -alkylamino, bis (Ci-Cg) -alkylamino, (Ci-Cg) -alkyl, (Ci-Cg) -haloalkyl, (C 2 -Cg) -alkenyl , (C 3 -C 6) -alkynyl, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkyl, (C 1 -C 9) -haloalkoxy- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylthio (Ci-Cg) -alkyl, (Ci-Cg) -alkylsulfinyl- (Ci-Cg) -alkyl, (Ci-Cg) -alkylsulfonyl- (Ci-Cg) -alkyl, (Ci
  • Heteroarylcarbonylamino, (Ci-C 8) alkoxy (Ci-C8) alkylcarbonylamino, (Ci-C 8) - Hydroxyalkylcarbonylamino, (Ci-C 8) is trialkylsilyl, with the exception of the compounds mentioned below:
  • 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, HsPO i 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 a basic group, e.g. Amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts. These salts then contain the conjugate base of the acid as an anion. Suitable substituents which are in deprotonated form, e.g. Sulfonic acids, certain
  • Sulfonklareamide or carboxylic acids may form internal salts with their turn protonatable groups, such as amino groups. Salt formation can also be due to the action of a base
  • Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine and ammonium, alkali or
  • Potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate are compounds in which the azide hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or
  • Alkaline earth metal salts in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula
  • R a to R d are each independently an organic radical, in particular alkyl, aryl, arylalkyl or alkylaryl. Also suitable are alkylsulfonium and
  • Alkylsulfoxoniumsalze such as (Ci-C ij-Trialkylsulfonium- and (Ci-C ij-Trialkylsulfoxoniumsalze.
  • the substituted succinimide-3-carboxamides 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).
  • Q is an optionally substituted aryl, heteroaryl, (C3-C9) -cycloalkyl or (C3-C9) -
  • W is oxygen or sulfur
  • R 1 represents hydrogen, hydroxy, amino, (Ci-Cr,) - alkoxy, (Ci-G,) - haloalkoxy, (C3-C8) cycloalkoxy, (Ci-Cej alkylamino, (C 2 -C 8) dialkylamino, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (Ci-C6) - 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, (C 3 -C 6) -cycloalkyl - (Ci-C 6 ) -alkyl, (C 3 -C 6 ) - Halocycloalkyl, (C 3
  • R 3 is an optionally substituted aryl and heteroaryl, each ring or ring system optionally being substituted with up to 5 substituents from the group R 5 , or an optionally substituted (C 3 -C 9 ) -cycloalkyl, (C 3 -C 9) halocycloalkyl, (C 3 -C 9) - Cyanocycloalkyl, (Ci-C9) alkyl - (C 3 -C 9) cycloalkyl, (Ci-C9) alkoxy (C 3 - C 9) cycloalkyl, (Ci-C 9), haloalkoxy (C 3 -C 9) cycloalkyl, (Ci-C 9) -alkylthio- (C 3 -C 9) cycloalkyl, aryl (C 3 - C 9) - cycloalkyl, heteroaryl (C 3 -C 9) cycloalkyl, (Ci-C9) al
  • R 4 is hydrogen, amino, (C 1 -C 6 -alkylamino, bis (C 1 -C 6 ) -alkylamino, (C 1 -Cr) -alkyl, (GG) -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 (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfinyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfonyl- (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -dial
  • R 5 is hydrogen, nitro, amino, cyano, thiocyanato, lsothiocyanato, halogen, (GG) - alkyl, (C 3- C 7) cycloalkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, aryl, aryl (Ci-C7) alkyl, aryl (C 2 -C 7) - alkenyl, aryl- (C 2 -C 7) alkynyl, aryl (Ci-C7) alkoxy , heteroaryl, (Ci-C7) alkoxy (Ci-C7) alkyl, (Ci-C7) hydroxyalkyl, (Ci-C7) haloalkyl, (C 3 -C 7) halocycloalkyl, ( Ci-C7) alkoxy, (Ci-C7) - haloalkoxy, aryloxy, heteroaryloxy, (C 3
  • Q is an optionally substituted aryl, heteroaryl, (C3-Cg) -cycloalkyl or (C3-C8) -
  • W is oxygen or sulfur
  • R 1 represents hydrogen, hydroxy, amino, (Ci-Cej alkoxy, (Ci-Cej -haloalkoxy, (C3-C8) cycloalkoxy, (Ci-Cej alkylamino, (C 2 -C 8) dialkylamino, ( Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (Ci-C6) - 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, (C 3 -C 6) -cycloalkyl- (Ci C 6) alkyl, (C 3 -C 6) -halocycloalkyl, (C 3 -C 6) -Halocycl
  • R 2 represents hydrogen, fluorine, chlorine, bromine, iodine, (C i -Cr,) - alkyl, (Ci-Cej -haloalkyl, (C I -C ⁇ ) - hydroxyalkyl, (Ci-C 6) alkoxy ( Ci-C 6 ) -alkyl
  • R 3 is an optionally substituted aryl and heteroaryl, each ring or ring system optionally being substituted by up to 5 substituents from the group R 5 , or an optionally substituted (-G) -cycloalkyl, (-G) - halocycloalkyl, (CN-Cx) - Cyanocycloalkyl, (C 'i-Cx) alkyl - (Cx-Cx) cycloalkyl, (Ci-C 8) alkoxy (C 3 -C 8) cycloalkyl, (Ci- C 8) haloalkoxy (C 3
  • R 4 is hydrogen, amino, (GG) -alkylamino, bis (C 1 -C 5 ) -alkylamino, (C 1 -Cr,) -alkyl, (GG) -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 (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfinyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfonyl- (C 1 -C 6 ) -alkyl, ( C 2 -C 6 ) dialkylaminos
  • R 5 is hydrogen, nitro, amino, cyano, thiocyanato, lsothiocyanato, halogen, (C i -Cr,) - alkyl, (C 3- C 6) cycloalkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, aryl, aryl (Ci-C 6) alkyl, aryl (C 2 -C 6) - alkenyl, aryl- (C 2 -C 6) alkynyl, aryl (Ci-C6) alkoxy, heteroaryl, (Ci-C6) alkoxy (Ci-C6) alkyl, (Ci-C6) hydroxyalkyl, (Ci-Cej -haloalkyl, (C 3 -C 6) halocycloalkyl, (GC ö j Alkoxy, (GG) - haloalkoxy, aryloxy, heteroary
  • Q is an optionally substituted aryl, heteroaryl, (C3-Cv) -cycloalkyl or (C3-C7) -
  • W is oxygen or sulfur, preferably oxygen
  • R 1 represents hydrogen, hydroxy, amino, (C 1 -C 6 ) -alkoxy, (C 3 -C 6 ) -cycloalkoxy, (C 1 -C 4 ) -alkylamino, (C 2 -C 6 ) -dialkylamino, (C 1 -C 6 ) -cycloalkoxy, C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, aryl- (C 1 -C 4 ) -alkyl, heteroaryl- (C 1 -C 4 ) -alkyl, heterocyclyl- (Ci -C 4 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (Ci-C 6 ) -alkyl, (C 3 -C 6 ) -halocyclo
  • R 2 is hydrogen, fluorine, chlorine, (Ci-C i) -alkyl
  • R 3 is an optionally substituted aryl and heteroaryl, each ring or ring system optionally being substituted with up to 5 substituents from the group R 5 , or an optionally substituted (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7) halocycloalkyl, (C 3 -C 7) - Cyanocycloalkyl, (Ci-C 7) alkyl - (C 3 -C 7) cycloalkyl, (Ci-C7) alkoxy (C 3 - C 7) cycloalkyl, (Ci-C7) haloalkoxy (C 3 -C 7) cycloalkyl, (Ci-C 7) alkylthio (C 3 -C 7) cycloalkyl, aryl (C 3 - C 7) - cycloalkyl, heteroaryl (C 3 -C 7) cycloalkyl, (Ci-C 7) alkoxy
  • R 4 is hydrogen, amino, (Ci-C 4) alkylamino, bis (Ci-C4) alkylamino, (Ci-C 6) -alkyl, (C 'iG) - haloalkyl, (C 2 -C 6 ) alkenyl, (C 3 -C 6) alkynyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C6) - haloalkoxy is (Ci-C 6) alkyl .
  • R 5 is hydrogen, nitro, amino, cyano, thiocyanato, lsothiocyanato, halogen, (Ci-C 4) -alkyl, (C 3 -C 5) cycloalkyl, (C 2 -C 4) alkenyl, (C 2 - C 4 ) -alkynyl, aryl, aryl- (C 1 -C 4 ) -alkyl, aryl- (C 2 -C 3 ) -alkenyl, aryl- (C 2 -C 3 ) -alkynyl, aryl- (C 1 -C 4 ) -alkoxy, heteroaryl, (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -hydroxyalkyl, (C 1 -C 4 ) -haloalkyl, (C 6 -C 4 -halo
  • Q is an optionally substituted aryl, heteroaryl, (C3-Cv) -cycloalkyl or (C3-C7) -
  • W is oxygen or sulfur, preferably oxygen
  • R 1 is hydrogen, hydroxy, amino, (C 1 -C 3 ) -alkoxy, (C 3 -C 6 ) -cycloalkoxy, (C 1 -C 3 ) -alkylamino, (C 2 -C 6 ) -dialkylamino, C 3 ) -alkyl, aryl- (C 1 -C 3 ) -alkyl, heteroaryl- (C 1 -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, trimethylsilyl,
  • R 2 is hydrogen, fluorine or chlorine
  • R 3 is an optionally substituted aryl and heteroaryl, each ring or ring system optionally being substituted with up to 5 substituents from the group R 5 , or an optionally substituted (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7) halocycloalkyl, (C 3 -C 7) - Cyanocycloalkyl, (Ci-C 6) -alkyl- (C 3 -C 7) cycloalkyl, (Ci-C 6) alkoxy (C 3 - C 7) cycloalkyl, (C 1 -6 haloalkoxy (C 3 -C 7) cycloalkyl, (Ci-C 6) alkylthio (C 3 -C 7) cycloalkyl, aryl (C 3 -C 7 ) cycloalkyl, heteroaryl (C 3 -C 7 ) cycloalkyl, (C 1 -C 6 )
  • R 4 is hydrogen, amino, (Ci-C ij-alkylamino, bis (Ci-C4) alkylamino, (C 1 -Cr,) - alkyl, (C I -C ⁇ ) - 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 stands, R 5 is hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci-C i) alkyl, (C 3 -C 5) cycloalkyl, (C 2 -C 4) alkenyl, (C 2 - C 4 ) -alkynyl, aryl, aryl- (C 1 -C 4 ) -alky
  • Q represents the groups Q-1.l to Q-1.293
  • W is oxygen
  • R 1 is hydrogen, hydroxy, amino, methoxy, methylamino, dimethylamino, methyl, ethyl, cyclopropyl, benzyl, p-methoxy-benzyl, allyl, propargyl or trimethylsilyl, and
  • R 2 is hydrogen, fluorine or chlorine. except for the following connections:
  • Q is any of those specifically mentioned in the above-mentioned groups Q-1 .1 to Q-1 .293.
  • Z stands for one of the groups Z-I.1 to Z-1.97 mentioned above specifically,
  • R 1 is hydrogen, methyl, ethyl, hydroxy, amino, methoxy or dimethylamino
  • R 2 is hydrogen. Except for the following connections:
  • 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 eg (but not limited to) (C 1 -C 6 ) alkylsulfonyl such as methylsulfonyl, ethyl sulfonyl, 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
  • 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) -, (GG) - or (Ci-C i) -alkylthio, for example (but not limited to) (Ci- C 6 ) -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-dimethyl
  • Cycloalkylthio means according to the invention a bonded via a sulfur atom
  • (C 1 -C 6 ) alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl,
  • Alkoxy means an alkyl radical bonded via an oxygen atom, e.g. (But not limited to) (Ci-Cs) alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, l, l-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, l, l 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,
  • Alkenyloxy is an alkenyl radical bonded 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 ) -alkynoxy.
  • Cycloalkyloxy means a cycloalkyl group bonded via an oxygen atom.
  • the number of C atoms refers to the alkyl radical in the
  • the number of C atoms refers to the alkyl radical in the alkoxycarbonyl group.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkene or alkynyloxycarbonyl group.
  • 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 also includes polycyclic systems, such as
  • Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkylthio, haloalkyl, alkoxy, haloalkoxy, Cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bis-alkylaminoalkoxy, tris [alkyl] silyl, bis [alkyl] arylsilyl, bis [alkyl] alkylsilyl, tris [alkyl] silylalkyny
  • 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-pyrrole-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; l, 2,3,4-tetrahydropyridine-1 or 2 or 3- or 4- or 5- or 6-yl; 1, 4-dihydropyridine-1 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 5- or
  • 3-membered ring and 4-membered ring heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl,
  • 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; Hexahydropyrimidine-1- or 2- or 3- or 4-yl; 1, 4,5,6-tetrahydropyrimidine-1- or 2- or 4- or 5- or 6-yl; l, 2,5,6-tetrahydropyrimidine-1- or 2- or 4- or 5- or 6-yl; 1, 2,3,4-tetrahydropyrimidine-1- or 2- or 3- or 4- or 5- or 6-yl; 1, 6-dihydropyrim
  • 1,2-dithiolan-3 or 4-yl 1,2-dithiolan-3 or 4-yl; 3H-1,2-dithiol-3- or 4- or 5-yl; l, 3-dithiolan-2 or 4-yl; l, 3-dithiol-2- or 4-yl; 1, 2-dithian-3 or 4-yl; 3,4-dihydro-1,2-dithiin-3 or 4 or 5 or 6-yl; 3,6-dihydro-
  • 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
  • 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,
  • 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 can also occur at the hetero ring atoms, which can exist in different oxidation states, for example at N and S, and then form, for example, the divalent groups N (O), S (O) (also SO for short) and S (O) 2 (also short SO2) in the heterocyclic ring
  • N (O), S (O) (also SO for short) and S (O) 2 (also short SO2) in the heterocyclic ring
  • both enantiomers are included in each case.
  • heteroaryl 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 eg isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl
  • quinoxaline quinazoline
  • cinnoline l, 5-naphthyridine; l, 6-naphthyridine; l, 7-naphthyridine; l, 8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyrido
  • 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-benzothiophene-3-yl, 1-benzothiophene-4-yl, 1-benzothiophene-5 yl, 1-benzothiophene-6-yl, 1-benzothiophene-7-yl, 1H-indazole
  • 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 is referred to in the latter case as “substituted alkyl".
  • Preferred substituents are halogen, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, particularly preferred are methoxy, methyl, fluoroalkyl, cyano, nitro, fluoro, chloro, bromo or iodo.
  • the prefix "bis” also includes the combination of different alkyl radicals, e.g. For example, methyl (ethyl) or ethyl (methyl).
  • Haloalkyl means the same or different halogen atoms, partially or fully substituted alkyl, alkenyl and alkynyl, e.g. monohaloalkyl
  • ( Monohaloalkyl) such. CH 2 CH 2 Cl, CH 2 CH 2 Br, CHCICH 3 , CH 2 Cl, CH 2 F; Perhaloalkyl such. B. CCl 3, CClF 2, CFC1 2 CF 2 CC1F 2, CF 2 CCIFCF3; 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, wherein the corresponding fluorine atoms may be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain, such as. CHFCH 3 , CH 2 CH 2 F, CH 2 CH 2 CF 3 , CHF 2 , CH 2 F, CHFCF 2 CF 3
  • Partially fluorinated haloalkyl means a straight-chain or branched, saturated one
  • Hydrocarbon which is substituted by various halogen atoms having at least one fluorine atom, wherein all other optional halogen atoms are selected from the group fluorine, chlorine or bromine, iodine.
  • the corresponding halogen atoms may be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain.
  • Partially fluorinated haloalkyl also includes the complete substitution of halogen with the participation of at least one fluorine atom of the straight-chain or branched chain.
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl; The same applies to haloalkenyl and other halogen-substituted radicals.
  • (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-C 6 ) 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.
  • hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, even in assembled radicals, are the lower carbon skeletons, e.g. with 1 to 6 C atoms or with unsaturated groups having 2 to 6 C atoms, preferred.
  • 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 means e.g.
  • Vinyl which may optionally be substituted by further alkyl radicals, for example (but not limited to) (CF-G0-alkynyl, 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-1-propeny
  • alkynyl in particular also includes straight-chain or branched open-chain
  • -alkynyl means e.g. 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 having preferably 3-8 ring C atoms, e.g. 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 [1,11] butan-2-yl, bicyclo [2.1.0] pentane-1-ol yl, bicyclo [1.1.1] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2.ll] 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 l-yl and adamantan-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,
  • 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, l, 3-cyclohexadienyl or 1, 4-cyclohexadienyl, wherein also substituents having a double bond on the cycloalkenyl, z.
  • an alkylidene group such as methylidene, are included.
  • the explanations for substituted cycloalkyl apply correspondingly.
  • alkylidene for. B. in the form of (Ci-Cio) alkylidene, means the radical of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond.
  • 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 group bonded via an alkyl group, e.g. B. (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 is - alone or as part of a chemical group - represents straight-chain or branched S haloalkyl, preferably having from 1 to 8, or with 1 to 6 carbon atoms, such as (Ci-Cs) -, (C 'iG) 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-l-ylthio.
  • Halocycloalkyl and “Halocycloalkenyl” mean by the same or different halogen atoms, such as. B. F, CI and Br, or by haloalkyl, such as. Trifluoromethyl or difluoromethyl, partially or fully substituted cycloalkyl or cycloalkenyl, e.g.
  • trialkylsilyl alone or as part of a chemical group - is straight-chain or branched Si-alkyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms such as tri - [(Ci-C 8 ) -, (Ci-Cr,) - or (Ci-C i) -alkyl] silyl, for example (but not limited to) trimethylsilyl, triethylsilyl, tri- (n-) propyl) silyl, tri (isopropyl) 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 (1) 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 (1). 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 prepared by using stereoselective Reactions can be selectively prepared using optically active starting materials and / or auxiliaries.
  • 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 general formula (I) are those which are well known to those skilled in the art from analogous cases, e.g. by physical methods such as crystallization, chromatographic methods, especially column chromatography and HPLC (high performance liquid chromatography), distillation, optionally under reduced pressure, extraction and other methods, residual mixtures may optionally be removed by chromatographic separation, e.g. at chiral solid phases, to be separated.
  • chromatographic separation e.g. at chiral solid phases
  • the substituted succinimide-3-carboxamides of the general formula (I) according to the invention can be prepared starting from known processes. The used and examined
  • Synthetic routes are based on commercially available or easily prepared amines, of appropriately substituted aldehydes and of commercially available chemicals such as
  • the synthesis of the compounds of general formula (Ia) according to the invention is carried out via an amide coupling of an acid of general formula (II) with an amine of general formula (III) in the presence of an amide coupling reagent such as T3P, dicyclohexylcarbodiimide, N- (3-Dimcthylaminopropyl ) - / ⁇ '- cylcarbodiimide, / V,, VC abony 1 diimide azo 1, 2-chloro-1, 3-dimethylimidazolium chloride or 2-chloro-1-methylpyridinium iodide (see Chemistry of Peptide Synthsis, Ed Benoiton, Taylor & Francis, 2006, ISBN 10: 1-57444-454-9) Reagents such as polymer-bound dicyclohexylcarbodiimide are also suitable for this coupling reaction.
  • an amide coupling reagent such as T3P, dicyclohexyl
  • 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 5 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 5 l , 8-diazabicyclo [5.4.0] undec-7-cene (see Scheme 1).
  • a base such as triethylamine, N, N-diisopropylethylamine or 5 l , 8
  • the synthesis of the acid of the general formula (II) can be prepared by hydrolysis of the compound of the general formula (IV) according to or analogously to methods known to the person skilled in the art (see Scheme 2).
  • 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), in the case where R 1 is alkyl, benzyl, alkenyl, alkynyl, can be obtained by alkylating the compound of general formula (V) with a Alkylating agent R'-X in the presence of a suitable base, such as sodium hydride or potassium carbonate perform.
  • a suitable base such as sodium hydride or potassium carbonate perform.
  • the reaction is preferably carried out in a temperature range between -10 ° C and 70 ° C, in an adequate solvent, such as tetrahydrofuran or
  • the synthesis of the compound of general formula (IV), in the case where R 1 is hydroxy, alkoxy, amino, alkylamino or dialkylamino, can be effected by reaction of the compound of general formula (V) with an appropriately substituted hydrazine, hydroxylamine or the like perform substituted alkoxyamine.
  • the reaction preferably takes place in the temperature range between -10 ° C and 150 ° C, in an adequate solvent, such as tetrahydrofuran or dimethylformamide (see Scheme 4).
  • the synthesis of the compound of the general formula (V) can be carried out by cyclization of the compound of the general formula (VI) in the presence of a base such as potassium carbonate.
  • the reaction preferably takes place in the temperature range between -10 ° C and 100 ° C, in an adequate solvent, such as acetone (see Scheme 5).
  • R ' (C 1 -C 4 ) -alkyl.
  • the synthesis of the compound of the general formula (VI) can be carried out by hydrolysis of the compound of the general formula (VII) in the presence of a palladium catalyst, such as
  • Palladium (II) chloride perform.
  • the reaction preferably takes place in the temperature range between -10 ° C and 80 ° C, in an adequate inert solvent, such as
  • Scheme 7 shows the synthesis of the compound of general formula (VII) by reaction of a compound of general formula (VIII) with a cyanide, for example sodium cyanide or potassium cyanide.
  • a cyanide for example sodium cyanide or potassium cyanide.
  • the reaction preferably takes place in the temperature range between -10 ° C and 120 ° C, in an adequate solvent, such as ethanol.
  • the compounds of general formula (VIII) can be prepared by Knoevenagel condensation of an aldehyde of general formula (IX) with malonic esters of general formula (X) (see Scheme 8, G. Jones, Organic Reactions Volume 15, John Wiley and Sons, 1967 ).
  • R ' (C 1 -C 4 ) -alkyl.
  • Table 1.1 Preferred compounds of the formula (1.1) are the compounds 1.1-1 to 1.1-293, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.1-1 to 1.1-293 of Table 1.1 are thus by the meaning of the respective entries no. 1 to 293 for Q the
  • Table 1.2 Preferred compounds of the formula (1.2) are the compounds 1.2-1 to 1.2-293, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.2-1 to 1.2-293 of Table 1.2 are thus determined by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.3 Preferred compounds of the formula (1.3) are the compounds 1.3-1 to 1.3-293, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.3-1 to 1.3-293 of Table 1.3 are thus determined by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.4 Preferred compounds of the formula (1.4) are the compounds 1.4-1 to 1.4-293, wherein Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.4-1 to 1.4-293 of Table 1.4 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.5 Preferred compounds of the formula (1.5) are the compounds 1.5-1 to 1.5-293, 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 293 for Q of Table 1 defined.
  • Table 1.6 Preferred compounds of the formula (1.6) are the compounds 1.6-1 to 1.6-293, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.6-1 to 1.6-293 of Table 1.6 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.7 Preferred compounds of the formula (1.7) are the compounds 1.7-1 to 1.7-293, wherein Q has the meanings indicated in the respective line of Table 1.
  • the compounds 1.7-1 to 1.7-293 of Table 1.7 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q the
  • Table 1.8 Preferred compounds of the formula (1.8) are the compounds 1.8-1 to 1.8-293, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.8-1 to 1.8-293 of Table 1.8 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.9 Preferred compounds of the formula (1.9) are the compounds 1.9-1 to 1.9-293, wherein Q has the meanings indicated in the respective line of Table 1.
  • the compounds 1.9-1 to 1.9-293 of Table 1.9 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q the
  • Table 1.10 Preferred compounds of the formula (1.10) are the compounds 1.10-1 to 1.10-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.10-1 to 1.10-293 of Table 1.10 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.11 Preferred compounds of the formula (1.11) are the compounds 1.11-1 to 1.11-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.11-1 to 1.11-293 of Table 1.11 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.12 Preferred compounds of the formula (1.12) are the compounds 1.12-1 to 1.12-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.12-1 to 1.12-293 of Table 1.12 are thus distinguished by the meaning of the respective entries no. 1 to
  • Table 1.13 Preferred compounds of the formula (1.13) are the compounds 1.13-1 to 1.13-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.13-1 to 1.13-293 of Table 1.13 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.14 Preferred compounds of the formula (1.14) are the compounds 1.14-1 to 1.14-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.14-1 to 1.14-293 of Table 1.14 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.15 Preferred compounds of the formula (1.15) are the compounds 1.15-1 to 1.15-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.15-1 to 1.15-293 of Table 1.15 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.16 Preferred compounds of the formula (1.16) are the compounds 1.16-1 to 1.16-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.16-1 to 1.16-293 of Table 1.16 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.17 Preferred compounds of the formula (1.17) are the compounds 1.17-1 to 1.17-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.17-1 to 1.17-293 of Table 1.17 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.18 Preferred compounds of the formula (1.18) are the compounds 1.18-1 to 1.18-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.18-1 to 1.18-293 of Table 1.18 are thus characterized by the meaning of the respective entries no. 1 to
  • Table 1.19 Preferred compounds of the formula (1.19) are the compounds 1.19-1 to 1.19-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.19-1 to 1.19-293 of Table 1.19 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.20 Preferred compounds of the formula (1.20) are the compounds 1.20-1 to 1.20-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.20-1 to 1.20-293 of Table 1.20 are thus distinguished by the meaning of the respective entries no. 1 to
  • Table 1.21 Preferred compounds of the formula (1.21) are the compounds 1.21-1 to 1.21-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.21-1 to 1.21-293 of Table 1.21 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.22 Preferred compounds of the formula (1.22) are the compounds 1.22-1 to 1.22-293, in which Q has the meanings given in Table 1 in the respective line.
  • the compounds 1.22-1 to 1.22-293 of Table 1.22 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.23 Preferred compounds of the formula (1.23) are the compounds 1.23-1 to 1.23-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.23-1 to 1.23-293 of Table 1.23 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.24 Preferred compounds of the formula (1.24) are the compounds 1.24-1 to 1.24-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.24-1 to 1.24-293 of Table 1.24 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.25 Preferred compounds of the formula (1.25) are the compounds 1.25-1 to 1.25-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.25-1 to 1.25-293 of Table 1.25 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.26 Preferred compounds of the formula (1.26) are the compounds 1.26-1 to 1.26-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.26-1 to 1.26-293 of Table 1.26 are thus distinguished by the meaning of the respective entries no. 1 to
  • Table 1.27 Preferred compounds of the formula (1.27) are the compounds 1.27-1 to 1.27-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.27-1 to 1.27-293 of Table 1.27 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.28 Preferred compounds of the formula (1.28) are the compounds 1.28-1 to 1.28-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.28-1 to 1.28-293 of Table 1.28 are thus characterized by the meaning of the respective entries no. 1 to
  • Table 1.29 Preferred compounds of the formula (1.29) are the compounds 1.29-1 to 1.29-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.29-1 to 1.29-293 of Table 1.29 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.30 Preferred compounds of the formula (1.30) are the compounds 1.30-1 to 1.30-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.30-1 to 1.30-293 of Table 1.30 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.31 Preferred compounds of the formula (1.31) are the compounds 1.31-1 to 1.31-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.31-1 to 1.31-293 of Table 1.31 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.32 Preferred compounds of the formula (1.32) are the compounds 1.32-1 to 1.32-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.32-1 to 1.32-293 of Table 1.32 are thus distinguished by the meaning of the respective entries no. 1 to
  • Table 1.33 Preferred compounds of the formula (1.33) are the compounds 1.33-1 to 1.33-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.33-1 to 1.33-293 of Table 1.33 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.34 Preferred compounds of the formula (1.34) are the compounds 1.34-1 to 1.34-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.34-1 to 1.34-293 of Table 1.34 are thus distinguished by the meaning of the respective entries no. 1 to
  • Table 1.35 Preferred compounds of the formula (1.35) are the compounds 1.35-1 to 1.35-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.35-1 to 1.35-293 of Table 1.35 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.36 Preferred compounds of the formula (1.36) are the compounds 1.36-1 to 1.36-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.36-1 to 1.36-293 of Table 1.36 are thus characterized by the meaning of the respective entries no. 1 to
  • Table 1.37 Preferred compounds of the formula (1.37) are the compounds 1.37-1 to 1.37-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.37-1 to 1.37-293 of Table 1.37 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.38 Preferred compounds of the formula (1.38) are the compounds 1.38-1 to 1.38-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the connections 1.38-1 to 1.38-293 of Table 1.38 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.39 Preferred compounds of the formula (1.39) are the compounds 1.39-1 to 1.39-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.39-1 to 1.39-293 of Table 1.39 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.40 Preferred compounds of the formula (1.40) are the compounds 1.40-1 to 1.40-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.40-1 to 1.40-293 of Table 1.40 are therefore distinguished by the meaning of the respective entries no. 1 to
  • Table 1.41 Preferred compounds of the formula (1.41) are the compounds 1.41-1 to 1.41-293, in which Q has the meanings given in Table 1 in the respective line.
  • the compounds 1.41-1 to 1.41-293 of Table 1.41 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.42 Preferred compounds of the formula (1.42) are the compounds 1.42-1 to 1.42-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.42-1 to 1.42-293 of Table 1.42 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.43 Preferred compounds of the formula (1.43) are the compounds 1.43-1 to 1.43-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.43-1 to 1.43-293 of Table 1.43 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.44 Preferred compounds of the formula (1.44) are the compounds 1.44-1 to 1.44-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.44-1 to 1.44-293 of Table 1.44 are thus distinguished by the meaning of the respective entries no. 1 to
  • Table 1.45 Preferred compounds of the formula (1.45) are the compounds 1.45-1 to 1.45-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.45-1 to 1.45-293 of Table 1.45 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.46 Preferred compounds of the formula (1.46) are the compounds 1.46-1 to 1.46-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.46-1 to 1.46-293 of Table 1.46 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.47 Preferred compounds of the formula (1.47) are the compounds 1.47-1 to 1.47-293, in which Q has the meanings given in Table 1 in each line.
  • the compounds 1.47-1 to 1.47-293 of Table 1.47 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.48 Preferred compounds of the formula (1.48) are the compounds 1.48-1 to 1.48-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.48-1 to 1.48-293 of Table 1.48 are thus distinguished by the meaning of the respective entries no. 1 to
  • Table 1.49 Preferred compounds of the formula (1.49) are the compounds 1.49-1 to 1.49-293, in which Q has the meanings of Table 1 indicated in the respective line. The connections
  • Table 1.50 Preferred compounds of the formula (1.50) are the compounds 1.50-1 to 1.50-293, in which Q has the meanings of Table 1 indicated in the respective line. The connections
  • Table 1.51 Preferred compounds of the formula (1.51) are the compounds 1.51-1 to 1.51-293, in which Q has the meanings of Table 1 indicated in the respective line. The connections
  • Table 1.52 Preferred compounds of the formula (1.52) are the compounds 1.52-1 to 1.52-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.52-1 to 1.52-293 of Table 1.52 are thus characterized by the meaning of the respective entries no. 1 to
  • Table 1.53 Preferred compounds of the formula (1.53) are the compounds 1.53-1 to 1.53-293, in which Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.53-1 to 1.53-293 of Table 1.53 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.54 Preferred compounds of the formula (1.54) are the compounds 1.54-1 to 1.54-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.54-1 to 1.54-293 of Table 1.54 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.55 Preferred compounds of the formula (1.55) are the compounds 1.55-1 to 1.55-293, in which Q has the meanings given in Table 1 of each Table.
  • the compounds 1.55-1 to 1.55-293 of Table 1.55 are thus characterized by the meaning of the respective entries no. 1 to
  • Table 1.56 Preferred compounds of the formula (1.56) are the compounds 1.56-1 to 1.56-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.56-1 to 1.56-293 of Table 1.56 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.57 Preferred compounds of the formula (1.57) are the compounds 1.57-1 to 1.57-293, in which Q has the meanings given in Table 1 of each Table.
  • the connections 1.57-1 to 1.57-293 of Table 1.57 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.58 Preferred compounds of the formula (1.58) are the compounds 1.58-1 to 1.58-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.58-1 to 1.58-293 of Table 1.58 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.59 Preferred compounds of the formula (1.59) are the compounds 1.59-1 to 1.59-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.59-1 to 1.59-293 of Table 1.59 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.60 Preferred compounds of the formula (1.60) are the compounds 1.60-1 to 1.60-293, in which Q has the meanings of Table 1 indicated in the respective line. The connections
  • Table 1.61 Preferred compounds of the formula (1.61) are the compounds 1.61-1 to 1.61-293, in which Q has the meanings of Table 1 indicated in the respective line. The connections
  • Preferred compounds of the formula (1.62) are the compounds 1.62-1 to 1.62-293, in which Q has the meanings of Table 1 indicated in the respective line. The connections
  • Table 1.63 Preferred compounds of the formula (1.63) are the compounds 1.63-1 to 1.63-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.63-1 to 1.63-293 of Table 1.63 are thus characterized by the meaning of the respective entries no. 1 to
  • Table 1.64 Preferred compounds of the formula (1.64) are the compounds 1.64-1 to 1.64-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.64-1 to 1.64-293 of Table 1.64 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.65 Preferred compounds of the formula (1.65) are the compounds 1.65-1 to 1.65-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.65-1 to 1.65-293 of Table 1.65 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.66 Preferred compounds of the formula (1.66) are the compounds 1.66-1 to 1.66-293, wherein Q has the meanings given in Table 1 of each line.
  • the compounds 1.66-1 to 1.66-293 of Table 1.66 are thus distinguished by the meaning of the respective entries no. 1 to
  • Table 1.67 Preferred compounds of the formula (1.67) are the compounds 1.67-1 to 1.67-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.67-1 to 1.67-293 of Table 1.67 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.68 Preferred compounds of the formula (1.68) are the compounds 1.68-1 to 1.68-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.68-1 to 1.68-293 of Table 1.68 are therefore distinguished by the meaning of the respective entries no. 1 to
  • Table 1.69 Preferred compounds of the formula (1.69) are the compounds 1.69-1 to 1.69-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.69-1 to 1.69-293 of Table 1.69 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.70 Preferred compounds of the formula (1.70) are the compounds 1.70-1 to 1.70-293, in which Q has the meanings of Table 1 indicated in the respective line. The connections
  • Table 1.71 Preferred compounds of the formula (1.71) are the compounds 1.71-1 to 1.71-293, in which Q has the meanings of Table 1 indicated in the respective line. The connections
  • Preferred compounds of the formula (1.72) are the compounds 1.72-1 to 1.72-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • Table 1.73 Preferred compounds of the formula (1.73) are the compounds 1.73-1 to 1.73-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.73-1 to 1.73-293 of Table 1.73 are therefore distinguished by the meaning of the respective entries no. 1 to
  • Table 1.74 Preferred compounds of the formula (1.74) are the compounds 1.74-1 to 1.74-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.74-1 to 1.74-293 of Table 1.74 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.75 Preferred compounds of the formula (1.75) are the compounds 1.75-1 to 1.75-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.75-1 to 1.75-293 of Table 1.75 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.76 Preferred compounds of the formula (1.76) are the compounds 1.76-1 to 1.76-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.76-1 to 1.76-293 of Table 1.76 are therefore distinguished by the meaning of the respective entries no. 1 to
  • Table 1.77 Preferred compounds of the formula (1.77) are the compounds 1.77-1 to 1.77-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.77-1 to 1.77-293 of Table 1.77 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.78 Preferred compounds of the formula (1.78) are the compounds 1.78-1 to 1.78-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.78-1 to 1.78-293 of Table 1.78 are thus characterized by the meaning of the respective entries no. 1 to
  • Table 1.79 Preferred compounds of the formula (1.79) are the compounds 1.79-1 to 1.79-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.79-1 to 1.79-293 of Table 1.79 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.80 Preferred compounds of the formula (1.80) are the compounds 1.80-1 to 1.80-293, in which Q has the meanings of Table 1 indicated in the respective line. The connections
  • Table 1.81 Preferred compounds of the formula (1.81) are the compounds 1.81-1 to 1.81-293, in which Q has the meanings of Table 1 indicated in the respective line. The connections
  • Preferred compounds of the formula (1.82) are the compounds 1.82-1 to 1.82-293, in which Q has the meanings of Table 1 indicated in the respective line. The connections
  • Table 1.83 Preferred compounds of the formula (1.83) are the compounds 1.83-1 to 1.83-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.83-1 to 1.83-293 of Table 1.83 are thus distinguished by the meaning of the respective entries no. 1 to
  • Table 1.84 Preferred compounds of the formula (1.84) are the compounds 1.84-1 to 1.84-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.84-1 to 1.84-293 of Table 1.84 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.85 Preferred compounds of the formula (1.85) are the compounds 1.85-1 to 1.85-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.85-1 to 1.85-293 of Table 1.85 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.86 Preferred compounds of the formula (1.86) are the compounds 1.86-1 to 1.86-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.86-1 to 1.86-293 of Table 1.86 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.87 Preferred compounds of the formula (1.87) are the compounds 1.87-1 to 1.87-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.87-1 to 1.87-293 of Table 1.87 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.88 Preferred compounds of the formula (1.88) are the compounds 1.88-1 to 1.88-293, in which Q has the meanings of Table 1 given in the respective line.
  • the compounds 1.88-1 to 1.88-293 of Table 1.88 are thus distinguished by the meaning of the respective entries no. 1 to
  • Table 1.89 Preferred compounds of the formula (1.89) are the compounds 1.89-1 to 1.89-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.89-1 to 1.89-293 of Table 1.89 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.90 Preferred compounds of the formula (1.90) are the compounds 1.90-1 to 1.90-293, in which Q has the meanings of Table 1 indicated in the respective line. The connections
  • Table 1.91 Preferred compounds of the formula (1.91) are the compounds 1.91-1 to 1.91-293, in which Q has the meanings of Table 1 indicated in the respective line. The connections
  • Preferred compounds of the formula (1.92) are the compounds 1.92-1 to 1.92-293, in which Q has the meanings given in Table 1 in each line. The connections
  • Table 1.93 Preferred compounds of the formula (1.93) are the compounds 1.93-1 to 1.93-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.93-1 to 1.93-293 of Table 1.93 are thus distinguished by the meaning of the respective entries no. 1 to
  • Table 1.94 Preferred compounds of the formula (1.94) are the compounds 1.94-1 to 1.94-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.94-1 to 1.94-293 of Table 1.94 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.95 Preferred compounds of the formula (1.95) are the compounds 1.95-1 to 1.95-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.95-1 to 1.95-293 of Table 1.95 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.96 Preferred compounds of the formula (1.96) are the compounds 1.96-1 to 1.96-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.96-1 to 1.96-293 of Table 1.96 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.97 Preferred compounds of the formula (1.97) are the compounds 1.97-1 to 1.97-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.97-1 to 1.97-293 of Table 1.97 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.98 Preferred compounds of the formula (1.98) are the compounds 1.98-1 to 1.98-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.98-1 to 1.98-293 of Table 1.98 are therefore distinguished by the meaning of the respective entries no. 1 to
  • Table 1.99 Preferred compounds of the formula (1.99) are the compounds 1.99-1 to 1.99-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.99-1 to 1.99-293 of Table 1.99 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.100 Preferred compounds of the formula (1.100) are the compounds 1.100-1 to 1.100-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.100-1 to 1.100-293 of Table 1.100 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.101 Preferred compounds of the formula (1.101) are the compounds 1.101-1 to 1.101-293, in which Q has the meanings of Table 1 indicated in the respective line. The connections
  • Table 1.102 Preferred compounds of the formula (1.102) are the compounds 1.102-1 to 1.102-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.102-1 to 1.102-293 of Table 1.102 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.103 Preferred compounds of the formula (1.103) are the compounds 1.103-1 to 1.103-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.103-1 to 1.103-293 of Table 1.103 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.104 Preferred compounds of the formula (1.104) are the compounds 1.104-1 to 1.104-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.104-1 to 1.104-293 of Table 1.104 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.105 Preferred compounds of the formula (1.105) are the compounds 1.105-1 to 1.105-293, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.105-1 to 1.105-293 of Table 1.105 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.106 Preferred compounds of the formula (1.106) are the compounds 1.106-1 to 1.106-293, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.106-1 to 1.106-293 of Table 1.106 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.107 Preferred compounds of the formula (1.107) are the compounds 1.107-1 to 1.107-293, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.107-1 to 1.107-293 of Table 1.107 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.108 Preferred compounds of the formula (1.108) are the compounds 1.108-1 to 1.108-293, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.108-1 to 1.108-293 of Table 1.108 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.109 Preferred compounds of the formula (1.109) are the compounds 1.109-1 to 1.109-293, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.109-1 to 1.109-293 of Table 1.109 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.110 Preferred compounds of the formula (1.110) are the compounds 1.110-1 to 1.110-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the connections 1.110-1 to 1.110-293 of Table 1.110 are thus by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.111 Preferred compounds of the formula (1.111) are the compounds 1.111-1 to 1.111-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.111-1 to 1.111-293 of Table 1.111 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.112 Preferred compounds of the formula (1.112) are the compounds 1.112-1 to 1.112-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.112-1 to 1.112-293 of Table 1.112 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.113 Preferred compounds of the formula (1.113) are the compounds 1.113-1 to 1.113-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.113-1 to 1.113-293 of Table 1.113 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.114 Preferred compounds of the formula (1.114) are the compounds 1.114-1 to 1.114-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.114-1 to 1.114-293 of Table 1.114 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.115 Preferred compounds of the formula (1.115) are the compounds 1.115-1 to 1.115-293, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.115-1 to 1.115-293 of Table 1.115 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.116 Preferred compounds of the formula (1.116) are the compounds 1.116-1 to 1.116-293, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.116-1 to 1.116-346 of Table 1.116 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.117 Preferred compounds of the formula (I. ll 7) are the compounds 1.117-1 to 1.117-293, wherein Q has the meanings indicated in the respective line of Table 1.
  • the compounds 1.117-1 to 1.117-293 of Table 1.117 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.118 Preferred compounds of the formula (1.118) are the compounds 1.118-1 to 1.118-293, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.118-1 to 1.118-293 of Table 1.118 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.119 Preferred compounds of the formula (1.119) are the compounds 1.119-1 to 1.119-293, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.119-1 to 1.119-346 of Table 1.119 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.120 Preferred compounds of the formula (1.120) are the compounds 1,120-1 to 1,120-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.120-1 to 1.120-293 of Table 1.120 are thus distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.121 Preferred compounds of the formula (1.121) are the compounds 1.121-1 to 1.121-293, in which Q has the meanings given in Table 1 in each line.
  • the compounds 1.121-1 to 1.121-293 of Table 1.121 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.122 Preferred compounds of the formula (1.122) are the compounds 1.122-1 to 1.122-293, in which Q has the meanings given in Table 1 in each line.
  • the compounds 1.122-1 to 1.122-346 of Table 1.122 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.123 Preferred compounds of the formula (1.123) are the compounds 1.123-1 to 1.123-293, wherein Q has the meanings indicated in Table 1 of each Table.
  • the compounds 1.123-1 to 1.123-293 of Table 1.123 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.124 Preferred compounds of the formula (1.124) are the compounds 1.124-1 to 1.124-293, wherein Q has the meanings indicated in Table 1 of each Table. The connections
  • Table 1.125 Preferred compounds of the formula (1.125) are the compounds 1.125-1 to 1.125-293, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.125-1 to 1.125-346 of Table 1.125 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.126 Preferred compounds of the formula (1.126) are the compounds 1.126-1 to 1.126-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.126-1 to 1.126-293 of Table 1.126 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.127 Preferred compounds of the formula (1.127) are the compounds 1.127-1 to 1.127-293, wherein Q has the meanings indicated in Table 1 of each Table.
  • the compounds 1.127-1 to 1.127-293 of Table 1.127 are therefore distinguished by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • Table 1.128 Preferred compounds of the formula (1.128) are the compounds 1.128-1 to 1.128-293, in which Q has the meanings of Table 1 indicated in the respective line.
  • the compounds 1.128-1 to 1.128-346 of Table 1.128 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 defined.
  • Table 1.129 Preferred compounds of the formula (1.129) are the compounds 1.129-1 to 1.129-293, wherein Q has the meanings given in Table 1 of each Table.
  • the compounds 1.129-1 to 1.129-293 of Table 1.129 are thus characterized by the meaning of the respective entries no. 1 to 293 for Q of Table 1 above.
  • the present invention furthermore relates to the use of one or more
  • 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 (1.1) to (1.129) and / or salts thereof, each as defined above, or an agent according to the invention, as defined below, on the (harmful) plants, (Schad) 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 method for controlling undesirable plants, preferably in crops, characterized in that an effective amount of one or more compounds of the general formula (1) and / or their salts, as defined above, preferably in one of preferred or particularly preferred marked
  • Embodiment in particular one or more compounds of the formulas (1.1) to (1.129) and / or salts thereof, each as defined above, or a mitel according to the invention, as defined below, to undesired plants (eg harmful plants such as monocotyledonous or dicotyledonous weeds or undesired crop plants), the seed of the unwanted plants (ie plant seeds, eg grains, seeds or vegetative propagation organs such as tubers or sprouts with buds), the soil in which or on which the unwanted plants grow, (eg the soil of cultivated land or non-cultivated land) or the cultivated area (ie area on which the unwanted plants will grow) is applied.
  • undesired plants eg harmful plants such as monocotyledonous or dicotyledonous weeds or undesired crop plants
  • the seed of the unwanted plants ie plant seeds, eg grains, seeds or vegetative propagation organs such as tubers or sprouts with buds
  • the present invention is also a method for controlling
  • Embodiment in particular one or more compounds of the general formulas (1.1) to (1.129) 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 the general formula (I) according to the invention and / or salts thereof 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,
  • 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 constituents and to alleviate embarrassment, for example 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. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops, since, for example, storage formation can thereby 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 Emtegut 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
  • 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.
  • 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, for example, 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
  • Fatty acid composition of Emteguts known.
  • Other particular properties may include tolerance or resistance to abiotic stressors, e.g. Heat, cold, drought, salt and ultraviolet radiation are present.
  • cereals such as wheat, barley, rye, oats, triticale, millet, rice, manioc and maize or also crops of sugar beet, cotton, soya, rapeseed, potato, tomato, pea and other vegetables.
  • 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 which may be present, as well as DNA molecules which comprise only parts of the coding sequence, whereby these parts have to be long enough, to cause an antisense effect in the cells. 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 is linked to DNA sequences which 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. Acetylactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), respectively, which are resistant to herbicides from the group of sulfonylureas, glyphosate, glufosinate or benzoylisoxazole and analogues.
  • ALS Acetylactate synthases
  • EPSP synthases glutamine synthases
  • HPPD hydroxyphenylpyruvate dioxygenases
  • the active compounds according to the invention in addition to the effects observed in other crops on harmful plants, 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 the general formula (1) or its salt is formed from a precursor substance ("prodrug") after plant, plant or soil application.
  • the invention also provides the use of one or more compounds of the general formula (1) 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 (1) or their salts on the plants (harmful plants, 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 (1.1) to (1.129) and / or salts thereof, each as defined above,
  • the other agrochemical active substances of constituent (i) of an agent according to the invention are preferably selected from the group of substances described in "The Pesticide Manual", 16 th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 are mentioned.
  • a herbicidal or plant growth-regulating agent according to the invention preferably comprises one, two, three or more plant protection formulation auxiliaries (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, anti-foaming agents, water, organic solvents, preferably at 25 ° C and 1013 mbar with water in any ratio miscible organic solvents.
  • auxiliaries 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, anti-foaming agents, water
  • the compounds of the general formula (I) according to the invention can be used in the form of spray 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.
  • Injectable powders are preparations which are uniformly dispersible in water and contain surfactants of the ionic and / or nonionic type (wetting agents, dispersants) in addition to the active ingredient except a diluent or inert substance.
  • 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, colloid mills and / or static mixers using aqueous organic solvent
  • Granules can either be prepared by spraying the active ingredient onto adsorptive, granulated inert material or by applying active substance concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils, to the surface of carriers such as sand, kaolinites or granulated inert material. Also suitable adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils, to the surface of carriers such as sand, kaolinites or granulated inert material. Also suitable
  • Water dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, high speed mixing and extrusion without solid inert material.
  • the agrochemical compositions preferably herbicidal or plant growth regulating agents of the present invention, preferably contain a total amount of from 0.1 to 99% by weight, preferably from 0.5 to 95% by weight, more preferably from 1 to 90% by weight, most preferably 2 to 80 wt .-%, of active compounds of the general formula (I) and their salts.
  • the drug concentration is e.g. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients.
  • the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%.
  • Formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient.
  • the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used.
  • the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active substance formulations mentioned optionally contain the customary adhesion, wetting, dispersing, emulsifying, penetrating, preserving, antifreeze and solvent, fillers, carriers and dyes, antifoams, evaporation inhibitors and the pH and the Viscosity-influencing agent.
  • formulation auxiliaries are described, inter alia, in "Chemistry and Technology of Agrochemical Formulations", ed. DA Knowles, Kluwer Academic Publishers (1998).
  • the compounds of general formula (I) or their salts may be used as such or in the form of their formulations (formulations) with other pesticidally active substances, e.g. Insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or
  • Growth regulators can be used in combination, e.g. as finished formulation or as
  • Tank mixes The combination formulations can be prepared on the basis of the above-mentioned formulations, taking into account the physical properties and stabilities of the active ingredients to be combined.
  • combination partners for the compounds of general formula (I) according to the invention in mixture formulations or in tank mix are known active compounds which are based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate Synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase are based, can be used, such as in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16 th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein.
  • Compounds (I) of particular interest which contain the compounds of general formula (I) or their combinations with other herbicides or pesticides and safeners.
  • the safeners which are used in an antidote effective content, reduce the phytotoxic side effects of the herbicides / pesticides used, eg in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugar cane, oilseed rape, cotton and soy, preferably cereals.
  • the weight ratios of herbicide (mixture) to safener generally depends on the
  • herbicide and the effectiveness of each safener can vary within wide limits, for example in the range of 200: 1 to 1: 200, preferably 100: 1 to 1: 100, in particular 20: 1 to 1:20.
  • the safeners can be formulated analogously to the compounds of the general formula (I) or mixtures thereof with further herbicides / pesticides and as
  • the herbicidal or herbicidal safener formulations present in commercial form are optionally diluted in a customary manner, e.g. for Spritzpulvem, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dust-like preparations, ground or scattered granules and sprayable solutions are usually no longer diluted with other inert substances before use.
  • Application rate can vary within wide limits.
  • the total amount of compounds of general formula (1) and salts thereof is preferably in the range of 0.001 to 10.0 kg / ha, preferably in the range of 0.005 to 5 kg / ha, more preferably in Range of 0.01 to 1.5 kg / ha, particularly preferably in the range of 0.05 to 1 kg / ha. This applies both to pre-emergence or post-emergence applications.
  • Plant growth regulator for example as Halmverkürzer in crops, as mentioned above, preferably in cereal plants such as wheat, barley, rye, triticale, millet, rice or corn, the total application rate is preferably in the range of 0.001 to 2 kg / ha, preferably in the range of 0.005 to 1 kg / ha, in particular in the range of 10 to 500 g / ha, most preferably in the range of 20 to 250 g / ha. This applies to both the application in the
  • Halmverkürzer can be done in various stages of growth of the plants. For example, the application after bestockung at the beginning of the
  • seed treatment when used as a plant growth regulator, seed treatment may be considered, including the different seed dressing and coating techniques.
  • the application rate depends on the individual techniques and can be determined in preliminary tests.
  • Suitable combination partners for the compounds of the general formula (1) according to the invention in compositions according to the invention are, for example, known active compounds which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvyl shikimate 3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem 11 or
  • Protoporphyrinogen oxidase can be used, as e.g. from Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16 th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and cited therein.
  • herbicidal mixture partners examples include:
  • flucarbazone flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazine, fluometuron, flurenol, flurenol-butyl, - dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-p-s
  • methabenzothiazuron metam, metamifop, metamitron, metazachlor, metazosulfuron,
  • met.zthiazuron methiopyrsulfuron, methiozoline, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron ester, MT-5950, ie N- [3-chloro -4- (1-methylethyl) phenyl] -2-methylpentanamide, NGGC-011, napropamide, NC-310, ie 4- (2,4-dichlorobenzoyl) -l-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiar
  • plant growth regulators as possible mixing partners are:
  • Sl d compounds of the type of triazolecarboxylic acids (Sl d ), preferably compounds such as
  • Sl e compounds of the type of 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid, or of 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (Sl e ), preferably compounds such as
  • S2 a compounds of the 8-quinolinoxyacetic acid type (S2 a ), preferably
  • S2 b compounds of the type of (5-chloro-8-quinolinoxy) malonic acid (S2 b ), preferably
  • Benoxacor (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4),
  • PPG-1292 N-allyl-N - [(1,3-dioxolan-2-yl) -methyl] -dichloroacetamide
  • TI-35 (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8),
  • RA 2 halogen (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3; n 1 or 2;
  • VA is 0, 1, 2 or 3;
  • RB 1, RB 2 are independently hydrogen, (Ci-C 6) alkyl, (C3-C6) cycloalkyl, (C 3 C 6) alkenyl, (C 3 -C 6) alkynyl,
  • RB 3 is halogen, (Ci-C4) alkyl, (Ci-C4) haloalkyl or (Ci-C4) alkoxy and ms is 1 or 2, for example those in which
  • RB 1 cyclopropyl
  • RB 2 hydrogen
  • (RB 3 ) 2-OMe
  • RB 1 cyclopropyl
  • RB 2 hydrogen
  • (RB 3 ) 5-Cl-2-OMe (S4-2)
  • RB 1 isopropyl
  • RB 2 hydrogen
  • (RB 3 ) 5-Cl-2-OMe is (S4-4) and
  • Rc 1, Rc 2 are independently hydrogen, (Ci-Cg) alkyl, (C3-Cg) cycloalkyl, (C 3 C 6) alkenyl, (C 3 -C 6) alkynyl,
  • Rc 3 is halogen, (Ci-C4) alkyl, (Ci-C4) alkoxy, CF 3 and mc is 1 or 2; for example, 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,
  • RD 4 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3; m D 1 or 2;
  • RD 5 is hydrogen, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 5 -
  • Carboxylic acid derivatives (S5) e.g.
  • Methyl diphenylmethoxyacetate (CAS No. 41858-19-9) (S7-1), Diphenylmethoxyessigklareethylester or Diphenylmethoxyessigklare as described in WO-A-98/38856.
  • RD 1 is halogen, (Ci-C i) alkyl, (Ci-C i) haloalkyl, (Ci-C i) alkoxy, (Ci-C4) haloalkoxy,
  • R D 2 is hydrogen or (Ci-C4) alkyl
  • R D 3 is hydrogen, (Ci-CsjAlkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, or aryl, wherein each of the aforementioned C-containing radicals unsubstituted or by one or more, preferably up to three identical or different Radicals from the group consisting of halogen and alkoxy, or their salts, n D is an integer from 0 to 2.
  • YE, ZE independently of one another O or S, he is an integer from 0 to 4,
  • RE 3 is hydrogen or (Ci-C 6 ) alkyl.
  • Sl 1 active substances of the type of oxyimino compounds (Sl 1), which are known as seed dressings, such as. B.
  • Oxabetrinil ((Z) -1,3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (Sl l-1), which is known as a seed safener for millet against damage by metolachlor,
  • Fluorofenim (1- (4-chlorophenyl) -2,2,2-trifluoro-1-ethanone-0- (1,3-dioxolan-2-ylmethyl) -oxime) (S1-2) used as seed dressing -Safener for millet is known against damage from metolachlor, and
  • Cyometrinil or “CGA-43089” ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (Sl l-3), which is known as a seed dressing safener for millet against damage from metolachlor.
  • S12 Isothiochromanone (S12) class agents, e.g. Methyl- [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Reg. No. 205121-04-6) (Sl2-I) and related compounds of WO-A- 1998/13361.
  • S12 Isothiochromanone (S12) class agents, e.g. Methyl- [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Reg. No. 205121-04-6) (Sl2-I) and related compounds of WO-A- 1998/13361.
  • S13 One or more compounds from group (S13): "naphthalene anhydride” (l, 8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed safener for corn against damage by thiocarbamate herbicides,
  • Cyanamide which is known as safener for maize against damage of imidazolinones
  • MG 191 (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as safener for corn,
  • Mephenate (4-chlorophenyl methylcarbamate) (St 3-9). Active substances which, in addition to having a herbicidal action against harmful plants, also have safener action on cultivated plants such as rice, such as, for example, rice. B.
  • RH 1 represents a (C 1 -C 12 haloalkyl radical
  • RH 2 is hydrogen or halogen
  • R H 3 , R H 4 are each independently hydrogen, (Ci-Ci 6 ) alkyl, (C 2 -C 16) alkenyl or
  • (C 2 -C 6 ) alkynyl where each of the last-mentioned 3 radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, hydroxy, cyano, (C 1 -C 10) alkoxy, (C 1 -C 12) haloalkoxy, C ijAlkylthio, (Ci-C ijAlkylamino, di [(Ci-C4) alkyl] amino, [(Ci-C4) alkoxy] - carbonyl, [(Ci-C-t jHaloalkoxyj carbonyl, (C3-C6) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, or (C3-C6) cycloalkyl, (C4-C6) cycloalkenyl, (C3-
  • RH 3 is (C 1 -C 4) alkoxy, (C 2 -C 4) alkenyloxy, (C 2 -C 6) alkynyloxy or (C 2 -C 4) haloalkoxy and R H 4 is hydrogen or (Ci-CQ-alkyl or
  • R H 3 and R H 4 together with the directly attached N atom form a four- to eight-membered one
  • heterocyclic ring which, in addition to the N atom, may also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group consisting of N, O and S, and which may be unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy and (C 1 -C 4 ) alkylthio, is substituted.
  • Preferred safeners in combination with the compounds according to the invention of the formula (I) and / or salts thereof, in particular with the compounds of the formulas (1.1) to (1.202) and / or salts thereof are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole ethyl ester, isoxadifen and particularly preferred safeners are: cloquintocetmexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.
  • Seeds of monocotyledonous or dicotyledonous weed plants were placed in 96-well microtiter plates in quartz sand and grown in the climatic chamber under controlled growth conditions.
  • the test plants were treated at the cotyledon stage 5 to 7 days after sowing.
  • the compounds of the invention formulated in the form of emulsion concentrates (EC) were applied at a rate of 2200 liters per hectare. After 9 to 12 days Life of the test plants in the climatic chamber under optimal growth conditions, the effect of the preparations was scored visually compared to untreated controls.
  • the abovementioned compounds have a very good herbicidal action (ie an 80% to 100% herbicidal action) against harmful plants such as Agrostis tenuis (AGSTE), Lolium perenne (LOLPE), Poa annua (POAAN), Setaria viridis (SETVI ), Stellaria media (STEME), Diplotaxis tenuifola (DIPTE) and Matricaria chamomilla (MATCH) at an application rate of 1900 g of active ingredient per hectare.
  • Agrostis tenuis AGSTE
  • LPE Lolium perenne
  • POAAN Poa annua
  • POAAN Setaria viridis
  • SETVI Setaria viridis
  • STEMVI Stellaria media
  • DITE Diplotaxis tenuifola
  • MATCH Matricaria chamomilla
  • Tables C1 to C2 show the effects of selected compounds of the general formula (I) according to Tables 1.1 to 1.129 on various harmful plants and an application rate corresponding to 1280 g / ha, which were obtained in accordance with the above-mentioned test procedure.
  • the compounds of the invention no. 1.2-55, 1.37-55 and 1.5-55 have a good herbicidal activity against the harmful plants Echinochloa crus-galli (ECHCG) and Stellaria media (STEME) at an application rate of post-emergence treatment 1280 g of active ingredient per hectare.
  • EHCG Echinochloa crus-galli
  • STME Stellaria media

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

Abstract

L'invention concerne des succinimide-3-carboxamides substitués représentés par la formule générale (I) ou leurs sels, les radicaux de la formule générale (I) étant tels que définis dans la description, 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. La présente invention concerne en outre des agents herbicides et/ou régulateurs de croissance végétale comprenant un ou plusieurs composés de formule générale (I).
PCT/EP2019/056681 2018-03-20 2019-03-18 Succinimide-3-carboxamides substitués, leurs sels et leur utilisation comme agents herbicides Ceased WO2019179928A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022029019A1 (fr) * 2020-08-05 2022-02-10 Syngenta Crop Protection Ag Composés herbicides
RU2852147C1 (ru) * 2020-08-05 2025-12-04 Сингента Кроп Протекшн Аг Гербицидные соединения

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022029019A1 (fr) * 2020-08-05 2022-02-10 Syngenta Crop Protection Ag Composés herbicides
CN116096711A (zh) * 2020-08-05 2023-05-09 先正达农作物保护股份公司 除草化合物
RU2852147C1 (ru) * 2020-08-05 2025-12-04 Сингента Кроп Протекшн Аг Гербицидные соединения
CN116096711B (zh) * 2020-08-05 2025-12-23 先正达农作物保护股份公司 除草化合物

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