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WO2020064260A1 - 5-(sulfanyl)-3,4-dihydro-2h-pyrrol-4-carboxamides substitués et leurs sels et leur utilisation comme agents herbicides - Google Patents

5-(sulfanyl)-3,4-dihydro-2h-pyrrol-4-carboxamides substitués et leurs sels et leur utilisation comme agents herbicides Download PDF

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Publication number
WO2020064260A1
WO2020064260A1 PCT/EP2019/073090 EP2019073090W WO2020064260A1 WO 2020064260 A1 WO2020064260 A1 WO 2020064260A1 EP 2019073090 W EP2019073090 W EP 2019073090W WO 2020064260 A1 WO2020064260 A1 WO 2020064260A1
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alkyl
ring
aryl
optionally substituted
compounds
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PCT/EP2019/073090
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German (de)
English (en)
Inventor
Uwe Döller
Hendrik Helmke
Stefan Lehr
Michael Charles MCLEOD
Thomas Müller
Olaf Peters
Anu Bheemaiah MACHETTIRA
Dirk Schmutzler
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Bayer Aktiengesellschaft
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Publication of WO2020064260A1 publication Critical patent/WO2020064260A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings

Definitions

  • the invention relates to the technical field of crop protection agents, in particular that of herbicides for the selective control of weeds and weeds in crops of useful plants.
  • this invention relates to substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides and their salts, processes for their preparation and their use as herbicides.
  • Crop crops or active ingredients to combat undesirable plant growth sometimes have disadvantages when used, either because they (a) have no or an inadequate herbicidal activity against certain harmful plants, (b) the spectrum of the harmful plants is too small to combat with an active ingredient can be (c) insufficient selectivity in crops and / or (d) have a toxicologically unfavorable profile.
  • active ingredients which can be used as plant growth regulators in some crop plants lead to undesirably reduced crop yields in other crop plants or are incompatible or only compatible with the crop plant in a narrow range of application rates.
  • Some of the known active ingredients cannot be economically manufactured on an industrial scale because of precursors and reagents that are difficult to access, or they have insufficient chemical stabilities. For other active substances, the effect depends too much on environmental conditions, such as weather and soil conditions.
  • WO2016 / 182780 describes certain substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides as intermediates in the synthesis of aryl-substituted bicyclic compounds with herbicidal properties.
  • WO2015 / 084796 describes certain substituted 2-oxo-N, 4-diphenylpyrrolidine-3-carboxamides and N, 4-diphenyl-2-sulfanylidene-pyrrolidine-3-carboxamides with herbicidal properties, the underlying central ring system always being a lactam or thiolactam group
  • substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides or their salts as herbicidal active ingredients has not yet been described.
  • selected substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides or their salts are particularly suitable as herbicidal active compounds as herbicides.
  • the present invention relates to the use of substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides of the general formula (1) or their salts as herbicidal active ingredients
  • Q represents an optionally substituted aryl, heteroaryl, with each ring or each
  • Z represents an optionally substituted aryl, heteroaryl, with each ring or each
  • R 2 is hydrogen, nitro, amino, cyano, thiocyanato, lsothiocyanato, halogen, (Ci-C 8) alkyl, (C 3- C 8) cycloalkyl, (C 2 -C 8) -alkenyl, (C 2 - C 8 ) -alkynyl, aryl, aryl- (Ci-C 8 ) -alkyl, aryl- (C 2 -C 8 ) -alkenyl, aryl- (C 2 -C 8 ) -alkynyl, aryl- (Ci-C 8 ) -alkoxy, heteroaryl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) - hydroxyalkyl, (Ci-C 8 ) -haloalkyl, (C 3 -C 8 ) - Halocycloalkyl
  • the compounds of general formula (1) can be added by adding a suitable one
  • inorganic or organic acid such as mineral acids such as HCl, HBr, H 2 SO 4 , ftPO i or HNO 3 , or organic acids, e.g. B. carboxylic acids, such as formic acid, acetic acid, Propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids, such as, for example, p-toluenesulfonic acid, form salts to a basic group, such as, for example, amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino. These salts then contain the conjugate base of the acid as an anion. Suitable substituents determined in deprotonated form, such as sulfonic acids
  • Sulphonic acid amides or carboxylic acids can form internal salts with protonatable groups such as amino groups. Salt formation can also be caused by exposure to 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 hydrogen carbonate are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or
  • Alkaline earth metal salts especially sodium and potassium salts, or also ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula
  • R a to R d each independently represent an organic radical, in particular alkyl, aryl, arylalkyl or alkylaryl.
  • Alkylsulfoxonium salts such as (Ci-C ij-trialkylsulfonium and (Ci-C ij-trialkylsulfoxonium salts.
  • substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides of the general formula (I) to be used according to the invention can be present in various tautomeric structures depending on external conditions, such as pH, solvent and temperature all of which are intended to be encompassed by the general formula (I).
  • a preferred subject of the invention is the use according to the invention of compounds of the general formula (I) in which
  • Q represents an optionally substituted aryl, heteroaryl, with each ring or each
  • Z represents an optionally substituted aryl, heteroaryl, with each ring or each
  • R 2 for hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, Alkyl, (C 3 -Cvj-cycloalkyl, (C 2 -Cv) alkenyl, (C 2 -Cv) alkynyl, aryl, aryl- (Ci-Cv) alkyl, aryl- (C 2 -Cv) alkenyl , Aryl- (C 2 -C 7 ) alkynyl, aryl- (Ci-C 7 ) -alkoxy, heteroaryl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkyl, (C 1 -C 7 ) - Hydroxyalkyl, (Ci-C 7 ) haloalkyl, (C 3 -C 7 ) halocycloalkyl, (Ci-C 7 ) alkoxy, (Ci-C 7 )
  • a particularly preferred subject of the invention is the use according to the invention of compounds of the general formula (I) in which
  • Q represents an optionally substituted aryl, heteroaryl, with each ring or each
  • Z represents an optionally substituted aryl, heteroaryl, with each ring or each
  • R 2 is hydrogen, nitro, amino, cyano, thiocyanato, lsothiocyanato, halogen, (Ci -Ce) - alkyl, (C3- C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, Aryl, aryl- (Ci-C 6 ) -alkyl, aryl- (C2-C6) -alkenyl, aryl- (C2-C6) -alkynyl, aryl- (Ci-C 6 ) -alkoxy, heteroaryl, (Ci-C 6 ) -alkoxy- (Ci-C 6 ) -alkyl, (Ci-Cr,) - Hydroxyalkyl, (Ci-C 6 ) haloalkyl, (C3-C6) halocycloalkyl, (Ci-C 6 ) alkoxy, (Ci-C 6 )
  • a very particularly preferred subject of the invention is the use of
  • Q represents an optionally substituted aryl, heteroaryl, with each ring or each
  • Z represents an optionally substituted aryl, heteroaryl, with each ring or each
  • R 2 for hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci-C i) alkyl, (C 3 -Csj-cycloalkyl, (C 2 -C i) alkenyl, (C 2 -C 4 ) -Alkynyl, aryl, aryl- (Ci-C 4 ) -alkyl, aryl- (C 2 -C 3 ) -alkenyl, aryl- (C 2 -C 3 ) -alkynyl, aryl- (Ci-C 4 ) - alkoxy, heteroaryl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, (C 1 -C 4 ) hydroxyalkyl, (Ci-C 4 ) haloalkyl, (C 3 -C 5 ) halocycloalkyl , (Ci-
  • R 1 represents methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclopropylmethyl, benzyl, p-methoxybenzyl, 2-phenethyl, allyl, propargyl,
  • Q represents one of the groups Q- 1.1 to Q- 10.14 specifically mentioned above,
  • Z stands for one of the groups Z-1 .1 to Z-4.3 specifically mentioned above, and
  • R 1 represents methyl, ethyl, cyclopropylmethyl, benzyl, 2-phenethyl, allyl, propargyl,
  • Q represents an optionally substituted aryl, heteroaryl, with each ring or each
  • Z represents an optionally substituted aryl, heteroaryl, with each ring or each
  • R 2 for hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci-C 8 ) alkyl, (C3-C 8 ) cycloalkyl, (C2-C 8 ) alkenyl, (C2-C 8 ) -Alkynyl, aryl, aryl- (Ci-C 8 ) -alkyl, aryl- (C2-C 8 ) -alkenyl, aryl- (C2-C 8 ) -alkynyl, aryl- (Ci-C 8 ) -alkoxy, heteroaryl , (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) - hydroxyalkyl, (Ci-C 8 ) -haloalkyl, (C3-C 8 ) -halocycloalkyl, (Ci-C 8
  • Q represents an optionally substituted aryl, heteroaryl, with each ring or each
  • Z represents an optionally substituted aryl, heteroaryl, with each ring or each
  • R 2 represents hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci-Cv) alkyl, (C 3 -Cv) cycloalkyl, (C2-Cv) alkenyl, (C2-Cv) alkynyl, Aryl, aryl- (Ci-Cv) -alkyl, aryl- (C2-Cv) -alkenyl, aryl- (C2-C7) -alkynyl, aryl- (Ci-C7) -alkoxy, heteroaryl, (Ci-C7) - Alkoxy- (Ci-C7) -alkyl, (C1-C7) -hydroxyalkyl, (Ci-C7) -haloalkyl, (C 3 -C7) -halocycloalkyl, (Ci-C7) -alkoxy, (Ci-C7) -haloalkoxy , Aryloxy
  • Particularly preferred subject matter of the invention are compounds of the general formula (I), in which Q represents an optionally substituted aryl, heteroaryl, with each ring or each
  • Z represents an optionally substituted aryl, heteroaryl, with each ring or each
  • R 2 represents hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci -Ce) - alkyl, (C3- C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, Aryl, aryl- (Ci-C 6 ) -alkyl, aryl- (C2-C6) -alkenyl, aryl- (C2-C6) -alkynyl, aryl- (Ci-C 6 ) -alkoxy, heteroaryl, (Ci-C 6 ) -alkoxy- (Ci-C 6 ) -alkyl, (GG,) - hydroxyalkyl, (GG) -haloalkyl, (C3-C6) -halocycloalkyl, (GG) -alkoxy, (GG) -haloalkoxy, aryloxy, heteroaryloxy
  • Q represents an optionally substituted aryl, heteroaryl, with each ring or each
  • R 2 for hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci-C i) alkyl, (C 3 -Csj-cycloalkyl, (C 2 -C i) alkenyl, (C 2 -C 4 ) -Alkynyl, aryl, aryl- (Ci-C 4 ) -alkyl, aryl- (C 2 -C 3 ) -alkenyl, aryl- (C 2 -C 3 ) -alkynyl, aryl- (Ci-C 4 ) - alkoxy, heteroaryl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, (C 1 -C 4 ) hydroxyalkyl, (Ci-C 4 ) haloalkyl, (C 3 -C 5 ) halocycloalkyl , (Ci-
  • Particularly preferred subject matter of the invention are compounds of the general formula (I) in which Q is for the groups Q-1.1 to Q-10.14
  • R 1 represents methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclopropylmethyl, benzyl, p-methoxybenzyl, 2-phenethyl, allyl, propargyl, except for the compounds mentioned below:
  • Q represents one of the groups Q- 1.1 to Q- 10.14 specifically mentioned above,
  • Z stands for one of the groups Z-1 .1 to Z-4.3 specifically mentioned above, and
  • R 1 represents methyl, ethyl, cyclopropylmethyl, benzyl, 2-phenethyl, allyl, propargyl, except for the compounds mentioned below:
  • alkylsulfonyl alone or as part of a chemical group - stands for straight-chain or branched alkylsulfonyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms for example (but not limited to) (Ci-C 6 ) alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, l, l-dimethylethylsulfonyl, pentyl 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, l, l-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonylsulfonyl, 1-methyl 3-
  • heteroarylsulfonyl stands for 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 - stands for straight-chain or branched S-alkyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms such as (Ci-Cio) -, (C i-Cr,) - 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, l, l-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, l, l-dimethylpropylthio, 1, 2-dimethylpropylthio, 2,2- Dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio
  • cycloalkylthio means one bonded via a sulfur atom
  • (but not limited to) (Ci-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, eg. B. (but not limited to) (Ci-C 6 ) 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, l, 2-dimethylbutoxy, l, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, l
  • Alkenyloxy means an alkenyl radical bonded via an oxygen atom
  • alkynyloxy means an alkynyl radical bonded via an oxygen atom, such as (C2-C10) -, (C2-C6) - or (C2-C4) -alkenoxy or (C3-C10) -, (C3 -C6) - or (C3-C 4 ) alkynoxy.
  • Cycloalkyloxy means a cycloalkyl radical bonded via an oxygen atom.
  • the number of carbon atoms refers to the alkyl radical in the
  • the number of carbon atoms relates to the alkyl radical in the alkoxycarbonyl group.
  • alkenyloxycarbonyl and “alkynyloxycarbonyl”, unless otherwise defined elsewhere, according to the invention stand for alkenyl or alkynyl radicals which are bonded to the structure via -0-C ( 0) -, such as (C2-C 10) -, (C2-C6) - or (C2-C 4 ) alkenyloxycarbonyl or (C3-C 10) -, (C3-C6) - or (C3-C4) - alkynyloxycarbonyl.
  • the number of carbon atoms relates to the alkenyl or alkynyl radical in the alkene or alkynyloxycarbonyl group.
  • the number of carbon atoms relates to the alkyl radical in the alkylcarbonyloxy group.
  • aryl means an optionally substituted mono-, bi- or polycyclic aromatic system with preferably 6 to 14, in particular 6 to 10 ring carbon atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
  • optionally substituted aryl also includes multi-cyclic 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, haloalkylthoxy, haloalkyl, haloalkyl Cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroraryloxy, 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
  • ( carbocyclic ring in which at least one C atom is replaced by a hetero atom, preferably by a hetero atom from the group N, O, S, P) which is saturated, unsaturated, partially saturated or heteroaromatic and can be unsubstituted or substituted, where the binding site is located on a ring atom.
  • the heterocyclyl radical or the heterocyclic ring is optionally substituted, it can be fused with other carbocyclic or heterocyclic rings.
  • heterocyclyl In the case of optionally substituted heterocyclyl, multi-cyclic systems are also included, such as 8-aza-bicyclo [3.2.1] octanyl, 8-aza-bicyclo [2.2.2] octanyl or l-azabicyclo [2.2.l] heptyl. In the case of optionally substituted heterocyclyl also
  • 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 should be directly adjacent, such as with a heteroatom from the group N, O and S 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2- or 3-yl, 2,3- Dihydro-lH-pyrrole
  • 3-ring and 4-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 with two heteroatoms from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazol-3- or 4- or 5-yl; 4,5-dihydro-1H-pyrazole-l- or 3- or 4- or 5-yl; 2,3-dihydro-1H-pyrazole-1 or 2- or
  • 6-yl l, 4,5,6-tetrahydropyridazin-l- or 3- or 4- or 5- or 6-yl; 3,4,5,6-tetrahydropyridazin-3- or 4- or 5-yl; 4,5-dihydropyridazin-3- or 4-yl; 3,4-dihydropyridazin-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazin-3- or 4-yl; l, 6-dihydropyriazin-l- or 3- or 4- or 5- or 6-yl;
  • 1,2-dithiolan-3- or 4-yl 1,2-dithiolan-3- or 4-yl; 3H-l, 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-l, 2-dithiin-3- or 4- or 5- or 6-yl; 3,6-dihydro
  • 6- or 7-yl 2,5-dihydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-l, 3-oxazepine 2- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; l, 3-oxazepin-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-l, 4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2, 3, 4, 7-tetrahydro-l, 4-oxazepin-2
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical with 3 heteroatoms from the group N, O and S, such as l, 4,2-dioxazolidin-2- or 3- or 5-yl; l, 4,2-dioxazol-3- or 5-yl; 1, 4,2-dioxazinan-2- or -3- or 5- or 6-yl; 5,6-dihydro-l, 4,2-dioxazin-3- or 5- or 6-yl; l, 4,2-dioxazin-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-dioxazepin-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-l, 4,2-dioxa
  • heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxyl, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl,
  • Alkylaminocarbonyl bis-alkylaminocarbonyl, cycloalkylaminocarbonyl,
  • nitrogen heterocycle is partially or fully saturated, it can be linked to the rest of the molecule via carbon as well as nitrogen.
  • Possible substituents for a substituted heterocyclic radical are the substituents mentioned below, and also oxo and thioxo.
  • the oxo group as a substituent on a ring carbon atom then means, for example, a carbonyl group in the heterocyclic ring. Lactones and lactams are thereby preferably also included.
  • the oxo group can also occur on the hetero ring atoms, which can exist in various oxidation states, for example N and S, and then form, for example, the divalent groups N (O), S (O) (also SO for short) and S (0) 2 (also SO2) in the heterocyclic ring. In the case of -N (O) - and -S (0) groups, both enantiomers are included.
  • heteroaryl stands for heteroaromatic compounds, ie. H.
  • heteroaryls are, for example, 1H-pyrrol-l-yl; 1H-pyrrol-2-yl; lH-pyrrole
  • Carbon atoms are part of another aromatic ring, so they are fused heteroaromatic systems, such as benzo-fused or multi-fused heteroaromatic.
  • quinolines e.g. quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • Isoquinolines e.g. quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • Isoquinolines e.g.
  • heteroaryl are also 5- or 6-membered benzo-fused rings from the group lH-indol-l-yl, lH-indol-2-yl, lH-indol-3-yl, lH-indol-4-yl, lH- Indol-5-yl, 1H-indol-6-yl, lH-indol-7-yl, l-benzofuran-2-yl, l-benzofuran-3-yl, l-benzofuran-4-yl, l-benzofuran 5- yl, l-benzofuran-6-yl, l-benzofuran-7-yl, l-benzothiophene-2-yl, l-benzothiophene-3-yl, 1-benzothiophene-4-yl, l-benzothiophene-5- yl, l-benzothiophene-6-yl, l-benz
  • 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 substituted one or more times and is referred to in the latter case as “substituted alkyl”.
  • Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups; methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine are particularly preferred.
  • the prefix "bis” also includes the combination of different alkyl residues, e.g. B. methyl (ethyl) or ethyl (methyl).
  • Haloalkyl “Haloalkyl”, “- alkenyl” and “- alkynyl” mean alkyl, alkenyl or alkynyl, for example monohaloalkyl, which is partially or completely substituted by identical or different halogen atoms
  • ( Monohalogenalkyl) such as B. CH 2 CH 2 CI, CH 2 CH 2 Br, CHCICH 3 , CH 2 CI, CH 2 F; Perhaloalkyl such as B. CCI3, CCIF 2 , CFC1 2 , CF 2 CC1F 2 , CF 2 CCIFCF3; Polyhaloalkyl such as B. CH 2 CHFC1, CF 2 CC1FH, CF 2 CBrFH, CH 2 CF 3 ;
  • perhaloalkyl also includes the term perfluoroalkyl.
  • Partially fluorinated alkyl means a straight-chain or branched, saturated hydrocarbon which is mono- or polysubstituted by fluorine, and the corresponding fluorine atoms can be located as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain, such as, for example, B. 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
  • Hydrocarbon which is substituted by different halogen atoms with at least one fluorine atom, all other halogen atoms which may be present being selected from the group consisting of fluorine, chlorine or bromine, iodine.
  • the corresponding halogen atoms can be located 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 the straight or branched chain by halogen with the participation of at least one fluorine atom.
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 CI; The same applies to haloalkenyl and other halogen-substituted radicals.
  • (Ci-C4) -alkyl mentioned here by way of example means a shorthand notation for straight-chain or branched alkyl having one to 4 carbon atoms corresponding to the
  • Range specification for carbon atoms includes the residues methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl.
  • General alkyl radicals with a larger specified range of carbon atoms e.g. B. "(Ci-C 6 ) alkyl”, also include straight-chain or branched alkyl radicals with a larger number of carbon atoms, ie, according to the example, also the alkyl radicals with 5 and 6 carbon atoms.
  • the lower carbon skeletons for example with 1 to 6 C atoms or, in the case of unsaturated groups, with 2 to 6 C atoms, are preferred for the hydrocarbon radicals, such as alkyl, alkenyl and alkynyl radicals, even in composite radicals.
  • Alkyl radicals also in the composite radicals such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i -Hexyl and 1,3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1, 4-dimethylpentyl;
  • Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, at least one double bond or triple bond being present. Residues with a double bond or
  • alkenyl also includes straight-chain or branched open-chain ones
  • Hydrocarbon radicals with more than one double bond such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals with one or more cumulative double bonds, such as, for example, allenyl (1,2-propadienyl), 1,1 2-butadienyl and l, 2,3-pentatrienyl.
  • Alkenyl means e.g.
  • Vinyl which may optionally be substituted by further alkyl radicals, for example (but not limited to) (CAGO-alkyl, 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, l, l-dimethyl-2-propenyl, l, 2-dimethyl-l-prop
  • alkynyl also includes straight-chain or branched open-chain ones
  • C2-C6 alkynyl means, for example, ethynyl, l-propynyl, 2-propynyl, l-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, l-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, l-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-penty
  • cycloalkyl means a carbocyclic, saturated ring system with 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 with substituents are included, substituents also having a double bond on
  • Cycloalkyl radical e.g. B. an alkylidene group such as methylidene are included.
  • alkylidene group such as methylidene
  • multicyclic aliphatic systems are also included, such as, for example, bicyclo [1.0] butan-1-yl, bicyclo [1.0] butan-2-yl, bicyclo [2.1.0] pentan-1 - yl, bicyclo [l.
  • (C3-C7) cycloalkyl means a shorthand notation for cycloalkyl of three to seven
  • spirocyclic aliphatic systems are also included, such as, for example, spiro [2.2] pent-l-yl, spiro [2.3] hex-l-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl,
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system with preferably 4-8 C atoms, e.g. 1-Cyclobutenyl, 2-Cyclobutenyl, 1-Cyclopentenyl, 2-Cyclopentenyl, 3-Cyclopentenyl, or 1-Cyclohexenyl, 2-Cyclohexenyl, 3-Cyclohexenyl, l, 3-Cyclohexadienyl or 1, 4-Cyclohexadienyl, whereby also substituents with a Double bond on the cycloalkenyl radical, e.g. B.
  • the explanations for substituted cycloalkyl apply accordingly.
  • alkylidene e.g. B. also in the form (Ci-Cio) alkylidene, means the remainder of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond.
  • Cycloalkylidene means a
  • alkoxyalkyl stands for an alkoxy radical bonded via an alkyl group and "alkoxyalkoxy” means an alkoxyalkyl radical bonded via an oxygen atom, for example (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy.
  • Alkylthioalkyl stands for an alkylthio radical bonded via an alkyl group
  • Alkylthioalkylthio means an alkylthioalkyl radical bonded via an oxygen atom.
  • Arylalkoxyalkyl stands for an aryloxy radical bonded via an alkyl group
  • Heteroaryloxyalkyl means a heteroaryloxy radical bonded via an alkyl group.
  • Haloalkoxyalkyl stands for a bound haloalkoxy radical and “Haloalkylthioalkyl” means a haloalkylthio radical bound via an alkyl group.
  • Arylalkyl stands for an aryl radical bonded via an alkyl group
  • heteroarylalkyl means a heteroaryl radical bonded via an alkyl group
  • heterocyclylalkyl means a heterocyclyl radical bonded via an alkyl group.
  • Cycloalkylalkyl stands for a cycloalkyl radical bonded via an alkyl group, eg. 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 alone or as part of a chemical group - stands for straight-chain or branched S -haloalkyl, preferably with 1 to 8 or with 1 to 6 carbon atoms, such as (Ci-Cs) -, (C ' iG,) - or (Ci-C4) -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 identical or different halogen atoms, such as. B. F, CI and Br, or by haloalkyl, such as. B. trifluoromethyl or difluoromethyl partially or fully substituted cycloalkyl or cycloalkenyl, e.g.
  • l-fluorocycloprop-l-yl 2-fluorocycloprop-l-yl, 2,2-difluorocycloprop-l-yl, l-fluorocyclobut-l-yl, l-trifluoromethylcycloprop-l-yl, 2-trifluoromethylcycloprop-1-yl, 1-chloro-cycloprop-1-yl, 2-chlorocycloprop-1-yl, 2,2-dichlorocycloprop-1-yl, 3,3-difluorocyclobutyl.
  • trialkylsilyl alone or as part of a chemical group - stands for straight-chain or branched Si-alkyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms such as tri - [(Ci-C 8 ) -, (C i-Cr,) - or (Ci-C i) alkyl] silyl, for example (but not limited to) Trimethylsilyl, triethylsilyl, tri- (n-propyl) silyl, tri- (iso-propyl) silyl, tri- (n-butyl) silyl, tri- (l-methylprop-l-yl) silyl, tri- (2-methylprop -l-yl) silyl, tri (l, l-dimethyleth-l-yl) silyl, tri (2,2-dimethyleth-1-yl) silyl.
  • Carbonyl compounds are present both in the keto form and in the enol form, both forms being encompassed by the definition of the compound of the general formula (I).
  • the compounds of the general formula (I) can be present as stereoisomers.
  • the possible stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the general formula (I).
  • enantiomers, diastereomers, Z and E isomers are all encompassed by the general formula (I).
  • diastereomers Z and E isomers
  • enantiomers and diastereomers can occur.
  • Stereoisomers can be derived from the at
  • Stereoisomers can also be prepared selectively by using stereoselective reactions using optically active starting materials and / or auxiliary substances.
  • the invention thus also relates to all stereoisomers which are encompassed by the general formula (I) but are not specified with their specific stereoform, and to their mixtures.
  • the cleaning can also be carried out by
  • the substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides of the general formula (I) according to the invention can be prepared starting from known processes.
  • the synthetic routes used and investigated are based on commercially available or easily produced amines, on appropriately substituted aldehydes and on commercially available chemicals such as malonic acid derivatives and nitromethane.
  • the groupings Q, Z, R 1 and R 2 of the general formula (I) have the meanings previously defined in the following schemes, unless exemplary but not restrictive definitions are given.
  • the compounds of the general formula (I) according to the invention are synthesized via an alkylation of an amide of the general formula (II) with an alkylating compound of the general formula (III) in the presence of a base such as, for example, potassium carbonate or
  • the reaction preferably takes place in the temperature range between 0 ° C and 100 ° C, in an adequate solvent such as dichloromethane, acetonitrile, W-dimethylformamide or ethyl acetate (see Scheme 1). Take the amide group and the rest Q.
  • the cis isomer can be detected in small amounts by NMR.
  • the compounds of the general formula (II) are synthesized by aminolysis of an ester of the general formula (IV) with an amine of the general formula (V).
  • the reaction preferably takes place in the temperature range between 20 ° C and 180 ° C (see scheme 2) and can be carried out without solvent by melting. Take the amide group and the rest Q. predominantly the trans configuration. In some cases, the cis isomer can be detected in small amounts by NMR.
  • R ' (Ci-C 4 ) alkyl
  • the compounds of the general formula (IV) are synthesized by reacting the general formula (VI) with a sulfurization reagent, such as, for example, phosphorus pentasulfide or Lawesson's reagent.
  • a sulfurization reagent such as, for example, phosphorus pentasulfide or Lawesson's reagent.
  • the reaction preferably takes place in the temperature range between 20 ° C and 180 ° C, in an adequate solvent such as toluene, chlorobenzene or dichlorobenzene (see scheme 3).
  • the amide group and the rest Q predominantly assume the trans configuration.
  • the cis isomer can be detected in small amounts by NMR.
  • R ' (Ci-C 4 ) alkyl
  • the synthesis of the compound of the general formula (VI) can be prepared by reduction of the compound of the general formula (VII) and subsequent in situ cyclization of the amine intermediate formed by or analogously to methods known to the person skilled in the art (see Scheme 4).
  • the reduction of aliphatic nitro groups by catalytic hydrogenolysis is in the literature
  • Presence of palladium on coal or RaneyNickel, iron or zinc in the acidic medium (see for example reports of the German Chemical Society 1904, 37, 3520-3525), and lithium alanate.
  • the reduction can also be carried out with samarium (II) iodide in the presence of a proton source such as, for example, methanol (see, for example, Tetrahedron Leiters 1991, 32 (14), 1699-1702).
  • a proton source such as, for example, methanol
  • the reduction of the aliphatic nitro group with sodium borohydride can be carried out in the presence of nickel (II) acetate or nickel (II) chloride (see, for example, Tetrahedron Leiters 1985, 26 (52), 6413-6416).
  • R ' (Ci-C 4 ) alkyl
  • the base may be an alkanolate salt of an alkali metal (such as sodium methylate or sodium ethylate) in an adequate solvent such as methanol or ethanol.
  • the reaction can be carried out with bases such as lithium hexamethyldisilazane,
  • R ' (Ci-C 4 ) alkyl
  • the compounds of general formula (VIII) can be prepared by Knoevenagel condensation of an aldehyde of general formula (XI) and malonic esters of general formula (XII) (see Scheme 6; G. Jones, Organic Reactions Volume 15, John Wiley and Sons, 1967 ).
  • R ' (Ci-C 4 ) alkyl
  • Scheme 7 describes the synthesis of the compound of the general formula (VII) by reacting a malonic ester of the general formula (XII) with a nitroolefin of the general formula (XIII) in the presence of a base.
  • the base may be an alkanolate salt or hydroxide of an alkali metal (such as sodium methylate or sodium ethylate) in an adequate solvent such as methanol or ethanol, or bases such as lithium hexamethyldisilazane,
  • R ' (Ci-C 4 ) alkyl
  • the compounds of the general formula (XIII) can be prepared by condensing an aldehyde of the general formula (XI) and compounds of the general formula (IX) in the presence of a base such as sodium hydride in an adequate solvent such as tetrahydrofuran (see Scheme 8 ).
  • the compounds of the general formula (II) are synthesized by reacting the general formula (XV) with a sulfurization reagent, such as, for example, phosphorus pentasulfide or Lawesson's reagent.
  • a sulfurization reagent such as, for example, phosphorus pentasulfide or Lawesson's reagent.
  • the reaction preferably takes place in the temperature range between 20 ° C and 180 ° C, in an adequate solvent such as toluene, chlorobenzene or dichlorobenzene (see scheme 9).
  • the amide group and the rest Q predominantly assume the trans configuration.
  • the cis isomer can be detected in small amounts by NMR.
  • the compound of the general formula (XIV) can also be formed in the reaction.
  • the compounds of the general formula (XV) are synthesized via an amide coupling of an acid of the general formula (XVI) with an amine of the general formula (V) in the presence of an amide coupling reagent such as, for example, T3P, dicyclohexylcarbodiimide, N- (3-dimcthylaminopropyl) - / ⁇ "- cthylcarbodiimide, / V,, VC abony 1 diimid azo 1, 2-chloro-l, 3-dimethyl-imidazolium chloride or 2-chloro-l-methylpyridinium iodide (see Chemistry of Peptide Synthsis, Ed. N.
  • Polymer-bound reagents such as polymer-bound dicyclohexylcarbodiimide are also suitable for this coupling reaction.
  • the reaction takes place preferably in the temperature range between 0 ° C.
  • the synthesis of the acid of the general formula (XVI) can be prepared by saponification of the compound of the general formula (VI) according to or analogously to methods known to the skilled worker (Scheme 11).
  • the saponification can be carried out in the presence of a base or a Lewis acid.
  • the base can 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 can be boron tribromide and the reaction can be carried out in a temperature range between -20 ° C and 100 ° C, preferably -5 ° C and 50 ° C.
  • R ' (Ci-C 4 ) alkyl
  • Polymer-bound reagents such as polymer-bound dicyclohexylcarbodiimide are also suitable for this coupling reaction.
  • the reaction preferably takes place in the temperature range between 0 ° C and 80 ° C, in an adequate solvent such as dichloromethane, acetonitrile,, V,, V- D imct hy 1 - for ma mid or ethyl acetate and in the presence of a base such as triethylamine, / V,, V- D iisop ro py 1 c t h y 1 a m i n or l, 8-diazabicyclo [5.4.0] undec-7-cen instead (see Scheme 12).
  • T3P peptide coupling conditions see Organic Process Research & Development 2009, 13, 900-906.
  • the amide group and the rest Q predominantly assume the trans configuration. In some cases, the
  • the synthesis of the acid of the general formula (XVII) can be prepared by saponification of the compound of the general formula (XVIII) according to or analogously to methods known to the person skilled in the art (Scheme 13).
  • 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
  • the Lewis acid can be boron tribromide and the reaction can be carried out in a temperature range between -20 ° C and 100 ° C, preferably -5 ° C and 50 ° C.
  • R ' (Ci-C 4 ) alkyl
  • R ' (Ci-C 4 ) alkyl
  • reaction mixture was stirred at room temperature overnight and then sat.
  • Ammonium chloride solution (20ml) and ethyl acetate (20ml) added and stirred for a further hour at room temperature.
  • the insoluble constituents were filtered off over Celite and the phases were subsequently separated.
  • the aqueous phase was extracted several times with ethyl acetate, and the combined organic phases were then washed with sat.
  • Ammonium chloride solution and sat. Washed sodium chloride solution, dried over magnesium sulfate, filtered and concentrated.
  • the resulting crude product was dissolved in ethanol (40 ml) and a solution of sodium hydroxide (1.12 g, 27.8 mmol, 3.0 equiv) in water (40 ml) was added.
  • the resulting reaction mixture was stirred at room temperature overnight and then water (50 ml) and diethyl ether (50 ml) were added.
  • the organic phase was discarded and the aqueous phase with conc. HCl adjusted to pH 2.
  • the aqueous phase was extracted several times with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated.
  • Table 1.1 Preferred compounds of the formula (1.1) are the compounds 1.1-1 to 1.1-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.1-1 to 1.1-247 of table 1.1 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1.
  • Table 1.2 Preferred compounds of the formula (1.2) are the compounds 1.2-1 to 1.2-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.2-1 to 1.2-247 of table 1.2 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.3 Preferred compounds of the formula (1.3) are the compounds 1.3-1 to 1.3-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.3-1 to 1.3-247 of table 1.3 are thus by the meaning of the respective entries no. 1 to 247 defined for Q of Table 1.
  • Table 1.4 Preferred compounds of the formula (1.4) are the compounds 1.4-1 to 1.4-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.4-1 to 1.4-247 of table 1.4 are thus by the meaning of the respective entries no. 1 to 247 defined for Q of Table 1 above.
  • Table 1.5 Preferred compounds of the formula (1.5) are the compounds 1.5-1 to 1.5-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.5-1 to 1.5-247 of table 1.5 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.6 Preferred compounds of the formula (1.6) are the compounds 1.6-1 to 1.6-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.6-1 to 1.6-247 of table 1.6 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.7 Preferred compounds of the formula (1.7) are the compounds 1.7-1 to 1.7-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.7-1 to 1.7-247 of table 1.7 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.8 Preferred compounds of the formula (1.8) are the compounds 1.8-1 to 1.8-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.8-1 to 1.8-247 in Table 1.8 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.9 Preferred compounds of the formula (1.9) are the compounds 1.9-1 to 1.9-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.9-1 to 1.9-247 of table 1.9 are thus by the meaning of the respective entries no. 1 to 247 defined for Q of Table 1 above.
  • Table 1.10 Preferred compounds of the formula (1.10) are the compounds 1.10-1 to 1.10-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.10-1 to 1.10-247 of table 1.10 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.11 Preferred compounds of the formula (1.11) are the compounds 1.11-1 to 1.11-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.11-1 to 1.11-247 of table 1.11 are thus by the meaning of the respective entries No. 1 to
  • Table 1.12 Preferred compounds of the formula (1.12) are the compounds 1.12-1 to 1.12-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.12-1 to 1.12-247 of table 1.12 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.13 Preferred compounds of the formula (1.13) are the compounds 1.13-1 to 1.13-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.13-1 to 1.13-247 of table 1.13 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.14 Preferred compounds of the formula (1.14) are the compounds 1.14-1 to 1.14-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.14-1 to 1.14-247 of table 1.14 are thus by the meaning of the respective entries No. 1 to
  • Table 1.15 Preferred compounds of the formula (1.15) are the compounds 1.15-1 to 1.15-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.15-1 to 1.15-247 of table 1.15 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.16 Preferred compounds of the formula (1.16) are the compounds 1.16-1 to 1.16-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.16-1 to 1.16-247 of table 1.16 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.17 Preferred compounds of the formula (1.17) are the compounds 1.17-1 to 1.17-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.17-1 to 1.17-247 of table 1.17 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.18 Preferred compounds of the formula (1.18) are the compounds 1.18-1 to 1.18-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.18-1 to 1.18-247 of table 1.18 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.19 Preferred compounds of the formula (1.19) are the compounds 1.19-1 to 1.19-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.19-1 to 1.19-247 of table 1.19 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.20 Preferred compounds of the formula (1.20) are the compounds 1.20-1 to 1.20-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.20-1 to 1.20-247 of table 1.20 are thus 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 1.21-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.21-1 to 1.21-247 of table 1.21 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Preferred compounds of the formula (1.22) are the compounds 1.22-1 to 1.22-247, in which Q has the meanings of Table 1 given in the respective row.
  • Table 1.23 Preferred compounds of the formula (1.23) are the compounds 1.23-1 to 1.23-247, in which Q has the meanings of Table 1 given in the respective row.
  • Table 1.24 Preferred compounds of the formula (1.24) are the compounds 1.24-1 to 1.24-247, in which Q has the meanings of Table 1 given in the respective row. The connections
  • Table 1.25 Preferred compounds of the formula (1.25) are the compounds 1.25-1 to 1.25-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.25-1 to 1.25-247 of table 1.25 are thus by the meaning of the respective entries No. 1 to
  • Table 1.26 Preferred compounds of the formula (1.26) are the compounds 1.26-1 to 1.26-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.26-1 to 1.26-247 of table 1.26 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.27 Preferred compounds of the formula (1.27) are the compounds 1.27-1 to 1.27-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.27-1 to 1.27-247 of table 1.27 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.28 Preferred compounds of the formula (1.28) are the compounds 1.28-1 to 1.28-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.28-1 to 1.28-247 of table 1.28 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.29 Preferred compounds of the formula (1.29) are the compounds 1.29-1 to 1.29-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.29-1 to 1.29-247 of table 1.29 are thus by the meaning of the respective entries No. 1 to
  • Table 1.30 Preferred compounds of the formula (1.30) are the compounds 1.30-1 to 1.30-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.30-1 to 1.30-247 of table 1.30 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.31 Preferred compounds of the formula (1.31) are the compounds 1.31-1 to 1.31-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.31-1 to 1.31-247 of table 1.31 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.32 Preferred compounds of the formula (1.32) are the compounds 1.32-1 to 1.32-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.32-1 to 1.32-247 of table 1.32 are thus 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 1.33-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.33-1 to 1.33-247 of table 1.33 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.34 Preferred compounds of the formula (1.34) are the compounds 1.34-1 to 1.34-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.34-1 to 1.34-247 of table 1.34 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.35 Preferred compounds of the formula (1.35) are the compounds 1.35-1 to 1.35-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.35-1 to 1.35-247 in table 1.35 are thus by the meaning of the respective entries No. 1 to
  • Table 1.36 Preferred compounds of the formula (1.36) are the compounds 1.36-1 to 1.36-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.36-1 to 1.36-247 of table 1.36 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.37 Preferred compounds of the formula (1.37) are the compounds 1.37-1 to 1.37-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.37-1 to 1.37-247 of table 1.37 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.38 Preferred compounds of the formula (1.38) are the compounds 1.38-1 to 1.38-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.38-1 to 1.38-247 of table 1.38 are thus by the meaning of the respective entries No. 1 to
  • Table 1.39 Preferred compounds of the formula (1.39) are the compounds 1.39-1 to 1.39-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.39-1 to 1.39-247 of table 1.39 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.40 Preferred compounds of the formula (1.40) are the compounds 1.40-1 to 1.40-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.40-1 to 1.40-247 of table 1.40 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.41 Preferred compounds of the formula (1.41) are the compounds 1.41-1 to 1.41-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.41-1 to 1.41-247 of table 1.41 are thus by the meaning of the respective entries No. 1 to
  • Table 1.42 Preferred compounds of the formula (1.42) are the compounds 1.42-1 to 1.42-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.42-1 to 1.42-247 in table 1.42 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.43 Preferred compounds of the formula (1.43) are the compounds 1.43-1 to 1.43-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.43-1 to 1.43-247 of table 1.43 are thus by the meaning of the respective entries No. 1 to
  • Table 1.44 Preferred compounds of the formula (1.44) are the compounds 1.44-1 to 1.44-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.44-1 to 1.44-247 of table 1.44 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.45 Preferred compounds of the formula (1.45) are the compounds 1.45-1 to 1.45-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.45-1 to 1.45-247 in table 1.45 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.46 Preferred compounds of the formula (1.46) are the compounds 1.46-1 to 1.46-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.46-1 to 1.46-247 in table 1.46 are thus by the meaning of the respective entries No. 1 to
  • Table 1.47 Preferred compounds of the formula (1.47) are the compounds 1.47-1 to 1.47-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.47-1 to 1.47-247 of table 1.47 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.48 Preferred compounds of the formula (1.48) are the compounds 1.48-1 to 1.48-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.48-1 to 1.48-247 of table 1.48 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.49 Preferred compounds of the formula (1.49) are the compounds 1.49-1 to 1.49-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.49-1 to 1.49-247 of table 1.49 are thus by the meaning of the respective entries No. 1 to
  • Table 1.50 Preferred compounds of the formula (1.50) are the compounds 1.50-1 to 1.50-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.50-1 to 1.50-247 of table 1.50 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.51 Preferred compounds of the formula (1.51) are the compounds 1.51-1 to 1.51-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.51-1 to 1.51-247 of table 1.51 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.52 Preferred compounds of the formula (1.52) are the compounds 1.52-1 to 1.52-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.52-1 to 1.52-247 of table 1.52 are thus 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 1.53-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.53-1 to 1.53-247 of table 1.53 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.54 Preferred compounds of the formula (1.54) are the compounds 1.54-1 to 1.54-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.54-1 to 1.54-247 of table 1.54 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.55 Preferred compounds of the formula (1.55) are the compounds 1.55-1 to 1.55-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.55-1 to 1.55-247 of table 1.55 are thus 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 1.56-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.56-1 to 1.56-247 of table 1.56 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.57 Preferred compounds of the formula (1.57) are the compounds 1.57-1 to 1.57-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.57-1 to 1.57-247 of table 1.57 are thus by the meaning of the respective entries No. 1 to
  • Table 1.58 Preferred compounds of the formula (1.58) are the compounds 1.58-1 to 1.58-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.58-1 to 1.58-247 of table 1.58 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.59 Preferred compounds of the formula (1.59) are the compounds 1.59-1 to 1.59-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.59-1 to 1.59-247 of table 1.59 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.60 Preferred compounds of the formula (1.60) are the compounds 1.60-1 to 1.60-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.60-1 to 1.60-247 of table 1.60 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.61 Preferred compounds of the formula (1.61) are the compounds 1.61-1 to 1.61-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.61-1 to 1.61-247 of table 1.61 are thus by the meaning of the respective entries No. 1 to
  • Table 1.62 Preferred compounds of the formula (1.62) are the compounds 1.62-1 to 1.62-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.62-1 to 1.62-247 of table 1.62 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.63 Preferred compounds of the formula (1.63) are the compounds 1.63-1 to 1.63-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.63-1 to 1.63-247 of table 1.63 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.64 Preferred compounds of the formula (1.64) are the compounds 1.64-1 to 1.64-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.64-1 to 1.64-247 of table 1.64 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.65 Preferred compounds of the formula (1.65) are the compounds 1.65-1 to 1.65-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.65-1 to 1.65-247 of table 1.65 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.66 Preferred compounds of the formula (1.66) are the compounds 1.66-1 to 1.66-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.66-1 to 1.66-247 of table 1.66 are thus 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 1.67-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.67-1 to 1.67-247 of table 1.67 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.68 Preferred compounds of the formula (1.68) are the compounds 1.68-1 to 1.68-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.68-1 to 1.68-247 of table 1.68 are thus 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 1.69-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.69-1 to 1.69-247 of table 1.69 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.70 Preferred compounds of the formula (1.70) are the compounds 1.70-1 to 1.70-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.70-1 to 1.70-247 of table 1.70 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.71 Preferred compounds of the formula (1.71) are the compounds 1.71-1 to 1.71-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.71-1 to 1.71-247 of table 1.71 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.72 Preferred compounds of the formula (1.72) are the compounds 1.72-1 to 1.72-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.72-1 to 1.72-247 in table 1.72 are thus by the meaning of the respective entries No. 1 to
  • Table 1.73 Preferred compounds of the formula (1.73) are the compounds 1.73-1 to 1.73-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.73-1 to 1.73-247 of table 1.73 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.74 Preferred compounds of the formula (1.74) are the compounds 1.74-1 to 1.74-247, in which Q has the meanings of Table 1 given in the respective row. The connections
  • Table 1.75 Preferred compounds of the formula (1.75) are the compounds 1.75-1 to 1.75-247, in which Q has the meanings of Table 1 given in the respective row. The connections
  • Table 1.76 Preferred compounds of the formula (1.76) are the compounds 1.76-1 to 1.76-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.76-1 to 1.76-247 of table 1.76 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.77 Preferred compounds of the formula (1.77) are the compounds 1.77-1 to 1.77-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.77-1 to 1.77-247 of table 1.77 are thus by the meaning of the respective entries No. 1 to
  • Table 1.78 Preferred compounds of the formula (1.78) are the compounds 1.78-1 to 1.78-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.78-1 to 1.78-247 of table 1.78 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.79 Preferred compounds of the formula (1.79) are the compounds 1.79-1 to 1.79-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.79-1 to 1.79-247 of table 1.79 are thus by the meaning of the respective entries No. 1 to
  • Table 1.80 Preferred compounds of the formula (1.80) are the compounds 1.80-1 to 1.80-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.80-1 to 1.80-247 of table 1.80 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.81 Preferred compounds of the formula (1.81) are the compounds 1.81-1 to 1.81-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.81-1 to 1.81-247 of table 1.81 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.82 Preferred compounds of the formula (1.82) are the compounds 1.82-1 to 1.82-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.82-1 to 1.82-247 in table 1.82 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • NMR peak list method The 1 H-NMR data of selected examples are noted in the form of 1 H-NMR peak lists. For each signal peak, the d-value is shown in ppm and then the signal intensity in round brackets. The d-value - signal intensity-number pairs of different signal peaks are listed separated from each other by semicolons.
  • the peak list of an example therefore has the form: di (intensity ⁇ ; d2 (intensity2);.; D; (intensity ⁇ ;.; D h (intensity n )
  • the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the real relationships of the signal intensities. With wide signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum.
  • the peaks of stereoisomers of the target compounds and / or peaks of impurities usually have a lower intensity on average than the peaks of the target compounds (for example with a purity of> 90%).
  • stereoisomers and / or impurities can be typical of each
  • the present invention thus relates to the use of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one of the configurations characterized as preferred or particularly preferred, in particular one or more compounds of the formulas (1.1 ) to (1.82) and / or their salts, each as defined above, as a herbicide and / or plant growth regulator, preferably in crops of useful and / or ornamental plants.
  • the present invention also relates to a method for controlling harmful plants and / or for regulating the growth of plants, characterized in that an effective amount one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one of the configurations characterized as preferred or particularly preferred, in particular one or more compounds of the formulas (1.1) to (1.82) and / or the salts thereof, in each case as defined above, or an agent according to the invention, as defined below, to which (harmful) plants, (harmful) plant seeds, the soil in or on which the (harmful) plants grow, or the cultivated area is applied.
  • an agent according to the invention as defined below
  • the present invention also relates to a method for controlling unwanted plants, preferably in crops, 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 of the as preferably or particularly preferably characterized embodiment, in particular one or more compounds of the formulas (1.1) to (1.82) and / or their salts, each as defined above, or an agent according to the invention, as defined below, on undesired plants (for example harmful plants such as mono - or dicotyledonous weeds or unwanted crops), the seeds of the unwanted plants (ie plant seeds, e.g. grains, seeds or vegetative propagation organs such as tubers or shoots with buds), the soil in or on which the unwanted plants grow (e.g. the soil of cultivated land or non-cultivated land) or the acreage surface (i.e. the area on which the unwanted plants will grow) is applied.
  • undesired plants for example harmful plants such as mono - or dicotyledonous weeds
  • the present invention also relates to methods for combating
  • Regulating the growth of plants preferably useful plants, 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 the configurations which are characterized as preferred or particularly preferred, in particular one or several compounds of the general formulas (1.1) to (1.82) and / or their salts, each as defined above, or an agent according to the invention as defined below, the plant, the seed of the plant (ie plant seeds, e.g. grains, seeds or vegetative propagation organs such as tubers or shoots with buds), the soil in or on which the plants grow (e.g. the soil of cultivated or non-cultivated land) or the area under cultivation (ie the area on which the plants will grow) is applied.
  • the seed of the plant ie plant seeds, e.g. grains, seeds or vegetative propagation organs such as tubers or shoots with buds
  • the soil in or on which the plants grow e.g. the soil of cultivated or non-cultivated land
  • the area under cultivation
  • the compounds according to the invention or the agents according to the invention can e.g. in pre-sowing (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 preferably used for controlling harmful plants or for regulating growth in crops of useful plants or ornamental plants, the useful plants or ornamental plants in a preferred embodiment are transgenic plants.
  • the compounds of general formula (1) and / or their salts according to the invention are suitable for combating the following genera of monocotyledonous and dicotyledonous harmful plants:
  • the compounds according to the invention are applied to the surface of the earth prior to germination of the harmful plants (grasses and / or weeds) (pre-emergence method), either the emergence of the weed or weed seedlings is completely prevented or they grow to the cotyledon stage approach, but then stop growing and eventually die completely after three to four weeks.
  • Post-emergence treatment stops growing after the treatment and the harmful plants remain in the growth stage at the time of application or die completely after a certain time, so that this is harmful to the crop plants
  • the compounds of the invention have excellent herbicidal activity against mono- and dicotyledon weeds, crops of economically important crops e.g. dicotyledon cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, lpomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus,
  • the compounds according to the invention (depending on their respective structure and the application rate applied) have excellent growth-regulating properties in crop plants. They intervene regulating the plant's own metabolism and can thus be used to influence plant constituents in a targeted manner and to facilitate the harvest, e.g. by triggering desiccation and stunted growth. Furthermore, they are also suitable for general control and inhibition of undesirable vegetative growth without killing the plants. Inhibiting vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, since, for example, this can reduce or completely prevent stock formation.
  • the compounds according to the invention can also be used to control harmful plants in crops of plants which have been modified by genetic engineering or by conventional mutagenesis.
  • the transgenic plants are generally distinguished by special advantageous properties, for example 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.
  • Transgenic plants with an increased starch content or altered starch quality or those with a different fatty acid composition of the crop are known.
  • transgenic cultures Preferred with respect to transgenic cultures is the use of the compounds according to the invention and / or their salts in economically important transgenic cultures of useful and ornamental plants, e.g. of cereals such as wheat, barley, rye, oats, millet, rice and corn or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.
  • cereals such as wheat, barley, rye, oats, millet, rice and corn or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.
  • the compounds according to the invention can preferably also be used as herbicides
  • Crop crops are used which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
  • the compounds according to the invention can also be used to control harmful plants in crops of known or still to be developed genetically modified plants.
  • the transgenic plants are generally distinguished by special advantageous properties, for example resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties concern e.g. the crop in terms of quantity, quality, shelf life, composition and special ingredients.
  • Transgenic plants with an increased starch content or altered starch quality or those with a different fatty acid composition of the crop are known.
  • Other special properties can include tolerance or resistance to abiotic stressors e.g. There is heat, cold, dryness, salt and ultraviolet radiation.
  • cereals such as wheat, barley, rye, oats, triticale, millet, rice, manioc and maize or also crops of sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetables.
  • the compounds of the general formula (I) can preferably be used as herbicides in
  • Crop crops are used which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
  • nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of standard procedures e.g. Base exchanges made, partial sequences removed or natural or synthetic sequences added. To connect the DNA fragments to one another, adapters or linkers can be attached to the fragments.
  • the production of plant cells with a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to achieve a cosuppression effect or the expression of at least one appropriately constructed ribozyme which specifically cleaves transcripts of the gene product mentioned above.
  • DNA molecules can be used that comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules that only comprise parts of the coding sequence, these parts having to be long enough to be in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but which are not completely identical.
  • the synthesized protein When nucleic acid molecules are expressed in plants, the synthesized protein can be located in any compartment of the plant cell. However, in order to achieve localization in a certain compartment, e.g. the coding region is linked to DNA sequences which ensure localization in a specific compartment. Such 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 into whole plants using known techniques.
  • the transgenic plants can be any plants
  • the compounds (I) according to the invention can preferably be used in transgenic cultures which are active against growth substances, e.g. Dicamba or against herbicides, the essential
  • Plant enzymes e.g. Inhibit acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydoxyphenylpyruvate dioxygenases (HPPD), or are resistant to herbicides from the group of sulfonylureas, glyphosates, glufosinates or benzoylisoxazoles and analogous active ingredients.
  • ALS Inhibit acetolactate synthases
  • EPSP synthases glutamine synthases
  • HPPD hydoxyphenylpyruvate dioxygenases
  • the active compounds according to the invention are used in transgenic crops, in addition to the effects on harmful plants which can be observed in other crops, there are often effects which are specific to the application in the respective transgenic culture, for example a changed or specially expanded weed spectrum which can be controlled changed Application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influencing the growth and yield of the transgenic crop plants.
  • the invention therefore also relates to the use of the compounds of the general formula (I) and / or their salts as herbicides for controlling harmful plants in crops of useful or ornamental plants, if appropriate in transgenic crop plants.
  • cereals preferably maize, wheat, barley, rye, oats, millet or rice, in the pre- or post-emergence.
  • Pre-or post-soya use is also preferred.
  • Plant growth regulation also includes the case in which the active ingredient of the general formula (I) or its salt is formed from a precursor substance ("prodrug") only after application to the plant, in the plant or in the soil.
  • the invention also relates to the use of one or more compounds of the general formula (I) or their salts or an agent according to the invention (as defined below) (in a process) for controlling harmful plants or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) or their salts on the plants (harmful plants, if appropriate together with the useful plants) plant seeds, the soil in or on which the plants grow, or the cultivated area applied.
  • the invention also relates to a herbicidal and / or plant growth-regulating agent, characterized in that the agent
  • (a) contains one or more compounds of the general formula (I) and / or their salts as defined above, preferably in one of those identified as preferred or particularly preferred
  • one or more further agrochemically active substances preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides (ie those which do not correspond to the general formula (I) defined above), fungicides, safeners, fertilizers and / or other growth regulators,
  • component (i) of an agent according to the invention are preferably selected from the group of substances described in "The Pesticide Manual”, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.
  • a herbicidal or plant growth-regulating agent according to the invention preferably comprises one, two, three or more formulation auxiliaries (ii) customary in crop protection selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusts, at 25 ° C. and 1013 mbar solid carriers, preferably adsorbable, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoams, water, organic solvents, preferably at 25 ° C. and 1013 mbar, organic solvents miscible with water in any ratio.
  • formulation auxiliaries customary in crop protection selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusts, at 25 ° C. and 1013 mbar solid carriers, preferably adsorbable, granulated inert materials, wetting agents, antioxidants, stabilizers
  • the compounds of the general formula (I) according to the invention can be used in the customary formulations in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules.
  • the invention therefore also relates to herbicides and Plant growth regulating agents which contain compounds of the general formula (I) and / or their salts.
  • the compounds of general formula (I) and / or their salts can be formulated in various ways, depending on which biological and / or chemical-physical parameters are specified. Possible formulation options are, for example: wettable powder (WP), water-soluble powder (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions ,
  • SC Suspension concentrates
  • CS Capsule suspensions
  • DP dusts
  • pickling agents granules for the litter
  • 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.
  • Spray powders are preparations which are uniformly dispersible in water.
  • they contain surfactants of an ionic and / or non-ionic type (wetting agents,
  • Dispersants e.g. polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, ligninsulfonic acid sodium, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, sodium dibutylnaphthalene-sulfonic acid sodium or also contain sodium acid.
  • the herbicidal active ingredients are finely ground, for example in conventional apparatus such as hammer mills, fan mills and air jet mills, and mixed at the same time or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are obtained by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or several surfactants of ionic and / or nonionic type (emulsifiers).
  • organic solvent for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or several surfactants of ionic and / or nonionic type (emulsifiers).
  • emulsifiers which can be used are: alkylarylsulfonic acid calcium salts such as
  • Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters
  • Alkylaryl polyglycol ether fatty alcohol polyglycol ether, propylene oxide-ethylene oxide condensation products, alkyl polyether, sorbitan esters such as e.g. Sorbitan fatty acid esters or
  • Polyoxethylene sorbitan esters such as e.g. Polyoxyethylene sorbitan fatty acid esters.
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g.
  • Talc natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates can be water or oil based. You can, for example, by wet grinding using commercially available bead mills and optionally adding surfactants, such as those e.g. already listed above for the other types of formulation.
  • Emulsions e.g. Oil-in-water emulsions (EW) can be mixed using stirrers,
  • Solvents and optionally surfactants e.g. already listed above for the other types of formulation.
  • Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, e.g. Polyvinyl alcohol, sodium polyacrylic acid or mineral oils, on the surface of carriers such as sand, kaolinite or granulated inert material. Also suitable ones
  • Active ingredients are granulated in the manner customary for the production of fertilizer granules - if desired in a mixture with fertilizers.
  • Water-dispersible granules are generally produced using the customary processes, such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations preferably herbicidal or plant growth-regulating agents of the present invention preferably contain a total amount of 0.1 to 99% by weight, preferably 0.5 to 95% by weight, more preferably 1 to 90% by weight, particularly preferably 2 to 80% by weight of compounds of the general formula (I) according to the invention and their salts.
  • the active substance concentration in wettable powders is e.g. about 10 to 90 wt .-%, the rest of 100 wt .-% consists of conventional formulation components. In the case of emulsifiable concentrates, the active substance concentration can be about 1 to 90, preferably 5 to 80,% by weight. Dusty
  • Formulations contain 1 to 30% by weight of active ingredient, preferably mostly 5 to 20% by weight of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50% by weight of active ingredient.
  • the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulating aids, fillers, etc. are used.
  • the active ingredient content of the water-dispersible granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active ingredient formulations mentioned may contain the usual adhesives, wetting agents, dispersing agents, emulsifying agents, penetration agents, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH and Agents influencing viscosity.
  • formulation auxiliaries are described, inter alia, in "Chemistry and Technology of Agrochemical Formulations", ed. D. A. Knowles, Kluwer Academic Publishers (1998).
  • the compounds of the general formula (I) or their salts can be used as such or in the form of their preparations (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 a finished formulation or as
  • Tank mixes The combination formulations can be prepared on the basis of the formulations mentioned above, taking into account the physical properties and stabilities of the active compounds to be combined.
  • Compounds (I) according to the invention of particular interest which contain the compounds of the 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, e.g. in economically important crops such as cereals (wheat, barley, rye, maize, rice, millet), sugar beet, sugar cane, rapeseed, cotton and soybeans, preferably cereals.
  • the weight ratio of herbicide (mixture) to safener generally depends on the
  • herbicide and the effectiveness of the respective safener can vary within wide limits, for example in the range from 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 their mixtures with further herbicides / pesticides and as
  • the herbicide or herbicide safener formulations present in commercially available form are optionally diluted in the customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water.
  • Preparations in the form of dust, ground granules or scattering granules and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the application rate can vary within wide limits.
  • the total amount of compounds of the general formula (I) and their salts is preferably in the range from 0.001 to 10.0 kg / ha, preferably in the range from 0.005 to 5 kg / ha, more preferably in Range from 0.01 to 1.5 kg / ha, particularly preferably in the range from 0.05 to 1 kg / ha. This applies to both pre-emergence and post-emergence applications.
  • compounds of general formula (I) and / or their salts as
  • Plant growth regulator for example as a stalk shortener in crop plants 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 from 0.001 to 2 kg / ha, preferably in the range from 0.005 to 1 kg / ha, in particular in the range from 10 to 500 g / ha, very particularly preferably in the range from 20 to 250 g / ha. This applies both to the application in
  • the application as a straw shortener can take place in different stages of the growth of the plants. For example, use after planting at the beginning of the
  • the treatment of the seed which includes the different seed dressing and coating techniques, can also be used.
  • the application rate depends on the individual techniques and can be determined in preliminary tests.
  • agents according to the invention for example mixture formulations or in a tank mix
  • active ingredients which are based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate -3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoendesaturase, Photosystem I, Photosystem II or
  • Protoporphyrinogen oxidase are used, such as those e.g. from Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein.
  • known herbicides or plant growth regulators are mentioned by way of example, which can be combined with the compounds according to the invention, these active compounds either with their "common name" in the English-language variant according to the International Organization for Standardization (ISO) or with the chemical name or with the code number are designated.
  • ISO International Organization for Standardization
  • herbicidal mixture partners examples include:
  • flucarbazone flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonoglypane-cyanogen flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate ammonium, pufosinate ammonium P-ammonium, glufosinate-P-sodium, glyphosate, glyph
  • metdicazthiazuron metam, metamifop, metamitron, metazachlor, metazosulfuron,
  • plant growth regulators as possible mix partners are:
  • Sl d compounds of the triazole carboxylic acid type (Sl d ), preferably compounds such as
  • Fenchlorazole ethyl ester
  • S1-7 2,4-triazole-3-carboxylic acid ethyl ester
  • Sl e compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid type, or the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (Sl e ), preferably compounds such as
  • R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2)
  • R-28725" (3-dichloroacetyl-2,2, -dimethyl- 1,3-oxazolidine) from Stauffer (S3-3)
  • PPG-1292 N-allyl-N - [(1,3-dioxolan-2-yl) methyl] dichloroacetamide
  • TI-35 (l-dichloroacetyl-azepan) from TRI-Chemical RT (S3-8),
  • RA 2 halogen (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, CF 3; m A 1 or 2;
  • VA is 0, 1, 2 or 3;
  • RB 1 , RB 2 independently of one another hydrogen, (Ci-C 6 ) alkyl, (C3-C6) cycloalkyl, (C3-C 6 ) alkenyl, (C3-C 6 ) alkynyl,
  • RB 3 is halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl or (Ci-C 4 ) alkoxy and me is 1 or 2, for example those in which
  • RB 1 cyclopropyl
  • RB 2 hydrogen
  • (RB 3 ) 2-OMe
  • RB 1 cyclopropyl
  • R B 1 ethyl
  • R B 1 isopropyl
  • R B 2 hydrogen
  • (R B 3 ) 5-Cl-2-OMe is (S4-4) and
  • R B 1 isopropyl
  • R B 2 hydrogen
  • (R B 3 ) 2-OMe is (S4-5);
  • Rc 1 , Rc 2 independently of one another hydrogen, (Ci-Cg) alkyl, (C3-Cg) cycloalkyl, (C3-
  • Rc 3 is halogen, (Ci-C i) alkyl, (Ci-C4) alkoxy, CF 3 and m c 1 or 2; for example 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,
  • R D 4 halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, CF 3; m D 1 or 2; RD 5 is hydrogen, (Ci-C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 5 - C 6 ) cycloalkenyl.
  • Carboxylic acid derivatives (S5) e.g.
  • Dihydroxybenzoic acid 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004/084631, WO-A-2005/015994, WO-A-2005/016001.
  • 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-C i) alkyl
  • R D 3 is hydrogen, (Ci-CsjAlkyl, (C 2 -C4) alkenyl, (C 2 -C4) alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or by one or more, preferably up to three of the same or various radicals from the group consisting of halogen and alkoxy, or their salts, n D is an integer from 0 to 2.
  • S9 active substances from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g.
  • YE, ZE independently of one another O or S, n ß an integer from 0 to 4,
  • RE 2 (Ci-Ci 6 ) alkyl, (C2-C6) alkenyl, (C3-C6) cycloalkyl, aryl; Benzyl, halobenzyl, RE 3 is hydrogen or (Ci-C 6 ) alkyl.
  • Sl l active substances of the oxyimino compound type (Sl l), which are known as seed dressings, such as. B.
  • Oxabetrinil ((Z) -l, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (Sl l-l), which is known as a seed dressing safener for millet against damage to metolachlor,
  • Fluorofenim (1- (4-chlorophenyl) -2,2,2-trifluoro-l-ethanone-0- (1,3-dioxolan-2-ylmethyl) -oxime) (Sl 1-2), which is used as a seed dressing -Safeer is known for millet against damage from metolachlor, and
  • Naphthalic anhydride (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed dressing safener for maize against damage from thiocarbamate herbicides,
  • Cyanamide known as a safener for corn against damage to imidazolinones
  • MG 191 (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for corn,
  • Mephenate (4-chlorophenyl methyl carbamate) (S13-9).
  • Active substances which, in addition to a herbicidal action against harmful plants, also have safener action on crop plants such as rice, such as, for. B.
  • COD l-bromo-4- (chloromethylsulfonyl) benzene
  • Kumiai CAS Reg. No. 54091-06-4
  • S15 compounds of the formula (S15) or their tautomers
  • RH 1 represents a (Ci-C 6 ) haloalkyl radical and R H 2 represents hydrogen or halogen and
  • R H 3 , R H 4 independently of one another are hydrogen, (Ci-Ci 6 ) alkyl, (C2-Ci6) alkenyl or
  • (C 2 -Ci 6 ) alkynyl each of the latter 3 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, (Ci-C i) alkoxy, (Ci-C i) haloalkoxy, (Ci C ij alkylthio, (Ci-C ij alkylamino, di [(Ci-C4) alkyl] amino, [(Ci-C i) alkoxy] carbonyl, [(Ci-C t j haloalkoxyj-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-C6) cycloalkyl
  • R H 3 is (Ci-C 4 ) alkoxy, (C2-C 4 ) alkenyloxy, (C2-C6) alkynyloxy or (C2-C 4 ) haloalkoxy and R H 4 is hydrogen or (Ci-C 4 ) alkyl or
  • R H 3 and R H 4 together with the directly bound N atom form a four- to eight-membered group
  • 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 N, O and S, and which is unsubstituted or by one or more radicals from the group halogen, cyano, nitro, (Ci C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkoxy and (Ci-C 4 ) alkylthio is substituted.
  • Preferred safeners in combination with the compounds of the formula (I) and / or their salts are: cloquintocet-mexyl, cyprosulfamide, ethyl fenchlorazole, isoxadifene -ethyl, mefenpyr-diethyl, fenclorim, cumyluron, S4-1 and S4-5, and particularly preferred safeners are: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.
  • Biological examples are: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyrrole Compounds (AREA)

Abstract

L'invention concerne des 5-(sulfanyl)-3,4-dihydro-2H-pyrrol-4-carboxamides substitués de formule générale (I), ainsi que leurs sels et leur utilisation comme agents herbicides. L'invention concerne notamment 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 des plantes comprenant un ou plusieurs composés de formule générale (I).
PCT/EP2019/073090 2018-09-24 2019-08-29 5-(sulfanyl)-3,4-dihydro-2h-pyrrol-4-carboxamides substitués et leurs sels et leur utilisation comme agents herbicides WO2020064260A1 (fr)

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EP4483714A2 (fr) 2021-12-15 2025-01-01 Adama Agan Ltd. Composés utiles pour la préparation de divers produits agrochimiques et marqueurs associés

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