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WO2020002083A1 - Hétérocyclylpyrrolones substituées, leurs sels et leur utilisation comme agents herbicides - Google Patents

Hétérocyclylpyrrolones substituées, leurs sels et leur utilisation comme agents herbicides Download PDF

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Publication number
WO2020002083A1
WO2020002083A1 PCT/EP2019/066188 EP2019066188W WO2020002083A1 WO 2020002083 A1 WO2020002083 A1 WO 2020002083A1 EP 2019066188 W EP2019066188 W EP 2019066188W WO 2020002083 A1 WO2020002083 A1 WO 2020002083A1
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phenyl
methyl
fluoro
alkyl
bromo
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German (de)
English (en)
Inventor
Jana FRANKE
Hendrik Helmke
Jens Frackenpohl
Uwe Döller
Thomas Müller
Dirk Schmutzler
Elisabeth ASMUS
Anu Bheemaiah MACHETTIRA
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Bayer AG
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

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 heterocyclylpyrrolones 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.
  • One object of the present invention is therefore to provide compounds with herbicidal activity (herbicides) which are highly effective against economically important harmful plants even at relatively low application rates and preferably against good activity
  • Harmful plants can be used selectively in crop plants and preferably show good tolerance to crop plants.
  • these herbicidal compounds should, in particular, be effective and efficient against a wide range of grasses, and preferably also have good effectiveness against many weeds.
  • pyrrolones which carry heterocyclic substituents on the nitrogen, for example also optionally further substituted isoxazolines.
  • Substituted pyrrolones and their herbicidal or pesticidal properties are also described in CH633678, DE 2735841, EP0297378, EP0334133, EP0339390 and EP0286816 carry heterocyclic substituents, for example optionally further substituted isoxazolines.
  • Selected specially substituted 1,3,4-thiadiazolyl- and 1,2,4-thiadiazolyl-2,5-dioxoimidazolines and their herbicidal activity are described in DE2247266. Substituted pyrazolylpyrrolones and their use as herbicides
  • Active ingredients are described, for example, in WO2015 / 018434.
  • the present invention therefore relates to compounds of the general formula (1)
  • R U R 12 where R 10 , R 1 1 and R 12 in the groupings NR 10 or CR U R 12 each have the same or different meanings according to the definition below,
  • X and Y independently of one another represent CH or the grouping CR 1 , where
  • X stands for CH if Y stands for the grouping CR 1 and
  • X stands for the grouping CR 1 , if Y stands for CH,
  • R 1 for halogen, cyano, (Ci-Cg) alkyl, (Ci-C8) haloalkyl, (Ci-Cg) hydroxyalkyl, (C i - C s) -
  • R 2 for hydroxy, hydrothio, halogen, NR 13 R 14 , (Ci-Cg) alkoxy, (C3-Cio) cycloalkyl- (Ci-C8) alkoxy, aryl- (Ci-Cg) -alkoxy, (Ci -C8) alkoxy- (Ci-C8) alkoxy, arylcarbonyloxy, (Ci-Cs) - alkylcarbonyloxy, aryl- (Ci-C8) alkylcarbonyloxy, heteroarylcarbonyloxy, (C 3 -C 10 ) - cycloalkylcarbonyloxy, heterocyclylcarbonyloxy, (Ci -C8) haloalkylcarbonyloxy, (C 2 -C 8 ) alkenylcarbonyloxy, OC (0) OR 15 , OC (0) SR 16 , OC (S) OR 15 , OC (S) SR 16 , OSO 2 R 16
  • R 3 represents hydrogen, (Ci-Cg) alkyl
  • R 4 , R 5 , R 6 , R 7 , R 8 and R 9 independently of one another for hydrogen, hydroxy, halogen, (Ci-C8) -alkyl, (Ci-C 8 ) -hydroxyalkyl, (Ci-C 8 ) - Haloalkyl, (C 3 -Cio) cycloalkyl, (C 3 -Cio) cycloalkyl- (Ci-C 8 ) - alkyl, (Ci-Csj-alkoxy, aryl, heteroaryl, heterocyclyl, aryl- (Ci-Cg) - alkyl, heteroaryl- (Ci-Cg) -alkyl, heterocyclyl- (Ci-C8) -alkyl, (C 2 -Cg) -alkenyl, (C 2 -C 8 ) -alkynyl, (Ci-C8) -alkoxycarbonyl- (Ci-Cs)
  • R 10 is hydrogen, (Ci-Cg) -alkyl, (Ci-Cg) -haloalkyl, (C 3 -Cio) -cycloalkyl, (C3-C10) - cycloalkyl- (Ci-Cg) -alkyl, aryl, heteroaryl, Heterocyclyl, aryl- (Ci-Cg) -alkyl, heteroaryl- (Ci-Cg) -alkyl, heterocyclyl- (Ci-Cg) -alkyl, (C 2 -Cg) -alkenyl, (C 2 -Cg) -alkynyl, (C 2 -Cg) haloalkenyl, (C 2 -Cg) haloalkynyl, (C4-Cio) cycloalkenyl, aryl- (C 2 -Cg) alkenyl, heteroaryl- (C 2 -Cg)
  • R 11 and R 12 independently of one another for hydrogen, hydroxy, halogen, (Ci-Cs) - alkyl, (Ci-Cs) - haloalkyl, (C3-Cio) -cycloalkyl, (C3-Cio) -cycloalkyl- (Ci-Cs ) alkyl, (Ci-Cs) alkoxy, aryl, heteroaryl, heterocyclyl, aryl (Ci-Cs) alkyl, heteroaryl (Ci-Cs) alkyl, heterocyclyl (Ci-Cs) alkyl, (C 2 -Cs) alkenyl, (C 2 -Cs) alkynyl, (Ci-C 8 ) alkoxycarbonyl- (Ci-Cs) alkyl, (Ci-Cs) - alkoxy- (Ci-Cs) alkyl, arylcarbonyloxy - (Ci-Cs) -
  • R 13 and R 14 are the same or different and are independently hydrogen, (Ci-Cs) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (Ci-C 8 ) - Cyanoalkyl, (Ci-C 8 ) haloalkyl, (C 2 -C 8 ) haloalkenyl, (C 2 -C 8 ) haloalkynyl, (C 3 -Cio) cycloalkyl, (C 4 -C 8 ) cycloalkenyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -haloalkoxy- (Ci-C 8 ) -alkyl, (Ci-C8) -alkylthio- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -haloal
  • R 15 represents (Ci-C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C2-C 8 ) -alkyl, (Ci-C 8 ) -cyanoalkyl, (Ci-C 8 ) -haloalkyl,
  • R 16 is for (Ci-C 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C2-C 8 ) alkyl, (Ci-C 8 ) cyanoalkyl, (Ci-Cio) haloalkyl, (C 2 -C 8 ) haloalkenyl, (C 2 -C 8 ) haloalkynyl, (C 3 -Cio) cycloalkyl, (C 4 -Cio) cycloalkenyl, (Ci-C 8 ) alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -haloalkyl, aryl, aryl- (Ci-C 8 ) -alkyl, heteroaryl, heteroaryl- (Ci-C 8 ) -alkyl, heterocyclyl- (Ci-C 8 ) -
  • the compounds of the general formula (1) can form salts. Salt formation can take place by the action of a base on those compounds of the general formula (1) which are acidic
  • Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine or pyridine, and ammonium, alkali or
  • These salts 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 (quaternary) ammonium salts, for example with cations of the formula [NRR ' R '' R '' ] + +, where R to R '"are each independent an organic residue from each other,
  • Alkyl sulfonium and alkyl sulfoxonium salts such as (Ci-C 4 ) -trialkyl sulfonium and (Ci-C 4 ) -trialkyl sulfoxonium salts are also suitable.
  • the compounds of the general formula (I) can be added by adding a suitable organic compound.
  • inorganic or organic acid such as mineral acids, such as HCl, HBr, H 2 SO 4 , H 3 PO 4 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 p-toluenesulfonic acid, to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts. These salts then contain the conjugate base of the acid as an anion.
  • mineral acids such as HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3
  • 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 p
  • Suitable substituents which are in deprotonated form e.g. Sulphonic acids or carboxylic acids can exist, internal salts with protonatable groups such as amino groups.
  • substituted heteroarylpyrrolones of the general formula (I) according to the invention can, depending on external conditions, such as pH, solvent and temperature, be present in various tautomeric structures, all of which are intended to be encompassed by the general formula (I).
  • a independently of one another represents O (oxygen), or the grouping NR 10 or CR U R 12 , where R 10 , R 11 and R 12 in the groupings NR 10 or CR U R 12 each have the same or different meanings according to the definition below to have,
  • X and Y independently of one another represent CH or the grouping CR 1 , where
  • X stands for CH if Y stands for the grouping CR 1 and
  • X stands for the grouping CR 1 , if Y stands for CH,
  • R 1 for halogen, cyano, (Ci-Cv) -alkyl, (Ci-Cvj-haloalkyl, (Ci-Cv) -hydroxyalkyl, (C 1-C7) -
  • R 2 for hydroxy, hydrothio, halogen, NR 13 R 14 , (Ci-C7) alkoxy, (C 3 -C 9 ) cycloalkyl- (Ci-C 7 ) alkoxy, aryl- (Ci-C7) alkoxy , (Ci-C7) alkoxy- (Ci-C7) alkoxy, (Ci-C7) alkylcarbonyloxy, phenylcarbonyloxy, p-chlorophenylcarbonyloxy, m-chlorophenylcarbonyloxy, 0-chlorophenylcarbonyloxy, p-fluorophenylcarbonyloxy, m-fluorophenylcarbonyloxy, 0-fluorophenylcarbonyloxy , Benzylcarbonyloxy, (C3-C9) -cycloalkylcarbonyloxy,
  • R 3 represents hydrogen, (Ci-C7) -alkyl
  • R 4 , R 5 , R 6 , R 7 , R 8 and R 9 independently of one another for hydrogen, hydroxy, halogen, (Ci-C7) -alkyl, (Ci-C 7 ) -hydroxyalkyl, (Ci-C 7 ) - Haloalkyl, (C 3 -C 9 ) cycloalkyl, (C 3 -C 9 ) cycloalkyl- (Ci-C 7 ) alkyl, (Ci-C7) alkoxy, (Ci-C7) alkoxy- (Ci C7) alkyl, phenyl, 2-fluoro-phenyl, 3-fluoro-phenyl, 4-fluoro-phenyl, 2,4-difluoro-phenyl, 2,5-difluoro-phenyl, 2,6-difluoro-phenyl, 2 , 3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluoroph
  • R 11 and R 12 independently of one another for hydrogen, hydroxy, halogen, (Ci-C7) -alkyl, (C1-C7) -
  • R 13 and R 14 are the same or different and are independently hydrogen, (Ci-Cv) alkyl, (Ci-Cv) cyanoalkyl, (Ci-Cv) haloalkyl, (Ci-C7) alkoxy- (Ci Cv) alkyl, phenyl, 2-fluoro-phenyl,
  • X and Y independently of one another represent CH or the grouping CR 1 , where
  • X stands for CH if Y stands for the grouping CR 1 and
  • X stands for the grouping CR 1 , if Y stands for CH,
  • R 1 for fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1 -
  • R 2 for hydroxy, fluorine, chlorine, bromine, iodine, hydrothio, methoxy, ethoxy, n-propyloxy, isopropyloxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1 - methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy , l, l-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy, 1, 2-dimethylpropylcarbonyloxy, 2,2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, n -Methylpentylcarbonyloxy, 2-
  • R 3 represents hydrogen, methyl, ethyl
  • Q stands for one of the groupings Ql .1 to Ql .69 specifically mentioned in the following table
  • Very particularly preferred subject matter of the invention are compounds of general formula (I), wonn X and Y independently of one another represent CH or the grouping CR 1 , where
  • X stands for CH if Y stands for the grouping CR 1 and
  • X stands for the grouping CR 1 , if Y stands for CH,
  • R 1 for fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-
  • R 2 for hydroxy, fluorine, chlorine, bromine, iodine, hydrothio, methoxy, ethoxy, n-propyloxy, isopropyloxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1 - methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy , l, l-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy, 1, 2-dimethylpropylcarbonyloxy, 2,2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, n-hexylcarbonyloxy, 1-methylpentyl
  • R 3 represents hydrogen
  • X and Y independently of one another represent CH or the grouping CR 1 , where
  • X stands for CH if Y stands for the grouping CR 1 and
  • X stands for the grouping CR 1 , if Y stands for CH,
  • R 1 for fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-
  • R 2 for hydroxy, fluorine, chlorine, bromine, iodine, hydrothio, methoxy, ethoxy, n-propyloxy, isopropyloxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1 - methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy , l, l-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy, 1, 2-dimethylpropylcarbonyloxy, 2,2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, n -Methylpentylcarbonyloxy, 2-
  • Q stands for one of the groupings Q-1 .1 to Q-1 .69 specifically mentioned in the table above.
  • X and Y independently of one another represent CH or the grouping CR 1 , where
  • X stands for CH if Y stands for the grouping CR 1 and
  • X stands for the grouping CR 1 , if Y stands for CH,
  • R 1 represents chlorine, bromine, methyl, ethyl, 1-methylethyl, l, l-dimethylethyl, trifluoromethyl, methoxy, ethoxy, methoxymethyl, methylthio, ethylthio, phenyl,
  • R 2 for hydroxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1 -
  • Methylethylcarbonyloxy 1, 1-dimethylethylcarbonyloxy, 2-methylpropylcarbonyloxy, cyclopropylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, 1,1-dimethylethyloxycarbonyloxy, 2-methylpropyloxycarbonyloxy, benzyloxycarbonyloxy,
  • R 3 represents hydrogen
  • Q stands for one of the groupings Q-1 .1 to Q-1 .69 specifically mentioned in the table above.
  • 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-methyls
  • heteroarylsulfonyl represents 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) -, (GG,) - or (Ci-C4) -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 Ethylpropyl
  • alkenylthio means an alkenyl radical bonded via a sulfur atom
  • alkynylthio means an alkynyl radical bonded via a sulfur atom
  • cycloalkylthio means a cycloalkyl radical bonded via a sulfur atom
  • cycloalkenylthio means one via a
  • (but not limited to) (Ci-C 6 ) alkylsulfinyl such as methylsulfinyl, ethylsulfmyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfmyl, 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), (C 2 -C 6 ) or (C 2 -C 4 ) alkenoxy or (C3-C10) -, (C3-C 6 ) - or (C3-C 4 ) alkynoxy.
  • Cycloalkyloxy means a cycloalkyl radical bonded via an oxygen atom and cycloalkenyloxy means a cycloalkenyl 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 alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyl group.
  • the number of carbon atoms relates to the alkyl radical in the alkoxycarbonyl group.
  • 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.
  • the number of carbon atoms relates to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyloxy 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, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkyl, haloalkyl, haloalkyl Haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroraryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bis-alkylaminoalkoxy, tris [alkyl] silyl, bis [alkyl] arylsilyl, bis [alkyl] alkylsilyl, tris [alky
  • Alkylaminocarbonyl cycloalkylaminocarbonyl, bis-alkylaminocarbonyl, heteroarylalkoxy,
  • 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 is heteroaromatic and can be unsubstituted or substituted, the binding site being 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, for example, 8-azabicyclo [3.2.l] octanyl, 8-azabicyclo [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 are said to be directly adjacent, for example 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 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-
  • 1,2-dithiin-3- or 4-yl 1,2-dithiin-3- or 4-yl; 1,2-dithiin-3- or 4-yl; l, 3-dithian-2- or 4- or 5-yl; 4H-l, 3-dithiin-2- or 4- or 5- or 6-yl; Isoxazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydroisoxazole-2- or 3- or
  • 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, by hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl,
  • Alkylaminocarbonyl bis-alkylaminocarbonyl, cycloalkylaminocarbonyl,
  • 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. This preferably also includes lactones and lactams.
  • the oxo group can also occur on the hetero ring atoms, which can exist in different oxidation states, for example in the case of N and S, and then form, for example, the divalent groups N (O), S (O) (also SO for short) and S (0) 2 (also briefly 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; lH-pyrrol-2-yl; lH-pyrrole
  • Carbon atoms are part of a further aromatic ring, so they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatics.
  • 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-benzothioph
  • halogen means fluorine, chlorine, bromine or iodine. If the term is used for a radical, "halogen" means 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 means alkyl or alkenyl or alkynyl which is partially or completely substituted by identical or different halogen atoms, e.g. monohaloalkyl
  • ( 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
  • the term 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-chain 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 radicals 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.
  • hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, even in composite radicals, are the lower carbon skeletons, e.g. with 1 to 6 carbon atoms or in the case of unsaturated groups with 2 to 6 carbon atoms, preferred.
  • 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, for example, vinyl, which can optionally be substituted by further alkyl radicals, for example (but not limited to) (C2-C6) alkenyl such as ethenyl, l-propenyl, 2-propenyl, 1-methylethenyl, l-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, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, l, 2-d
  • alkynyl also includes straight-chain or branched open-chain ones
  • alkynyl means e.g. Ethynyl, l-propynyl, 2-propynyl, l-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, l-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl- 2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, l-ethyl-2-propynyl, l-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-p
  • 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
  • multi-cyclic 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
  • Cycloalkylalkyloxy means a cycloalkylalkyl radical bonded via an oxygen atom and “arylalkyloxy” means an arylalkyl radical bonded via an oxygen atom.
  • Alkoxyalkyl stands for an alkoxy radical bonded via an alkyl group and "alkoxyalkoxy” means an alkoxyalkyl radical bonded via an oxygen atom, e.g. (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-l -yl, 2-cyclopropyleth-l-yl, l-cyclopropylprop-l-yl, 3-cyclopropylprop-l-yl.
  • Arylalkenyl stands for an aryl radical bonded via an alkenyl group
  • heteroarylalkenyl means a heteroaryl radical bonded via an alkenyl group
  • heterocyclylalkenyl means a heterocyclyl radical bonded via an alkenyl group
  • Arylalkynyl stands for an aryl group bonded via an alkynyl group
  • heteroarylalkynyl means a heteroaryl group bonded via an alkynyl group
  • heterocyclylalkynyl means a heterocyclyl group bonded via an alkynyl group.
  • 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-l-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.
  • 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 be produced 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 mixtures thereof. For the sake of simplicity, however, the following always refers to compounds of the general formula (I), although both the pure compounds and, if appropriate, mixtures with different proportions of isomeric compounds are meant.
  • the cleaning can also be carried out by
  • the substituted heterocyclylpyrrolones of the general formula (I) according to the invention can be prepared starting from known processes. The used and examined
  • Synthesis routes are based on commercially available or easily prepared partially saturated heterocyclic amines and on appropriately substituted furanones or furandions.
  • the groupings Q, X, Y, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 R 13 , R 14 , R 15 and R 16 of the general formula (I) have the meanings defined above in the diagrams below.
  • An optionally further substituted heterocyclic amine Q-NFb (IV) is prepared as the first key intermediate for the synthesis of the compounds of the general formula (I) according to the invention.
  • This is shown by way of example, but not by way of limitation, in the synthesis of an optionally further substituted 2-amino-isoxazoline (IVa).
  • an aldehyde or ketone (II) is reacted with diethyl (cyanomethyl) phosphonate in the corresponding substituted nitrile (III) in an olefinization reaction and into the by reaction with V-hydroxycarbamide using a suitable base (e.g. NaOMe) desired substituted heterocyclic amine Q-NFb (IV) transferred (see. Bioorg. Med. Chem. 2003, 11, 4093; Bull. Chim. Soc. France 1973, 1138).
  • R 6 and R 7 are exemplary but not restrictive of hydrogen, and R 4 and R 5 have the meaning previously defined.
  • the monosubstituted furan-2,5-diones (VI), which are also referred to as maleic anhydrides, can be prepared via synthesis instructions known from the literature (cf. J. Chem. Soc., Perkin Trans. 1, 1982, 215; EP1426365; J. Org Chem. 1998, 63, 2646; WO2015 / 018431; Tetrahedron 2012, 68, 5863; Russian J. Org. Chem. 2007, 43, 801), for example compounds (VI-1) and (VI-2) in the following scheme 2 in several steps from a suitable acetylenedicarboxylic acid ester (V).
  • Substituted heterocyclylpyrrolone of the general formula (I) can in two steps
  • a suitable optionally substituted partially saturated heterocyclylamine Q-NFh (IV) with a suitable optionally further substituted maleic anhydride (VI) using a suitable base (e.g. pyridine) in a suitable polar aprotic solvent (e.g. acetonitrile) or under acidic conditions using a suitable acid (e.g.
  • Acetic acid or p-toluenesulfonic acid in toluene as solvent and subsequent reduction of a carbonyl group of the substituted maleimide (VII) formed.
  • the reduction can be carried out in a suitable solvent (e.g. tetrahydrofuran and methanol) with the aid of a suitable reducing agent and can lead to regioisomers (VIII).
  • a suitable solvent e.g. tetrahydrofuran and methanol
  • Reducing agents are, for example, sodium hydride, lithium aluminum hydride, sodium borohydride or other hydrogen-generating metal hydrides. Alternatively, it can be one
  • Transition metal-mediated hydrogenation can be carried out (cf. CH633678, DE2247266,
  • substituted heterocyclylpyrrolones of the general formula (Ia) can be prepared starting from the reaction of a hydroxy- or bromolactone (IX) with a suitable, optionally substituted, partially saturated heterocyclylamine Q-NH2 (IV) in a suitable solvent (for example toluene) at elevated temperature become.
  • a suitable solvent for example toluene
  • acetic anhydride using a suitable base (e.g. pyridine) at elevated
  • Acetic acid and water can be converted into the corresponding heterocyclylpyrrolone of the general formula (Ia) with a free OH group.
  • R 2 of the general formula (1) is exemplary but not restricting OH, OC (0) CH 3 and R 3 of the general formula (1) is an example, but not limiting, of hydrogen.
  • substituted heterocyclylpyrrolones of the general formula (I) have a free hydroxy function
  • this can be acylated with suitable reagents (for example using a suitable acid chloride and with the aid of a suitable base such as triethylamine in a suitable polar-aprotic solvent), sulfonylated (e.g. using a suitable sulfonyl chloride and using a suitable base such as triethylamine in a suitable polar aprotic solvent), alkylated (e.g.
  • R 2 of the general formula (1) is exemplary but not restrictive of OH, OCH3, OSO2CH3, OC (0) CH 3 and OC (0) OCH 3 and R 3 of the general formula (1) represents, by way of example, but not by way of limitation, hydrogen.
  • N-Hydroxyurea (17.185 g, 221.4 mmol, 1.05 equiv) was dissolved in methanol (442 mL) and solid NaOMe (11.96 g 221.4 mmol, 1.05 equiv) was added. The solution was stirred for 15 min and a solution consisting of 3-ethylcrotonitrile (20.07 g, 210.9 mmol, 1.00 equiv) in MeOH (210 mL) was added dropwise. The reaction mixture was heated under reflux for a total of 27 h.
  • N-Hydroxyurea (2,993 g, 38.6 mmol, 1.05 equiv) was dissolved in methanol (77 mL) and solid NaOMe (2.13 g 38.6 mmol, 1.05 equiv) was added. The solution was stirred for 15 min and a solution consisting of 3-tert-butylacrylonitrile (4.01 g, 36.7 mmol, 1.00 equiv) in MeOH (36.7 mL) was added dropwise. The reaction mixture was heated under reflux for a total of 22 h.
  • N-Hydroxyurea (3,143 g, 40.5 mmol, 1.05 equiv) was dissolved in methanol (81 mL) and solid NaOMe (2.23 g 40.5 mmol, 1.05 equiv) was added. The solution was stirred for 15 min and a solution consisting of tetrahydro-4H-pyran-4-ylidene) acetonitrile (5.00 g, 38.6 mmol, 1.00 equiv) in MeOH (38.5 mL) was added dropwise. The reaction mixture was heated under reflux for a total of 6 h.
  • IV-hydroxyurea (0.398 g, 5.13 mmol, 1.10 equiv) was dissolved in methanol (10-2 mL) and solid NaOMe (0.277 g, 5.13 mmol, 1.10 equiv) was added. The solution was stirred for 15 min and then a solution consisting of cyclohexene-1-carbonitrile (0.5 g, 4.67 mmol, 1.00 equiv) in MeOH (4.6 mL) was added. The reaction mixture was transferred to a microwave vessel and irradiated in the microwave at 120-140 ° C. for 6.5 hours. After adding more
  • Citraconic anhydride (308 mg, 2.69 mmol, 1.05 equiv), and 5,5-dimcthyl-4/7-isoxazol-3-amine (380 mg, 2.56 mmol, 1.00 equiv) were dissolved in acetic acid (10 ml) and for 10 h heated under reflux. After cooling to room temperature, water was added to the reaction mixture and the aqueous phase was extracted several times with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and the solvent removed under reduced pressure.
  • Citraconic anhydride (1,074 g, 9.4 mmol, 1.05 equiv), and 4/7-isoxazol-3-amine (1,000 g, 8.9 mmol, 1.00 equiv) were dissolved in acetic acid (6.6 ml) and heated under reflux for 3 h. After cooling to room temperature, water was added to the reaction mixture and the aqueous phase was extracted several times with ethyl acetate. The combined organic phases were washed with saturated NaCl solution and dried over sodium sulfate, filtered and the solvent removed under reduced pressure. By column chromatography purification (gradient
  • Citraconic anhydride 1,000 g, 9.4 mmol, 1.0 equiv
  • 5-ethyl-5-methyl-4 // - isoxazol-3-amine (1,177 g, 9.2 mmol, 1.05 equiv) were dissolved in acetic acid (40 ml) and 1.5 for hours at reflux heated. After about 5 minutes. the solution turns orange and then turns brownish. After this
  • Citraconic anhydride (167 mg, 1.46 mmol, 1.05 equiv), and 3a, 4,5,6,7,7a-hexahydro-1,2-benzoxazol-3-amine (212 mg, 1.39 mmol, 1.00 equiv) were dissolved in acetic acid ( 10 ml) dissolved and heated under reflux for a total of 17.5 h. After cooling to room temperature, water was added to the reaction mixture and the aqueous phase was extracted several times with ethyl acetate. The combined organic phases were washed with saturated NaCl solution and dried over sodium sulfate, filtered and the solvent removed under reduced pressure.
  • Citraconic anhydride (235 mg, 2.06 mmol, 1.05 equiv), and 5- (4-chlorophenyl) -4H-isoxazol-3-amine (500 mg, 1.96 mmol, 1.00 equiv) were dissolved in acetic acid (6.6 ml) and combined for 3.5 h heated under reflux for a long time. After cooling to room temperature, water was added to the reaction mixture and the aqueous phase was extracted several times with ethyl acetate. The combined organic phases were washed with saturated NaCl solution and dried over sodium sulfate, filtered and the solvent removed under reduced pressure.
  • Bromomaleic anhydride (854 mg, 4.7 mmol, 1.2 equiv), and 5-ethyl-5-methyl-4 // - isoxazol-3-amine (500 mg, 3.9 mmol, 1.0 equiv) were in dry toluene under protective gas (10 ml) mixed and stirred for 10.5 h at room temperature with the addition of Amberlyst 15 (50 mg). The reaction mixture was filtered and the solvent removed under reduced pressure.
  • the reaction mixture was stirred for 20 min at room temperature and propionic acid chloride (0.06 mL, 0.68 mmol, 1.10 equiv) was added dropwise.
  • Table 1.1 Particularly preferred compounds of the formula (1.1) are the compounds 1.1-1 to 1.1-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.1-1 to 1.1-69 of Table 1.1 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.2 Preferred compounds of the formula (1.2) are the compounds 1.2-1 to 1.2-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.2-1 to 1.2- 69 of table 1.2 are thus by the meaning of the respective entries no. 1 to 69 defined for Q of Table 1 above.
  • Table 1.3 Preferred compounds of the formula (1.3) are the compounds 1.3-1 to 1.3-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.3-1 to 1.3- 69 of table 1.3 are thus by the meaning of the respective entries no. 1 to 69 defined for Q of Table 1.
  • Table 1.4 Preferred compounds of the formula (1.4) are the compounds 1.4-1 to 1.4-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.4-1 to 1.4- 69 of table 1.4 are thus by the meaning of the respective entries no. 1 to 69 defined for Q of Table 1 above.
  • Table 1.5 Preferred compounds of the formula (1.5) are the compounds 1.5-1 to 1.5-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.5-1 to 1.5- 69 of Table 1.5 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.6 Preferred compounds of the formula (1.6) are the compounds 1.6-1 to 1.6-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.6-1 to 1.6- 69 of table 1.6 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.7 Preferred compounds of the formula (1.7) are the compounds 1.7-1 to 1.7-69, in which Q has the meanings of Table 1 given in the respective row.
  • Table 1.8 Preferred compounds of the formula (1.8) are the compounds 1.8-1 to 1.8-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.8-1 to 1.8- 69 of Table 1.8 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.9 Preferred compounds of the formula (1.9) are the compounds 1.9-1 to 1.9-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.9-1 to 1.9- 69 of Table 1.9 are thus by the meaning of the respective entries No. 1 to 69 for Q of the table
  • Table 1.10 Preferred compounds of the formula (1.10) are the compounds 1.10-1 to 1.10-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.10-1 to 1.10-69 of table 1.10 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.11 Preferred compounds of the formula (1.11) are the compounds 1.11-1 to 1.11-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.11-1 to 1.11-69 of table 1.11 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.12 Preferred compounds of the formula (1.12) are the compounds 1.12-1 to 1.12-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.12-1 to 1.12-69 of table 1.12 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.13 Preferred compounds of the formula (1.13) are the compounds 1.13-1 to 1.13-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.13-1 to 1.13-69 of table 1.13 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.14 Preferred compounds of the formula (1.14) are the compounds 1.14-1 to 1.14-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.14-1 to 1.14-69 of table 1.14 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.15 Preferred compounds of the formula (1.15) are the compounds 1.15-1 to 1.15-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.15-1 to 1.15-69 of table 1.15 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.16 Preferred compounds of the formula (1.16) are the compounds 1.16-1 to 1.16-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.16-1 to 1.16-69 of table 1.16 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.17 Preferred compounds of the formula (1.17) are the compounds 1.17-1 to 1.17-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.17-1 to 1.17-69 of table 1.17 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.18 Preferred compounds of the formula (1.18) are the compounds 1.18-1 to 1.18-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.18-1 to 1.18-69 of table 1.18 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.19 Preferred compounds of the formula (1.19) are the compounds 1.19-1 to 1.19-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.19-1 to 1.19-69 of table 1.19 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.20 Preferred compounds of the formula (1.20) are the compounds 1.20-1 to 1.20-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.20-1 to 1.20-69 of table 1.20 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.21 Preferred compounds of the formula (1.21) are the compounds 1.21-1 to 1.21-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.21-1 to 1.21-69 of table 1.21 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.22 Preferred compounds of the formula (1.22) are the compounds 1.22-1 to 1.22-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.22-1 to 1.22-69 of table 1.22 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.23 Preferred compounds of the formula (1.23) are the compounds 1.23-1 to 1.23-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.23-1 to 1.23-69 of table 1.23 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.24 Preferred compounds of the formula (1.24) are the compounds 1.24-1 to 1.24-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.24-1 to 1.24-69 of table 1.24 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.25 Preferred compounds of the formula (1.25) are the compounds 1.25-1 to 1.25-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.25-1 to 1.25-69 of table 1.25 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.26 Preferred compounds of the formula (1.26) are the compounds 1.26-1 to 1.26-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.26-1 to 1.26-69 of table 1.26 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.27 Preferred compounds of the formula (1.27) are the compounds 1.27-1 to 1.27-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.27-1 to 1.27-69 of table 1.27 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.28 Preferred compounds of the formula (1.28) are the compounds 1.28-1 to 1.28-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.28-1 to 1.28-69 of table 1.28 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.29 Preferred compounds of the formula (1.29) are the compounds 1.29-1 to 1.29-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.29-1 to 1.29-69 of table 1.29 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.30 Preferred compounds of the formula (1.30) are the compounds 1.30-1 to 1.30-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.30-1 to 1.30-69 of table 1.30 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.31 Preferred compounds of the formula (1.31) are the compounds 1.31-1 to 1.31-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.31-1 to 1.31-69 of table 1.31 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.32 Preferred compounds of the formula (1.32) are the compounds 1.32-1 to 1.32-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.32-1 to 1.32-69 of table 1.32 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.33 Preferred compounds of the formula (1.33) are the compounds 1.33-1 to 1.33-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.33-1 to 1.33-69 of table 1.33 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.34 Preferred compounds of the formula (1.34) are the compounds 1.34-1 to 1.34-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.34-1 to 1.34-69 of table 1.34 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.35 Preferred compounds of the formula (1.35) are the compounds 1.35-1 to 1.35-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.35-1 to 1.35-69 of table 1.35 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.36 Preferred compounds of the formula (1.36) are the compounds 1.36-1 to 1.36-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.36-1 to 1.36-69 of table 1.36 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.37 Preferred compounds of the formula (1.37) are the compounds 1.37-1 to 1.37-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.37-1 to 1.37-69 of table 1.37 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.38 Preferred compounds of the formula (1.38) are the compounds 1.38-1 to 1.38-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.38-1 to 1.38-69 of table 1.38 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.39 Preferred compounds of the formula (1.39) are the compounds 1.39-1 to 1.39-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.39-1 to 1.39-69 of table 1.39 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.40 Preferred compounds of the formula (1.40) are the compounds 1.40-1 to 1.40-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.40-1 to 1.40-69 of table 1.40 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.41 Preferred compounds of the formula (1.41) are the compounds 1.41-1 to 1.41-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.41-1 to 1.41-69 of table 1.41 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.42 Preferred compounds of the formula (1.42) are the compounds 1.42-1 to 1.42-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.42-1 to 1.42-69 of table 1.42 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.43 Preferred compounds of the formula (1.43) are the compounds 1.43-1 to 1.43-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.43-1 to 1.43-69 of table 1.43 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.44 Preferred compounds of the formula (1.44) are the compounds 1.44-1 to 1.44-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.44-1 to 1.44-69 in Table 1.44 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.45 Preferred compounds of the formula (1.45) are the compounds 1.45-1 to 1.45-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.45-1 to 1.45-69 of table 1.45 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.46 Preferred compounds of the formula (1.46) are the compounds 1.46-1 to 1.46-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.46-1 to 1.46-69 of table 1.46 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.47 Preferred compounds of the formula (1.47) are the compounds 1.47-1 to 1.47-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.47-1 to 1.47-69 of table 1.47 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.48 Preferred compounds of the formula (1.48) are the compounds 1.48-1 to 1.48-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.48-1 to 1.48-69 of table 1.48 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.49 Preferred compounds of the formula (1.49) are the compounds 1.49-1 to 1.49-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.49-1 to 1.49-69 in table 1.49 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.50 Preferred compounds of the formula (1.50) are the compounds 1.50-1 to 1.50-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.50-1 to 1.50-69 of table 1.50 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.51 Preferred compounds of the formula (1.51) are the compounds 1.51-1 to 1.51-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.51-1 to 1.51-69 of table 1.51 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.52 Preferred compounds of the formula (1.52) are the compounds 1.52-1 to 1.52-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.52-1 to 1.52-69 of table 1.52 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.53 Preferred compounds of the formula (1.53) are the compounds 1.53-1 to 1.53-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.53-1 to 1.53-69 of table 1.53 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.54 Preferred compounds of the formula (1.54) are the compounds 1.54-1 to 1.54-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.54-1 to 1.54-69 of table 1.54 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.55 Preferred compounds of the formula (1.55) are the compounds 1.55-1 to 1.55-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.55-1 to 1.55-69 of table 1.55 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.56 Preferred compounds of the formula (1.56) are the compounds 1.56-1 to 1.56-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.56-1 to 1.56-69 of table 1.56 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.57 Preferred compounds of the formula (1.57) are the compounds 1.57-1 to 1.57-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.57-1 to 1.57-69 of table 1.57 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.58 Preferred compounds of the formula (1.58) are the compounds 1.58-1 to 1.58-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.58-1 to 1.58-69 of table 1.58 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.59 Preferred compounds of the formula (1.59) are the compounds 1.59-1 to 1.59-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.59-1 to 1.59-69 of table 1.59 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.60 Preferred compounds of the formula (1.60) are the compounds 1.60-1 to 1.60-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.60-1 to 1.60-69 of table 1.60 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.61 Preferred compounds of the formula (1.61) are the compounds 1.61-1 to 1.61-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.61-1 to 1.61-69 in table 1.61 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.62 Preferred compounds of the formula (1.62) are the compounds 1.62-1 to 1.62-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.62-1 to 1.62-69 of table 1.62 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.63 Preferred compounds of the formula (1.63) are the compounds 1.63-1 to 1.63-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.63-1 to 1.63-69 of table 1.63 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.64 Preferred compounds of the formula (1.64) are the compounds 1.64-1 to 1.64-69, in which Q has the meanings of Table 1 given in the respective row. The connections
  • Table 1.65 Preferred compounds of the formula (1.65) are the compounds 1.65-1 to 1.65-69, in which Q has the meanings of Table 1 given in the respective row. The connections
  • Table 1.66 Preferred compounds of the formula (1.66) are the compounds 1.66-1 to 1.66-69, in which Q has the meanings of Table 1 given in the respective row. The connections
  • Table 1.67 Preferred compounds of the formula (1.67) are the compounds 1.67-1 to 1.67-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.67-1 to 1.67-69 of table 1.67 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.68 Preferred compounds of the formula (1.68) are the compounds 1.68-1 to 1.68-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.68-1 to 1.68-69 of table 1.68 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.69 Preferred compounds of the formula (1.69) are the compounds 1.69-1 to 1.69-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.69-1 to 1.69-69 in table 1.69 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.70 Preferred compounds of the formula (1.70) are the compounds 1.70-1 to 1.70-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.70-1 to 1.70-69 of table 1.70 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.71 Preferred compounds of the formula (1.71) are the compounds 1.71-1 to 1.71-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.71-1 to 1.71-69 of table 1.71 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.72 Preferred compounds of the formula (1.72) are the compounds 1.72-1 to 1.72-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.72-1 to 1.72-69 in table 1.72 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.73 Preferred compounds of the formula (1.73) are the compounds 1.73-1 to 1.73-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.73-1 to 1.73-69 of table 1.73 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.74 Preferred compounds of the formula (1.74) are the compounds 1.74-1 to 1.74-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.74-1 to 1.74-69 of table 1.74 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.75 Preferred compounds of the formula (1.75) are the compounds 1.75-1 to 1.75-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.75-1 to 1.75-69 of table 1.75 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.76 Preferred compounds of the formula (1.76) are the compounds 1.76-1 to 1.76-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.76-1 to 1.76-69 of table 1.76 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.77 Preferred compounds of the formula (1.77) are the compounds 1.77-1 to 1.77-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.77-1 to 1.77-69 of table 1.77 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.78 Preferred compounds of the formula (1.78) are the compounds 1.78-1 to 1.78-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.78-1 to 1.78-69 of table 1.78 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.79 Preferred compounds of the formula (1.79) are the compounds 1.79-1 to 1.79-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.79-1 to 1.79-69 of table 1.79 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.80 Preferred compounds of the formula (1.80) are the compounds 1.80-1 to 1.80-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.80-1 to 1.80-69 of table 1.80 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.81 Preferred compounds of the formula (1.81) are the compounds 1.81-1 to 1.81-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.81-1 to 1.81-69 of table 1.81 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.82 Preferred compounds of the formula (1.82) are the compounds 1.82-1 to 1.82-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.82-1 to 1.82-69 of table 1.82 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.83 Preferred compounds of the formula (1.83) are the compounds 1.83-1 to 1.83-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.83-1 to 1.83-69 in Table 1.83 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.84 Preferred compounds of the formula (1.84) are the compounds 1.84-1 to 1.84-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.84-1 to 1.84-69 of table 1.84 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.85 Preferred compounds of the formula (1.85) are the compounds 1.85-1 to 1.85-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.85-1 to 1.85-69 of table 1.85 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.86 Preferred compounds of the formula (1.86) are the compounds 1.86-1 to 1.86-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.86-1 to 1.86-69 in table 1.86 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.87 Preferred compounds of the formula (1.87) are the compounds 1.87-1 to 1.87-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.87-1 to 1.87-69 in Table 1.87 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.88 Preferred compounds of the formula (1.88) are the compounds 1.88-1 to 1.88-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.88-1 to 1.88-69 in table 1.88 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.89 Preferred compounds of the formula (1.89) are the compounds 1.89-1 to 1.89-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.89-1 to 1.89-69 of table 1.89 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.90 Preferred compounds of the formula (1.90) are the compounds 1.90-1 to 1.90-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.90-1 to 1.90-69 of table 1.90 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.91 Preferred compounds of the formula (1.91) are the compounds 1.91-1 to 1.91-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.91-1 to 1.91-69 of table 1.91 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.92 Preferred compounds of the formula (1.92) are the compounds 1.92-1 to 1.92-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.92-1 to 1.92-69 in table 1.92 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.93 Preferred compounds of the formula (1.93) are the compounds 1.93-1 to 1.93-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.93-1 to 1.93-69 in table 1.93 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.94 Preferred compounds of the formula (1.94) are the compounds 1.94-1 to 1.94-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.94-1 to 1.94-69 in table 1.94 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.95 Preferred compounds of the formula (1.95) are the compounds 1.95-1 to 1.95-69, in which Q has the meanings of Table 1 given in the respective row.
  • Table 1.96 Preferred compounds of the formula (1.96) are the compounds 1.96-1 to 1.96-69, in which Q has the meanings of Table 1 given in the respective row. The connections
  • Table 1.97 Preferred compounds of the formula (1.97) are the compounds 1.97-1 to 1.97-69, in which Q has the meanings of Table 1 given in the respective row. The connections
  • Table 1.98 Preferred compounds of the formula (1.98) are the compounds 1.98-1 to 1.98-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.98-1 to 1.98-69 of table 1.98 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.99 Preferred compounds of the formula (1.99) are the compounds 1.99-1 to 1.99-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.99-1 to 1.99-69 of table 1.99 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.100 Preferred compounds of the formula (I. 100) are the compounds I. 100-1 to I. 100- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 100-1 to I. 100-69 of Table I. 100 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.101 Preferred compounds of the formula (1.101) are the compounds 1. 101-1 to 1. 101- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 101-1 to I. 101-69 of Table I. 101 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1. (1,102)
  • Preferred compounds of the formula (I. 102) are the compounds I. 102-1 to I. 102- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 102-1 to I. 102-69 of table I. 102 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.103 Preferred compounds of the formula (1.103) are the compounds I. 103-1 to I. 103- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 103-1 to I. 103-69 of table I. 103 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.104 Preferred compounds of the formula (1. 104) are the compounds 1. 104-1 to 1. 104- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1. 104-1 to 1. 104-69 of table 1. 104 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.105 Preferred compounds of the formula (I. 105) are the compounds I. 105-1 to I. 105- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 105-1 to I. 105-69 of Table I. 105 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Preferred compounds of the formula (I. 106) are the compounds I. 106-1 to I. 106- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 106-1 to I. 106-69 of Table I. 106 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Preferred compounds of the formula (I. 107) are the compounds I. 107-1 to I. 107- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the compounds I. 107-1 to I. 107-69 of Table I. 107 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above. (1.108)
  • Table 1.108 Preferred compounds of the formula (I. 108) are the compounds I. 108-1 to I. 108- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 108-1 to I. 108-69 of Table I. 108 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.109 Preferred compounds of the formula (1. 109) are the compounds 1. 109-1 to 1. 109- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1. 109-1 to 1. 109-69 of table 1. 109 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.110 Preferred compounds of the formula (I.110) are the compounds I.110-1 to I.110-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I.110-1 to I.110-69 of Table I.110 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.111 Preferred compounds of the formula (I. 111) are the compounds I. 111-1 to I. 111- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the compounds I. 111-1 to I. 111-69 of Table I. 111 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.112 Preferred compounds of the formula (I. 112) are the compounds I. 112-1 to I. 112- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 112-1 to I. 112-69 of Table I. 112 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.113 Preferred compounds of the formula (1. 113) are the compounds 1. 113-1 to 1. 113- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1. 113-1 to 1. 113-69 of Table 1. 113 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.114 Preferred compounds of the formula (1. 114) are the compounds 1. 114-1 to 1. 114- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1. 114-1 to 1. 114-69 of Table 1. 114 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.115 Preferred compounds of the formula (I. 115) are the compounds I. 115-1 to I. 115- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the compounds I. 115-1 to I. 115-69 of Table I. 115 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.116 Preferred compounds of the formula (I. 116) are the compounds I. 116-1 to I. 116- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 116-1 to I. 116-69 of Table I. 116 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Preferred compounds of the formula (I. 117) are the compounds I. 117-1 to I. 117- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 117-1 to I. 117-69 of Table I. 117 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.118 Preferred compounds of the formula (I. 118) are the compounds I. 118-1 to I. 118- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 118-1 to I. 118-69 of Table I. 118 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1,119 Preferred compounds of the formula (1,119) are the compounds 1,119-1 to 1,119-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1. 119-1 to 1. 119-69 of Table 1. 119 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above. (1,120)
  • Table 1.120 Preferred compounds of the formula (I.120) are the compounds I.120-1 to I.120-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 120-1 to I. 120-69 of Table I. 120 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1,121 Preferred compounds of the formula (I. 121) are the compounds I. 121-1 to I. 121- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 121-1 to I. 121-69 of Table I. 121 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Preferred compounds of the formula (I. 122) are the compounds I. 122-1 to I. 122- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 122-1 to I. 122-69 of Table I. 122 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.123 Preferred compounds of the formula (I. 123) are the compounds I. 123-1 to I. 123- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the compounds I. 123-1 to I. 123-69 of Table I. 123 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1,124 Preferred compounds of the formula (I. 124) are the compounds I. 124-1 to I. 124- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the compounds I. 124-1 to I. 124-69 of Table I. 124 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1,125 Preferred compounds of the formula (1,125) are the compounds 1,125-1 to 1,125-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1. 125-1 to 1. 125-69 of Table 1. 125 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above. (1.126)
  • Table 1,126 Preferred compounds of the formula (I. 126) are the compounds I. 126-1 to I. 126- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 126-1 to I. 126-69 of Table I. 126 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1,127 Preferred compounds of the formula (I 127) are the compounds I 127-1 to I 127- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 127-1 to I. 127-69 of Table I. 127 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.128 Preferred compounds of the formula (I. 128) are the compounds I. 128-1 to I. 128- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 128-1 to I. 128-69 of Table I. 128 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above. (1,129)
  • Table 1,129 Preferred compounds of the formula (I. 129) are the compounds I. 129-1 to I. 129- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 129-1 to I. 129-69 of Table I. 129 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.130 Preferred compounds of the formula (I.130) are the compounds I.130-1 to I.130-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 130-1 to I. 130-69 of Table I. 130 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.131 Preferred compounds of the formula (1. 131) are the compounds 1. 131-1 to 1. 131- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1. 131-1 to 1. 131-69 of table 1. 131 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above. (1,132)
  • Preferred compounds of the formula (I. 132) are the compounds I. 132-1 to I. 132- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 132-1 to I. 132-69 of Table I. 132 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Preferred compounds of the formula (I. 133) are the compounds I. 133-1 to I. 133- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 133-1 to I. 133-69 of Table I. 133 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.134 Preferred compounds of the formula (I. 134) are the compounds I. 134-1 to I. 134- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 134-1 to I. 134-69 of Table I. 134 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above. (1.135)
  • Table 1.135 Preferred compounds of the formula (I. 135) are the compounds I. 135-1 to I. 135- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 135-1 to I. 135-69 of Table I. 135 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.136 Preferred compounds of the formula (I. 136) are the compounds I. 136-1 to I. 136- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 136-1 to I. 136-69 of Table I. 136 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.137 Preferred compounds of the formula (1. 137) are the compounds 1. 137-1 to 1. 137- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1. 137-1 to 1. 137-69 of Table 1. 137 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • the peak list of an example therefore has the form: di (intensity ⁇ ; d2 (intensity2);; d; (intensity ⁇ ;; d (intensity ⁇ ).
  • 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. For 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
  • An expert who calculates the peaks of the target compounds using known methods can isolate the peaks of the target compounds as required, using additional intensity filters if necessary. This isolation would be similar to the relevant peak picking in the classic 1H NMR interpretation.
  • the present invention furthermore relates to the use of one or more
  • herbicide and / or plant growth regulator preferably in crops of useful and / or ornamental plants.
  • the present invention 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 preferred or particularly preferred
  • the present invention also relates to a method for controlling unwanted plants, preferably in crops of useful plants, characterized in that an effective amount of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one of the as preferably or particularly preferably marked
  • the present invention also relates to methods for combating
  • 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 i.e. the area on which the plants will grow
  • the compounds according to the invention or the agents according to the invention can e.g. are applied in the pre-sowing (possibly also by incorporation into the soil), pre-emergence and / or post-emergence methods.
  • Some representatives of the mono- and dicotyledons are examples
  • Weed flora which can be used to control the compounds according to the invention, without any restriction to certain species being mentioned.
  • the present invention therefore also relates to a method for combating
  • Plant crops in which one or more compound (s) according to the invention is applied to the plants for example harmful plants such as monocotyledonous or dicotyledon weeds or undesirable crop plants
  • the seeds for example grains, seeds or vegetative propagation organs such as tubers or shoots with buds
  • the area which the plants grow e.g. the area under cultivation.
  • the compounds according to the invention can e.g. are applied in the pre-sowing (possibly also by incorporation into the soil), pre-emergence or post-emergence methods.
  • Some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned in detail, which can be controlled by the compounds according to the invention, without any intention that the name should limit them to certain species.
  • the compounds according to the invention are applied to the earth's surface prior to germination of the harmful plants (grasses and / or weeds) (pre-emergence method), then either the emergence of the weed or weed seedlings is completely prevented or they grow to the cotyledon stage, but then they grow and eventually die completely after three to four weeks.
  • the compounds according to the invention can have selectivities in crops and can also be used as non-selective herbicides.
  • crop plants of economically important crops are e.g. dicotyledon cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, lpomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus,
  • the active compounds 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 notable for particularly advantageous properties, for example resistance to certain active ingredients used in the agricultural industry, especially certain herbicides,
  • Resistance to plant diseases or pathogens such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties relate to the crop, for example, in terms of quantity, quality, storability, composition and special ingredients.
  • transgenic plants with an increased starch content or altered starch quality or with a different fatty acid composition of the crop are known.
  • Further special properties are tolerance or resistance to abiotic stressors such as heat, cold, dryness, salt and ultraviolet radiation.
  • the compounds of the general formula (I) can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
  • 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.
  • new plants with modified properties can be created using genetic engineering methods (see e.g. EP 0221044, EP 0131624).
  • genetic engineering modifications of crop plants for the purpose of modifying the starch synthesized in the plants for example WO 92/011376 A, WO 92/014827 A, WO 91/019806 A
  • transgenic crop plants which are active against certain herbicides of the glufosinate see, for example, EP 0242236 A, EP 0242246 A) or glyphosate (WO 92/000377 A) or the sulfonylureas (EP 0257993 A, US 5,013,659) or against combinations or
  • transgenic crop plants for example cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to certain pests (EP 0142924 A, EP 0193259 A).
  • Bacillus thuringiensis toxins Bacillus thuringiensis toxins
  • transgenic crop plants with modified fatty acid composition (WO 91/013972 A).
  • transgenic crops that are characterized by higher yields or better quality transgenic crop plants which are characterized by a combination of, for example, the new properties mentioned above (“gene stacking”)
  • nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by recombining DNA sequences.
  • standard procedures e.g. Base exchanges made, partial sequences removed or natural or synthetic sequences added.
  • Adapters or linkers can be attached to the fragments for connecting the DNA fragments to one another, see e.g. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Gene and Clones", VCH Weinheim 2nd edition 1996
  • 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 above-mentioned gene product.
  • 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 can be located in any compartment of the plant cell.
  • the coding region can be linked, for example, to DNA sequences which ensure localization in a specific compartment.
  • sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1: 95-106 (1991).
  • 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. In principle, the transgenic plants can be any plants
  • the compounds of the general formula (I) according to the invention can preferably be used in transgenic cultures which are active against growth substances, e.g. 2,4-D, dicamba or against herbicides, the essential plant enzymes, e.g. Inhibit acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydoxyphenyl pyruvate dioxygenases (HPPD), respectively against herbicides from the group of the sulfonylureas, the glyphosates, glufosinates or benzoylisoxazoles and analogous active substances, or against any combination of these active substances, or against any combination of these active substances.
  • the essential plant enzymes e.g. Inhibit acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydoxyphenyl pyruvate dioxygenases (HPPD)
  • ALS Inhibit acetolactate
  • the compounds according to the invention can particularly preferably be used in transgenic crop plants which are resistant to a combination of glyphosates and glufosinates, glyphosates and sulfonylureas or imidazolinones.
  • the compounds according to the invention can very particularly preferably be used in transgenic crop plants such as, for. B. corn or soy with the trade name or the designation OptimumTM GATTM (Glyphosate ALS Tolerant) can be used.
  • the invention therefore also relates to the use of the compounds of the general formula (I) according to the invention as herbicides for controlling harmful plants 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 is applied to 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.
  • 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) selected in plant 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, anti-foaming agents, water, organic solvents, preferably at 25 ° C and 1013 mbar with water in any ratio miscible organic solvents.
  • formulation auxiliaries selected in plant 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,
  • the compounds 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 herbicidal and plant growth-regulating compositions which comprise the compounds according to the invention.
  • the compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are specified. As
  • Formulation options are possible, 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, Suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions, capsule suspensions (CS), dusts (DP), pickling agents, granules for spreading and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
  • WP wettable powder
  • SP water-soluble powder
  • EC emulsifiable concentrates
  • EW emulsions
  • SC Suspension concentrates
  • SC dispersions based on oil or water, oil
  • the necessary formulation auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen,
  • combinations with other pesticidally active substances such as insecticides, acaricides, herbicides, fungicides, as well as with safeners and fertilizers, can also be carried out and / or produce growth regulators, for example in the form of a finished formulation or as a tank mix.
  • Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain not only a diluent or an inert substance, but also ionic and / or nonionic surfactants (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 else sodium.
  • the herbicidal active ingredients are, for example, finely ground in customary equipment, 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 made by dissolving the active ingredient in an organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents
  • surfactants of ionic and / or nonionic type emulsifiers
  • alkylarylsulfonic acid calcium salts such as
  • Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters
  • Alkylaryl polyglycol ether fatty alcohol polyglycol ether
  • Sorbitan fatty acid esters or polyoxethylene sorbitan esters such as e.g. Polyoxyethylene.
  • 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 formulation types.
  • Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates using adhesives, for example polyvinyl alcohol, polyacrylic acid sodium or mineral oils, to the surface of Carriers such as sand, kaolinite or granulated inert material.
  • Suitable active ingredients can also be 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 generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of compounds according to the invention.
  • 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. Powdery
  • sprayable solutions contain about 0.05 to 80, preferably 2 to 50% by weight of active ingredient.
  • Water-dispersible granules the active ingredient content depends in part on whether the active compound is liquid or solid and which granulation 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 customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreezes and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH and Agents influencing viscosity.
  • a wettable powder which is readily dispersible in water is obtained by 25
  • alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight
  • Isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of
  • a water-dispersible granulate is also obtained by
  • the compounds of 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.
  • acetolactate synthase As a combination partner for the compounds according to the invention in mixture formulations or in a tank mix, there are, for example, known active ingredients which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenyl pyruvate dioxygenase, phytoendesaturase,
  • Photosystem I, Photosystem 11 or protoporphyrinogen oxidase are used, 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, 2006 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 (1SO) or with the chemical name or with the code number are designated. All forms of use such as acids, salts, esters and also all isomeric forms such as stereoisomers and optical isomers are always included, even if these are not explicitly mentioned.
  • herbicidal mixture partners examples include:
  • metdicazthiazuron metam, metamifop, metamitron, metazachlor, metazosulfuron,
  • plant growth regulators as possible mixing partners are:
  • Safeners which, in combination with the compounds of the general formula (I) according to the invention and, if appropriate, in combinations with other active compounds, Insecticides, acaricides, herbicides,
  • Fungicides as listed above can preferably be selected from the group consisting of:
  • n A is a natural number from 0 to 5, preferably 0 to 3;
  • R A 1 is halogen, (Ci-C 4 ) alkyl, (Ci-C i) alkoxy, nitro or (Ci-C 4 ) haloalkyl;
  • W A is an unsubstituted or substituted divalent heterocyclic radical from the group of the unsaturated or aromatic five-membered heterocycles having 1 to 3 hetero ring atoms from the group N and O, with at least one N atom and at most one O atom being contained in the ring, preferably a residue from the group (W A 1 ) to (W A 4 ),
  • n 0 or 1
  • R A 2 is OR A 3 , SR A 3 or NR A 3 R A 4 or a saturated or unsaturated 3- to 7-membered
  • Heterocycle with at least one N atom and up to 3 heteroatoms preferably from the groups O and S, which is connected via the N atom to the carbonyl group in (S1) and is unsubstituted or by residues from the group (Ci-C i) Alkyl, (Ci-C i) alkoxy or optionally substituted phenyl is substituted, preferably a radical of the formula OR A 3 , NHR A 4 or N (CH3) 2, in particular of the formula ORA 3 ;
  • R A 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably with a total of 1 to 18 carbon atoms;
  • R A 4 is hydrogen, (Ci-C 6 ) alkyl, (Ci-C 6 ) alkoxy or substituted or unsubstituted phenyl;
  • R A 5 is H, (Ci-C 8 ) alkyl, (Ci-C 8 ) haloalkyl, (Ci-C 4 ) alkoxy (Ci-C 8 ) alkyl, cyano or COOR A 9 , where R A 9 is hydrogen, ( Ci-C 8 ) alkyl, (Ci-C 8 ) haloalkyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, (Ci-C 6 ) hydroxyalkyl, (C3-Ci2) cycloalkyl or tri- (Ci -C 4 ) alkyl silyl;
  • R A 6 , R A 7 , R A 8 are identical or different hydrogen, (Ci-Cs) alkyl, (Ci-Cs) haloalkyl, (C3-Ci2) cycloalkyl or substituted or unsubstituted phenyl; preferably: a) compounds of the dichlorophenylpyrazoline-3-carboxylic acid (Sl a ) type, preferably compounds such as 1 - (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid,
  • Ethyl 5- (2,4-dichlorobenzyl) -2-isoxazoline-3-carboxylate (Sl-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (Sl-9) and related compounds as described in WO-A- 91/08202 are described, or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1-10) or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-L 1) ("Isoxadifen- ethyl ") or -n-propyl ester (S1-12) or the
  • Patent application WO-A-95/07897 are described.
  • RB 1 is halogen, (Ci-C i) alkyl, (Ci-C4) alkoxy, nitro or (Ci-C4) haloalkyl;
  • ne is a natural number from 0 to 5, preferably 0 to 3;
  • R B 2 is OR B 3 , SR B 3 or NR B 3 R B 4 or a saturated or unsaturated 3 to 7-membered heterocycle with at least one N atom and up to 3
  • Heteroatoms preferably from the group O and S, which is connected via the N atom to the carbonyl group in (S2) and is unsubstituted or by radicals from the group (Ci-C4) alkyl, (Ci-C4) alkoxy or optionally substituted phenyl is substituted, preferably a radical of the formula OR B 3 , NHR B 4 or N (CH3) 2, in particular of the formula OR B 3 ;
  • RB 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably with a total of 1 to 18 carbon atoms;
  • RB 4 is hydrogen, (Ci-C 6 ) alkyl, (Ci-C 6 ) alkoxy or substituted or unsubstituted phenyl;
  • T B is a (Ci or C2) alkanediyl chain which is unsubstituted or substituted with one or two (Ci-C4) alkyl radicals or with [(Ci-C3) alkoxy] carbonyl; preferably: a) compounds of the 8-quinolineoxyacetic acid (S2 a ) type, preferably
  • Rc 1 is (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 3 -C 7 ) cycloalkyl, preferably dichloromethyl;
  • Rc 2 , Rc 3 are the same or different hydrogen, (Ci-C 4 ) alkyl, (C2-C 4 ) alkenyl, (C2-C 4 ) alkynyl, (Ci-C 4 ) haloalkyl, (C2-C 4 ) haloalkenyl , (Ci-C 4 ) alkylcarbamoyl- (Ci-C 4 ) alkyl, (C2-C 4 ) alkenylcarbamoyl- (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, dioxolanyl - (Ci-C 4 ) alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or Rc 2 and Rc 3 together form a substituted or unsubstituted heterocyclic ring
  • 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),
  • a D is S0 2 -NR D 3 -C0 or C0-NR D 3 -S0 2
  • X D is CH or N
  • RD 1 is CO-NR D 5 R D 6 or NHCO-R D 7 ;
  • R D 2 is halogen, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) haloalkoxy, nitro, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) alkylsulfonyl, (Ci -C 4 ) alkoxycarbonyl or (Ci-C 4 ) alkylcarbonyl;
  • R D 3 is hydrogen, (Ci-C 4 ) alkyl, (C 2 -C 4 ) alkenyl or (C 2 -C 4 ) alkynyl;
  • R D 4 is halogen, nitro, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) haloalkoxy, (C 3 -C 6 ) cycloalkyl, phenyl, (Ci-C 4 ) alkoxy , Cyano, (Ci-C 4 ) alkylthio, (Ci-C 4 ) alkylsulfinyl, (Ci-C 4 ) alkylsulfonyl, (Ci-C 4 ) alkoxycarbonyl or (Ci-C 4 ) alkylcarbonyl;
  • R D 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, Phenyl or 3- to 6-membered heterocyclyl containing V D heteroatoms from the group consisting of nitrogen, oxygen and sulfur, the last seven radicals being represented by V D
  • R D 6 is hydrogen, (Ci-C 6 ) alkyl, (C 2 -C ' 6 ) alkynyl or (C 2 -C 6 ) alkynyl, the latter three radicals being substituted by V D radicals from the group halogen, hydroxy, ( Ci-C 4 ) alkyl, (Ci
  • R D 5 and R D 6 together with the nitrogen atom carrying them form a pyrrolidinyl or piperidinyl radical;
  • R D 7 is hydrogen, (Ci-C4) alkylamino, di- (Ci-C4) alkylamino, (Ci-C 6 ) alkyl, (C3-C6) cycloalkyl, the latter 2 radicals being substituted by V D substituents from the group halogen , (Ci-C4) alkoxy, (Ci- C 6) haloalkoxy and (Ci-C4) alkylthio and in case of cyclic radicals, also (Ci-C4) alkyl and
  • haloalkyl are substituted; n D is 0, 1 or 2; m D is 1 or 2;
  • V D is 0, 1, 2 or 3; Of these, preference is given to compounds of the N-acylsulfonamide type, for example the following formula (S4 a ), which, for. B. are known from WO-A-97/45016
  • R D 7 (Ci-C 6 ) alkyl, (C3-C6) cycloalkyl, the latter 2 radicals being substituted by V D substituents from the group halogen, (Ci-C4) alkoxy, (Ci-C 6 ) haloalkoxy and (Ci C4) alkylthio and in the case of cyclic radicals also (Ci-C4) alkyl and (Ci-C4) haloalkyl are substituted; R d 4 halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, CF 3; m D 1 or 2;
  • VD is 0, 1, 2 or 3; such as
  • RD 8 and RD 9 independently of one another are hydrogen, (Ci-Cg) alkyl, (C3-Cg) cycloalkyl, (C3-C6) alkenyl, (C 3 -C 6 ) alkynyl,
  • RD 4 is halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, CF 3 m D 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; ni D 1 or 2;
  • R D 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.
  • R E 1 , R E 2 are independently halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkyl,
  • a E is COOR E 3 or COSR E 4 RE 3 , RE 4 are independently hydrogen, (Ci-C4) alkyl, (CF-GOalknyl,
  • RF 1 halogen, (Ci-C4) alkyl, (Ci-C4) haloalkyl, (Ci-C4) alkoxy, (Ci-C4) haloalkoxy, nitro, (Ci-C4) alkylthio, (Ci-C4) alkylsulfonyl, ( Ci-C4) alkoxycarbonyl, optionally substituted. Phenyl, optionally
  • RF 2 hydrogen or (Ci-C4) alkyl RF 3 hydrogen, (Ci-CsjAlkyl, (C2-C4) alkenyl, (C2-C4) alkynyl, or aryl, each of the aforementioned C-containing radicals unsubstituted or by one or more , preferably up to three identical or different radicals from the group consisting of halogen and alkoxy, or their salts, preferably compounds in which XF CH, n F is an integer from 0 to 2,
  • RF 1 halogen, (Ci-C4) alkyl, (Ci-C4) haloalkyl, (Ci-C4) alkoxy, (Ci-C4) haloalkoxy,
  • RF 2 hydrogen or (Ci-C4) alkyl
  • RF 3 hydrogen, (Ci-Cg) alkyl, (C2-C4) alkenyl, (C2-C4) alkynyl, or aryl, each of the aforementioned C-containing radicals being unsubstituted or by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy substituted,
  • S9 active substances from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g.
  • Y G , Z G independently of one another O or S, no an integer from 0 to 4,
  • RG 2 is (Ci-Ciejalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkyl, aryl; benzyl, halobenzyl, RG 3 is hydrogen or (C 1 -Cr,) alkyl.
  • Sl 1 Active substances of the oxyimino compound type (Sl 1), which are known as seed dressings, such as. B.
  • Cyometrinil or “CGA-43089” ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (Sl l-3), which is known as a seed dressing safener for millet against damage to metolachlor.
  • Naphthalic anhydride (1,8-naphthalenedicarboxylic acid anhydride) (S13-1), which is known as a seed dressing safener for maize against damage by thiocarbamate herbicides
  • Fenclorim (4,6-dichloro-2-phenylpyrimidine) (S13-2) known as a safener for pretilachlor in sown rice
  • 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,
  • COD l-bromo-4- (chloromethylsulfonyl) benzene
  • RH 1 denotes a (Ci-C 6 ) haloalkyl radical
  • RH 2 is hydrogen or halogen
  • R H 3 , R H 4 independently of one another are hydrogen, (Ci-Ci 6 ) alkyl, (C2-Ci6) alkenyl or
  • RH 3 is (Ci-C4) alkoxy, (C2-C4) alkenyloxy, (C2-C6) alkynyloxy or (C2-C4) haloalkoxy and RH 4 is hydrogen or (Ci-C4) alkyl or
  • RH 3 and RH 4 together with the directly bound N atom have a four- to eight-membered structure
  • heterocyclic ring which, in addition to the N atom, can 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 C4) alkyl, (Ci-C4) haloalkyl, (Ci-C4) alkoxy, (Ci-C4) haloalkoxy and (Ci-C4) alkylthio is substituted.
  • Particularly preferred safeners in combination with the compounds according to the invention of the general formula (I) and / or their salts, in particular with the compounds of the formulas (1.1) to (1,137) and / or their salts are: mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl, dichlormid and metcamifene.
  • herbicides or pesticides and safeners which contain the compounds of the general formula (1) or their combinations with other herbicides or pesticides and safeners.
  • the safeners which are used in an antidotically effective content, reduce the phytotoxic side effects of the herbicides / pesticides used, e.g. in economically important crops such as cereals (wheat, barley, rye, corn, 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 (1) or their mixtures with further herbicides / pesticides and as
  • the formulations present in the commercial form are optionally diluted in the customary manner, for example for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water. Dust-like preparations, soil or
  • Scatter granules and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the required application rate of the compounds of general formula (1) and their salts varies. It can fluctuate within wide limits, e.g. between 0.001 and 10.0 kg / ha or more
  • Active substance but preferably it is between 0.005 to 5 kg / ha, more preferably in the range from 0.01 to 1.5 kg / ha, particularly preferably in the range from 0.05 to 1 kg / ha g / ha. This applies to both pre-emergence and post-emergence applications.
  • Carrier means a natural or synthetic, organic or inorganic substance, with which the active ingredients for better applicability, especially for application to plants or Parts of plants or seeds, mixed or combined.
  • the carrier which can be solid or liquid, is generally inert and should be useful in agriculture.
  • Solid or liquid carriers are possible: e.g. Ammonium salts and natural rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flours, such as highly disperse silica, aluminum oxide and natural or synthetic silicates, resins, waxes, solid fertilizers, water, alcohols, especially butanol , organic solvents, mineral and vegetable oils and derivatives thereof. Mixtures of such
  • Carriers can also be used. Solid carriers for granules are possible: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems.
  • solid carriers for granules are possible: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems.
  • Liquids which can be used as liquefied gaseous extenders or carriers are those which are gaseous at normal temperature and under normal pressure, e.g. Aerosol propellants, such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide.
  • Aerosol propellants such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or dichloromethane
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils
  • Alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl formamide and dimethyl sulfoxide, and water.
  • the agents according to the invention can additionally contain further constituents, e.g.
  • Suitable surface-active substances are emulsifiers and / or foam-generating agents, dispersants or wetting agents with ionic or nonionic
  • Naphthalenesulphonic acid polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyl taurate derivatives), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of the compounds containing sulfates, sulfonates and phosphates, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, protein hydrolyzates, lignin sulfite waste liquors and methyl cellulose.
  • substituted phenols preferably alkylphenols or arylphenols
  • salts of sulphosuccinic acid esters preferably alkyl taurate derivatives
  • the presence of a surface-active substance is necessary if one of the active ingredients and / or one of the inert carriers is not soluble in water and if the application takes place in water.
  • the proportion of surface-active substances is between 5 and 40 percent by weight of the agent according to the invention.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • protective colloids e.g. protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration enhancers, stabilizers,
  • the active ingredients can be combined with any solid or liquid additive that is commonly used for formulation purposes.
  • the agents and formulations according to the invention contain between 0.05 and 99% by weight, 0.01 and 98% by weight, preferably between 0.1 and 95% by weight, particularly preferably between 0.5 and 90% Active ingredient, very particularly preferably between 10 and 70 percent by weight.
  • the active compounds or agents according to the invention as such or depending on their respective physical and / or chemical properties in the form of their formulations or the use forms prepared therefrom, such as aerosols, capsule suspensions, cold mist concentrates, hot mist concentrates, encapsulated granules, fine granules, flowable concentrates for the
  • the formulations mentioned can be prepared in a manner known per se, for example by mixing the active compounds with at least one conventional extender, solvent or diluent, emulsifier, dispersant and / or binder or fixative, wetting agent, water repellent, if appropriate Drying agents and UV stabilizers and, if appropriate, dyes and pigments, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and other processing aids.
  • the compositions according to the invention include not only formulations which are already ready for use and can be applied to the plant or the seed using suitable apparatus, but also commercial concentrates which must be diluted with water before use.
  • the active compounds according to the invention can be used as such or in their (commercially available) formulations and in the use forms prepared from these formulations in a mixture with other (known) active compounds, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides , Fertilizers, safeners or semiochemicals are available.
  • active compounds such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides , Fertilizers, safeners or semiochemicals are available.
  • the treatment of the plants and parts of plants according to the invention with the active compounds or agents is carried out directly or by acting on their surroundings, living space or storage space according to the usual treatment methods, e.g. by dipping, (spraying) spraying, (spraying) spraying, sprinkling, evaporating, atomizing, atomizing, (scattering) scattering, foaming, brushing, spreading, watering (drenching), drip irrigation and with propagation material, in particular with seeds by dry pickling, wet pickling, slurry pickling, incrustation, single- or multi-layer coating, etc. It is also possible to apply the active ingredients using the ultra-low-volume process or to inject the active ingredient preparation or the active ingredient into the soil itself.
  • transgenic seeds with the active substances or agents according to the invention are of particular importance.
  • This relates to the seeds of plants which contain at least one heterologous gene which enables the expression of a polypeptide or protein with insecticidal properties.
  • the heterologous gene in transgenic seeds can e.g. from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • This heterologous gene preferably comes from Bacillus sp., The gene product having an action against the European corn borer (European comborer) and / or Western Com rootworm.
  • the heterologous gene particularly preferably comes from Bacillus thuringiensis.
  • the agent according to the invention is applied to the seed alone or in a suitable formulation.
  • the seed is preferably treated in a state in which it is so stable that no damage occurs during the treatment.
  • the seed can be treated at any time between harvesting and sowing.
  • seeds are used that have been separated from the plant and freed of pistons, shells, stems, husk, wool or pulp.
  • seeds can be used that have been harvested, cleaned and dried to a moisture content of less than 15% by weight.
  • seeds can be used that have been treated with water after drying and then dried again.
  • care must be taken that the amount of the agent and / or other additives according to the invention applied to the seed is selected so that the germination of the seed is not impaired or the resulting plant is not damaged. This is particularly important for active substances that can show phytotoxic effects at certain application rates.
  • the agents according to the invention can be applied directly, that is, without further ones
  • Suitable formulations and methods for seed treatment are known to the person skilled in the art and are e.g. described in the following documents: US 4,272,417 A, US 4,245,432 A, US 4,808,430, US 5,876,739, US 2003/0176428 A1, WO 2002/080675 A1, WO 2002/028186 A2.
  • the active compounds according to the invention can be converted into the customary mordant formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating compositions for seeds, and also ULV formulations.
  • customary mordant formulations such as solutions, emulsions, suspensions, powders, foams, slurries or other coating compositions for seeds, and also ULV formulations.
  • formulations are prepared in a known manner by mixing the active ingredients with conventional additives, such as conventional extenders and solvents or
  • Diluents dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water.
  • Suitable dyes which can be contained in the mordant formulations which can be used according to the invention are all dyes customary for such purposes. Both pigments that are sparingly soluble in water and dyes that are soluble in water can be used. Examples include those under the names Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes.
  • Suitable wetting agents which can be contained in the mordant formulations which can be used according to the invention are all substances which promote wetting and are customary for the formulation of agrochemical active ingredients.
  • Alkyl naphthalene sulfonates such as diisopropyl or diisobutyl naphthalene sulfonates, can preferably be used.
  • the dispersants and / or emulsifiers which can be contained in the mordant formulations which can be used according to the invention are all used to formulate agrochemicals
  • Nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants can preferably be used.
  • Suitable nonionic dispersants are especially ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are, in particular, lignin sulfonates, polyacrylic acid salts and aryl sulfonate-formaldehyde condensates.
  • the mordant formulations which can be used according to the invention can contain, as defoamers, all of the foam-inhibiting substances which are customary for the formulation of agrochemical active compounds. Silicone defoamers and magnesium stearate can preferably be used.
  • All substances which can be used for such purposes in agrochemical compositions can be present as preservatives in the mordant formulations which can be used according to the invention.
  • Examples include dichlorophene and benzyl alcohol hemiform.
  • Secondary thickeners which can be contained in the mordant formulations which can be used according to the invention are all substances which can be used in agrochemical compositions for such purposes. Cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and highly disperse silica are preferred.
  • Suitable adhesives which can be contained in the mordant formulations which can be used according to the invention are all binders customarily used in mordants.
  • Polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose are preferred.
  • mordant formulations which can be used according to the invention can be used either directly or after prior dilution with water for treating a wide variety of seeds, including seeds of transgenic plants. In cooperation with the substances formed by expression, additional synergistic effects can also occur.
  • the dressing is carried out by placing the seeds in a mixer which Add the desired amount of seed dressing formulations either as such or after prior dilution with water and mix until the formulation is evenly distributed on the seed. If necessary, a drying process follows.
  • the active compounds according to the invention are more suitable if they are well tolerated by plants
  • plants which can be treated according to the invention maize, soybean, cotton, Brassica oilseeds such as Brassica napus (for example Canola), Brassica rapa, B. juncea (for example (field) mustard) and Brassica carinata, rice, Wheat sugar beet, sugar cane,
  • Rosaceae sp. for example pome fruits such as apple and pear, but also stone fruits such as apricots, cherries, almonds and peaches and berries such as strawberries
  • Rosaceae sp. for example pome fruits such as apple and pear, but also stone fruits such as apricots, cherries, almonds and peaches and berries such as strawberries
  • Ribesioidae sp. Juglandaceae sp.
  • Betulaceae sp. Anacardiaceae sp.
  • Fagaceae sp. Moraceae sp.
  • Oleaceae sp. Actinidaceae sp.
  • Lauraceae sp. Musaceae sp.
  • Rubiaceae sp. e.g. coffee
  • Theaceae sp. Sterculiceae sp.
  • Rutaceae sp. e.g. lemons, organs and grapefruit
  • Solanaceae sp. for example tomatoes, potatoes, pepper, eggplants
  • Liliaceae sp. Compositae sp.
  • lettuce, artichoke and chicory including root chicory, endive or common chicory
  • Umbelliferae sp. e.g. carrot, parsley, celery and tuber celery
  • Cucurbitaceae sp. for example cucumber - including pickled cucumber, pumpkin, watermelon, bottle gourd and melons
  • Alliaceae sp. for example leek and onion
  • Leguminosae sp. e.g. peanuts, peas, and beans - such as runner bean and field bean
  • Chenopodiaceae sp. for example Swiss chard, beet, spinach, beet
  • Malvaceae for example okra
  • Asparagaceae for example asparagus
  • all plants and their parts can be treated.
  • wild plant species and plant cultivars and their parts obtained by conventional organic breeding methods, such as hybridization or protoplast fusion are treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated.
  • the term “parts” or “parts of plants” or “parts of plants” was explained above. Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention. Plant varieties are plants with new ones
  • the treatment method according to the invention can be used for the treatment of genetically modified organisms (GMOs), e.g. B. plants or seeds can be used.
  • GMOs genetically modified organisms
  • Genetically modified plants are plants in which a heterologous gene has been stably integrated into the genome.
  • heterologous gene essentially means a gene which is provided or assembled outside the plant and which, when introduced into the cell nucleus genome, the
  • Chloropiastene genome or the mitochondrial genome gives the transformed plant new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by down-regulating or genes in the plant or genes in the plant switches off (for example by means of antisense technology, cosuppression technology or RNAi technology [RNA interference]).
  • a heterologous gene that is present in the genome is also called a transgene.
  • a transgene that is defined by its specific presence in the plant genome is called a transformation or transgenic event.
  • Treatment conditions according to the invention can also lead to superadditive ("synergistic") effects in growth conditions (soils, climate, growing season, nutrition).
  • superadditive additive
  • the following effects are possible that go beyond the effects that are actually to be expected: reduced application rates and / or expanded spectrum of activity and / or increased effectiveness of the active compounds and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low Temperatures, increased tolerance to
  • Dryness or water or soil salt content increased flowering performance, easier harvesting,
  • Plants and plant varieties which are preferably treated according to the invention include all plants which have genetic material which gives these plants particularly advantageous, useful traits (regardless of whether this was achieved by breeding and / or biotechnology).
  • nematode-resistant plants are described, for example, in the following US patent applications: 11 / 765,491, 11 / 765,494, 10 / 926,819, 10 / 782,020, 12 / 032,479, 10 / 783,417, 10 / 782,096, 11 / 657,964, 12 / 192,904, 11 / 396.808, 12 / 166.253, 12 / 166.239, 12 / 166.124, 12 / 166.209, 11 / 762.886, 12 / 364.335, 11 / 763.947, 12 / 252.453, 12 / 209.354, 12 / 491.396 and 12 / 497.221. Plants that can be treated according to the invention are hybrid plants that already have the
  • Such plants are typically created by crossing one inbred male-sterile parent line (the female crossing partner) with another inbred male-sterile parent line (the female crossing partner) with another inbred male-sterile parent line (the female crossing partner) with another inbred male-sterile parent line (the female crossing partner) with another inbred male-sterile parent line (the female crossing partner) with another inbred male-sterile parent line (the female crossing partner) with another inbred male-sterile parent line (the female crossing partner) with another
  • hybrid seeds are typically harvested from the male-sterile plants and sold to propagators.
  • Pollen-sterile plants can sometimes (e.g. in maize) be produced by detasseling (i.e. mechanically removing the male genital organs or the male flowers); however, it is more common for pollen sterility to be based on genetic determinants in the plant genome. In this case, especially when the desired product is seeds because one wants to harvest from the hybrid plants, it is usually beneficial to ensure that pollen fertility in hybrid plants contains the genetic determinants responsible for pollen sterility , is completely restored.
  • Genetic determinants for male sterility can be localized in the cytoplasm. Examples of cytoplasmic pollen sterility (CMS) have been described, for example, for Brassica species. However, genetic determinants for male sterility can also be localized in the cell core genome. Pollen-sterile plants can also be obtained using methods of plant biotechnology, such as genetic engineering.
  • a ribonuclease such as a bamase is selectively expressed in the tapetum cells in the stamens. Fertility can then be restored in the tapetum cells by expression of a ribonuclease inhibitor such as Barstar.
  • Plants or plant cultivars which are obtained using methods of plant biotechnology, such as genetic engineering which can be treated according to the invention are herbicide-tolerant plants, i.e. H. Plants that have been made tolerant to one or more specified herbicides. Such plants can be obtained either by genetic transformation or by selection of plants containing a mutation that confers such herbicide tolerance.
  • Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, ie plants which have been made tolerant to the herbicide glyphosate or its salts. Plants can be made tolerant of glyphosate using various methods. For example, glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., 1983, Science 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp.
  • EPSPS 5-enolpyruvylshikimate-3-phosphate synthase
  • EPSPS EPSPS from the petunia (Shah et al., 1986, Science 233, 478-481) for an EPSPS code from the tomato (Gasser et al., 1988, J. Biol. Chem. 263, 4280-4289) or for an EPSPS from Eleusine (WO 01/66704). It can also be a mutated EPSPS. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate oxidoreductase enzyme.
  • Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme. Glyphosate-tolerant plants can also be obtained by selecting plants that contain naturally occurring mutations in the above-mentioned genes. Plants that express EPSPS genes that confer glyphosate tolerance are described. Plants which have other genes which confer glyphosate tolerance, for example decarboxylase genes, have been described.
  • herbicide-resistant plants are, for example, plants which have been made tolerant to herbicides which inhibit the enzyme glutamine synthase, such as bialaphos, phosphinotricin or glufosinate. Such plants can be obtained by expressing an enzyme that detoxifies the herbicide or a mutant of the enzyme glutamine synthase, which is resistant to inhibition.
  • an effective detoxifying enzyme is, for example, an enzyme that is used for a
  • phosphinotricin acetyltransferase such as the bar or pat protein from Streptomyces species. Plants that express an exogenous phosphinotricin acetyltransferase have been described.
  • Hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogenate.
  • Plants that are tolerant to HPPD inhibitors can be transformed with a gene encoding a naturally occurring resistant HPPD enzyme or a gene encoding a mutated or chimeric HPPD enzyme, as in WO 96/38567 , WO 99/24585, WO 99/24586, WO 2009/144079, WO 2002/046387 or US 6,768,044.
  • Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes that code for certain enzymes that enable the formation of homogenate despite the inhibition of the native HPPD enzyme by the HPPD inhibitor.
  • plants are described in WO 99/34008 and WO 02/36787.
  • the tolerance of plants to HPPD inhibitors can also be improved by transforming plants, in addition to a gene which codes for an HPPD-tolerant enzyme, with a gene which codes for a prephenate dehydrogenase enzyme, as in WO 2004/024928 is described.
  • plants can be made more tolerant of HPPD inhibitors by using inserts a gene into their genome which codes for an enzyme which metabolizes or degrades HPPD inhibitors, such as CYP450 enzymes (see WO 2007/103567 and WO 2008/150473).
  • ALS inhibitors include, for example, sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides. It is known that various mutations in the enzyme ALS (also known as
  • Acetohydroxy acid synthase (AHAS, known) impart tolerance to different herbicides or groups of herbicides, such as in Tranel and Wright (Weed Science 2002, 50, 700 - 712).
  • AHAS Acetohydroxy acid synthase
  • imidazo linon-tolerant plants is described.
  • Other sulfonylurea and imidazo linone tolerant plants are also described.
  • Further plants which are tolerant to imidazolinones and / or sulfonylureas can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutation breeding (cf. for example for soybean US 5,084,082, for rice WO 97/41218, for sugar beet US 5,773,702 and WO 99/057965, for salad US 5,198,599 or for sunflower WO 01/065922).
  • Plants or plant cultivars which were obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are tolerant of abiotic stress factors. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation that confers such stress resistance. Particularly useful plants with stress tolerance include the following:
  • Plants which contain a transgene which is able to reduce the expression and / or activity of the gene for the poly (ADP-ribose) polymerase (PARP) in the plant cells or plants.
  • PARP poly (ADP-ribose) polymerase
  • Plants that contain a stress-tolerant transgene that encodes a plant-functional enzyme of the nicotinamide adenine dinucleotide salvage biosynthetic pathway including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyltransferase, nicotinamidinamide transidiboribinotinosinodidase niborotinosinodinase diborobenzylase.
  • Plants or plant cultivars which were obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, have a changed amount, quality and / or storability of the edged product and / or changed properties of certain constituents of the edged product, such as: 1) Transgenic plants that synthesize a modified starch, the chemical-physical properties, in particular the amylose content or the amylose / amylopectin ratio, the degree of branching, the average chain length, the distribution of the side chains, the
  • Viscosity behavior, the gel strength, the starch size and / or starch comorphology is changed compared to the synthesized starch in wild type plant cells or plants, so that this modified starch is more suitable for certain applications.
  • Non-starch carbohydrate polymers the properties of which have changed in comparison to wild type plants without genetic modification. Examples are plants which produce polyfructose, in particular of the inulin and levan type, plants which produce alpha-1,4-glucans, plants which produce alpha-1,4-branched alpha-1,4-glucans and plants which Produce Alteman.
  • Transgenic plants or hybrid plants such as onions with certain properties such as "high soluble solids content” (“high soluble solids content”), low sharpness (“low pungency”, LP) and / or long shelf life (“long storage", LS ).
  • Plants or plant varieties which were obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are plants such as
  • Cotton plants with changed fiber properties Such plants can be obtained by genetic transformation or by selection of plants which contain a mutation which confers such modified fiber properties; these include:
  • Plants such as cotton plants which contain a modified form of rsw2 or rsw3 homologous nucleic acids, such as cotton plants with an increased expression of sucrose phosphate synthase;
  • plants such as cotton plants with an increased expression of sucrose synthase
  • Plants such as cotton plants in which the timing of the passage control of the plasmodesms at the base of the fiber cell is changed, e.g. B. by down-regulating the fiber-selective ⁇ -1,3-glucanase; e) Plants such as cotton plants with fibers with changed reactivity, e.g. B. by expression of the N-acetylglucosamine transferase gene, including nodC, and of chitin synthase genes.
  • Plants or plant cultivars which were obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are plants such as oilseed rape or related Brassica plants with changed properties of the oil composition. Such plants can be obtained by genetic transformation or by selection of plants which contain a mutation which imparts such altered oil properties; these include:
  • Plants such as oilseed rape plants that produce oil with a high oleic acid content
  • Plants such as rapeseed plants that produce oil with a low linolenic acid content.
  • Plants such as oilseed rape plants that produce oil with a low saturated fatty acid content.
  • Plants or plant varieties which can be obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are plants such as potatoes which are virus-resistant, e.g. against the potato virus Y (event SY230 and SY233 from Tecnoplant, Argentina), or which are resistant to diseases such as late blight (potato late blight) (e.g. RB gene), or which show a reduced cold-induced sweetness (which the genes Nt- Inh, carry II-INV) or which show the dwarf phenotype (gene A-20 oxidase).
  • viruses which are virus-resistant, e.g. against the potato virus Y (event SY230 and SY233 from Tecnoplant, Argentina), or which are resistant to diseases such as late blight (potato late blight) (e.g. RB gene), or which show a reduced cold-induced sweetness (which
  • Plants or plant cultivars which were obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are plants such as oilseed rape or related Brassica plants with altered properties in seed loss (seed shattering). Such plants can be genetically transformed or selected from plants containing a mutation that confer such altered properties and include plants such as oilseed rape with delayed or reduced seed loss.
  • transgenic plants which can be treated according to the invention are plants with transformation events or combinations of transformation events which have been issued or pending petitions by the Animal and Plant Health Inspection Service (APHIS) of the United States Department of Agriculture (USDA) for the unregulated status. Information on this is available at any time from APHIS (4700 River Road Riverdale, MD 20737, USA), e.g. via the website http://www.aphis.usda.gov/brs/not_reg.html. On the filing date of this
  • Transgenic phenotype the trait that is given to the plant by the transformation event.
  • transgenic plants which can be treated according to the invention are plants with one or more genes which code for one or more toxins, are the transgenic plants which are offered under the following trade names: YIELD GARD® (for example corn, cotton, Soybeans), KnockOut® (e.g. corn), BiteGard® (e.g. corn), BT-Xtra® (e.g. corn), StarLink® (e.g. corn), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (e.g.
  • Herbicide-tolerant plants to be mentioned are, for example, maize varieties, cotton varieties and soybean varieties, which are offered under the following trade names: Roundup Ready® (glyphosate tolerance, for example maize, cotton, soybean), Liberty Link® (phosphinotricine tolerance, for example rapeseed) , IMI® (imidazolinone tolerance) and SCS® (Sylfonylurstoffioleranz), for example maize.
  • the herbicide-resistant plants (plants bred traditionally to herbicide tolerance) that should be mentioned include the varieties offered under the name Clearfield® (for example maize).
  • transgenic plants which can be treated according to the invention are plants which contain transformation events or a combination of transformation events and which are listed, for example, in the files of various national or regional authorities (see, for example, http: / /gmoinfo.jrc.it/gmp_browse.aspx and

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Abstract

La présente invention concerne des hétérocyclylpyrrolones substituées représentées par la formule générale (I) ou leurs sels, (I) les radicaux de la formule générale (I) étant tels que définis dans la description, ainsi que leur utilisation comme herbicides, en particulier, pour lutter contre les mauvaises herbes et/ou graminées indésirables dans les cultures de plantes utiles et/ou comme régulateurs de croissance des plantes pour influencer la croissance des cultures de plantes utiles.
PCT/EP2019/066188 2018-06-25 2019-06-19 Hétérocyclylpyrrolones substituées, leurs sels et leur utilisation comme agents herbicides Ceased WO2020002083A1 (fr)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016071359A1 (fr) * 2014-11-07 2016-05-12 Syngenta Participations Ag Composés herbicides
WO2016071360A1 (fr) * 2014-11-07 2016-05-12 Syngenta Participations Ag Dérivés de pyrrolone herbicides
WO2018029104A1 (fr) * 2016-08-11 2018-02-15 Bayer Cropscience Aktiengesellschaft Dérivés de pyrazolinyle substitués, procédés de production de ces dérivés et leur utilisation comme herbicides et/ou régulateurs de croissance des plantes

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016071359A1 (fr) * 2014-11-07 2016-05-12 Syngenta Participations Ag Composés herbicides
WO2016071360A1 (fr) * 2014-11-07 2016-05-12 Syngenta Participations Ag Dérivés de pyrrolone herbicides
WO2018029104A1 (fr) * 2016-08-11 2018-02-15 Bayer Cropscience Aktiengesellschaft Dérivés de pyrazolinyle substitués, procédés de production de ces dérivés et leur utilisation comme herbicides et/ou régulateurs de croissance des plantes

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