WO2020002090A1 - Thiazolylpyrrolones substituées, leurs sels et leur utilisation comme agents herbicides - Google Patents

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

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WO2020002090A1
WO2020002090A1 PCT/EP2019/066198 EP2019066198W WO2020002090A1 WO 2020002090 A1 WO2020002090 A1 WO 2020002090A1 EP 2019066198 W EP2019066198 W EP 2019066198W WO 2020002090 A1 WO2020002090 A1 WO 2020002090A1
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phenyl
methyl
alkyl
butenyl
dimethyl
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PCT/EP2019/066198
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German (de)
English (en)
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Hendrik Helmke
Thomas Müller
Jens Frackenpohl
Jana FRANKE
Benjamin Anthony CHALMERS
Uwe Döller
Dirk Schmutzler
Elisabeth ASMUS
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Bayer Aktiengesellschaft
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

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 thiazolylpyrrolones 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.
  • Isoxazolines Substituted pyrrolones and their herbicidal or pesticidal properties are also described in CH633678, DE 2735841, EP0297378, EP0334133, EP0339390 and EP0286816.
  • WO2016 / 071361, WO2016 / 071362, WO2016 / 071363 and WO2016 / 071364 also describe substituted hydantoins which also carry heterocyclic substituents on the nitrogen, for example optionally further substituted isoxazolines.
  • Selected specially substituted 1,3,4-thiadiazolyl and l, 2,4-thiadiazolyl-2,5-dioxoimidazolines and their herbicidal activity are described in DE2247266 described.
  • Active ingredients are described, for example, in WO2015 / 018434.
  • 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-C 8 ) -haloalkyl, (Ci-Cg) -hydroxyalkyl, (C i - C s) -
  • a 1 and A 2 independently of one another represent CH or the grouping CR 2 , where
  • a 1 stands for CH if A 2 stands for the grouping CR 2 and
  • a 1 stands for the grouping CR 2 , if A 2 stands for CH,
  • R 2 for hydrothio, hydroxy, halogen, (Ci-Cg) alkyl, (Ci-Cg) haloalkyl, (C 3 -Cio) cycloalkyl, (C 3 -Cio) cycloalkyl (Ci-Cg) alkyl , Aryl, heteroaryl, heterocyclyl, aryl- (Ci-Cg) -alkyl,
  • R 3 for hydroxy, hydrothio, halogen, NR 5 R 6 , (Ci-Cs) alkoxy, (C 3 -Cio) cycloalkyl- (Ci-C 8 ) alkoxy, aryl- (Ci-C 8 ) alkoxy , (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkoxy, arylcarbonyloxy, (Ci-C 8 ) -alkylcarbonyloxy, aryl- (Ci-C 8 ) -alkylcarbonyloxy, heteroarylcarbonyloxy, (C 3 -C 10 ) - Cycloalkylcarbonyloxy, heterocyclylcarbonyloxy, (Ci-C 8 ) -haloalkyl-carbonyloxy, (C 2 -C 8 ) - alkenylcarbonyloxy, OC (0) OR 5 , OC (0) SR 9 , OC (S)
  • R 4 represents hydrogen, (Ci-Cs) -alkyl
  • R 5 and R 6 are identical or different and independently of one another are hydrogen, (C 1 -C 8 ) -alkyl
  • R 7 is H, (Ci-C 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (Ci-C 8 ) cyanoalkyl, (Ci-Cio) haloalkyl , (C 2 -C 8 ) haloalkenyl, (C 2 -C 8 ) haloalkynyl, (C 3 -Cio) cycloalkyl, (C 3 -C 10 ) halocycloalkyl, (C 4 -Cio) cycloalkenyl, ( C 4 -Cio) halocycloalkenyl, (Ci-C 8 ) alkoxy- (Ci-C 8 ) alkyl, (Ci-C 8 ) alkoxy- (Ci-C 8 ) haloalkyl, aryl, aryl- (Ci -C 8 ) -alky
  • R 8 and R 9 are identical or different and independently of one another for (Ci-C 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (Ci-C 8 ) cyanoalkyl , (Ci-Cio) haloalkyl, (C 2 -C 8 ) haloalkenyl, (C 2 -C 8 ) haloalkynyl, (C 3 -Cio) cycloalkyl, (C 3 -Cio) halocycloalkyl, (C 4 -Cio) cycloalkenyl, (C 4 -Cio) halocycloalkenyl, (Ci-C 8 ) alkoxy- (Ci-C 8 ) alkyl, (Ci-C 8 ) alkoxy- (Ci-C 8 ) haloalkyl , Aryl, aryl- (Ci
  • the compounds of general formula (1) can be added by adding a suitable one
  • inorganic or organic acid such as mineral acids such as HCl, HBr, H2SO4, H3P04 or HNO3, 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 a basic group such as e.g. Amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, form salts. These salts then contain the conjugate base of the acid as an anion. Suitable substituents which are in deprotonated form, e.g. Sulfonic acids, certain
  • Sulphonic acid amides or carboxylic acids are present, inner salts with protonatable groups such as amino groups can form. Salt formation can also be caused by exposure to a base
  • Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine, and ammonium, alkali or
  • Potassium hydroxide, sodium and potassium carbonate and sodium and potassium hydrogen carbonate are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or
  • Alkaline earth metal salts especially sodium and potassium salts, or also ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula
  • R a to R d each independently represent an organic radical, in particular alkyl, aryl, arylalkyl or alkylaryl.
  • Alkylsulfoxonium salts such as (Ci-C4) -trialkylsulfonium and (Ci-C4) -trialkylsulfoxonium salts.
  • the substituted thiazolylpyrrolones of the general formula (1) according to the invention can be present in various tautomeric structures, all of which are intended to be encompassed by the general formula (1).
  • the compounds of the formula (1) and their salts used according to the invention are referred to below as "compounds of the general formula (1)".
  • Preferred subject matter of the invention are compounds of the general formula (1), in which
  • 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-C 7 ) haloalkyl, (Ci-Cv) hydroxyalkyl, (C 1 -C 7 ) -
  • a 1 and A 2 independently of one another represent CH or the grouping CR 2 , where
  • a 1 stands for CH if A 2 stands for the grouping CR 2 and
  • a 1 stands for the grouping CR 2 , if A 2 stands for CH,
  • R 2 for hydrothio, hydroxy, halogen, (Ci-C 7 ) alkyl, (Ci-C 7 ) haloalkyl, (C 3 -Cio) cycloalkyl, (C 3 -Cio) cycloalkyl- (Ci-C 7 ) alkyl, aryl, heteroaryl, heterocyclyl, aryl (Ci-C 7 ) alkyl, heteroaryl (Ci-C 7 ) alkyl, heterocyclyl (Ci-C 7 ) alkyl, (C 2 -C 7 ) Alkenyl, (C 2 -C 7 ) alkynyl, (C 2 -C 7 ) haloalkenyl, (C 2 -C 7 ) haloalkynyl, (C 3 -Cio) halocycloalkyl, (C 4 -Cio) cycloalkenyl , (C 4 -Cio)
  • R 3 for hydroxy, hydrothio, halogen, NR 5 R 6 , (Ci-C 7 ) alkoxy, (C3-Cio) cycloalkyl- (Ci-C 7 ) alkoxy, aryl- (Ci-C 7 ) alkoxy , (Ci-C 7 ) alkoxy- (Ci-C 7 ) alkoxy, arylcarbonyloxy, (Ci-C 7 ) alkylcarbonyloxy, aryl- (Ci-C 7 ) alkylcarbonyloxy, heteroarylcarbonyloxy, (C3-C10) - cycloalkylcarbonyloxy , Heterocyclylcarbonyloxy, (Ci-C 7 ) -haloalkyl-carbonyloxy, (C 2 -C 7 ) - alkenylcarbonyloxy, OC (0) OR 5 , OC (0) SR 9 , OC (S) OR 8 , OC (
  • R 4 represents hydrogen, (Ci-C 7 ) alkyl
  • R 5 and R 6 are identical or different and independently of one another are hydrogen, (C 1 -C 7 ) -alkyl,
  • R 7 for H, (Ci-C 7 ) alkyl, (C 2 -C 7 ) alkenyl, (C 2 -C 7 ) alkynyl, (Ci-C 7 ) cyanoalkyl, (Ci-C 7 ) - Haloalkyl, (C 2 -C 7 ) haloalkenyl, (C 2 -C 7 ) haloalkynyl, (C3-Cio) cycloalkyl, (C3-Cio) halocycloalkyl, (C 4 -Cio) cycloalkenyl, (C 4 -Cio) halocycloalkenyl, (Ci-C 7 ) alkoxy- (Ci-C 7 ) alkyl, (Ci-C 7 ) - alkoxy- (Ci-C 7 ) haloalkyl, aryl, aryl- (Ci-C 7 ) -alkyl
  • R 8 and R 9 are identical or different and independently of one another for (Ci-C 7 ) -alkyl, (C 2 -C 7 ) -
  • 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 halogen, cyano, (Ci-C 6 ) -alkyl, (Ci-Cej-haloalkyl, (Ci-Cej-hydroxyalkyl, (GG) -
  • a 1 and A 2 independently of one another represent CH or the grouping CR 2 , where
  • a 1 stands for CH if A 2 stands for the grouping CR 2 and A 1 stands for the grouping CR 2 , if A 2 stands for CH,
  • R 2 for cyano, halogen, (Ci-C6) alkyl, (G-C6) haloalkyl, (Ci-C6) hydroxyalkyl, (GG) -
  • R 3 for hydroxy, hydrothio, halogen, NR 5 R 6 , (Ci-Ce) alkoxy, (C 3 -Cio) cycloalkyl- (Ci-C 6 ) alkoxy, aryl- (Ci-C6) alkoxy, (Ci-C6) alkoxy- (Ci-C6) alkoxy, arylcarbonyloxy, (GG) - alkylcarbonyloxy, aryl- (Ci-C6) alkylcarbonyloxy, heteroarylcarbonyloxy, (C 3 -G 0 ) - cycloalkylcarbonyloxy, heterocyclylcarbonyloxy, (Ci -C6) haloalkylcarbonyloxy, (C 2 -C 6 ) alkenylcarbonyloxy, OC (0) OR 5 , OC (0) SR 9 , OC (S) OR 8 , OC (S) SR 9 , OSO 2 R 8 , OSO
  • R 4 represents hydrogen, (G-Ce) alkyl
  • R 5 and R 6 are identical or different and independently of one another are hydrogen, (G-Ce) -alkyl,
  • R 7 for H, (Ci-C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (Ci-C 6 ) cyanoalkyl, (Ci-C 6 ) - Haloalkyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) haloalkynyl, (C 3 -Cio) cycloalkyl, (C 3 -Cio) halocycloalkyl, (C 4 -Cio) cycloalkenyl, ( C 4 -Cio) halocycloalkenyl, (GC 6 ) alkoxy- (GC 6 ) alkyl, (Ci-C 6 ) alkoxy- (Ci-C6) haloalkyl, aryl, aryl- (Ci-C6) alkyl , Heteroaryl, heteroaryl-
  • 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 -
  • Cyclohexylmethyl methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, iso-propylcarbonyl, n-butylcarbonyl, tert-butylcarbonyl, ethenyl, l-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-l-propenyl, 2-methyl-l-propenyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, l-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, 2-methyl-3-butenyl, 3-methyl
  • a 1 and A 2 independently of one another represent CH or the grouping CR 2 , where
  • a 1 stands for CH if A 2 stands for the grouping CR 2 and
  • a 1 stands for the grouping CR 2 , if A 2 stands for CH,
  • R 2 for fluorine, chlorine, bromine, iodine, hydroxy, hydrothio, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1 -Methylbutyl, 2-methylbutyl, 3 -methylbutyl, 1,1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4 -Methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbuty
  • R 3 for hydroxy, hydrothio, fluorine, chlorine, bromine, iodine, amino, methoxy, ethoxy, n-propyloxy, 1-methylethoxy, n-butyloxy, 1-methylpropyloxy, 2-methylpropyloxy, l, l-dimethylethoxy, n-pentyloxy , 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, l, l-dimethylpropyloxy,
  • Difluoromethylcarbonyloxy methoxycarbonyloxy, ethoxycarbonyloxy, n-propyloxycarbonyloxy, iso-propyloxycarbonyloxy, n-butyloxycarbonyloxy, 1,1-dimethylethyloxycarbonyloxy, 2,2-dimethylpropyloxycarbonyloxy, benzyloxycarbonyloxy, allylcarbonyloxy, methylsulfonyloxy, ethylylsulfonyloxy, ethylylsulfonyloxy, Cyclopentylsulfonyloxy Cyclohexylsulfonyloxy, phenylsulfonyloxy, p-chlorophenylsulfonyloxy, m-chlorophenylsulfonyloxy, o-chlorophenylsulfonyloxy, p-fluorophenylsulfonyloxy
  • R 4 represents hydrogen, methyl, ethyl.
  • 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 chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, l, l-dimethylethyl, n-pentyl, 1-methylbutyl, 2 -Methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1 - methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, l , l-dimethylbutyl, 1,2-dimethylbutyl, l, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl,
  • R 3 for hydroxy, chlorine, amino, methoxy, ethoxy, n-propyloxy, 1-methylethoxy, n-butyloxy, 1 -
  • Methyl propyloxy 2-methyl propyloxy, l, l-dimethylethoxy, n-pentyloxy, cyclopropyl methoxy, cyclobutyl methoxy, cyclopentyl methoxy, cyclohexyl methoxy, benzyloxy, p-chlorophenyl methoxy, m-chlorophenyl methoxy, o-chlorophenyl methoxy, p-methoxyphenyl methoxy, methoxy methoxy, methoxymoxy meth propyloxy,
  • Difluoromethylcarbonyloxy methoxycarbonyloxy, ethoxycarbonyloxy, n-propyloxycarbonyloxy, iso-propyloxycarbonyloxy, n-butyloxycarbonyloxy, 1,1-dimethylethyloxycarbonyloxy, benzyloxycarbonyloxy, 2,2-dimethylpropyloxycarbonyloxy, allylcarbonyloxy, methylsulfonyloxy, ethylylsulfonyloxy, ethylylsulfonyl
  • R 4 represents hydrogen
  • Q stands for one of the groupings Q-1 .1 to Q-1 .68 specifically mentioned in the following table:
  • 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 chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, l, l-dimethylethyl, n-pentyl, 1-methylbutyl, 2 -Methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1 -ethylpropyl, n-hexyl, 1 - Methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, l, l-dimethylbutyl, 1,2-dimethylbutyl, l, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3- dimethylbutyl,
  • Pentafluoroethylthio phenyl, phenyloxy, p-Cl-phenyloxy, thiophene-2-yl, thiophene-3-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, furan-2-yl, furan 3-yl, cyclopropylmethyl,
  • R 3 for hydroxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1 -
  • R 4 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 chlorine, bromine, methyl, ethyl, 1-methylethyl, l, l-dimethylethyl, methoxy, ethoxy,
  • R 3 for hydroxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1 -
  • R 4 represents hydrogen
  • Q stands for one of the groupings Q-1 .1 to Q-1 .68 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) -, (C I -C ⁇ ) - or (Ci-C i) -alkylthio, for example (but not limited to) (Ci-C 6 ) -alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, l, l-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, l, l-dimethylpropylthio, 1, 2-dimethylpropylthio, 2,2- Dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpent
  • 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, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl,
  • Alkoxy means an alkyl radical bonded via an oxygen atom, eg. B. (but not limited to) (Ci-C 6 ) alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, l, l-dimethylethoxy, pentoxy, 1-methylbutoxy, 2 -Methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1 - methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, l, l -Dimethylbutoxy, l, 2-dimethylbutoxy, l, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, l
  • Alkenyloxy means an alkenyl radical bonded via an oxygen atom
  • alkynyloxy means an alkynyl radical bonded via an oxygen atom, such as (C2-C10) -, (C2-C6) - or (C2-C 4 ) -alkenoxy or (C3-C10) -, ( C3-C6) 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 heteroaromatic and can be unsubstituted or substituted, where the binding site is located on a ring atom.
  • the heterocyclyl radical or the heterocyclic ring is optionally substituted, it can be fused with other carbocyclic or heterocyclic rings.
  • heterocyclyl In the case of optionally substituted heterocyclyl, multi-cyclic systems are also included, such as 8-aza-bicyclo [3.2.l] octanyl, 8-aza- bicyclo [2.2.2] octanyl or l-azabicyclo [2.2.l] heptyl. In the case of optionally substituted heterocyclyl also
  • the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but not two
  • Oxygen atoms 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 the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazol-3- or 4- or 5-yl; 4,5-dihydro-1H-pyrazole-l- or 3- or 4- or 5-yl; 2,3-dihydro-1H-pyrazole-1 or 2- or
  • 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,
  • 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.
  • N (O), S (O) also SO for short
  • S (0) 2 also briefly SO2
  • 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-benz
  • halogen means, for example, fluorine, chlorine, bromine or iodine.
  • halogen means for example a fluorine, chlorine, bromine or iodine atom.
  • alkyl means a straight-chain or branched, open-chain, saturated hydrocarbon radical which is optionally substituted one or more times and is referred to in the latter case as “substituted alkyl”.
  • Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups; methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine are particularly preferred.
  • the prefix "bis” also includes the combination of different alkyl residues, e.g. B. methyl (ethyl) or ethyl (methyl).
  • Haloalkyl 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 B. CCI3, CCIF 2 , CFC1 2 , CF 2 CC1F 2 , CF 2 CCIFCF3; Polyhaloalkyl such as B. CH 2 CHFC1, CF 2 CC1FH, CF 2 CBrFH, CH 2 CF 3 ;
  • perhaloalkyl also includes the term perfluoroalkyl.
  • Partially fluorinated alkyl means a straight-chain or branched, saturated hydrocarbon which is substituted one or more times 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 chains, 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 various halogen atoms with at least one fluorine atom, all other halogen atoms which may be present being selected from the group consisting of fluorine, chlorine or bromine, iodine.
  • the corresponding halogen atoms can be located as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain.
  • Partially fluorinated haloalkyl also includes the complete substitution of the straight or branched ketene 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 for C atoms, d. H. includes the residues methyl, ethyl, 1-propyl, 2-propyl, 1-butyl,
  • 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 e.g.
  • Vinyl which may 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, 1, 2-dimethyl-l-propen
  • alkynyl also includes straight-chain or branched open-chain ones
  • C2-C6 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, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-2-pentynyl
  • 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
  • Carbon atoms according to the range for carbon atoms.
  • 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, for example 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2- Cyclohexenyl, 3-cyclohexenyl, l, 3-cyclohexadienyl or 1, 4-cyclohexadienyl, where also substituents with a double bond on the cycloalkenyl radical, e.g. B. an alkylidene group such as methylidene are included.
  • substituents with a double bond on the cycloalkenyl radical e.g.
  • an alkylidene group such as methylidene are included.
  • 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.
  • cyclopropylmethyl (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 I -C ⁇ ) - 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 formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E Isomers) occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers can occur.
  • Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods.
  • the chromatographic separation can be carried out on an analytical scale to determine the enantiomeric excess or the diastereomeric excess, as well as on a preparative scale for the production of test samples for biological testing.
  • 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.
  • the cleaning can also be carried out by
  • Methods for isolation, purification and stereoisomer separation of compounds of the general formula (I) are those which are generally known to the person skilled in the art from analogous cases, e.g. by physical processes such as crystallization, chromatography processes, especially column chromatography and HPLC (high pressure liquid chromatography), distillation, optionally under reduced pressure, extraction and other processes, any remaining mixtures can usually be separated by chromatographic separation, e.g. on chiral solid phases.
  • the substituted thiazolylpyrrolones 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 manufactured substituted 2-aminothiazoles and on appropriately substituted furanones or furandions.
  • the compounds of the general formula (Ib) according to the invention are synthesized via a reaction of a hydroxypyrrolone of the general formula (Ia) with a halogen formic acid derivative of the general formula (II).
  • the reaction preferably takes place in the temperature range between -20 ° C and 80 ° C, in an adequate solvent such as dichloromethane, acetonitrile, NN-
  • the compounds of the general formula (Ic) according to the invention are synthesized by reacting a hydroxypyrrolone of the general formula (Ia) with an acid halide derivative of the general formula (III).
  • the reaction preferably takes place in the temperature range between -20 ° C and 80 ° C, in an adequate solvent such as dichloromethane, acetonitrile, N, N-dimethylformamide or ethyl acetate and in the presence of a base such as triethylamine, V, V - diisopropylethylamine or 1,8-diazabicyclo [5.4.0] undec-7-cene instead (see Scheme 2).
  • the synthesis of the compounds of the general formula (Id) according to the invention takes place via a reaction of a hydroxypyrrolone of the general formula (Ia) with an isocyanate of the general formula (IV).
  • the reaction preferably takes place in the temperature range between -20 ° C and 120 ° C, in an adequate solvent such as dichloromethane, acetonitrile,, V,, V-D imct hy 1 - form am id or ethyl acetate and in the presence of a base such as triethylamine, / V,, V- diisopro py 1 cthy 1 amine or l, 8-diazabicyclo [5.4.0] undec-7-cene instead (see Scheme 3).
  • R (Ci-C 4 ) alkyl
  • the compounds of the general formula (Ia) and (Ie) according to the invention are synthesized by reducing a substituted maleimide of the general formula (V) with a
  • Reducing agents such as sodium hydride, lithium aluminum hydride, sodium borohydride or other hydrogen-generating metal hydrides.
  • a transition metal-mediated hydrogenation can also be carried out (cf. CH633678, DE2247266, WO2015 / 018434). Since the groups X and Y are different, the reduction of the carbonyl group can be mixtures of
  • the reaction preferably takes place in the temperature range between -20 ° C and 120 ° C in an adequate solvent such as tetrahydrofuran, methanol or ethanol.
  • Substituted maleimides of the general formula (V) can be obtained by condensation of a substituted aminothiazole of the general formula (VI) with a substituted furan-2,5-dione of the general formula (VII) in the presence of a Broensted acid such as acetic acid or
  • the monosubstituted furan-2,5-diones (VII), 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 (VII. A) and (Vll.b) im
  • Mono-substituted thiazoles can be prepared by literature known synthetic procedures (see Bioorg & MedChem Let 2004, 14, 5521-5525;.... Heterocyclic Chemistry, Ed JA Joule and K. Mills, 4th Edition, Blackwell Publishing, 2000. 418-420; W02008 / 55840; US2012 / 22067;
  • the compound (Vl.a) can be made from a haloketone (X) and thiourea (XI).
  • the aminothiazole (Vl.b) can be prepared from the haloaldehyde (XII) and thiourea (XI) (Scheme 7).
  • Acetic anhydride using a suitable base forms the monosubstituted thiazolylpyrrolone of the general formula (XV) with O-acetyl group, which can be obtained by heating under acidic conditions (e.g. in a mixture of acetic acid and Water) can be converted into the corresponding monosubstituted thiazolylpyrrolone of the general formula (Ia) with a free OH group.
  • a suitable base e.g. pyridine
  • the reaction preferably takes place in the temperature range between -20 ° C and 80 ° C, in an adequate solvent such as dichloromethane, acetonitrile, NN-dimethylformamide or ethyl acetate and in the presence of a base such as triethylamine, V, V-diisopropylethylamine or 1,8-diazabicyclo [5.4.0] undec-7-cene instead (see Scheme 9).
  • Synthesis stage 1 2-bromo-l- (l -methylcyclopropyl) ethanone l- (l-Methylcyclopropyl) ethanone (6.00 g, 61.13 mmol, 1.0 equiv.) was dissolved in methanol (40 mL) and cooled to approx. 4 ° C with an ice bath. Bromine (3.15 mL, 61.13 mmol,
  • reaction temperature does not exceed 10 ° C.
  • the reaction mixture was stirred at about 4 ° C. for 45 min and then water (10 mL) was added. The mixture was then stirred at room temperature for 1 h, during which the reaction solution decolorized.
  • the reaction mixture was diluted with water and diethyl ether was added and extracted. The combined organic phases were then dried over magnesium sulfate, filtered and the solvent was distilled off via a short path column. The distillation still contained the desired product 2-bromo-1- (1-methylcyclopropyl) ethanone in the form of a slightly yellow liquid (11.00 g, 90%, 91% of theory). The crude product was used in the next step without further purification.
  • Thiazolylpyrrolone gives the compounds mentioned below. If in Table 1 a structural element is defined by a structural formula which contains a dashed line, this dashed line means that the group in question is connected to the rest of the molecule at this position.
  • Table 1.1 Preferred compounds of the formula (1.1) are the compounds 1.1-1 to 1.1-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.1-1 to 1.1- 68 of Table 1.1 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.2 Preferred compounds of the formula (1.2) are the compounds 1.2-1 to 1.2-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.2-1 to 1.2- 68 of table 1.2 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.3 Preferred compounds of the formula (1.3) are the compounds 1.3-1 to 1.3-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.3-1 to 1.3- 68 of table 1.3 are thus by the meaning of the respective entries no. 1 to 68 defined for Q of Table 1.
  • Table 1.4 Preferred compounds of the formula (1.4) are the compounds 1.4-1 to 1.4-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.4-1 to 1.4- 68 of Table 1.4 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.5 Preferred compounds of the formula (1.5) are the compounds 1.5-1 to 1.5-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.5-1 to 1.5- 68 of Table 1.5 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.6 Preferred compounds of the formula (1.6) are the compounds 1.6-1 to 1.6-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.6-1 to 1.6- 68 of table 1.6 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.7 Preferred compounds of the formula (1.7) are the compounds 1.7-1 to 1.7-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.7-1 to 1.7- 68 of table 1.7 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.8 Preferred compounds of the formula (1.8) are the compounds 1.8-1 to 1.8-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.8-1 to 1.8- 68 of Table 1.8 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.9 Preferred compounds of the formula (1.9) are the compounds 1.9-1 to 1.9-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.9-1 to 1.9- 68 of Table 1.9 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.10 Preferred compounds of the formula (1.10) are the compounds 1.10-1 to 1.10-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.10-1 to 1.10-68 of table 1.10 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.11 Preferred compounds of the formula (1.11) are the compounds 1.11-1 to 1.11-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.11-1 to 1.11-68 of table 1.11 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.12 Preferred compounds of the formula (1.12) are the compounds 1.12-1 to 1.12-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.12-1 to 1.12-68 of table 1.12 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.13 Preferred compounds of the formula (1.13) are the compounds 1.13-1 to 1.13-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.13-1 to 1.13-68 of table 1.13 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.14 Preferred compounds of the formula (1.14) are the compounds 1.14-1 to 1.14-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.14-1 to 1.14-68 of table 1.14 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.15 Preferred compounds of the formula (1.15) are the compounds 1.15-1 to 1.15-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.15-1 to 1.15-68 of table 1.15 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.16 Preferred compounds of the formula (1.16) are the compounds 1.16-1 to 1.16-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.16-1 to 1.16-68 of table 1.16 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.17 Preferred compounds of the formula (1.17) are the compounds 1.17-1 to 1.17-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.17-1 to 1.17-68 of table 1.17 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.18 Preferred compounds of the formula (1.18) are the compounds 1.18-1 to 1.18-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.18-1 to 1.18-68 of table 1.18 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.19 Preferred compounds of the formula (1.19) are the compounds 1.19-1 to 1.19-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.19-1 to 1.19-68 of table 1.19 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.20 Preferred compounds of the formula (1.20) are the compounds 1.20-1 to 1.20-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.20-1 to 1.20-68 of Table 1.20 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.21 Preferred compounds of the formula (1.21) are the compounds 1.21-1 to 1.21-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.21-1 to 1.21-68 of table 1.21 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.22 Preferred compounds of the formula (1.22) are the compounds 1.22-1 to 1.22-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.22-1 to 1.22-68 of table 1.22 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.23 Preferred compounds of the formula (1.23) are the compounds 1.23-1 to 1.23-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.23-1 to 1.23-68 of table 1.23 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.24 Preferred compounds of the formula (1.24) are the compounds 1.24-1 to 1.24-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.24-1 to 1.24-68 of table 1.24 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.25 Preferred compounds of the formula (1.25) are the compounds 1.25-1 to 1.25-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.25-1 to 1.25-68 of table 1.25 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.26 Preferred compounds of the formula (1.26) are the compounds 1.26-1 to 1.26-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.26-1 to 1.26-68 of table 1.26 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.27 Preferred compounds of the formula (1.27) are the compounds 1.27-1 to 1.27-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.27-1 to 1.27-68 of table 1.27 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.28 Preferred compounds of the formula (1.28) are the compounds 1.28-1 to 1.28-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.28-1 to 1.28-68 of table 1.28 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.29 Preferred compounds of the formula (1.29) are the compounds 1.29-1 to 1.29-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.29-1 to 1.29-68 of table 1.29 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.30 Preferred compounds of the formula (1.30) are the compounds 1.30-1 to 1.30-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.30-1 to 1.30-68 of table 1.30 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.31 Preferred compounds of the formula (1.31) are the compounds 1.31-1 to 1.31-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.31-1 to 1.31-68 of table 1.31 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.32 Preferred compounds of the formula (1.32) are the compounds 1.32-1 to 1.32-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.32-1 to 1.32-68 of table 1.32 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.33 Preferred compounds of the formula (1.33) are the compounds 1.33-1 to 1.33-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.33-1 to 1.33-68 of table 1.33 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.34 Preferred compounds of the formula (1.34) are the compounds 1.34-1 to 1.34-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.34-1 to 1.34-68 of table 1.34 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.35 Preferred compounds of the formula (1.35) are the compounds 1.35-1 to 1.35-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.35-1 to 1.35-68 of table 1.35 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.36 Preferred compounds of the formula (1.36) are the compounds 1.36-1 to 1.36-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.36-1 to 1.36-68 of table 1.36 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.37 Preferred compounds of the formula (1.37) are the compounds 1.37-1 to 1.37-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.37-1 to 1.37-68 of table 1.37 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.38 Preferred compounds of the formula (1.38) are the compounds 1.38-1 to 1.38-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.38-1 to 1.38-68 of table 1.38 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.39 Preferred compounds of the formula (1.39) are the compounds 1.39-1 to 1.39-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.39-1 to 1.39-68 of table 1.39 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.40 Preferred compounds of the formula (1.40) are the compounds 1.40-1 to 1.40-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.40-1 to 1.40-68 of table 1.40 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.41 Preferred compounds of the formula (1.41) are the compounds 1.41-1 to 1.41-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.41-1 to 1.41-68 of Table 1.41 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.42 Preferred compounds of the formula (1.42) are the compounds 1.42-1 to 1.42-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.42-1 to 1.42-68 of table 1.42 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.43 Preferred compounds of the formula (1.43) are the compounds 1.43-1 to 1.43-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.43-1 to 1.43-68 of table 1.43 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.44 Preferred compounds of the formula (1.44) are the compounds 1.44-1 to 1.44-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.44-1 to 1.44-68 in Table 1.44 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.45 Preferred compounds of the formula (1.45) are the compounds 1.45-1 to 1.45-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.45-1 to 1.45-68 of table 1.45 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.46 Preferred compounds of the formula (1.46) are the compounds 1.46-1 to 1.46-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.46-1 to 1.46-68 in Table 1.46 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.47 Preferred compounds of the formula (1.47) are the compounds 1.47-1 to 1.47-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.47-1 to 1.47-68 in Table 1.47 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.48 Preferred compounds of the formula (1.48) are the compounds 1.48-1 to 1.48-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.48-1 to 1.48-68 of table 1.48 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.49 Preferred compounds of the formula (1.49) are the compounds 1.49-1 to 1.49-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.49-1 to 1.49-68 of table 1.49 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.50 Preferred compounds of the formula (1.50) are the compounds 1.50-1 to 1.50-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.50-1 to 1.50-68 of table 1.50 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.51 Preferred compounds of the formula (1.51) are the compounds 1.51-1 to 1.51-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.51-1 to 1.51-68 of table 1.51 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.52 Preferred compounds of the formula (1.52) are the compounds 1.52-1 to 1.52-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.52-1 to 1.52-68 of table 1.52 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.53 Preferred compounds of the formula (1.53) are the compounds 1.53-1 to 1.53-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.53-1 to 1.53-68 of table 1.53 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.54 Preferred compounds of the formula (1.54) are the compounds 1.54-1 to 1.54-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.54-1 to 1.54-68 of table 1.54 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.55 Preferred compounds of the formula (1.55) are the compounds 1.55-1 to 1.55-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.55-1 to 1.55-68 of table 1.55 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.56 Preferred compounds of the formula (1.56) are the compounds 1.56-1 to 1.56-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.56-1 to 1.56-68 of table 1.56 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.57 Preferred compounds of the formula (1.57) are the compounds 1.57-1 to 1.57-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.57-1 to 1.57-68 of table 1.57 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.58 Preferred compounds of the formula (1.58) are the compounds 1.58-1 to 1.58-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.58-1 to 1.58-68 of table 1.58 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.59 Preferred compounds of the formula (1.59) are the compounds 1.59-1 to 1.59-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.59-1 to 1.59-68 of table 1.59 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.60 Preferred compounds of the formula (1.60) are the compounds 1.60-1 to 1.60-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.60-1 to 1.60-68 of table 1.60 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.61 Preferred compounds of the formula (1.61) are the compounds 1.61-1 to 1.61-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.61-1 to 1.61-68 of table 1.61 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.62 Preferred compounds of the formula (1.62) are the compounds 1.62-1 to 1.62-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.62-1 to 1.62-68 of table 1.62 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.63 Preferred compounds of the formula (1.63) are the compounds 1.63-1 to 1.63-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.63-1 to 1.63-68 of table 1.63 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.64 Preferred compounds of the formula (1.64) are the compounds 1.64-1 to 1.64-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.64-1 to 1.64-68 of table 1.64 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.65 Preferred compounds of the formula (1.65) are the compounds 1.65-1 to 1.65-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.65-1 to 1.65-68 of table 1.65 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.66 Preferred compounds of the formula (1.66) are the compounds 1.66-1 to 1.66-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.66-1 to 1.66-68 of table 1.66 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.67 Preferred compounds of the formula (1.67) are the compounds 1.67-1 to 1.67-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.67-1 to 1.67-68 in Table 1.67 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.68 Preferred compounds of the formula (1.68) are the compounds 1.68-1 to 1.68-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.68-1 to 1.68-68 of table 1.68 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.69 Preferred compounds of the formula (1.69) are the compounds 1.69-1 to 1.69-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.69-1 to 1.69-68 of table 1.69 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.70 Preferred compounds of the formula (1.70) are the compounds 1.70-1 to 1.70-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.70-1 to 1.70-68 of table 1.70 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.71 Preferred compounds of the formula (1.71) are the compounds 1.71-1 to 1.71-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.71-1 to 1.71-68 of table 1.71 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.72 Preferred compounds of the formula (1.72) are the compounds 1.72-1 to 1.72-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.72-1 to 1.72-68 of table 1.72 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.73 Preferred compounds of the formula (1.73) are the compounds 1.73-1 to 1.73-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.73-1 to 1.73-68 of table 1.73 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.74 Preferred compounds of the formula (1.74) are the compounds 1.74-1 to 1.74-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.74-1 to 1.74-68 of table 1.74 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.75 Preferred compounds of the formula (1.75) are the compounds 1.75-1 to 1.75-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.75-1 to 1.75-68 of table 1.75 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.76 Preferred compounds of the formula (1.76) are the compounds 1.76-1 to 1.76-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.76-1 to 1.76-68 of table 1.76 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.77 Preferred compounds of the formula (1.77) are the compounds 1.77-1 to 1.77-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.77-1 to 1.77-68 of table 1.77 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.78 Preferred compounds of the formula (1.78) are the compounds 1.78-1 to 1.78-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.78-1 to 1.78-68 of table 1.78 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.79 Preferred compounds of the formula (1.79) are the compounds 1.79-1 to 1.79-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.79-1 to 1.79-68 of table 1.79 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.80 Preferred compounds of the formula (1.80) are the compounds 1.80-1 to 1.80-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.80-1 to 1.80-68 of table 1.80 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.81 Preferred compounds of the formula (1.81) are the compounds 1.81-1 to 1.81-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.81-1 to 1.81-68 of table 1.81 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.82 Preferred compounds of the formula (1.82) are the compounds 1.82-1 to 1.82-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.82-1 to 1.82-68 of table 1.82 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.83 Preferred compounds of the formula (1.83) are the compounds 1.83-1 to 1.83-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.83-1 to 1.83-68 of table 1.83 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.84 Preferred compounds of the formula (1.84) are the compounds 1.84-1 to 1.84-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.84-1 to 1.84-68 of table 1.84 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.85 Preferred compounds of the formula (1.85) are the compounds 1.85-1 to 1.85-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.85-1 to 1.85-68 of table 1.85 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.86 Preferred compounds of the formula (1.86) are the compounds 1.86-1 to 1.86-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.86-1 to 1.86-68 of table 1.86 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.87 Preferred compounds of the formula (1.87) are the compounds 1.87-1 to 1.87-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.87-1 to 1.87-68 of table 1.87 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.88 Preferred compounds of the formula (1.88) are the compounds 1.88-1 to 1.88-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.88-1 to 1.88-68 of table 1.88 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.89 Preferred compounds of the formula (1.89) are the compounds 1.89-1 to 1.89-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.89-1 to 1.89-68 of table 1.89 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.90 Preferred compounds of the formula (1.90) are the compounds 1.90-1 to 1.90-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.90-1 to 1.90-68 of table 1.90 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.91 Preferred compounds of the formula (1.91) are the compounds 1.91-1 to 1.91-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.91-1 to 1.91-68 of table 1.91 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.92 Preferred compounds of the formula (1.92) are the compounds 1.92-1 to 1.92-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.92-1 to 1.92-68 in Table 1.92 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.93 Preferred compounds of the formula (1.93) are the compounds 1.93-1 to 1.93-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.93-1 to 1.93-68 in Table 1.93 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.94 Preferred compounds of the formula (1.94) are the compounds 1.94-1 to 1.94-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.94-1 to 1.94-68 of table 1.94 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.95 Preferred compounds of the formula (1.95) are the compounds 1.95-1 to 1.95-68, in which Q has the meanings of Table 1 given in the respective row. The connections
  • Table 1.96 Preferred compounds of the formula (1.96) are the compounds 1.96-1 to 1.96-68, 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 1.97-68, 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 1.98-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.98-1 to 1.98-68 of Table 1.98 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.99 Preferred compounds of the formula (1.99) are the compounds 1.99-1 to 1.99-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.99-1 to 1.99-68 of table 1.99 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.100 Preferred compounds of the formula (I.100) are the compounds I.100-1 to I.100-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 100-1 to I. 100-68 of Table I. 100 are thus by the meaning of the respective entries No. 1 to 68 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- 68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 101-1 to I. 101-68 of Table I. 101 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1. (1,102)
  • Preferred compounds of the formula (I. 102) are the compounds I. 102-1 to I. 102- 68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 102-1 to I. 102-68 of table I. 102 are thus by the meaning of the respective entries No. 1 to 68 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- 68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 103-1 to I. 103-68 of Table I. 103 are thus by the meaning of the respective entries No. 1 to 68 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- 68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1. 104-1 to 1. 104-68 of Table 1. 104 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.105 Preferred compounds of the formula (1. 105) are the compounds 1. 105-1 to 1. 105- 68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1. 105-1 to 1. 105-68 of Table 1. 105 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Preferred compounds of the formula (I. 106) are the compounds I. 106-1 to I. 106- 68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 106-1 to I. 106-68 of Table I. 106 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Preferred compounds of the formula (I. 107) are the compounds I. 107-1 to I. 107- 68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 107-1 to I. 107-68 of Table I. 107 are thus by the meaning of the respective entries No. 1 to 68 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.108-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 108-1 to I. 108-68 of Table I. 108 are thus by the meaning of the respective entries No. 1 to 68 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- 68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1. 109-1 to 1. 109-68 of table 1. 109 are thus by the meaning of the respective entries No. 1 to 68 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.110-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I.110-1 to I.110-68 of Table I.110 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.111 Preferred compounds of the formula (1.111) are the compounds 1.111-1 to 1.111-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1. 111-1 to 1. 111-68 of Table 1. 111 are thus by the meaning of the respective entries No. 1 to 68 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.112-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 112-1 to I. 112-68 of Table I. 112 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.113 Preferred compounds of the formula (I. 113) are the compounds I. 113-1 to I. 113- 68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 113-1 to I. 113-68 of Table I. 113 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above. (1,114)
  • Table 1.114 Preferred compounds of the formula (1. 114) are the compounds 1. 114-1 to 1. 114- 68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1. 114-1 to 1. 114-68 of Table 1. 114 are thus by the meaning of the respective entries No. 1 to 68 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- 68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 115-1 to I. 115-68 of Table I. 115 are thus by the meaning of the respective entries No. 1 to 68 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- 68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 116-1 to I. 116-68 of Table I. 116 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Preferred compounds of the formula (I. 117) are the compounds I. 117-1 to I. 117- 68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 117-1 to I. 117-68 of Table I. 117 are thus by the meaning of the respective entries No. 1 to 68 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- 68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 118-1 to I. 118-68 of Table I. 118 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1,119 Preferred compounds of the formula (1,119) are the compounds 1,119-1 to 1,119-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1. 119-1 to 1. 119-68 of Table 1. 119 are thus by the meaning of the respective entries No. 1 to 68 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.120-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 120-1 to I. 120-68 of Table I. 120 are thus by the meaning of the respective entries No. 1 to 68 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- 68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 121-1 to I. 121-68 of Table I. 121 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.122 Preferred compounds of the formula (I. 122) are the compounds I. 122-1 to I. 122- 68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 122-1 to I. 122-68 of Table I. 122 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above. (1.123)
  • Table 1.123 Preferred compounds of the formula (1.123) are the compounds 1.123-1 to 1.123-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.123-1 to 1.123-68 of table 1.123 are thus by the meaning of the respective entries No. 1 to
  • Table 1.124 Preferred compounds of the formula (1.124) are the compounds 1.124-1 to 1.124-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.124-1 to 1.124-68 of table 1.124 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • Table 1.125 Preferred compounds of the formula (1.125) are the compounds 1.125-1 to 1.125-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.125-1 to 1.125-68 of table 1.125 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1,126 Preferred compounds of the formula (1,126) are the compounds 1,126-1 to 1,126-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.126-1 to 1.126-68 of table 1.126 are thus by the meaning of the respective entries No. 1 to
  • Table 1,127 Preferred compounds of the formula (1,127) are the compounds 1,127-1 to 1,127-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.127-1 to 1.127-68 of table 1.127 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1.
  • Table 1.128 Preferred compounds of the formula (1.128) are the compounds 1.128-1 to 1.128-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.128-1 to 1.128-68 of table 1.128 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above. (1,129)
  • Table 1,129 Preferred compounds of the formula (1,129) are the compounds 1,129-1 to 1,129-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.129-1 to 1.129-68 of table 1.129 are thus by the meaning of the respective entries No. 1 to
  • Table 1.130 Preferred compounds of the formula (1.130) are the compounds 1.130-1 to 1.130-68, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.130-1 to 1.130-68 of table 1.130 are thus by the meaning of the respective entries No. 1 to 68 defined for Q of Table 1 above.
  • the present invention furthermore relates to the use of one or more
  • herbicide and / or plant growth regulator preferably in crops of useful and / or ornamental plants.
  • the present invention furthermore relates to a process for controlling harmful plants and / or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one those marked as preferred or particularly preferred
  • the present invention also relates to a process for controlling unwanted plants, preferably in crops, characterized in that an effective amount of one or more compounds of the general formula (1) and / or their salts, as defined above, preferably in one of the as preferably or particularly preferably marked Design, in particular one or more compounds of the formulas (1.1) to (1.130) and / or their salts, in each case as defined above, or an agent according to the invention, as defined below, on undesired plants (for example harmful plants such as mono- or dicotyledon weeds or undesirable plants Crops), the seeds of the unwanted plants (ie plant seeds, e.g.
  • the soil in or on which the unwanted plants grow e.g. the soil of cultivated or non-cultivated land
  • the cultivated area ie area on which the unwanted plants will grow
  • 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
  • agents according to the invention e.g. in the pre-sowing (possibly also by incorporation into the soil), pre-emergence and / or post-emergence methods.
  • Some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned by way of example, which can be controlled by the compounds according to the invention without being mentioned a restriction to certain types should be made.
  • one or more compounds of the general formula (1) and / or their salts are preferably used for controlling harmful plants or for regulating growth in crops of useful plants or ornamental plants, the useful plants or ornamental plants in a preferred embodiment being transgenic plants.
  • the compounds of the general formula (I) and / or their salts according to the invention are suitable for combating the following genera of monocotyledonous and dicotyledonous harmful plants:
  • the compounds of the general formula (I) according to the invention are applied to the earth's surface before the germination of the harmful plants (grasses and / or weeds) (pre-emergence method), either the weed or weed seedlings are prevented from emerging completely or these grow up to the cotyledon stage However, they stop growing and eventually die completely after three to four weeks.
  • the compounds of the general formula (1) according to the invention have an excellent herbicidal activity against mono- and dicotyledon weeds
  • 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,
  • the compounds of the general formula (1) according to the invention have excellent properties (depending on their structure and the application rate applied)
  • Phytonutrients and to ease the crop, e.g. by triggering desiccation and stunted growth. Furthermore, they are also suitable for general control and inhibition of undesirable vegetative growth without killing the plants. Inhibiting vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, since, for example, this can reduce or completely prevent stock formation.
  • the active compounds can also be used to control harmful plants in crops of plants modified by genetic engineering or by conventional mutagenesis.
  • the transgenic plants are generally distinguished by special advantageous properties, for example resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties concern e.g. the crop in terms of quantity, quality, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or changed starch quality or those with others
  • transgenic cultures is the use of the compounds according to the invention and / or their salts in economically important transgenic cultures of useful and ornamental plants, e.g. of cereals such as wheat, barley, rye, oats, millet, rice and corn or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.
  • cereals such as wheat, barley, rye, oats, millet, rice and corn or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.
  • the compounds according to the invention can preferably also be used as herbicides
  • Crop crops are used which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
  • the 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 distinguished by special advantageous properties, for example by resistance to them certain pesticides, 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, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or changed starch quality or those with others
  • Other special properties can include tolerance or resistance to abiotic stressors e.g. There is heat, cold, dryness, salt and ultraviolet radiation.
  • cereals such as wheat, barley, rye, oats, triticale, millet, rice, manioc and corn or also crops of sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetables.
  • the compounds of the general formula (I) can preferably be used as herbicides in
  • Crop crops are used which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
  • nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by recombining DNA sequences. With the help of standard procedures e.g. Base exchanges made, partial sequences removed or natural or synthetic sequences added. For connecting the DNA fragments
  • adapters or linkers can be attached to the fragments.
  • DNA molecules can be used that comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules that only comprise parts of the coding sequence, these parts having to be long enough to be in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but which are not completely identical.
  • the synthesized protein When nucleic acid molecules are expressed in plants, the synthesized protein can be located in any compartment of the plant cell. However, in order to achieve localization in a certain compartment, e.g. the coding region is linked to DNA sequences which ensure localization in a specific compartment. Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227). The expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
  • the transgenic plant cells can be regenerated into whole plants using known techniques.
  • the transgenic plants can be any plants
  • the compounds (I) according to the invention can preferably be used in transgenic cultures which are active against growth substances, e.g. Dicamba or against herbicides, the essential
  • Plant enzymes e.g. Inhibit acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydoxyphenyl pyruvate dioxygenases (HPPD), or are resistant to herbicides from the group of sulfonylureas, glyphosate, glufosinate or benzoylisoxazole and analogous active ingredients.
  • ALS Inhibit acetolactate synthases
  • EPSP synthases glutamine synthases
  • HPPD hydoxyphenyl pyruvate dioxygenases
  • the active compounds according to the invention are used in transgenic crops, in addition to the effects on harmful plants which can be observed in other crops, effects often occur which are specific to the application in the respective transgenic culture, for example a changed or specially expanded weed spectrum which can be controlled changed Application rates that can be used for the application, preferably good combinability with the herbicides to which the transgenic culture is resistant, and influencing the growth and yield of the transgenic crop plants.
  • the invention therefore also relates to the use of the compounds of the general formula (I) according to the invention and / or their salts as herbicides for controlling harmful plants in crops of useful or ornamental plants, optionally 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 (1) 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 formula (1) or their salts or an agent according to the invention (as defined below) (in one
  • 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 are 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 is applied.
  • the invention also relates to a herbicidal and / or plant growth-regulating agent, characterized in that the agent
  • (a) contains one or more compounds of the general formula (I) and / or their salts as defined above, preferably in one of those identified as preferred or particularly preferred
  • insecticides acaricides, nematicides, further herbicides (ie those which do not correspond to the general formula (I) defined above), fungicides, safeners, fertilizers and / or further growth regulators, (ii) one or more formulation auxiliaries customary in crop protection.
  • component (i) of an agent according to the invention are preferably selected from the group of substances described in "The Pesticide Manual”, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.
  • a herbicidal or plant growth-regulating agent according to the invention preferably comprises one, two, three or more formulation auxiliaries (ii) customary in crop protection selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusts, at 25 ° C. and 1013 mbar solid carriers, preferably adsorbable, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoams, water, organic solvents, preferably at 25 ° C. and 1013 mbar, organic solvents miscible with water in any ratio.
  • formulation auxiliaries customary in crop protection selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusts, at 25 ° C. and 1013 mbar solid carriers, preferably adsorbable, granulated inert materials, wetting agents, antioxidants, stabilizers
  • the compounds of the general formula (I) according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations.
  • the invention therefore also relates to herbicidal and plant growth-regulating compositions which comprise compounds of the general formula (I) and / or their salts.
  • the compounds of general formula (I) and / or their salts can be formulated in various ways, depending on which biological and / or chemical-physical parameters are specified. Possible formulation options are, for example: wettable powder (WP), water-soluble powder (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions .
  • WP wettable powder
  • SP water-soluble powder
  • EC emulsifiable concentrates
  • EW emulsions
  • sprayable solutions such as oil-in-water and water-in-oil emulsions, sprayable solutions .
  • SC Suspension concentrates
  • CS Capsule suspensions
  • DP dusts
  • pickling agents granules for the litter
  • granules in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations,
  • Microcapsules and waxes are Microcapsules and waxes.
  • Spray powders are preparations which are uniformly dispersible in water 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, dispersing agents), e.g.
  • 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, propylene oxide-ethylene oxide condensation products, alkyl polyether, sorbitan esters such as e.g. Sorbitan fatty acid esters or
  • Polyoxethylene sorbitan esters such as e.g. Polyoxyethylene.
  • 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 used, for example, using stirrers, colloid mills and / or static mixers using aqueous organic ones
  • 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. Also suitable ones
  • Active ingredients are granulated in the manner customary for the production of fertilizer granules - if desired in a mixture with fertilizers.
  • Water-dispersible granules are generally produced using the customary processes, such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations preferably herbicidal or plant growth-regulating agents of the present invention preferably contain a total amount of 0.1 to 99% by weight, preferably 0.5 to 95% by weight, more preferably 1 to 90% by weight, particularly preferably 2 to 80% by weight of active compounds of the general formula (I) and their salts.
  • the active substance concentration in wettable powders is e.g. about 10 to 90 wt .-%, the rest of 100 wt .-% consists of conventional formulation components. In the case of emulsifiable concentrates, the active substance concentration can be about 1 to 90, preferably 5 to 80,% by weight. Powdery
  • Formulations contain 1 to 30% by weight of active ingredient, preferably mostly 5 to 20% by weight of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50% by weight of active ingredient.
  • the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulating aids, fillers, etc. are used.
  • the active ingredient content of the water-dispersible granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active ingredient formulations mentioned may contain the 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.
  • formulation auxiliaries are described, inter alia, in “Chemistry and Technology of Agrochemical Formulations", ed. DA Knowles, Kluwer Academic Publishers (1998).
  • the compounds of general formula (I) or their salts 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.
  • 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,
  • Mixture formulations or in the tank mix 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-hydroxyphenylpyruvate dioxygenase, and , Photosystem I, Photosystem II, protoporphyrinogen oxidase, can be used, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein.
  • Compounds (1) according to the invention of particular interest which contain the compounds (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 herbicide or herbicide safener formulations present in commercially available form are optionally diluted in the customary manner, for example for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water.
  • Preparations in the form of dust, ground granules or granules as well as sprayable solutions are usually no longer diluted with other inert substances before use.
  • the application rate can vary within wide limits.
  • the total amount of compounds of the general formula (1) and their salts is preferably in the range from 0.001 to 10.0 kg / ha, preferably in the range from 0.005 to 5 kg / ha, more preferably in Range from 0.01 to 1.5 kg / ha, particularly preferably in the range from 0.05 to 1 kg / ha. This applies to both pre-emergence and post-emergence applications.
  • Plant growth regulator for example as a straw shortener in crop plants as mentioned above, preferably in cereal plants such as wheat, barley, rye, triticale, millet, rice or corn, the total application rate is preferably in the range from 0.001 to 2 kg / ha, preferably in the range from 0.005 to 1 kg / ha, in particular in the range from 10 to 500 g / ha, very particularly preferably in the range from 20 to 250 g / ha. This applies both to the application in
  • the application as a straw shortener can take place in different stages of the growth of the plants. For example, use after planting at the beginning of the
  • the treatment of the seed which includes the different seed dressing and coating techniques, can also be used.
  • the application rate depends on the individual techniques and can be determined in preliminary tests.
  • compositions according to the invention for example mixture formulations or in a tank mix
  • active substances which are based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate -3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoendesaturase, Photosystem I, Photosystem II or
  • Protoporphyrinogen oxidase are used, such as those e.g. from Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein.
  • Known herbicides or plant growth regulators are mentioned below by way of example, which can be combined with the compounds according to the invention, these active compounds either with their "common name" in the English-language variant according to the International Organization for Standardization (ISO) or with the chemical name or with the code number are designated.
  • herbicidal mixture partners examples include:
  • flucarbazone flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonoglypane, and -methyl-fluorine-cyanogen flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate ammonium, pufosinate ammonium P-ammonium, glufosinate-P-sodium
  • metdicazthiazuron metam, metamifop, metamitron, metazachlor, metazosulfuron,
  • plant growth regulators as possible mixing partners are:
  • Sl d compounds of the triazole carboxylic acid type (Sl d ), preferably compounds such as
  • Fenchlorazole ethyl ester
  • ethyl ester i.e. 1- (2,4-dichlorophenyl) -5-trichloromethyl- (lH) -l, 2,4-triazole-3-carboxylic acid ethyl ester (S1-7), and related compounds as described in EP-A-174562 and EP- A-346620;
  • Sl e compounds of the type of 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid, or of 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (Sl e ), preferably compounds such as
  • R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2)
  • R-28725" (3-dichloroacetyl-2,2, -dimethyl- 1,3-oxazolidine) from Stauffer (S3-3)
  • PPG-1292 N-allyl-N - [(1,3-dioxolan-2-yl) methyl] dichloroacetamide
  • TI-35 (l-dichloroacetyl-azepan) from TRI-Chemical RT (S3-8),
  • RA 2 halogen (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, CF 3; m A 1 or 2;
  • VA is 0, 1, 2 or 3;
  • RB 1 , RB 2 independently of one another hydrogen, (Ci-C 6 ) alkyl, (C3-C6) cycloalkyl, (C3-C 6 ) alkenyl, (C3-C 6 ) alkynyl,
  • RB 3 represents halogen, (Ci-C4) alkyl, (Ci-C4) haloalkyl or (Ci-C4) alkoxy and ms 1 or 2, for example those in which
  • RB 1 cyclopropyl
  • RB 2 hydrogen
  • (RB 3 ) 2-OMe
  • RB 1 cyclopropyl
  • R B 1 ethyl
  • R B 1 isopropyl
  • R B 2 hydrogen
  • (R B 3 ) 5-Cl-2-OMe is (S4-4) and
  • R B 1 isopropyl
  • R B 2 hydrogen
  • (R B 3 ) 2-OMe is (S4-5);
  • Rc 1 , Rc 2 independently of one another hydrogen, (Ci-Cg) alkyl, (C3-Cg) cycloalkyl, (C3-
  • Rc 3 is halogen, (Ci-C i) alkyl, (Ci-C4) alkoxy, CF 3 and m c 1 or 2; for example 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,
  • R D 4 halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, CF 3; m D 1 or 2; RD 5 is hydrogen, (Ci-C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 5 - C 6 ) cycloalkenyl.
  • Carboxylic acid derivatives (S5) e.g.
  • Dihydroxybenzoic acid 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004/084631, WO-A-2005/015994, WO-A-2005/016001.
  • RD 1 is halogen, (Ci-C i) alkyl, (Ci-C i) haloalkyl, (Ci-C i) alkoxy, (Ci-C4) haloalkoxy,
  • R D 2 is hydrogen or (Ci-C i) alkyl
  • R D 3 is hydrogen, (Ci-Csjalkyl, (C 2 -C4) alkenyl, (C 2 -C4) alkynyl, or aryl, where each of the abovementioned C-containing radicals is unsubstituted or by one or more, preferably up to three of the same or various radicals from the group consisting of halogen and alkoxy, or their salts, n D is an integer from 0 to 2.
  • S9 active substances from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g.
  • Y E , Z E independently of one another O or S, he is an integer from 0 to 4,
  • RE 2 (Ci-Ci 6 ) alkyl, (C2-C6) alkenyl, (C3-C6) cycloalkyl, aryl; Benzyl, halobenzyl, RE 3 is hydrogen or (Ci-C 6 ) alkyl.
  • Sl 1 Active substances of the oxyimino compound type (Sl 1), which are known as seed dressings, such as. B.
  • Oxabetrinil ((Z) -l, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (Sl l-l), which is known as a seed dressing safener for millet against damage to metolachlor,
  • Seed pickle safener is known for millet against damage from metolachlor.
  • Naphthalic anhydride (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed dressing safener for maize against damage from thiocarbamate herbicides,
  • Cyanamide which is known as a safener for corn against damage to imidazolinones
  • MG 191 (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for corn,
  • Mephenate (4-chlorophenyl methyl carbamate) (S13-9).
  • Active ingredients which, in addition to a herbicidal action against harmful plants, also have safener action on crop plants such as rice, such as, for. B.
  • COD l-bromo-4- (chloromethylsulfonyl) benzene
  • RH 1 represents a (Ci-C 6 ) haloalkyl radical and R H 2 represents hydrogen or halogen and
  • R H 3 , R H 4 independently of one another are hydrogen, (Ci-Ci 6 ) alkyl, (C2-Ci6) alkenyl or
  • (C 2 -Ci 6 ) alkynyl each of the latter 3 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, (Ci-C i) alkoxy, (Ci-C i) haloalkoxy, (Ci C ij alkylthio, (Ci-C ij alkylamino, di [(Ci-C4) alkyl] amino, [(Ci-C i) alkoxy] carbonyl, [(Ci-C t j haloalkoxyj-carbonyl, (C3-C6) cycloalkyl, which is unsubstituted or substituted, phenyl which is unsubstituted or substituted and heterocyclyl which is unsubstituted or substituted, or (C3-C6) cycloalkyl, (C4-C6) cycloalkenyl, (C3-C6) cycloalkyl
  • R H 3 is (Ci-C 4 ) alkoxy, (C2-C 4 ) alkenyloxy, (C2-C6) alkynyloxy or (C2-C 4 ) haloalkoxy and R H 4 is hydrogen or (Ci-C 4 ) alkyl or
  • R H 3 and R H 4 together with the directly bound N atom form a four- to eight-membered group
  • heterocyclic ring which, in addition to the N atom, 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 C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkoxy and (Ci-C 4 ) alkylthio is substituted.
  • Preferred safeners in combination with the compounds according to the invention of the formula (I) and / or their salts, in particular with the compounds of the formulas (1.1) to (1.130) and / or their salts are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole ethyl ester, isoxadifene -ethyl, mefenpyr-diethyl, fenclorim, cumyluron, S4-1 and S4-5, and particularly preferred safeners are: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.
  • Biological examples are:
  • the amount of water applied is equivalent to 2200 liters per hectare. After 9 to 12 days
  • Seeds of monocotyledonous or dicotyledonous weeds and crops were placed in plastic or organic plant pots and covered with soil.
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) were then applied to the surface of the covering earth as an aqueous suspension or emulsion with the addition of 0.5% additive with a water application rate of the equivalent of 600 l / ha.
  • WP wettable powders
  • EC emulsion concentrates
  • the following tablets B1 to B5 show the effects of selected compounds of the general formula (I) according to Tables 1.1 to 1.130 on various harmful plants and an application rate corresponding to 320 g / ha or less, which were obtained in accordance with the aforementioned test instructions.
  • Compounds 1.2-8, 1.2-1 and 1.4-8 and other compounds of the general formula (I) according to the invention have a good herbicidal activity against harmful plants, e.g. B. against harmful plants such as Abutilon theophrasti, Alopecurus myosuroides, Setaria viridis, Avena fatua, Amaranthus retroflexus, Polygonum convolvulus and Viola tricolor at a rate of 320 g of active ingredient per hectare.
  • harmful plants such as Abutilon theophrasti, Alopecurus myosuroides, Setaria viridis, Avena fatua, Amaranthus retroflexus, Polygonum convolvulus and Viola tricolor at a rate of 320 g of active ingredient per hectare.

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

Abstract

La présente invention concerne des thiazolylpyrrolones 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/EP2019/066198 2018-06-25 2019-06-19 Thiazolylpyrrolones substituées, leurs sels et leur utilisation comme agents herbicides WO2020002090A1 (fr)

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