Substituted 2-heteroarylaminobenzenes and their salts and their use as herbicides

Description

[0001] The invention relates to the technical field of plant protection products, in particular herbicides for the selective control of weeds and grasses in crop crops.

[0002] This invention specifically relates to substituted 2-heteroarylaminobenzenes and their salts, processes for their production and their use as herbicides.

[0003] Existing plant protection products for the selective control of weeds in crops, or active ingredients for controlling unwanted plant growth, sometimes have disadvantages in their application. These disadvantages include (a) no or insufficient herbicidal activity against certain weeds, (b) too narrow a spectrum of weeds that can be controlled with a single active ingredient, (c) insufficient selectivity in crops, and / or (d) an unfavorable toxicological profile. Furthermore, some active ingredients that can be used as plant growth regulators in certain crops lead to undesirably reduced yields in other crops or are incompatible with the crop or only compatible within a narrow application rate range.Some of the known active ingredients cannot be produced economically on an industrial scale due to the difficulty in obtaining precursors and reagents, or they possess insufficient chemical stability. For other active ingredients, their efficacy depends too heavily on environmental conditions such as weather and soil conditions.

[0004] The herbicidal effect of these known compounds, especially at low application rates, and their compatibility with cultivated plants still need improvement.

[0005] Heteroaryloxybenzenes were described in AU535637, EP8192, EP61913, JP61236766 and WO2016 / 010731, and were attributed with herbicidal activity.

[0006] Substituted 2-heteroarylaminobenzenes or their salts as herbicidal agents, on the other hand, have not yet been described.

[0007] Surprisingly, it has now been found that certain substituted 2-heteroarylaminobenzenes or their salts are particularly well suited as herbicidal agents.

[0008] The present invention relates to substituted 2-heteroarylaminobenzenes of general formula (I) or their salts. wherein A stands for nitrogen or -CX-, X stands for hydrogen or halogen, R 1< stands for an optionally substituted aryl or heteroaryl, wherein each ring or ring system is optionally substituted with up to 5 substituents, independently selected from the group R 5<, R 2< independently stands for halogen, cyano, nitro, formyl, formamide, (C 1-C 8 )-alkyl, (C 1-C 8 )-haloalkyl, (C 2-C 8 )-alkenyl, (C 2-C 8 )-alkynyl, (C 2-C 8 )-haloalkenyl, (C 2-C 8 )-haloalkynyl, (C 3-C 8 )-cycloalkyl, (C 3-C 6 )-halocycloalkyl, (C 3-C 6 )-cycloalkyl-(C 1-C 6 )-alkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkoxy-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkylthio-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkylsulfinyl-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkylsulfonyl-(C 1 -C 4 )-alkyl, (C 1 -C 8 )-alkylcarbonyl, (C 1 -C 8 )-haloalkylcarbonyl, (C 3 -C 8 )-cycloalkylcarbonyl, carboxyl, (C 1 -C 8 )-Alkoxycarbonyl, (C 1 -C 8 )-Haloalkoxycarbonyl, (C 3 -C 8 )-Cycloalkoxycarbonyl,Carbamoyl, (C 2 -C 8 )-Alkylaminocarbonyl, (C 2 -C 10 )-Dialkylaminocarbonyl, (C 3 -C 10 )-Cycloalkylaminocarbonyl, (C 1 -C 4 )-Alkoxycarbonyl-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-Haloalkoxycarbonyl-(C 1 -C 4 )-alkyl, Carboxy-(C 1 -C 4 )-alkyl, Hydroxy, NR 4< R 6< , (C 1 -C 8 )-Alkoxy, (C 1 -C 8 )-Haloalkoxy, (C 1 -C 8 )-Alkylthio, (C 1 -C 8 )-Haloalkylthio, (C 3 -C 8 )-Cycloalkylthio, (C 1 -C 4 )-Alkoxy-(C 1 -C 4 )-alkylthio, (C 1 -C 8 )-Alkylsulfinyl, (C 1 -C 8 )-Haloalkylsulfinyl, (C 3 -C 8 )-Cycloalkylsulfinyl, (C 1 -C 4 )-Alkoxy-(C 1 -C 4 )-alkylsulfinyl, (C 1 -C 8 )-Alkylsulfonyl, (C 1 -C 8 )-Haloalkylsulfonyl, (C 3 -C 8 )-Cycloalkylsulfonyl, (C 1 -C 4 )-Alkoxy-(C 1 -C 4 )-alkylsulfonyl, (C 1 -C 8 )-Alkylaminosulfonyl, (C 2 -C 8 )-Dialkylaminosulfonyl oder (C 3 -C 8 )-Trialkylsilyl steht, mist gleich 0, 1, 2, oder 3, R 3< für Wasserstoff, Halogen, Cyano, Nitro, (C 1 -C 8 )-Alkyl, (C 1 -C 8 )-Haloalkyl, (C 2 -C 4 )-Alkenyl, (C 2 -C 4 )-Alkinyl, (C 3 -C 6 )-Cycloalkyl,(C 3 -C 6 )-Cycloalkyl-(C 1 -C 6 )-alkyl, (C 1 -C 8 )-Alkoxy, (C 1 -C 8 )-Haloalkoxy, (C 1 -C 8 )-Alkylthio, (C 1 -C 8 )-Haloalkylthio, (C 1 -C 8 )-Alkylsulfinyl, (C 1 -C 8 )-Haloalkylsulfinyl, (C 1 -C 8 )-Alkylsulfonyl, (C 1 -C 8 )-Haloalkylsulfonyl steht, R 4< , R 6< unabhängig voneinander für Wasserstoff, (C 1 -C 8 )-Alkyl, (C 1 -C 8 )-Haloalkyl, Aryl-(C 1 -C 6 )-alkyl, Heteroaryl-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-Cycloalkyl, (C 3 -C 6 )-Cycloalkyl-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-Halocycloalkyl, (C 3 -C 6 )-Halocycloalkyl-(C 1 -C 4 )-alkyl, (C 2 -C 8 )-Alkenyl, (C 2 -C 8 )-Alkinyl, (C 1 -C 4 )-Alkoxy-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-Haloalkoxy-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-Alkylthio-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-Alkylsulfinyl-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-Alkylsulfonyl-(C 1 -C 4 )-alkyl, (C 1 -C 8 )-Alkylcarbonyl, (C 1 -C 8 )-Haloalkylcarbonyl, (C 3 -C 8 )-Cycloalkylcarbonyl, Formyl, (C 1 -C 8 )-Alkoxycarbonyl, (C 1 -C 8 )-Haloalkoxycarbonyl, (C 3 -C 8 )-Cycloalkoxycarbonyl,(C 1 -C 8 )-Alkylaminocarbonyl, (C 2 -C 8 )-Dialkylaminocarbonyl, (C 3 -C 8 )-Cycloalkylaminocarbonyl steht, und R 5< für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (C 1 -C 8 )-Alkyl, (C 1 -C 8 )-Haloalkyl, (C 2 -C 8 )-Alkenyl, (C 2 -C 8 )-Alkinyl, (C 2 -C 8 )-Haloalkenyl, (C 2 -C 8 )-Haloalkinyl, (C 1 -C 4 )-Alkoxy-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-Haloalkoxy-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-Alkylthio-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-Alkylsulfinyl-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-Alkylsulfonyl-(C 1 -C 4 )-alkyl, (C 1 -C 8 )-Alkylcarbonyl, (C 1 -C 8 )-Haloalkylcarbonyl, (C 3 -C 8 )-Cycloalkylcarbonyl, Carboxyl, (C 1 -C 8 )-Alkoxycarbonyl, (C 1 -C 8 )- Haloalkoxycarbonyl, (C 3 -C 8 )-Cycloalkoxycarbonyl, (C 1 -C 8 )-Alkylaminocarbonyl, (C 2 -C 8 )-Dialkylaminocarbonyl, (C 3 -C 8 )-Cycloalkylaminocarbonyl, Hydroxy, (C 1 -C 8 )-Alkoxy, (C 1 -C 8 )-Haloalkoxy, (C 1 -C 8 )-Alkylthio, (C 1 -C 8 )-Haloalkylthio, (C 3 -C 8 )-Cycloalkylthio, (C 1 -C 8 )-Alkylsulfinyl, (C 1 -C 8 )-Haloalkylsulfinyl,(C 3 -C 8 )-cycloalkylsulfinyl, (C 1 -C 8 )-alkylsulfonyl, (C 1 -C 8 )-haloalkylsulfonyl, (C 3 -C 8 )-cycloalkylsulfonyl, (C 1 -C 8 )-alkylaminosulfonyl, (C 2 -C 8 )-Dialkylaminosulfonyl or (C 3 -C 8 )-Trialkylsilyl, , except for the following compounds: 2-(2-phenoxyphenylamino)pyridine 5-bromo-2-(2-phenoxyphenylamino)pyridine 5-chloro-2-(2-phenoxyphenylamino)pyridine 2-(2-phenoxyphenylamino)pyrimidine 5-bromo-2-(2-phenoxyphenylamino)pyrimidine 5-Iodo-2-(2-phenoxyphenylamino)pyrimidine 2-(2-(2-pyridyloxy)phenylamino)pyridine.

[0009] The compounds of general formula (I) can be modified by the addition of a suitable inorganic or organic acid, such as mineral acids, HCl, HBr, H₂SO₄, H₃PO₄, or HNO₃, or organic acids such as carboxylic acids (formic, acetic, propionic, oxalic, lactic, or salicylic acid) or sulfonic acids (p-toluenesulfonic acid) react with a basic group, such as an amino, alkylamino, dialkylamino, piperidino, morpholino, or pyridino, to form salts. These salts then contain the conjugate base of the acid as an anion. Suitable substituents present in deprotonated form, such as sulfonic acids, certain sulfonamides, or carboxylic acids, can form internal salts with their own protonatable groups, such as amino groups. Salt formation can also occur through the action of a base on compounds of the general formula (I).Suitable bases are organic amines, such as trialkylamines, morpholine, piperidine, and pyridine, as well as ammonium, alkali, or alkaline earth metal hydroxides, carbonates, and hydrogen carbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate, and sodium and potassium hydrogen carbonate. These salts are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, such as 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, such as with cations of the formula [NR a< R b< R c< R d< ] +< , wherein R a< to R d< each independently represent an organic residue, in particular alkyl, aryl, arylalkyl, or alkylaryl. Alkylsulfonium and alkylsulfoxonium salts, such as (C 1 -C 4 )-trialkylsulfonium and (C 1 -C 4 )-trialkylsulfoxonium salts, are also suitable.

[0010] The substituted 2-heteroarylaminobenzenes of general formula (I) according to the invention may, depending on external conditions such as pH, solvent and temperature, possibly exist in different tautomeric structures, all of which are encompassed by general formula (I).

[0011] In the following, the compounds of formula (I) and their salts used according to the invention are referred to as "compounds of general formula (I)".

[0012] Particularly preferred subject matter of the invention is compounds of the general formula (I), wherein A stands for nitrogen or -CX-, X stands for hydrogen or halogen, R 1< stands for an optionally substituted aryl or heteroaryl, wherein each ring or ring system is optionally substituted with up to 5 substituents, independently selected from the group R 5<, R 2< independently stands for halogen, cyano, nitro, formyl, formamide, (C 1-C 4 )-alkyl, (C 1-C 4 )-haloalkyl, (C 2-C 4 )-alkenyl, (C 2-C 4 )-alkynyl, (C 2-C 4 )-haloalkenyl, (C 3-C 8 )-cycloalkyl, (C 1-C 4 )-alkoxy-(C 1-C 4 )-alkyl, (C 1-C 4 )-haloalkoxy-(C 1-C 4 )-alkyl, (C 1-C 4 )-alkylcarbonyl, (C 1 -C 4 )-haloalkylcarbonyl, carboxyl, (C 1 -C 4 )-alkoxycarbonyl, (C 1 -C 4 )-haloalkoxycarbonyl, (C 3 -C 6 )-cycloalkoxycarbonyl, carbamoyl, (C 2 -C 4 )-alkylaminocarbonyl, (C 2 -C 6 )-Dialkylaminocarbonyl, (C 1 -C 4 )-alkoxycarbonyl-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkoxycarbonyl-(C 1 -C 4 )-alkyl, carboxy-(C 1 -C 4 )-alkyl, hydroxy, NR 4< R 6< , (C 1 -C 4 )-alkoxy,(C 1 -C 4 )-Haloalkoxy, (C 1 -C 4 )-Alkylthio, (C 1 -C 4 )-Alkylsulfinyl, (C 1 -C 4 )-Alkylsulfonyl, (C 1 -C 4 )-Alkylaminosulfonyl, (C 2 -C 6 )-Dialkylaminosulfonyl oder (C 3 -C 6 )-Trialkylsilyl steht, mist gleich 0, 1, 2, oder 3, R 3< für Wasserstoff, Halogen, Cyano, Nitro, (C 1 -C 4 )-Alkyl, (C 2 -C 4 )-Alkenyl, (C 2 -C 4 )-Alkinyl, (C 1 -C 4 )-Haloalkyl, (C 3 -C 6 )-Cycloalkyl, (C 3 -C 6 )-Cycloalkylmethyl, (C 1 -C 4 )-Alkoxy, (C 1 -C 4 )-Haloalkoxy, (C 1 -C 4 )-Alkylthio, (C 1 -C 4 )-Haloalkylthio, (C 1 -C 4 )-Alkylsulfinyl, (C 1 -C 4 )-Haloalkylsulfinyl, (C 1 -C 4 )-Alkylsulfonyl, (C 1 -C 4 )-Haloalkylsulfonyl steht, R 4< , R 6< unabhängig voneinander für Wasserstoff, (C 1 -C 4 )-Alkyl, (C 1 -C 4 )-Haloalkyl, Aryl-(C 1 -C 4 )-alkyl, Heteroaryl-(C 1 -C 4 )-alkyl, (C 2 -C 4 )-Alkenyl, (C 2 -C 4 )-Alkinyl, (C 1 -C 4 )-Alkylcarbonyl, Formyl oder (C 1 -C 4 )-Alkoxycarbonyl steht, und R 5< für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (C 1 -C 4 )-Alkyl, (C 1 -C 4 )-Haloalkyl,(C 2 -C 4 )-Alkenyl, (C 2 -C 4 )-Alkinyl, (C 2 -C 4 )-Haloalkenyl, (C 2 -C 4 )-Haloalkinyl, (C 1 -C 4 )-Alkoxy-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-Haloalkoxy-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-Alkylcarbonyl, (C 1 -C 4 )-Haloalkylcarbonyl, Carboxyl, (C 1 -C 4 )-Alkoxycarbonyl, (C 1 -C 4 )- Haloalkoxycarbonyl, (C 3 -C 6 )-Cycloalkoxycarbonyl, (C 1 -C 4 )-Alkylaminocarbonyl, (C 2 -C 6 )-Dialkylaminocarbonyl, (C 3 -C 6 )-Cycloalkylaminocarbonyl, Hydroxy, (C 1 -C 4 )-Alkoxy, (C 1 -C 4 )-Haloalkoxy, (C 1 -C 4 )-Alkylthio, (C 1 -C 4 )-Haloalkylthio, (C 1 -C 4 )-Alkylsulfinyl, (C 1 -C 4 )-Haloalkylsulfinyl, (C 1 -C 4 )-Alkylsulfonyl, (C 1 -C 4 )-Haloalkylsulfonyl, (C 1 -C 4 )-Alkylaminosulfonyl, (C 2 -C 6 )-Dialkylaminosulfonyl oder (C 3 -C 6 )-Trialkylsilyl steht, , except for the following compounds: 2-(2-phenoxyphenylamino)pyridine 5-bromo-2-(2-phenoxyphenylamino)pyridine 5-chloro-2-(2-phenoxyphenylamino)pyridine 2-(2-phenoxyphenylamino)pyrimidine 5-bromo-2-(2-phenoxyphenylamino)pyrimidine 5-Iodo-2-(2-phenoxyphenylamino)pyrimidine 2-(2-(2-pyridyloxy)phenylamino)pyridine.

[0013] A particularly preferred subject matter of the invention is compounds of the general formula (I), wherein A stands for nitrogen or -CX-, X stands for hydrogen, fluorine or chlorine, R 1< stands for an optionally substituted phenyl, pyridyl or pyrimidyl, wherein each ring or ring system is optionally substituted with up to 5 substituents, independently selected from the group R 5< , R 2< independently stands for halogen, cyano, nitro, (C 1-C 4 )-alkyl, (C 1-C 4 )-haloalkyl, NR 4< R 6< , (C 1-C 4 )-alkoxycarbonyl, (C 1-C 4 )-alkylthio or (C 1-C 4 )-alkoxy, measured as 0, 1, 2, or 3, R 3< stands for hydrogen, halogen, cyano, nitro, (C 1-C 4 )-alkyl, (C 1-C 4 )-haloalkyl, (C 2-C 4 )-Alkenyl, (C 2 -C 4 )-Alkynyl, (C 2 -C 4 )-Haloalkenyl, (C 2 -C 4 )-Haloalkynyl, Cyclpropyl, Cyclopropylmethyl, (C 1 -C 4 )-Alkoxy, (C 1 -C 4 )-Haloalkoxy, (C 1 -C 4 )-Alkylthio or (C 1 -C 4 )-Haloalkylthio, R 4< , R 6< independently of each other represents hydrogen, (C 1 -C 4 )-Alkyl, (C 1 -C 4 )-Alkylcarbonyl or (C 1 -C 4 )-Alkoxycarbonyl,and R 5< stands for hydrogen, halogen, cyano, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkoxy or (C 1 -C 4 )-haloalkoxy, , except for the following compounds: 2-(2-phenoxyphenylamino)pyridine 5-bromo-2-(2-phenoxyphenylamino)pyridine 5-chloro-2-(2-phenoxyphenylamino)pyridine 2-(2-phenoxyphenylamino)pyrimidine 5-bromo-2-(2-phenoxyphenylamino)pyrimidine 5-Iodo-2-(2-phenoxyphenylamino)pyrimidine 2-(2-(2-pyridyloxy)phenylamino)pyridine.

[0014] Another preferred subject matter of the invention is compounds of the general formula (I), wherein A stands for nitrogen or -CX-, X stands for hydrogen, fluorine or chlorine, R 1< stands for an optionally substituted phenyl, pyridyl or pyrimidyl, wherein each ring or ring system is optionally substituted with up to 5 substituents, independently selected from the group R 5<, R 2< independently stands for halogen, cyano, nitro, (C 1-C 4 )-alkyl, (C 1-C 4 )-haloalkyl, (C 1-C 4 )-alkoxycarbonyl, (C 1-C 4 )-alkylthio, NR 4< R 6< or (C 1-C 4 )-alkoxy, equal to 0, 1, 2, or 3, R 3< stands for hydrogen, halogen, cyano, (C 1-C 4 )-alkyl, (C 1-C 4 )-haloalkyl, cyclopropyl, cyclopropylmethyl, (C 1 -C 4 )-Alkoxy, (C 1 -C 4 )-Haloalkoxy, (C 1 -C 4 )-Alkylthio or (C 1 -C 4 )-Haloalkylthio, R 4< , R 6< independently stand for hydrogen or methyl, and R 5< stand for hydrogen, halogen, cyano, (C 1 -C 4 )-Alkyl, (C 1 -C 4 )-Haloalkyl, (C 1 -C 4 )-Alkylthio, (C 1 -C 4 )-Alkoxy or (C 1 -C 4 )-Haloalkoxy, except for the following compounds: 2-(2-phenoxyphenylamino)pyridine 5-bromo-2-(2-phenoxyphenylamino)pyridine 5-chloro-2-(2-phenoxyphenylamino)pyridine 2-(2-phenoxyphenylamino)pyrimidine 5-bromo-2-(2-phenoxyphenylamino)pyrimidine 5-Iodo-2-(2-phenoxyphenylamino)pyrimidine 2-(2-(2-pyridyloxy)phenylamino)pyridine.

[0015] Another preferred subject matter of the invention is compounds of the general formula (I), wherein A stands for nitrogen or -CX-, X for hydrogen, fluorine or chlorine, R 1< stands for a possibly substituted phenyl, pyridyl or pyrimidyl, each ring optionally substituted with up to 5 substituents independently selected from the group R 5<, R 2< independently stands for fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, methylthio or amino, equal to 0, 1, 2, or 3, R 3< stands for hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy, methylthio or trifluoromethylthio, and R 5< stands for hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy or trifluoromethoxy. except for the following compounds: 2-(2-phenoxyphenylamino)pyridine 5-bromo-2-(2-phenoxyphenylamino)pyridine 5-chloro-2-(2-phenoxyphenylamino)pyridine 2-(2-phenoxyphenylamino)pyrimidine 5-bromo-2-(2-phenoxyphenylamino)pyrimidine 5-Iodo-2-(2-phenoxyphenylamino)pyrimidine 2-(2-(2-pyridyloxy)phenylamino)pyridine.

[0016] The general residue definitions listed above, or those listed in preferred areas, apply both to the final products of the general formula (I) and, correspondingly, to the starting materials or intermediates required for their production. These residue definitions can be combined with each other as desired, including between the specified preferred areas.

[0017] Especially for reasons of higher herbicidal activity, better selectivity and / or better manufacturability, compounds of the general formula (I) mentioned above or their salts or their use according to the invention are of particular interest, wherein individual residues have one of the preferred meanings already mentioned or mentioned below, or in particular those in which one or more of the preferred meanings already mentioned or mentioned below occur in combination.

[0018] With regard to the compounds according to the invention, the designations used above and below are explained. These are familiar to those skilled in the art and have, in particular, the meanings explained below: Unless otherwise defined, the designation of chemical groups generally assumes that the connection to the framework or the rest of the molecule is effected via the last-mentioned structural element of the chemical group in question, i.e., in the case of (C 2 -C 8 )-alkenyloxy via the oxygen atom, and in the case of heteroaryl-(C 1 -C 6 )-alkyl or (C 1 -C 4 )-alkylthio-(C 1 -C 4 )-alkyl, in each case via the carbon atom of the alkyl group.

[0019] Erfindungsgemäß steht "Alkylsulfonyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes Alkylsulfonyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 Kohlenstoffatomen, wie (C 1 -C 6 )-Alkylsulfonyl wie Methylsulfonyl, Ethylsulfonyl, Propylsulfonyl, 1-Methylethylsulfonyl, Butylsulfonyl, 1-Methylpropylsulfonyl, 2-Methylpropylsulfonyl, 1,1-Dimethylethylsulfonyl, Pentylsulfonyl, 1-Methylbutylsulfonyl, 2-Methylbutylsulfonyl, 3-Methylbutylsulfonyl, 1,1-Dimethylpropylsulfonyl, 1,2-Dimethylpropylsulfonyl, 2,2-Dimethylpropylsulfonyl, 1-Ethylpropylsulfonyl, Hexylsulfonyl, 1-Methylpentylsulfonyl, 2-Methylpentylsulfonyl, 3-Methylpentylsulfonyl, 4-Methylpentylsulfonyl, 1,1-Dimethylbutylsulfonyl, 1,2-Dimethylbutylsulfonyl, 1,3-Dimethylbutylsulfonyl, 2,2-Dimethylbutylsulfonyl, 2,3-Dimethylbutylsulfonyl, 3,3-Dimethylbutylsulfonyl, 1-Ethylbutylsulfonyl, 2-Ethylbutylsulfonyl, 1,1,2-Trimethylpropylsulfonyl, 1,2,2-Trimethylpropylsulfonyl,1-Ethyl-1-methylpropylsulfonyl und 1-Ethyl-2-methylpropylsulfonyl.,

[0020] According to the invention, "alkylthio" – either alone or as part of a chemical group – represents straight-chain or branched S-alkyl, preferably with 1 to 8, or with 1 to 6 carbon atoms, such as (C1-C10), (C1-C6) or (C1-C4)-alkylthio, such as (C1-C6)-alkylthio, methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio. 3-Methylpentylthio, 4-Methylpentylthio, 1,1-Dimethylbutylthio, 1,2-Dimethylbutylthio, 1,3-Dimethylbutylthio, 2,2-Dimethylbutylthio, 2,3-Dimethylbutylthio, 3,3-Dimethylbutylthio, 1-Ethylbutylthio, 2-Ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio.

[0021] "Alkylsulfinyl (Alkyl-S(=O)-)", soweit nicht an anderer Stelle anders definiert steht erfindungsgemäß für Alkylreste, die über -S(=O)- an das Gerüst gebunden sind, wie (C 1 -C 10 )-, (C 1 -C 6 )- oder (C 1 -C 4 )-Alkylsulfinyl, wie (C 1 -C 6 )-Alkylsulfinyl wie Methylsulfinyl, Ethylsulfinyl, Propylsulfinyl, 1-Methylethylsulfinyl, Butylsulfinyl, 1-Methylpropylsulfinyl, 2-Methylpropylsulfinyl, 1,1-Dimethylethylsulfinyl, Pentylsulfinyl, 1-Methylbutylsulfinyl, 2-Methylbutylsulfinyl, 3-Methylbutylsulfinyl, 1,1-Dimethylpropylsulfinyl, 1,2-Dimethylpropylsulfinyl, 2,2-Dimethylpropylsulfinyl, 1-Ethylpropylsulfinyl, Hexylsulfinyl, 1-Methylpentylsulfinyl, 2-Methylpentylsulfinyl, 3-Methylpentylsulfinyl, 4-Methylpentylsulfinyl, 1,1-Dimethylbutylsulfinyl, 1,2-Dimethylbutylsulfinyl, 1,3-Dimethylbutylsulfinyl, 2,2-Dimethylbutylsulfinyl, 2,3-Dimethylbutylsulfinyl, 3,3-Dimethylbutylsulfinyl, 1-Ethylbutylsulfinyl, 2-Ethylbutylsulfinyl, 1,1,2-Trimethylpropylsulfinyl, 1,2,2-Trimethylpropylsulfinyl,1-Ethyl-1-methylpropylsulfinyl und 1-Ethyl-2-methylpropylsulfinyl.,

[0022] "Alkoxy" means an alkyl radical bonded via an oxygen atom, such as (C 1 -C 6 )-alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-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, 1,1-Dimethylbutoxy, 1,2-Dimethylbutoxy, 1,3-Dimethylbutoxy, 2,2-Dimethylbutoxy, 2,3-Dimethylbutoxy, 3,3-Dimethylbutoxy, 1-Ethylbutoxy, 2-Ethylbutoxy, 1,1,2-Trimethylpropoxy, 1,2,2-Trimethylpropoxy, 1-Ethyl-1-methylpropoxy, and 1-Ethyl-2-methylpropoxy. Alkenyloxy refers to an alkenyl group bonded via an oxygen atom, while alkynyloxy refers to an alkynyl group bonded via an oxygen atom, such as (C₂-C₁₀), (C₂-C₆), or (C₂-C₄)-alkenoxy or (C₃-C₁₀), respectively.

[0023] Unless otherwise defined elsewhere, "alkylcarbonyl" (alkyl-C(=O)-) according to the invention refers to alkyl groups that are bonded to the framework via -C(=O)-, such as (C 1 -C 10 )-, (C 1 -C 6 )- or (C 1 -C 4 )-alkylcarbonyl. The number of carbon atoms refers to the alkyl group within the alkylcarbonyl group.

[0024] "Alkoxycarbonyl (alkyl-OC(=O)-)", unless otherwise defined elsewhere: alkyl groups bonded to the skeleton via -OC(=O)-, such as (C1-C10)-, (C1-C6)-, or (C1-C4)-alkoxycarbonyl. The number of carbon atoms refers to the alkyl group within the alkoxycarbonyl group. Similarly, unless otherwise defined elsewhere, "alkenyloxycarbonyl" and "alkynyloxycarbonyl" are, according to the invention, alkenyl and alkynyl residues, respectively, that are bonded to the framework via -OC(=O)-, such as (C₂-C₁₀), (C₂-C₆), or (C₂-C₄)-alkenyloxycarbonyl or (C₃-C₁₀), respectively. The number of carbon atoms refers to the alkenyl or alkynyl residue within the alkene or alkynyloxycarbonyl group.

[0025] The term "aryl" means an optionally substituted mono-, bi- or polycyclic aromatic system with preferably 6 to 14, in particular 6 to 10 ring carbon atoms, phenyl, naphthyl, anthryl, phenanthrenyl, preferably phenyl.

[0026] If a basic field is substituted "by one or more residues" from an enumeration of residues (= group) or a generically defined group of residues, this in each case includes the simultaneous substitution by several identical and / or structurally different residues.

[0027] According to the invention, the term "heteroaryl" refers to heteroaromatic compounds, i.e., fully unsaturated aromatic heterocyclic compounds, preferably 5- to 7-membered rings with 1 to 4, preferably 1 or 2 identical or different heteroatoms, preferably O, S, or N. Heteroaryls according to the invention are 1H-pyrrol-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl; furan-2-yl; furan-3-yl; thien-2-yl; thien-3-yl; 1H-imidazol-1-yl; 1H-imidazol-2-yl; 1H-imidazol-4-yl; 1H-imidazol-5-yl; 1H-pyrazol-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1H-pyrazol-5-yl, 1H-1,2,3-triazol-1-yl, 1H-1,2,3-triazol-4-yl, 1H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1,2,4-triazol-1-yl, 1H-1,2,4-triazol-3-yl, 4H-1,2,4-triazol-4-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,5-oxadiazol-3-yl, Azepinyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl, pyrimidin-4-yl,Pyrimidin-5-yl, Pyridazin-3-yl, Pyridazin-4-yl, 1,3,5-Triazin-2-yl, 1,2,4-Triazin-3-yl, 1,2,4-Triazin-5-yl, 1,2,4-Triazin-6-yl, 1,2,3-Triazin-4-yl, 1,2,3-Triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 1,3-oxazol-2-yl, 1,3-oxazol-4-yl, 1,3-oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,3-Thiazol-2-yl, 1,3-Thiazol-4-yl, 1,3-Thiazol-5-yl, oxepinyl, thiepinyl, 1,2,4-triazolonyl and 1,2,4-diazepinyl, 2H-1,2,3,4-tetrazole-5-yl, 1H-1,2,3,4-tetrazole-5-yl, 1,2,3,4-oxatriazol-5-yl, 1,2,3,4-thiatriazol-5-yl, 1,2,3,5-oxatriazol-4-yl, 1,2,3,5-thiatriazol-4-yl. The heteroaryl groups according to the invention can further be substituted with one or more identical or different substituents. If two adjacent carbon atoms are part of another aromatic ring, then the systems are fused heteroaromatic.wie benzokondensierte oder mehrfach annellierte Heteroaromaten. Bevorzugt sind Chinoline (z. B. Chinolin-2-yl, Chinolin-3-yl, Chinolin-4-yl, Chinolin-5-yl, Chinolin-6-yl, Chinolin-7-yl, Chinolin-8-yl); Isochinoline (z. B. Isochinolin-1-yl, Isochinolin-3-yl, Isochinolin-4-yl, Isochinolin-5-yl, Isochinolin-6-yl, Isochinolin-7-yl, Isochinolin-8-yl); Chinoxalin; Chinazolin; Cinnolin; 1,5-Naphthyridin; 1,6-Naphthyridin; 1,7-Naphthyridin; 1,8-Naphthyridin; 2,6-Naphthyridin; 2,7-Naphthyridin; Phthalazin; Pyridopyrazine; Pyridopyrimidine; Pyridopyridazine; Pteridine; Pyrimidopyrimidine. Heteroaryl sind auch 5- oder 6-gliedrige benzokondensierte Ringe aus der Gruppe 1H-Indol-1-yl, 1H-Indol-2-yl, 1H-Indol-3-yl, 1H-Indol-4-yl, 1H-Indol-5-yl, 1H-Indol-6-yl, 1H-Indol-7-yl, 1-Benzofuran-2-yl, 1-Benzofuran-3-yl, 1-Benzofuran-4-yl, 1-Benzofuran-5-yl, 1-Benzofuran-6-yl, 1-Benzofuran-7-yl, 1-Benzothiophen-2-yl, 1-Benzothiophen-3-yl, 1-Benzothiophen-4-yl, 1-Benzothiophen-5-yl, 1-Benzothiophen-6-yl,1-Benzothiophen-7-yl, 1H-Indazol-1-yl, 1H-Indazol-3-yl, 1H-Indazol-4-yl, 1H-Indazol-5-yl, 1H-Indazol-6-yl, 1H-Indazol-7-yl, 2H-Indazol-2-yl, 2H-Indazol-3-yl, 2H-Indazol-4-yl, 2H-Indazol-5-yl, 2H-Indazol-6-yl, 2H-Indazol-7-yl, 2H-Isoindol-2-yl, 2H-Isoindol-1-yl, 2H-Isoindol-3-yl, 2H-Isoindol-4-yl, 2H-Isoindol-5-yl, 2H-Isoindol-6-yl; 2H-Isoindol-7-yl, 1H-Benzimidazol-1-yl, 1H-Benzimidazol-2-yl, 1H-Benzimidazol-4-yl, 1H-Benzimidazol-5-yl, 1H-Benzimidazol-6-yl, 1H-Benzimidazol-7-yl, 1,3-Benzoxazol-2-yl, 1,3-Benzoxazol-4-yl, 1,3-Benzoxazol-5-yl, 1,3-Benzoxazol-6-yl, 1,3-Benzoxazol-7-yl, 1,3-Benzthiazol-2-yl, 1,3-Benzthiazol-4-yl, 1,3-Benzthiazol-5-yl, 1,3-Benzthiazol-6-yl, 1,3-Benzthiazol-7-yl, 1,2-Benzisoxazol-3-yl, 1,2-Benzisoxazol-4-yl, 1,2-Benzisoxazol-5-yl, 1,2-Benzisoxazol-6-yl, 1,2-Benzisoxazol-7-yl, 1,2-Benzisothiazol-3-yl, 1,2-Benzisothiazol-4-yl, 1,2-Benzisothiazol-5-yl, 1,2-Benzisothiazol-6-yl, 1,2-Benzisothiazol-7-yl.,

[0028] The term "halogen" refers to fluorine, chlorine, bromine, or iodine. When used for a residue, "halogen" means a fluorine, chlorine, bromine, or iodine atom.

[0029] According to the invention, "alkyl" means a straight-chain or branched open-chain saturated hydrocarbon residue, which is optionally single- or multiply substituted and in the latter case is referred to 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 combinations of different alkyl residues, e.g., methyl(ethyl) or ethyl(methyl).

[0030] "Haloalkyl", "-alkenyl" and "-alkynyl" mean alkyl, alkenyl or alkynyl compounds that are partially or completely substituted by the same or different halogen atoms, such as monohaloalkyl (= monohaloalkyl) e.g. CH₂CH₂Cl, CH₂CH₂Br, CHClCH₃, CH₂Cl, CH₂F; perhaloalkyl e.g. CCl₃, CClF₂, CFCl₂, CF₂CClF₂, CF₂CClFCF₃; polyhaloalkyl e.g. CH₂CH₂Cl, CF₂CClFH, CF₂CBrFH, CH₂CF₃; the term perhaloalkyl also includes the term perfluoroalkyl.

[0031] "Haloalkoxy" is e.g. OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl; the same applies to haloalkenyl and other halogen-substituted residues.

[0032] The term "(C1-C4)-alkyl" used here is a shorthand notation for straight-chain or branched alkyl with one to four carbon atoms, depending on the specified range of carbon atoms. This includes the groups methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl, or tert-butyl. General alkyl groups with a larger specified range of carbon atoms, e.g., "(C1-C6)-alkyl," also include straight-chain or branched alkyl groups with a larger number of carbon atoms, i.e., as in the example, also alkyl groups with five and six carbon atoms.

[0033] Unless otherwise specified, the lower carbon skeletons of hydrocarbon groups such as alkyl, alkenyl, and alkynyl groups, including those in compound groups, are preferred, with 1 to 6 carbon atoms, or, in the case of unsaturated groups, with 2 to 6 carbon atoms. Alkyl groups, including those in compound groups such as alkoxy, haloalkyl, etc., mean methyl, ethyl, n- or i-propyl, n-, i-, t-, or 2-butyl, pentyl, hexyl, such as n-hexyl, i-hexyl, and 1,3-dimethylbutyl, and heptyl, such as n-heptyl, 1-methylhexyl, and 1,4-dimethylpentyl. Alkenyl and alkynyl groups represent the corresponding unsaturated groups, including at least one double bond or triple bond, respectively. Residues with a double or triple bond are preferred.

[0034] The term "alkenyl" includes in particular straight-chain or branched open-chain hydrocarbon residues with more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl residues with one or more cumulated double bonds, such as allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl. Alkenyl means vinyl, which may be substituted by further alkyl groups, such as (C2-C6)-alkenyl, like ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl 1-Methyl-3-butenyl, 2-Methyl-3-butenyl, 3-Methyl-3-butenyl, 1,1-Dimethyl-2-propenyl, 1,2-Dimethyl-1-propenyl, 1,2-Dimethyl-2-propenyl, 1-Ethyl-1-propenyl, 1-Ethyl-2-propenyl, 1-Hexenyl, 2-hexenyl,3-Hexenyl, 4-Hexenyl, 5-Hexenyl, 1-Methyl-1-pentenyl, 2-Methyl-1-pentenyl, 3-Methyl-1-pentenyl, 4-Methyl-1-pentenyl, 1-Methyl-2-pentenyl, 2-Methyl-2-pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl, 1-Methyl-3-pentenyl, 2-Methyl-3-pentenyl, 3-Methyl-3-pentenyl, 4-Methyl-3-pentenyl, 1-Methyl-4-pentenyl, 2-Methyl-4-pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1,1-Dimethyl-2-butenyl, 1,1-Dimethyl-3-butenyl, 1,2-Dimethyl-1-butenyl, 1,2-Dimethyl-2-butenyl, 1,2-Dimethyl-3-butenyl, 1,3-Dimethyl-1-butenyl, 1,3-Dimethyl-2-butenyl, 1,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3-Dimethyl-1-butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3-Dimethyl-1-butenyl, 3,3-Dimethyl-2-butenyl, 1-Ethyl-1-butenyl, 1-Ethyl-2-butenyl, 1-Ethyl-3-butenyl, 2-Ethyl-1-butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, 1,1,2-Trimethyl-2-propenyl, 1-Ethyl-1-methyl-2-propenyl, 1-Ethyl-2-methyl-1-propenyl und 1-Ethyl-2-methyl-2-propenyl.,

[0035] The term "alkynyl" also includes, in particular, straight-chain or branched open-chain hydrocarbon residues with more than one triple bond or with one or more triple bonds and one or more double bonds, such as 1,3-butatrienyl or 3-penten-1-in-1-yl.(C 2 -C 6 )-Alkinyl bedeutet Ethinyl, 1-Propinyl, 2-Propinyl, 1-Butinyl, 2-Butinyl, 3-Butinyl, 1-Methyl-2-propinyl, 1-Pentinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, 1-Methyl-2-butinyl, 1-Methyl-3-butinyl, 2-Methyl-3-butinyl, 3-Methyl-1-butinyl, 1,1-Dimethyl-2-propinyl, 1-Ethyl-2-propinyl, 1-Hexinyl, 2-Hexinyl, 3-Hexinyl, 4-Hexinyl, 5-Hexinyl, 1-Methyl-2-pentinyl, 1-Methyl-3-pentinyl, 1-Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl-4-pentinyl, 3-Methyl-1-pentinyl, 3-Methyl-4-pentinyl, 4-Methyl-1-pentinyl, 4-Methyl-2-pentinyl, 1,1-Di-methyl-2-butinyl, 1,1-Dimethyl-3-butinyl, 1,2-Dimethyl-3-butinyl, 2,2-Dimethyl-3-butinyl, 3,3-Dimethyl-1-butinyl, 1-Ethyl-2-butinyl, 1-Ethyl-3-butinyl, 2-Ethyl-3-butinyl und 1-Ethyl-1-methyl-2-propinyl.

[0036] The term "cycloalkyl" means a carbocyclic, saturated ring system with preferably 3-8 ring carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl, optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, alkoxycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, or cycloalkylaminocarbonyl. In the case of optionally substituted cycloalkyl, cyclic systems with substituents are included, including substituents with a double bond on the cycloalkyl group, e.g., an alkylidene group such as methylidene. In the case of optionally substituted cycloalkyl, multicyclic aliphatic systems are also included, such as Bicyclo[1.1.0]butan-1-yl, Bicyclo[1.1.0]butan-2-yl, Bicyclo[2.1.0]pentan-1-yl, Bicyclo[1.1.1]pentan-1-yl, Bicyclo[2.1.0]pentan-2-yl, Bicyclo[2.1.0]pentan-5-yl, Bicyclo[2.1.1]hexyl, Bicyclo[2.2.1]hept-2-yl, Bicyclo[2.2.2]octan-2-yl, Bicyclo[3.2.1]octan-2-yl, Bicyclo[3.2.2]nonan-2-yl, Adamantan-1-yl and Adamantan-2-yl, but also systems such as 1,1'-Bi(cyclopropyl)-1-yl, 1,1'-Bi(cyclopropyl)-2-yl. The term "(C 3 -C 7 )-cycloalkyl" is a shorthand notation for cycloalkyl with three to seven carbon atoms, corresponding to the range specified for the number of carbon atoms.

[0037] In the case of substituted cycloalkyl, spirocyclic aliphatic systems are also included, such as Spiro[2.2]pent-1-yl, Spiro[2.3]hex-1-yl, Spiro[2.3]hex-4-yl, 3-Spiro[2.3]hex-5-yl, Spiro[3.3]hept-1-yl, Spiro[3.3]hept-2-yl.

[0038] "Arylalkyl" refers to an aryl residue bound via an alkyl group and "Heteroarylalkyl" refers to a heteroaryl residue bound via an alkyl group.

[0039] According to the invention, "haloalkylthio" - on its own 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 (C 1 -C 8 )-, (C 1 -C 6 )- or (C 1 -C 4 )-haloalkylthio, such as trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio, 3,3,3-prop-1-ylthio.

[0040] "Halocycloalkyl" means a cycloalkyl partially or fully substituted by the same or different halogen atoms, such as F, Cl and Br, or by haloalkyl, such as trifluoromethyl or difluoromethyl, such as 1-fluorocycloprop-1-yl, 2-fluorocycloprop-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocyclobut-1-yl, 1-trifluoromethylcycloprop-1-yl, 2-trifluoromethylcycloprop-1-yl, 1-chlorocycloprop-1-yl, 2-chlorocycloprop-1-yl, 2,2-dichlorocycloprop-1-yl, 3,3-difluorocyclobutyl.

[0041] According to the invention, "trialkylsilyl" - on its own or as part of a chemical group - represents straight-chain or branched Si-alkyl, preferably with 1 to 8, or with 1 to 6 carbon atoms, such as tri-[(C 1 -C 8 )-, (C 1 -C 6 )- or (C 1 -C 4 )-alkyl]silyl, such as trimethylsilyl, triethylsilyl, tri-(n-propyl)silyl, tri-(isopropyl)silyl, tri-(n-butyl)silyl, tri-(1-methylprop-1-yl)silyl, tri-(2-methylprop-1-yl)silyl, tri(1,1-dimethyleth-1-yl)silyl, tri(2,2-dimethyleth-1-yl)silyl.

[0042] If the compounds can form tautomers through hydrogen shifts, which would not be formally covered by the general formula (I), these tautomers are nevertheless included in the definition of the compounds of the invention with general formula (I), unless a specific tautomer is the subject of consideration. Thus, many carbonyl compounds can exist in both the keto and enol forms, both of which are covered by the definition of the compound with general formula (I).

[0043] Compounds of general formula (I) can exist as stereoisomers depending on the type and arrangement of the substituents. The possible stereoisomers, defined by their specific spatial configuration, such as enantiomers, diastereomers, Z-isomers, and E-isomers, are all encompassed by general formula (I). If one or more alkenyl groups are present, diastereomers (Z-isomers and E-isomers) can occur. If one or more asymmetric carbon atoms are present, enantiomers and diastereomers can occur. Stereoisomers can be obtained from the mixtures obtained during preparation using standard separation methods. Chromatographic separation can be performed both on an analytical scale to determine the enantiomeric or diastereomeric excess, and on a preparative scale to prepare test samples for biological testing.Likewise, stereoisomers can be selectively produced by using stereoselective reactions with optically active starting materials and / or auxiliary substances. The invention therefore also relates to all stereoisomers included in the general formula (I) but not specified with their specific stereoform, as well as their mixtures.

[0044] If the compounds are obtained as solids, purification can also be carried out by recrystallization or digestion. If individual compounds (I) are not satisfactorily accessible by the methods described below, they can be prepared by derivatization of other compounds (I).

[0045] Methods suitable for isolating, purifying, and separating compounds of general formula (I) include those generally known to those skilled in the art from analogous cases, e.g., physical processes such as crystallization, chromatographic methods, especially column chromatography and HPLC (high-performance liquid chromatography), distillation, optionally under reduced pressure, extraction, and other methods. Any remaining mixtures can generally be separated by chromatographic separation, e.g., on chiral solid phases. For preparative quantities or on an industrial scale, methods such as crystallization are suitable, e.g., of diastereomeric salts, which can be obtained from the diastereomeric mixtures with optically active acids and, optionally, with optically active bases if acidic groups are present.

[0046] The present invention also claims methods for producing the compounds of general formula (I) according to the invention.

[0047] The compounds of general formula (I) according to the invention can be prepared, among other methods, starting from known processes. The synthesis routes used and investigated are based on commercially available or readily producible building blocks. The groups X, A, R1<, R2<, R3< and m of general formula (I) have the meanings defined above in the following schemes, unless exemplary, but not limiting, definitions are given.

[0048] The compounds according to the invention can be produced, for example, according to the method shown in Scheme 1.

[0049] The pyri(mi)dines of general formula (I) can be prepared by coupling the corresponding anilines (EI) with the pyri(mi)dines (EII), where LG is a leaving group, in the presence of a palladium catalyst. The required base can be a carbonate salt of an alkali metal (such as sodium or potassium). The reactions are generally carried out in an organic solvent, such as dioxane, dimethyl sulfoxide, or dimethylformamide, at temperatures between 0°C and the boiling point of the solvent.

[0050] The anilines of general formula (EI) are known from the literature and can be prepared according to the methods described in Organic Letters, 19(14), 3855-3858; 2017 and similarly.

[0051] Selected detailed synthesis examples for the compounds of general formula (I) according to the invention are listed below. The <1H NMR, <13C NMR, and <19F NMR spectroscopic data given for the chemical examples described in the following sections (400 MHz for <1H NMR, 150 MHz for <13C NMR, and 375 MHz for <19F NMR, solvents CDCl₃, CD₃OD, or d₆-DMSO, internal standard: tetramethylsilane δ = 0.00 ppm) were obtained using a Bruker instrument, and the signals indicated have the following meanings: br = broad; s = singlet, d = doublet, t = triplet, dd = double doublet, ddd = doublet of a double doublet, m = multiplet, q = quartet, quint = quintet, sext = sextet, sept = septet, dq = double quartet, dt = double triplet.For diastereomeric mixtures, either the significant signals of both diastereomers or the characteristic signal of the main diastereomer are given. The abbreviations used for chemical groups have, for example, the following meanings: Me = CH₃, Et = CH₂CH₃, t-Hex = C(CH₃)₂CH(CH₃)₂, t-Bu = C(CH₃)₃, n-Bu = unbranched butyl, n-Pr = unbranched propyl, i-Pr = branched propyl, c-Pr = cyclopropyl, c-Hex = cyclohexyl. Synthesis examples: Table example number 1-246 : Synthesis step 1: 2-(2-fluorophenoxy)-3-nitrobenzonitrile

[0052]

[0053] A solution of 741 mg 2-fluoro-3-nitrobenzonitrile (4.46 mmol, 1.0 eq), 500 mg 2-fluorophenol (4.46 mmol, 1.0 eq), and 1.23 g potassium carbonate (8.92 mmol, 2.0 eq) in 10 ml DMF was stirred for 2 h at 100 °C. The solution was then diluted with 100 ml DCM and washed with water (100 mL × 3), dried over sodium sulfate, and concentrated under vacuum. The yield was 950 mg (87%). Synthesis step 2: 3-amino-2-(2-fluorophenoxy)benzonitrile

[0054]

[0055] A solution of 950 mg 2-(2-fluorophenoxy)-3-nitrobenzonitrile (3.68 mmol, 1.0 eq) and 2.49 g SnCl₂·2H₂O (11.05 mmol, 3.0 eq) in 30 ml EtOH was stirred for 16 h at 80 °C. The solution was then concentrated under vacuum, adjusted to pH 7–8 with 2 N sodium hydroxide solution, and extracted with ethyl acetate. The organic phase was dried over sodium sulfate, concentrated under vacuum, and the residue was purified by column chromatography. The yield of the yellow solid was 750 mg (90%). Synthesis step 3: 2-(2-Fluorphenoxy)-3-(pyrimidin-2-ylamino)benzonitrile (Table example 1-246)

[0056]

[0057] A solution of 250 mg 3-Amino-2-(2-fluorophenoxy)benzonitrile (1.09 mmol, 1.0 eq), 24.4 mg Pd(AcO)₂ (0.11 mmol, 0.1 eq), 136.9 mg BINAP (0.22 mmol, 0.2 eq), 244 mg t-BuOK (2.18 mmol, 2 eq), and 125 mg 2-chloropyrimidine (1.09 mmol, 1.0 eq) in 8 ml toluene was stirred under argon at 100 °C for 12 h. The solvent was concentrated under vacuum, and the residue was purified by column chromatography. The yield of the yellow solid was 65 mg. Table example number 2-141: Synthesis step 1: 4-(5-Chloropyrimidin-2-ylamino)-3-fluorobenzoic acid methyl ester

[0058]

[0059] A solution of 2 g of methyl 4-amino-3-fluorobenzoate (11.8 mmol), 541 mg of Pd₂ dba₃ (0.59 mmol, 0.05 eq), 341 mg of xantphos (0.59 mmol, 0.05 eq), 5.78 g of Cs₂CO₃ (17.7 mmol, 1.5 eq), and 1.94 g of 2,5-dichloropyrimidine (13 mmol, 1.1 eq) in 25 ml of dioxane was stirred under reflux for 3 h in argon. The solvent was concentrated under vacuum, and the residue was purified by column chromatography. The yield was 2.9 g (87%). Synthesis step 2: 4-(5-chloropyrimidin-2-ylamino)-3-fluorobenzoic acid

[0060]

[0061] A solution of 2.8 g of 4-(5-chloropyrimidine-2-ylamino)-3-fluorobenzoic acid methyl ester (9.9 mmol) in 30 ml of methanol was treated with 6.5 ml of 2N sodium hydroxide solution (12.9 mmol, 1.3 eq) and heated for 10 h at 50°C. The mixture was then diluted with water and washed with ethyl acetate. The aqueous solution was acidified with hydrochloric acid and the product was collected by filtration. Yield: 1.8 g (68%). Synthesis step 3: Ethyl (4-(5-chloropyrimidin-2-ylamino)-3-fluorophenyl)carbamate

[0062]

[0063] A solution of 1.8 g of 4-(5-chloropyrimidin-2-ylamino)-3-fluorobenzoic acid (6.73 mmol), 1.13 mL of triethylamine (8.1 mmol, 1.2 eq), and 1.74 mL of diphenylphosphoryl azide (8.1 mmol, 1.2 eq) in 45 mL of ethanol and 45 mL of dioxane was heated under reflux. After completion of the reaction, the mixture was concentrated under vacuum and treated with 2N hydrochloric acid and ethyl acetate. The organic phase was washed with sodium chloride, dried over sodium sulfate, concentrated, and the residue was purified by column chromatography. Yield: 1.5 g (72%, impurities). Synthesis step 4: Ethyl (4-(5-chloropyrimidin-2-ylamino)-5-fluoro-2-nitrophenyl) carbamate

[0064]

[0065] To a solution of 1.3 g ethyl-(4-(5-chloropyrimidin-2-ylamino)-3-fluorophenyl)carbamate (4.18 mmol) in 5 ml acetic acid, a solution prepared under cooling from 365 mg nitric acid (60%, 3.8 mmol) and 1.74 ml acetic anhydride was added. After stirring for 1 h at room temperature, the solution was made basic with sodium bicarbonate solution and extracted with ethyl acetate. The organic phase was washed with sodium chloride, dried over sodium sulfate, concentrated, and the residue was purified by column chromatography. Yield: 550 mg (40%). Synthesis step 5: Ethyl-(4-(5-chloropyrimidin-2-ylamino)-5-(4-fluorphenoxy)-2-nitrophenyl)carbamate (Table example number 2-141)

[0066]

[0067] A solution of 410 mg ethyl-(4-(5-chloropyrimidin-2-ylamino)-5-fluoro-2-nitrophenyl)carbamate (1.15 mmol), 155 mg 4-fluorophenol (1.38 mmol, 1.2 eq), and 239 mg potassium carbonate (1.73 mmol, 1.5 eq) in 10 ml DMF was stirred for 3 h at room temperature. After adding water, the product was filtered off. Yield: 440 mg (84%). Table example number 2-130: 4-(5-Chloropyrimidin-2-ylamino)-5-(4-fluorophenoxy)-2-nitroaniline

[0068]

[0069] A solution of 160 mg ethyl-(4-(5-chloropyrimidin-2-ylamino)-5-(4-fluorphenoxy)-2-nitrophenyl)carbamate (0.36 mmol) in 3 ml ethanol was treated with 0.7 ml 2N sodium hydroxide solution. After completion of the reaction, the solution was treated with water, extracted with DCM, concentrated, and the residue was purified by column chromatography. Yield: 35 mg (26%). Table example number 2-101: 2-Chloro-4-(5-chloropyrimidine-2-ylamino)-3-(4-fluorophenoxy)-6-nitroaniline

[0070]

[0071] A solution of 145 mg of 4-(5-chloropyrimidine-2-ylamino)-5-(4-fluorphenoxy)-2-nitroaniline (0.38 mmol) in 2 ml of DMF was treated with 51 mg of NCS (0.38 mmol, 1 eq). After 2 days at room temperature, the mixture was diluted with ethyl acetate and washed with water and saline solution, dried over sodium sulfate, concentrated, and the residue purified by column chromatography. Yield: 25 mg (16%).

[0072] By analogy to the manufacturing examples mentioned above and cited at the appropriate point, the following compounds of the general formula, shown in Table 1, are obtained. Table 1 Beispielnummer R 2< R 3< A R 1< 1-1 F H CH Phenyl 1-2 F H CH 2-Fluorphenyl 1-3 F H CH 3-Fluorphenyl 1-4 F H CH 4-Fluorphenyl 1-5 F H CH 3-Chlorphenyl 1-6 F H CH 4-Chlorphenyl 1-7 F H CH 2,4-Difluorphenyl 1-8 F H CH 2,5-Difluorphenyl 1-9 F H CH 3,4-Difluorphenyl 1-10 F H CH 3,5-Difluorphenyl 1-11 F H CH 2-Chlor-4-Fluorphenyl 1-12 F H CH 4-Methylphenyl 1-13 F H CH 4-Ethylphenyl 1-14 F H CH 3-(Trifluormethyl)phenyl 1-15 F H CH 4-(Trifluormethyl)phenyl 1-16 F H CH 4-Cyanophenyl 1-17 F H CH 3-Methoxyphenyl 1-18 F H CH 4-Methylthiophenyl 1-19 F F CH Phenyl 1-20 F F CH 2-Fluorphenyl 1-21 F F CH 3-Fluorphenyl 1-22 F F CH 4-Fluorphenyl 1-23 F F CH 3-Chlorphenyl 1-24 F F CH 4-Chlorphenyl 1-25 F F CH 2,4-Difluorphenyl 1-26 F F CH 2,5-Difluorphenyl 1-27 F F CH 3,4-Difluorphenyl 1-28 F F CH 3,5-Difluorphenyl 1-29 F F CH 2-Chlor-4-Fluorphenyl 1-30 F F CH 4-Methylphenyl 1-31 F F CH 4-Ethylphenyl 1-32 F F CH 3-(Trifluormethyl)phenyl 1-33 F F CH 4-(Trifluormethyl)phenyl 1-34 F F CH 4-Cyanophenyl 1-35 F F CH 3-Methoxyphenyl 1-36 F F CH 4-Methylthiophenyl 1-37 F Cl CH Phenyl 1-38 F Cl CH 2-Fluorphenyl 1-39 F Cl CH 3-Fluorphenyl 1-40 F Cl CH 4-Fluorphenyl 1-41 F Cl CH 3-Chlorphenyl 1-42 F Cl CH 4-Chlorphenyl 1-43 F Cl CH 2,4-Difluorphenyl 1-44 F Cl CH 2,5-Difluorphenyl 1-45 F Cl CH 3,4-Difluorphenyl 1-46 F Cl CH 3,5-Difluorphenyl 1-47 F Cl CH 2-Chlor-4-Fluorphenyl 1-48 F Cl CH 3-(Trifluormethyl)phenyl 1-49 F Cl CH 4-(Trifluormethyl)phenyl 1-50 F Cl CH 3-Methoxyphenyl 1-51 F Cl CH 4-Cyanophenyl 1-52 F Cl CH 4-Methylphenyl 1-53 F Cl CH 4-Ethylphenyl 1-54 F Cl CH 4-Methylthiophenyl 1-55 F Cl CF 4-Fluorphenyl 1-56 F Cl CF 3,4-Difluorphenyl 1-57 F Cl CCl 4-Fluorphenyl 1-58 F Cl CCl 3,4-Difluorphenyl 1-59 F Br CH 4-Fluorphenyl 1-60 F Br CH 3,4-Difluorphenyl 1-61 F CN CH 4-Fluorphenyl 1-62 F CN CH 3,4-Difluorphenyl 1-63 F NO 2 CH 4-Fluorphenyl 1-64 F NO 2 CH 3,4-Difluorphenyl 1-65 F Me CH 4-Fluorphenyl 1-66 F Me CH 3,4-Difluorphenyl 1-67 F Et CH 4-Fluorphenyl 1-68 F Et CH 3,4-Difluorphenyl 1-69 F MeO CH 4-Fluorphenyl 1-70 F MeO CH 3,4-Difluorphenyl 1-71 F MeS CH 4-Fluorphenyl 1-72 F MeS CH 3,4-Difluorphenyl 1-73 Cl F CH 4-Fluorphenyl 1-74 Cl F CH 3,4-Difluorphenyl 1-75 Cl Cl CH 4-Fluorphenyl 1-76 Cl Cl CH 3,4-Difluorphenyl 1-77 Me F CH 4-Fluorphenyl 1-78 Me F CH 3,4-Difluorphenyl 1-79 Me Cl CH 4-Fluorphenyl 1-80 Me Cl CH 3,4-Difluorphenyl 1-81 Et F CH 4-Fluorphenyl 1-82 Et F CH 3,4-Difluorphenyl 1-83 Et Cl CH 4-Fluorphenyl 1-84 Et Cl CH 3,4-Difluorphenyl 1-85 CN H CH Phenyl 1-86 CN H CH 2-Fluorphenyl 1-87 CN H CH 3-Fluorphenyl 1-88 CN H CH 4-Fluorphenyl 1-89 CN H CH 3-Chlorphenyl 1-90 CN H CH 4-Chlorphenyl 1-91 CN H CH 2,4-Difluorphenyl 1-92 CN H CH 2,5-Difluorphenyl 1-93 CN H CH 3,4-Difluorphenyl 1-94 CN H CH 3,5-Difluorphenyl 1-95 CN H CH 2-Chlor-4-Fluorphenyl 1-96 CN H CH 4-Methylphenyl 1-97 CN H CH 4-Ethylphenyl 1-98 CN H CH 3-(Trifluormethyl)phenyl 1-99 CN H CH 4-(Trifluormethyl)phenyl 1-100 CN H CH 4-Cyanophenyl 1-101 CN H CH 3-Methoxyphenyl 1-102 CN H CH 4-Methylthiophenyl 1-103 CN F CH Phenyl 1-104 CN F CH 2-Fluorphenyl 1-105 CN F CH 3-Fluorphenyl 1-106 CN F CH 4-Fluorphenyl 1-107 CN F CH 3-Chlorphenyl 1-108 CN F CH 4-Chlorphenyl 1-109 CN F CH 2,4-Difluorphenyl 1-110 CN F CH 2,5-Difluorphenyl 1-111 CN F CH 3,4-Difluorphenyl 1-112 CN F CH 3,5-Difluorphenyl 1-113 CN F CH 2-Chlor-4-Fluorphenyl 1-114 CN F CH 4-Methylphenyl 1-115 CN F CH 4-Ethylphenyl 1-116 CN F CH 3-(Trifluormethyl)phenyl 1-117 CN F CH 4-(Trifluormethyl)phenyl 1-118 CN F CH 4-Cyanophenyl 1-119 CN F CH 3-Methoxyphenyl 1-120 CN F CH 4-Methylthiophenyl 1-121 CN Cl CH Phenyl 1-122 CN Cl CH 2-Fluorphenyl 1-123 CN Cl CH 3-Fluorphenyl 1-124 CN Cl CH 4-Fluorphenyl 1-125 CN Cl CH 3-Chlorphenyl 1-126 CN Cl CH 4-Chlorphenyl 1-127 CN Cl CH 2,4-Difluorphenyl 1-128 CN Cl CH 2,5-Difluorphenyl 1-129 CN Cl CH 3,4-Difluorphenyl 1-130 CN Cl CH 3,5-Difluorphenyl 1-131 CN Cl CH 2-Chlor-4-Fluorphenyl 1-132 CN Cl CH 4-Methylphenyl 1-133 CN Cl CH 4-Ethylphenyl 1-134 CN Cl CH 3-(Trifluormethyl)phenyl 1-135 CN Cl CH 4-(Trifluormethyl)phenyl 1-136 CN Cl CH 4-Cyanophenyl 1-137 CN Cl CH 3-Methoxyphenyl 1-138 CN Cl CH 4-Methylthiophenyl 1-139 CN Cl CF 4-Fluorphenyl 1-140 CN Cl CF 3,4-Difluorphenyl 1-141 CN Cl CCl 4-Fluorphenyl 1-142 CN Cl CCl 3,4-Difluorphenyl 1-143 CN Br CH 4-Fluorphenyl 1-144 CN Br CH 3,4-Difluorphenyl 1-145 CN CN CH 4-Fluorphenyl 1-146 CN CN CH 3,4-Difluorphenyl 1-147 CN NO 2 CH 4-Fluorphenyl 1-148 CN NO 2 CH 3,4-Difluorphenyl 1-149 CN Me CH 4-Fluorphenyl 1-150 CN Me CH 3,4-Difluorphenyl 1-151 CN Et CH 4-Fluorphenyl 1-152 CN Et CH 3,4-Difluorphenyl 1-153 CN MeO CH 4-Fluorphenyl 1-154 CN MeO CH 3,4-Difluorphenyl 1-155 CN MeS CH 4-Fluorphenyl 1-156 CN MeS CH 3,4-Difluorphenyl 1-157 MeO F CH 4-Fluorphenyl 1-158 MeO F CH 3,4-Difluorphenyl 1-159 MeO Cl CH 4-Fluorphenyl 1-160 MeO Cl CH 3,4-Difluorphenyl 1-161 MeS F CH 4-Fluorphenyl 1-162 MeS F CH 3,4-Difluorphenyl 1-163 MeS Cl CH 4-Fluorphenyl 1-164 MeS Cl CH 3,4-Difluorphenyl 1-165 F H N Phenyl 1-166 F H N 2-Fluorphenyl 1-167 F H N 3-Fluorphenyl 1-168 F H N 4-Fluorphenyl 1-169 F H N 3-Chlorphenyl 1-170 F H N 4-Chlorphenyl 1-171 F H N 2,4-Difluorphenyl 1-172 F H N 2,5-Difluorphenyl 1-173 F H N 3,4-Difluorphenyl 1-174 F H N 3,5-Difluorphenyl 1-175 F H N 4-Methylphenyl 1-176 F H N 4-Ethylphenyl 1-177 F H N 2-Chlor-4-Fluorphenyl 1-178 F H N 3-(Trifluormethyl)phenyl 1-179 F H N 4-(Trifluormethyl)phenyl 1-180 F H N 4-Cyanophenyl 1-181 F H N 3-Methoxyphenyl 1-182 F H N 4-Methylthiophenyl 1-183 F F N Phenyl 1-184 F F N 2-Fluorphenyl 1-185 F F N 3-Fluorphenyl 1-186 F F N 4-Fluorphenyl 1-187 F F N 3-Chlorphenyl 1-188 F F N 4-Chlorphenyl 1-189 F F N 2,4-Difluorphenyl 1-190 F F N 2,5-Difluorphenyl 1-191 F F N 3,4-Difluorphenyl 1-192 F F N 3,5-Difluorphenyl 1-193 F F N 2-Chlor-4-fluorphenyl 1-194 F F N 4-Methylphenyl 1-195 F F N 4-Ethylphenyl 1-196 F F N 3-(Trifluormethyl)phenyl 1-197 F F N 4-(Trifluormethyl)phenyl 1-198 F F N 4-Cyanophenyl 1-199 F F N 3-Methoxyphenyl 1-200 F F N 4-Methylthiophenyl 1-201 F Cl N Phenyl 1-202 F Cl N 2-Fluorphenyl 1-203 F Cl N 3-Fluorphenyl 1-204 F Cl N 4-Fluorphenyl 1-205 F Cl N 3-Chlorphenyl 1-206 F Cl N 4-Chlorphenyl 1-207 F Cl N 2,4-Difluorphenyl 1-208 F Cl N 2,5-Difluorphenyl 1-209 F Cl N 3,4-Difluorphenyl 1-210 F Cl N 3,5-Difluorphenyl 1-211 F Cl N 2-Chlor-4-fluorphenyl 1-212 F Cl N 4-Methylphenyl 1-213 F Cl N 4-Ethylphenyl 1-214 F Cl N 3-(Trifluormethyl)phenyl 1-215 F Cl N 4-(Trifluormethyl)phenyl 1-216 F Cl N 4-Cyanophenyl 1-217 F Cl N 3-Methoxyphenyl 1-218 F Cl N 4-Methylthiophenyl 1-219 F Br N 4-Fluorphenyl 1-220 F Br N 3,4-Difluorphenyl 1-221 F CN N 4-Fluorphenyl 1-222 F CN N 3,4-Difluorphenyl 1-223 F NO 2 N 4-Fluorphenyl 1-224 F NO 2 N 3,4-Difluorphenyl 1-225 F Me N 4-Fluorphenyl 1-226 F Me N 3,4-Difluorphenyl 1-227 F Et N 4-Fluorphenyl 1-228 F Et N 3,4-Difluorphenyl 1-229 F MeO N 4-Fluorphenyl 1-230 F MeO N 3,4-Difluorphenyl 1-231 F MeS N 4-Fluorphenyl 1-232 F MeS N 3,4-Difluorphenyl 1-233 Cl F N 4-Fluorphenyl 1-234 Cl F N 3,4-Difluorphenyl 1-235 Cl Cl N 4-Fluorphenyl 1-236 Cl Cl N 3,4-Difluorphenyl 1-237 Me F N 4-Fluorphenyl 1-238 Me F N 3,4-Difluorphenyl 1-239 Me Cl N 4-Fluorphenyl 1-240 Me Cl N 3,4-Difluorphenyl 1-241 Et F N 4-Fluorphenyl 1-242 Et F N 3,4-Difluorphenyl 1-243 Et Cl N 4-Fluorphenyl 1-244 Et Cl N 3,4-Difluorphenyl 1-245 CN H N Phenyl 1-246 CN H N 2-Fluorphenyl 1-247 CN H N 3-Fluorphenyl 1-248 CN H N 4-Fluorphenyl 1-249 CN H N 3-Chlorphenyl 1-250 CN H N 4-Chlorphenyl 1-251 CN H N 2,4-Difluorphenyl 1-252 CN H N 2,5-Difluorphenyl 1-253 CN H N 3,4-Difluorphenyl 1-254 CN H N 3,5-Difluorphenyl 1-255 CN H N 2-Chlor-4-Fluorphenyl 1-256 CN H N 4-Chlor-2-Fluorphenyl 1-257 CN H N 4-Methylphenyl 1-258 CN H N 4-Ethylphenyl 1-259 CN H N 3-(Trifluormethyl)phenyl 1-260 CN H N 4-(Trifluormethyl)phenyl 1-261 CN H N 4-Cyanophenyl 1-262 CN H N 3-Methoxyphenyl 1-263 CN H N 4-Methylthiophenyl 1-264 CN F N Phenyl 1-265 CN F N 2-Fluorphenyl 1-266 CN F N 3-Fluorphenyl 1-267 CN F N 4-Fluorphenyl 1-268 CN F N 3-Chlorphenyl 1-269 CN F N 4-Chlorphenyl 1-270 CN F N 2,4-Difluorphenyl 1-271 CN F N 2,5-Difluorphenyl 1-272 CN F N 3,4-Difluorphenyl 1-273 CN F N 3,5-Difluorphenyl 1-274 CN F N 2-Chlor-4-Fluorphenyl 1-275 CN F N 4-Chlor-2-Fluorphenyl 1-276 CN F N 4-Methylphenyl 1-277 CN F N 4-Ethylphenyl 1-278 CN F N 3-(Trifluormethyl)phenyl 1-279 CN F N 4-(Trifluormethyl)phenyl 1-280 CN F N 4-Cyanophenyl 1-281 CN F N 3-Methoxyphenyl 1-282 CN F N 4-Methylthiophenyl 1-283 CN Cl N Phenyl 1-284 CN Cl N 2-Fluorphenyl 1-285 CN Cl N 3-Fluorphenyl 1-286 CN Cl N 4-Fluorphenyl 1-287 CN Cl N 3-Chlorphenyl 1-288 CN Cl N 4-Chlorphenyl 1-289 CN Cl N 2,4-Difluorphenyl 1-290 CN Cl N 2,5-Difluorphenyl 1-291 CN Cl N 3,4-Difluorphenyl 1-292 CN Cl N 3,5-Difluorphenyl 1-293 CN Cl N 2-Chlor-4-Fluorphenyl 1-294 CN Cl N 4-Chlor-2-Fluorphenyl 1-295 CN Cl N 4-Methylphenyl 1-296 CN Cl N 4-Ethylphenyl 1-297 CN Cl N 3-(Trifluormethyl)phenyl 1-298 CN Cl N 4-(Trifluormethyl)phenyl 1-299 CN Cl N 4-Cyanophenyl 1-300 CN Cl N 3-Methoxyphenyl 1-301 CN Cl N 4-Methylthiophenyl 1-302 CN Br N 4-Fluorphenyl 1-303 CN Br N 3,4-Difluorphenyl 1-304 CN CN N 4-Fluorphenyl 1-305 CN CN N 3,4-Difluorphenyl 1-306 CN NO 2 N 4-Fluorphenyl 1-307 CN NO 2 N 3,4-Difluorphenyl 1-308 CN Me N 4-Fluorphenyl 1-309 CN Me N 3,4-Difluorphenyl 1-310 CN Et N 4-Fluorphenyl 1-311 CN Et N 3,4-Difluorphenyl 1-312 CN MeO N 4-Fluorphenyl 1-313 CN MeO N 3,4-Difluorphenyl 1-314 CN CHF 2 O N 4-Fluorphenyl 1-315 CN CHF 2 O N 3,4-Difluorphenyl 1-316 CN CF 3 O N 4-Fluorphenyl 1-317 CN CF 3 O N 3,4-Difluorphenyl 1-318 CN MeS N 4-Fluorphenyl 1-319 CN MeS N 3,4-Difluorphenyl 1-320 CN CF 3 S N 4-Fluorphenyl 1-321 CN CF 3 S N 3,4-Difluorphenyl 1-322 MeO F N 4-Fluorphenyl 1-323 MeO F N 3,4-Difluorphenyl 1-324 MeO Cl N 4-Fluorphenyl 1-325 MeO Cl N 3,4-Difluorphenyl 1-326 MeS F N 4-Fluorphenyl 1-327 MeS F N 3,4-Difluorphenyl 1-328 MeS Cl N 4-Fluorphenyl 1-329 MeS Cl N 3,4-Difluorphenyl 1-330 CN CHF 2 O CH 4-Fluorphenyl 1-331 CN CHF 2 O CH 3,4-Difluorphenyl 1-332 CN CF 3 O CH 4-Fluorphenyl 1-333 CN CF 3 O CH 3,4-Difluorphenyl 1-334 CN CF 3 S CH 4-Fluorphenyl 1-335 CN CF 3 S CH 3,4-Difluorphenyl 1-336 H Cl N Phenyl 1-337 H Cl N 4-Fluorphenyl 1-338 H Cl N 3,4-Difluorphenyl 1-339 H Cl N 4-Cyanophenyl 1-340 Cl Cl N Phenyl 1-341 Cl Cl N 4-Chlorphenyl 1-342 CN OiPr CH 4-Fluorphenyl 1-343 CN OiPr CH 3,4-Difluorphenyl 1-344 CN OiPr N 4-Fluorphenyl 1-345 CN OiPr N 3,4-Difluorphenyl 1-346 H Cl CH 4-Fluorphenyl 1-347 H Cl CH 3,4-Difluorphenyl 1-348 NO2 Cl CH 4-Fluorphenyl 1-349 NO2 Cl CH 3,4-Difluorphenyl 1-350 NO2 Cl N 4-Fluorphenyl 1-351 NO2 Cl N 3,4-Difluorphenyl 1-352 NH2 Cl CH 4-Fluorphenyl 1-353 NH2 Cl CH 3,4-Difluorphenyl 1-354 NH2 Cl N 4-Fluorphenyl 1-355 NH2 Cl N 3,4-Difluorphenyl 1-356 Br Cl CH 4-Fluorphenyl 1-357 Br Cl CH 3,4-Difluorphenyl 1-358 Br Cl N 4-Fluorphenyl 1-359 Br Cl N 3,4-Difluorphenyl 1-360 CN EtO CH 4-Fluorphenyl 1-361 CN EtO CH 3,4-Difluorphenyl 1-362 CN EtO N 4-Fluorphenyl 1-363 CN EtO N 3,4-Difluorphenyl 1-364 CN Cl N 4-Cyano-3-fluorphenyl 1-365 NHMe Cl N 4-Fluorphenyl 1-366 NMe 2 Cl N 4-Fluorphenyl 1-367 NHC(O)H Cl N 4-Fluorphenyl 1-368 NHAc Cl N 4-Fluorphenyl 1-369 NMeAc Cl N 4-Fluorphenyl 1-370 I Cl CH 4-Fluorphenyl 1-371 I Cl CH 3,4-Difluorphenyl 1-372 I Cl N 4-Fluorphenyl 1-373 I Cl N 3,4-Difluorphenyl 1-374 CN F N 2,3,4-Trifluorphenyl 1-375 CN F N 2,4,5-Trifluorphenyl 1-376 SEt Cl N 4-Fluorphenyl

[0073] By analogy to the manufacturing examples mentioned above and cited at the appropriate point, the following compounds of the general formula are obtained and shown in Table 2. Table 2 Beispielnummer R 2a< R 2b< R 2c< R 3< A R 1< 2-1 F NH 2 H F CH 4-Fluorphenyl 2-2 F NH 2 H F CH 3,4-Difluorphenyl 2-3 F NH 2 Cl F CH 4-Fluorphenyl 2-4 F NH 2 Cl F CH 3,4-Difluorphenyl 2-5 F NH 2 Br F CH 4-Fluorphenyl 2-6 F NH 2 Br F CH 3,4-Difluorphenyl 2-7 F NH 2 NO 2 F CH 4-Fluorphenyl 2-8 F NH 2 NO 2 F CH 3,4-Difluorphenyl 2-9 F NHCOOEt H F CH 4-Fluorphenyl 2-10 F NHCOOEt H F CH 3,4-Difluorphenyl 2-11 F NH 2 H Cl CH 4-Fluorphenyl 2-12 F NH 2 H Cl CH 3,4-Difluorphenyl 2-13 F NH 2 Cl Cl CH 4-Fluorphenyl 2-14 F NH 2 Cl Cl CH 3,4-Difluorphenyl 2-15 F NH 2 Br Cl CH 4-Fluorphenyl 2-16 F NH 2 Br Cl CH 3,4-Difluorphenyl 2-17 F NH 2 NO 2 Cl CH 4-Fluorphenyl 2-18 F NH 2 NO 2 Cl CH 3,4-Difluorphenyl 2-19 F NHCOOEt H Cl CH 4-Fluorphenyl 2-20 F NHCOOEt H Cl CH 3,4-Difluorphenyl 2-21 Cl NH 2 H F CH 4-Fluorphenyl 2-22 Cl NH 2 H F CH 3,4-Difluorphenyl 2-23 Cl NH 2 Cl F CH 4-Fluorphenyl 2-24 Cl NH 2 Cl F CH 3,4-Difluorphenyl 2-25 Cl NH 2 Br F CH 4-Fluorphenyl 2-26 Cl NH 2 Br F CH 3,4-Difluorphenyl 2-27 Cl NH 2 NO 2 F CH 4-Fluorphenyl 2-28 Cl NH 2 NO 2 F CH 3,4-Difluorphenyl 2-29 Cl NHCOOEt H F CH 4-Fluorphenyl 2-30 Cl NHCOOEt H F CH 3,4-Difluorphenyl 2-31 Cl NH 2 H Cl CH 4-Fluorphenyl 2-32 Cl NH 2 H Cl CH 3,4-Difluorphenyl 2-33 Cl NH 2 Cl Cl CH 4-Fluorphenyl 2-34 Cl NH 2 Cl Cl CH 3,4-Difluorphenyl 2-35 Cl NH 2 Br Cl CH 4-Fluorphenyl 2-36 Cl NH 2 Br Cl CH 3,4-Difluorphenyl 2-37 Cl NH 2 NO 2 Cl CH 4-Fluorphenyl 2-38 Cl NH 2 NO 2 Cl CH 3,4-Difluorphenyl 2-39 Cl COOH H Cl CH 4-Fluorphenyl 2-40 Cl COOH H Cl CH 3,4-Difluorphenyl 2-41 Cl COOMe H Cl CH 4-Fluorphenyl 2-42 Cl COOMe H Cl CH 3,4-Difluorphenyl 2-43 Cl NHCOOEt H Cl CH 4-Fluorphenyl 2-44 Cl NHCOOEt H Cl CH 3,4-Difluorphenyl 2-45 CN NH 2 H F CH 4-Fluorphenyl 2-46 CN NH 2 H F CH 3,4-Difluorphenyl 2-47 CN NH 2 Cl F CH 4-Fluorphenyl 2-48 CN NH 2 Cl F CH 3,4-Difluorphenyl 2-49 CN NH 2 Br F CH 4-Fluorphenyl 2-50 CN NH 2 Br F CH 3,4-Difluorphenyl 2-51 CN NH 2 NO 2 F CH 4-Fluorphenyl 2-52 CN NH 2 NO 2 F CH 3,4-Difluorphenyl 2-53 CN NHCOOEt H F CH 4-Fluorphenyl 2-54 CN NHCOOEt H F CH 3,4-Difluorphenyl 2-55 CN NH 2 H Cl CH 4-Fluorphenyl 2-56 CN NH 2 H Cl CH 3,4-Difluorphenyl 2-57 CN NH 2 Cl Cl CH 4-Fluorphenyl 2-58 CN NH 2 Cl Cl CH 3,4-Difluorphenyl 2-59 CN NH 2 Br Cl CH 4-Fluorphenyl 2-60 CN NH 2 Br Cl CH 3,4-Difluorphenyl 2-61 CN NH 2 NO 2 Cl CH 4-Fluorphenyl 2-62 CN NH 2 NO 2 Cl CH 3,4-Difluorphenyl 2-63 CN NHCOOEt H Cl CH 4-Fluorphenyl 2-64 CN NHCOOEt H Cl CH 3,4-Difluorphenyl 2-65 F NH 2 H F N 4-Fluorphenyl 2-66 F NH 2 H F N 3,4-Difluorphenyl 2-67 F NH 2 Cl F N 4-Fluorphenyl 2-68 F NH 2 Cl F N 3,4-Difluorphenyl 2-69 F NH 2 Br F N 4-Fluorphenyl 2-70 F NH 2 Br F N 3,4-Difluorphenyl 2-71 F NH 2 NO 2 F N 4-Fluorphenyl 2-72 F NH 2 NO 2 F N 3,4-Difluorphenyl 2-73 F NHCOOEt H F N 4-Fluorphenyl 2-74 F NHCOOEt H F N 3,4-Difluorphenyl 2-75 F NH 2 H Cl N 4-Fluorphenyl 2-76 F NH 2 H Cl N 3,4-Difluorphenyl 2-77 F NH 2 Cl Cl N 4-Fluorphenyl 2-78 F NH 2 Cl Cl N 3,4-Difluorphenyl 2-79 F NH 2 Br Cl N 4-Fluorphenyl 2-80 F NH 2 Br Cl N 3,4-Difluorphenyl 2-81 F NH 2 NO 2 Cl N 4-Fluorphenyl 2-82 F NH 2 NO 2 Cl N 3,4-Difluorphenyl 2-83 F NHCOOEt H Cl N 4-Fluorphenyl 2-84 F NHCOOEt H Cl N 3,4-Difluorphenyl 2-85 Cl NH 2 H F N 4-Fluorphenyl 2-86 Cl NH 2 H F N 3,4-Difluorphenyl 2-87 Cl NH 2 Cl F N 4-Fluorphenyl 2-88 Cl NH 2 Cl F N 3,4-Difluorphenyl 2-89 Cl NH 2 Br F N 4-Fluorphenyl 2-90 Cl NH 2 Br F N 3,4-Difluorphenyl 2-91 Cl NH 2 NO 2 F N 4-Fluorphenyl 2-92 Cl NH 2 NO 2 F N 3,4-Difluorphenyl 2-93 Cl NHCOOEt H F N 4-Fluorphenyl 2-94 Cl NHCOOEt H F N 3,4-Difluorphenyl 2-95 Cl NH 2 H Cl N 4-Fluorphenyl 2-96 Cl NH 2 H Cl N 3,4-Difluorphenyl 2-97 Cl NH 2 Cl Cl N 4-Fluorphenyl 2-98 Cl NH 2 Cl Cl N 3,4-Difluorphenyl 2-99 Cl NH 2 Br Cl N 4-Fluorphenyl 2-100 Cl NH 2 Br Cl N 3,4-Difluorphenyl 2-101 Cl NH 2 NO 2 Cl N 4-Fluorphenyl 2-102 Cl NH 2 NO 2 Cl N 3,4-Difluorphenyl 2-103 Cl COOH H Cl N 4-Fluorphenyl 2-104 Cl COOH H Cl N 3,4-Difluorphenyl 2-105 Cl COOMe H Cl N 4-Fluorphenyl 2-106 Cl COOMe H Cl N 3,4-Difluorphenyl 2-107 Cl NHCOOEt H Cl N 4-Fluorphenyl 2-108 Cl NHCOOEt H Cl N 3,4-Difluorphenyl 2-109 CN NH 2 H F N 4-Fluorphenyl 2-110 CN NH 2 H F N 3,4-Difluorphenyl 2-111 CN NH 2 Cl F N 4-Fluorphenyl 2-112 CN NH 2 Cl F N 3,4-Difluorphenyl 2-113 CN NH 2 Br F N 4-Fluorphenyl 2-114 CN NH 2 Br F N 3,4-Difluorphenyl 2-115 CN NH 2 NO 2 F N 4-Fluorphenyl 2-116 CN NH 2 NO 2 F N 3,4-Difluorphenyl 2-117 CN NHCOOEt H F N 4-Fluorphenyl 2-118 CN NHCOOEt H F N 3,4-Difluorphenyl 2-119 CN NH 2 H Cl N 4-Fluorphenyl 2-120 CN NH 2 H Cl N 3,4-Difluorphenyl 2-121 CN NH 2 Cl Cl N 4-Fluorphenyl 2-122 CN NH 2 Cl Cl N 3,4-Difluorphenyl 2-123 CN NH 2 Br Cl N 4-Fluorphenyl 2-124 CN NH 2 Br Cl N 3,4-Difluorphenyl 2-125 CN NH 2 NO 2 Cl N 4-Fluorphenyl 2-126 CN NH 2 NO 2 Cl N 3,4-Difluorphenyl 2-127 CN NHCOOEt H Cl N 4-Fluorphenyl 2-128 CN NHCOOEt H Cl N 3,4-Difluorphenyl 2-129 H H NO 2 Cl N 4-Fluorphenyl 2-130 H NH 2 NO 2 Cl N 4-Fluorphenyl 2-131 H NH 2 H Cl N 4-Fluorphenyl 2-132 H NHCOOEt H Cl N 4-Fluorphenyl 2-133 H COOH H Cl N 4-Fluorphenyl 2-134 H COOMe H Cl N 4-Fluorphenyl 2-135 H NH 2 H F N 4-Fluorphenyl 2-136 H NHCOOEt H F N 4-Fluorphenyl 2-137 H COOH H F N 4-Fluorphenyl 2-138 H COOMe H F N 4-Fluorphenyl 2-139 Br Br H Cl N 4-Fluorphenyl 2-140 H NH 2 Br Cl N 4-Fluorphenyl 2-141 H NHCOOEt NO 2 Cl N 4-Fluorphenyl

[0074] By analogy to the manufacturing examples mentioned above and cited at the appropriate point, the following compounds of the general formula, shown in Table 3, are obtained. Table 3 Beispielnummer R 2< R 3< A R 1< 3-1 H F CH Pyridin-2-yl 3-2 H F CH 5-Fluorpyridin-2-yl 3-3 H F CH 5-Chlorpyridin-2-yl 3-4 H Cl CH Pyridin-2-yl 3-5 H Cl CH 5-Fluorpyridin-2-yl 3-6 H Cl CH 5-Chlorpyridin-2-yl 3-7 F F CH Pyridin-2-yl 3-8 F F CH 5-Fluorpyridin-2-yl 3-9 F F CH 5-Chlorpyridin-2-yl 3-10 F Cl CH Pyridin-2-yl 3-11 F Cl CH 5-Fluorpyridin-2-yl 3-12 F Cl CH 5-Chlorpyridin-2-yl 3-13 Cl F CH Pyridin-2-yl 3-14 Cl F CH 5-Fluorpyridin-2-yl 3-15 Cl F CH 5-Chlorpyridin-2-yl 3-16 Cl Cl CH Pyridin-2-yl 3-17 Cl Cl CH 5-Fluorpyridin-2-yl 3-18 Cl Cl CH 5-Chlorpyridin-2-yl 3-19 CN F CH Pyridin-2-yl 3-20 CN F CH 5-Fluorpyridin-2-yl 3-21 CN F CH 5-Chlorpyridin-2-yl 3-22 CN Cl CH Pyridin-2-yl 3-23 CN Cl CH 5-Fluorpyridin-2-yl 3-24 CN Cl CH 5-Chlorpyridin-2-yl 3-25 H F N Pyridin-2-yl 3-26 H F N 5-Fluorpyridin-2-yl 3-27 H F N 5-Chlorpyridin-2-yl 3-28 H Cl N Pyridin-2-yl 3-29 H Cl N 5-Fluorpyridin-2-yl 3-30 H Cl N 5-Chlorpyridin-2-yl 3-31 F F N Pyridin-2-yl 3-32 F F N 5-Fluorpyridin-2-yl 3-33 F F N 5-Chlorpyridin-2-yl 3-34 F Cl N Pyridin-2-yl 3-35 F Cl N 5-Fluorpyridin-2-yl 3-36 F Cl N 5-Chlorpyridin-2-yl 3-37 Cl F N Pyridin-2-yl 3-38 Cl F N 5-Fluorpyridin-2-yl 3-39 Cl F N 5-Chlorpyridin-2-yl 3-40 Cl Cl N Pyridin-2-yl 3-41 Cl Cl N 5-Fluorpyridin-2-yl 3-42 Cl Cl N 5-Chlorpyridin-2-yl 3-43 CN F N Pyridin-2-yl 3-44 CN F N 5-Fluorpyridin-2-yl 3-45 CN F N 5-Chlorpyridin-2-yl 3-46 CN Cl N Pyridin-2-yl 3-47 CN Cl N 5-Fluorpyridin-2-yl 3-48 CN Cl N 5-Chlorpyridin-2-yl 3-49 H Cl N Pyridin-3-yl 3-50 H Cl N 2-Fluorpyridin-5-yl 3-51 H Cl N 2-Chlorpyridin-5-yl 3-52 H Cl N 2-Trifluormethyl-pyridin-5-yl 3-53 CN F N 2-Fluorpyridin-5-yl 3-54 CN F N 2-Chlorpyridin-5-yl 3-55 CN Cl N 2-Fluorpyridin-5-yl 3-56 CN Cl N 2-Chlorpyridin-5-yl

[0075] The NMR data of disclosed examples are listed in classical form (δ values, number of H atoms, multiplet splitting). NMR data of the final products (classical form)

[0076] 1-40: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 8.83 (s,1H); 8.12 (dd,1H); 8.03 (m,1H); 7.63 (dd,1H); 7.22 (dt,1H); 7.13 (m,2H); 7.01 (dd,1H); 6.97 (m,1H); 6.68 (m,2H) 1-75: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 8.77 (s,1H); 8.14 (dd,1H); 8.12 (m,1H); 7.62 (dd,1H); 7.26 (t,1H); 7.20 (dd,1H); 7.11 (m,2H); 6.95 (dd,1H); 6.79 (m,2H) 1-79: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 8.47 (s,1H); 8.07 (dd,1H); 7.93 (d,1H); 7.56 (dd,1H); 7.13 (t,1H); 7.08 (m,2H); 6.96 (m,1H); 6.87 (dd,1H); 6.74 (m,2H); 2.06 (s,3H) 1-88: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.71 (s,1H); 8.61 (dd,1H); 8.13 (dd,1H); 7.56 (m,1H); 7.46 (dd,1H); 7.39 (t,1H); 7.15 (m,2H); 6.94 (d,1H); 6.87 (m,2H); 6.81 (t,1H) 1-106: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.81 (s,1H); 8.52 (dd,1H); 8.1 (d,1H); 7.55 (ddd,1H); 7.46 (dd,1H); 7.39 (t,1H); 7.14 (m,2H); 6.99 (dd,1H); 6.86 (m,2H) 1-111: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 8.81 (s,1H); 8.48 (dd,1H); 8.21 (d,1H); 7.55 (ddd,1H); 7.46 (dd,1H); 7.43-7.31 (m,2H); 7.04 (m,1H); 6.97 (dd,1H); 6.67 (m,1H) 1-124: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.94 (s,1H); 8.47 (dd,1H); 8.14 (d,1H); 7.64 (dd,1H); 7.52 (dd,1H); 7.41 (t,1H); 7.14 (m,2H); 6.95 (d,1H); 6.85 (m,2H) 1-129: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 8.82 (s,1H); 8.48 (dd,1H); 8.13 (d,1H); 7.66 (dd,1H); 7.54 (dd,1H); 7.44-7.30 (m,2H); 7.03 (m,1H); 6.92 (d,1H); 6.60 (m,1H) 1-139: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.64 (s,1H); 7.97 (d,1H); 7.93 (dd,1H); 7.68 (dd,1H); 7.44 (t,1H); 7.38 (d,1H); 7.08 (m,2H); 6.72 (m,2H) 1-143: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.94 (s,1H); 8.46 (d,1H); 8.20 (d,1H); 7.73 (dd,1H); 7.51 (dd,1H); 7.41 (t,1H); 7.14 (m,2H); 6.90 (d,1H); 6.85 (m,2H) 1-144: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 8.95 (s,1H); 8.44 (dd,1H); 8.21 (d,1H); 7.75 (dd,1H); 7.55 (dd,1H); 7.47-7.32 (m,2H); 7.04 (m,1H); 6.89 (d,1H); 6.61 (m,1H) 1-145: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.46 (s,1H); 8.51 (d,1H); 8.29 (dd,1H); 7.88 (dd,1H); 7.67 (dd,1H); 7.46 (t,1H); 7.12 (m,2H); 6.88 (d,1H); 6.82 (m,2H) 1-146: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 10.98 (s,1H); 8.68 (d,1H); 8.14 (d,1H); 8.04 (dd,1H); 7.83 (dd,1H); 7.57 (t,1H); 7.28-7.19 (m,2H); 6.96-6.86 (m,1H); 6.54 (m,1H) 1-147: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.83 (s,1H); 8.95 (d,1H); 8.27 (dd,1H); 8.25 (dd,1H); 7.73 (dd,1H); 7.49 (t,1H); 7.11 (m,2H); 6.87 (d,1H); 6.83 (m,2H) 1-149: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.62 (dd,1H); 8.58 (s,1H); 7.98 (s,1H); 7.42-7.36 (m,3H); 7.15 (m,2H); 6.90-6.86 (m,3H); 2.17 (s,3H) 1-153: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.58 (dd,1H); 8.53 (s,1H); 7.98 (d,1H); 7.37-7.31 (m,2H); 7.30 (dd,1H); 7.15 (m,2H); 6.98 (d,1H); 6.88 (m,2H); 3.75 (s,3H) 1-155: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.81 (s,1H); 8.55 (dd,1H); 8.10 (d,1H); 7.60 (dd,1H); 7.47 (dd,1H); 7.39 (t,1H); 7.14 (m,2H); 6.93 (d,1H); 6.86 (m,2H); 2.42 (s,3H) 1-204: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.21 (s,1H); 8.44 (s,2H); 7.66 (m,1H); 7.28 (m,1H); 7.15 (m,1H); 7.10 (m,2H); 6.83 (m,2H) 1-235: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.12 (s,1H); 8.45 (s,2H); 7.82 (dd,1H); 7.37 (dd,1H); 7.31 (t,1H); 7.08 (m,2H); 6.73 (m,2H) 1-239: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.78 (s,1H); 8.42 (s,2H); 7.70 (dd,1H); 7.18 (t,1H); 7.09 (d,1H); 7.07 (m,2H); 6.72 (m,2H); 2.09 (s,3H) 1-246: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.10 (s,11H); 8.42 (d,2H); 8.21 (d,1H); 7.74 (d,1H); 7.47 (t.1H); 7.27 (m,1H); 7.08-6.99 (m,2H); 6.86 (m,1H); 6.65 (m,1H) 1-247: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.05 (s,1H); 8.40 (d,2H); 8.25 (d,1H); 7.69 (d,1H); 7.47 (t.1H); 7.30 (m,1H); 6.91-6.85 (m,2H); 6.68 (m,1H); 6.61 (m,1H) 1-248: 1< H-NMR (400.0 MHz, MeOD): δ= 8.64 (dd,1H); 8.43 (d,2H); 7.49-7.41 (m,2H); 7.03 (m,2H); 6.92-6.87 (m,3H) 1-249: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.11 (s,1H); 8.40 (d,2H); 8.23 (d,1H); 7.68 (d,1H); 7.49 (t.1H); 7.30 (m,1H); 7.10 (m,1H); 6.86 (m,2H); 6.75 dd,1H) 1-250: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.04 (s,1H); 8.40 (d,2H); 8.26 (d,1H); 7.68 (d,1H); 7.47 (t.1H); 7.33 (m,2H); 6.86 (m,1H); 6.81 (d,2H) 1-251: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.17 (s,1H); 8.40 (d,2H); 8.17 (d,1H); 7.68 (d,1H); 7.47 (t.1H); 7.37 (m,1H); 6.92 (m,1H); 6.86 (m,1H); 6.74 (m,1H) 1-252: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.24 (s,1H); 8.39 (d,2H); 8.12 (d,1H); 7.71 (d,1H); 7.46 (t.1H); 7.31 (m,1H); 6.92 (m,1H); 6.85 (m,1H); 6.54 (m,1H) 1-253: 1< H-NMR (400.0 MHz, CDCl 3 ): δ= 9.01 (dd,11H); 8.48 (d,2H); 7.52 (s,1H); 7.41-7.28 (m,2H); 7.12 (m,1H); 6.87 (m,1H); 6.81 (m,1H); 6.70 (m,1H) 1-254: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.16 (s,1H); 8.40 (d,2H); 8.20 (d,1H); 7.69 (d,1H); 7.50 (t.1H); 6.92 (m,1H); 6.85 (m,1H); 6.55 (m,2H) 1-255: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.06 (s,1H); 8.40 (d,2H); 8.18 (d,1H); 7.68 (d,1H); 7.54-7.46 (m,2H); 7.06 (m,1H); 6.86 (m,1H); 6.65 (dd,1H) 1-256: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.24 (s,1H); 8.40 (d,2H); 8.19 (d,1H); 7.70 (d,1H); 7.53 (d,1H); 7.46 (t,1H); 7.10 (m,1H); 6.86 (m,1H); 6.69 (m,1H) 1-259: 1< H-NMR (400.0 MHz, CDCl 3 ): δ= 9.00 (dd,1H); 8.48 (d,2H); 7.52 (s,1H); 7.48-7.34 (m,4H); 7.20 (s,1H); 7.12 (dd,1H); 6.86 (m,1H) 1-260: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.17 (s,1H); 8.39 (d,2H); 8.28 (d,1H); 7.68 (d,1H); 7.64 (d,2H); 7.51 (t,1H); 6.98 (d,2H); 6.86 (m,1H) 1-261: 1< H-NMR (300.0 MHz, d 6 -DMSO): δ= 9.17 (s,1H); 8.34 (d,2H); 8.22 (d,1H); 7.76 (d,2H); 7.68 (d,1H); 7.49 (t,1H); 6.93 (d,2H); 6.83 (m,1H) 1-262: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 8.87 (s,1H); 8.42 (d,2H); 8.29 (d,1H); 7.65 (d,1H); 7.44 (t.1H); 7.15 (m,1H); 6.86 (m,1H); 6.61 (m,1H); 6.38 (s,1H); 6.31 (d,1H); 3.34 (s,3H) 1-265: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.29 (s,1H); 8.49 (s,2H); 8.10 (d,1H); 7.68 (d,1H); 7.48 (t.1H); 7.26 (m,11H); 7.10-7.00 (m,2H); 6.64 (m,1H) 1-266: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.24 (s,1H); 8.49 (s,2H); 8.16 (d,1H); 7.70 (d,1H); 7.46 (t.1H); 7.31 (m,1H); 6.89 (m,H); 6.67 (m,1H); 6.60 (m,1H) 1-267: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.15 (s,1H); 8.48 (s,2H); 8.14 (dd,1H); 7.65 (dd,1H); 7.45 (t,1H); 7.10 (m,2H); 6.79 (m,2H) 1-268: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.28 (s,1H); 8.49 (s,2H); 8.14 (d,1H); 7.74 (d,1H); 7.49 (t.1H); 7.30 (m,11H); 7.10 (m,1H); 6.84 (m,1H); 6.74 dd,1H) 1-269: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.23 (s,1H); 8.49 (s,2H); 8.15 (d,1H); 7.69 (d,1H); 7.45 (t.1H); 7.32 (m,2H); 6.79 (d,2H) 1-270: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.33 (s,1H); 8.50 (s,2H); 8.07 (d,1H); 7.68 (d,1H); 7.48 (t.1H); 7.36 (m,1H); 6.92 (m,1H); 6.74 (m,1H) 1-271: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.39 (s,1H); 8.49 (s,2H); 8.06 (d,1H); 7.73 (d,1H); 7.48 (t.1H); 7.31 (m,1H); 6.90 (m,1H); 6.55 (m,1H) 1-272: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.25 (s,1H); 8.49 (s,2H); 8.11 (dd,1H); 7.68 (dd,1H); 7.47 (t,1H); 7.33 (m,1H); 6.96 (m,1H); 6.58 (m,1H) 1-273: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.33 (s,1H); 8.50 (s,2H); 8.11 (d,1H); 7.70 (d,1H); 7.49 (t.1H); 6.94 (m,1H); 6.54 (m,2H) 1-274: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.25 (s,1H); 8.50 (s,2H); 8.06 (d,1H); 7.68 (d,1H); 7.54-7.46 (m,2H); 7.06 (m,1H); 6.63 (dd,1H) 1-275: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.39 (s,1H); 8.51 (s,2H); 8.09 (d,1H); 7.71 (d,1H); 7.53 (m,1H); 7.46 (t,1H); 7.11 (m,1H); 6.69 (m,1H) 1-278: 1< H-NMR (400.0 MHz, CDCl 3 ): δ= 8.90 (dd,1H); 8.35 (s,2H); 7.51-7.34 (m,5H); 7.19 (s,1H); 7.12 (m,1H) 1-279: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.34 (s,1H); 8.49 (s,2H); 8.18 (d,1H); 7.68 (d,1H); 7.64 (d,2H); 7.51 (t,1H); 6.96 (d,2H) 1-280: 1< H-NMR (300.0 MHz, d 6 -DMSO): δ= 9.34 (s,1H); 8.45 (s,2H); 8.12 (d,1H); 7.76 (d,2H); 7.68 (d,1H); 7.47 (t,1H); 6.92 (d,2H) 1-281: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.08 (s,1H); 8.50 (s,2H); 8.17 (d,1H); 7.66 (d,1H); 7.45 (t.1H); 7.14 (m,1H); 6.62 (m,1H); 6.35 (s,1H); 6.28 (d,1H); 3.34 (s,3H) 1-284: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.46 (s,1H); 8.46 (s,2H); 8.03 (d,1H); 7.72 (d,1H); 7.48 (t.1H); 7.30 (m,11H); 7.10-7.00 (m,2H); 6.65 (m,1H) 1-285: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.43 (s,1H); 8.47 (s,2H); 8.08 (d,1H); 7.70 (d,1H); 7.49 (t.1H); 7.29 (m,1H); 6.89 (m,H); 6.66 (m,1H); 6.59 (m,1H) 1-286: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.35 (s,1H); 8.45 (s,2H); 8.08 (dd,1H); 7.69 (dd,1H); 7.45 (t,1H); 7.10 (m,2H); 6.79 (m,2H) 1-287: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.47 (s,1H); 8.46 (s,2H); 8.07 (d,1H); 7.74 (d,1H); 7.49 (t.1H); 7.32 (m,1H); 7.10 (m,1H); 6.83 (s,1H); 6.75 d,1H) 1-288: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.43 (s,1H); 8.47 (s,2H); 8.09 (d,1H); 7.71 (d,1H); 7.45 (t.1H); 7.31 (d,2H); 6.79 (d,2H) 1-289: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.51 (s,1H); 8.47 (s,2H); 8.02 (d,1H); 7.72 (d,1H); 7.48 (t.1H); 7.35 (m,1H); 6.93 (m,1H); 6.74 (m,1H) 1-290: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.56 (s,1H); 8.47 (s,2H); 8.01 (d,1H); 7.75 (d,1H); 7.48 (t.1H); 7.31 (m,1H); 6.93 (m,1H); 6.55 (m,1H) 1-291: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.43 (s,1H); 8.46 (s,2H); 8.06 (dd,2H); 7.72 (dd,1H); 7.48 (t,1H); 7.33 (m,1H); 6.95 (m,1H); 6.58 (m,1H) 1-292: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.51 (s,1H); 8.47 (s,2H); 8.06 (d,1H); 7.74 (d,1H); 7.49 (t.1H); 6.94 (m,1H); 6.54 (m,2H) 1-293: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.43 (s,1H); 8.47 (s,2H); 8.01 (d,1H); 7.74 (d,1H); 7.54-7.46 (m,2H); 7.06 (m,1H); 6.63 (dd,1H) 1-294: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.55 (s,1H); 8.47 (s,2H); 8.03 (d,1H); 7.75 (d,1H); 7.53 (m,1H); 7.46 (t,1H); 7.11 (m,1H); 6.70 (m,1H) 1-297: 1< H-NMR (400.0 MHz, CDCl 3 ): δ= 8.89 (dd,1H); 8.40 (s,2H); 7.52-7.35 (m,5H); 7.19 (s,1H); 7.11 (m,1H) 1-298: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.51 (s,1H); 8.46 (s,2H); 8.11 (d,1H); 7.67 (d,1H); 7.64 (d,2H); 7.50 (t,1H); 6.96 (d,2H) 1-299: 1< H-NMR (300.0 MHz, d 6 -DMSO): δ= 9.50 (s,1H); 8.42 (s,2H); 8.07 (d,1H); 7.74-7.66 (m,3H); 7.47 (t,1H); 6.91 (d,2H) 1-300: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.30 (s,1H); 8.47 (s,2H); 8.08 (d,1H); 7.70 (d,1H); 7.45 (t.1H); 7.13 (m,1H); 6.62 (m,1H); 6.33 (s,1H); 6.28 (d,1H); 3.34 (s,3H) 1-304: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 10.11 (s,1H); 8.76 (s,2H); 8.92 (d,1H); 7.80 (d,1H); 7.48 (t,1H); 7.08 (m,2H); 6.77 (m,2H) 1-305: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 10.14 (s,1H); 8.76 (s,2H); 7.92 (dd,1H); 7.82 (dd,1H); 7.48 (t,1H); 7.30 m,1H); 6.94 (m,1H); 6.56 (m,1H) 1-306: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 10.50 (s,1H); 9.12 (s,2H); 7.94 (dd,1H); 7.86 (d,1H); 7.51 (t,1H); 7.09 (m,2H); 6.79 (m,2H) 1-308: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.73 (s,1H); 8.35 (dd,1H); 8.28 (s,2H); 7.59 (dd,1H); 7.44 (t,1H); 7.12 (m,2H); 6.84 (m,2H); 2.12 (s,3H) 1-310: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.76 (s,1H); 8.35 (dd,1H); 8.31 (s,2H); 7.59 (dd,1H); 7.44 (t,1H); 7.11 (m,2H); 6.83 (m,2H); 2.49 (q,2H); 1.14 (s,3H) 1-312: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.66 (s,1H); 8.35 (dd,1H); 8.25 (s,2H); 7.55 (dd,1H); 7.43 (t,1H); 7.12 (m,2H); 6.83 (m,2H); 3.80 (s,3H) 1-314: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.26 (s,1H); 8.37 (s,2H); 8.13 (dd,1H); 7.67 (dd,1H); 7.45 (t,1H); 7.12 (t,1H); 7.09 (m,2H); 6.79 (m,2H) 1-318: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.17 (s,1H); 8.42 (s,2H); 8.17 (dd,1H); 7.66 (dd,1H); 7.45 (t,1H); 7.10 (m,2H); 6.80 (m,2H); 2.42 (s,3H) 1-324: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 8.78 (s,1H); 8.42 (s,2H); 7.49 (dd,1H); 7.22 (t,1H); 7.05 (m,2H); 6.95 (dd,1H); 6.73 (m,2H); 3.71 (s,3H) 1-328: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 8.89 (s,1H); 8.42 (s,2H); 7.62 (dd,1H); 7.28 (t,1H); 7.12 (dd,1H); 7.04 (m,2H); 6.69 (m,2H); 2.39 (s,3H) 1-330: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.88 (s,1H); 8.52 (dd,1H); 8.04 (d,1H); 7.51 (dd,1H); 7.48 (dd,1H); 7.40 (t,1H); 7.14 (m,2H); 7.10 (t,1H); 6.99 (d,1H); 6.86 (m,2H) 1-332: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.03 (s,1H); 8.46 (dd,1H); 8.18 (d,1H); 7.65 (dd,1H); 7.54 (dd,1H); 7.42 (t,1H); 7.13 (m,2H); 6.99 (d,1H); 6.84 (m,2H) 1-334: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.28 (s,1H); 8.36 (dd,1H); 8.32 (d,1H); 7.81 (dd,1H); 7.62 (dd,1H); 7.45 (t,1H); 7.11 (m,2H); 6.93 (d,1H); 6.82 (m,2H) 1-336: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.91 (s,1H); 8.44 (s,2H); 7.80 (dd,1H); 7.33 (m,2H); 7.17-7.07 (m,3H); 6.95-6.92 (m,3H) 1-337: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 8.99 (s,1H); 8.44 (s,2H); 7.77 (m,1H); 7.19-7.10 (m,3H); 6.99 (m,2H); 6.90 (m,1H) 1-339: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.16 (s,1H); 8.39 (s,2H); 7.77-7.75 (m,3H); 7.27 (m,1H); 7.22 (m,1H); 7.14 dd,1H); 6.99 (dd,2H) 1-340: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.03 (s,1H); 8.45 (s,2H); 7.84 (dd,1H); 7.36 (dd,1H); 7.31 (t,1H); 7.25 (dd,2H); 6.99 (t,1H); 6.72 (d,2H) 1-341: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.18 (s,1H); 8.45 (s,2H); 7.81 (dd,1H); 7.38 (dd,1H); 7.33-7.29 (m,3H); 6.99 (t,1H); 6.73 (ddd,2H) 1-342: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.58 (dd,1H); 8.52 (s,1H); 7.86 (d,1H); 7.37-7.35 (m,2H); 7.29 (dd,1H); 7.15 (m,2H); 6.95 (d,1H); 6.88 (m,2H); 4.45 (m,1H); 1.24 (d,6H) 1-344: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.66 (s,1H); 8.35 (dd,1H); 8.22 (s,2H); 7.56 (dd,1H); 7.43 (t,1H); 7.12 (m,2H); 6.83 (m,2H); 4.45 (m,1H); 1.25 (d,6H) 1-350: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.36 (s,1H); 8.47 (d,2H); 8.10 (dd,1H); 7.83 (dd,1H); 7.50 (t,1H); 7.07 (m,2H); 6.75 (m,2H) 1-354: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.53 (s,1H); 8.39 (s,2H); 7.06-7.03 (m,3H); 6.94 (t,1H); 6.77 (m,2H); 6.59 (dd,1H); 4.93 (s,2H) 1-358: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.10 (s,1H); 8.45 (s,2H); 7.83 (dd,1H); 7.51 (dd,1H); 7.24 (t,1H); 7.08 (m,2H); 6.70 (m,2H) 1-360: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.58 (dd,1H); 8.52 (s,1H); 7.88 (d,1H); 7.37-7.34 (m,2H); 7.29 (dd,1H); 7.15 (m,2H); 6.97 (d,1H); 6.88 (m,2H); 4.01 (q,2H); 1.30 (t,3H) 1-362: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.64 (s,1H); 8.35 (dd,1H); 8.23 (s,2H); 7.56 (dd,1H); 7.43 (t,1H); 7.12 (m,2H); 6.83 (m,2H); 4.06 (q,2H); 1.31 (t,3H) 1-364: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 10.98 (s,1H); 8.64 (s,2H); 7.83 (t,1H); 7.70 (d,1H); 7.67 (d,1H); 7.56 (d,1H); 7.14 (dd,1H); 7.07 (t,1H) 1-365: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.57 (s,1H); 8.39 (s,2H); 7.08-7.02 (m,4H); 6.73 (m,2H); 6.47 (d,2H); 5.23 (q,1H); 2.68 (d,3H) 1-366: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.64 (s,1H); 8.41 (s,2H); 7.70 (d,1H); 7.47 (dd,1H); 7.15 (t,1H); 7.03 (m,2H); 6.81 (dd,1H); 6.7 (m,2H); 2.68 (s,6H) 1-367: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.87 (s,1H); 9.82 (d,1H); 8.91 (s,1H); 8.40 (s,2H); 8.05 (d.1H); 7.46 (d,1H); 7.22 (t,1H); 7.04 (m,2H); 6.70 (m,2H) 1-368: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.44 (s,1H); 8.95 (s,1H); 8.40 (s,2H); 7.70 (d,1H); 7.48 (d.1H); 7.21 (t,1H); 7.04 (m,2H); 6.72 (m,2H); 1.90 (s,3H) 1-369: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.11 (s,1H); 8.46 (s,2H); 7.87 (dd,1H); 7.33 (t,1H); 7.22 (dd,1H); 7.06 (m,2H); 6.72 (m,2H); 2.84 (s,3H); 1.71 (s,3H) 1-372: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.02 (s,1H); 8.43 (s,2H); 7.84 (dd,1H); 7.68 (dd,1H); 7.08 (t,1H); 7.07 (m,2H); 6.70 (m,2H) 1-374: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.41 (s,1H); 8.51 (s,2H); 8.11 (dd,1H); 7.70 (dd,1H); 7.48 (t,1H); 7.17 (m,1H); 6.56 (m,1H) 1-375: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.35 (s,1H); 8.49 (s,2H); 8.04 (dd,1H); 7.70 (dd,1H); 7.68 (m,1H); 7.46 (t,1H); 6.95 (m,1H) 1-376: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.87 (s,1H); 8.42 (s,2H); 7.63 (dd,1H); 7.28 (t,1H); 7.18 (dd,1H); 7.03 (m,2H); 6.69 (m,2H); 2.93 (q,2H); 1.20 (t,3H) 2-101: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.08 (s,1H); 8.39 (s,2H); 8.27 (s,1H); 7.43 (s,2H); 7.07 (m,2H); 6.76 (m,2H) 2-103: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 13.29 (brs,1H); 9.26 (s,1H); 8.56 (s,2H); 8.11 (d,1H); 7.80 (d,1H); 7.11 (m,2H); 6.78 (m,2H) 2-105: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.32 (s,1H); 8.57 (s,2H); 8.18 (d,1H); 7.82 (d,1H); 7.12 (m,2H); 6.77 (m,2H); 3.85 (s,3H) 2-130: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.02 (s,1H); 8.47 (s,2H); 8.21 (s,1H); 7.40 (s,2H); 7.31 (m,2H); 7.21 (m,2H); 6.24 (s,1H) 2-131: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 8.63 (s,1H); 8.29 (s,2H); 7.14 (m,2H); 7.08 (d,1H); 6.96 (m,2H); 6.32 (dd,1H); 6.08 (d,1H); 5.12 (s,2H) 2-132: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.62 (s,1H); 8.91 (s,1H); 8.38 (s,2H); 7.49 (d,1H); 7.19-7.13 (m,4H); 6.98 (m,2H); 4.06 (q,2H); 1.20 (t,3H) 2-133: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 12.88 (brs,1H); 9.18 (s,1H); 8.58 (s,2H); 8.16 (d,1H); 7.71 (dd,1H); 7.30 (d,1H); 7.25 (m,2H); 7.13 (m,2H) 2-134: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.23 (s,1H); 8.60 (s,2H); 8.22 (d,1H); 7.76 (dd,1H); 7.32 (d,1H); 7.26 (m,2H); 7.12 (m,2H); 3.78 (s,3H) 2-135: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.37 (s,1H); 8.31 (s,2H); 7.14-7.11 (m,3H); 6.94 (m,2H); 6.31 (dd,1H); 6.08 (d,1H); 5.07 (s,2H) 2-136: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.59 (s,1H); 8.67 (s,1H); 8.41 (s,2H); 7.57 (d,1H); 7.19-7.14 (m,4H); 6.98 (m,2H); 4.06 (q,2H); 1.20 (t,3H) 2-137: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.98 (s,1H); 8.62 (s,2H); 8.27 (d,1H); 7.72 (dd,1H); 7.30 (d,1H); 7.25 (m,2H); 7.13 (m,2H) 2-138: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.04 (s,1H); 8.63 (d,2H); 8.32 (d,1H); 7.75 (dd,1H); 7.32 (d,1H); 7.26 (m,2H); 7.13 (m,2H); 3.78 (s,3H) 2-139: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.19 (s,1H); 8.48 (d,2H); 7.86 dd,1H); 7.70 (d,1H); 7.09 (m,2H); 6.73 (m,2H) 2-140: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 8.55 (s,1H); 8.38 (s,2H); 7.55 (s,1H); 7.16 (m,2H); 6.99 (m,2H); 6.34 (s,1H) 2-141: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.72 (s,1H); 9.33 (s,1H); 8.56 (s,2H); 8.56 (s,1H); 7.32 (m,2H); 7.28 (s,1H); 7.23 (m,2H); 4.07 (q,2H); 1.18 (t,3H) 3-49: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.15 (s,1H); 8.41 (s,2H); 8.29-8.27 (m,2H); 7.75 (dd,1H); 7.34 (dd,1H); 7.29 (m,1H); 7.23-7.16 (m,2H); 7.02 (m,1H) 3-53: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.39 (s,1H); 8.48 (s,2H); 8.11 (dd,1H); 7.78 (m,1H); 7.69 (d,1H); 7.48 (t,1H); 7.42 (m,1H); 7.11 (dd,1H) 3-54: 1< H-NMR (400.0 MHz, d 6 -DMSO): δ= 9.44 (s, 11H); 8.49 (d,2H); 8.13 (dd,1H); 8.01 (d,1H); 7.70 (dd,1H); 7.48 (t,11H); 7.40 (dd,1H); 7.28 (dd,1H) 3-55: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.56 (s,1H); 8.46 (s,2H); 8.06 (dd,1H); 7.78 (m,1H); 7.72 (d,1H); 7.48 (t,1H); 7.42 (m,1H); 7.10 (dd,1H) 3-56: 1< H-NMR (600.0 MHz, d 6 -DMSO): δ= 9.59 (s,1H); 8.46 (s,2H); 8.08 (dd,1H); 8.01 (d,1H); 7.74 (dd,1H); 7.49 (t,1H); 7.41 (d,1H); 7.28 (dd,1H)

[0077] The present invention further relates to the use of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of formulas 1-1 to 1-376, 2-1 to 2-141, 3-1 to 3-56 and / or their salts, each as defined above, as a herbicide and / or plant growth regulator, preferably in crops of useful and / or ornamental plants.

[0078] The present invention further relates to a method for controlling harmful plants and / or for regulating plant growth, characterized in that an effective quantity one or more compounds of general formula (I) and / or their salts, as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of formulas 1-1 to 1-376, 2-1 to 2-141, 3-1 to 3-56 and / or their salts, each as defined above, or an agent according to the invention, as defined below, is applied to the (harmful) plants, (harmful) plant seeds, the soil in which or on which the (harmful) plants grow, or the cultivation area.

[0079] The present invention also relates to a method for controlling unwanted plants, preferably in crop crops, characterized in that an effective quantity one or more compounds of general formula (I) and / or their salts, as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of formulas 1-1 to 1-376, 2-1 to 2-141, 3-1 to 3-56 and / or their salts, each as defined above, or of an agent according to the invention, as defined below, is applied to unwanted plants (such as pest plants like mono- or dicotyledonous weeds or unwanted cultivated plants), the seed of the unwanted plants (i.e. plant seeds, such as grains, seeds or vegetative propagating organs such as tubers or shoot parts with buds), the soil in which or on which the unwanted plants grow (such as the soil of cultivated land or non-cultivated land) or the cultivation area (i.e. area on which the unwanted plants will grow).

[0080] The present invention further relates to a method for combating and regulating the growth of plants, preferably crop plants, characterized in that an effective quantity one or more compounds of general formula (I) and / or their salts, as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of formulas 1-1 to 1-376, 2-1 to 2-141, 3-1 to 3-56 and / or their salts, each as defined above, or an agent according to the invention, as defined below, is applied to the plant, the seed of the plant (i.e. plant seeds, such as grains, seeds or vegetative propagating organs such as tubers or shoot parts with buds), the soil in which or on which the plants grow (such as the soil of cultivated land or non-cultivated land) or the cultivation area (i.e. area on which the plants will grow).

[0081] The compounds or agents according to the invention can be applied, for example, by pre-sowing (optionally also by incorporation into the soil), pre-emergence, and / or post-emergence methods. Specifically, some representatives of the monocotyledonous and dicotyledonous weed flora that can be controlled by the compounds according to the invention are mentioned below.

[0082] Preferably, in a method according to the invention for controlling pests or for regulating plant growth, one or more compounds of the general formula (I) and / or their salts are used for controlling pests or for regulating plant growth in crops of useful plants or ornamental plants, wherein the useful plants or ornamental plants are, in a preferred embodiment, transgenic plants.

[0083] The compounds of general formula (I) and / or their salts according to the invention are suitable for controlling the following genera of monocotyledonous and dicotyledonous weeds: Monocotyledonous pest plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

[0084] Dicotyledonous pest plants of the genera:Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

[0085] If the compounds of general formula (I) according to the invention are applied to the soil surface before the germination of the harmful plants (grasses and / or weeds) (pre-emergence method), either the emergence of the grass or weed seedlings is completely prevented or they grow up to the cotyledon stage, but then stop growing and finally die completely after three to four weeks.

[0086] When the active ingredients of the general formula (I) are applied to the green parts of the plants in the post-emergence method, growth stops after treatment and the weeds remain in the growth stage present at the time of application or die completely after a certain time, so that in this way weed competition harmful to the crop plants is eliminated very early and sustainably.

[0087] Although the compounds of the general formula (I) according to the invention exhibit excellent herbicidal activity against mono- and dicotyledonous weeds, cultivated plants of economically important crops such as dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea are only minimally damaged or not damaged at all, depending on the structure of the respective compound according to the invention and the amount applied. For these reasons, the compounds presented here are very well suited for the selective control of unwanted plant growth in plant crops such as agricultural crops or ornamental plantings.

[0088] Furthermore, the compounds of general formula (I) according to the invention (depending on their respective structure and the amount applied) exhibit excellent growth-regulating properties in cultivated plants. They have a regulatory effect on the plant's own metabolism and can therefore be used to selectively influence plant constituents and to facilitate harvesting by triggering desiccation and growth stunting. They are also suitable for the general control and inhibition of undesirable vegetative growth without killing the plants. Inhibition of vegetative growth plays a major role in many monocot and dicot crops, as lodging can be reduced or completely prevented as a result.

[0089] Due to their herbicidal and plant growth-regulating properties, the active ingredients of general formula (I) can also be used to control weeds in crops of genetically engineered or conventionally mutagenic plants. These transgenic plants are generally characterized by particularly advantageous properties, such as resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens such as certain insects or microorganisms like fungi, bacteria, or viruses. Other special properties relate to the harvested crop in terms of quantity, quality, storability, composition, and specific constituents. For example, transgenic plants with increased starch content or altered starch quality, or those with a different fatty acid composition of the harvested crop, are known.

[0090] With regard to transgenic crops, the application of the compounds of the general formula (I) and / or their salts according to the invention is preferred in economically important transgenic crops of useful and ornamental plants, e.g. of cereals such as wheat, barley, rye, oats, millet, rice and maize or also crops of sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetables.

[0091] Preferably, the compounds of general formula (I) according to the invention can also be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made resistant by genetic engineering.

[0092] Due to their herbicidal and plant growth-regulating properties, the compounds of general formula (I) according to the invention can also be used to control weeds in crops of known or yet-to-be-developed genetically modified plants. The transgenic plants are generally characterized by particularly 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 relate to the harvested crop with regard to quantity, quality, storability, composition, and specific constituents. For example, transgenic plants with increased starch content or altered starch quality, or those with a different fatty acid composition of the harvested crop, are known.Other special properties may include tolerance or resistance to abiotic stressors such as heat, cold, dryness, salt and ultraviolet radiation.

[0093] Preferred is the application of the compounds of general formula (I) or their salts according to the invention in economically important transgenic crops of useful and ornamental plants, e.g. cereals such as wheat, barley, rye, oats, triticale, millet, rice, cassava and maize or crops of sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetables.

[0094] Preferably, the compounds of general formula (I) can be used as herbicides in crops that are resistant to the phytotoxic effects of the herbicides or have been made resistant by genetic engineering.

[0095] Conventional methods for producing new plants with modified characteristics compared to existing plants include classical breeding techniques and the creation of mutants. Alternatively, new plants with altered characteristics can be produced using genetic engineering.

[0096] Numerous molecular biological techniques for producing new transgenic plants with altered properties are well known to experts. For such genetic manipulations, nucleic acid molecules can be introduced into plasmids, allowing mutagenesis or sequence modification through recombination of DNA sequences. Standard procedures can be used to perform base exchanges, remove partial sequences, or add natural or synthetic sequences. Adaptors or linkers can be attached to the DNA fragments to join them together.

[0097] The production of plant cells with reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to achieve a cosuppression effect, or the expression of at least one appropriately designed ribozyme that specifically cleaves transcripts of the aforementioned gene product.

[0098] This can be achieved using either DNA molecules that comprise the entire coding sequence of a gene product, including any flanking sequences, or DNA molecules that comprise only parts of the coding sequence, provided these parts are long enough to produce an antisense effect in the cells. It is also possible to use DNA sequences that exhibit a high degree of homology to the coding sequences of a gene product, but are not completely identical.

[0099] During the expression of nucleic acid molecules in plants, the synthesized protein can be localized in any compartment of the plant cell. However, to achieve localization in a specific compartment, the coding region can be linked to DNA sequences that ensure localization in that compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227). The expression of nucleic acid molecules can also take place in the organelles of plant cells.

[0100] The transgenic plant cells can be regenerated into entire plants using known techniques. In principle, the transgenic plants can be of any plant species, i.e., both monocotyledonous and dicotyledonous plants.

[0101] Thus, transgenic plants are available that exhibit altered properties through overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.

[0102] Preferably, the compounds of general formula (I) according to the invention can be used in transgenic cultures which are resistant to growth regulators such as dicamba or to herbicides that inhibit essential plant enzymes, e.g. acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), respectively, or to herbicides from the group of sulfonylureas, glyphosates, glufosinates or benzoylisoxazoles and analogous active substances.

[0103] When the compounds of the general formula (I) according to the invention are applied in transgenic crops, in addition to the effects observed in other crops against weeds, effects often occur that are specific to the application in the respective transgenic crop, for example, an altered or specifically extended weed spectrum that can be controlled, altered application rates that can be used for application, preferably good compatibility with the herbicides to which the transgenic crop is resistant, as well as influencing the growth and yield of the transgenic crop plants.

[0104] The invention therefore also relates to the use of the compounds of the general formula (I) and / or their salts as herbicides for controlling pests in crops of useful or ornamental plants, optionally in transgenic crops.

[0105] The use of compounds of general formula (I) in cereals, preferably maize, wheat, barley, rye, oats, millet or rice, in pre- or post-emergence is preferred.

[0106] The use of compounds of general formula (I) in soybeans in pre- or post-emergence applications is also preferred.

[0107] The use of compounds of formula (I) according to the invention for controlling pests or for regulating plant growth also includes the case in which a compound of general formula (I) or its salt is formed from a precursor substance (“prodrug”) only after application to the plant, in the plant or in the soil.

[0108] The invention also relates to the use of one or more compounds of the general formula (I) or their salts or of an agent according to the invention (as defined below) (in a method) for controlling pests or for regulating plant growth, characterized in that an effective amount of one or more compounds of the general formula (I) or their salts is applied to the plants (pests, optionally together with the crops), plant seeds, the soil in which or on which the plants grow, or the cultivation area. The invention also relates to a herbicidal and / or plant growth regulator, characterized in that the agent

[0109] (a) comprising one or more compounds of general formula (I) and / or their salts as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of formulas 1-1 to 1-376, 2-1 to 2-141, 3-1 to 3-56 and / or their salts, each as defined above, and (b) comprising one or more further substances selected from groups (i) and / or (ii): (i) comprising one or more further agrochemically active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides (i.e. those not corresponding to general formula (I) defined above), fungicides, safeners, fertilizers and / or further growth regulators, (ii) comprising one or more formulation aids commonly used in plant protection.

[0110] The other agrochemical active substances of component (i) of a composition according to the invention are preferably selected from the group of substances mentioned in "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.

[0111] A herbicidal or plant growth-regulating agent according to the invention preferably comprises one, two, three or more formulation aids (ii) commonly used in plant protection, selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusting agents, carriers solid at 25 °C and 1013 mbar, preferably adsorbable, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoaming agents, water, organic solvents, preferably organic solvents miscible with water in any proportion at 25 °C and 1013 mbar.

[0112] The compounds of general formula (I) according to the invention can be used in the form of sprayable powders, emulsifiable concentrates, sprayable solutions, dusts, or granules in conventional preparations. The invention therefore also relates to herbicidal and plant growth regulator agents containing compounds of general formula (I) and / or their salts.

[0113] The compounds of general formula (I) according to the invention and / or their salts can be formulated in various ways, depending on the biological and / or physicochemical parameters required. Possible formulations include: sprayable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusting agents (DP), pickling agents, granules for broadcast and ground application, granules (GR) in the form of micro-, sprayable, lift-off and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

[0114] These individual formulation types and formulation aids such as inert materials, surfactants, solvents, and other additives are known to those skilled in the art and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell NJ, Hv Olphen; "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, NY; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, NY 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; Schönfeldt, "Interfacially Active Ethylene Oxide Adducts", Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th edition 1986.

[0115] Spray powders are preparations that are uniformly dispersible in water and, in addition to the active ingredient, contain a diluent or inert substance as well as ionic and / or non-ionic surfactants (wetting agents, dispersants), such as polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium ligninsulfonic acid, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, sodium dibutylnaphthalenesulfonic acid, or sodium oleoylmethyltauric acid. To produce the spray powders, the herbicidal active ingredients are finely ground in conventional equipment such as hammer mills, blower mills, and air jet mills and simultaneously or subsequently mixed with the formulation excipients.

[0116] Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent such as butanol, cyclohexanone, dimethylformamide, xylene, or even higher-boiling aromatics or hydrocarbons, or mixtures of organic solvents, with the addition of one or more ionic and / or non-ionic surfactants (emulsifiers). Emulsifiers that can be used include: alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate, or non-ionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters, or polyoxyethylene sorbitan esters such as polyoxyethylene sorbitan fatty acid esters.

[0117] Dusting agents are obtained by grinding the active ingredient with finely dispersed solid substances such as talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

[0118] Suspension concentrates can be water- or oil-based. They can be produced by wet milling using commercially available bead mills and, if necessary, the addition of surfactants, as already listed above for the other formulation types.

[0119] Emulsions, such as oil-in-water emulsions (EW), can be prepared using stirrers, colloid mills and / or static mixers, with aqueous organic solvents and, if necessary, surfactants, as already listed above for the other formulation types.

[0120] Granules can be produced either by atomizing the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates to the surface of carrier materials such as sand, kaolinite, or granulated inert material using adhesives such as polyvinyl alcohol, sodium polyacrylate, or mineral oils. Alternatively, suitable active ingredients can be granulated in the manner customary for the production of fertilizer granules – optionally in mixture with fertilizers.

[0121] Water-dispersible granules are typically produced using standard methods such as spray drying, fluidized bed granulation, disc granulation, mixing with high-speed mixers, and extrusion without solid inert material.

[0122] For the production of disc-shaped, fluidized bed, extruded and spray-dried granules, see, for example, the processes in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff; "Perry's Chemical Engineer's Handbook", 5th ed., McGraw-Hill, New York 1973, pp. 8-57.

[0123] For further details on the formulation of plant protection products, see, for example, GC Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pages 81-96 and JD Freyer, SA Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

[0124] The agrochemical preparations, preferably herbicidal or plant growth regulators of the present invention, preferably contain a total amount of 0.1 to 99 wt.%, preferably 0.5 to 95 wt.%, more preferably 1 to 90 wt.%, and in particular preferably 2 to 80 wt.%, of active ingredients of general formula (I) and their salts.

[0125] In sprayable powders, the active ingredient concentration is approximately 10 to 90 wt%, with the remainder to 100 wt% consisting of usual formulation components. In emulsifiable concentrates, the active ingredient concentration can be approximately 1 to 90 wt%, preferably 5 to 80 wt%. Powder formulations contain 1 to 30 wt% active ingredient, preferably usually 5 to 20 wt%; sprayable solutions contain approximately 0.05 to 80 wt%, preferably 2 to 50 wt% active ingredient. In water-dispersible granules, the active ingredient content depends in part on whether the active compound is liquid or solid and which granulation aids, fillers, etc., are used. For water-dispersible granules, the active ingredient content is between 1 and 95 wt%, preferably between 10 and 80 wt%.

[0126] In addition, the aforementioned active ingredient formulations may contain the usual adhesives, wetting agents, dispersants, emulsifiers, penetrating agents, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, defoamers, evaporation inhibitors, and agents that affect pH and viscosity. Examples of formulation aids are described, among other places, in "Chemistry and Technology of Agrochemical Formulations", ed. D.A. Knowles, Kluwer Academic Publishers (1998).

[0127] The compounds of general formula (I) or their salts according to the invention can be used as such or in the form of their preparations (formulations) in combination with other pesticides, such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators, e.g. as finished formulations 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 ingredients to be combined.

[0128] Known active ingredients based on the inhibition of acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate 3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoendesaturase, photosystem I, photosystem II, and protoporphyrinogen oxidase, 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, can be used as combination partners for the compounds of general formula (I) according to the invention in mixture formulations or in tank mixes.

[0129] Of particular interest is the selective control of weeds in crops of useful and ornamental plants. Although the compounds of general formula (I) according to the invention already exhibit very good to sufficient selectivity in many crops, phytotoxicity can, in principle, occur in some crops, and especially in the case of mixtures with other herbicides that are less selective. In this respect, combinations of compounds (I) according to the invention are of particular interest, which contain the compounds of general formula (I) or their combinations with other herbicides or pesticides and safeners.Safeners, used in an antidote-effective concentration, reduce the phytotoxic side effects of the herbicides / pesticides used in economically important crops such as cereals (wheat, barley, rye, maize, rice, millet), sugar beet, sugar cane, rapeseed, cotton and soybeans, preferably cereals.

[0130] The weight ratio of herbicide (mixture) to safener generally depends on the application rate of herbicide and the efficacy of the respective safener and can vary within wide limits, i.e., in the range of 200:1 to 1:200, preferably 100:1 to 1:100, and particularly 20:1 to 1:20. The safeners can be formulated analogously to the compounds of general formula (I) or their mixtures with other herbicides / pesticides and can be supplied and applied as a ready-to-use formulation or tank mix with the herbicides.

[0131] For application, commercially available herbicide or herbicide-safener formulations are diluted as necessary in the usual manner, e.g., in the case of spray powders, emulsifiable concentrates, dispersions, and water-dispersible granules, with water. Powdery preparations, soil or granular coatings, and sprayable solutions are not usually diluted with further inert substances before application.

[0132] External conditions such as temperature, humidity, etc., influence to some extent the application rate of the compounds of general formula (I) and / or their salts. The application rate can vary within wide limits. For use as a herbicide to control weeds, the total amount of compounds of general formula (I) and their salts is preferably in the range of 0.001 to 10.0 kg / ha, more preferably in the range of 0.005 to 5 kg / ha, more preferably in the range of 0.01 to 1.5 kg / ha, and particularly preferably in the range of 0.05 to 1 kg / ha. This applies to both pre-emergence and post-emergence applications.

[0133] When using compounds of general formula (I) and / or their salts according to the invention as plant growth regulators or as stem shorteners in crops such as those mentioned above, preferably cereal crops like wheat, barley, rye, triticale, millet, rice, or maize, the total application rate is preferably in the range of 0.001 to 2 kg / ha, more preferably in the range of 0.005 to 1 kg / ha, particularly in the range of 10 to 500 g / ha, and most preferably in the range of 20 to 250 g / ha. This applies to both pre-emergence and post-emergence application.

[0134] The application as a stem shortener can take place at various stages of plant growth. Application after tillering, at the beginning of stem elongation, is preferred.

[0135] Alternatively, when used as a plant growth regulator, seed treatment is also an option, encompassing various seed dressing and coating techniques. The application rate depends on the specific technique and can be determined through preliminary trials.

[0136] Known active ingredients based on the inhibition of acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate 3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoendesaturase, photosystem I, photosystem II or protoporphyrinogen oxidase, 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, can be used as combination partners for the compounds of the general formula (I) according to the invention (e.g. mixture formulations or in tank mixes).The following is a list of known herbicides or plant growth regulators that can be combined with the compounds according to the invention. These active ingredients are identified either by their common name according to the International Organization for Standardization (ISO) or by their chemical name or code number. All application forms, such as acids, salts, esters, and all isomeric forms, such as stereoisomers and optical isomers, are included, even if not explicitly mentioned.

[0137] Examples of such herbicidal mixing partners are:

[0138] Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydimsodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlorpotassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate und -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenacsodium, chlorfenprop,chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, - dimethylammonium, -diolamin, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, - potassium, -triisopropanolammonium und -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium und -sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl,diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyrsodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9600, F-5231, i.e. N-[2-Chlor-4-fluor-5-[4-(3-fluorpropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]-ethansulfonamid, F-7967, i.e. 3-[7-Chlor-5-fluor-2-(trifluormethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluormethyl)pyrimidin-2,4(1H,3H)-dion, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet,flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, - dimethylammonium und -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, - potassium, -sodium und -trimesium, H-9201, i.e. O-(2,4-Dimethyl-6-nitrophenyl)-O-ethyl-isopropylphosphoramidothioat, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuronmethyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e. 1-(Dimethoxyphosphoryl)-ethyl-(2,4-dichlorphenoxy)acetat,imazamethabenz, Imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquinammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium und sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e. 3-({[5-(Difluormethyl)-1-methyl-3-(trifluormethyl)-1H-pyrazol-4-yl] methyl} sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazol, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, - isopropylammonium, -potassium und -sodium, MCPB, MCPB-methyl, -ethyl und -sodium, mecoprop, mecoprop-sodium, und -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl und -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron,methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e. N-[3-chlor-4-(1-methylethyl)-phenyl]-2-methylpentanamid, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-Dichlorbenzoyl)-1-methyl-5-benzyloxypyrazol, neburon, nicosulfuron, nonanoic acid (Pelargonsäure), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium,propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuronethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, , SYN-523, SYP-249, i.e. 1-Ethoxy-3-methyl-1-oxobut-3-en-2-yl-5-[2-chlor-4-(trifluormethyl)phenoxy]-2-nitrobenzoat, SYP-300, i.e. 1-[7-Fluor-3-oxo-4-(prop-2-in-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidin-4,5-dion, 2,3,6-TBA, TCA (Trifluoressigsäure), TCA-sodium, tebuthiuron,tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazonemethyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, i.e. 3,4-Dichlor-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}anilin, sowie die folgenden Verbindungen: ,

[0139] Examples of plant growth regulators as potential mixing partners are: acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechin, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothaldipotassium, -disodium, and mono(N,N-dimethylalkylammonium), ethephon, flumetraline, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indole-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid methyl ester. maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, 4-Oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazol, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol,trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.,

[0140] The following safeners are also suitable as combination partners for the compounds of general formula (I) according to the invention: S1) Compounds from the group of heterocyclic carboxylic acid derivatives: S1 a< ) Compounds of the dichlorophenylpyrazolin-3-carboxylic acid type (S1 a< ), preferably compounds such as 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carboxylic acid, 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carboxylic acid ethyl ester (S1-1) (“Mefenpyr-diethyl”), and related compounds as described in WO-A-91 / 07874; S1 b< ) Derivatives of dichlorophenylpyrazole carboxylic acid (S1 b< ), preferably compounds such as 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylic acid ethyl ester (S1-2), 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylic acid ethyl ester (S1-3), 1-(2,4-dichlorophenyl)-5-(1,1-dimethyl-ethyl)pyrazole-3-carboxylic acid ethyl ester (S1-4) and related compounds as described in EP-A-333131 and EP-A-269806; S1 c< ) Derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1 c< ), preferably compounds such as 1-(2,4-Dichlorophenyl)-5-phenylpyrazole-3-carboxylic acid ethyl ester (S1-5), 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylic acid methyl ester (S1-6) and related compounds as described in EP-A-268554; S1 d< ) compounds of the triazole carboxylic acid type (S1 d< ), preferably compounds such as fenchlorazole(-ethyl ester), i.e. 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylic acid ethyl ester (S1-7), and related compounds as described in EP-A-174562 and EP-A-346620; S1 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 (S1 e< ), preferably compounds such as 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylic acid ethyl ester (S1-8) or 5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-9) and related compounds as described in WO-A-91 / 08202, or 5,5-diphenyl-2-isoxazoline-carboxylic acid (S1-10) or 5,5-Diphenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-11) ("Isoxadifen-ethyl") or -n-propyl ester (S1-12) or 5-(4-Fluorphenyl)-5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-13), as described in patent application WO-A-95 / 07897. S2) Compounds from the group of 8-quinoline oxide derivatives (S2): S2 a< ) Compounds of the type of 8-quinoline oxyacetic acid (S2 a< ), preferably (5-chloro-8-quinoline oxy)acetic acid (1-methylhexyl) ester ("Cloquintocet-mexyl") (S2-1), (5-chloro-8-quinoline oxy)acetic acid (1,3-dimethyl-but-1-yl) ester (S2-2), (5-chloro-8-quinoline oxy)acetic acid 4-allyl-oxy-butyl ester (S2-3), (5-chloro-8-quinoline oxy)acetic acid 1-allyloxy-prop-2-yl ester (S2-4), (5-chloro-8-quinoline oxy)acetic acid ethyl ester (S2-5), (5-chloro-8-quinoline oxy)acetic acid methyl ester (S2-6), (5-Chloro-8-quinolineoxy)acetic acid allyl ester(S2-7), (5-Chloro-8-quinolineoxy)acetic acid 2-(2-propylidene-iminoxy)-1-ethyl ester(S2-8), (5-Chloro-8-quinolineoxy)acetic acid 2-oxo-prop-1-yl ester(S2-9) and related compounds,as described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0 492 366, as well as (5-chloro-8-quinoline oxy)acetic acid(S2-10), its hydrates and salts, such as its lithium, sodium, potassium, calcium, magnesium, aluminium, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts as described in WO-A-2002 / 34048; S2 b< ) Compounds of the type of (5-chloro-8-quinolineoxy)malonic acid (S2 b< ), preferably compounds such as (5-chloro-8-quinolineoxy)malonic acid diethyl ester, (5-chloro-8-quinolineoxy)malonic acid diallyl ester, (5-chloro-8-quinolineoxy)malonic acid methyl ethyl ester and related compounds as described in EP-A-0 582 198. S3) Active ingredients of the type of dichloroacetamides (S3), which are frequently used as pre-emergence safeners (soil-active safeners), such as e.g. B. "Dichlormid" (N,N-diallyl-2,2-dichloroacetamide) (S3-1), "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), "Benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4), "PPG-1292" (N-allyl-N-[(1,3-dioxolan-2-yl)-methyl]-dichloroacetamide) from PPG Industries (S3-5), "DKA-24" (N-allyl-N-[(allylaminocarbonyl)methyl]-dichloroacetamide) from Sagro-Chem (S3-6), "AD-67" or "MON 4660" (3-dichloroacetyl-1-oxa-3-aza-spiro[4,5]decane) from Nitrokemia or Monsanto (S3-7), "TI-35" (1-Dichloroacetyl-azepane) from the company TRI-Chemical RT (S3-8), "Diclonon" (Dicyclonone) or "BAS145138" or "LAB145138" (S3-9) ((RS)-1-Dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one) of BASF, "Furilazol" or "MON 13900" ((RS)-3-Dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10), and its (R)-isomer (S3-11). S4) Compounds of the class of acylsulfonamides (S4): S4 a< ) N-acylsulfonamides of the formula (S4 a< ) and their salts as described in WO-A-97 / 45016, , wherein RA 1< (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, the latter two substituents being substituted by v A substituents from the group halogen, (C 1 -C 4 )-alkoxy, (C 1 -C 6 )-haloalkoxy and (C 1 -C 4 )-alkylthio and, in the case of cyclic substituents, also by (C 1 -C 4 )-alkyl and (C 1 -C 4 )-haloalkyl; RA 2< halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, CF 3 ; m A 1 or 2; v A is 0, 1, 2 or 3; S4 b< ) Compounds of the type of 4-(benzoylsulfamoyl)benzamides of formula (S4 b< ) and their salts, as described in WO-A-99 / 16744, where RB1<, RB2< independently denote hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl, RB3< halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl or (C1-C4)-alkoxy and m B1 or 2, e.g., where RB1< = cyclopropyl, RB2< = hydrogen and (RB3<) = 2-OMe (“Cyprosulfamide”, S4-1), RB1< = cyclopropyl, RB2< = hydrogen and (RB3<) = 5-Cl-2-OMe (S4-2), RB1< = ethyl, RB2< = hydrogen and (RB 3< ) = 2-OMe is (S4-3), RB 1< = isopropyl, RB 2< = hydrogen and (RB 3< ) = 5-Cl-2-OMe is (S4-4) and RB 1< = isopropyl, RB 2< = hydrogen and (RB 3< ) = 2-OMe is (S4-5); S4 c< ) compounds from the class of benzoylsulfamoylphenylureas of the formula (S4 c< ), as described in EP-A-365484, where RC1< , RC2< independently denote hydrogen, (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl, RC3< halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3 and mC1 or C2; such as 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea; S4 d< ) Compounds of the type of N-phenylsulfonyl terephthalamides of the formula (S4 d< ) and their salts, which are known e.g. from CN 101838227, where RD 4< halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, CF 3 ; m D 1 or 2; RD 5< hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 5 -C 6 )-cycloalkenyl. S5) Active substances from the class of hydroxyaromatics and aromatic-aliphatic carboxylic acid derivatives (S5), e.g. 3,4,5-triacetoxybenzoic acid ethyl ester, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-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. S6) Active substances from the class of 1,2-dihydroquinoxalin-2-ones (S6), e.g. 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydro-quinoxalin-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydro-quinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydro-quinoxalin-2-one, as described in WO-A-2005 / 112630.S7) Compounds from the class of diphenylmethoxyacetic acid derivatives (S7), e.g., methyl diphenylmethoxyacetic acid ester (CAS Reg. No. 41858-19-9) (S7-1), ethyl diphenylmethoxyacetic acid ester, or diphenylmethoxyacetic acid as described in WO-A-98 / 38856. S8) Compounds of formula (S8) as described in WO-A-98 / 27049. wherein the symbols and indices have the following meanings: RD 1< is halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, RD 2< is hydrogen or (C 1 -C 4 )-alkyl, RD 3< is hydrogen, (C 1 -C 8 )-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, or aryl, wherein each of the aforementioned C-containing residues is unsubstituted or substituted by one or more, preferably up to three identical or different, residues 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. 1,2-Dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No.: 219479-18-2), 1,2-Dihydro-4-hydroxy-1-methyl-3-(5-tetrazolyl-carbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-1999 / 000020.S10) Compounds of the formulas (S10 a< ) or (S10 b< ) as described in WO-A-2007 / 023719 and WO-A-2007 / 023764, . where RE 1< halogen, (C 1 - C 4 )-alkyl, methoxy, nitro, cyano, CF 3 , OCF 3 YE , ZE independently O or S, n E an integer from 0 to 4, RE 2< (C 1 - C 16 )-alkyl, (C 2 - C 6 )-alkenyl, (C 3 - C 6 )-cycloalkyl, aryl, benzyl, halogenbenzyl, RE 3< hydrogen or (C 1 - C 6 )-alkyl. S11) Active ingredients of the type of oxyimino compounds (S11) known as seed dressings, such as e.g. B. "Oxabetrinil" ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), known as a seed treatment safener for millet against metolachlor damage, "Fluxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone-O-(1,3-dioxolan-2-ylmethyl)-oxime) (S11-2), known as a seed treatment safener for millet against metolachlor damage, and "Cyometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), known as a seed treatment safener for millet against metolachlor damage. S12) Active substances from the class of isothiochromanones (S12), such asMethyl-[(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds from WO-A-1998 / 13361. S13) One or more compounds from group (S13): "Naphthalic anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), known as a seed treatment safener for maize against damage from thiocarbama herbicides; "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), known as a safener for pretilachlor in seeded rice; "Flurazole" (benzyl-2-chloro-4-trifluoromethyl-1,3-thiazol-5-carboxylate) (S13-3), known as a seed treatment safener for millet against damage from alachlor and metolachlor; "CL 304415" (CAS Reg. No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) of the company American Cyanamide, known as a safener for maize against damage from imidazolinones, "MG 191" (CAS Reg. No. 96420-72-3) (2-Dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) of Nitrokemia, known as a safener for maize, "MG 838" (CAS Reg.No. 133993-74-5) (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) of the company Nitrokemia "Disulfoton" (O,O-Diethyl S-2-ethylthioethyl phosphordithioate) (S13-7), "Dietholate" (O,O-Diethyl-O-phenylphosphorothioate) (S13-8), "Mephenate" (4-Chlorophenyl-methylcarbamate) (S13-9). S14) Active ingredients which, in addition to a herbicidal effect against weeds, also have a safener effect on cultivated plants such as rice, such as "Dimepiperate" or "MY-93" (. S-1-Methyl-1-phenylethyl-piperidine-1-carbothioate), known as a safener for rice against damage from the herbicide Molinate, "Daimuron" or "SK 23" (1-(1-Methyl-1-phenylethyl)-3-p-tolyl-urea), known as a safener for rice against damage from the herbicide Imazosulfuron, "Cumyluron" = "JC-940" (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenyl-ethyl)urea, see JP-A-60087270), known as a safener for rice against damage from some herbicides, "Methoxyphenone" or "NK 049" (3,3'-Dimethyl-4-methoxy-benzophenone), known as a safener for rice against damage from some herbicides, "CSB" (1-Bromo-4-(chloromethylsulfonyl)benzene) of Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage caused by some herbicides in rice. S15) Compounds of formula (S15) or their tautomers, as described in WO-A-2008 / 131861 and WO-A-2008 / 131860, wherein RH 1< represents a (C 1 - C 6 )-haloalkyl group and RH 2< represents hydrogen or halogen and RH 3< , RH 4< independently represent hydrogen, (C 1 - C 16 )-alkyl, (C 2 - C 16 )-alkenyl or (C 2 - C 16 )-alkynyl, each of the latter 3 groups being unsubstituted or by one or more groups from the group consisting of halogen, hydroxy, cyano, (C 1 - C 4 )-alkoxy, (C 1 - C 4 )-haloalkoxy, (C 1 - C 4 )-alkylthio, (C 1 - C 4 )-alkylamino, di[(C 1 - C 4 )-alkyl]amino, [(C1-C4)-alkoxy]carbonyl, [(C1-C4)-haloalkoxy]carbonyl, (C3-C6)-cycloalkyl, unsubstituted or substituted, phenyl, unsubstituted or substituted, and heterocyclyl, unsubstituted or substituted, or (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl,that is condensed on one side of the ring with a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)-cycloalkenyl, which is condensed on one side of the ring with a 4- to 6-membered saturated or unsaturated carbocyclic ring, wherein each of the latter 4 residues is unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]amino, [(C1-C4 )-Alkoxy]-carbonyl, [(C 1 -C 4 )-Haloalkoxy]-carbonyl, (C 3 -C 6 )-Cycloalkyl, unsubstituted or substituted, phenyl, unsubstituted or substituted, and heterocyclyl, unsubstituted or substituted, means or RH 3< (C 1 -C 4 )-Alkoxy, (C 2 -C 4 )-Alkenyloxy-,(C 2 -C 6 )-alkynyloxy or (C 2 -C 4 )-haloalkoxy means and RH 4< means hydrogen or (C 1 -C 4 )-alkyl or RH 3< and RH 4< together with the directly bonded N atom a four- to eight-membered heterocyclic ring which, in addition to the N atom, may also contain further heteroring atoms, preferably up to two further heteroring atoms from the group N, O and S and which is unsubstituted or substituted by one or more residues from the group halogen, cyano, nitro, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy and (C 1 -C 4 )-alkylthio. S16) Active substances primarily used as herbicides, but which also have a safener effect on crops, e.g. (2,4-Dichlorophenoxy)acetic acid (2,4-D), (4-Chlorphenoxy)acetic acid, (R,S)-2-(4-Chloro-o-tolyloxy)propionic acid (Mecoprop), 4-(2,4-Dichlorophenoxy)butyric acid (2,4-DB), (4-Chloro-o-tolyloxy)acetic acid (MCPA), 4-(4-Chloro-o-tolyloxy)butyric acid,4-(4-chlorophenoxy)butyric acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba), 1-(ethoxycarbonyl)ethyl-3,6-dichloro-2-methoxybenzoate (lactidichloro-ethyl). ,

[0141] Preferred safeners in combination with the compounds of the general formula (I) according to the invention and / or their salts, in particular with the compounds of formulas (I-1) to (I-229) and / or their salts are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole ethyl ester, isoxadifen-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

[0142] The following abbreviations are used in the examples and tables below: Undesirable plants / weeds: ABUTH:Abutilon theophrasti AGSTE:Agrostis tenuis AMAREAmaranthus retroflexus ECHCG:Echinochloa crus-galli LOLRI:Lolium rigidum MATIN:Matricaria inodora POAAN:Poa annua SETVI:Setaria viridis STEME:Stellaria media A. Herbicidal activity in early post-emergence

[0143] Seeds of monocotyledonous and dicotyledonous weeds were sown in quartz sand in 96-well microtiter plates and cultivated in a climate chamber under controlled growth conditions. Five to seven days after sowing, the plants were treated at the cotyledon stage. The compounds according to the invention, formulated as emulsion concentrates (EC), were applied with a water volume equivalent to 2200 liters per hectare. After nine to twelve days of the plants remaining in the climate chamber under optimal growth conditions, the effect of the preparations was visually assessed in comparison to untreated controls.

[0144] Here, 100% effect means plants have died, 0% effect means the same as untreated control plants.

[0145] Tables A1 to A2 below show the effects of selected compounds of the general formula (I) according to Table 1 above on various weeds and an application rate corresponding to 1900 g / ha, obtained according to the aforementioned experimental procedure. Table A1 Example number Dosage [g / ha] AGSTE 1-40 1900 80 1-75 1900 100 1-79 1900 80 1-88 1900 100 1-106 1900 100 1-111 1900 100 1-124 1900 100 1-129 1900 100 1-139 1900 100 1-143 1900 80 1-144 1900 100 1-146 1900 80 1-149 1900 100 1-204 1900 100 1-235 1900 100 1-239 1900 80 1-246 1900 80 1-247 1900 80 1-248 1900 100 1-250 1900 80 1-251 1900 80 1-253 1900 100 1-255 1900 80 1-256 1900 80 1-260 1900 100 1-261 1900 80 1-265 1900 80 1-266 1900 80 1-267 1900 100 1-268 1900 100 1-269 1900 80 1-270 1900 80 1-271 1900 80 1-272 1900 100 1-273 1900 80 1-274 1900 80 1-275 1900 80 1-278 1900 100 1-279 1900 80 1-280 1900 100 1-281 1900 100 1-284 1900 100 1-286 1900 100 1-287 1900 80 1-288 1900 80 1-289 1900 80 1-290 1900 80 1-291 1900 100 1-292 1900 100 1-293 1900 80 1-294 1900 80 1-297 1900 100 1-298 1900 80 1-299 1900 80 1-300 1900 80 1-304 1900 100 1-305 1900 100 1-306 1900 100 1-308 1900 100 1-310 1900 80 1-312 1900 100 1-314 1900 100 1-324 1900 100 1-328 1900 80 1-336 1900 100 1-337 1900 100 1-339 1900 100 1-340 1900 80 1-341 1900 100 1-350 1900 80 1-358 1900 100 1-365 1900 100 1-366 1900 100 1-369 1900 80 1-372 1900 100 1-374 1900 100 1-375 1900 100 1-376 1900 80 2-101 1900 100 2-136 1900 80 2-139 1900 80 3-49 1900 80 3-53 1900 100 3-54 1900 100 3-55 1900 100 3-56 1900 100 Table A2 Example number Dosage [g / ha] POAAN 1-40 1900 80 1-75 1900 80 1-79 1900 100 1-88 1900 80 1-106 1900 100 1-111 1900 100 1-124 1900 100 1-139 1900 80 1-144 1900 100 1-145 1900 80 1-204 1900 100 1-235 1900 100 1-239 1900 100 1-248 1900 100 1-250 1900 80 1-251 1900 80 1-253 1900 100 1-255 1900 80 1-256 1900 80 1-260 1900 100 1-261 1900 80 1-266 1900 100 1-267 1900 100 1-268 1900 80 1-269 1900 100 1-270 1900 80 1-271 1900 80 1-272 1900 100 1-274 1900 100 1-275 1900 100 1-278 1900 100 1-279 1900 100 1-280 1900 100 1-284 1900 100 1-286 1900 100 1-288 1900 80 1-289 1900 80 1-291 1900 100 1-292 1900 80 1-293 1900 80 1-294 1900 100 1-297 1900 80 1-298 1900 80 1-299 1900 100 1-304 1900 100 1-305 1900 100 1-306 1900 80 1-308 1900 100 1-312 1900 100 1-314 1900 80 1-324 1900 80 1-328 1900 80 1-336 1900 100 1-337 1900 100 1-339 1900 100 1-340 1900 100 1-341 1900 100 1-350 1900 100 1-358 1900 100 1-366 1900 80 1-369 1900 80 1-372 1900 100 1-374 1900 100 1-375 1900 100 1-376 1900 80 2-101 1900 80 3-53 1900 100 3-54 1900 100 3-55 1900 100 3-56 1900 100

[0146] The test results demonstrate that compounds of the general formula (I) according to the invention exhibit good herbicidal efficacy against selected weeds such as Agrostis tenuis and Poa annua when applied in early post-emergence, at a respective application rate of 1900 g of active substance per hectare. B. Herbicidal effect in post-emergence

[0147] Seeds of monocot and dicot weeds were sown in plastic pots in sandy loam soil (double sowings with one species of monocot and one of dicot weeds per pot), covered with soil, and cultivated in a greenhouse under controlled growing conditions. Two to three weeks after sowing, the experimental plants were treated at the single-leaf stage. The compounds according to the invention, formulated as wettable powders (WP) or emulsion concentrates (EC), were applied to the green parts of the plants as an aqueous suspension or emulsion, with the addition of 0.5% additive, at a water volume equivalent to 600 liters per hectare. After approximately three weeks of the experimental plants remaining in the greenhouse under optimal growing conditions, the effect of the preparations was visually assessed in comparison to untreated controls.

[0148] Here, 100% effect means plants have died, 0% effect means the same as untreated control plants.

[0149] Tables B1-B8 below show the effects of selected compounds of general formula (I) according to Table 1 above on various weeds and an application rate corresponding to 1280 g / ha, obtained according to the aforementioned experimental procedure. Table B1: Example number Dosage [g / ha] ECHCG 1-204 1280 100 1-235 1280 100 1-248 1280 100 1-253 1280 100 1-266 1280 100 1-267 1280 100 1-269 1280 90 1-270 1280 90 1-272 1280 100 1-275 1280 90 1-278 1280 90 1-286 1280 100 1-288 1280 100 1-289 1280 100 1-291 1280 100 1-308 1280 100 1-337 1280 90 1-374 1280 100 3-53 1280 100 3-53 1280 100 3-56 1280 100 Table B2: Example number Dosage [g / ha] LOLRI 1-204 1280 90 1-267 1280 90 1-272 1280 100 1-286 1280 90 3-53 1280 90 3-55 1280 90 Table B3: Example number Dosage [g / ha] POAAN 1-139 1280 100 1-204 1280 100 1-235 1280 100 1-239 1280 100 1-248 1280 100 1-267 1280 100 1-269 1280 90 1-272 1280 100 1-279 1280 100 1-286 1280 100 1-288 1280 100 1-291 1280 100 1-294 1280 100 1-298 1280 90 1-308 1280 100 1-350 1280 100 1-369 1280 100 1-372 1280 100 1-374 1280 100 1-375 1280 100 3-53 1280 100 3-54 1280 100 3-55 1280 100 3-56 1280 100 Table B4: Example number Dosage [g / ha] SETVI 1-204 1280 100 1-253 1280 90 1-269 1280 90 1-270 1280 90 1-272 1280 100 1-275 1280 90 1-286 1280 100 1-288 1280 90 1-289 1280 90 1-291 1280 100 1-298 1280 90 1-299 1280 90 1-308 1280 100 3-53 1280 90 3-54 1280 90 3-55 1280 90 3-56 1280 100 Table B5: Example number Dosage [g / ha] ABUTH 1-111 1280 90 1-204 1280 100 1-235 1280 100 1-248 1280 100 1-253 1280 100 1-266 1280 100 1-267 1280 100 1-269 1280 90 1-270 1280 90 1-272 1280 100 1-275 1280 90 1-278 1280 90 1-286 1280 100 1-288 1280 90 1-289 1280 90 1-291 1280 100 1-293 1280 90 1-298 1280 90 1-308 1280 100 1-312 1280 100 1-314 1280 90 1-337 1280 90 1-340 1280 90 1-374 1280 100 1-375 1280 90 3-49 1280 90 3-53 1280 100 3-54 1280 100 3-55 1280 100 3-56 1280 100 Table B6: Example number Dosage [g / ha] AMARE 1-106 1280 100 1-111 1280 100 1-124 1280 100 1-129 1280 100 1-149 1280 100 1-235 1280 100 1-239 1280 100 1-246 1280 100 1-247 1280 100 1-248 1280 100 1-250 1280 100 1-251 1280 100 1-253 1280 100 1-254 1280 100 1-255 1280 100 1-256 1280 100 1-260 1280 100 1-261 1280 100 1-265 1280 100 1-266 1280 100 1-267 1280 100 1-268 1280 90 1-269 1280 100 1-270 1280 100 1-271 1280 100 1-272 1280 100 1-273 1280 100 1-274 1280 100 1-275 1280 100 1-278 1280 100 1-279 1280 100 1-280 1280 100 1-284 1280 100 1-285 1280 100 1-286 1280 100 1-287 1280 100 1-288 1280 100 1-289 1280 100 1-290 1280 100 1-291 1280 100 1-292 1280 100 1-293 1280 100 1-294 1280 100 1-297 1280 100 1-298 1280 100 1-299 1280 100 1-300 1280 100 1-304 1280 100 1-305 1280 100 1-308 1280 100 1-312 1280 100 1-314 1280 100 1-337 1280 90 1-339 1280 100 1-340 1280 100 1-341 1280 100 1-342 1280 100 1-350 1280 100 1-369 1280 100 1-374 1280 100 1-375 1280 100 3-49 1280 100 3-53 1280 100 3-54 1280 100 3-55 1280 100 3-56 1280 100 Table B7: Example number Dosage [g / ha] MATIN 1-139 1280 100 1-235 1280 80 1-272 1280 100 1-306 1280 100 1-310 1280 100 1-336 1280 100 1-374 1280 100 3-53 1280 90 3-55 1280 90 Table B8: Example number Dosage [g / ha] STEME 1-88 1280 100 1-106 1280 90 1-111 1280 90 1-204 1280 100 1-235 1280 100 1-239 1280 100 1-248 1280 100 1-250 1280 90 1-253 1280 100 1-255 1280 100 1-260 1280 90 1-266 1280 100 1-267 1280 100 1-269 1280 100 1-270 1280 100 1-272 1280 100 1-274 1280 90 1-275 1280 100 1-278 1280 100 1-279 1280 100 1-280 1280 100 1-286 1280 100 1-289 1280 100 1-291 1280 100 1-294 1280 100 1-298 1280 100 1-299 1280 100 1-305 1280 100 1-306 1280 100 1-308 1280 100 1-310 1280 90 1-312 1280 100 1-314 1280 100 1-336 1280 100 1-339 1280 100 1-340 1280 100 1-372 1280 90 1-374 1280 100 1-375 1280 100 3-53 1280 100 3-54 1280 90 3-55 1280 100 3-56 1280 100

[0150] The test results demonstrate that the compounds of the general formula (I) according to the invention exhibit good herbicidal efficacy against selected weeds such as Echinochloa crus-galli, Poa annua, Abutilon theophrasti, Amaranthus retroflexus, Lolium rigidum, Setaria viridis, Stellaria media and Matricaria inodora when applied post-emergence at a respective application rate of 1280 g of active substance per hectare. C. Herbicidal activity in pre-emergence

[0151] Seeds of monocotyledonous and dicotyledonous weeds were sown in plastic pots in sandy loam soil (double sowings with one species of monocotyledonous or dicotyledonous weed per pot) and covered with soil. The compounds according to the invention, formulated as wettable powders (WP) or as emulsion concentrates (EC), were then applied to the surface of the cover soil as an aqueous suspension or emulsion, with the addition of 0.5% additive, at a water volume of approximately 600 liters per hectare. After treatment, the pots were placed in the greenhouse and kept under good growing conditions for the test plants. After approximately three weeks, the effect of the preparations was visually assessed in percentage terms in comparison to untreated controls.

[0152] In this context, 100% effect means plants have died, 0% effect means the same as untreated control plants.

[0153] Tables C1-C8 below show the effects of selected compounds of general formula (I) according to Table 1 above on various weeds and an application rate corresponding to 1280 g / ha, obtained according to the aforementioned experimental procedure. Table C1: Example number Dosage [g / ha] ECHCG 1-204 1280 100 1-235 1280 90 1-247 1280 90 1-248 1280 100 1-253 1280 100 1-260 1280 90 1-261 1280 100 1-266 1280 90 1-267 1280 100 1-269 1280 90 1-270 1280 100 1-272 1280 100 1-275 1280 90 1-280 1280 100 1-285 1280 90 1-288 1280 90 1-291 1280 90 1-294 1280 90 1-308 1280 90 1-374 1280 100 1-375 1280 100 3-53 1280 100 3-54 1280 100 3-55 1280 100 3-56 1280 100 Table C2: Example number Dosage [g / ha] LOLRI 1-248 1280 100 1-253 1280 100 1-267 1280 100 1-269 1280 90 1-272 1280 100 1-278 1280 100 1-279 1280 90 1-286 1280 90 1-291 1280 100 1-299 1280 90 1-375 1280 90 3-53 1280 100 3-54 1280 100 3-55 1280 100 Table C3: Example number Dosage [g / ha] POAAN 1-79 1280 100 1-106 1280 100 1-204 1280 100 1-235 1280 100 1-239 1280 100 1-247 1280 100 1-248 1280 100 1-250 1280 100 1-253 1280 100 1-254 1280 90 1-256 1280 100 1-260 1280 90 1-261 1280 100 1-265 1280 100 1-266 1280 100 1-267 1280 100 1-269 1280 100 1-270 1280 100 1-271 1280 90 1-272 1280 100 1-274 1280 90 1-275 1280 100 1-278 1280 100 1-279 1280 100 1-280 1280 100 1-285 1280 100 1-286 1280 100 1-287 1280 100 1-288 1280 100 1-289 1280 100 1-290 1280 90 1-291 1280 100 1-294 1280 100 1-298 1280 100 1-299 1280 100 1-304 1280 100 1-305 1280 100 1-308 1280 100 1-312 1280 100 1-337 1280 100 1-340 1280 100 1-350 1280 100 1-374 1280 100 1-375 1280 100 3-53 1280 100 3-54 1280 100 3-55 1280 100 3-56 1280 100 Table C4: Example number Dosage [g / ha] SETVI 1-88 1280 90 1-111 1280 90 1-129 1280 90 1-204 1280 100 1-235 1280 100 1-246 1280 100 1-247 1280 100 1-248 1280 100 1-250 1280 90 1-251 1280 90 1-253 1280 100 1-254 1280 100 1-256 1280 90 1-260 1280 100 1-261 1280 100 1-265 1280 90 1-266 1280 100 1-267 1280 100 1-269 1280 100 1-270 1280 100 1-271 1280 90 1-272 1280 100 1-273 1280 90 1-275 1280 100 1-278 1280 100 1-279 1280 100 1-280 1280 100 1-284 1280 100 1-285 1280 100 1-286 1280 100 1-287 1280 100 1-288 1280 100 1-289 1280 100 1-291 1280 100 1-292 1280 90 1-293 1280 100 1-294 1280 100 1-297 1280 100 1-298 1280 100 1-299 1280 100 1-304 1280 100 1-305 1280 90 1-306 1280 100 1-308 1280 100 1-312 1280 90 1-314 1280 100 1-340 1280 100 1-342 1280 100 1-369 1280 100 1-372 1280 100 1-374 1280 100 1-375 1280 100 3-53 1280 100 3-54 1280 100 3-55 1280 100 3-56 1280 100 Table C5: Example number Dosage [g / ha] ABUTH 1-248 1280 100 1-261 1280 100 1-267 1280 100 1-268 1280 90 1-269 1280 90 1-272 1280 100 1-280 1280 100 1-286 1280 90 1-294 1280 90 1-308 1280 100 1-375 1280 100 3-53 1280 100 3-54 1280 100 3-55 1280 100 3-56 1280 100 Tables C6: Example number Dosage [g / ha] AMARE 1-88 1280 100 1-106 1280 100 1-111 1280 100 1-145 1280 90 1-149 1280 100 1-204 1280 100 1-235 1280 100 1-246 1280 100 1-247 1280 100 1-248 1280 100 1-250 1280 100 1-251 1280 100 1-252 1280 90 1-253 1280 100 1-254 1280 100 1-255 1280 100 1-256 1280 100 1-260 1280 100 1-261 1280 100 1-265 1280 100 1-266 1280 100 1-267 1280 100 1-268 1280 90 1-269 1280 100 1-270 1280 100 1-271 1280 100 1-272 1280 100 1-273 1280 100 1-274 1280 90 1-275 1280 100 1-278 1280 100 1-279 1280 100 1-280 1280 100 1-284 1280 100 1-285 1280 100 1-286 1280 100 1-287 1280 100 1-288 1280 100 1-289 1280 100 1-290 1280 90 1-291 1280 100 1-292 1280 100 1-293 1280 100 1-294 1280 100 1-298 1280 100 1-299 1280 100 1-300 1280 90 1-304 1280 100 1-305 1280 100 1-306 1280 100 1-308 1280 100 1-312 1280 100 1-337 1280 90 1-340 1280 100 1-342 1280 100 1-350 1280 100 1-369 1280 100 1-372 1280 100 1-374 1280 100 1-375 1280 100 3-53 1280 100 3-54 1280 100 3-55 1280 100 3-56 1280 100 Table C7: Example number Dosage [g / ha] MATIN 1-111 1280 90 1-204 1280 90 1-235 1280 100 1-239 1280 100 1-248 1280 100 1-251 1280 100 1-253 1280 100 1-256 1280 90 1-260 1280 90 1-261 1280 100 1-266 1280 100 1-267 1280 100 1-269 1280 100 1-270 1280 100 1-272 1280 100 1-275 1280 90 1-278 1280 100 1-279 1280 90 1-280 1280 100 1-286 1280 100 1-289 1280 100 1-291 1280 100 1-298 1280 90 1-300 1280 90 1-304 1280 100 1-305 1280 100 1-306 1280 90 1-308 1280 100 1-312 1280 100 1-350 1280 100 1-374 1280 100 1-375 1280 100 3-53 1280 100 3-54 1280 100 3-55 1280 100 3-56 1280 100 Table C8: Example number Dosage [g / ha] STEME 1-111 1280 100 1-129 1280 90 1-235 1280 100 1-246 1280 100 1-247 1280 100 1-248 1280 100 1-250 1280 100 1-251 1280 100 1-253 1280 100 1-255 1280 100 1-256 1280 100 1-260 1280 100 1-261 1280 100 1-265 1280 100 1-266 1280 100 1-267 1280 100 1-269 1280 100 1-270 1280 100 1-272 1280 100 1-274 1280 90 1-275 1280 100 1-278 1280 100 1-279 1280 100 1-280 1280 100 1-284 1280 90 1-285 1280 100 1-286 1280 100 1-288 1280 100 1-289 1280 100 1-291 1280 100 1-293 1280 90 1-294 1280 100 1-298 1280 100 1-299 1280 100 1-300 1280 100 1-304 1280 100 1-305 1280 100 1-306 1280 100 1-308 1280 100 1-312 1280 100 1-336 1280 100 1-340 1280 90 1-341 1280 90 1-369 1280 100 1-374 1280 100 1-375 1280 100 3-53 1280 100 3-54 1280 100 3-55 1280 100 3-56 1280 100

[0154] The test results demonstrate that compounds of the general formula (I) according to the invention exhibit good herbicidal efficacy against selected weeds such as Echinochloa crus-galli, Lolium rigidum, Setaria viridis, Poa annua, Abutilon theophrasti, Amaranthus retroflexus, Stellaria media and Matricaria inodora when applied pre-emergence at an application rate of 1280 g of active substance per hectare.

Claims

1. Substituted 2-heteroarylaminobenzenes of the general formula (I) or salts thereof wherein A is nitrogen or -CX-, X is hydrogen or halogen, R1 represents an optionally substituted aryl or heteroaryl, wherein each ring or ring system is optionally substituted with up to 5 substituents independently selected from the group R5, R2 is independently halogen, cyano, nitro, formyl, formamide, (C1-C8)alkyl, (C1-C8)haloalkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkenyl, (C2-C8)-haloalkynyl, (C3-C8)-cycloalkyl, (C3-C6)-halocycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C8)-alkylcarbonyl, (C1-C8)-haloalkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, carboxyl, (C1-C8)-alkoxycarbonyl, (C1-C8)-haloalkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, carbamoyl, (C2-C8)-alkylaminocarbonyl, (C2-C10)-dialkylaminocarbonyl, (C3-C10)-cycloalkylaminocarbonyl, (C1-C4)-alkoxycarbonyl-(C1-C4)-alkyl, (C1-C4)-haloalkoxycarbonyl-(C1-C4)-alkyl, carboxy-(C1-C4)-alkyl, hydroxy, NR4R6, (C1-C8)-alkoxy, (C1-C8)-haloalkoxy, (C1-C8)-alkylthio, (C1-C8)-haloalkylthio, (C3-C8)-cycloalkylthio, (C1-C4)-alkoxy-(C1-C4)-alkylthio, (C1-C8)-alkylsulfinyl, (C1-C8)-haloalkylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C1-C4)-alkoxy-(C1-C4)-alkylsulfinyl, (C1-C8)-alkylsulfonyl, (C1-C8)-haloalkylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C1-C4)-alkoxy-(C1-C4)-alkylsulfonyl, (C1-C8)-alkylaminosulfonyl, (C2-C8)-dialkylaminosulfonyl or (C3-C8)-trialkylsilyl, m is equal to 0, 1, 2, or 3, R3 is hydrogen, halogen, cyano, nitro, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C8)-alkoxy, (C1-C8)-haloalkoxy, (C1-C8)-alkylthio, (C1-C8)-haloalkylthio, (C1-C8)-alkylsulfinyl, (C1-C8)-haloalkylsulfinyl, (C1-C8)-alkylsulfonyl, (C1-C8)-haloalkylsulfonyl, R4, R6 independently of one another represent hydrogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, aryl-(C1-C6)-alkyl, heteroaryl-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C3-C6)-halocycloalkyl, (C3-C6)-halocycloalkyl-(C1-C4)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C8)-alkylcarbonyl, (C1-C8)-haloalkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, formyl, (C1-C8)-alkoxycarbonyl, (C1-C8)-haloalkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C1-C8)-alkylaminocarbonyl, (C2-C8)-dialkylaminocarbonyl, (C3-C3)-cycloalkylaminocarbonyl, and R5 represents hydrogen, halogen, cyano, nitro, formyl, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkenyl, (C2-C8)-haloalkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-alkylsulfinyl-(C1-C4)-alkyl, (C1-C4)-alkylsulfonyl-(C1-C4)-alkyl, (C1-C8)-alkylcarbonyl, (C1-C8)-haloalkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, carboxyl, (C1-C8)-alkoxycarbonyl, (C1-C8)-haloalkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C1-C8)-alkylaminocarbonyl, (C2-C8)-dialkylaminocarbonyl, (C3-C8)-cycloalkylaminocarbonyl, hydroxy, (C1-C8)-alkoxy, (C1-C8)-haloalkoxy, (C1-C8)-alkylthio, (C1-C8)-haloalkylthio, (C3-C8)-cycloalkylthio, (C1-C8)-alkylsulfinyl, (C1-C8)-haloalkylsulfinyl, (C3-C8)-cycloalkylsulfinyl, (C1-C8)-alkylsulfonyl, (C1-C8)-haloalkylsulfonyl, (C3-C8)-cycloalkylsulfonyl, (C1-C8)-alkylaminosulfonyl, (C2-C8)-dialkylaminosulfonyl or (C3-C8)-trialkylsilyl, with the exception of the compounds mentioned below: (2-phenoxyphenylamino)pyridine 5-Bromo-2-(2-phenoxyphenylamino)pyridine 5-chloro-2-(2-phenoxyphenylamino)pyridine 2-(2-phenoxyphenylamino)pyrimidine 5-bromo-2-(2-phenoxyphenylamino)pyrimidine 5-lodo-2-(2-phenoxyphenylamino)pyrimidine 2-(2-(2-pyridyloxy)phenylamino)pyrimidine.

2. A compound of the general formula (I) according to claim 1 or salts thereof, wherein A represents nitrogen or -CX-, X is hydrogen, fluorine or chlorine, R1 represents an optionally substituted phenyl, pyridyl or pyrimidyl, wherein each ring or ring system is optionally substituted with up to 5 substituents independently selected from the group R5, R2 is independently halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, NR4R6, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylthio or (C1-C4)-alkoxy, m is equal to 0, 1, 2 or 3, R3 is hydrogen, halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkenyl, (C2-C4)-haloalkynyl, cyclopropyl, cyclopropylmethyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio or (C1-C4)-haloalkylthio, R4, R6 independently of one another represent hydrogen, (C1-C4)-alkyl, (C1-C4)-alkylcarbonyl or (C1-C4)-alkoxycarbonyl, and R5 is hydrogen, halogen, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkylthio, (C1-C4)-alkoxy or (C1-C4)-haloalkoxy, with the exception of the following compounds: 2-(2-phenoxyphenylamino)pyridine 5-bromo-2-(2-phenoxyphenylamino)pyridine 5-chloro-2-(2-phenoxyphenylamino)pyridine 2-(2-phenoxyphenylamino)pyrimidine 5-bromo-2-(2-phenoxyphenylamino)pyrimidine 5-lodo-2-(2-phenoxyphenylamino)pyrimidine 2-(2-(2-pyridyloxy)phenylamino)pyrimidine.

3. A compound of the general formula (I) according to claim 1 or salts thereof, wherein A represents nitrogen or -CX-, X is hydrogen, fluorine or chlorine, R1 represents an optionally substituted phenyl, pyridyl or pyrimidyl, wherein each ring is optionally substituted with up to 5 substituents independently selected from the group R5, R2 independently of one another is fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, methylthio or amino, m is equal to 0, 1, 2 or 3, R3 is hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy, methylthio or trifluoromethylthio, and R5 represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy or trifluoromethoxy, with the exception of the following compounds: 2-(2-phenoxyphenylamino)pyridine 5-bromo-2-(2-phenoxyphenylamino)pyridine 5-chloro-2-(2-phenoxyphenylamino)pyridine 2-(2-phenoxyphenylamino)pyrimidine 5-bromo-2-(2-phenoxyphenylamino)pyrimidine 5-lodo-2-(2-phenoxyphenylamino)pyrimidine 2-(2-(2-pyridyloxy)phenylamino)pyrimidine.

4. Herbicidal agent, characterised by a herbicidally active content of at least one compound of the general formula (I) according to one of claims 1 to 3.

5. Herbicidal agent according to claim 4 in mixture with formulation adjuvants.

6. Herbicidal composition according to claim 4 or 5 containing at least one further pesticidally active substance from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.

7. Herbicidal agent according to claim 6 containing a safener.

8. Herbicidal agent according to claim 7 containing cyprosulfamide, cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl.

9. The herbicidal composition according to any one of claims 4 to 8 containing a further herbicide.

10. A method of controlling undesirable plants, characterised in that an effective amount of at least one compound of the general formula (I) according to any one of claims 1 to 3 or of a herbicidal agent according to any one of claims 4 to 9 is applied to the plants or to the site of the undesirable plant growth.

11. Use of compounds of the general formula (I) according to any one of claims 1 to 3 or of herbicidal agents according to any one of claims 4 to 9 for controlling undesirable plants.

12. Use according to claim 11, characterised in that the compounds of the general formula (I) are used to control undesirable plants in crops of useful plants.

13. Use according to claim 12, characterised in that the crop plants are transgenic crop plants.