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

Abstract

Described are substituted 2-heteroarylaminobenzenes of general formula (I) and the use thereof as herbicides, in particular for controlling weeds and / or weed grasses in crops of useful plants and / or as plant growth regulators for influencing the growth of crops of useful plants. The invention further relates to herbicidal and / or plant growth-regulating agents comprising one or more compounds of general formula (I).

Description

[0001] Bayer AG

[0002] Substituted 2-heteroarylaminobenzenes and their salts and their use as herbicidals

[0003] Active ingredients

[0004] Description

[0005] 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.

[0006] This invention specifically relates to substituted 2-heteroarylaminobenzenes and their salts, processes for their production and their use as herbicides.

[0007] Previously known plant protection products for the selective control of harmful plants in

[0008] Crop crops or active ingredients for controlling unwanted plant growth sometimes have disadvantages in their application, such as (a) lacking or having insufficient herbicidal activity against certain weeds, (b) having too narrow a spectrum of weeds that can be controlled with a single active ingredient, (c) having insufficient selectivity in crop crops, and / or (d) having an unfavorable toxicological profile. Furthermore, some active ingredients that can be used as plant growth regulators in some crops lead to undesirably reduced yields in other crops or are incompatible with the crop or only tolerated 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, the effect depends too much on environmental conditions, such as weather and soil conditions.

[0009] The herbicidal effect of these known compounds, especially at low application rates, and their compatibility with cultivated plants still need improvement.

[0010] Heteroaryloxybenzenes were described in AU535637, EP8192, EP61913, JP61236766 and WO2016 / 010731, and were attributed with herbicidal activity.

[0011] Substituted 2-heteroarylaminobenzenes or their salts as herbicidal agents, on the other hand, have not yet been described.

[0012] Surprisingly, it has now been found that certain substituted 2-heteroarylaminobenzenes or their salts are particularly well suited as herbicidal agents. The present invention therefore relates to substituted 2-heteroarylaminobenzenes of general formula (I) or their salts.

[0013]

[0014] wherein

[0015] A stands for nitrogen or -CX-

[0016] X stands for hydrogen or halogen

[0017] R 1 for an optionally substituted aryl or heteroaryl, wherein each ring or ring system is optionally equipped with up to 5 substituents, independently selected from the group R 5 , is substituted,

[0018] R 2 independently for halogen, cyano, nitro, formyl, formamide, (Ci-Cs)-alkyl, (Ci-Cs)-haloalkyl, (C2-C8)-alkenyl, (C2-C8)-alkyne> l. (C2-C8)-haloalkenyl, (C2-C8)-haloalkynyl, (C3-C8)-cycloalkyl, (C3-C6)-halocycloalkyl, (C3-C6)-cycloalkyl-(Ci-C6)-alkyl, (Ci-C4)-alkoxy-(Ci-C4)-alkyl, (Ci-C4)-haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-alkylthio-(Ci-C4)-alkyl, (Ci-C4)-alkylsulfinyl-(Ci-C4)-alkyl, (Ci-C4)-alkylsulfonyl-(Ci-C4)-alkyl, (Ci-Csj-alkylcarbonyl.

[0019] (Ci-Csj-Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, Carboxyl, (Ci-Cgj-Alkoxycarbonyl. (Ci-C8)- Haloalkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, Carbamoyl, (C2-C8)- Alkylaminocarbonyl, (C2-Cio)-Dialkylaminocarbonyl, (C3-Cio)-Cycloalkylaminocarbonyl, (Ci-C4)-Alkoxycarbonyl-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxycarbonyl-(Ci-C4)-alkyl, Carboxy- (Ci-C4)-alkyl, Hydroxy, NR 4 R 6 , (Ci-C8)-Alkoxy, (Ci-C8)-Haloalkoxy, (Ci-C8)-Alkylthio, (Ci-C8)-Haloalkylthio, (C3-C8)-Cycloalkylthio, (Ci-C4)-Alkoxy-(Ci-C4)-alkylthio, (Ci-C8)- Alkylsulfinyl, (Ci-Cgj-Haloalkylsulfinyl. (C3-C8)-Cycloalkylsulfinyl, (Ci-C4)-Alkoxy-(Ci-C4)- alkylsulfinyl, (Ci-Cgj-Alkylsulfonyl. (Ci-Cgj-Haloalkylsulfonyl. (C3-C8)-Cycloalkylsulfonyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkylsulfonyl, (Ci-Cgj-Alkylaminosulfonyl. (C2-C8)- Dialkylaminosulfonyl oder (C3-C8)-Trialkylsilyl steht, m ist gleich 0, 1, 2, oder 3,

[0020] R 3für Wasserstoff, Halogen, Cyano, Nitro, (Ci-Cs)-Alkyl, (Ci-Cs)-Haloalkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C8)-Alkoxy, (Ci-C8)-Haloalkoxy, (Ci-C8)-Alkylthio, (Ci-C8)-Haloalkylthio, (Ci-C8)-Alkylsulfinyl, (Ci-C8)- Haloalkylsulfinyl, (Ci-C8)-Alkylsulfonyl, (Ci-C8)-Haloalkylsulfonyl steht,

[0021] R 4 , R 6 unabhängig voneinander für Wasserstoff, (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl, Aryl-(C i-G,)-alkyl.

[0022] Heteroaryl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C3-C6)- Halocycloalkyl, (C3-C6)-Halocycloalkyl-(Ci-C4)-alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci- C4)-Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylthio-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfinyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfonyl-(Ci-C4)-alkyl, (Ci-C8)- Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, Formyl, (Ci-C8)- Alkoxycarbonyl, (Ci-C8)-Haloalkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (Ci-C8)- Alkylaminocarbonyl, (C2-C8)-Dialkylaminocarbonyl, (C3-C8)-Cycloalkylaminocarbonyl steht, und

[0023] R 5für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl, (C2-C8)- Alkenyl, (C2-C8)-Alkinyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (Ci-C4)-Alkoxy-(Ci-C4)- alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylthio-(Ci-C4)-alkyl, (Ci-C4)- Alkylsulfinyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfonyl-(Ci-C4)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, Carboxyl, (Ci-C8)-Alkoxycarbonyl, (Ci-C8)- Haloalkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (Ci-C8)-Alkylaminocarbonyl, (C2-C8)-Dialkylaminocarbonyl, (C3-C8)-Cycloalkylaminocarbonyl, Hydroxy, (Ci-C8)-Alkoxy, (Ci-C8)-Haloalkoxy, (Ci-C8)-Alkylthio, (Ci-C8)-Haloalkylthio, (C3-C8)-Cycloalkylthio, (Ci-C8)- Alkylsulfinyl, (Ci-C8)-Haloalkylsulfinyl, (C3-C8)-Cycloalkylsulfinyl, (Ci-C8)-Alkylsulfonyl, (Ci-C8)-Haloalkylsulfonyl, (C3-C8)-Cycloalkylsulfonyl, (Ci-C8)-Alkylaminosulfonyl, (C2-C8)- Dialkylaminosulfonyl oder (C3-C8)-Trialkylsilyl steht,excluding the following connections:,

[0024] 2-(2-Phenoxyphenylamino)pyridine

[0025] 5-Bromo-2-(2-phenoxyphenylamino)pyridine

[0026] 5-Chloro-2-(2-phenoxyphenylamino)pyridine

[0027] 2-(2-Phenoxyphenylamino)pyrimidine

[0028] 5-Bromo-2-(2-phenoxyphenylamino)pyrimidine 5-iodo-2-(2-phenoxyphenylamino)pyrimidine

[0029] 2-(2-(2-Pyridyloxy)phenylamino)pyridine.

[0030] The compounds of general formula (I) can be obtained by attachment of a suitable

[0031] Salts form when inorganic or organic acids, such as mineral acids like HCl, HBr, H₂SO₄, HsPCF, or HNO₃, or organic acids, such as carboxylic acids like formic acid, acetic acid, propionic acid, oxalic acid, lactic acid, or salicylic acid, or sulfonic acids like p-toluenesulfonic acid, are attached to a basic group, such as an amino, alkylamino, dialkylamino, piperidino, morpholino, or pyridino. These salts then contain the conjugate base of the acid as an anion. Suitable substituents, which in their deprotonated form, such as sulfonic acids, exhibit certain properties, can be used to form salts.

[0032] Sulfonamides or carboxylic acids can form internal salts with protonatable groups, such as amino groups. Salt formation can also occur through the action of a base on

[0033] Compounds of the general formula (I) are formed. Suitable bases include, for example, organic amines such as trialkylamines, morpholine, piperidine and pyridine, as well as ammonium, alkali or

[0034] Alkaline earth metal hydroxides, carbonates and hydrogen carbonates, in particular sodium and

[0035] Potassium hydroxide, sodium and potassium carbonate, and sodium and potassium bicarbonate. These salts are compounds in which the acidic hydrogen is replaced by a cation suitable for recycling, for example, metal salts, especially alkali metal salts, or

[0036] Alkaline earth metal salts, especially sodium and potassium salts, or also ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula

[0037] [NR a R b R c R d ] + , in which R a to R dEach independently represents an organic residue, in particular alkyl, aryl, arylalkyl, or alkylaryl. Alkylsulfonium and other compounds are also possible.

[0038] Alkylsulfoxonium salts, such as (Ci-C4)-trialkylsulfonium and (Ci-C4)-trialkylsulfoxonium salts.

[0039] The inventively substituted 2-heteroarylaminobenzenes of general formula (I) may exist in different tautomeric structures depending on external conditions such as pH, solvent and temperature, all of which are encompassed by general formula (I).

[0040] 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)".

[0041] Particularly preferred subject matter of the invention is compounds of the general formula (I), wherein A stands for nitrogen or -CX-,

[0042] X stands for hydrogen or halogen, R 1for an optionally substituted aryl or heteroaryl, wherein each ring or ring system is optionally equipped with up to 5 substituents, independently selected from the group R 5 , is substituted,

[0043] R 2 independently for halogen, cyano, nitro, formyl, formamide, (Ci-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkenyl, (C3-C8)-cycloalkyl, (C1-C4)- Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-alkylcarbonyl, (C1-C4)-haloalkylcarbonyl, carboxyl, (Ci-C4)-alkoxycarbonyl, (C1-C4)-haloalkoxycarbonyl, (C3-C Ö )- Cycloalkoxycarbonyl, carbamoyl, (C2-C4)-alkylaminocarbonyl, (C2-C6)-dialkylaminocarbonyl, (Ci-C4)-alkoxycarbonyl-(Ci-C4)-alkyl, (Ci-C4)-haloalkoxycarbonyl-(Ci-C4)-alkyl, carboxy-(Ci-C4)-alkyl, Hydroxy, NO 4 R 6, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, (Ci-C4)-Alkylthio, (Ci-C4)-Alkylsulfinyl, (Ci-C4)-Alkylsulfonyl, (Ci-C4)-Alkylaminosulfonyl, (CYG,)- Dialkylaminosulfonyl oder (C3-G,)-Trialkylsilyl steht, m ist gleich 0, 1, 2, oder 3,

[0044] R 3 für Wasserstoff, Halogen, Cyano, Nitro, (Ci-C4)-Alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl,

[0045] (Ci-C4)-Haloalkyl, (C3-G)-Cycloalkyl, (C3-G)-Cycloalkylmethyl, (Ci-C4)-Alkoxy, (G-G)- Haloalkoxy, (Ci-C4)-Alkylthio, (Ci-C4)-Haloalkylthio, (Ci-C4)-Alkylsulfinyl, (G-G)- Haloalkylsulfinyl, (Ci-C4)-Alkylsulfonyl, (Ci-C4)-Haloalkylsulfonyl steht,

[0046] R 4 , R 6 unabhängig voneinander für Wasserstoff, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, Aryl-(Ci-C4)-alkyl, Heteroaryl-(Ci-C4)-alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, (Ci-C4)-Alkylcarbonyl, Formyl oder (Ci-C4)-Alkoxycarbonyl steht, und

[0047] R 5für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, (G-G)- Alkenyl, (C2-C4)-Alkinyl, (C2-C4)-Haloalkenyl, (C2-C4)-Haloalkinyl, (Ci-G)-Alkoxy-(G-G)- alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylcarbonyl, (Ci-C4)-Haloalkylcarbonyl, Carboxyl, (Ci-C4)-Alkoxycarbonyl, (C1-C4)- Haloalkoxycarbonyl, (G-G)- Cycloalkoxycarbonyl, (Ci-C4)-Alkylaminocarbonyl, (G-G)-Dialkylaminocarbonyl, (G-G)- Cycloalkylaminocarbonyl, Hydroxy, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, (Ci-C4)-Alkylthio, (Ci-C4)-Haloalkylthio, (Ci-C4)-Alkylsulfinyl, (Ci-C4)-Haloalkylsulfinyl, (Ci-C4)-Alkylsulfonyl, (Ci-C- -Haloalkylsulfonyl, (Ci-C- -Alkylaminosulfonyl, (C2-C6)-Dialkylaminosulfonyl oder (C3-C6)-Trialkylsilyl steht, ausgenommen der nachfolgend genannten Verbindungen:

[0048] 2-(2-Phenoxyphenylamino)pyridin

[0049] 5-Brom-2-(2-phenoxyphenylamino)pyridin

[0050] 5-Chlor-2-(2-phenoxyphenylamino)pyridin

[0051] 2-(2-Phenoxyphenylamino)pyrimidine

[0052] 5-Bromo-2-(2-phenoxyphenylamino)pyrimidine

[0053] 5-Iodo-2-(2-phenoxyphenylamino)pyrimidine

[0054] 2-(2-(2-Pyridyloxy)phenylamino)pyridine.

[0055] Particularly preferred subject matter of invention are compounds of the general formula (I), wherein

[0056] A stands for nitrogen or -CX-

[0057] X stands for hydrogen, fluorine or chlorine,

[0058] R 1 for a possibly substituted phenyl, pyridyl or pyrimidyl, wherein each ring or ring system optionally has up to 5 substituents, independently selected from group R 5 , is substituted,

[0059] R 2 independently for halogen, cyano, nitro, (Ci-C4)-alkyl, (Ci-C- -haloalkyl, NR 4 R 6, (Ci-C- -Alkoxycarbonyl, (Ci-C- -Alkylthio or (Ci-C- -Alkoxy stands, m is equal to 0, 1, 2, or 3,

[0060] R 3 for hydrogen, halogen, cyano, nitro, (Ci-C4)-alkyl, (Ci-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkenyl, (C2-C4)-haloalkynyl, cyclpropyl, cyclopropylmethyl, (Ci-C4)-alkoxy, (Ci-C4)-haloalkoxy, (Ci-C4)-alkylthio or (Ci-C4)-haloalkylthio,

[0061] R 4 , R 6 independently of each other stands for hydrogen, (Ci-C4)-alkyl, (Ci-C4)-alkylcarbonyl or (C1-C4)-alkoxycarbonyl, and R 5 for hydrogen, halogen, cyano, (Ci-C4)-alkyl, (Ci-C- -haloalkyl, (Ci-C4)-alkylthio, (C1-C4)-alkoxy or (Ci-C4)-haloalkoxy, except for the following compounds:

[0062] 2-(2-Phenoxyphenylamino)pyridine

[0063] 5-Bromo-2-(2-phenoxyphenylamino)pyridine

[0064] 5-Chloro-2-(2-phenoxyphenylamino)pyridine

[0065] 2-(2-Phenoxyphenylamino)pyrimidine

[0066] 5-Bromo-2-(2-phenoxyphenylamino)pyrimidine

[0067] 5-Iodo-2-(2-phenoxyphenylamino)pyrimidine

[0068] 2-(2-(2-Pyridyloxy)phenylamino)pyridine.

[0069] Another preferred subject of invention is compounds of the general formula (I), wherein

[0070] A stands for nitrogen or -CX-

[0071] X stands for hydrogen, fluorine or chlorine,

[0072] R 1 for a possibly substituted phenyl, pyridyl or pyrimidyl, wherein each ring or ring system optionally has up to 5 substituents, independently selected from group R 5 , is substituted,

[0073] R 2 independently for halogen, cyano, nitro, (Ci-C4)-alkyl, (Ci-C4)-haloalkyl, (C1-C4)-alkoxycarbonyl, (Ci-C4)-alkylthio, NR 4 R 6or (Ci-C4)-alkoxy, m is equal to 0, 1, 2, or 3,

[0074] R 3 represents hydrogen, halogen, cyano, (Ci-C4)-alkyl, (Ci-C4)-haloalkyl, cyclpropyl, cyclopropyl-methyl, (Ci-C4)-alkoxy, (Ci-C4)-haloalkoxy, (Ci-C4)-alkylthio or (Ci-C4)-haloalkylthio,

[0075] R 4 , R 6 independently of each other stands for hydrogen or methyl, and R 5 for hydrogen, halogen, cyano, (Ci-C- alkyl, (Ci-C- -haloalkyl, (Ci-C4)-alkylthio, (C1-C4)-alkoxy or (Ci-C4)-haloalkoxy, except for the following compounds:

[0076] 2-(2-Phenoxyphenylamino)pyridine

[0077] 5-Bromo-2-(2-phenoxyphenylamino)pyridine

[0078] 5-Chloro-2-(2-phenoxyphenylamino)pyridine

[0079] 2-(2-Phenoxyphenylamino)pyrimidine

[0080] 5-Bromo-2-(2-phenoxyphenylamino)pyrimidine

[0081] 5-Iodo-2-(2-phenoxyphenylamino)pyrimidine

[0082] 2-(2-(2-Pyridyloxy)phenylamino)pyridine.

[0083] Another preferred subject of invention is compounds of the general formula (I), wherein

[0084] A stands for nitrogen or -CX-

[0085] X stands for hydrogen, fluorine or chlorine,

[0086] R 1 for a possibly substituted phenyl, pyridyl or pyrimidyl, each ring optionally with up to 5 substituents, independently selected from group R 5 , is substituted,

[0087] R 2 independently of each other, m stands for fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, methylthio or amino, where m is equal to 0, 1, 2, or 3.

[0088] R 3 stands for hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy, methylthio or trifluoromethylthio.

[0089] R 5for hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy or

[0090] Trifluoromethoxy stands, with the exception of the following compounds: 2-(2-Phenoxyphenylamino)pyridine

[0091] 5-Bromo-2-(2-phenoxyphenylamino)pyridine

[0092] 5-Chloro-2-(2-phenoxyphenylamino)pyridine

[0093] 2-(2-Phenoxyphenylamino)pyrimidine

[0094] 5-Bromo-2-(2-phenoxyphenylamino)pyrimidine

[0095] 5-Iodo-2-(2-phenoxyphenylamino)pyrimidine

[0096] 2-(2-(2-Pyridyloxy)phenylamino)pyridine.

[0097] The general or preferred residue definitions listed above apply both to the final products of the general formula (I) and, accordingly, to the starting materials or intermediates required for their production. These residue definitions can

[0098] They can be combined arbitrarily with each other, including between the specified preferred areas.

[0099] 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 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.

[0100] With regard to the compounds according to the invention, the terms used above and below are explained. These are familiar to those skilled in the art and have, in particular, the meanings explained below:

[0101] Unless otherwise defined, the general rule for the designation of chemical groups is that the connection to the framework or the rest of the molecule is made via the last mentioned structural element of the chemical group in question, i.e., for example, in the case of (C2-Cs)-alkenyloxy via the oxygen atom, and in the case of heteroaryl-(Ci-C6)-alkyl or (Ci-C4)-alkylthio-(Ci-C4)-alkyl, respectively, via the C atom of the alkyl group.

[0102] According to the invention, "alkylsulfonyl" - either alone or as part of a chemical group - stands for straight-chain or branched alkylsulfonyl, preferably with 1 to 8, or with 1 to 6

[0103] carbon atoms, e.g. (but not limited to) (CrG >)- Alkylsulfonyl wie Methylsulfonyl, Ethyl- sulfonyl, Propylsulfonyl, 1-Methylethylsulfonyl, Butylsulfonyl, 1-Methylpropylsulfonyl, 2-Methyl- propylsulfonyl, 1,1-Dimethylethylsulfonyl, Pentylsulfonyl, 1-Methylbutylsulfonyl, 2-Methylbutyl- sulfonyl, 3-Methylbutylsulfonyl, 1,1-Dimethylpropylsulfonyl, 1,2-Dimethylpropylsulfonyl, 2,2-Di- methylpropylsulfonyl, 1-Ethylpropylsulfonyl, Hexylsulfonyl, 1-Methylpentylsulfonyl, 2-Methyl- pentylsulfonyl, 3-Methylpentylsulfonyl, 4-Methylpentylsulfonyl, 1,1-Dimethylbutylsulfonyl, 1,2-Di- methylbutylsulfonyl, 1,3-Dimethylbutylsulfonyl, 2,2-Dimethylbutylsulfonyl, 2,3-Dimethylbutylsulfonyl, 3 ,3 -Dimethylbutylsulfonyl, 1 -Ethylbutylsulfonyl, 2-Ethylbutylsulfonyl, 1 , 1 ,2-Trimethylpropylsulfonyl,

[0104] 1 ,2,2-Trimethylpropylsulfonyl, 1 -Ethyl- 1 -methylpropylsulfonyl und 1 -Ethyl-2-methylpropylsulfonyl .

[0105] According to the invention, "alkylthio" - either alone or as part of a chemical group - stands for straight-chain or branched S-alkyl, preferably with 1 to 8, or with 1 to 6

[0106] Kohlenstoffatomen, wie (Ci-Cio)-, (C rG,)- oder (Ci-C -Alkylthio, z.B. (aber nicht beschränkt auf) (Ci- C6)-Alkylthio wie 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-Methyl- pentylthio, 1,1-Dimethylbutylthio, 1,2-Dimethylbutylthio, 1,3-Dimethylbutylthio, 2,2-Dimethylbutyl- thio, 2,3-Dimethylbutylthio, 3,3-Dimethylbutylthio, 1-Ethylbutylthio, 2-Ethylbutylthio, 1,1,2-Tri- methylpropylthio, 1,2,2-Trimethylpropylthio, 1 -Ethyl- 1 -methylpropylthio und l-Ethyl-2-methyl- propylthio.

[0107] “Alkylsulfinyl (Alkyl-S(=0)-)”, unless otherwise defined elsewhere, according to the invention stands for alkyl groups that are bonded to the skeleton via -S(=0)-, such as (Ci-Cio)-, (Ci-Ce)- or (C1-C4)- alkylsulfinyl, e.g.(aber nicht beschränkt auf) (Ci-C6)-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-Di- methylpropylsulfinyl, 1-Ethylpropylsulfinyl, Hexylsulfinyl, 1-Methylpentylsulfinyl, 2-Methylpentyl- sulfinyl, 3-Methylpentylsulfinyl, 4-Methylpentylsulfinyl, 1,1-Dimethylbutylsulfinyl, 1,2-Dimethyl- butylsulfinyl, 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 l-Ethyl-2-methylpropylsulfmyl.

[0108] "Alkoxy" means an alkyl group bonded via an oxygen atom, e.g. B. (but not limited to) (Ci-Ce)-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 means an alkenyl group bonded via an oxygen atom; alkynyloxy means an alkynyl group bonded via an oxygen atom, such as (C2-C 10 )-, (C2-C6)- or (C2-C4)-alkenoxy or (C3-C 10 )-, (C3-C6)- or (C3-C4)-alkynoxy.

[0109] Alkylcarbonyl (alkyl-C(=0)-), unless otherwise defined elsewhere, by invention refers to alkyl groups that are bonded to the skeleton via -C(=0)-, such as (C1-C10)-, (Ci-Ce)-, or (C1-C4)-alkylcarbonyl. The number of carbon atoms refers to the alkyl group in the

[0110] Alkylcarbonyl group.

[0111] “Alkoxycarbonyl (alkyl-0-C(=0)-)”, unless otherwise defined elsewhere: alkyl groups bonded to the framework via -0-C(=0)-, such as (C1-C10), (Ci-Ce), or (Ci-C4)-alkoxycarbonyl. The number of carbon atoms refers to the alkyl group within the alkoxycarbonyl chain. Similarly, “alkenyloxycarbonyl” and “alkynyloxycarbonyl”, unless otherwise defined elsewhere, are, according to the invention, alkenyl and alkynyl groups, respectively, bonded to the framework via -0-C(=0)-, such as (C2-C10), (C2-C6), or (C2-C4)-alkenyloxycarbonyl and (C3-C10), (C3-C6), or (C3-C4)-alkynyloxycarbonyl, respectively. The number of C atoms refers to the alkenyl or alkynyl residue in the alkene or alkynyloxycarbonyl group.

[0112] 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, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.

[0113] 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.

[0114] According to the invention, the term "heteroaryl" stands for heteroaromatic compounds, i.e.

[0115] vollständig ungesättigte aromatische heterocyclische Verbindungen, vorzugsweise für 5- bis 7-gliedrige Ringe mit 1 bis 4, vorzugsweise 1 oder 2 gleichen oder verschiedenen Heteroatomen, vorzugsweise O, S oder N. Erfmdungsgemäße Heteroaryle sind beispielsweise lH-Pyrrol-l-yl; lH-Pyrrol-2-yl; lH-Pyrrol-

[0116] 3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, lH-Imidazol-l-yl; lH-Imidazol-2-yl; lH-Imidazol-

[0117] 4-yl; lH-Imidazol-5-yl; lH-Pyrazol-l-yl; lH-Pyrazol-3-yl; lH-Pyrazol-4-yl; lH-Pyrazol-5-yl, 1H-1,2,3- Triazol-l-yl, lH-l,2,3-Triazol-4-yl, lH-l,2,3-Triazol-5-yl, 2H-l,2,3-Triazol-2-yl, 2H-l,2,3-Triazol-4-yl, lH-l,2,4-Triazol-l-yl, lH-l,2,4-Triazol-3-yl, 4H-l,2,4-Triazol-4-yl, l,2,4-Oxadiazol-3-yl, 1,2,4- Oxadiazol-5-yl, l,3,4-Oxadiazol-2-yl, l,2,3-Oxadiazol-4-yl, l,2,3-Oxadiazol-5-yl, l,2,5-Oxadiazol-3-yl, Azepinyl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Pyrazin-2-yl, Pyrazin-3-yl, Pyrimidin-2-yl,

[0118] Pyrimidin-4-yl, Pyrimidin-5-yl, Pyridazin-3-yl, Pyridazin-4-yl, l,3,5-triazin-2-yl, l,2,4-triazin-3-yl, l,2,4-triazin-5-yl, l,2,4-triazin-6-yl, l,2,3-triazin-4-yl, l,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, l,3-oxazol-2-yl, l,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-Tetrazol-5-yl, 1H-1,2,3,4-Tetrazol-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 residues. If two adjacent

[0119] If carbon atoms are part of another aromatic ring, then these are fused heteroaromatic systems, such as benzo-condensed or multiply fused heteroaromatics.

[0120] For example, quinolines are preferred (e.g. quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl); Isoquinolines (e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl); quinoxaline; quinazoline; cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; pyridopyrazines; pyridopyrimidines; pyridopyridazines; pteridines; Pyrimidopyrimidines. Examples of heteroaryls also include 5- or 6-membered benzo-condensed rings from the group 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indol-4-yl, 1H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1H-benzofüran-2-yl, 1H-benzofüran-3-yl, 1H-benzofüran-4-yl, 1H-benzofüran-5-yl, 1H-benzofüran-6-yl, 1H-benzofüran-7-yl, 1H-benzothiophen-2-yl, 1H-benzothiophen-3-yl, 1H-benzothiophen-4-yl, 1H-benzothiophen-5-yl, 1H-benzothiophen-6-yl, 1H-benzothiophen-7-yl, 1H-indazol-

[0121] 1-yl, lH-Indazol-3-yl, lH-Indazol-4-yl, lH-Indazol-5-yl, lH-Indazol-6-yl, lH-Indazol-7-yl, 2H-Indazol-

[0122] 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-l-yl, 2H-Isoindol-3-yl, 2H-Isoindol-4-yl, 2H-Isoindol-5-yl, 2H-Isoindol-6-yl; 2H-Isoindol-7-yl, lH-Benzimidazol-l-yl, lH-Benzimidazol-2-yl, lH-Benzimidazol-4-yl, 1H- Benzimidazol-5-yl, lH-Benzimidazol-6-yl, lH-Benzimidazol-7-yl, l,3-Benzoxazol-2-yl, 1,3- Benzoxazol-4-yl, l,3-Benzoxazol-5-yl, l,3-Benzoxazol-6-yl, l,3-Benzoxazol-7-yl, l,3-Benzthiazol-2-yl, l,3-Benzthiazol-4-yl, l,3-Benzthiazol-5-yl, l,3-Benzthiazol-6-yl, l,3-Benzthiazol-7-yl, 1,2- Benzisoxazol-3-yl, l,2-Benzisoxazol-4-yl, l,2-Benzisoxazol-5-yl, l,2-Benzisoxazol-6-yl, 1,2- Benzisoxazol-7-yl, l,2-Benzisothiazol-3-yl, l,2-Benzisothiazol-4-yl, l,2-Benzisothiazol-5-yl, 1,2- Benzisothiazol-6-yl, l,2-Benzisothiazol-7-yl.

[0123] The term "halogen" refers to substances such as fluorine, chlorine, bromine, or iodine. If the

[0124] When used as a term for a residue, "halogen" means, for example, a fluorine, chlorine, bromine or iodine atom.

[0125] According to the invention, "alkyl" means a straight-chain or branched open-chain saturated hydrocarbon residue, which may be single- or multiply substituted, in the latter case being 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).

[0126] “Haloalkyl”, “-alkenyl” and “-alkynyl” mean alkyl, alkenyl or alkynyl, respectively, partially or completely substituted by the same or different halogen atoms, e.g., monohaloalkyl

[0127] (= monohaloalkyl) such as. B. CH2CH2CI, CH2CH2Br, CHCICH3, CH2CI, CH2F; Perhaloalkyl such as E.g. CC1 3, CC1F 2, CFC12, CF2CCIF 2, CF2CCIFCF3; Polyhaloalkyl such as CH2CHFC1, CF2CC1FH, CF2CBrFH, CH2CF3; The term perhaloalkyl also includes the term perfluoroalkyl.

[0128] “Haloalkoxy” is, for example, OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 and OCH2CH2CI; the same applies to haloalkenyl and other halogen-substituted residues.

[0129] The expression "(Ci-C- -alkyl)" used here as an example is a shorthand notation for straight-chain or branched alkyl with one to four carbon atoms, according to the

[0130] The range specified for carbon atoms includes the residues methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl, or tert-butyl. General alkyl residues with a larger specified range of carbon atoms, e.g., "(Ci-C6)-alkyl," also include straight-chain or branched alkyl residues with a larger number of carbon atoms, i.e., as in the example, also the alkyl residues with 5 and 6 carbon atoms.

[0131] Unless otherwise specified, for hydrocarbon residues such as alkyl, alkenyl, and alkynyl groups, including those in compound groups, the lower carbon skeletons are preferred, e.g., 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, for example, methyl, ethyl, n- or i-propyl, n-, i-, t-, or 2-butyl, pentyls, hexyls such as n-hexyl, i-hexyl, and 1,3-dimethylbutyl, and heptyls such as n-heptyl, 1-methylhexyl, and 1,4-dimethylpentyl. Alkenyl and alkynyl groups have the meaning of the corresponding unsaturated groups, including at least one double or triple bond, respectively. Residues with a double bond are preferred.

[0132] Triple bond.

[0133] The term "alkenyl" specifically includes straight-chain or branched open-chain alkenyls.

[0134] 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, for example, vinyl, which may be substituted by further alkyl groups, e.g. (but not limited to) (C'2-G,)-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-l-propenyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-l-butenyl, 3-methyl-1-butenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, l,l-dimethyl-2-propenyl, 1,2-dimethyl-l-propenyl, l,2-dimethyl-2-propenyl, 1-ethyl-l-propenyl, l-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl,5- Hexenyl, 1 -Methyl- 1 -pentenyl, 2 -Methyl- 1 -pentenyl, 3-Methyl-l -pentenyl, 4-Methyl-l -pentenyl, 1- Methyl-2-pentenyl, 2-Methyl-2 -pentenyl, 3 -Methyl-2 -pentenyl, 4-Methyl-2-pentenyl, l-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, l,l-Dimethyl-2-butenyl, 1,1-Dimethyl- 3-butenyl, 1,2-Dimethyl- 1-butenyl, l,2-Dimethyl-2-butenyl, l,2-Dimethyl-3-butenyl, 1,3-Dimethyl-l- butenyl, l,3-Dimethyl-2-butenyl, l,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3-Dimethyl-l- butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3-Dimethyl-l-butenyl, 3,3-Dimethyl-2- butenyl, 1-Ethyl- 1-butenyl, l-Ethyl-2-butenyl, l-Ethyl-3-butenyl, 2-Ethyl- 1-butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, l,l,2-Trimethyl-2-propenyl, 1-Ethyl-l -methyl-2 -propenyl, l-Ethyl-2-methyl-l- propenyl und l-Ethyl-2 -methyl-2 -propenyl.,

[0135] The term "alkynyl" specifically includes straight-chain or branched open-chain

[0136] Hydrocarbon residues with more than one triple bond or with one or more

[0137] Dreifachbindungen und einer oder mehreren Doppelbindungen ein, wie beispielsweise 1,3-Butatrienyl bzw. 3-Penten-l-in-l-yl. (C2-Ce) -Alkinyl bedeutet z.B. 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, l-Methyl-4-pentinyl, 2 -Methyl-3 -pentinyl, 2-Methyl-4-pentinyl, 3-Methyl-l -pentinyl, 3- Methyl-4-pentinyl, 4-Methyl-l -pentinyl, 4-Methyl-2 -pentinyl, l,l-Di-methyl-2 -butinyl, l,l-Dimethyl-3- butinyl, l,2-Dimethyl-3 -butinyl, 2, 2-Dimethyl-3 -butinyl, 3,3-Dimethyl-l-butinyl, l-Ethyl-2 -butinyl, 1- Ethyl-3 -butinyl, 2-Ethyl-3 -butinyl und 1-Ethyl-l -methyl-2 -propinyl.

[0138] The term "cycloalkyl" means a carbocyclic, saturated ring system with preferably 3-8 ring carbon atoms, e.g., cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, or alkoxycarbonyl.

[0139] hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl,

[0140] Cycloalkylaminocarbonyl. In the case of optionally substituted cycloalkyl, cyclic systems with substituents are included, including substituents with a double bond at the

[0141] Cycloalkyl groups, e.g., an alkylidene group such as methylidene, are included. 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... B. l,l'-Bi(cyclopropyl)-l-yl, l,l'-Bi(cyclopropyl)-2-yl. The term "(C3-C7)-cycloalkyl" is a shorthand notation for cycloalkyl with three to seven nucleotides.

[0142] Carbon atoms according to the range specified for C atoms.

[0143] In the case of substituted cycloalkyl, spirocyclic aliphatic systems are also included, such as Spiro[2.2]pent-l-yl, Spiro[2.3]hex-l-yl, Spiro[2.3]hex-4-yl, 3-Spiro[2.3]hex-5-yl, Spiro[3.3]hept-l-yl, Spiro[3.3]hept-2-yl.

[0144] “Arylalkyl” refers to an aryl residue bound via an alkyl group and “Heteroarylalkyl” refers to a heteroaryl residue bound via an alkyl group.

[0145] According to the invention, "haloalkylthio" - either alone or as part of a chemical group - stands for straight-chain or branched S-haloalkyl, preferably with 1 to 8, or with 1 to 6

[0146] Carbon atoms, such as (Ci-Cs)-, (CrG,)- or (Ci-C- -haloalkylthio, e.g. (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-l-ylthio, 2,2,2-difluoroeth-l-ylthio, 3,3,3-prop-l-ylthio.

[0147] “Halocycloalkyl” means a cycloalkyl partially or fully substituted by the same or different halogen atoms, such as F, CI and Br, or by haloalkyl, such as trifluoromethyl or difluoromethyl, e.g. 1-fluorocycloprop-l-yl, 2-fluorocycloprop-l-yl, 2,2-difluorocycloprop-l-yl, 1-fluorocyclobut-l-yl, 1-trifluoromethylcycloprop-l-yl, 2-trifluoromethylcycloprop-l-yl, 1-chlorocycloprop-l-yl, 2-chlorocycloprop-l-yl, 2,2-dichlorocycloprop-l-yl, 3,3-difluorocyclobutyl.

[0148] According to the invention, "trialkylsilyl" – either alone or as part of a chemical group – stands for straight-chain or branched Si-alkyl, preferably with 1 to 8, or with 1 to 6

[0149] carbon atoms, such as tri-[(Ci-C8)-, (CrG,)- or (Ci-C4)-alkyl]silyl, e.g. (but not limited to) trimethylsilyl, triethylsilyl, tri-(n-propyl)silyl, tri-(isopropyl)silyl, tri-(n-butyl)silyl, tri-(1-methylprop-l-yl)silyl, tri-(2-methylprop-l-yl)silyl, tri(l,l-dimethyleth-l-yl)silyl, tri(2,2-dimethyleth-1-yl)silyl.

[0150] If the compounds can form tautomers through hydrogen shifts, which would not be formally covered by the general formula (I) in a structural sense, these tautomers are nevertheless included in the definition of the compounds of general formula (I) according to the invention, unless a specific tautomer is the subject of consideration. For example, many carbonyl compounds can exist in both the keto and enol forms, both of which are covered by the definition of the compound of general formula (I).

[0151] 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 shape, such as enantiomers, diastereomers, Z- and E-isomers, are all encompassed by general formula (I). For example, if one or more alkenyl groups are present, diastereomers (Z- and E-isomers) can occur. If, for example, one or more asymmetric carbon atoms are present, enantiomers and diastereomers can occur. Stereoisomers can be determined from the...

[0152] The resulting mixtures are obtained using conventional 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 prepared by using stereoselective reactions with optically active starting materials and / or auxiliary substances. The invention thus also relates to all stereoisomers included in the general formula (I) but not specified with their particular stereoform, as well as their mixtures.

[0153] Provided the compounds are obtained as solids, purification can also be carried out by

[0154] Recrystallization or digestion may be carried out. If individual compounds (I) are not satisfactorily accessible by the methods described below, they can be prepared by derivatization of other compounds (I).

[0155] 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 HPFC (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.

[0156] The present invention also claims methods for preparing the compounds of general formula (I) according to the invention. 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, R 1 , R 2 , R 3 and m of the general formula (I) have the previously defined meanings in the following schemes, unless exemplary but non-restrictive definitions are given.

[0157] The compounds according to the invention can be produced, for example, according to the method shown in Scheme 1.

[0158]

[0159] (El) (E-Il) (I)

[0160] Scheme 1.

[0161] The pyri(mi)dines of general formula (I) can be prepared by coupling the corresponding anilines (EI) with the pyri(mi)dines (EU), where LG is a leaving group, in the presence of, for example, a palladium catalyst. The required base can be, for example, 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. The anilines of general formula (EI) are known from the literature and can be prepared, for example, according to the methods described in Organic Letters, 19(14), 3855-3858; 2017 and similar methods.

[0162] Selected detailed synthesis examples for the compounds of general formula (I) according to the invention are listed below. The ^-NMR-, 13 C-NMR and 19F-NMR spectroscopic data given for the chemical examples described in the following sections, (400 MHz for ^-NMR and 150 MHz for 13 C-NMR and 375 MHz at 19¹⁹F NMR, solvent CDCE, CD3OD, or de-DMSO, internal standard: tetramethylsilane (d = 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 CEE^CEhGEEK, t-Bu = C^CEEK, n-Bu = unbranched butyl, n-Pr = unbranched propyl, i-Pr = branched propyl, c-Pr = cyclopropyl, c-Hex = cyclohexyl.

[0163] Synthesis examples:

[0164] Table example number 1-246 :

[0165] Synthesis stage 1: 2-(2-fluorophenoxy)-3-nitrobenzonitrile

[0166]

[0167] 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 of DMF was stirred for 2 h at 100 °C. It was then diluted with 100 mL of DCM and washed with water (100 mL). The mixture was dried over sodium sulfate and concentrated under vacuum. The yield was 950 mg (87%).

[0168] Synthesis step 2: 3-amino-2-(2-fluorophenoxy)benzonitrile

[0169]

[0170] A solution of 950 mg of 2-(2-fluorophenoxy)-3-nitrobenzonitrile (3.68 mmol, 1.0 eq) and 2.49 g of SnCE^EEO (11.05 mmol, 3.0 eq) in 30 ml of 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%).

[0171] Synthesis Step 3: 2-(2-Fluorphenoxy)-3-(pyrimidin-2-ylamino)benzonitrile (Table - Example 1-246) A solution of 250 mg 3-Amino-2-(2-fluorphenoxy)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 for 12 h at 100 °C under argon. The solvent was concentrated under vacuum and the residue

[0172] Purified by column chromatography. The yield of yellow pesticide was 65 mg.

[0173] Table example number 2-141:

[0174] Synthesis stage 1: 4-(5-Chloropyrimidin-2-ylamino)-3-fluorobenzoic acid methyl ester

[0175]

[0176] A solution of 2 g of methyl 4-amino-3-fluorobenzoate (11.8 mmol), 541 mg of Pd₂DBA₃ (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 with argon for 3 h. The solvent was concentrated under vacuum, and the residue was purified by column chromatography. The yield was 2.9 g (87%).

[0177] Synthesis step 2: 4-(5-chloropyrimidin-2-ylamino)-3-fluorobenzoic acid

[0178]

[0179] 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 removed by filtration. Yield: 1.8 g (68%). Synthesis step 3: Ethyl-(4-(5-chloropyrimidine-2-ylamino)-3-fluorophenyl)carbamate

[0180] 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).

[0181] Synthesis step 4: Ethyl (4-(5-chloropyrimidin-2-ylamino)-5-fluoro-2-nitrophenyl) carbamate

[0182]

[0183] 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 was prepared under cooling from 365 mg

[0184] Nitric acid (60%, 3.8 mmol) and 1.74 ml of acetic anhydride were added. After 1 h, stir at

[0185] Room temperature was alkalized with sodium bicarbonate solution and extracted with ethyl acetate. The organic phase was washed with saline solution, dried over sodium sulfate, concentrated, and the residue purified by column chromatography. Yield: 550 mg (40%).

[0186] Synthesis step 5: Ethyl-(4-(5-chloropyrimidin-2-ylamino)-5-(4-fluorphenoxy)-2-nitrophenyl)carbamate (Table example number 2-141)

[0187]

[0188] 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%).

[0189] Table example number 2-130:

[0190] 4-(5-Chloropyrimidin-2-ylamino)-5-(4-fluorophenoxy)-2-nitroaniline

[0191]

[0192] 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:

[0193] 2-Chloro-4-(5-chloropyrimidine-2-ylamino)-3-(4-fluorophenoxy)-6-nitroaniline

[0194]

[0195] A solution of 145 mg 4-(5-chloropyrimidine-2-ylamino)-5-(4-fluorphenoxy)-2-nitroaniline

[0196] (0.38 mmol) in 2 ml DMF was mixed with 51 mg NCS (0.38 mmol, 1 eq). After 2 days at

[0197] Room temperature solution 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%). By analogy to the preparation examples mentioned above and cited in the appropriate place, the following compounds of the general formula, listed in Table 1, were obtained.

[0198]

[0199] Table 1

[0200]

[0201] By analogy to the manufacturing examples mentioned above and cited at the appropriate point, the following compounds of the general formula, shown in Table 2, are obtained.

[0202]

[0203] 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.

[0204] Table 3

[0205]

[0206] The NMR data of disclosed examples are listed in classical form (d-values, number of H atoms, multiplet splitting). NMR data of the final products (classical form)

[0207]

[0208] The present invention further relates to the use of one or more

[0209] 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, as a herbicide and / or plant growth regulator, preferably in crops of useful and / or ornamental plants.

[0210] The present invention further relates to a method for controlling pests and / or regulating plant growth, characterized in that an effective amount of 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 used.

[0211] on the (harmful) plants, (harmful) plant seeds, the soil in which or on which the

[0212] (Harmful) plants grow, or the cultivation area is treated.

[0213] The present invention also relates to a method for controlling unwanted plants, preferably in crops, characterized in that an effective amount of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one of the 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 used.

[0214] applied to unwanted plants (e.g., pest plants such as mono- or dicotyledonous weeds or unwanted cultivated plants), the seed of the unwanted plants (i.e., plant seeds, e.g., grains, seeds, or vegetative reproductive organs such as tubers or shoot parts with buds), the soil in which or on which the unwanted plants grow (e.g., the soil of cultivated land or non-cultivated land), or the cultivation area (i.e., the area on which the unwanted plants will grow).

[0215] The present invention also relates to methods for combating

[0216] Growth regulation of plants, preferably of crop plants, characterized in that an effective amount of 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,

[0217] the plant, the plant's seed (i.e., plant seeds, e.g., grains, seeds, or vegetative reproductive organs such as tubers or shoots with buds), the soil in which or on which the plants grow (e.g., the soil of cultivated land or non-cultivated land), or the growing area (i.e., the area on which the plants will grow) is applied.

[0218] The inventive compounds or agents can be applied, for example, in pre-sowing (possibly also by incorporation into the soil), pre-emergence and / or

[0219] Post-emergence methods are used. Specifically, some representatives of the mono- and dicotyledonous weed flora are mentioned as examples, which can be controlled by the compounds according to the invention, without the mention of these being intended to restrict them to specific species.

[0220] Preferably, in an inventive method for controlling weeds or regulating plant growth, one or more compounds of general formula (I) and / or their salts are used to control weeds or to regulate plant growth in crops of useful or ornamental plants, wherein the useful or ornamental plants are, in a preferred embodiment, transgenic plants. The inventive compounds of general formula (I) and / or their salts are suitable for controlling the following genera of monocotyledonous and dicotyledonous weeds:

[0221] Monocot harmful plants of the species: 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.

[0222] Dicot harmful plants of the species: 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, Lindemia, 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.

[0223] If the inventive compounds of general formula (I) 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.

[0224] When applying the active ingredients of the general formula (I) to the green parts of the plant in

[0225] In post-emergence treatments, growth stops after application and the weeds remain at the growth stage they were at at the time of application or die completely after a certain period, thus preventing any harmful effects on the cultivated plants.

[0226] Weed competition is eliminated very early and sustainably.

[0227] Although the inventive compounds of general formula (I) exhibit excellent herbicidal activity against mono- and dicotyledonous weeds, cultivated plants of economically important crops, e.g. dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum,

[0228] 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 invented compound and its application rate. For these reasons, the compounds are very well suited for the selective control of unwanted plant growth in crops such as agricultural crops or ornamental plantings.

[0229] Furthermore, the compounds according to the invention of the general formula (I) (depending on their respective structure and the amount applied) exhibit excellent

[0230] Growth-regulating properties in cultivated plants. They intervene in a regulatory manner in the plant's own metabolism and can thus be used to selectively influence...

[0231] They are used to treat plant constituents and to facilitate harvesting, for example by triggering desiccation and growth retardation. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth without killing the plants. Inhibition of vegetative growth plays a significant role in many monocot and dicot crops, as it can, for example, reduce or completely prevent lodging.

[0232] 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, for example, to the harvested material in terms of quantity, quality, storability, composition, and specific constituents.

[0233] Transgenic plants with increased starch content or altered starch quality, or those with a different fatty acid composition of the output, are known.

[0234] The application of the compounds of the general formula (I) and / or their salts according to the invention is preferred with regard to transgenic cultures in economically important transgenic cultures of useful and ornamental plants, e.g. of cereals such as wheat, barley, rye, oats, millet, rice and maize or also cultures of sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetables.

[0235] 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.

[0236] 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

[0237] Herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms like fungi, bacteria, or viruses. Other special properties relate, for example, to the delivered goods in terms of quantity, quality, and storability.

[0238] Composition and specific ingredients. For example, transgenic plants with increased starch content or altered starch quality, or those with a different fatty acid composition of the output, are known. Further special properties can include tolerance or resistance to abiotic stressors such as heat, cold, drought, salt, and ultraviolet radiation.

[0239] 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.

[0240] Preferably, the compounds of general formula (I) can be used as herbicides in

[0241] Crops are used that are resistant to the phytotoxic effects of herbicides or have been made resistant through genetic engineering.

[0242] Conventional methods for producing new plants that have modified properties compared to previously existing plants include, for example, classical

[0243] Breeding methods and the creation of mutants. Alternatively, new plants with altered characteristics can be created using genetic engineering techniques.

[0244] Numerous molecular biological techniques for producing new transgenic plants with altered properties are 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, for example, to perform base exchanges, remove partial sequences, or add natural or synthetic sequences. For joining the DNA fragments...

[0245] Adaptors or linkers can be attached to each other between the fragments.

[0246] The production of plant cells with reduced activity of a gene product can

[0247] This can be achieved, for example, by expressing at least one corresponding antisense RNA, a sense RNA to achieve a cosuppression effect, or the expression of at least one appropriately engineered ribozyme that specifically cleaves transcripts of the aforementioned gene product. For this purpose, DNA molecules can be used 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.

[0248] 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.

[0249] The transgenic plant cells can be regenerated into entire plants using known techniques. In principle, the transgenic plants can be any type of plant.

[0250] Plant species are involved, i.e., both monocotyledonous and dicotyledonous plants.

[0251] 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.

[0252] 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, such as 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.

[0253] When the compounds of general formula (I) according to the invention are applied in transgenic crops, in addition to the effects on weeds observed in other crops, 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.

[0254] The invention therefore also relates to the use of the compounds of general formula (I) and / or their salts as herbicides for controlling pests in crops of useful or ornamental plants, optionally in transgenic crops.

[0255] 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.

[0256] The use of compounds of general formula (I) in soybeans in pre- or post-emergence applications is also preferred.

[0257] 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.

[0258] The invention also relates to the use of one or more compounds of the general formula (I) or their salts or an agent according to the invention (as defined below) (in a 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.

[0259] The invention also relates to a herbicidal and / or plant growth regulator, characterized in that the agent

[0260] (a) contains one or more compounds of general formula (I) and / or their salts as defined above, preferably in one of those characterized as preferred or particularly preferred

[0261] Design, in particular one or more combinations of the formulas

[0262] 1-1 to 1-376, 2-1 to 2-141, 3-1 to 3-56 and / or their salts, each as defined above, and

[0263] (b) one or more further substances selected from groups (i) and / or (ii): (i) 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 the general formula (I) defined above), fungicides, safeners, fertilizers and / or further growth regulators,

[0264] (ii) one or more formulation aids commonly used in plant protection.

[0265] The other agrochemical active substances of component (i) of an inventive product are preferably selected from the group of substances listed in "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.

[0266] 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-forming agents, 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.

[0267] 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 the usual preparations. The invention therefore also relates to herbicidal and plant growth regulator agents containing compounds of general formula (I) and / or their salts.

[0268] The compounds of general formula (I) and / or their salts can be formulated in various ways, depending on the biological and / or physicochemical parameters. Possible formulations include, for example:

[0269] 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,

[0270] Capsule suspensions (CS), dusting agents (DP), pickling agents, granules for spreading and

[0271] Soil application, granules (GR) in the form of micro-, spray-, lift- and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations,

[0272] Microcapsules and waxes. 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, "Solvent 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. Ine., NY 1964; Schönfeldt, "Interface Active Agents"

[0273] Ethylene oxide adducts", Scientific Publishing Company, Stuttgart 1976; Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hanser Publishing House Munich, 4th edition 1986.

[0274] 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 surfactants of an ionic and / or non-ionic nature (wetting agents,

[0275] Dispersing agents), e.g., 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. For the production of 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 aids.

[0276] Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, e.g., 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). Examples of emulsifiers that can be used include: alkylarylsulfonic acid calcium salts such as...

[0277] Ca-dodecylbenzenesulfonate or non-ionic emulsifiers such as fatty acid polyglycol esters,

[0278] Alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters or

[0279] Polyoxyethylene sorbitan esters such as polyoxyethylene sorbitan fatty acid esters.

[0280] Dusting agents are obtained by grinding the active ingredient with finely dispersed solid substances, e.g.

[0281] Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

[0282] Suspension concentrates can be water- or oil-based. They can be produced, for example, by wet milling using commercially available bead mills and, if necessary, the addition of surfactants, such as those already listed above for the other formulation types. Emulsions, e.g., oil-in-water emulsions (EW), can be prepared, for example, using stirrers,

[0283] Colloid mills and / or static mixers using aqueous organic

[0284] to produce solvents and, if necessary, surfactants, such as those already listed above for the other formulation types.

[0285] 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, e.g., polyvinyl alcohol, sodium polyacrylate, or mineral oils. Suitable

[0286] Active ingredients are granulated in the manner usual for the production of fertilizer granules - if desired in mixture with fertilizers.

[0287] Water-dispersible granules are usually produced using standard methods such as spray drying, fluidized bed granulation, disc granulation, high-speed mixing, and extrusion without solid inert material.

[0288] For the production of disc, fluid bed, extruder and spray 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.

[0289] For further details on the formulation of plant protection products, see, for example, GC Klingman, "Weed Control as a Science", John Wiley and Sons, Ine., New York, 1961, pages 81-96 and JD Freyer, SA Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

[0290] 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.

[0291] In sprayable powders, the active ingredient concentration is, for example, approximately 10 to 90 wt%, 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 form

[0292] 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. For 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 example, the active ingredient content of water-dispersible granules is between 1 and 95 wt%, preferably between 10 and 80 wt%.

[0293] 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).

[0294] The compounds of general formula (I) or their salts 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 a finished formulation or as

[0295] Tank mixtures. The combination formulations can be produced based on the formulations mentioned above, taking into account the physical properties and stabilities of the active ingredients to be combined.

[0296] For example, known active ingredients based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate 3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoendesaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as described 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.

[0297] Of particular interest is the selective control of weeds in crops of useful and ornamental plants. Although the inventive compounds of general formula (I) 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, less selective herbicides. In this regard, combinations

[0298] Compounds (I) of the invention are of particular interest, which are the compounds of general formula (I) or their combinations with other herbicides or pesticides and

[0299] They contain safeners. The safeners, which are used in an antidote-effective concentration, reduce the phytotoxic side effects of the herbicides / pesticides used, e.g. in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugar cane, rapeseed, cotton and soybeans, preferably cereals.

[0300] The weight ratio of herbicide (mixture) to safener generally depends on the

[0301] The application rate depends on the amount of herbicide and the efficacy of the respective safener and can vary within wide limits, for example in the range of 200:1 to 1:200, preferably 100:1 to 1:100, 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 as

[0302] Ready-to-use formulation or tank mix with the herbicides is provided and applied.

[0303] 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.

[0304] External conditions such as temperature, humidity, etc., influence to some extent the amount of compounds of general formula (I) and / or their salts required.

[0305] 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.

[0306] When using the compounds of general formula (I) and / or their salts as plant growth regulators, for example as stem shorteners in crops such as those mentioned above, preferably in 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 both to applications in

[0307] Pre-emergence or post-emergence.

[0308] The application as a stem shortener can take place at various stages of plant growth. For example, application after tillering at the beginning of the growing season is preferred.

[0309] Length growth. Alternatively, when used as a plant growth regulator, seed treatment is also an option, which includes various seed dressing and coating techniques. The application rate depends on the specific technique and can be determined in preliminary trials.

[0310] For example, known active ingredients based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytodesaturase, photosystem I, photosystem II, or

[0311] Protoporphyrinogen oxidase-based compounds can be used, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012, and the literature cited therein. The following are examples of known herbicides or plant growth regulators that can be combined with the compounds according to the invention, wherein these active ingredients are identified either by their common name in the English version according to the International Organization for Standardization (ISO) or by their chemical name or code number. All

[0312] Application forms such as acids, salts, esters as well as all isomeric forms such as stereoisomers and optical isomers are included, even if these are not explicitly mentioned.

[0313] Examples of such herbicidal mixing partners are:

[0314] Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim- sodium, ametryn, amicarbazone, amidochlor, amidosulfüron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3- methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor- potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfüron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfüresate, bensulfüron, bensulfüron-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, chlorfenac- sodium, chlorfenprop,chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfüron, cinidon, cinidon-ethyl, cinmethylin, cinosulfüron, 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-l,2-oxazolidin-3- one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-l,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl,diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr- sodium, 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- 1 H-tetrazol- 1 -yl] -phenyl] -ethansulfonamid, F - 7967, i.e. 3-[7 -Chlor-5 -fluor-2-(trifluormethyl)- lH-benzimidazol-4-yl] - 1 -methyl-6- (trifluormethyl)pyrimidin-2,4(lH,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,

[0315] 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.0-(2,4-Dimethyl-6-nitrophenyl)-0-ethyl- isopropylphosphoramidothioat, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron- methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e. l-(Dimethoxyphosphoryl)-ethyl-(2,4- dichlorphenoxy)acetat, imazamethabenz, Imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin- ammonium, 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)-l- methyl-3-(trifluormethyl)-lH-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-l,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,.

[0316] methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron,

[0317] methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulf iron-methyl, molinat, monolinuron, monosulfiiron, monosulfiiron-ester, MT-5950, i.e. N-[3-chlor-4-(l-methylethyl)- phenyl]-2-methylpentanamid, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-Dichlorbenzoyl)-l-methyl- 5-benzyloxypyrazol, neburon, nicosulfiiron, nonanoic acid (Pelargonsäure), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulf iron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulf iron, primisulf iron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium,propyrisulf iron, propyzamide, prosulfocarb, prosulf iron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulf iron- ethyl, 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-tefiiryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulf iron, , SYN-523, SYP-249, i.e. l-Ethoxy-3-methyl-l-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-TB A, TCA (Trifluoressigsäure),TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumetone, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulf iron-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, vemolate, XDE-848, ZJ-0862, ie 3,4-Dichloro-N-{2- [(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, and the following compounds:,

[0318] Examples of plant growth regulators as possible mixing partners are:

[0319] Acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine,

[0320] Brassinolid, Catechin, chlormequat Chloride, cloprop, cyclanilide, 3-(Cycloprop-l-enyl)propionsäure, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal- dipotassium, -disodium, und mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indol-3-acetic acid (IAA), 4- indol-3-ylbutyric acid, isoprothiolane, probenazole, Jasmonsäure, Jasmonsäuremethylester, maleic hydrazide, mepiquat Chloride, 1-methylcyclopropene, 2-(l-naphthyl)acetamide, 1-naphthylacetic acid, 2- naphthyloxyacetic acid, nitrophenolate-mixture, 4-Oxo-4[(2-phenylethyl)amino]buttersäure, paclobutrazol, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, Salicylsäure, Strigolacton, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

[0321] The following safeners, for example, are also suitable as combination partners for the compounds of general formula (I) according to the invention:

[0322] S 1) Compounds from the group of heterocyclic carboxylic acid derivatives:

[0323] S l a ) Compounds of the dichlorophenylpyrazolin-3-carboxylic acid type (S l a ), preferably

[0324] Connections such as

[0325] l-(2,4-Dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carboxylic acid,

[0326] l-(2,4-Dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carboxylic acid ethyl ester (S 1-1) ("Mefenpyr-diethyl"), and related compounds as described in WO-A-91 / 07874;

[0327] S l b ) Derivatives of dichlorophenylpyrazolecarboxylic acid (S l b ), preferably compounds such as l-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylic acid ethyl ester (Sl-2),

[0328] l-(2,4-Dichlorophenyl)-5-isopropylpyrazole-3-carboxylic acid ethyl ester (S 1-3),

[0329] 1-(2,4-Dichlorophenyl)-5-(1,1-dimethyl-ethyl)pyrazole-3-carboxylic acid ethyl esters (S1-4) and related compounds as described in EP-A-333131 and EP-A-269806;

[0330] Sl c ) Derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (Sl c ), preferably compounds such as l-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylic acid ethyl ester (S 1-5), l-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylic acid methyl ester (S 1-6) and related

[0331] Compounds such as those described in EP-A-268554;

[0332] S l d ) Compounds of the triazole carboxylic acid type (S l d ), preferably compounds such as

[0333] Fenchlorazole(-ethyl ester), i.e. l-(2,4-Dichlorophenyl)-5-trichloromethyl-(lH)-l,2,4-triazol-3-carboxylic acid ethyl ester (Sl-7), and related compounds as described in EP-A-174562 and EP-A-346620;

[0334] S l e ) Compounds of the type of 5-benzyl or 5-phenyl-2-isoxazoline-3-carboxylic acid, or of 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (Sl e ), preferably compounds such as

[0335] 5-(2,4-Dichlorobenzyl)-2-isoxazobn-3-carboxylic acid ethyl ester (S 1-8) or

[0336] 5-Phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S 1-9) and related compounds as described in WO-A-91 / 08202, or 5,5-Diphenyl-2-isoxazoline-carboxylic acid (Sl-10) or 5,5-Diphenyl-2-isoxazoline-3-carboxylic acid ethyl ester (Sl-11) ("Isoxadifen-ethyl")

[0337] or -n-propyl ester (S 1-12) or 5-(4-Fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S 1-13), as described in patent application WO-A-95 / 07897.

[0338] 52) Compounds from the group of 8-quinoline oxide derivatives (S2):

[0339] S2 a ) Compounds of the type of 8-quinoline oxyacetic acid (S2 a ), preferably

[0340] (5-Chloro-8-quinolinoxy)acetic acid (l-methylhexyl) ester ("Cloquintocet-mexyl") (S2-1), (5-chloro-8-quinolinoxy)acetic acid (l,3-dimethyl-but-l-yl) ester (S2-2),

[0341] (5-Chloro-8-quinolinoxy)acetic acid 4-allyl-oxy-butyl ester (S2-3),

[0342] (5-Chloro-8-quinolinoxy)acetic acid-l-allyloxy-prop-2-yl ester (S2-4),

[0343] (5-Chloro-8-quinolinoxy)acetate ethyl ester (S2-5),

[0344] (5-Chloro-8-quinolinoxy)methyl acetate (S2-6),

[0345] (5-Chloro-8-quinobnoxy)acetic acid allyl ester (S2-7),

[0346] (5-Chloro-8-quinolinoxy)acetic acid 2-(2-propylidene-iminoxy)-l-ethyl ester (S2-8),

[0347] (5-Chloro-8-quinolineoxy)acetic acid 2-oxo-prop-l-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-quinolineoxy)acetic acid (S2-10), its hydrates and salts, for example its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium, or phosphonium salts as described in WO-A-2002 / 34048;

[0348] S2 b ) Compounds of the type of (5-chloro-8-quinoline oxy)malonic acid (S2 b ), preferably

[0349] Compounds such as (5-chloro-8-quinoline oxy)malonic acid diethyl ester,

[0350] (5-Chloro-8-quinoline oxy)malonic acid diallyl esters,

[0351] (5-Chloro-8-quinoline oxy)malonic acid methyl ethyl ester and related compounds as described in EP-A-0 582 198.

[0352] 53) Active ingredients of the dichloroacetamide (S3) type, which are frequently used as pre-emergence safeners

[0353] (soil-active safeners) are used, such as "Dichlormide" (N,N-Diallyl-2,2-dichloroacetamide) (S3-1),

[0354] "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),

[0355] "Benoxacor" (4-Dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4),

[0356] “PPG-1292” (N-allyl-N-[(l,3-dioxolan-2-yl)-methyl]-dichloroacetamide) from PPG

[0357] Industries (S3-5),

[0358] “DKA-24” (N-allyl-N-[(allylaminocarbonyl)methyl]-dichloroacetamide) from Sagro-Chem (S3-6),

[0359] "AD-67" or "MON 4660" (3-Dichloroacetyl-l-oxa-3-aza-spiro[4,5]decane) of the company

[0360] Nitrokemia or Monsanto (S3-7),

[0361] "TI-35" (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8),

[0362] "Diclonon" (Dicyclonon) or "BAS 145138" or "LAB 145138" (S3-9)

[0363] ((RS)-l-Dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[l,2-a]pyrimidin-6-one) of BASF, "Furilazol" or "MON 13900" ((RS)-3-Dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazobdin) (S3-10), and its (R)-isomer (S3-11).

[0364] S4) Compounds from the class of acylsulfonamides (S4):

[0365] S4 a ) N-acylsulfonamides of the formula (S4 a ) and their salts as described in WO-A-97 / 45016

[0366] are described

[0367] wherein

[0368] R A 1 (Ci-C ö)-Alkyl, (C3-C6)-Cycloalkyl, wherein the last two substituents are replaced by VA

[0369] Substituents from the group halogen, (Ci-C- -alkoxy, (Ci-Ce)-haloalkoxy and (Ci- C4)-alkylthio and in the case of cyclic residues also by (Ci-C4)-alkyl and (C1-C4)-haloalkyl are substituted;

[0370] R A 2 Halogen, (Ci-C4)-alkyl, (Ci-C4)-alkoxy, CF 3;

[0371] ni A 1 or 2;

[0372] VA means 0, 1, 2 or 3;

[0373] S4 b ) Compounds of the type of 4-(benzoylsulfamoyl)benzamides of formula (S4 b ) and their salts, as described in WO-A-99 / 16744,

[0374] wonn

[0375] R B 1 , R B 2 independently of each other hydrogen, (Ci-Ce)-alkyl, (C3-C6)-cycloalkyl, (Cri-G,)-alkenyl, (GG)-alkynyl.

[0376] R B 3Halogen, (Ci-C--alkyl, (Ci-C4)-haloalkyl or (Ci-C4)-alkoxy and

[0377] me 1 or 2 mean,

[0378] e.g. such in which

[0379] R B 1 = Cyclopropyl, R B 2 = hydrogen and (R B 3 ) = 2-OMe ("Cyprosulfamide", S4-1),

[0380] R B 1 = Cyclopropyl, R B 2 = hydrogen and (R B 3 ) = 5-Cl-2-OMe is (S4-2),

[0381] R B 1 = Ethyl, R B 2 = hydrogen and (R B 3 ) = 2-OMe is(S4-3),

[0382] R B 1 = Isopropyl, R B 2 = hydrogen and (R B 3 ) = 5-Cl-2-OMe is (S4-4) and

[0383] R B 1 = Isopropyl, R B 2 = hydrogen and (R B 3 ) = 2-OMe is (S4-5);

[0384] S4 C ) Compounds from the class of benzoylsulfamoylphenyl amines of the formula (S4 C ), as described in EP-A-365484,

[0385]

[0386] wherein

[0387] RC 1 1 , Rnc 2 independently of each other hydrogen, (Ci-Cs)-alkyl, (C3-Cs)-cycloalkyl, (C 3

[0388] C6)-Alkenyl, (C3-C6)-Alkynyl,

[0389] RC 3 Halogen, (Ci-C4)-alkyl, (Ci-C4)-alkoxy, CF3 and

[0390] mc 1 or 2 mean;

[0391] for example

[0392] l-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methyl urea,

[0393] l-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,

[0394] l-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methyl urea;

[0395] S4 d ) Compounds of the type of N-phenylsulfonyl terephthalamides of formula (S4 d) and their salts, which are known, for example, from CN 101838227,

[0396]

[0397] wonn

[0398] R D 4 Halogen, (Ci-C4)-alkyl, (Ci-C4)-alkoxy, CF 3;

[0399] m D 1 or 2;

[0400] R D 5 Hydrogen, (Ci-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C5-

[0401] C6)-Cycloalkenyl means. 55) Active ingredients from the class of hydroxyaromatics and aromatic-aliphatic carboxylic acid derivatives (S5), e.g.

[0402] 3,4,5-Triacetoxybenzoic acid ethyl ester, 3,5-Dimethoxy-4-hydroxybenzoic acid, 3,5-Dihydroxybenzoic acid, 4-Hydroxysabcylic 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.

[0403] 56) Active substances from the class of l,2-dihydroquinoxabn-2-one (S6), e.g.

[0404] 1-Methyl-3-(2-thienyl)-1,2-dihydroquinoxabn-2-one, 1-Methyl-3-(2-thienyl)-1,2-dihydro-quinoxabn-2-thione, l-(2-Aminoethyl)-3-(2-thienyl)-l,2-dihydro-quinoxalin-2-one hydrochloride, l-(2-Methylsulfonylaminoethyl)-3-(2-thienyl)-l,2-dihydro-quinoxahn-2-one, as described in WO-A-2005 / 112630.

[0405] 57) Compounds from the class of diphenylmethoxyacetic acid derivatives (S7), e.g.

[0406] Diphenylmethoxyacetate methyl ester (CAS Reg. No. 41858-19-9) (S7-1),

[0407] Ethyl diphenylmethoxyacetic acid ester or diphenylmethoxyacetic acid as described in WO-A-98 / 38856.

[0408] 58) Compounds of formula (S8) as described in WO-A-98 / 27049,

[0409]

[0410] where the symbols and indices have the following meanings:

[0411] RD 1is halogen, (Ci-C- -alkyl, (Ci-C- -haloalkyl, (Ci-C- -alkoxy, (Ci-C- -haloalkoxy,

[0412] R D 2 is hydrogen or (Ci-C4)-alkyl,

[0413] RD 3 is hydrogen, (Ci-Cs)-alkyl, (C2-C4)-alkenyl, (C2-C4)-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,

[0414] n D is an integer from 0 to 2.

[0415] S9) Active substances from the class of 3-(5-tetrazolylcarbonyl)-2-quinolones (S9), e.g.

[0416] 1,2-Dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No.: 219479-18-2), l,2-Dihydro-4-hydroxy-1-methyl-3-(5-tetrazolyl-carbonyl)-2-quinolone (CAS Reg. No.

[0417] 95855-00-8), as described in WO-A- 1999 / 000020.

[0418] S10) Connections of the formulas (S10 a ) or (S10 b ),

[0419] as described in WO-A-2007 / 023719 and WO-A-2007 / 023764, in which

[0420] RE 1 Halogen, (Ci-C- -Alkyl, Methoxy, Nitro, Cyano, CF3, OCF3

[0421] YE, ZE independently of each other O or S,

[0422] P E an integer from 0 to 4,

[0423] RE 2 (Ci-Ci ö )-Alkyl, (Cri-Gd-Alkcnyl. (C3-C6)-Cycloalkyl, Aryl, Benzyl, Halobenzyl,

[0424] RE 3 hydrogen or (Ci-Ce) alkyl.

[0425] ) Active ingredients of the oxyimino compound type (Si l), which are known as seed dressings, such as e.g.

[0426] "Oxabetrinil" ((Z)-1,3-Dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (Sl l-1), known as a seed dressing safener for millet against damage from metolachlor,

[0427] "Fluxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone-0-(1,3-dioxolan-2-ylmethyl)-oxime)

[0428] (S 11-2), known as a seed treatment safener for millet against damage caused by metolachlor, and "Cyometrinil" or "CGA-43089" ((Z)-Cyanomethoxyimino(phenyl)acetonitrile) (Sl l-3), known as a seed treatment safener for millet against damage caused by metolachlor.

[0429] ) Active ingredients from the class of isothiochromanones (S12), such as methyl- [(3 -oxo- 1H-2- benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6) (S 12-1) and related compounds from WO-A-1998 / 13361.

[0430] ) One or more compounds from group (S13):

[0431] "Naphthalic anhydride" (1,8-Naphthalenedicarboxylic anhydride) (S 13-1), known as a seed treatment safener for maize against damage from thiocarbama herbicides,

[0432] "Fenclorim" (4,6-Dichloro-2-phenylpyrimidine) (S13-2), known as a safener for pretilachlor in seeded rice,

[0433] "Flurazole" (benzyl-2-chloro-4-trifluoromethyl-1,3-thiazol-5-carboxylate) (S13-3), known as a seed dressing safener for millet against damage from alachlor and metolachlor,

[0434] "CL 304415" (CAS Reg. No. 31541-57-8)

[0435] (4-Carboxy-3,4-dihydro-2H-l-benzopyran-4-acetic acid) (S13-4) of the company American

[0436] Cyanamide, known as a safener for maize against damage from imidazolinones,

[0437] "MG 191" (CAS Reg. No. 96420-72-3) (2-Dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, known as a safener for maize, "MG 838" (CAS Reg. No. 133993-74-5)

[0438] (2-propenyl l-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) from Nitrokemia "Disulfoton" (0,0-diethyl S-2-ethylthioethyl phosphorus dithioate) (S13-7),

[0439] "Dietholates" (O,O-diethyl-O-phenylphosphorothioate) (S 13-8),

[0440] "Mephenate" (4-chlorophenyl methyl carbamate) (S 13-9).

[0441] ) Active ingredients that, in addition to a herbicidal effect against weeds, also have a safener effect on cultivated plants such as rice, e.g.

[0442] "Dimepiperate" or "MY-93" (U-1-methyl-1-phenylethyl-piperidine-1-carbothioate), which is known as a safener for rice against damage from the herbicide molinate.

[0443] "Daimuron" or "SK 23" (l-(l-Methyl-l-phenylethyl)-3-p-tolyl-hamstoff), which is known as a safener for rice against damage caused by the herbicide imazosulfuron,

[0444] "Cumyluron" = "JC-940" (3-(2-chlorophenylmethyl)-l-(l-methyl-l-phenyl-ethyl) hydroxyl, 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,

[0445] "CSB" (l-Bromo-4-(chloromethylsulfonyl)benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage caused by some herbicides in rice.

[0446] ) Compounds of formula (S 15) or their tautomers,

[0447]

[0448] as described in WO-A-2008 / 131861 and WO-A-2008 / 131860,

[0449] wherein

[0450] RH 1 means a (Ci-Ce)-haloalkyl group and

[0451] RH 2 Hydrogen or halogen means and

[0452] R H 3 , R H 4independently of each other hydrogen, (Ci-Cie)-alkyl, (CYC ir,)-alkenyl or

[0453] (C2-Ci6)-Alkynyl,

[0454] wherein each of the last 3 residues is unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, (Ci-C- )alkoxy, (Ci-C- )haloalkoxy, (Ci-C- )alkylthio, (Ci-C- )alkylamino, di[(Ci-C4)-alkyl]amino, [(Ci-C4)-alkoxy]carbonyl, [(C1-C4)-haloalkoxy |-carbonyl. (C ’, -G,)-Cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted, substituted,

[0455] or (C3-C ö )-Cycloalkyl, (C4-C ö )-Cycloalkenyl, (C3-C ö )-Cycloalkyl fused to one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C ö)-Cycloalkenyl, which is condensed on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring,

[0456] wherein each of the latter 4 residues is unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, (Ci-C4)-alkyl, (Ci-C4)-haloalkyl, (Ci-C4)-alkoxy, (Ci-C4)-haloalkoxy, (Ci-C4)-alkylthio, (Ci-C4)-alkylamino, di[(Ci-C4)-alkyl]amino, [(C1-C4)-alkoxyj-carbonyl, [(Ci-C4)-haloalkoxy]-carbonyl, (CVC r ,)-Cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which

[0457] unsubstituted or substituted, substituted,

[0458] means or

[0459] R H 3 (Ci-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C6)-alkynyloxy or (C2-C4)-haloalkoxy means and

[0460] R H 4 Hydrogen or (Ci-C4) alkyl means or

[0461] 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, (Ci-C4)-alkyl, (Ci-C4)-haloalkyl, (Ci-C4)-alkoxy, (Ci-C4)-haloalkoxy and (Ci-C4)-alkylthio.

[0462] S 16) Active substances that are primarily used as herbicides, but also have a safener effect on cultivated plants, e.g.

[0463] (2,4-Dichlorophenoxy)acetic acid (2,4-D),

[0464] (4-Chlorphenoxy)acetic acid

[0465] (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop),

[0466] 4-(2,4-Dichlorophenoxy)butyric acid (2,4-DB),

[0467] (4-Chloro-o-tolyloxy)acetic acid (MCPA),

[0468] 4-(4-chloro-o-tolyloxy)butyric acid,

[0469] 4-(4-Chlorphenoxy)buheric acid,

[0470] 3,6-dichloro-2-methoxybenzoic acid (dicamba),

[0471] l-(Ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloro-ethyl).

[0472] Preferred safeners in combination with the compounds of general formula (I) and / or their salts, in particular with the compounds of formulas (1-1) to (1-229) 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

[0473] The following abbreviations are used in the examples and tables below:

[0474] Undesirable plants / weeds:

[0475] ABUTH: Abutilon theophrasti

[0476] BROADBOUND: Agrostis tenuis

[0477] BITTER Amaranthus retroflexus

[0478] ECHCG: Echinochloa crus-galli

[0479] LOLRI: Lolium rigidum

[0480] MORNING: Matricaria odorata

[0481] POAAN : Poa annua

[0482] SETVI: Green Setaria

[0483] STEMS: Stellaria media

[0484] A. Herbizide Wirkung im frühen Nachauflauf

[0485] Seeds of monocot and dicot weeds were sown in quartz sand in 96-well microtiter plates and cultivated in a climate chamber under controlled growing conditions. Five to seven days after sowing, the plants were treated at the cotyledon stage. The inventive compounds, formulated as emulsion concentrates (EC), were applied at a water rate equivalent to 2200 liters per hectare. After nine to twelve days of the plants remaining in the climate chamber under optimal growing conditions, the effect of the preparations was visually assessed in comparison to untreated controls.

[0486] For example, 100% effect means plants have died, 0% effect means the same as untreated control plants.

[0487] In the tables below, A1 to A2, the effects of selected compounds of the general formula (I) according to Table 1 above on various pest plants and a

[0488] Application rate corresponding to 1900 g / ha, obtained according to the aforementioned trial procedure, is shown. Table Al

[0489] Table A2

[0490]

[0491] The test results show that, when applied in early post-emergence, compounds of the general formula (I) exhibit good herbicidal efficacy against selected weeds such as Agrostis tenuis and Poa annua at a variable application rate of 1900 g of active substance per hectare.

[0492] B. Post-emergence herbicide effect: 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 grown in a greenhouse under controlled growing conditions. Two to three weeks after sowing, the plants were treated at the one-leaf stage. The compounds, 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 of approximately 600 liters per hectare. After approximately three weeks of the plants remaining in the greenhouse under optimal growing conditions, the effect of the preparations was visually assessed in comparison to untreated controls.

[0493] For example, 100% effect means plants have died, 0% effect means the same as untreated control plants.

[0494] 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.

[0495] Table Bl :

[0496] Table B2:

[0497] Table B3: Table B4:

[0498] Table B5:

[0499] Table B6: Table B7:

[0500] Table B8:

[0501] The experimental results demonstrate that, when applied post-emergence, the inventive compounds of the general formula (I) 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 at a respective application rate of 1280 g of active substance per hectare.

[0502] C. Herbicidal activity in pre-emergence

[0503] 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 inventive compounds, formulated as wettable powders (WP) or emulsion concentrates (EC), were then applied as an aqueous suspension or emulsion, with the addition of 0.5% additive, to the surface of the cover soil at a water volume equivalent to 600 liters per hectare. After treatment, the pots were placed in the greenhouse and kept under favorable growing conditions for the test plants. After approximately three weeks, the effect of the preparations was visually assessed in comparison to untreated controls, expressed as a percentage.

[0504] For example, 100% efficacy means plants are dead, 0% efficacy means the same as untreated control plants. 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.

[0505] Table C 1 :

[0506]

[0507] Table C2:

[0508]

[0509] Table C3:

[0510] Table C4: Table C5:

[0511] Table C6: Table C7:

[0512] Table C8:

[0513]

[0514] 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

Patent claims 1 Substituted 2-heteroarylaminobenzenes of general formula (I) or their salts wonn A stands for nitrogen or -CX- X stands for hydrogen or halogen R 1 for an optionally substituted aryl or heteroaryl, wherein each ring or ring system is optionally equipped with up to 5 substituents, independently selected from the group R 5 , is substituted, R 2unabhängig voneinander für Halogen, Cyano, Nitro, Formyl, Formamid, (Ci-Cs)-Alkyl, (Ci-Cs)-Haloalkyl, (C2-C8)-Alkenyl, (CA-Cs)- Alkiny l. (C2-C8)-Haloalkenyl, (C2-C8)- Haloalkinyl, (C3-C8)-Cycloalkyl, (C3-C6)-Halocycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)- alkyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)- Alkylthio-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfinyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfonyl- (Ci-C4)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C3-C8)- Cycloalkylcarbonyl, Carboxyl, (Ci-C8)-Alkoxycarbonyl, (Ci-C8)- Haloalkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, Carbamoyl, (C2-C8)-Alkylaminocarbonyl, (C2-C10)- Dialkylaminocarbonyl, (C3-Cio)-Cycloalkylaminocarbonyl, (Ci-C4)-Alkoxycarbonyl- (Ci-C4)-alkyl, (Ci-C4)-Haloalkoxycarbonyl-(Ci-C4)-alkyl, Carboxy-(Ci-C4)-alkyl, Hydroxy, NR 4 R 6, (Ci-C8)-Alkoxy, (Ci-C8)-Haloalkoxy, (Ci-C8)-Alkylthio, (Ci-C8)- Haloalkylthio, (C3-C8)-Cycloalkylthio, (Ci-C4)-Alkoxy-(Ci-C4)-alkylthio, (Ci-C8)- Alkylsulfinyl, (Ci-C8)-Haloalkylsulfinyl, (C3-C8)-Cycloalkylsulfinyl, (Ci-C4)-Alkoxy- (Ci-C4)-alkylsulfinyl, (Ci-C8)-Alkylsulfonyl, (Ci-C8)-Haloalkylsulfonyl, (C3-C8)- Cycloalkylsulfonyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkylsulfonyl, (Ci-C8)-Alkylaminosulfonyl, (C2-C8)-Dialkylaminosulfonyl oder (C3-C8)-Trialkylsilyl steht, m ist gleich 0, 1, 2, oder 3, R 3 für Wasserstoff, Halogen, Cyano, Nitro, (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl, (C2-C4)- Alkenyl, (C2-C4)-Alkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C8)-Alkoxy, (Ci-C8)-Haloalkoxy, (Ci-C8)-Alkylthio, (Ci-C8)-Haloalkylthio, (Ci-C8)- Alkylsulfinyl, (Ci-C8)-Haloalkylsulfinyl, (Ci-C8)-Alkylsulfonyl, (Ci-Cs)- Haloalkylsulfonyl steht, R 4 , R 6unabhängig voneinander für Wasserstoff, (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl, Aryl-(Ci- C6)-alkyl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)- alkyl, (C3-C6)-Halocycloalkyl, (C3-C6)-Halocycloalkyl-(Ci-C4)-alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylthio-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfinyl-(Ci-C4)-a]kyl, (C1-C4)- Alkylsulfonyl-(Ci-C4)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, Formyl, (Ci-C8)-Alkoxycarbonyl, (Ci-Cs)- Haloalkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (Ci-C8)-Alkylaminocarbonyl, (C2-C8)-Dialkylaminocarbonyl, (C3-C8)-Cycloalkylaminocarbonyl steht, R 5 für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C1-C4)- Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylthio-(Ci-C4)- alkyl, (Ci-C4)-Alkylsulfmyl-(Ci-C4)-a]kyl, (Ci-C4)-Alkylsulfonyl-(Ci-C4)-alkyl, (Ci-C8)- Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, Carboxyl, (Ci-C8)-Alkoxycarbonyl, (Ci-Cs)- Haloalkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (Ci-C8)-Alkylaminocarbonyl, (C2-C8)-Dialkylaminocarbonyl, (C3-C8)- Cycloalkylaminocarbonyl, Hydroxy, (Ci-Cs)-Alkoxy, (Ci-C8)-Haloalkoxy, (Ci-Cs)- Alkylthio, (Ci-C8)-Haloalkylthio, (C3-C8)-Cycloalkylthio, (Ci-C8)-Alkylsulfinyl, (Ci-C8)-Haloalkylsulfinyl, (C3-C8)-Cycloalkylsulfinyl, (Ci-C8)-Alkylsulfonyl, (Ci-C8)- Haloalkylsulfonyl, (C3-C8)-Cycloalkylsulfonyl, (Ci-C8)-Alkylaminosulfonyl, (C2-Cs)- Dialkylaminosulfonyl oder (C3-C8)-Trialkylsilyl steht, ausgenommen der nachfolgend genannten Verbindungen: 2-(2-Phenoxyphenylamino)pyridin 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.

2. Compound of general formula (I) according to claim 1 or salts thereof, wherein A stands for nitrogen or -CX- X stands for hydrogen, fluorine or chlorine, R 1 for a possibly substituted phenyl, pyridyl or pyrimidyl, wherein each ring or ring system optionally has up to 5 substituents, independently selected from group R 5 , is substituted, R 2 independently for halogen, cyano, nitro, (Ci-C4)-alkyl, (Ci-C- -haloalkyl, NR 4 R 6 , (Ci-C- -Alkoxycarbonyl, (Ci-C- -Alkylthio or (Ci-C- -Alkoxy stands, m is equal to 0, 1, 2, or 3, R 3 for hydrogen, halogen, cyano, nitro, (Ci-C4)-alkyl, (Ci-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkenyl, (C2-C4)-haloalkynyl, cyclpropyl, cyclopropylmethyl, (Ci-C4)-alkoxy, (Ci-C4)-haloalkoxy, (Ci-C4)-alkylthio or (Ci-C4)-haloalkylthio, R 4 , R 6 independently of each other stands for hydrogen, (Ci-C4)-alkyl, (Ci-C4)-alkylcarbonyl or (Ci-C4)-alkoxycarbonyl, R 5 stands for hydrogen, halogen, cyano, (Ci-C4)-alkyl, (Ci-C4)-haloalkyl, (Ci-C4)-alkylthio, (Ci-C4)-alkoxy or (Ci-C4)-haloalkoxy, excluding the following connections: 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.

3. Compound of general formula (I) according to claim 1 or its salts, wherein A represents nitrogen or -CX-, X stands for hydrogen, fluorine or chlorine, R 1 for a possibly substituted phenyl, pyridyl or pyrimidyl, each ring optionally with up to 5 substituents, independently selected from group R 5 , is substituted, R 2 independently for fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, Trifluoromethyl, methoxy, methylthio or amino is shown, m is 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. R 5stands for hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy or trifluoromethoxy, excluding 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.

4. Herbicidal agents characterized by a herbicidally active content of at least one compound of general formula (I) according to one of claims 1 to 3.

5. Herbicides according to claim 4 in a mixture with formulation aids.

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

7. Herbicide composition according to claim 6 comprising a safener.

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

9. Herbicidal compositions according to any one of claims 4 to 8 comprising a further herbicide.

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

11. Use of compounds of 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 unwanted plants.

12. Use according to claim 11, characterized in that the connections of the general formula (I) to be used to control unwanted plants in crops of useful plants.

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