[(1-PHENYL-5-HETEROARYL-1H-PYRAZOL-3-YL)OXY]ACETIC ACID DERIVATIVES AS SAFETY AGENTS FOR THE PROTECTION OF CULTIVATED AND USED PLANTS

Description

[0001] The present invention relates to crop-protecting compounds and compositions containing specific compounds as safeners for reducing the phytotoxic effects of agrochemicals, especially herbicides. In particular, the invention relates to {[1-(phenyl)-5-(heteroaryl)-1H-pyrazol-3-yl]oxy}acetic acid derivatives and their salts as safeners, and to processes for their preparation.

[0002] When pesticides are used to combat unwanted organisms in agricultural and forestry crops, the crops themselves are often damaged to a greater or lesser extent by the pesticides used, such as herbicides, insecticides, fungicides, and others. This undesirable phytotoxic side effect occurs particularly frequently with the use of numerous herbicides—primarily with post-emergence application—in crops such as corn, rice, or cereals. Through the use of so-called "safeners" or "antidotes," crops can in some cases be protected against the phytotoxic properties of the pesticides without diminishing or significantly impairing their pesticidal effect against the pests. In some cases, the presence of safeners has even been observed to improve pesticidal effect against pests such as weeds.

[0003] The compounds known to date as safeners belong to a large number of different chemical structural classes, whereby their suitability for safener application generally also depends on the chemical structures of the pesticides and the crops.

[0004] The safener effects of compounds from the group of derivatives of phenoxy- or heteroaryloxyalkanecarboxylic acids have long been known when used in combination with herbicides. Examples of such compounds are MCPA and similar compounds, which also have herbicidal activity against weeds, or cloquintocet-mexyl.

[0005] Safeners from the group of derivatives of N-phenyl-substituted heteroarylcarboxylic acid esters with multiple heteroatoms in the heteroaromatic compound are also known. Examples of such safeners are the safeners mefenpyr-diethyl and isoxadifen-ethyl, which are used in commercial products.

[0006] The use of hydroxy-substituted aromatic carboxylic acid derivatives is known from WO 2004 / 084631. WO 2005 / 015994 describes specific salicylic acid derivatives as safeners. These are particularly suitable for use as safeners in corn and soybean crops. Furthermore, 1,2-dihydroquinoxalin-2-one derivatives are known from WO 2005 / 112630 and pyridonecarboxamides from WO 2008 / 131860.

[0007] Active ingredients from the chemical class of 1,5-diphenyl-1H-pyrazole-3-carboxylic acid derivatives and 1,5-diphenyl-1H-pyrazole-3-carboxylic acid derivatives with plant-active properties as safeners are known from WO2006 / 040016.

[0008] Active ingredients from the chemical class of 1,5-diphenyl-1H-pyrazole-3-carboxylic acid derivatives with plant-active properties as safeners are also known from EP0268554.

[0009] Active ingredients from the chemical class of [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid derivatives with fungicidal properties are described in Molecules 2014, 19(1), 1302-1316, J. of Heterocyclic Chemistry 2012, 49(6) 1370-1375, Acta Crystallographica, Section E: Structure Reports Online 2012, 68(8), o2419, Acta Crystallographica, Section E: Structure Reports Online 2012, 68(1), o123, J. of Heterocyclic Chemistry 2010, 47(4) 897-902. Antibacterial agrochemical [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid derivatives are described in CN102093344 and CN101284815. Various publications describe [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives with medicinal properties. [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives are known from WO2008073825 and DE2828529.

[0010] The synthesis of [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid derivatives is described in the European Journal of Organic Chemistry 2011, 27, 5323-5339.

[0011] The synthesis of substituted {[1-phenyl-5-(2-thienyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid derivatives is described in WO2008 / 073825 as intermediates of LXR and FXR modulators for medical application.

[0012] When using safeners to protect crops from pesticide damage, it has been shown that known safeners can have disadvantages in many cases. These include: the crop-protective properties are insufficient, in combination with a specific herbicide the spectrum of crops in which the safener / herbicide is to be used is not sufficiently large, a specific safener can only be combined with a few herbicides, the use of safeners increases the application rate and the amount of formulation aids and can therefore cause application-related problems.

[0013] For the reasons mentioned above, there is an increased need to provide alternative compounds with safener effects.

[0014] The invention relates to novel crop-protecting compounds of the general formula (I) or salts thereof, for reducing the phytotoxic effects of pesticides, in particular herbicides, on crops or cultivated plants, in which R 1< represents heteroaryl, except thienyl, where the heteroaryl radical is unsubstituted or substituted by halogen, cyano, nitro, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 3 -C 8 )cycloalkyl, (C 3 -C 8 )cycloalkenyl, (C 1 -C 6 )alkoxy and (C 1 -C 6 )alkylS(O) p , where the last-mentioned seven radicals are unsubstituted, or by one or more radicals from the group halogen, cyano, (C 1 -C 6 )alkoxy and (C 1 -C 6 )alkylS(O) p , R 2< represents hydrogen, halogen, cyano, nitro, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 3 -C 8 )cycloalkyl, (C 3 -C 8 )cycloalkenyl, (C 1 -C 6 )alkoxy and (C 1 -C 6 )alkylS(O) p , where the last-mentioned seven radicals are unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, (C 1 -C 6 )alkoxy and (C 1 -C 6 )alkylS(O) p , R 3< represents hydrogen and (C 1 -C 6 )alkyl, R 4< represents hydrogen, (C 1 -C 18 )alkyl, (C 1 -C 18 )haloalkyl,(C 1 -C 18 )Cyanoalkyl, (C 2 -C 18 )Alkenyl, (C 2 -C 18 )Alkinyl, (C 3 -C 12 )Cycloalkyl, (C 3 -C 12 )Cycloalkenyl, Aryl, Heteroaryl, (C 1 -C 18 )Alkoxy-(C 1 -C 18 )alkyl, (C 1 -C 18 )Haloalkoxy-(C 1 -C 18 )alkyl, (C 1 -C 18 )Alkoxy-(C 1 -C 18 )haloalkyl, (C 1 -C 18 )Alkylthio-(C 1 -C 18 )alkyl, (C 1 -C 18 )Haloalkylthio-(C 1 -C 18 )alkyl, (C 2 -C 18 )Haloalkenyl, (C 2 -C 18 )Haloalkinyl, Heterocyclyl-(C 1 -C 18 )alkyl, Aryl-(C 1 -C 18 )alkyl, (C 3 -C 12 )Cycloalkyl-(C 1 -C 18 )alkyl, (C 1 -C 18 )Alkoxycarbonyl-(C 1 -C 18 )alkyl, und (C 1 -C 18 )Alkoxycarbonyl-(C 3 -C 12 )cycloalkyl-(C 1 -C 18 )alkyl, bedeutet, oder einen Rest der Formel -NR a< R b< oder -N=CR c< R d< , wobei in den vorgenannten 2 Resten jeder der Reste R a< , R b< , R c< und R d< unabhängig voneinander Wasserstoff, (C 1 -C 4 )Alkyl, (C 2 -C 4 )Alkenyl, (C 2 -C 4 )Alkinyl, Benzyl, substituiertes Benzyl,represents phenyl or substituted phenyl or R a< and R b< together with the N atom form a 3- to 8-membered heterocycle which may contain one or two further hetero ring atoms from the group N, O and S, and which is unsubstituted or substituted by one or more radicals from the group (C 1 -C 4 )alkyl and (C 1 -C 4 )haloalkyl, or R c< and R d< together with the C atom form a 3- to 8-membered carbocyclic or heterocyclic radical which may contain 1 to 3 hetero ring atoms from the group N, O and S, where the carbocyclic or heterocyclic radical is unsubstituted or substituted by one or more radicals from the group (C 1 -C 4 )alkyl and (C 1 -C 4 )haloalkyl, my number is from 0 to 5, and p0, 1 or 2 means. ,

[0015] The compounds of general formula (I) can form salts by addition of a suitable inorganic or organic acid, for example mineral acids such as HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3 , or organic acids, e.g. carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid, to a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino. These salts then contain the conjugate base of the acid as an anion. Suitable substituents which are present in deprotonated form, such as sulfonic acids, certain sulfonic acid amides 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 compounds of general formula (I).Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine, and pyridine, as well as ammonium, alkali, or alkaline earth metal hydroxides, carbonates, and bicarbonates, in particular sodium and 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 agriculture, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or ammonium salts, salts with organic amines, or quaternary ammonium salts, for example with cations of the formula [NR i< R ii< R iii< R iv< ] +< , where R i< to R iv< each independently represent an organic radical, in particular alkyl, aryl, arylalkyl, or alkylaryl. Alkylsulfonium and alkylsulfoxonium salts, such as (C 1 -C 4 )-trialkylsulfonium and (C 1 -C 4 )-trialkylsulfoxonium salts, are also suitable.

[0016] 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)".

[0017] Preferred subject matter of the invention are compounds of the general formula (I), in which R 1< represents heteroaryl, except thienyl, where the heteroaryl radical is unsubstituted or substituted by halogen, cyano, nitro, (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 4 )alkynyl, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkenyl, (C 1 -C 4 )alkoxy and (C 1 -C 4 )alkylS(O) p , where the last-mentioned seven radicals are unsubstituted, or by one or more radicals from the group consisting of halogen, cyano, (C 1 -C 4 )alkoxy and (C 1 -C 4 )alkylS(O) p , R 2< represents hydrogen, halogen, cyano, nitro, (C 1 -C 4 )alkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )alkynyl, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkenyl, (C 1 -C 4 )alkoxy and (C 1 -C 4 )alkylS(O) p , where the last-mentioned seven radicals are unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, (C 1 -C 4 )alkoxy and (C 1 -C 4 )alkylS(O) p , R 3< represents hydrogen and (C 1 -C 4 )alkyl, R 4< represents hydrogen, (C 1 -C 16 )alkyl, (C 1 -C 16 )haloalkyl,(C 1 -C 16 )cyanoalkyl, (C 2 -C 16 )alkenyl, (C 2 -C 16 )alkynyl, (C 3 -C 12 )cycloalkyl, (C 3 -C 12 )cycloalkenyl, aryl, heteroaryl, (C 1 -C 16 )alkoxy-(C 1 -C 16 )alkyl, (C 1 -C 16 )haloalkoxy-(C 1 -C 16 )alkyl, (C 1 -C 16 )alkoxy-(C 1 -C 16 )haloalkyl, (C 1 -C 16 )alkylthio-(C 1 -C 16 )alkyl, (C 1 -C 16 )Haloalkylthio-(C 1 -C 16 )alkyl, (C 2 -C 16 )Haloalkenyl, (C 2 -C 16 )haloalkynyl, heterocyclyl-(C 1 -C 16 )alkyl, aryl-(C 1 -C 16 )alkyl, (C 3 -C 12 )cycloalkyl-(C 1 -C 16 )alkyl, (C 1 -C 16 )alkoxycarbonyl-(C 1 -C 16 )alkyl, and (C 1 -C 16 )alkoxycarbonyl-(C 3 -C 12 )cycloalkyl-(C 1 -C 16 )alkyl, my represents a number from 0 to 4, and p represents 0, 1 or 2. ,

[0018] A particularly preferred subject of the invention are compounds of the general formula (I) in which R' represents heteroaryl, except thienyl, where the heteroaryl radical is unsubstituted, or is substituted once or multiple times by halogen, cyano, methyl, ethyl, CF 3 , CF 2 Cl, CH 2 F, CHF 2 , OCH 3 , OCF 3 , SCH 3 , SOCH 3 , SO 2 CH 3 and SCF 3, R 2< represents hydrogen, halogen, cyano, methyl, ethyl, CF 3 , CF 2 Cl, CH 2 F, CHF 2 , OCH 3 , OCF 3 , SCH 3 , SOCH 3 , SO 2 CH 3 and SCF 3, R 3< represents hydrogen, CH 2 CH 3 and CH 3, R 4< represents hydrogen, (C 1 -C 12 )alkyl, (C 1 -C 12 )haloalkyl, (C 1 -C 12 )Cyanoalkyl, (C 2 -C 12 )alkenyl, (C 2 -C 12 )alkynyl, (C 3 -C 12 )cycloalkyl, (C 3 -C 12 )cycloalkenyl, aryl, heteroaryl, (C 1 -C 12 )alkoxy-(C 1 -C 12 )alkyl, (C 1 -C 12 )haloalkoxy-(C 1 -C 12 )alkyl, (C 1 -C 12 )alkoxy-(C 1 -C 12 )haloalkyl, (Ci-C 12 )alkylthio-(C 1 -C 12 )alkyl, (C 1 -C 12 )haloalkylthio-(C 1 -C 12 )alkyl, (C 2 -C 12 )haloalkenyl, (C 2 -C 12 )haloalkynyl, heterocyclyl-(C 1 -C 12 )alkyl, aryl-(C 1 -C 12 )alkyl, (C 3 -C 12 )cycloalkyl-(C 1 -C 12 )alkyl,(C 1 -C 12 )alkoxycarbonyl-(C 1 -C 12 )alkyl, and (C 1 -C 12 )alkoxycarbonyl-(C 3 -C 12 )cycloalkyl-(C 1 -C 12 )alkyl, m represents a number of 0, 1, 2 or 3, and p represents 0, 1 or 2. ,

[0019] Particularly preferred subject matter of the invention are compounds of the general formula (I), in which R 1< für Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Pyrazin-2-yl, Pyrazin-3-yl, Pyrimidin-2-yl, Pyrimidin-4-yl, Pyrimidin-5-yl, Pyridazin-3-yl, Pyridazin-4-yl, 1,3,5-Triazin-2-yl, 1,2,4-Triazin-3-yl, 1,2,4-Triazin-5-yl, 1,2,4-Triazin-6-yl, 1,2,3-Triazin-4-yl, 1,2,3-Triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- und 1,2,6-Oxazinyl, Isoxazol-3-yl, Isoxazol-4-yl, Isoxazol-5-yl, 1,3-Oxazol-2-yl, 1,3-Oxazol-4-yl, 1,3-Oxazol-5-yl, Isothiazol-3-yl, Isothiazol-4-yl, Isothiazol-5-yl, 1,3-Thiazol-2-yl, 1,3-Thiazol-4-yl, 1,3-Thiazol-5-yl, 1H-Pyrrol-1-yl; 1H-Pyrrol-2-yl; 1H-Pyrrol-3-yl; Furan-2-yl; Furan-3-yl; 1H-Imidazol-1-yl; 1H-Imidazol-2-yl; 1H-Imidazol-4-yl; 1H-Imidazol-5-yl; 1H-Pyrazol-1-yl; 1H-Pyrazol-3-yl; 1H-Pyrazol-4-yl; 1H-Pyrazol-5-yl, 1H-1,2,3-Triazol-1-yl, 1H-1,2,3-Triazol-4-yl, 1H-1,2,3-Triazol-5-yl, 2H-1,2,3-Triazol-2-yl, 2H-1,2,3-Triazol-4-yl, 1H-1,2,4-Triazol-1-yl, 1H-1,2,4-Triazol-3-yl, 4H-1,2,4-Triazol-4-yl, 1,2,4-Oxadiazol-3-yl, 1,2,4-Oxadiazol-5-yl, 1,3,4-Oxadiazol-2-yl, 1,2,3-Oxadiazol-4-yl, 1,2,3-Oxadiazol-5-yl, 1,2,5-Oxadiazol-3-yl, 1,3,4-Thiadiazol-2-yl, 1,3,4-Thiadiazol-5-yl, 1,2,4-Thiadiazol-5-yl, 1,2,4-Thiadiazol-3-yl, 1,2,5-Thiadiazol-3-yl, 1,2,5-Thiadiazol-3-yl, 1,2,3-Thiadiazol-4-yl, 1,2,3-Thiadiazol-5-yl, which is unsubstituted, or substituted one or more times by halogen, cyano, methyl, CF 3 , CF 2 Cl, CH 2 F, CHF 2 , OCH 3 , OCF 3 , SCH 3 , SOCH 3 , SO 2 CH 3 and SCF 3 is substituted, R 2< represents hydrogen, fluorine, chlorine, bromine, iodine, CN, methyl, CF 3 , CF 2 Cl, CH 2 F, CHF 2 , OCH 3 , OCF 3 , SCH 3 , SOCH 3 , SO 2 CH 3 and SCF 3, R 3< represents hydrogen and CH 3, R 4< represents hydrogen, (C 1 -C 10 )alkyl, (C 1 -C 10 )haloalkyl, (C 1 -C 10 )cyanoalkyl, (C 2 -C 10 )alkenyl, (C 2 -C 10 )alkynyl, (C 3 -C 9 )cycloalkyl, (C 3 -C 9 )cycloalkenyl, aryl, heteroaryl, (C 1 -C 10 )alkoxy-(C 1 -C 10 )alkyl, (C 1 -C 10 )haloalkoxy-(C 1 -C 10 )alkyl, (C 1 -C 10 )alkoxy-(C 1 -C 10 )haloalkyl, (C 1 -C 10 )alkylthio-(C 1 -C 10 )alkyl,(C 1 -C 10 )haloalkylthio-(C 1 -C 10 )alkyl, (C 2 -C 18 )haloalkenyl, (C 2 -C 18 )haloalkynyl, heterocyclyl-(C 1 -C 10 )alkyl, aryl-(C 1 -C 10 )alkyl, (C 3 -C 9 )cycloalkyl-(C 1 -C 10 )alkyl, (C 1 -C 10 )alkoxycarbonyl-(C 1 -C 10 )alkyl and (C 1 -C 10 )alkoxycarbonyl-(C 3 -C 9 )cycloalkyl-(C 1 -C 10 )alkyl, m represents a number from 0, 1, 2 or 3, and p represents 0, 1 or 2. ,

[0020] In particular, preferred subject matter of the invention are compounds of the general formula (I), in which R 1< for groups Q-1.1 to Q-1.59 Q-1.1 Q-1.2 Q-1.3 Q-1.4 Q-1.5 Q-1.6 Q-1.7 Q-1.8 Q-1.9 Q-1.10 Q-1.11 Q-1.12 Q-1.13 Q-1.14 Q- 1. 15 Q-1.16 Q- 1. 17 Q-1.18 Q-1.19 Q-1.20 Q-1.21 Q-1.22 Q-1.23 Q-1.24 Q-1.25 Q-1.35 Q-1.36 Q-1.37 Q-1.38 Q-1.39 Q-1.40 Q-1.41 Q-1.42 Q-1.43 Q-1.44 Q-1.45 Q-1.46 Q-1.47 Q-1.48 Q-1.49 Q-1.50 Q-1.51 Q-1.52 Q-1.53 Q-1.54 Q-1.55 Q-1.56 Q-1.57 Q-1.58 Q-1.59 R 2< für Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, Methyl, CF 3 , CH 2 F, CHF 2 , OCH 3 , OCF 3 , SCH 3 , SOCH 3 , SO 2 CH 3 und SCF 3 steht, R 3< für Wasserstoff steht, R 4< für Wasserstoff, Methyl, Ethyl, n-Propyl, i-Propyl, n-Butyl, n-Pentyl, Phenyl, Benzyl, CH 2 (4-Cl-Ph), CH 2 (4-F-Ph), CH 2 (4-MeO-Ph), 2-Methoxyethyl, Tetrahydrofuran-2-yl-methyl, Tetrahydrofuran-3-yl-methyl, Tetrahydropyran-2-yl-methyl, Tetrahydropyran-3-yl-methyl, Tetrahydropyran-4-yl-methyl, Methylpropionat-3-yl, Ethylpropionat-3-yl, Methylacet-2-yl, Ethylacet-2-yl, Methylpivalat-2-yl, Ethylpivalat-3-yl, Methyl-2-methylpropanoat-3-yl, Methyl-2,2-dimethylpropanoat-3-yl, Ethyl-2-methylpropanoat-3-yl, Methyl-2-propanoat-2-yl, Ethyl-2-propanoat-2-yl, Methyl-acetat-2yl, Ethyl-acetat-2yl, Methyl-1-methylcyclopropancarboxylat-2yl, Ethyl-1-methylcyclopropancarboxylat-2yl, 2-(Dimethylamino)ethyl, Oxetan-3-yl, (3-Methyloxetan-3-yl)methyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, 2-Fluorethyl, 2,2,3,3,3-Pentafluorpropyl,Cyclopropylmethyl, 1-Cyclopropyl-ethyl, (1-Methyl-cyclopropyl)-methyl, (2,2-Dichlorocyclopropyl)-methyl, (2,2-Dimethyl-cyclopropyl)-methyl, Allyl, Propargyl (Prop-2-yn-1-yl), 2-Chloroprop-2-en-1-yl, 3-Phenylprop-2-yn-1-yl, 3,3-Dichloroprop-2-en-1-yl, 3,3-Dichloro-2-fluoro-prop-2-en-1-yl, Methylprop-2-yn-1-yl, 2-Methylprop-2-en-1-yl, But-2-en-1-yl, But-3-en-1-yl, But-2-yn-1-yl, But-3-yn-1-yl, 4-Chloro-but-2-yn-1-yl, 3-Methyl-but-2-en-1-yl, 3-methyl-but-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, heptan-2-yl, iso-butyl, 1,3-dioxolan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazol-4-methyl, m represents a number of 0, 1, 2 or 3. ,

[0021] The most particularly preferred subject matter of the invention are compounds of the general formula (I), wherein R 1< represents the groups Q-1.1 to Q-1.59 Q-1.1 Q-1.2 Q-1.3 Q-1.4 Q-1.5 Q-1.6 Q-1.7 Q-1.8 Q-1.9 Q-1.10 Q-1.11 Q-1.12 Q-1.13 Q-1.14 Q- 1. 15 Q-1.16 Q- 1. 17 Q-1.18 Q-1.19 Q-1.20 Q-1.21 Q-1.22 Q-1.23 Q-1.24 Q-1.25 Q-1.35 Q-1.36 Q-1.37 Q-1.38 Q-1.39 Q-1.40 Q-1.41 Q-1.42 Q-1.43 Q-1.44 Q-1.45 Q-1.46 Q-1.47 Q-1.48 Q-1.49 Q-1.50 Q-1.51 Q-1.52 Q-1.53 Q-1.54 Q-1.55 Q-1.56 Q-1.57 Q-1.58 Q-1.59 stands, and (R 2 ) m -Phenyl for groups Q-2.1 to Q-2.53 Q-2.1 Q-2.2 Q-2.3 Q-2.4 Q-2.5 Q-2.6 Q-2.7 Q-2.8 Q-2.9 Q-2.10 Q-2.11 Q-2.12 Q-2.13 Q-2.14 Q-2.15 Q-2.16 Q-2.17 Q-2.18 Q-2.19 Q-2.20 Q-2.21 Q-2.22 Q-2.23 Q-2.24 Q-2.25 Q-2.26 Q-2.27 Q-2.28 Q-2.29 Q-2.30 Q-2.31 Q-2.32 Q-2.33 Q-2.34 Q-2.35 Q-2.36 Q-2.37 Q-2.38 Q-2.39 Q-2.40 Q-2.41 Q-2.42 Q-2.43 Q-2.44 Q-2.45 Q-2.46 Q-2.47 Q-2.48 Q-2.49 Q-2.50 Q-2.51 Q-2.52 Q-2.53 stands. R 3< für Wasserstoff, steht, R 4< für Wasserstoff, Methyl, Ethyl, n-Propyl, i-Propyl, n-Butyl, n-Pentyl, Phenyl, Benzyl, CHz(4-Cl-Ph), CH 2 (4-F-Ph), CH 2 (4-MeO-Ph), 2-Methoxyethyl, Tetrahydrofuran-2-yl-methyl, Tetrahydrofuran-3-yl-methyl, Tetrahydropyran-2-yl-methyl, Tetrahydropyran-3-yl-methyl, Tetrahydropyran-4-yl-methyl, Methylpropionat-3-yl, Ethylpropionat-3-yl, Methylacetat-2-yl, Ethylacetat-2-yl, Methylpivalat-2-yl, Ethylpivalat-3-yl, Methyl-2-methylpropanoat-3-yl, Methyl-2,2-dimethylpropanoat-3-yl, Ethyl-2-methylpropanoat-3-yl, Methyl-2-propanoat-2-yl, Ethyl-2-propanoat-2-yl, Methylacet-2yl, Ethylacet-2yl, Methyl-1-methylcyclopropancarboxylat-2yl, Ethyl-1-methylcyclopropancarboxylat-2yl, 2-(Dimethylamino)ethyl, Oxetan-3-yl, (3-Methyloxetan-3-yl)methyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, 2-Fluorethyl, 2,2,3,3,3-Pentafluorpropyl, Cyclopropylmethyl, 1-Cyclopropyl-ethyl, (1-Methyl-cyclopropyl)-methyl, (2,2-Dichlorcyclopropyl)-methyl, (2,2-Dimethyl-cyclopropyl)-methyl, Allyl,Propargyl (Prop-2-yn-1-yl), 2-Chloroprop-2-en-1-yl, 3-Phenylprop-2-yn-1-yl, 3,3-Dichloroprop-2-en-1-yl, 3,3-Dichloro-2-fluoro-prop-2-en-1-yl, Methylprop-2-yn-1-yl, 2-Methylprop-2-en-1-yl, But-2-en-1-yl, But-3-en-1-yl, But-2-yn-1-yl, But-3-yn-1-yl, 4-chloro-but-2-yn-1-yl, 3-methyl-but-2-en-1-yl, 3-methyl-but-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-Pent-3-en-2-yl or (Z)-Pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, heptan-2-yl, iso-butyl, 1,3-dioxolan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl. ,

[0022] In particular, the invention particularly particularly prefers compounds of the general formula (I), wherein R' represents the following groups selected from Q-1.1 to Q-1.59 Q-1.1 Q-1.2 Q-1.3 Q-1.4 Q-1.5 Q-1.6 Q-1.7 Q-1.10 Q-1.11 Q-1.12 Q-1.13 Q-1.14 Q- 1. 15 Q- 1. 17 Q-1.18 Q-1.19 Q-1.21 Q-1.22 Q-1.24 Q-1.25 Q-1.56 Q-1.57 Q-1.59 stands, and (R 2 ) m -Phenyl for groups Q-2.1 to Q-2.53 Q-2.1 Q-2.2 Q-2.3 Q-2.4 Q-2.5 Q-2.6 Q-2.7 Q-2.8 Q-2.9 Q-2.10 Q-2.11 Q-2.12 Q-2.13 Q-2.14 Q-2.15 Q-2.16 Q-2.17 Q-2.18 Q-2.19 Q-2.20 Q-2.21 Q-2.22 Q-2.23 Q-2.24 Q-2.25 Q-2.26 Q-2.27 Q-2.28 Q-2.29 Q-2.30 Q-2.31 Q-2.32 Q-2.33 Q-2.34 Q-2.35 Q-2.36 Q-2.37 Q-2.38 Q-2.39 Q-2.40 Q-2.41 Q-2.42 Q-2.43 Q-2.44 Q-2.45 Q-2.46 Q-2.47 Q-2.48 Q-2.49 Q-2.50 Q-2.51 Q-2.52 Q-2.53 stands, R 3< für Wasserstoff steht, R 4< für Wasserstoff, Methyl, Ethyl, n-Propyl, i-Propyl, n-Butyl, n-Pentyl, Phenyl, Benzyl, CHz(4-Cl-Ph), CH 2 (4-F-Ph), CH 2 (4-OMe-Ph), 2-Methoxyethyl, Tetrahydrofuran-2-yl-methyl, Tetrahydrofuran-3-yl-methyl, Tetrahydropyran-2-yl-methyl, Tetrahydropyran-3-yl-methyl, Tetrahydropyran-4-yl-methyl, Methylpropionat-3-yl, Ethylpropionat-3-yl, Methylacetat-2-yl, Ethylacetat-2-yl, Methylpivalat-2-yl, Ethylpivalat-3-yl, Methyl-2-methylpropanoat-3-yl, Methyl-2,2-dimethylpropanoat-3-yl, Ethyl-2-methylpropanoat-3-yl, Methyl-2-propanoat-2-yl, Ethyl-2-propanoat-2-yl, Methylacet-2-yl, Ethylacet-2-yl, Methyl-1-methylcyclopropancarboxylat-2yl, Ethyl-1-methylcyclopropancarboxylat-2yl, 2-(Dimethylamino)ethyl, Oxetan-3-yl, (3-Methyloxetan-3-yl)methyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, 2-Fluorethyl, 2,2,3,3,3-Pentafluorpropyl, Cyclopropylmethyl, 1-Cyclopropyl-ethyl, (1-Methyl-cyclopropyl)-methyl, (2,2-Dichlorcyclopropyl)-methyl, (2,2-Dimethyl-cyclopropyl)-methyl, Allyl,Propargyl (Prop-2-yn-1-yl), 2-Chloroprop-2-en-1-yl, 3-Phenylprop-2-yn-1-yl, 3,3-Dichloroprop-2-en-1-yl, 3,3-Dichloro-2-fluoro-prop-2-en-1-yl, Methylprop-2-yn-1-yl, 2-Methylprop-2-en-1-yl, But-2-en-1-yl, But-3-en-1-yl, But-2-yn-1-yl, But-3-yn-1-yl, 4-chloro-but-2-yn-1-yl, 3-methyl-but-2-en-1-yl, 3-methyl-but-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-Pent-3-en-2-yl or (Z)-Pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, heptan-2-yl, iso-butyl, 1,3-dioxolan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl. ,

[0023] The radical definitions listed above, either general or in preferred ranges, apply both to the end products of general formula (I) and, accordingly, to the starting materials or intermediates required for their preparation. These radical definitions can be combined with each other, i.e., even within the specified preferred ranges.

[0024] Particularly for reasons of higher herbicidal activity, better selectivity and / or better preparability, compounds according to the invention of the general formula (I) mentioned or salts thereof or the use thereof according to the invention are of particular interest in which individual radicals 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.

[0025] With regard to the compounds according to the invention, the designations used above and below are explained. These are familiar to the person skilled in the art and have, in particular, the meanings explained below: Unless defined otherwise, the general rule for the designation of chemical groups is that the bond to the skeleton or the remainder of the molecule is via the last-mentioned structural element of the chemical group in question, ie, for example, in the case of (C 2 -C 8 )-alkenyloxy via the oxygen atom, and in the case of heterocyclyl-(C 1 -C 8 )-alkyl or alkylO(O)C-(C 1 -C 8 )-alkyl via the C atom of the alkyl group.

[0026] According to the invention, "alkylsulfonyl" - alone or as part of a chemical group - stands for straight-chain or branched alkylsulfonyl, preferably with 1 to 8, or with 1 to 6 carbon atoms, e.g.(aber nicht beschränkt auf) (C 1 -C 6 )-Alkylsulfonyl wie Methylsulfonyl, Ethylsulfonyl, Propylsulfonyl, 1-Methylethylsulfonyl, Butylsulfonyl, 1-Methylpropylsulfonyl, 2-Methylpropylsulfonyl, 1,1-Dimethylethylsulfonyl, Pentylsulfonyl, 1-Methylbutylsulfonyl, 2-Methylbutylsulfonyl, 3-Methylbutylsulfonyl, 1,1-Dimethylpropylsulfonyl, 1,2-Dimethylpropylsulfonyl, 2,2-Dimethylpropylsulfonyl, 1-Ethylpropylsulfonyl, Hexylsulfonyl, 1-Methylpentylsulfonyl, 2-Methylpentylsulfonyl, 3-Methylpentylsulfonyl, 4-Methylpentylsulfonyl, 1,1-Dimethylbutylsulfonyl, 1,2-Dimethylbutylsulfonyl, 1,3-Dimethylbutylsulfonyl, 2,2-Dimethylbutylsulfonyl, 2,3-Dimethylbutylsulfonyl, 3,3-Dimethylbutylsulfonyl, 1-Ethylbutylsulfonyl, 2-Ethylbutylsulfonyl, 1,1,2-Trimethylpropylsulfonyl, 1,2,2-Trimethylpropylsulfonyl, 1-Ethyl-1-methylpropylsulfonyl und 1-Ethyl-2-methylpropylsulfonyl.

[0027] According to the invention, "alkylthio" - alone or as part of a chemical group - stands for straight-chain or branched S-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as (C 1 -C 10 )-, (C 1 -C 6 )- or (C 1 -C 4 )-alkylthio, e.g. (but not limited to) (C 1 -C 6 )-alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methylpentylthio, 1,1-Dimethylbutylthio, 1,2-Dimethylbutylthio, 1,3-Dimethylbutylthio, 2,2-Dimethylbutylthio, 2,3-Dimethylbutylthio, 3,3-Dimethylbutylthio, 1-Ethylbutylthio, 2-Ethylbutylthio, 1,1,2-Trimethylpropylthio, 1,2,2-Trimethylpropylthio, 1-Ethyl-1-methylpropylthio and 1-Ethyl-2-methylpropylthio.

[0028] "Alkylsulfinyl (alkyl-S(=O)-)", unless defined otherwise elsewhere, stands according to the invention for alkyl radicals which are bonded to the skeleton via -S(=O)-, such as (C 1 -C 6 )- or (C 1 -C 4 )-alkylsulfinyl, e.g.(aber nicht beschränkt auf) (C 1 -C 6 )-Alkylsulfinyl wie Methylsulfinyl, Ethylsulfinyl, Propylsulfinyl, 1-Methylethylsulfinyl, Butylsulfinyl, 1-Methylpropylsulfinyl, 2-Methylpropylsulfinyl, 1,1-Dimethylethylsulfinyl, Pentylsulfinyl, 1-Methylbutylsulfinyl, 2-Methylbutylsulfinyl, 3-Methylbutylsulfinyl, 1,1-Dimethylpropylsulfinyl, 1,2-Dimethylpropylsulfinyl, 2,2-Dimethylpropylsulfinyl, 1-Ethylpropylsulfinyl, Hexylsulfinyl, 1-Methylpentylsulfinyl, 2-Methylpentylsulfinyl, 3-Methylpentylsulfinyl, 4-Methylpentylsulfinyl, 1,1-Dimethylbutylsulfinyl, 1,2-Dimethylbutylsulfinyl, 1,3-Dimethylbutylsulfinyl, 2,2-Dimethylbutylsulfinyl, 2,3-Dimethylbutylsulfinyl, 3,3-Dimethylbutylsulfinyl, 1-Ethylbutylsulfinyl, 2-Ethylbutylsulfinyl, 1,1,2-Trimethylpropylsulfinyl, 1,2,2-Trimethylpropylsulfinyl, 1-Ethyl-1-methylpropylsulfinyl und 1-Ethyl-2-methylpropylsulfinyl.

[0029] "Alkoxy" means an alkyl radical bonded via an oxygen atom, e.g. B. (but not limited to) (C 1 -C 6 )-alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-Dimethylpropoxy, 2,2-Dimethylpropoxy, 1-Ethylpropoxy, Hexoxy, 1-Methylpentoxy, 2-Methylpentoxy, 3-Methylpentoxy, 4-Methylpentoxy, 1,1-Dimethylbutoxy, 1,2-Dimethylbutoxy, 1,3-Dimethylbutoxy, 2,2-Dimethylbutoxy, 2,3-Dimethylbutoxy, 3,3-Dimethylbutoxy, 1-Ethylbutoxy, 2-Ethylbutoxy, 1,1,2-Trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, and 1-ethyl-2-methylpropoxy. Alkenyloxy means an alkenyl radical bonded via an oxygen atom. Alkynyloxy means an alkynyl radical bonded via an oxygen atom, such as (C 2 -C 10 ), (C 2 -C 6 ), or (C 2 -C 4 )-alkenoxy or (C 3 -C 6 )- or (C 3 -C 4 )-alkynoxy.

[0030] "Alkylcarbonyl" (alkyl-C(=O)-), unless defined otherwise elsewhere, refers to alkyl radicals bonded to the skeleton via -C(=O)-, such as (C 1 -C 10 ), (C 1 -C 6 ), or (C 1 -C 4 )-alkylcarbonyl. The number of C atoms refers to the alkyl radical in the alkylcarbonyl group.

[0031] "Alkoxycarbonyl (alkyl-OC(=O)-)", unless defined otherwise elsewhere: Alkyl radicals bonded to the skeleton via -OC(=O)-, such as (C 1 -C 10 )-, (C 1 -C 6 )-, or (C 1 -C 4 )-alkoxycarbonyl. The number of C atoms refers to the alkyl radical in the alkoxycarbonyl group. Analogously, "alkenyloxycarbonyl" and "alkynyloxycarbonyl", unless defined otherwise elsewhere, represent alkenyl or alkynyl radicals bonded to the skeleton via -OC(=O)-, such as (C 2 -C 10 ), (C 2 -C 6 ), or (C 2 -C 4 )-alkenyloxycarbonyl or (C 3 -C 10 ), (C 3 -C 6 ), or (C 3 -C 4 )-alkynyloxycarbonyl. The number of C atoms refers to the alkenyl or alkynyl radical in the alkene or alkynyloxycarbonyl group.

[0032] The term "aryl" means an optionally substituted mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring carbon atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.

[0033] The term "optionally substituted aryl" also encompasses polycyclic systems such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, and biphenylyl, where the bonding site is on the aromatic system. Systematically, "aryl" is generally also encompassed by the term "optionally substituted phenyl."Bevorzugte Aryl-Substituenten sind hier zum Beispiel Wasserstoff, Halogen, Alkyl, Cycloalkyl, Cycloalkylalkyl, Cycloalkenyl, Halocycloalkyl, Alkenyl, Alkinyl, Aryl, Arylalkyl, Heteroaryl, Heteroarylalkyl, Heterocyclyl, Heterocyclylalkyl, Alkoxyalkyl, Alkylthio, Haloalkylthio, Haloalkyl, Alkoxy, Haloalkoxy, Cycloalkoxy, Cycloalkylalkoxy, Aryloxy, Heteroraryloxy, Alkoxyalkoxy, Alkinylalkoxy, Alkenyloxy, Bis-alkylaminoalkoxy, Tris-[alkyl]silyl, Bis-[alkyl]arylsilyl, Bis-[alkyl]alkylsilyl, Tris-[alkyl]silylalkinyl, Alkylalkinyl, Cycloalkylalkinyl, Haloalkylalkinyl, Heterocyclyl-N-alkoxy, Nitro, Cyano, Amino, Alkylamino, Bis-alkylamino, Alkylcarbonylamino, Cycloalkylcarbonylamino, Arylcarbonylamino, Alkoxycarbonylamino, Alkoxycarbonylalkylamino, Arylalkoxycarbonylalkylamino, Hydroxycarbonyl, Alkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Cycloalkylaminocarbonyl, Bis-Alkylaminocarbonyl, Heteroarylalkoxy, Arylalkoxy.

[0034] A heterocyclic radical (heterocyclyl) contains at least one heterocyclic ring (=carbocyclic ring in which at least one C atom is replaced by a heteroatom, preferably by a heteroatom from the group N, O, S, P) which is saturated, unsaturated, partially saturated or heteroaromatic and may be unsubstituted or substituted, with the bonding site being located on a ring atom. If the heterocyclyl radical or the heterocyclic ring is optionally substituted, it may be fused to other carbocyclic or heterocyclic rings. In the case of optionally substituted heterocyclyl, polycyclic systems are also included, such as, for example, 8-azabicyclo[3.2.1]octanyl, 8-azabicyclo[2.2.2]octanyl or 1-azabicyclo[2.2.1]heptyl. In the case of optionally substituted heterocyclyl, spirocyclic systems are also included, such as 1-oxa-5-aza-spiro[2.3]hexyl. Unless otherwise defined,the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, although two oxygen atoms should not be directly adjacent, such as, for example, with a heteroatom from the group N, O and S 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2- or 3-yl, 2,3-dihydro-1H-pyrrol-1- or 2- or 3- or 4- or 5-yl; 2,5-dihydro-1H-pyrrol-1- or 2- or 3-yl, 1- or 2- or 3- or 4-piperidinyl; 2,3,4,5-Tetrahydropyridin-2- or 3- or 4- or 5-yl or 6-yl; 1,2,3,6-Tetrahydropyridin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2,3,4-Tetrahydropyridin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4-Dihydropyridin-1- or 2- or 3- or 4-yl; 2,3-Dihydropyridin-2- or 3- or 4- or 5- or 6-yl; 2,5-Dihydropyridin-2- or 3- or 4- or 5- or 6-yl,1- or 2- or 3- or 4-azepanyl; 2,3,4,5-tetrahydro-1H-azepin-1- or 2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1H-azepin-1- or 2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1H-azepin-1- or 2- or 3- or 4-yl; 3,4,5,6-tetrahydro-2H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-1H-azepin-1- or 2- or 3- or 4-yl; 2,5-Dihydro-1H-azepin-1- or -2- or 3- or 4- or 5- or 6- or 7-yl; 2,7-Dihydro-1H-azepin-1- or -2- or 3- or 4-yl; 2,3-Dihydro-1H-azepin-1- or -2- or 3- or 4- or 5- or 6- or 7-yl; 3,4-Dihydro-2H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 3,6-Dihydro-2H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 5,6-Dihydro-2H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-Dihydro-3H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 1H-azepin-1- or -2- or 3- or 4- or 5- or 6- or 7-yl; 2H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 3H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl, 2- or 3-oxolanyl (= 2- or 3-tetrahydrofuranyl); 2,3-dihydrofuran-2- or 3- or 4- or 5-yl; 2,5-Dihydrofuran-2- or 3-yl, 2- or 3- or 4-oxanyl (= 2- or 3- or 4-tetrahydropyranyl); 3,4-Dihydro-2H-pyran-2- or 3- or 4- or 5- or 6-yl; 3,6-Dihydro-2H-pyran-2- or 3- or 4- or 5- or 6-yl; 2H-Pyran-2- or 3- or 4- or 5- or 6-yl; 4H-Pyran-2- or 3- or 4-yl, 2- or 3- or 4-oxepanyl; 2,3,4,5-Tetrahydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-Tetrahydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-Tetrahydrooxepin-2- or 3- or 4-yl; 2,3-Dihydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-Dihydrooxepin-2- or 3- or 4-yl; 2,5-Dihydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl; Oxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2- or 3-Tetrahydrothiophenyl; 2,3-Dihydrothiophen-2- or 3- or 4- or 5-yl; 2,5-Dihydrothiophen-2- or 3-yl; Tetrahydro-2H-thiopyran-2- or 3- or 4-yl; 3,4-Dihydro-2H-thiopyran-2- or 3- or 4- or 5- or 6-yl; 3,6-Dihydro-2H-thiopyran-2- or 3- or 4- or 5- or 6-yl; 2H-Thiopyran-2- or 3- or 4- or 5- or 6-yl; 4H-Thiopyran-2- or 3- or 4-yl. Preferred 3-membered and 4-membered ring heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, and 1,3-dioxetan-2-yl. Further examples of "heterocyclyl" are a partially or fully hydrogenated heterocyclic radical having two heteroatoms from the group consisting of N, O, and S, such as, for example, 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazol-3- or 4- or 5-yl; 4,5-Dihydro-1H-pyrazol-1- or 3- or 4- or 5-yl; 2,3-Dihydro-1H-pyrazol-1- or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 4- imidazolidinyl; 2,3-Dihydro-1H-imidazol-1- or 2- or 3- or 4-yl; 2,5-Dihydro-1H-imidazol-1- or 2- or 4- or 5-yl; 4,5-Dihydro-1H-imidazol-1- or 2- or 4- or 5-yl; Hexahydropyridazin-1- or 2- or 3- or 4-yl; 1,2,3,4-Tetrahydropyridazin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2,3,6-Tetrahydropyridazin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4,5,6-Tetrahydropyridazin-1- or 3- or 4- or 5- or 6-yl; 3,4,5,6-Tetrahydropyridazin-3- or 4- or 5-yl; 4,5-Dihydropyridazin-3- or 4-yl; 3,4-Dihydropyridazin-3- or 4- or 5- or 6-yl; 3,6-Dihydropyridazin-3- or 4-yl; 1,6-Dihydropyriazin-1- or 3- or 4- or 5- or 6-yl; Hexahydropyrimidin-1- or 2- or 3- or 4-yl; 1,4,5,6-Tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2,5,6-Tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2,3,4-Tetrahydropyrimidin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,6-Dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2-Dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 2,5-Dihydropyrimidin-2- or 4- or 5-yl; 4,5-Dihydropyrimidin- 4- or 5- or 6-yl; 1,4-Dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1- or 2- or 3-Piperazinyl; 1,2,3,6-Tetrahydropyrazin-1- or 2- or 3- or 5- or 6-yl; 1,2,3,4-Tetrahydropyrazin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2-Dihydropyrazin-1- or 2- or 3- or 5- or 6-yl; 1,4-Dihydropyrazin-1- or 2- or 3-yl; 2,3-Dihydropyrazin-2- or 3- or 5- or 6-yl; 2,5-Dihydropyrazin-2- or 3-yl; 1,3-Dioxolan-2- or 4- or 5-yl; 1,3-Dioxol-2- or 4-yl; 1,3-Dioxan-2- or 4- or 5-yl; 4H-1,3-Dioxin-2- or 4- or 5- or 6-yl; 1,4-dioxan-2- or 3- or 5- or 6-yl; 2,3-dihydro-1,4-dioxin-2- or 3- or 5- or 6-yl; 1,4-dioxin-2- or 3-yl; 1,2-dithiolan-3- or 4-yl; 3H-1,2-Dithiol-3- or 4- or 5-yl; 1,3-Dithiolan-2- or 4-yl; 1,3-Dithiol-2- or 4-yl; 1,2-Dithian-3- or 4-yl; 3,4-Dihydro-1,2-dithiin-3- or 4- or 5- or 6-yl; 3,6-Dihydro-1,2-dithiin-3- or 4-yl; 1,2-Dithiin-3- or 4-yl; 1,3-Dithian-2- or 4- or 5-yl; 4H-1,3-Dithiin-2- or 4- or 5- or 6-yl; isoxazolidin-2- or 3- or 4- or 5-yl; 2,3-Dihydroisoxazol-2- or 3- or 4- or 5-yl; 2,5-Dihydroisoxazol-2- or 3- or 4- or 5-yl; 4,5-Dihydroisoxazol-3- or 4- or 5-yl; 1,3-Oxazolidin-2- or 3- or 4- or 5-yl; 2,3-Dihydro-1,3-oxazol-2- or 3- or 4- or 5-yl; 2,5-Dihydro-1,3-oxazol-2- or 4- or 5-yl; 4,5-Dihydro-1,3-oxazol-2- or 4- or 5-yl; 1,2-Oxazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-Dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-Dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-Dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-Dihydro-4H-1,2-oxazin-3- or 4- or 5- or 6-yl; 2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 6H-1,2-oxazin-3- or 4- or 5- or 6-yl; 4H-1,2-oxazin-3- or 4- or 5- or 6-yl; 1,3-oxazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,3-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,3-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-1,3-oxazin-2- or 4- or 5- or 6-yl; 5,6-Dihydro-4H-1,3-oxazin-2- or 4- or 5- or 6-yl; 2H-1,3-oxazin-2- or 4- or 5- or 6-yl; 6H-1,3-oxazin-2- or 4- or 5- or 6-yl; 4H-1,3-oxazin-2- or 4- or 5- or 6-yl; Morpholin-2- or 3- or 4-yl; 3,4-Dihydro-2H-1,4-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-Dihydro-2H-1,4-oxazin-2- or 3- or 5- or 6-yl; 2H-1,4-oxazin-2- or 3- or 5- or 6-yl; 4H-1,4-oxazin-2- or 3-yl; 1,2-oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-Tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7-Tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5,6,7-Tetrahydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 2,3-Dihydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5-Dihydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,7-Dihydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-Dihydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 4,7-Dihydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 6,7-Dihydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 1,2-Oxazepin-3- or 4- or 5- or 6- or 7-yl; 1,3-Oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,5-Tetrahydro-1,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-Tetrahydro-1,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-Tetrahydro-1,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7-Tetrahydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,5,6,7-Tetrahydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 2,3-Dihydro-1,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5-Dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 2,7-Dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,5-Dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,7-Dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 6,7-Dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 1,4-oxazepan-2- or 3- or 5- or 6- or 7-yl; 2,3,4,5-Tetrahydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-Tetrahydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-Tetrahydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 2,5,6,7-Tetrahydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 4,5,6,7-Tetrahydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3-Dihydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 2,5-dihydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 2,7-dihydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 4,5-dihydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 1,4-Oxazepin-2- or 3- or 5- or 6- or 7-yl; Isothiazolidin-2- or 3- or 4- or 5-yl; 2,3-Dihydroisothiazol-2- or 3- or 4- or 5-yl; 2,5-Dihydroisothiazol-2- or 3- or 4- or 5-yl; 4,5-Dihydroisothiazol-3- or 4- or 5-yl; 1,3-Thiazolidin-2- or 3- or 4- or 5-yl; 2,3-Dihydro-1,3-thiazol-2- or 3- or 4- or 5-yl; 2,5-Dihydro-1,3-thiazol-2- or 4- or 5-yl; 4,5-Dihydro-1,3-thiazol-2- or 4- or 5-yl; 1,3-Thiazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-Dihydro-2H-1,3-thiazin-2- or 3- or 4- or 5- or 6-yl; 3,6-Dihydro-2H-1,3-thiazin-2- or 3- or 4- or 5- or 6-yl; 5,6-Dihydro-2H-1,3-thiazin-2- or 4- or 5- or 6-yl; 5,6-Dihydro-4H-1,3-thiazin-2- or 4- or 5- or 6-yl; 2H-1,3-thiazin-2- or 4- or 5- or 6-yl; 6H-1,3-thiazin-2- or 4- or 5- or 6-yl; 4H-1,3-thiazin-2- or 4- or 5- or 6-yl. Further examples of "heterocyclyl" are a partially or fully hydrogenated heterocyclic radical with 3 heteroatoms from the group N, O, and S, such as 1,4,2-dioxazolidin-2- or 3- or 5-yl; 1,4,2-dioxazol-3- or 5-yl; 1,4,2-dioxazinan-2- or -3- or 5- or 6-yl; 5,6-dihydro-1,4,2-dioxazin-3- or 5- or 6-yl; 1,4,2-dioxazin-3- or 5- or 6-yl; 1,4,2-dioxazepan-2- or 3- or 5- or 6- or 7-yl; 6,7-dihydro-5H-1,4,2-dioxazepin-3- or 5- or 6- or 7-yl; 2,3-dihydro-7H-1,4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl; 2,3-dihydro-5H-1,4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl; 5H-1,4,2-dioxazepine-3- or 5- or 6- or 7-yl; 7H-1,4,2-Dioxazepin-3- or 5- or 6- or 7-yl. Structural examples of optionally further substituted heterocycles are also listed below: ,

[0035] Die oben aufgeführten Heterocyclen sind bevorzugt beispielsweise durch Wasserstoff, Halogen, Alkyl, Haloalkyl, Hydroxy, Alkoxy, Cycloalkoxy, Aryloxy, Alkoxyalkyl, Alkoxyalkoxy, Cycloalkyl, Halocycloalkyl, Aryl, Arylalkyl, Heteroaryl, Heterocyclyl, Alkenyl, Alkylcarbonyl, Cycloalkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, Alkoxycarbonyl, Hydroxycarbonyl, Cycloalkoxycarbonyl, Cycloalkylalkoxycarbonyl, Alkoxycarbonylalkyl, Arylalkoxycarbonyl, Arylalkoxycarbonylalkyl, Alkinyl, Alkinylalkyl, Alkylalkinyl, Tris-alkylsilylalkinyl, Nitro, Amino, Cyano, Haloalkoxy, Haloalkylthio, Alkylthio, Hydrothio, Hydroxyalkyl, Oxo, Heteroarylalkoxy, Arylalkoxy, Heterocyclylalkoxy, Heterocyclylalkylthio, Heterocyclyloxy, Heterocyclylthio, Heteroaryloxy, Bis-alkylamino, Alkylamino, Cycloalkylamino, Hydroxycarbonylalkylamino, Alkoxycarbonylalkylamino, Arylalkoxycarbonylalkylamino, Alkoxycarbonylalkyl(alkyl)amino, Aminocarbonyl, Alkylaminocarbonyl, Bis-alkylaminocarbonyl, Cycloalkylaminocarbonyl,Hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl, arylalkoxycarbonylalkylaminocarbonyl substituted.,

[0036] If a basic structure is substituted "by one or more residues" from a list of residues (= group) or a generically defined group of residues, this includes the simultaneous substitution by several identical and / or structurally different residues.

[0037] If it is a partially or fully saturated nitrogen heterocycle, it can be linked to the rest of the molecule via either carbon or nitrogen.

[0038] Possible substituents for a substituted heterocyclic radical are the substituents listed below, as well as oxo and thioxo. The oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring. This preferably also includes lactones and lactams. The oxo group can also occur on the hetero ring atoms, which can exist in different oxidation states, e.g. N and S, and then form, for example, the divalent groups N(O), S(O) (also abbreviated SO) and S(O) 2 (also abbreviated SO 2 ) in the heterocyclic ring. In the case of -N(O)- and -S(O)- groups, both enantiomers are included.

[0039] According to the invention, the term "heteroaryl" stands for heteroaromatic compounds, ie fully unsaturated aromatic heterocyclic compounds, preferably for 5- to 7-membered rings with 1 to 4, preferably 1 or 2 identical or different heteroatoms, preferably O, S or N. Heteroaryls according to the invention are, for example, 1H-pyrrol-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl; furan-2-yl; furan-3-yl; thien-2-yl; thien-3-yl, 1H-imidazol-1-yl; 1H-imidazol-2-yl; 1H-imidazol-4-yl; 1H-imidazol-5-yl; 1H-pyrazol-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1H-pyrazol-5-yl, 1H-1,2,3-triazol-1-yl, 1H-1,2,3-triazol-4-yl, 1H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1,2,4-triazol-1-yl, 1H-1,2,4-triazol-3-yl, 4H-1,2,4-triazol-4-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,5-oxadiazol-3-yl, azepinyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl,Pyrimidin-4-yl, Pyrimidin-5-yl, Pyridazin-3-yl, Pyridazin-4-yl, 1,3,5-Triazin-2-yl, 1,2,4-Triazin-3-yl, 1,2,4-Triazin-5-yl, 1,2,4-Triazin-6-yl, 1,2,3-Triazin-4-yl, 1,2,3-Triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- und 1,2,6-Oxazinyl, Isoxazol-3-yl, Isoxazol-4-yl, Isoxazol-5-yl, 1,3-Oxazol-2-yl, 1,3-Oxazol-4-yl, 1,3-Oxazol-5-yl, Isothiazol-3-yl, Isothiazol-4-yl, Isothiazol-5-yl, 1,3-Thiazol-2-yl, 1,3-Thiazol-4-yl, 1,3-Thiazol-5-yl, 1,3,4-Thiadiazol-2-yl, 1,3,4-Thiadiazol-5-yl, 1,2,4-Thiadiazol-5-yl, 1,2,4-Thiadiazol-3-yl, 1,2,5-Thiadiazol-3-yl, 1,2,5-Thiadiazol-3-yl, 1,2,3-Thiadiazol-4-yl, 1,2,3-Thiadiazol-5-yl, Oxepinyl, Thiepinyl, 1,2,4-Triazolonyl und 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. Die erfindungsgemäßen Heteroarylgruppen können ferner mit einem oder mehreren,identical or different radicals. If two adjacent carbon atoms are part of another aromatic ring, these are fused heteroaromatic systems, such as benzofused or multiply fused heteroaromatics. Preferred examples are quinolines (e.g. quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl); isoquinolines (e.g. 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 heteroaryl are also 5- or 6-membered benzofused 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,1-Benzofuran-2-yl, 1-Benzofuran-3-yl, 1-Benzofuran-4-yl, 1-Benzofuran-5-yl, 1-Benzofuran-6-yl, 1-Benzofuran-7-yl, 1-Benzothiophen-2-yl, 1-Benzothiophen-3-yl, 1-Benzothiophen-4-yl, 1-Benzothiophen-5-yl, 1-Benzothiophen-6-yl, 1-Benzothiophen-7-yl, 1H-Indazol-1-yl, 1H-Indazol-3-yl, 1H-Indazol-4-yl, 1H-Indazol-5-yl, 1H-Indazol-6-yl, 1H-Indazol-7-yl, 2H-Indazol-2-yl, 2H-Indazol-3-yl, 2H-Indazol-4-yl, 2H-Indazol-5-yl, 2H-Indazol-6-yl, 2H-Indazol-7-yl, 2H-Isoindol-2-yl, 2H-Isoindol-1-yl, 2H-Isoindol-3-yl, 2H-Isoindol-4-yl, 2H-Isoindol-5-yl, 2H-Isoindol-6-yl; 2H-Isoindol-7-yl, 1H-Benzimidazol-1-yl, 1H-Benzimidazol-2-yl, 1H-Benzimidazol-4-yl, 1H-Benzimidazol-5-yl, 1H-Benzimidazol-6-yl, 1H-Benzimidazol-7-yl, 1,3-Benzoxazol-2-yl, 1,3-Benzoxazol-4-yl, 1,3-Benzoxazol-5-yl, 1,3-Benzoxazol-6-yl, 1,3-Benzoxazol-7-yl, 1,3-Benzthiazol-2-yl, 1,3-Benzthiazol-4-yl, 1,3-Benzthiazol-5-yl, 1,3-Benzthiazol-6-yl, 1,3-Benzthiazol-7-yl, 1,2-Benzisoxazol-3-yl, 1,2-Benzisoxazol-4-yl, 1,2-Benzisoxazol-5-yl, 1,2-Benzisoxazol-6-yl, 1,2-Benzisoxazol-7-yl, 1,2-Benzisothiazol-3-yl, 1,2-Benzisothiazol-4-yl, 1,2-Benzisothiazol-5-yl, 1,2-Benzisothiazol-6-yl, 1,2-Benzisothiazol-7-yl.,

[0040] The term "halogen" means, for example, fluorine, chlorine, bromine, or iodine. When used for a radical, "halogen" means, for example, a fluorine, chlorine, bromine, or iodine atom.

[0041] According to the invention, "alkyl" means a straight-chain or branched, open-chain, saturated hydrocarbon radical, which is optionally mono- or polysubstituted and, in the latter case, is referred to as "substituted alkyl." Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, cycloalkyl, alkoxycarbonyl, hydroxycarbonyl, heterocyclyl, hetaryl, aryl, amino, or nitro groups; particularly preferred are methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine, or iodine. The prefix "bis" also includes combinations of different alkyl radicals, e.g., methyl(ethyl) or ethyl(methyl).

[0042] "Haloalkyl", "-alkenyl" and "-alkynyl" mean alkyl, alkenyl or alkynyl which are partially or fully substituted by identical or different halogen atoms, e.g. monohaloalkyl (= monohaloalkyl) such as CH 2 CH 2 Cl, CH 2 CH 2 Br, CHClCH 3 , CH 2 Cl, CH 2 F; perhaloalkyl such as CCl 3 , CClF 2 , CFCl 2 , CF 2 CClF 2 , CF 2 CClFCF 3 ; polyhaloalkyl such as CH 2 CHFCl, CF 2 CClFH, CF 2 CBrFH, CH 2 CF 3 ; the term perhaloalkyl also includes the term perfluoroalkyl.

[0043] "Haloalkoxy" is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl; the same applies to haloalkenyl and other halogen-substituted radicals.

[0044] The term "(C 1 -C 4 )-alkyl" used here as an example is a shorthand notation for straight-chain or branched alkyl having one to four carbon atoms, corresponding to the range specified for C atoms, i.e., it includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl, or tert-butyl. General alkyl radicals with a larger specified range of C atoms, e.g., "(C 1 -C 6 )-alkyl," correspondingly also include straight-chain or branched alkyl radicals with a larger number of C atoms, i.e., according to the example, also the alkyl radicals with 5 and 6 C atoms.

[0045] Unless specifically stated, lower carbon skeletons, e.g., those with 1 to 6 C atoms, or unsaturated groups with 2 to 6 C atoms, are preferred for hydrocarbon radicals such as alkyl, alkenyl, and alkynyl, even in compound radicals. Alkyl radicals, even in compound radicals such as alkoxy, haloalkyl, etc., are, 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 radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, wherein at least one double bond or triple bond is contained. Preferred are residues with a double bond or triple bond.

[0046] The term "alkenyl" includes in particular straight-chain or branched open-chain hydrocarbon radicals with more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals with one or more cumulated double bonds, such as allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl. Alkenyl means, for example, vinyl, which may optionally be substituted by further alkyl radicals, for example (but not limited to) (C 2 -C 6 )-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-Methyl-2-butenyl, 1-Methyl-3-butenyl, 2-Methyl-3-butenyl, 3-Methyl-3-butenyl, 1,1-Dimethyl-2-propenyl, 1,2-Dimethyl-1-propenyl, 1,2-Dimethyl-2-propenyl,1-Ethyl-1-propenyl, 1-Ethyl-2-propenyl, 1-Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5-Hexenyl, 1-Methyl-1-pentenyl, 2-Methyl-1-pentenyl, 3-Methyl-1-pentenyl, 4-Methyl-1-pentenyl, 1-Methyl-2-pentenyl, 2-Methyl-2-pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl, 1-Methyl-3-pentenyl, 2-Methyl-3-pentenyl, 3-Methyl-3-pentenyl, 4-Methyl-3-pentenyl, 1-Methyl-4-pentenyl, 2-Methyl-4-pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1,1-Dimethyl-2-butenyl, 1,1-Dimethyl-3-butenyl, 1,2-Dimethyl-1-butenyl, 1,2-Dimethyl-2-butenyl, 1,2-Dimethyl-3-butenyl, 1,3-Dimethyl-1-butenyl, 1,3-Dimethyl-2-butenyl, 1,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3-Dimethyl-1-butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3-Dimethyl-1-butenyl, 3,3-Dimethyl-2-butenyl, 1-Ethyl-1-butenyl, 1-Ethyl-2-butenyl, 1-Ethyl-3-butenyl, 2-Ethyl-1-butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, 1,1,2-Trimethyl-2-propenyl, 1-Ethyl-1-methyl-2-propenyl, 1-Ethyl-2-methyl-1-propenyl und 1-Ethyl-2-methyl-2-propenyl.,

[0047] The term "alkynyl" includes, in particular, straight-chain or branched open-chain hydrocarbon radicals with more than one triple bond or with one or more triple bonds and one or more double bonds, such as 1,3-butatrienyl or 3-penten-1-yn-1-yl. (C 2 -C 6 )-Alkynyl means, for example,Ethinyl, 1-Propinyl, 2-Propinyl, 1-Butinyl, 2-Butinyl, 3-Butinyl, 1-Methyl-2-propinyl, 1-Pentinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, 1-Methyl-2-butinyl, 1-Methyl-3-butinyl, 2-Methyl-3-butinyl, 3-Methyl-1-butinyl, 1,1-Dimethyl-2-propinyl, 1-Ethyl-2-propinyl, 1-Hexinyl, 2-Hexinyl, 3-Hexinyl, 4-Hexinyl, 5-Hexinyl, 1-Methyl-2-pentinyl, 1-Methyl-3-pentinyl, 1-Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl-4-pentinyl, 3-Methyl-1-pentinyl, 3-Methyl-4-pentinyl, 4-Methyl-1-pentinyl, 4-Methyl-2-pentinyl, 1,1-Di-methyl-2-butinyl, 1,1-Dimethyl-3-butinyl, 1,2-Dimethyl-3-butinyl, 2,2-Dimethyl-3-butinyl, 3,3-Dimethyl-1-butinyl, 1-Ethyl-2-butinyl, 1-Ethyl-3-butinyl, 2-Ethyl-3-butinyl und 1-Ethyl-1-methyl-2-propinyl.

[0048] 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, alkoxycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, or cycloalkylaminocarbonyl. In the case of optionally substituted cycloalkyl, cyclic systems with substituents are included, including substituents with a double bond on the cycloalkyl radical, e.g., an alkylidene group such as methylidene. In the case of optionally substituted cycloalkyl, polycyclic aliphatic systems are also included, such as bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-1-yl, bicyclo[1.1.1]pentan-1-yl, bicyclo[2.1.0]pentan-2-yl, bicyclo[2.1.0]pentan-5-yl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]hept-2-yl, bicyclo[2.2.2]octan-2-yl, bicyclo[3.2.1]octan-2-yl, bicyclo[3.2.2]nonan-2-yl, adamantan-1-yl, and adamantan-2-yl, but also systems such as 1,1'-bi(cyclopropyl)-1-yl and 1,1'-bi(cyclopropyl)-2-yl. The term "(C 3 -C 7 )-cycloalkyl" is a shorthand notation for cycloalkyl with three to seven carbon atoms, corresponding to the range of carbon atoms.

[0049] In the case of substituted cycloalkyl, spirocyclic aliphatic systems are also included, such as spiro[2.2]pent-1-yl, spiro[2.3]hex-1-yl, spiro[2.3]hex-4-yl, 3-spiro[2.3]hex-5-yl, spiro[3.3]hept-1-yl, spiro[3.3]hept-2-yl.

[0050] "Cycloalkenyl" means a carbocyclic, non-aromatic, partially unsaturated ring system with preferably 4-8 carbon atoms, e.g., 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl, or 1,4-cyclohexadienyl, which also includes substituents with a double bond on the cycloalkenyl radical, e.g., an alkylidene group such as methylidene. In the case of optionally substituted cycloalkenyl, the explanations for substituted cycloalkyl apply accordingly.

[0051] The term "alkylidene," also in the form (C 1 -C 10 )-alkylidene, refers to the residue of a straight-chain or branched open-chain hydrocarbon radical bonded by a double bond. Naturally, only positions on the parent structure where two hydrogen atoms can be replaced by a double bond are possible as bonding sites for alkylidene; examples include =CH 2 , =CH-CH 3 , =C(CH 3 )-CH 3 , =C(CH 3 )-C 2 H 5 , or =C(C 2 H 5 )-C 2 H 5 . Cycloalkylidene refers to a carbocyclic radical bonded by a double bond.

[0052] "Alkoxyalkyl" means an alkoxy radical bonded via an alkyl group and "alkoxyalkoxy" means an alkoxyalkyl radical bonded via an oxygen atom, e.g. (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy.

[0053] "Arylalkyl" means an aryl radical bonded via an alkyl group, "heteroarylalkyl" means a heteroaryl radical bonded via an alkyl group, and "heterocyclylalkyl" means a heterocyclyl radical bonded via an alkyl group.

[0054] "Cycloalkylalkyl" means a cycloalkyl radical bonded via an alkyl group, for example (but not limited to) cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropyleth-1-yl, 2-cyclopropyleth-1-yl, 1-cyclopropylprop-1-yl, 3-cyclopropylprop-1-yl.

[0055] According to the invention, "haloalkylthio" - alone or as part of a chemical group - stands for straight-chain or branched S-haloalkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as (C 1 -C 8 )-, (C 1 -C 6 )- or (C 1 -C 4 )-haloalkylthio, e.g. (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio, 3,3,3-prop-1-ylthio.

[0056] "Halocycloalkyl" means cycloalkyl or cycloalkenyl partially or fully substituted by identical or different halogen atoms, such as F, Cl and Br, or by haloalkyl, such as trifluoromethyl or difluoromethyl, e.g. 1-fluorocycloprop-1-yl, 2-fluorocycloprop-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocyclobut-1-yl, 1-trifluoromethylcycloprop-1-yl, 2-trifluoromethylcycloprop-1-yl, 1-chlorocycloprop-1-yl, 2-chlorocycloprop-1-yl, 2,2-dichlorocycloprop-1-yl, 3,3-difluorocyclobutyl.

[0057] If the compounds can form tautomers through hydrogen shift that are not structurally covered by the general formula (I), these tautomers are nevertheless encompassed by the definition of the compounds of the general formula (I) according to the invention, unless a specific tautomer is considered. For example, many carbonyl compounds can exist in both the keto and enol forms, with both forms being encompassed by the definition of the compound of the general formula (I).

[0058] The compounds of general formula (I) can exist as stereoisomers depending on the nature and linkage 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). If, for example, 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 obtained from the mixtures obtained during production using conventional separation methods. Chromatographic separation can be carried out both on an analytical scale to determine the enantiomeric excess or diastereomeric excess, and on a preparative scale to produce test samples for biological testing.Likewise, stereoisomers can be selectively prepared by employing stereoselective reactions using optically active starting materials and / or auxiliaries. The invention thus also relates to all stereoisomers encompassed by the general formula (I) but not indicated with their specific stereoform, as well as mixtures thereof.

[0059] If the compounds are obtained as solids, purification can also be carried out by recrystallization or digestion. If individual compounds (I) are not satisfactorily accessible by the routes described below, they can be prepared by derivatization of other compounds (I).

[0060] Suitable methods for the isolation, purification, and stereoisomer separation of compounds of general formula (I) include methods generally known to the person skilled in the art from analogous cases, e.g., physical processes such as crystallization, chromatography, especially column chromatography and HPLC (high-pressure liquid chromatography), distillation, optionally under reduced pressure, extraction, and other processes. Any remaining mixtures can generally be separated by chromatographic separation, e.g., on chiral solid phases. For preparative quantities or on an industrial scale, processes such as crystallization, e.g., of diastereomeric salts, which can be obtained from the diastereomer mixtures with optically active acids and, if acidic groups are present, with optically active bases, are suitable. Synthesis of {[1-(Phenyl)-5-(Heteroaryl)-1H-pyrazol-3-yl]oxy}acetic acid derivatives of the general formula (I)

[0061]

[0062] The {[1-(phenyl)-5-(heteroaryl)-1H-pyrazol-3-yl]oxy}acetic acid derivatives of the general formula (I) according to the invention can be prepared using known processes. The synthetic routes used and investigated start from commercially available or easily prepared substituted 3-heteroarylprop-2-acids or substituted heteroarycinnamic acids, from correspondingly substituted 3-heteroarylprop-2-acid esters or substituted heteroarycinnamic acid esters, and from commercially available chemicals such as substituted phenylhydrazines and substituted iodobenzenes. The groups R 1< , R 2< , R 3< , R 4< and m of the general formula (I) have the previously defined meanings in the following schemes, unless exemplary but non-limiting definitions are given.

[0063] The synthesis of the compounds of general formula (Ia) according to the invention is carried out by reacting the compound of general formula (II) with a compound of general formula (III) in the presence of a base, such as potassium carbonate. The reaction preferably takes place in the temperature range between 0 °C and 120 °C, in an appropriate solvent such as acetonitrile (see Scheme 1).

[0064] The synthesis of the compounds of general formula (II) is carried out via an amide coupling followed by cyclization of an acid of general formula (IV) with a phenylhydrazine hydrohalide of general formula (V) in the presence of a coupling reagent such as T3P, dicyclohexylcarbodiimide, N -(3-Dimethylaminopropyl)- N '-ethylcarbodiimide, N,N'-Carbonyldiimidazole, 2-chloro-1,3-dimethylimidazolium chloride, or 2-chloro-1-methylpyridinium iodide (see Chemistry of Peptide Synthesis, Ed. N. Leo Benoiton, Taylor & Francis, 2006, ISBN-10: 1-57444-454-9). Polymer-bound reagents such as polymer-bound dicyclohexylcarbodiimide are also suitable for this coupling reaction. The reaction preferably takes place in the temperature range between 0 °C and 80 °C, in an appropriate solvent such as dichloromethane, acetonitrile, N,N-dimethylformamide, or ethyl acetate, and in the presence of a base such as triethylamine. N,N -Diisopropylethylamine or 1,8-diazabicyclo[5.4.0]undec-7-cene (see Scheme 2). For the T3P coupling conditions, see Organic Process Research & Development 2009, 13, 900-906. Alternatively to the phenylhydrazine hydrohalide of general formula (V), an appropriately substituted phenylhydrazine (VI) can be used in the reaction.

[0065] The synthesis of compounds of general formula (IV) can be achieved by reacting the compound of general formula (VII) with propiolic acid (VIII) in the presence of an adequate amount of a transition metal catalyst, in particular palladium catalysts such as palladium(0)tetrakis(triphenylphosphine) or palladium diacetate or bis(triphenylphosphine)palladium(II) dichloride, or nickel catalysts such as nickel(II) acetylacetonate or bis(triphenylphosphine)nickel(II) chloride, preferably at elevated temperature in an organic solvent such as 1,2-dimethoxyethane or N,N-dimethylformamide (Scheme 3). The radical "M" represents, for example, magnesium, zinc, lithium, or sodium. In general, cross-coupling methods are suitable, as described in RD Larsen, Organometallics in Process Chemistry 2004 Springer Verlag, or in I. Tsuji, Palladium Reagents and Catalysts 2004 Wiley or in M. Belier, C.Bolm, Transition Metals for Organic Synthesis 2004 VCH-Wiley. Other suitable synthetic methods are described in Chem. Rev. 2006, 106, 2651; Platinum Metals Review, 2009, 53, 183; Platinum Metals Review 2008, 52, 172 and Acc. Chem. Res. 2008, 41, 1486.

[0066] The synthesis of the acid of general formula (IX) is carried out by saponification of the compound of general formula (Ia) by or analogously to methods known to those skilled in the art and is shown below in Scheme 4. The saponification can be carried out in the presence of a base or a Lewis acid. The base can be a hydroxide salt of an alkali metal (such as lithium, sodium, or potassium), and the saponification reaction preferably takes place in the temperature range between room temperature and 100°C. The Lewis acid can be boron tribromide, and the reaction can be carried out in a temperature range between -20°C and 100°C, preferably -5°C and 50°C.

[0067] The synthesis of the compounds of general formula (X) according to the invention is carried out by esterification of an acid of general formula (IX) with an alcohol of general formula (XI) in the presence of a coupling reagent such as T3P, dicyclohexylcarbodiimide, N- (3-Dimethylaminopropyl)- N '-ethylcarbodiimide, N,N '-Carbonyldiimidazole, 2-chloro-1,3-dimethylimidazolium chloride, or 2-chloro-1-methylpyridinium iodide (see Chemistry of Peptide Synthesis, Ed. N. Leo Benoiton, Taylor & Francis, 2006, ISBN-10: 1-57444-454-9). Polymer-bound reagents such as polymer-bound dicyclohexylcarbodiimide are also suitable for this coupling reaction. The reaction preferably takes place in the temperature range between 0 °C and 80 °C, in an appropriate solvent such as dichloromethane, acetonitrile, N,N-Dimethylformamide or ethyl acetate and in the presence of a base such as triethylamine, N,N -Diisopropylethylamine or 1,8-diazabicyclo[5.4.0]undec-7-cene (see Scheme 5). For the T3P coupling conditions, see Organic Process Research & Development 2009,13, 900-906.

[0068] The synthesis of the compounds of general formula (II) is alternatively carried out by oxidation of the compounds of general formula (XII) in the presence of an iron halide such as iron(III) chloride. The reaction preferably takes place in the temperature range between 0 °C and 120 °C, in an appropriate solvent such as 1,2-dichloroethane, acetonitrile, N,N- Dimethylformamide or ethyl acetate (Scheme 6).

[0069] Compounds of general formula (XII) can be prepared by an amide coupling of an acid of general formula (XIII) with an arylhydrazine of general formula (VI) in the presence of an amide coupling reagent, such as T3P, dicyclohexylcarbodiimide, N- (3-Dimethylaminopropyl)-N'-ethylcarbodiimide, I,I -Carbonyldiimidazole, 2-chloro-1,3-dimethylimidazolium chloride, or 2-chloro-1-methylpyridinium iodide (see Chemistry of Peptide Synthesis, Ed. N. Leo Benoiton, Taylor & Francis, 2006, ISBN-10: 1-57444-454-9), followed by cyclization. Polymer-bound reagents such as polymer-bound dicyclohexylcarbodiimide are also suitable for this coupling reaction. The reaction preferably takes place in the temperature range between 0 °C and 80 °C, in an appropriate solvent such as dichloromethane, acetonitrile, N,N-dimethylformamide, or ethyl acetate, and in the presence of a base such as triethylamine. N,N-Diisopropylethylamine or 1,8-diazabicyclo[5.4.0]undec-7-cene (see Scheme 7). For the T3P peptide coupling conditions, see Organic Process Research & Development 2009, 13, 900-906.

[0070] Selected detailed synthesis examples for the compounds of general formula (I) according to the invention are listed below. The example numbers given correspond to the numbering in Tables 1.1 to 1.77 below. The 1< H-NMR, 13< C-NMR and 19< F-NMR spectroscopic data given for the chemical examples described in the following sections (400 MHz for 1< H-NMR and 150 MHz for 13< C-NMR and 375 MHz for 19< F-NMR, solvent CDCl 3 , CD 3 OD or d 6 -DMSO, internal standard: tetramethylsilane δ = 0.00 ppm) were obtained using an instrument from Bruker, and the designated signals have the meanings listed below: br = broad(es); 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 mixtures of diastereomers, either the significant signals of both diastereomers or the characteristic signal of the major diastereomer are given. The abbreviations used for chemical groups have, for example, the following meanings: Me = CH 3 , Et = CH 2 CH 3 , t-Hex = C(CH 3 ) 2 CH(CH 3 ) 2 , t-Bu = C(CH 3 ) 3 , n-Bu = unbranched butyl, n-Pr = unbranched propyl, i-Pr = branched propyl, c-Pr = cyclopropyl, c-Hex = cyclohexyl. Synthesis examples: Synthesis example No.: I.50-2 Synthesis step 1: 3-(5-Fluoropyridin-3-yl)prop-2-ic acid

[0071]

[0072] 3-Fluoro-5-iodopyridine (5.00 g, 22.40 mmol, 1.0 equiv) was dissolved in THF (105 mL) under an argon atmosphere. Propiolic acid (1.58 g, 22.40 mmol, 1.0 equiv), bis(triphenylphosphine)palladium(II) dichloride (310 mg, 0.89 mmol, 0.04 equiv), copper(I) iodide (310 mg, 0.04 equiv), and diisopropylamine (7.9 g, 78.4 mmol, 3.5 equiv) were then added to the solution. The reaction mixture was stirred at room temperature for 2 h, then added dropwise to water (100 mL), and the mixture was acidified with 2 M hydrochloric acid (30 mL). The mixture was extracted twice with ethyl acetate (150 mL). The combined organic phases were dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was treated with diethyl ether (50 ml) and treated in an ultrasonic bath at room temperature for 10 min, then filtered. The filtrate was concentrated in vacuo. 3-(5-Fluoropyridin-3-yl)prop-2-oic acid was isolated as a solid (4.38 g, 75% of theory).1< H-NMR (400 MHz, DMSO-d 6< δ, ppm) 14.00 (bs, 1H), 8.57 (m, 1H), 8.32-8.28 (m, 1H), 7.52 (m, 1H). Synthesestufe 2: 1-(2-Fluorphenyl)-5-(5-fluorpyridin-3-yl)-1H-pyrazol-3-ol

[0073]

[0074] 3-(5-Fluoropyridin-3-yl)prop-2-oic acid (4.38 g, 26.50 mmol, 1.0 equiv) was dissolved in THF (20 mL). The solution was treated with (2-fluorophenyl)hydrazine hydrochloride (1:1) (4.90 g, 29.10 mmol, 1.1 equiv) and triethylamine (9.20 ml, 66.3 mmol). A 50% T3P solution in THF (31 ml, 53 mmol, 2.0 equiv) was then added dropwise, and the reaction mixture was stirred for 1 h at room temperature. The reaction mixture was extracted with water (50 ml) and twice with ethyl acetate (100 ml). The combined organic phases were dried over sodium sulfate, and the solvent was removed in vacuo. 1-(2-fluorophenyl)-5-(5-fluoropyridin-3-yl)-1H-pyrazol-3-ol was isolated as an oil (7.00 g, 85% of theory). The reaction product was used in the next synthesis step without further purification. Synthesis step 3: Ethyl {[1-(2-fluorophenyl)-5-(5-fluoropyridin-3-yl)-1H-pyrazol-3-yl]oxy}acetate (synthesis example I.50-2)

[0075]

[0076] 1-(2-Fluorophenyl)-5-(5-fluoropyridin-3-yl)-1H-pyrazol-3-ol (2.45 g, 8.96 mmol, 1.0 equiv) and potassium carbonate (3.78 g, 26.91 mmol, 3 equiv) were suspended in acetone (10 ml), and then ethyl bromoacetate (1.49 g, 8.96 mmol, 1.0 equiv) was added. The suspension was then heated to 80 °C for 2 h, the solid was filtered off, and the reaction mixture was concentrated in vacuo. The residue was extracted with DCM and water and then purified by column chromatography (gradient ethyl acetate / heptane). Ethyl {[1-(2-fluorophenyl)-5-(5-fluoropyridin-3-yl)-1H-pyrazol-3-yl]oxy}acetate was isolated as a colorless solid (14.20 g, 44% of theory). 1< H NMR (400 MHz, CDCl 3 δ, ppm) 1.23 (t, 3H), 4.31 (q, 2H), 6.21 (s, 1H), 5.1 (t, 1H), 7.2 (m, 2H), 7.4 (m, 1H), 7.5 (m, 1H), 8.4 (s, 1H), 8.5 (s, 1H).

[0077] In analogy to the preparation examples given above and recited at the appropriate point and taking into account the general information on the preparation of {[1-(phenyl)-5-(heteroaryl)-1H-pyrazol-3-yl]oxy}acetic acid derivatives, the following compounds are obtained:

[0078] Table I.1: Preferred compounds of formula (I.1) are compounds I.1-1 to I.1-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.1-1 to I.1-53 of Table 1.1 are thus defined by the meaning of the respective entries No. 1 to 53 for Q of Table 1. Table 1: No. Q 1 Q-2.1 2 Q-2.2 3 Q-2.3 4 Q-2.4 5 Q-2.5 6 Q-2.6 7 Q-2.7 8 Q-2.8 9 Q-2.9 10 Q-2.10 11 Q-2.11 12 Q-2.12 13 Q-2.13 14 Q-2.14 15 Q-2.15 16 Q-2.16 17 Q-2.17 18 Q-2.18 19 Q-2.19 20 Q-2.20 21 Q-2.21 22 Q-2.22 23 Q-2.23 24 Q-2.24 25 Q-2.25 26 Q-2.26 27 Q-2.27 28 Q-2.28 29 Q-2.29 30 Q-2.30 31 Q-2.31 32 Q-2.32 33 Q-2.33 34 Q-2.34 35 Q-2.35 36 Q-2.36 37 Q-2.37 38 Q-2.38 39 Q-2.39 40 Q-2.40 41 Q-2.41 42 Q-2.42 43 Q-2.43 44 Q-2.44 45 Q-2.45 46 Q-2.46 47 Q-2.47 48 Q-2.48 49 Q-2.49 50 Q-2.50 51 Q-2.51 52 Q-2.52 53 Q-2.53

[0079] Table I.2: Preferred compounds of formula (I.2) are compounds I.2-1 to I.2-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.2-1 to I.2-53 of Table I.2 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0080] Table I.3: Preferred compounds of formula (I.3) are compounds I.3-1 to I.3-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.3-1 to I.3-53 of Table I.3 are thus defined by the meaning of the respective entries No. 1 to 53 for Q of Table 1.

[0081] Table I.4: Preferred compounds of formula (I.4) are compounds I.4-1 to I.4-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.4-1 to I.4-53 of Table I.4 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0082] Table I.5: Preferred compounds of formula (I.5) are compounds I.5-1 to I.5-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.5-1 to I.5-53 of Table I.5 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0083] Table I.6: Preferred compounds of formula (I.6) are compounds I.6-1 to I.6-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.6-1 to I.6-53 of Table I.6 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0084] Table I.7: Preferred compounds of formula (I.7) are compounds I.7-1 to I.7-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.7-1 to I.7-53 of Table I.7 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0085] Table I.8: Preferred compounds of formula (I.8) are compounds I.8-1 to I.8-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.8-1 to I.8-53 of Table 1.8 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0086] Table I.9: Preferred compounds of formula (I.9) are compounds I.9-1 to I.9-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.9-1 to I.9-53 of Table I.9 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0087] Table I.10: Preferred compounds of formula (I.10) are compounds I.10-1 to I.10-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.10-1 to I.10-53 of Table I.10 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0088] Table 1.11: Preferred compounds of formula (I.11) are compounds I.11-1 to I.11-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.11-1 to I.11-53 of Table I.11 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0089] Table I.12: Preferred compounds of formula (I.12) are compounds 1.12-1 to 1.12-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.12-1 to 1.12-53 of Table 1.12 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0090] Table I.13: Preferred compounds of formula (I.13) are compounds I.13-1 to I.13-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.13-1 to I.13-53 of Table I.13 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0091] Table I.14: Preferred compounds of formula (I.14) are compounds I.14-1 to I.14-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.14-1 to I.14-53 of Table I.14 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0092] Table I.15: Preferred compounds of formula (I.15) are compounds I.15-1 to I.15-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.15-1 to I.15-53 of Table I.15 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0093] Table I.16: Preferred compounds of formula (I.16) are compounds I.16-1 to I.16-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.16-1 to I.16-53 of Table I.16 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0094] Table I.17: Preferred compounds of formula (I.17) are compounds I.17-1 to I.17-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.17-1 to I.17-53 of Table I.17 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0095] Table I.18: Preferred compounds of formula (I.18) are compounds I.18-1 to I.18-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.18-1 to I.18-53 of Table I.18 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0096] Table I.19: Preferred compounds of formula (I.19) are compounds I.19-1 to I.19-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.19-1 to I.19-53 of Table I.19 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0097] Table I.20: Preferred compounds of formula (I.20) are compounds I.20-1 to I.20-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.20-1 to I.20-53 of Table I.20 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0098] Table I.21: Preferred compounds of formula (I.21) are compounds I.21-1 to I.21-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.21-1 to I.21-53 of Table I.21 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0099] Table I.22: Preferred compounds of formula (I.22) are compounds I.22-1 to I.22-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.22-1 to I.22-53 of Table I.22 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0100] Table I.23: Preferred compounds of formula (I.23) are compounds I.23-1 to I.23-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.23-1 to I.23-53 of Table I.23 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0101] Table I.24: Preferred compounds of formula (I.24) are compounds I.24-1 to I.24-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.24-1 to I.24-53 of Table I.24 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0102] Table I.25: Preferred compounds of formula (I.25) are compounds I.25-1 to I.25-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.25-1 to I.25-53 of Table I.25 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0103] Table I.26: Preferred compounds of formula (I.26) are compounds I.26-1 to I.26-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.26-1 to I.26-53 of Table I.26 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0104] Table I.27: Preferred compounds of formula (I.27) are compounds I.27-1 to I.27-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.27-1 to I.27-53 of Table I.27 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0105] Table I.28: Preferred compounds of formula (I.28) are compounds I.28-1 to I.28-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.28-1 to I.28-53 of Table I.28 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0106] Table I.29: Preferred compounds of formula (I.29) are compounds I.29-1 to I.29-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.29-1 to I.29-53 of Table I.29 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0107] Table 1.30: Preferred compounds of formula (I.30) are compounds I.30-1 to I.30-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.30-1 to I.30-53 of Table I.30 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0108] Table I.31: Preferred compounds of formula (I.31) are compounds I.31-1 to I.31-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.31-1 to I.31-53 of Table I.31 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0109] Table I.32: Preferred compounds of formula (I.32) are compounds I.32-1 to I.32-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.32-1 to I.32-53 of Table I.32 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0110] Table I.33: Preferred compounds of formula (I.33) are compounds I.33-1 to I.33-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.33-1 to I.33-53 of Table I.33 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0111] Table I.34: Preferred compounds of formula (I.34) are compounds I.34-1 to I.34-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.34-1 to I.34-53 of Table I.34 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0112] Table I.35: Preferred compounds of formula (I.35) are compounds I.35-1 to I.35-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.35-1 to I.35-53 of Table I.35 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0113] Table I.36: Preferred compounds of formula (I.36) are compounds I.36-1 to I.36-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.36-1 to I.36-53 of Table I.36 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0114] Table I.37: Preferred compounds of formula (I.37) are compounds I.37-1 to I.37-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.37-1 to I.37-53 of Table I.37 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0115] Table I.38: Preferred compounds of formula (I.38) are compounds I.38-1 to I.38-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.38-1 to I.38-53 of Table I.38 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0116] Table I.39: Preferred compounds of formula (I.39) are compounds I.39-1 to I.39-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.39-1 to I.39-53 of Table I.39 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0117] Table I.40: Preferred compounds of formula (I.40) are compounds I.40-1 to I.40-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.40-1 to I.40-53 of Table I.40 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0118] Table I.41: Preferred compounds of formula (I.41) are compounds I.41-1 to I.41-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.41-1 to I.41-53 of Table I.41 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0119] Table I.42: Preferred compounds of formula (I.42) are compounds I.42-1 to I.42-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.42-1 to I.42-53 of Table I.42 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0120] Table I.43: Preferred compounds of formula (I.4) are compounds I.43-1 to I.43-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.43-1 to I.43-53 of Table I.43 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0121] Table I.44: Preferred compounds of formula (I.44) are compounds I.44-1 to I.44-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.44-1 to I.44-53 of Table I.44 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0122] Table I.45: Preferred compounds of formula (I.45) are compounds I.45-1 to I.45-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.45-1 to I.45-53 of Table I.45 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0123] Table I.46: Preferred compounds of formula (I.46) are compounds I.46-1 to I.46-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.46-1 to I.46-53 of Table I.46 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0124] Table I.47: Preferred compounds of formula (I.47) are compounds I.47-1 to I.47-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.47-1 to I.47-53 of Table I.47 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0125] Table I.48: Preferred compounds of formula (I.48) are compounds I.48-1 to I.48-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.48-1 to I.48-53 of Table I.48 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0126] Table I.49: Preferred compounds of formula (I.49) are compounds I.49-1 to I.49-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.49-1 to I.49-53 of Table I.49 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0127] Table I.50: Preferred compounds of formula (I.50) are compounds I.50-1 to I.50-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.50-1 to I.50-53 of Table I.50 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0128] Table I.51: Preferred compounds of formula (I.51) are compounds I.51-1 to I.51-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.51-1 to I.51-53 of Table I.51 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0129] Table I.52: Preferred compounds of formula (I.52) are compounds I.52-1 to I.52-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.52-1 to I.52-53 of Table I.52 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0130] Table I.53: Preferred compounds of formula (I.53) are compounds I.53-1 to I.53-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.53-1 to I.53-53 of Table I.53 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0131] Table I.54: Preferred compounds of formula (I.54) are compounds I.54-1 to I.54-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.54-1 to I.54-53 of Table I.54 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0132] Table I.55: Preferred compounds of formula (I.55) are compounds I.55-1 to I.55-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.55-1 to I.55-53 of Table I.55 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0133] Table I.56: Preferred compounds of formula (I.56) are compounds I.56-1 to I.56-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.56-1 to I.56-53 of Table I.56 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0134] Table I.57: Preferred compounds of formula (I.57) are compounds I.57-1 to I.57-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.57-1 to I.57-53 of Table I.57 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0135] Table I.58: Preferred compounds of formula (I.58) are compounds I.58-1 to I.58-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.58-1 to I.58-53 of Table I.58 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0136] Table I.59: Preferred compounds of formula (I.59) are compounds I.59-1 to I.59-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.59-1 to I.59-53 of Table I.59 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0137] Table I.60: Preferred compounds of formula (I.60) are compounds I.60-1 to I.60-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.60-1 to I.60-53 of Table I.60 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0138] Table I.61: Preferred compounds of formula (I.61) are compounds I.61-1 to I.61-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.61-1 to I.61-53 of Table I.61 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0139] Table I.62: Preferred compounds of formula (I.62) are compounds I.62-1 to I.62-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.62-1 to I.62-53 of Table I.62 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0140] Table I.63: Preferred compounds of formula (I.63) are compounds I.63-1 to I.63-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.63-1 to I.63-53 of Table I.63 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0141] Table I.64: Preferred compounds of formula (I.64) are compounds I.64-1 to I.64-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.64-1 to I.64-53 of Table I.64 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0142] Table I.65: Preferred compounds of formula (I.65) are compounds I.65-1 to I.65-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.65-1 to I.65-53 of Table I.65 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0143] Table I.66: Preferred compounds of formula (I.66) are compounds I.66-1 to I.66-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.66-1 to I.66-53 of Table I.66 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0144] Table I.67: Preferred compounds of formula (I.67) are compounds I.67-1 to I.67-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.67-1 to I.67-53 of Table I.67 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0145] Table I.68: Preferred compounds of formula (I.68) are compounds I.68-1 to I.68-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.68-1 to I.68-53 of Table I.68 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0146] Table I.69: Preferred compounds of formula (I.69) are compounds I.69-1 to I.69-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.69-1 to I.69-53 of Table I.69 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0147] Table I.70: Preferred compounds of formula (I.70) are compounds I.70-1 to I.70-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.70-1 to I.70-53 of Table I.70 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0148] Table I.71: Preferred compounds of formula (I.71) are compounds I.71-1 to I.71-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.71-1 to I.71-53 of Table I.71 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0149] Table I.72: Preferred compounds of formula (I.72) are compounds I.72-1 to I.72-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.72-1 to I.72-53 of Table I.72 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0150] Table I.73: Preferred compounds of formula (I.73) are compounds I.73-1 to I.73-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.73-1 to I.73-53 of Table I.73 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0151] Table I.74: Preferred compounds of formula (I.74) are compounds I.74-1 to I.74-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.74-1 to I.74-53 of Table I.74 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0152] Table I.75: Preferred compounds of formula (I.75) are compounds I.75-1 to I.75-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.75-1 to I.75-53 of Table I.75 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0153] Table I.76: Preferred compounds of formula (I.76) are compounds I.76-1 to I.76-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.76-1 to I.76-53 of Table I.76 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0154] Table I.77: Preferred compounds of formula (I.77) are compounds I.77-1 to I.77-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.77-1 to I.77-53 of Table I.77 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0155] Table I.78: Preferred compounds of formula (I.78) are compounds I.78-1 to I.78-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.78-1 to I.78-53 of Table I.78 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0156] Table I.79: Preferred compounds of formula (I.79) are compounds I.79-1 to I.79-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.79-1 to I.79-53 of Table I.79 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0157] Table I.80: Preferred compounds of formula (I.80) are compounds I.80-1 to I.80-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.80-1 to I.80-53 of Table I.80 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0158] Table I.81: Preferred compounds of formula (I.81) are compounds I.81-1 to I.81-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.81-1 to I.81-53 of Table I.81 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0159] Table I.82: Preferred compounds of formula (I.82) are compounds I.82-1 to I.82-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.82-1 to I.82-53 of Table I.82 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0160] Table I.83: Preferred compounds of formula (I.83) are compounds I.83-1 to I.83-53, wherein Q has the meanings given in the respective row of Table 1. The compounds I.83-1 to I.83-53 of Table I.83 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1. Spectroscopic data of selected table examples:

[0161] Selected detailed synthesis examples for the compounds of general formula (I) according to the invention are listed below. The 1< H-NMR, 13< C-NMR and 19< F-NMR spectroscopic data given for the chemical examples described in the following sections (400 MHz for 1< H-NMR and 150 MHz for 13< C-NMR and 375 MHz for 19< F-NMR, solvent CDCl 3 , CD 3 OD or d 6 -DMSO, internal standard: tetramethylsilane δ = 0.00 ppm) were obtained using a Bruker instrument, and the designated signals have the meanings listed below: br = broad(es); 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 mixtures of diastereomers, either the significant signals of both diastereomers or the characteristic signal of the major diastereomer are given. The abbreviations used for chemical groups have, for example, the following meanings: Me = CH 3 , Et = CH 2 CH 3 , t-Hex = C(CH 3 ) 2 CH(CH 3 ) 2 , t-Bu = C(CH 3 ) 3 , n-Bu = unbranched butyl, n-Pr = unbranched propyl, i-Pr = branched propyl, c-Pr = cyclopropyl, c-Hex = cyclohexyl.

[0162] The spectroscopic data of selected table examples listed below were evaluated using classical 1< H NMR interpretation or NMR peak list methods. Classical 1< H NMR interpretation Example No. I.77-49:

[0163] 1< H-NMR (400 MHz, CDCl 3 δ, ppm) 7.59 (m, 1H), 7.37 (t, 1H), 7.22 (m, 1H), 7.14 (dd, 1H), 6.97 (m, 1H), 6.77 (m, 1H), 4.92 (s, 2H), 4.20 (t, 2H), 1.67-1.63 (m, 2H), 1.32-1.26 (m, 4H), 0.87 (t, 3H). Beispiel No. I.71-49:

[0164] 1< H-NMR (400 MHz, CDCl 3 δ, ppm) 7.59 (m, 1H), 7.40 (t, 1H), 7.22 (dd, 1H), 7.14 (dd, 1H), 6.97 (dt, 1H), 6.77 (dt, 1H), 5.24 (q, 1H), 5.01 (s, 2H), 3.74 (s, 3H). Beispiel No. I.70-49:

[0165] 1< H-NMR (400 MHz, CDCl 3 δ, ppm) 7.60 (m, 1H), 7.40 (t, 1H), 7.21 (m, 1H), 7.14 (m, 1H), 6.96 (m, 1H), 6.77 (m, 1H), 5.05 (s, 2H), 4.75 (s, 2H), 3.77 (s, 3H). Beispiel No. I.72-49:

[0166] 1< H-NMR (400 MHz, CDCl 3 δ, ppm) 7.57 (m, 1H), 7.37 (t, 1H), 7.21 (m, 1H), 7.14 (dd, 1H), 6.96 (dt, 1H), 6.77 (dt, 1H), 4.93 (s, 2H), 3.99 (d, 2H), 1.95 (m, 1H), 0.90 (d, 6H). NMR-Peak-Listenverfahren

[0167] The 1H NMR data of selected examples are recorded in the form of 1H NMR peak lists. For each signal peak, the δ value in ppm is listed first, followed by the signal intensity in parentheses. The δ value - signal intensity pairs of different signal peaks are listed, separated by semicolons.

[0168] The peak list of an example therefore has the form: δ 1 (intensity 1 )< ; δ 2 (intensity 2 );........; δ i (intensity i )< ; ...... ; δ n (intensity n )

[0169] The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum can be shown.

[0170] To calibrate the chemical shift of 1H NMR spectra, we use tetramethylsilane and / or the solvent chemical shift, especially for spectra measured in DMSO. Therefore, the tetramethylsilane peak may or may not be present in NMR peak lists.

[0171] The lists of 1H NMR peaks are similar to the classical 1H NMR printouts and thus usually contain all peaks listed in a classical NMR interpretation.

[0172] In addition, like classical 1H-NMR printouts, they can show solvent signals, signals of stereoisomers of the target compounds, which are also the subject of the invention, and / or peaks of impurities.

[0173] When reporting compound signals in the delta region of solvents and / or water, our lists of 1H NMR peaks show the common solvent peaks, for example, peaks of DMSO in DMSO-D 6 and the peak of water, which usually have high intensity on average.

[0174] The peaks of stereoisomers of the target compounds and / or peaks of impurities usually have, on average, lower intensity than the peaks of the target compounds (for example, with a purity of >90%).

[0175] Such stereoisomers and / or impurities may be typical for the respective manufacturing process. Their peaks can thus help identify the reproduction of our manufacturing process based on "byproduct fingerprints."

[0176] An expert who calculates the peaks of the target compounds using known methods (MestreC, ACD simulation, but also empirically evaluated expected values) can isolate the peaks of the target compounds as needed, applying additional intensity filters if necessary. This isolation would be similar to the peak picking involved in classical 1H NMR interpretation.

[0177] Further details on 1H NMR peak lists can be found in the Research Disclosure Database Number 564025. I.15-2: 1< H-NMR(400.0 MHz, d 6 -DMSO): δ= 9.1400 (2.9); 8.6611 (6.7); 7.5917 (0.6); 7.5874 (0.6); 7.5272 (1.5); 7.5255 (1.6); 7.4632 (0.6); 7.4597 (0.6); 7.4150 (0.7); 7.3819 (0.6); 7.3784 (0.6); 7.3622 (0.7); 7.3591 (0.8); 7.3473 (0.6); 7.3440 (0.7); 7.3267 (0.6); 7.3211 (0.7); 7.3181 (0.6); 7.3003 (0.6); 7.2971 (0.6); 7.2891 (1.1); 7.2867 (1.1); 6.4864 (3.0); 5.9281 (0.6); 5.8395 (0.5); 5.1558 (0.6); 4.8406 (0.5); 4.4983 (2.8); 4.0385 (1.3); 4.0206 (2.4); 3.1836 (1.0); 3.1657 (1.1); 2.9442 (1.2); 2.9262 (3.4); 2.9083 (3.4); 2.8904 (1.3); 2.5274 (0.8); 2.5227 (1.2); 2.5140 (15.0); 2.5095 (32.0); 2.5049 (44.3); 2.5003 (31.1); 2.4958 (14.4); 1.9886 (5.8); 1.9013 (1.6); 1.3240 (0.7); 1.3060 (1.4); 1.2879 (0.6); 1.1925 (1.7); 1.1747 (3.4); 1.1570 (1.7); 1.1407 (7.9); 1.1226 (16.0); 1.1045 (7.6); −0.0002 (3.8) I.25-2: 1< H-NMR(400.0 MHz, CDCl3): δ= 8.0855 (1.2); 8.0812 (1.0); 8.0792 (1.2); 7.6130 (0.7); 7.6067 (0.7); 7.5942 (0.8); 7.5918 (0.8); 7.5879 (0.8); 7.5855 (0.8); 7.5730 (0.7); 7.5667 (0.7); 7.4657 (0.5); 7.4613 (0.6); 7.4465 (1.0); 7.4421 (1.1); 7.4275 (0.6); 7.4231 (0.7); 7.3506 (0.5); 7.3422 (0.5); 7.2619 (6.8); 7.2408 (0.6); 7.2392 (0.6); 7.2374 (0.6); 7.2362 (0.6); 7.2179 (1.0); 7.0817 (0.7); 7.0784 (0.7); 7.0609 (0.6); 7.0570 (1.1); 7.0533 (0.7); 7.0358 (0.6); 7.0325 (0.6); 6.8719 (0.9); 6.8705 (0.9); 6.8644 (0.9); 6.8630 (0.9); 6.8506 (0.9); 6.8492 (0.9); 6.8431 (0.8); 6.8417 (0.8); 6.1255 (6.2); 4.8781 (9.1); 3.8097 (16.0); 2.0053 (1.2); -0.0002 (7.0) I.26-4: 1< H-NMR(400.6 MHz, CDCl3): δ= 8.1389 (1.2); 8.1370 (1.7); 8.1349 (1.4); 8.1328 (1.4); 8.1307 (1.8); 8.1286 (1.3); 7.5656 (1.1); 7.5592 (1.1); 7.5468 (1.2); 7.5444 (1.2); 7.5405 (1.2); 7.5381 (1.2); 7.5256 (1.1); 7.5194 (1.3); 7.2610 (29.4); 7 / 1938 (2.4); 7.1881 (0.8); 7.1819 (2.6); 7.1766 (1.4); 7.1710 (3.3); 7.1649 (1.0); 7.1628 (0.6); 7.1591 (3.2); 7.0508 (3.4); 7.0449 (1.0); 7.0337 (1.0); 7.0306 (3.7); 7.0280 (2.8); 7.0248 (1.1); 7.0136 (0.9); 7.0078 (2.5); 6.8985 (1.3); 6.8970 (1.4); 6.8910 (1.4); 6.8894 (1.4); 6.8774 (1.3); 6.8757 (1.3); 6.8697 (1.3); 6.8681 (1.3); 6.0919 (10.2); 4.8579 (14.6); 4.3079 (1.8); 4.2901 (5.6); 4.2723 (5.7); 4.2545 (1.9); 1.5486 (7.1); 1.3227 (7.7); 1.3049 (16.0); 1.2871 (7.5); 0.0079 (1.1); -0.0002 (40.3); -0.0027 (2.0); -0.0052 (0.6); -0.0059 (0.6); -0.0085 (1.2) I.26-38: 1< H-NMR(400.2 MHz, d 6 -DMSO): δ= 8.1838 (3.4); 8.1778 (3.5); 7.8232 (1.2); 7.8169 (1.2); 7.8024 (2.0); 7.7965 (1.8); 7.7826 (1.3); 7.7762 (1.3); 7.6657 (1.0); 7.6506 (1.1); 7.6436 (2.0); 7.6286 (2.0); 7.6215 (1.2); 7.6065 (1.0); 7.4513 (1.0); 7.4443 (1.1); 7.4285 (1.3); 7.4247 (1.6); 7.4221 (1.6); 7.4182 (1.4); 7.4024 (1.1); 7.3955 (1.1); 7.2720 (0.8); 7.2687 (0.9); 7.2652 (0.9); 7.2624 (0.8); 7.2484 (1.6); 7.2291 (2.9); 7.2224 (2.8); 7.2076 (2.1); 7.2010 (2.0); 6.4670 (0.8); 6.4521 (11.1); 4.9750 (0.8); 4.8352 (14.5); 4.7697 (0.8); 4.1867 (2.2); 4.1689 (6.9); 4.1512 (7.0); 4.1335 (2.4); 4.1187 (0.5); 3.3202 (36.1); 3.2967 (0.5); 2.5091 (15.2); 2.5048 (30.2); 2.5003 (40.6); 2.4959 (30.1); 2.4916 (15.1); 1.2340 (0.4); 1.2058 (7.8); 1.1880 (16.0); 1.1703 (7.6); 1.1489 (0.5); 0.0066 (0.9); -0.0015 (18.8); -0.0096 (0.9) I.25-43: 1< H-NMR(400.6 MHz, CDCl3): δ= 8.1102 (1.1); 8.1040 (1.1); 7.6728 (0.6); 7.6665(0.6); 7.6541(0.7); 7.6517(0.7); 7.6478(0.7); 7.6454 (0.7); 7.6330 (0.6); 7.6267(0.6); 7.3829(0.6); 7.3615 (1.2); 7.3402 (0.7); 7.2616(10.5); 6.9859 (0.6); 6.9832 (1.7); 6.9647 (2.2); 6.9618 (2.1); 6.9435 (1.5); 6.9406 (0.5); 6.8925 (0.9); 6.8909 (0.9); 6.8850 (0.9); 6.8834 (0.9); 6.8713 (0.8); 6.8698 (0.8); 6.8638 (0.9); 6.8622 (0.8); 6.1577 (6.4); 4.8680 (8.6); 3.8020 (16.0); 3.7732 (0.6); 1.5555 (5.3); -0.0002 (13.8) I.26-2: 1< H-NMR(400.2 MHz, d 6 -DMSO): δ= 8.3755 (4.2); 8.3684 (4.2); 7.8429 (1.1); 7.8357 (1.1); 7.8211 (2.6); 7.8138 (2.5); 7.7993 (1.7); 7.7920 (1.6); 7.7333 (2.5); 7.7223 (2.7); 7.7113 (1.8); 7.7003 (1.7); 7.4886 (1.1); 7.4847 (1.3); 7.4691 (2.8); 7.4653 (3.3); 7.4562 (1.2); 7.4497 (2.7); 7.4459 (2.8); 7.4368 (1.7); 7.4305 (1.5); 7.4253 (1.0); 7.4169 (1.1); 7.4127 (0.8); 7.3103 (1.7); 7.3076 (1.9); 7.2913 (2.7); 7.2883 (3.1); 7.2801 (2.0); 7.2723 (1.5); 7.2692 (1.5); 7.2595 (1.7); 7.2539 (2.0); 7.2329 (1.4); 6.5840 (0.4); 6.5693 (10.8); 4.9853 (0.4); 4.8447 (15.4); 4.7760 (0.4); 4.1900 (2.3); 4.1723 (7.1); 4.1545 (7.3); 4.1367 (2.6); 3.3319 (14.4); 2.5069 (36.9); 2.5025 (48.5); 2.4982 (35.7); 1.2065 (7.8); 1.1888 (16.0); 1.1710 (7.7); 1.1486 (0.4); 0.0000 (4.5) I.26-17: 1< H-NMR(400.0 MHz, CDCl3): δ= 8.0535 (2.1); 8.0471 (2.1); 7.4836 (1.1); 7.4772 (1.1); 7.4648 (1.3); 7.4623 (1.4); 7.4584 (1.3); 7.4559 (1.3); 7.4435 (1.2); 7.4371 (1.2); 7.3253(0.6); 7.3217(0.6); 7.3064 (1.5); 7.3031 (1.5); 7.2883 (1.6); 7.2848 (1.6); 7.2613(45.0); 7.2418 (1.0); 7.2202(0.7); 7.2011 (1.4); 7.1969 (1.3); 7.1821 (0.9); 7.1788 (0.8); 7.1464 (2.2); 7.1431 (2.2); 7.1269 (1.2); 7.1235 (1.2); 6.8055 (1.5); 6.7991 (1.6); 6.7841 (1.5); 6.7777 (1.5); 6.1237 (10.2); 4.8511 (15.8); 4.7564 (2.6); 4.2830 (2.3); 4.2650 (6.4); 4.2471 (6.3); 4.2292 (2.0); 2.0270 (16.0); 1.3322 (1.2); 1.3143 (2.5); 1.3039 (7.8); 1.2965 (1.5); 1.2861 (15.7); 1.2682 (8.4); 0.8989 (0.7); 0.8819 (2.3); 0.8641 (0.9); 0.0080 (0.7); -0.0002 (25.3); -0.0085 (0.8) I.27-2: 1< H-NMR(400.0 MHz, d 6 -DMSO): δ= 8.1486 (1.2); 8.1422 (1.2); 7.8137 (0.5); 7.8073 (0.5); 7.7942 (0.7); 7.7924 (0.7); 7.7879 (0.7); 7.7860 (0.7); 7.7729 (0.6); 7.7666 (0.6); 7.5681 (0.8); 7.5637 (1.0); 7.5485 (0.5); 7.5441 (0.6); 7.3613 (0.5); 7.3583 (0.7); 7.3425 (0.8); 7.3389 (1.4); 7.3196 (0.6); 7.3156 (0.6); 7.3102 (0.7); 7.3069 (0.6); 7.2145 (0.8); 7.2087 (0.8); 7.1930 (0.8); 7.1874 (0.7); 7.1860 (0.7); 6.4261 (6.4); 4.7472 (6.6); 2.5234 (0.7); 2.5187 (1.0); 2.5100 (13.3); 2.5054 (28.6); 2.5008 (39.7); 2.4962 (27.6); 2.4916 (12.2); 2.0730 (16.0); 1.9880 (0.6); 1.9084 (1.6); 1.3557 (0.6); 0.0080 (0.9); -0.0002 (31.1); -0.0085 (0.9) 1.25-41: 1< H-NMR(400.0 MHz, CDCl3): δ= 8.0970 (1.3); 8.0907 (1.3); 7.6405 (0.7); 7.6342 (0.6); 7.6218 (0.8); 7.6193 (0.8); 7.6155 (0.8); 7.6130 (0.8); 7.6006 (0.7); 7.5943 (0.7); 7.2621 (7.0); 7.2426 (0.5); 7.2357 (0.5); 7.2285 (0.9); 7.2223 (0.5); 7.2076 (0.5); 7.0615 (0.5); 7.0539 (0.6); 7.0520 (0.6); 7.0437 (0.8); 7.0358 (0.6); 7.0321 (0.8); 7.0196 (0.7); 7.0091 (0.9); 6.9970 (0.9); 6.9092 (0.9); 6.9079 (0.9); 6.9017 (0.9); 6.9004 (0.9); 6.8880 (0.9); 6.8867 (0.9); 6.8805 (0.9); 6.8791 (0.8); 6.1286 (6.2); 4.8717 (9.0); 3.8181 (16.0); 2.0451 (1.1); 1.5586 (2.0); 1.2594 (0.9); 0.8818 (0.8); - 0.0002 (9.0) I.37-41: 1< H-NMR(400.0 MHz, CDCl3): δ= 8.1677 (1.6); 8.1546 (1.7); 7.2758 (0.6); 7.2599 (34.7); 7.2478 (0.6); 7.2411 (0.5); 7.2333 (0.5); 7.0952 (0.6); 7.0866 (0.8); 7.0786 (0.6); 7.0690 (1.0); 7.0568 (0.7); 7.0464 (0.9); 7.0345 (0.9); 6.9863(0.8); 6.9822 (1.2); 6.9786 (0.8); 6.9734 (0.8); 6.9694 (1.2); 6.9655 (0.7); 6.7395 (1.9); 6.2291 (6.2); 4.8705 (9.2); 3.8176 (16.0); 1.5397 (16.0); 0.0080 (1.4); -0.0002 (40.5); -0.0085 (1.2) I.32-38: 1< H-NMR(400.2 MHz, d 6 -DMSO): δ= 8.3869 (4.8); 8.3802 (4.7); 7.8591 (0.9); 7.8521 (0.9); 7.8373 (2.6); 7.8303 (2.4); 7.8157 (2.0); 7.8088 (1.9); 7.7931 (3.1); 7.7818 (3.3); 7.7712 (1.7); 7.7599 (1.4); 7.5526 (1.0); 7.5373 (1.2); 7.5306 (2.2); 7.5155 (2.2); 7.5088 (1.3); 7.4936 (1.1); 7.3928 (1.2); 7.3860 (1.2); 7.3652 (2.0); 7.3438 (1.2); 7.3371 (1.2); 7.2074 (1.1); 7.2035 (1.1); 7.1865 (2.0); 7.1651 (1.0); 6.6184 (0.8); 6.6045 (10.7); 4.9806 (0.9); 4.8401 (16.0); 4.7738 (1.0); 4.1855 (2.3); 4.1678 (7.2); 4.1500 (7.3); 4.1323 (2.5); 4.1189 (0.5); 3.3457 (59.8); 2.5018 (34.9); 1.2022 (7.7); 1.1844 (16.0); 1.1666 (8.3); 1.1481 (0.6); -0.0023 (2.2) I.26-2: 1< H-NMR(400.0 MHz, CDCl3): δ= 8.0839 (2.2); 8.0778 (2.2); 7.6117 (1.1); 7.6054 (1.1); 7.5929 (1.4); 7.5905 (1.4); 7.5866 (1.3); 7.5842 (1.3); 7.5717 (1.2); 7.5654 (1.1); 7.4650 (0.9); 7.4606 (1.0); 7.4457 (1.7); 7.4414 (1.8); 7.4267 (1.1); 7.4223 (1.2); 7.3791(0.5); 7.3748 (0.5); 7.3670(0.6); 7.3623 (0.7); 7.3603 (0.9); 7.3559 (0.8); 7.3480 (0.9); 7.3437 (0.9); 7.3417 (0.8); 7.3396 (0.9); 7.3352 (0.7); 7.3274 (0.8); 7.3230 (0.6); 7.2602 (21.0); 7.2369 (1.1); 7.2351 (1.2); 7.2158 (1.7); 7.1984 (0.8); 7.0794 (1.2); 7.0762 (1.1); 7.0586 (1.2); 7.0548 (1.9); 7.0511 (1.2); 7.0336 (1.0); 7.0303 (1.0); 6.8696 (1.6); 6.8621 (1.6); 6.8484 (1.6); 6.8470 (1.5); 6.8409 (1.5); 6.1251 (9.9); 4.8553 (16.0); 4.3023 (1.9); 4.2845 (6.0); 4.2666 (6.1); 4.2488 (2.0); 2.0442 (1.1); 1.5430 (4.6); 1.3131 (7.4); 1.2952 (15.3); 1.2774 (7.7); 1.2655 (0.8); 1.2590 (1.1); 0.8821 (1.2); 0.0080 (1.1); -0.0002 (27.7); -0.0085 (0.9) I.47-1: 1< H-NMR(400.6 MHz, d 6 -DMSO): δ= 8.6105 (3.1); 8.6060 (3.1); 8.4835 (2.2); 8.4810 (1.9); 8.4713 (2.2); 8.4687 (2.0); 7.4147 (1.7); 7.4066 (1.0); 7.4027 (3.1); 7.3988 (2.4); 7.3858 (5.0); 7.3813 (1.9); 7.3703 (1.4); 7.3665 (3.6); 7.3650 (2.4); 7.3597 (0.5); 7.3480 (1.0); 7.3445 (2.2); 7.3410 (1.3); 7.3325 (0.7); 7.3266 (2.1); 7.3082 (0.7); 7.2071 (3.0); 7.2034 (4.9); 7.1980 (1.0); 7.1900 (1.7); 7.1859 (3.1); 7.1842 (2.6); 7.1831 (2.4); 6.4246 (5.4); 6.4230 (5.1); 5.7571 (1.9); 4.8832 (12.0); 4.2072 (1.9); 4.1895 (6.1); 4.1717 (6.2); 4.1540 (2.0); 3.3202 (14.7); 2.5240 (1.1); 2.5193 (1.5); 2.5106 (20.6); 2.5060 (46.0); 2.5014 (65.0); 2.4969 (45.8); 2.4923 (20.7); 1.2234 (7.5); 1.2142 (0.6); 1.2057 (16.0); 1.1965 (0.8); 1.1880 (7.3); 0.0080 (1.4); -0.0002 (56.7); -0.0085 (1.8) I.50-41: 1< H-NMR(400.6 MHz, CDCl3): δ= 8.4354 (2.4); 8.4288 (2.4); 8.2962 (2.8); 7.2610 (21.6); 7.2512 (2.6); 7.2446 (2.6); 7.2371 (1.4); 7.2337 (1.7); 7.2294 (2.3); 7.2225 (2.1); 7.0878 (0.5); 7.0796 (0.7); 7.0744 (1.0); 7.0667 (1.1); 7.0567 (1.4); 7.0441 (1.5); 7.0390 (0.9); 7.0319 (1.3); 7.0213 (1.7); 7.0093 (1.6); 6.9984 (0.7); 6.9864 (0.5); 6.1767 (9.7); 4.8520 (16.0); 4.3111 (2.0); 4.2933 (6.0); 4.2755 (6.1); 4.2577 (2.0); 2.0454 (1.8); 1.5586 (1.0); 1.3226 (7.4); 1.3048 (14.8); 1.2870 (7.4); 1.2773 (1.0); 1.2596 (1.7); 1.2417 (0.6); 0.8986 (0.5); 0.8819 (1.5); 0.8643 (0.6); 0.0079 (1.6); - 0.0002 (31.4); -0.0084 (1.2) I.26-39: 1< H-NMR(400.6 MHz, CDCl3): δ= 8.0878 (1.9); 8.0858 (1.6); 8.0836 (1.6); 8.0815 (2.1); 7.6393 (1.1); 7.6330 (1.1); 7.6206 (1.2); 7.6181 (1.3); 7.6143 (1.2); 7.6118 (1.3); 7.5995 (1.1); 7.5932 (1.1); 7.2615(15.0); 7.2238 (0.6); 7.2210 (0.6); 7.2167 (0.5); 7.2110 (0.5); 7.2048 (1.8); 7 / 2006 (2.5); 7.1952 (0.6); 7.1932 (0.6); 7.1885 (1.6); 7.1860 (2.4); 7.1790 (0.7); 7.1726 (1.3); 7.1698 (1.5); 7.1595 (1.5); 7.1573 (1.3); 7.1511 (0.6); 7.1414 (0.6); 7.1380 (0.8); 6.9111 (1.4); 6.9096 (1.5); 6.9036 (1.5); 6.9021 (1.5); 6.8899 (1.3); 6.8884 (1.5); 6.8824 (1.4); 6.8808 (1.4); 6.1434 (10.6); 4.8486 (15.8); 4.3040 (1.9); 4.2862 (6.0); 4.2684 (6.1); 4.2506 (2.0); 2.0452 (0.6); 1.5525 (4.6); 1.3157 (7.8); 1.2979 (16.0); 1.2800 (7.6); 1.2595 (0.6); 0.8818 (0.5); 0.0079 (0.5); -0.0002 (22.1); -0.0085 (0.8) I.27-5: 1< H-NMR(400.6 MHz, d 6 -DMSO): δ= 12.9229 (1.6); 8.1123 (2.8); 8.1078 (2.3); 8.1060 (2.9); 7.7682 (1.4); 7.7618 (1.3); 7.7487 (1.7); 7.7468 (1.8); 7.7423 (1.7); 7.7404 (1.8); 7.7274 (1.5); 7.7210 (1.5); 7.6501 (2.1); 7.6452 (1.8); 7.6426 (1.8); 7.6324 (3.2); 7.6265 (3.0); 7.5858 (1.5); 7.5804 (2.2); 7.5688 (2.2); 7.5661 (2.6); 7.5622 (3.8); 7.5430 (1.1); 7.5377 (1.7); 7.5246 (3.7); 7.5194 (3.0); 7.5117 (3.2); 7.5068 (3.4); 7.5054 (3.4); 7.5001 (2.1); 7.4933 (3.1); 7.4885 (2.4); 7.4749 (1.0); 7.4702 (0.7); 7.1991 (1.9); 7.1980 (1.9); 7.1922 (2.0); 7.1909 (1.9); 7.1779 (1.8); 7.1765 (1.9); 7.1708 (1.9); 7.1695 (1.8); 6.4309 (15.4); 5.7575 (6.3); 4.7331 (16.0); 3.3271 (1.0); 2.5210 (0.7); 2.5122 (9.8); 2.5077 (21.9); 2.5031 (30.8); 2.4985 (21.6); 2.4940 (9.8); 0.0080 (0.8); -0.0002 (28.8); -0.0085 (0.8) I.26-5: 1< H-NMR(400.6 MHz, CDCl3): δ= 8.0606 (0.8); 8.0589 (1.1); 8.0566 (0.9); 8.0545 (0.9); 8.0526 (1.1); 8.0505 (0.7); 7.5757(0.7); 7.5694(0.7); 7.5570(0.7); 7.5545(0.8); 7.5507(0.8); 7.5481(0.8); 7.5358(0.7); 7.5294(0.7); 7.4245 (1.2); 7.4188 (1.2); 7.4153 (0.8); 7.4088 (1.1); 7.4062 (1.4); 7.4013 (2.5); 7.4001 (2.3); 7.3766 (0.7); 7.3639 (1.8); 7.3575 (1.0); 7.3534 (1.6); 7.3476 (1.4); 7.3464 (1.7); 7.3392 (0.8); 7.3354 (1.2); 7.3305 (0.9); 7.2651 (2.6); 6.8417 (0.9); 6.8401 (0.8); 6.8341 (0.9); 6.8326 (0.8); 6.8204 (0.8); 6.8188 (0.8); 6.8128 (0.8); 6.8113 (0.8); 6.1361 (6.0); 5.2995 (16.0); 4.8556 (8.5); 4.2910 (1.1); 4.2732 (3.4); 4.2553 (3.4); 4.2375 (1.1); 1.3058 (4.5); 1.2880 (9.3); 1.2701 (4.4); -0.0002 (3.5) I.27-2: 1< H-NMR(400.0 MHz, d 6 -DMSO): δ= 8.1486 (1.2); 8.1422 (1.2); 7.8137 (0.5); 7.8073 (0.5); 7.7942 (0.7); 7.7924 (0.7); 7.7879 (0.7); 7.7860 (0.7); 7.7729 (0.6); 7.7666 (0.6); 7.5681 (0.8); 7.5637 (1.0); 7.5485 (0.5); 7.5441 (0.6); 7.3613 (0.5); 7.3583 (0.7); 7.3425 (0.8); 7.3389 (1.4); 7.3196 (0.6); 7.3156 (0.6); 7.3102 (0.7); 7.3069 (0.6); 7.2145 (0.8); 7.2087 (0.8); 7.1930 (0.8); 7.1874 (0.7); 7.1860 (0.7); 6.4261 (6.4); 4.7472 (6.6); 2.5234 (0.7); 2.5187 (1.0); 2.5100 (13.3); 2.5054 (28.6); 2.5008 (39.7); 2.4962 (27.6); 2.4916 (12.2); 2.0730 (16.0); 1.9880 (0.6); 1.9084 (1.6); 1.3557 (0.6); 0.0080 (0.9); -0.0002 (31.1); -0.0085 (0.9) I.50-39: 1< H-NMR(400.6 MHz, CDCl3): δ= 8.4341 (2.4); 8.4273 (2.4); 8.2897 (1.6); 8.2862 (2.6); 7.2616 (13.6); 7.2535 (1.2); 7.2490 (1.3); 7.2465 (1.7); 7.2421 (1.7); 7.2371 (0.6); 7.2312 (1.7); 7.2267 (2.0); 7.2244 (2.0); 7.2201 (3.6); 7.2136 (0.7); 7.2061 (2.5); 7.1997 (1.2); 7.1947 (0.6); 7.1899 (1.3); 7.1875 (1.2); 7.1846 (1.2); 7.1764 (1.8); 7.1648 (0.5); 7.1587 (0.6); 7.1552 (0.8); 6.1912 (10.0); 4.8516 (16.0); 4.3054 (1.9); 4.2876 (6.0); 4.2697 (6.1); 4.2519 (2.0); 1.5668 (2.2); 1.3163 (7.3); 1.2985 (14.8); 1.2807 (7.2); 0.0080 (0.6); -0.0002 (20.0); -0.0085 (0.6) I.26-7: 1< H-NMR(400.6 MHz, CDCl3): δ= 8.1546 (1.9); 8.1526 (1.6); 8.1504 (1.6); 8.1483 (2.0); 7.5822 (1.1); 7.5758 (1.1); 7.5635 (1.2); 7.5610 (1.3); 7.5572 (1.3); 7.5547 (1.3); 7.5423 (1.2); 7.5360 (1.2); 7.3166 (0.5); 7.3094 (5.4); 7.3040 (1.9); 7.2926 (2.0); 7.2871 (7.2); 7.2800 (0.8); 7.2614 (15.4); 7.1492 (0.8); 7.1420 (7.1); 7.1366 (2.0); 7.1252 (1.8); 7.1199 (5.4); 7.1126 (0.5); 6.9167 (1.4); 6.9152 (1.5); 6.9091 (1.5); 6.9076 (1.5); 6.8955 (1.4); 6.8940 (1.4); 6.8879 (1.4); 6.8864 (1.3); 6.0966 (10.1); 5.3001 (0.9); 4.8573 (15.5); 4.3085 (1.9); 4.2906 (6.0); 4.2728 (6.0); 4.2550 (2.0); 1.5509 (3.7); 1.3241 (7.7); 1.3063 (16.0); 1.2885 (7.6); 0.0697 (0.7); 0.0080 (0.7); -0.0002 (24.7); -0.0085 (0.7) I.50-43: 1< H-NMR(400.6 MHz, CDCl3): δ= 8.4137 (2.7); 8.4068 (2.7); 8.3193 (1.6); 8.3155 (2.7); 8.3117 (1.5); 7.3974 (1.0); 7.3911 (0.8); 7.3822 (0.5); 7.3760 (1.9); 7.3699 (0.6); 7.3606 (0.8); 7.3547 (1.1); 7.3395 (0.5); 7.2774 (1.1); 7.2729 (1.2); 7.2705 (1.3); 7.2660 (1.3); 7.2614 (19.2); 7.2552 (1.2); 7.2507 (1.3); 7.2483 (1.2); 7.2438 (1.1); 7.0031 (0.7); 7.0013 (0.9); 6.9985 (2.8); 6.9801 (3.6); 6.9771 (3.4); 6.9588 (2.5); 6.9558 (0.8); 6.9540 (0.6); 6.2073 (10.8); 4.8487 (16.0); 4.2951 (1.9); 4.2773 (6.0); 4.2595 (6.0); 4.2417 (2.0); 1.5842 (0.9); 1.3020 (7.7); 1.2842 (16.0); 1.2664 (7.7); 0.0080 (0.8); -0.0002 (28.0); -0.0085 (0.8) I.26-20: 1< H-NMR(400.6 MHz, CDCl3): δ= 8.0933 (1.2); 8.0913 (1.0); 8.0893 (1.0); 8.0870 (1.2); 8.0851 (0.9); 7.5662 (0.7); 7.5599 (0.7); 7.5473 (0.8); 7.5450 (0.9); 7.5410 (0.8); 7.5387 (0.9); 7.5261 (0.8); 7.5198 (0.8); 7.4111 (1.1); 7.4068 (1.3); 7.3917 (1.3); 7.3875 (1.4); 7.3613 (0.7); 7.3570 (0.7); 7.3425 (1.0); 7.3406 (1.0); 7.3382 (0.9); 7.3363 (0.9); 7.3217 (0.9); 7.3174 (0.8); 7.2612 (12.1); 7.0448 (0.9); 7.0418 (1.0); 7.0257 (1.4); 7.0226 (1.5); 7.0067 (0.8); 7.0036 (0.8); 6.8537 (1.2); 6.8508 (1.2); 6.8329 (1.1); 6.8300 (1.1); 6.8134 (0.9); 6.8119 (1.0); 6.8059 (0.9); 6.8044 (0.9); 6.7923 (0.8); 6.7907 (0.9); 6.7847 (0.8); 6.7832 (0.9); 6.0891 (6.5); 5.2998 (0.7); 4.8615 (8.8); 4.2969 (1.2); 4.2791 (3.8); 4.2613 (3.8); 4.2435 (1.2); 3.4897 (16.0); 1.5579 (0.7); 1.3115 (4.9); 1.2938 (10.2); 1.2759 (4.9); 0.0695 (0.7); 0.0080 (0.5); -0.0002 (18.8); -0.0084 (0.6) I.50-17: 1< H-NMR(400.6 MHz, CDCl3): δ= 8.3443 (2.6); 8.3376 (2.5); 8.2719 (2.7); 7.3455 (0.7); 7.3421 (0.7); 7.3267 (1.6); 7.3235 (1.7); 7.3086 (1.7); 7.3052 (1.7); 7.2771 (2.3); 7.2619 (9.0); 7.2362 (0.9); 7.2320 (0.7); 7.2168 (1.6); 7.2138 (1.4); 7.1988 (1.0); 7.1947 (0.9); 7.1563 (2.2); 7.1533 (2.2); 7.1369 (1.3); 7.1339 (1.2); 7.0708 (1.2); 7.0662 (1.3); 7.0642 (1.3); 7.0595 (1.1); 7.0475 (1.2); 7.0430 (1.2); 7.0409 (1.3); 7.0363 (1.1); 6.1817 (9.3); 4.8540 (14.9); 4.2837 (2.0); 4.2658 (5.9); 4.2480 (6.0); 4.2302 (2.0); 2.0370 (16.0); 1.3043 (7.1); 1.2864 (14.1); 1.2686 (7.5); 0.8983 (0.6); 0.8816 (1.7); 0.8639 (0.7); -0.0002 (10.7) I.26-17: 1< H-NMR(400.0 MHz, CDCl3): δ= 8.0535 (2.1); 8.0471 (2.1); 7.4836 (1.1); 7.4772 (1.1); 7.4648 (1.3); 7.4623 (1.4); 7.4584 (1.3); 7.4559 (1.3); 7.4435 (1.2); 7.4371 (1.2); 7.3253 (0.6); 7.3217(0.6); 7.3064 (1.5); 7.3031 (1.5); 7.2883 (1.6); 7.2848 (1.6); 7.2613(45.0); 7.2418 (1.0); 7.2202(0.7); 7.2011 (1.4); 7.1969 (1.3); 7.1821 (0.9); 7.1788 (0.8); 7.1464 (2.2); 7.1431 (2.2); 7.1269 (1.2); 7.1235 (1.2); 6.8055 (1.5); 6.7991 (1.6); 6.7841 (1.5); 6.7777 (1.5); 6.1237 (10.2); 4.8511 (15.8); 4.7564 (2.6); 4.2830 (2.3); 4.2650 (6.4); 4.2471 (6.3); 4.2292 (2.0); 2.0270 (16.0); 1.3322 (1.2); 1.3143 (2.5); 1.3039 (7.8); 1.2965 (1.5); 1.2861 (15.7); 1.2682 (8.4); 0.8989 (0.7); 0.8819 (2.3); 0.8641 (0.9); 0.0080 (0.7); -0.0002 (25.3); -0.0085 (0.8) I.27-50: 1< H-NMR(400.6 MHz, d 6 -DMSO): δ= 12.9575 (0.6); 8.1243 (2.4); 8.1225 (2.0); 8.1200 (2.0); 8.1179 (2.6); 7.7840 (1.2); 7.7775 (1.2); 7.7647 (1.4); 7.7626 (1.6); 7.7583 (1.4); 7.7562 (1.6); 7.7434 (1.3); 7.7369 (1.3); 7.6396 (1.0); 7.6248 (1.0); 7.6188 (2.4); 7.6041 (2.5); 7.5979 (1.7); 7.5833 (1.7); 7.5263 (1.7); 7.5230 (3.3); 7.5200 (2.0); 7.5057 (1.3); 7.5024 (2.2); 7.4994 (1.2); 7.4773 (1.6); 7.4740 (1.4); 7.4562 (1.5); 7.4540 (2.1); 7.4508 (1.8); 7.4332 (1.3); 7.4298 (1.2); 7.2412 (1.7); 7.2397 (1.9); 7.2341 (1.8); 7.2326 (1.8); 7.2198 (1.7); 7.2183 (1.8); 7.2127 (1.7); 7.2112 (1.7); 6.5033 (16.0); 5.7576 (6.6); 4.7336 (14.6); 3.3256 (0.7); 2.5256 (0.6); 2.5209 (0.7); 2.5121 (12.4); 2.5075 (27.6); 2.5029 (39.3); 2.4983 (27.5); 2.4937 (12.4); 0.0080 (1.5); -0.0002 (59.5); -0.0085 (1.8)

[0178] The invention also relates to the method for protecting crops or useful plants from phytotoxic effects of agrochemicals, such as pesticides, or in particular herbicides, which cause damage to the crops or useful plants, characterized in that compounds of the general formula (I) or salts thereof are used as safeners, preferably an effective amount of the compounds of the general formula (I) or salts thereof is applied to the plants, parts of the plants or their seeds (or seed).

[0179] The compounds of general formula (I) (= safeners) as mentioned above are suitable for use together with active ingredients (pesticides) for the selective control of pests in a range of plant crops, for example in economically important crops such as cereals (wheat, barley, triticale, rye, rice, maize, millet), sugar beet, sugar cane, rapeseed, cotton, sunflower, peas, beans, and soybeans. The herbicide-safener combinations with safeners of general formula (I) are also suitable for controlling harmful plants in beds and areas of crops and ornamental plants, such as lawns with crop or ornamental turf, especially ryegrass, meadow grass, or Bermuda grass.

[0180] Among the crops and plants in which the herbicide-safener combinations with the aforementioned compounds of general formula (I) can be used, mutant crops or transgenic crops that are fully or partially tolerant to certain pesticides are also of interest, e.g., maize crops that are resistant to glufosinate or glyphosate, or soybean crops that are resistant to plant-damaging imidazolinones. However, the particular advantage of the novel safeners of general formula (I) is their effective action in crops that are normally not sufficiently tolerant to the pesticides to be applied.

[0181] The compounds of general formula (I) can be applied simultaneously or in any sequence with the active ingredients for joint use with pesticides. They are then able to reduce or completely eliminate harmful side effects of these active ingredients in crops without impairing or significantly reducing the effectiveness of these active ingredients against unwanted pests. Damage caused by the use of multiple pesticides, e.g., multiple herbicides or herbicides in combination with insecticides or fungicides, can also be significantly reduced or completely eliminated. This can significantly expand the range of applications of conventional pesticides.In the event that the compositions according to the invention contain pesticides, these compositions are applied after appropriate dilution either directly to the cultivation area, to the already germinated harmful and / or beneficial plants or to the already emerged harmful and / or beneficial plants. In the event that the compositions according to the invention do not contain a pesticide, these compositions can be used in the so-called tank mix method - i.e. immediately before application to the area to be treated, the user mixes and dilutes the separately formulated products (= crop protection agent and pesticide) - or before or after the application of a pesticide, or for seed pretreatment, i.e. for example for dressing the crop seed. Preference is given to applying the safener at the same time as the pesticide, in particular if the safener is applied to the plants after the herbicide.The beneficial effects of the compounds of general formula (I) are observed when they are used together with the pesticides pre-emergence or post-emergence, for example when applied simultaneously as a tank mix or as a co-formulation or when applied separately in parallel or sequentially (split application). It is also possible to repeat the application several times. Sometimes it may be useful to combine a pre-emergence application with a post-emergence application. In most cases, post-emergence application to the crop or plant with simultaneous or subsequent application of the pesticide is suitable. The use of the compounds (I) according to the invention is also possible in the seed dressing, the (dip) treatment of seedlings (e.g. rice) or the treatment of other propagating material (e.g. potato tubers).

[0182] When compounds of general formula (I) are used in combination with herbicides, not only the safener effect but also enhanced herbicidal activity against weeds is often observed. Furthermore, the growth of crops and cultivated plants is improved in many cases, and crop yields can be increased.

[0183] The compositions according to the invention may contain one or more pesticides. Examples of suitable pesticides are herbicides, insecticides, fungicides, acaricides, and nematicides, each of which, if used alone, would cause phytotoxic damage to the crops or where damage would be likely. Of particular interest are corresponding pesticidal active ingredients from the groups of herbicides, insecticides, acaricides, nematicides, and fungicides, especially herbicides.

[0184] The weight ratio of safener (of general formula (I)) to pesticide can be varied within wide limits and is generally in the range of 1:100 to 100:1, preferably 1:20 to 20:1, in particular 1:10 to 10:1. The optimal weight ratio of safener to pesticide generally depends on the specific safener and pesticide used, as well as on the type of crop or plant to be protected. The required application rate of safener can be varied within wide limits depending on the pesticide used and the type of crop to be protected and is generally in the range of 0.001 to 10 kg, preferably 0.01 to 1 kg, in particular 0.01 to 0.2 kg of safener per hectare. The quantities and weight ratios necessary for successful treatment can be determined by simple preliminary tests.

[0185] In the case of seed dressing, for example, 0.005 to 20 g of safener (of the general formula (I)) per kilogram of seed, preferably 0.01 to 10 g of safener per kilogram of seed, in particular 0.05 to 5 g of safener per kilogram of seed are used.

[0186] When solutions of safeners (of general formula (I)) are used in seed treatment and the seeds or seedlings are wetted with the solutions, the appropriate concentration is generally in the range of 1 to 10,000 ppm, preferably 100 to 1,000 ppm by weight. The quantities and weight ratios necessary for successful treatment can be determined by simple preliminary tests.

[0187] The compounds of general formula (I) can be formulated in the usual way, either separately or together with the pesticides. Therefore, the subject matter also includes agents for protecting crops or plants.

[0188] The preferred application is the combined use of safener and pesticide, in particular the use of safener and herbicide as a ready-to-use formulation or the use in the tank mix process.

[0189] Likewise preferred is the use of a compound of general formula (I) in seed treatment with subsequent application of pesticides, preferably herbicides, after sowing by pre- or post-emergence method.

[0190] 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 pesticidally active substances, such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers, and / or growth regulators, e.g., as a ready-to-use formulation or as tank mixes. The combination formulations can be prepared based on the above-mentioned formulations, taking into account the physical properties and stability of the active ingredients to be combined.

[0191] As combination partners for the compounds according to the invention in mixture formulations or in the tank mix, known active ingredients which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate 3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or protoporphyrinogen oxidase can be used, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006 and literature cited therein.The following are examples of known herbicides or plant growth regulators that can be combined with the compounds of the invention. These active ingredients are designated 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. This always includes all application forms, such as acids, salts, esters, as well as all isomeric forms such as stereoisomers and optical isomers, even if these are not explicitly mentioned. Examples of such herbicidal mixture partners are:

[0192] Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydimsodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlorpotassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate und -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenacsodium, chlorfenprop,chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, - dimethylammonium, -diolamin, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, - potassium, -triisopropanolammonium und -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium und -sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl,diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyrsodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9600, F-5231, i.e. N-[2-Chlor-4-fluor-5-[4-(3-fluorpropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]-ethansulfonamid, F-7967, i.e. 3-[7-Chlor-5-fluor-2-(trifluormethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluormethyl)pyrimidin-2,4(1H,3H)-dion, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet,flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, - dimethylammonium und -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, - potassium, -sodium und -trimesium, H-9201, i.e. O-(2,4-Dimethyl-6-nitrophenyl)-O-ethyl-isopropylphosphoramidothioat, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuronmethyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e. 1-(Dimethoxyphosphoryl)-ethyl-(2,4-dichlorphenoxy)acetat,imazamethabenz, Imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquinammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium und sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e. 3-({[5-(Difluormethyl)-1-methyl-3-(trifluormethyl)-1H-pyrazol-4-yl] methyl} sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazol, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, - isopropylammonium, -potassium und -sodium, MCPB, MCPB-methyl, -ethyl und -sodium, mecoprop, mecoprop-sodium, und -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl und -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron,methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e. N-[3-chlor-4-(1-methylethyl)-phenyl]-2-methylpentanamid, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-Dichlorbenzoyl)-1-methyl-5-benzyloxypyrazol, neburon, nicosulfuron, nonanoic acid (Pelargonsäure), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium,propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuronethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYP-249, i.e. 1-Ethoxy-3-methyl-1-oxobut-3-en-2-yl-5-[2-chlor-4-(trifluormethyl)phenoxy]-2-nitrobenzoat, SYP-300, i.e. 1-[7-Fluor-3-oxo-4-(prop-2-in-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidin-4,5-dion, 2,3,6-TBA, TCA (Trifluoressigsäure), TCA-sodium, tebuthiuron, tefuryltrione,tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazonemethyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazine, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, ie 3,4-Dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, as well as the following compounds: , Examples of plant growth regulators as possible mixing partners are:

[0193] Acibenzolar, acibenzolar-S-methyl, 5-Aminolävulinsäure, ancymidol, 6-benzylaminopurine, Brassinolid, Catechin, chlormequat chloride, cloprop, cyclanilide, 3-(Cycloprop-1-enyl)propionsäure, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothaldipotassium, -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-(1-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.

[0194] When used as active ingredient formulations or co-formulations, these may contain the usual adhesives, wetting agents, dispersing agents, emulsifying agents, penetration agents, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents which influence the pH and viscosity.

[0195] The compounds of general formula (I) and their combinations with one or more of the above-mentioned pesticides can be formulated in various ways depending on the given chemical-physical and biological parameters. Suitable formulation types include, for example: Emulsifiable concentrates produced by dissolving the active ingredients in an organic solvent, e.g., butanol, cyclohexanone, dimethylformamide, xylene, or higher-boiling hydrocarbons or mixtures of organic solvents with the addition of one or more ionic and / or non-ionic surfactants (emulsifiers). Suitable emulsifiers include, for example, calcium alkylarylsulfonate salts, fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, and polyoxyethylene sorbitan fatty acid esters; dusts obtained by grinding the active ingredients with finely divided solid inorganic or organic substances, e.g., talc, natural clays such as kaolin, bentonite, and pyrophyllite, diatomaceous earth, or flours.Water- or oil-based suspension concentrates, which can be produced, for example, by wet grinding using bead mills; water-soluble powders; water-soluble concentrates; granules, such as water-soluble granules, water-dispersible granules and granules for broadcast and soil application; wettable powders which, in addition to the active ingredient, also contain diluents or inert substances and surfactants; capsule suspensions and microcapsules; ultra-low-volume formulations.

[0196] The above-mentioned formulation types are known to the person skilled in the art and are described, for example, in: K. Martens, "Spray Drying Handbook," 3rd Ed., G. Goodwin Ltd., London, 1979; W. van Valkenburg, "Pesticide Formulations," Marcel Dekker, NY, 1973; Winacker-Küchler, "Chemische Technologie," Volume 7, C. Hanser Verlag, Munich, 4th Edition, 1986; "Perry's Chemical Engineer's Handbook," 5th Ed., McGraw-Hill, NY, 1973, pages 8-57.

[0197] The necessary formulation aids such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in: McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; C. Marsden, "Solvents Guide", 2nd Ed., Interscience, NY 1963; H. von Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, NY; Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte", Wiss. Verlagsgesellschaft, Stuttgart 1976; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell NJ; Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th edition 1986.

[0198] In addition to the formulation aids mentioned above, the crop protection agents may optionally contain conventional adhesives, wetting agents, dispersing agents, penetrating agents, emulsifying agents, preservatives, antifreeze agents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents which influence the pH or viscosity.

[0199] Depending on the type of formulation, the crop protection agents generally contain 0.1 to 99% by weight, in particular 0.2 to 95% by weight, of one or more safeners of the general formula (I) or a combination of safener and pesticide. They also contain 1 to 99.9% by weight, in particular 4 to 99.5% by weight, of one or more solid or liquid additives and 0 to 25% by weight, in particular 0.1 to 25% by weight of a surfactant. In emulsifiable concentrates, the active ingredient concentration, i.e. the concentration of safener and / or pesticide, is generally 1 to 90% by weight, in particular 5 to 80% by weight. Dusts usually contain 1 to 30% by weight, preferably 5 to 20% by weight of active ingredient. In wettable powders, the active ingredient concentration is generally 10 to 90% by weight. In the case of water-dispersible granules, the active ingredient content is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.

[0200] For application, the formulations available in commercial form are diluted, if necessary, in the usual way, e.g., with water in the case of wettable powders, emulsifiable concentrates, dispersions, and water-dispersible granules. Dust-like preparations, granules, and sprayable solutions are not normally diluted with other inert substances prior to application. The required application rate of the safeners of general formula (I) varies depending on external conditions such as temperature, humidity, the type of herbicide used, and others.

[0201] In the following examples, which illustrate but do not limit the invention, the quantities given are by weight unless otherwise specified. EXAMPLES 1. Formulation example 1.1 Dust

[0202] A dust is obtained by mixing 10 parts by weight of a compound of general formula (I) (safener) or an active ingredient mixture of a pesticide (e.g. a herbicide) and a safener of general formula (I) and 90 parts by weight of talc as an inert substance and comminuting in a hammer mill. 1.2 Water-dispersible powder

[0203] A wettable powder which is easily dispersible in water is obtained by mixing 25 parts by weight of a compound of the general formula (I) or of an active ingredient mixture of a pesticide (e.g. a herbicide) and a safener of the general formula (I), 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurine as a wetting and dispersing agent and grinding in a pin mill. 1.3 Water-dispersible concentrate

[0204] A dispersion concentrate which is easily dispersible in water is obtained by mixing 20 parts by weight of a compound of the general formula (I) or of an active ingredient mixture of a pesticide (e.g. a herbicide) and a safener of the formula (I) with 6 parts by weight of alkylphenol polyglycol ether (®< Triton X 207), 3 parts by weight of isotridecanol polyglycol ether and 71 parts by weight of paraffinic mineral oil and grinding in a ball mill to a fineness of less than 5 microns. 1.4 Emulsifiable concentrate

[0205] An emulsifiable concentrate is obtained from 15 parts by weight of a compound of general formula (I) or an active ingredient mixture of a pesticide (e.g. herbicide) and a safener of general formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier. 1.5 Water-dispersible granules

[0206] A water-dispersible granulate is obtained by 75 parts by weight a safener of general formula (I) or a mixture of a pesticide and a safener of general formula (I), 10 " calcium ligninsulfonate, 5 " Sodium lauryl sulfate, 3 " Polyvinyl alcohol and 7 " Polyvinyl alcohol and 7 " kaolin mixed, ground in a pin mill and granulated in a fluidized bed by spraying water as a granulating liquid.

[0207] A water-dispersible granulate is also obtained by 25 parts by weight a safener of general formula (I) or a mixture of a pesticide and a safener of general formula (I), 5 " 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, 2 " oleoylmethyltaurine sodium, 17 " Calcium carbonate, 50 " Water and 1 Part by weight Polyvinyl alcohol homogenized on a colloid mill, crushed, then ground in a bead mill and the resulting suspension is atomized and dried in a spray tower using a single-component nozzle. 2. Biological examples 2.1 Relative effect of selected compounds according to the invention using the example of the pest reduction of mesosulfuron-methyl on spring wheat (TRZAS)

[0208] The seeds of the crops to be treated were sown in plastic pots (diameter ~4 cm) in sandy loam soil, covered with soil, and grown in a greenhouse under favorable conditions for germination and growth. The test plants were treated at the early leaf stage (BBCH10 - BBCH12). The compounds of the invention, formulated as wettable powders (WP), were sprayed onto the above-ground plant parts as an aqueous suspension at a water application rate corresponding to 800 l / ha, with the addition of a wetting agent (e.g., 0.2% Genapol-LRO or 0.2% Mero) at the specified dose.

[0209] The herbicide was then applied. Mesosulfuron-methyl, formulated as water-dispersible granules (WG), was sprayed onto the above-ground plant parts as an aqueous dispersion at a water application rate equivalent to 800 l / ha with the addition of a wetting agent (e.g., 0.2% Genapol-LRO or 1 l / ha Biopower) at a dose of 40-60 g / ha. The herbicide dose was selected to cause moderate, visually clearly detectable damage (min. 30%, max. 75%) compared to untreated crops at the time of evaluation on a control group of crops included in the same trial without safener treatment.

[0210] After application, the plants were cultivated in a greenhouse under favorable growth conditions. 9-13 days after application, a visual assessment of the efficacy of the test compounds was performed. For this purpose, the appearance of the plants treated with the test compound and herbicide was compared with the corresponding herbicide controls (without safener; with clearly visible damage) and the untreated controls (without damage). The pest-reducing effect of the test compounds was recorded in "efficacy codes" according to the following scheme: 0: no damage reduction (appearance corresponding to the herbicide control) 1: weak damage reduction 2: significant damage reduction 3: strong damage reduction 4: complete damage reduction (appearance corresponding to the untreated control)

[0211] The experiments show a clear effectiveness of exemplary selected compounds according to the invention with regard to the reduction of damage caused by herbicides, such as mesosulfuron-methyl, to crop plants such as spring wheat (TRZAS; cv. Triso): Example No. Dosage of the safener of formula (I) (g / ha) cultivated plant Effectiveness of the safener (efficacy code) I.27-2 100 TRZAS 4 I.25-2 100 TRZAS 3 I.26-17 100 TRZAS 2 I.25-43 500 TRZAS 2 I.26-2 500 TRZAS 4 I.26-2 100 TRZAS 3 2.2 Relative effect of selected compounds according to the invention using the example of the pest reduction of mesosulfuron-methyl on spring barley (HORVS)

[0212] The seeds of the crops to be treated were sown in plastic pots (diameter ~4 cm) in sandy loam soil, covered with soil, and grown in a greenhouse under favorable conditions for germination and growth. The test plants were treated at the early leaf stage (BBCH10 - BBCH12). The compounds of the invention, formulated as wettable powders (WP), were sprayed onto the above-ground plant parts as an aqueous suspension at a water application rate corresponding to 800 l / ha, with the addition of a wetting agent (e.g., 0.2% Genapol-LRO or 0.2% Mero) at the specified dose.

[0213] The herbicide was then applied. For this purpose, mesosulfuron-methyl, formulated as water-dispersible granules (WG), was sprayed onto the above-ground plant parts as an aqueous dispersion at a water application rate equivalent to 800 l / ha with the addition of a wetting agent (e.g., 0.2% Genapol-LRO or 1 l / ha Biopower) at a dose of 40–60 g / ha. The herbicide dose was selected so that, at the time of evaluation, it caused moderate, visually clearly detectable damage (min. 30%, max. 75%) in a control group of crops included in the same trial without safener treatment, compared to untreated crops. After application, the plants were cultivated in a greenhouse under favorable growth conditions. The efficacy of the test compounds was visually assessed 9–13 days after application.For this purpose, the appearance of the plants treated with the test compound and herbicide was compared with the corresponding herbicide controls (without safener; with clearly visible damage) and the untreated controls (without damage). The pest-reducing effect of the test compounds was recorded separately for two replicates using "efficacy codes" according to the following scheme: . 0: no damage reduction (appearance corresponding to the herbicide control) 1: weak damage reduction 2: significant damage reduction 3: strong damage reduction 4: complete damage reduction (appearance corresponding to the untreated control)

[0214] The experiments show a clear effectiveness of exemplary selected compounds according to the invention with regard to the reduction of damage to crop plants caused by herbicides such as mesosulfuron-methyl, such as spring barley (HORVS; cv. Montoya): Example No. Dosage of the safener of formula (I) (g / ha) cultivated plant Effectiveness of the safener (efficacy code) I.26-17 100 HORVS 2

Claims

1. Compounds of the general formula (I) or salts thereof in which R1 is heteroaryl, excluding thienyl, where the heteroaryl radical is unsubstituted or substituted by halogen, cyano, nitro, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C8) cycloalkyl, (C3-C8) cycloalkenyl, (C1-C6)alkoxy and (C1-C6)alkylS(O)p, where the latter seven radicals are unsubstituted or are substituted by one or more radicals from the group of halogen, cyano, (C1-C6)alkoxy and (C1-C6)alkylS(O)p, R2 is hydrogen, halogen, cyano, nitro, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C8) cycloalkyl, (C3-C8)cycloalkenyl, (C1-C6)alkoxy and (C1-C6)alkyls (O)p, where the latter seven radicals are unsubstituted or substituted by one already more radicals from the group of halogen, cyano, (C1-C6)alkoxy and (C1-C6)alkylS (O)p, R3 is hydrogen and (C1-C6)alkyl, R4 is hydrogen, (C1-C18)alkyl, (C1-C18)haloalkyl, (C1-C18)cyanoalkyl, (C2-C18)alkenyl, (C2-C18)alkynyl, (C3-C12)cycloalkyl, (C3-C12)cycloalkenyl, aryl, heteroaryl, (C1-C18)alkoxy- (C1-C18)alkyl, (C1-C18)haloalkoxy - (C1-C18)alkyl, (C1-C18)alkoxy- (C1-C18)haloalkyl, (C1-C18)alkylthio- (C1-C18)alkyl, (C1-C18)haloalkylthio- (C1-C18)alkyl, (C2-C18)haloalkenyl, (C2-C18)haloalkynyl, heterocyclyl- (C1-C18)alkyl, aryl-(C1-C18)alkyl, (C3-C12)cycloalkyl - (C1-C18)alkyl, (C1-C18)alkoxycarbonyl - (C1-C18)alkyl, and (C1-C18)alkoxycarbonyl- (C3-C12)cycloalkyl - (C1-C18)alkyl, or a radical of the formula -NRaRb or - N=CRcRd, where, in the former 2 radicals, each of the Ra, Rb, Rc and Rd radicals is independently hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, benzyl, substituted benzyl, phenyl or substituted phenyl or Ra and Rb together with the nitrogen atom may form a 3- to 8-membered heterocycle which may contain one or two further ring heteroatoms from the group of N, O and S and which is unsubstituted or substituted by one or more radicals from the group of (C1-C4)-alkyl and (C1-C4)-haloalkyl, or Rc and Rd together with the carbon atom are a 3- to 8-membered carbocyclic or heterocyclic radical which may contain 1 to 3 ring heteroatoms from the group of N, O and S, where the carbocyclic or heterocyclic radical is unsubstituted or substituted by one or more radicals from the group of (C1-C4)-alkyl and (C1-C4)-haloalkyl, m is a number from 0 to 5, and p is 0, 1 or 2.

2. Compounds of the general formula (I) according to Claim 1 or salts thereof, in which R1 is heteroaryl, excluding thienyl, where the heteroaryl radical is unsubstituted or substituted by halogen, cyano, nitro, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C4)alkynyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkenyl, (C1-C4)alkoxy and (C1-C6)alkylS(O)p, where the latter seven radicals are unsubstituted or are substituted by one already more radicals from the group of halogen, cyano, (C1-C4)alkoxy and (C1-C4)alkylS (O)p, R2 is hydrogen, halogen, cyano, nitro, (C1-C4) alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkenyl, (C1-C4)alkoxy and (C1-C4)alkyls (O)p, where the latter seven radicals are unsubstituted or substituted by one already more radicals from the group of halogen, cyano, (C1-C4)alkoxy and (C1-C4)alkylS(O)p, R3 is hydrogen and (C1-C4)alkyl, R4 is hydrogen, (C1-C16)alkyl, (C1-C16)haloalkyl, (C1-C16)cyanoalkyl, (C2-C16)alkenyl, (C2-C16)alkynyl, (C3-C12)cycloalkyl, (C3-C12)cycloalkenyl, aryl, heteroaryl, (C1-C16)alkoxy- (C1-C16)alkyl, (C1- C16)haloalkoxy- (C1-C16)alkyl, (C1-C16)alkoxy- (C1-C16)haloalkyl, (C1-C16)alkylthio- (C1-C16)alkyl, (C1-C16)haloalkylthio- (C1-C16)alkyl, (C2-C16)haloalkenyl, (C2-C16)haloalkynyl, heterocyclyl- (C1-C16)alkyl, aryl- (C1-C16)alkyl, (C3-C12)cycloalkyl - (C1-C16)alkyl, (C1-C16)alkoxycarbonyl - (C1-C16)alkyl and (C1-C16)alkoxycarbonyl- (C3-C12)cycloalkyl-(C1-C16)alkyl, m is a number from 0 to 4, and p is 0, 1 or 2.

3. Compounds of the general formula (I) according to Claim 1 or salts thereof, in which R1 is heteroaryl, excluding thienyl, where the heteroaryl radical is unsubstituted or mono- or polysubstituted by halogen, cyano, methyl, ethyl, CF3,CF2Cl, CH2F, CHF2, OCH3, OCF3, SCH3, SOCH3, SO2CH3 and SCF3, R2 is hydrogen, halogen, cyano, methyl, ethyl, CF3, CF2Cl, CH2F, CHF2, OCH3, OCF3, SCH3, SOCH3, SO2CH3 and SCF3, R3 is hydrogen, CH2CH3 and CH3, R4 is hydrogen, (C1-C12)alkyl, (C1-C12)haloalkyl, (C1-C12)cyanoalkyl, (C2-C12)alkenyl, (C2-C12)alkynyl, (C3-C12)cycloalkyl, (C3-C12)cycloalkenyl, aryl, heteroaryl, (C1-C12)alkoxy- (C1-C12)alkyl, (C1-C12)haloalkoxy- (C1-C12)alkyl, (C1-C12)alkoxy- (C1-C12)haloalkyl, (C1-C12)alkylthio- (C1-C12)alkyl, (C1-C12)haloalkylthio- (C1-C12)alkyl, (C2-C12)haloalkenyl, (C2-C12)haloalkynyl, heterocyclyl- (C1-C12)alkyl, aryl- (C1-C12)alkyl, (C3-C12)cycloalkyl-(C1-C12)alkyl, (C1-C12)alkoxycarbonyl-(C1-C12)alkyl and (C1-C12)alkoxycarbonyl- (C3-C12)cycloalkyl-(C1-C12)alkyl, m is a number 0, 1, 2 or 3, and p is 0, 1 or 2.

4. Compounds of the general formula (I) according to Claim 1 or salts thereof, in which R1 is pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl, pyridazin-4-yl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl, 1,2,3-triazin-4-yl, 1,2,3-triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 1,3-oxazol-2-yl, 1,3-oxazol-4-yl, 1,3-oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,3-thiazol-2-yl, 1,3-thiazol-4-yl, 1,3-thiazol-5-yl, 1H-pyrrol-1-yl, 1H-pyrrol-2-yl, 1H-pyrrol-3-yl, furan-2-yl, furan-3-yl, 1H-imidazol-1-yl; 1H-imidazol-2-yl; 1H-imidazol-4-yl; 1H-imidazol-5-yl, 1H-pyrazol-1-yl, 1H-pyrazol-3-yl, 1H-pyrazol-4-yl, 1H-pyrazol-5-yl, 1H-1,2,3-triazol-1-yl, 1H-1,2,3-triazol-4-yl, 1H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1,2,4-triazol-1-yl, 1H-1,2,4-triazol-3-yl, 4H-1,2,4-triazol-4-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,5-oxadiazol-3-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-thiadiazol-5-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,5-thiadiazol-3-yl, 1,2,5-thiadiazol-3-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, which is unsubstituted or mono- or polysubstituted by halogen, cyano, methyl, CF3, CF2Cl, CH2F, CHF2, OCH3, OCF3, SCH3, SOCH3, SO2CH3 and SCF3, R2 is hydrogen, fluorine, chlorine, bromine, iodine, CN, methyl, CF3, CF2Cl, CH2F, CHF2, OCH3, OCF3, SCH3, SOCH3, SO2CH3 and SCF3, R3 is hydrogen and CH3, R4 is hydrogen, (C1-C10)alkyl, (C1-C10)haloalkyl, (C1-C10)cyanoalkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C3-C9)cycloalkyl, (C3-C9)cycloalkenyl, aryl, heteroaryl, (C1-C10)alkoxy- (C1-C10)alkyl, (C1-C10)haloalkoxy- (C1-C10)alkyl, (C1-C10)alkoxy- (C1-C10)haloalkyl, (C1-C10)alkylthio - (C1-C10)alkyl, (C1-C10)haloalkylthio-(C1-C10)alkyl, (C2-C18)haloalkenyl, (C2-C18)haloalkynyl, heterocyclyl- (C1-C10)alkyl, aryl - (C1-C10)alkyl, (C3-C9)cycloalkyl - (C1-C10)alkyl, (C1-C10)alkoxycarbonyl- (C1-C10)alkyl and (C1-C10)alkoxycarbonyl- (C3-C9)cycloalkyl- (C1-C10)alkyl, m is a number 0, 1, 2 or 3, and p is 0, 1 or 2.

5. Compounds of the general formula (I) according to Claim 1 or salts thereof, in which R1 represents the Q-1.1 to Q-1.59 groups Q-1.1Q-1.2Q-1.3Q-1.4Q-1.5 Q-1.6Q-1.7Q-1.8Q-1.9Q-1.10 Q-1.11Q-1.12Q-1.13Q-1.14Q-1.15 Q-1.16Q-1.17Q-1.18Q-1.19Q-1.20 Q-1.21Q-1.22Q-1.23Q-1.24Q-1.25 Q-1.35 Q-1.36Q-1.37Q-1.38Q-1.39Q-1.40 Q-1.41Q-1.42Q-1.43Q-1.44Q-1.45 Q-1.46Q-1.47Q-1.48Q-1.49Q-1.50 Q-1.51Q-1.52Q-1.53Q-1.54Q-1.55 Q-1.56Q-1.57Q-1.58Q-1.59 R2 is hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, CF3, CH2F, CHF2, OCH3, OCF3, SCH3, SOCH3, SO2CH3 and SCF3, R3 is hydrogen, R4 is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, n-pentyl, phenyl, benzyl, CH2(4-Cl-Ph), CH2(4-F-Ph), CH2(4-MeO-Ph), 2-methoxyethyl, tetrahydrofuran-2-ylmethyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl, methylpropionate-3-yl, ethylpropionate-3-yl, methylacet-2-yl, ethylacet-2-yl, methylpivalate-2-yl, ethylpivalate-3-yl, methyl-2-methylpropanoate-3-yl, methyl-2,2-dimethylpropanoate-3-yl, ethyl-2-methylpropanoate-3-yl, methyl-2-propanoate-2-yl, ethyl-2-propanoate-2-yl, methylacetate-2-yl, ethylacetate-2-yl, methyl-1-methylcyclopropanecarboxylate-2-yl, ethyl-1-methylcyclopropanecarboxylate-2-yl, 2-(dimethylamino)ethyl, oxetan-3-yl, (3-methyloxetan-3-yl)methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl, cyclopropylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl, allyl, propargyl (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl, 3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl, 1- (2E) -1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z) -pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, heptan-2-yl, isobutyl, 1,3-dioxolan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazol-4-methyl, m is a number 0, 1, 2 or 3.

6. Compounds of the general formula (I) according to Claim 1 or salts thereof, in which R1 is the groups selected below from Q-1.1 to Q-1.59 Q-1.1Q-1.2Q-1.3Q-1.4Q-1.5 Q-1.6Q-1.7Q-1.10Q-1.11Q-1.12 Q-1.13Q-1.14Q-1.15Q-1.17Q-1.18 Q-1.19Q-1.21Q-1.22Q-1.24Q-1.25 Q-1.56Q-1.57Q-1.59 and (R2)m-phenyl represents the Q-2.1 to Q-2.53 groups Q-2.1Q-2.2Q-2.3Q-2.4Q-2.5 Q-2.6Q-2.7Q-2.8Q-2.9Q-2.10 Q-2.11Q-2.12Q-2.13Q-2.14Q-2.15 Q-2.16Q-2.17Q-2.18Q-2.19Q-2.20 Q-2.21Q-2.22Q-2.23Q-2.24Q-2.25 Q-2.26Q-2.27Q-2.28Q-2.29Q-2.30 Q-2.31Q-2.32Q-2.33Q-2.34Q-2.35 Q-2.36Q-2.37Q-2.38Q-2.39Q-2.40 Q-2.41Q-2.42Q-2.43Q-2.44Q-2.45 Q-2.46Q-2.47Q-2.48Q-2.49Q-2.50 Q-2.51Q-2.52Q-2.53 R3 is hydrogen, R4 is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, n-pentyl, phenyl, benzyl, CH2(4-Cl-Ph), CH2(4-F-Ph), CH2(4-MeO-Ph), 2-methoxyethyl, tetrahydrofuran-2-ylmethyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl, methylpropionate-3-yl, ethylpropionate-3-yl, methylacet-2-yl, ethylacet-2-yl, methylpivalate-2-yl, ethylpivalate-3-yl, methyl-2-methylpropanoate-3-yl, methyl-2,2-dimethylpropanoate-3-yl, ethyl-2-methylpropanoate-3-yl, methyl-2-propanoate-2-yl, ethyl-2-propanoate-2-yl, methylacetate-2-yl, ethylacetate-2-yl, methyl-1-methylcyclopropanecarboxylate-2-yl, ethyl-1-methylcyclopropanecarboxylate-2-yl, 2-(dimethylamino)ethyl, oxetan-3-yl, (3-methyloxetan-3-yl)methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl, cyclopropylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl, allyl, propargyl (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl, 3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl, 1- (2E) -1-methylbut-2-en-1-yl, (E)-pent- 3 -en- 2-yl or (Z) -pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, heptan-2-yl, isobutyl, 1,3-dioxolan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazol-4-methyl.

7. Useful plant- or crop plant-protecting composition, characterized by a content of at least one compound of the general formula (I) or salts thereof according to any of Claims 1 to 6 in combination with further agrochemicals and optionally formulation auxiliaries.

8. Composition according to Claim 7, comprising at least one herbicide.

9. Method of reducing phytotoxic effects of pesticides on useful plants or crop plants by use of one or more compounds of Claims 1-6 or of the compositions according to Claim 7 or 8.

10. Method of reducing phytotoxic effects of pesticides on useful plants or crop plants, characterized in that one or more inventive compounds of the general formula (I) according to any of Claims 1 to 6 for joint use with pesticides is deployed simultaneously or in any sequence with the pesticides.

11. Method according to Claim 10, wherein the pesticides are one or more herbicides.

12. Method according to either of Claims 10 and 11, characterized in that compounds of the formula (I) or salts thereof according to Claims 1 to 6 are applied to the plants, parts of the plants, or the seeds or seed material thereof.