[(1-phenyl-5-(heteroaryl)-1h-1,2,4-triazol-3-yl)oxy]acetic acid derivatives as safeners for protecting useful and crop plants

Abstract

The present invention relates to crop protection compounds and to compositions comprising certain compounds as safeners for reducing the phytotoxic effects of agrochemicals, in particular herbicides. More specifically, the present invention relates to certain [(1-phenyl-5-(heteroaryl)-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives of general formula (I) and salts thereof, to processes for their preparation, and to their use as crop protection compounds (safeners).

Description

TECHNICAL FIELD

[0001] The present invention relates to useful plant-protecting compounds and compositions comprising specific compounds as safeners for reducing the phytotoxic effects of agrochemicals, in particular herbicides. More specifically, the present invention relates to specific substituted [(1-phenyl-5-(heteroaryl)-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives and salts thereof as safeners and to a process for their preparation. BACKGROUND

[0002] When using pesticides for controlling unwanted organisms in crops of useful plants in horticulture and forestry, the useful plants are also frequently or more or less damaged by the pesticides used (for example herbicides, insecticides and especially fungicides). This unwanted phytotoxic side effect occurs to a particular extent when using large amounts of herbicides in crops of useful plants such as corn, rice or cereals, mainly in post-emergence application. In some cases, the use of "safeners" or "detoxifiers" can protect the useful plants from the phytotoxicity of the pesticides without reducing or significantly impairing the action of the pesticides against the harmful organisms. In some cases, even an improved action of the pesticides against the harmful organisms (for example weeds) is observed in the presence of safeners.

[0003] The compounds known hitherto as safeners belong to a large number of different chemical structural classes, the applicability of which as safeners also depends in general on the chemical structure of the pesticide and the crop of useful plants.

[0004] The safener effect of phenoxy- or heteroaryloxyalkanecarboxylic acid derivative compounds is known for a long time when used in combination with herbicides. Examples of such compounds are MCPA and similar compounds, which at the same time still have herbicidal activity against harmful plants; or cloquintocet-mexyl.

[0005] Also known are safeners which are N-phenyl-substituted heteroarylcarboxylic acid ester derivatives having multiple heteroatoms in the heteroaromatic system. Examples of such safeners are mefenpyr-diethyl and isoxadifen-ethyl safeners which are used in commercial products.

[0006] WO 2004 / 084631 discloses the use of hydroxy-substituted aromatic carboxylic acid derivatives. WO 2005 / 015994 describes specific salicylic acid derivatives as safeners. These are particularly suitable as safeners for corn and soybean crops.

[0007] Furthermore, WO 2005 / 112630 discloses 1,2-dihydroquinoxalin-2-one derivatives and WO 2008 / 131860 discloses pyridinone carboxamides as safeners.

[0008] Active ingredients from the chemical class of substituted [(1-phenyl-5-(heteroaryl)-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives with plant active properties are unknown in the literature.

[0009] Various literature describes [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives with medical properties. Polish J. Chem. 2006, 80, 889-897 and Bioorganic & Medicinal Chemistry 2018, 26, 3321-3344 disclose [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives.

[0010] When safeners are used to protect crop plants from damage by pesticides, it has been found that the known safeners have disadvantages in many cases. These disadvantages include:

[0011] - insufficient useful plant protection properties,

[0012] - combination with specific herbicides, where the range of useful plants in which the safener / herbicide combination is used is not sufficiently large,

[0013] - specific safeners can only be used in combination with a small number of herbicides,

[0014] - the use of safeners increases the rate of application and the amount of formulation adjuvants used, and thus can lead to problems associated with application.

[0015] For the above reasons, there is an increasing need to provide alternative compounds with safener action. SUMMARY

[0016] The present application provides new useful plant protection compounds of the general formula (I)

[0017]

[0018] for reducing the phytotoxic action of pesticides, in particular herbicides, on useful plants or crop plants,

[0019] wherein

[0020] R 1 is heteroaryl, where heteroaryl 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) psubstituted or by one or more radicals from the group halogen, cyano, (C1-C6)alkoxy and (C1-C6)alkylS(O) p ,

[0021] R 2 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 , wherein the last seven radicals are unsubstituted or substituted by one or more radicals from the group halogen, cyano, (C1-C6)alkoxy and (C1-C6)alkylS(O) p ,

[0022] R 3 is hydrogen and (C1-C6)alkyl,

[0023] R 4 is hydrogen, (C1-C 18 )alkyl, (C1-C 18 )haloalkyl, (C1-C 18 )cya noalkyl, (C2-C 18 )alkenyl, (C2-C 18 )alkynyl, (C3-C 12 )cycloalkyl, (C3-C 12 )cycloalkenyl, aryl, heteroaryl, (C1-C 18 )alkoxy-(C1-C 18 )alkyl, (C1-C 18 )haloalkoxy-(C1-C 18 )alkyl, (C1-C 18 )alkoxy-(C1-C 18 )haloalkyl, (C1-C 18 )alkylthio-(C1-C 18 )alkyl, (C1-C 18 )haloalkylthio-(C1-C 18 )alkyl, (C2-C 18 )haloalkenyl, (C2-C 18 )haloalkynyl, heterocyclyl-(C1-C 18 )alkyl, aryl-(C1-C 18 )alkyl, (C3-C 12 )cycloalkyl-(C1-C 18 )alkyl, (C1-C 18 )alkoxycarbonyl-(C1-C 18 )alkyl and (C1-C 18 )alkoxycarbonyl-(C3-C12 ) cycloalkyl-(Ci-C 18 ) alkyl, or

[0024] of the formula -NR a R b or -N=CR c R d group,

[0025] wherein, in the first two groups, each of the R a , R b , R c and R d groups is independently hydrogen, (Ci-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, benzyl, substituted benzyl, phenyl or substituted phenyl,

[0026] Alternatively, R a and R b together with the nitrogen atom can form a 3- to 8-membered heterocyclic ring which, in addition to the nitrogen atom, can contain one or two further ring heteroatoms from N, O and S, and which is unsubstituted or substituted by one or more groups from (Ci-C4)alkyl and (Ci-C4)haloalkyl,

[0027] Alternatively, R c and R d together with the carbon atom are a 3- to 8-membered carbocyclic or heterocyclic radical which can contain 1 to 3 ring heteroatoms from N, O and S, wherein the carbocyclic or heterocyclic radical is unsubstituted or substituted by one or more groups from (Ci-C4)alkyl and (Ci-C4)haloalkyl,

[0028] m is a number from 0 to 5,

[0029] and

[0030] p is 0, 1 or 2.

[0031] The compounds of general formula (I) can form salts by addition of suitable mineral or organic acids to basic groups, for example mineral acids, such as HCI, HBr, H2SO4, H3PO4 or HNO3, or organic acids, such as carboxylic acids, for example formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid, or sulfonic acids, for example p-toluenesulfonic acid, for example piperidinyl, morpholinyl or pyridyl groups. These salts then contain the conjugate base of the acid as anion. Suitable deprotonated forms of substituents, for example sulfonic acids, in particular sulfonamides or carboxylic acids, are able to form internal salts with groups which can themselves be protonated, such as amino groups. Salts can also be formed by the action of bases on the compounds of general formula (I). Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine, and also ammonium, alkali metal or alkaline earth metal hydroxides, carbonates and hydrogen carbonates, in particular sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate. These salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, for example metal salts, in particular alkali metal or alkaline earth metal salts, in particular sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary ammonium salts, for example cations of the formula [NR i ii iii iv + i R iv each independently is an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl. Also useful are alkylsulfonium and alkylsulfoxonium salts, for example (Ci-C4)-trialkylsulfonium and (Ci-C4)-trialkylsulfoxonium salts.

[0032] The compounds of formula (I) and their salts used according to the application are hereinafter referred to as "compounds of general formula (I)".

[0033] The present application preferably provides compounds of general formula (I), wherein

[0034] R 1 is heteroaryl, wherein heteroaryl is unsubstituted or substituted by halogen, cyano, nitro, (Ci-C6)alkyl, (C2-C6)alkenyl, (C2-C4)alkynyl, (C3-C7)cycloalkyl, (C3-C7)cycloalkenyl, (Ci-C4)alkoxy and (Ci-C4)alkylS(O) p , wherein the last seven radicals are unsubstituted or substituted by one or more radicals from the group halogen, cyano, (Ci-C4)alkoxy and (Ci-C4)alkylS(O) p ,

[0035] R 2 ​​​​​haloalkyl, haloalkenyl, haloalkynyl, heterocyclyl-(Ci-C4)alkyl, aryl-(Ci-C4)alkyl, (C3-C6)cycloalkyl-(Ci-C4)alkyl, (Ci-C4)alkoxycarbonyl-(Ci-C4)alkyl and (Ci-C4)alkoxycarbonyl-(C3-C6)cycloalkyl-(Ci-C4)alkyl, wherein the last 16 groups are unsubstituted or substituted by one or more radicals from the group of halogen, cyano, (Ci-C4)alkoxy and (Ci-C4)alkylS(O)n- with n = 0 to 2, p wherein the last seven groups are unsubstituted or substituted by one or more radicals from the group of halogen, cyano, (Ci-C4)alkoxy and (Ci-C4)alkylS(O)n- with n = 0 to 2, p wherein the last seven groups are unsubstituted or substituted by one or more radicals from the group of halogen, cyano, (Ci-C4)alkoxy and (Ci-C4)alkylS(O)n- with n = 0 to 2,

[0036] R 3 is hydrogen and (Ci-C4)alkyl,

[0037] R 4 is hydrogen, (Ci-C 16 )alkyl, (Ci-C 16 )haloalkyl, (Ci-C 16 )cya-noalkyl, (C2-C 16 )alkenyl, (C2-C 16 )alkynyl, (C3-C 12 )cycloalkyl, (C3-C 12 )cycloalkenyl, aryl, heteroaryl, (Ci-C 16 )alkoxy-(Ci-C 16 )alkyl, (Ci-C 16 )haloalkoxy-(Ci-C 16 )alkyl, (Ci-C 16 )alkoxy-(Ci-C 16 )haloalkyl, (Ci-C 16 )alkylthio-(Ci-C 16 )alkyl, (Ci-C 16 )haloalkylthio-(Ci-C 16 )alkyl, (C2-C 16 )haloalkenyl, (C2-C 16 )haloalkynyl, heterocyclyl-(Ci-C 16 )alkyl, aryl-(Ci-C 16 )alkyl, (C3-C 12 )cycloalkyl-(Ci-C 16 )alkyl, (Ci-C 16 )alkoxycarbonyl-(Ci-C 16 )alkyl and (Ci-C 16 )alkoxycarbonyl-(C3-C 12 )cycloalkyl-(Ci-C 16 )alkyl,

[0038] m is a number from 0 to 4,

[0039] and

[0040] p is 0, 1 or 2.

[0041] The application very particularly preferably provides compounds of the general formula (I), in which

[0042] R 1 is heteroaryl, which is unsubstituted or mono- or poly-substituted by halogen, cyano, methyl, ethyl, CF3, CF2Cl, CH2F, CHF2, OCH3, OCF3, SCH3, SOCH3, SO2CH3and SCF3,

[0043] R 2 is hydrogen, halogen, cyano, methyl, ethyl, CF3, CF2Cl, CH2F, CHF2, OCH3, OCF3, SCH3, SOCH3, SO2CH3and SCF3,

[0044] R 3 is hydrogen, CH2CH3and CH3,

[0045] R 4 is hydrogen, (C1-C 12 )alkyl, (C1-C 12 )haloalkyl, (C1-C 12 )cya-noalkyl, (C2-C 12 )alkenyl, (C2-C 12 )alkynyl, (C3-C 12 )cycloalkyl, (C3-C 12 )cycloalkenyl, aryl, heteroaryl, (C1-C 12 )alkoxy-(C1-C 12 )alkyl, (C1-C 12 )haloalkoxy-(C1-C 12 )alkyl, (C1-C 12 )alkoxy-(C1-C 12 )haloalkyl, (C1-C 12 )alkylthio-(C1-C 12 )alkyl, (C1-C 12 )haloalkylthio-(C1-C 12 )alkyl, (C2-C 12 )haloalkenyl, (C2-C 12 )haloalkynyl, heterocyclyl-(C1-C 12 )alkyl, aryl-(C1-C 12 )alkyl, (C3-C 12 )cycloalkyl-(C1-C 12 )alkyl, (C1-C 12 )alkoxycarbonyl-(C1-C 12 )alkyl and (C1-C12 )alkylcarbonyl-(C3-C6)cycloalkyl, 12 )alkylcarbonyl-(C3-C6)cycloalkyl, 12 )alkyl,

[0046] m is 0, 1, 2 or 3.

[0047] The application is especially preferred to provide compounds of general formula (I), wherein

[0048] R 1is 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-oxadiazinyl, 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 H-pyrrol-1 -yl, 1 H-pyrrol-2-yl, 1 H-pyrrol-3-yl, furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, 1 H-imidazol-1 -yl, 1 H-imidazol-2-yl, 1 H-imidazol-4-yl, 1 H-imidazol-5-yl, 1 H-pyrazol-1 -yl, 1 H-pyrazol-3-yl, 1 H-pyrazol-4-yl, 1 H-pyrazol-5-yl, 1 H-1,2,3-triazol-1 -yl, 1 H-1,2,3-triazol-4-yl, 1 H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1 H-1,2,4-triazol-1 -yl, 1 H-1,2,4-triazol-5-yl, 4H-1,2,4-triazol-3-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-2-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-3-yl, wherein the aforementioned radicals are unsubstituted or mono- or poly-substituted by halogen, cyano, methyl, CF3, CF2CI, CH2F, CHF2, OCH3, OCF3, SCH3, SOCH3, SO2CH3and SCF3,

[0049] R 2 is hydrogen, fluorine, chlorine, bromine, iodine, CN, methyl, CF3, CF2CI, CH2F, CHF2, OCH3, OCF3, SCH3, SOCH3, SO2CH3and SCF3,

[0050] R 3 is hydrogen and CH3,

[0051] R 4 is hydrogen, (Ci-C 10 )alkyl, (Ci-C 10 )haloalkyl, (Ci-C 10 )cya noalkyl, (C2-C 10 )alkenyl, (C2-C 10 )alkynyl, (C3-C9)cycloalkyl, (C3-C9)cycloalkenyl, aryl, heteroaryl, (Ci-C 10 )alkoxy-(Ci-C 10 )alkyl, (Ci-C 10 )haloalkoxy-(Ci-C 10 )alkyl, (Ci-C 10 )alkoxy-(Ci-C 10 )haloalkyl, (Ci-C 10 )alkylthio-(Ci-C 10 )alkyl, (Ci-C 10 )haloalkylthio-(Ci-C 10 )alkyl, (C2-C 18 )haloalkenyl, (C2-C 18 )haloalkynyl, heterocyclyl-(Ci-C 10 )alkyl, aryl-(Ci-C 10 )alkyl, (C3-C9)cycloalkyl-(Ci-C 10 )alkyl, (Ci-C 10 )alkoxycarbonyl-(Ci-C 10 )alkyl and (Ci-C 10 )alkoxycarbonyl-(C3-C9)cycloalkyl-(Ci-C 10 )alkyl,

[0052] and

[0053] m is 0, 1, 2 or 3.

[0054] The application very particularly provides compounds of general formula (I), wherein

[0055] R 1 is a group Q-1.1 to Q-1.59,

[0056]

[0057]

[0058]

[0059] R 2hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, CF3, CH2F, CHF2, OCH3, OCF3, SCH3, SOCH3, SO2CH3and SCF3,

[0060] R 3 hydrogen,

[0061] R 4 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-yl-methyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl, methylpropionate-3-yl, ethylpropionate-3-yl, methylethanoate-2-yl, ethylethanoate-2-yl, methylneopentanoate-2-yl, ethylneopentanoate-3-yl, methyl-2-methylpropionate-3-yl, methyl-2,2-dimethylpropionate-3-yl, ethyl-2-methylpropionate-3-yl, methyl-2-propionate-2-yl, ethyl-2-propionate-2-yl, methylacetyl-2-yl, ethylacetyl-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-chloro-prop-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, (2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, hept-2-yl, isobutyl, 1,3-dioxolan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazol-4-methyl,

[0062] m is 0, 1, 2 or 3.

[0063] The application very particularly preferably provides compounds of the general formula (I), in which

[0064] R 1 is a radical Q-1.1 to Q-1.59

[0065]

[0066]

[0067] and (R 2 ) m - phenyl is a radical Q-2.1 to Q-2.53

[0068]

[0069]

[0070] R 3 is hydrogen,

[0071] R 4hydrogen, 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-yl-methyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl, methylpropionate-3-yl, ethylpropionate-3-yl, methylethylacetate-2-yl, ethylethylacetate-2-yl, methylneopentanoate-2-yl, ethylneopentanoate-3-yl, methyl-2-methylpropionate-3-yl, methyl-2,2-dimethylpropionate-3-yl, ethyl-2-methylpropionate-3-yl, methyl-2-propionate-2-yl, ethyl-2-propionate-2-yl, methylethylacetate-2-yl, ethylethylacetate-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, (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.

[0072] The application provides especially very particularly preferred compounds of the general formula (I), in which

[0073] R 1 are Q-1.1 to Q-1.59

[0074]

[0075] and (R 2 ) m - phenyl is the radical Q-2.1 to Q-2.53,

[0076]

[0077]

[0078] R 3 It is hydrogen.

[0079] R 4 The following are the compounds: hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, phenyl, benzyl, CH2(4-Cl-Ph), CH2(4-F-Ph), CH2(4-MeO-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl, methylpropionate-3-yl, ethylpropionate-3-yl, methylacetate-2-yl, ethylacetate-2-yl, methylneoplastate-2-yl, ethylneoplastate. -3-yl, methyl-2-methylpropionate-3-yl, methyl-2,2-dimethylpropionate-3-yl, ethyl-2-methylpropionate-3-yl, methyl-2-propionate-2-yl, ethyl-2-propionate-2-yl, methyl acetate-2-yl, ethyl acetate-2-yl, methyl-1-methylcyclopropanecarboxylate-2-yl, ethyl-1-methylcyclopropanecarboxylate-2-yl, 2-(dimethylamino)ethyl, oxetane-3-yl, (3-methyloxetane-3-yl)methyl, 2,2,2-trifluoroethyl, 2,2-di- Fluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl, cyclopropylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl, allyl, propyne (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, (2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, hept-2-yl, isobutyl, 1,3-dioxacyclopentan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl.

[0080] The definitions of the above-mentioned general or preferred radicals apply both to the end products of the general formula (I) and, correspondingly, to the starting materials or intermediates used in each case for the preparation of the desired products. The definitions of these radicals can be combined with one another as desired, i.e. combinations between the given preferred ranges are included.

[0081] Of particular interest, mainly for reasons of higher herbicidal activity, better selectivity and / or better preparability, are the compounds of the general formula (I) or salts thereof or their use according to the application, wherein the individual radicals have one of the indicated or below-mentioned preferred meanings, or in particular those wherein one or more of the indicated or below-mentioned preferred meanings are combined.

[0082] With respect to the compounds according to the application, the terms used above and below will be elucidated. These are familiar to the person skilled in the art and in particular have the definitions elucidated below:

[0083] Unless defined differently, the names of chemical groups are generally to be understood as being attached to the remainder of the skeleton or molecule by the last-mentioned structural element of the relevant chemical group, i.e. for example in the case of (C2-C8)-alkenyloxy by the oxygen atom and in the case of heterocyclyl-(Ci-C8)-alkyl or MeO(O)C-(Ci-C8)-alkyl in each case by the carbon atom of the alkyl group.

[0084] According to the application, "alkylsulfonyl", alone or as part of a chemical group, means straight-chain or branched alkylsulfonyl, preferably having 1 to 8 or 1 to 6 carbon atoms, for example, but not limited to, (Ci-C6)-alkylsulfonyl such as 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 and 1-ethyl-2-methylpropylsulfonyl.

[0085] According to the present invention, "alkathioyl"—either alone or as part of a chemical group—refers to a straight-chain or branched S-alkyl group, preferably having 1 to 8 or 1 to 6 carbon atoms, for example (C1-C6). 10 (C1-C6)- or (C1-C4)-alkylthio, such as (but not limited to) (C1-C6)-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-dimethylbutyrothio, 1,2-dimethylbutyrothio, 1,3-dimethylbutyrothio, 2,2-dimethylbutyrothio, 2,3-dimethylbutyrothio, 3,3-dimethylbutyrothio, 1-ethylbutyrothio, 2-ethylbutyrothio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio, and 1-ethyl-2-methylpropylthio.

[0086] According to the present invention, unless otherwise defined, "alkylsulfinyl (alkyl-S(=O)-)" means an alkyl group bonded to the skeleton by -S(=O)-, for example (C1-C 10 (C1-C6)- or (C1-C4)-alkylsulfinyl groups, such as (but not limited to) (C1-C6)-alkylsulfinyl groups, such as 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, Hexyl sulfinyl, 1-methylpentyl sulfinyl, 2-methylpentyl sulfinyl, 3-methylpentyl sulfinyl, 4-methylpentyl sulfinyl, 1,1-dimethylbutyl sulfinyl, 1,2-dimethylbutyl sulfinyl, 1,3-dimethylbutyl sulfinyl, 2,2-dimethylbutyl sulfinyl, 2,3-dimethylbutyl sulfinyl, 3,3-dimethylbutyl sulfinyl, 1-ethylbutyl sulfinyl, 2-ethylbutyl sulfinyl, 1,1,2-trimethylpropyl sulfinyl, 1,2,2-trimethylpropyl sulfinyl, 1-ethyl-1-methylpropyl sulfinyl, and 1-ethyl-2-methylpropyl sulfinyl.

[0087] "Alkoxy" refers to an alkyl group linked by an oxygen atom, such as (but not limited to) (C1-C6) alkoxy groups, 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, etc. 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 groups represent alkenyl groups linked by oxygen atoms, and alkynyloxy groups represent alkynyl groups linked by oxygen atoms, for example (C2-C...). 10 )-, (C2-C6)- or (C2-C4)-olefins and (C3-C 10 )-, (C3-C6)- or (C3-C4)-acetyloxy.

[0088] Unless otherwise defined, "alkoxycarbonyl (alkyl-OC(=O)-)" refers to an alkyl group bonded to the skeleton via -OC(=O)-, such as (C1-C 10 (C1-C6)- or (C1-C4)-alkoxycarbonyl. The number of carbon atoms here is related to the alkyl group in the alkoxycarbonyl group. Similarly, according to the present invention, unless otherwise defined, "alkenoxycarbonyl" and "alkynoxycarbonyl" refer to alkenyl and alkynyl groups bonded to the skeleton by -OC (=O)-, such as (C2-C4)-alkoxycarbonyl. 10 )-, (C2-C6)- or (C2-C4)-olefin carbonyl and (C3-C 10 (C3-C6)- or (C3-C4)-alkynoxycarbonyl. The number of carbon atoms here is related to the alkenyl or alkynyl group in the alkenyloxycarbonyl or alkynoxycarbonyl group.

[0089] The term "aryl" refers to an optionally substituted monocyclic, bicyclic, or polycyclic aromatic system, preferably having 6 to 14, particularly 6 to 10, cyclic carbon atoms, such as phenyl, naphthyl, anthracene, phenanthryl, etc., with phenyl being the most preferred.

[0090] The term "optionally substituted aryl" also includes polycyclic ring systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenyl, wherein the point of attachment is on the aromatic system. In systematic terms, "aryl" is also covered by the term "optionally substituted phenyl". Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halogencycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, halogenalkylthio, halogenalkyl, alkoxy, halogenalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, dialkylaminoalkoxy, trialkylsilyl, dialkylarylsilyl, dialkylalkylsilyl, trialkylsilylalkynyl, alkylalkynyl, cycloalkylalkynyl, halogenalkylalkynyl, heterocyclyl-N-alkoxy, nitro, cyano, amino, alkylamino, dialkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino, alkoxycarbonylamino, alkoxy- carbonylalkylamino, arylalkyloxycarbonylalkylamino, hydroxycarbonyl, alkoxy- carbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl, dialkylaminocarbonyl, heteroarylalkoxy, arylalkoxy.

[0091] Heterocyclyl groups (heterocyclyl) comprise at least one heterocyclic ring (= carbocyclic ring in which at least one carbon atom has been replaced by a heteroatom, preferably by a heteroatom from N, O, S, P), which is saturated, unsaturated, partially saturated or heteroaromatic and can be unsubstituted or substituted, in which case the point of attachment is on a ring atom. If the heterocyclyl group or the heterocyclic ring is optionally substituted, it can be fused with other carbocyclic or heterocyclic rings. In the case of an optionally substituted heterocyclyl group, polycyclic systems are also included, for example 8-azabicyclo[3.2.1]octyl, 8-azabicyclo[2.2.2]octyl or 1-azabicyclo[2.2.1]heptyl. An optionally substituted heterocyclyl group also includes spirocyclic systems, for example 1-oxa-5-azaspiro[2.3]hexyl. Unless defined differently, a heterocyclic ring preferably comprises 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and comprises one or more, preferably 1 to 4, in particular 1, 2 or 3, heteroatoms, preferably heteroatoms from N, O and S, but not two oxygen atoms directly adjacent, for example containing one heteroatom from N, O and S: 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2- or -3-yl, 2,3-dihydro-1 H-pyrrol-1- or -2- or -3- or -4- or 5-yl, 2,5-dihydro-1 H-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-1 H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,4,7-tetrahydro-1 H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,6,7-tetrahydro-1 H-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-1 H-azepin-1- or -2- or -3- or -4-yl, 2,5-dihydro-1 H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl, 2,7-dihydro-1 H-azepin-1- or -2- or -3- or -4-yl, 2,3-dihydro-1 H-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, 1 H-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-tetrahydrooxazepin-2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,4,7-tetrahydrooxazepin-2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,6,7-tetrahydrooxazepin-2- or -3- or -4-yl, 2,3-dihydrooxazepin-2- or -3- or -4- or -5- or -6- or -7-yl, 4,5-dihydrooxazepin-2- or -3- or -4-yl, 2,5-dihydrooxazepin-2- or -3- or -4- or -5- or -6- or -7-yl, oxazepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2- or 3-tetrahydrothiophenyl, 2,3-dihydrothiophene-2- or -3- or -4- or -5-yl, 2,5-dihydrothiophene-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- and 4-membered heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-aziridinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3-dioxolan-2-yl. Other examples of "heterocyclyl" are partially or fully hydrogenated heterocyclyl groups having two heteroatoms from N, O and S, 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-dihydropyridazin-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-dithiane-3- or 4-yl, 3,4-dihydro-1,2-dithine-3- or 4- or 5- or 6-yl, 3,6-dihydro-1,2-dithine-3- or 4-yl, 1,2-dithine-3- or 4-yl, 1,3-dithiane-2- or 4- or 5-yl, 4H-1,3-dithine-2- or 4- or 5- or 6-yl; isoxazolidin-2- or 3- or 4- or 5-yl, 2,3-dihydroisoxazole-2- or 3- or 4- or 5-yl, 2,5-dihydroisoxazole-2- or 3- or 4- or 5-yl, 4,5-dihydroisoxazole-3- or 4- or 5-yl, 1,3-oxazolidin-2- or 3- or 4 or 5-yl, 2,3-dihydro-1,3-oxazole-2- or 3- or 4- or 5-yl, 2,5-dihydro-1,3-oxazole-2- or 4- or 5-yl, 4,5-dihydro-1,3-oxazole-2- or 4- or 5-yl, 1,2-oxazepan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl, 3,6-dihydro-2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl, 5,6-dihydro-2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl, 5,6-dihydro-4H-1,2-oxazine-3- or 4- or 5- or 6-yl, 2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl, 6H-1,2-oxazine-3- or 4- or 5- or 6-yl, 4H-1,2-oxazine-3- or 4- or 5- or 6-yl, 1,3-oxazepan-2- or 3- or 4- or 5- or 6-yl, 3,4-dihydro-2H-1,3-oxazine-2- or 3- or 4- or 5- or 6-yl, 3,6-dihydro-2H-1,3-oxazine-2- or 3- or 4- or 5- or 6-yl, 5,6-dihydro-2H-1,3-oxazine-2- or 4- or 5- or 6-yl, 5,6-dihydro-4H-1,3-oxazine-2- or 4- or 5- or 6-yl, 2H-1,3-oxazine-2- or 4- or 5- or 6-yl, 6H-1,3-oxazine-2- or 4- or 5- or 6-yl, 4H-1,3-oxazine-2- or 4- or 5- or 6-yl, morpholine-2- or 3- or 4-yl, 3,4-dihydro-2H-1,4-oxazine-2- or 3- or 4- or 5- or 6-yl, 3,6-dihydro-2H-1,4-oxazine-2- or 3- or 5- or 6-yl, 2H-1,4-oxazine-2- or 3- or 5- or 6-yl, 4H-1,4-oxazine-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-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,4,7-tetrahydro-1,2-oxaazepan-2-, 3-, 4-, 5-, 6-, or 7-yl, 2,3,6,7-tetrahydro-l,2-oxaazepan-2-, 3-, 4-, 5-, 6-, or 7-yl, 2,5,6,7-tetrahydro-l,2-oxaazepan-2-, 3-, 4-, 5-, 6-, or 7-yl, 4,5,6,7-tetrahydro-l,2-oxaazepan-3-, 4-, 5-, 6-, or 7-yl, 2,3-dihydro-l,2-oxaazepan-2-, 3-, 4-, 5-, 6-, or 7-yl, 2,5-dihydro-l,2-oxaazepan-2-, 3-, 4-, 5-, 6-, or 7-yl, 2,7-dihydro-l,2-oxaazepan-2-, 3-, 4-, 5-, 6-, or 7-yl, 4,5-dihydro-l,2-oxaazepan-3-, 4-, 5-, 6-, or 7-yl, 4,7-dihydro-l,2-oxaazepan-3-, 4-, 5-, 6-, or 7-yl, 6,7-dihydro-l,2-oxaazepan-3-, 4-, 5-, 6-, or 7-yl, l,2-oxaazepan-3-, 4-, 5-, 6-, or 7-yl, l,3-oxaazepan-2-, 3-, 4-, 5-, 6-, or 7-yl, 2,3,4,5-tetrahydro-l,3-oxaazepan-2-, 3-, 4-, 5-, 6-, or 7-yl, 2,3,4,7-tetrahydro-l,3-oxaazepan-2-, 3-, 4-, 5-, 6-, or 7-yl, 2,3,6,7-tetrahydro-l,3-oxaazepan-2-, 3-, 4-, 5-, 6-, or 7-yl, 2,5,6,7-tetrahydro-l,3-oxaazepan-2-, 4-, 5-, 6-, or 7-yl, 4,5,6,7-tetrahydro-l,3-oxaazepan-2-, 4-, 5-, 6-, or 7-yl, 2,3-dihydro-l,3-oxaazepan-2-, 3-, 4-, 5-, 6-, or 7-yl, 2,5-dihydro-l,3-oxaazepan-2-, 4-, 5-, 6-, or 7-yl, 2,7-dihydro-l,3-oxaazepan-2-, 4-, 5-, 6-, or 7-yl, 4,5-dihydro-l,3-oxaazepan-2-, 4-, 5-, 6-, or 7-yl, 4,7-dihydro-l,3-oxaazepan-2-, 4-, 5-, 6-, or 7-yl, 6,7-dihydro-l,3-oxaazepan-2-, 4-, 5-, 6-, or 7-yl, l,3-oxaazepan-2-, 4-, 5-, 6-, or 7-yl, l,4-oxaazepan-2-, 3-, 5-, 6-, or 7-yl, 2,3,4,5-tetrahydro-l,4-oxaazepan-2-, 3-, 4-, 5-, 6-, or 7-yl, 2,3,4,7-tetrahydro-l,4-oxaazepan-2-, 3-, 4-, 5-, 6-, or 7-yl, 2,3,6,7-tetrahydro-l,4-oxaazepan-2-, 3-, 5-, 6-, or 7-yl, 2,5,6,7-tetrahydro-l,4-oxaazepan-2-, 3-, 5-, 6-, or 7-yl, 4,5,6,7-tetrahydro-l,4-oxaazepan-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3-dihydro-l,4-oxaazepan-2- or 3- or 5- or 6- or 7-yl, 2,5-dihydro-l,4-oxaazepan-2- or 3- or 5- or 6- or 7-yl, 2,7-dihydro-l,4-oxaazepan-2- or 3- or 5- or 6- or 7-yl, 4,5-dihydro-l,4-oxaazepan-2- or 3- or 4- or 5- or 6- or 7-yl, 4,7-dihydro-l,4-oxaazepan-2- or 3- or 4- or 5- or 6- or 7-yl, 6,7-dihydro-l,4-oxaazepan-2- or 3- or 5- or 6- or 7-yl, l,4-oxaazepan-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, l,3-thiazolidin-2- or 3- or 4- or 5-yl, 2,3-dihydro-l,3-thiazol-2- or 3- or 4- or 5-yl, 2,5-dihydro-l,3-thiazol-2- or 4- or 5-yl, 4,5-dihydro-l,3-thiazol-2- or 4- or 5-yl; l,3-thiazinan-2- or 3- or 4- or 5- or 6-yl, 3,4-dihydro-2H-l,3-thiazin-2- or 3- or 4- or 5- or 6-yl, 3,6-dihydro-2H-l,3-thiazin-2- or 3- or 4- or 5- or 6-yl, 5,6-dihydro-2H-l,3-thiazin-2- or 4- or 5- or 6-yl, 5,6-dihydro-4H-l,3-thiazin-2- or 4- or 5- or 6-yl, 2H-l,3-thiazin-2- or 4- or 5- or 6-yl, 6H-l,3-thiazin-2- or 4- or 5- or 6-yl, 4H-l,3-thiazin-2- or 4- or 5- or 6-yl. Other examples of "heterocyclyl" are partially or fully hydrogenated heterocyclic groups having 3 heteroatoms from N, O and S, for example 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-l,4,2-dioxazin-3- or 5- or 6-yl, 1,4,2-dioxazine-3- or 5- or 6-yl, 1,4,2-dioxepan-2- or 3- or 5- or 6- or 7-yl, 6,7-dihydro-5H-l,4,2-dioxepin-3- or 5- or 6- or 7-yl, 2,3-dihydro-7H-l,4,2-dioxepin-2- or 3- or 5- or 6- or 7-yl, 2,3-dihydro-5H-l,4,2-dioxepin-2- or 3- or 5- or 6- or 7-yl, 5H-l,4,2-dioxepin-3- or 5- or 6- or 7-yl, 7H-l,4,2-dioxepin-3- or 5- or 6- or 7-yl, 1,4,2-dioxan-2- or 3- or 5- or 6- or 7-yl, 2,3-dihydro-l,4,2-dioxan-2- or 3- or 5- or 6- or 7-yl, 2,5-dihydro-l,4,2-dioxan-2- or 3- or 5- or 6- or 7-yl, 2,7-dihydro-l,4,2-dioxan-2- or 3- or 5- or 6- or 7-yl, 4,5-dihydro-l,4,2-dioxan-2- or 3- or 4- or 5- or 6- or 7-yl, 4,7-dihydro-l,4,2-dioxan-2- or 3- or 4- or 5- or 6- or 7-yl, 6,7-dihydro-l,4,2-dioxan-2- or 3- or 5- or 6- or 7-yl, l,4,2-dioxan-2- or 3- or 5- or 6- or 7-yl.2-Dioxazono-3- or 5- or 6- or 7-yl. Structural examples of heterocycles with optional further substitutions are also listed below:

[0092]

[0093]

[0094] The heterocycles listed above are preferably substituted with the following groups: for example, hydrogen, halogen, alkyl, haloalkyl, hydroxyl, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclic, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, trialkylsilylalkynyl, nitro, amino, cyano. Halogenated alkoxy, halogenated alkylthio, alkylthio, hydrogen thio, hydroxyalkyl, oxo, heteroarylalkoxy, arylalkoxy, heterocyclic alkoxy, heterocyclic alkylthio, heterocyclic thio, heteroaryloxy, dialkylamino, alkylamino, cycloalkylamino, hydroxycarbonylalkylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, alkoxycarbonylalkyl(alkyl)amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, cycloalkylaminocarbonyl, hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl, arylalkoxycarbonylalkylaminocarbonyl.

[0095] When the basic structure is replaced by "one or more groups" from a list of groups or a group of groups as generally defined, in each case this includes being replaced by multiple identical and / or structurally different groups simultaneously.

[0096] In the case of partially or fully saturated nitrogen heterocycles, this can be attached to the rest of the molecule via carbon or nitrogen.

[0097] Suitable substituents for the heterocyclic group are those further specified below, as well as oxo and thio groups. The oxo group, then, as a substituent on the ring carbon atom, is, for example, a carbonyl group in the heterocycle. Therefore, lactones and lactams are preferably also included. The oxo group can also appear on the ring heteroatom, which can exist in different oxidation states, for example in the cases of N and S, and in this case, divalent -N(O)-, S(O)- (also simply SO), and -S(O)2- (also simply SO2) groups are formed in the heterocycle. In the cases of -N(O)- and -S(O)- groups, both enantiomers are included in each case.

[0098] According to the present application, the expression "heteroaryl" denotes a heteroaromatic compound, i.e. a fully unsaturated aromatic heterocyclic compound, preferably a 5- to 7-membered ring having 1 to 4, preferably 1, 2 or 3, identical or different heteroatoms (preferably O, S or N). Heteroaryl groups according to the present application are, for example, 1 H-pyrrol-1 -yl, 1 H-pyrrol-2-yl, 1 H-pyrrol-3-yl, furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, 1 H-imidazol-1 -yl, 1 H-imidazol-2-yl, 1 H-imidazol-4-yl, 1 H-imidazol-5-yl, 1 H-pyrazol-1 -yl, 1 H-pyrazol-3-yl, 1 H-pyrazol-4-yl, 1 H-pyrazol-5-yl, 1 H-1,2,3-triazol-1 -yl, 1 H-1,2,3-triazol-4-yl, 1 H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1 H-1,2,4-triazol-1 -yl, 1 H-1,2,4-triazol-3-yl, 4H-1,2,4-triazol-4-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,5-oxadiazol-3-yl, azepinyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl, pyridazin-4-yl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl, 1,2,3-triazin-4-yl, 1,2,3-triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 1,3-oxazol-2-yl, 1,3-oxazol-4-yl, 1,3-oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,3-thiazol-2-yl, 1,3-thiazol-4-yl, 1,3-thiazol-5-yl, 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 and 1,2,4-diazepinyl, 2H-1,2,3,4-tetrazol-5-yl, 1 H-1,2,3,4-tetrazol-5-yl, 1,2,3,4-oxatriazol-5-yl, 1,2,3,4-thiatriazol-5-yl, 1,2,3,5-oxatriazol-4-yl, 1,2,3,5-thiatriazol-4-yl.The heteroaryl groups of the present application can also be substituted with one or more groups, which are the same or different. If two adjacent carbon atoms are part of another aromatic ring, the system is a fused heteroaromatic system, for example benzo-fused or polycyclic heteroaromatic compounds. Preferred examples are quinoline (e.g. quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl), isoquinoline (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, phtalazine, pyrido-pyrazine, pyrido-pyrimidine, pyrido-pyridazine, pteridine, pyrimido-pyrimidine.Examples of heteroaryl groups are also 5- or 6-membered benzo-fused rings from the group consisting of 1 H-indol-1 -yl, 1 H-indol-2-yl, 1 H-indol-3-yl, 1 H-indol-4-yl, 1 H-indol-5-yl, 1 H-indol-6-yl, 1 H-indol-7-yl, 1 -benzo furan-2-yl, 1 -benzo furan-3-yl, 1 -benzo furan-4-yl, 1 -benzo furan-5-yl, 1 -benzo furan-6-yl, 1 -benzo furan-7-yl, 1 -benzo thiophen-2-yl, 1 -benzo thiophen-3-yl, 1 -benzo thiophen-4-yl, 1 -benzo thiophen-5-yl, 1 -benzo thiophen-6-yl, 1 -benzo thiophen-7-yl, 1 H-indazol-1 -yl, 1 H-indazol-3-yl, 1 H-indazol-4-yl, 1 H-indazol-5-yl, 1 H-indazol-6-yl, 1 H-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, 1 H-benzimidazol-1 -yl, 1 H-benzimidazol-2-yl, 1 H-benzimidazol-4-yl, 1 H-benzimidazol-5-yl, 1 H-benzimidazol-6-yl, 1 H-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-benzothiazol-2-yl, 1,3-benzothiazol-4-yl, 1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl, 1,3-benzothiazol-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.

[0099] The term "halogen" denotes, for example, fluorine, chlorine, bromine or iodine. If the term is used for a group, "halogen" denotes, for example, a fluorine, chlorine, bromine or iodine atom.

[0100] According to the present application, "alkyl" means straight-chain or branched-chain open-chain saturated hydrocarbon radicals, which are optionally mono- or polysubstituted and in the latter case are referred to as "substituted alkyl". Preferred substituents are halogen atoms, alkoxy radicals, halogenalkoxy radicals, cyano radicals, alkylthio radicals, halogenalkylthio radicals, cycloalkyl radicals, alkoxycarbonyl radicals, hydroxycarbonyl radicals, heterocyclyl radicals, heteroaryl radicals, aryl radicals, amino radicals or nitro radicals, particularly preferred are methoxy radicals, methyl radicals, fluoroalkyl radicals, cyano radicals, nitro radicals, fluorine, chlorine, bromine or iodine. The prefix "di" also includes combinations of different alkyl radicals, for example methyl(ethyl) or ethyl(methyl).

[0101] "Haloalkyl", "haloalkenyl" and "haloalkynyl" mean alkyl, alkenyl and alkynyl radicals, respectively, which are partially or completely substituted by identical or different halogen atoms, for example monohaloalkyl such as CH2CH2CI, CH2CH2Br, CHC1CH3, CH2CI, CH2F; perhaloalkyl such as CCI3, CCIF2, CFCI2, CF2CCIF2, CF2CCIFCF3; polyhaloalkyl, for example CH2CHFCl, CF2CCIFH, CF2CBrFH, CH2CF3; the term perhaloalkyl also includes the term perfluoroalkyl.

[0102] "Haloalkoxy" is, for example, OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3and OCH2CH2CI; this applies correspondingly to haloalkenyl and other halogen-substituted radicals.

[0103] The expression "(C1-C4)-alkyl" mentioned herein by way of example is a shorthand for straight-chain or branched-chain alkyl radicals having from 1 to 4 carbon atoms according to the stated carbon atom range, i.e. includes methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radicals. General alkyl radicals having a greater specified carbon atom range, for example "(C1-C6)-alkyl", also include straight-chain or branched-chain alkyl radicals having a greater number of carbon atoms accordingly, i.e. according to the example also include alkyl radicals having 5 and 6 carbon atoms.

[0104] Unless stated otherwise, in the case of hydrocarbon radicals, for example alkyl, alkenyl and alkynyl, including hydrocarbon radicals in complex radicals, lower carbon skeletons are preferred, for example having from 1 to 6 carbon atoms, or in the case of unsaturated radicals having from 2 to 6 carbon atoms. Alkyl radicals, including alkyl radicals in complex radicals such as alkoxy, haloalkyl and the like, are, for example, methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, tert-butyl or 2-butyl, pentyl, hexyl such as n-hexyl, isohexyl and 1,3-dimethylbutyl, heptyl such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl are defined as the possible unsaturated radicals corresponding to the alkyl radicals, in which at least one double or triple bond is present. Radicals having one double or triple bond are preferred.

[0105] The term "alkenyl" also specifically includes straight-chain or branched-chain open-chain hydrocarbon radicals having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, and propadienyl or cumulated polyenyl radicals having one or more cumulated double bonds, such as propadienyl (1,2- propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl. Alkenyl denotes, for example, vinyl, which can optionally be substituted by a further alkyl group, such as, but not limited to, (C2-C6)-alkenyl, for example vinyl, 1-propenyl, 2-propenyl, 1-methylvinyl, 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 and 1-ethyl-2-methyl-2-propenyl.

[0106] The term "alkynyl" also includes, in particular, straight-chain or branched-chain open-chain hydrocarbon radicals which have more than one triple bond, or which have one or more triple bonds and one or more double bonds, for example 1,3-butynyl or 3-pent-1 -yn-1 -yl. (C2-C6)-Alkynyl denotes, for example, ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2-propynyl, 1 -pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1 -methyl-2-butynyl, 1 -methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1 -butynyl, 1,1 -dimethyl-2-propynyl, 1 -ethyl-2-propynyl, 1 -hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1 -methyl-2-pentynyl, 1 -methyl-3-pentynyl, 1 -methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1 -pentynyl, 3-methyl-4-pentynyl, 4-methyl-1 -pentynyl, 4-methyl-2-pentynyl, 1,1 -dimethyl-2-butynyl, 1,1 -dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1 -butynyl, 1 -ethyl-2-butynyl, 1 -ethyl-3-butynyl, 2-ethyl-3-butynyl and 1 -ethyl-1 -methyl-2-propynyl.

[0107] The term "cycloalkyl" refers to a carbocyclic, saturated ring system, preferably having 3 to 8 ring carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio, halogenalkylthio, halogen, alkenyl, alkynyl, halogenalkyl, amino, alkylamino, dialkylamino, alkoxycarbonyl, hydroxycarbonyl, arylalkyloxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl. In the case of optionally substituted cycloalkyl, ring systems with substituents are included, which also include substituents with double bonds on the cycloalkyl group, such as alkylene, e.g. methylene. 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]heptan-2-yl, bicyclo[2.2.2]octan-2-yl, bicyclo[3.2.1]octan-2-yl, bicyclo[3.2.2]nonan-2-yl, adamant-1-yl and adamant-2-yl, as well as systems such as 1,1'-di(cyclopropyl)-1-yl, 1,1'-di(cyclopropyl)-2-yl. The term "(C3-C7)-cycloalkyl" is a shortening of cycloalkyl with 3 to 7 carbon atoms corresponding to the specified range of carbon atoms.

[0108] In the case of substituted cycloalkyl, spiro aliphatic systems are also included, such as spiro[2.2]pentan-1-yl, spiro[2.3]hexan-1-yl, spiro[2.3]hexan-4-yl, 3-spiro[2.3]hexan-5-yl, spiro[3.3]heptan-1-yl, spiro[3.3]heptan-2-yl.

[0109] "Cycloalkenyl" denotes a carbocyclic, non-aromatic, partially unsaturated ring system, preferably having 4 to 8 carbon atoms, such as 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1,4-cyclohexadienyl, also including substituents with double bonds on the cycloalkenyl group, such as alkylene, e.g. methylene. In the case of optionally substituted cycloalkenyl, the explanations for substituted cycloalkyl apply accordingly.

[0110] The term "alkylene", such as also (C1-C 10) in the form of alkylene denotes a straight-chain or branched-chain open-chain hydrocarbon group which is bonded via a double bond. The possible bonding sites of the alkylene group are naturally only the positions on the basic structure at which two hydrogen atoms can be replaced by a double bond; the group is, for example, =CH2, =CH-CH3, =C(CH3)-CH3, =C(CH3)-C2H5or =C(C2H5)-C2H5. Cycloalkylene denotes a carbocyclic group which is bonded via a double bond.

[0111] "Partially fluorinated alkyl" denotes a straight-chain or branched-chain saturated hydrocarbon which is mono- or poly-substituted by fluorine, wherein the fluorine atoms in question can be present as substituents on one or more different carbon atoms of the straight-chain or branched-chain hydrocarbon chain, for example CHFCH3, CH2CH2F, CH2CH2CF3, CHF2, CH2F, CHFCF2CF3.

[0112] "Aryloxyalkyl" denotes an aryloxy group which is bonded via an alkyl group, "heteroaryloxyalkyl" denotes a heteroaryloxy group which is bonded via an alkyl group, and "heterocyclyloxyalkyl" denotes a heterocyclyloxy group which is bonded via an alkyl group.

[0113] "Aryloxyalkyl" denotes an aryloxy group which is bonded via an alkyl group, "heteroaryloxyalkyl" denotes a heteroaryloxy group which is bonded via an alkyl group, and "heterocyclyloxyalkyl" denotes a heterocyclyloxy group which is bonded via an alkyl group.

[0114] "Cycloalkylalkyl" denotes a cycloalkyl group which is 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.

[0115] "Halogenocycloalkyl" denotes a cycloalkyl group which is partially or completely substituted by identical or different halogen atoms (for example F, Cl and Br) or halogenated alkyl groups (for example trifluoromethyl or difluoromethyl), for example 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.

[0116] According to the application, "haloalkylthio", by itself or as a constituent of a chemical group, is a straight-chain or branched S-haloalkyl radical, preferably having from 1 to 8 or having from 1 to 6 carbon atoms, for example (Ci-C8)-, (Ci-C6)- or (Ci-C4)-haloalkylthio, such as, but not limited to, trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio, 3,3,3-prop-1-ylthio.

[0117] If a compound can form tautomers, which are not structurally covered by the general formula (I) in form, these tautomers are still included in the definition of the compounds of the general formula (I) of the present application, unless a specific tautomer is under investigation. For example, many carbonyl compounds can exist in the keto form and in the enol form, both forms being included in the definition of the compounds of the general formula (I).

[0118] Depending on the nature of the substituents and the way they are attached, the compounds of the general formula (I) can exist in the form of stereoisomers. The possible stereoisomers, such as enantiomers, diastereomers, Z and E isomers, which are defined by their specific three-dimensional form, are all encompassed by the general formula (I). For example, if one or more alkenyl groups are present, diastereomeric (Z and E isomers) can occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers can occur. The stereoisomers can be obtained from mixtures obtained in the preparation process by conventional separation methods. Analytical scale chromatographic separation can be carried out to find enantiomeric or diastereomeric excess, or preparative scale chromatographic separation can be carried out to prepare test samples for biological testing. Likewise, the stereoisomers can be prepared selectively by using optically active starting materials and / or auxiliaries in stereoselective reactions. The present application therefore also relates to all stereoisomers encompassed by the general formula (I) but not shown in their specific stereoisomeric form, and mixtures thereof.

[0119] If the compounds are obtained in solid form, they can also be purified by recrystallization or leaching. If the individual compounds (I) cannot be obtained in a satisfactory manner by the routes described below, they can be prepared by derivatization of other compounds (I).

[0120] Suitable separation methods, purification methods and methods for separating the stereoisomers of the compounds of general formula (I) are those generally known to the person skilled in the art from analogous situations, for example by physical methods such as crystallization, chromatography, in particular column chromatography and HPLC (high-performance liquid chromatography), distillation, optionally under reduced pressure, extraction and other methods, any remaining mixtures usually being separable by chromatographic separation methods, for example on chiral solid phases. Suitable for preparative amounts or on an industrial scale are, for example, methods of crystallization, for example crystallization of diastereomeric salts, which can be obtained from diastereomeric mixtures using optically active acids, and if appropriate, using optically active bases (provided that acidic groups are present).

[0121] Synthesis of [(1-phenyl-5-(heteroaryl)-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives of general formula (I)

[0122]

[0123] The [(1-phenyl-5-(heteroaryl)-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives of general formula (I) according to the application can be prepared from known methods. The synthesis routes used and investigated start from commercially available or easily prepared substituted heteroaryl carboxylic acids, corresponding substituted heteroaryl carboxamides and commercially available chemicals such as substituted phenylhydrazines and diphenyl carbonate. In the following schemes, the moieties R 1 , R 2 , R 3 , R 4 , m and p have the meanings defined above.

[0124] The compounds according to the application of general formula (Ia) are synthesized by reaction of a compound of general formula (II) with a compound of general formula (III) in the presence of a base, for example potassium carbonate. The reaction is preferably carried out in a suitable solvent, for example acetonitrile, at a temperature in the range from 0 °C to 120 °C (see Scheme 1).

[0125]

[0126] wherein X = halogen and R = (Ci-C4)-alkyl.

[0127] Scheme 1.

[0128] The compounds of general formula (II) are synthesized by cyclization of a compound of general formula (IV) in the presence of a condensing agent, for example polyphosphoric acid. The reaction is preferably carried out in neat form at a temperature in the range from 0 °C to 180 °C (see Scheme 2).

[0129]

[0130] Scheme 2.

[0131] The synthesis of compounds of general formula (IV) can be prepared by reaction of compounds of general formula (V) with phenylhydrazine of general formula (VI) in a suitable solvent (e.g. acetonitrile) at a temperature range of -20 °C to 100 °C, preferably -5 °C to 50 °C. The reaction is carried out in the presence of a base (e.g. triethylamine). Instead of phenylhydrazine of general formula (VI), phenylhydrazine hydrohalides of general formula (VII) can also be used (Scheme 3).

[0132]

[0133] wherein X = halogen.

[0134] Scheme 3.

[0135] The synthesis of compounds of general formula (V) can be prepared by reaction of compounds of general formula (VIII) with diphenyl carbonate (IX) in the presence of a base (e.g. sodium hydride) (see Scheme 4). The reaction is preferably carried out in a suitable solvent (e.g. THF) at a temperature range of -20 °C to 150 °C. Compounds of general formula (VIII) and (IX) are commercially available or can be prepared analogously to methods known to the person skilled in the art.

[0136]

[0137] Scheme 4.

[0138] The synthesis of acids of general formula (X) is prepared by hydrolysis of compounds of general formula (la) or by analogous methods known to the person skilled in the art.

[0139] The hydrolysis 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 (e.g. lithium, sodium or potassium; Scheme 5), the hydrolysis reaction is preferably carried out at a temperature range of room temperature to 100 °C. The Lewis acid can be boron tribromide, the reaction can be carried out at a temperature range of -20 °C to 100 °C, preferably -5 °C to 50 °C.

[0140]

[0141] wherein R = (Ci-C4)-alkyl.

[0142] Scheme 5.

[0143] The compounds of the application of general formula (XI) are synthesized by esterification of an acid of general formula (X) with an alcohol of general formula (XII) in the presence of a coupling reagent (such as T3P, dicyclohexylcarbodiimide, N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide, N,N'- carbonyldiimidazole, 2-chloro-l,3-dimethylimidazolium chloride or 2-chloro-l- 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 is preferably carried out in a suitable 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-ene) at a temperature ranging from 0 °C to 80 °C (see Scheme 6). For T3P coupling conditions, see Organic Process Research & Development 2009, 13, 900-906.

[0144]

[0145] Scheme 6.

[0146] Scheme 7 illustrates the synthesis of compounds of general formula (II); the synthesis is carried out by reaction of a compound of general formula (XIII) in the presence of a Bronsted acid (such as 33% HBr in acetic acid). The reaction is preferably carried out at a temperature ranging from 0 °C to 180 °C. See Bioorganic & Medicinal Chemistry 2018, 26, 3321-3344.

[0147]

[0148] Scheme 7.

[0149] Compounds of general formula (XIII) can be prepared by reaction of a compound of general formula (XIV) and a phenylhydrazine of general formula (VI) in a suitable solvent (such as ethanol) (see Scheme 8). The reaction is preferably carried out at a temperature ranging from 0 °C to 150 °C.

[0150]

[0151] Scheme 8.

[0152] Compounds of general formula (XIV) can be prepared by reacting heteroaryl carboxyl chlorides of general formula (XV) with thiocyanates of general formula (XVI) in the presence of methanol in a suitable solvent (e.g., acetone) (see Scheme 9). The heteroaryl carboxyl chlorides are commercially available or can be prepared by methods similar to those known to those skilled in the art. See Tetrahedron 1968, 24, 5205-5214; J. Chem. Soc. 1957, 1091; JP81 53, 664 (1981); Justus Liebigs Ann. Chem. 1964, 675, 180 and J. heterocycl. Chem. 1983, 20, 1533.

[0153]

[0154] Where X = fluorine, chlorine, bromine.

[0155] Option 9.

[0156] Detailed synthetic examples of the compounds of the present invention of general formula (I) are given below. The referenced example numbers correspond to the numbering scheme in Tables I.1 to I.83 below. The chemical examples described in the following sections record... 1 H NMR, 13 CNMR and 19 F NMR spectral data ( 1 H NMR is 400MHz 13 C NMR at 150 MHz and 19 F NMR (375 MHz, solvents CDCl3, CD3OD, or d6-DMSO, internal standard: tetramethylsilane δ = 0.00 ppm) was obtained on a Bruker instrument, and the listed signals have the following meanings: br = broad peak, s = singlet, d = doublet, t = triplet, dd = doublet, ddd = double doublet, m = multiplet, q = quartet, quintet, sext = sextet, sept = septet, dq = double quartet, dt = double triplet. In the case of diastereomer mixtures, significant signals for each of the two diastereomers were recorded, or the characteristic signal of the dominant diastereomer was recorded. The abbreviations used for chemical groups have, for example, the following meanings: Me = CH3, Et = CH2CH3, t-Hex = C(CH3)2CH(CH3)2, t-Bu = C(CH3)3, n-Bu = unbranched butyl, n-Pr = unbranched propyl, i-Pr = branched propyl, c-Pr = cyclopropyl, c-Hex = cyclohexyl.

[0157] Synthesis Example:

[0158] Synthesis Example No.: I.80-38

[0159] Synthesis Step 1 : 5-Chloropyridine-2-carboxamide

[0160]

[0161] Synthesis Step 1 : 5-Chloropyridine-2-carboxamide 1 H-NMR (400 MHz, DMSO-d 6 δ, ppm) 8.68 (bs, 1 H), 8.18-8.10 (m, 2H), 8.05 (m, 1 H), 7.73 (bs, 1 H).

[0162] Synthesis Step 2: [(5-Chloropyridin-2-yl)carbonyl]phenylcarbamate

[0163]

[0164] Under an argon atmosphere, 5-chloropyridin-2-carboxamide (2.50 g, 15.97 mmol, 1.0 equivalent) and diphenyl carbonate (5.13 g, 23.95 mmol, 1.5 equivalent) were dissolved in THF (50 mL) and cooled to 0 °C in an ice bath. Sodium hydride (60%, in mineral oil, 0.64 g, 63.65 mmol, 1.0 equivalent) was added to the solution in portions. Note: Gas escape! Subsequently, the ice bath was removed and the reaction mixture was stirred at room temperature for 1 h. The reaction mixture was then concentrated to 1 / 3 under reduced pressure to form a flaky white solid. The resulting solid was filtered off and dried in air. [(5-chloropyridin-2-yl)carbonyl]phenyl carbamate (3.94 g, 89% of theoretical value) was isolated as a white solid. 1H-NMR (400MHz, DMSO-d6δ, ppm) 9.38 (bs, 1H), 8.68 (d, 1H), 8.13-8.03 (m, 2H), 7.17-7.13 (m, 2H), 6.77-6.74 (m, 3H).

[0165] Synthesis Step 3: 5-Chloro-N-{[2-(2,4-difluorophenyl)hydrazino]carbonyl}pyridine-2-carboxamide

[0166]

[0167] [(5-chloropyridin-2-yl)carbonyl]phenyl carbamate (1.00 g, 3.61 mmol, 1.0 equivalent) was dissolved in acetonitrile (50 mL), and then the following substances were added at room temperature: (2,4-difluorophenyl)hydrazine hydrochloride (1:1) (0.72 g, 3.98 mmol, 1.1 equivalent) and triethylamine (1.51 mL, 10.84 mmol, 2.0 equivalent). After about 15–30 min, the solution turned pink and a beige solid precipitated. The reaction mixture was stirred at room temperature for 1 h, and then the resulting precipitate was filtered off and dried in air. 5-chloro-N-{[2-(2,4-difluorophenyl)hydrazine]carbonyl}pyridin-2-carboxamide (0.87 g, 66% of theoretical value, 90% purity) was isolated as a beige solid. 1 H-NMR (400MHz, DMSO-d) 6 δ,ppm)9.69(bs,1H),8.80(m,1H),8.25-8.10(m,4H),7.83(m,1H),7.16(m,1H),6.92-6.86(m,1H).

[0168] Synthetic step 4: 5-(5-chloropyridin-2-yl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-ol

[0169]

[0170] 5-chloro-N-{[2-(2,4-difluorophenyl)hydrazono]carbonyl}pyridine-2-carboxamide (0.4 g, 1.22 mmol, 1.0 equiv) was blended in polyphosphoric acid (10 g) and then left to liquefy the reaction mixture at 100 °C for 2 h. After cooling to room temperature, the reaction mixture was added dropwise to ice water and the light beige precipitate was suction filtered. The suction filtered precipitate was dried in a vacuum oven at 55 °C. 5-(5-chloropyridin-2-yl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-ol was isolated as a light beige solid (294 mg, 70% of theory, 90% purity).1H-NMR (400 MHz, CDC13 δ, ppm) 13.25 (bs, 1H), 8.32 (s, 1H), 8.05 (d, 1H), 7.82 (dd, 1H), 7.55 (m, 1H), 7.03 (m, 1H), 6.91 (m, 1H).

[0171] Synthesis Step 5: {[5-(5-chloropyridin-2-yl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3- yl]oxy}acetic acid methyl ester (Synthesis Example 1.28-38)

[0172]

[0173] 5-(5-chloropyridin-2-yl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-ol (250 mg, 0.81 mmol, 1.0 equiv) and potassium carbonate (336 mg, 2.43 mmol, 3 equiv) were suspended in acetonitrile (25 ml) and then methyl bromoacetate (149 mg, 0.97 mmol, 1.2 equiv) was added. The suspension was then stirred at room temperature overnight, the solids were filtered off and the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate / heptane gradient). {[5-(5-chloropyridin-2-yl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid methyl ester was isolated as a colorless oil (290 mg, 94% of theory).1H-NMR (400 MHz, CDC13 δ, ppm) 8.26 (d, 1H), (.11 (dd, 1H), 7.76 (dd, 1H), 7.49 (m, 1H), 6.98 (m, 1H), 6.89 (m, 1H), 4.94 (s, 2H), 3.81 (s, 3H).

[0174] Synthesis Step 6: {[5-(5-chloropyridin-2-yl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3- yl]oxy}acetic acid (Synthesis Example 1.30-38)

[0175]

[0176] Methyl {[5-(5-chloropyridin-2-yl)-l-(2,4-difluorophenyl)-lH-l,2,4-triazol-3- yl]oxy}acetate (290 mg, 0.76 mmol, 1.0 equiv) and lithium hydroxide (55 mg, 2.29 mmol, 1 equiv) were dissolved in a THF / water mixture (7:2, 20 ml) and stirred at room temperature for 1 h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in water, adjusted to pH = 2 with 2M hydrochloric acid, and a light yellow solid precipitated. The precipitate was suction filtered and dried in a vacuum oven at 55 °C. {[5-(5-Chloropyridin-2-yl)-l-(2,4-difluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetic acid was isolated as a light yellow solid (267 mg, 86% of theory). 1 H-NMR (400 MHz, DMSO-d 6 δ, ppm) 13.13 (bs, 1H), 8.45 (d, 1H), 8.14-8.07 (m, 2H), 7.69 (m, 1H), 7.50 (m, 1H), 7.25 (m, 1H), 4.88 (s, 2H).

[0177] Synthesis Step 7: {[5-(5-Chloropyridin-2-yl)-l-(2,4-difluorophenyl)-lH-l,2,4-triazol-3- yl]oxy}acetyl chloride

[0178]

[0179] {[5-(5-Chloropyridin-2-yl)-l-(2,4-difluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetic acid (270 mg, 0.74 mmol, 1.0 equiv) and one drop of DMF were dissolved in DCM (12 ml) followed by the addition of oxalyl chloride (0.13 ml, 1.47 mmol, 2 equiv) (note: gas evolution). Subsequently, the reaction mixture was stirred at 40 °C until gas evolution ceased. The reaction mixture was concentrated under reduced pressure. The residue was used in the next step of the synthesis without further purification. {[5-(5-Chloropyridin-2-yl)-l-(2,4-difluorophenyl)-lH-l,2,4-triazol-3- yl]oxy}acetyl chloride was isolated as a yellow oil (320 mg).

[0180] Synthesis Step 8: {[5-(5-Chloropyridin-2-yl)-l-(2,4-difluorophenyl)-lH-l,2,4-triazol-3- yl]oxy}acetic acid cyclopropylmethyl ester (Synthesis Example 1.80 - 38)

[0181]

[0182] Cyclopropylmethanol (38 mg, 0.52 mmol, 2.50 equiv), triethylamine (0.203 ml, 1.45 mmol, 7 equiv) and one grain of DMAP were dissolved in DCM (6 ml) and then {[5-(5-chloropyridin-2-yl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetyl chloride (250 mg, 0.81 mmol, 1.0 equiv) dissolved in DCM (1 ml) was added. Then the reaction mixture was stirred at room temperature overnight, water (3 ml) was added and the organic phase was separated and dried over sodium sulfate. Then the organic phase was concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate / heptane gradient). {[5-(5-Chloropyridin-2-yl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3- yl]oxy}cyclopropylmethyl acetate was isolated as a colorless oil (42 mg, 45% of theory). 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.26 (s, 1H), 8.11 (d, 1H), 7.26 (dd, 1H), 7.48 (m, 1H), 6.98 (m, 1H), 6.89 (m, 1H), 4.95 (s, 2H), 4.05 (d, 2H), 1.15 (m, 1H), 0.57-0.52 (m, 2H), 0,30-0.26 (m, 2H).

[0183] In analogy to the preparation examples cited above and stated in the appropriate places, and taking into account the general details relating to the preparation of [(1-phenyl-5-(heteroaryl)-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives, the following compounds were obtained:

[0184]

[0185] Table I.1: Preferred compounds of formula (I.1) are compounds I.1-1 to I.1-53 in which Q has the meaning indicated in each row of the table. Thus, the compounds I.1-1 to I.1-53 of Table I.1 are defined by the meaning of each entry number 1 to 53 of Q in the table.

[0186] Table 1:

[0187]

[0188]

[0189]

[0190]

[0191] Table I.2: Preferred compounds of formula (I.2) are the compounds I.2-1 to I.2-53 in which Q has the meanings indicated in the respective lines of Table 1. Thus, the compounds I.2-1 to I.2-53 of Table I.2 are defined by the meanings of the respective entry numbers 1 to 53 of Q in Table 1.

[0192]

[0193] Table I.3: Preferred compounds of formula (I.3) are the compounds I.3-1 to I.3-53 in which Q has the meanings indicated in the respective lines of Table 1. Thus, the compounds I.3-1 to I.3-53 of Table I.3 are defined by the meanings of the respective entry numbers 1 to 53 of Q in Table 1.

[0194]

[0195] Table I.4: Preferred compounds of formula (I.4) are the compounds I.4-1 to I.4-53 in which Q has the meanings indicated in the respective lines of Table 1. Thus, the compounds I.4-1 to I.4-53 of Table I.4 are defined by the meanings of the respective entry numbers 1 to 53 of Q in Table 1.

[0196]

[0197] Table I.5: Preferred compounds of formula (I.5) are the compounds I.5-1 to I.5-53 in which Q has the meanings indicated in the respective lines of Table 1. Thus, the compounds I.5-1 to I.5-53 of Table I.5 are defined by the meanings of the respective entry numbers 1 to 53 of Q in Table 1.

[0198]

[0199] Table I.6: Preferred compounds of formula (I.6) are the compounds I.6-1 to I.6-53 in which Q has the meanings indicated in the respective lines of Table 1. Thus, the compounds I.6-1 to I.6-53 of Table I.6 are defined by the meanings of the respective entry numbers 1 to 53 of Q in Table 1.

[0200]

[0201] Table I.7: Preferred compounds of formula (I.7) are the compounds I.7-1 to I.7-53 in which Q has the meanings indicated in the respective lines of Table 1. Thus, the compounds I.7-1 to I.7-53 of Table I.7 are defined by the meanings of the respective entry numbers 1 to 53 of Q in Table 1.

[0202]

[0203] Table I.8: Preferred compounds of formula (I.8) are the compounds I.8-1 to I.8-53 in which Q has the meanings indicated in the respective lines of Table 1. Thus, the compounds I.8-1 to I.8-53 of Table I.8 are defined by the meanings of the respective entry numbers 1 to 53 of Q in Table 1.

[0204]

[0205] Table I.9: Preferred compounds of formula (I.9) are the compounds I.9-1 to I.9-53 in which Q has the meanings indicated in the respective lines of Table 1. Thus, the compounds I.9-1 to I.9-53 of Table I.9 are defined by the meanings of the respective entry numbers 1 to 53 of Q in Table 1.

[0206]

[0207] Table I.10: Preferred compounds of formula (I.10) are the compounds I.10-1 to I.10-53 in which Q has the meanings indicated in the respective lines of Table 1. Thus, the compounds I.10-1 to I.10-53 of Table I.10 are defined by the meanings of the respective entry numbers 1 to 53 of Q in Table 1.

[0208]

[0209] Table I.11: Preferred compounds of formula (I.11) are the compounds I.11-1 to I.11-53 in which Q has the meanings indicated in the respective lines of Table 1. Thus, the compounds I.11-1 to I.11-53 of Table I.11 are defined by the meanings of the respective entry numbers 1 to 53 of Q in Table 1.

[0210]

[0211] Table I.12: Preferred compounds of formula (I.12) are the compounds I.12-1 to I.12-53 in which Q has the meanings indicated in the respective lines of Table 1. Thus, the compounds I.12-1 to I.12-53 of Table I.12 are defined by the meanings of the respective entry numbers 1 to 53 of Q in Table 1.

[0212]

[0213] Table I.13: Preferred compounds of formula (I.13) are the compounds I.13-1 to I.13-53 in which Q has the meanings indicated in the respective lines of Table 1. Thus, the compounds I.13-1 to I.13-53 of Table I.13 are defined by the meanings of the respective entry numbers 1 to 53 of Q in Table 1.

[0214]

[0215] Table I.14: Preferred compounds of formula (I.14) are the compounds I.14-1 to I.14- 53, wherein Q has the meaning as indicated in each line of Table 1. Thus, the compounds I.14-1 to I.14-53 of Table I.14 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0216]

[0217] Table I.15: Preferred compounds of formula (I.15) are the compounds I.15-1 to I.15- 53, wherein Q has the meaning as indicated in each line of Table 1. Thus, the compounds I.15-1 to I.15-53 of Table I.15 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0218]

[0219] Table I.16: Preferred compounds of formula (I.16) are the compounds I.16-1 to I.16- 53, wherein Q has the meaning as indicated in each line of Table 1. Thus, the compounds I.16-1 to I.16-53 of Table I.16 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0220]

[0221] Table I.17: Preferred compounds of formula (I.17) are the compounds I.17-1 to I.17- 53, wherein Q has the meaning as indicated in each line of Table 1. Thus, the compounds I.17-1 to I.17-53 of Table I.17 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0222]

[0223] Table I.18: Preferred compounds of formula (I.18) are the compounds I.18-1 to I.18- 53, wherein Q has the meaning as indicated in each line of Table 1. Thus, the compounds I.18-1 to I.18-53 of Table I.18 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0224]

[0225] Table I.19: Preferred compounds of formula (I.19) are the compounds I.19-1 to I.19- 53, wherein Q has the meaning as indicated in each line of Table 1. Thus, the compounds I.19-1 to I.19-53 of Table I.19 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0226]

[0227] Table I.20: The preferred compounds of formula (I.20) are compounds I.20-1 to I.20-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.20-1 to I.20-53 of Table I.20 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0228]

[0229] Table I.21: The preferred compounds of formula (I.21) are compounds I.21-1 to I.21-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.21-1 to I.21-53 in Table I.21 are defined by the meaning of each entry numbered 1 to 53 of Q in Table 1.

[0230]

[0231] Table I.22: The preferred compounds of formula (I.22) are compounds I.22-1 to I.22-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.22-1 to I.22-53 of Table I.22 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0232]

[0233] Table I.23: The preferred compounds of formula (I.23) are compounds I.23-1 to I.23-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.23-1 to I.23-53 in Table I.23 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0234]

[0235] Table I.24: The preferred compounds of formula (I.24) are compounds I.24-1 to I.24-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.24-1 to I.24-53 of Table I.24 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0236]

[0237] Table I.25: The preferred compounds of formula (I.25) are compounds I.25-1 to I.25-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.25-1 to I.25-53 in Table I.25 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0238]

[0239] Table I.26: Preferred compounds of formula (I.26) are the compounds I.26-1 to I.26- 53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.26-1 to I.26-53 of Table I.26 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0240]

[0241] Table I.27: Preferred compounds of formula (I.27) are the compounds I.27-1 to I.27- 53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.27-1 to I.27-53 of Table I.27 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0242]

[0243] Table I.28: Preferred compounds of formula (I.28) are the compounds I.28-1 to I.28- 53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.28-1 to I.28-53 of Table I.28 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0244]

[0245] Table I.29: Preferred compounds of formula (I.29) are the compounds I.29-1 to I.29- 53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.29-1 to I.29-53 of Table I.29 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0246]

[0247] Table I.30: Preferred compounds of formula (I.30) are the compounds I.30-1 to I.30- 53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.30-1 to I.30-53 of Table I.30 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0248]

[0249] Table I.31 : Preferred compounds of formula (I.31 ) are the compounds I.31 -1 to I.31 - 53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.31 -1 to I.31 -53 of Table I.31 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0250]

[0251] Table I.32: Preferred compounds of formula (I.32) are the compounds I.32-1 to I.32-53, wherein Q has the meaning as indicated in each line of Table 1. Thus, the compounds I.32-1 to I.32-53 of Table I.32 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0252]

[0253] Table I.33: Preferred compounds of formula (I.33) are the compounds I.33-1 to I.33-53, wherein Q has the meaning as indicated in each line of Table 1. Thus, the compounds I.33-1 to I.33-53 of Table I.33 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0254]

[0255] Table I.34: Preferred compounds of formula (I.34) are the compounds I.34-1 to I.34-53, wherein Q has the meaning as indicated in each line of Table 1. Thus, the compounds I.34-1 to I.34-53 of Table I.34 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0256]

[0257] Table I.35: Preferred compounds of formula (I.35) are the compounds I.35-1 to I.35-53, wherein Q has the meaning as indicated in each line of Table 1. Thus, the compounds I.35-1 to I.35-53 of Table I.35 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0258]

[0259] Table I.36: Preferred compounds of formula (I.36) are the compounds I.36-1 to I.36-53, wherein Q has the meaning as indicated in each line of Table 1. Thus, the compounds I.36-1 to I.36-53 of Table I.36 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0260]

[0261] Table I.37: Preferred compounds of formula (I.37) are the compounds I.37-1 to I.37-53, wherein Q has the meaning as indicated in each line of Table 1. Thus, the compounds I.37-1 to I.37-53 of Table I.37 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0262]

[0263] Table I.38: Preferred compounds of formula (I.38) are the compounds I.38-1 to I.38- 53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.38-1 to I.38-53 of Table I.38 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0264]

[0265] Table I.39: Preferred compounds of formula (I.39) are the compounds I.39-1 to I.39- 53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.39-1 to I.39-53 of Table I.39 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0266]

[0267] Table I.40: Preferred compounds of formula (I.40) are the compounds I.40-1 to I.40- 53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.40-1 to I.40-53 of Table I.40 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0268]

[0269] Table I.41 : Preferred compounds of formula (I.41 ) are the compounds I.41 -1 to I.41 - 53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.41 -1 to I.41 -53 of Table I.41 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0270]

[0271] Table I.42: Preferred compounds of formula (I.42) are the compounds I.42-1 to I.42- 53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.42-1 to I.42-53 of Table I.42 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0272]

[0273] Table I.43: Preferred compounds of formula (I.43) are the compounds I.43-1 to I.43- 53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.43-1 to I.43-53 of Table I.43 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0274]

[0275] Table I.44: Preferred compounds of formula (I.44) are the compounds I.44-1 to I.44-53 in which Q has the meanings as indicated in the respective lines of Table 1. Thus, the compounds I.44-1 to I.44-53 of Table I.44 are defined by the meanings of the respective entry numbers 1 to 53 of Q in Table 1.

[0276]

[0277] Table I.45: Preferred compounds of formula (I.45) are the compounds I.45-1 to I.45-53 in which Q has the meanings as indicated in the respective lines of Table 1. Thus, the compounds I.45-1 to I.45-53 of Table I.45 are defined by the meanings of the respective entry numbers 1 to 53 of Q in Table 1.

[0278]

[0279] Table I.46: Preferred compounds of formula (I.46) are the compounds I.46-1 to I.46-53 in which Q has the meanings as indicated in the respective lines of Table 1. Thus, the compounds I.46-1 to I.46-53 of Table I.46 are defined by the meanings of the respective entry numbers 1 to 53 of Q in Table 1.

[0280]

[0281] Table I.47: Preferred compounds of formula (I.47) are the compounds I.47-1 to I.47-53 in which Q has the meanings as indicated in the respective lines of Table 1. Thus, the compounds I.47-1 to I.47-53 of Table I.47 are defined by the meanings of the respective entry numbers 1 to 53 of Q in Table 1.

[0282]

[0283] Table I.48: Preferred compounds of formula (I.48) are the compounds I.48-1 to I.48-53 in which Q has the meanings as indicated in the respective lines of Table 1. Thus, the compounds I.48-1 to I.48-53 of Table I.48 are defined by the meanings of the respective entry numbers 1 to 53 of Q in Table 1.

[0284]

[0285] Table I.49: Preferred compounds of formula (I.49) are the compounds I.49-1 to I.49-53 in which Q has the meaning as indicated in each line of Table 1. Thus, the compounds I.49-1 to I.49-53 of Table I.49 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0286]

[0287] Table I.50: Preferred compounds of formula (I.50) are the compounds I.50-1 to I.50-53 in which Q has the meaning as indicated in each line of Table 1. Thus, the compounds I.50-1 to I.50-53 of Table I.50 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0288]

[0289] Table I.51 : Preferred compounds of formula (I.51 ) are the compounds I.51 -1 to I.51 -53 in which Q has the meaning as indicated in each line of Table 1. Thus, the compounds I.51 -1 to I.51 -53 of Table I.51 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0290]

[0291] Table I.52: Preferred compounds of formula (I.52) are the compounds I.52-1 to I.52-53 in which Q has the meaning as indicated in each line of Table 1. Thus, the compounds I.52-1 to I.52-53 of Table I.52 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0292]

[0293] Table I.53: Preferred compounds of formula (I.53) are the compounds I.53-1 to I.53-53 in which Q has the meaning as indicated in each line of Table 1. Thus, the compounds I.53-1 to I.53-53 of Table I.53 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0294]

[0295] Table I.54: Preferred compounds of formula (I.54) are the compounds I.54-1 to I.54-53 in which Q has the meaning as indicated in each line of Table 1. Thus, the compounds I.54-1 to I.54-53 of Table I.54 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0296]

[0297] Table I.55: Preferred compounds of formula (I.55) are the compounds I.55-1 to I.55- 53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.55-1 to I.55-53 of Table I.55 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0298]

[0299] Table I.56: Preferred compounds of formula (I.56) are the compounds I.56-1 to I.56- 53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.56-1 to I.56-53 of Table I.56 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0300]

[0301] Table I.57: Preferred compounds of formula (I.57) are the compounds I.57-1 to I.57- 53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.57-1 to I.57-53 of Table I.57 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0302]

[0303] Table I.58: Preferred compounds of formula (I.58) are the compounds I.58-1 to I.58- 53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.58-1 to I.58-53 of Table I.58 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0304]

[0305] Table I.59: Preferred compounds of formula (I.59) are the compounds I.59-1 to I.59- 53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.59-1 to I.59-53 of Table I.59 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0306]

[0307] Table I.60: Preferred compounds of formula (I.60) are the compounds I.60-1 to I.60- 53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.60-1 to I.60-53 of Table I.60 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0308]

[0309] Table I.61 : Compounds of formula (I.61) which are preferred are compounds I.61-1 to I.61-53, wherein Q has the meaning as indicated in each row of Table 1. Thus, the compounds I.61-1 to I.61-53 of Table I.61 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0310]

[0311] Table I.62: Compounds of formula (I.62) which are preferred are compounds I.62-1 to I.62-53, wherein Q has the meaning as indicated in each row of Table 1. Thus, the compounds I.62-1 to I.62-53 of Table I.62 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0312]

[0313] Table I.63: Compounds of formula (I.63) which are preferred are compounds I.63-1 to I.63-53, wherein Q has the meaning as indicated in each row of Table 1. Thus, the compounds I.63-1 to I.63-53 of Table I.63 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0314]

[0315] Table I.64: Compounds of formula (I.64) which are preferred are compounds I.64-1 to I.64-53, wherein Q has the meaning as indicated in each row of Table 1. Thus, the compounds I.64-1 to I.64-53 of Table I.64 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0316]

[0317] Table I.65: Compounds of formula (I.65) which are preferred are compounds I.65-1 to I.65-53, wherein Q has the meaning as indicated in each row of Table 1. Thus, the compounds I.65-1 to I.65-53 of Table I.65 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0318]

[0319] Table I.66: Compounds of formula (I.66) which are preferred are compounds I.66-1 to I.66-53, wherein Q has the meaning as indicated in each row of Table 1. Thus, the compounds I.66-1 to I.66-53 of Table I.66 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0320]

[0321] Table I.67: Preferred compounds of formula (I.67) are the compounds I.67-1 to I.67-53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.67-1 to I.67-53 of Table I.67 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0322]

[0323] Table I.68: Preferred compounds of formula (I.68) are the compounds I.68-1 to I.68-53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.68-1 to I.68-53 of Table I.68 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0324]

[0325] Table I.69: Preferred compounds of formula (I.69) are the compounds I.69-1 to I.69-53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.69-1 to I.69-53 of Table I.69 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0326]

[0327] Table I.70: Preferred compounds of formula (I.70) are the compounds I.70-1 to I.70-53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.70-1 to I.70-53 of Table I.70 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0328]

[0329] Table I.71 : Preferred compounds of formula (I.71 ) are the compounds I.71 -1 to I.71 -53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.71 -1 to I.71 -53 of Table I.71 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0330]

[0331] Table I.72: Preferred compounds of formula (I.72) are the compounds I.72-1 to I.72-53, wherein Q has the meaning as given in each row of Table 1. Thus, the compounds I.72-1 to I.72-53 of Table I.72 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0332]

[0333] Table I.73: Preferred compounds of formula (I.73) are the compounds I.73-1 to I.73-53, wherein Q has the meaning as indicated in each row of Table 1. Thus, the compounds I.73-1 to I.73-53 of Table I.73 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0334]

[0335] Table I.74: Preferred compounds of formula (I.74) are the compounds I.74-1 to I.74-53, wherein Q has the meaning as indicated in each row of Table 1. Thus, the compounds I.74-1 to I.74-53 of Table I.74 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0336]

[0337] Table I.75: Preferred compounds of formula (I.75) are the compounds I.75-1 to I.75-53, wherein Q has the meaning as indicated in each row of Table 1. Thus, the compounds I.75-1 to I.75-53 of Table I.75 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0338]

[0339] Table I.76: Preferred compounds of formula (I.76) are the compounds I.76-1 to I.76-53, wherein Q has the meaning as indicated in each row of Table 1. Thus, the compounds I.76-1 to I.76-53 of Table I.76 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0340]

[0341] Table I.77: Preferred compounds of formula (I.77) are the compounds I.77-1 to I.77-53, wherein Q has the meaning as indicated in each row of Table 1. Thus, the compounds I.77-1 to I.77-53 of Table I.77 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0342]

[0343] Table I.78: Preferred compounds of formula (I.78) are the compounds I.78-1 to I.78-53, wherein Q has the meaning as indicated in each row of Table 1. Thus, the compounds I.78-1 to I.78-53 of Table I.78 are defined by the meaning of each entry No. 1 to 53 of Q in Table 1.

[0344]

[0345] Table I.79: Preferred compounds of formula (I.79) are the compounds I.79-1 to I.79-53 in which Q has the meanings indicated in each row of Table 1. Thus, the compounds I.79-1 to I.79-53 of Table I.79 are defined by the meanings of the individual entries No. 1 to 53 of Q in Table 1.

[0346]

[0347] Table I.80: Preferred compounds of formula (I.80) are the compounds I.80-1 to I.80-53 in which Q has the meanings indicated in each row of Table 1. Thus, the compounds I.80-1 to I.80-53 of Table I.80 are defined by the meanings of the individual entries No. 1 to 53 of Q in Table 1.

[0348]

[0349] Table I.81 : Preferred compounds of formula (I.81 ) are the compounds I.81 -1 to I.81 -53 in which Q has the meanings indicated in each row of Table 1. Thus, the compounds I.81 -1 to I.81 -53 of Table I.81 are defined by the meanings of the individual entries No. 1 to 53 of Q in Table 1.

[0350]

[0351] Table I.82: Preferred compounds of formula (I.82) are the compounds I.82-1 to I.82-53 in which Q has the meanings indicated in each row of Table 1. Thus, the compounds I.82-1 to I.82-53 of Table I.82 are defined by the meanings of the individual entries No. 1 to 53 of Q in Table 1.

[0352]

[0353] Table I.83: Preferred compounds of formula (I.83) are the compounds I.83-1 to I.83-53 in which Q has the meanings indicated in each row of Table 1. Thus, the compounds I.83-1 to I.83-53 of Table I.83 are defined by the meanings of the individual entries No. 1 to 53 of Q in Table 1.

[0354] Spectral data of selected table examples:

[0355] Selected detailed synthesis examples of compounds of the present application of general formula (I) are listed below. The chemical examples described in the following sections are recorded in the order of their appearance. 1 H NMR, 13 C-NMR and 19F-NMR spectral data 1 HNMR is 400 MHz, 13 C-NMR is 150 MHz and 19 F-NMR is 375 MHz, solvent CDCl3, CD3OD or d6-DMSO, internal standard: tetramethylsilane δ = 0.00 ppm) were obtained on Bruker instruments and the listed signals have the meanings given below: br = broad, s = singlet, d = doublet, t = triplet, dd = doublet of doublets, ddd = doublet of doublet of doublets, m = multiplet, q = quartet, quint = quintet, sext = sextet, sept = septet, dq = doublet of quartet, dt = doublet of triplet. In the case of diastereomeric mixtures, the individual significant signals of the two diastereomers were recorded, or the characteristic signals of the main diastereomer were recorded. The abbreviations for chemical groups have, for example, the following meanings: Me = CH3, Et = CH2CH3, t-Hex = C(CH3)2CH(CH3)2, t-Bu = C(CH3)3, n-Bu = unbranched butyl, n-Pr = unbranched propyl, i-Pr = branched propyl, c-Pr = cyclopropyl, c-Hex = cyclohexyl.

[0356] The spectral data of the selected table examples listed below were obtained by conventional 1 H NMR interpretation or by NMR peak list method.

[0357] Conventional 1 H NMR interpretation

[0358] Example No. I.29-48:

[0359] 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.22 (d, 1H), 8.11 (d, 1H), 7.75 (dd, 1H), 7.46 (dd, 1H), 7.21 (dd, 1H), 7.09 (m, 1H), 4.92 (s, 2H), 4.27 (q, 2H), 1.29 (t, 3H).

[0360] Example No. I.28-4:

[0361] 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.33 (d, 1H), 7.98 (dd, 1H), 7.75 (dd, 1H), 7.37-7.33 (m, 2H), 7.11-7.07 (m, 2H), 4.95 (s, 2H), 3.81 (s, 3H).

[0362] Example No. I.32-48:

[0363] 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.18 (dd, 1H), 8.12 (d, 1H), 7.50-7.45 (m, 2H), 7.20 (dd, 1H), 7.09 (m, 1H), 4.92 (s, 2H), 4.27 (q, 2H), 1.29 (t, 3H).

[0364] Example No. I.32-2:

[0365] 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.17-8.14 (m, 2H), 7.54-7.39 (m, 3H), 7.25 (m, 1H), 7.12 (m, 1H), 4.93 (s, 2H), 4.28 (q, 2H), 1.29 (t, 3H).

[0366] Example No. I.32-4:

[0367] 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.24 (d, 1H), 8.04 (dd, 1H), 7.48 (m, 1H), 7.36-7.33 (m, 2H), 7.11-7.06 (m, 2H), 4.93 (s, 2H), 4.27 (q, 2H), 1.30 (t, 3H).

[0368] Example No. I.30-49:

[0369] 1 H-NMR (400 MHz, DMSO-d6 δ, ppm) 8.47 (d, 1H), 8.15-8.07 (m, 2H), 7.70-7.63 (m, 2H), 7.45 (m, 1H), 4.85 (s, 2H).

[0370] Example No. I.30-7:

[0371] 1 H-NMR (400 MHz, DMSO-d6 δ, ppm) 13.12 (bs, 1H), 8.51 (d, 1H), 8.12 (dd, 1H), 7.99 (d, 1H), 7.52 (d, 2H), 7.42 (d, 2H), 4.87 (s, 2H).

[0372] Example No. I.29-2:

[0373] 1H-NMR (400 MHz, CDC13 δ, ppm) 8.25 (d, 1H), 8.08 (dd, 1H), 7.75 (dd, 1H), 7.52 (m, 1H), 7.43 (m, 1H), 7.24 (m, 1H), 7.12 (m, 1H), 4.93 (s, 2H), 4.28 (q, 2H), 1.29 (t, 3H).

[0374] Example No. I.33-48:

[0375] 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.25 (d, 1H), 8.08 (dd, 1H), 7.75 (dd, 1H), 7.52 (m, 1H), 7.43 (m, 1H), 7.24 (m, 1H), 7.12 (m, 1H), 4.93 (s, 2H), 4.28 (q, 2H), 1.29 (t, 3H).

[0376] Example No. I.71-38:

[0377] 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.25 (d, 1H), 8.08 (dd, 1H), 7.75 (dd, 1H), 7.52 (m, 1H), 7.43 (m, 1H), 7.24 (m, 1H), 7.12 (m, 1H), 4.93 (s, 2H), 4.28 (q, 2H), 1.29 (t, 3H).

[0378] Example No. I.33-2:

[0379] 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.25 (d, 1H), 8.08 (dd, 1H), 7.75 (dd, 1H), 7.52 (m, 1H), 7.43 (m, 1H), 7.24 (m, 1H), 7.12 (m, 1H), 4.93 (s, 2H), 4.28 (q, 2H), 1.29 (t, 3H).

[0380] Example No. I.31-49:

[0381] 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.25 (d, 1H), 8.08 (dd, 1H), 7.75 (dd, 1H), 7.52 (m, 1H), 7.43 (m, 1H), 7.24 (m, 1H), 7.12 (m, 1H), 4.93 (s, 2H), 4.28 (q, 2H), 1.29 (t, 3H).

[0382] Example No. I.31-38:

[0383] 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.20-8.16 (m, 2H), 7.52-7.46 (m, 2H), 6.99 (m, 1H), 6.88 (m, 1H), 4.94 (s, 2H), 3.81 (s, 3H).

[0384] Example No. I.29-4:

[0385] 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.20-8.16 (m, 2H), 7.52-7.46 (m, 2H), 6.99 (m, 1H), 6.88 (m, 1H), 4.94 (s, 2H), 3.81 (s, 3H).

[0386] Example No. I.29-38:

[0387] 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.20-8.16 (m, 2H), 7.52-7.46 (m, 2H), 6.99 (m, 1H), 6.88 (m, 1H), 4.94 (s, 2H), 3.81 (s, 3H).

[0388] Example No. I.30-38:

[0389] 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.20-8.16 (m, 2H), 7.52-7.46 (m, 2H), 6.99 (m, 1H), 6.88 (m, 1H), 4.94 (s, 2H), 3.81 (s, 3H).

[0390] Example No. I.28-49:

[0391] 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.20-8.16 (m, 2H), 7.52-7.46 (m, 2H), 6.99 (m, 1H), 6.88 (m, 1H), 4.94 (s, 2H), 3.81 (s, 3H).

[0392] Example No. I.30-48:

[0393] 1H-NMR (400 MHz, DMSO-d6 δ, ppm) 13.10 (bs, 1H), 8.40 (m, 1H), 8.13-8.07 (m, 2H), 7.73-7.67 (m, 2H), 7.39 (m, 1H), 4.87 (s, 2H).

[0394] Example No. I.30-4:

[0395] 1 H-NMR (400 MHz, DMSO-d6 δ, ppm) 13.10 (bs, 1H), 8.40 (m, 1H), 8.13-8.07 (m, 2H), 7.73-7.67 (m, 2H), 7.39 (m, 1H), 4.87 (s, 2H).

[0396] Example No. I.28-7:

[0397] 1 H-NMR (400 MHz, DMSO-d6 δ, ppm) 13.10 (bs, 1H), 8.40 (m, 1H), 8.13-8.07 (m, 2H), 7.73-7.67 (m, 2H), 7.39 (m, 1H), 4.87 (s, 2H).

[0398] Example No. I.31-48:

[0399] 1 H-NMR (400 MHz, DMSO-d6 δ, ppm) 13.10 (bs, 1H), 8.40 (m, 1H), 8.13-8.07 (m, 2H), 7.73-7.67 (m, 2H), 7.39 (m, 1H), 4.87 (s, 2H).

[0400] Example No. I.67-38:

[0401] 1 H-NMR (400 MHz, DMSO-d6 δ, ppm) 13.10 (bs, 1H), 8.40 (m, 1H), 8.13-8.07 (m, 2H), 7.73-7.67 (m, 2H), 7.39 (m, 1H), 4.87 (s, 2H).

[0402] Example No. I.32-7:

[0403] 1H-NMR (400 MHz, CDC13 δ, ppm) 8.18 (d, 1H), 7.98 (dd, 1H), 7.42 (m, 1H), 7.31-7.28 (m, 2H), 7.24-7.19 (m, 2H), 4.85 (s, 2H), 4.20 (q, 2H), 1.22 (t, 3H).

[0404] Example No. I.31-7:

[0405] 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.18 (d, 1H), 7.98 (dd, 1H), 7.42 (m, 1H), 7.31-7.28 (m, 2H), 7.24-7.19 (m, 2H), 4.85 (s, 2H), 4.20 (q, 2H), 1.22 (t, 3H).

[0406] Example No. I.28-48:

[0407] 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.18 (d, 1H), 7.98 (dd, 1H), 7.42 (m, 1H), 7.31-7.28 (m, 2H), 7.24-7.19 (m, 2H), 4.85 (s, 2H), 4.20 (q, 2H), 1.22 (t, 3H).

[0408] Example No. I.33-49:

[0409] 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.18 (d, 1H), 7.98 (dd, 1H), 7.42 (m, 1H), 7.31-7.28 (m, 2H), 7.24-7.19 (m, 2H), 4.85 (s, 2H), 4.20 (q, 2H), 1.22 (t, 3H).

[0410] Example No. I.33-38:

[0411] 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.18 (d, 1H), 7.98 (dd, 1H), 7.42 (m, 1H), 7.31-7.28 (m, 2H), 7.24-7.19 (m, 2H), 4.85 (s, 2H), 4.20 (q, 2H), 1.22 (t, 3H).

[0412] Example No. I.31-2:

[0413] 1H-NMR (400 MHz, CDC13 δ, ppm) 8.17-8.14 (m, 2H), 7.54-7.41 (m, 3H), 7.27 (m, 1H), 7.12 (m, 1H), 4.95 (s, 2H), 3.81 (s, 3H).

[0414] Example No. I.32-49:

[0415] 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.17-8.14 (m, 2H), 7.54-7.41 (m, 3H), 7.27 (m, 1H), 7.12 (m, 1H), 4.95 (s, 2H), 3.81 (s, 3H).

[0416] Example No. I.30-2:

[0417] 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.17-8.14 (m, 2H), 7.54-7.41 (m, 3H), 7.27 (m, 1H), 7.12 (m, 1H), 4.95 (s, 2H), 3.81 (s, 3H).

[0418] Example No. I.28-2:

[0419] 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.17-8.14 (m, 2H), 7.54-7.41 (m, 3H), 7.27 (m, 1H), 7.12 (m, 1H), 4.95 (s, 2H), 3.81 (s, 3H).

[0420] Example No. I.68-38:

[0421] 1 H-NMR (400 MHz, CDC13 δ, ppm) 8.17-8.14 (m, 2H), 7.54-7.41 (m, 3H), 7.27 (m, 1H), 7.12 (m, 1H), 4.95 (s, 2H), 3.81 (s, 3H).

[0422] Example No. I.33-7:

[0423] 1H-NMR (400MHz, DMSO-d6δ, ppm) 13.10 (bs, 1H), 8.47 (d, 1H), 8.05 (m, 1H), 7.92 (m, 1H), 7.53-7.49 (m, 2H), 7.42-7.38 (m, 2H), 4.87 (s, 2H).

[0424] Example 1 number I.33-4:

[0425] 1 H-NMR (400MHz, DMSO-d) 6 δ,ppm)13.10(bs,1H),8.45(d,1H),8.04(m,1H),7.92(m,1H),7.45-7.40(m,2H),7.32-7.27(m,2H),4.86(s,2H).

[0426] Example 1 numbered I.31-4:

[0427] 1 H-NMR (400MHz, CDCl3δ, ppm) 8.24 (d, 1H), 8.04 (dd, 1H), 7.49 (m, 1H), 7.36-7.33 (m, 2H), 7.11-7.07 (m, 2H), 4.95 (s, 2H), 3.81 (s, 3H).

[0428] Example 1 number I.29-7:

[0429] 1 H-NMR (400MHz, CDCl3δ, ppm) 8.36 (m, 1H), 7.99 (m, 1H), 7.76 (dd, 1H), 7.38-7.36 (m, 2H), 7.32-7.29 (m, 2H), 4.92 (s, 2H), 4.28 (q, 2H), 1.30 (t, 3H).

[0430] Example numbers I.32-38:

[0431] 1 H-NMR (400MHz, CDCl3δ, ppm) 8.20-8.16 (m, 2H), 7.52-7.46 (m, 2H), 6.99 (m, 1H), 6.89 (m, 1H), 4.92 (s, 2H), 4.28 (q, 2H), 1.29 (t, 3H).

[0432] NMR peak listing method

[0433] by 1 The selected embodiment is represented in the form of an H NMR peak list. 1H NMR data. For each signal peak, first the delta value in ppm is listed, then within parentheses the signal intensity is listed. For different signal peaks, the delta value / intensity number pairs are listed spaced from each other by a semicolon.

[0434] Thus, the peak list of one embodiment takes the following form:

[0435] δ1(intensity1); δ2(intensity2);...; δ i (intensity i );...; δ n (intensity n )

[0436] The intensities of the peak signals correlate with the signal heights (in cm) in the printed embodiments of the NMR spectra and show the true proportions of the signal intensities. In the case of broad peak signals, several peaks or midsections of the signal can be shown and their relative intensities compared to the strongest signal in the spectrum.

[0437] To correct 1 the chemical shifts of the1H NMR spectra, the chemical shifts of tetramethylsilane and / or the solvent are used, in particular in the case of spectra measured in DMSO. Thus, in the NMR peak lists, the tetramethylsilane peak can but does not have to appear.

[0438] 1 The1H NMR peak lists are similar to the conventional 1 H NMR prints and thus generally contain all the peaks listed in the conventional NMR specifications.

[0439] In addition, like the conventional 1 H NMR prints, they can show signals of the solvent signals, stereoisomers of the target compound (also provided by the present application) and / or impurity peaks.

[0440] In the reporting of the signals of the compound in the delta range of the solvent and / or water, 1 the standard solvent peaks (for example the peak of DMSO and the peak of water in DMSO-d6) are shown in the1H NMR peak lists, which, on average, generally have a high intensity.

[0441] The peaks of the stereoisomers of the target compound and / or the peaks of the impurities generally have a lower average intensity than the peaks of the target compound (for example a purity > 90%).

[0442] Such stereoisomers and / or impurities can be specific to the particular preparation method. Thus, by reference to the "by-product fingerprints", their peaks can help to identify the reproducibility of the preparation method.

[0443] The peaks of the target compounds are calculated by the skilled person by known methods (MestreC, ACD simulation, and expected values using empirical estimates) and the peaks of the target compounds are optionally separated as required using additional intensity filters. This separation is analogous to that in conventional 1 The relevant peak picking in the H NMR description is analogous.

[0444] Further details of the H NMR peak list can be found in Research Disclosure Database No. 564025 1 Further details of the H NMR peak list can be found in Research Disclosure Database No. 564025

[0445]

[0446]

[0447]

[0448]

[0449]

[0450]

[0451] The present application also provides a method for protecting crop plants or useful plants from the phytotoxic action of agrochemicals, such as pesticides or in particular herbicides, which cause damage to the crop plants or useful plants, characterized in that a compound of the general formula (I) or a salt thereof is used as a safener, preferably an effective amount of a compound of the general formula (I) or a salt thereof is applied to the plants, to the plant parts or to their seeds (or seed material).

[0452] The compounds of the general formula (I) (= safeners) mentioned above are suitable for use together with active ingredients (pesticides) for the selective control of harmful organisms in a variety of crop cultures, for example in economically important crops such as cereals (wheat, barley, triticale, rye, rice, maize, millet / sorghum), sugar beet, sugar cane, rape, cotton, sunflower, peas, legumes and soybeans.

[0453] The herbicide-safener combinations with the safeners of the general formula (I) are also suitable for controlling harmful plants on seedbeds and areas of useful plants and ornamental plants, for example on lawn areas of utility or decorative lawns, in particular on ryegrass, bluegrass or Bermuda grass.

[0454] Of interest in this connection are also mutant crops which are completely or partially tolerant to certain pesticides or transgenic crops which are completely or partially tolerant to certain pesticides, such as corn crops which are resistant to glufosinate-ammonium or glyphosate, or soybean crops which are resistant to imidazolinones having a plant-destroying effect.

[0455] However, the particular benefit of the safeners of the general formula (I) used in a new way is their effective action in crops which are not normally sufficiently tolerant to the pesticides used.

[0456] When used in conjunction with pesticides, the compounds of the general formula (I) can be applied simultaneously with the active ingredients or in any order and are thus able to reduce or completely prevent the damaging side effects of these active ingredients in the case of crop plants without impairing or significantly reducing the efficacy of these active ingredients against unwanted pests.

[0457] Here, too, it is possible to reduce or completely prevent damage caused by the use of more than one pesticide, for example more than one herbicide or a combination of herbicides with insecticides or fungicides.

[0458] This can considerably extend the field of use of conventional pesticides.

[0459] If the compositions according to the application contain a pesticide, these compositions are applied directly to the area of growth, to the already germinated harmful plants and / or to the useful plants, or to the already emerged harmful plants and / or to the useful plants, in a suitable dilution.

[0460] If the compositions according to the application do not contain any pesticide, these compositions can be used by means of the so-called tank-mix method, which means that the user mixes and dilutes the separately formulated products (= useful plant protective compositions and pesticides) immediately before application to the area to be treated, or before application of the pesticide, or after application of the pesticide, or for seed pre-treatment (i.e. for example for coating of seeds of useful plants).

[0461] It is preferred to use the safeners in time with the pesticides, in particular to apply the safeners to the plants after the herbicides.

[0462] When the compounds of the general formula (I) are used together with a pesticide by pre- or post-emergence methods, their advantageous effects can be observed, for example, in the case of simultaneous application as a tank mix or co-formulation, or in the case of parallel or successive separate application (split application). Multiple repeated applications are also possible. It is sometimes reasonable to combine pre-emergence application with post-emergence application. A frequently chosen option is post-emergence application to the useful or crop plants, simultaneous or later application of the pesticide. Another option is the use of the compounds (I) of the present application for seed dressing, (dip) treatment of seedlings (for example rice) or treatment of other propagation material (for example potato tubers).

[0463] When the compounds of the general formula (I) are used in combination with herbicides, it is generally observed not only a safener effect but also an enhanced herbicidal action on the harmful plants. In addition, in many cases the growth of the useful and crop plants is improved and the harvest yield can be increased.

[0464] The compositions of the present application can comprise one or more pesticides. Examples of useful pesticides include herbicides, insecticides, fungicides, acaricides and nematicides, each of which, when used alone, would cause phytotoxic damage to the crop plants or can cause damage.

[0465] Of particular interest are the respective active pesticide ingredients from the group of herbicides, insecticides, acaricides, nematicides and fungicides, in particular herbicides.

[0466] The weight ratio of the safener (general formula (I)) to the pesticide can vary within wide ranges, typically from 1 : 100 to 100: 1, preferably from 1 :20 to 20: 1, in particular from 1 : 10 to 10: 1. The optimum weight ratio of the safener to the pesticide depends on the respective safener and the respective pesticide used and on the type of useful or crop plants to be protected. Depending on the pesticide used and on the type of useful plants to be protected, the required application rate of the safener can vary within wide ranges, typically from 0.001 to 10 kg, preferably from 0.01 to 1 kg, in particular from 0.01 to 0.2 kg of safener per hectare. The amounts and weight ratios required for a successful treatment can be determined by simple preliminary tests.

[0467] In the case of seed dressing, for example, from 0.005 to 20 g of safener (general formula (I)) per kg of seed are used, preferably from 0.01 to 10 g of safener per kg of seed, in particular from 0.05 to 5 g of safener per kg of seed.

[0468] When solutions of the safener (general formula (I)) are used in seed treatment and the seeds or seedlings are moistened with the solution, suitable concentrations are typically from 1 to 10 000 ppm by weight, preferably from 100 to 1000 ppm by weight.

[0469] The amounts and weight ratios required for successful treatment can be determined by simple preliminary tests.

[0470] The safeners of general formula (I) can be formulated in the customary manner, alone or together with the pesticides. Thus, there are also provided protective compositions for useful plants or crop plants.

[0471] Preference is given to the combined use of the safeners and the pesticides, in particular of the safeners and herbicides, as finished formulations or by the tank-mix method.

[0472] Preference is also given to the use of the safeners of general formula (I) in seed treatment, followed by the application of the pesticides, preferably herbicides, after sowing by pre- or post-emergence methods.

[0473] The compounds of general formula (I) or salts thereof can be used on their own or in the form of their formulations (preparations) in combination with other pesticidal active substances, such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators (for example in the form of finished formulations or tank mixes).

[0474] On the basis of the formulations described above, it is possible to prepare the combination preparations taking into account the physical and intrinsic stability of the active ingredients to be combined.

[0475] Combination partners with which the compounds of general formula (I) of the present application can be used in mixed formulations or tank mixes are, for example, known active ingredients which inhibit the following ingredients, 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, 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 the literature cited therein. Known herbicides or plant growth regulators which can be combined with the compounds of the present application are, for example, the following, where the active ingredients are indicated by their "common name" or chemical name or code according to International Nomenclature Standard (ISO). They always comprise all application forms, for example acids, salts, esters, and all isomeric forms, for example stereoisomers and optical isomers, even if they are not explicitly mentioned.

[0476] Examples of such herbicidal combination partners are:

[0477] acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, 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, bromoxynil-potassium, bromoxynil-heptanoate and bromoxynil-octanoate, busoxinone,butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, 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, 2,4-D-dimethylammonium, 2,4-D-diolamin, 2,4-D-ethyl, 2,4-D-2-ethylhexyl, 2,4-D-isobutyl, 2,4-D- isooctyl, 2,4-D-isopropylammonium,2,4-D-potassium salt, 2,4-D-triisopropanolammonium salt and 2,4-D-trolamine, 2,4-DB, 2,4-DB-butyl ester, 2,4-DB-dimethylammonium salt, 2,4-DB-isoctyl ester, 2,4-DB-potassium salt and 2,4-DB-sodium salt, 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, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9600,F-5231 (i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H- tetrazol-1-yl]-phenyl]ethanesulfonamide), F-7967 (i.e. 3-[7-chloro-5-fluoro-2- (trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine- 2,4(1H,3H)-dione), 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, flurenol-dimethylammonium and flurenol-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 Glyphosate, glufosinate-P-ammonium, glufosinate-sodium, glyphosate, glyphosate-ammonium, glyphosate-isopropylammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-potassium, and glyphosate-sodium. And glyphosate-trimesium, H-9201 (i.e., O-(2,4-dimethyl-6-nitrophenyl)O-ethylisopropylthiophosphoramide ester), halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl Haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02 (i.e., (2,4-dichlorophenoxy)acetic acid 1-(dimethoxyphosphoryl)ethyl ester), imidacloprid, imidacloprid-methyl, imazamox, imazamox-ammonium, imazapicammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, ioxynil-potassium and ioxynil-sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043 (i.e. 3-({[5-(difluoromethyl)-1 -methyl-3-(trifluoromethyl)-1 H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole), ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, MCPA-dimethylammonium, MCPA-2-ethylhexyl, MCPA-isopropylammonium, MCPA-potassium and MCPA-sodium, MCPB, MCPB-methyl, MCPB-ethyl and MCPB-sodium, mecoprop, mecoprop-sodium and mecoprop-butotyl, mecoprop-P, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl and mecoprop-P-potassium, mefenacet,fluorosulfamid, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950 (i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide), NGGC-011, napropamide, NC-310 (i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxy-pyrazole), neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, mineral oil, phenmedipham, picloram, picolinafen, pinoxaden,piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, prometon, prometon, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinocloryl, 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. 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid 1 -ethoxy-3-methyl- 1 -oxobutan-3-en-2-yl ester), SYP-300 (i.e. 1 -[7-fluoro-3-oxo-4-(prop-2-yn-1 -yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3- propyl-2-thioxoimidazolidine-4,5-dione), 2,3,6-TBA, TCA (trichloroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron,triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862 (i.e., 3,4-dichloro-N-{2-[(4,6-dimethoxy-pyrimidin-2-yl)oxy]benzyl}aniline), and the following compounds:

[0478]

[0479] Examples of plant growth regulators as possible mixing partners are:

[0480] acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechol, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dymron, n-decyl alcohol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, endothal-disodium and mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurprimidol, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, methyl jasmonate, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthoxyacetic acid, nitrophenolate mixture, 4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazole, N-phenylphthalamic acid, prohexadione, prohexadione-calcium salt, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

[0481] In the case of use as active ingredient preparations or co-preparations, these will as appropriate usually contain various customary binders, wetting agents, dispersants, emulsifiers, penetration agents, preservatives, antifreezes and solvents, fillers, carriers and dyes, antifoams, evaporation inhibitors, and pH and viscosity regulators.

[0482] The compounds of general formula (I) and their combinations with one or more of the mentioned pesticides can be formulated in various ways depending on the defined physical-chemical and biological parameters.

[0483] Suitable examples of the type of preparation include:

[0484] - emulsifiable concentrates, prepared by dissolving the active ingredient in an organic solvent, such as butanol, cyclohexanone, dimethylformamide, xylene, or a mixture of relatively high-boiling hydrocarbons or organic solvents, and adding one or more ionic and / or non-ionic surfactants (emulsifiers).

[0485] Suitable emulsifiers are, for example, calcium alkylaryl sulfonates, 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;

[0486] - dusting products, obtained by grinding the active ingredient with finely divided solid inorganic or organic substances, such as talc, natural clays, such as kaolin, bentonite and pyrophyllite, diatomaceous earth or diatomaceous earth flour;

[0487] - water-based or oil-based suspension concentrates, which can be prepared, for example, by wet-milling in a pearl mill;

[0488] - water-soluble powders;

[0489] - water-soluble concentrates;

[0490] - granules, such as water-soluble granules, water-dispersible granules and granules for broadcasting and soil application;

[0491] - wettable powders, which, in addition to the active ingredient, comprise diluents or inert substances and surfactants;

[0492] - capsule suspensions and microcapsules;

[0493] - ultra-low dosage formulations.

[0494] The above-mentioned types of preparation are known to the person skilled in the art and are described, for example, in:

[0495] K. Martens, "Spray Drying Handbook", 3rd ed., G. Goodwin Ltd., London. 1979; W. van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y. 1973; Winacker-Kϋchler, "Chemische Technologie"

[0496] [Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th edition 1986; "Perry's Chemical Engineer's Handbook", 5th ed., McGraw-Hill, N.Y. 1973, pages 8-57.

[0497] The necessary formulation adjuvants, such as inert materials, surfactants, solvents and other additives, are likewise known and described, for example, in:

[0498] McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; C. Marsden, "Solvents Guide", 2nd ed., Interscience, N.Y. 1963; H. von Olphen, "Introduction to Clay Colloid Chemistry", 2nd ed., J. Wiley & Sons, N.Y.; ​"Surface Active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell N.J.; Winnacker-Kuchler, "Chemische Technologie", volume 7, C. Hanser Verlag Munich, 4th edition 1986.

[0499] In addition to the abovementioned formulation assistants, the useful plant protection compositions can, if appropriate, also comprise the customary wetting agents, adhesives, dispersants, penetration agents, emulsifiers, preservatives, antifreezes, fillers, carriers and dyes, antifoams, evaporation inhibitors, and also pH and viscosity regulators.

[0500] Depending on the type of formulation, the useful plant protection compositions usually comprise from 0.1 to 99% by weight, in particular from 0.2 to 95% by weight, of one or more safeners of the general formula (I) or a combination of safeners and pesticides.

[0501] They also comprise from 1 to 99.9% by weight, in particular from 4 to 99.5% by weight, of one or more solid or liquid additives and from 0 to 25% by weight, in particular from 0.1 to 25% by weight, of surfactants. In emulsifiable concentrates, the active ingredient concentration, i.e. the concentration of safener and / or pesticide, is usually from 1 to 90% by weight, in particular from 5 to 80% by weight.

[0502] Dusts usually comprise from 1 to 30% by weight, preferably from 5 to 20% by weight, of active ingredient.

[0503] In wettable powders, the concentration of active ingredient is usually from 10 to 90% by weight.

[0504] In water-dispersible granules, the active ingredient content is, for example, from 1 to 95% by weight, preferably from 10 to 80% by weight.

[0505] For application, the formulations in the form as commercially available, e.g. in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules, are diluted in the customary manner, if appropriate with the addition of water.

[0506] The formulations in the form of powders, granules and sprayable solutions are usually not further diluted before application.

[0507] The desired rate of application of the safeners of the general formula (I) varies depending on external conditions, including temperature, humidity and the type of herbicide used.

[0508] In the examples which follow, but do not limit the application, the expressions of amount are based on weight, unless defined otherwise. Examples

[0509] 1. Formulation examples

[0510] 1.1 Dusting products

[0511] Dusting products are obtained by mixing and comminuting in a bead mill 10 parts by weight of a compound of the general formula (I) (safener) or of an active ingredient mixture consisting of a pesticide, for example a herbicide, and a safener of the general formula (I) and 90 parts by weight of talc as inert substance.

[0512] 1.2 Water-dispersible powders

[0513] Water-dispersible powders are obtained by mixing 25 parts by weight of a compound of the general formula (I) or of an active ingredient mixture consisting of a pesticide, for example a herbicide, and a safener of the general formula (I), 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium lignosulphonate and 1 part by weight of sodium oleoylmethyltaurinate as wetting agent and dispersant, and grinding the mixture in a pinned-disk mill.

[0514] 1.3 Water-dispersible concentrates

[0515] Water-dispersible concentrates are obtained by mixing 20 parts by weight of a compound of the general formula (I) or of an active ingredient mixture consisting of a pesticide, for example a herbicide, and a safener of the general formula (I), with 6 parts by weight of alkylphenol polyglycol ether (X207), 3 parts by weight of isotridecyl alcohol polyglycol ether and 71 parts by weight of paraffin mineral oil, and grinding in a friction ball mill to a fineness of less than 5 micrometres.

[0516] 1.4 Emulsifiable concentrates

[0517] ​Emulsifiable concentrates are obtained from 15 parts by weight of a compound of the general formula (I) or of an active ingredient mixture consisting of a pesticide, such as a herbicide, and a safener of the general formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.

[0518] 1.5 Water-dispersible granules

[0519] Water-dispersible granules are obtained by mixing the following ingredients:

[0520] 75 parts by weight of a safener of the general formula (I) or of a mixture of a pesticide and a safener of the general formula (I),

[0521] 10 parts by weight of calcium lignosulphonate,

[0522] 5 parts by weight of sodium dodecylsulphate,

[0523] 3 parts by weight of polyvinyl alcohol, and

[0524] 7 parts by weight of polyvinyl alcohol, and

[0525] 7 parts by weight of kaolin,

[0526] The mixture is ground in a pin mill and the powder is granulated in a fluid bed by spraying water as granulation liquid.

[0527] Water-dispersible granules are also obtained by homogenizing and comminuting in a colloid mill the following ingredients:

[0528] 25 parts by weight of a safener of the general formula (I) or of a mixture of a pesticide and a safener of the general formula (I),

[0529] 5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulphonate,

[0530] 2 parts by weight of sodium oleylmethyltaurinate,

[0531] 17 parts by weight of calcium carbonate

[0532] 50 parts by weight of water, and

[0533] 1 part by weight of polyvinyl alcohol,

[0534] The mixture is then ground in a bead mill and the suspension thus obtained is atomized and dried in a spray tower by means of a single-phase nozzle.

[0535] 2. Biological examples

[0536] 2.1 Reduction of damage to winter wheat (TRZAS) by mesosulfuron-methyl as an example, relative action of selected compounds of the application

[0537] The crop plant seeds to be treated are arranged on sand loam in plastic pots (diameter ca. 4 cm), covered with soil and grown in a greenhouse under good germination and growth conditions. The test plants are treated at the early leaf stage (BBCH 10 - BBCH 12). In the process, the compounds of the present application of the general formula (I) are sprayed on the aerial parts of the plants as aqueous suspensions, formulated as wettable powders (WP), with an amount of water corresponding to 800 1 / ha and addition of the indicated dosage of wetting agent (e.g. 0.2% Genapol-LRO or 0.2% Mero).

[0538] Subsequently, the herbicide is applied. For this purpose, mesosulfuron-methyl, formulated as water dispersible granules (WG), is sprayed on the aerial parts of the plants as an aqueous dispersion with an amount of water corresponding to 800 1 / ha and addition of a dosage of 40 - 60 g / ha of wetting agent (e.g. 0.2% Genapol-LRO or 1 1 / ha Biopower). The herbicide dosage chosen here should cause a visually noticeable damage (min. 30%, max. 75%) to the crop plants not treated with the safener in the same test compared to the untreated crop plants at the time of evaluation.

[0539] After the application, the plants are incubated in a greenhouse under good growth conditions. 9 - 13 days after the application, the efficacy of the test compounds is evaluated visually. For this purpose, the appearance of the plants treated with the test compounds and the herbicide is compared with the corresponding herbicide control (without safener; with clearly visible damage) and the untreated control (without damage). The damage mitigation effect of the test compounds here is indicated with a graded efficacy code according to the following scheme:

[0540] 0: no damage mitigation (appearance corresponds to herbicide control)

[0541] 1 : slight damage mitigation

[0542] 2: clear damage mitigation

[0543] 3: pronounced damage mitigation

[0544] 4: complete damage mitigation (appearance corresponds to untreated control)

[0545] The test shows that the compounds of the present application selected by way of example have a clear efficacy in mitigating the damage to the summer wheat crop plants (TRZAS; cv. Triso) caused by the herbicide mesosulfuron-methyl:

[0546]

[0547] 2.2 Relative action of selected compounds of the present application in the mitigation of the damage to summer barley (HORVS) caused by mesosulfuron-methyl

[0548] The crop plant seeds to be treated are arranged on sand loam in plastic pots (diameter ca. 4 cm), covered with soil and grown in a greenhouse under good germination and growth conditions. The test plants are treated at the early leaf stage (BBCH 10 - BBCH 12). In the process, the compounds of the present application of general formula (I) are sprayed on the aerial parts of the plants as aqueous suspensions, formulated as wettable powders (WP), with an amount of water corresponding to 800 l / ha, and with the addition of the specified dosage of wetting agent (e.g. 0.2% Genapol-LRO or 0.2% Mero).

[0549] Subsequently, the herbicide is applied. For this purpose, mesosulfuron-methyl, formulated as water-dispersible granules (WG), is sprayed on the aerial parts of the plants as an aqueous dispersion, with an amount of water corresponding to 800 l / ha, and with the addition of a dosage of 40 - 60 g / ha of wetting agent (e.g. 0.2% Genapol-LRO or 1 1 / ha Biopower). The herbicide dosage chosen here should cause a visually noticeable damage (min. 30%, max. 75%) to the crop plants not treated with the safener in the same test compared to the untreated crop plants at the time of evaluation.

[0550] After the application, the plants are cultivated in a greenhouse under good growth conditions. 9 - 13 days after the application, the efficacy of the test compounds is assessed visually. For this purpose, the appearance of the plants treated with the test compounds and the herbicide is compared with the corresponding herbicide control (without safener; with clearly visible damage) and the untreated control (without damage). The damage mitigation effect of the test compounds here is indicated according to the following scheme with the grading efficacy code:

[0551] 0: no damage mitigation (appearance corresponds to herbicide control)

[0552] 1 : slight damage mitigation

[0553] 2: clear damage mitigation

[0554] 3: pronounced damage mitigation

[0555] 4: complete damage mitigation (appearance corresponds to untreated control)

[0556] The test shows that the compounds of the present application selected by way of example have a clear efficacy in mitigating the damage to the crop plants of summer barley (HORVS; cv. Montoya) caused by the herbicide mesosulfuron-methyl:

[0557]

[0558]

Claims

1. Compounds of general formula (I) or their salts in R 1 For Q-1.12, Q-1.13, Q-1.18, or Q-1.57 And (R) 2 ) m -Phenyl groups are Q-2.1, Q-2.2, Q-2.4, Q-2.7, Q-2.38, Q-2.48, or Q-2.

49. R 3 It is hydrogen. R 4 It can be hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-methoxyethyl, tetrahydrofuran-2-yl-methyl, or 1,3-dioxacyclopentane-2-ylmethyl.

2. A useful plant or crop plant protection composition, characterized in that, Contains at least one compound of general formula (I) according to claim 1 or a salt thereof, as well as other agrochemicals and optionally formulation adjuvants.

3. The composition according to claim 2, wherein it comprises at least one herbicide.

4. A method for reducing the phytotoxic effects of pesticides on useful plants or crop plants by using one or more compounds of claim 1 or compositions of claim 2 or 3.

5. A method for reducing the phytotoxic effects of pesticides on useful plants or crops, characterized in that, One or more compounds of general formula (I) of claim 1, used in combination with pesticides, are applied simultaneously or in any order with the pesticides.

6. The method according to claim 5, wherein the pesticide is one or more herbicides.

7. The method according to any one of claims 5 or 6, characterized in that, Apply the compound of formula (I) of claim 1 or a salt thereof to a plant or its seeds.

8. The method according to claim 7, characterized in that, Apply the compound of formula (I) of claim 1 or a salt thereof to plant parts or seed material.

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