[(1-phenyl-5-heteroaryl-1h-pyrazol-3-yl)oxy] acetic acid derivatives as safeners for useful and crop plants

Abstract

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

Description

[0001] This invention relates to useful plant-protective compounds for reducing the phytotoxicity of agricultural chemicals, particularly herbicides, and compositions comprising specific compounds as safeners. More specifically, this invention relates to {[1-(phenyl)-5-(heteroaryl)-1H-pyrazol-3-yl]oxy}acetic acid derivatives and their salts as safeners, and to methods for their preparation.

[0002] When pesticides are used to control unwanted organisms in horticultural and sivicultural crops, the beneficial plants are often also more or less harmed by the pesticides used (e.g., herbicides, insecticides, and especially fungicides). This unwanted phytotoxicity occurs to a certain degree when large amounts of herbicides are used in beneficial crops such as corn, rice, or cereals (primarily in post-emergence application). In some cases, the use of “safeners” or “antidotes” can protect beneficial plants from the phytotoxicity of pesticides without reducing or significantly impairing pesticide efficacy against pests. In some cases, even enhanced pesticide efficacy against pests such as weeds has been observed in the presence of safeners.

[0003] To date, compounds known as safeners belong to a wide range of different chemical structures, and their suitability as safeners often depends on the chemical structure of the pesticide and the useful plant crop.

[0004] The safener effects of phenoxy or heteroaryloxyalkane carboxylic acid derivatives when used in combination with herbicides are well-known. Examples of such compounds are MCPA and similar compounds that still possess herbicidal activity against harmful plants, or cloquintocet-mexyl.

[0005] Also known are safeners for N-phenyl-substituted heteroaryl carboxylic acid ester derivatives having multiple heteroatoms in heteroaromatic systems. Examples of such safeners are mefenpyr-diethyl and isoxadifen-ethyl, which are used in commercially available products.

[0006] WO 2004 / 084631 discloses the use of hydroxylated 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. Furthermore, WO 2005 / 112630 discloses 1,2-dihydroquinoxalin-2-one derivatives, and WO 2008 / 131860 discloses pyridone formamide as a safener.

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

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

[0009] Active ingredients derived from the chemical category of [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid derivatives with bactericidal properties are described in Molecules 2014, 19(1), 1302-1316, J. of Heterocyclic Chemistry 2012, 49(6) 1370-1375, Acta Crystallographica, Section E: Structure Reports Online 2012, 68(8), o2419, Acta Crystallographica, Section E: Structure Reports Online 2012, 68(1), o123, J. of Heterocyclic Chemistry 2010, 47(4) 897-902. Antibacterial agricultural chemicals [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid derivatives are described in CN102093344 and CN101284815.

[0010] Various literatures document [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives with pharmaceutical properties. WO2008073825 and DE2828529 disclose [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives.

[0011] The synthesis of the [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid derivative is described in the European Journal of Organic Chemistry 2011, 27, 5323-5339.

[0012] The synthesis of substituted {[1-phenyl-5-(2-thienyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid derivatives is described in WO2008 / 073825 as intermediates for pharmaceutical LXR and FXR modulators.

[0013] When safeners are used to protect crops from pesticide damage, known drawbacks have been found in many cases. These drawbacks include:

[0014] - Insufficient useful plant protection characteristics

[0015] - When combined with a specific herbicide, where the useful plant spectrum of the safener / herbicide is not broad enough.

[0016] - Certain safeners can only be used in combination with a limited number of herbicides.

[0017] The use of safety agents increases the application rate and the amount of formulation adjuvants used, which may lead to application-related problems.

[0018] For the reasons mentioned above, there is an increasing need to provide alternative compounds that act as safety agents.

[0019] This invention provides new useful plant protective compounds of general formula (I) or salts thereof.

[0020]

[0021] It is used to reduce the phytotoxic effects of pesticides, especially herbicides, on beneficial plants or crops.

[0022] in

[0023] R 1 It is a heteroaryl group, excluding thiophene groups, wherein the heteroaryl group is unsubstituted or converted by halogen, cyano, nitro, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)ynyl, (C3-C8)cycloalkyl,

[0024] (C3-C8)cycloalkenyl, (C1-C6)alkoxy, and (C1-C6)alkyl S(O) p Substitution, wherein the last seven groups are either unsubstituted or replaced by one or more groups derived from halogen, cyano, (C1-C6).

[0025] Alkoxy and (C1-C6)alkyl S(O) p Substitution of groups,

[0026] R 2 It can be hydrogen, halogen, cyano, nitro, (C1-C6)alkyl, (C2-C6)alkenyl, or (C2-C6)

[0027] Alkynyl, (C3-C8)cycloalkyl, (C3-C8)cycloalkenyl, (C1-C6)alkoxy, and (C1-C6)

[0028] Alkyl S(O) pThe last seven groups are either unsubstituted or replaced by one or more groups derived from halogen, cyano, (C1-C6)alkoxy, and (C1-C6)alkyl S(O). p Substitution of groups,

[0029] R 3 It consists of hydrogen and (C1-C6) alkyl groups.

[0030] R 4 For hydrogen, (C1-C 18 )alkyl, (C1-C 18 ) Haloalkyl, (C1-C 18 )cyanoalkyl, (C2-C 18 )

[0031] alkenyl, (C2-C 18 ) ynyl group, (C3-C 12 )cycloalkyl, (C3-C 12 )cycloalkenyl, aryl, heteroaryl, (C1-C 18 )alkoxy-(C1-C 18 )alkyl, (C1-C 18 ) Haloalkoxy

[0032] -(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, heterocyclic -(C1-C 18 )alkyl, aryl-(C1-C 18 )

[0033] Alkyl, (C3-C) 12 )cycloalkyl-(C1-C 18 )alkyl, (C1-C 18 )alkoxycarbonyl-(C1-C 18 )

[0034] Alkyl and (C1-C) 18 )alkoxycarbonyl-(C3-C 12 )cycloalkyl-(C1-C 18 )alkyl, or of the formula -NR a R b Or -N = CR c R d group,

[0035] Among the first two groups, R a R b R c and R d Each of the groups is independently hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)ynyl, benzyl, substituted benzyl, phenyl, or substituted phenyl.

[0036] Or, R a and R b Together with a nitrogen atom, it can form a 3- to 8-membered heterocycle, which may contain one or two other cyclic heteroatoms from N, O, and S, and the heterocycle is either unsubstituted or substituted by one or more groups from (C1-C4) alkyl and (C1-C4) haloalkyl groups.

[0037] Or, R c and R d Together with carbon atoms, it forms a 3- to 8-membered carbocyclic or heterocyclic group, which may contain 1 to 3 cyclic heteroatoms from N, O, and S, wherein the carbocyclic or heterocyclic group is unsubstituted or substituted by one or more groups from (C1-C4) alkyl and (C1-C4) haloalkyl groups.

[0038] m is a number from 0 to 5

[0039] and

[0040] p is 0, 1, or 2.

[0041] Compounds of general formula (I) can form salts by adding a suitable inorganic or organic acid to a basic group, such as mineral acids like HCl, HBr, H₂SO₄, H₃PO₄, or HNO₃, or organic acids like carboxylic acids like formic acid, acetic acid, propionic acid, oxalic acid, lactic acid, or salicylic acid, or sulfonic acids like p-toluenesulfonic acid, where the basic group is, for example, amino, alkylamino, dialkylamino, piperidinyl, morpholinyl, or pyridinyl. These salts then contain a conjugate base as an anionic acid. A suitable deprotonated form of the substituent (e.g., sulfonic acids, especially sulfonamides or carboxylic acids) can form an inner salt with a self-protonable group (such as an amino group). Salts can also be formed by the action of a base on a compound of general formula (I). For example, suitable bases are organic amines (such as trialkylamines, morpholine, piperidine, and pyridine) and ammonium, alkali metal or alkaline earth metal hydroxides, carbonates, and bicarbonates, particularly sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, and potassium bicarbonate. These salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, such as metal salts, particularly alkali metal or alkaline earth metal salts, especially sodium and potassium salts, or ammonium salts, with salts of organic amines or quaternary ammonium salts, such as those containing [NR]. i Rii R iii R iv ] + The cation, wherein R i To R iv Each is an independent organic group, particularly alkyl, aryl, aralkyl, or alkylaryl. Also useful are alkyl sulfonium and alkyl oxide sulfonium salts, such as (C1-C4)-trialkyl sulfonium and (C1-C4)-trialkyl oxide sulfonium salts.

[0042] The compounds of formula (I) and their salts used in this invention are referred to hereinafter as "compounds of formula (I)".

[0043] The present invention preferably provides compounds of general formula (I), wherein

[0044] R 1 It is a heteroaryl group, excluding thiophene group, wherein the heteroaryl group is unsubstituted or converted by halogen, cyano, nitro, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C4)alkynyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkenyl, (C1-C4)alkoxy, and (C1-C4)alkyl S(O). p Substitution, wherein the last seven groups are not substituted or are replaced by one or more groups derived from halogen, cyano,

[0045] (C1-C4)alkoxy and (C1-C4)alkyl S(O) p Substitution of groups,

[0046] R 2 It can be hydrogen, halogen, cyano, nitro, (C1-C4)alkyl, (C2-C4)alkenyl, or (C2-C4)

[0047] Alkynyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkenyl, (C1-C4)alkoxy, and (C1-C4)

[0048] Alkyl S(O) p The last seven groups are either unsubstituted or replaced by one or more groups derived from halogen, cyano, (C1-C4)alkoxy, and (C1-C4)alkyl S(O). p Substitution of groups,

[0049] R 3 It consists of hydrogen and (C1-C4) alkyl groups.

[0050] R 4 For hydrogen, (C1-C 16 )alkyl, (C1-C 16 ) Haloalkyl, (C1-C 16 )cyanoalkyl, (C2-C 16 )

[0051] alkenyl, (C2-C 16 ) ynyl group, (C3-C 12 )cycloalkyl, (C3-C 12 )cycloalkenyl, aryl, heteroaryl, (C1-C 16 )alkoxy-(C1-C 16 )alkyl, (C1-C 16 ) Haloalkoxy

[0052] -(C1-C 16 )alkyl, (C1-C 16 )alkoxy-(C1-C 16 ) Haloalkyl, (C1-C 16 )alkylthio-(C1-C 16 )alkyl, (C1-C 16 ) Haloalkylthio-(C1-C 16 )alkyl, (C2-C 16 ) Haloalkenyl, (C2-C 16 ) Haloalkynyl, heterocyclic -(C1-C 16 )alkyl, aryl-(C1-C 16 )

[0053] Alkyl, (C3-C) 12 )cycloalkyl-(C1-C 16 )alkyl, (C1-C 16 )alkoxycarbonyl-(C1-C 16 )

[0054] Alkyl and (C1-C) 16 )alkoxycarbonyl-(C3-C 12 )cycloalkyl-(C1-C 16 )alkyl,

[0055] m is a number from 0 to 4

[0056] and

[0057] p is 0, 1, or 2.

[0058] The present invention particularly preferably provides compounds of general formula (I), wherein

[0059] R 1 It is a heteroaryl group, excluding thiophene group, wherein the heteroaryl group is unsubstituted or monosubstituted or polysubstituted by halogen, cyano, methyl, ethyl, CF3, CF2Cl, CH2F, CHF2, OCH3, OCF3, SCH3, SOCH3, SO2CH3 and SCF3.

[0060] R 2The radicals are hydrogen, halogen, cyano, methyl, ethyl, CF3, CF2Cl, CH2F, CHF2, OCH3, OCF3, SCH3, SOCH3, SO2CH3, and SCF3.

[0061] R 3 For hydrogen, CH2CH3 and CH3,

[0062] R 4 For hydrogen, (C1-C 12 )alkyl, (C1-C 12 ) Haloalkyl, (C1-C 12 )cyanoalkyl, (C2-C 12 )alkenyl, (C2-C 12 ) ynyl group, (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, heterocyclic -(C1-C 12 )alkyl, aryl-(C1-C 12 )alkyl, (C3-C 12 )cycloalkyl-(C1-C 12 )alkyl, (C1-C 12 )alkoxycarbonyl-(C1-C 12 )

[0063] Alkyl and (C1-C) 12 )alkoxycarbonyl-(C3-C 12 )cycloalkyl-(C1-C 12 ) alkyl group, where m is a number from 0 to 3.

[0064] and

[0065] p is 0, 1, or 2.

[0066] The present invention particularly preferably provides compounds of general formula (I), wherein

[0067] R1 The following are pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl, pyridazin-4-yl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl, 1,2,3-triazin-4-yl, 1,2,3-triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl 1,3-Oxazol-2-yl, 1,3-Oxazol-4-yl, 1,3-Oxazol-5-yl, Isothiazol-3-yl, Isothiazol-4-yl, Isothiazol-5-yl, 1,3-Thiazol-2-yl, 1,3-Thiazol-4-yl, 1,3-Thiazol-5-yl, 1H-Pyrrole-1-yl, 1H-Pyrrole-2-yl, 1H-Pyrrole-3-yl, Furan-2-yl, Furan-3-yl, 1H-Imidazol-1-yl, 1H-Imidazol-2-yl, 1H-Imidazol-4-yl, 1H-Imidazol-5-yl, 1H-Pyrazole-1-yl, 1H-Pyrazole-3-yl, 1H-Pyrazole-4-yl 1H-pyrazole-5-yl, 1H-1,2,3-triazol-1-yl, 1H-1,2,3-triazol-4-yl, 1H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1,2,4-triazol-1-yl, 1H-1,2,4-triazol-3-yl, 4H-1,2,4-triazol-4-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-4-yl Diazol-5-yl, 1,2,5-oxadiazol-3-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-thiadiazol-5-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,5-thiadiazol-3-yl, 1,2,5-thiadiazol-3-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, which are unsubstituted or replaced by halogen, cyano, methyl, CF3, CF2Cl, CH2F, CHF2, OCH3, OCF3, SCH3, SOCH3, SO2CH3 and SCF3 alone.

[0068] Replacement or substitution

[0069] R 2 The compounds are hydrogen, fluorine, chlorine, bromine, iodine, CN, methyl, CF3, CF2Cl, CH2F, CHF2, OCH3, OCF3, SCH3, SOCH3, SO2CH3, and SCF3.

[0070] R3 It consists of hydrogen and CH3.

[0071] R 4 For hydrogen, (C1-C 10 )alkyl, (C1-C 10 ) Haloalkyl, (C1-C 10 )cyanoalkyl, (C2-C 10 )alkenyl, (C2-C 10 ) alkynyl, (C3-C9)cycloalkyl, (C3-C9)cycloalkenyl, aryl, heteroaryl, (C1-C 10 )alkoxy-(C1-C 10 )alkyl, (C1-C 10 ) Haloalkoxy-(C1-C 10 )alkyl, (C1-C 10 )alkoxy-(C1-C 10 ) Haloalkyl, (C1-C 10 )alkylthio-(C1-C 10 )alkyl, (C1-C 10 ) Haloalkylthio-(C1-C 10 )alkyl, (C2-C 18 ) Haloalkenyl,

[0072] (C2-C 18 ) Haloalkynyl, heterocyclic -(C1-C 10 )alkyl, aryl-(C1-C 10 )alkyl,

[0073] (C3-C9)cycloalkyl-(C1-C 10 )alkyl, (C1-C 10 )alkoxycarbonyl-(C1-C 10 )alkyl and (C1-C 10 )alkoxycarbonyl-(C3-C9)cycloalkyl-(C1-C 10 ) alkyl group, where m is a number from 0 to 3.

[0074] and

[0075] p is 0, 1, or 2.

[0076] The present invention particularly preferably provides compounds of general formula (I), wherein

[0077] R 1 The group is Q-1.1 to Q-1.59.

[0078]

[0079]

[0080] R 2 The following are possible combinations of radicals: hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, CF3, CH2F, CHF2, OCH3, OCF3, SCH3, SOCH3, SO2CH3, and SCF3.

[0081] R 3 It is hydrogen.

[0082] 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, methylacetyl-2-yl, ethylacetyl-2-yl, methylneoplastate-2-yl, ethylneoplastate-3-yl, methyl-2 3-methylpropionate, methyl-2,2-dimethylpropionate, ethyl-2-methylpropionate, methyl-2-propionate, ethyl-2-propionate, methyl acetate, ethyl acetate, methyl-1-methylcyclopropanecarboxylate, ethyl-1-methylcyclopropanecarboxylate, 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, Protyne (Prop-2-yn-1-yl), 2-Chloro-prop-2-en-1-yl, 3-Phenyprop-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- , but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl, 1-(2E)-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-pyrazole-4-methyl, where m is a number of 0, 1, 2 or 3.

[0083] The present invention particularly preferably provides compounds of general formula (I), wherein

[0084] R 1 The group is Q-1.1 to Q-1.59.

[0085]

[0086]

[0087]

[0088] And (R) 2 ) m -Phenyl group, Q-2.1 to Q-2.53

[0089]

[0090]

[0091] R 3 It is hydrogen.

[0092] R 4The following are 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, ethylneoplastic acid Ester-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, oxetane-3-yl, (3-methyloxetane-3-yl)methyl, 2,2,2-trifluoroethyl, 2,2-difluoro Ethyl, 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-dichloroprop-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl, 2-methylprop-2-en-1-yl, but-2 -en-1-yl, but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl, 1-(2E)-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.

[0093] The present invention particularly and especially preferably provides compounds of general formula (I), wherein

[0094] R 1 The group is selected from Q-1.1 to Q-1.59 below.

[0095]

[0096]

[0097] And (R) 2 )m -Phenyl group, Q-2.1 to Q-2.53

[0098]

[0099]

[0100] R 3 It is hydrogen.

[0101] 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, Methylacetyl-2-yl, Ethylacetyl-2-yl, Methyl-1-methylcyclopropanecarboxylate-2-yl, Ethyl-1-methylcyclopropanecarboxylate-2-yl, 2-(dimethylamino)ethyl, Oxycyclobutane-3-yl, (3-methyloxetane-3-yl)methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2-fluoroethyl,

[0102] 2,2,3,3,3-Pentafluoropropyl, Cyclopropylmethyl, 1-Cyclopropylethyl, (1-Methylcyclopropyl)

[0103] 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

[0104] 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,

[0105] 3-Methylbut-1-en-1-yl, 1-(2E)-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.

[0106] The definitions of the general or preferred groups described above can be applied to the final product of general formula (I) as well as, correspondingly, to the raw materials or intermediates used in each case for preparation. These definitions can be combined as needed, i.e., combinations between given preferred ranges.

[0107] Primarily for reasons of higher herbicidal activity, better selectivity and / or better preparability, there is particular interest in compounds of general formula (I) given in this invention or salts thereof or uses thereof in this invention, wherein the various groups have one of the preferred meanings described below, or particularly those that are a combination of one or more of the preferred meanings described below.

[0108] Regarding the compounds of the present invention, the terms used above and below will be clarified. These are familiar to those skilled in the art and are particularly defined as follows:

[0109] Unless otherwise defined, the name of a chemical group should generally be understood as being attached to the skeleton or the rest of the molecule by the structural element of the relevant chemical group mentioned last, i.e., by the oxygen atom in the case of (C2-C8)-olefin, and by the carbon atom of the alkyl group in the cases of heterocyclic-(C1-C8)-alkyl and alkylO(O)C-(C1-C8)-alkyl.

[0110] According to the present invention, "alkylsulfonyl" – alone or as part of a chemical group – refers to a straight-chain or branched alkylsulfonyl group, preferably having 1 to 8 or 1 to 6 carbon atoms, such as (but not limited to) (C1-C6)-alkylsulfonyl groups 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-dimethylpropyl Sulfonyl, 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.

[0111] 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.

[0112] According to the present invention, unless otherwise defined, "alkyl sulfinyl (alkyl-S(=O)-)" means an alkyl group bonded to the skeleton by -S(=O)-, such as (C1-C6)- or (C1-C4)-alkyl sulfinyl, such as (but not limited to) (C1-C6)-alkyl sulfinyl, such as methyl sulfinyl, ethyl sulfinyl, propyl sulfinyl, 1-methylethyl sulfinyl, butyl sulfinyl, 1-methylpropyl sulfinyl, 2-methylpropyl sulfinyl, 1,1-dimethylethyl sulfinyl, pentyl sulfinyl, 1-methylbutyl sulfinyl, 2-methylbutyl sulfinyl, 3-methylbutyl sulfinyl, 1,1-dimethylpropyl sulfinyl, 1,2-dimethylpropyl sulfinyl 2,2-Dimethylpropylsulfinyl, 1-Ethylpropylsulfinyl, Hexylsulfinyl, 1-Methylpentylsulfinyl, 2-Methylpentylsulfinyl, 3-Methylpentylsulfinyl, 4-Methylpentylsulfinyl, 1,1-Dimethylbutylsulfinyl, 1,2-Dimethylbutylsulfinyl, 1,3-Dimethylbutylsulfinyl, 2,2-Dimethylbutylsulfinyl, 2,3-Dimethylbutylsulfinyl, 3,3-Dimethylbutylsulfinyl, 1-Ethylbutylsulfinyl, 2-Ethylbutylsulfinyl, 1,1,2-Trimethylpropylsulfinyl, 1,2,2-Trimethylpropylsulfinyl, 1-Ethyl-1-Methylpropylsulfinyl and 1-Ethyl-2-Methylpropylsulfinyl.

[0113] "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)-olefin and (C3-C6)- or (C3-C4)-alkynyloxy.

[0114] According to the present invention, unless otherwise defined, "alkyl carbonyl" (alkyl-C(=O)-) means an alkyl group bonded to the skeleton by -C(=O)-, for example (C1-C... 10 (C1-C6)- or (C1-C4)-alkylcarbonyl. The number of carbon atoms here is related to the alkyl group in the alkylcarbonyl group.

[0115] 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.

[0116] 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.

[0117] The term "optionally substituted aryl" also includes polycyclic systems such as tetrahydronaphthyl, indenyl, indenyl, fluorenyl, and biphenyl, wherein the bonding site is located on an aromatic system. In systematic terminology, "aryl" is often also covered by the term "optionally substituted phenyl." Preferred aryl substituents herein are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclic, heterocyclic alkyl, alkoxyalkyl, alkylthio, haloalkylthio, haloalkyl, alkoxy, haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, dialkylaminoalkoxy, tri[alkyl]silyl, di[alkyl]arylsilyl, Di[alkyl]alkylsilyl, Tri[alkyl]silylynyl, Alkylynyl, Cycloalkylynyl, Halogenated Alkylynyl, Heterocyclic -N-alkoxy, Nitro, Cyano, Amino, Alkylamino, Dialkylamino, Alkylcarbonylamino, Cycloalkylcarbonylamino, Arylcarbonylamino, Alkoxycarbonylamino, Alkoxycarbonylalkylamino, Arylalkoxycarbonylalkylamino, Hydroxylcarbonyl, Alkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Cycloalkylaminocarbonyl, Dialkylaminocarbonyl, Heteroarylalkoxy, Arylalkoxy.

[0118] A heterocyclic group (heterocyclic group) comprises at least one heterocycle (= carbocyclic ring, wherein at least one carbon atom is substituted with a heteroatom, preferably a heteroatom from N, O, S, or P), said heterocycle being saturated, unsaturated, partially saturated, or heteroaromatic and may be unsubstituted or substituted, in which case the bonding site is located on a ring atom. If the heterocyclic group or heterocycle is optionally substituted, it may be fused with other carbocyclic rings or heterocycles. In the case of optionally substituted heterocyclic groups, polycyclic systems are also included, such as 8-azabicyclo[3.2.1]octyl, 8-azabicyclo[2.2.2]octyl, or 1-azabicyclo[2.2.1]heptyl. Optionally substituted heterocyclic groups also include spirocyclic systems, such as 1-oxa-5-azaspiro[2.3]hexyl. Unless otherwise defined, heterocycles preferably contain 3 to 9 ring atoms, particularly 3 to 6 ring atoms, and may contain one or more, preferably 1 to 4, particularly 1, 2 or 3 heteroatoms, preferably heteroatoms from N, O and S, but should not have two oxygen atoms directly adjacent to each other, for example, containing one heteroatom from N, O and S: 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrolidin-2- or -3-yl, 2,3-dihydro-1H-pyrrolidin-1- or -2- or -3- or -4- or 5-yl, 2,5-di Hydrogen-1H-pyrrole-1- or -2- or -3-yl, 1- or 2- or 3- or 4-piperidinyl, 2,3,4,5-tetrahydropyridine-2- or -3- or -4- or -5- or -6-yl, 1,2,3,6-tetrahydropyridine-1- or -2- or -3- or -4- or -5- or -6-yl, 1,2,3,4-tetrahydropyridine-1- or -2- or -3- or -4- or -5- or -6-yl, 1,4-dihydropyridine-1- or -2- or -3- or -4-yl, 2,3-dihydropyridine-2- or -3- or - 4- or 5- or 6-yl, 2,5-dihydropyridine-2- or 3- or 4- or 5- or 6-yl, 1- or 2- or 3- or 4-azacycloheptyl, 2,3,4,5-tetrahydro-1H-azacycloheptylene-1- or 2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,4,7-tetrahydro-1H-azacycloheptylene-1- or 2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,6,7-tetrahydro -1H-azacycloheptene-1- or -2- or -3- or -4-yl, 3,4,5,6-tetrahydro-2H-azacycloheptene-2- or -3- or -4- or -5- or -6- or -7-yl, 4,5-dihydro-1H-azacycloheptene-1- or -2- or -3- or -4-yl, 2,5-dihydro-1H-azacycloheptene-1- or -2- or -3- or -4- or -5- or -6- or -7-yl, 2,7-dihydro-1H-azacycloheptene-1- or -2- or -3- or -4-yl, 2,3-Dihydro-1H-azacycloheptene-1-or-2-or-3-or-4-or-5-or-6-or-7-yl, 3,4-Dihydro-2H-azacycloheptene-2-or-3-or-4-or-5-or-6-or-7-yl, 3,6-Dihydro-2H-azacycloheptene-2-or-3-or-4-or-5-or-6-or-7-yl, 5,6-Dihydro-2H-azacycloheptene-2-or-3-or-4-or-5-or-6-or-7-yl, 4,5-Dihydro-3H-azacycloheptene-2-or-3-or-4-or-5-or-6-or-7-yl, 1H-azacycloheptene-1-or-2-or-3-or-4-or-5-or-6-or-7 -yl, 2H-azacyclohepten-2- or -3- or -4- or -5- or -6- or -7-yl, 3H-azacyclohepten-2- or -3- or -4- or -5- or -6- or -7-yl, 4H-azacyclohepten-2- or -3- or -4- or -5- or -6- or -7-yl, 2- or 3-oxacyclopentyl (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-oxacyclohexyl (oxanyl) (=2- or 3- or 4-tetrahydropyranyl), 3,4-dihydro-2H-pyran-2- or -3- or -4-yl - or -5- or -6-yl, 3,6-dihydro-2H-pyran-2- or -3- or -4- or -5- or -6-yl, 2H-pyran-2- or -3- or -4- or -5- or -6-yl, 4H-pyran-2- or -3- or -4-yl, 2- or -3- or -4-oxepanyl, 2,3,4,5-tetrahydrooxepin-2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,4,7-tetrahydrooxepin-2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,6,7-tetrahydrooxepin-2- or -3- or -4-yl -yl, 2,3-dihydrooxetane-2-or-3-or-4-or-5-or-6-or-7-yl, 4,5-dihydrooxetane-2-or-3-or-4-yl, 2,5-dihydrooxetane-2-or-3-or-4-or-5-or-6-or-7-yl, oxetane-2-or-3-or-4-or-5-or-6-or-7-yl, 2-or-3-or-4-or-5-or-6-or-7-yl, 2-or-3-tetrahydrothiopheneyl, 2,3-dihydrothiophene-2-or-3-or-4-or-5-yl, 2,5-dihydrothiophene-2-or-3-yl, tetrahydro-2H-thiaran-2-or-3-or-4-yl, 3,4-dihydro-2H-thiaran-2-or-3-or-4-or-5-or-6-yl, 3,6-Dihydro-2H-thiaran-2- or -3- or -4- or -5- or -6-yl, 2H-thiaran-2- or -3- or -4- or -5- or -6-yl, 4H-thiaran-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-oxetane, 2- or 3-thietanyl, and 1,3-dioxetane-2-yl. Other examples of “heterocyclic groups” are partially or fully hydrogenated heterocyclic groups having two heteroatoms from N, O, and S, such as 1- or 2- or 3- or 4-pyrazolyl groups, 4,5-dihydro-3H-pyrazol-3- or 4- or 5-yl groups, 4,5-dihydro-1H-pyrazol-1- or 3- or 4- or 5-yl groups, 2,3-dihydro-1H-pyrazol-1- or 2- or 3- or 4- or 5-yl groups, 1- or 2- or 3- or 4-imidazolyl groups, 2,3-dihydro-1H-imidazolyl groups, and 2,5-dihydro-1H-imidazolyl groups. -1- or 2- or 4- or 5-yl, 4,5-dihydro-1H-imidazol-1- or 2- or 4- or 5-yl, hexahydropyridazine-1- or 2- or 3- or 4-yl, 1,2,3,4-tetrahydropyridazine-1- or 2- or 3- or 4- or 5- or 6-yl, 1,2,3,6-tetrahydropyridazine-1- or 2- or 3- or 4- or 5- or 6-yl, 1,4,5,6-tetrahydropyridazine-1- or 3- or 4- or 5- or 6-yl, 3,4,5,6-tetrahydropyridazine-3- or 4- or 5-yl, 4,5-dihydropyridazine-3- or 4-yl, 3 4-Dihydropyridazine-3, 4, 5, or 6-yl, 3,6-Dihydropyridazine-3, 4-yl, 1,6-Dihydropyridazine-1, 3, 4, 5, or 6-yl, Hexahydropyrimidine-1, 2, 3, or 4-yl, 1,4,5,6-Tetrahydropyrimidine-1, 2, 5,6-Tetrahydropyrimidine-1, 2, 4, 5, or 6-yl, 1,2,3,4-Tetrahydropyrimidine-1, 2, 3,4-Tetrahydropyrimidine-1, 2, 3, 4, 5, or 6-yl, 1,6-Dihydropyrimidine-1, 2, 4, 5, or 6-yl -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-tetrahydropyrazine-1- or 2- or 3- or 5- or 6-yl, 1,2,3,4-tetrahydropyrazine-1- or 2- or 3- or 4- 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-Dioxol-2- or 4- or 5-yl, 1,3-Dioxol-2- or 4- or 5-yl, 4H-1,3-Dioxin-2- or 4- or 5- or 6-yl, 1,4-Dioxane-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-dithiopentane-2- or 4-yl, 1,3-dithiol-2- or 4-yl, 1,2-dithiane-3- or 4-yl, 3,4-dihydro-1,2-dithiain-3- or 4- or 5- or 6-yl, 3,6-dihydro-1,2-dithiain-3- or 4-yl, 1,2-dithiane Indo-3- or 4-yl, 1,3-dithiazide-2- or 4- or 5-yl, 4H-1,3-dithiazide-2- or 4- or 5- or 6-yl, isoxazolidine-2- or 3- or 4- or 5-yl, 2,3-dihydroisoxazol-2- or 3- or 4- or 5-yl, 2,5-dihydroisoxazol-2- or 3- or 4- or 5-yl, 4,5-dihydroisoxazol- 3- or 4- or 5-yl, 1,3-oxazolidine-2- or 3- or 4- or 5-yl, 2,3-dihydro-1,3-oxazol-2- or 3- or 4- or 5-yl, 2,5-dihydro-1,3-oxazol-2- or 4- or 5-yl, 4,5-dihydro-1,3-oxazol-2- or 4- or 5-yl, 1,2-oxazinan-2- or 3- or 4- or 5- or 6-yl, 3,4-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl, 3,6-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl, 5,6-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl, 5,6-dihydro-4H -1,2-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-oxazacyclohexane-2-or-3-or-4-or-5-or-6-yl, 3,4-di Hydrogen-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-Oxazin-2- or 4- or 5- or 6-yl, 6H-1,3-Oxazin-2- or 4- or 5- or 6-yl, 4H-1,3-Oxazin-2- or 4- or 5- or 6-yl, morpholin-2- or 3- or 4-yl, 3,4-dihydro-2H-1,4-Oxazin-2- or 3- or 4- or 5- or 6-yl, 3,6-dihydro-2H-1,4-Oxazin-2- or 3- or 5- or 6-yl, 2H-1,4-Oxazin-2- or 3- or 5- or 6-yl, 4H-1,4-Oxazin-2- or 3-yl, 1,2-oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,4,5-tetrahydro-1,2-oxazepan ... (in)-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,4,7-tetrahydro-1,2-oxazetene-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,6,7-tetrahydro-1,2-oxazetene-2- or 3- or 4- or 5- or 6- or 7-yl, 2,5,6,7-tetrahydro-1,2-oxazetene Heterocyclic heptanyl-2, 3, 4, 5, 6, 7-yl; 4,5, 6, 7-tetrahydro-1,2-oxazocyclic heptanyl-3, 4, 5, 6, 7-yl; 2,3-dihydro-1,2-oxazocyclic heptanyl-2, 3, 4, 5, 6, 7-yl; 2,5-dihydro-1,2-oxazocyclic heptanyl-2, 3-yl; 4- or 5- or 6- or 7-yl, 2,7-dihydro-1,2-oxazetane-heptene-2- or 3- or 4- or 5- or 6- or 7-yl, 4,5-dihydro-1,2-oxazetane-heptene-3- or 4- or 5- or 6- or 7-yl, 4,7-dihydro-1,2-oxazetane-heptene-3- or 4- or 5- or 6- or 7-yl, 6,7 -Dihydro-1,2-oxazetane-3-or-4-or-5-or-6-or-7-yl, 1,2-oxazetane-3-or-4-or-5-or-6-or-7-yl, 1,3-oxazetane-2-or-3-or-4-or-5-or-6-or-7-yl, 2,3,4,5-tetrahydro-1,3-oxazetane-2-or-3-or-4-or-5-or-7-yl 6- or 7-yl, 2,3,4,7-tetrahydro-1,3-oxazetrazine-heptene-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,6,7-tetrahydro-1,3-oxazetrazine-heptene-2- or 3- or 4- or 5- or 6- or 7-yl, 2,5,6,7-tetrahydro-1,3-oxazetrazine-heptene-2- or 4- or 5- or 6-yl Or 7-yl, 4,5,6,7-tetrahydro-1,3-oxazetane-heptene-2- or 4- or 5- or 6- or 7-yl, 2,3-dihydro-1,3-oxazetane-heptene-2- or 3- or 4- or 5- or 6- or 7-yl, 2,5-dihydro-1,3-oxazetane-heptene-2- or 4- or 5- or 6- or 7-yl, 2,7-dihydro-1,3-Oxazolidinyl-2- or 4- or 5- or 6- or 7-yl, 4,5-dihydro-1,3-oxazolidinyl-2- or 4- or 5- or 6- or 7-yl, 4,7-dihydro-1,3-oxazolidinyl-2- or 4- or 5- or 6- or 7-yl, 6,7-dihydro-1,3-oxazolidinyl-2- or 4- or 5- or 6- or 7-yl, 1,3-oxazolidinyl-2- or 4- or 5- or 6- or 7-yl, 1,4-oxazolidinyl-2- or 3- or 5- or 6- or 7-yl, 2,3,4,5-tetrahydro-1,4-oxazolidinyl-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,4,7-tetrahydro-1,4-oxazolidinyl Heterocyclic heptene-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,6,7-tetrahydro-1,4-oxazocyclic heptene-2- or 3- or 5- or 6- or 7-yl, 2,5,6,7-tetrahydro-1,4-oxazocyclic heptene-2- or 3- or 5- or 6- or 7-yl, 4,5,6,7-tetrahydro-1,4-oxazocyclic heterocycles Heptene-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3-dihydro-1,4-oxazetene-2- or 3- or 5- or 6- or 7-yl, 2,5-dihydro-1,4-oxazetene-2- or 3- or 5- or 6- or 7-yl, 2,7-dihydro-1,4-oxazetene-2- or 3- or 5- or 6- or 7-yl, 4,5-dihydro-1,4-oxazolidinyl-2- or 3- or 4- or 5- or 6- or 7-yl, 4,7-dihydro-1,4-oxazolidinyl-2- or 3- or 4- or 5- or 6- or 7-yl, 6,7-dihydro-1,4-oxazolidinyl-2- or 3- or 5- or 6- or 7-yl, 1,4-oxazolidinyl Heterocyclic heptazoline-2- or 3- or 5- or 6- or 7-yl, isothiazolidine-2- or 3- or 4- or 5-yl, 2,3-dihydroisothiazoline-2- or 3- or 4- or 5-yl, 2,5-dihydroisothiazoline-2- or 3- or 4- or 5-yl, 4,5-dihydroisothiazoline-3- or 4- or 5-yl, 1,3-thiazoline-2- or 3- or 4- or 5-yl, 2,3-dihydro-1,3-thiazol-2- or 3- or 4- or 5-yl, 2,5-dihydro-1,3-thiazol-2- or 4- or 5-yl, 4,5-dihydro-1,3-thiazol-2- or 4- or 5-yl, 1,3-thiazinan-2- or 3- or 4- or 5- or 6-yl, 3,4-dihydro-2H-1,3-thiazinan-2- or 3- or 4- or 5- or 6-yl, 3,6-dihydro-2H-1,3-thiazinan-2- or 3- or 4- or 5- or 6-yl, 5,6-dihydro-2H-1,3-thiazinan-2- or 4- or 5- or 6-yl, 5,6-dihydro-4H-1,3-thiazinan-2- or 4- or 5- or 6-yl, 2H-1,3-Thiazin-2-, 4-, 5-, or 6-yl, 6H-1,3-thiazin-2-, 4-, 5-, or 6-yl, 4H-1,3-thiazin-2-, 4-, 5-, or 6-yl. Other examples of "heterocyclic groups" are partially or fully hydrogenated heterocyclic groups having three heteroatoms from N, O, and S, such as 1,4,2-dioxazolidine-2-, 3-, or 5-yl, 1,4,2-dioxazolidine-3-, 5-, or 6-yl, 5,6-dihydro-1,4,2-dioxazin-3-, 5-, or 6-yl, 1,4,2-dioxazin-3-, 5-, or 6-yl, 1,4,2-dioxazin-3-, 5-, or 6-yl, 1,4,2-dioxazine-2-, 3-, 5-, 6-, or 7-yl. 6,7-Dihydro-5H-1,4,2-dioxazo-heptan-3- or 5- or 6- or 7-yl, 2,3-dihydro-7H-1,4,2-dioxazo-heptan-2- or 3- or 5- or 6- or 7-yl, 2,3-dihydro-5H-1,4,2-dioxazo-heptan-2- or 3- or 5- or 6- or 7-yl, 5H-1,4,2-dioxazo-heptan-3- or 5- or 6- or 7-yl, 7H-1,4,2-dioxazo-heptan-3- or 5- or 6- or 7-yl. Structural examples of optionally further substituted heterocycles are also listed below:

[0119]

[0120]

[0121]

[0122] 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.

[0123] When the basic structure is replaced by "one or more groups" from a list of groups (= groups) or a group of groups as generally defined, this in each case includes being replaced by multiple identical and / or structurally different groups simultaneously.

[0124] In the case of partially or fully saturated nitrogen heterocycles, this can be attached to the rest of the molecule via carbon or nitrogen.

[0125] 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.

[0126] According to the present invention, the term "heteroaryl" refers to a heteroaromatic compound, that is, a fully unsaturated aromatic heterocyclic compound, preferably having 1 to 4 (preferably 1 or 2) identical or different heteroatoms (preferably O, S or N) 5- to 7-membered rings.The heteroaryl groups of the present invention are, for example, 1H-pyrrolo-1-yl, 1H-pyrrolo-2-yl, 1H-pyrrolo-3-yl, furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, 1H-imidazol-1-yl, 1H-imidazol-2-yl, 1H-imidazol-4-yl, 1H-imidazol-5-yl, 1H-pyrazole-1-yl, 1H-pyrazole-3-yl, 1H-pyrazole-4-yl, 1H-pyrazole-5-yl, 1H-pyrazole-1-yl, 1H-pyrazole-3-yl, 1H-pyrazole-4-yl, 1H-pyrazole-5-yl, 1H-1,2,3-triazol-1-yl, 1H-1,2,3-triazol-4-yl, 1H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1, 2,4-Triazol-1-yl, 1H-1,2,4-Triazol-3-yl, 4H-1,2,4-Triazol-4-yl, 1,2,4-Oxadiazol-3-yl, 1,2,4-Oxadiazol-5-yl, 1,3,4-Oxadiazol-2-yl, 1,2,3-Oxadiazol-4-yl, 1,2,3-Oxadiazol-5-yl, 1,2,5-Oxadiazol-3-yl, azirmonenyl, 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-thiadiazole-2-yl, 1,3,4-thiadiazole-5-yl, 1,2,4-thiadiazole-5-yl, 1 2,4-Thiadiazole-3-yl, 1,2,5-Thiadiazole-3-yl, 1,2,5-Thiadiazole-3-yl, 1,2,3-Thiadiazole-4-yl, 1,2,3-Thiadiazole-5-yl, oxazolidinyl, thiepinyl, 1,2,4-triazoloneyl, and 1,2,4-diazabolyl-heptene, 2H-1,2,3,4-tetrazolyl, 1H-1,2,3,4-tetrazolyl, 1,2,3,4-oxatriazolyl, 1,2,3,4-thiatriazolyl, 1,2,3,5-oxatriazolyl-4-yl, 1,2,3,5-thiatriazolyl-4-yl. The heteroaryl groups of the present invention can also be substituted with one or more identical or different groups.If two adjacent carbon atoms are part of another aromatic ring, the system is a fused heteroaromatic system, such as benzofused or polyannelated heteroaromatic compounds. Preferred examples are quinolines (e.g., quinoline-2-yl, quinoline-3-yl, quinoline-4-yl, quinoline-5-yl, quinoline-6-yl, quinoline-7-yl, quinoline-8-yl), isoquinolines (e.g., isoquinoline-1-yl, isoquinoline-3-yl, isoquinoline-4-yl, isoquinoline-5-yl, isoquinoline-6-yl, isoquinoline-7-yl, isoquinoline-8-yl), quinoxaline, quinazolinine, zoline, 1,5-naphthoidine, 1,6-naphthoidine, 1,7-naphthoidine, 1,8-naphthoidine, 2,6-naphthoidine, 2,7-naphthoidine, phthalazine, pyridopyrazine, pyridopyrimidine, pyridopyridazine, pteridine, and pyrimidinepyrimidine.Examples of heteroaryl groups also include those derived from the following 5- or 6-membered benzo[a]-fused rings: 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indol-4-yl, 1H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl 1-Benzothiophene-5-yl, 1-Benzothiophene-6-yl, 1-Benzothiophene-7-yl, 1H-Indazole-1-yl, 1H-Indazole-3-yl, 1H-Indazole-4-yl, 1H-Indazole-5-yl, 1H-Indazole-6-yl, 1H-Indazole-7-yl, 2H-Indazole-2-yl, 2H-Indazole-3-yl, 2H-Indazole-4-yl, 2H-Indazole-5-yl, 2H-Indazole-6-yl, 2H-Indazole-7-yl, 2H-Isoindol-2-yl, 2H-Isoindol-1-yl, 2H-Isoindol-3-yl, 2H-Isoindol-2-yl Indole-4-yl, 2H-isoindole-5-yl, 2H-isoindole-6-yl, 2H-isoindole-7-yl, 1H-benzimidazol-1-yl, 1H-benzimidazol-2-yl, 1H-benzimidazol-4-yl, 1H-benzimidazol-5-yl, 1H-benzimidazol-6-yl, 1H-benzimidazol-7-yl, 1,3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl, 1,3-benzoxazol-7-yl, 1,3-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-benzoisoxazole-3-yl, 1,2-benzoisoxazole-4-yl, 1,2-benzoisoxazole-5-yl, 1,2-benzoisoxazole-6-yl, 1,2-benzoisoxazole-7-yl, 1,2-benzoisothiazol-3-yl, 1,2-benzoisothiazol-4-yl, 1,2-benzoisothiazol-5-yl, 1,2-benzoisothiazol-6-yl, 1,2-benzoisothiazol-7-yl.

[0127] The term "halogen" refers to, for example, fluorine, chlorine, bromine, or iodine. If the term is used with a group, then "halogen" refers to, for example, a fluorine, chlorine, bromine, or iodine atom.

[0128] According to the present invention, "alkyl" means a straight-chain or branched open-chain saturated hydrocarbon group, which is optionally monosubstituted or polysubstituted, and in the latter case is referred to as "substituted alkyl". Preferred substituents are halogen atoms, alkoxy groups, haloalkoxy groups, cyano groups, alkylthio groups, haloalkoxythio groups, cycloalkyl groups, alkoxycarbonyl groups, hydroxycarbonyl groups, heterocyclic groups, heteroaryl groups, aryl groups, amino groups, or nitro groups, with methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine, or iodine groups being particularly preferred. The prefix "di" also includes combinations of different alkyl groups, such as methyl (ethyl) or ethyl (methyl).

[0129] "Haloalkyl", "haloalkenyl", and "haloalkynyl" respectively refer to alkyl, alkenyl, and alkynyl groups that are partially or completely substituted with the same or different halogen atoms. Examples include monohaloalkyl groups such as CH2CH2Cl, CH2CH2Br, CHClCH3, CH2Cl, and CH2F; perhaloalkyl groups such as CCl3, CClF2, CFCl2, CF2CClF2, and CF2CClFCF3; and polyhaloalkyl groups such as CH2CHFCl, CF2CClFH, CF2CBrFH, and CH2CF3. The term perhaloalkyl also includes the term perfluoroalkyl.

[0130] "Haloalkoxy" is, for example, OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 and OCH2CH2Cl; this applies accordingly to haloalkenyl and other halogen-substituted groups.

[0131] The term "(C1-C4)-alkyl" as used by way of example herein is an abbreviation for a straight-chain or branched alkyl group having 1 to 4 carbon atoms according to the stated carbon atom range, including methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl, or tert-butyl groups. General alkyl groups having a larger specified carbon atom range, such as "(C1-C6)-alkyl," correspondingly also include straight-chain or branched alkyl groups having more carbon atoms, i.e., according to examples, also including alkyl groups having 5 and 6 carbon atoms.

[0132] Unless otherwise specified, in the case of hydrocarbon groups such as alkyl, alkenyl, and alkynyl groups, including hydrocarbon groups in complex groups, a lower carbon skeleton is preferred, for example, having 1 to 6 carbon atoms, or 2 to 6 carbon atoms in the case of unsaturated groups. Alkyl groups, including alkyl groups in complex groups such as alkoxy, haloalkyl, etc., 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 groups are defined as possible unsaturated groups corresponding to alkyl groups, wherein at least one double or triple bond is present. Groups having one double or triple bond are preferred.

[0133] The term "alkenyl" also specifically includes straight-chain or branched open-chain hydrocarbon groups having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, as well as allenyl or cumulenyl groups having one or more cumulative double bonds, such as allenyl (1,2-alkenyl), 1,2-butadienyl and 1,2,3-penttrienyl. Alkenyl means, for example, vinyl, which may optionally be substituted with other alkyl groups, such as (but not limited to) (C2-C6)-alkenyl, such as 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.

[0134] The term "alkynyl" also specifically includes straight-chain or branched open-chain hydrocarbon groups that have more than one triple bond, or have one or more triple bonds and one or more double bonds, such as 1,3-buttrienyl or 3-pent-1-yn-1-yl. (C2-C6)-alkynyl groups, such as 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.

[0135] 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 substituted with the following groups: hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, dialkylamino, alkoxycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, and cycloalkylaminocarbonyl. In the case of optionally substituted cycloalkyl groups, this includes ring systems with substituents, and also includes substituents having a double bond on the cycloalkyl group, such as alkylene groups, like methylene. In the case of optionally substituted cycloalkyl groups, polycyclic aliphatic systems are also included, such as bicyclo[1.1.0]but-1-yl, bicyclo[1.1.0]but-2-yl, bicyclo[2.1.0]pent-1-yl, bicyclo[1.1.1]pent-1-yl, bicyclo[2.1.0]pent-2-yl, bicyclo[2.1.0]pent-5-yl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]hept-2-yl, bicyclo[2.2.2]oct-2-yl, bicyclo[3.2.1]oct-2-yl, bicyclo[3.2.2]non-2-yl, adamantane-1-yl and adamantane-2-yl, as well as systems such as 1,1'-di(cyclopropyl)-1-yl, such as 1,1'-di(cyclopropyl)-2-yl. The term "(C3-C7)-cycloalkyl" is an abbreviation for cycloalkyl groups having 3 to 7 carbon atoms within a specified range of carbon atoms.

[0136] In the case of substituted cycloalkyl groups, spirocycloaliphatic systems are also included, such as spiro[2.2]pent-1-yl, spiro[2.3]hex-1-yl, spiro[2.3]hex-4-yl, 3-spiro[2.3]hex-5-yl, spiro[3.3]hept-1-yl, and spiro[3.3]hept-2-yl.

[0137] "Cycloalkenyl" preferably refers to a non-aromatic, partially unsaturated cyclic system having a carbon ring with 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, and also includes substituents having a double bond on the cycloalkenyl group, such as alkylene groups, like methylene groups. In the case of optionally substituted cycloalkenyl groups, the description of substituted cycloalkyl groups applies accordingly.

[0138] The term "alkylene", for example, also refers to (C1-C 10The alkylene group (=)- is a straight-chain or branched open-chain hydrocarbon group linked by a double bond. The possible bonding sites for alkylene groups are naturally only those positions on the basic structure where two hydrogen atoms can be replaced by a double bond; the group is, for example, =CH2, =CH-CH3, =C(CH3)-CH3, =C(CH3)-C2H5, or =C(C2H5)-C2H5. Cycloalkylene groups (=)- are carbocyclic groups linked by a double bond.

[0139] "Alkoxyalkyl" refers to an alkoxy group bonded by an alkyl group, and "alkoxyalkyl" refers to an alkoxyalkyl group bonded by an oxygen atom, such as (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, and methoxypropoxy.

[0140] "Arylalkyl" refers to an aryl group bonded by an alkyl group, "heteroarylalkyl" refers to a heteroaryl group bonded by an alkyl group, and "heterocyclicalkyl" refers to a heterocyclic group bonded by an alkyl group.

[0141] “Cycloalkylalkyl” means a cycloalkyl group bonded by an alkyl group, such as (but not limited to) cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropylethyl-1-yl, 2-cyclopropylethyl-1-yl, 1-cyclopropylpropyl-1-yl, 3-cyclopropylpropyl-1-yl.

[0142] According to the present invention, “haloalkylthio” – either on its own or as part of a chemical group – preferably refers to a straight-chain or branched S-haloalkyl group having 1 to 8 or 1 to 6 carbon atoms, such as (C1-C8)-, (C1-C6)- or (C1-C4)-haloalkylthio, such as (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroethyl-1-ylthio, 2,2,2-difluoroethyl-1-ylthio, 3,3,3-propyl-1-ylthio.

[0143] "Halocycloalkyl" refers to a cycloalkyl or cycloalkenyl group that is partially or completely substituted with the same or different halogen atoms (e.g., F, Cl, and Br) or halogenated alkyl groups (e.g., trifluoromethyl or difluoromethyl), such as 1-fluorocyclopropyl-1-yl, 2-fluorocyclopropyl-1-yl, 2,2-difluorocyclopropyl-1-yl, 1-fluorocyclobutyl-1-yl, 1-trifluoromethylcyclopropyl-1-yl, 2-trifluoromethylcyclopropyl-1-yl, 1-chlorocyclopropyl-1-yl, 2-chlorocyclopropyl-1-yl, 2,2-dichlorocyclopropyl-1-yl, and 3,3-difluorocyclobutyl.

[0144] If a compound can form tautomers whose structures are not formally covered by general formula (I) through hydrogen transposition, such tautomers are still included in the definition of compounds of general formula (I) of this invention, unless a specific tautomer is under investigation. For example, many carbonyl compounds can exist in ketone form and enol form, both of which are included in the definition of compounds of general formula (I).

[0145] Compounds of general formula (I) can exist as stereoisomers, depending on the nature of the substituents and their linkage. Possible stereoisomers defined by their specific three-dimensional forms, such as enantiomers, diastereomers, Z-isomers, and E-isomers, are all covered by general formula (I). For example, diastereomers (Z-isomers) may occur if one or more alkenyl groups are present. For example, enantiomers and diastereomers may occur if one or more asymmetric carbon atoms are present. Stereoisomers can be obtained from mixtures obtained during preparation processes using conventional separation methods. Analytical-grade chromatographic separation can be performed to detect enantiomer or diastereomer excesses, or preparative-grade chromatographic separation can be performed to prepare test samples for bioassays. Stereoisomers can also be selectively prepared by stereoselective reactions using optically active raw materials and / or auxiliaries. Therefore, the present invention also relates to all stereoisomers covered by general formula (I) but not shown in their specific stereoisomer forms, and mixtures thereof.

[0146] If the compound is obtained in solid form, it can also be purified by recrystallization or extraction. If a single compound (I) cannot be obtained satisfactorily by the following methods, it can be prepared by derivatization of other compounds (I).

[0147] Suitable methods for separation, purification, and separation of stereoisomers of compounds of general formula (I) are methods commonly known to those skilled in the art from similar cases, such as by physical methods like crystallization, chromatography, particularly column chromatography and HPLC (high performance liquid chromatography), distillation (optionally under reduced pressure), extraction, and other methods. Any remaining mixture can generally be separated by chromatographic methods, such as on a chiral solid phase. Suitable for preparations or industrial scales are methods such as crystallization, for example, crystallizing diastereomeric salts, which can be obtained from diastereomeric mixtures using optically active acids, and, if appropriate, using optically active bases (provided an acidic group is present).

[0148] Synthesis of {[1-(phenyl)-5-(heteroaryl)-1H-pyrazol-3-yl]oxy}acetic acid derivatives of general formula (I)

[0149]

[0150] The {[1-(phenyl)-5-(heteroaryl)-1H-pyrazol-3-yl]oxy}acetic acid derivatives of general formula (I) of this invention can be prepared by known methods. The synthetic routes used and studied begin with commercially available or readily prepared substituted 3-heteroarylprop-2-ynyl acids or substituted heteroarylcinnamic acids, from correspondingly substituted 3-heteroarylprop-2-ynyl esters or substituted heteroarylcinnamic esters, and commercially available chemicals, such as substituted phenylhydrazines and substituted iodobenzenes. In the following schemes, unless a illustrative but non-limiting definition is given, the R portion of general formula (I) refers to... 1 R 2 R 3 R 4 And m have the meanings defined above.

[0151] The compounds of general formula (Ia) of the present invention are synthesized by reacting a compound of general formula (II) with a compound of general formula (III) in the presence of a base (e.g., potassium carbonate). The reaction is preferably carried out in a suitable solvent, such as acetonitrile, within a temperature range of 0°C to 120°C (see Scheme 1).

[0152]

[0153] Where X = halogen and R = (C1-C4)-alkyl.

[0154] Option 1.

[0155] Compounds of general formula (II) are synthesized by amide coupling of an acid of general formula (IV) with a phenylhydrazine hydrogen halide of general formula (V) in the presence of a coupling agent (e.g., T3P, dicyclohexylcarbodiimide, N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide, N,N′-carbonyldiimidazole, 2-chloro-1,3-dimethylimidazolium chloride, or 2-chloro-1-methylpyridinium iodide), followed by cyclization (see Chemistry of Peptide Synthesis, Ed. N. Leo Benoiton, Taylor & Francis, 2006, ISBN-10: 1-57444-454-9). Reagents bound to polymers (e.g., dicyclohexylcarbodiimide bound to polymers) are also suitable for this coupling reaction. The reaction is preferably carried out in a temperature range of 0°C to 80°C in a suitable solvent (e.g., dichloromethane, acetonitrile, N,N-dimethylformamide, or ethyl acetate) and in the presence of a base (e.g., triethylamine, N,N-diisopropylethylamine, or 1,8-diazabicyclo[5.4.0]undec-7-ene) (see Scheme 2). For T3P coupling conditions, see Organic Process Research & Development 2009, 13, 900-906. As an alternative to the phenylhydrazine hydrohalide of general formula (V), the correspondingly substituted phenylhydrazine (VI) can be used in the reaction.

[0156]

[0157] Where X = halogen.

[0158] Option 2.

[0159] Compounds of formula (IV) can be reacted with propane (VIII) by the addition of a suitable transition metal catalyst, particularly palladium catalysts such as tetra(triphenylphosphine)palladium (0) or palladium diacetate or bis(triphenylphosphine)palladium dichloride (II), or nickel catalysts such as nickel acetylacetonate (II) or bis(triphenylphosphine)nickel chloride (II), preferably in an organic solvent (e.g., 1,2-dimethoxyethane or N,N-dimethylformamide) at high temperature (Scheme 3). The “M” group represents, for example, magnesium, zinc, lithium or sodium. Generally, suitable cross-coupling methods are described in RDLarsen, Organometallics in Process Chemistry 2004 Springer Verlag, or I. Tsuji, Palladium Reagents and Catalysts 2004 Wiley, or M. Beller, C. Bolm, Transition Metals for Organic Synthesis 2004 VCH-Wiley. Other suitable synthetic methods are described in Chem. Rev. 2006, 106, 2651; Platinum Metals Review, 2009, 53, 183; Platinum Metals Review 2008, 52, 172 and Acc. Chem. Res. 2008, 41, 1486.

[0160]

[0161] Option 3.

[0162] The acid of general formula (IX) is synthesized by hydrolysis of a compound of general formula (Ia) or by a similar method known to those skilled in the art, as shown in Scheme 4 of the figure below. 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), and the hydrolysis reaction is preferably carried out in a temperature range from room temperature to 100°C. The Lewis acid can be boron tribromide, and the reaction can be carried out in a temperature range from -20°C to 100°C, preferably from -5°C to 50°C.

[0163]

[0164] Where R = (C1-C4)-alkyl.

[0165] Option 4.

[0166] The compounds of general formula (X) of the present invention are synthesized by esterification of an acid of general formula (IX) with an alcohol of general formula (XI) in the presence of a coupling agent (e.g., T3P, dicyclohexylcarbodiimide, N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide, N,N′-carbonyldiimidazole, 2-chloro-1,3-dimethylimidazolium chloride, or 2-chloro-1-methylpyridinium iodide) (see Chemistry of Peptide Synthesis, Ed. N. Leo Benoiton, Taylor & Francis, 2006, ISBN-10: 1-57444-454-9). Polymer-supported agents (e.g., polymer-supported dicyclohexylcarbodiimide) are also suitable for this coupling reaction. The reaction is preferably carried out in a temperature range of 0°C to 80°C in a suitable solvent (e.g., dichloromethane, acetonitrile, N,N-dimethylformamide, or ethyl acetate) and in the presence of a base (e.g., triethylamine, N,N-diisopropylethylamine, or 1,8-diazabicyclo[5.4.0]undec-7-ene) (see Scheme 5). For T3P coupling conditions, see Organic Process Research & Development 2009, 13, 900-906.

[0167]

[0168] Where R′=(C1-C4)-alkyl

[0169] Option 5.

[0170] Compounds of general formula (II) can also be synthesized by oxidizing compounds of general formula (XII) in the presence of ferric halides, such as ferric chloride (III). The reaction is preferably carried out in a temperature range of 0°C to 120°C in a suitable solvent (such as 1,2-dichloroethane, acetonitrile, N,N-dimethylformamide, or ethyl acetate) (Scheme 6).

[0171]

[0172] Option 6.

[0173] Compounds of general formula (XII) can be prepared by amide coupling of an acid of general formula (XIII) with an arylhydrazine of general formula (VI) in the presence of an amide coupling agent (e.g., T3P, dicyclohexylcarbodiimide, N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide, N,N′-carbonyldiimidazole, 2-chloro-1,3-dimethylimidazolium chloride, or 2-chloro-1-methylpyridinium iodide), followed by cyclization (see Chemistry of Peptide Synthesis, Ed. N. Leo Benoiton, Taylor & Francis, 2006, ISBN-10: 1-57444-454-9). Polymer-bound agents (e.g., polymer-bound dicyclohexylcarbodiimide) are also suitable for this coupling reaction. The reaction is preferably carried out in a temperature range of 0°C to 80°C, in a suitable solvent (e.g., dichloromethane, acetonitrile, N,N-dimethylformamide, or ethyl acetate), and in the presence of a base (e.g., triethylamine, N,N-diisopropylethylamine, or 1,8-diazabicyclo[5.4.0]undec-7-ene) (see Scheme 7). For T3P peptide coupling conditions, see Organic Process Research & Development 2009, 13, 900-906.

[0174]

[0175] Option 7.

[0176] 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.77 below. The chemical examples described in the following sections record… 1 H NMR, 13 C NMR and 19 F NMR spectral data ( 1 H NMR is 400MHz 13 C NMR at 150 MHz and 19F NMR was performed at 375 MHz using CDCl3, CD3OD, or d6-DMSO as solvents, with an internal standard of tetramethylsilane (δ = 0.00 ppm) on a Bruker instrument. 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.

[0177] Synthesis Example:

[0178] Synthesis Example Number: I.50-2

[0179] Synthesis Stage 1: 3-(5-Fluoropyridin-3-yl)prop-2-ynetic acid

[0180]

[0181] Under an argon atmosphere, 3-fluoro-5-iodopyridine (5.00 g, 22.40 mmol, 1.0 equivalent) was dissolved in THF (105 mL). Then, propanol (1.58 g, 22.40 mmol, 1.0 equivalent), bis(triphenylphosphine)palladium(II) dichloride (310 mg, 0.89 mmol, 0.04 equivalent), copper(I) iodide (310 mg, 0.04 equivalent), and diisopropylamine (7.9 g, 78.4 mmol, 3.5 equivalent) were added to the solution. The reaction mixture was stirred at room temperature for 2 hours, then added dropwise to water (100 mL), and the mixture was acidified with 2 M hydrochloric acid (30 mL). The mixture was extracted twice with ethyl acetate (150 mL). The combined organic phases were dried over magnesium sulfate and the solvent was removed under reduced pressure. Diethyl ether (50 mL) was added to the residue, and the mixture was sonicated in a bath at room temperature for 10 minutes, then filtered. The filtrate was concentrated under reduced pressure. 3-(5-fluoropyridin-3-yl)prop-2-ynyl acid was separated in solid form (4.38 g, 75% of the theoretical value). 1 H-NMR (400MHz, DMSO-d) 6δ,ppm)14.00(bs,1H),8.57(m,1H),8.32-8.28(m,1H),7.52(m,1H).

[0182] Synthesis Stage 2: 1-(2-fluorophenyl)-5-(5-fluoropyridin-3-yl)-1H-pyrazole-3-ol

[0183]

[0184] 3-(5-fluoropyridin-3-yl)prop-2-ynyl acid (4.38 g, 26.50 mmol, 1.0 equivalent) was dissolved in THF (20 mL). The following substances were added to this solution: (2-fluorophenyl)hydrazine hydrochloride (1:1) (4.90 g, 29.10 mmol, 1.1 equivalent) and triethylamine (9.20 mL, 66.3 mmol). Then, a 50% solution of T3P in THF (31 mL, 53 mmol, 2.0 equivalent) was added dropwise, and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was extracted twice with water (50 mL) and ethyl acetate (100 mL). The combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. 1-(2-fluorophenyl)-5-(5-fluoropyridin-3-yl)-1H-pyrazol-3-ol (7.00 g, 85% of theoretical value) was isolated in oil form. The reaction product does not require further purification and can be used directly in the next synthesis stage.

[0185] Synthesis Stage 3: Ethyl {[1-(2-fluorophenyl)-5-(5-fluoropyridin-3-yl)-1H-pyrazol-3-yl]oxy} (Synthetic Examples I.50-2)

[0186]

[0187] 1-(2-fluorophenyl)-5-(5-fluoropyridin-3-yl)-1H-pyrazol-3-ol (2.45 g, 8.96 mmol, 1.0 equivalent) and potassium carbonate (3.78 g, 26.91 mmol, 3 equivalent) were suspended in acetone (10 mL), and then ethyl bromoacetate (1.49 g, 8.96 mmol, 1.0 equivalent) was added. The suspension was then heated to 80 °C for 2 hours, the solid was filtered off, and the reaction mixture was concentrated under reduced pressure. The residue was extracted with DCM and water, and then purified by column chromatography (ethyl acetate / heptane gradient). Ethyl {5-(3-fluorophenyl)-1-(3-fluoropyridin-2-yl)-1H-pyrazol-3-yl]oxy}acetate (14.20 g, 44% of theoretical value) was isolated as a colorless solid. 1H-NMR (400MHz, CDCl3δ, ppm)1.23(t,3H),4.31(q,2H),6.21(s,1H),5.1(t,1H),7.2(m,2H),7.4(m,1H),7.5(m,1H),8.4(s,1H),8.5(s,1H).

[0188] Similar to the preparation examples cited above and listed in the appropriate places, and taking into account the general details relating to the preparation of {[1-(phenyl)-5-(heteroaryl)-1H-pyrazol-3-yl]oxy}acetic acid derivatives, the following compounds were obtained:

[0189]

[0190] Table I.1: The preferred compounds of formula (I.1) are compounds I.1-1 to I.1-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.1-1 to I.1-53 in Table I.1 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0191] Table 1:

[0192]

[0193]

[0194]

[0195] Table I.2: The preferred compounds of formula (I.2) are compounds I.2-1 to I.2-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.2-1 to I.2-53 in Table I.2 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0196]

[0197] Table I.3: The preferred compounds of formula (I.3) are compounds I.3-1 to I.3-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.3-1 to I.3-53 in Table I.3 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0198]

[0199] Table I.4: The preferred compounds of formula (I.4) are compounds I.4-1 to I.4-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.4-1 to I.4-53 in Table I.4 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0200]

[0201] Table I.5: The preferred compounds of formula (I.5) are compounds I.5-1 to I.5-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.5-1 to I.5-53 in Table I.5 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0202]

[0203] Table I.6: The preferred compounds of formula (I.6) are compounds I.6-1 to I.6-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.6-1 to I.6-53 in Table I.6 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0204]

[0205] Table I.7: The preferred compounds of formula (I.7) are compounds I.7-1 to I.7-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.7-1 to I.7-53 in Table I.7 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0206]

[0207] Table I.8: The preferred compounds of formula (I.8) are compounds I.8-1 to I.8-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.8-1 to I.8-53 in Table I.8 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0208]

[0209] Table I.9: The preferred compounds of formula (I.9) are compounds I.9-1 to I.9-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.9-1 to I.9-53 in Table I.9 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0210]

[0211] Table I.10: The preferred compounds of formula (I.10) are compounds I.10-1 to I.10-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.10-1 to I.10-53 in Table I.10 are...

[0212] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0213]

[0214] Table I.11: The preferred compounds of formula (I.11) are compounds I.11-1 to I.11-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.11-1 to I.11-53 in Table I.11 are...

[0215] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0216]

[0217] Table I.12: The preferred compounds of formula (I.12) are compounds I.12-1 to I.12-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.12-1 to I.12-53 in Table I.12 are...

[0218] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0219]

[0220] Table I.13: The preferred compounds of formula (I.13) are compounds I.13-1 to I.13-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.13-1 to I.13-53 in Table I.13 are...

[0221] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0222]

[0223] Table I.14: The preferred compounds of formula (I.14) are compounds I.14-1 to I.14-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.14-1 to I.14-53 in Table I.14 are...

[0224] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0225]

[0226] Table I.15: The preferred compounds of formula (I.15) are compounds I.15-1 to I.15-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.15-1 to I.15-53 in Table I.15 are...

[0227] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0228]

[0229] Table I.16: The preferred compounds of formula (I.16) are compounds I.16-1 to I.16-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.16-1 to I.16-53 in Table I.16 are...

[0230] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0231]

[0232] Table I.17: The preferred compounds of formula (I.17) are compounds I.17-1 to I.17-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.17-1 to I.17-53 in Table I.17 are...

[0233] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0234]

[0235] Table I.18: The preferred compounds of formula (I.18) are compounds I.18-1 to I.18-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.18-1 to I.18-53 in Table I.18 are...

[0236] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0237]

[0238] Table I.19: The preferred compounds of formula (I.19) are compounds I.19-1 to I.19-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.19-1 to I.19-53 in Table I.19 are...

[0239] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0240]

[0241] Table I.20: The preferred compounds of formula (I.20) are compounds I.20-1 to I.20-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.20-1 to I.20-53 in Table I.20 are...

[0242] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0243]

[0244] Table I.21: The preferred compounds of formula (I.21) are compounds I.21-1 to I.21-53, where 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...

[0245] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0246]

[0247] Table I.22: The preferred compounds of formula (I.22) are compounds I.22-1 to I.22-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.22-1 to I.22-53 in Table I.22 are...

[0248] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0249]

[0250] Table I.23: The preferred compounds of formula (I.23) are compounds I.23-1 to I.23-53, where 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...

[0251] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0252]

[0253] Table I.24: The preferred compounds of formula (I.24) are compounds I.24-1 to I.24-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.24-1 to I.24-53 in Table I.24 are...

[0254] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0255]

[0256] Table I.25: The preferred compounds of formula (I.25) are compounds I.25-1 to I.25-53, where 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...

[0257] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0258]

[0259] Table I.26: The preferred compounds of formula (I.26) are compounds I.26-1 to I.26-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.26-1 to I.26-53 in Table I.26 are...

[0260] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0261]

[0262] Table I.27: The preferred compounds of formula (I.27) are compounds I.27-1 to I.27-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.27-1 to I.27-53 in Table I.27 are...

[0263] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0264]

[0265] Table I.28: The preferred compounds of formula (I.28) are compounds I.28-1 to I.28-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.28-1 to I.28-53 in Table I.28 are...

[0266] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0267]

[0268] Table I.29: The preferred compounds of formula (I.29) are compounds I.29-1 to I.29-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.29-1 to I.29-53 in Table I.29 are...

[0269] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0270]

[0271] Table I.30: The preferred compounds of formula (I.30) are compounds I.30-1 to I.30-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.30-1 to I.30-53 of Table I.30 are...

[0272] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0273]

[0274] Table I.31: The preferred compounds of formula (I.31) are compounds I.31-1 to I.31-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.31-1 to I.31-53 in Table I.31 are...

[0275] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0276]

[0277] Table I.32: The preferred compounds of formula (I.32) are compounds I.32-1 to I.32-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.32-1 to I.32-53 in Table I.32 are...

[0278] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0279]

[0280] Table I.33: The preferred compounds of formula (I.33) are compounds I.33-1 to I.33-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.33-1 to I.33-53 in Table I.33 are...

[0281] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0282]

[0283] Table I.34: The preferred compounds of formula (I.34) are compounds I.34-1 to I.34-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.34-1 to I.34-53 in Table I.34 are...

[0284] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0285]

[0286] Table I.35: The preferred compounds of formula (I.35) are compounds I.35-1 to I.35-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.35-1 to I.35-53 in Table I.35 are...

[0287] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0288]

[0289] Table I.36: The preferred compounds of formula (I.36) are compounds I.36-1 to I.36-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.36-1 to I.36-53 in Table I.36 are...

[0290] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0291]

[0292] Table I.37: Preferred compounds of formula (I.37) are compounds I.37-1 to I.37-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.37-1 to I.37-53 in Table I.37 are...

[0293] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0294]

[0295] Table I.38: The preferred compounds of formula (I.38) are compounds I.38-1 to I.38-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.38-1 to I.38-53 in Table I.38 are...

[0296] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0297]

[0298] Table I.39: Preferred compounds of formula (I.39) are compounds I.39-1 to I.39-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.39-1 to I.39-53 in Table I.39 are...

[0299] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0300]

[0301] Table I.40: Preferred compounds of formula (I.40) are compounds I.40-1 to I.40-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.40-1 to I.40-53 of Table I.40 are...

[0302] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0303]

[0304] Table I.41: The preferred compounds of formula (I.41) are compounds I.41-1 to I.41-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.41-1 to I.41-53 in Table I.41 are...

[0305] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0306]

[0307] Table I.42: The preferred compounds of formula (I.42) are compounds I.42-1 to I.42-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.42-1 to I.42-53 in Table I.42 are...

[0308] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0309]

[0310] Table I.43: The preferred compounds of formula (I.43) are compounds I.43-1 to I.43-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.43-1 to I.43-53 in Table I.43 are...

[0311] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0312]

[0313] Table I.44: The preferred compounds of formula (I.44) are compounds I.44-1 to I.44-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.44-1 to I.44-53 in Table I.44 are...

[0314] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0315]

[0316] Table I.45: The preferred compounds of formula (I.45) are compounds I.45-1 to I.45-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.45-1 to I.45-53 in Table I.45 are...

[0317] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0318]

[0319] Table I.46: The preferred compounds of formula (I.46) are compounds I.46-1 to I.46-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.46-1 to I.46-53 in Table I.46 are...

[0320] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0321]

[0322] Table I.47: Preferred compounds of formula (I.47) are compounds I.47-1 to I.47-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.47-1 to I.47-53 in Table I.47 are...

[0323] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0324]

[0325] Table I.48: The preferred compounds of formula (I.48) are compounds I.48-1 to I.48-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.48-1 to I.48-53 in Table I.48 are...

[0326] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0327]

[0328] Table I.49: The preferred compounds of formula (I.49) are compounds I.49-1 to I.49-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.49-1 to I.49-53 in Table I.49 are...

[0329] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0330]

[0331] Table I.50: The preferred compounds of formula (I.50) are compounds I.50-1 to I.50-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.50-1 to I.50-53 of Table I.50 are...

[0332] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0333]

[0334] Table I.51: The preferred compounds of formula (I.51) are compounds I.51-1 to I.51-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.51-1 to I.51-53 in Table I.51 are...

[0335] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0336]

[0337] Table I.52: The preferred compounds of formula (I.52) are compounds I.52-1 to I.52-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.52-1 to I.52-53 in Table I.52 are...

[0338] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0339]

[0340] Table I.53: The preferred compounds of formula (I.53) are compounds I.53-1 to I.53-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.53-1 to I.53-53 in Table I.53 are...

[0341] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0342]

[0343] Table I.54: The preferred compounds of formula (I.54) are compounds I.54-1 to I.54-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.54-1 to I.54-53 in Table I.54 are...

[0344] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0345]

[0346] Table I.55: The preferred compounds of formula (I.55) are compounds I.55-1 to I.55-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.55-1 to I.55-53 in Table I.55 are...

[0347] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0348]

[0349] Table I.56: The preferred compounds of formula (I.56) are compounds I.56-1 to I.56-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.56-1 to I.56-53 in Table I.56 are...

[0350] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0351]

[0352] Table I.57: The preferred compounds of formula (I.57) are compounds I.57-1 to I.57-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.57-1 to I.57-53 in Table I.57 are...

[0353] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0354]

[0355] Table I.58: The preferred compounds of formula (I.58) are compounds I.58-1 to I.58-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.58-1 to I.58-53 in Table I.58 are...

[0356] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0357]

[0358] Table I.59: The preferred compounds of formula (I.59) are compounds I.59-1 to I.59-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.59-1 to I.59-53 in Table I.59 are...

[0359] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0360]

[0361] Table I.60: The preferred compounds of formula (I.60) are compounds I.60-1 to I.60-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.60-1 to I.60-53 of Table I.60 are...

[0362] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0363]

[0364] Table I.61: The preferred compounds of formula (I.61) are compounds I.61-1 to I.61-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.61-1 to I.61-53 in Table I.61 are...

[0365] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0366]

[0367] Table I.62: The preferred compounds of formula (I.62) are compounds I.62-1 to I.62-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.62-1 to I.62-53 in Table I.62 are...

[0368] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0369]

[0370] Table I.63: The preferred compounds of formula (I.63) are compounds I.63-1 to I.63-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.63-1 to I.63-53 in Table I.63 are...

[0371] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0372]

[0373] Table I.64: The preferred compounds of formula (I.64) are compounds I.64-1 to I.64-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.64-1 to I.64-53 in Table I.64 are...

[0374] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0375]

[0376] Table I.65: The preferred compounds of formula (I.65) are compounds I.65-1 to I.65-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.65-1 to I.65-53 in Table I.65 are...

[0377] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0378]

[0379] Table I.66: The preferred compounds of formula (I.66) are compounds I.66-1 to I.66-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.66-1 to I.66-53 in Table I.66 are...

[0380] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0381]

[0382] Table I.67: The preferred compounds of formula (I.67) are compounds I.67-1 to I.67-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.67-1 to I.67-53 in Table I.67 are...

[0383] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0384]

[0385] Table I.68: The preferred compounds of formula (I.68) are compounds I.68-1 to I.68-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.68-1 to I.68-53 in Table I.68 are...

[0386] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0387]

[0388] Table I.69: The preferred compounds of formula (I.69) are compounds I.69-1 to I.69-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.69-1 to I.69-53 in Table I.69 are...

[0389] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0390]

[0391] Table I.70: Preferred compounds of formula (I.70) are compounds I.70-1 to I.70-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.70-1 to I.70-53 of Table I.70 are...

[0392] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0393]

[0394] Table I.71: The preferred compounds of formula (I.71) are compounds I.71-1 to I.71-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.71-1 to I.71-53 in Table I.71 are...

[0395] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0396]

[0397] Table I.72: The preferred compounds of formula (I.72) are compounds I.72-1 to I.72-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.72-1 to I.72-53 in Table I.72 are...

[0398] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0399]

[0400] Table I.73: The preferred compounds of formula (I.73) are compounds I.73-1 to I.73-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.73-1 to I.73-53 in Table I.73 are...

[0401] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0402]

[0403] Table I.74: Preferred compounds of formula (I.74) are compounds I.74-1 to I.74-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.74-1 to I.74-53 in Table I.74 are...

[0404] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0405]

[0406] Table I.75: The preferred compounds of formula (I.75) are compounds I.75-1 to I.75-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.75-1 to I.75-53 in Table I.75 are...

[0407] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0408]

[0409] Table I.76: The preferred compounds of formula (I.76) are compounds I.76-1 to I.76-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.76-1 to I.76-53 in Table I.76 are...

[0410] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0411]

[0412] Table I.77: The preferred compounds of formula (I.77) are compounds I.77-1 to I.77-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.77-1 to I.77-53 in Table I.77 are...

[0413] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0414]

[0415] Table I.78: The preferred compounds of formula (I.78) are compounds I.78-1 to I.78-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.78-1 to I.78-53 in Table I.78 are...

[0416] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0417]

[0418] Table I.79: The preferred compounds of formula (I.79) are compounds I.79-1 to I.79-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.79-1 to I.79-53 in Table I.79 are...

[0419] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0420]

[0421] Table I.80: The preferred compounds of formula (I.80) are compounds I.80-1 to I.80-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.80-1 to I.80-53 of Table I.80 are...

[0422] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0423]

[0424] Table I.81: The preferred compounds of formula (I.81) are compounds I.81-1 to I.81-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.81-1 to I.81-53 in Table I.81 are...

[0425] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0426]

[0427] Table I.82: The preferred compounds of formula (I.82) are compounds I.82-1 to I.82-53, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.82-1 to I.82-53 in Table I.82 are...

[0428] The meanings of the entries 1 to 53 of Q in Table 1 are defined by their respective meanings.

[0429]

[0430] Table I.83: The preferred compounds of formula (I.83) are compounds I.83-1 to I.83-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.83-1 to I.83-53 of Table I.83 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0431] Spectral data for the selected table example:

[0432] Detailed synthetic examples of the selected compounds of the present invention, of general formula (I), are listed below. The chemical examples described in the following sections record... 1 H NMR, 13 C-NMR and 19 F-NMR spectral data ( 1 H NMR is 400MHz 13 C-NMR at 150MHz and 19F-NMR was performed at 375 MHz using CDCl3, CD3OD, or d6-DMSO as solvents, with an internal standard of tetramethylsilane (δ = 0.00 ppm). The obtained signals were acquired 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.

[0433] The spectral data of the selected table examples listed below are obtained through conventional methods. 1 H NMR description or evaluation can be performed using NMR peak listing methods.

[0434] conventional 1 H NMR Explanation

[0435] Example 1 number I.77-49:

[0436] 1 H-NMR (400MHz, CDCl3δ, ppm)7.59(m,1H),7.37(t,1H),7.22(m,1H),7.14(dd,1H),6.97(m,1H ),6.77(m,1H),4.92(s,2H),4.20(t,2H),1.67-1.63(m,2H),1.32-1.26(m,4H),0.87(t,3H).

[0437] Example number I.71-49:

[0438] 1 H-NMR (400MHz, CDCl3δ, ppm)7.59(m,1H),7.40(t,1H),7.22(dd,1H),7.14( dd,1H),6.97(dt,1H),6.77(dt,1H),5.24(q,1H),5.01(s,2H),3.74(s,3H).

[0439] Example 1 number I.70-49:

[0440] 1 H-NMR(400MHz,,CDCl3δ,ppm)7.60(m,1H),7.40(t,1H),7.21(m,1H),7.14(m,1H),6.96(m,1H),6.77(m,1H),5.05(s,2H),4.75(s,2H),3.77(s,3H).

[0441] Example 1 number I.72-49:

[0442] 1 H-NMR (400MHz, CDCl3δ, ppm)7.57(m,1H),7.37(t,1H),7.21(m,1H),7.14(dd,1H) ,6.96(dt,1H),6.77(dt,1H),4.93(s,2H),3.99(d,2H),1.95(m,1H),0.90(d,6H).

[0443] NMR peak listing method

[0444] by 1 The selected embodiment is represented in the form of an H NMR peak list. 1 H NMR data. For each signal peak, the δ value in ppm is listed first, followed by the signal intensity in parentheses. For different signal peaks, the δ value / signal intensity pairs are listed alternately with semicolons.

[0445] Therefore, the peak list in one embodiment takes the following form:

[0446] δ1 (Intensity 1); δ2 (Intensity 2); ...; δ i (strength i );……;δ n (strength n )

[0447] The intensity of the spike signal is related to the signal height (in cm) in the printed NMR spectrum example, and the true proportion of the signal intensity is shown. In the case of a broad-peak signal, several peaks or intermediate portions of the signal and their relative intensities compared to the strongest signal in the spectrum can be shown.

[0448] In order to correct 1 The chemical shifts in 1H NMR spectra are determined using the chemical shifts of tetramethylsilane and / or the solvent, especially when the spectra are measured in DMSO. Therefore, the tetramethylsilane peak may, but is not required, appear in the NMR peak list.

[0449] 1 H NMR peak list compared to conventional 1The H NMR prints are similar and therefore typically include all the peaks listed in a standard NMR description.

[0450] In addition, compared with the conventional 1 Like H NMR prints, they can display solvent signals, stereoisomers of the target compound (also provided by this invention), and / or signals of impurity peaks.

[0451] In the reporting of compound signals in the δ range of solvents and / or water, 1 The H NMR peak list shows standard solvent peaks (e.g., peaks for DMSO and water in DMSO-D6), which, on average, typically have high intensity.

[0452] The average intensity of the peaks of the stereoisomers of the target compound and / or the peaks of impurities is usually lower than that of the peaks of the target compound (e.g., purity > 90%).

[0453] Such stereoisomers and / or impurities can be specific to a particular preparation method. Therefore, their peaks can help identify the reproducibility of the preparation method by referring to "by-product fingerprints".

[0454] Professionals calculate the peaks of the target compound using known methods (MestreC, ACD simulation, and expected values ​​estimated using experience), and optionally use additional intensity filters to separate the peaks of the target compound as needed. This separation is different from conventional methods. 1 The peak picking is similar to that described in the H NMR description.

[0455] It can be found at Research Disclosure Database No. 564025 1 Additional details regarding the HNMR peak list.

[0456]

[0457]

[0458]

[0459]

[0460]

[0461] The present invention also provides a method for protecting crop plants or useful plants from the phytotoxic effects of agrochemicals such as pesticides or, in particular, herbicides, which cause damage to crop plants or useful plants, characterized in that a compound of general formula (I) or a salt thereof is used as a safener, preferably by applying an effective amount of a compound of general formula (I) or a salt thereof to the plant, plant parts or its seeds (or seed material).

[0462] Compounds of general formula (I) above (=safeners) are suitable for use with active ingredients (pesticides) for the selective control of pests in a variety of crop cultures, such as economically important crops like cereals (wheat, barley, rye, rice, corn, millet / sorghum), sugar beets, sugarcane, rapeseed, cotton, sunflowers, peas, legumes, and soybeans. Herbicide-safener compositions with safeners of general formula (I) are also suitable for controlling harmful plants in nurseries and areas of useful and ornamental plants, such as lawn areas of practical or decorative turfgrasses, particularly ryegrass, Kentucky bluegrass, or Bermuda grass.

[0463] With regard to useful plants and crop plants in which herbicide-safety compositions containing compounds of general formula (I) can be used, there is also interest in mutant crops or transgenic crops that are fully or partially resistant to certain pesticides, such as corn crops resistant to glufosinate or glyphosate, or soybean crops resistant to imidazolinones that have phytotoxic effects. However, a particular benefit of safeties of general formula (I) used in a novel manner is their effectiveness in crops that are not normally sufficiently resistant to the pesticides used.

[0464] When used in conjunction with pesticides, compounds of general formula (I) can be applied simultaneously with or in any order to the active ingredients, and thus can reduce or completely prevent the destructive side effects of these active ingredients in the case of crop plants without impairing or significantly reducing their efficacy against unwanted pests. This can also significantly reduce or completely prevent damage caused by the use of more than one pesticide, such as more than one herbicide or a combination of herbicide and insecticide or fungicide. This can considerably expand the application scope of conventional pesticides. If the compositions of the present invention contain pesticides, these compositions are applied directly to the growing area at an appropriate dilution, to germinated harmful plants and / or beneficial plants, or to seedlings of harmful plants and / or beneficial plants. If the compositions of the present invention do not contain any pesticides, these compositions can be used by a so-called tankmix method, meaning that the user mixes and dilutes the separately formulated products (= useful plant protection composition and pesticide) before application to the area to be treated, or before or after pesticide application, or for seed pretreatment (i.e., for coating seeds of beneficial plants). It is preferable to apply the safener promptly with pesticides, especially after herbicides. The beneficial effects can be observed when the compound of general formula (I) is used with pesticides via pre-emergence or post-emergence methods, for example, when applied simultaneously as a tank mix or co-formulation, or when applied alone (in multiple applications) in parallel or consecutively. Multiple applications are also possible. Sometimes combining pre-emergence and post-emergence applications is also reasonable. A common option is post-emergence application to the useful plant or crop, simultaneously or later with the pesticide. Another option is to use the compound (I) of the present invention for seed dressing, (dipping) treatment of seedlings (e.g., rice), or treatment of other propagation materials (e.g., potato tubers).

[0465] When compounds of general formula (I) are used in combination with herbicides, enhanced herbicidal activity against harmful plants is typically observed, in addition to the effects of the safener. Furthermore, in many cases, the growth of beneficial plants and crop plants is improved, and harvest yields can be increased.

[0466] The compositions of the present invention may comprise one or more pesticides. Examples of useful pesticides include herbicides, insecticides, fungicides, acaricides, and nematicides, each of which, when used alone, causes or may cause phytotoxic damage to crop plants. Of particular interest are the respective active pesticide components from herbicides, insecticides, acaricides, nematicides, and fungicides (especially herbicides).

[0467] The weight ratio of the safener (general formula (I)) to the pesticide can vary widely, typically from 1:100 to 100:1, preferably from 1:20 to 20:1, and particularly from 1:10 to 10:1. The optimal weight ratio of safener to pesticide depends on the appropriate safener and pesticide used, as well as the type of beneficial plant or crop to be protected. Depending on the pesticide used and the type of beneficial plant to be protected, the required safener application rate can vary widely, typically from 0.001 to 10 kg per hectare, preferably from 0.01 to 1 kg, and particularly from 0.01 to 0.2 kg of safener. The amount and weight ratio required for successful treatment can be determined by simple preliminary testing.

[0468] In the case of seed dressing, for example, 0.005 to 20 g of safety agent (general formula (I)) per kilogram of seeds is used, preferably 0.01 to 10 g of safety agent per kilogram of seeds, and particularly 0.05 to 5 g of safety agent per kilogram of seeds.

[0469] When using a solution of a safener (general formula (I)) in seed treatment and wetting seeds or seedlings with the solution, the appropriate concentration, based on weight, is typically 1 to 10,000 ppm, preferably 100 to 1,000 ppm. The amount and weight ratio required for successful treatment can be determined by simple preliminary testing.

[0470] Compounds of general formula (I) can be formulated alone or in combination with pesticides in a conventional manner. Therefore, useful plant or crop plant protection compositions are also provided.

[0471] The combined use of safeners and pesticides is preferred, especially when safeners and herbicides are used as finished formulations or by tank mixing.

[0472] Also preferred are compounds of general formula (I) used in seed treatment, followed by application of pesticides, preferably herbicides, after sowing via pre- or post-emergence methods.

[0473] Compounds of general formula (I) or their salts may be used alone or in formulation form in combination with other pesticide actives such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers, and / or growth regulators (e.g., in the form of finished formulations or tank mixes). Considering the physical properties and stability of the active ingredients to be combined, combined formulations can be prepared based on the above formulations.

[0474] Combination agents of the compounds of the present invention that can be used in mixed formulations or tank mixes are, for example, known active ingredients based on inhibition of the following: acetyllactate synthase, acetyl-CoA carboxylase, cellulase, enolpyruvate-shikimate-3-phosphate synthase, glutamine synthase, p-hydroxyphenylpyruvate dioxygenase, phytopenic acid desaturase, photosynthetic system I, photosynthetic system II, or protoporphyrinogen oxidase, as known 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 references cited therein. Known herbicides or plant growth regulators that can be combined with the compounds of the present invention include, for example, those active ingredients represented by their “common name” or chemical name or code as specified by the International Organization for Standardization (ISO). They always include all forms of use, such as acids, salts, esters, and all isomers, such as stereoisomers and optical isomers, even if they are not explicitly mentioned.

[0475] An example of such a herbicide mixture is:

[0476] Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicabazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5- Flupyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutami d) Herbicides including benzolin, benzolin-ethyl, benzfluralin, benzuresate, benzsulfuron, benzsulfuron-methyl, benzulide, benzazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, and bilanafos sodium salt. The following herbicides are listed: nafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, bromoxynil-potassium, bromoxynil-heptanoate, bromoxynil-octanoate, and busoxinone.Butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, and chlorfenuron. Sodium chlorfenac, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, cinidon, cinidon-ethyl, cinmethylin, cetylsulfuron-methyl Inosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, cromazine, clonyluron, cyanamide, cyanazine, cycloate, cyclopyr Imorate, 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 ester, 2,4-D-2-ethylhexyl ester, 2,4-D-isobutyl ester, 2,4-D-isooctyl ester, 2,4-D-isopropylammonium salt,2,4-D-potassium salt, 2,4-D-triisopropanol ammonium salt and 2,4-D-trolamine, 2,4-DB, 2,4-DB-butyl ester, 2,4-DB-dimethylammonium salt, 2,4-DB-isooctyl ester, 2,4-DB-potassium salt and 2,4-DB-sodium salt, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosylpyrazolate (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, 2,4-D-propionic acid (dichlorprop), dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr sodium salt pyr-sodium), dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron uron), dinitrocresol (DNOC), endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, etiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9960,F-5231 (i.e., N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazole-1-yl]-phenyl]ethanesulfonamide), F-7967 (i.e., 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidin-2,4(1H,3H)-dione), fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfon e), fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, floraulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazine Bazone), flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, and flurenol. Flurenol-butyl, flurenol-dimethylammonium, flurenol-methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, and flurochloridone.Fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P- glyphosate sodium, glufosinate-P-ammonium, glyphosate sodium, glyphosate, glyphosate ammonium, glyphosate isopropylammonium, glyphosate diammonium, glyphosate dimethylammonium, glyphosate potassium, glyphosate sodium and Glyphosate-trimesium, H-9201 (O-(2,4-dimethyl-6-nitrophenyl)O-ethylisopropylthiophosphoramide ester), halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, and more. Haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02 (i.e., 1-(dimethoxyphosphoryl)ethyl-(2,4-dichlorophenoxy)acetic acid), imidacloprid, imidacloprid-methyl, imazamox, imazamox-ammonium, imazapicImazopyr ammonium salt, imazopyr, isopropylammonium imazopyr, imazopyr quinolinic acid, imazopyr ammonium salt, imazethapyr, imazethapyr immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron Iodofuron-methyl-sodium, ioxynil, ioxynil-octanoate, ioxynil-potassium, and ioxynil-sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, and KUH-043 (i.e., 3-({[5-(difluoromethyl)-1-methyl)) (3-(trifluoromethyl)-1H-pyrazol-4-yl]methylsulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole), ketospiradox, lactoferrin, lenacil, linuron, MCPA, MCPA-butotyl, MCPA-dimethylammonium salt, MCPA-2-ethylhexyl ester, MCPA-isopropylammonium salt, MCPA-potassium salt and MCPA-sodium salt, MCPB, MCPB-methyl ester, MCPB-ethyl ester and MCPB-sodium salt, 2-methyl-4-chloropropionic acid (mecoprop), 2-methyl-4-chloropropionate sodium (mecoprop) The following are listed: coprop-sodium, mecoprop-butotyl, mecoprop-P, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, and mefenacet.Mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, metiozolin, methyl isothiocyanate, metobromuron, metolachlor chlor), S-metolachlor, metosulam, metoxuron, metribuzin, molinat, monolinuron, monosulfuron-ester, MT-5950 (N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide), NGGC-011, napropamide, NC-310 (4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole), neburon, nicosulfuron, nonanoic acid acid (pelargonic acid), norflurazon, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, mineral oil, phenmedipham, picloram, picolinafen, pinoxadenPiperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, probenzylsulfuron The following are listed: poxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), and pyrazosulfuron. Pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfa n. Pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefurylRimsulfuron, 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-oxobut-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-thioimidazolidine-4,5-dione), 2,3,6-TBA, TCA (trichloroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbutazine rbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, toramezone, tralkoxydim, trifluralin afamone, tri-allate, triasulfuron, triaziflam, tribenuron-methyl, tribenuron-methyl, trilopyr, trietazine, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuronTriflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862 (i.e., 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline), and the following compounds:

[0477]

[0478] Examples of plant growth regulators that can be used as possible mixed formulations include:

[0479] Acibenzolar, benzothiadiazole (acibenzolar-S-methyl), 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolid, catechol, chlormequat chloride chloride), cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, endothal-disodium, and N,N-dimethylalkylammonium endothal, ethephon, flumetralin, butyl fluorene, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indole-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid acid), methyl jasmonic acid, maleic hydrazine, 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-phenylphthalamicacid, prohexadione, calcium prohexadione, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

[0480] When used as active ingredient formulations or co-formulations, these typically contain a variety of commonly used binders, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors, as well as pH and viscosity adjusters, depending on the situation.

[0481] Compounds of general formula (I) and their combinations with one or more of the aforementioned pesticides can be formulated in various ways according to defined physicochemical and biological parameters. Suitable examples of formulation types include:

[0482] - An emulsifiable concentrate prepared by dissolving an 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 nonionic surfactants (emulsifiers). Suitable emulsifiers include, for example, calcium alkyl aryl sulfonate, fatty acid polyethylene glycol esters, alkyl aryl polyethylene glycol ethers, fatty alcohol polyethylene glycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, and polyoxyethylene sorbitan fatty acid esters;

[0483] - A powdered product obtained by grinding an active ingredient with a finely dispersed solid inorganic or organic substance, such as talc, natural clay, such as kaolin, bentonite, pyrophyllite, diatomaceous earth, or diatomaceous earth powder.

[0484] - Aqueous or oil-based suspension concentrates, which can be prepared by, for example, wet milling using a bead mill;

[0485] -Water-soluble powder;

[0486] -Water-soluble concentrate;

[0487] - Particles, such as water-soluble particles, water-dispersible particles, and particles for broadcasting and soil application;

[0488] - Wettable powders, which, in addition to active ingredients, also contain diluents or inert substances and surfactants;

[0489] -Capsule suspensions and microcapsules;

[0490] -Ultra-low dose formulation.

[0491] The aforementioned formulation types are known to those skilled in the art and are described, for example, in K. Martens, “Spray Drying Handbook”, 3rd ed., G. Goodwin Ltd., London, 1979; W. van Valkenburg, “Pesticide Formulations”, Marcel Dekker, NY, 1973; Winacker-Küchler, “Chemische Technologie”.

[0492] [Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th edition 1986; "Perry's Chemical Engineer's Handbook", 5th ed., McGraw-Hill, NY1973, pages 8-57.

[0493] Necessary formulation adjuvants, such as inert materials, surfactants, solvents, and other additives, are also known and documented in, for example, McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; C. Marsden, "Solvents Guide", 2nd ed., Interscience, NY 1963; H. von Olphen, "Introduction to Clay Colloid Chemistry", 2nd ed., J. Wiley & Sons, NY;

[0494] [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY1964; Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell N.J.; Winnacker-Küchler, "Chemische Technologie", volume 7, C. Hanser Verlag Munich, 4th edition 1986.

[0495] In addition to the formulation adjuvants mentioned above, useful plant protection compositions may, as appropriate, contain commonly used wetting agents, binders, dispersants, penetrants, emulsifiers, preservatives, antifreeze agents, fillers, carriers and dyes, defoamers, evaporation inhibitors, as well as pH and viscosity adjusters.

[0496] Depending on the type of formulation, useful plant protection compositions typically contain 0.1% to 99% by weight, particularly 0.2% to 95% by weight, of one or more of a safener of general formula (I) or a combination of a safener and a pesticide. They also contain 1% to 99.9% by weight, particularly 4% to 99.5% by weight, of one or more solid or liquid additives and 0% to 25% by weight, particularly 0.1% to 25% by weight, of a surfactant. In emulsifiable concentrates, the concentration of the active ingredient, i.e., the concentration of the safener and / or pesticide, is typically 1% to 90% by weight, particularly 5% to 80% by weight. Powdered products typically contain 1% to 30% by weight, preferably 5% to 20% by weight, of the active ingredient. In wettable powders, the concentration of the active ingredient is typically 10% to 90% by weight. In water-dispersible granules, the content of the active ingredient is, for example, 1% to 95% by weight, preferably 10% to 80% by weight.

[0497] For application, commercially available formulations are diluted in the usual manner, if applicable, such as with water in the case of wettable powders, emulsifiable concentrates, dispersants, and water-dispersible granules. Powder, granule, and sprayable solutions are generally not further diluted with other inert substances before application. The required application rate for safeners of general formula (I) varies depending on external conditions, including temperature, humidity, and the type of herbicide used.

[0498] In the embodiments described below, but not limiting of the invention, unless otherwise defined, the expressions of quantity are based on weight. Example

[0499] 1. Formulation Examples

[0500] 1.1 Powdered Products

[0501] The powdered product is obtained by mixing 10 parts by weight of a compound of general formula (I) (safest agent) or a mixture of active ingredients consisting of a pesticide (e.g., a herbicide) and a safest agent of general formula (I) with 90 parts by weight of talc as an inert substance and pulverizing the mixture in a bead mill.

[0502] 1.2 Water-dispersible powder

[0503] A water-dispersible wettable powder is obtained by mixing 25 parts by weight of a compound of general formula (I) or a mixture of active ingredients consisting of a pesticide (e.g., a herbicide) and a safener of general formula (I), 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignin sulfonate and 1 part by weight of sodium oleoylmethyl taurate as a wetting agent and dispersant, and grinding the mixture in a fixed disc mill.

[0504] 1.3 Water-dispersible concentrates

[0505] By mixing 20 parts by weight of a compound of general formula (I) or a mixture of active ingredients consisting of a pesticide (e.g., a herbicide) and a safener of general formula (I) with 6 parts by weight of alkylphenol polyethylene glycol ether ( X 207), 3 parts by weight of isotridecyl alcohol polyethylene glycol ether and 71 parts by weight of paraffin mineral oil were mixed and ground in a friction ball mill to a fineness of less than 5 micrometers to obtain an easily water-dispersible concentrate.

[0506] 1.4 emulsifiable concentrate

[0507] An emulsifiable concentrate is obtained from 15 parts by weight of a compound of general formula (I) or a mixture of active ingredients consisting of a pesticide (e.g., a herbicide) and a safener of general formula (I), 75 parts by weight of cyclohexanone as a solvent, and 10 parts by weight of ethoxylated nonylphenol as an emulsifier.

[0508] 1.5 Water-dispersible particles

[0509] Water-dispersible particles are obtained by mixing the following components:

[0510] 75 parts by weight of a safener of formula (I) or a mixture of a pesticide and a safener of formula (I),

[0511] 10 parts by weight of calcium lignosulfonate,

[0512] 5 parts by weight of sodium dodecyl sulfate,

[0513] 3 parts by weight of polyvinyl alcohol, and

[0514] 7 parts by weight of polyvinyl alcohol, and

[0515] 7 parts by weight of kaolin,

[0516] The mixture is ground in a pin mill and the powder is granulated in a fluidized bed by spraying water as the granulation liquid.

[0517] Water-dispersible particles can also be obtained by homogenizing and pulverizing the following components in a colloid mill:

[0518] 25 parts by weight of a safener of formula (I) or a mixture of a pesticide and a safener of formula (I),

[0519] 5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate

[0520] 2 parts by weight of sodium oleoylmethyl taurate,

[0521] 17 parts by weight of calcium carbonate

[0522] 50 parts by weight of water, and

[0523] 1 part by weight of polyvinyl alcohol,

[0524] The mixture is then ground in a bead mill and atomized and dried in a spray tower through a single-phase nozzle to obtain the suspension.

[0525] 2. Biological Examples

[0526] 2.1 Taking the reduction of damage to summer wheat (TRZAS) by mesosulfuron-methyl as an example, the relative effects of the selected compounds of the present invention are as follows:

[0527] The crop seeds to be treated were arranged on sandy loam soil in plastic pots (approximately 4 cm in diameter), covered with soil, and grown in a greenhouse under favorable germination and growth conditions. The test plants were treated at the early leaf stage (BBCH10-BBCH12). During this process, the compound of the invention, formulated as a wettable powder (WP), was sprayed onto the aboveground parts of the plants as an aqueous suspension at a rate equivalent to 800 l / ha, with the addition of a specified dose of wetting agent (e.g., 0.2% Genapol-LRO or 0.2% Mero).

[0528] Herbicides were then applied. For this purpose, mesosulfuron-methyl, formulated as water-dispersible granules (WG), was sprayed onto the aboveground parts of the plants in aqueous dispersion form at a rate equivalent to 800 l / ha of water, with the addition of a wetting agent at a dose of 40-60 g / ha (e.g., 0.2%).

[0529] (Genapol-LRO or 1 l / ha Biopower). The herbicide dosage selected here should cause visually significant damage (minimum 30%, maximum 75%) to control crop plants included in the same trial that were not treated with the safener, compared to untreated crop plants at the time of evaluation.

[0530] After application, the plants were cultured in a greenhouse with good growing conditions. Nine to 13 days after application, the efficacy of the test compound was visually assessed. For this purpose, the appearance of plants treated with the test compound and herbicide was compared with the corresponding herbicide control (no safener; visible damage) and the untreated control (no damage). The damage-reducing effect of the test compound is expressed here using a graded efficacy code according to the following scheme:

[0531] 0: No damage reduction (appearance equivalent to herbicide control)

[0532] 1: The damage has been slightly reduced.

[0533] 2: The damage was significantly reduced.

[0534] 3: Damage significantly reduced

[0535] 4: No damage (appearance is equivalent to the untreated control)

[0536] Experiments have shown that the compounds of the present invention selected as examples are significantly effective in mitigating damage to summer wheat crops (TRZAS; cv. Triso) caused by herbicides (such as mesosulfuron-methyl).

[0537]

[0538]

[0539] 2.2 Taking the reduction of damage to summer barley (HORVS) by mesosulfuron-methyl as an example, the relative effects of the selected compounds of the present invention are as follows:

[0540] The crop seeds to be treated were arranged on sandy loam soil in plastic pots (approximately 4 cm in diameter), covered with soil, and grown in a greenhouse under favorable germination and growth conditions. The test plants were treated at the early leaf stage (BBCH10-BBCH12). During this process, the compound of the invention, formulated as a wettable powder (WP), was sprayed onto the aboveground parts of the plants as an aqueous suspension at a rate equivalent to 800 l / ha, with the addition of a specified dose of wetting agent (e.g., 0.2% Genapol-LRO or 0.2% Mero).

[0541] Herbicides were then applied. For this purpose, mesosulfuron-methyl, formulated as water-dispersible granules (WG), was sprayed onto the aboveground parts of the plants in aqueous dispersion form at a rate equivalent to 800 l / ha of water, with the addition of a wetting agent at a dose of 40-60 g / ha (e.g., 0.2%).

[0542] (Genapol-LRO or 1 l / ha Biopower). The herbicide dosage selected here should cause visually significant damage (minimum 30%, maximum 75%) to control crop plants included in the same trial that were not treated with the safener, compared to untreated crop plants at the time of evaluation.

[0543] After application, the plants were cultured in a greenhouse with good growing conditions. Nine to 13 days after application, the efficacy of the test compound was visually evaluated. For this purpose, the appearance of plants treated with the test compound and herbicide was compared with the corresponding herbicide control (no safener; visible damage) and the untreated control (no damage). The damage-reducing effect of the test compound was repeated twice and expressed using the graded efficacy code according to the following scheme:

[0544] 0: No damage reduction (appearance equivalent to herbicide control)

[0545] 1: The damage has been slightly reduced.

[0546] 2: The damage was significantly reduced.

[0547] 3: Damage significantly reduced

[0548] 4: No damage (appearance is equivalent to the untreated control)

[0549] Experiments have shown that the compounds of the present invention selected as examples are significantly effective in mitigating damage to summer barley crops (HORVS; cv. Montoya) caused by herbicides (such as mesosulfuron-methyl).

[0550]

Claims

1. Compounds of general formula (I) or their salts in R 1 Selected from groups (R 2 ) m -Phenyl group is selected from radicals R 3 It is hydrogen or (C1-C6) alkyl. R 4 It can be hydrogen or methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl or isobutyl.

2. The compound of general formula (I) according to claim 1, or a salt thereof, in R 3 It is hydrogen or (C1-C4) alkyl.

3. The compound of general formula (I) according to claim 1, or a salt thereof, in R 3 It can be hydrogen, CH2CH3, or CH3.

4. The compound of general formula (I) according to claim 1, or a salt thereof, in R 3 It is hydrogen or CH3.

5. The compound of general formula (I) according to claim 1, or a salt thereof, in R 3 It is hydrogen.

6. The compound of general formula (I) according to claim 1, or a salt thereof, in R 1 Selected from groups (R 2 ) m -Phenyl group is selected from radicals R 3 It is hydrogen. and R 4 It can be hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, or isobutyl.

7. The compound of general formula (I) according to claim 1, or a salt thereof, in R 1 Selected from groups (R 2 ) m -Phenyl group is selected from radicals R 3 It is hydrogen. and R 4 It can be hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, or isobutyl.

8. The compound of general formula (I) according to claim 1, or a salt thereof, in R 1 for (R 2 ) m -Phenyl group is selected from radicals R 3 It is hydrogen. and R 4 It can be hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, or isobutyl.

9. A compound of general formula (I) according to any one of claims 1 to 8, or a salt thereof. in R 4 It can be hydrogen, methyl, or ethyl.

10. A compound is selected from the following compounds or their salts. 。 11. A useful plant or crop plant protection composition, characterized in that, It contains at least one compound or salt thereof according to any one of claims 1 to 10, in combination with other agrochemicals and optionally formulation adjuvants.

12. The composition according to claim 11, comprising at least one herbicide.

13. A method for reducing the phytotoxic effects of pesticides on useful plants or crop plants, comprising using one or more compounds according to any one of claims 1 to 10 or salts thereof or compositions according to claims 11 or 12.

14. A method for reducing the phytotoxic effects of pesticides on useful plants or crops, characterized in that, One or more of the compounds or salts thereof according to any one of claims 1 to 10, applied in combination with pesticides, are applied simultaneously or in any order with the pesticides.

15. The method according to claim 14, wherein the pesticide is one or more herbicides.

16. The method according to claim 14 or 15, characterized in that, The compound or salt thereof as described in any one of claims 1 to 10 is applied to a plant or its seeds.

17. The method according to claim 14 or 15, characterized in that, The compound or salt thereof as described in any one of claims 1 to 10 is applied to plant parts or seed material.

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