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

Abstract

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

Description

[0001] This invention relates to useful plant protection compounds and compositions comprising specific compounds as safeners for reducing the phytotoxicity of agricultural chemicals, particularly herbicides. More specifically, this invention relates to specific [(1,5-di(heteroaryl)-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives as safeners, their salts, and methods for their preparation.

[0002] When pesticides are used to control unwanted organisms in horticultural and forestry crops, the beneficial plants are often also more or less harmed by the pesticides used (e.g., herbicides, insecticides, fungicides, etc.). This unwanted phytotoxicity occurs to a certain degree when large amounts of herbicides are used in beneficial crops (e.g., 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 effect of compounds selected from phenoxy or heteroaryloxyalkane carboxylic acid derivatives when used in combination with herbicides is well known. Examples of such compounds are MCPA and similar compounds that still retain herbicidal activity against harmful plants, or cloquintocet-mexyl.

[0005] Also known are safeners selected from 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 for use as safeners in corn and soybean crops.

[0007] In addition, WO 2005 / 112630 discloses 1,2-dihydroquinoxalin-2-one derivatives, and WO 2008 / 131860 discloses pyridone formamide as a safer agent.

[0008] The active ingredients, which are derived from the chemical categories of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxylic acid derivatives and 1,5-diphenyl-1H-pyrazole-3-carboxylic acid derivatives with plant-active properties, and are used as safeners, are known from WO2006 / 040016.

[0009] The active ingredient, which is a chemical class of 1,5-diphenyl-1H-pyrazole-3-carboxylic acid derivatives with plant-active properties, is also known as a safener from EP0268554.

[0010] The active ingredients derived from the chemical category of [(1,5-di(heteroaryl)-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives with plant-active properties are unknown in the literature.

[0011] Various literatures document pharmaceutically valuable derivatives of [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid. Polish J. Chem. 2006, 80, 889-897 and Bioorganic & Medicinal Chemistry 2018, 26, 3321-3344 disclose derivatives of [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid.

[0012] When safeners are used to protect crops from pesticide damage, it has been found that known safeners have drawbacks in many cases. These drawbacks include:

[0013] - Insufficient useful plant protection characteristics

[0014] - When used in combination with a specific herbicide, the range of beneficial plants for the safener / herbicide to be used is not large enough.

[0015] - Certain safeners can only be combined with a few herbicides.

[0016] The use of safety agents increases the application rate and dosage of formulation adjuvants, which can lead to application-related problems.

[0017] For the reasons stated above, there is an increasing need to provide alternative compounds that act as safety agents.

[0018] This invention provides novel useful plant protection compounds of general formula (I) or salts thereof.

[0019]

[0020] Used to reduce the phytotoxicity of pesticides, especially herbicides, to beneficial plants or crops.

[0021] in

[0022] R 1 and R 2 Independently, it is a heteroaryl group, wherein the heteroaryl group is unsubstituted or halogenated, cyano, nitro, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)ynyl, (C3-C8)cycloalkyl, (C3-C8)cycloalkenyl, (C1-C6)alkoxy, and (C1-C6)alkyl S(O). p Substitution, wherein the last seven groups are unsubstituted or replaced by one or more groups selected from halogens, cyano groups, (C1-C6)alkoxy groups, and (C1-C6)alkyl groups (S(O)). p Substitution of groups,

[0023] R 3 It consists of hydrogen and (C1-C6) alkyl groups.

[0024] R 4 For hydrogen, (C1-C 18 )alkyl, (C1-C 18 ) Haloalkyl, (C1-C 18 )cyanoalkyl, (C2-C 18 )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-(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 )alkyl, (C3-C 12 )cycloalkyl-(C1-C 18 )alkyl, (C1-C 18 )alkoxycarbonyl-(C1-C 18 )alkyl and (C1-C 18 )alkoxycarbonyl-(C3-C 12 )cycloalkyl-(C1-C 18 )alkyl, or

[0025] Formula-NR a R b Or -N = CR c R d group,

[0026] Among the aforementioned two groups, R a R b R c and R d Each group is independently hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)ynyl, benzyl, substituted benzyl, phenyl, or substituted phenyl.

[0027] Or R a and R b Together with the nitrogen atom, it can form a 3- to 8-membered heterocycle, which may contain one or two other cyclic heteroatoms selected from N, O, and S, and is either unsubstituted or substituted by one or more groups selected from (C1-C4) alkyl and (C1-C4) haloalkyl groups, or R c and R d Together with carbon atoms, they form 3- to 8-membered carbocyclic or heterocyclic groups, which may contain 1 to 3 cyclic heteroatoms selected from N, O, and S, wherein the carbocyclic or heterocyclic group is unsubstituted or substituted by one or more groups selected from (C1-C4) alkyl and (C1-C4) haloalkyl groups.

[0028] and

[0029] p is 0, 1, or 2.

[0030] Compounds of general formula (I) can be salted by adding a suitable inorganic or organic acid, such as inorganic acids like HCl, HBr, H2SO4, H3PO4, or HNO3, or organic acids like carboxylic acids (e.g., formic acid, acetic acid, propionic acid, oxalic acid, lactic acid, or salicylic acid) or sulfonic acids (e.g., p-toluenesulfonic acid), to a basic group, such as an amino, alkylamino, dialkylamino, piperidinyl, morpholinyl, or pyridinyl group. These salts then contain the conjugate base of the acid as an anion. A suitable deprotonated form of the substituent (e.g., sulfonic acid, particularly sulfonamides or carboxylic acids) can form an inner salt with a self-protonable group (e.g., an amino group). Salts can also be formed by the action of a base on compounds of general formula (I). Suitable bases are, for example, organic amines such as trialkylamines, morpholine, piperidinium, and pyridine, as well as 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, especially alkali metal or alkaline earth metal salts, particularly sodium and potassium salts, or ammonium salts, salts with organic amines, or quaternary ammonium salts, for example having the formula [NR].i R ii R iii R iv ] + The cation, wherein R i To R iv Each is an independent organic group, especially alkyl, aryl, arylalkyl, or alkylaryl. Alkyl sulfonate salts and alkyl oxide sulfonate salts are also used, such as (C1-C4)-trialkyl sulfonate salts and (C1-C4)-trialkyl oxide sulfonate salts.

[0031] The compounds of formula (I) and their salts used in this invention are referred to below as "compounds of general formula (I)".

[0032] The present invention preferably provides compounds of general formula (I), wherein

[0033] R 1 and R 2 Independently, it is a heteroaryl group, wherein the heteroaryl group is unsubstituted or halogenated, cyano, nitro, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C4)ynyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkenyl, (C1-C4)alkoxy, and (C1-C4)alkyl S(O). p Substitution, wherein the last seven groups are unsubstituted or replaced by one or more groups selected from halogens, cyano groups, (C1-C4)alkoxy groups, and (C1-C4)alkyl groups (S(O)). p Substitution of groups,

[0034] R 3 It consists of hydrogen and (C1-C4) alkyl groups.

[0035] R 4 For hydrogen, (C1-C 16 )alkyl, (C1-C 16 ) Haloalkyl, (C1-C 16 )cyanoalkyl, (C2-C 16 )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-(C1-C 16 )alkyl, (C1-C 16 )alkoxy-(C1-C 16 ) Haloalkyl, (C1-C 16 )alkylthio-(C1-C 16 )alkyl, (C1-C16 ) Haloalkylthio-(C1-C 16 )alkyl, (C2-C 16 ) Haloalkenyl, (C2-C 16 ) Haloalkynyl, heterocyclic -(C1-C 16 )alkyl, aryl-(C1-C 16 )alkyl, (C3-C 12 )cycloalkyl-(C1-C 16 )alkyl, (C1-C 16 )alkoxycarbonyl-(C1-C 16 )alkyl and (C1-C 16 )alkoxycarbonyl-(C3-C 12 )cycloalkyl-(C1-C 16 )alkyl,

[0036] and

[0037] p is 0, 1, or 2.

[0038] The present invention particularly preferably provides compounds of general formula (I), wherein

[0039] R 1 and R 2 Independently, it is a heteroaryl 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.

[0040] R 3 For hydrogen, CH2CH3 and CH3,

[0041] 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-C12 )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 )alkyl and (C1-C 12 )alkoxycarbonyl-(C3-C 12 )cycloalkyl-(C1-C 12 )alkyl,

[0042] and

[0043] p is 0, 1, or 2.

[0044] The present invention particularly preferably provides compounds of general formula (I), wherein

[0045] R 1 and R 2The 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-oxazinyl, 1,3,2-oxazinyl, 1,3,6-oxazinyl 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, Thiophene-2-yl, Thiophene-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- Pyrazol-4-yl, 1H-pyrazol-5-yl, 1H-1,2,3-triazol-1-yl, 1H-1,2,3-triazol-4-yl, 1H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1,2,4-triazol-1-yl, 1H-1,2,4-triazol-3-yl, 4H-1,2,4-triazol-4-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5 -yl, 1,2,5-oxadiazol-3-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-thiadiazol-5-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,5-thiadiazol-3-yl, 1,2,5-thiadiazol-3-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, which are unsubstituted or mono- or polysubstituted with hydrogen, fluorine, chlorine, bromine, iodine, CN, methyl, CF3, CF2Cl, CH2F, CHF2, OCH3, OCF3, SCH3, SOCH3, SO2CH3 and SCF3.

[0046] R 3 It consists of hydrogen and CH3.

[0047] and

[0048] R 4 For hydrogen, (C1-C 10 )alkyl, (C1-C10 ) 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, (C2-C 18 ) Haloalkynyl, heterocyclic -(C1-C 10 )alkyl, aryl-(C1-C 10 )alkyl, (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.

[0049] The present invention particularly preferably provides compounds of general formula (I), wherein

[0050] R 1 The group is Q-1.1 to Q-1.60.

[0051]

[0052]

[0053]

[0054] R 2 The groups are Q-2.1 to Q-2.61.

[0055]

[0056]

[0057]

[0058] R 3 It is hydrogen.

[0059] R 4 The 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, methyl-pivalate-2-yl, ethyl-pivalate-2-yl 3-yl, methyl-2-methylpropionate-3-yl, methyl-2,2-dimethylpropionate-3-yl, ethyl-2-methylpropionate-3-yl, methyl-2-propionate-2-yl, ethyl-2-propionate-2-yl, methylacetyl-2-yl, ethylacetyl-2-yl, methyl-1-methylcyclopropanecarboxylate-2-yl, ethyl-1-methylcyclopropanecarboxylate-2-yl, 2-(dimethylamino)ethyl, oxetan-3-yl, (3-methyloxetan-3-yl)methyl, 2,2,2-trifluoroethyl, 2, 2-Difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl, cyclopropylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl, allyl, 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)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, hept-2-yl, isobutyl, 1,3-dioxacyclopentan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl.

[0060] The present invention particularly and especially preferably provides compounds of general formula (I), wherein

[0061] R 1 The group is Q-1.1 to Q-1.60.

[0062]

[0063]

[0064] and

[0065] R 2 The groups are Q-2.1 to Q-2.61.

[0066]

[0067] R 3 It is hydrogen.

[0068] R 4 The 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, methyl-pivalate-2-yl, ethylpivalic 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)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, hept-2-yl, isobutyl, 1,3-dioxacyclopentan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl.

[0069] The definitions of the general or preferred groups described above apply both to the final product of general formula (I) and, correspondingly, to the preparation of the desired raw materials or intermediates in each case. These definitions can be combined as needed, i.e., combinations between given preferred ranges.

[0070] Firstly, the compounds of general formula (I) of the present invention or their salts, or their uses in the present invention, are of particular importance due to their higher herbicidal activity, better selectivity, and / or better preparability, wherein each group has one of the preferred meanings specified or given below, or in particular, wherein one or more of the preferred meanings specified or given below appear in combination.

[0071] Regarding the compounds of the present invention, the terms used above and further used below will be explained. These terms are well known to those skilled in the art and, in particular, have the definitions set forth below:

[0072] Unless otherwise defined, the name of a chemical group should generally be understood as such that the connection to the skeleton or the rest of the molecule is through the last mentioned structural element of the relevant chemical group, i.e., through the oxygen atom in the case of (C2-C8)-olefin, and through the carbon atom of the alkyl group in the case of heterocyclic-(C1-C8)-alkyl or MeO(O)C-(C1-C8)-alkyl.

[0073] According to the present invention, "alkylsulfonyl" – alone or as part of a chemical group – refers preferably to a straight-chain or branched alkylsulfonyl group having 1 to 8 or 1 to 6 carbon atoms, such as (but not limited to) (C1-C6)-alkylsulfonyl, such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentyl-sulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethyl-propylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethyl Propylsulfonyl, 1-ethylpropylsulfonyl, hexyl-sulfonyl, 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-methyl-propylsulfonyl, and 1-ethyl-2-methylpropylsulfonyl.

[0074] According to the present invention, "alkylthio"—alone or as part of a chemical group—preferably refers to a straight-chain or branched S-alkyl group having 1 to 8 or 1 to 6 carbon atoms, for example (C1-C2). 10 (C1-C6)-alkylthio, (C1-C4)-alkylthio, such as (but not limited to) (C1-C6)-alkylthio, including methylthio, ethylthio, propanethio, 1-methylethylthio, butylthio, 1-methylpropanethio, 2-methylpropanethio, 1,1-dimethylethylthio, pentanethio, 1-methylbutanethio, 2-methylbutanethio, 3-methylbutanethio, 1,1-dimethylpropanethio, 1,2-dimethylpropanethio, 2,2-dimethylpropanethio, 1-ethylpropanethio, Hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutyrothio, 1,2-dimethylbutyrothio, 1,3-dimethyl-butyrothio, 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.

[0075] According to the present invention, unless otherwise defined, "alkylsulfinyl (alkyl-S(=O)-)" means an alkyl group bonded to the skeleton by -S(=O)-, for example (C1-C 10 (C1-C6)-alkylsulfinyl, (C1-C4)-alkylsulfinyl, such as (but not limited to) (C1-C6)-alkylsulfinyl, including methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropyl Sulphinyl, 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.

[0076] "Alkoxy" refers to an alkyl group linked by an oxygen atom, such as (but not limited to) (C1-C6)-alkoxy groups, including 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 an oxygen atom, and alkynyloxy groups represent alkynyl groups linked by an oxygen atom, for example (C2-C...). 10 (C2-C6)-olefin, (C2-C4)-olefin, or (C2-C4)-olefin, and (C3-C 10 (C3-C6)-acetyloxy, (C3-C4)-acetyloxy, or (C3-C4)-acetyloxy.

[0077] 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)-alkylcarbonyl, (C1-C4)-alkylcarbonyl. Here, the number of carbon atoms is related to the alkyl group in the alkylcarbonyl group.

[0078] Unless otherwise defined, "alkoxycarbonyl (alkyl-OC(=O)-)" means: an alkyl group bonded to the skeleton by -OC(=O)-, for example (C1-C 10 (C1-C4)-alkoxycarbonyl, (C1-C6)-alkoxycarbonyl, or (C1-C4)-alkoxycarbonyl. Here, the number of carbon atoms is related to the alkyl group in the alkoxycarbonyl group. Similarly, according to the invention, unless otherwise defined, "alkenyloxycarbonyl" and "alkynyloxycarbonyl" respectively represent an alkenyl group and an alkynyl group bonded to the skeleton by -OC (=O)-, for example (C2-C4)-alkoxycarbonyl. 10 (C2-C4)-olefin carbonyl, (C2-C6)-olefin carbonyl or (C2-C4)-olefin carbonyl, and (C3-C4)-olefin carbonyl 10 (C3-C6)-alkynoxycarbonyl, (C3-C4)-alkynoxycarbonyl. Here, the number of carbon atoms refers to the alkenyl or alkynyl group in the alkenyloxycarbonyl or alkynoxycarbonyl group.

[0079] The term "aryl" refers to a monocyclic, bicyclic, or polycyclic aromatic system having optionally substituted 6 to 14, particularly 6 to 10, cyclic carbon atoms, such as phenyl, naphthyl, anthracene, phenanthryl, etc., with phenyl being preferred.

[0080] The expression "optionally substituted aryl" also includes polycyclic systems such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, and biphenyl, wherein the bonding site is located on an aromatic system. In systematic terminology, "aryl" is often also encompassed by the expression "optionally substituted phenyl". Preferred aryl substituents in this document are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclic, heterocyclic alkyl, alkoxyalkyl, alkathioyl, alkylthio, haloalkylthio, haloalkyl, alkoxy, haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, dialkyl-aminoalkoxy, 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, Alkoxycarbonyl-amino, Alkoxycarbonylalkylamino, Arylalkoxycarbonylalkylamino, Hydroxylcarbonyl, Alkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Cycloalkylaminocarbonyl, Dialkylaminocarbonyl, Heteroaryl-alkoxy, Arylalkoxy.

[0081] A heterocyclic group (heterocyclic group) comprises at least one heterocycle (i.e., a carbon ring in which at least one carbon atom is replaced by a heteroatom, preferably a heteroatom selected from N, O, S, 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 carbon 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, the heterocycle preferably comprises 3 to 9 ring atoms, particularly 3 to 6 ring atoms, and contains one or more, preferably 1 to 4, particularly 1, 2 or 3 heteroatoms, said heteroatoms preferably selected from N, O and S, but two oxygen atoms should not be directly adjacent, for example having one heteroatom selected 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-Dihydro-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-azacycloheptene-1- or 2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,4,7-tetrahydro-1H-azacycloheptene-1- or 2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,6, 7-Tetrahydro-1H-azacyclohepten-1- or -2- or -3- or -4-yl, 3,4,5,6-Tetrahydro-2H-azacyclohepten-2- or -3- or -4- or -5- or -6- or -7-yl, 4,5-Dihydro-1H-azacyclohepten-1- or -2- or -3- or -4-yl, 2,5-Dihydro-1H-azacyclohepten-1- or -2- or -3- or -4- or -5- or -6- or -7-yl, 2,7-Dihydro-1H-azacyclohepten-1- or -2- or -3- or -4-yl, 2,3-Dihydro-1H-azacyclohepten-1-or-2-or-3-or-4-or-5-or-6-or-7-yl, 3,4-Dihydro-2H-azacyclohepten-2-or-3-or-4-or-5-or-6-or-7-yl, 3,6-Dihydro-2H-azacyclohepten-2-or-3-or-4-or-5-or-6-or-7-yl, 5,6-Dihydro-2H-azacyclohepten-2-or-3-or-4-or-5-or-6-or-7-yl, 4,5-Dihydro-3H-azacyclohepten-2-or-3-or-4-or-5-or-6-or-7-yl, 1H-azacyclohepten-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-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-oxolanyl (=2- or 3- or 4-tetrahydropyranyl), 3,4-dihydro-2H-pyranyl- 2- or 3- or 4- or 5- or 6-yl, 3,6-dihydro-2H-pyran-2- or 3- or 4- or 5- or 6-yl, 2H-pyran-2- or 3- or 4- or 5- or 6-yl, 4H-pyran-2- or 3- or 4-yl, 2- or 3- or 4-oxepanyl, 2,3,4,5-tetrahydrooxecyclohepten-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,4,7-tetrahydrooxecyclohepten-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,6,7-tetrahydrooxecyclohepten-2- or 3- or 4-yl, 2 3-Dihydrooxetrazine-2- or 3- or 4- or 5- or 6- or 7-yl, 4,5-Dihydrooxetrazine-2- or 3- or 4-yl, 2,5-Dihydrooxetrazine-2- or 3- or 4- or 5- or 6- or 7-yl, oxetrazine-2- or 3- or 4- or 5- or 6- or 7-yl, 2- or 3-tetrahydrothiophene, 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-aziridobutyl, 2- or 3-oxetyl, 2- or 3-thietyl, and 1,3-dioxetane-2-yl. Other examples of "heterocyclic groups" are partially or fully hydrogenated heterocyclic groups having two heteroatoms selected 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-1- or 2- or 3- or 4-yl groups, 2,5-dihydro-1H-imidazolyl-1- or 2- or 3- or 4-yl groups. -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- or 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-, 4-, 5-, or 6-yl; 1,2,5,6-tetrahydropyrimidine-1-, 2-, 4-, 5-, or 6-yl; 1,2,3,4-tetrahydropyrimidine-1-, 2-, 3-, 4-, 5-, or 6-yl; 1,6-dihydropyrimidine-1-, 2-, 4-, 5-, or 6-yl; 1,2-dihydropyrimidine-1- 2,5-dihydropyrimidin-2,4,5-dihydropyrimidin-4,5,6-dihydropyrimidin-1,2,4,5,5-dihydropyrimidin-1,2,4,5,5,5-dihydropyrimidin-1,2,4,5,5,5-dihydropyrimidin-1,2,4,5,5,5-dihydropyrimidin-1,2,3,4 ...3-Dihydropyrazine-2- or 3- or 5- or 6-yl, 2,5-Dihydropyrazine-2- or 3-yl, 1,3-dioxolane-2- or 4- or 5-yl, 1,3-dioxol-2- or 4-yl, 1,3-dioxan-2- or 4- or 5-yl, 4H-1,3-dioxan-2- or 4- or 5- or 6-yl, 1,4-dioxan-2- or 3- or 5- or 6-yl, 2,3-dihydro-1,4-dioxan-2- or 3- or 5- or 6-yl, 1,4-dioxan-2- or 3-yl, 1,2-dithiolan-3- or 4-yl 3H-1,2-dithiol-3- or 4- or 5-yl, 1,3-dithiol-2- or 4-yl, 1,3-dithiol-2- or 4-yl, 1,2-dithiol-3- or 4-yl, 3,4-dihydro-1,2-dithiol-3- or 4- or 5- or 6-yl, 3,6-dihydro-1,2-dithiol-3- or 4-yl, 1,2-dithiol-3- or 4-yl, 1,3-dithiol-2- or 4- or 5-yl, 4H-1,3-dithiol-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-Oxazinan-2- or 3- or 4- or 5- or 6-yl, 3,6-Dihydro-2H-1,2-Oxazinan-2- or 3- -or 4-or 5-or 6-yl, 5,6-dihydro-2H-1,2-oxazine-2-or 3-or 4-or 5-or 6-yl, 5,6-dihydro-4H-1,2-oxazine-3-or 4-or 5-or 6-yl, 2H-1,2-oxazine-2-or 3-or 4-or 5-or 6-yl, 6H-1,2-oxazine-3-or 4-or 5-or 6-yl, 4H-1,2-oxazine-3- or 4- or 5- or 6-yl, 1,3-oxazine-2- or 3- or 4- or 5- or 6-yl, 3,4-dihydro-2H-1,3-oxazine-2- or 3- or 4- or 5- or 6-yl, 3,6-dihydro-2H-1,3-oxazine-2- or 3- or 4- or 5- or 6-yl, 5,6-dihydro-2H-1,3-Oxazin-2- or 4- or 5- or 6-yl, 5,6-dihydro-4H-1,3-oxazin-2- or 4- or 5- or 6-yl, 2H-1,3-oxazin-2- or 4- or 5- or 6-yl, 6H-1,3-oxazin-2- or 4- or 5- or 6-yl, 4H-1,3-oxazin-2- or 4- or 5- or 6-yl, morpholine-2- or 3- -or 4-yl, 3,4-dihydro-2H-1,4-oxazine-2-or 3-or 4-or 5-or 6-yl, 3,6-dihydro-2H-1,4-oxazine-2-or 3-or 5-or 6-yl, 2H-1,4-oxazine-2-or 3-or 5-or 6-yl, 4H-1,4-oxazine-2-or 3-yl, 1,2-oxazacycloheptane (oxaze pan)-2-or 3-or 4-or 5-or 6-or 7-yl, 2,3,4,5-tetrahydro-1,2-oxazepin-2-or 3-or 4-or 5-or 6-or 7-yl, 2,3,4,7-tetrahydro-1,2-oxazepin-2-or 3-or 4-or 5-or 6-or 7-yl, 2,3,6,7-tetrahydro-1,2-oxazepin-2-or 3-or 4-or 5-or 6-or 7-yl, 4,5,6,7-tetrahydro-1,2-oxazepin-3-or 4-or 5-or 6-or 7-yl, 2,3-dihydro-1,2-oxazepin Cyclohepten-2- or 3- or 4- or 5- or 6- or 7-yl, 2,5-dihydro-1,2-oxazacyclohepten-2- or 3- or 4- or 5- or 6- or 7-yl, 2,7-dihydro-1,2-oxazacyclohepten-2- or 3- or 4- or 5- or 6- or 7-yl, 4,5-dihydro-1,2-oxazacyclohepten-3- or 4- or 5- or 6 or 7-yl, 4,7-dihydro-1,2-oxazetene-3- or 4- or 5- or 6- or 7-yl, 6,7-dihydro-1,2-oxazetene-3- or 4- or 5- or 6- or 7-yl, 1,2-oxazetene-3- or 4- or 5- or 6- or 7-yl, 1,3-oxazetene-2- or 3- or 4- or 5- or 6-yl -or 7-yl, 2,3,4,5-tetrahydro-1,3-oxazetene-2-or 3-or 4-or 5-or 6-or 7-yl, 2,3,4,7-tetrahydro-1,3-oxazetene-2-or 3-or 4-or 5-or 6-or 7-yl, 2,3,6,7-tetrahydro-1,3-oxazetene-2-or 3-or 4-or 5-or 6-or 7-yl, 2,5,6,7-tetrahydro-1,3-oxazetene-2- or 4- or 5- or 6- or 7-yl, 4,5,6,7-tetrahydro-1,3-oxazetene-2- or 4- or 5- or 6- or 7-yl, 2,3-dihydro-1,3-oxazetene-2- or 3- or 4- or 5- or 6- or 7-yl, 2,5-dihydro-1,3-Oxazolidinyl-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-oxazetane-2- or 4- or 5- or 6- or 7-yl, 1,3-oxazetane-2- or 4- or 5- or 6- or 7-yl, 1,4-oxazetane-2- or 3- or 5- or 6- or 7-yl, 2,3,4,5-tetrahydro-1,4-oxazetane-2- or 3- or 4- or 5- or 6-yl -or 7-yl, 2,3,4,7-tetrahydro-1,4-oxazetene-2-or 3-or 4-or 5-or 6-or 7-yl, 2,3,6,7-tetrahydro-1,4-oxazetene-2-or 3-or 5-or 6-or 7-yl, 2,5,6,7-tetrahydro-1,4-oxazetene-2-or 3-or 5-or 6-or 7-yl, 4, 5,6,7-Tetrahydro-1,4-oxazetane-heptene-2-or-3-or-4-or-5-or-6-or-7-yl, 2,3-dihydro-1,4-oxazetane-heptene-2-or-3-or-5-or-6-or-7-yl, 2,5-dihydro-1,4-oxazetane-heptene-2-or-3-or-5-or-6-or-7-yl, 2,7-dihydro-1,4-oxazetane-heptene- 2- or 3- or 5- or 6- or 7-yl, 4,5-dihydro-1,4-oxazetene-2- or 3- or 4- or 5- or 6- or 7-yl, 4,7-dihydro-1,4-oxazetene-2- or 3- or 4- or 5- or 6- or 7-yl, 6,7-dihydro-1,4-oxazetene-2- or 3- or 5- or 6- or 7-yl, 1,4-oxazetene-2- or 3- or 5- or 6- or 7-yl, isothiazolidine-2- or 3- or 4- or 5-yl, 2,3-dihydroisothiazolidine-2- or 3- or 4- or 5-yl, 2,5-dihydroisothiazolidine-2- or 3- or 4- or 5-yl, 4,5-dihydroisothiazolidine-3- or 4- or 5-yl 1,3-Thiazolidin-2- or 3- or 4- or 5-yl, 2,3-dihydro-1,3-thiazolidin-2- or 3- or 4- or 5-yl, 2,5-dihydro-1,3-thiazolidin-2- or 4- or 5-yl, 4,5-dihydro-1,3-thiazolidin-2- or 4- or 5-yl, 1,3-thiazinidine-2- or 3- or 4- or 5- or 6-yl, 3,4- Dihydro-2H-1,3-thiazin-2- or 3- or 4- or 5- or 6-yl, 3,6-dihydro-2H-1,3-thiazin-2- or 3- or 4- or 5- or 6-yl, 5,6-dihydro-2H-1,3-thiazin-2- or 4- or 5- or 6-yl, 5,6-dihydro-4H-1,3-thiazin-2- or 4- or 5- or 6-yl, 2H-13-Thiazin-2- or 4- or 5- or 6-yl, 6H-1,3-thiazin-2- or 4- or 5- or 6-yl, 4H-1,3-thiazin-2- or 4- or 5- or 6-yl. Other examples of "heterocyclic groups" are partially or fully hydrogenated heterocyclic groups having three heteroatoms selected from N, O, and S, such as 1,4,2-dioxazolidine 2- or 3- or 5-yl, 1,4,2-dioxazolidine 3- or 5-yl, 1,4,2-dioxazinidine 2- or 3- or 5- or 6-yl, 5,6-dihydro-1,4,2-dioxazin-3- or 5- or 6-yl, 1,4,2-dioxazin-3- or 5- or 6-yl, 1,4,2-dioxazine-2- or 3- or 5- or 6- or 7-yl. 6,7-dihydro-5H-1,4,2-dioxazohepten-3- or 5- or 6- or 7-yl, 2,3-dihydro-7H-1,4,2-dioxazohepten-2- or 3- or 5- or 6- or 7-yl, 2,3-dihydro-5H-1,4,2-dioxazohepten-2- or 3- or 5- or 6- or 7-yl, 5H-1,4,2-dioxazohepten-3- or 5- or 6- or 7-yl, 7H-1,4,2-dioxazohepten-3- or 5- or 6- or 7-yl. Examples of heterocycles that may be further substituted are also listed below:

[0082]

[0083]

[0084]

[0085] The heterocycles listed above are preferably substituted with, for example, the following groups: 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, halogen Alkoxy, haloalkylthio, alkylthio, hydrogen thio, hydroxyalkyl, oxo, heteroarylalkoxy, arylalkoxy, heterocyclic alkoxy, heterocyclic alkylthio, heterocyclic thio, heteroaryloxy, dialkylamino, alkylamino, cycloalkylamino, hydroxycarbonyl-alkylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, alkoxycarbonylalkyl(alkyl)-amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, cycloalkylaminocarbonyl, hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl, arylalkoxycarbonylalkyl-aminocarbonyl.

[0086] When the basic structure is replaced by "one or more groups" selected from a list of groups (= groups) or a group defined by a category, this in each case includes being replaced by multiple identical and / or structurally different groups simultaneously.

[0087] In the case of partially or fully saturated nitrogen heterocycles, they can be attached to the rest of the molecule via carbon or nitrogen.

[0088] Suitable substituents for the heterocyclic group used for substitution 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 also preferably 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, two enantiomers are included in each case.

[0089] 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, more 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, azacycloheptenyl, 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-oxazinyl, 1,3,2-oxazinyl, 1,3,6-oxazinyl and 1,2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 1,3-oxazol-2-yl, 1,3-oxazol-4-yl, 1,3-oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,3-thiazol-2-yl, 1,3-thiazol-4-yl, 1,3-thiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-thiazol-2-yl, 1,3,4-thiazol-4-yl, 1,3-thiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-thiazol-2-yl Diazol-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, oxazheptenyl, thioheptenyl, 1,2,4-triazoloneyl and 1,2,4-diazaheptenyl, 2H-1,2,3,4-tetrazol-5-yl, 1H-1,2,3,4-tetrazol-5-yl, 1,2,3,4-oxatriazol-5-yl, 1,2,3,4-thiatriazol-5-yl, 1,2,3,5-oxatriazol-4-yl, 1,2,3,5-thiatriazol-4-yl.The heteroaryl groups of the present invention can also be substituted by 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, quinazolin, zoline, 1,5-naphthoidine, 1,6-naphthoidine, 1,7-naphthoidine, 1,8-naphthoidine, 2,6-naphthoidine, 2,7-naphthoidine, phthalazine, pyridopyrazine, pyridopyrimidine, pyridopyridazine, pteridine, pyrimidine.Examples of heteroaryl groups are also 5- or 6-membered benzofused rings selected from 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.

[0090] 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.

[0091] According to the present invention, "alkyl" refers to a straight-chain or branched open-chain saturated hydrocarbon group, which is optionally monosubstituted or polysubstituted, and in the case of monosubstituted or polysubstituted, it is called "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).

[0092] "Haloalkyl", "haloalkenyl", and "haloalkynyl" respectively refer to alkyl, alkenyl, and alkynyl groups that are partially or completely substituted by the same or different halogen atoms, such as monohaloalkyl, like CH2CH2Cl, CH2CH2Br, CHClCH3, CH2Cl, CH2F; perhaloalkyl, like CCl3, CClF2, CFCl2, CF2CClF2, CF2CClFCF3; and polyhaloalkyl, like CH2CHFCl, CF2CClFH, CF2CBrFH, CH2CF3. The term perhaloalkyl also includes the term perfluoroalkyl.

[0093] "Partially fluorinated alkyl" refers to a straight-chain or branched saturated hydrocarbon that is mono- or poly-substituted with fluorine, wherein the fluorine atom may be present as a substituent on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain, such as CHFCH3, CH2CH2F, CH2CH2CF3, CHF2, CH2F, CHFCF2CF3.

[0094] "Haloalkoxy" is, for example, OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 and OCH2CH2Cl; this applies accordingly to haloalkenyl and other halogen-substituted groups.

[0095] The term "(C1-C4)-alkyl" used in this article is an abbreviation for straight-chain or branched alkyl groups 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 with a larger specified carbon atom range, such as "(C1-C6)-alkyl," also include straight-chain or branched alkyl groups having a greater number of carbon atoms, i.e., according to the examples, also include alkyl groups having 5 and 6 carbon atoms.

[0096] 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.

[0097] 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 refers to vinyl groups, for example, that may optionally be substituted with other alkyl groups, such as (but not limited to) (C2-C6)-alkenyl groups, including 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 ... 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.

[0098] The term "alkynyl" also specifically includes open-chain hydrocarbon groups, either straight or branched, having more than one triple bond or having 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 represent, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3- Pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl.

[0099] The term "cycloalkyl" refers to a carbocyclic saturated ring system having preferably 3-8 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 cyclic 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 and 1,1'-di(cyclopropyl)-2-yl. The term "(C3-C7)-cycloalkyl" is an abbreviation for cycloalkyl groups with 3 to 7 carbon atoms, corresponding to a specified range of carbon atoms.

[0100] 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.

[0101] "Cycloalkenyl" refers to a non-aromatic, partially unsaturated cyclic system having a carbocyclic ring, preferably with 4-8 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. In the case of optionally substituted cycloalkenyl groups, the description of substituted cycloalkyl groups applies accordingly.

[0102] The term "alkylene", for example (C1-C 10The alkylene group (=) also refers to 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 in 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 represent carbocyclic groups linked by a double bond.

[0103] "Alkoxyalkyl" means an alkoxy group bonded by an alkyl group, and "alkoxyalkoxy" means an alkoxyalkyl group bonded by an oxygen atom, such as (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, and methoxypropoxy.

[0104] "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.

[0105] “Cycloalkylalkyl” refers to 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.

[0106] According to the present invention, "haloalkylthio" – either on its own or as part of a chemical group – is preferably a straight-chain or branched S-haloalkyl group having 1 to 8 or 1 to 6 carbon atoms, such as (C1-C8)-haloalkylthio, (C1-C6)-haloalkylthio 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.

[0107] "Halocycloalkyl" refers to a cycloalkyl or cycloalkenyl group that is partially or completely substituted with the same or different halogen atoms (such as F, Cl, and Br) or a halogenated alkyl group (such as trifluoromethyl or difluoromethyl), for example, 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.

[0108] If a compound can form tautomers whose structures are not formally covered by general formula (I) through hydrogen transposition, these tautomers are still covered by the definition of compounds of general formula (I) of this invention, unless a specific tautomer is considered. For example, many carbonyl compounds can exist in ketone form and enol form, both of which are covered by the definition of compounds of general formula (I).

[0109] Compounds of general formula (I) can exist in 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- and E-isomers, are all covered by general formula (I). For example, the presence of one or more alkenyl groups can produce diastereomers (Z- and E-isomers). Similarly, the presence of one or more asymmetric carbon atoms can produce enantiomers and diastereomers. 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.

[0110] 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).

[0111] Suitable separation, purification, and methods for separating 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), distillation (optionally under reduced pressure), extraction, and other methods. Any residual mixtures can generally be separated chromatographically, for example, 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, optically active bases (provided an acidic group is present).

[0112] Synthesis of [(1,5-di(heteroaryl)-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives of general formula (I)

[0113]

[0114] The [(1,5-di(heteroaryl)-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives of general formula (I) of the present invention can be prepared by known methods. The synthetic routes used and studied begin with commercially available or readily prepared substituted heteroaryl carboxylic acids, correspondingly substituted heteroaryl acid amides, and commercially available chemicals (such as substituted heteroaryl hydrazides and diphenyl carbonates). In the following schemes, unless defined illustratively and non-limitingly, the R in general formula (I) refers to... 1 R 2 R 3 R 4 p has the meaning defined above.

[0115] 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 (e.g., acetonitrile) at a temperature range of 0°C to 120°C (see Scheme 1).

[0116]

[0117] Where X = halogen and R = (C1-C4)-alkyl.

[0118] Option 1

[0119] Compounds of general formula (II) are synthesized by cyclizing compounds of general formula (IV) in the presence of a condensing agent (e.g., polyphosphoric acid). The reaction is preferably carried out in pure form in a temperature range of 0°C to 180°C (see Scheme 2).

[0120]

[0121] Option 2

[0122] The synthesis of compounds of general formula (IV) can be achieved by reacting a compound of general formula (V) with a heteroarylhydrazine of general formula (VI) in a suitable solvent (e.g., acetonitrile) at a temperature ranging from -20°C to 100°C, preferably from -5°C to 50°C. This reaction is carried out in the presence of a base (e.g., triethylamine). In addition to heteroarylhydrazines of general formula (VI), heteroarylhydrazine hydrohalides of general formula (VII) can also be used (Scheme 3).

[0123]

[0124] Where X = halogen.

[0125] Option 3

[0126] The synthesis of compounds of general formula (V) can be achieved by reacting a compound of general formula (VIII) with diphenyl carbonate (IX) in the presence of a base (e.g., sodium hydride) (see Scheme 4). The reaction is preferably carried out in a suitable solvent (e.g., THF) at a temperature range of -20°C to 150°C. Compounds of general formulas (VIII) and (IX) are commercially available or can be prepared by methods known to those skilled in the art.

[0127]

[0128] Option 4

[0129] The synthesis of acids of general formula (X) can be achieved by hydrolyzing compounds of general formula (Ia) using methods known to those skilled in the art or similar to those described in the art.

[0130] Hydrolysis can be carried out in the presence of a base or a Lewis acid. The base can be a hydroxide salt of an alkali metal (e.g., lithium, sodium, or potassium; Scheme 5), 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.

[0131]

[0132] Where R = (C1-C4)-alkyl.

[0133] Option 5

[0134] The compounds of general formula (XI) of the present invention are synthesized by esterification of an acid of general formula (X) with an alcohol of general formula (XII) 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, such as 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 6). For T3P coupling conditions, see Organic Process Research & Development 2009, 13, 900-906.

[0135]

[0136] Option 6

[0137] Scheme 7 shows the synthesis of compounds of general formula (II); this synthesis is achieved by reacting compounds of general formula (XIII) with Brønsted acid ( The reaction is carried out in the presence of an acid (e.g., 33% HBr in acetic acid). The reaction is preferably carried out in a temperature range of 0°C to 180°C. See Bioorganic & Medicinal Chemistry 2018, 26, 3321-3344.

[0138]

[0139] Option 7

[0140] Compounds of general formula (XIII) can be prepared by reacting a compound of general formula (XIV) with a heteroarylhydrazine of general formula (VI) in a suitable solvent (e.g., ethanol) (see Scheme 8). The reaction is preferably carried out in a temperature range of 0°C to 150°C.

[0141]

[0142] Option 8

[0143] Compounds of general formula (XIV) can be prepared by reacting a heteroaryl carbonyl halide of general formula (XV) with a thiocyanate of general formula (XVI) in the presence of methanol in a suitable solvent (e.g., acetone) (see Scheme 9). The heteroaryl carbonyl halide is commercially available or can be prepared by or similar methods known to those skilled in the art. See Tetrahedron 1968, 24, 5205-5214; J. Chem. Soc. 1957, 1091; JP81 53, 664 (1981); Justus Liebigs Ann. Chem. 1964, 675, 180 and J. heterocycl. Chem. 1983, 20, 1533.

[0144]

[0145] Where X = fluorine, chlorine, bromine.

[0146] Option 9

[0147] The following are selected detailed synthetic examples of compounds of general formula (I) of the present invention. The example numbers mentioned correspond to the numbering scheme in Tables I.1 to I.77 below. The chemical examples described in the following sections... 1 H NMR, 13 C-NMR and 19 F-NMR spectral data ( 1 H-NMR is 400MHz 13 C-NMR is 150MHz 19 F-NMR was performed at 375 MHz using CDCl3, CD3OD, or d6-DMSO as solvents, with 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 the following meanings, for example: 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.

[0148] Synthesis Example:

[0149] Synthesis Example Number: I.33-10

[0150] Synthesis Stage 1: 5-Fluoropyridine-2-carboxamide

[0151]

[0152] 5-Fluoropyridine-2-carboxylic acid (2.50 g, 17.72 mmol, 1.0 equivalent) and DMF (1 drop) were suspended in DCM (100 ml). Oxaloyl chloride (3.09 ml, 35.44 mmol, 2.0 equivalent) was added dropwise to the suspension over 45 minutes. Note: Gas escape! The reaction mixture was then stirred at 40 °C for 1 hour. After cooling to room temperature, the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (150 ml), and ammonia (35%, 150 ml) was added in portions over 15 minutes. The reaction mixture was stirred at room temperature for 45 minutes. The organic phase was separated, and the aqueous phase was extracted with ethyl acetate (100 ml). The combined organic phases were washed with saturated sodium chloride solution and dried over sodium sulfate. The solvent was removed under reduced pressure, and the residue was stirred with n-heptane / ethyl acetate (4:1, 20 ml). The resulting solid was filtered off and dried in air. 5-Fluoropyridine-2-carboxamide was isolated as a white solid (1.58 g, 60% of the theoretical value). 1 H-NMR (400MHz, DMSO-d) 6 δ,ppm)8.62(d,1H),8.13-8.09(m,2H),7.89(m,1H),7.68(bs,1H).

[0153] Synthesis Stage 2: [(5-Fluoropyridin-2-yl)carbonyl]phenyl carbamate

[0154]

[0155] 5-Fluoropyridin-2-carboxamide (1.54 g, 10.99 mmol, 1.0 equivalent) and diphenyl carbonate (3.53 g, 16.49 mmol, 1.5 equivalent) were suspended in THF (120 ml) under an argon atmosphere and cooled to 0 °C in an ice bath. Sodium hydride (60% in mineral oil, 0.44 g, 10.99 mmol, 1.0 equivalent) was added to the solution in portions. Note: Gas escape! Subsequently, the ice bath was removed, and the reaction mixture was stirred at room temperature for 4.5 hours. The reaction mixture was then concentrated to 1 / 3 under reduced pressure to form a flaky white solid. The resulting solid was filtered off and dried in air. [(5-Fluoropyridin-2-yl)carbonyl]phenyl carbamate was separated as a white solid (2.58 g, 90% of the theoretical value). 1 H-NMR (400MHz, DMSO-d) 6δ,ppm)9.61(bs,1H),8.62(d,1H),8.02(m,1H),7.89(m,1H),7.16-7.12(m,2H),6.75-6.71(m,3H).

[0156] Synthesis Stage 3: N-{[2-(5-chloropyridin-2-yl)hydrazino]carbonyl}-5-fluoropyridin-2-carboxamide

[0157]

[0158] [(5-fluoropyridin-2-yl)carbonyl]phenyl carbamate (2.58 g, 9.92 mmol, 1.0 equivalent) was dissolved in pyridine (60 mL), and then 5-chloro-2-hydrazinopyridine (1.57 g, 10.91 mmol, 1.1 equivalent) was added at room temperature. The reaction mixture was stirred at room temperature for 2 days, the solvent was removed under reduced pressure, and the residue was stirred twice with acetonitrile (25 mL). Subsequently, the precipitate was filtered off, washed twice with acetonitrile (6 mL each time), and dried in air. N-{[2-(5-chloropyridin-2-yl)hydrazino]carbonyl}-5-fluoropyridin-2-carboxamide was separated as a pale yellow solid (1.93 g, 56% of the theoretical value). 1 H-NMR (400MHz, DMSO-d) 6 δ,ppm)10.39(bs,1H),9.78(bs,1H),8.81(bs,1H),8.75(bs,1H),8.25(m,1H),8.16-8.02(m,2H),7.63(m,1H),6.71(m,1H).

[0159] Synthesis Stage 4: 1-(5-chloropyridin-2-yl)-5-(5-fluoropyridin-2-yl)-1H-1,2,4-triazol-3-ol

[0160]

[0161] N-{[2-(5-chloropyridin-2-yl)hydrazino]carbonyl}-5-fluoropyridin-2-carboxamide (1 g, 3.23 mmol, 1.0 equivalent) was suspended in 10% potassium hydroxide solution (50 mL) and stirred at 70 °C for 2 h. After cooling to room temperature, the reaction mixture was added dropwise to a mixture of ice-water buffer (pH = 4.65, 1 M). The solution was extracted with ethyl acetate (40 mL), and the aqueous phase was adjusted to pH = 3 with 2 M hydrochloric acid. The mixture was stirred for another 20 min, and a pale beige solid was filtered off. The precipitate was filtered off and dried in a vacuum oven at 55 °C. 1-(5-chloropyridin-2-yl)-5-(5-fluoropyridin-2-yl)-1H-1,2,4-triazol-3-ol was separated as a pale beige solid (348 mg, 35% of theoretical value). 1 H-NMR (400MHz, DMSO-d) 6 δ,ppm)13.21(bs,1H),8.24(d,1H),7.99(m,1H),7.86(dd,1H),7.66(dd,1H),7.56(m,1H).

[0162] Synthesis Stage 5: Methyl acetate {[1-(5-chloropyridin-2-yl)-5-(5-fluoropyridin-2-yl)-1H-1,2,4-triazol-3-yl]oxy} (Synthetic Examples I.31-10)

[0163]

[0164] 1-(5-chloropyridin-2-yl)-5-(5-fluoropyridin-2-yl)-1H-1,2,4-triazol-3-ol (250 mg, 0.86 mmol, 1.0 equivalent) and potassium carbonate (355 g, 2.57 mmol, 3 equivalent) were dissolved in DMF (10 mL), and then methyl bromoacetate (170 mg, 1.11 mmol, 1.3 equivalent) was added. The solution was then stirred at room temperature for 2 hours, the solid was filtered off, and the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate / heptane gradient). Methyl acetate {[1-(5-chloropyridin-2-yl)-5-(5-fluoropyridin-2-yl)-1H-1,2,4-triazol-3-yl]oxy}acetate was separated as a pale yellow solid (258 mg, 78% of theoretical value). 1 H-NMR (400MHz, CDCl3δ, ppm) 8.26-8.24 (m, 2H), 8.01 (m, 1H), 7.82 (m, 1H), 7.58 (m, 1H), 7.52 (m, 1H), 4.97 (s, 2H), 3.81 (s, 3H).

[0165] Synthesis Stage 6: {[1-(5-chloropyridin-2-yl)-5-(5-fluoropyridin-2-yl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid (Synthetic Examples I.33-10)

[0166]

[0167] Methyl acetate {[1-(5-chloropyridin-2-yl)-5-(5-fluoropyridin-2-yl)-1H-1,2,4-triazol-3-yl]oxy}acetate (142 mg, 0.39 mmol, 1.0 equivalent) and lithium hydroxide (19 mg, 0.78 mmol, 1 equivalent) were dissolved in a THF / water mixture (7:2, 15 mL) and stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in water and adjusted to pH 2 with 2 M hydrochloric acid, precipitating a pale yellow solid. The precipitate was filtered off and dried in a vacuum oven at 55 °C. {[1-(5-chloropyridin-2-yl)-5-(5-fluoropyridin-2-yl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid was separated as a pale yellow solid (131 mg, 92% of theoretical value). 1 H-NMR (400MHz, DMSO-d) 6 δ,ppm)13.06(bs,1H),8.44(m,1H),8.16(m,1H),8.03(m,1H),7.91(m,1H),7.69(dd,1H),4.89(s,2H).

[0168] 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 [(1,5-di(heteroaryl)-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives, the following compounds were obtained:

[0169]

[0170] Table I.1: The preferred compounds of formula (I.1) are compounds I.1-1 to I.1-25, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.1-1 to I.1-25 of Table I.1 are defined by the meaning of the corresponding entries 1 to 25 of Q in Table 1.

[0171] Table 1:

[0172]

[0173]

[0174]

[0175] Table I.2: The preferred compounds of formula (I.2) are compounds I.2-1 to I.2-25, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.2-1 to I.2-25 in Table I.2 are defined by the meaning of the corresponding entries 1 to 25 of Q in Table 1.

[0176]

[0177] Table I.3: The preferred compounds of formula (I.3) are compounds I.3-1 to I.3-25, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.3-1 to I.3-25 of Table I.3 are defined by the meaning of the corresponding entries 1 to 25 of Q in Table 1.

[0178]

[0179] Table I.4: The preferred compounds of formula (I.4) are compounds I.4-1 to I.4-25, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.4-1 to I.4-25 of Table I.4 are defined by the meaning of the corresponding entries 1 to 25 of Q in Table 1.

[0180]

[0181] Table I.5: The preferred compounds of formula (I.5) are compounds I.5-1 to I.5-25, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.5-1 to I.5-25 in Table I.5 are defined by the meaning of the corresponding entries 1 to 25 of Q in Table 1.

[0182]

[0183] Table I.6: The preferred compounds of formula (I.6) are compounds I.6-1 to I.6-25, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.6-1 to I.6-25 of Table I.6 are defined by the meaning of the corresponding entries 1 to 25 of Q in Table 1.

[0184]

[0185] Table I.7: The preferred compounds of formula (I.7) are compounds I.7-1 to I.7-25, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.7-1 to I.7-25 of Table I.7 are defined by the meaning of the corresponding entries 1 to 25 of Q in Table 1.

[0186]

[0187] Table I.8: The preferred compounds of formula (I.8) are compounds I.8-1 to I.8-25, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.8-1 to I.8-25 of Table I.8 are defined by the meaning of the corresponding entries 1 to 25 of Q in Table 1.

[0188]

[0189] Table I.9: The preferred compounds of formula (I.9) are compounds I.9-1 to I.9-25, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.9-1 to I.9-25 of Table I.9 are defined by the meaning of the corresponding entries 1 to 25 of Q in Table 1.

[0190]

[0191] Table I.10: The preferred compounds of formula (I.10) are compounds I.10-1 to I.10-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.10-1 to I.10-25 in Table I.10 are...

[0192] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0193]

[0194] Table I.11: The preferred compounds of formula (I.11) are compounds I.11-1 to I.11-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.11-1 to I.11-25 in Table I.11 are...

[0195] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0196]

[0197] Table I.12: The preferred compounds of formula (I.12) are compounds I.12-1 to I.12-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.12-1 to I.12-25 in Table I.12 are...

[0198] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0199]

[0200] Table I.13: The preferred compounds of formula (I.13) are compounds I.13-1 to I.13-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.13-1 to I.13-25 in Table I.13 are...

[0201] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0202]

[0203] Table I.14: The preferred compounds of formula (I.14) are compounds I.14-1 to I.14-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.14-1 to I.14-25 in Table I.14 are...

[0204] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0205]

[0206] Table I.15: The preferred compounds of formula (I.15) are compounds I.15-1 to I.15-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.15-1 to I.15-25 in Table I.15 are...

[0207] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0208]

[0209] Table I.16: The preferred compounds of formula (I.16) are compounds I.16-1 to I.16-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.16-1 to I.16-25 in Table I.16 are...

[0210] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0211]

[0212] Table I.17: Preferred compounds of formula (I.17) are compounds I.17-1 to I.17-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.17-1 to I.17-25 in Table I.17 are...

[0213] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0214]

[0215] Table I.18: The preferred compounds of formula (I.18) are compounds I.18-1 to I.18-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.18-1 to I.18-25 in Table I.18 are...

[0216] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0217]

[0218] Table I.19: The preferred compounds of formula (I.19) are compounds I.19-1 to I.19-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.19-1 to I.19-25 in Table I.19 are...

[0219] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0220]

[0221] Table I.20: The preferred compounds of formula (I.20) are compounds I.20-1 to I.20-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.20-1 to I.20-25 of Table I.20 are...

[0222] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0223]

[0224] Table I.21: The preferred compounds of formula (I.21) are compounds I.21-1 to I.21-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.21-1 to I.21-25 in Table I.21 are...

[0225] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0226]

[0227] Table I.22: The preferred compounds of formula (I.22) are compounds I.22-1 to I.22-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.22-1 to I.22-25 in Table I.22 are...

[0228] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0229]

[0230] Table I.23: The preferred compounds of formula (I.23) are compounds I.23-1 to I.23-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.23-1 to I.23-25 ​​in Table I.23 are...

[0231] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0232]

[0233] Table I.24: The preferred compounds of formula (I.24) are compounds I.24-1 to I.24-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.24-1 to I.24-25 in Table I.24 are...

[0234] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0235]

[0236] Table I.25: The preferred compounds of formula (I.25) are compounds I.25-1 to I.25-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.25-1 to I.25-25 in Table I.25 are...

[0237] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0238]

[0239] Table I.26: The preferred compounds of formula (I.26) are compounds I.26-1 to I.26-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.26-1 to I.26-25 in Table I.26 are...

[0240] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0241]

[0242] Table I.27: The preferred compounds of formula (I.27) are compounds I.27-1 to I.27-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.27-1 to I.27-25 in Table I.27 are...

[0243] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0244]

[0245] Table I.28: The preferred compounds of formula (I.28) are compounds I.28-1 to I.28-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.28-1 to I.28-25 in Table I.28 are...

[0246] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0247]

[0248] Table I.29: The preferred compounds of formula (I.29) are compounds I.29-1 to I.29-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.29-1 to I.29-25 in Table I.29 are...

[0249] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0250]

[0251] Table I.30: The preferred compounds of formula (I.30) are compounds I.30-1 to I.30-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.30-1 to I.30-25 of Table I.30 are...

[0252] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0253]

[0254] Table I.31: The preferred compounds of formula (I.31) are compounds I.31-1 to I.31-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.31-1 to I.31-25 in Table I.31 are...

[0255] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0256]

[0257] Table I.32: The preferred compounds of formula (I.32) are compounds I.32-1 to I.32-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.32-1 to I.32-25 in Table I.32 are...

[0258] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0259]

[0260] Table I.33: The preferred compounds of formula (I.33) are compounds I.33-1 to I.33-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.33-1 to I.33-25 in Table I.33 are...

[0261] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0262]

[0263] Table I.34: Preferred compounds of formula (I.34) are compounds I.34-1 to I.34-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.34-1 to I.34-25 in Table I.34 are...

[0264] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0265]

[0266] Table I.35: The preferred compounds of formula (I.35) are compounds I.35-1 to I.35-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.35-1 to I.35-25 in Table I.35 are...

[0267] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0268]

[0269] Table I.36: The preferred compounds of formula (I.36) are compounds I.36-1 to I.36-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.36-1 to I.36-25 in Table I.36 are...

[0270] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0271]

[0272] Table I.37: Preferred compounds of formula (I.37) are compounds I.37-1 to I.37-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.37-1 to I.37-25 in Table I.37 are...

[0273] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0274]

[0275] Table I.38: The preferred compounds of formula (I.38) are compounds I.38-1 to I.38-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.38-1 to I.38-25 in Table I.38 are...

[0276] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0277]

[0278] Table I.39: Preferred compounds of formula (I.39) are compounds I.39-1 to I.39-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.39-1 to I.39-25 in Table I.39 are...

[0279] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0280]

[0281] Table I.40: The preferred compounds of formula (I.40) are compounds I.40-1 to I.40-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.40-1 to I.40-25 of Table I.40 are...

[0282] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0283]

[0284] Table I.41: The preferred compounds of formula (I.41) are compounds I.41-1 to I.41-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.41-1 to I.41-25 in Table I.41 are...

[0285] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0286]

[0287] Table I.42: The preferred compounds of formula (I.42) are compounds I.42-1 to I.42-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.42-1 to I.42-25 in Table I.42 are...

[0288] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0289]

[0290] Table I.43: The preferred compounds of formula (I.4) are compounds I.43-1 to I.43-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.43-1 to I.43-25 in Table I.43 are...

[0291] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0292]

[0293] Table I.44: The preferred compounds of formula (I.44) are compounds I.44-1 to I.44-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.44-1 to I.44-25 in Table I.44 are...

[0294] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0295]

[0296] Table I.45: The preferred compounds of formula (I.45) are compounds I.45-1 to I.45-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.45-1 to I.45-25 in Table I.45 are...

[0297] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0298]

[0299] Table I.46: The preferred compounds of formula (I.46) are compounds I.46-1 to I.46-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.46-1 to I.46-25 in Table I.46 are...

[0300] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0301]

[0302] Table I.47: Preferred compounds of formula (I.47) are compounds I.47-1 to I.47-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.47-1 to I.47-25 in Table I.47 are...

[0303] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0304]

[0305] Table I.48: The preferred compounds of formula (I.48) are compounds I.48-1 to I.48-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.48-1 to I.48-25 in Table I.48 are...

[0306] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0307]

[0308] Table I.49: The preferred compounds of formula (I.49) are compounds I.49-1 to I.49-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.49-1 to I.49-25 in Table I.49 are...

[0309] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0310]

[0311] Table I.50: The preferred compounds of formula (I.50) are compounds I.50-1 to I.50-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.50-1 to I.50-25 of Table I.50 are...

[0312] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0313]

[0314] Table I.51: The preferred compounds of formula (I.51) are compounds I.51-1 to I.51-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.51-1 to I.51-25 in Table I.51 are...

[0315] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0316]

[0317] Table I.52: The preferred compounds of formula (I.52) are compounds I.52-1 to I.52-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.52-1 to I.52-25 in Table I.52 are...

[0318] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0319]

[0320] Table I.53: The preferred compounds of formula (I.53) are compounds I.53-1 to I.53-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.53-1 to I.53-25 in Table I.53 are...

[0321] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0322]

[0323] Table I.54: The preferred compounds of formula (I.54) are compounds I.54-1 to I.54-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.54-1 to I.54-25 in Table I.54 are...

[0324] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0325]

[0326] Table I.55: The preferred compounds of formula (I.55) are compounds I.55-1 to I.55-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.55-1 to I.55-25 in Table I.55 are...

[0327] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0328]

[0329] Table I.56: The preferred compounds of formula (I.56) are compounds I.56-1 to I.56-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.56-1 to I.56-25 in Table I.56 are...

[0330] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0331]

[0332] Table I.57: The preferred compounds of formula (I.57) are compounds I.57-1 to I.57-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.57-1 to I.57-25 in Table I.57 are...

[0333] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0334]

[0335] Table I.58: The preferred compounds of formula (I.58) are compounds I.58-1 to I.58-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.58-1 to I.58-25 in Table I.58 are...

[0336] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0337]

[0338] Table I.59: The preferred compounds of formula (I.59) are compounds I.59-1 to I.59-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.59-1 to I.59-25 in Table I.59 are...

[0339] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0340]

[0341] Table I.60: The preferred compounds of formula (I.60) are compounds I.60-1 to I.60-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.60-1 to I.60-25 of Table I.60 are...

[0342] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0343]

[0344] Table I.61: The preferred compounds of formula (I.61) are compounds I.61-1 to I.61-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.61-1 to I.61-25 in Table I.61 are...

[0345] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0346]

[0347] Table I.62: The preferred compounds of formula (I.62) are compounds I.62-1 to I.62-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.62-1 to I.62-25 in Table I.62 are...

[0348] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0349]

[0350] Table I.63: The preferred compounds of formula (I.63) are compounds I.63-1 to I.63-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.63-1 to I.63-25 in Table I.63 are...

[0351] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0352]

[0353] Table I.64: The preferred compounds of formula (I.64) are compounds I.64-1 to I.64-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.64-1 to I.64-25 in Table I.64 are...

[0354] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0355]

[0356] Table I.65: The preferred compounds of formula (I.65) are compounds I.65-1 to I.65-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.65-1 to I.65-25 in Table I.65 are...

[0357] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0358]

[0359] Table I.66: The preferred compounds of formula (I.66) are compounds I.66-1 to I.66-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.66-1 to I.66-25 in Table I.66 are...

[0360] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0361]

[0362] Table I.67: The preferred compounds of formula (I.67) are compounds I.67-1 to I.67-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.67-1 to I.67-25 in Table I.67 are...

[0363] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0364]

[0365] Table I.68: The preferred compounds of formula (I.68) are compounds I.68-1 to I.68-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.68-1 to I.68-25 in Table I.68 are...

[0366] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0367]

[0368] Table I.69: The preferred compounds of formula (I.69) are compounds I.69-1 to I.69-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.69-1 to I.69-25 in Table I.69 are...

[0369] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0370]

[0371] Table I.70: The preferred compounds of formula (I.70) are compounds I.70-1 to I.70-25, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.70-1 to I.70-25 of Table I.70 are...

[0372] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0373]

[0374] Table I.71: The preferred compounds of formula (I.71) are compounds I.71-1 to I.71-25, where Q has the meaning shown in each row of Table 1. Therefore, compounds I.71-1 to I.71-25 in Table I.71 are...

[0375] The meaning of the corresponding entries 1 to 25 of Q in Table 1 is defined.

[0376]

[0377] Table I.72: The preferred compounds of formula (I.72) are compounds I.72-1 to I.72-25, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.72-1 to I.72-25 of Table I.72 are defined by the meaning of the corresponding entries 1 to 25 of Q in Table 1.

[0378] Spectral data of the selected tabular example:

[0379] The following are selected detailed synthetic examples of compounds of general formula (I) of the present invention. The chemical examples described in the following sections... 1 H NMR, 13 C-NMR and 19 F-NMR spectral data ( 1 H-NMR is 400MHz 13 C-NMR is 150MHz 19F-NMR was performed at 375 MHz using CDCl3, CD3OD, or d6-DMSO as solvents, with 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 the following meanings, for example: 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.

[0380] The spectral data of the selected tabular examples listed below are obtained through conventional methods. 1 H NMR description or evaluation using NMR peak listing methods.

[0381] conventional 1 H NMR Explanation

[0382] Example 1 number I.28-10:

[0383] 1 H-NMR (400MHz, DMSO-d6δ, ppm) 8.50 (d, 1H), 8.45 (d, 1H), 8.19-8.11 (m, 2H), 7.96 (dd, 1H), 7.71 (dd, 1H), 5.03 (s, 2H), 3.72 (s, 3H).

[0384] Example 1, No. I.32-10:

[0385] 1 H-NMR (400MHz, CDCl3δ, ppm)8.26-8.24(m,2H),8.02(m,1H),7.82(dd,1H),7.58-7.49(m,2H),4.94(s,2H),4.27(q,2H),1.29(t,3H).

[0386] Example 1.30-10:

[0387] 1H-NMR (400MHz, CDCl3δ, ppm) 8.36 (d, 1H), 8.27 (d, 1H), 7.94 (d, 1H), 7.84-7.78 (m, 2H), 7.58 (m, 1H), 4.98 (s, 2H).

[0388] NMR peak listing method

[0389] The 1H NMR data for the selected examples are presented as a list of 1H NMR peaks. For each signal peak, the δ value in ppm is listed first, followed by the signal intensity in parentheses. δ value / signal intensity pairs for different signal peaks are separated by semicolons.

[0390] Therefore, the peak list for an instance takes the following form:

[0391] δ1 (Intensity 1); δ2 (Intensity 2); ...; δ i (strength i );……;δ n (strength n )

[0392] The intensity of the spike signal is highly correlated with the signal in cm in the printed example of the NMR spectrum, showing the true proportion of the signal intensity. In the case of a broad-peak signal, several peaks or the middle portion of the signal can be displayed, along with their relative intensities compared to the strongest signal in the spectrum.

[0393] In order to correct 1 Chemical shifts in 1H NMR spectra, using the chemical shifts of tetramethylsilane and / or solvent, especially in the case of spectra measured in DMSO. Therefore, a tetramethylsilane peak may, but is not necessarily, appear in the NMR peak list.

[0394] 1 H NMR peak list and conventional 1 The 1H NMR printouts are similar, therefore, they typically include all the peaks listed in a standard NMR description.

[0395] In addition, as usual 1 1H NMR prints can show solvent signals, signals of stereoisomers of the target compound (which are also provided by this invention), and / or peaks of impurities.

[0396] When recording compound signals in the δ range of solvent and / or water, 1 The H NMR peak list shows standard solvent peaks, such as peaks for DMSO in DMSO-d6 and peaks for water, which, on average, typically have high intensity.

[0397] 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., with a purity of >90%).

[0398] 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 the "by-product fingerprint".

[0399] A specialist who has calculated the peaks of the target compound using known methods (MestreC, ACD simulation, and expected values ​​using empirical estimations) can, as needed, separate the peaks of the target compound, optionally using additional intensity filters. This separation is similar to conventional methods. 1 Peak selection as described in the H NMR specification.

[0400] 1 Further details on the H NMR peak list can be found in Research Disclosure Database No. 564025.

[0401]

[0402]

[0403] 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 by the use of a compound of general formula (I) or a salt thereof as a safe agent, 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).

[0404] Compounds of general formula (I) specified above (=safeners) are suitable for use with active ingredients (pesticides) to selectively control pests in a variety of crop cultures, such as economically important crops, including, for example, cereals (wheat, barley, rye, rice, corn, millet / sorghum), sugar beets, sugarcane, rapeseed, cotton, sunflower, peas, beans, and soybeans. Herbicide-safener combinations containing 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.

[0405] With regard to useful plants and crops in which herbicide-safety agent combinations containing compounds of the above general formula (I) can be used, it is equally important to mutant crops or genetically modified crops that are fully or partially resistant to some pesticides, such as corn crops resistant to glufosinate or glyphosate, or soybean crops resistant to imidazolinones with phytotoxic effects. However, a particular benefit of safeties of general formula (I) used in novel ways is their effectiveness in crops that are not normally sufficiently resistant to the pesticides used.

[0406] When used in conjunction with pesticides, compounds of general formula (I) can be applied simultaneously with or in any order to the active ingredients, thereby reducing or completely preventing the detrimental side effects of these active ingredients on crop plants without impairing or significantly reducing their efficacy against unwanted pests. This also significantly reduces or completely prevents 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.

[0407] 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 the so-called tank mixing method, which means that the user mixes and dilutes the separately formulated products (= plant protection composition and pesticide) before application to the area to be treated, before or after application of pesticides, or for seed pretreatment (i.e., for coating of seeds of beneficial plants). It is preferred that the safener be applied promptly with the pesticide, especially when the safener is applied to the plants after a herbicide. The beneficial effects of compounds of general formula (I) can be observed when used with pesticides via pre-emergence or post-emergence methods, for example, when applied simultaneously as tank mixes or co-formulations, or when applied separately in parallel or consecutively (multiple applications). Repeated applications are also possible. Sometimes it is also reasonable to combine pre-emergence and post-emergence applications. One option is to apply the compound (I) of the invention to the useful plant or crop plant in a post-emergence form, and to apply the pesticide simultaneously or later. Another option is to use the compound (I) of the invention for seed dressing, (dipping) treatment of seedlings (e.g., rice), or treatment of other propagation materials (e.g., potato tubers).

[0408] When compounds of general formula (I) are used in combination with herbicides, not only is a safener effect typically observed, but also an enhanced herbicidal effect on harmful plants is observed. Furthermore, in many cases, the growth of beneficial plants and crop plants is improved, and harvest yield can be increased.

[0409] 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, can cause or may cause phytotoxic damage to crop plants. Of particular importance are the respective active pesticide components selected from herbicides, insecticides, acaricides, nematicides, and fungicides (especially herbicides).

[0410] The weight ratio of the safener to the pesticide (of general formula (I)) can vary over a wide range, and is typically 1:100 to 100:1, preferably 1:20 to 20:1, and particularly 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 useful plant or crop to be protected. Depending on the pesticide used and the type of useful plant to be protected, the required safener application rate can vary over a wide range, and is typically 0.001 to 10 kg per hectare, preferably 0.01 to 1 kg, and particularly 0.01 to 0.2 kg of safener. The amount and weight ratio required for successful treatment can be determined by simple preliminary testing.

[0411] In the case of seed dressing, for example, 0.005 to 20 g of safener (of general formula (I)) per kilogram of seed is used, preferably 0.01 to 10 g of safener per kilogram of seed, and particularly 0.05 to 5 g of safener per kilogram of seed.

[0412] When using a solution of a safener (of 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.

[0413] Safes of general formula (I) can be formulated alone or in combination with pesticides in a conventional manner. Therefore, useful plant or crop protection compositions are also provided.

[0414] It is preferable to use safeners and pesticides in combination, especially in the form of finished formulations or by tank mixing.

[0415] It is also preferred to apply a safer of formula (I) during seed treatment and then apply the pesticide, preferably a herbicide, after sowing via pre- or post-emergence methods.

[0416] Compounds of general formula (I) or their salts can be used as is or in combination with other pesticide active substances in the form of formulations (formulated formulations), such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers, and / or growth regulators, for example, 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.

[0417] Combination formulations of the compounds of the present invention that can be used in mixed formulations or tank mixes are, for example, based on known active ingredients that inhibit the following: for example, acetyllactate synthase, acetyl-CoA carboxylase, cellulase, enolpyruvate-3-phosphate synthase, glutamine synthase, p-hydroxyphenylpyruvate dioxygenase, phytopenic oleoresin, photosystem I, photosystem 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.

[0418] For example, known herbicides or plant growth regulators that can be combined with the compounds of the present invention are as follows, wherein the active ingredient is represented by its "common name" or chemical name or code number 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.

[0419] An example of such a herbicide mixture is:

[0420] Acetochlor, acifluorfen (acifluorfen-sodium), aclofen (aclonifen), alachlor (alachlor), allidochlor (allidochlor), alloxydim (alloxydim-sodium), ametryn (ametryn), amicabazone (amidochlor), amoxicillin (amidosulfuron), 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, cyclopropionic acid (a The following herbicides are listed: minocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrol, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, and beflubutamid. Herbicides including benzolin (benazolin-ethyl), benzfluralin, benzurates, benzsulfuron (bensulfuron-methyl), benzulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos (bilanafos-sodium), and bispyrib. Acetate, bispyribac-sodium), bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, bromoxynil-potassium, bromoxynil-heptanoate, bromoxynil-octanoate, busoxinone, butachlor, and butafenacil.Butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, methyl chlorfluorene (rflurenol, chlorflurenol-methyl), chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos Clethodim, clodinafop, clodinafop-propargyl, clonzone, clonprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, thiamethoxam Cyclooxydim), cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butoxyethyl ester, 2,4-D-butyl ester, 2,4-D-dimethylammonium, 2,4-D-diethanolamine, 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, 2,4-D-potassium ester,2,4-D-triisopropanol ammonium and 2,4-D-triethanolamine, 2,4-DB, 2,4-DB-butyl ester, 2,4-DB-dimethylammonium, 2,4-DB-isooctyl ester, 2,4-DB-potassium and 2,4-DB-sodium, 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), dimefuron, dimepiper ate), dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb ), etalfluralin, ethametsulfuron, ethametsulfuron-methyl, etiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9600, F-5231 (i.e., N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide),F-7967 (i.e., 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidin-2,4(1H,3H)-dione), fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, and flamprop-M-i (a type of methyl methacrylate). Sopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, fluorine Flufenacet, flufenpyr (flufenpyr-ethyl), flumetsulam, flumiclorac (flumiclorac-pentyl), flumioxazin, fluometuron, flurenol, flurenol-butyl, flurenol-dimethylammonium, flurenol-methyl, and fluoroglyphosate. Cofen, fluoroglycofen-ethyl, tetrafluoropropionic acid (flupropanate), flupyrsulfuron (flupyrsulfuron, flupyrsulfuron-methyl-sodium), fluridone, flurochloridone, fluroxypyr (fluroxypyr, fluroxypyr-meptyl), flurtamone, fluthiacet, fluthiacet-methyl, fomesafenFomesafen-sodium, foramsulfuron, fosamine, glufosinate-P-sodium, glufosinate-P-sodium, glufosinate-P-sodium, glyphosate, glyphosate ammonium, glyphosate isopropylammonium, glyphosate diammonium, glyphosate dimethylammonium, glyphosate potassium, glyphosate sodium, and glyphosate-trimesium, H-9201 (i.e., O-(2,4-dimethyl-6-nitrophenyl)O-ethyl isopropyl thiophosphoramide ester) isopropylphosphoramidothioate), halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02 (i.e., (2,4-dichlorophenoxy)acetic acid 1-(dimethoxyphosphoryl)ethyl ester), imazalil, imazamethabenz-methyl, imazamox, imazamox, imazamoxane. pic), imidacloprid ammonium, imidacloprid, imidacloprid isopropylammonium, imidazoquin, imidazoquinoline ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, potassium and sodium iodobenzonil, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilateKUH-043 (i.e., 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole), ketospiradox, lactoferrin, lenacil, linuron, MCPA, MCPA-butoxyethyl ester, MCPA-dimethylammonium, MCPA-2-ethylhexyl ester, MCPA-isopropylammonium, MCPA-potassium and MCPA-sodium, MCPB, MCPB-methyl ester, MCPB-ethyl ester and MCPB-sodium, 2-methyl-4-chloropropionic acid (mecoprop), sodium 2-methyl-4-chloropropionate and 2-methyl-4-chloropropionic acid butoxyethyl ester, purified 2-methyl-4-chloropropionic acid (mecoprop-P), purified 2-methyl-4-chloropropionic acid butoxyethyl ester Ester, dimethylammonium 2-methyl-4-chloropropionate, 2-ethylhexyl 2-methyl-4-chloropropionate and potassium 2-methyl-4-chloropropionate, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methylbenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, 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, pelargonic acid.Norflurazon, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, penoxazone, pethoxamid, petroleum oils), phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone Propoxycarbazone-sodium), propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen (pyraflufen-ethyl), pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron (pyrazosulfuron-ethyl), pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propylPyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, and cyhalothrin. Quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, mesotrione Amine (sulfentrazone), sulfometuron (sulfometuron-methyl), sulfosulfuron, SYP-249 (i.e., 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate), 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 (trifluoroacetic acid), TCA-sodium, butyrate Tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuronthifensulfuron-methyl), thiobencarb, tiafenacil, tolpyralate, toramezone, tralkoxydim, triafamone, triallate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, trilopyr, trietazine Trifloxysulfuron (trifloxysulfuron-sodium), trifludimoxazin, trifluralin, triflusulfuron (triflusulfuron-methyl), tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862 (i.e., 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline), and the following compounds:

[0421]

[0422] Examples of plant growth regulators that can be used as possible mixed formulations include:

[0423] Acibenzolar, benzothiadiazole (acibenzolar-S-methyl), 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, 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 mono(N,N-dimethylalkylammonium), ethephon, flumetralin, chlorpyrifos, fluorenyl butyl ester, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indole-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid (acid), methyl jasmonate, maleic hydrazine, mepiquat chloride, 1-methylcyclopropene, 2-(1-naphthyl)acetamide, 1-naphthaleneacetic acid, 2-naphthoxyacetic acid, nitrophenolate mixture, 4-oxo-4-[(2-phenylethyl)amino]butyric acid, paclobutrazole, N-phenylphthalic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

[0424] When used as active ingredient formulations or co-formulations, these typically contain a variety of conventional binders, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and pH and viscosity modifiers, depending on the case.

[0425] Compounds of general formula (I) and their combinations with one or more of the aforementioned pesticides can be formulated in different ways according to defined physicochemical and biological parameters. Suitable examples of formulation types include:

[0426] - 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;

[0427] - Powdered products are obtained by grinding active ingredients together with finely dispersed solid inorganic or organic substances, such as talc, natural clay (e.g., kaolin, bentonite, and pyrophyllite), diatomaceous earth, or diatomaceous earth powder.

[0428] -Water-based or oil-based suspension concentrates, which can be prepared by means of a bead mill, for example by wet milling;

[0429] - Water-soluble powder;

[0430] - Water-soluble concentrate;

[0431] - Granules, such as water-soluble granules, water-dispersible granules, and granules for broadcasting and soil application;

[0432] - Wettable powders, which, in addition to active ingredients, also contain diluents or inert substances and surfactants;

[0433] -Capsule suspensions and microcapsules;

[0434] -Ultra-low dose formulation.

[0435] The aforementioned formulation types are known to those skilled in the art and are described, for example, in the following literature: K. Martens, “Spray Drying Handbook”, 3rd edition, G. Goodwin Ltd., London, 1979; W. van Valkenburg, “Pesticide Formulations”, Marcel Dekker, NY, 1973; Winacker-Küchler, “Chemische Technologie” [Chemical Technology], Vol. 7, C. Hanser Verlag Munich, 4th edition, 1986; “Perry’s Chemical Engineer’s Handbook”, 5th edition, McGraw-Hill, NY, 1973, pp. 8-57.

[0436] Necessary formulation adjuvants (such as inert materials, surfactants, solvents, and other additives) are also known and documented in, for example, the following literature: McCutcheon's "Detergents and Emulsifiers Annual", MCPubl. Corp., Ridgewood NJ; C. Marsden, "Solvents Guide", 2nd edition, Interscience, NY 1963; H. von Olphen, "Introduction to Clay Colloid Chemistry", 2nd edition, J. Wiley & Sons, NY; [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart1976; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY1964; Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd edition, Darland Books, Caldwell NJ; Winnacker-Küchler, "Chemische Technologie", Volume 7, C. Hanser Verlag Munich, 4th Edition 1986.

[0437] In addition to the formulation adjuvants mentioned above, useful plant protection compositions may also include, as appropriate, conventional wetting agents, binders, dispersants, penetrants, emulsifiers, preservatives, antifreeze agents, fillers, carriers and dyes, defoamers, evaporation inhibitors and pH or viscosity adjusters.

[0438] 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 general formula (I) safeners or combinations of safeners with pesticides. 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 surfactants. 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.

[0439] For application, commercially available formulations are diluted in the usual manner, if appropriate, such as with water in the case of wettable powders, emulsifiable concentrates, dispersants, and water-dispersible granules. Powdered formulations, granules, and sprayable solutions are generally not further diluted with other inert substances before application. The required application rate of safeners of general formula (I) varies with external conditions, including temperature, humidity, and the type of herbicide used.

[0440] In the following illustrative and non-limiting embodiments of the invention, unless otherwise defined, the quantities are expressed based on weight. Example

[0441] 1. Formulation Examples

[0442] 1.1 Powdered Products

[0443] The powder 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 it in a bead mill.

[0444] 1.2 Water-dispersible powders

[0445] A wettable powder that is easily dispersible in water 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 pin mill.

[0446] 1.3 Water-dispersible concentrates

[0447] A water-dispersible concentration is obtained 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. Triton X 207), 3 parts by weight of isotriadecyl 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 microns.

[0448] 1.4 Emulsifiable Concentrate

[0449] The 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.

[0450] 1.5 Water-dispersible granules

[0451] Water-dispersible granules are obtained in the following ways:

[0452] Mix the following components

[0453] 75 parts by weight of a safer of general formula (I) or a mixture of pesticide and a safer of general formula (I),

[0454] 10 parts by weight of calcium lignosulfonate,

[0455] 5 parts by weight of sodium dodecyl sulfate,

[0456] 3 parts by weight of polyvinyl alcohol, and

[0457] 7 parts by weight of polyvinyl alcohol, and

[0458] 7 parts by weight of kaolin,

[0459] The mixture is ground in a pin mill and the powder is granulated in a fluidized bed by spraying water, which is applied as the granulation liquid.

[0460] Water-dispersible granules are also obtained by the following means:

[0461] The following components were homogenized and pulverized in a colloid mill.

[0462] 25 parts by weight of a safener of general formula (I) or a mixture of pesticide and a safener of general formula (I),

[0463] 5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate

[0464] 2 parts by weight of sodium oleoylmethyl taurate,

[0465] 17 parts by weight of calcium carbonate,

[0466] 50 parts by weight of water, and

[0467] 1 part by weight of polyvinyl alcohol,

[0468] 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 resulting suspension.

[0469] 2. Biological Example:

[0470] 2.1 Taking the reduction of damage to summer wheat (TRZAS) by mesosulfuron-methyl as an example, the relevant effects of the compounds selected in this invention are described.

[0471] Seeds of the crop to be treated were placed in sandy loam soil in plastic pots (~4 cm in diameter), covered with soil, and grown in a greenhouse under good germination and growth conditions. The test plants were treated at the early leaf stage (BBCH10-BBCH12). During this process, the compound of general formula (I) of the present invention, formulated as a wettable powder (WP), was sprayed onto the aboveground parts of the plant as an aqueous suspension with a water application rate equivalent to 800 l / ha and the addition of a specified dose of wetting agent (e.g., 0.2% Genapol-LRO or 0.2% Mero).

[0472] Herbicides were then applied. For this purpose, mesosulfuron-methyl, formulated as a water-dispersible granule (WG), was sprayed onto the aboveground parts of the plants as a water dispersion, with a water application rate equivalent to 800 l / ha and the addition of a wetting agent at a dose of 40–60 g / ha (e.g., 0.2% Genapol-LRO or 1 l / ha Biopower). The dosage of the herbicide was chosen such that, at the time of evaluation, it caused visually significant damage (minimum 30%, maximum 75%) to the control crop plants included in the same experiment that were not treated with a safener, compared to untreated crop plants.

[0473] Following application, the plants were cultivated in a greenhouse under favorable growing conditions. The efficacy of the test compound was visually assessed 9–13 days post-application. For this purpose, the appearance of plants treated with the test compound and herbicide was compared to that of the corresponding herbicide control group (without safener; showing clearly visible damage) and the untreated control group (without damage). The damage-reducing effect of the test compound in this paper is expressed using graded efficacy codes according to the following scheme:

[0474] 0: No reduction in damage (appearance corresponds to the herbicide control group)

[0475] 1: Slightly reduce damage

[0476] 2: Significantly reduces damage

[0477] 3: Significantly reduces damage

[0478] 4: Complete reduction of damage (appearance compared to the untreated control group)

[0479] Experiments have shown that the selected compounds of the present invention are significantly effective in mitigating damage to summer wheat crops (TRZAS; cultivar Triso) caused by the herbicide mesosulfuron-methyl:

[0480]

Claims

1. Compounds of general formula (I) or their salts in R 1 Selected from groups R 2 Selected from groups R 3 It is hydrogen or (C1-C6) alkyl. and R 4 It can be hydrogen, 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 1 Selected from groups R 2 Selected from groups R 3 It is hydrogen, CH2CH3 or CH3, and R 4 It can be hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, or isobutyl.

3. The compound of general formula (I) according to claim 1, or a salt thereof, in R 1 Selected from groups R 2 Selected from groups R 3 It is hydrogen or CH3. and R 4 It can be hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, or isobutyl.

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

5. The compound of general formula (I) according to claim 1, or a salt thereof, wherein R 1 Selected from groups R 2 Selected from groups R 3 hydrogen, and R 4 It can be hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, or isobutyl.

6. A compound is selected from the following compounds or their salts.

7. A crop protection composition, characterized in that... It contains at least one compound or salt thereof as described in any one of claims 1 to 6, and at least one herbicide and optionally a formulation adjuvant.

8. A method for reducing the phytotoxicity of mesosulfuron-methyl to crop plants by using one or more compounds according to any one of claims 1 to 6 or salts thereof, or the composition according to claim 7.

9. A method for reducing the phytotoxicity of mesosulfuron-methyl to crops, characterized in that... One or more of the compounds of any one of claims 1 to 6, or salts thereof, used in combination with mesosulfuron-methyl, are applied simultaneously or in any order with mesosulfuron-methyl.

Images