Use of a compound and salts thereof for reducing phytotoxicity of an agrochemical

Abstract

The present invention relates to [(1,5-diphenyl-1 H-pyrazol-3-yl)oxy] acetic acid derivatives of the formula (I) and salts thereof (I) and to compositions containing them for reducing the phytotoxic action of agrochemicals, in particular of herbicides, in useful plants and crop plants. The invention also relates in particular to specific [(1,5-diphenyl-1 H-pyrazol-3-yl)oxy] acetic acid derivatives of the formula (I) and to methods for their preparation.

Description

[0001] This invention relates to the use of [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid derivatives and their salts, as well as compositions comprising them, in reducing the phytotoxicity of agrochemicals, particularly herbicides, in useful plants and crop plants.

[0002] Similarly, and particularly, the present invention relates to specific [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid derivatives and methods for their preparation.

[0003] When pesticides are used to control unwanted organisms in horticultural and sivicultural crops, the beneficial plants are often also more or less harmed by the pesticides used (e.g., herbicides, insecticides, and especially fungicides). This unwanted phytotoxicity occurs to a certain degree when large amounts of herbicides are used in beneficial crops such as corn, rice, or cereals (primarily in post-emergence application). In some cases, the use of “safeners” or “antidotes” can protect beneficial plants from the phytotoxicity of pesticides without reducing or significantly impairing pesticide efficacy against pests. In some cases, even enhanced pesticide efficacy against pests such as weeds has been observed in the presence of safeners.

[0004] 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.

[0005] The safener effects of phenoxyalkane carboxylic acids or heteroaryloxyalkane carboxylic acids when used in combination with herbicides are well-known. Examples of such compounds are MCPA and similar compounds that still retain herbicidal activity against harmful plants, or cloquintocet-mexyl.

[0006] Also known are safeners for N-phenyl-substituted heteroaryl carboxylic acid ester derivatives having multiple heteroatoms in heteroaromatic systems. Examples of such safeners are mefenpyr-diethyl and isoxadifen-ethyl, which are used in commercially available products.

[0007] 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.

[0008] WO 2005 / 112630 also discloses 1,2-dihydroquinoxalin-2-one derivatives, and

[0009] WO 2008 / 131860 discloses pyridone formamide as a safer agent.

[0010] The active ingredients of the chemical category of [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid derivatives with antifungal properties are described in Molecules 2014, 19(1), 1302-1316, J. of Heterocyclic Chemistry 2012, 49(6) 1370-1375, Acta Crystallographica, Section E: Structure Reports Online 2012, 68(8), o2419, Acta Crystallographica, Section E: Structure Reports Online 2012, 68(1), o123, J. of Heterocyclic Chemistry 2010, 47(4) 897-902. Antimicrobial pesticides [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid derivatives are described in CN102093344 and CN101284815.

[0011] Various documents document [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives with medicinal properties. WO2008073825 and DE2828529 disclose [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives.

[0012] The synthesis of the [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid derivative is described in the European Journal of Organic Chemistry 2011, 27, 5323-5339.

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

[0014] - Insufficient useful plant protection characteristics

[0015] - When combined with a specific herbicide, the range of useful plants for which the safener / herbicide to be used is not large enough.

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

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

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

[0019] Therefore, the present invention provides the use of plant protective compounds of general formula (I) or salts thereof for reducing the phytotoxic effects of pesticides, especially herbicides, on beneficial plants or crop plants.

[0020]

[0021] in

[0022] R 1 and R 2 Independently hydrogen, halogen, 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 The last seven groups are either 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,

[0025] (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

[0026] -(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

[0027] -(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

[0028] Formula-NR a R b Or -N = CR c R d group,

[0029] 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.

[0030] 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.

[0031] Or R c and R d Together with the carbon atom, it is a 3- to 8-membered carbocyclic or heterocyclic group, said heterocyclic group 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, and n and m are independently values ​​from 0 to 5.

[0032] and

[0033] p is 0, 1, or 2.

[0034] Compounds of general formula (I) can form salts by adding a suitable inorganic or organic acid to a basic group, such as mineral acids like HCl, HBr, H₂SO₄, H₃PO₄, or HNO₃, or organic acids like carboxylic acids like formic acid, acetic acid, propionic acid, oxalic acid, lactic acid, or salicylic acid, or sulfonic acids like p-toluenesulfonic acid, where the basic group is, for example, amino, alkylamino, dialkylamino, piperidinyl, morpholinyl, or pyridinyl. These salts then contain a conjugate base as an anionic acid. A suitable deprotonated form of the substituent (e.g., sulfonic acid, particularly sulfonamides or carboxylic acids) can form an internal salt with a self-protonable group (such as an amino group). Salts can also be formed by the action of a base on a compound of general formula (I). For example, suitable bases are organic amines (such as trialkylamines, morpholines, piperidine, and pyridine) and ammonium, alkali metal or alkaline earth metal hydroxides, carbonates, and bicarbonates, particularly sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, and potassium bicarbonate. These salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, such as metal salts, particularly alkali metal or alkaline earth metal salts, especially sodium and potassium salts, or ammonium salts, with salts of organic amines or quaternary ammonium salts, such as those containing [NR]. i R ii R iii R iv ] + Salts of cations, wherein R i To R iv Each is an independent organic group, particularly alkyl, aryl, aralkyl, or alkylaryl. Also useful are alkyl sulfonium and alkyl oxide sulfonium salts, such as (C1-C4)-trialkyl sulfonium and (C1-C4)-trialkyl oxide sulfonium salts.

[0035] The compounds of formula (I) and their salts used in this invention are referred to hereinafter as "compounds of formula (I)".

[0036] The preferred use of compounds of general formula (I) in this invention, wherein

[0037] R 1 and R 2 Independently hydrogen, halogen, cyano, nitro, (C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)ynyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkenyl, (C1-C4)alkoxy, and (C1-C4)alkyl S(O). p The last seven groups are either 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,

[0038] R 3 It consists of hydrogen and (C1-C4) alkyl groups.

[0039] R4 is hydrogen, (C1-C 16 )alkyl, (C1-C 16 ) Haloalkyl, (C1-C 16 )cyanoalkyl,

[0040] (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-C 16 ) Haloalkylthio

[0041] -(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

[0042] basal-(C3-C) 12 )cycloalkyl-(C1-C 16 )alkyl,

[0043] n and m are independent values ​​from 0 to 4.

[0044] and

[0045] p is 0, 1, or 2.

[0046] The use of compounds of general formula (I) in this invention is particularly preferred, wherein R 1 and R 2 Independently hydrogen, halogen, cyano, methyl, ethyl, CF3, CF2Cl, CH2F,

[0047] CHF2, OCH3, OCF3, SCH3, SOCH3, SO2CH3 and SCF3, R 3 For hydrogen, CH2CH3 and CH3,

[0048] R 4 For hydrogen, (C1-C 12 )alkyl, (C1-C 12 ) Haloalkyl, (C1-C 12 )cyanoalkyl,

[0049] (C2-C 12 )alkenyl, (C2-C 12 ) ynyl group, (C3-C 12 )cycloalkyl, (C3-C 12 )cycloalkenyl, aryl, heteroaryl, (C1-C 12 )alkoxy-(C1-C 12 )alkyl, (C1-C 12 ) Haloalkoxy-(C1-C 12 )alkyl, (C1-C 12 )alkoxy-(C1-C 12 ) Haloalkyl, (C1-C 12 )alkylthio-(C1-C 12 )alkyl, (C1-C 12 ) Haloalkylthio

[0050] -(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

[0051] -(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 group, where n and m are independently 0, 1, 2, or 3.

[0052] and

[0053] p is 0, 1, or 2.

[0054] The present invention particularly preferably provides the use of compounds of general formula (I) in the present invention, wherein R 1 and R2 Independently, it can be hydrogen, fluorine, chlorine, bromine, iodine, CN, methyl, CF3, CF2Cl,

[0055] CH2F, CHF2, OCH3, OCF3, SCH3, SOCH3, SO2CH3, and SCF3,

[0056] R 3 It consists of hydrogen and CH3.

[0057] R 4 For hydrogen, (C1-C 10 )alkyl, (C1-C 10 ) Haloalkyl, (C1-C 10 )cyanoalkyl,

[0058] (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,

[0059] n and m are independently 0, 1, 2 or 3.

[0060] and

[0061] p is 0, 1, or 2.

[0062] The present invention particularly preferably provides the use of compounds of general formula (I) in the present invention, wherein...

[0063] R 1 and R 2 Independently, it can be hydrogen, fluorine, chlorine, bromine, iodine, CN, methyl, CF3, CH2F, CHF2, OCH3, OCF3, SCH3, SOCH3, SO2CH3, and SCF3.

[0064] R 3 It is hydrogen.

[0065] R 4 The following are the compounds: hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, phenyl, benzyl, CH2(4-Cl-Ph), CH2(4-F-Ph), CH2(4-MeO-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl, methylpropionate-3-yl, ethylpropionate-3-yl, methylacetyl-2-yl, ethylacetyl-2-yl, methylneoplastate-2-yl, ethylneoplastate-3-yl , Methyl-2-methylpropionate-3-yl, Methyl-2,2-dimethylpropionate-3-yl, Ethyl-2-methylpropionate-3-yl, Methyl-2-propionate-2-yl, Ethyl-2-propionate-2-yl, Methylacetate-2-yl, Ethylacetate-2-yl, Methyl-1-methylcyclopropanecarboxylate-2-yl, Ethyl-1-methylcyclopropanecarboxylate-2-yl, 2-(dimethylamino)ethyl, Oxetan-3-yl, (3-methyloxetan-3-yl)methyl, 2,2,2-trifluoroethyl, 2,2 -Difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl, cyclopropylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl, allyl, propyne 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

[0066] n and m are independently 0, 1, 2 or 3, where m and n must not both be 0.

[0067] The present invention particularly preferably provides the use of compounds of general formula (I) in the present invention, wherein...

[0068] (R 1 ) n -Phenyl groups are in the range of Q-1.1 to Q-1.53.

[0069]

[0070]

[0071] and (R) 2 ) m -Phenyl groups are in the range of Q-2.1 to Q-2.53.

[0072]

[0073]

[0074]

[0075] R 3 It is hydrogen.

[0076] and

[0077] R 4 The following are the possible values: hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, phenyl, benzyl, CH2(4-Cl-Ph), CH2(4-F-Ph), CH2(4-OMe-Ph).

[0078] 2-Methoxyethyl, Tetrahydrofuran-2-yl-methyl, Tetrahydrofuran-3-ylmethyl, Tetrahydropyran-2-ylmethyl, Tetrahydropyran-3-ylmethyl, Tetrahydropyran-4-ylmethyl, Methylpropionate-3-yl, Ethylpropionate-3-yl, Methylacetyl-2-yl, Ethylacetyl-2-yl, Methylneoplastate-2-yl, Ethylneoplastate-3-yl, Methyl-2-methylpropionate-3-yl, Methyl-2,2-dimethylpropionate-3-yl, Ethyl-2-methylpropionate-3-yl, Methyl-2-propionate-2-yl, Ethyl-2-propionate

[0079] 2-yl, methyl acetate-2-yl, ethyl acetate-2-yl, methyl-1-methylcyclopropane carboxylate-2-yl, ethyl-1-methylcyclopropane carboxylate-2-yl, 2-(dimethylamino)ethyl, oxetane-3-yl, (3-methyloxetane-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-propynyl (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl, 3-phenylpropane

[0080] -2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, heptyl-2-yl, isobutyl, 1,3-

[0081] Dioxacyclopentane-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl.

[0082] Novel and useful plant-protective compounds of general formula (I) or salts thereof for reducing the phytotoxicity of pesticides, especially herbicides, to beneficial plants or crops are not known in the prior art and are therefore also part of the subject matter of this invention.

[0083]

[0084] in

[0085] R 1 and R 2 Independently hydrogen, halogen, 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 The last seven groups are either 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,

[0086] R 3It consists of hydrogen and (C1-C6) alkyl groups.

[0087] R 4 For hydrogen, (C1-C 18 )alkyl, (C1-C 18 ) Haloalkyl, (C1-C 18 )cyanoalkyl,

[0088] (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

[0089] -(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

[0090] -(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 -NR a R b Or -N = CR c R d group,

[0091] Among the aforementioned two groups, R a R b R c and R dEach of the functional groups is independently hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)ynyl, benzyl,

[0092] Substituted benzyl, phenyl, or substituted phenyl,

[0093] 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.

[0094] Or R c and R d Together with the carbon atom, it is a 3- to 8-membered carbon ring or heterocyclic group, wherein the heterocyclic group may contain 1 to 3 cyclic heteroatoms selected from N, O, and S.

[0095] Where the carbocyclic or heterocyclic group is not substituted or is selected from one or more...

[0096] Substitution of (C1-C4)-alkyl and (C1-C4)-haloalkyl groups,

[0097] n and m are independent values ​​from 0 to 5.

[0098] and

[0099] p is 0, 1, or 2.

[0100] The following compounds are not included:

[0101] {[5-(4-methoxyphenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS [1310875-73-0])

[0102] {[5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS [1310875-75-2])

[0103] {[5-(3-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS [1310875-76-3])

[0104] {[5-(3-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-77-4])

[0105] {[5-(4-methoxyphenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-85-4])

[0106] {[5-(4-fluorophenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076207-91-4])

[0107] [(1,5-Diphenyl-1H-pyrazol-3-yl)oxy]acetic acid (CAS[73457-62-2])

[0108] Sodium [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetate (CAS[73457-94-0])

[0109] {[5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-74-1])

[0110] {[5-(4-bromophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076207-89-0])

[0111] {[1,5-bis(4-fluorophenyl)-1H-pyrazole-3-yl]oxy}acetic acid (CAS[1076208-05-3])

[0112] {[5-(4-chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-79-6])

[0113] {[1-(4-fluorophenyl)-5-(4-methoxyphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076208-00-8])

[0114] [(1,5-Diphenyl-1H-pyrazol-3-yl)oxy]ethyl acetate (CAS [1246513-41-6])

[0115] {[1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS[1076207-99-2])

[0116] ({1-Phenylacetyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1076207-90-3])

[0117] Ethyl {[5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy} (CAS [1246513-42-7])

[0118] {[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076208-04-2])

[0119] {[1-Phenylacetyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076207-88-9])

[0120] {[5-(2,4-dichlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-84-3])

[0121] {[5-(4-methoxyphenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}ethyl acetate (CAS [1076207-87-8])

[0122] Ethyl {[5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy} (CAS [1246513-43-8])

[0123] {[5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1246513-44-9])

[0124] Ethyl {[1-(4-isopropylphenyl)-5-phenyl-1H-pyrazole-3-yl]oxy} (CAS [1246513-47-2])

[0125] Ethyl {[5-(3-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy} (CAS [1338378-37-2])

[0126] Ethyl {[5-(3-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy} (CAS [1246513-46-1])

[0127] {[1-(4-tert-butylphenyl)-5-(3,4-dimethoxyphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076208-01-9])

[0128] {[5-(2,4-dichlorophenyl)-1-(4-isopropylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-80-9])

[0129] ({1-(4-chlorophenyl)-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1310875-83-2])

[0130] ({1-(4-fluorophenyl)-5-[3-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1310875-81-0])

[0131] {[1-(4-tert-butylphenyl)-5-phenyl-1H-pyrazole-3-yl]oxy}ethyl acetate (CAS [1076207-93-6])

[0132] {[5-(4-bromophenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1076208-03-1])

[0133] Ethyl {[1-(4-fluorophenyl)-5-(4-methylphenyl)-1H-pyrazol-3-yl]oxy} (CAS [1076207-98-1])

[0134] {[1-(4-isopropylphenyl)-5-(4-methoxyphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1246513-48-3])

[0135] {[1-(4-isopropylphenyl)-5-(4-methoxyphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS[1246513-50-7])

[0136] ({1-(2,4-dichlorophenyl)-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1310875-86-5])

[0137] {[1-(4-tert-butylphenyl)-5-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS[1076207-97-0])

[0138] {[1-(4-tert-butylphenyl)-5-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS[1310875-82-1])

[0139] Ethyl {[1-(2,4-dichlorophenyl)-5-(4-methylphenyl)-1H-pyrazol-3-yl]oxy} (CAS [1076207-94-7])

[0140] {[1-Phenylacetyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1246513-45-0])

[0141] {[1-(4-methylphenyl)-5-(3,4,5-trimethoxyphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS[1076208-02-0])

[0142] {[1-(4-fluorophenyl)-5-(4-phenoxyphenyl)-1H-pyrazole-3-yl]oxy}ethyl acetate (CAS[1076208-06-4])

[0143] {[5-(3,4-dimethoxyphenyl)-1-(2,4-dinitrophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-78-5])

[0144] {[5-(3,4-dimethoxyphenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS[1076207-92-5])

[0145] Ethyl {[1-(2,4-dichlorophenyl)-5-(4-phenoxyphenyl)-1H-pyrazole-3-yl]oxy}ethyl acetate

[0146] (CAS[1076207-95-8])

[0147] {[5-(4-chlorophenyl)-1-(2,4-dinitrophenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1076207-96-9]).

[0148] The compounds of formula (I) and their salts used in this invention are referred to below as "compounds of general formula (I)".

[0149] The present invention preferably provides compounds of general formula (I), wherein

[0150] R 1 and R 2 Independently hydrogen, halogen, cyano, nitro, (C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)ynyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkenyl, (C1-C4)alkoxy, and (C1-C4)alkyl S(O). p The last seven groups are either 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,

[0151] R 3 It consists of hydrogen and (C1-C4) alkyl groups.

[0152] R 4 For hydrogen, (C1-C 18 )alkyl, (C1-C 18 ) Haloalkyl, (C1-C 18 )cyanoalkyl,

[0153] (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

[0154] -(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,

[0155] n and m are independent values ​​from 0 to 4.

[0156] and

[0157] p is 0, 1, or 2.

[0158] The following compounds are not included:

[0159] {[5-(4-methoxyphenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS [1310875-73-0])

[0160] {[5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS [1310875-75-2])

[0161] {[5-(3-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS [1310875-76-3])

[0162] {[5-(3-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-77-4])

[0163] {[5-(4-methoxyphenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-85-4])

[0164] {[5-(4-fluorophenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076207-91-4])

[0165] [(1,5-Diphenyl-1H-pyrazol-3-yl)oxy]acetic acid (CAS[73457-62-2])

[0166] Sodium [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetate (CAS[73457-94-0])

[0167] {[5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-74-1])

[0168] {[5-(4-bromophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076207-89-0])

[0169] {[1,5-bis(4-fluorophenyl)-1H-pyrazole-3-yl]oxy}acetic acid (CAS[1076208-05-3])

[0170] {[5-(4-chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-79-6])

[0171] {[1-(4-fluorophenyl)-5-(4-methoxyphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076208-00-8])

[0172] [(1,5-Diphenyl-1H-pyrazol-3-yl)oxy]ethyl acetate (CAS [1246513-41-6])

[0173] {[1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS[1076207-99-2])

[0174] ({1-Phenylacetyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1076207-90-3])

[0175] Ethyl {[5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy} (CAS [1246513-42-7])

[0176] {[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076208-04-2])

[0177] {[1-Phenylacetyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076207-88-9])

[0178] {[5-(2,4-dichlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-84-3])

[0179] {[5-(4-methoxyphenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}ethyl acetate (CAS [1076207-87-8])

[0180] Ethyl {[5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy} (CAS [1246513-43-8])

[0181] {[5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1246513-44-9])

[0182] Ethyl {[1-(4-isopropylphenyl)-5-phenyl-1H-pyrazole-3-yl]oxy} (CAS [1246513-47-2])

[0183] Ethyl {[5-(3-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy} (CAS [1338378-37-2])

[0184] Ethyl {[5-(3-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy} (CAS [1246513-46-1])

[0185] {[1-(4-tert-butylphenyl)-5-(3,4-dimethoxyphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076208-01-9])

[0186] {[5-(2,4-dichlorophenyl)-1-(4-isopropylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-80-9])

[0187] ({1-(4-chlorophenyl)-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1310875-83-2])

[0188] ({1-(4-fluorophenyl)-5-[3-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1310875-81-0])

[0189] {[1-(4-tert-butylphenyl)-5-phenyl-1H-pyrazole-3-yl]oxy}ethyl acetate (CAS [1076207-93-6])

[0190] {[5-(4-bromophenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1076208-03-1])

[0191] Ethyl {[1-(4-fluorophenyl)-5-(4-methylphenyl)-1H-pyrazol-3-yl]oxy} (CAS [1076207-98-1])

[0192] {[1-(4-isopropylphenyl)-5-(4-methoxyphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1246513-48-3])

[0193] {[1-(4-isopropylphenyl)-5-(4-methoxyphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS[1246513-50-7])

[0194] ({1-(2,4-dichlorophenyl)-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1310875-86-5])

[0195] {[1-(4-tert-butylphenyl)-5-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS[1076207-97-0])

[0196] {[1-(4-tert-butylphenyl)-5-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS[1310875-82-1])

[0197] Ethyl {[1-(2,4-dichlorophenyl)-5-(4-methylphenyl)-1H-pyrazol-3-yl]oxy} (CAS [1076207-94-7])

[0198] {[1-Phenylacetyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1246513-45-0])

[0199] {[1-(4-methylphenyl)-5-(3,4,5-trimethoxyphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS[1076208-02-0])

[0200] {[1-(4-fluorophenyl)-5-(4-phenoxyphenyl)-1H-pyrazole-3-yl]oxy}ethyl acetate (CAS[1076208-06-4])

[0201] {[5-(3,4-dimethoxyphenyl)-1-(2,4-dinitrophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-78-5])

[0202] Ethyl [5-(3,4-dimethoxyphenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate

[0203] (CAS[1076207-92-5])

[0204] Ethyl {[1-(2,4-dichlorophenyl)-5-(4-phenoxyphenyl)-1H-pyrazole-3-yl]oxy}ethyl acetate

[0205] (CAS[1076207-95-8])

[0206] {[5-(4-chlorophenyl)-1-(2,4-dinitrophenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1076207-96-9]).

[0207] The present invention particularly preferably provides compounds of general formula (I), wherein

[0208] R 1 and R 2 Independently hydrogen, halogen, cyano, methyl, ethyl, CF3, CF2Cl, CH2F,

[0209] CHF2, OCH3, OCF3, SCH3, SOCH3, SO2CH3, and SCF3,

[0210] R 3 For hydrogen, CH2CH3 and CH3,

[0211] R 4 For hydrogen, (C1-C 16 )alkyl, (C1-C 16 ) Haloalkyl, (C1-C16 )cyanoalkyl,

[0212] (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-C 16 ) Haloalkylthio

[0213] -(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,

[0214] n and m are independently 0, 1, 2 or 3.

[0215] and

[0216] p is 0, 1, or 2.

[0217] The following compounds are not included:

[0218] {[5-(4-methoxyphenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS [1310875-73-0])

[0219] {[5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS [1310875-75-2])

[0220] {[5-(3-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS [1310875-76-3])

[0221] {[5-(3-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-77-4])

[0222] {[5-(4-methoxyphenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-85-4])

[0223] {[5-(4-fluorophenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076207-91-4])

[0224] [(1,5-Diphenyl-1H-pyrazol-3-yl)oxy]acetic acid (CAS[73457-62-2])

[0225] Sodium (1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetate (CAS [73457-94-0])

[0226] {[5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-74-1])

[0227] {[5-(4-bromophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076207-89-0])

[0228] {[1,5-bis(4-fluorophenyl)-1H-pyrazole-3-yl]oxy}acetic acid (CAS[1076208-05-3])

[0229] {[5-(4-chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-79-6])

[0230] {[1-(4-fluorophenyl)-5-(4-methoxyphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076208-00-8])

[0231] [(1,5-Diphenyl-1H-pyrazol-3-yl)oxy]ethyl acetate (CAS [1246513-41-6])

[0232] {[1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS[1076207-99-2])

[0233] ({1-Phenylacetyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1076207-90-3])

[0234] Ethyl {[5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy} (CAS [1246513-42-7])

[0235] {[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076208-04-2])

[0236] {[1-Phenylacetyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076207-88-9])

[0237] {[5-(2,4-dichlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-84-3])

[0238] {[5-(4-methoxyphenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}ethyl acetate (CAS [1076207-87-8])

[0239] Ethyl {[5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy} (CAS [1246513-43-8])

[0240] {[5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1246513-44-9])

[0241] Ethyl {[1-(4-isopropylphenyl)-5-phenyl-1H-pyrazole-3-yl]oxy} (CAS [1246513-47-2])

[0242] Ethyl {[5-(3-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy} (CAS [1338378-37-2])

[0243] Ethyl {[5-(3-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy} (CAS [1246513-46-1])

[0244] {[1-(4-tert-butylphenyl)-5-(3,4-dimethoxyphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076208-01-9])

[0245] {[5-(2,4-dichlorophenyl)-1-(4-isopropylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-80-9])

[0246] ({1-(4-chlorophenyl)-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1310875-83-2])

[0247] ({1-(4-fluorophenyl)-5-[3-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1310875-81-0])

[0248] {[1-(4-tert-butylphenyl)-5-phenyl-1H-pyrazole-3-yl]oxy}ethyl acetate (CAS [1076207-93-6])

[0249] {[5-(4-bromophenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1076208-03-1])

[0250] Ethyl {[1-(4-fluorophenyl)-5-(4-methylphenyl)-1H-pyrazol-3-yl]oxy} (CAS [1076207-98-1])

[0251] {[1-(4-isopropylphenyl)-5-(4-methoxyphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1246513-48-3])

[0252] {[1-(4-isopropylphenyl)-5-(4-methoxyphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS[1246513-50-7])

[0253] ({1-(2,4-dichlorophenyl)-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1310875-86-5])

[0254] {[1-(4-tert-butylphenyl)-5-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS[1076207-97-0])

[0255] {[1-(4-tert-butylphenyl)-5-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS[1310875-82-1])

[0256] Ethyl {[1-(2,4-dichlorophenyl)-5-(4-methylphenyl)-1H-pyrazol-3-yl]oxy} (CAS [1076207-94-7])

[0257] {[1-Phenylacetyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1246513-45-0])

[0258] {[1-(4-methylphenyl)-5-(3,4,5-trimethoxyphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS[1076208-02-0])

[0259] {[1-(4-fluorophenyl)-5-(4-phenoxyphenyl)-1H-pyrazole-3-yl]oxy}ethyl acetate (CAS[1076208-06-4])

[0260] {[5-(3,4-dimethoxyphenyl)-1-(2,4-dinitrophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-78-5])

[0261] {[5-(3,4-dimethoxyphenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS[1076207-92-5])

[0262] {[1-(2,4-dichlorophenyl)-5-(4-phenoxyphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS[1076207-95-8])

[0263] {[5-(4-chlorophenyl)-1-(2,4-dinitrophenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1076207-96-9]).

[0264] The present invention particularly preferably provides compounds of general formula (I), wherein

[0265] R 1 and R 2 Independently hydrogen, halogen, cyano, methyl, ethyl, CF3, CF2Cl, CH2F,

[0266] CHF2, OCH3, OCF3, SCH3, SOCH3, SO2CH3, and SCF3,

[0267] R 3 It consists of hydrogen and CH3.

[0268] R 4 For hydrogen, (C1-C 10)alkyl, (C1-C 10 ) Haloalkyl, (C1-C 10 )cyanoalkyl,

[0269] (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

[0270] -(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,

[0271] n and m are independently 0, 1, 2 or 3.

[0272] and

[0273] p is 0, 1, or 2.

[0274] The following compounds are not included:

[0275] {[5-(4-methoxyphenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS [1310875-73-0])

[0276] {[5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS [1310875-75-2])

[0277] {[5-(3-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS [1310875-76-3])

[0278] {[5-(3-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-77-4])

[0279] {[5-(4-methoxyphenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-85-4])

[0280] {[5-(4-fluorophenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076207-91-4])

[0281] [(1,5-Diphenyl-1H-pyrazol-3-yl)oxy]acetic acid (CAS[73457-62-2])

[0282] Sodium [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetate (CAS[73457-94-0])

[0283] {[5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-74-1])

[0284] {[5-(4-bromophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076207-89-0])

[0285] {[1,5-Di(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076208-05-3])

[0286] {[5-(4-chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-79-6])

[0287] {[1-(4-fluorophenyl)-5-(4-methoxyphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076208-00-8])

[0288] [(1,5-Diphenyl-1H-pyrazol-3-yl)oxy]ethyl acetate (CAS [1246513-41-6])

[0289] {[1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS[1076207-99-2])

[0290] ({1-Phenylacetyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1076207-90-3])

[0291] Ethyl {[5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy} (CAS [1246513-42-7])

[0292] {[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076208-04-2])

[0293] {[1-Phenylacetyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076207-88-9])

[0294] {[5-(2,4-dichlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-84-3])

[0295] {[5-(4-methoxyphenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}ethyl acetate (CAS [1076207-87-8])

[0296] Ethyl {[5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy} (CAS [1246513-43-8])

[0297] {[5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1246513-44-9])

[0298] Ethyl {[5-(3-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy} (CAS [1338378-37-2])

[0299] Ethyl {[5-(3-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy} (CAS [1246513-46-1])

[0300] ({1-(4-chlorophenyl)-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1310875-83-2])

[0301] ({1-(4-fluorophenyl)-5-[3-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1310875-81-0])

[0302] {[5-(4-bromophenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1076208-03-1])

[0303] Ethyl {[1-(4-fluorophenyl)-5-(4-methylphenyl)-1H-pyrazol-3-yl]oxy} (CAS [1076207-98-1])

[0304] ({1-(2,4-dichlorophenyl)-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1310875-86-5])

[0305] Ethyl {[1-(2,4-dichlorophenyl)-5-(4-methylphenyl)-1H-pyrazol-3-yl]oxy} (CAS [1076207-94-7])

[0306] {[1-Phenylacetyl-5-(3,4,5-trimethoxyphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1246513-45-0])

[0307] {[1-(4-methylphenyl)-5-(3,4,5-trimethoxyphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS[1076208-02-0])

[0308] {[5-(3,4-dimethoxyphenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1076207-92-5]).

[0309] The present invention particularly preferably provides compounds of general formula (I), wherein

[0310] R 1 and R 2 Independently hydrogen, halogen, cyano, methyl, ethyl, CF3, CF2Cl, CH2F,

[0311] CHF2, OCH3, OCF3, SCH3, SOCH3, SO2CH3, and SCF3,

[0312] R 3 It is hydrogen.

[0313] R 4The following are the compounds: hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, phenyl, benzyl, CH2(4-Cl-Ph), CH2(4-F-Ph), CH2(4-MeO-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl, methylpropionate-3-yl, ethylpropionate-3-yl, methyl acetate-2-yl, ethyl acetate-2-yl, methyl neopentanoate-2-yl, ethyl neopentanoate-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

[0314] -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,

[0315] 2,2,2-Trifluoroethyl, 2,2-Difluoroethyl, 2-Fluoroethyl, 2,2,3,3,3-Pentafluoropropyl, Cyclopropylmethyl, 1-Cyclopropylethyl, (1-Methylcyclopropyl)methyl, (2,2-

[0316] (2,2-Dimethylcyclopropyl)methyl, allyl, propynyl (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl, 3-phenylprop-2-yn-1-yl

[0317] 3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-

[0318] alken-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl,

[0319] 3-Methylbut-2-en-1-yl, 3-Methylbut-1-en-1-yl, 1-(2E)-1-methylbutane

[0320] -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,

[0321] n and m are independently 0, 1, 2, or 3, where m and n must not both be 0.

[0322] The following compounds are not included:

[0323] {[5-(4-methoxyphenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS [1310875-73-0])

[0324] {[5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS [1310875-75-2])

[0325] {[5-(3-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS [1310875-76-3])

[0326] {[5-(3-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-77-4])

[0327] {[5-(4-methoxyphenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-85-4])

[0328] {[5-(4-fluorophenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076207-91-4])

[0329] [(1,5-Diphenyl-1H-pyrazol-3-yl)oxy]acetic acid (CAS[73457-62-2])

[0330] Sodium [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetate (CAS[73457-94-0])

[0331] {[5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-74-1])

[0332] {[5-(4-bromophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076207-89-0])

[0333] {[1,5-bis(4-fluorophenyl)-1H-pyrazole-3-yl]oxy}acetic acid (CAS[1076208-05-3])

[0334] {[5-(4-chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-79-6])

[0335] {[1-(4-fluorophenyl)-5-(4-methoxyphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076208-00-8])

[0336] [(1,5-Diphenyl-1H-pyrazol-3-yl)oxy]ethyl acetate (CAS [1246513-41-6])

[0337] {[1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS[1076207-99-2])

[0338] ({1-Phenylacetyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1076207-90-3])

[0339] Ethyl {[5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy} (CAS [1246513-42-7])

[0340] {[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076208-04-2])

[0341] {[5-(2,4-dichlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-84-3])

[0342] {[5-(4-methoxyphenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}ethyl acetate (CAS [1076207-87-8])

[0343] Ethyl {[5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy} (CAS [1246513-43-8])

[0344] {[5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1246513-44-9])

[0345] Ethyl {[5-(3-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy} (CAS [1338378-37-2])

[0346] Ethyl {[5-(3-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy} (CAS [1246513-46-1])

[0347] ({1-(4-chlorophenyl)-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1310875-83-2])

[0348] ({1-(4-fluorophenyl)-5-[3-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1310875-81-0])

[0349] {[5-(4-bromophenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1076208-03-1])

[0350] Ethyl {[1-(4-fluorophenyl)-5-(4-methylphenyl)-1H-pyrazol-3-yl]oxy} (CAS [1076207-98-1])

[0351] ({1-(2,4-dichlorophenyl)-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1310875-86-5])

[0352] Ethyl {[1-(2,4-dichlorophenyl)-5-(4-methylphenyl)-1H-pyrazol-3-yl]oxy} (CAS [1076207-94-7])

[0353] {[5-(3,4-dimethoxyphenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1076207-92-5]).

[0354] The present invention particularly preferably provides compounds of general formula (I), wherein

[0355] (R 1 ) n -Phenyl groups are in the range of Q-1.1 to Q-1.53.

[0356]

[0357]

[0358] and (R) 2 ) m -Phenyl groups are in the range of Q-2.1 to Q-2.53.

[0359]

[0360] R 3 It is hydrogen.

[0361] and

[0362] R 4 The following are the possible values: hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, phenyl, benzyl, CH2(4-Cl-Ph), CH2(4-F-Ph), CH2(4-MeO-Ph).

[0363] 2-Methoxyethyl, Tetrahydrofuran-2-yl-methyl, Tetrahydrofuran-3-ylmethyl, Tetrahydropyran-2-ylmethyl, Tetrahydropyran-3-ylmethyl, Tetrahydropyran-4-ylmethyl, Methylpropionate-3-yl, Ethylpropionate-3-yl, Methylacetyl-2-yl, Ethylacetyl-2-yl, Methylneoplastate-2-yl, Ethylneoplastate-3-yl, Methyl-2-methylpropionate-3-yl, Methyl-2,2-dimethylpropionate-3-yl, Ethyl-2-methylpropionate-3-yl, Methyl-2-propionate-2-yl, Ethyl-2-propionate

[0364] -2-yl, methyl acetate-2-yl, ethyl acetate-2-yl, methyl-1-methylcyclopropane carboxylate-2-yl, ethyl-1-methylcyclopropane carboxylate-2-yl, 2-(dimethylamino)ethyl, oxetane-3-yl, (3-methyloxetane-3-yl)methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-

[0365] 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-phenylpropyne

[0366] -2-ynyl-1-yl, 3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl

[0367] 2-methylprop-2-en-1-yl, but-2-en-1-yl, methylprop-2-en-1-yl

[0368] But-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-

[0369] 1-(2E)-1-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-

[0370] Dioxacyclopentane-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl.

[0371] The following compounds are not included:

[0372] {[5-(4-methoxyphenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS [1310875-73-0])

[0373] {[5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS [1310875-75-2])

[0374] {[5-(3-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS [1310875-76-3])

[0375] {[5-(3-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-77-4])

[0376] {[5-(4-methoxyphenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-85-4])

[0377] {[5-(4-fluorophenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076207-91-4])

[0378] [(1,5-Diphenyl-1H-pyrazol-3-yl)oxy]acetic acid (CAS[73457-62-2])

[0379] Sodium [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetate (CAS[73457-94-0])

[0380] {[5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid (CAS [1310875-74-1])

[0381] {[5-(4-bromophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076207-89-0])

[0382] {[1,5-bis(4-fluorophenyl)-1H-pyrazole-3-yl]oxy}acetic acid (CAS[1076208-05-3])

[0383] {[5-(4-chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-79-6])

[0384] {[1-(4-fluorophenyl)-5-(4-methoxyphenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076208-00-8])

[0385] [(1,5-Diphenyl-1H-pyrazol-3-yl)oxy]ethyl acetate (CAS [1246513-41-6])

[0386] {[1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazole-3-yl]oxy}acetic acid (CAS[1076207-99-2])

[0387] ({1-Phenylacetyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1076207-90-3])

[0388] Ethyl {[5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy} (CAS [1246513-42-7])

[0389] {[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076208-04-2])

[0390] {[5-(2,4-dichlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-84-3])

[0391] {[5-(4-methoxyphenyl)-1-phenyl-1H-pyrazole-3-yl]oxy}ethyl acetate (CAS [1076207-87-8])

[0392] Ethyl {[5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy} (CAS [1246513-43-8])

[0393] {[5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1246513-44-9])

[0394] Ethyl {[5-(3-chlorophenyl)-1-phenyl-1H-pyrazole-3-yl]oxy} (CAS [1338378-37-2])

[0395] Ethyl {[5-(3-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy} (CAS [1246513-46-1])

[0396] ({1-(4-chlorophenyl)-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1310875-83-2])

[0397] ({1-(4-fluorophenyl)-5-[3-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1310875-81-0])

[0398] {[5-(4-bromophenyl)-1-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS [1076208-03-1])

[0399] Ethyl {[1-(4-fluorophenyl)-5-(4-methylphenyl)-1H-pyrazol-3-yl]oxy} (CAS [1076207-98-1])

[0400] ({1-(2,4-dichlorophenyl)-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)acetic acid (CAS[1310875-86-5])

[0401] Ethyl {[1-(2,4-dichlorophenyl)-5-(4-methylphenyl)-1H-pyrazol-3-yl]oxy} (CAS [1076207-94-7])

[0402] {[5-(3,4-dimethoxyphenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (CAS[1076207-92-5])

[0403] The present invention very, extremely, particularly preferably provides compounds of general formula (I), wherein

[0404] (R 1 ) n -Phenyl is a group selected from Q-1.2 to Q-1.53.

[0405]

[0406]

[0407] and (R) 2 ) m -Phenyl is a group selected from Q-2.2 to Q-2.53.

[0408] R 3 It is hydrogen.

[0409] and

[0410] R4 For hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl,

[0411] Phenyl, benzyl, CH2(4-Cl-Ph), CH2(4-F-Ph), CH2(4-MeO-Ph)

[0412] 2-Methoxyethyl, Tetrahydrofuran-2-yl-methyl, Tetrahydrofuran-3-ylmethyl,

[0413] Tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl, methylpropionate-3-yl, ethylpropionate-3-yl, methylacetyl-2-yl

[0414] Ethylacetyl-2-yl, methylneoprolate-2-yl, ethylneoprolate-3-yl

[0415] 3-methyl-2-methylpropionate, 3-methyl-2,2-dimethylpropionate, 3-ethyl-2-methylpropionate, 2-methyl-2-propionate, ethyl-2-propionate

[0416] -2-yl, methyl acetate-2-yl, ethyl acetate-2-yl, methyl-1-methylcyclopropane carboxylate-2-yl, ethyl-1-methylcyclopropane carboxylate-2-yl, 2-(dimethylamino)ethyl, oxetane-3-yl, (3-methyloxetane-3-yl)methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-

[0417] 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-phenylpropyne

[0418] -2-ynyl-1-yl, 3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl

[0419] 2-methylprop-2-en-1-yl, but-2-en-1-yl, methylprop-2-en-1-yl

[0420] But-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-

[0421] 1-(2E)-1-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-

[0422] Dioxacyclopentane-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl

[0423] The following compounds are not included:

[0424] {[1,5-bis(4-fluorophenyl)-1H-pyrazole-3-yl]oxy}acetic acid (CAS[1076208-05-3])

[0425] {[5-(4-chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-79-6])

[0426] {[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1076208-04-2])

[0427] {[5-(2,4-dichlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (CAS[1310875-84-3])

[0428] The present invention most particularly preferably provides a compound of general formula (I), wherein

[0429] (R 1 ) n -Phenyl groups are selected from the following groups from Q-1.2 to Q-1.53:

[0430] Q-1.2, Q-1.3, Q-1.4, Q-1.5, Q-1.6, Q-1.7, Q-1.32, Q-1.33, Q-1.34, Q-1.3, Q-1.36, Q-1.37, Q-1.38, Q-1.39, Q-1.40, Q-1.41, Q-1.42, Q-1.43, Q-1.45, Q-1.46, Q-1.47, Q-1.48, Q-1.49, Q-1.50, Q-1.51, Q-1.52, Q-1.53,

[0431] (R 2 ) m -Phenyl groups are selected from the following groups from Q-2.2 to Q-2.53:

[0432] Q-2.2, Q-2.3, Q-2.5, Q-2.6, Q-2.7, Q-2.33, Q-2.34, Q-2.35, Q-2.36, Q-2.37, Q-2.38, Q-2.39, Q-2.4 0. Q-2.41, Q-2.42, Q-2.43, Q-2.45, Q-2.46, Q-2.47, Q-2.48, Q-24, Q-2.50, Q-2.51, Q-2.52, Q-2.53,

[0433] R 3 It is hydrogen.

[0434] and

[0435] R 4 The following are the compounds: hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, phenyl, benzyl, CH2(4-Cl-Ph), CH2(4-F-Ph), CH2(4-MeO-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl, methylpropionate-3-yl, ethylpropionate-3-yl, methylacetyl-2-yl, ethylacetyl-2-yl, methylneoplastate-2-yl, ethylneoplastate-3-yl, methyl-2-methylpropionate-3-yl, methyl-2,2-dimethylpropionate-3-yl, ethyl-2-methylpropionate-3-yl, methyl-2-propionate-2-yl, ethyl-2-propionate-2-yl, methyl Acetate-2-yl, Ethyl acetate-2-yl, Methyl-1-methylcyclopropanecarboxylate-2-yl, Ethyl-1-methylcyclopropanecarboxylate-2-yl, 2-(dimethylamino)ethyl, Oxycyclobutane-3-yl, (3-methyloxetane-3-yl)methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl, Cyclopropylmethyl, 1-Cyclopropylethyl, (1-methylcyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl, Allyl, Protyne (prop-2-yn-1-yl), 2-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

[0436] 2-methylprop-2-en-1-yl, but-2-en-1-yl, methylprop-2-en-1-yl

[0437] But-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-

[0438] 1-(2E)-1-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-

[0439] Dioxacyclopentane-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl.

[0440] The above general or preferred group definitions can be applied to the final product of general formula (I) and, correspondingly, to the raw materials or intermediates required for preparation in each case. These group definitions can be combined with each other as needed, i.e., combinations between given preferred ranges.

[0441] Primarily for reasons of higher herbicidal activity, better selectivity and / or better preparability, there is particular interest in compounds of general formula (I) given in this invention or salts thereof, or uses thereof in this invention, wherein each group has one of the preferred meanings described above or below, or particularly those that are a combination of one or more of the preferred meanings described above or below.

[0442] Regarding the compounds of the present invention, the terms used above and below will be clarified. These are familiar to those skilled in the art and are particularly defined as follows:

[0443] Unless otherwise defined, the name of a chemical group should generally be understood as being connected to the skeleton or the rest of the molecule by the structural element of the relevant chemical group mentioned last, i.e., by the oxygen atom in the case of (C2-C8)-olefin, and by the carbon atom of the alkyl group in the case of heterocyclic-(C1-C8)-alkyl or alkylO(O)C-(C1-C8)-alkyl.

[0444] According to the present invention, "alkylsulfonyl" – alone or as part of a chemical group – refers to a straight-chain or branched alkylsulfonyl group, preferably having 1 to 8 or 1 to 6 carbon atoms, such as (but not limited to) (C1-C6)-alkylsulfonyl groups such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropyl Sulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl, and 1-ethyl-2-methylpropylsulfonyl.

[0445] According to the present invention, "alkathioyl"—either alone or as part of a chemical group—refers to a straight-chain or branched S-alkyl group, preferably having 1 to 8 or 1 to 6 carbon atoms, for example (C1-C6). 10 (C1-C6)- or (C1-C4)-alkylthio, such as (but not limited to) (C1-C6)-alkylthio, such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio 1-Methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methylpentylthio, 1,1-dimethylbutyrothio, 1,2-dimethylbutyrothio, 1,3-dimethylbutyrothio, 2,2-dimethylbutyrothio, 2,3-dimethylbutyrothio, 3,3-dimethylbutyrothio, 1-ethylbutyrothio, 2-ethylbutyrothio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio, and 1-ethyl-2-methylpropylthio.

[0446] According to the present invention, unless otherwise defined, "alkyl sulfinyl (alkyl-S(=O)-)" means an alkyl group bonded to the skeleton by -S(=O)-, such as (C1-C6)- or (C1-C4)-alkyl sulfinyl, such as (but not limited to) (C1-C6)-alkyl sulfinyl, such as methyl sulfinyl, ethyl sulfinyl, propyl sulfinyl, 1-methylethyl sulfinyl, butyl sulfinyl, 1-methylpropyl sulfinyl, 2-methylpropyl sulfinyl, 1,1-dimethylethyl sulfinyl, pentyl sulfinyl, 1-methylbutyl sulfinyl, 2-methylbutyl sulfinyl, 3-methylbutyl sulfinyl, 1,1-dimethylpropyl sulfinyl, 1,2-dimethylpropyl sulfinyl 2,2-Dimethylpropylsulfinyl, 1-Ethylpropylsulfinyl, Hexylsulfinyl, 1-Methylpentylsulfinyl, 2-Methylpentylsulfinyl, 3-Methylpentylsulfinyl, 4-Methylpentylsulfinyl, 1,1-Dimethylbutylsulfinyl, 1,2-Dimethylbutylsulfinyl, 1,3-Dimethylbutylsulfinyl, 2,2-Dimethylbutylsulfinyl, 2,3-Dimethylbutylsulfinyl, 3,3-Dimethylbutylsulfinyl, 1-Ethylbutylsulfinyl, 2-Ethylbutylsulfinyl, 1,1,2-Trimethylpropylsulfinyl, 1,2,2-Trimethylpropylsulfinyl, 1-Ethyl-1-Methylpropylsulfinyl and 1-Ethyl-2-Methylpropylsulfinyl.

[0447] "Alkoxy" refers to an alkyl group linked by an oxygen atom, such as (but not limited to) (C1-C6) alkoxy groups, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, etc. 1-Methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, and 1-ethyl-2-methylpropoxy. Alkenyloxy groups represent alkenyl groups linked by oxygen atoms, and alkynyloxy groups represent alkynyl groups linked by oxygen atoms, for example (C2-C...). 10 )-, (C2-C6)- or (C2-C4)-olefin and (C3-C6)- or (C3-C4)-alkynyloxy.

[0448] According to the present invention, unless otherwise defined, "alkyl carbonyl" (alkyl-C(=O)-) means an alkyl group bonded to the skeleton by -C(=O)-, for example (C1-C... 10 (C1-C6)- or (C1-C4)-alkylcarbonyl. The number of carbon atoms here is related to the alkyl group in the alkylcarbonyl group.

[0449] Unless otherwise defined, "alkoxycarbonyl (alkyl-OC(=O)-)" refers to an alkyl group bonded to the skeleton via -OC(=O)-, such as (C1-C 10 (C1-C6)- or (C1-C4)-alkoxycarbonyl. The number of carbon atoms here is related to the alkyl group in the alkoxycarbonyl group. Similarly, according to the present invention, unless otherwise defined, "alkenoxycarbonyl" and "alkynoxycarbonyl" refer to alkenyl and alkynyl groups bonded to the skeleton by -OC (=O)-, such as (C2-C4)-alkoxycarbonyl. 10 )-, (C2-C6)- or (C2-C4)-olefin carbonyl and (C3-C 10 (C3-C6)- or (C3-C4)-alkynoxycarbonyl. The number of carbon atoms here is related to the alkenyl or alkynyl group in the alkenyloxycarbonyl or alkynoxycarbonyl group.

[0450] The term "aryl" refers to an optionally substituted monocyclic, bicyclic, or polycyclic aromatic system, preferably having 6 to 14, particularly 6 to 10, cyclic carbon atoms, such as phenyl, naphthyl, anthracene, phenanthryl, etc., with phenyl being the most preferred.

[0451] The term "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 covered by the term "optionally substituted phenyl." Preferred aryl substituents herein are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclic, heterocyclic alkyl, alkoxyalkyl, alkylthio, haloalkylthio, haloalkyl, alkoxy, haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, dialkylaminoalkoxy, tri[alkyl]silyl, di[alkyl]arylsilyl, Di[alkyl]alkylsilyl, Tri[alkyl]silylynyl, Alkylynyl, Cycloalkylynyl, Halogenated Alkylynyl, Heterocyclic -N-alkoxy, Nitro, Cyano, Amino, Alkylamino, Dialkylamino, Alkylcarbonylamino, Cycloalkylcarbonylamino, Arylcarbonylamino, Alkoxycarbonylamino, Alkoxycarbonylalkylamino, Arylalkoxycarbonylalkylamino, Hydroxylcarbonyl, Alkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Cycloalkylaminocarbonyl, Dialkylaminocarbonyl, Heteroarylalkoxy, Arylalkoxy.

[0452] A heterocyclic group (heterocyclic group) comprises at least one heterocycle (= carbocyclic ring, wherein 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, wherein, in the case of substitution, the bonding site is located on a ring atom. If the heterocyclic group or heterocycle is optionally substituted, it may be fused with other carbocyclic rings or heterocycles. In the case of optionally substituted heterocyclic groups, polycyclic systems are also included, such as 8-azabicyclo[3.2.1]octyl, 8-azabicyclo[2.2.2]octyl, or 1-azabicyclo[2.2.1]heptyl. Optionally substituted heterocyclic groups also include spirocyclic systems, such as 1-oxa-5-azaspiro[2.3]hexyl. Unless otherwise defined, heterocycles preferably contain 3 to 9 ring atoms, particularly 3 to 6 ring atoms, and may contain one or more, preferably 1 to 4, particularly 1, 2 or 3 heteroatoms, preferably selected from N, O and S, but should not have two oxygen atoms directly adjacent to each other, for example containing 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-yl 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 Azinyl-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-azepin-1- or 2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,4,7-tetrahydro-1H-azepin-1- or 2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,6,7-Tetrahydro-1H-azapheno-1-or-2-or-3-or-4-yl, 3,4,5,6-Tetrahydro-2H-azapheno-2-or-3-or-4-or-5-or-6-or-7-yl, 4,5-Dihydro-1H-azapheno-1-or-2-or-3-or-4-yl, 2,5-Dihydro-1H-azapheno-1-or-2-or-3-or-4-or-5-or-6-or-7-yl, 2,7-Dihydro-1H-azapheno-1-or-2-or-3-or-4-yl, 2,3-Dihydro-1H-azaphene-1-or-2-or-3-or-4-or-5-or-6-or-7-yl, 3,4-Dihydro-2H-azaphene-2-or-3-or-4-or-5-or-6-or-7-yl, 3,6-Dihydro-2H-azaphene-2-or-3-or-4-or-5-or-6-or-7-yl, 5,6-Dihydro-2H-azaphene-2-or-3-or-4-or-5-or-6-or-7-yl, 4,5-Dihydro-3H-azaphene-2-or-3-or-4-or-5-or-6-or-7-yl, 1H-azaphene-1-or-2-or-3-or-4-or-5-or-6-or-7-yl, 2H- Azaphen-2- or 3- or 4- or 5- or 6- or 7-yl, 3H-azaphen-2- or 3- or 4- or 5- or 6- or 7-yl, 4H-azaphen-2- or 3- or 4- or 5- or 6- or 7-yl, 2- or 3-oxacyclopentyl (=2- or 3-tetrahydrofuranyl), 2,3-dihydrofuran-2- or 3- or 4- or 5-yl, 2,5-dihydrofuran-2- or 3-yl, 2- or 3- or 4-oxacyclohexyl (=2- or 3- or 4-tetrahydropyranyl), 3,4-dihydro-2H-pyran-2- or 3- or 4- or 7-yl 5- or -6-yl, 3,6-dihydro-2H-pyran-2- or -3- or -4- or -5- or -6-yl, 2H-pyran-2- or -3- or -4- or -5- or -6-yl, 4H-pyran-2- or -3- or -4-yl, 2- or -3- or -4-oxepanyl, 2,3,4,5-tetrahydrooxepin-2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,4,7-tetrahydrooxepin-2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,6,7-tetrahydrooxepin-2- or -3- or -4-yl - 2,3-dihydrooxopheno-2- or -3- or -4- or -5- or -6- or -7-yl, 4,5-dihydrooxopheno-2- or -3- or -4-yl, 2,5-dihydrooxopheno-2- or -3- or -4- or -5- or -6- or -7-yl, oxopheno-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-aziridinyl, 2- or 3-oxetane, 2- or 3-thietanyl, and 1,3-dioxetane-2-yl. Other examples of "heterocyclic groups" are partially or fully hydrogenated heterocyclic groups having two heteroatoms 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 groups, and 2,5-dihydro-1H-imidazolyl groups. -1- or 2- or 4- or 5-yl, 4,5-dihydro-1H-imidazol-1- or 2- or 4- or 5-yl, hexahydropyridazine-1- or 2- or 3- or 4-yl, 1,2,3,4-tetrahydropyridazine-1- or 2- or 3- or 4- or 5- or 6-yl, 1,2,3,6-tetrahydropyridazine-1- or 2- or 3- or 4- or 5- or 6-yl, 1,4,5,6-tetrahydropyridazine-1- or 3- or 4- or 5- or 6-yl, 3,4,5,6-tetrahydropyridazine-3- or 4- or 5-yl, 4,5-dihydropyridazine-3- or 4-yl, 3 4-Dihydropyridazine-3, 4, 5, or 6-yl, 3,6-Dihydropyridazine-3, 4-yl, 1,6-Dihydropyridazine-1, 3, 4, 5, or 6-yl, Hexahydropyrimidine-1, 2, 3, or 4-yl, 1,4,5,6-Tetrahydropyrimidine-1, 2, 5,6-Tetrahydropyrimidine-1, 2, 4, 5, or 6-yl, 1,2,3,4-Tetrahydropyrimidine-1, 2, 3,4-Tetrahydropyrimidine-1, 2, 3, 4, 5, or 6-yl, 1,6-Dihydropyrimidine-1, 2, 4, 5, or 6-yl -yl, 1,2-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl, 2,5-dihydropyrimidin-2- or 4- or 5-yl, 4,5-dihydropyrimidin-4- or 5- or 6-yl, 1,4-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl, 1- or 2- or 3-piperazinyl, 1,2,3,6-tetrahydropyrazine-1- or 2- or 3- or 5- or 6-yl, 1,2,3,4-tetrahydropyrazine-1- or 2- or 3- or 4- or 5- or 6-yl, 1,4-Dihydropyrazin-1- or 2- or 3-yl, 2,3-Dihydropyrazin-2- or 3- or 5- or 6-yl, 2,5-Dihydropyrazin-2- or 3-yl, 1,3-Dioxol-2- or 4- or 5-yl, 1,3-Dioxol-2- or 4- or 5-yl, 4H-1,3-Dioxin-2- or 4- or 5- or 6-yl, 1,4-Dioxane-2- or 3- or 5- or 6-yl, 2,3-Dihydro-1,4-Dioxin-2- or 3- or 5- or 6-yl, 1,4-Dioxin-2- or 3-yl, 1,2-Dithiolan-3- or 4-yl, 3H -1,2-Dithiol-3-or-4-or-5-yl, 1,3-Dithiol-2-or-4-yl, 1,3-Dithiol-2-or-4-yl, 1,2-Dithiacol-3-or-4-yl, 3,4-Dihydro-1,2-Dithiain-3-or-4-or-5-or-6-yl, 3,6-Dihydro-1,2-Dithiain-3-or-4-yl, 1,2-Dithiain-3-or-4-yl, 1,3-Dithiacol-2-or-4-or-5-yl, 4H-1,3-Dithiain-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 -or 5-yl, 4,5-dihydroisoxazol-3-or 4-or 5-yl, 1,3-oxazolidine-2-or 3-or 4-or 5-yl, 2,3-dihydro-1,3-oxazol-2-or 3-or 4-or 5-yl, 2,5-dihydro-1,3-oxazol-2-or 4-or 5-yl, 4,5-dihydro-1,3-oxazol-2-or 4-or 5-yl, 1,2-oxazinan-2-or 3-or 4-or 5-or 6-yl, 3,4-dihydro-2H-1,2-oxazin-2-or 3-or 4-or 5-or 6-yl, 3,6-dihydro-2H-1,2-oxazin-2-or 3-or 4-or 5-or 6-yl, 5,6-dihydro-2H-1,2-oxazin-2-or 3-or 4-or 5-or 6-yl 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-oxazine-2- or 4- or 5- or 6-yl, 5,6-dihydro-4H-1,3-Oxazin-2- or 4- or 5- or 6-yl, 2H-1,3-Oxazin-2- or 4- or 5- or 6-yl, 6H-1,3-Oxazin-2- or 4- or 5- or 6-yl, 4H-1,3-Oxazin-2- or 4- or 5- or 6-yl, morpholin-2- or 3- or 4-yl, 3,4-dihydro-2H-1,4-Oxazin-2- or 3- or 4- or 5- or 6-yl, 3,6-dihydro-2H-1,4-Oxazin-2- or 3- or 5- or 6-yl, 2H-1,4-Oxazin-2- or 3- or 5- or 6-yl, 4H-1,4-Oxazin-2- or 3-yl, 1,2-oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,4 5-Tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,4,7-Tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,6,7-Tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl, 2,5,6,7-Tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl, 4,5,6,7-Tetrahydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl, 2,3-Dihydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl, 2,5-Dihydro-1,2-oxazepin-2- 3- or 4- or 5- or 6- or 7-yl, 2,7-dihydro-1,2-oxadiazophen-2- or 3- or 4- or 5- or 6- or 7-yl, 4,5-dihydro-1,2-oxadiazophen-3- or 4- or 5- or 6- or 7-yl, 4,7-dihydro-1,2-oxadiazophen-3- or 4- or 5- or 6- or 7-yl, 6,7-dihydro-1, 2-Oxazapyro-3-or-4-or-5-or-6-or-7-yl, 1,2-Oxazapyro-3-or-4-or-5-or-6-or-7-yl, 1,3-Oxazapyro-2-or-3-or-4-or-5-or-6-or-7-yl, 2,3,4,5-Tetrahydro-1,3-Oxazapyro-2-or-3-or-4-or-5-or-6-or-7-yl, 2,3,4,7- Tetrahydro-1,3-oxazaporphyrin-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,6,7-tetrahydro-1,3-oxazaporphyrin-2- or 3- or 4- or 5- or 6- or 7-yl, 2,5,6,7-tetrahydro-1,3-oxazaporphyrin-2- or 4- or 5- or 6- or 7-yl, 4,5,6,7-tetrahydro-1,3-oxazaporphyrin Zoro-2- or 4- or 5- or 6- or 7-yl, 2,3-dihydro-1,3-oxadiazo-2- or 3- or 4- or 5- or 6- or 7-yl, 2,5-dihydro-1,3-oxadiazo-2- or 4- or 5- or 6- or 7-yl, 2,7-dihydro-1,3-oxadiazo-2- or 4- or 5- or 6- or 7-yl, 4,5-dihydro-1,3-Oxazapyro-2- or 4- or 5- or 6- or 7-yl, 4,7-dihydro-1,3-oxazapyro-2- or 4- or 5- or 6- or 7-yl, 6,7-dihydro-1,3-oxazapyro-2- or 4- or 5- or 6- or 7-yl, 1,3-oxazapyro-2- or 4- or 5- or 6- or 7-yl, 1,4-oxazapyro-2- or 3- or 5- or 6- or 7-yl, 2,3,4,5-tetrahydro-1,4-oxazapyro-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,4,7-tetrahydro-1,4-oxazapyro-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3,6 ... Zoro-2- or 3- or 5- or 6- or 7-yl, 2,5,6,7-tetrahydro-1,4-oxaazazo-2- or 3- or 5- or 6- or 7-yl, 4,5,6,7-tetrahydro-1,4-oxaazazo-2- or 3- or 4- or 5- or 6- or 7-yl, 2,3-dihydro-1,4-oxaazazo-2- or 3- or 5- or 6- or 7-yl, 2,5-dihydro-1,4-oxaazazo-2- or 3- or 5- or 6- or 7-yl, 2,7-dihydro-1,4-oxaazazo-2- or 3- or 5- or 6- or 7-yl, 4,5-dihydro-1,4-oxaazazo-2- or 3- or 4- or 5- or 6- or 7-yl, 4,7 ... Azazolide-2-or-3-or-4-or-5-or-6-or-7-yl, 6,7-dihydro-1,4-oxazazolide-2-or-3-or-5-or-6-or-7-yl, 1,4-oxazazolide-2-or-3-or-5-or-6-or-7-yl, isothiazolidine-2-or-3-or-4-or-5-yl, 2,3-dihydroisothiazolide-2-or-3-or-4-or-5-yl, 2,5-dihydroisothiazolide-2-or-3-or-4-or-5-yl, 4,5-dihydroisothiazolide-3-or-4-or-5-yl, 1,3-thiazolide-2-or-3-or-4-or-5-yl, 2,3-dihydro-1,3-thiazolide-2-or-3-or-4-or-5-yl, 2,5-dihydro-1,3-thiazolide-2-or-4-or-5-yl 4,5-Dihydro-1,3-thiazol-2- or 4- or 5-yl, 1,3-thiazinan-2- or 3- or 4- or 5- or 6-yl, 3,4-dihydro-2H-1,3-thiazinan-2- or 3- or 4- or 5- or 6-yl, 3,6-dihydro-2H-1,3-thiazinan-2- or 3- or 4- or 5- or 6-yl, 5,6-dihydro-2H-1,3-thiazinan-2- or 4- or 5- or 6-yl, 5,6-dihydro-4H-1,3-thiazinan-2- or 4- or 5- or 6-yl, 2H-1,3-thiazinan-2- or 4- or 5- or 6-yl, 6H-1,3-thiazinan-2- or 4- or 5- or 6-yl, 4H-1,3-Thiazine-2-, 4-, 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-, 3-, or 5-yl, 1,4,2-dioxazolidine-3-, or 5-yl, 1,4,2-dioxazine-2-, 3-, 5-, or 6-yl, 5,6-dihydro-1,4,2-dioxazine-3-, 5-, or 6-yl, 1,4,2-dioxazine-3-, 5-, or 6-yl, 1,4,2-dioxazine-3-, 5-, or 6-yl, 1,4,2-dioxazine-2-, 3-, or 5-yl, and 1,4,2-dioxazine-2-, 3-, or 5-yl. Or 6- or 7-yl, 6,7-dihydro-5H-1,4,2-dioxadiazepto-3- or 5- or 6- or 7-yl, 2,3-dihydro-7H-1,4,2-dioxadiazepto-2- or 3- or 5- or 6- or 7-yl, 2,3-dihydro-5H-1,4,2-dioxadiazepto-2- or 3- or 5- or 6- or 7-yl, 5H-1,4,2-dioxadiazepto-3- or 5- or 6- or 7-yl, 7H-1,4,2-dioxadiazepto-3- or 5- or 6- or 7-yl. Structural examples of optionally further substituted heterocycles are also listed below:

[0453]

[0454]

[0455]

[0456] The heterocycles listed above are preferably substituted with the following groups: for example, hydrogen, halogen, alkyl, haloalkyl, hydroxyl, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclic, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, trialkylsilylalkynyl, nitro, amino, cyano. Halogenated alkoxy, halogenated alkylthio, alkylthio, hydrogen thio, hydroxyalkyl, oxo, heteroarylalkoxy, arylalkoxy, heterocyclic alkoxy, heterocyclic alkylthio, heterocyclic alkylthio, heterocyclic thio, heteroaryloxy, dialkylamino, alkylamino, cycloalkylamino, hydroxycarbonylalkylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, alkoxycarbonylalkyl(alkyl)amino, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, cycloalkylaminocarbonyl, hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl, arylalkoxycarbonylalkylaminocarbonyl.

[0457] When the basic structure is replaced by "one or more groups" selected from a list (= group) of groups or a group of groups as generally defined, in each case this includes being replaced by multiple identical and / or structurally different groups simultaneously.

[0458] In the case of partially or fully saturated nitrogen heterocycles, this can be attached to the rest of the molecule via carbon or nitrogen.

[0459] Suitable substituents for the substituted heterocyclic group are those further specified below, as well as oxo and thio groups. The oxo group, then, as a substituent on the ring carbon atom, is, for example, a carbonyl group in the heterocycle. Therefore, lactones and lactams are preferably also included. The oxo group can also appear on the ring heteroatom, which can exist in different oxidation states, for example in the cases of N and S, and in this case, divalent -N(O)-, -S(O)- (also simply SO), and -S(O)2- (also simply SO2) groups are formed in the heterocycle. In the cases of -N(O)- and -S(O)- groups, both enantiomers are included in each case.

[0460] According to the present invention, the term "heteroaryl" refers to a heteroaromatic compound, that is, a fully unsaturated aromatic heterocyclic compound, preferably having 1 to 4 (preferably 1 or 2) identical or different heteroatoms (preferably O, S or N) 5- to 7-membered rings.The heteroaryl groups of the present invention are, for example, 1H-pyrrolo-1-yl, 1H-pyrrolo-2-yl, 1H-pyrrolo-3-yl, furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, 1H-imidazol-1-yl, 1H-imidazol-2-yl, 1H-imidazol-4-yl, 1H-imidazol-5-yl, 1H-pyrazole-1-yl, 1H-pyrazole-3-yl, 1H-pyrazole-4-yl, 1H-pyrazole-5-yl, 1H-pyrazole-1-yl, 1H-pyrazole-3-yl, 1H-pyrazole-4-yl, 1H-pyrazole-5-yl, 1H-1,2,3-triazol-1-yl, 1H-1,2,3-triazol-4-yl, 1H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H -1,2,4-triazol-1-yl, 1H-1,2,4-triazol-3-yl, 4H-1,2,4-triazol-4-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,5-oxadiazol-3-yl, aziridine, 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-Triazine-5-yl, 1,2,4-Triazine-6-yl, 1,2,3-Triazine-4-yl, 1,2,3-Triazine-5-yl, 1,2,4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 1,3-oxazol-2-yl, 1,3-oxazol-4-yl, 1,3-oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,3-thiazole-2-yl, 1,3-thiazole-4-yl, 1,3-thiazole-5-yl, 1,3,4-thiadiazole-2-yl, 1,3,4-thiadiazole-5-yl, 1,2,4-thiadiazole -5-yl, 1,2,4-thiadiazole-3-yl, 1,2,5-thiadiazole-3-yl, 1,2,5-thiadiazole-3-yl, 1,2,3-thiadiazole-4-yl, 1,2,3-thiadiazole-5-yl, oxazophenyl, thiepinyl, 1,2,4-triazoloneyl, and 1,2,4-diazazophenyl, 2H-1,2,3,4-tetrazol-5-yl, 1H-1,2,3,4-tetrazol-5-yl, 1,2,3,4-oxatriazole-5-yl, 1,2,3,4-thiatriazole-5-yl, 1,2,3,5-oxatriazole-4-yl, 1,2,3,5-thiatriazole-4-yl. The heteroaryl groups of the present invention can also be substituted with one or more identical or different groups.If two adjacent carbon atoms are part of another aromatic ring, the system is a fused heteroaromatic system, such as benzofused or polyannelated heteroaromatic compounds. Preferred examples are quinolines (e.g., quinoline-2-yl, quinoline-3-yl, quinoline-4-yl, quinoline-5-yl, quinoline-6-yl, quinoline-7-yl, quinoline-8-yl), isoquinolines (e.g., isoquinoline-1-yl, isoquinoline-3-yl, isoquinoline-4-yl, isoquinoline-5-yl, isoquinoline-6-yl, isoquinoline-7-yl, isoquinoline-8-yl), quinoxaline, 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 also include 5- or 6-membered benzo[a]-fused rings selected from the following: 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.

[0461] 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.

[0462] According to the present invention, "alkyl" means a straight-chain or branched open-chain saturated hydrocarbon group, which is optionally monosubstituted or polysubstituted, and in the latter case is referred to as "substituted alkyl". Preferred substituents are halogen atoms, alkoxy groups, haloalkoxy groups, cyano groups, alkylthio groups, haloalkoxythio groups, cycloalkyl groups, alkoxycarbonyl groups, hydroxycarbonyl groups, heterocyclic groups, heteroaryl groups, aryl groups, amino groups, or nitro groups, with methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine, or iodine groups being particularly preferred. The prefix "di" also includes combinations of different alkyl groups, such as methyl (ethyl) or ethyl (methyl).

[0463] "Haloalkyl", "haloalkenyl", and "haloalkynyl" respectively refer to alkyl, alkenyl, and alkynyl groups that are partially or completely substituted with the same or different halogen atoms. Examples include monohaloalkyl groups such as CH2CH2Cl, CH2CH2Br, CHClCH3, CH2Cl, and CH2F; perhaloalkyl groups such as CCl3, CClF2, CFCl2, CF2CClF2, and CF2CClFCF3; and polyhaloalkyl groups such as CH2CHFCl, CF2CClFH, CF2CBrFH, and CH2CF3. The term perhaloalkyl also includes the term perfluoroalkyl.

[0464] "Haloalkoxy" is, for example, OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 and OCH2CH2Cl; this applies accordingly to haloalkenyl and other halogen-substituted groups.

[0465] The term "(C1-C4)-alkyl" as used by way of example herein is an abbreviation for a straight-chain or branched alkyl group having 1 to 4 carbon atoms according to the stated carbon atom range, including methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl, or tert-butyl groups. General alkyl groups having a larger specified carbon atom range, such as "(C1-C6)-alkyl," correspondingly also include straight-chain or branched alkyl groups having more carbon atoms, i.e., according to examples, also including alkyl groups having 5 and 6 carbon atoms.

[0466] 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.

[0467] 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, for example, vinyl groups optionally substituted with other alkyl groups, such as (but not limited to) (C2-C6)-alkenyl groups, such as vinyl, 1-propenyl, 2-propenyl, 1-methylvinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3- Methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl 4-Methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2 2-Dimethyl-3-butenyl, 2,3-Dimethyl-1-butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3-Dimethyl-1-butenyl, 3,3-Dimethyl-2-butenyl, 1-Ethyl-1-butenyl, 1-Ethyl-2-butenyl, 1-Ethyl-3-butenyl, 2-Ethyl-1-butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, 1,1,2-Trimethyl-2-propenyl, 1-Ethyl-1-methyl-2-propenyl, 1-Ethyl-2-methyl-1-propenyl and 1-Ethyl-2-methyl-2-propenyl.

[0468] The term "alkynyl" also specifically includes straight-chain or branched open-chain hydrocarbon groups that have more than one triple bond, or have one or more triple bonds and one or more double bonds, such as 1,3-buttrienyl or 3-pent-1-yn-1-yl. (C2-C6)-alkynyl groups 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.

[0469] The term "cycloalkyl" refers to a carbocyclic saturated ring system, preferably having 3 to 8 ring carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl, which is optionally further substituted, preferably substituted with the following groups: hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, dialkylamino, alkoxycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, and cycloalkylaminocarbonyl. In the case of optionally substituted cycloalkyl groups, this includes ring systems with substituents, and also includes substituents having a double bond on the cycloalkyl group, such as alkylene groups, like methylene. In the case of optionally substituted cycloalkyl groups, polycyclic aliphatic systems are also included, such as bicyclo[1.1.0]but-1-yl, bicyclo[1.1.0]but-2-yl, bicyclo[2.1.0]pent-1-yl, bicyclo[1.1.1]pent-1-yl, bicyclo[2.1.0]pent-2-yl, bicyclo[2.1.0]pent-5-yl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]hept-2-yl, bicyclo[2.2.2]oct-2-yl, bicyclo[3.2.1]oct-2-yl, bicyclo[3.2.2]non-2-yl, adamantane-1-yl and adamantane-2-yl, as well as systems such as 1,1'-di(cyclopropyl)-1-yl and 1,1'-di(cyclopropyl)-2-yl. The term "(C3-C7)-cycloalkyl" is an abbreviation for cycloalkyl groups having 3 to 7 carbon atoms within a specified range of carbon atoms.

[0470] 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.

[0471] "Cycloalkenyl" preferably refers to a non-aromatic, partially unsaturated cyclic system having a carbon ring with 4 to 8 carbon atoms, such as 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1,4-cyclohexadienyl, and also includes substituents having a double bond on the cycloalkenyl group, such as alkylene groups, like methylene groups. In the case of optionally substituted cycloalkenyl groups, the description of substituted cycloalkyl groups applies accordingly.

[0472] The term "alkylene", for example, also refers to (C1-C 10 The alkylene group () represents 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 ...

[0473] =CH-CH3, =C(CH3)-CH3, =C(CH3)-C2H5, or =C(C2H5)-C2H5. Cycloalkylene groups represent carbocyclic groups bonded by double bonds.

[0474] "Alkoxyalkyl" refers to an alkoxy group bonded by an alkyl group, and "alkoxyalkyl" refers to an alkoxyalkyl group bonded by an oxygen atom, such as (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, and methoxypropoxy.

[0475] "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.

[0476] “Cycloalkylalkyl” means a cycloalkyl group bonded by an alkyl group, such as (but not limited to) cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropylethyl-1-yl, 2-cyclopropylethyl-1-yl, 1-cyclopropylpropyl-1-yl, 3-cyclopropylpropyl-1-yl.

[0477] According to the present invention, “haloalkylthio” – either on its own or as part of a chemical group – preferably refers to a straight-chain or branched S-haloalkyl group having 1 to 8 or 1 to 6 carbon atoms, such as (C1-C8)-, (C1-C6)- or (C1-C4)-haloalkylthio, such as (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroethyl-1-ylthio, 2,2,2-difluoroethyl-1-ylthio, 3,3,3-propyl-1-ylthio.

[0478] "Halocycloalkyl" refers to a cycloalkyl or cycloalkenyl group that is partially or completely substituted with the same or different halogen atoms (e.g., F, Cl, and Br) or halogenated alkyl groups (e.g., trifluoromethyl or difluoromethyl), such as 1-fluorocyclopropyl-1-yl, 2-fluorocyclopropyl-1-yl, 2,2-difluorocyclopropyl-1-yl, 1-fluorocyclobutyl-1-yl, 1-trifluoromethylcyclopropyl-1-yl, 2-trifluoromethylcyclopropyl-1-yl, 1-chlorocyclopropyl-1-yl, 2-chlorocyclopropyl-1-yl, 2,2-dichlorocyclopropyl-1-yl, and 3,3-difluorocyclobutyl.

[0479] If a compound can form tautomers whose structures are not formally covered by general formula (I) through hydrogen transposition, such tautomers are still included in the definition of compounds of general formula (I) of this invention, unless a specific tautomer is under investigation. For example, many carbonyl compounds can exist in ketone form and enol form, both of which are included in the definition of compounds of general formula (I).

[0480] Compounds of general formula (I) can exist as stereoisomers, depending on the nature of the substituents and their linkage. Possible stereoisomers defined by their specific three-dimensional forms, such as enantiomers, diastereomers, Z-isomers, and E-isomers, are all covered by general formula (I). For example, diastereomers (Z-isomers) may occur if one or more alkenyl groups are present. For example, enantiomers and diastereomers may occur if one or more asymmetric carbon atoms are present. Stereoisomers can be obtained from mixtures obtained during preparation processes using conventional separation methods. Analytical-grade chromatographic separation can be performed to detect enantiomer or diastereomer excesses, or preparative-grade chromatographic separation can be performed to prepare test samples for bioassays. Stereoisomers can also be selectively prepared by stereoselective reactions using optically active raw materials and / or auxiliaries. Therefore, the present invention also relates to all stereoisomers covered by general formula (I) but not shown in their specific stereoisomer forms, and mixtures thereof.

[0481] If the compound is obtained in solid form, it can also be purified by recrystallization or digestion. If a single compound (I) cannot be obtained satisfactorily by the following methods, it can be prepared by derivatization of other compounds (I).

[0482] Suitable methods for separation, purification, and separation of stereoisomers of compounds of general formula (I) are methods commonly known to those skilled in the art from similar cases, such as physical methods like crystallization, chromatography, particularly column chromatography and HPLC (high-performance liquid chromatography), distillation (optionally under reduced pressure), extraction, and other methods. Any remaining mixture can generally be separated by chromatographic methods, such as on a chiral solid phase. Suitable for preparations or industrial scales are methods such as crystallization, for example, crystallizing diastereomeric salts, which can be obtained from diastereomeric mixtures using optically active acids, and, if appropriate, using optically active bases (provided an acidic group is present).

[0483] Synthesis of [(1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid derivatives of general formula (I)

[0484]

[0485] The [(1,5-diphenyl-1H-pyrazol-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 3-phenylprop-2-ynetic acids or substituted cinnamic acids, corresponding substituted 3-phenylprop-2-ynetic esters or substituted cinnamic esters, and commercially available chemicals such as substituted phenylhydrazines and substituted iodobenzenes.

[0486] In the following schemes, unless a descriptive but non-restrictive definition is given, the part R of general formula (I) is... 1 R 2 R 3 R 4 m, n, and p have the meanings defined above.

[0487] 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, such as potassium carbonate. The reaction is preferably carried out in a suitable solvent, such as acetonitrile, within a temperature range of 0°C to 120°C (see Scheme 1).

[0488]

[0489] Where X = halogen and R = (C1-C4)-alkyl.

[0490] Option 1.

[0491] Compounds of general formula (II) are synthesized by amide coupling of an acid of general formula (IV) with a phenylhydrazine hydrohalide of general formula (V) followed by cyclization in the presence of coupling agents such as T3P, dicyclohexylcarbodiimide, N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide, N,N'-carbonyldiimidazole, 2-chloro-1,3-dimethylimidazole chloride, or 2-chloro-1-methylpyridine iodide (see Chemistry of Peptide Synthesis, Ed. N. Leo Benoiton, Taylor & Francis, 2006, ISBN-10: 1-57444-454-9). Polymer-supported reagents, 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 such as dichloromethane, acetonitrile, N,N-dimethylformamide, or ethyl acetate, and in the presence of a base such as triethylamine, N,N-diisopropylethylamine, or 1,8-diazabicyclo[5.4.0]undec-7-ene (see Scheme 2). For T3P coupling conditions, see Organic Process Research & Development 2009, 13, 900-906. As an alternative to the phenylhydrazine hydrohalide of general formula (V), the corresponding substituted phenylhydrazine (VI) can be used in the reaction.

[0492]

[0493] X = Halogen.

[0494] Option 2.

[0495] The synthesis of compounds of general formula (IV) can be carried out by reacting compounds of general formula (VII) with propargyl acid (VIII) in the presence of a suitable transition metal catalyst, particularly palladium catalysts, such as palladium(O)tetra(triphenylphosphine) or palladium diacetate or bis(triphenylphosphine)palladium(II) dichloride, or nickel catalysts such as nickel acetylacetonate (II) or bis(triphenylphosphine) nickel(II) chloride, preferably at high temperatures in an organic solvent such as 1,2-dimethoxyethane or N,N-dimethylformamide (Scheme 3). The “M” group represents, for example, magnesium, zinc, lithium or sodium. Cross-coupling methods are generally suitable, as described in R.D. Larsen, Organometallics in Process Chemistry 2004 Springer Verlag, I. Tsuji, Palladium Reagents and Catalysts 2004 Wiley, and M. Beller, C. Bolm, Transition Metals for Organic Synthesis 2004 VCH-Wiley. Other suitable synthetic methods are described in Chem. Rev. 2006, 106, 2651; Platinum Metals Review, 2009, 53, 183; Platinum Metals Review 2008, 52, 172 and Acc. Chem. Res. 2008, 41, 1486.

[0496]

[0497] Option 3.

[0498] The synthesis of acids of general formula (IX) can be carried out by hydrolysis of compounds of general formula (Ia) using methods known to those skilled in the art, as shown in Scheme 4 below. Hydrolysis can be carried out in the presence of a base or a Lewis acid. The base can be a hydroxide salt of an alkali metal (e.g., lithium, sodium, or potassium), and the hydrolysis reaction is preferably carried out in a temperature range from room temperature to 100°C. The Lewis acid can be boron tribromide, and the reaction can be carried out in a temperature range from -20°C to 100°C, preferably from -5°C to 50°C.

[0499]

[0500] Where R = (C1-C4)-alkyl

[0501] Option 4.

[0502] The compounds of general formula (X) of the present invention are synthesized by esterification of an acid of general formula (IX) with an alcohol of general formula (XI) in the presence of a coupling agent such as T3P, dicyclohexylcarbodiimide, N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide, N,N'-carbonyldiimidazole, 2-chloro-1,3-dimethylimidazole chloride, or 2-chloro-1-methylpyridine iodide (see Chemistry of Peptide Synthesis, Ed. N. Leo Benoiton, Taylor & Francis, 2006, ISBN-10: 1-57444-454-9). Polymer-supported reagents, 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 such as dichloromethane, acetonitrile, N,N-dimethylformamide, or ethyl acetate, and in the presence of a base such as triethylamine, N,N-diisopropylethylamine, or 1,8-diazabicyclo[5.4.0]undec-7-ene (see Scheme 5). For T3P coupling conditions, please refer to Organic Process Research & Development 2009, 13, 900-906.

[0503]

[0504] R′=(C1-C4)-alkyl

[0505] Option 5.

[0506] Alternatively, 3-hydroxypyrazoles of general formula (II) are synthesized by oxidation of compounds of general formula (XII) in the presence of ferric halides, such as ferric chloride (III). This reaction is preferably carried out in a suitable solvent, such as 1,2-dichloroethane, acetonitrile, N,N-dimethylformamide, or ethyl acetate, in a temperature range of 0°C to 120°C (Scheme 6).

[0507]

[0508] Option 6.

[0509] Compounds of general formula (XII) can be prepared by amide coupling of an acid of general formula (XIII) with an arylhydrazine of general formula (VI) in the presence of an amide coupling agent such as T3P, dicyclohexylcarbodiimide, N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide, N,N'-carbonyldiimidazole, 2-chloro-1,3-dimethylimidazole chloride, or 2-chloro-1-methylpyridine iodide (see Chemistry of Peptide Synthesis, Ed. N. Leo Benoiton, Taylor & Francis, 2006, ISBN-10:1-57444-454-9), followed by cyclization. Polymer-bound reagents, such as polymer-bound dicyclohexylcarbodiimide, are also suitable for this coupling reaction. The reaction is preferably carried out in a temperature range of 0°C to 80°C in a suitable solvent such as dichloromethane, acetonitrile, N,N-dimethylformamide, or ethyl acetate, and in the presence of a base such as triethylamine, N,N-diisopropylethylamine, or 1,8-diazabicyclo[5.4.0]undec-7-ene (see Scheme 7). For T3P peptide coupling conditions, please refer to Organic Process Research & Development 2009, 13, 900-906.

[0510]

[0511] Detailed synthetic examples of the compounds of the present invention of general formula (I) are given below. The referenced example numbers correspond to the numbering scheme in Tables I.1 to I.77 below. The chemical examples described in the following sections record… 1 H NMR, 13 C-NMR and 19 F-NMR spectral data ( 1 H-NMR is 400MHz 13 C-NMR at 150MHz and 19F-NMR was performed at 375 MHz using CDCl3, CD3OD, or d6-DMSO as solvents, with an internal standard of tetramethylsilane (δ = 0.00 ppm). The obtained signals were acquired on a Bruker instrument, and the listed signals have the following meanings: br = broad peak, s = singlet, d = doublet, t = triplet, dd = doublet, ddd = double doublet, m = multiplet, q = quartet, quintet, sext = sextet, sept = septet, dq = double quartet, dt = double triplet. In the case of diastereomer mixtures, significant signals for each of the two diastereomers were recorded, or the characteristic signal of the dominant diastereomer was recorded. The abbreviations used for chemical groups have 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.

[0512] Synthesis Example:

[0513] Synthesis Example Number: I.48-32

[0514] Synthesis Stage 1: 3-(4-chloro-2-fluorophenyl)-N'-(2,4-dichlorophenyl)prop-2-acetylacetylhydrazine

[0515]

[0516] 3-(4-chloro-2-fluorophenyl)propyl-2-acetylic acid (2.98 g, 15.00 mmol, 1.0 equivalent) and DMF (0.10 mL, 1.35 mmol, 0.1 equivalent) were dissolved in DCM (120 mL) and cooled to 0 °C in an ice bath. Oxygenyl chloride (2.28 g, 18.00 mmol, 1.2 equivalent) was added to the solution in portions. Note: Gas release! Subsequently, the ice bath was removed and the reaction mixture was stirred at room temperature for 1 hour. The solvent was then removed under reduced pressure and the residue was dissolved in DCM (150 mL). (2,4-Dichlorophenyl)hydrazine (5.31 g, 30 mmol, 2.0 equivalent) and triethylamine (3.04 g, 30.00 mmol, 2 equivalent) were added to the solution, and the reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was extracted with water (150 mL). The aqueous phase was extracted twice with DCM (200 mL each time). The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. 3-(4-chloro-2-fluorophenyl)-N'-(2,4-dichlorophenyl)prop-2-acetylacetylhydrazine (3.20 g, 59% of theoretical value) was isolated as a white solid. 1 H NMR (400MHz, DMSO-d) 6δ, ppm)

[0517] Synthesis Stage 2: 5-(4-chloro-2-fluorophenyl)-1-(2,4-dichlorophenyl)-1,2-dihydro-3H-pyrazole-3-one

[0518]

[0519] 3-(4-chloro-2-fluorophenyl)-N'-(2,4-dichlorophenyl)prop-2-acetylacetylhydrazine (2.86 g, 8.00 mmol, 1.0 equivalent) was dissolved in n-butanol (60 mL), and then potassium carbonate (1.66 g, 12.00 mmol, 2.0 equivalent) was added at room temperature. After about 15–30 minutes, the solution turned pink and a pale yellow solid precipitated. The reaction mixture was heated to boiling for 2 hours and cooled to room temperature, and the solvent was removed under reduced pressure. The residue was dissolved in DCM (150 mL) and water (100 mL). The organic phase was then washed with saturated sodium chloride solution and dried over sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography (ethyl acetate / heptane gradient). 5-(4-chloro-2-fluorophenyl)-1-(2,4-dichlorophenyl)-1,2-dihydro-3H-pyrazole-3-one (1.53 g, 71% of theoretical value) was isolated as a light yellow solid. 1 H NMR (400MHz, DMSO-d) 6 δ, ppm)

[0520] Synthesis Stage 3: Ethyl {[5-(4-chloro-2-fluorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy} (Synthetic Examples I.47-32)

[0521]

[0522] 1-(4-chlorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-ol (1.7 g, 5.53 mmol, 1.0 equivalent) and potassium carbonate (1.53 g, 11.05 mmol, 2 equivalent) were suspended in acetonitrile (20 mL), and then ethyl bromoacetate (0.48 g, 6.63 mmol, 1.2 equivalent) was added. The suspension was then stirred overnight at room temperature, the solids were filtered off, and the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate / heptane gradient). Ethyl {[5-(4-chloro-2-fluorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (1.62 g, 76% of theoretical value) was isolated as a colorless oil. 1 H NMR (400MHz, CDCl3δ, ppm)

[0523] Synthesis Stage 4: {[5-(4-chloro-2-fluorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}acetic acid (Synthetic Examples I.48-32)

[0524]

[0525] Methyl methyl acetate {[1-(4-chlorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (1.6 g, 4.21 mmol, 1.0 equivalent) and lithium hydroxide (101 mg, 4.21 mmol, 1 equivalent) were dissolved in a THF / water mixture (7:2, 20 mL) and stirred at room temperature for 1 h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in water and adjusted to pH 2 with 2 M hydrochloric acid, precipitating a pale yellow solid. The precipitate was filtered and dried in a vacuum oven at 55 °C. {[1-(4-chlorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid (1.44 g, 92% of theoretical value) was isolated as a pale yellow solid. 1 H NMR (400MHz, DMSO-d) 6 δ, ppm)

[0526] 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-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid derivatives, the following compounds were obtained:

[0527]

[0528] Table I.1: Preferred compounds of formula (I.1) are compounds I.1-1 to I.1-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.1-1 to I.1-53 in Table I.1 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0529] Table 1:

[0530]

[0531]

[0532]

[0533]

[0534] Table I.2: The preferred compounds of formula (I.2) are compounds I.2-1 to I.2-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.2-1 to I.2-53 in Table I.2 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0535]

[0536] Table I.3: The preferred compounds of formula (I.3) are compounds I.3-1 to I.3-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.3-1 to I.3-53 in Table I.3 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0537]

[0538] Table I.4: The preferred compounds of formula (I.4) are compounds I.4-1 to I.4-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.4-1 to I.4-53 in Table I.4 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0539]

[0540] Table I.5: The preferred compounds of formula (I.5) are compounds I.5-1 to I.5-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.5-1 to I.5-53 in Table I.5 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0541]

[0542] Table I.6: The preferred compounds of formula (I.6) are compounds I.6-1 to I.6-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.6-1 to I.6-53 in Table I.6 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0543]

[0544] Table I.7: The preferred compounds of formula (I.7) are compounds I.7-1 to I.7-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.7-1 to I.7-53 in Table I.7 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0545]

[0546] Table I.8: The preferred compounds of formula (I.8) are compounds I.8-1 to I.8-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.8-1 to I.8-53 in Table I.8 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0547]

[0548] Table I.9: The preferred compounds of formula (I.9) are compounds I.9-1 to I.9-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.9-1 to I.9-53 in Table I.9 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0549]

[0550] Table I.10: The preferred compounds of formula (I.10) are compounds I.10-1 to I.10-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.10-1 to I.10-53 of Table I.10 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0551]

[0552] Table I.11: The preferred compounds of formula (I.11) are compounds I.11-1 to I.11-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.11-1 to I.11-53 in Table I.11 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0553]

[0554] Table I.12: The preferred compounds of formula (I.12) are compounds I.12-1 to I.12-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.12-1 to I.12-53 in Table I.12 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0555]

[0556] Table I.13: The preferred compounds of formula (I.13) are compounds I.13-1 to I.13-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.13-1 to I.13-53 in Table I.13 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0557]

[0558] Table I.14: The preferred compounds of formula (I.14) are compounds I.14-1 to I.14-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.14-1 to I.14-53 in Table I.14 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0559]

[0560] Table I.15: The preferred compounds of formula (I.15) are compounds I.15-1 to I.15-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.15-1 to I.15-53 in Table I.15 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0561]

[0562] Table I.16: The preferred compounds of formula (I.16) are compounds I.16-1 to I.16-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.16-1 to I.16-53 in Table I.16 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0563]

[0564] Table I.17: The preferred compounds of formula (I.17) are compounds I.17-1 to I.17-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.17-1 to I.17-53 in Table I.17 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0565]

[0566] Table I.18: The preferred compounds of formula (I.18) are compounds I.18-1 to I.18-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.18-1 to I.18-53 in Table I.18 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0567]

[0568] Table I.19: The preferred compounds of formula (I.19) are compounds I.19-1 to I.19-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.19-1 to I.19-53 in Table I.19 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0569]

[0570] Table I.20: The preferred compounds of formula (I.20) are compounds I.20-1 to I.20-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.20-1 to I.20-53 of Table I.20 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0571]

[0572] Table I.21: The preferred compounds of formula (I.21) are compounds I.21-1 to I.21-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.21-1 to I.21-53 in Table I.21 are defined by the meaning of each entry numbered 1 to 53 of Q in Table 1.

[0573]

[0574] Table I.22: The preferred compounds of formula (I.22) are compounds I.22-1 to I.22-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.22-1 to I.22-53 of Table I.22 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0575]

[0576] Table I.23: The preferred compounds of formula (I.23) are compounds I.23-1 to I.23-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.23-1 to I.23-53 in Table I.23 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0577]

[0578] Table I.24: The preferred compounds of formula (I.24) are compounds I.24-1 to I.24-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.24-1 to I.24-53 of Table I.24 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0579]

[0580] Table I.25: The preferred compounds of formula (I.25) are compounds I.25-1 to I.25-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.25-1 to I.25-53 in Table I.25 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0581]

[0582] Table I.26: The preferred compounds of formula (I.26) are compounds I.26-1 to I.26-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.26-1 to I.26-53 of Table I.26 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0583]

[0584] Table I.27: The preferred compounds of formula (I.27) are compounds I.27-1 to I.27-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.27-1 to I.27-53 of Table I.27 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0585]

[0586] Table I.28: The preferred compounds of formula (I.28) are compounds I.28-1 to I.28-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.28-1 to I.28-53 in Table I.28 are defined by the meaning of each entry numbered 1 to 53 of Q in Table 1.

[0587]

[0588] Table I.29: The preferred compounds of formula (I.29) are compounds I.29-1 to I.29-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.29-1 to I.29-53 in Table I.29 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0589]

[0590] Table I.30: The preferred compounds of formula (I.30) are compounds I.30-1 to I.30-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.30-1 to I.30-53 of Table I.30 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0591]

[0592] Table I.31: The preferred compounds of formula (I.31) are compounds I.31-1 to I.31-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.31-1 to I.31-53 in Table I.31 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0593]

[0594] Table I.32: The preferred compounds of formula (I.32) are compounds I.32-1 to I.32-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.32-1 to I.32-53 of Table I.32 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0595]

[0596] Table I.33: The preferred compounds of formula (I.33) are compounds I.33-1 to I.33-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.33-1 to I.33-53 in Table I.33 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0597]

[0598] Table I.34: The preferred compounds of formula (I.34) are compounds I.34-1 to I.34-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.34-1 to I.34-53 of Table I.34 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0599]

[0600] Table I.35: The preferred compounds of formula (I.35) are compounds I.35-1 to I.35-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.35-1 to I.35-53 in Table I.35 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0601]

[0602] Table I.36: The preferred compounds of formula (I.36) are compounds I.36-1 to I.36-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.36-1 to I.36-53 of Table I.36 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0603]

[0604] Table I.37: The preferred compounds of formula (I.37) are compounds I.37-1 to I.37-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.37-1 to I.37-53 of Table I.37 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0605]

[0606] Table I.38: The preferred compounds of formula (I.38) are compounds I.38-1 to I.38-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.38-1 to I.38-53 in Table I.38 are defined by the meaning of each entry numbered 1 to 53 of Q in Table 1.

[0607]

[0608] Table I.39: The preferred compounds of formula (I.39) are compounds I.39-1 to I.39-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.39-1 to I.39-53 in Table I.39 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0609]

[0610] Table I.40: The preferred compounds of formula (I.40) are compounds I.40-1 to I.40-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.40-1 to I.40-53 of Table I.40 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0611]

[0612] Table I.41: The preferred compounds of formula (I.41) are compounds I.41-1 to I.41-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.41-1 to I.41-53 in Table I.41 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0613]

[0614] Table I.42: The preferred compounds of formula (I.42) are compounds I.42-1 to I.42-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.42-1 to I.42-53 of Table I.42 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0615]

[0616] Table I.43: The preferred compounds of formula (I.4) are compounds I.43-1 to I.43-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.43-1 to I.43-53 in Table I.43 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0617]

[0618] Table I.44: The preferred compounds of formula (I.44) are compounds I.44-1 to I.44-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.44-1 to I.44-53 of Table I.44 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0619]

[0620] Table I.45: The preferred compounds of formula (I.45) are compounds I.45-1 to I.45-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.45-1 to I.45-53 in Table I.45 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0621]

[0622] Table I.46: The preferred compounds of formula (I.46) are compounds I.46-1 to I.46-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.46-1 to I.46-53 of Table I.46 are defined by the meaning of each entry numbered 1 to 53 of Q in Table 1.

[0623]

[0624] Table I.47: The preferred compounds of formula (I.47) are compounds I.47-1 to I.47-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.47-1 to I.47-53 of Table I.47 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0625]

[0626] Table I.48: The preferred compounds of formula (I.48) are compounds I.48-1 to I.48-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.48-1 to I.48-53 in Table I.48 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0627]

[0628] Table I.49: The preferred compounds of formula (I.49) are compounds I.49-1 to I.49-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.49-1 to I.49-53 of Table I.49 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0629]

[0630] Table I.50: The preferred compounds of formula (I.50) are compounds I.50-1 to I.50-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.50-1 to I.50-53 of Table I.50 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0631]

[0632] Table I.51: The preferred compounds of formula (I.51) are compounds I.51-1 to I.51-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.51-1 to I.51-53 of Table I.51 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0633]

[0634] Table I.52: The preferred compounds of formula (I.52) are compounds I.52-1 to I.52-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.52-1 to I.52-53 of Table I.52 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0635]

[0636] Table I.53: The preferred compounds of formula (I.53) are compounds I.53-1 to I.53-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.53-1 to I.53-53 in Table I.53 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0637]

[0638] Table I.54: The preferred compounds of formula (I.54) are compounds I.54-1 to I.54-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.54-1 to I.54-53 of Table I.54 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0639]

[0640] Table I.55: The preferred compounds of formula (I.55) are compounds I.55-1 to I.55-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.55-1 to I.55-53 of Table I.55 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0641]

[0642] Table I.56: The preferred compounds of formula (I.56) are compounds I.56-1 to I.56-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.56-1 to I.56-53 of Table I.56 are defined by the meaning of each entry numbered 1 to 53 of Q in Table 1.

[0643]

[0644] Table I.57: The preferred compounds of formula (I.57) are compounds I.57-1 to I.57-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.57-1 to I.57-53 of Table I.57 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0645]

[0646] Table I.58: The preferred compounds of formula (I.58) are compounds I.58-1 to I.58-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.58-1 to I.58-53 of Table I.58 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0647]

[0648] Table I.59: The preferred compounds of formula (I.59) are compounds I.59-1 to I.59-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.59-1 to I.59-53 of Table I.59 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0649]

[0650] Table I.60: The preferred compounds of formula (I.60) are compounds I.60-1 to I.60-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.60-1 to I.60-53 of Table I.60 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0651]

[0652] Table I.61: The preferred compounds of formula (I.61) are compounds I.61-1 to I.61-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.61-1 to I.61-53 in Table I.61 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0653]

[0654] Table I.62: The preferred compounds of formula (I.62) are compounds I.62-1 to I.62-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.62-1 to I.62-53 of Table I.62 are defined by the meaning of each entry numbered 1 to 53 of Q in Table 1.

[0655]

[0656] Table I.63: The preferred compounds of formula (I.63) are compounds I.63-1 to I.63-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.63-1 to I.63-53 in Table I.63 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0657]

[0658] Table I.64: The preferred compounds of formula (I.64) are compounds I.64-1 to I.64-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.64-1 to I.64-53 in Table I.64 are defined by the meaning of each entry numbered 1 to 53 of Q in Table 1.

[0659]

[0660] Table I.65: The preferred compounds of formula (I.65) are compounds I.65-1 to I.65-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.65-1 to I.65-53 in Table I.65 are defined by the meaning of each entry numbered 1 to 53 of Q in Table 1.

[0661]

[0662] Table I.66: The preferred compounds of formula (I.66) are compounds I.66-1 to I.66-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.66-1 to I.66-53 of Table I.66 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0663]

[0664] Table I.67: The preferred compounds of formula (I.67) are compounds I.67-1 to I.67-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.67-1 to I.67-53 of Table I.67 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0665]

[0666] Table I.68: The preferred compounds of formula (I.68) are compounds I.68-1 to I.68-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.68-1 to I.68-53 in Table I.68 are defined by the meaning of each entry numbered 1 to 53 of Q in Table 1.

[0667]

[0668] Table I.69: The preferred compounds of formula (I.69) are compounds I.69-1 to I.69-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.69-1 to I.69-53 in Table I.69 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0669]

[0670] Table I.70: The preferred compounds of formula (I.70) are compounds I.70-1 to I.70-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.70-1 to I.70-53 of Table I.70 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0671]

[0672] Table I.71: The preferred compounds of formula (I.71) are compounds I.71-1 to I.71-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.71-1 to I.71-53 of Table I.71 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0673]

[0674] Table I.72: The preferred compounds of formula (I.72) are compounds I.72-1 to I.72-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.72-1 to I.72-53 of Table I.72 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0675]

[0676] Table I.73: The preferred compounds of formula (I.73) are compounds I.73-1 to I.73-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.73-1 to I.73-53 in Table I.73 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0677]

[0678] Table I.74: The preferred compounds of formula (I.74) are compounds I.74-1 to I.74-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.74-1 to I.74-53 of Table I.74 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0679]

[0680] Table I.75: The preferred compounds of formula (I.75) are compounds I.75-1 to I.75-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.75-1 to I.75-53 of Table I.75 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0681]

[0682] Table I.76: The preferred compounds of formula (I.76) are compounds I.76-1 to I.76-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.76-1 to I.76-53 of Table I.76 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0683]

[0684] Table I.77: The preferred compounds of formula (I.77) are compounds I.77-1 to I.77-53, wherein Q has the meaning shown in each row of Table 1. Therefore, compounds I.77-1 to I.77-53 of Table I.77 are defined by the meaning of each entry number 1 to 53 of Q in Table 1.

[0685] Spectral data of the selected table example:

[0686] Detailed synthetic examples of the selected compounds of the present invention, of general formula (I), are listed below. The chemical examples described in the following sections record... 1 H NMR, 13 C-NMR and 19 F-NMR spectral data (1 H-NMR is 400MHz 13 C-NMR at 150MHz and 19 F-NMR was performed at 375 MHz using CDCl3, CD3OD, or d6-DMSO as solvents, with an internal standard of tetramethylsilane (δ = 0.00 ppm). The obtained signals were acquired on a Bruker instrument, and the listed signals have the following meanings: br = broad peak, s = singlet, d = doublet, t = triplet, dd = doublet, ddd = double doublet, m = multiplet, q = quartet, quintet, sext = sextet, sept = septet, dq = double quartet, dt = double triplet. In the case of diastereomer mixtures, significant signals for each of the two diastereomers were recorded, or the characteristic signal of the dominant diastereomer was recorded. The abbreviations used for chemical groups have 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.

[0687] The spectral data of the selected tabular examples listed below are obtained through conventional methods. 1 H NMR description or evaluation can be performed using NMR peak listing methods.

[0688] conventional 1 H NMR Explanation

[0689] Example 1 number I.77-49:

[0690] 1 H-NMR (400MHz, CDCl3δ, ppm)7.59(m,1H),7.37(t,1H),7.22(m,1H),7.14(dd,1H),6.97(m,1H ),6.77(m,1H),4.92(s,2H),4.20(t,2H),1.67-1.63(m,2H),1.32-1.26(m,4H),0.87(t,3H).

[0691] Example number I.71-49:

[0692] 1 H-NMR (400MHz, CDCl3δ, ppm)7.59(m,1H),7.40(t,1H),7.22(dd,1H),7.14( dd,1H),6.97(dt,1H),6.77(dt,1H),5.24(q,1H),5.01(s,2H),3.74(s,3H).

[0693] Example 1 number I.70-49:

[0694] 1 H-NMR (400MHz, CDCl3δ, ppm)7.60(m,1H),7.40(t,1H),7.21(m,1H),7.14(m,1H),6.96(m,1H),6.77(m,1H),5.05(s,2H),4.75(s,2H),3.77(s,3H).

[0695] Example number I.72-49:

[0696] 1 H-NMR (400MHz, CDCl3δ, ppm)7.57(m,1H),7.37(t,1H),7.21(m,1H),7.14(dd,1H) ,6.96(dt,1H),6.77(dt,1H),4.93(s,2H),3.99(d,2H),1.95(m,1H),0.90(d,6H).

[0697] NMR peak listing method

[0698] by 1 The selected embodiment is represented in the form of an H NMR peak list. 1 H NMR data. For each signal peak, the δ value in ppm is listed first, followed by the signal intensity in parentheses. For different signal peaks, the δ value / signal intensity pairs are listed alternately with semicolons.

[0699] Therefore, the peak list of one embodiment takes the following form:

[0700] δ1 (Intensity 1); δ2 (Intensity 2); ...; δ i (strength i );……;δ n (strength n )

[0701] The intensity of the spike signal is related to the signal height (in cm) in the printed NMR spectrum example, and the true proportion of the signal intensity is shown. In the case of a broad-peak signal, several peaks or intermediate portions of the signal and their relative intensities compared to the strongest signal in the spectrum can be shown.

[0702] In order to correct 1 The chemical shifts in 1H NMR spectra are determined using the chemical shifts of tetramethylsilane and / or the solvent, especially when the spectra are measured in DMSO. Therefore, the tetramethylsilane peak may, but is not required, appear in the NMR peak list.

[0703] 1 H NMR peak list compared to conventional 1 The H NMR prints are similar and therefore typically include all the peaks listed in a standard NMR description.

[0704] In addition, compared with the conventional 1 Like H NMR prints, they can display solvent signals, stereoisomer signals of the target compound (which also form part of the subject of this invention), and / or signals of impurity peaks.

[0705] In the reporting of compound signals in the δ range of solvents and / or water, 1 The H NMR peak list shows peaks for common solvents (e.g., peaks for DMSO and water in DMSO-D6), which, on average, typically have high intensity.

[0706] The average intensity of the peaks of the stereoisomers of the target compound and / or the peaks of impurities is usually lower than that of the peaks of the target compound (e.g., purity > 90%).

[0707] Such stereoisomers and / or impurities can be specific to a particular preparation method. Therefore, their peaks can help identify the reproducibility of the preparation method by referring to "by-product fingerprints".

[0708] Professionals calculate the peaks of the target compound using known methods (MestreC, ACD simulation, and expected values ​​estimated using experience), and optionally use additional intensity filters to separate the peaks of the target compound as needed. This separation is different from conventional methods. 1 The peak picking is similar to that described in the H NMR description.

[0709] It can be found at Research Disclosure Database No. 564025 1 Additional details regarding the HNMR peak list.

[0710]

[0711]

[0712]

[0713]

[0714]

[0715]

[0716]

[0717]

[0718]

[0719]

[0720]

[0721]

[0722]

[0723]

[0724]

[0725]

[0726]

[0727]

[0728]

[0729] The present invention also provides a method for protecting crop plants or useful plants from the phytotoxic effects of agrochemicals such as pesticides or, in particular, herbicides, which cause damage to crop plants or useful plants, characterized in that a compound of general formula (I) or a salt thereof is used as a safener, preferably an effective amount of a compound of general formula (I) or a salt thereof is applied to the plant, plant parts or its seeds (or seed material).

[0730] Compounds of general formula (I) above (=safeners) are suitable for use with active ingredients (pesticides) for the selective control of pests in a variety of crop cultures, such as economically important crops like cereals (wheat, barley, rye, rice, corn, millet / sorghum), sugar beets, sugarcane, rapeseed, cotton, sunflowers, peas, beans, and soybeans. Herbicide-safener compositions with safeners of general formula (I) are also suitable for controlling harmful plants in nurseries and areas of useful and ornamental plants, such as lawn areas of practical or decorative turfgrasses, particularly ryegrass, Kentucky bluegrass, or Bermuda grass.

[0731] Of particular interest, with regard to useful plants and crops in which herbicide-safety compositions comprising compounds of general formula (I) can be used, are mutant crops or transgenic crops that are fully or partially resistant to certain pesticides, such as corn crops resistant to glufosinate or glyphosate, or soybean crops resistant to imidazolinones 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 adequately resistant to the pesticides used.

[0732] When used in conjunction with pesticides, compounds of general formula (I) can be applied simultaneously with or in any order to the active ingredients, and thus can reduce or completely prevent the detrimental side effects of these active ingredients in the case of crop plants without impairing or significantly reducing their efficacy against unwanted pests. This can also significantly reduce or completely prevent damage caused by the use of more than one pesticide, such as more than one herbicide or a combination of herbicide and insecticide or fungicide. This can considerably expand the application scope of traditional pesticides.

[0733] If the compositions of the present invention contain pesticides, these compositions are applied directly to the growing area at an appropriate dilution, to germinated harmful plants and / or beneficial plants, or to seedlings of harmful plants and / or beneficial plants. If the compositions of the present invention do not contain any pesticides, these compositions can be used by a so-called tankmix method, meaning that the user mixes and dilutes the separately formulated products (= useful plant protection composition and pesticide) before application to the area to be treated, or before or after application of pesticides, or for seed pretreatment (i.e., for coating seeds of beneficial plants). It is preferable to apply the safener promptly with the pesticide, especially after the 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 tankmixes or co-formulations, or when applied separately in parallel or consecutively (multiple applications). Repeated application more than once is also possible. Sometimes it is also reasonable to combine pre-emergence and post-emergence applications. A common option is to apply the compound (I) of the present invention post-emergence to the useful plant or crop plant, simultaneously or later with the application of the pesticide. Another option is to use the compound (I) of the present invention for seed dressing, (dipping) treatment of seedlings (e.g., rice), or treatment of other propagation materials (e.g., potato tubers).

[0734] When compounds of general formula (I) are used in combination with herbicides, enhanced herbicidal activity against harmful plants is typically observed, in addition to the effects of the safener. Furthermore, in many cases, the growth of beneficial plants and crop plants is improved, and harvest yields can be increased.

[0735] The compositions of the present invention may comprise one or more pesticides. Examples of useful pesticides include herbicides, insecticides, fungicides, acaricides, and nematicides, each of which, when used alone, causes phytotoxic damage to crop plants, or is likely to cause damage. Of particular interest are the respective active pesticide components from herbicides, insecticides, acaricides, nematicides, and fungicides (especially herbicides).

[0736] The weight ratio of the safener (general formula (I)) to the pesticide can vary widely, typically from 1:100 to 100:1, preferably from 1:20 to 20:1, and particularly from 1:10 to 10:1. The optimal weight ratio of safener to pesticide depends on the appropriate safener and pesticide used, as well as the type of beneficial plant or crop to be protected. Depending on the pesticide used and the type of beneficial plant to be protected, the required safener application rate can vary widely, typically from 0.001 to 10 kg per hectare, preferably from 0.01 to 1 kg, and particularly from 0.01 to 0.2 kg of safener. The amount and weight ratio required for successful treatment can be determined by simple preliminary testing.

[0737] In the case of seed dressing, for example, 0.005 to 20 g of safety agent (general formula (I)) per kilogram of seeds is used, preferably 0.01 to 10 g of safety agent per kilogram of seeds, and particularly 0.05 to 5 g of safety agent per kilogram of seeds.

[0738] When a solution of a safener (general formula (I)) is used in seed treatment and the seeds or seedlings are moistened with the solution, the appropriate concentration is generally 1 to 10,000 ppm by weight, preferably 100 to 1,000 ppm.

[0739] The required quantity and weight ratio for successful processing can be determined through simple preliminary tests.

[0740] Safeners of general formula (I) can be formulated alone or in combination with pesticides in a conventional manner. Therefore, useful plant or crop plant protection compositions are also provided.

[0741] The combined use of safeners and pesticides is preferred, especially when safeners and herbicides are used as finished formulations or by tank mixing.

[0742] Also preferred is the use of a safer agent of general formula (I) in seed treatment, followed by application of pesticides, preferably herbicides, after sowing via pre- or post-emergence methods.

[0743] Compounds of general formula (I) or their salts may be used alone or in formulation form in combination with other pesticide actives such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers, and / or growth regulators, 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.

[0744] Combination formulations of the compounds of the present invention that can be used in mixed formulations or tank mixes are, for example, known active ingredients based on inhibition of the following: acetyllactate synthase, acetyl-CoA carboxylase, cellulase, enolpyruvate-shikimate-3-phosphate synthase, glutamine synthase, p-hydroxyphenylpyruvate dioxygenase, phytopenic acid desaturase, photosynthetic system I, photosynthetic system II, or protoporphyrinogen oxidase, as known, for example, in Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006, and the references cited therein.

[0745] 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 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.

[0746] An example of such a herbicide mixture is:

[0747] Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicabazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5- Fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrol, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, flubutin Beflubutamid, benzolin, benzolin-ethyl, benzfluralin, benzuresate, benzsulfuron, benzsulfuron-methyl, benzulide, benztazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanaf (os), bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, bromoxynil-potassium, bromoxynil-heptanoate, and bromoxynil-octanoate.Busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cabenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, and chlorpyrifos. (chlorfenac), chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron ), indoleone (cinidon), indoleone-ethyl (cinidon), cinmethylin (cinmethylin), cinosulfuron (cinosulfuron), clacyfos (clacyfos), clethodim (cledinafop), clodinafop-propargyl (clodinafop-propargyl), cromazine (clomazone), cromazine (clomeprop), cromazine-methyl (clopyralid), cromazine-methyl (cloransulam), cumyl (cumyl) Luron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, 2,4-D-butyl, 2,4-D-dimethylammonium2,4-D-diolamin, 2,4-D-ethyl ester, 2,4-D-2-ethylhexyl ester, 2,4-D-isobutyl ester, 2,4-D-isooctyl ester, 2,4-D-isopropylammonium salt, 2,4-D-potassium salt, 2,4-D-triisopropanolammonium salt and 2,4-D-trolamine, 2,4-DB, 2,4-DB-butyl ester, 2,4-DB-dimethylammonium salt, 2,4-DB-isooctyl ester, 2,4-DB-potassium salt and 2,4-DB-sodium salt, daimuron (dymron), dalapon, dazomet, n-decyl alcohol, betaine (de) smedipham), detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2,4-D-propionic acid (dichlorprop), dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, dichlorfenapyr (dic... losulam), difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, d... Inoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethametsulfuron, ethiozin, ethofumesateEthoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9960, F-5231 (i.e., N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-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, and fenoxaprop-methyl Fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, floxacin The following herbicides are listed: quizalofop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, and flumetsulam. Flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, flurenol-dimethylammonium, flurenol-methyl, fluoroglycofen, fluoroglycofen-ethyl, and flupropanate.Flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium Foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glyphosate, glyphosate-ammonium, glyphosate-isopropylammonium, glyphosate-diammonium glyphosate dimethylammonium, glyphosate potassium, glyphosate sodium, and glyphosate trimethyl sulfonium; H-9201 (O-(2,4-dimethyl-6-nitrophenyl)O-ethylisopropylthiophosphoramide ester); halauxifen; halauxifen-methyl; halosafen; halos... ulfuron), halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02 (i.e., 1-(dimethoxyphosphoryl)ethyl(2,4-dichlorophenoxy)acetic acid ester),Imidacloprid (imazamethabenz), methyl imidacloprid (imazamethabenz-methyl), methoxyimidacloprid (imazamox), methoxyimidacloprid ammonium (imazamox-ammonium), imidazopic (imazapic), imidazopic ammonium (imazapic), imidazopyr (imazapyr-isopropylammonium), imidazoquinolone (imazaquin), imidazoquinolone ammonium (imazaquin), imidazonic acid (i mazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, ioxynil-potassium, and ioxynil-sodium, triazole oxychloride ( ipfencarbazone), isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-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, MCP A-Butoxyethyl ester (MCPA-butotyl), MCPA-dimethylammonium salt, MCPA-2-ethylhexyl ester, MCPA-isopropylammonium salt, MCPA-potassium salt and MCPA-sodium salt, MCPB, MCPB-methyl ester, MCPB-ethyl ester and MCPB-sodium salt, 2-methyl-4-chloropropionic acid (mecoprop), 2-methyl-4-chloropropionic acid sodium (mecoprop-sodium) and 2-methyl-4-chloropropionic acid butoxyethyl ester (mecoprop-butotyl), purified 2-methyl-4-chloropropionic acid (mecoprop-P), purified 2-methyl-4-chloropropionic acid butoxyethyl ester (mecoprop-P-butotyl)Mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methioz Olin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, 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, nonanoic acid (pelargonic acid) Herbicides such as oxadiazon, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, and paraquat are mentioned.Paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, mineral oil, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primis ulfuron), primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazon sodium salt e-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl ), pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobacPyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron n), saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfurtrazone, sulfometuron, sulfometuron-methyl, sulfurosulfuron, SYP-249 (i.e., 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid 1-ethoxy-3-methyl-1-oxobut-3-ene-2- - ester), SYP-300 (i.e., 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioimidazolidine-4,5-dione), 2,3,6-TBA, TCA (trichloroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin Terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, toramezone, tralkoxydim, triafamoneTriallate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, trilopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, 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:

[0748]

[0749] Examples of plant growth regulators that can be used as possible mixed formulations include:

[0750] Acibenzolar, benzothiadiazole (acibenzolar-S-methyl), 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolid, catechol, chlormequat chloride chloride), cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, endothal-disodium, and N,N-dimethylalkylammonium endothal, ethephon, flumetralin, butyl fluorene, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indole-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid (acid), methyl jasmonate, maleic hydrazine, mepiquat chloride, 1-methylcyclopropene, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthoxyacetic acid, nitrophenolate mixture, 4-oxo-4-[(2-phenylethyl)amino]butyric acid, paclobutrazole, N-phenylphthalamicacid, prohexadione, calcium prohexadione, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

[0751] 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 adjusters, depending on the case.

[0752] Compounds of general formula (I) and their combinations with one or more of the aforementioned pesticides can be formulated in various ways according to defined physicochemical and biological parameters. Suitable examples of formulation types include:

[0753] - 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;

[0754] - A powdered product obtained by grinding an active ingredient with a finely dispersed solid inorganic or organic substance, such as talc, natural clay, such as kaolin, bentonite, pyrophyllite, diatomaceous earth, or diatomaceous earth powder.

[0755] - Aqueous or oil-based suspension concentrates, which can be prepared by, for example, wet milling in a bead mill;

[0756] -Water-soluble powder;

[0757] -Water-soluble concentrate;

[0758] - Particles, such as water-soluble particles, water-dispersible particles, and particles for broadcasting and soil application;

[0759] - Wettable powders, which, in addition to active ingredients, also contain diluents or inert substances and surfactants;

[0760] -Capsule suspensions and microcapsules;

[0761] -Ultra-low dose formulation.

[0762] The aforementioned formulation types are known to those skilled in the art and are described, for example, K. Martens, “Spray Drying Handbook”, 3rd ed., G. Goodwin Ltd., London, 1979; W. van Valkenburg, “Pesticide Formulations”, Marcel Dekker, NY, 1973; Winacker-Küchler, “Chemische Technologie” [Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th edition, 1986;

[0763] "Perry's Chemical Engineer's Handbook", 5th ed., McGraw-Hill, NY1973, pages 8-57.

[0764] Necessary formulation adjuvants, such as inert materials, surfactants, solvents, and other additives, are also known and documented in, for example, McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; C. Marsden, "Solvents Guide", 2nd ed., Interscience, NY 1963; H. von Olphen, "Introduction to Clay Colloid Chemistry", 2nd ed., J. Wiley & Sons, NY;

[0765] [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY1964; Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell NJ; Winnacker-Küchler, "Chemische Technologie", volume 7, C. Hanser Verlag Munich, 4th edition 1986.

[0766] In addition to the formulation adjuvants mentioned above, useful plant protective compositions may, as appropriate, contain conventional wetting agents, binders, dispersants, penetrants, emulsifiers, preservatives, antifreeze agents, fillers, carriers and dyes, defoamers, evaporation inhibitors, and pH and viscosity adjusters.

[0767] Depending on the type of formulation, useful plant protection compositions typically contain 0.1% to 99% by weight, particularly 0.2% to 95% by weight, of one or more of a safener of general formula (I) or a combination of a safener and a pesticide. They also contain 1% to 99.9% by weight, particularly 4% to 99.5% by weight, of one or more solid or liquid additives and 0% to 25% by weight, particularly 0.1% to 25% by weight, of a surfactant. In emulsifiable concentrates, the concentration of the active ingredient, i.e., the concentration of the safener and / or pesticide, is typically 1% to 90% by weight, particularly 5% to 80% by weight.

[0768] Powdered products typically contain 1% to 30% by weight, preferably 5% to 20% by weight, of an 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.

[0769] For application, commercially available formulations are diluted in the usual manner, if applicable, such as with water in the case of wettable powders, emulsifiable concentrates, dispersants, and water-dispersible granules. Powder, granule, and sprayable solutions are generally not further diluted with other inert substances before application. The required application rate for safeners of general formula (I) varies depending on external conditions, including temperature, humidity, and the type of herbicide used.

[0770] In the embodiments described below, but not limiting of the invention, unless otherwise defined, the expressions of quantity are based on weight. Example

[0771] 1. Formulation Examples

[0772] 1.1 Powdered Products

[0773] The powdered product is obtained by mixing 10 parts by weight of a compound of general formula (I) (safest agent) or a mixture of active ingredients consisting of a pesticide (e.g., a herbicide) and a safest agent of general formula (I) with 90 parts by weight of talc as an inert substance and pulverizing the mixture in a bead mill.

[0774] 1.2 Water-dispersible powder

[0775] A water-dispersible wettable powder is obtained by mixing 25 parts by weight of a compound of general formula (I) or a mixture of active ingredients consisting of a pesticide (e.g., a herbicide) and a safener of general formula (I), 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignin sulfonate and 1 part by weight of sodium oleoylmethyl taurate as a wetting agent and dispersant, and grinding the mixture in a pinned-disk mill.

[0776] 1.3 Water-dispersible concentrates

[0777] By mixing 20 parts by weight of a compound of general formula (I) or a mixture of active ingredients consisting of a pesticide (e.g., a herbicide) and a safener of general formula (I) with 6 parts by weight of alkylphenol polyethylene glycol ether ( X 207), 3 parts by weight of isotridecyl alcohol polyethylene glycol ether and 71 parts by weight of paraffin mineral oil were mixed and ground in a friction ball mill to a fineness of less than 5 micrometers to obtain a water-dispersible concentrate.

[0778] 1.4 Emulsifiable Concentrate

[0779] An emulsifiable concentrate is obtained by comprising 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.

[0780] 1.5 Water-dispersible particles

[0781] Water-dispersible particles are obtained by mixing the following substances:

[0782]

[0783]

[0784] The mixture is ground in a pin-disc mill and the powder is granulated in a fluidized bed by spraying water as the granulation liquid.

[0785] Water-dispersible particles are also obtained by homogenizing and pulverizing the following substances in a colloid mill:

[0786]

[0787] The mixture is then ground in a bead mill and atomized and dried in a spray tower through a single-phase nozzle to obtain the suspension.

[0788] 2. Biological Examples

[0789] 2.1 Taking the reduction of damage to summer wheat (TRZAS) by mesosulfuron-methyl as an example, the absolute effect of the selected compounds of the present invention.

[0790] The crop seeds to be treated were arranged on sandy loam soil in wood fiber or plastic pots (approximately 4 cm in diameter), covered with soil, and grown in a greenhouse under favorable germination and growth conditions. The test plants were treated at the early leaf stage (BBCH10-BBCH12). During this process, the compound of the present invention, formulated as a wettable powder (WP), of general formula (I), was sprayed as an aqueous suspension onto the aboveground parts of the plants at a water application rate equivalent to 800 l / ha, with the addition of a specified dose of wetting agent (e.g., 0.2% agrotin).

[0791] Herbicides were then applied. For this purpose, mesosulfuron-methyl, formulated as water-dispersible granules (WG), was sprayed onto the aboveground parts of the plants at a dose of 20 g / ha, with an application rate equivalent to 800 l / ha of water, and a wetting agent (e.g., 0.2% agrotin) was added. The herbicide dosage chosen here caused visually significant damage (minimum 30%, maximum 75%) to control crops included in the same trial that were not treated with a safener, compared to untreated crop plants at the time of evaluation.

[0792] After application, cultivate the plants in a greenhouse under favorable growing conditions. Visually assess the damage 14-21 days after application.

[0793] Damage effects were visually assessed at 0-100% levels compared to untreated control plants, with each treatment repeated 2-3 times and the average value taken. Example:

[0794] 0% = No significant effect compared to untreated plants

[0795] 20% = Compared to the untreated control population, the treated plant population showed 20% damage (e.g., growth height, leaf damage, etc.).

[0796] 100% = Complete damage / death of the treated plants.

[0797] Experiments show that treatment with selected compounds from the embodiments of the present invention (= herbicide damage using compounds of formula (I) of the present invention in the table below) significantly reduced damage to summer wheat crops (TRZAS; cv. Triso) caused by the herbicide mesosulfuron-methyl (= herbicide damage not using compounds of formula (I) in the table below):

[0798]

[0799]

[0800] 2.2 Taking the reduction of damage to summer barley (HORVS) by mesosulfuron-methyl as an example, the absolute effect of the selected compounds of the present invention.

[0801] The seeds of the crop to be treated were arranged on sandy loam soil in wood fiber or plastic pots (approximately 4 cm in diameter), covered with soil, and grown in a greenhouse under favorable germination and growth conditions. The test plants were treated at the early leaf stage (BBCH10-BBCH12). During this process, the compound of general formula (I) of the present invention, formulated as a wettable powder (WP), was sprayed as an aqueous suspension onto the aboveground parts of the plants at a specified dosage, with a water application rate equivalent to 800 l / ha, and a wetting agent (e.g., 0.2% agrotin) was added.

[0802] Herbicides were then applied. For this purpose, mesosulfuron-methyl, formulated as water-dispersible granules (WG), was sprayed onto the aboveground parts of the plants at a dose of 20 g / ha, with an application rate equivalent to 800 l / ha of water, and a wetting agent (e.g., 0.2% agrotin) was added. The herbicide dosage chosen here caused visually significant damage (minimum 30%, maximum 75%) to control crops included in the same trial that were not treated with a safener, compared to untreated crop plants at the time of evaluation.

[0803] After application, cultivate the plants in a greenhouse under favorable growing conditions. Visually assess the damage 14-21 days after application.

[0804] Damage effects were visually assessed at 0-100% levels compared to untreated control plants, with each treatment repeated 2-3 times and the average value taken. Example:

[0805] 0% = No significant effect compared to untreated plants

[0806] 20% = Compared to the untreated control population, the treated plant population showed 20% damage (e.g., growth height, leaf damage, etc.).

[0807] 100% = Complete damage / death of the treated plants.

[0808] Experiments show that treatment with selected compounds from the embodiments of the present invention (= herbicide damage using compounds of formula (I) of the present invention in the table below) significantly reduced damage to summer barley crops (HORVS; cv. Montoya) caused by the herbicide mesosulfuron-methyl (= herbicide damage not using compounds of formula (I) in the table below):

[0809]

[0810] 2.3 Taking the reduction of damage to summer wheat (TRZAS) by mesosulfuron-methyl as an example, the relative effects of the selected compounds of the present invention are as follows:

[0811] The crop seeds to be treated were arranged on sandy loam soil in plastic pots (approximately 4 cm in diameter), covered with soil, and grown in a greenhouse under favorable germination and growth conditions. The test plants were treated at the early leaf stage (BBCH10-BBCH12). During this process, the compound of the present invention, formulated as a wettable powder (WP), of general formula (I), was sprayed as an aqueous suspension onto the aboveground parts of the plants at a specified dosage, with a water application rate equivalent to 800 l / ha, and a wetting agent (e.g., 0.2% Genapol-LRO or 0.2% Mero) was added.

[0812] Herbicides were then applied. For this purpose, mesosulfuron-methyl, formulated as water-dispersible granules (WG), was sprayed onto the aboveground parts of the plants at a dose of 40–60 g / ha, with an application rate equivalent to 800 l / ha of water, and a wetting agent (e.g., 0.2% Genapol-LRO or 1 l / ha Biopower) was added. The herbicide dosage chosen here caused visually significant damage (minimum 30%, maximum 75%) to control crops included in the same trial that were not treated with a safener, compared to untreated crop plants at the time of evaluation.

[0813] Following application, the plants were cultivated in a greenhouse under favorable growing conditions. Nine to 13 days after application, the efficacy of the test compound was visually assessed. For this purpose, the appearance of plants treated with the test compound and herbicide was compared with that of the corresponding herbicide control group (no safener; visible damage) and the untreated control group (no damage). Here, the damage reduction effect of the test compound is expressed using a graded efficacy code according to the following protocol:

[0814] 0: No reduction in damage (appearance equivalent to the herbicide control group)

[0815] 1: Damage slightly reduced

[0816] 2: Damage significantly reduced

[0817] 3: Damage significantly reduced

[0818] 4: Damage was completely reduced (appearance was equivalent to the untreated control group).

[0819] Experiments have shown that the compounds of the present invention selected in the examples are significantly effective in reducing damage to summer wheat crops (TRZAS; cv. Triso) caused by the herbicide mesosulfuron-methyl.

[0820]

[0821] 2.4 Taking the reduction of damage to summer barley (HORVS) by mesosulfuron-methyl as an example, the relative effects of the selected compounds of the present invention are as follows:

[0822] The crop seeds to be treated were arranged on sandy loam soil in plastic pots (approximately 4 cm in diameter), covered with soil, and grown in a greenhouse under favorable germination and growth conditions. The test plants were treated at the early leaf stage (BBCH10-BBCH12). During this process, the compound of the present invention, formulated as a wettable powder (WP), of general formula (I), was sprayed as an aqueous suspension onto the aboveground parts of the plants at a specified dosage, with a water application rate equivalent to 800 l / ha, and a wetting agent (e.g., 0.2% Genapol-LRO or 0.2% Mero) was added.

[0823] Herbicides were then applied. For this purpose, mesosulfuron-methyl, formulated as water-dispersible granules (WG), was sprayed onto the aboveground parts of the plants at a dose of 40–60 g / ha, with an application rate equivalent to 800 l / ha of water, and a wetting agent (e.g., 0.2% Genapol-LRO or 1 l / ha Biopower) was added. The herbicide dosage chosen here should cause visually significant damage (minimum 30%, maximum 75%) to the control crop plants included in the same trial that were not treated with a safener, compared to untreated crop plants at the time of evaluation.

[0824] Following application, plants were cultivated in a greenhouse under favorable growing conditions. Nine to 13 days post-application, the efficacy of the test compound was visually assessed. For this purpose, the appearance of plants treated with the test compound and herbicide was compared to that of the corresponding herbicide control group (no safener; visible damage) and the untreated control group (no damage). Here, the damage-reducing effect of the test compound was represented by a graded efficacy code with two replicates, according to the following protocol:

[0825] 0: No reduction in damage (appearance equivalent to the herbicide control group)

[0826] 1: Damage slightly reduced

[0827] 2: Damage significantly reduced

[0828] 3: Damage significantly reduced

[0829] 4: Damage was completely reduced (appearance was equivalent to the untreated control group).

[0830] Experiments have shown that the compounds of the present invention selected in the examples are significantly effective in reducing damage to summer barley (HORVS; cv. Montoya) caused by the herbicide mesosulfuron-methyl.

[0831]

[0832]

Claims

1. Use of compounds of general formula (I) or salts thereof for reducing the phytotoxicity of herbicides to beneficial plants. in R 1 It can be hydrogen, halogen, cyano or nitro. R 2 It can be hydrogen, halogen, cyano, nitro, or (C1-C6) alkoxy. R 3 It is hydrogen or (C1-C6) alkyl. R 4 It is hydrogen, (C1-C6)alkyl, or (C1-C6)haloalkyl. and n and m are independently 0, 1, or 2, where m and n must not both be 0.

2. The use as described in claim 1, wherein, In the compound of general formula (I) of claim 1, wherein R 1 It can be hydrogen, halogen, or cyano. R 2 It can be hydrogen, halogen, cyano, or (C1-C6) alkoxy. R 3 It can be hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, or 2-butyl. R 4 It is hydrogen, (C1-C6)alkyl, or (C1-C6)haloalkyl. and n and m are independently 0, 1, or 2, where m and n must not both be 0.

3. The use as described in claim 1, wherein, In the compound of general formula (I) of claim 1, wherein R 1 It can be hydrogen, halogen, or cyano. R 2 It can be hydrogen, halogen, cyano, or (C1-C6) alkoxy. R 3 It can be hydrogen, methyl, ethyl, n-propyl, or isopropyl. R 4 It is hydrogen, (C1-C6)alkyl, or (C1-C6)haloalkyl. and n and m are independently 0, 1, or 2, where m and n must not both be 0.

4. The use as described in claim 1, wherein, In the compound of general formula (I) of claim 1, wherein R 1 It can be hydrogen, fluorine, chlorine, bromine, iodine or cyano. R 2 It can be hydrogen, fluorine, chlorine, bromine, iodine, cyano, or OCH3. R 3 It is hydrogen or CH3. R 4 It is hydrogen or (C1-C6) alkyl. and n and m are independently 0, 1 or 2, and m and n are not both 0.

5. The use as described in claim 1, wherein, In the compound of general formula (I) of claim 1, wherein R 1 It can be hydrogen, fluorine, chlorine, bromine, or iodine. R 2 It can be hydrogen, fluorine, chlorine, bromine, iodine, or OCH3. R 3 It is hydrogen or CH3. R 4 It is hydrogen or (C1-C6) alkyl. and n and m are independently 0, 1 or 2, and m and n are not both 0.

6. The use as described in claim 1, wherein, In the compound of general formula (I) of claim 1, wherein R 1 It is hydrogen, fluorine or chlorine. R 2 It can be hydrogen, fluorine, chlorine, or OCH3. R 3 It is hydrogen. R 4 It can be hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, or n-pentyl. and n and m are independently 0, 1, or 2, where m and n must not both be 0.

7. The use as described in claim 1, wherein, In the compound of general formula (I) of claim 1, (R 1 ) n -Phenyl groups are selected from (R 2 ) m -Phenyl groups are selected from R 3 It is hydrogen. and R 4 It can be hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, or n-pentyl, and n and m are independently 0, 1, or 2, where m and n must not both be 0.

8. A compound is selected from the following compounds or their salts. 。 9. The use of a compound selected from the group consisting of compounds or salts thereof for reducing the phytotoxicity of herbicides to beneficial plants. 。 10. A method for reducing the phytotoxic effects of herbicides on useful plants, which is carried out by using one or more of the compounds of any one of claims 1 to 9 or salts thereof.

11. A method for reducing the phytotoxic effects of herbicides on useful plants, characterized in that, One or more of the compounds of any one of claims 1 to 9 or their salts, applied in combination with a herbicide, are applied simultaneously or in any order with the herbicide.

12. The method of claim 11, wherein the herbicide is mesosulfuron-methyl.

13. The method according to claim 11 or 12, characterized in that, Apply the compound or salt thereof of any one of claims 1 to 9 to a plant, a plant part or its seed or seed material.

14. The use as described in claim 1 or the method as described in claim 10 or 11, characterized in that, The useful plants are crop plants.

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