[(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives and their salts, crop protection compositions containing them, processes for their preparation and their use as safeners

Abstract

FIELD OF THE INVENTION The present invention relates to crop protection compounds and compositions containing certain compounds as safeners for reducing the phytotoxic effects of pesticides, especially herbicides. More specifically, the present invention relates to certain [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives of general formula (I) and their salts, methods for preparing them, and their use as crop protection compounds (safeners). TIFF2023503604000145.tif56166

Description

[Technical field]

[0001] The present invention relates to useful plant protection compounds and compositions comprising certain compounds as safeners for reducing the phytotoxic effects of pesticides, especially herbicides. More specifically, the present invention relates to certain [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives and their salts as safeners, and methods for preparing same. [Background technology]

[0002] In the control of undesirable organisms in horticultural and forestry useful plant crops by pesticides, the useful plants are also frequently more or less damaged by the pesticides used, especially herbicides, insecticides, fungicides, etc. This undesirable phytotoxic side effect occurs to a certain extent when many herbicides are used, mainly in post-emergence application, in useful plant crops, such as corn, rice or cereals. The use of "safeners" or "antidotes" can, in some cases, protect useful plants from the phytotoxic properties of pesticides without reducing or significantly impairing the pesticidal action against pests. In some cases, improved pesticidal action against pests, such as weeds, has even been observed in the presence of safeners.

[0003] The compounds known to date as safeners are in a number of different chemical structure classes, and their suitability for use as safeners generally depends on the chemical structure of the pesticide and also on the useful plant crop.

[0004] Compounds from the group of derivatives of phenoxy- or heteroaryloxyalkanecarboxylic acids have long been known for their safener effect when used in combination with herbicides. Examples of such compounds are MCPA and similar compounds, which at the same time remain herbicidally active against harmful plants, or cloquintocet-mexyl.

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

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

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

[0008] No active ingredients of the chemical class of [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives with phytoactive properties are known from the literature.

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

[0010] [(1,5-diaryl-1H-pyrazol-3-yl)oxy]acetic acid derivatives are known from J. Heterocyclic Chemistry 2010, 47(4), 897-902 and J. Heterocyclic Chemistry 2012, 49(6), 1370-1375.

[0011] EP 0 310 555 describes 1,5-diphenyl-1H-1,2,4-triazole-3-carboxylic acid derivatives for protecting crop plants from the phytotoxic effects of herbicides.

[0012] When safeners are used to protect crop plants from damage by pesticides, it has been found that known safeners can often have drawbacks, including, for example, (a) insufficient useful plant protection properties, or (b) when combined with a particular herbicide, the useful plant range for which the safener / herbicide combination is used is not large enough.

[0013] For the reasons stated above, there is an increasing need to provide alternative compounds with safener activity. [Prior art documents] [Patent documents]

[0014] [Patent Document 1] International Publication No. 2004 / 084631 [Patent Document 2] International Publication No. 2005 / 015994 [Patent Document 3] International Publication No. 2005 / 112630 [Patent Document 4] International Publication No. 2008 / 131860 [Patent Document 5] European Patent No. 0310555 [Non-patent literature]

[0015] [Non-Patent Document 1] Polish J.Chem.2006,80,889-897 [Non-Patent Document 2] Bioorganic&Medicinal Chemistry 2018,26,3321-3344 [Non-Patent Document 3] J.Heterocyclic Chemistry 2010,47(4),897-902 [Non-Patent Document 4] J.Heterocyclic Chemistry 2012,49(6),1370-1375 Summary of the Invention [Problem to be solved by the invention]

[0016] The present invention relates to novel useful plant protection compounds of general formula (I) or salts thereof for reducing the phytotoxic effect of pesticides, especially herbicides, on useful plants or crop plants, except for ethyl [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetate (CAS [931426-67-4]) [ka]

[0017] (In the formula, R 1 and R 2 are independently hydrogen, halogen, cyano, nitro, (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C3-C8) cycloalkyl, (C3-C8) cycloalkenyl, (C1-C6) alkoxy or (C1-C6) alkylS(O) p and the latter seven groups are unsubstituted or selected from halogen, cyano, (C1-C6)alkoxy and (C1-C6)alkylS(O) p and is substituted by one already more radicals from the group R 3 is hydrogen or (C1-C6) alkyl, R 4 is hydrogen, (C1-C 18 ) Alkyl, (C1-C 18 )Haloalkyl, (C1-C 18 ) cyanoalkyl, (C2-C 18 ) alkenyl, (C2-C 18) alkynyl, (C3-C 12 )Cycloalkyl, (C3-C 12 ) Cycloalkenyl, aryl, heteroaryl, (C1-C 18 )Alkoxy-(C1-C 18 ) Alkyl, (C1-C 18 )Haloalkoxy-(C1-C 18 ) Alkyl, (C1-C 18 )Alkoxy-(C1-C 18 )Haloalkyl, (C1-C 18 )Alkylthio-(C1-C 18 ) Alkyl, (C1-C 18 )Haloalkylthio-(C1-C 18 ) Alkyl, (C2-C 18 ) haloalkenyl, (C2-C 18 )Haloalkynyl, heterocyclyl-(C1-C 18 )Alkyl, aryl-(C1-C 18 ) Alkyl, (C3-C 12 )Cycloalkyl-(C1-C 18 ) Alkyl, (C1-C 18 )Alkoxycarbonyl-(C1-C 18 ) alkyl or (C1-C 18 )Alkoxycarbonyl-(C3-C 12 )Cycloalkyl-(C1-C 18 ) alkyl, or Formula-NR a R b or -N=CR c R d Based on In the first two groups, R a , R b , R c and R d each of the groups is independently hydrogen, (C1-C4) alkyl, (C2-C4) alkenyl, (C2-C4) alkynyl, benzyl, substituted benzyl, phenyl, or substituted phenyl; or R a and R bforms, together with the nitrogen atom, a 3-8 membered heterocyclic ring which, in addition to the nitrogen atom, may contain one or two further ring heteroatoms from the group N, O and S, and which is unsubstituted or substituted by one or more radicals from the group (C1-C4)-alkyl and (C1-C4)-haloalkyl, or R c and R d together with the carbon atom form a 3-8 membered carbocyclic or heterocyclic group which may contain 1-3 ring heteroatoms of the group N, O and S, the carbocyclic or heterocyclic group being unsubstituted or substituted by one or more radicals of the group (C1-C4)-alkyl and (C1-C4)-haloalkyl, n and m are independently a number from 0 to 5; p is 0, 1 or 2) to provide.

[0018] Compounds of general formula (I) can form salts by the addition of suitable inorganic or organic acids, such as mineral acids, for example HCl, HBr, H2SO4, H3PO4 or HNO3, or organic acids, such as carboxylic acids, for example formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid, or sulfonic acids, for example p-toluenesulfonic acid, to basic groups, for example amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino. In such cases, these salts contain the conjugate base of the acid as the anion. The deprotonated form of suitable substituents, for example sulfonic acids, certain sulfonamides or carboxylic acids, can form inner salts with groups such as amino groups that are themselves protonatable. Salts can also be formed by the action of a base on compounds of general formula (I). Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine, as well as ammonium, alkali metal or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate. These salts are prepared by converting the acidic hydrogen to an agriculturally suitable cation, such as a metal salt, in particular an alkali metal salt or alkaline earth metal salt, in particular a sodium and potassium salt, or an ammonium salt, a salt with an organic amine or a quaternary ammonium salt, for example of the formula [NR e R f R g R h ] + (In the formula, R e ~R h are each independently substituted with a cation of an organic group, especially alkyl, aryl, arylalkyl or alkylaryl. Also suitable are alkylsulfonium and alkylsulfoxonium salts, such as (C1-C4)-trialkylsulfonium and (C1-C4)-trialkylsulfoxonium salts.

[0019] The compounds of formula (I) and their salts used according to the present invention are hereinafter referred to as "compounds of general formula (I)".

[0020] The present invention preferably relates to a compound other than ethyl [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetate. R 1 and R 2 are independently hydrogen, halogen, cyano, nitro, (C1-C4) alkyl, (C2-C4) alkenyl, (C2-C4) alkynyl, (C3-C6) cycloalkyl, (C3-C6) cycloalkenyl, (C1-C4) alkoxy or (C1-C4) alkylS(O) p and the latter seven groups are unsubstituted or selected from halogen, cyano, (C1-C4)alkoxy and (C1-C4)alkylS(O) p and is substituted by one or more groups from the group R 3 is hydrogen or (C1-C4) alkyl; R 4 Hydrogen, (C1-C 18 ) Alkyl, (C1-C 18 )Haloalkyl, (C1-C 18 ) cyanoalkyl, (C2-C 18 ) alkenyl, (C2-C 18 ) alkynyl, (C3-C 12 )Cycloalkyl, (C3-C 12 ) Cycloalkenyl, aryl, heteroaryl, (C1-C 18 )Alkoxy-(C1-C 18 ) Alkyl, (C1-C 18 )Haloalkoxy-(C1-C 18 ) Alkyl, (C1-C 18 )Alkoxy-(C1-C 18 )Haloalkyl, (C1-C 18 )Alkylthio-(C1-C 18 ) Alkyl, (C1-C 18 )Haloalkylthio-(C1-C 18 ) Alkyl, (C2-C 18 ) haloalkenyl, (C2-C 18 )Haloalkynyl, heterocyclyl-(C1-C 18 )Alkyl, aryl-(C1-C 18 ) Alkyl, (C3-C 12)Cycloalkyl-(C1-C 18 ) Alkyl, (C1-C 18 )Alkoxycarbonyl-(C1-C 18 ) alkyl or (C1-C 18 )Alkoxycarbonyl-(C3-C 12 )Cycloalkyl-(C1-C 18 ) alkyl, n and m are independently a number from 0 to 4; p is 0, 1 or 2; A compound of general formula (I) is provided:

[0021] The present invention very particularly preferably relates to the preparation of ethyl [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetate, with the exception of R 1 and R 2 are independently hydrogen, halogen, cyano, methyl, CF3, CH2F, CHF2, OCH3, OCF3, SCH3 or SCF3; R 3 is hydrogen, CH2CH3 or CH3, R 4 Hydrogen, (C1-C 18 ) Alkyl, (C1-C 18 )Haloalkyl, (C1-C 18 ) cyanoalkyl, (C2-C 18 ) alkenyl, (C2-C 18 ) alkynyl, (C3-C 12 )Cycloalkyl, (C3-C 12 ) Cycloalkenyl, aryl, heteroaryl, (C1-C 18 )Alkoxy-(C1-C 18 ) Alkyl, (C1-C 18 )Haloalkoxy-(C1-C 18 ) Alkyl, (C1-C 18 )Alkoxy-(C1-C 18 )Haloalkyl, (C1-C 18 )Alkylthio-(C1-C 18 ) Alkyl, (C1-C 18 )Haloalkylthio-(C1-C 18 ) Alkyl, (C2-C18 ) haloalkenyl, (C2-C 18 )Haloalkynyl, heterocyclyl-(C1-C 18 )Alkyl, aryl-(C1-C 18 ) Alkyl, (C3-C 12 )Cycloalkyl-(C1-C 18 ) Alkyl, (C1-C 18 )Alkoxycarbonyl-(C1-C 18 ) alkyl or (C1-C 18 )Alkoxycarbonyl-(C3-C 12 )Cycloalkyl-(C1-C 18 ) alkyl, n and m are independently the numbers 0, 1, 2, or 3; A compound of general formula (I) is provided:

[0022] The present invention particularly preferably relates to compounds other than ethyl [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetate. R 1 and R 2 are independently hydrogen, fluorine, chlorine, bromine, iodine, CN, methyl, CF3, CH2F, CHF2, OCH3, OCF3, SCH3 or SCF3; R 3 is hydrogen or CH3, R 4 Hydrogen, (C1-C 10 ) Alkyl, (C1-C 10 )Haloalkyl, (C1-C 10 ) cyanoalkyl, (C2-C 10 ) alkenyl, (C2-C 10 )alkynyl, (C3-C9)cycloalkyl, (C3-C9)cycloalkenyl, aryl, heteroaryl, (C1-C 10 )Alkoxy-(C1-C 10 ) Alkyl, (C1-C 10 )Haloalkoxy-(C1-C 10 ) Alkyl, (C1-C 10 )Alkoxy-(C1-C 10 )Haloalkyl, (C1-C 10)Alkylthio-(C1-C 10 ) Alkyl, (C1-C 10 )Haloalkylthio-(C1-C 10 ) Alkyl, (C2-C 18 ) haloalkenyl, (C2-C 18 )Haloalkynyl, heterocyclyl-(C1-C 10 )Alkyl, aryl-(C1-C 10 ) alkyl, (C3-C9) cycloalkyl-(C1-C 10 ) Alkyl, (C1-C 10 )Alkoxycarbonyl-(C1-C 10 ) alkyl or (C1-C 10 )Alkoxycarbonyl-(C3-C9)Cycloalkyl-(C1-C 10 ) alkyl, n and m are independently the numbers 0, 1, 2, or 3; A compound of general formula (I) is provided:

[0023] The present invention very particularly preferably relates to the preparation of ethyl [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetate, with the exception of R 1 and R 2 are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, CF3, CH2F, CHF2, OCH3, OCF3, SCH3 or SCF3; R 3 is hydrogen, R 4is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, n-pentyl, phenyl, benzyl, CH2(4-Cl-Ph), CH2(4-F-Ph), CH2(4-OMe-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl methylpropionate-3-yl, ethylpropionate-3-yl, methylacetate-2-yl, ethylacetate-2-yl, methylpivalate-2-yl, ethylpivalate-3-yl, methyl-2-methylpropanoate-3-yl, methyl-2,2-dimethylpropanoate-3-yl, ethyl-2-methylpropanoate-3-yl, methyl-2-propanoate-2-yl, ethyl-2-propanoate 2-(dimethylamino)ethyl, oxetan-3-yl, (3-methyloxetan-3-yl)methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl, cyclopropylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl, allyl, propargyl (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl, 3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, heptan-2-yl, isobutyl, 1,3-dioxolan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl, n and m are independently the numbers 0, 1, 2, or 3; A compound of general formula (I) is provided:

[0024] The present invention very particularly preferably relates to the preparation of ethyl [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetate, with the exception of (R 1 ) n -Phenyl is Q-1.1 to Q-1.53 [Table 1] TIFF0007654654000003.tif92165

[0025] and (R 2 ) m -Phenyl is Q-2.1 to Q-2.53 [Table 2] TIFF0007654654000005.tif217162 TIFF0007654654000006.tif35145

[0026] and R3 is hydrogen, R 4is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, n-pentyl, phenyl, benzyl, CH2(4-Cl-Ph), CH2(4-F-Ph), CH2(4-OMe-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl methylpropionate-3-yl, ethylpropionate-3-yl, methylacetate-2-yl, ethylacetate-2-yl, methylpivalate-2-yl, ethylpivalate-3-yl, methyl-2-methylpropanoate-3-yl, methyl-2,2-dimethylpropanoate-3-yl, ethyl-2-methylpropanoate-3-yl, methyl-2-propanoate-2-yl, ethyl-2-propanoate 2-(dimethylamino)ethyl, oxetan-3-yl, (3-methyloxetan-3-yl)methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl, cyclopropylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl, allyl, propargyl (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl, 3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, heptan-2-yl, isobutyl, 1,3-dioxolan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl, A compound of general formula (I) is provided:

[0027] The above general or preferred radical definitions apply both to the final products of general formula (I) and likewise to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another if desired, i.e. include combinations between the given preferred ranges.

[0028] The given inventive compounds of general formula (I) or salts thereof, or the inventive uses thereof, in which the individual radicals have one of the preferred meanings already specified or specified below, or in particular those in which one or more of the preferred meanings already specified or specified below occur in combination, are of particular interest, primarily for reasons of higher herbicidal activity, better selectivity and / or better preparability.

[0029] With respect to the compounds according to the invention, the terms used above and further below are explained. They are well known to those skilled in the art and have the definitions explained, inter alia, below: Unless otherwise defined, names of chemical groups are generally to be understood such that the bond to the backbone or the rest of the molecule is via the structural element of the last-mentioned relevant chemical group, i.e., for example, in the case of (C2-C8)-alkenyloxy, via the oxygen atom, and in the case of heterocyclyl-(C1-C8)-alkyl or alkylO(O)C-(C1-C8)-alkyl, in each case via a carbon atom of the alkyl group.

[0030] According to the present invention, "alkylsulfonyl", alone or as part of a chemical group, unless otherwise defined, refers to straight-chain or branched alkylsulfonyl, preferably having 1 to 8 or 1 to 6 carbon atoms, such as (but not limited to) methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1 ... It refers to (C1-C6)-alkylsulfonyl such as phenylsulfonyl, 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.

[0031] According to the present invention, "alkylthio", alone or as part of a chemical group, means any of the following alkyl groups: (C1-C 10)-, (C1-C6)- or (C1-C4)-alkylthio, preferably straight chain or branched S-alkyl having 1 to 8 or 1 to 6 carbon atoms, such as (C1-C6)-, (C1-C6)- or (C1-C4)-alkylthio, for example (but not limited to) methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio , hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio, and 1-ethyl-2-methylpropylthio.

[0032] According to the present invention, "alkylsulfinyl (alkyl-S(=O)-)" means, unless otherwise defined, an alkyl group attached to the backbone via -S(=O)-, such as (C1-C6)- or (C1-C4)-alkylsulfinyl, for example (but not limited to) methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2 ... It represents (C1-C6)-alkylsulfinyl such as 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.

[0033] "Alkoxy" refers to an alkyl group attached through an oxygen atom, including, but not limited to, methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylprop ...3-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, 3-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, 3-methylbutoxy, 3-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, 3-methylbutoxy, 3-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, 3-methylbutoxy, 3-methylbutoxy, 3-methylbutoxy, 3-methylbutoxy, 3-methylbutoxy, 3-methylbutoxy, 3-methylbutoxy, 3-methylbutoxy, 3-methylbutoxy The term "alkenyloxy" refers to an alkenyl group bonded via an oxygen atom, and the term "alkynyloxy" refers to an alkynyl group bonded via an oxygen atom, for example (C2-C6)-alkoxy such as (C1-C6)-ethylpentoxy, 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. The term "alkenyloxy" refers to an alkenyl group bonded via an oxygen atom, and the term "alkynyloxy" refers to an alkynyl group bonded via an oxygen atom, for example (C2-C6)-alkoxy. 10 )-, (C2-C6)- or (C2-C4)-alkenoxy and (C3-C6)- or (C3-C4)-alkynoxy.

[0034] According to the present invention, "alkylcarbonyl" (alkyl-C(=O)-), unless otherwise defined, is any of the following: (C1-C 10 It represents an alkyl group bonded to the backbone via -C(=O)-, such as (C1-C6)- or (C1-C4)-alkylcarbonyl, where the number of carbon atoms relates to the alkyl group in the alkylcarbonyl group.

[0035] According to the present invention, "alkoxycarbonyl (alkyl-OC(=O)-)" means, unless otherwise defined, (C1-C 10represents an alkyl group bonded to the backbone via -OC(=O)-, such as (C1-C6)-, (C1-C4)-alkoxycarbonyl, where the number of carbon atoms relates to the alkyl group in the alkoxycarbonyl group. Similarly, "alkenyloxycarbonyl" and "alkynyloxycarbonyl" are, unless otherwise defined, according to the present invention, respectively, defined as (C2-C 10 )-, (C2-C6)- or (C2-C4)-alkenyloxycarbonyl and (C3-C 10 represents alkenyl and alkynyl groups attached to the backbone via -OC(=O)-, such as (C3-C6)-, (C3-C4)-alkynyloxycarbonyl, where the number of carbon atoms refers to the alkenyl or alkynyl group in the alkenyloxycarbonyl or alkynyloxycarbonyl group.

[0036] According to the present invention, the term "alkylcarbonyloxy" (alkyl-C(=O)-O-), unless otherwise defined, refers to any of the following alkyl groups: (C1-C 10 It represents an alkyl group bonded to the backbone via the oxygen of a carbonyloxy group (-C(=O)-O-), such as (C1-C6)-, (C1-C4)-alkylcarbonyloxy, where the number of carbon atoms relates to the alkyl group in the alkylcarbonyloxy group.

[0037] The term "aryl" denotes an optionally substituted monocyclic, bicyclic or polycyclic aromatic system preferably having 6 to 14, especially 6 to 10, ring carbon atoms, such as phenyl, naphthyl, anthryl, phenanthrenyl, etc., preferably phenyl.

[0038] The term "optionally substituted aryl" also includes polycyclic ring systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, etc., where the attachment site is on the aromatic system. In systematic terms, "aryl" is also generally encompassed 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, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkylthio, haloalkyl, alkoxy, haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bisalkylaminoalkoxy, tris[alkyl]silyl, bis[alkyl]arylsilyl, bis[aryl ... [alkyl]alkylsilyl, tris[alkyl]silylalkynyl, alkylalkynyl, cycloalkylalkynyl, haloalkylalkynyl, heterocyclyl-N-alkoxy, nitro, cyano, amino, alkylamino, bisalkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino, alkoxycarbonylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl, bisalkylaminocarbonyl, heteroarylalkoxy, arylalkoxy.

[0039] Heterocyclic groups (heterocyclyls) contain at least one heterocyclic ring (= a carbocyclic ring in which at least one carbon atom is replaced by a heteroatom, preferably from the group N, O, S, P), which may be saturated, unsaturated, partially saturated or heteroaromatic, and may be unsubstituted or substituted (in which case the attachment site is located on a ring atom). If a heterocyclyl group or heterocyclic ring is optionally substituted, it may be fused to other carbocyclic or heterocyclic rings. In the case of optionally substituted heterocyclyls, polycyclic rings such as 8-azabicyclo[3.2.1]octanyl, 8-azabicyclo[2.2.2]octanyl or 1-azabicyclo[2.2.1]heptyl are also included. Optionally substituted heterocyclyls also include spiro ring systems such as 1-oxa-5-azaspiro[2.3]hexyl. Unless otherwise defined, the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and in the heterocyclic ring one or more, preferably 1 to 4, in particular 1, 2 or 3, heteroatoms, preferably of the group N, O and S, but two oxygen atoms should not be directly adjacent, for example one heteroatom of the group N, O and S: 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2- or -3-yl, 2,3-dihydro-1H-pyrrol-1- or -2- or -3- or -4- or -5-yl; 2,5-dihydro-1H-pyrrol-1- or -2- or -3-yl, 1- or 2- or 3- or 4- piperidinyl;2,3,4,5-tetrahydropyridin-2- or -3- or -4- or -5-yl or -6-yl;1,2,3,6-tetrahydropyridin-1- or -2- or -3- or -4- or -5- or -6-yl;1,2,3,4-tetrahydropyridin-1- or -2- or -3- or -4- or -5- or -6-yl;1,4-dihydropyridin-1- or -2- or -3- or -4-yl;2,3-dihydropyridin-2- or -3- or -4- or -5- or -6-yl;2,5-dihydropyridin-2- or -3- or -4- or -5- or -6-yl, 1- or 2- or 3- or 4-azepanyl;2,3,4,5-Tetrahydro-1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl;2,3,4,7-Tetrahydro-1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl;2,3,6,7-Tetrahydro-1H-azepin-1- or -2- or -3- or -4-yl;3,4,5,6-Tetrahydro-2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl;4,5-Dihydro-1H-azepin -1- or -2- or -3- or -4-yl;2,5-dihydro-1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl;2,7-dihydro-1H-azepin-1- or -2- or -3- or -4-yl;2,3-dihydro-1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl;3,4-dihydro-2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl;3,6-dihydro-2H-azepin- 2- or -3- or -4- or -5- or -6- or -7-yl;5,6-dihydro-2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl;4,5-dihydro-3H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl;1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl;2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl;3H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl or -4- or -5- or -6- or -7-yl; 4H-azepine-2- or -3- or -4- or -5- or -6- or -7-yl, 2- or 3-oxolanyl (= 2- or 3-tetrahydrofuranyl); 2,3-dihydrofuran-2- or -3- or -4- or -5-yl; 2,5-dihydrofuran-2- or -3-yl, 2- or 3- or 4-oxanyl (= 2- or 3- or 4-tetrahydropyranyl); 3,4-dihydro-2H-pyran-2- or -3- or -4- or -5- or -6-yl;3,6-Dihydro-2H-pyran-2- or -3- or -4- or -5- or -6-yl; 2H-pyran-2- or -3- or -4- or -5- or -6-yl; 4H-pyran-2- or -3- or -4-yl, 2- or 3- or 4-oxepanyl; 2,3,4,5-tetrahydrooxepin-2- or -3- or -4- or -5- or -6- or -7-yl ;2,3,4,7-Tetrahydrooxepin-2- or -3- or -4- or -5- or -6- or -7-yl;2,3,6,7-Tetrahydrooxepin-2- or -3- or -4-yl;2,3-Dihydrooxepin-2- or -3- or -4- or -5- or -6- or -7-yl;4,5-Dihydrooxepin-2- or -3- or -4-yl;2,5-Dihydrooxepin-2- or -3- or -4-yl 2- or 3- or 4- or 5- or 6- or 7-yl; oxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2- or 3-tetrahydrothiophenyl; 2,3-dihydrothiophene-2- or 3- or 4- or 5-yl; 2,5-dihydrothiophene-2- or 3-yl; tetrahydro-2H-thio Pyran-2- or -3- or -4-yl; 3,4-dihydro-2H-thiopyran-2- or -3- or -4- or -5- or -6-yl; 3,6-dihydro-2H-thiopyran-2- or -3- or -4- or -5- or -6-yl; 2H-thiopyran-2- or -3- or -4- or -5- or -6-yl; 4H-thiopyran-2- or -3- or -4-yl. Preferred 3- and 4-membered heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1-, 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3-dioxetan-2-yl. Further examples of "heterocyclyl" are partially or fully hydrogenated heterocyclic groups having two heteroatoms of the groups N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazol-3- or 4- or 5-yl; 4,5-dihydro-1H-pyrazol-1- or 3- or 4- or 5-yl;2,3-Dihydro-1H-pyrazol-1- or 2- or 3- or 4- or 5-yl;1- or 2- or 3- or 4-imidazolidinyl;2,3-Dihydro-1H-imidazol-1- or 2- or 3- or 4-yl;2,5-Dihydro-1H-imidazol-1- or 2- or 4- or 5-yl;4,5-Dihydro-1H-imidazol-1- or 2- or 4- or 5-yl;Hexahydropyridazin-1- or 2- or 3- or 4-yl;1,2,3,4-Tetrahydropyridazin-1- or 2 - or 3- or 4- or 5- or 6-yl;1,2,3,6-tetrahydropyridazin-1- or 2- or 3- or 4- or 5- or 6-yl;1,4,5,6-tetrahydropyridazin-1- or 3- or 4- or 5- or 6-yl;3,4,5,6-tetrahydropyridazin-3- or 4- or 5-yl;4,5-dihydropyridazin-3- or 4-yl;3,4-dihydropyridazin-3- or 4- or 5- or 6-yl;3,6-dihydropyridazin-3- or 4-yl;1,6-dihydropyridazin ridazine-1- or 3- or 4- or 5- or 6-yl;hexahydropyrimidin-1- or 2- or 3- or 4-yl;1,4,5,6-tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl;1,2,5,6-tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl;1,2,3,4-tetrahydropyrimidin-1- or 2- or 3- or 4- or 5- or 6-yl;1,6-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl;1,2 -dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl;2,5-dihydropyrimidin-2- or 4- or 5-yl;4,5-dihydropyrimidin-4- or 5- or 6-yl;1,4-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl;1- or 2- or 3-piperazinyl;1,2,3,6-tetrahydropyrazin-1- or 2- or 3- or 5- or 6-yl;1,2,3,4-tetrahydropyrazin-1- or 2- or 3- or 4- or 5- or 6-yl;1,2-Dihydropyrazine-1- or 2- or 3- or 5- or 6-yl;1,4-Dihydropyrazine-1- or 2- or 3-yl;2,3-Dihydropyrazine-2- or 3- or 5- or 6-yl;2,5-Dihydropyrazine-2- or 3-yl;1,3-Dioxolane-2- or 4- or 5-yl;1,3-Dioxol-2- or 4-yl;1,3-Dioxane-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-dithiolane-3- or 4-yl;3H-1,2-dithiol-3- or 4- or 5-yl;1,3-dithiolane-2- or 4-yl;1,3-dithiol-2- or 4-yl;1,2-dithiane-3- or 4-yl;3,4-dihydro-1,2-dithiin-3- or 4- or 5- or 6-yl;3,6-dihydro-1,2-dithiin-3- or 4- yl;1,2-dithiin-3- or 4-yl;1,3-dithiane-2- or 4- or 5-yl;4H-1,3-dithiin-2- or 4- or 5- or 6-yl;isoxazolidine-2- or 3- or 4- or 5-yl;2,3-dihydroisoxazol-2- or 3- or 4- or 5-yl;2,5-dihydroisoxazol-2- or 3- or 4- or 5-yl;4,5-dihydroisoxazol-3- or 4- or 5-yl;1,3-oxazolidine-2- or 3- or 4- or 5-yl yl;2,3-dihydro-1,3-oxazol-2- or 3- or 4- or 5-yl;2,5-dihydro-1,3-oxazol-2- or 4- or 5-yl;4,5-dihydro-1,3-oxazol-2- or 4- or 5-yl;1,2-oxazinan-2- or 3- or 4- or 5- or 6-yl;3,4-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl;3,6-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl;5,6-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,2-oxazin-3- or 4- or 5- or 6-yl; 2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 6H-1,2-oxazin-3- or 4- or 5- or 6-yl; 4H-1,2-oxazin-3- or 4- or 5- or 6-yl; 1,3-oxazinane-2- or 3- or 4- or 5- or 6-yl; or 4- or 5- or 6-yl;3,4-dihydro-2H-1,3-oxazin-2- or 3- or 4- or 5- or 6-yl;3,6-dihydro-2H-1,3-oxazin-2- or 3- or 4- or 5- or 6-yl;5,6-dihydro-2H-1,3-oxazin-2- or 4- or 5- or 6-yl;5,6-dihydro-4H-1,3-oxazin-2- or 4- or 5- or 6-yl;2H-1,3-oxazin-2- or 4- or 5- or 6-yl;6H-1,3-oxazin-2 - or 4- or 5- or 6-yl;4H-1,3-oxazin-2- or 4- or 5- or 6-yl;morpholin-2- or 3- or 4-yl;3,4-dihydro-2H-1,4-oxazin-2- or 3- or 4- or 5- or 6-yl;3,6-dihydro-2H-1,4-oxazin-2- or 3- or 5- or 6-yl;2H-1,4-oxazin-2- or 3- or 5- or 6-yl;4H-1,4-oxazin-2- or 3-yl;1,2-oxazepane-2- or 3- or 4- or 5- or 6- or 7-yl;2,3,4,5-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;2,3,4,7-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;2,3,6,7-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;2,5,6,7-tetrahydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;4,5 ,6,7-tetrahydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl;2,3-dihydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;2,5-dihydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;2,7-dihydro-1,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;4,5-dihydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl;4,7-dihydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl;6,7-dihydro-1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl;1,2-oxazepin-3- or 4- or 5- or 6- or 7-yl;1,3-oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl;2,3,4,5-tetrahydro-1,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;2,3,4,7-tetrahydro-1,3-oxazepin- 2- or 3- or 4- or 5- or 6- or 7-yl;2,3,6,7-tetrahydro-1,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;2,5,6,7-tetrahydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl;4,5,6,7-tetrahydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl;2,3-dihydro-1,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;2,5-dihydro-1,3 -oxazepin-2- or 4- or 5- or 6- or 7-yl;2,7-dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl;4,5-dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl;4,7-dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl;6,7-dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl;1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 1,4-Oxazepan-2- or 3- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl;4,5,6,7-tetrahydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 2,5-dihydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 2,7-dihydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 4,5-dihydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl;4,7-dihydro-1,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;6,7-dihydro-1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl;1,4-oxazepin-2- or 3- or 5- or 6- or 7-yl;isothiazolidine-2- or 3- or 4- or 5-yl;2,3-dihydroisothiazol-2- or 3- or 4- or 5-yl;2,5-dihydroisothiazol-2- or 3- or 4- or 5-yl;4,5-dihydroisothiazol-3- or 4- or 5-yl;1,3-thiazolidine-2- or 3- or 4- or 5-yl;2,3-dihydro-1,3-thiazol-2- or 3- or 4- or 5-yl;2,5-dihydro-1,3-thiazol-2- or 4- or 5-yl;4,5-dihydro-1,3-thiazol-2- or 4- or 5-yl;1,3-thiazinane-2- or 3- or 4- or 5- or 6-yl;3,4-dihydro- 2H-1,3-thiazin-2- or 3- or 4- or 5- or 6-yl;3,6-dihydro-2H-1,3-thiazin-2- or 3- or 4- or 5- or 6-yl;5,6-dihydro-2H-1,3-thiazin-2- or 4- or 5- or 6-yl;5,6-dihydro-4H-1,3-thiazin-2- or 4- or 5- or 6-yl;2H-1,3-thiazin-2- or 4- or 5- or 6-yl;6H-1,3-thiazin-2- or 4- or 5- or 6-yl;Further examples of "heterocyclyl" are partially or fully hydrogenated heterocyclic groups having three heteroatoms of the groups N, O and S, such as 1,4,2-dioxazolidine-2- or 3- or 5-yl; 1,4,2-dioxazol-3- or 5-yl; 1,4,2-dioxazinan-2- or -3- or 5- or 6-yl; 5,6-dihydro-1,4,2-dioxazin-3- or 5- or 6-yl; 1,4,2-dioxazin-3- or 5- or 6-yl; 1,4,2-dioxazepane-2- or 3- or 5-yl. or 6- or 7-yl; 6,7-dihydro-5H-1,4,2-dioxazepin-3- or 5- or 6- or 7-yl; 2,3-dihydro-7H-1,4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl; 2,3-dihydro-5H-1,4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl; 5H-1,4,2-dioxazepin-3- or 5- or 6- or 7-yl; 7H-1,4,2-dioxazepin-3- or 5- or 6- or 7-yl. Examples of the structure of the heterocycle which may be further substituted are also listed below:; [Table 3] TIFF0007654654000008.tif234170 TIFF0007654654000009.tif38168

[0040] The heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxyl, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, trisalkylsilylalkynyl, nitro, amino, cyano, haloalkoxy, haloalkenyl, cycloalkoxy, cycloalkylalkoxy, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, trisalkylsilylalkynyl, nitro, amino, cyano, haloalkoxy, haloalkenyl, cycloalkoxy ... Substituted by alkylthio, alkylthio, hydrothio, hydroxyalkyl, oxo, heteroarylalkoxy, arylalkoxy, heterocyclylalkoxy, heterocyclylalkylthio, heterocyclyloxy, heterocyclylthio, heteroaryloxy, bisalkylamino, alkylamino, cycloalkylamino, hydroxycarbonylalkylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, alkoxycarbonylalkyl(alkyl)amino, aminocarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl, cycloalkylaminocarbonyl, hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl, arylalkoxycarbonylalkylaminocarbonyl.

[0041] Where a base structure is substituted "by one or more radicals" from a list of radicals (= groups) or generally defined groups of radicals, this includes in each case simultaneous substitution by several identical and / or structurally different radicals.

[0042] In the case of a partially or fully saturated nitrogen heterocycle, it may be attached to the remainder of the molecule through either the carbon or the nitrogen.

[0043] Suitable substituents for substituted heterocyclic groups are those further specified below, and also oxo and thioxo. In that case, the oxo group as a substituent on a ring carbon atom is, for example, a carbonyl group in a heterocyclic ring. As a result, preferably, lactones and lactams are also included. The oxo group may also be present on a ring heteroatom, for example, in the case of N and S, in different oxidation states, and in that case, for example, form divalent -N(O)-, -S(O)- (also abbreviated SO) and -S(O)2- (also abbreviated SO2) groups in a heterocyclic ring. In the case of -N(O)- and -S(O)- groups, in each case, both enantiomers are included.

[0044] According to the present invention, the expression "heteroaryl" denotes a heteroaromatic compound, i.e. a fully unsaturated aromatic heterocyclic compound, preferably a 5-7 membered ring having 1 to 4, preferably 1 or 2 identical or different heteroatoms, preferably O, S or N. Heteroaryls according to the present invention are, for example, 1H-pyrrol-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl; furan-2-yl; furan-3-yl; thien-2-yl; thien-3-yl, 1H-imidazol-1-yl; 1H-imidazol-2-yl; 1H-imidazol-4-yl; 1H-imidazol-5-yl; 1H-pyrazol-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1H-pyrazol-5-yl, 1H-1,2,3-triphenylphosphine, 1H-pyrazole ... Azol-1-yl, 1H-1,2,3-triazol-4-yl, 1H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1,2,4-triazol-1-yl, 1H-1,2,4-triazol-3-yl, 4H-1,2,4-triazol-4-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1, 2,3-Oxadiazol-4-yl, 1,2,3-Oxadiazol-5-yl, 1,2,5-Oxadiazol-3-yl, Azepinyl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Pyrazin-2-yl, Pyrazin-3-yl, Pyrimidin-2-yl, Pyrimidin-4-yl, Pyrimidin-5-yl, Pyridazin-3-yl, Pyridazin-4-yl, 1,3,5-Triazin-2-yl, 1,2,4-Triazin-3-yl, 1,2,4-Triazin-5-yl , 1,2,4-triazin-6-yl, 1,2,3-triazin-4-yl, 1,2,3-triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 1,3-oxazol-2-yl, 1,3-oxazol-4-yl, 1,3-oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,3-thiazol-2-yl, 1,3-thiazol-4-yl, 1,3-thiazol-5-yl, oxepinyl, thiepinyl, 1,2,4-triazolonyl and 1,2,4-diazepinyl, 2H-1,2,3,4-tetrazol-5-yl, 1H-1,2,3,4-tetrazol-5-yl, 1,2,3,4-oxatriazol-5-yl, 1,2,3,4-thiatriazol-5-yl, 1,2,3,5-oxatriazol-4-yl, 1,2,3,5-thiatriazol-4-yl. The heteroaryl groups of the present invention may also be substituted by one or more identical or different groups. When two adjacent carbon atoms are part of an additional aromatic ring, these systems are fused heteroaromatic systems, such as benzo-fused or poly-fused heteroaromatic rings. Preferred examples are quinolines (e.g., quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl); isoquinolines (e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl); quinoxalines; quinazolines; cinnolines; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,Examples of heteroaryls are also 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-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-benzofuran-5-yl, 1-benzofuran ...furan-2- 1H-indazol-4-yl, 1-benzothiophen-5-yl, 1-benzothiophen-6-yl, 1-benzothiophen-7-yl, 1H-indazol-1-yl, 1H-indazol-3-yl, 1H-indazol-4-yl, 1H-indazol-5-yl, 1H-indazol-6-yl, 1H-indazol-7-yl, 2H-indazol-2-yl, 2H-indazol-3-yl, 2H-indazol-4-yl, 2H-indazol-5-yl, 2H-indazol-6-yl, 2H-indazol-7-yl , 2H-isoindol-2-yl, 2H-isoindol-1-yl, 2H-isoindol-3-yl, 2H-isoindol-4-yl, 2H-isoindol-5-yl, 2H-isoindol-6-yl; 2H-isoindol-7-yl, 1H-benzimidazol-1-yl, 1H-benzimidazol-2-yl, 1H-benzimidazol-4-yl, 1H-benzimidazol-5-yl, 1H-benzimidazol-6-yl, 1H-benzimidazol-7-yl, 1,3-benzoxazole- 2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl, 1,3-benzoxazol-7-yl, 1,3-benzothiazol-2-yl, 1,3-benzothiazol-4-yl, 1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl, 1,3-benzothiazol-7-yl, 1,2-benzisoxazol-3-yl, 1,2-benzisoxazol-4-yl, 1,2-benzisoxazol-5-yl, 1,5- or 6-membered benzo-fused rings from the group: 2-benzisoxazol-6-yl, 1,2-benzisoxazol-7-yl, 1,2-benzisothiazol-3-yl, 1,2-benzisothiazol-4-yl, 1,2-benzisothiazol-5-yl, 1,2-benzisothiazol-6-yl, 1,2-benzisothiazol-7-yl.

[0045] The term "halogen" refers, for example, to a fluorine, chlorine, bromine or iodine atom. When used in accordance with this terminology, "halogen" refers, for example, to a fluorine, chlorine, bromine or iodine atom.

[0046] According to the present invention, "alkyl" means a linear or branched open-chain saturated hydrocarbon group which may be mono- or polysubstituted, in the latter case it is called "substituted alkyl". Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, cycloalkyl, alkoxycarbonyl, hydroxycarbonyl, heterocyclyl, hetaryl, aryl, amino or nitro groups, with methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine being particularly preferred. The prefix "bis" also includes combinations of different alkyl groups, such as methyl (ethyl) or ethyl (methyl).

[0047] "Haloalkyl", "-alkenyl" and "-alkynyl" refer respectively to alkyl, alkenyl and alkynyl partially or fully substituted with the same or different halogen atoms, e.g. monohaloalkyl, such as CH2CH2Cl, CH2CH2Br, CHClCH3, CH2Cl, CH2F; perhaloalkyl, such as CCl3, CClF2, CFCl2, CF2CClF2, CF2CClFCF3; polyhaloalkyl, such as CH2CHFCl, CF2CClFH, CF2CBrFH, CH2CF3; the term perhaloalkyl also encompasses the term perfluoroalkyl.

[0048] "Partially fluorinated alkyl" denotes a linear or branched saturated hydrocarbon that is mono- or polysubstituted with fluorine, the fluorine atoms in question may be present as substituents on one or more different carbon atoms of the linear or branched hydrocarbon chain, e.g., CHFCH3, CH2CH2F, CH2CH2CF3, CHF2, CH2F, CHFCF2CF3.

[0049] "Partially fluorinated haloalkyl" refers to a linear or branched saturated hydrocarbon group substituted with at least one fluorine atom by different halogen atoms, the other halogen atoms which may be present being selected from the group consisting of fluorine, chlorine or bromine, iodine. The corresponding halogen atoms may be present as substituents on one or more different carbon atoms of the linear or branched hydrocarbon chain. Partially fluorinated haloalkyl also includes the complete substitution of the linear or branched chain with halogens, including at least one fluorine atom.

[0050] "Haloalkoxy" is, for example, OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3, and OCH2CH2Cl; this applies equally to haloalkenyl and other halogen substituents.

[0051] The expression "(C1-C4)-alkyl" mentioned herein by way of example is a shorthand notation for linear or branched alkyl groups having 1 to 4 carbon atoms according to the stated range of carbon atoms, i.e. encompasses methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl groups. General alkyl groups having a larger specified range of carbon atoms, such as "(C1-C6)-alkyl", likewise encompass linear or branched alkyl groups having a higher number of carbon atoms, i.e. by way of example, alkyl groups having 5 and 6 carbon atoms.

[0052] Unless specifically stated otherwise, in the case of hydrocarbon groups such as alkyl, alkenyl and alkynyl groups, including complex groups, in the case of unsaturated groups, low carbon skeletons, for example with 1 to 6 carbon atoms or with 2 to 6 carbon atoms, are preferred. Alkyl groups, including complex groups such as alkoxy, haloalkyl, are for example methyl, ethyl, n-propyl or i-propyl, n-, i-, t- or 2-butyl, pentyl, hexyl, for example n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyl, for example n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl groups are defined as possible unsaturated groups corresponding to the alkyl group, in which at least one double or triple bond is present. Groups with one double or triple bond are preferred.

[0053] The term "alkenyl" also includes linear or branched open-chain hydrocarbon groups with two or more double bonds, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl groups with one or more cumulative double bonds, such as allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl. Alkenyl includes, for example, vinyl, which may be substituted by further alkyl groups, such as (but not limited to) ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-but ...methyl-2-propenyl, 2-methyl-2-propenyl -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.

[0054] The term "alkynyl" also includes, in particular, straight or branched open-chain hydrocarbon groups having two or more triple bonds, or having one or more triple bonds and one or more double bonds, such as 1,3-butatrienyl or 3-penten-1-yn-1-yl. Examples of (C2-C6)-alkynyl include 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- The examples include 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.

[0055] 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 may be further substituted, preferably with hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, alkoxycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl. In the case of optionally substituted cycloalkyl, substituted ring systems are included, including also substituents having a double bond on the cycloalkyl group, for example alkylidene groups such as methylidene. In the case of optionally substituted cycloalkyl, polycyclic aliphatic systems such as bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-1-yl, bicyclo[1.1.1]pentan-1-yl, bicyclo[2.1.0]pentan-2-yl, bicyclo[2.1.0]pentan-5-yl, bicyclo[2.1.1]hexyl, etc. Bicyclo[2.2.1]hept-2-yl, bicyclo[2.2.2]octan-2-yl, bicyclo[3.2.1]octan-2-yl, bicyclo[3.2.2]nonan-2-yl, adamantan-1-yl and adamantan-2-yl are also included, but also systems such as 1,1'-bi(cyclopropyl)-1-yl, 1,1'-bi(cyclopropyl)-2-yl. The term "(C3-C7)-cycloalkyl" is a shorthand notation for cycloalkyl having 3 to 7 carbon atoms, corresponding to the range specified for carbon atoms.

[0056] Substituted cycloalkyl also includes spirocyclic aliphatic systems 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.

[0057] "Cycloalkenyl" refers to a carbocyclic, non-aromatic, partially unsaturated ring system, preferably having 4 to 8 carbon atoms, such as 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl, or 1,4-cyclohexadienyl, and also includes substituents having a double bond on the cycloalkenyl group, such as alkylidene groups, for example methylidene. In the case of an optionally substituted cycloalkenyl, the explanation of the substituted cycloalkyl applies in the same way.

[0058] For example, (C1~C 10 The term "alkylidene", in the form )-alkylidene, also denotes a radical of a straight or branched open chain hydrocarbon group bonded through a double bond. Possible bonding sites for alkylidene are, of course, only those positions on the base structure where two hydrogen atoms can be replaced by a double bond; radicals are, for example, =CH2, =CH-CH3, =C(CH3)-CH3, =C(CH3)-C2H5 or =C(C2H5)-C2H5. Cycloalkylidene denotes a carbocyclic radical bonded through a double bond.

[0059] "Alkoxyalkyl" refers to an alkoxy group bonded through an alkyl group and "alkoxyalkoxy" refers to an alkoxyalkyl group bonded through an oxygen atom, such as, but not limited to, methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy.

[0060] "Alkylthioalkyl" refers to an alkylthio group bonded through an alkyl group and "alkylthioalkylthio" refers to an alkylthioalkyl group bonded through an oxygen atom.

[0061] "Arylalkoxyalkyl" refers to an aryloxy group bonded through an alkyl group, and "heteroaryloxyalkyl" refers to a heteroaryloxy group bonded through an alkyl group.

[0062] "Haloalkoxyalkyl" refers to a haloalkoxy group bonded and "haloalkylthioalkyl" refers to a haloalkylthio group bonded through an alkyl group.

[0063] "Arylalkyl" refers to an aryl group bonded through an alkyl group, "heteroarylalkyl" refers to a heteroaryl group bonded through an alkyl group, and "heterocyclylalkyl" refers to a heterocyclyl group bonded through an alkyl group.

[0064] "Cycloalkylalkyl" refers to a cycloalkyl group bonded through an alkyl group, such as, but not limited to, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropyleth-1-yl, 2-cyclopropyleth-1-yl, 1-cyclopropylprop-1-yl, 3-cyclopropylprop-1-yl.

[0065] According to the present invention, "haloalkylthio", alone or as part of a chemical group, denotes a straight or branched S-haloalkyl, preferably having 1 to 8 carbon atoms, or having 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-difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio, 3,3,3-prop-1-ylthio.

[0066] "Halocycloalkyl" and "halocycloalkenyl" refer to cycloalkyl and cycloalkenyl, respectively, that are partially or fully substituted with the same or different halogen atoms, such as F, Cl and Br, or with haloalkyls, such as trifluoromethyl or difluoromethyl, e.g., 1-fluorocycloprop-1-yl, 2-fluorocycloprop-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocyclobut-1-yl, 1-trifluoromethylcycloprop-1-yl, 2-trifluoromethylcycloprop-1-yl, 1-chlorocycloprop-1-yl, 2-chlorocycloprop-1-yl, 2,2-dichlorocycloprop-1-yl, 3,3-difluorocyclobutyl.

[0067] According to the present invention, "trialkylsilyl", alone or as part of a chemical group, denotes a linear or branched Si-alkyl, preferably having 1 to 8 carbon atoms, or having 1 to 6 carbon atoms, such as tri[(C1-C8)-, (C1-C6)- or (C1-C4)-alkyl]silyl, such as (but not limited to) trimethylsilyl, triethylsilyl, tri(n-propyl)silyl, tri(isopropyl)silyl, tri(n-butyl)silyl, tri(1-methylprop-1-yl)silyl, tri(2-methylprop-1-yl)silyl, tri(1,1-dimethyleth-1-yl)silyl, tri(2,2-dimethyleth-1-yl)silyl.

[0068] Where a compound can form, through hydrogen shift, tautomers whose structures are not formally encompassed by general formula (I), these tautomers are nevertheless encompassed within the definition of the compounds of the invention of general formula (I), unless a specific tautomer is being discussed. For example, many carbonyl compounds can exist in both keto and enol forms, and both forms are encompassed within the definition of the compounds of general formula (I).

[0069] Depending on the nature of the substituents and the way in which they are attached, the compounds of general formula (I) may exist as stereoisomers. All possible stereoisomers defined by their specific three-dimensional form, such as enantiomers, diastereomers, Z and E isomers, are encompassed by general formula (I). For example, when one or more alkenyl groups are present, diastereomers (Z and E isomers) may occur. For example, when one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur. Stereoisomers can be obtained by conventional separation methods from the mixtures obtained in the preparation. Chromatographic separation can be carried out on an analytical scale to find the enantiomeric or diastereomeric excess, or on a preparative scale to prepare test specimens for biological testing. Similarly, it is possible to selectively prepare stereoisomers by using stereoselective reactions using optically active starting materials and / or auxiliaries. Thus, the present invention also relates to all stereoisomers that are encompassed by general formula (I) but are not shown in their specific stereoisomeric form, and mixtures thereof.

[0070] If the compounds are obtained as solids, purification can also be carried out by recrystallization or digestion. If the individual compounds (I) cannot be obtained satisfactorily by the routes described below, they can be prepared by derivatization of other compounds of general formula (I).

[0071] Suitable methods for isolation, purification and separation of the stereoisomers of the compounds of general formula (I) are generally known to those skilled in the art from similar cases, for example by physical methods such as crystallization, chromatographic methods, in particular column chromatography and HPLC (High Performance Liquid Chromatography), distillation, possibly under reduced pressure, extraction and other methods, and any remaining mixtures can generally be separated, for example by chromatographic separation on chiral solid phases. Methods such as crystallization of diastereomeric salts, which can be obtained from diastereomeric mixtures, for example using optically active acids and, where appropriate, when acidic groups are present, optically active bases, are suitable for preparative or industrial scale.

[0072] Synthesis of [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives of general formula (I) [ka]

[0073] The [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives of the present invention of general formula (I) can be prepared proceeding from known methods. The synthetic routes used and tested proceed from commercially available chemicals such as commercially available or easily preparable substituted benzoic acids, the corresponding substituted benzamides, and substituted phenylhydrazines and diphenyl carbonates. In the following scheme, the moiety R of general formula (I) 1 , R 2 , R 3 , R 4 , m, n and p have the meanings defined above, unless exemplary and non-limiting definitions are given.

[0074] The compound of the present invention of general formula (Ia) is synthesized via the reaction of 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, at a temperature range between 0° C. and 120° C. (see Scheme 1). [ka]

[0075] Scheme 1. Compounds of general formula (II) are synthesized via cyclization of compounds of general formula (IV) in the presence of a condensation reagent, such as polyphosphoric acid. The reaction is preferably carried out in neat form within a temperature range between 0° C. and 180° C. (see Scheme 2). [ka]

[0076] Scheme 2. The synthesis of the compound of general formula (IV) can be prepared by the reaction of the compound of general formula (V) with the phenylhydrazine of general formula (VI) in a suitable solvent, such as acetonitrile, at a temperature range between -20°C and 100°C, preferably between -5°C and 50°C. The reaction is carried out in the presence of a base, such as triethylamine. It is also possible to use the phenylhydrazine hydrohalide of general formula (VII) instead of the phenylhydrazine of general formula (VI) (Scheme 3). [ka]

[0077] Scheme 3. The synthesis of compounds of general formula (V) can be prepared by the reaction of compounds of general formula (VIII) with diphenyl carbonate (IX) in the presence of a base, such as sodium hydride (see Scheme 4). The reaction is preferably carried out in a suitable solvent, such as THF, at a temperature range between -20°C and 150°C. Compounds of general formula (VIII) and (IX) are commercially available or can be prepared similarly to methods known to those skilled in the art. [ka]

[0078] Scheme 4. The synthesis of the acids of general formula (X) can be prepared by hydrolysis of the compounds of general formula (Ia) or similarly by methods known to those skilled in the art.

[0079] The hydrolysis can be carried out in the presence of a base or a Lewis acid. The base can be a hydroxide salt of an alkali metal (e.g., lithium, sodium or potassium; Scheme 5), and the hydrolysis reaction is preferably carried out at a temperature range between room temperature and 100° C. The Lewis acid can be boron tribromide, and the reaction can be carried out at a temperature range between −20° C. and 100° C., preferably between −5° C. and 50° C. [ka]

[0080] Scheme 5. The compounds of the present invention of general formula (Ia) are synthesized via esterification of an acid of general formula (X) with an alcohol of general formula (XII) in the presence of a coupling reagent such as T3P, dicyclohexylcarbodiimide, N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide, N,N'-carbonyldiimidazole, 2-chloro-1,3-dimethylimidazolium chloride or 2-chloro-1-methylpyridinium iodide (see Chemistry of Peptide Synthesis, Ed. N. Leo Benoiton, Taylor & Francis, 2006, ISBN-10:1-57444-454-9). Polymer-supported reagents such as polymer-supported dicyclohexylcarbodiimide are also suitable for this coupling reaction. The reaction is preferably carried out in a suitable solvent such as dichloromethane, acetonitrile, N,N-dimethylformamide or ethyl acetate, and in the presence of a base such as triethylamine, N,N-diisopropylethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene, at a temperature range between 0° C. and 80° C. (see Scheme 6). For T3P coupling conditions, see Organic Process Research & Development 2009, 13, 900-906. [ka]

[0081] Scheme 6. Scheme 7 shows the synthesis of a compound of general formula (II); the synthesis is carried out by reaction of a compound of general formula (XIII) in the presence of a Bronsted acid, for example 33% HBr in acetic acid. The reaction is preferably carried out at a temperature range between 0° C. and 180° C. See Bioorganic & Medicinal Chemistry 2018, 26, 3321-3344. [ka]

[0082] Scheme 7. Compounds of general formula (XIII) can be prepared by reaction of compounds of general formula (XIV) with phenylhydrazines of general formula (VI) in a suitable solvent, such as ethanol (see Scheme 8). The reaction is preferably carried out at a temperature range between 0° C. and 150° C. [ka]

[0083] Scheme 8. Compounds of general formula (XIV) can be prepared by reacting benzoyl halides of general formula (XV) with thiocyanate salts of general formula (XVI) in a suitable solvent, such as acetone, in the presence of methanol (see scheme 9). Benzoyl halides are commercially available or can be prepared in analogy to methods known to those skilled in the art. See Tetrahedron 1968,24,5205-5214; J.Chem.Soc.1957,1091; JP81 53,664(1981); Justus Liebigs Ann.Chem.1964,675,180 and J.heterocycl.Chem.1983,20,1533. [ka]

[0084] Scheme 9. Selected detailed synthetic examples for the compounds of the present invention of general formula (I) are given below. The example numbers mentioned correspond to the numbering schemes in Tables I.1 to I.77 below. The chemical examples described in the following sections are reported. 1 H NMR, 13 C-NMR and 19 F-NMR spectroscopic data ( 1 H NMR: 400MHz, 13 C-NMR is 150MHz, 19F-NMR was obtained on a Bruker instrument at 375 MHz, solvents CDCl3, CD3OD or d6-DMSO, internal standard: tetramethylsilane (δ = 0.00 ppm), and the listed signals have the meanings given below: br = broad; s = singlet, d = doublet, t = triplet, dd = doublet of doublets, ddd = doublet of doublets of doublets, m = multiplet, q = quartet, quint = quintet, sext = sextet, sept = septet, dq = doublet of quartets, dt = doublet of triplets. In case of diastereomeric mixtures, significant signals are reported for each of the two diastereomers or the characteristic signal of the major diastereomer is reported. The abbreviations used for the chemical groups have, for example, the following meanings: Me=CH3, Et=CH2CH3, t-Hex=C(CH3)2CH(CH3)2, t-Bu=C(CH3)3, n-Bu=unbranched butyl, n-Pr=unbranched propyl, i-Pr=branched propyl, c-Pr=cyclopropyl, c-Hex=cyclohexyl.

[0085] [Synthesis Example] Synthesis Example Number: I.42-7 Synthesis Step 1: Phenyl(2,4-difluorobenzoyl)carbamate [ka]

[0086] 2,4-Difluorobenzamide (10 g, 63.65 mmol, 1.0 eq.) and diphenyl carbonate (20.45 g, 1.5 eq.) were dissolved in THF (100 ml) under an argon atmosphere and cooled to 0° C. in an ice bath. Sodium hydride (60% in mineral oil, 2.55 g, 63.65 mmol, 1.0 eq.) was added in portions to the solution. Caution: gas evolution! The ice bath was then removed and the reaction mixture was stirred at room temperature for 1 h. The reaction mixture was then concentrated to 1 / 3 under reduced pressure, forming a flaky white solid. The solid obtained was filtered off with suction and dried under air. Phenyl (2,4-difluorobenzoyl) carbamate was isolated in the form of a white solid (11.51 g, 61% of theory). 1 H NMR (400 MHz, DMSO-d6 δ,ppm)7.76(m,1H),7.36-7.28(m,2H),7.18-6.99(m,4H),6.77-6.74(m,2H). Synthesis step 2: 2-(4-chlorophenyl)-N-(2,4-difluorobenzoyl)hydrazinecarboxamide [ka]

[0087] Phenyl(2,4-difluorobenzoyl)carbamate (8 g, 28.86 mmol, 1.0 equiv.) was dissolved in acetonitrile (85 ml) and then the following was added at room temperature: (4-chlorophenyl)hydrazine hydrochloride (1:1) (5.68 g, 31.74 mmol, 1.1 equiv.) and triethylamine (8.04 ml, 57.72 mmol, 2.0 equiv.). The solution turned pink after about 15-30 min and a beige solid precipitated. The reaction mixture was stirred at room temperature for 1 h, then the resulting precipitate was filtered off and dried under air. 2-(4-chlorophenyl)-N-(2,4-difluorobenzoyl)hydrazinecarboxamide was isolated in the form of a beige solid (3.67 g, 38% of theory). 1 H NMR (400 MHz, DMSO-d 6 δ,ppm)9.74(bs,1H),8.11(bs,1H),7.75(m,1H),7.48-7.29(m,2H),7.18(d,2H),6.73(d,2H). Synthesis step 3: 1-(4-chlorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-ol [ka]

[0088] 2-(4-Chlorophenyl)-N-(2,4-difluorobenzoyl)hydrazinecarboxamide (3 g, 11.21 mmol, 1.0 eq.) was blended in polyphosphoric acid (50 ml) and then at 100° C. for 2 hours to liquefy the reaction mixture. After cooling to room temperature, the reaction mixture was added dropwise to ice water and the pale beige precipitate was filtered off with suction. The precipitate filtered off with suction was dried at 55° C. in a vacuum drying cabinet. 1-(4-Chlorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-ol was isolated in the form of a pale beige solid (1.73 g, 49% of theory). 1 H NMR (400 MHz, DMSO-d 6 δ,ppm)11.57(bs,1H),7.68(m,1H),7.49(d,2H),7.37(m,1H),7.32-7.24(m,3H). Synthesis Step 4: Methyl {[1-(4-chlorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (Synthetic Example I.40-7) [ka]

[0089] 1-(4-chlorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-ol (1.7 g, 5.53 mmol, 1.0 eq.) and potassium carbonate (1.53 g, 11.05 mmol, 2 eq.) were suspended in acetonitrile (20 ml) and then methyl bromoacetate (0.48 g, 6.63 mmol, 1.2 eq.) was added. The suspension was then stirred overnight at room temperature, the solid was filtered off and the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate / heptane gradient). Methyl {[1-(4-chlorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate was isolated in the form of a colorless oil (1.62 g, 76% of theory). 1H MR(400 MHz,CDCl3δ,ppm)7.59(m,1H),7.33(d,2H),7.20(d,2H),7.00(m,1H),6.79(m,1H),4.94(s,2H),3.81(s,3H). Synthesis Step 5: {[1-(4-chlorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid (Synthetic Example I.42-7) [ka]

[0090] Methyl {[1-(4-chlorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (1.6 g, 4.21 mmol, 1.0 eq.) and lithium hydroxide (101 mg, 4.21 mmol, 1 eq.) were dissolved in a THF / water mixture (7:2, 20 ml) and then 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 2M hydrochloric acid, whereupon a pale yellow solid precipitated. The precipitate was filtered off with suction and dried at 55° C. in a vacuum drying cabinet. {[1-(4-chlorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid was isolated in the form of a pale yellow solid (1.44 g, 92% of theory). 1 H NMR (400 MHz, DMSO-d 6 δ,ppm)13.09(bs,1H),7.77(m,1H),7.53(d,2H),7.41-7.26(m,4H),4.87(s,2H). Synthesis Example Number: I.61-49 Synthesis Step 1: 2,4-Dichlorobenzoyl Isothiocyanate [ka]

[0091] 2,4-Dichlorobenzoyl chloride (10 g, 47.74 mmol, 1.0 eq.) was dissolved in toluene (70 ml). Potassium thiocyanate (5.57 g, 1.2 eq.) was added in portions to the solution. The reaction mixture was then heated to boiling for 3 hours. The solvent was then removed under reduced pressure. The crude product was used in the next step without further purification. 2,4-Dichlorobenzoyl isothiocyanate was isolated in the form of a yellow solid (15.63 g, 68% of theory, 70% pure). 1 H NMR(400 MHz,CDCl3δ,ppm)7.97(d,1H),7.53(d,1H),7.34(d,1H). Synthesis step 2: S-allyl (2,4-dichlorobenzoyl)carbamothioate [ka]

[0092] 2,4-Dichlorobenzoyl isothiocyanate (15.6 g, 67.22 mmol, 1.0 eq.) was dissolved in toluene (250 ml). Allyl alcohol (4.69 g, 80.66 mmol, 1.2 eq.) was added in portions to the solution. The reaction mixture was then heated to boiling for 4 hours. The solvent was then removed under reduced pressure. The crude product was used in the next step without further purification. S-Allyl(2,4-dichlorobenzoyl)carbamothioate was isolated in the form of a yellow solid (17.75 g, 81% of theory, 90% pure). 1 H NMR(400 MHz,CDCl3δ,ppm)8.82(bs,1H),7.78(d,1H),7.48(s,1H),7.36(d,1H),5.89(m,1H),5.33(m,1H),5.18(m,1H),3.61(d,1H). Synthesis step 3: 2-(4-chloro-2-fluorophenyl)-N-(2,4-dichlorobenzoyl)hydrazinecarboxamide [ka]

[0093] S-allyl(2,4-dichlorobenzoyl)carbamothioate (17.75 g, 61.17 mmol, 1.0 eq.) was dissolved in toluene (180 ml) and then the following was added at room temperature: (4-chloro-2-fluorophenyl)hydrazine hydrochloride (1:1) (12.05 g, 61.17 mmol, 1.0 eq.) and triethylamine (8.53 ml, 61.17 mmol, 1.0 eq.). The reaction mixture was stirred at boiling for 2 hours, cooled, then the precipitate formed was filtered off and dried at 55° C. in a vacuum drying cabinet for 2 hours. 2-(4-chloro-2-fluorophenyl)-N-(2,4-dichlorobenzoyl)hydrazinecarboxamide was isolated in the form of a pale yellow solid (27.33 g, 94% of theory, 80% pure). 1 H NMR (400 MHz, DMSO-d 6 δ,ppm)11.18(bs,1H),10.41(bs,1H),9.68(bs,1H),8.02(s,1H),7.71(s,1 H),7.62(d,1H),7.53(d,1H),7,31-7,12(m,2H),8.86(t,1H). Synthesis step 4: 1-(4-chloro-2-fluorophenyl)-5-(2,4-dichlorophenyl)-1H-1,2,4 triazol-3-ol [ka]

[0094] 2-(4-chloro-2-fluorophenyl)-N-(2,4-dichlorobenzoyl)hydrazinecarboxamide (110.30 g, 234.31 mmol, 1.0 eq.) was blended in polyphosphoric acid (1100 ml) and then at 100° C. for 2 hours to liquefy the reaction mixture. After cooling to room temperature, the reaction mixture was added dropwise to ice water and the pale beige precipitate was filtered off with suction. The precipitate filtered off with suction was dried at 55° C. in a vacuum drying cabinet. 1-(4-chloro-2-fluorophenyl)-5-(2,4-dichlorophenyl)-1H-1,2,4-triazol-3-ol was isolated in the form of a pale beige solid (70.88 g, 83% of theory). 1H NMR (400 MHz, DMSO-d 6 δ,ppm)7.75(s,1H),7.63(d,1H),7.59(d,1H),7.55-7.51(m,2H),7.39(t,1H),3.83(bs,1H). Synthesis Step 5: Methyl {[1-(4-chloro-2-fluorophenyl)-5-(2,4-dichlorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (Synthetic Examples I.43-49) [ka]

[0095] 1-(4-chloro-2-fluorophenyl)-5-(2,4-dichlorophenyl)-1H-1,2,4-triazol-3-ol (70.80 g, 197.44 mmol, 1.0 eq.) and potassium carbonate (54.57 g, 394.88 mmol, 2 eq.) were suspended in acetonitrile (700 ml) and then methyl bromoacetate (36.25 g, 236.93 mmol, 1.2 eq.) was added. The suspension was then stirred overnight at room temperature, the solid was filtered off and the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate / heptane gradient). Methyl {[1-(4-chloro-2-fluorophenyl)-5-(2,4-dichlorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate was isolated in the form of a light brown oil (57.91 g, 67% of theory). 1 H NMR(400 MHz, CDCl3δ, ppm)7.40-7.29(m,4H),7.19(dd,1H),7.12(dd,1H),4.94(s,2H),3.81(s,3H). Synthesis Step 6: {[1-(4-chloro-2-fluorophenyl)-5-(2,4-dichlorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid (Synthetic Examples I.45-49) [ka]

[0096] Methyl {[1-(4-chloro-2-fluorophenyl)-5-(2,4-dichlorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (5.0 g, 11.61 mmol, 1.0 eq.) and lithium hydroxide (417 mg, 17.42 mmol, 1.5 eq.) were dissolved in a THF / water mixture (7:2, 20 ml) and then 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 2M hydrochloric acid, whereupon a pale yellow solid precipitated. The precipitate was filtered off with suction and dried at 55° C. in a vacuum drying cabinet. {[1-(4-chloro-2-fluorophenyl)-5-(2,4-dichlorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid was isolated in the form of a pale beige solid (2.99 g, 61% of theory). 1 H NMR(400 MHz, CDCl3δ, ppm)7.41-7.27(m,4H),7.18(d,1H),7.11(d,1H),4.94(s,2H). Synthesis Step 7: Methyl 3-(2-{[1-(4-chloro-2-fluorophenyl)-5-(2,4-dichlorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetoxy)propanoate (Synthetic Example I.61-49) [ka]

[0097] Methyl 3-hydroxypropanoate (47 mg, 0.39 mmol, 1.1 equiv.) was dissolved in dichloromethane (3 ml) and then {[1-(4-chloro-2-fluorophenyl)-5-(2,4-dichlorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid (150 mg, 0.36 mmol, 1.0 equiv.) was added. T3P (0.32 ml, 0.54 mmol, 1.5 equiv.) was pipetted into this solution and the reaction mixture was stirred at room temperature for 1 h. Then, triethylamine (0.13 ml, 0.90 mmol, 2.5 equiv.) and DMAP (9 mg, 0.072 mmol, 0.2 equiv.) were added to the reaction mixture and the reaction mixture was stirred at room temperature overnight. Then, the reaction solution was extracted with water and dichloromethane and the phases were separated using a phase separator. The organic phase was concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate / heptane gradient). Methyl 3-(2-{[1-(4-chloro-2-fluorophenyl)-5-(2,4-dichlorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetoxy)propanoate was isolated in the form of a colorless oil (100 mg, 53% of theory). 1 H NMR(400 MHz, CDCl3δ, ppm)7.41-7.29(m,4H),7.19(d,1H),7.12(d,1H),4.92(s,2H),4.49(t,2H),4.14(q,2H),2.67(t,2H),1.25(t,3H). The general details for the preparation of substituted [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives, as well as the preparative examples cited above and recited at the appropriate points, are taken into consideration to obtain the compounds recited below. [ka]

[0098] Table I.1: Preferred compounds of formula (I.1) are compounds I.1-1 to I.1-53, in which Q has the meaning of Table 1 indicated in the respective row. Thus, compounds I.1-1 to I.1-53 in Table I.1 are defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [Table 4] TIFF0007654654000034.tif228157 [ka]

[0099] Table I.2: Preferred compounds of formula (I.2) are compounds I.2-2 to I.2-53, in which Q has the meaning of Table 1 indicated in the respective row. Thus, compounds I.2-2 to I.2-53 in Table I.2 are defined by the meaning of the respective entry numbers 2 to 53 for Q in Table 1. [ka]

[0100] Table I.3: Preferred compounds of formula (I.3) are compounds I.3-1 to I.3-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.3-1 to I.3-53 in Table I.3 are thus defined by the meanings of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0101] Table I.4: Preferred compounds of formula (I.4) are compounds I.4-1 to I.4-53, in which Q has the meaning of Table 1 indicated in the respective row. Thus, compounds I.4-1 to I.4-53 in Table I.4 are defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0102] Table I.5: Preferred compounds of formula (I.5) are compounds I.5-1 to I.5-53, in which Q has the meaning of Table 1 indicated in the respective row. Thus, compounds I.5-1 to I.5-53 in Table I.5 are defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0103] Table I.6: Preferred compounds of formula (I.6) are compounds I.6-1 to I.6-53, in which Q has the meaning of Table 1 indicated in the respective row. Thus, compounds I.6-1 to I.6-53 in Table I.6 are defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0104] Table I.7: Preferred compounds of formula (I.7) are compounds I.7-1 to I.7-53, in which Q has the meaning of Table 1 indicated in the respective row. Thus, compounds I.7-1 to I.7-53 in Table I.7 are defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0105] Table I.8: Preferred compounds of formula (I.8) are compounds I.8-1 to I.8-53, in which Q has the meaning of Table 1 indicated in the respective row. Thus, compounds I.8-1 to I.8-53 in Table I.8 are defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0106] Table I.9: Preferred compounds of formula (I.9) are compounds I.9-1 to I.9-53, in which Q has the meaning of Table 1 indicated in the respective row. Thus, compounds I.9-1 to I.9-53 in Table I.9 are defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0107] Table I.10: Preferred compounds of formula (I.10) are compounds I.10-1 to I.10-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.10-1 to I.10-53 of Table I.10 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0108] Table I.11: Preferred compounds of formula (I.11) are compounds I.11-1 to I.11-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.11-1 to I.11-53 of Table I.11 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0109] Table I.12: Preferred compounds of formula (I.12) are compounds I.12-1 to I.12-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.12-1 to I.12-53 of Table I.12 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0110] Table I.13: Preferred compounds of formula (I.13) are compounds I.13-1 to I.13-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.13-1 to I.13-53 of Table I.13 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0111] Table I.14: Preferred compounds of formula (I.14) are compounds I.14-1 to I.14-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.14-1 to I.14-53 of Table I.14 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0112] Table I.15: Preferred compounds of formula (I.15) are compounds I.15-1 to I.15-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.15-1 to I.15-53 of Table I.15 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0113] Table I.16: Preferred compounds of formula (I.16) are compounds I.16-1 to I.16-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.16-1 to I.16-53 of Table I.16 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0114] Table I.17: Preferred compounds of formula (I.17) are compounds I.17-1 to I.17-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.17-1 to I.17-53 of Table I.17 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0115] Table I.18: Preferred compounds of formula (I.18) are compounds I.18-1 to I.18-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.18-1 to I.18-53 of Table I.18 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0116] Table I.19: Preferred compounds of formula (I.19) are compounds I.19-1 to I.19-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.19-1 to I.19-53 of Table I.19 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0117] Table I.20: Preferred compounds of formula (I.20) are compounds I.20-1 to I.20-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.20-1 to I.20-53 of Table I.20 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0118] Table I.21: Preferred compounds of formula (I.21) are compounds I.21-1 to I.21-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.21-1 to I.21-53 of Table I.21 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0119] Table I.22: Preferred compounds of formula (I.22) are compounds I.22-1 to I.22-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.22-1 to I.22-53 of Table I.22 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0120] Table I.23: Preferred compounds of formula (I.23) are compounds I.23-1 to I.23-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.23-1 to I.23-53 of Table I.23 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0121] Table I.24: Preferred compounds of formula (I.24) are compounds I.24-1 to I.24-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.24-1 to I.24-53 of Table I.24 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0122] Table I.25: Preferred compounds of formula (I.25) are compounds I.25-1 to I.25-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.25-1 to I.25-53 of Table I.25 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0123] Table I.26: Preferred compounds of formula (I.26) are compounds I.26-1 to I.26-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.26-1 to I.26-53 of Table I.26 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0124] Table I.27: Preferred compounds of formula (I.27) are compounds I.27-1 to I.27-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.27-1 to I.27-53 of Table I.27 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0125] Table I.28: Preferred compounds of formula (I.28) are compounds I.28-1 to I.28-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.28-1 to I.28-53 of Table I.28 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0126] Table I.29: Preferred compounds of formula (I.29) are compounds I.29-1 to I.29-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.29-1 to I.29-53 of Table I.29 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0127] Table I.30: Preferred compounds of formula (I.30) are compounds I.30-1 to I.30-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.30-1 to I.30-53 of Table I.30 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0128] Table I.31: Preferred compounds of formula (I.31) are compounds I.31-1 to I.31-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.31-1 to I.31-53 of Table I.31 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0129] Table I.32: Preferred compounds of formula (I.32) are compounds I.32-1 to I.32-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.32-1 to I.32-53 of Table I.32 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0130] Table I.33: Preferred compounds of formula (I.33) are compounds I.33-1 to I.33-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.33-1 to I.33-53 of Table I.33 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0131] Table I.34: Preferred compounds of formula (I.34) are compounds I.34-1 to I.34-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.34-1 to I.34-53 of Table I.34 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0132] Table I.35: Preferred compounds of formula (I.35) are compounds I.35-1 to I.35-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.35-1 to I.35-53 of Table I.35 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0133] Table I.36: Preferred compounds of formula (I.36) are compounds I.36-1 to I.36-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.36-1 to I.36-53 of Table I.36 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0134] Table I.37: Preferred compounds of formula (I.37) are compounds I.37-1 to I.37-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.37-1 to I.37-53 of Table I.37 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0135] Table I.38: Preferred compounds of formula (I.38) are compounds I.38-1 to I.38-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.38-1 to I.38-53 of Table I.38 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0136] Table I.39: Preferred compounds of formula (I.39) are compounds I.39-1 to I.39-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.39-1 to I.39-53 of Table I.39 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0137] Table I.40: Preferred compounds of formula (I.40) are compounds I.40-1 to I.40-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.40-1 to I.40-53 of Table I.40 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0138] Table I.41: Preferred compounds of formula (I.41) are compounds I.41-1 to I.41-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.41-1 to I.41-53 of Table I.41 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0139] Table I.42: Preferred compounds of formula (I.42) are compounds I.42-1 to I.42-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.42-1 to I.42-53 of Table I.42 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0140] Table I.43: Preferred compounds of formula (I.4) are compounds I.43-1 to I.43-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.43-1 to I.43-53 of Table I.43 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0141] Table I.44: Preferred compounds of formula (I.44) are compounds I.44-1 to I.44-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.44-1 to I.44-53 of Table I.44 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0142] Table I.45: Preferred compounds of formula (I.45) are compounds I.45-1 to I.45-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.45-1 to I.45-53 of Table I.45 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0143] Table I.46: Preferred compounds of formula (I.46) are compounds I.46-1 to I.46-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.46-1 to I.46-53 of Table I.46 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0144] Table I.47: Preferred compounds of formula (I.47) are compounds I.47-1 to I.47-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.47-1 to I.47-53 of Table I.47 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0145] Table I.48: Preferred compounds of formula (I.48) are compounds I.48-1 to I.48-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.48-1 to I.48-53 of Table I.48 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0146] Table I.49: Preferred compounds of formula (I.49) are compounds I.49-1 to I.49-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.49-1 to I.49-53 of Table I.49 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0147] Table I.50: Preferred compounds of formula (I.50) are compounds I.50-1 to I.50-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.50-1 to I.50-53 of Table I.50 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0148] Table I.51: Preferred compounds of formula (I.51) are compounds I.51-1 to I.51-53, in which Q has the meaning of Table 1 indicated in the respective row. Thus, compounds I.51-1 to I.51-53 in Table I.2 are defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0149] Table I.52: Preferred compounds of formula (I.52) are compounds I.52-1 to I.52-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.52-1 to I.52-53 of Table I.52 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0150] Table I.53: Preferred compounds of formula (I.53) are compounds I.53-1 to I.53-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.53-1 to I.53-53 of Table I.53 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0151] Table I.54: Preferred compounds of formula (I.54) are compounds I.54-1 to I.54-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.54-1 to I.54-53 of Table I.54 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0152] Table I.55: Preferred compounds of formula (I.55) are compounds I.55-1 to I.55-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.55-1 to I.55-53 of Table I.55 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0153] Table I.56: Preferred compounds of formula (I.56) are compounds I.56-1 to I.56-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.56-1 to I.56-53 of Table I.56 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0154] Table I.57: Preferred compounds of formula (I.57) are compounds I.57-1 to I.57-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.57-1 to I.57-53 of Table I.57 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0155] Table I.58: Preferred compounds of formula (I.58) are compounds I.58-1 to I.58-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.58-1 to I.58-53 of Table I.58 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0156] Table I.59: Preferred compounds of formula (I.59) are compounds I.59-1 to I.59-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.59-1 to I.59-53 of Table I.59 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0157] Table I.60: Preferred compounds of formula (I.60) are compounds I.60-1 to I.60-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.60-1 to I.60-53 of Table I.60 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0158] Table I.61: Preferred compounds of formula (I.61) are compounds I.61-1 to I.61-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.61-1 to I.61-53 of Table I.61 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0159] Table I.62: Preferred compounds of formula (I.62) are compounds I.62-1 to I.62-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.62-1 to I.62-53 of Table I.62 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0160] Table I.63: Preferred compounds of formula (I.63) are compounds I.63-1 to I.63-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.63-1 to I.63-53 of Table I.63 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0161] Table I.64: Preferred compounds of formula (I.64) are compounds I.64-1 to I.64-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.64-1 to I.64-53 of Table I.64 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0162] Table I.65: Preferred compounds of formula (I.65) are compounds I.65-1 to I.65-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.65-1 to I.65-53 of Table I.65 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0163] Table I.66: Preferred compounds of formula (I.66) are compounds I.66-1 to I.66-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.66-1 to I.66-53 of Table I.66 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0164] Table I.67: Preferred compounds of formula (I.67) are compounds I.67-1 to I.67-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.67-1 to I.67-53 of Table I.67 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0165] Table I.68: Preferred compounds of formula (I.68) are compounds I.68-1 to I.68-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.68-1 to I.68-53 of Table I.68 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0166] Table I.69: Preferred compounds of formula (I.69) are compounds I.69-1 to I.69-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.69-1 to I.69-53 of Table I.69 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0167] Table I.70: Preferred compounds of formula (I.70) are compounds I.70-1 to I.70-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.70-1 to I.70-53 of Table I.70 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0168] Table I.71: Preferred compounds of formula (I.71) are compounds I.71-1 to I.71-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.71-1 to I.71-53 of Table I.71 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0169] Table I.72: Preferred compounds of formula (I.72) are compounds I.72-1 to I.72-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.72-1 to I.72-53 of Table I.72 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0170] Table I.73: Preferred compounds of formula (I.73) are compounds I.73-1 to I.73-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.73-1 to I.73-53 of Table I.73 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0171] Table I.74: Preferred compounds of formula (I.74) are compounds I.74-1 to I.74-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.74-1 to I.74-53 of Table I.74 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0172] Table I.75: Preferred compounds of formula (I.75) are compounds I.75-1 to I.75-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.75-1 to I.75-53 of Table I.75 are thus defined by the meanings of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0173] Table I.76: Preferred compounds of formula (I.76) are compounds I.76-1 to I.76-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.76-1 to I.76-53 of Table I.76 are thus defined by the meaning of the respective entry numbers 1 to 53 for Q in Table 1. [ka]

[0174] Table I.77: Preferred compounds of formula (I.77) are compounds I.77-1 to I.77-53, in which Q has the meaning of Table 1 indicated in the respective row. Compounds I.77-1 to I.77-53 of Table I.77 are thus defined by the meanings of the respective entry numbers 1 to 53 for Q in Table 1.

[0175] Spectroscopic data for selected table examples: Selected detailed synthetic examples for the compounds of the invention of general formula (I) are given below. The chemical examples described in the following sections are reported. 1 H NMR, 13 C-NMR and 19 F-NMR spectroscopic data ( 1 H NMR: 400MHz, 13 C-NMR is 150MHz, 19 F-NMR was obtained on a Bruker instrument at 375 MHz, solvents CDCl3, CD3OD or d6-DMSO, internal standard: tetramethylsilane (δ = 0.00 ppm), and the listed signals have the meanings given below: br = broad; s = singlet, d = doublet, t = triplet, dd = doublet of doublets, ddd = doublet of doublets of doublets, m = multiplet, q = quartet, quint = quintet, sext = sextet, sept = septet, dq = doublet of quartets, dt = doublet of triplets. In case of diastereomeric mixtures, significant signals are reported for each of the two diastereomers or the characteristic signal of the major diastereomer is reported. The abbreviations used for the chemical groups have, for example, the following meanings: Me=CH3, Et=CH2CH3, t-Hex=C(CH3)2CH(CH3)2, t-Bu=C(CH3)3, n-Bu=unbranched butyl, n-Pr=unbranched propyl, i-Pr=branched propyl, c-Pr=cyclopropyl, c-Hex=cyclohexyl.

[0176] The spectroscopic data listed below for selected tabular examples are based on conventional 1 The results were evaluated via 1 H NMR interpretation or NMR peak list methods.

[0177] Idiomatic1 H NMR interpretation Example No. I.77-49: 1 H NMR(400 MHz, 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). Example No. I.71-49: 1 H NMR(400 MHz, 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). Example No. I.70-49: 1 H NMR(400 MHz,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). Example No. I.72-49: 1 H NMR(400 MHz, 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). NMR peak list method The 1H NMR data of selected examples is recorded in the form of 1H NMR peak list. For each signal peak, first the δ value (ppm) is listed, then the signal intensity in parentheses. The δ value / signal intensity number pairs for different signal peaks are listed, separated from each other by semicolons.

[0178] Thus, an example peak list takes the following form: δ1 (Intensity 1); δ2 (Intensity 2);........;δ i (strength i );......;δ n (strength n ) The intensity of sharp signals correlates with the signal height (cm) in the printed example of the NMR spectrum to give the true ratio of signal intensities. In the case of broad signals, several peaks or signal centers and their relative intensities compared to the most intense signal in the spectrum can be shown.

[0179] For the calibration of chemical shifts of 1H NMR spectra, especially for spectra measured in DMSO, the chemical shifts of tetramethylsilane and / or the solvent are used. Thus, the tetramethylsilane peak may be present in the NMR peak list, but does not have to be.

[0180] The 1H NMR peak listing is similar to a conventional 1H NMR printout and therefore typically includes all peaks that are listed in a conventional NMR interpretation.

[0181] Moreover, like conventional 1H NMR printouts, these may show solvent signals, signals of stereoisomers of the target compounds which also form part of the subject-matter of the present invention, and / or peaks of impurities.

[0182] In reporting compound signals in the solvent and / or water delta range, our 1H NMR peak listings show the usual solvent peaks, e.g., the DMSO peak in DMSO-D6, and the water peak, which usually have high intensity on average.

[0183] The peaks of stereoisomers of the target compound and / or the peaks of impurities usually have lower intensity on average than the peaks of the target compound (eg, having a purity of greater than 90%).

[0184] Such stereoisomers and / or impurities may be typical for a particular preparation process, and therefore these peaks may be useful in identifying the reproduction of our preparation process by referencing the "by-product fingerprint".

[0185] The expert, who calculates the peaks of the target compounds by known methods (using MestreC, ACD simulations, but also empirically evaluated expectations), can optionally use additional intensity filters to isolate the peaks of the target compounds, which would be similar to relevant peak picking in conventional 1H NMR interpretation.

[0186] Further details of the 1H NMR peak list can be found in Research Disclosure Database Number 564025. [Table 5] TIFF0007654654000112.tif230170 TIFF0007654654000113.tif229170 TIFF0007654654000114.tif234170 TIFF0007654654000115.tif231170 TIFF0007654654000116.tif236170 TIFF0007654654000117.tif232170 TIFF0007654654000118.tif228170 TIFF0007654654000119.tif232170 TIFF0007654654000120.tif230170 TIFF0007654654000121.tif232170 TIFF0007654654000122.tif232170 TIFF0007654654000123.tif232170 TIFF0007654654000124.tif230170 TIFF0007654654000125.tif228170 TIFF0007654654000126.tif230170 TIFF0007654654000127.tif229170 TIFF0007654654000128.tif228170 TIFF0007654654000129.tif229170 TIFF0007654654000130.tif231170 TIFF0007654654000131.tif194170

[0187] 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, causing damage to said crop plants or useful plants, characterized in that a compound of general formula (I) or a salt thereof is used as a safener, preferably by applying an effective amount of a compound of general formula (I) or a salt thereof to the plant, to a part of a plant or to the seed (or seed material) thereof.

[0188] The compounds of general formula (I) (= safeners) specified above are suitable for use with active ingredients (pesticides) for the selective control of pests in some crop cultures, economically important crops such as cereals (wheat, barley, triticale, rye, rice, maize, millet / sorghum), sugar beet, sugarcane, oilseed rape, cotton, sunflower, pea, bean and soybean. Herbicide-safener combinations with safeners of general formula (I) are also suitable for the control of harmful plants on beds and areas of useful and ornamental plants, for example lawn areas containing practical or ornamental grasses, in particular ryegrass, bluegrass or bermuda grass.

[0189] Mutant crops that are completely or partially resistant to some pesticides, or transgenic crops that are completely or partially resistant, such as maize crops that are resistant to glufosinate or glyphosate, or soybean crops that are resistant to imidazolinones that have a plant-damaging effect, are also of interest for useful plants and crop plants that can use the herbicide-safener combinations that contain the compounds of general formula (I) above.However, a particular benefit of the safeners of general formula (I) used in a novel manner is their effective action in crops that are not normally sufficiently resistant to the pesticides used.

[0190] For general use with pesticides, the compounds of general formula (I) can be deployed simultaneously with the active ingredients or in any order, so that in the case of crop plants, the harmful side effects of these active ingredients can be reduced or completely prevented without impairing or significantly reducing the effectiveness of these active ingredients against undesirable pests. Here, it is also possible to significantly reduce or completely prevent the damage caused by the use of two or more pesticides, for example by two or more herbicides or herbicides combined with insecticides or fungicides. This allows the field of use of conventional pesticides to be considerably expanded. When the compositions of the present invention contain pesticides, these compositions are applied in suitable dilution directly to the cultivation area, to already emerged harmful plants and / or useful plants, or to already emerged harmful plants and / or useful plants. If the compositions of the invention do not contain any pesticides, they may be used by the so-called tank mix method, which means that the user mixes and dilutes the separately formulated products (= useful plant protection composition and pesticide) immediately before application to the area to be treated, or before application of the pesticide, or after application of the pesticide, or for seed pretreatment, i.e., for example, for dressing useful plant seeds. It is preferable to apply the safener promptly together with the pesticide, especially when the safener is applied to the plant after the herbicide. The advantageous effect of the compounds of general formula (I) is observed when they are used together with the pesticide by the pre-emergence or post-emergence method, for example when applied simultaneously as a tank mix or as a co-formulation, or in parallel or successive separate applications (split application). It is also possible to repeat the application two or more times. It may also be advisable sometimes to combine pre-emergence and post-emergence applications. One option is to use the compounds (I) of the present invention as post-emergence application to useful plants or crop plants, usually in conjunction with the simultaneous or subsequent application of a pesticide.Another option is to use the compounds (I) of the present invention in seed dressing, in (dipping) treatment of seedlings (for example rice) or in treatment of other propagation materials (for example potato tubers).

[0191] When the compounds of formula (I) are used in combination with herbicides, not only a safener effect but also an enhanced herbicidal action against harmful plants is often observed. Furthermore, the growth of useful plants and crop plants is often improved, making it possible to increase the yield.

[0192] The composition of the present invention may contain one or more pesticides.Examples of useful pesticides include herbicides, insecticides, fungicides, acaricides and nematicides, which, when used alone, may cause or cause phytotoxic damage to crop plants.Particularly interesting are the corresponding active pesticide components of the group of herbicides, insecticides, acaricides, nematicides and fungicides, especially herbicides.

[0193] The weight ratio of safener (of general formula (I)) to pesticide can vary within wide limits, generally lying in the range of 1:100 to 100:1, preferably 1:20 to 20:1, in particular 1:10 to 10:1. The optimum weight ratio of safener to pesticide depends on both the respective safener used and the respective pesticide and the type of useful plant or crop plant to be protected. Depending on the pesticide used and the type of useful plant to be protected, the application rate of safener required can vary within wide limits, generally lying in the range of 0.001 to 10 kg, preferably 0.01 to 1 kg, in particular 0.01 to 0.2 kg of safener per hectare. The amounts and weight ratios required for successful treatment can be ascertained by simple preliminary tests.

[0194] In the case of seed dressing, for example, 0.005 to 20 g of safener (of general formula (I)) is used per kilogram of seed, preferably 0.01 to 10 g of safener per kilogram of seed, and especially 0.05 to 5 g of safener per kilogram of seed.

[0195] When a solution of safener (of general formula (I)) is applied for seed treatment and the seeds or seedlings are wetted with the solution, suitable concentrations are generally in the range of 1 to 10,000 ppm by weight, preferably 100 to 1,000 ppm. The amounts and weight ratios required for successful treatment can be ascertained by simple preliminary tests.

[0196] The safeners of general formula (I) can be formulated in a conventional manner, separately or together with the pesticides.Therefore, useful plants or crop plant protection compositions are also provided.

[0197] The use of a safener in combination with a pesticide is preferred, especially in the final formulation or by tank-mix method.

[0198] The use of safeners of general formula (I) in seed treatment by subsequent application of a pesticide, preferably a herbicide, after sowing by the pre- or post-emergence method is likewise preferred.

[0199] The compound of general formula (I) or its salt can be used as it is or in the form of its preparation (formulation) in combination with other pesticidal active substances, such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators, for example in the form of a final formulation or tank mix. The combination formulation can be prepared based on the above formulation, taking into account the physical properties and stability of the active ingredients to be combined.

[0200] Combination partners that can be used for the compounds of the present invention in mixed formulations or tank mixes are known active ingredients, for example, based on the inhibition of acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or protoporphyrinogen oxidase, known, for example, from 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 documents cited therein. Known herbicides or plant growth regulators that can be combined with the compounds of the present invention are, for example, the following, where the active ingredients are referred to either by their "common name" or chemical name or code number according to the International Organization for Standardization (ISO): These always include all use forms, eg acids, salts, esters and all isomers, such as stereoisomers and optical isomers, even if not mentioned explicitly.

[0201] Examples of such herbicide mixing partners are: Acetochlor, acifluorfen, acifluorfen sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor potassium, aminocyclopyrachlor methyl, aminopyralid, amitrole, ammonium sulfamate, anilophore s, ashram, atrazine, azafenidine, azimsulfuron, beflubutamid, benazolin, benazolin ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron methyl, bensulide, bentazon, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanaphos, bilanaphos sodium, bispyribac, bispyribac sodium, bromacil, bromobutide, bromofenoxime, bromoxynil, bromoxynil-butyrate, potassium, heptagonist Butanoate and -octanoate, busoxinone, butachlor, butafenacil, butamiphos, butenachlor, butralin, butroxydim, butyrate, cafenstrole, carbetamide, carfentrazone, carfentrazone ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac sodium, chlorfenprop, chlorflurenol, chlorflurenol methyl, chloridazon, chlorimuron, chlorimuron ethyl, chlorofen Talim, chlorotoluron, chlorthal dimethyl, chlorsulfuron, cinidon, cinidon ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop propargyl, clomazone, clomeprop, clopyralid, chloransulam, cloransulam methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop butyl, cyprazine, 2,4-D, 2,4-D-butotyl (2,4-D-butotyl), -butyl, -dimethylammonium, -diolamine, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium, dymron (dymron), dalapon, dazomet, n-decanol, desmedipham , detosylpyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyrnat lium, dimefuron, dimepiperate, dimethachlor, dimethamethrin, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamide, diquat, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsurfuron, ethametsurfuron methyl, ethiozin, ethofumesate, ethoxyphene, ethoxyphene ethyl, Ethoxysulfuron, etobenzanide, F-9600, F-5231, i.e., N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]ethanesulfonamide, F-7967, i.e., 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone sodium, flucetosulfuron, fluazifop Flucloralin, Flufenacet, Flufenpyr, Flufenpyr-ethyl, Flumetsulam, Flumiclorac, Flumiclorac-pentyl, Flumioxazin, Fluometuron, Flurenol, Flurenol-butyl, -dimethylammonium and -methyl, Fluoroglycofen, Fluoroglycofen-ethyl, Flupropanate, Flupyrsulfuron, Flupyrsulfuron-methyl sodium, Fluridone, Flurochloridone, Fluroxypyr, Fluroxypyr-meptyl, Flurtamone, Fluthiacet, Fluthiacet-methyl, Fomesafen, Fomesafen sodium, Foramsulfuron, Fosamine, Glufosinate, Glufosinate-ammonium, Glufosinate-P-sodium, Glufosinate-P-ammonium, Glufosinate-P-sodium, Glyphosate, Glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium and -trimesium, H-9201, i.e. O-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropyl phosphoramidothioate, haloxifene, haloxifene-methyl, halosafen, halosulfuron, 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)acetate, imazamethabenz, imazamethabenz methyl, imazamox, imazamox ammonium, imazapic, imazapic ammonium, imazapyr, imazapyr isopropyl ammonium, imazaquin, imazaquin ammonium, imazethapyr, imazethapyr immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron methyl sodium, ioxynil, ioxynil octanoate, -potassium ammonium and sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, carbutyrate, 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, lactofen, lenacil, linuron, MCPA, MCPA-butyric acid, -dimethylammonium, -2-ethylhexylamine, -dimethylammonium, - ...hexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, -dimethylhexylamine, - xyl, -isopropylammonium, -potassium and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium and -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, meth opirsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metoslam, methoxron, metribuzin, metsulfuron, metsulfuron methyl, molinat, monolinuron, monosulfuron, monosulfuron ester, MT-5950, i.e., N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e., 4-(2,4-Dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, nebulon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorphe, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, petoxamide, petroleum, phenmedipham, picloram, picolinafen, Pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron methyl, prodiamine, propoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolinate (pyrazolate), pyrazosulfuron, pyrazosulfuron Ethyl, pyrazoxyfen, pyribambenz, pyribambenzisopropyl, pyribambenzpropyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, piroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P- Tefuril, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrione, sulfentrazone, sulfometuron, sulfometuron methyl, sulfosulfuron, SYP-249, i.e., 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e., 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-Benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trifluoroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, trienecarbazone, trienecarbazone methyl, thifensulfuron, thifensulfuron methyl, thiobencarb, thiaphenacyl, tolpyralate, topramezone, tralco Xydim, triafamone, triallate, trisulfuron, triaziflam, tribenuron, tribenuron methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron sodium, trifludimoxazine, trifuralin, triflusulfuron, triflusulfuron methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, i.e., 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, and the following compounds: [ka]

[0202] Examples of plant growth regulators as possible mixing partners are: Acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechol, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac sodium, endothal, endothal-dipotassium, -disodium, and mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indole-3- butyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid methyl ester, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, 4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazol, N-phenylphthalamic acid, prohexadione, prohexadione calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

[0203] When used as active ingredient formulations or co-formulations, these generally contain, where appropriate, the respective customary spreading agents, wetting agents, dispersing agents, emulsifying agents, penetrating agents, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, antifoaming agents, evaporation inhibitors and pH and viscosity adjusters.

[0204] The compound of general formula (I) and its combination with one or more of the mentioned pesticides can be formulated in various ways depending on the defined physicochemical and biological parameters. Suitable examples of the types of formulations include: - emulsions, which are prepared by dissolving the active ingredient in an organic solvent, such as butanol, cyclohexanone, dimethylformamide, xylene or a relatively high-boiling hydrocarbon, or a mixture of organic solvents, with the addition of one or more ionic and / or non-ionic surfactants (emulsifiers). Suitable emulsifiers are, for example, calcium alkylarylsulfonates, fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters and polyoxyethylene sorbitan fatty acid esters; - dusts obtained by grinding the active ingredient with finely divided solid inorganic or organic substances, for example talc, natural clays, for example kaolin, bentonite and pyrophyllite, diatomaceous earth or wheat flour; - Water- or oil-based flowables which can be prepared by wet grinding, for example in a bead mill; -Water soluble; -Water-soluble concentrate; - granules, such as water-soluble granules, water dispersible granules and granules for spraying and soil application; - wettable powders which, as well as the active ingredient, also contain diluents or inert substances and surfactants; - Capsule suspensions and microcapsules; -Ultra-low volume formulation.

[0205] The above formulation types are known to those skilled in the art and are described, for example, in K. Martens, "Spray Drying Handbook", 3rd ed., G. Goodwin Ltd., London. 1979; W. van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY 1973; Winacker-Kuchler, "Chemische Technologie" [Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th edition 1986; and "Perry's Chemical Engineer's Handbook", 5th ed., McGraw-Hill, NY 1973, pages 8-57.

[0206] The necessary formulation auxiliaries, such as inert materials, surfactants, solvents and further additives, are likewise known and are described, for example, in McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; C. Marsden, "Solvents Guide", 2nd ed., Interscience, NY 1963; H. von Olphen, "Introduction to Clay Colloid Chemistry", 2nd ed., J. Wiley & Sons, NY; Schonfeldt, "Grenzflachenaktive Athylenoxidaddukte" [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed. ed., Darland Books, Caldwell NJ; Winnacker-Kuchler, "Chemische Technologie", volume 7, C. Hanser Verlag Munich, 4th edition 1986.

[0207] Apart from the abovementioned formulation auxiliaries, useful plant protection compositions may optionally contain customary wetting agents, spreading agents, dispersing agents, penetrating agents, emulsifying agents, preservatives, antifreeze agents, fillers, carriers and dyes, antifoaming agents, evaporation inhibitors, and pH or viscosity adjusters.

[0208] Depending on the type of formulation, useful plant protection compositions generally contain 0.1% to 99% by weight, in particular 0.2% to 95% by weight, of one or more safeners of general formula (I) or combinations of safeners and pesticides. They further contain 1% to 99.9% by weight, in particular 4% to 99.5% by weight, of one or more solid or liquid additives and 0% to 25% by weight, in particular 0.1 to 25% by weight, of surfactants. In emulsifiable concentrates, the active ingredient concentration, i.e. the concentration of safeners and / or pesticides, is generally 1% to 90% by weight, in particular 5% to 80% by weight. Dusts typically contain 1% to 30% by weight, preferably 5% to 20% by weight, of active ingredient. In wettable powders, the active ingredient concentration is generally 10% to 90% by weight. In the water dispersible granule, the content of the active ingredient is, for example, between 1% by weight and 95% by weight, and preferably between 10% by weight and 80% by weight.

[0209] For application, the commercial formulations are diluted in the customary manner, if necessary, for example with water in the case of wettable powders, emulsifiable concentrates, dispersions and wettable powders. Preparations of dust forms, granules and sprayable solutions are usually not further diluted with other inert substances before application. The required application rate of the safener of general formula (I) varies depending on the external conditions, including temperature, humidity and the type of herbicide used. In one aspect, the present invention provides the following. [Item 1] Except for ethyl [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetate (CAS [931426-67-4]), A compound of formula (I) or a salt thereof TIFF0007654654000133.tif66160 (In the formula, R 1 and R 2 are independently hydrogen, halogen, cyano, nitro, (C 1 ~C 6 ) alkyl, (C 2 ~C 6 ) alkenyl, (C 2 ~C 6 ) alkynyl, (C 3 ~C 8 ) cycloalkyl, (C 3 ~C 8 ) cycloalkenyl, (C 1~C 6 )alkoxy or (C 1 ~C 6 )AlkylS(O) p and the latter seven groups are unsubstituted or substituted with halogen, cyano, (C 1 ~C 6 )alkoxy and (C 1 ~C 6 )AlkylS(O) p and is substituted by one or more groups from the group R 3 is hydrogen or (C 1 ~C 6 ) alkyl, R 4 is hydrogen, (C 1 ~C 18 ) alkyl, (C 1 ~C 18 ) haloalkyl, (C 1 ~C 18 ) cyanoalkyl, (C 2 ~C 18 ) alkenyl, (C 2 ~C 18 ) alkynyl, (C 3 ~C 12 ) cycloalkyl, (C 3 ~C 12 ) cycloalkenyl, aryl, heteroaryl, (C 1 ~C 18 )Alkoxy-(C 1 ~C 18 ) alkyl, (C 1 ~C 18 )Haloalkoxy-(C 1 ~C 18 ) alkyl, (C 1 ~C 18 )Alkoxy-(C 1 ~C 18 ) haloalkyl, (C 1 ~C 18 )Alkylthio-(C 1 ~C 18 ) alkyl, (C 1 ~C 18 )Haloalkylthio-(C 1 ~C 18 ) alkyl, (C 2 ~C 18 ) haloalkenyl, (C 2 ~C 18 )Haloalkynyl, heterocyclyl-(C 1 ~C 18 )Alkyl, aryl-(C 1 ~C 18 ) alkyl, (C 3 ~C 12 )Cycloalkyl-(C 1 ~C 18 ) alkyl, (C 1 ~C 18 )Alkoxycarbonyl-(C 1 ~C 18 ) alkyl, and (C 1 ~C 18 )Alkoxycarbonyl-(C 3 ~C 12 )Cycloalkyl-(C 1 ~C 18 ) alkyl, or Formula-NR a R b Or -N=CR c R d Based on In the first two groups, R a 、R b 、R c and R d Each of the groups is independently hydrogen, (C 1 ~C 4 ) alkyl, (C 2 ~C 4 ) alkenyl, (C 2 ~C 4 ) alkynyl, benzyl, substituted benzyl, phenyl or substituted phenyl; or R a and R b may contain, together with the nitrogen atom, in addition to the nitrogen atom, one or two further ring heteroatoms from the group N, O and S, and may be unsubstituted or (C 1 ~C 4 )-Alkyl and (C 1 ~C 4 )-haloalkyl, or R c and R d together with the carbon atom form a 3-8 membered carbocyclic or heterocyclic group which may contain 1-3 ring heteroatoms of the group N, O and S, said carbocyclic or heterocyclic group being unsubstituted or (C 1 ~C 4 )-Alkyl and (C 1~C 4 )-haloalkyl, n and m are independently a number from 0 to 5; where p is 0, 1 or 2). [Item 2] Except for ethyl [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetate, R 1 and R 2 In the upright position, hydrogen, halogen, cyano, nitro, (C 1 ~C 4 ) alkyl, (C 2 ~C 4 ) alkenyl, (C 2 ~C 4 ) alkynyl, (C 3 ~C 6 ) cycloalkyl, (C 3 ~C 6 ) cycloalkenyl, (C 1 ~C 4 )alkoxy or (C 1 ~C 4 )AlkylS(O) p and the latter seven groups are unsubstituted or substituted with halogen, cyano, (C 1 ~C 4 )alkoxy and (C 1 ~C 4 )AlkylS(O) p and is substituted by one or more groups from the group R 3 is hydrogen or (C 1 ~C 4 ) alkyl, R 4 But hydrogen, (C 1 ~C 18 ) alkyl, (C 1 ~C 18 ) haloalkyl, (C 1 ~C 18 ) cyanoalkyl, (C 2 ~C 18 ) alkenyl, (C 2 ~C 18 ) alkynyl, (C 3 ~C 12 ) cycloalkyl, (C 3 ~C 12 ) cycloalkenyl, aryl, heteroaryl, (C 1 ~C 18 )Alkoxy-(C 1 ~C 18 ) alkyl, (C1 ~C 18 )Haloalkoxy-(C 1 ~C 18 ) alkyl, (C 1 ~C 18 )Alkoxy-(C 1 ~C 18 ) haloalkyl, (C 1 ~C 18 )Alkylthio-(C 1 ~C 18 ) alkyl, (C 1 ~C 18 )Haloalkylthio-(C 1 ~C 18 ) alkyl, (C 2 ~C 18 ) haloalkenyl, (C 2 ~C 18 )Haloalkynyl, heterocyclyl-(C 1 ~C 18 )Alkyl, aryl-(C 1 ~C 18 ) alkyl, (C 3 ~C 12 )Cycloalkyl-(C 1 ~C 18 ) alkyl, (C 1 ~C 18 )Alkoxycarbonyl-(C 1 ~C 18 ) alkyl or (C 1 ~C 18 )Alkoxycarbonyl-(C 3 ~C 12 )Cycloalkyl-(C 1 ~C 18 ) alkyl, n and m are independently a number from 0 to 4; p is 0, 1 or 2; Item 1. A compound of formula (I) or a salt thereof. [Item 3] Except for ethyl [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetate, R 1 and R 2 are independently hydrogen, halogen, cyano, methyl, CF 3 , C.H. 2 F, CHF 2 , O.C.H. 3 , OCF 3 , S.C.H. 3 or SCF 3 and R 3 is hydrogen, CH 2 CH 3 or CH 3 and R 4 But hydrogen, (C 1 ~C 18 ) alkyl, (C 1 ~C 18 ) haloalkyl, (C 1 ~C 18 ) cyanoalkyl, (C 2 ~C 18 ) alkenyl, (C 2 ~C 18 ) alkynyl, (C 3 ~C 12 ) cycloalkyl, (C 3 ~C 12 ) cycloalkenyl, aryl, heteroaryl, (C 1 ~C 18 )Alkoxy-(C 1 ~C 18 ) alkyl, (C 1 ~C 18 )Haloalkoxy-(C 1 ~C 18 ) alkyl, (C 1 ~C 18 )Alkoxy-(C 1 ~C 18 ) haloalkyl, (C 1 ~C 18 )Alkylthio-(C 1 ~C 18 ) alkyl, (C 1 ~C 18 )Haloalkylthio-(C 1 ~C 18 ) alkyl, (C 2 ~C 18 ) haloalkenyl, (C 2 ~C 18 )Haloalkynyl, heterocyclyl-(C 1 ~C 18 )Alkyl, aryl-(C 1 ~C 18 ) alkyl, (C 3 ~C 12 )Cycloalkyl-(C 1 ~C 18 ) alkyl, (C 1 ~C 18 )Alkoxycarbonyl-(C 1 ~C 18 ) alkyl or (C 1 ~C 18 )Alkoxycarbonyl-(C 3 ~C 12 )Cycloalkyl-(C 1 ~C 18 ) alkyl, n and m are independently the numbers 0, 1, 2, or 3; Item 1. A compound of formula (I) or a salt thereof. [Item 4] Except for ethyl [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetate, R 1 and R 2 are independently hydrogen, fluorine, chlorine, bromine, iodine, CN, methyl, CF 3 , C.H. 2 F, CHF 2 , O.C.H. 3 , OCF 3 , S.C.H. 3 or SCF 3 and R 3 is hydrogen or CH 3 and R 4 But hydrogen, (C 1 ~C 10 ) alkyl, (C 1 ~C 10 ) haloalkyl, (C 1 ~C 10 ) cyanoalkyl, (C 2 ~C 10 ) alkenyl, (C 2 ~C 10 ) alkynyl, (C 3 ~C 9 ) cycloalkyl, (C 3 ~C 9 ) cycloalkenyl, aryl, heteroaryl, (C 1 ~C10 )Alkoxy-(C 1 ~C 10 ) alkyl, (C 1 ~C 10 )Haloalkoxy-(C 1 ~C 10 ) alkyl, (C 1 ~C 10 )Alkoxy-(C 1 ~C 10 ) haloalkyl, (C 1 ~C 10 )Alkylthio-(C 1 ~C 10 ) alkyl, (C 1 ~C 10 )Haloalkylthio-(C 1 ~C 10 ) alkyl, (C 2 ~C 18 ) haloalkenyl, (C 2 ~C 18 )Haloalkynyl, heterocyclyl-(C 1 ~C 10 )Alkyl, aryl-(C 1 ~C 10 ) alkyl, (C 3 ~C 9 )Cycloalkyl-(C 1 ~C 10 ) alkyl, (C 1 ~C 10 )Alkoxycarbonyl-(C 1 ~C 10 ) alkyl or (C 1 ~C 10 )Alkoxycarbonyl-(C 3 ~C 9 )Cycloalkyl-(C 1 ~C 10 ) alkyl, n and m are independently the numbers 0, 1, 2, or 3; Item 1. A compound of formula (I) or a salt thereof. [Item 5] Except for ethyl [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetate, R 1 and R 2 are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, CF 3 , C.H. 2 F, CHF 2 , O.C.H. 3 , OCF 3 , S.C.H. 3 or SCF 3 and R 3 is hydrogen, R 4 is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, n-pentyl, phenyl, benzyl, CH 2 (4-Cl-Ph), CH 2 (4-F-Ph), CH 2 (4-OMe-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl, methylpropionate-3-yl, ethylpropionate-3-yl, methylacetate-2-yl, ethylacetate-2-yl, methylpivalate-2-yl, ethylpivalate-3-yl, methyl-2-methylpropanoate-3-yl, methyl-2,2-dimethylpropanoate 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 Allyl, 2,2,3,3,3-pentafluoropropyl, cyclopropylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl, allyl, propargyl (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl, 3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl , 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, heptan-2-yl, isobutyl, 1,3-dioxolan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl, n and m are independently the numbers 0, 1, 2, or 3; Item 1. A compound of formula (I) or a salt thereof. [Item 6] Except for ethyl [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetate, (R 1 ) n -Phenyl is Q-1.1 to Q-1.53 TIFF0007654654000134.tif205162TIFF0007654654000135.tif114162 and (R 2 ) m -Phenyl is Q-2.1 to Q-2.53 TIFF0007654654000136.tif111162TIFF0007654654000137.tif248161TIFF0007654654000138.tif34156 and R 3 is hydrogen, R 4 is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, n-pentyl, phenyl, benzyl, CH 2 (4-Cl-Ph), CH 2 (4-F-Ph), CH 2 (4-OMe-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl, methylpropionate-3-yl, ethylpropionate-3-yl, methylacetate-2-yl, ethylacetate-2-yl, methylpivalate-2-yl, ethylpivalate-3-yl, methyl-2-methylpropanoate-3-yl, methyl-2,2-dimethylpropanoate 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 Allyl, 2,2,3,3,3-pentafluoropropyl, cyclopropylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl, allyl, propargyl (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl, 3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl , 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, heptan-2-yl, isobutyl, 1,3-dioxolan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl, Item 1. A compound of formula (I) or a salt thereof. [Item 7] 7. Useful plants or crop plant protection compositions, characterized by a content of at least one compound of general formula (I) or a salt thereof according to any one of items 1 to 6, in combination with further pesticides and optionally formulation auxiliaries. [Item 8] 8. The composition according to item 7, comprising at least one herbicide. [Item 9] A method for reducing the phytotoxic effect of pesticides on useful or crop plants by use of one or more compounds according to items 1 to 6 or a composition according to items 7 or 8. [Item 10] A method for reducing the phytotoxic effect of a pesticide on useful or crop plants, characterized in that one or more inventive compounds of general formula (I) according to any one of items 1 to 6 for use in combination with a pesticide are deployed simultaneously or in any order with said pesticide. [Item 11] 11. The method of claim 10, wherein the pesticide is one or more herbicides. [Item 12] 12. The method according to item 10 or 11, characterized in that a compound of formula (I) or a salt thereof according to items 1 to 6 is applied to a plant, a part of said plant, or a seed or seed material thereof.

[0210] In the following examples, which illustrate but do not limit the invention, amounts given are by weight unless otherwise defined.

[0211] [Example] 1. Formulation Examples 1.1 Powder The dusts are obtained by mixing 10 parts by weight of a compound of general formula (I) (safener) or an active ingredient mixture consisting of a pesticide (e.g. herbicide) and a safener of general formula (I) with 90 parts by weight of talc as an inert substance and grinding in a bead mill.

[0212] 1.2 Water-dispersible powder The easily water-dispersible wettable powder is obtained by mixing 25 parts by weight of a compound of general formula (I) or an active ingredient mixture of a pesticide (e.g. herbicide) and a safener of general formula (I), 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoyl methyl taurate as wetting and dispersing agents, and grinding the mixture in a pin-disk mill.

[0213] 1.3 Water Dispersant Concentrates The water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of a compound of general formula (I) or an active ingredient mixture of a pesticide (e.g. herbicide) and a safener of general formula (I) with 6 parts by weight of an alkylphenol polyglycol ether (Triton X 207), 3 parts by weight of an isotridecanol polyglycol ether and 71 parts by weight of a paraffinic mineral oil and grinding in an antifriction ball mill to a fineness of less than 5 microns.

[0214] 1.4 Emulsions The emulsifiable concentrate is obtained from 15 parts by weight of a compound of general formula (I) or an active ingredient mixture consisting of a pesticide (e.g. 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.

[0215] 1.5 Water dispersible granules Water dispersible granules are 75 parts by weight of a safener of general formula (I) or a mixture of a pesticide and a safener of general formula (I), 10'' calcium lignosulfonate, 5'' sodium lauryl sulfate, 3'' polyvinyl alcohol and 7'' polyvinyl alcohol and 7'' Kaolin Mix the It is obtained by grinding the mixture in a pin disc mill and granulating the powder in a fluidized bed by spray application of water as the granulating fluid.

[0216] The WG may also be mixed in a colloid mill. 25 parts by weight of a safener of general formula (I) or a mixture of a pesticide with a safener of general formula (I), 5'' Sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, 2'' Sodium oleoyl methyl taurate, 17'' calcium carbonate, 50'' of water and 1 part by weight of polyvinyl alcohol It can also be obtained by homogenizing and grinding the above-mentioned mixture, then grinding the mixture in a bead mill and atomizing and drying the suspension thus obtained in a spray tower by means of a single-phase nozzle.

[0217] 2. Biological Examples 2.1 Absolute action of selected compounds of the invention using the example of the reduction of damage caused by mesosulfuron-methyl to summer wheat (TRZAS) Seeds of the crop plants to be treated are arranged in sandy loam in wood fibre or plastic pots (diameter approx. 4 cm), covered with soil and cultivated in a greenhouse under good conditions for germination and growth. The test plants were treated at the early leaf stage (BBCH10-BBCH12). In this process, the compounds of the invention of general formula (I) formulated in the form of wettable powders (WP) were sprayed onto the above-ground parts of the plants as aqueous suspensions with the addition of a specified dose of wetting agent (e.g. 0.2% agrotin) at a water application rate equivalent to 800 l / ha.

[0218] This was followed by the application of herbicide. For this purpose, mesosulfuron-methyl, formulated in the form of water dispersible granules (WG), was sprayed onto the above-ground parts of the plants in the form of an aqueous dispersion with the addition of a wetting agent (e.g. 0.2% Agrotin) at a dose of 20 g / ha, at a water application rate equivalent to 800 l / ha. The dose of herbicide was selected here so as to cause visually evident damage (minimum 30%, maximum 75%) compared to untreated crop plants, as assessed against a control group of crop plants without safener treatment included in the same test.

[0219] After application, the plants were grown under good growing conditions in a greenhouse. Damage was visually assessed 14-21 days after application.

[0220] Damage effects were visually assessed on a scale of 0-100% compared to untreated control plants and averaged over 2-3 replicates per treatment. 0% = no significant effect compared to untreated plants 20% = treated plant population has 20% damage (e.g., growth height, leaf damage, etc.) compared to untreated control population 100% = treated plants completely damaged / dead.

[0221] The tests show that the damage to summer wheat crop plants (TRZAS; cv. Triso) caused by the herbicide mesosulfuron-methyl (= herbicide damage in the absence of the compound of formula (I) in the table below) is significantly reduced by treatment with the substances of the invention (= herbicide damage in the presence of the compound of formula (I) in the table below): [Table 6] TIFF0007654654000140.tif154170

[0222] 2.2 Absolute action of selected compounds of the invention using the example of the reduction of damage caused by mesosulfuron-methyl to summer barley (HORVS) Seeds of the crop plants to be treated are arranged in sandy loam in wood fibre or plastic pots (diameter approx. 4 cm), covered with soil and cultivated in a greenhouse under good conditions for germination and growth. The test plants were treated at the early leaf stage (BBCH10-BBCH12). In this process, the compounds of the invention of general formula (I) formulated in the form of wettable powders (WP) were sprayed onto the above-ground parts of the plants as aqueous suspensions with the addition of a specified dose of wetting agent (e.g. 0.2% agrotin) at a water application rate equivalent to 800 l / ha.

[0223] This was followed by the application of herbicide. For this purpose, mesosulfuron-methyl, formulated in the form of water dispersible granules (WG), was sprayed onto the above-ground parts of the plants in the form of an aqueous dispersion with the addition of a wetting agent (e.g. 0.2% Agrotin) at a dose of 20 g / ha, at a water application rate equivalent to 800 l / ha. The dose of herbicide was selected here so as to cause visually evident damage (minimum 30%, maximum 75%) compared to untreated crop plants, as assessed against a control group of crop plants without safener treatment included in the same test.

[0224] After application, the plants were grown under good growing conditions in a greenhouse. Damage was visually assessed 14-21 days after application.

[0225] Damage effects were visually assessed on a scale of 0-100% compared to untreated control plants and averaged over 2-3 replicates per treatment. 0% = no significant effect compared to untreated plants 20% = treated plant population has 20% damage (e.g., growth height, leaf damage, etc.) compared to untreated control population 100% = treated plants completely damaged / dead.

[0226] The tests show that the damage to summer barley crop plants (HORVS; cv. Montoya) caused by the herbicide mesosulfuron-methyl (= herbicide damage in the absence of the compound of formula (I) in the table below) is significantly reduced by treatment with the substances of the invention (= herbicide damage in the presence of the compound of formula (I) in the table below): [Table 7] TIFF0007654654000142.tif144170

[0227] 2.3 Relative Effects of Selected Compounds of the Invention Using the Example of Reduction of Damage to Summer Wheat (TRZAS) by Mesosulfuron-methyl Seeds of the crop plants to be treated are arranged in sandy loam in plastic pots (diameter about 4 cm), covered with soil and cultivated in a greenhouse under good conditions for germination and growth. The test plants were treated at the early leaf stage (BBCH10-BBCH12). In this process, the compounds of the invention of general formula (I) formulated in the form of wettable powders (WP) were sprayed onto the above-ground parts of the plants as aqueous suspensions with the addition of a specified dose of wetting agent (e.g. 0.2% Genapol-LRO or 0.2% Mero) at a water application rate equivalent to 800 l / ha.

[0228] This was followed by the application of herbicides. For this purpose, mesosulfuron-methyl, formulated in the form of water dispersible granules (WG), was sprayed on the above-ground parts of the plants in the form of an aqueous dispersion with the addition of a wetting agent (e.g. 0.2% Genapol-LRO or 1 l / ha) at a dose of 40-60 g / ha, at a water application rate equivalent to 800 l / ha. The doses of herbicide were selected here to cause visually evident damage (minimum 30%, maximum 75%) compared to untreated crop plants, as assessed against a control group of crop plants without safener treatment included in the same test.

[0229] After application, the plants were grown under good growing conditions in a greenhouse. 9-13 days after application, the efficacy of the test compounds was visually evaluated. For this purpose, the appearance of the plants treated with the test compounds and herbicides was compared with the corresponding herbicide controls (without safener; clearly visible damage) and with untreated controls (no damage). The damage-reducing effect of the test compounds was expressed here in a graded efficacy code according to the following scheme: 0: No reduction in damage (appearance equivalent to herbicide control) 1: Slight reduction in damage 2: Significant reduction in damage 3: Significant reduction in damage 4: Complete reduction of damage (appearance comparable to untreated control) The tests show a clear efficacy of the substance of the invention in reducing the damage caused by the herbicide mesosulfuron-methyl to summer wheat crop plants (TRZAS; cv. Triso): [Table 8]

[0230] 2.4 Relative Effects of Selected Compounds of the Invention Using the Example of Reduction of Damage to Summer Barley (HORVS) by Mesosulfuron-methyl Seeds of the crop plants to be treated are arranged in sandy loam in plastic pots (diameter about 4 cm), covered with soil and cultivated in a greenhouse under good conditions for germination and growth. The test plants were treated at the early leaf stage (BBCH10-BBCH12). In this process, the compounds of the invention of general formula (I) formulated in the form of wettable powders (WP) were sprayed onto the above-ground parts of the plants as aqueous suspensions with the addition of a specified dose of wetting agent (e.g. 0.2% Genapol-LRO or 0.2% Mero) at a water application rate equivalent to 800 l / ha.

[0231] This was followed by the application of herbicides. For this purpose, mesosulfuron-methyl, formulated in the form of water dispersible granules (WG), was sprayed on the above-ground parts of the plants in the form of an aqueous dispersion with the addition of a wetting agent (e.g. 0.2% Genapol-LRO or 1 l / ha) at a dose of 40-60 g / ha, at a water application rate equivalent to 800 l / ha. The doses of herbicide were selected here to cause visually evident damage (minimum 30%, maximum 75%) compared to untreated crop plants, as assessed against a control group of crop plants without safener treatment included in the same test.

[0232] After application, the plants were grown under good growing conditions in a greenhouse. 9-13 days after application, the efficacy of the test compounds was visually evaluated. For this purpose, the appearance of the plants treated with the test compounds and herbicides was compared with the corresponding herbicide controls (without safener; clearly visible damage) and with the untreated controls (no damage). The damage-reducing effect of the test compounds was expressed here separately for the two replicates with a graded efficacy code according to the following scheme: 0: No reduction in damage (appearance equivalent to herbicide control) 1: Slight reduction in damage 2: Significant reduction in damage 3: Significant reduction in damage 4: Complete reduction of damage (appearance comparable to untreated control) The tests show a clear efficacy of the substance of the invention in reducing the damage caused by the herbicide mesosulfuron-methyl to summer barley crop plants (HORVS; cv. Montoya):

Table 9

Claims

1. Except for ethyl [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetate (CAS [931426-67-4]), A compound of formula (I) or a salt thereof (In the formula, R １ and R ２ are independently hydrogen, halogen, cyano, nitro, (C １ ~C ６ ) alkyl, (C ２ ~C ６ ) alkenyl, (C ２ ~C ６ ) alkynyl, (C ３ ~C ８ ) cycloalkyl, (C ３ ~C ８ ) cycloalkenyl, (C １ ~C ６ ) alkoxy or (C １ ~C ６ ) alkylS(O) ｐ and the latter seven groups are unsubstituted or selected from halogen, cyano, (C １ ~C ６ ) alkoxy and (C １ ~C ６ ) alkylS(O) ｐ and is substituted by one or more groups from the group R ３ is hydrogen or (C １ ~C ６ ) alkyl; R ４ is hydrogen, (C １ ~C １８ ) alkyl, (C １ ~C １８ ) haloalkyl, (C １ ~C １８ ) cyanoalkyl, (C ２ ~C １８ ) alkenyl, (C ２ ~C １８ ) alkynyl, (C ３ ~C １２ ) cycloalkyl, (C ３ ~C １２ ) cycloalkenyl, aryl, heteroaryl, (C １ ~C １８ ) alkoxy-(C １ ~C １８ ) alkyl, (C １ ~C １８ ) haloalkoxy-(C １ ~C １８ ) alkyl, (C １ ~C １８ ) alkoxy-(C １ ~C １８ ) haloalkyl, (C １ ~C １８ ) alkylthio-(C １ ~C １８ ) alkyl, (C １ ~C １８ ) haloalkylthio-(C １ ~C １８ ) alkyl, (C ２ ~C １８ ) haloalkenyl, (C ２ ~C １８ ) haloalkynyl, heterocyclyl-(C １ ~C １８ ) alkyl, aryl-(C １ ~C １８ ) alkyl, (C ３ ~C １２ ) cycloalkyl-(C １ ~C １８ ) alkyl, (C １ ~C １８ ) alkoxycarbonyl-(C １ ~C １８ ) alkyl, and (C １ ~C １８ ) alkoxycarbonyl-(C ３ ~C １２ ) cycloalkyl-(C １ ~C １８ ) alkyl, or Formula-NR ａ R ｂ Or -N=CR ｃ R ｄ Based on In the former two groups, R ａ , R ｂ , R ｃ and R ｄ Each of the groups is independently hydrogen, (C １ ~C ４ ) alkyl, (C ２ ~C ４ ) alkenyl, (C ２ ~C ４ ) alkynyl, benzyl, substituted benzyl, phenyl or substituted phenyl, where the substituents are hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkylthio, haloalkyl, alkoxy, haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bisalkylaminoalkoxy, tris[alkyl]silyl, bis[alkyl]aryl. arylsilyl, bis[alkyl]alkylsilyl, tris[alkyl]silylalkynyl, alkylalkynyl, cycloalkylalkynyl, haloalkylalkynyl, heterocyclyl-N-alkoxy, nitro, cyano, amino, alkylamino, bisalkylamino, alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino, alkoxycarbonylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl, bisalkylaminocarbonyl, heteroarylalkoxy, arylalkoxy; Or R ａ and R ｂ may contain, together with the nitrogen atom, in addition to the nitrogen atom, one or two further ring heteroatoms from the group N, O and S, and may be unsubstituted or (C １ ~C ４ )-alkyl and (C １ ~C ４ )-haloalkyl, forming a 3- to 8-membered heterocyclic ring substituted by one or more radicals from the group Or R ｃ and R ｄ together with the carbon atom form a 3-8 membered carbocyclic or heterocyclic group which may contain 1-3 ring heteroatoms of the group N, O and S, said carbocyclic or heterocyclic group being unsubstituted or (C １ ~C ４ )-alkyl and (C １ ~C ４ )-haloalkyl, n and m are independently numbers from 0 to 5; p is 0, 1 or 2).

2. Except for ethyl [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetate, R １ and R ２ are independently hydrogen, halogen, cyano, nitro, (C １ ~C ４ ) alkyl, (C ２ ~C ４ ) alkenyl, (C ２ ~C ４ ) alkynyl, (C ３ ~C ６ ) cycloalkyl, (C ３ ~C ６ ) cycloalkenyl, (C １ ~C ４ ) alkoxy or (C １ ~C ４ ) alkylS(O) ｐ and the latter seven groups are unsubstituted or selected from halogen, cyano, (C １ ~C ４ ) alkoxy and (C １ ~C ４ ) alkylS(O) ｐ and is substituted by one or more groups from the group R ３ is hydrogen or (C １ ~C ４ ) alkyl; R ４ is hydrogen, (C １ ~C １８ ) alkyl, (C １ ~C １８ ) haloalkyl, (C １ ~C １８ ) cyanoalkyl, (C ２ ~C １８ ) alkenyl, (C ２ ~C １８ ) alkynyl, (C ３ ~C １２ ) cycloalkyl, (C ３ ~C １２ ) cycloalkenyl, aryl, heteroaryl, (C １ ~C １８ ) alkoxy-(C １ ~C １８ ) alkyl, (C １ ~C １８ ) haloalkoxy-(C １ ~C １８ ) alkyl, (C １ ~C １８ ) alkoxy-(C １ ~C １８ ) haloalkyl, (C １ ~C １８ ) alkylthio-(C １ ~C １８ ) alkyl, (C １ ~C １８ ) haloalkylthio-(C １ ~C １８ ) alkyl, (C ２ ~C １８ ) haloalkenyl, (C ２ ~C １８ ) haloalkynyl, heterocyclyl-(C １ ~C １８ ) alkyl, aryl-(C １ ~C １８ ) alkyl, (C ３ ~C １２ ) cycloalkyl-(C １ ~C １８ ) alkyl, (C １ ~C １８ ) alkoxycarbonyl-(C １ ~C １８ ) alkyl or (C １ ~C １８ ) alkoxycarbonyl-(C ３ ~C １２ ) cycloalkyl-(C １ ~C １８ ) alkyl; n and m are independently numbers from 0 to 4; p is 0, 1 or 2; A compound of the general formula (I) according to claim 1 or a salt thereof.

3. Except for ethyl [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetate, R １ and R ２ are independently hydrogen, halogen, cyano, methyl, CF ３ , C.H. ２ F, C.H.F. ２ , O.C.H. ３ , O.C.F. ３ , S.C.H. ３ or SCF ３ and R ３ is hydrogen, CH ２ CH ３ or CH ３ and R ４ is hydrogen, (C １ ~C １８ ) alkyl, (C １ ~C １８ ) haloalkyl, (C １ ~C １８ ) cyanoalkyl, (C ２ ~C １８ ) alkenyl, (C ２ ~C １８ ) alkynyl, (C ３ ~C １２ ) cycloalkyl, (C ３ ~C １２ ) cycloalkenyl, aryl, heteroaryl, (C １ ~C １８ ) alkoxy-(C １ ~C １８ ) alkyl, (C １ ~C １８ ) haloalkoxy-(C １ ~C １８ ) alkyl, (C １ ~C １８ ) alkoxy-(C １ ~C １８ ) haloalkyl, (C １ ~C １８ ) alkylthio-(C １ ~C １８ ) alkyl, (C １ ~C １８ ) haloalkylthio-(C １ ~C １８ ) alkyl, (C ２ ~C １８ ) haloalkenyl, (C ２ ~C １８ ) haloalkynyl, heterocyclyl-(C １ ~C １８ ) alkyl, aryl-(C １ ~C １８ ) alkyl, (C ３ ~C １２ ) cycloalkyl-(C １ ~C １８ ) alkyl, (C １ ~C １８ ) alkoxycarbonyl-(C １ ~C １８ ) alkyl or (C １ ~C １８ ) alkoxycarbonyl-(C ３ ~C １２ ) cycloalkyl-(C １ ~C １８ ) alkyl; n and m are independently the numbers 0, 1, 2 or 3; A compound of the general formula (I) according to claim 1 or a salt thereof.

4. Except for ethyl [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetate, R １ and R ２ are independently hydrogen, fluorine, chlorine, bromine, iodine, CN, methyl, CF ３ , C.H. ２ F, C.H.F. ２ , O.C.H. ３ , O.C.F. ３ , S.C.H. ３ or SCF ３ and R ３ is hydrogen or CH ３ and R ４ is hydrogen, (C １ ~C １０ ) alkyl, (C １ ~C １０ ) haloalkyl, (C １ ~C １０ ) cyanoalkyl, (C ２ ~C １０ ) alkenyl, (C ２ ~C １０ ) alkynyl, (C ３ ~C ９ ) cycloalkyl, (C ３ ~C ９ ) cycloalkenyl, aryl, heteroaryl, (C １ ~C １０ ) alkoxy-(C １ ~C １０ ) alkyl, (C １ ~C １０ ) haloalkoxy-(C １ ~C １０ ) alkyl, (C １ ~C １０ ) alkoxy-(C １ ~C １０ ) haloalkyl, (C １ ~C １０ ) alkylthio-(C １ ~C １０ ) alkyl, (C １ ~C １０ ) haloalkylthio-(C １ ~C １０ ) alkyl, (C ２ ~C １８ ) haloalkenyl, (C ２ ~C １８ ) haloalkynyl, heterocyclyl-(C １ ~C １０ ) alkyl, aryl-(C １ ~C １０ ) alkyl, (C ３ ~C ９ ) cycloalkyl-(C １ ~C １０ ) alkyl, (C １ ~C １０ ) alkoxycarbonyl-(C １ ~C １０ ) alkyl or (C １ ~C １０ ) alkoxycarbonyl-(C ３ ~C ９ ) cycloalkyl-(C １ ~C １０ ) alkyl; n and m are independently the numbers 0, 1, 2 or 3; A compound of the general formula (I) according to claim 1 or a salt thereof.

5. Except for ethyl [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetate, R １ and R ２ are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, CF ３ , C.H. ２ F, C.H.F. ２ , O.C.H. ３ , O.C.F. ３ , S.C.H. ３ or SCF ３ and R ３ is hydrogen, R ４ is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, n-pentyl, phenyl, benzyl, CH ２ (4-Cl-Ph), CH ２ (4-F-Ph), CH ２ (4-OMe-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl, methylpropionate-3-yl, ethylpropionate-3-yl, methylacetate-2-yl, ethylacetate-2-yl, methylpivalate-2-yl, ethylpivalate-3-yl, methyl-2-methylpropanoate-3-yl, methyl-2,2-dimethylpropanoate 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 aryl, 2,2,3,3,3-pentafluoropropyl, cyclopropylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl, allyl, propargyl (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl, 3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl , 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, heptan-2-yl, isobutyl, 1,3-dioxolan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl, n and m are independently the numbers 0, 1, 2 or 3; A compound of the general formula (I) according to claim 1 or a salt thereof.

6. Except for ethyl [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetate, (R １ ) ｎ -phenyl is Q-1.1 to Q-1.53 ​​groups and (R ２ ) ｍ -phenyl is Q-2.1 to Q-2.53 groups and R ３ is hydrogen, R ４ is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, n-pentyl, phenyl, benzyl, CH ２ (4-Cl-Ph), CH ２ (4-F-Ph), CH ２ (4-OMe-Ph), 2-methoxyethyl, tetrahydrofuran-2-yl-methyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl, methylpropionate-3-yl, ethylpropionate-3-yl, methylacetate-2-yl, ethylacetate-2-yl, methylpivalate-2-yl, ethylpivalate-3-yl, methyl-2-methylpropanoate-3-yl, methyl-2,2-dimethylpropanoate 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 aryl, 2,2,3,3,3-pentafluoropropyl, cyclopropylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl, allyl, propargyl (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl, 3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl , 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, heptan-2-yl, isobutyl, 1,3-dioxolan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl, A compound of the general formula (I) according to claim 1 or a salt thereof.

7. 10. A useful plant or crop plant protection composition, characterized by a content of at least one compound of general formula (I) or a salt thereof according to any one of claims 1 to 6 in combination with further pesticides and optionally formulation auxiliaries.

8. 8. The composition of claim 7 comprising at least one herbicide.

9. 10. Method for reducing the phytotoxic effect of pesticides on useful or crop plants by use of one or more compounds according to claims 1 to 6 or compositions according to claims 7 or 8.

10. A method for reducing the phytotoxic effect of a pesticide on useful or crop plants, characterized in that one or more inventive compounds of general formula (I) according to any one of claims 1 to 6 for use in combination with a pesticide are deployed simultaneously or in any order with said pesticide.

11. 11. The method of claim 10, wherein the pesticide is one or more herbicides.

12. 12. Method according to claim 10 or 11, characterized in that a compound of formula (I) as defined in claims 1 to 6 or a salt thereof is applied to a plant, a part of said plant, or a seed or seed material thereof.

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