Bromine- or iodine-para-substituted [(1,5-diphenyl-1h-1,2,4-triazol-3-yl)oxy]acetic acid derivatives and salts thereof, protection agents comprising them, for useful plants or crop plants, methods for producing them and use thereof as safeners

Abstract

The invention relates to bromine- or iodine-para-substituted [(1,5-Diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives and salts thereof, protection agents comprising them, for useful plants or crop plants, and methods for producing them and use thereof as safeners. The present invention relates to protection compounds and agents for useful plants, which compounds and agents comprise specific compounds as safeners for reducing phytotoxic effects of agrochemicals, especially herbicides. The invention relates more particularly to bromine- or iodine-para-substituted [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives of the general formula (I) and salts thereof, to methods for producing them and to the use thereof as protection compounds (safeners) for useful plants.

Description

[0001] Bayer AG

[0002] Bromine- or iodine-para-substituted [(l,5-diphenyl-lH-l,2,4-triazol-3-yl)oxy]acetic acid derivatives and their salts, crop-protecting agents containing them, processes for their preparation and their use as safeners

[0003] Description

[0004] The present invention relates to crop-protecting compounds and compositions containing specific compounds as safeners for reducing the phytotoxic effects of agrochemicals, especially herbicides. In particular, the invention relates to certain [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives and their salts as safeners, and to processes for their preparation.

[0005] When pesticides are used to combat unwanted organisms in agricultural and forestry crops, the crops themselves are often damaged to a greater or lesser extent by the pesticides used, such as herbicides, insecticides, fungicides, and others. This undesirable phytotoxic side effect occurs particularly frequently with the use of numerous herbicides—primarily with post-emergence application—in crops such as corn, rice, or cereals. Through the use of so-called "safeners" or "antidotes," crops can sometimes be protected against the phytotoxic properties of the pesticides without diminishing or significantly impairing their pesticidal effect against the pests. In some cases, the presence of safeners has even been observed to improve pesticidal effect against pests such as weeds.

[0006] The compounds known to date as safeners belong to a large number of different chemical structural classes, whereby their suitability for use as safeners generally also depends on the chemical structures of the pesticides and the crops.

[0007] The safener effects of compounds from the group of derivatives of phenoxy- or heteroaryloxyalkanecarboxylic acids have long been known when used in combination with herbicides. Examples of such compounds are MCPA and similar compounds, which also have herbicidal activity against weeds, or cloquintocet-mexyl.

[0008] Safeners from the group of derivatives of N-phenyl-substituted heteroaromatic carboxylic acid esters with multiple heteroatoms in the heterocycle are also known. Examples of such safeners are the safeners mefenpyr-diethyl and isoxadifen-ethyl used in commercial products. The use of hydroxy-substituted aromatic carboxylic acid derivatives is known from W02004 / 084631. W02005 / 015994 describes special derivatives of salicylic acid as safeners. These are particularly suitable for use as safeners in corn and soybean crops. Furthermore, 1,2-dihydroquinoxalin-2-one derivatives are known from W02005 / 112630 and pyridone carboxamides from W02008 / 131860.

[0009] Active ingredients from the chemical class of [(l,5-diphenyl-lH-l,2,4-triazol-3-yl)oxy]acetic acid derivatives with plant-active properties are known from WO2021105101.

[0010] Heterocyclic substituted derivatives with plant-active properties are described in WO2022 / 96449, WO2022 / 96446 and WO2022 / 96442.

[0011] Various publications describe [(l,5-diphenyl-lH-l,2,4-triazol-3-yl)oxy]acetic acid derivatives with medicinal properties. [(l,5-diphenyl-lH-l,2,4-triazol-3-yl)oxy]acetic acid derivatives are known from Polish J. Chem. 2006, 80, 889-897 and Bioorganic & Medicinal Chemistry 2018, 26, 3321-3344.

[0012] When using safeners to protect crops from pesticide damage, it has been shown that known safeners can have disadvantages in many cases. These include, for example, that (a) their crop-protective properties are insufficient, or (b) when combined with a specific herbicide, the range of crops in which the safener / herbicide is to be used is not sufficiently broad.

[0013] For the reasons mentioned above, there is an increased need to provide alternative compounds with safener effects.

[0014] The invention relates to novel crop-protecting compounds of the general formula (I) or salts thereof, for reducing the phytotoxic effects of pesticides, in particular herbicides, on crops or plants, wherein R 1 independently halogen, cyano, nitro, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkenyl, (C1-C6)-alkoxy or (C1-C6)-alkyl-S(O) p ,wherein the last seven radicals are unsubstituted or substituted by one or more radicals from the group halogen, cyano, (C1-C6)-alkoxy and (C1-C6)-alkyl-S(O) p are substituted, R 2independently of one another, halogen, cyano, nitro, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkenyl, (C1-C6)-alkoxy or (C1-C6)-alkyl-S(O)p, where the last-mentioned seven radicals are unsubstituted or are substituted by one or more radicals from the group consisting of halogen, cyano, (C1-C6)-alkoxy and (C1-C6)-alkyl-S(O)p, R 3 represents hydrogen or (C1-C6)-alkyl, R 4Hydrogen, (C1-C18)-alkyl, (C1-C18)-haloalkyl, (C1-C18)-cyanoalkyl, (C2-C18)-alkenyl, (C2-C18)-alkynyl, (C3-C12)-cycloalkyl, (C3-C12)-cycloalkenyl, aryl, heteroaryl, (C1- C18)-alkoxy-(C1-C18)-alkyl, (C1-C18)-haloalkoxy-(C1-C18)-alkyl, (C1-C18)-alkoxy-(C1-C18)-haloalkyl, (C1-C18)-alkylthio-(C1-C18)-alkyl, (C1-C18)-haloalkylthio-(C1-C18)-alkyl, (C2-C18)-haloalkenyl, (C2-C18)-haloalkynyl, heterocyclyl-(C1-C18)-alkyl, aryl-(C1-C18)-alkyl, (C3-C12)-cycloalkyl-(C1-C18)-alkyl, (C1-C18)-alkoxycarbonyl-(C1-C18)-alkyl, or (C1-C18)-alkoxycarbonyl-(C3-C12)-cycloalkyl-(C1-C18)-alkyl, or a radical of the formula -NR a R b or -N=CR c R d means, where in the above-mentioned 2 residues each of the residues R a , R b , R c and R d independently of one another represents hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, benzyl, substituted benzyl, phenyl or substituted phenyl, or R a and Rb together with the N atom form a 3- to 8-membered heterocycle which, in addition to the N atom, may contain one or two further hetero ring atoms 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 C atom, a 3- to 8-membered carbocyclic or heterocyclic radical which may contain 1 to 3 hetero ring atoms from the group N, O and S, where the carbocyclic or heterocyclic radical is unsubstituted or substituted by one or more radicals from the group (C1-C4)-alkyl and (C1-C4)-haloalkyl, R 5stands for bromine and iodine, n stands for a number from 1 to 4, m stands for a number from 0 to 5, and p is 0, 1 or 2. The compounds of the general formula (I) can form salts by addition of a suitable inorganic or organic acid, such as, for example, mineral acids, e.g. HCl, HBr, H2SO4, H3PO4 or HNO3, or organic acids, e.g. carboxylic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids, such as, for example, p-toluenesulfonic acid, to a basic group, such as, for example, amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino. These salts then contain the conjugate base of the acid as an anion. Suitable substituents which are present in deprotonated form, such as sulfonic acids, certain sulfonic acid amides or carboxylic acids, can form inner salts with protonatable groups, such as amino groups.Salt formation can also occur through 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, or alkaline earth metal hydroxides, carbonates, and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate, and sodium and potassium bicarbonate. These salts are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or ammonium salts, salts with organic amines, or quaternary ammonium salts, for example with cations of the formula [NR. e R f R g R h ] + , where R e to R heach independently of one another represents an organic radical, in particular alkyl, aryl, arylalkyl, or alkylaryl. Alkylsulfonium and alkylsulfoxonium salts, such as (C1-C4)-trialkylsulfonium and (C1-C4)-trialkylsulfoxonium salts, are also suitable. The compounds of formula (I) and their salts used according to the invention are referred to below as "compounds of the general formula (I)". Preferred subject matter of the invention are compounds of the general formula (I), wherein R 1 independently halogen, cyano, nitro, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, (C1-C4)-alkoxy or (C1-C4)-alkyl-S(O) p ,wherein the last-mentioned seven radicals are unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, (C1-C4)-alkoxy or (C1-C4)-alkyl-S(O) p are substituted, R 2independently of one another, halogen, cyano, nitro, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, (C1-C4)-alkoxy or (C1-C4)-alkyl-S(O)p, where the last-mentioned seven radicals are unsubstituted or are substituted by one or more radicals from the group consisting of halogen, cyano, (C1-C4)-alkoxy or (C1-C4)-alkyl-S(O)p, R 3 represents hydrogen or (C1-C4)-alkyl, R 4Hydrogen, (C1-C18)-alkyl, (C1-C18)-haloalkyl, (C1-C18)-cyanoalkyl, (C2-C18)-alkenyl, (C2-C18)-alkynyl, (C3-C12)-cycloalkyl, (C3-C12)-cycloalkenyl, aryl, heteroaryl, (C1- C18)-alkoxy-(C1-C18)-alkyl, (C1-C18)-haloalkoxy-(C1-C18)-alkyl, (C1-C18)-alkoxy-(C1-C18)-haloalkyl, (C1-C18)-alkylthio-(C1-C18)-alkyl, (C1-C18)-haloalkylthio-(C1-C18)-alkyl, (C2-C18)-haloalkenyl, (C2-C18)-haloalkynyl, heterocyclyl-(C1-C18)-alkyl, aryl-(C1-C18)-alkyl, (C3-C12)-cycloalkyl-(C1-C18)-alkyl, (C1-C18)-alkoxycarbonyl-(C1-C18)-alkyl, or (C1-C18)-Alkoxycarbonyl-(C3-C12)-cycloalkyl-(C1-C18)-alkyl means, R 5 represents bromine and iodine, n represents a number from 1 to 3, m represents a number from 0 to 4, and p represents 0, 1 or 2. Very particularly preferred subject matter of the invention are compounds of the general formula (I), wherein R 1 independently of one another halogen, cyano, methyl, CF3, CH2F, CHF2, OCH3, OCF3, SCH3 or SCF3, R 2independently of one another is halogen, cyano, methyl, CF3, CH2F, CHF2, OCH3, OCF3, SCH3 or SCF3, R 3 represents hydrogen, CH2CH3 or CH3, R 4 Hydrogen, (C1-C18)-alkyl, (C1-C18)-haloalkyl, (C1-C18)-cyanoalkyl, (C2-C18)-alkenyl, (C2-C18)-alkynyl, (C3-C12)-cycloalkyl, (C3-C12)-cycloalkenyl, aryl, heteroaryl, (C1- C18)-alkoxy-(C1-C18)-alkyl, (C1-C18)-haloalkoxy-(C1-C18)-alkyl, (C1-C18)-alkoxy-(C1-C18)-haloalkyl, (C1-C18)-alkylthio-(C1-C18)-alkyl, (C1-C18)-haloalkylthio-(C1-C18)-alkyl, (C2-C18)-haloalkenyl, (C2-C18)-haloalkynyl, heterocyclyl-(C1-C18)-alkyl, aryl-(C1-C18)-alkyl, (C3-C12)-cycloalkyl-(C1-C18)-alkyl, (C1-C18)-alkoxycarbonyl-(C1-C18)-alkyl, or (C1-C18)-alkoxycarbonyl-(C3-C12)-cycloalkyl-(C1-C18)-alkyl means. R 5 represents bromine and iodine, n represents a number from 1 to 2, m represents a number from 0 to 3, and p represents 0, 1 or 2. Particularly preferred subject matter of the invention are compounds of the general formula (I), wherein R1 unabhängig voneinander Fluor, Chlor, Brom, Iod, CN, Methyl, CF3, CH2F, CHF2, OCH3, OCF3, SCH3oder SCF3bedeutet, R 2 unabhängig voneinander Fluor, Chlor, Brom, Iod, CN, Methyl, CF3, CH2F, CHF2, OCH3, OCF3, SCH3oder SCF3bedeutet, R 3 für Wasserstoff oder CH3steht, R 4 Wasserstoff, (C1-C 10 )-Alkyl, (C1-C 10 )-Haloalkyl, (C1-C 10 )-Cyanoalkyl, (C2-C 10 )- Alkenyl, (C2-C 10 )-Alkinyl, (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 )-Haloalkinyl, Heterocyclyl-(C1-C 10)-alkyl, aryl-(C1-C10)-alkyl, (C3-C9)-cycloalkyl-(C1-C10)-alkyl, (C1-C10)-alkoxycarbonyl-(C1-C10)-alkyl or (C1-C10)-Alkoxycarbonyl-(C3-C9)-cycloalkyl-(C1-C10)-alkyl means, R 5 represents bromine and iodine, n represents a number from 1 to 2, m represents a number from 0 to 2, and p represents 0, 1 or 2. The invention particularly relates to compounds of the general formula (I), wherein R 1 Fluorine, chlorine, bromine, iodine, cyano, methyl, CF3, CH2F, CHF2, OCH3, OCF3, SCH3or SCF3 means, R 2 independently of one another represents fluorine, chlorine, bromine, iodine, cyano, methyl, CF3, CH2F, CHF2, OCH3, OCF3, SCH3 or SCF3, R 3 stands for hydrogen, R 4für Wasserstoff, 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-yl-methyl, Tetrahydropyran-2-yl-methyl, Tetrahydropyran-3- yl-methyl, Tetrahydropyran-4-yl-methyl, Methylpropionat-3-yl, Ethylpropionat-3-yl, Methylacetat-2-yl, Ethylacetat-2-yl, Methylpivalat-2-yl, Ethylpivalat-3-yl, Methyl-2- methylpropanoat-3-yl, Methyl-2,2-dimethylpropanoat-3-yl, Ethyl-2-methylpropanoat-3- yl, Methyl-2-propanoat-2-yl, Ethyl-2-propanoat-2-yl, Methyl-acetat-2yl, Ethyl-acetat- 2yl, Methyl- 1 -methylcyclopropancarboxylat-2yl, Ethyl- 1 -methylcyclopropan- carboxylat-2yl, 2-(Dimethylamino)ethyl, Oxetan-3-yl, (3-Methyloxetan-3-yl)methyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, 2-Fluorethyl, 2,2,3,3,3-Pentafluorpropyl, Cyclopropylmethyl, 1-Cyclopropyl-ethyl, (l-Methyl-cyclopropyl)-methyl, (2,2- Dichlorcyclopropyl)-methyl, (2,2-Dimethyl-cyclopropyl)-methyl, Allyl,Propargyl (Prop-2-yn-l-yl), 2-Chloroprop-2-en-l-yl, 3-Phenylprop-2-yn-l-yl, 3,3-Dichloroprop-2-en-1-yl, 3,3-Dichloro-2-fluoro-prop-2-en-l-yl, Methylprop-2-yn-l-yl, 2-Methylprop-2-en-l-yl, But-2-en-l-yl, But-3-en-l-yl, But-2-yn-l-yl, But-3-yn-l-yl, 4-Chloro-but-2-yn-l-yl, 3-Methyl-but-2-en-l-yl, 3-Methyl-but-l-en-l-yl, 1-(2E)-l-methylbut-2-en-l-yl, (E)-Pent- 3-en-2-yl or (Z)-Pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, heptan-2-yl, iso-butyl, l,3-dioxolan-2-ylmethyl or l-ethyl-5-methyl-1H-pyrazole-4-methyl,

[0015] R 5 stands for bromine and iodine, n stands for the number 1, m stands for a number from 0 to 2.

[0016] The most particularly preferred subject matter of the invention are compounds of the general formula (I) in which para-R 5 -(R') n -Phenyl for groups Ql.l to Q-1.2 stands, and (R 2 ) m -Phenyl for groups Q-2.1 to Q-2.53 0 . 0 . S . i S • 0 . S stands, R 3 stands for hydrogen, and R 4für Wasserstoff, 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-yl-methyl, Tetrahydropyran-2-yl-methyl, Tetrahydropyran-3- yl-methyl, Tetrahydropyran-4-yl-methyl, Methylpropionat-3-yl, Ethylpropionat-3-yl, Methylacetat-2-yl, Ethylacetat-2-yl, Methylpivalat-2-yl, Ethylpivalat-3-yl, Methyl-2- methylpropanoat-3-yl, Methyl-2,2-dimethylpropanoat-3-yl, Ethyl-2-methylpropanoat-3- yl, Methyl-2-propanoat-2-yl, Ethyl-2-propanoat-2-yl, Methyl-acetat-2yl, Ethyl-acetat- 2yl, Methyl-1-methylcyclopropancarboxylat-2yl, Ethyl-1-methylcyclopropan- carboxylat-2yl, 2-(Dimethylamino)ethyl, Oxetan-3-yl, (3-Methyloxetan-3-yl)methyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, 2-Fluorethyl, 2,2,3,3,3-Pentafluorpropyl, Cyclopropylmethyl, 1-Cyclopropyl-ethyl, (l-Methyl-cyclopropyl)-methyl, (2,2- Dichlorcyclopropyl)-methyl, (2,2-Dimethyl-cyclopropyl)-methyl, Allyl,Propargyl (Prop-2-yn-l-yl), 2-Chloroprop-2-en-l-yl, 3-Phenylprop-2-yn-l-yl, 3,3-Dichloroprop-2-en-1-yl, 3,3-Dichloro-2-fluoro-prop-2-en-l-yl, Methylprop-2-yn-l-yl, 2-Methylprop-2-en-l-yl, But-2-en-l-yl, But-3-en-l-yl, But-2-yn-l-yl, But-3-yn-l-yl, 4-Chloro-but-2-yn-l-yl, 3-Methyl-but-2-en-l-yl, 3-Methyl-but-l-en-l-yl, 1-(2E)-l-methylbut-2-en-l-yl, (E)-Pent- 3-en-2-yl or (Z)-Pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, heptan-2-yl, iso-butyl, l,3-dioxolan-2-ylmethyl or l-ethyl-5-methyl-lHpyrazole-4-methyl.

[0017] The above general or preferred radical definitions apply both to the end products of general formula (I) and, accordingly, to the starting materials or intermediates required for their preparation. These radical definitions can be combined with each other, including within the given preferred ranges.

[0018] Particularly for reasons of higher herbicidal activity, better selectivity and / or better producibility, compounds according to the invention of the general formula (I) mentioned or salts thereof or the use thereof according to the invention are of particular interest in which individual radicals have one of the preferred meanings already mentioned or mentioned below, or in particular those in which one or more of the preferred meanings already mentioned or mentioned below occur in combination.

[0019] With regard to the compounds according to the invention, the terms used above and below are explained. These are familiar to the person skilled in the art and have, in particular, the meanings explained below:

[0020] Unless otherwise defined, the general rule for the designation of chemical groups is that the connection to the skeleton or the rest of the molecule is via the last-mentioned structural element of the chemical group in question, ie for example in the case of (C2-Cs)-alkenyloxy via the oxygen atom, and in the case of heterocyclyl-(Ci-Cs)-alkyl or alkylO(O)C-(Ci-Cs)-alkyl via the C atom of the alkyl group.

[0021] According to the invention, "alkylsulfonyl", unless defined otherwise elsewhere, - alone or as part of a chemical group - stands for straight-chain or branched alkylsulfonyl, preferably with 1 to 8, or with 1 to 6 carbon atoms, e.g.(aber nicht beschränkt auf) (Ci-Ce) -Alkylsulfonyl wie Methylsulfonyl, Ethylsulfonyl, Propylsulfonyl, 1 -Methylethylsulfonyl, Butylsulfonyl, 1 -Methylpropylsulfonyl, 2-Methylpropylsulfonyl, 1,1 -Dimethylethylsulfonyl, Pentylsulfonyl, 1-Methylbutylsulfonyl, 2-Methylbutylsulfonyl, 3-Methylbutylsulfonyl, 1,1- Dimethylpropylsulfonyl, 1,2-Dimethylpropylsulfonyl, 2,2-Dimethylpropylsulfonyl, 1- Ethylpropylsulfonyl, Hexylsulfonyl, 1-Methylpentylsulfonyl, 2-Methylpentylsulfonyl, 3- Methylpentylsulfonyl, 4-Methylpentylsulfonyl, 1,1-Dimethylbutylsulfonyl, 1,2-Dimethylbutylsulfonyl, 1,3-Dimethylbutylsulfonyl, 2,2-Dimethylbutylsulfonyl, 2,3-Dimethylbutylsulfonyl, 3,3- Dimethylbutylsulfonyl, 1-Ethylbutylsulfonyl, 2-Ethylbutylsulfonyl, 1,1,2-Trimethylpropylsulfonyl, 1,2,2-Trimethylpropylsulfonyl, 1-Ethyl-1-methylpropylsulfonyl und 1-Ethyl-2-methylpropylsulfonyl.According to the invention, "alkylthio", unless defined otherwise elsewhere, - alone or as part of a chemical group - stands for straight-chain or branched S-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as (C1-C10)-, (C1-C6)- or (C1-C4)-alkylthio, e.g.(but not limited to) (C1-C6)-alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-Dimethylpropylthio, 1,2-Dimethylpropylthio, 2,2-Dimethylpropylthio, 1-Ethylpropylthio, Hexylthio, 1-Methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methylpentylthio, 1,1-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. "Alkylsulfinyl (alkyl-S(=O)-)", unless defined otherwise elsewhere, represents, according to the invention, alkyl radicals that are bonded to the skeleton via -S(=O)-, such as (C1-C6)- or (C1-C4)-alkylsulfinyl, e.g.(aber nicht beschränkt auf) (C1-C6)-Alkylsulfinyl wie 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-Di- methylpropylsulfinyl, 1-Ethylpropylsulfinyl, Hexylsulfinyl, 1-Methylpentylsulfinyl, 2-Methylpentyl- sulfinyl, 3-Methylpentylsulfinyl, 4-Methylpentylsulfinyl, 1,1-Dimethylbutylsulfinyl, 1,2-Dimethyl- butylsulfinyl, 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 und 1-Ethyl-2-methylpropylsulfinyl. „Alkoxy“ bedeutet ein über ein Sauerstoffatom gebundenen Alkylrest, z. B.(but not limited to) (C1-C6)-alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-Trimethylpropoxy, 1,2,2-Trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy. Alkenyloxy means an alkenyl radical bonded via an oxygen atom, alkynyloxy means an alkynyl radical bonded via an oxygen atom such as (C2-C6). 10)-, (C2-C6)- or (C2-C4)-alkenoxy or (C3-C6)- or (C3-C4)-alkynoxy. “Alkylcarbonyl” (alkyl-C(=O)-), unless defined otherwise elsewhere, stands according to the invention for alkyl radicals that are bonded to the skeleton via -C(=O)-, such as (C1-C10)-, (C1-C6)- or (C1-C4)-alkylcarbonyl. The number of C atoms refers to the alkyl radical in the alkylcarbonyl group. “Alkoxycarbonyl (alkyl-OC(=O)-)” stands according to the invention, unless defined otherwise elsewhere, for alkyl radicals that are bonded to the skeleton via -OC(=O)-, such as (C1-C10)-, (C1-C6)- or (C1-C4)-alkoxycarbonyl. The number of C atoms refers to the alkyl radical in the alkoxycarbonyl group. Analogously, unless defined otherwise elsewhere, "alkenyloxycarbonyl" and "alkynyloxycarbonyl" represent, according to the invention, alkenyl or alkynyl radicals bonded to the skeleton via -OC(=O)-, such as (C2-C10)-, (C2-C6)-, or (C2-C4)-alkenyloxycarbonyl, respectively.(C3-C10)-, (C3-C6)-, or (C3-C4)-alkynyloxycarbonyl. The number of C atoms refers to the alkenyl or alkynyl radical in the alkene or alkynyloxycarbonyl group. The term "alkylcarbonyloxy" (alkyl-C(=O)-O-) stands for alkyl radicals that are bonded to the skeleton via a carbonyloxy group (-C(=O)-O-), such as (C1-C10)-, (C1-C6)-, or (C1-C4)-alkylcarbonyloxy. The number of C atoms refers to the alkyl radical in the alkylcarbonyloxy group. The term “aryl” means an optionally substituted mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring carbon atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.The term "optionally substituted aryl" also encompasses polycyclic systems such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, and biphenylyl, where the bonding site is on the aromatic system. Systematically, "aryl" is generally also encompassed by the term "optionally substituted phenyl."Bevorzugte Aryl-Substituenten sind hier zum Beispiel Wasserstoff, Halogen, Alkyl, Cycloalkyl, Cycloalkylalkyl, Cycloalkenyl, Halocycloalkyl, Alkenyl, Alkinyl, Aryl, Arylalkyl, Heteroaryl, Heteroarylalkyl, Heterocyclyl, Heterocyclylalkyl, Alkoxyalkyl, Alkylthio, Haloalkylthio, Haloalkyl, Alkoxy, Haloalkoxy, Cycloalkoxy, Cycloalkylalkoxy, Aryloxy, Heteroraryloxy, Alkoxyalkoxy, Alkinylalkoxy, Alkenyloxy, Bis-alkylaminoalkoxy, Tris-[alkyl]silyl, Bis- [alkyl] arylsilyl, Bis- [alkyl] alkylsilyl, Tris- [alkyl] silylalkinyl, Alkylalkinyl, Cycloalkylalkinyl, Haloalkylalkinyl, Heterocyclyl-N-alkoxy, Nitro, Cyano, Amino, Alkylamino, Bis-alkylamino, Alkylcarbonylamino, Cycloalkylcarbonylamino, Arylcarbonylamino, Alkoxycarbonylamino, Alkoxycarbonylalkylamino, Arylalkoxycarbonylalkylamino, Hydroxycarbonyl, Alkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Cycloalkylaminocarbonyl, Bis-Alkylaminocarbonyl, Heteroarylalkoxy, Arylalkoxy.

[0022] A heterocyclic radical (heterocyclyl) contains at least one heterocyclic ring (=carbocyclic ring in which at least one C atom is replaced by a heteroatom, preferably by a heteroatom from the group N, O, S, P) which is saturated, unsaturated, partially saturated or heteroaromatic and may be unsubstituted or substituted, with the bonding site being located on a ring atom. If the heterocyclyl radical or the heterocyclic ring is optionally substituted, it may be fused to other carbocyclic or heterocyclic rings. In the case of optionally substituted heterocyclyl, polycyclic systems are also included, such as, for example, 8-azabicyclo[3.2.1]octanyl, 8-azabicyclo[2.2.2]octanyl or 1-azabicyclo[2.2.1]heptyl. In the case of optionally substituted heterocyclyl, spirocyclic systems are also included, such as l-oxa-5-aza-spiro[2.3]hexyl.Unless otherwise defined, the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, although two oxygen atoms should not be directly adjacent, such as, for example, with a heteroatom from 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-pyrrole-.

[0023] 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-

[0024] 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-

[0025] 1- or -2- or 3- or 4- or 5- or 6- or 7-yl; 2,7-Dihydro-lH-azepin-l- or -2- or 3- or 4- yl; 2,3-Dihydro-lH-azepin-l- or -2- or 3- or 4- or 5- or 6- or 7-yl; 3,4-Dihydro-2H-azepin-

[0026] 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; 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

[0027] 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

[0028] 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- 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-dihydrothiophen-2- or 3- or 4- or 5-yl; 2,5-dihydrothiophen-2- or 3-yl; Tetrahydro-2H-thiopyran-2- or 3- or 4-yl; 3,4-Dihydro-2H-thiopyran-2- or 3- or 4- or

[0029] 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-membered and 4-membered ring heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl,

[0030] 2- or 3-oxetanyl, 2- or 3-thietanyl, l,3-dioxetan-2-yl. Further examples of “heterocyclyl” are a partially or fully hydrogenated heterocyclic radical with two heteroatoms from the group 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-lH-pyrazol-l- or 3- or 4- or 5-yl; 2,3-dihydro-lH-pyrazol-l- or 2- or

[0031] 3- or 4- or 5-yl; 1- or 2- or 3- or 4- imidazolidinyl; 2,3-dihydro-lH-imidazol-l- or 2- or

[0032] 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

[0033] 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-dihydropyriazin-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-l- 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-l- or 2- or

[0034] 4- or 5- or 6-yl; 1,2-Dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 2,5-Dihydropyrimidin-

[0035] 2- or 4- or 5-yl; 4,5-Dihydropyrimidin- 4- or 5- or 6-yl; 1,4-Dihydropyrimidin-l- or 2- or 4- or 5- or 6-yl; 1- or 2- or 3-piperazinyl; 1,2,3,6-Tetrahydropyrazin-l- or 2- or 3- or 5- or 6-yl; 1,2,3,4-Tetrahydropyrazin-l- or 2- or 3- or 4- or 5- or 6-yl; 1,2-Dihydropyrazin-l- or 2- or 3- or 5- or 6-yl; 1,4-Dihydropyrazin-l- or 2- or 3-yl; 2,3-Dihydropyrazin-2- or

[0036] 3- or 5- or 6-yl; 2,5-Dihydropyrazin-2- or 3-yl; l,3-dioxolan-2- or 4- or 5-yl; l,3-dioxol-2- or 4-yl; l,3-dioxan-2- or 4- or 5-yl; 4H-l,3-dioxin-2- or 4- or 5- or 6-yl; 1,4-dioxan-2- or 3- or 5- or 6-yl; 2,3-Dihydro-l,4-dioxin-2- or 3- or 5- or 6-yl; 1,4-dioxin-2- or 3-yl; l,2-Dithiolan-3- or 4-yl; 3H-l,2-Dithiol-3- or 4- or 5-yl; l,3-Dithiolan-2- or 4-yl; 1,3-Dithiol-2- or 4-yl; l,2-Dithian-3- or 4-yl; 3,4-Dihydro-1,2-dithiin-3- or 4- or 5- or 6-yl; 3,6-dihydro

[0037] 1,2-dithiin-3- or 4-yl; l,2-dithiin-3- or 4-yl; l,3-dithian-2- or 4- or 5-yl; 4H-l,3-dithiin-2- or 4- or 5- or 6-yl; isoxazolidin-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;

[0038] 1,3-oxazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydro-l,3-oxazol-2- or 3- or 4- or 5-yl; 2,5-dihydro-l,3-oxazol-2- or 4- or 5-yl; 4,5-dihydro-l,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-l,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-l,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-Dihydro-2H-l,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-Dihydro-4H-l,2-oxazin-3- or 4- or 5- or 6-yl; 2H-l,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 6H-l,2-oxazin-3- or 4- or 5- or 6-yl; 4H-l,2-oxazin-3- or 4- or 5- or 6-yl; l,3-Oxazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-Dihydro-2H-l,3-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-Dihydro-2H-l,3-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-Dihydro-2H-

[0039] 1,3-oxazin-2- or 4- or 5- or 6-yl; 5,6-dihydro-4H-l,3-oxazin-2- or 4- or 5- or 6-yl; 2H-

[0040] 1,3-Oxazin-2- or 4- or 5- or 6-yl; 6H-1,3-Oxazin-2- or 4- or 5- or 6-yl; 4H-1,3-Oxazin-2- or 4- or 5- or 6-yl; Morpholin-2- or 3- or 4-yl; 3,4-Dihydro-2H-1,4-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-Dihydro-2H-1,4-oxazin-2- or 3- or 5- or 6-yl; 2H-1,4-oxazin-2- or 3- or 5- or 6-yl; 4H-1,4-oxazin-2- or 3-yl; 1,2-Oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,5-Tetrahydro-l,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-Tetrahydro-l,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-Tetrahydro-l,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7-Tetrahydro-l,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5,6,7-Tetrahydro-l,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 2,3-Dihydro-l,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5-Dihydro-l,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;2,7-Dihydro-l,2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-Dihydro-l,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 4,7-Dihydro-l,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 6,7-Dihydro-l,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; l,2-oxazepin-3- or 4- or 5- or 6- or 7-yl; l,3-Oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,5-Tetrahydro-l,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-Tetrahydro-l,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-Tetrahydro-l,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7-Tetrahydro-l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,5,6,7-Tetrahydro-l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 2,3-Dihydro-l,3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5-Dihydro-l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 2,7-Dihydro-l,3-oxazepin- 2- or 4- or 5- or 6- or 7-yl;4,5-Dihydro-l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,7-Dihydro-l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 6,7-Dihydro-l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; l,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-l,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2, 3,4,7-Tetrahydro-l,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-Tetrahydro-l,4-oxazepin- 2- or 3- or 5- or 6- or 7-yl; 2,5,6,7-Tetrahydro-l,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 4,5,6,7-Tetrahydro-l,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3-Dihydro-l,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 2,5-Dihydro-l,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 2,7-Dihydro-l,4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 4,5-Dihydro-l,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl;4,7-Dihydro-l,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 6,7-Dihydro-l,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; Isothiazolidin-2- or 3- or 4- or 5-yl; 2,3-Dihydroisothiazol-2- or 3- or 4- or 5-yl; 2,5-Dihydroisothiazol-2- or 3- or 4- or 5-yl; 4,5-Dihydroisothiazol-3- or 4- or 5-yl; 1,3-Thiazolidin-2- or 3- or 4- or 5-yl; 2,3-Dihydro-l,3-thiazol-2- or 3- or 4- or 5-yl; 2,5-Dihydro-l,3-thiazol-2- or 4- or 5-yl; 4,5-Dihydro-l,3-thiazol-2- or 4- or 5-yl; l,3-Thiazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-Dihydro-2H-l,3-thiazin-2- or 3- or 4- or 5- or 6-yl; 3,6-Dihydro-2H-l,3-thiazin-2- or 3- or 4- or 5- or 6-yl; 5,6-Dihydro-2H-l,3-thiazin-2- or 4- or 5- or 6-yl; 5,6-Dihydro-4H-l,3-thiazin-2- or 4- or 5- or 6-yl; 2H-l,3-thiazin-2- or 4- or 5- or 6-yl; 6H-l,3-thiazin-2- or 4- or 5- or 6-yl;4H-l,3-Thiazin-2- or 4- or 5- or 6-yl. Further examples of “heterocyclyl” are a partially or fully hydrogenated heterocyclic radical with 3 heteroatoms from the group N, O and S, such as, for example, 1,4,2-dioxazolidin-2- or 3- or 5-yl; l,4,2-dioxazol-3- or 5-yl; 1,4,2-dioxazinan-2- or -3- or 5- or 6-yl; 5,6-dihydro-l,4,2-dioxazin-3- or 5- or 6-yl; l,4,2-dioxazin-3- or 5- or 6-yl; 1,4,2-dioxazepan-2- or 3- or 5- or 6- or 7-yl; 6,7-Dihydro-5H-l,4,2-dioxazepin-3- or 5- or 6- or 7-yl; 2,3-Dihydro-7H-l,4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl; 2,3-Dihydro-5H-l,4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl; 5H-l,4,2-dioxazepin-3- or 5- or 6- or 7-yl; 7H-l,4,2-dioxazepin-3- or 5- or 6- or 7-yl. Structural examples of optionally further substituted heterocycles are also listed below:;

[0041]

[0042] Die oben auf geführten Heterocyclen sind bevorzugt beispielsweise durch Wasserstoff, Halogen, Alkyl, Haloalkyl, Hydroxy, Alkoxy, Cycloalkoxy, Aryloxy, Alkoxyalkyl, Alkoxyalkoxy, Cycloalkyl, Halocycloalkyl, Aryl, Arylalkyl, Heteroaryl, Heterocyclyl, Alkenyl, Alkylcarbonyl, Cycloalkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, Alkoxycarbonyl, Hydroxycarbonyl, Cycloalkoxycarbonyl, Cycloalkylalkoxycarbonyl, Alkoxycarbonylalkyl, Arylalkoxycarbonyl, Arylalkoxycarbonylalkyl, Alkinyl, Alkinylalkyl, Alkylalkinyl, Tris-alkylsilylalkinyl, Nitro, Amino, Cyano, Haloalkoxy, Haloalkylthio, Alkylthio, Hydrothio, Hydroxyalkyl, Oxo, Heteroarylalkoxy, Arylalkoxy, Heterocyclylalkoxy, Heterocyclylalkylthio, Heterocyclyloxy, Heterocyclylthio, Heteroaryloxy, Bisalkylamino, Alkylamino, Cycloalkylamino, Hydroxycarbonylalkylamino, Alkoxycarbonylalkylamino, Arylalkoxycarbonylalkylamino, Alkoxycarbonylalkyl(alkyl)amino, Aminocarbonyl, Alkylaminocarbonyl, Bis-alkylaminocarbonyl, Cycloalkylaminocarbonyl,Hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl, arylalkoxycarbonylalkylaminocarbonyl substituted.,

[0043] If a basic structure is substituted "by one or more residues" from a list of residues (= group) or a generically defined group of residues, this includes the simultaneous substitution by several identical and / or structurally different residues.

[0044] If it is a partially or fully saturated nitrogen heterocycle, it can be linked to the rest of the molecule via either carbon or nitrogen.

[0045] Possible substituents for a substituted heterocyclic radical are the substituents listed below, as well as oxo and thioxo. The oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring. This preferably also includes lactones and lactams. The oxo group can also occur on the hetero ring atoms, which can exist in different oxidation states, e.g. N and S, and then forms, for example, the divalent groups N(O), S(O) (also abbreviated SO) and S(O)2 (also abbreviated SO2) in the heterocyclic ring. In the case of -N(O)- and -S(O)- groups, both enantiomers are included.

[0046] According to the invention, the term “heteroaryl” stands for heteroaromatic compounds, ie completely unsaturated aromatic heterocyclic compounds, preferably for 5- to 7-membered rings with 1 to 4, preferably 1 or 2 identical or different heteroatoms, preferably O, S or N. Heteroaryls according to the invention are, for example, IH-pyrrol-1-yl; IH-pyrrol-2-yl; IH-pyrrol-

[0047] 3-yl; furan-2-yl; furan-3-yl; thien-2-yl; Thien-3-yl, IH-imidazol-l-yl; lH-imidazol-2-yl; IH-imidazole

[0048] 4-yl; lH-Imidazol-5-yl; IH-Pyrazol-l-yl; lH-Pyrazol-3-yl; lH-Pyrazol-4-yl; lH-Pyrazol-5-yl, 1H-1,2,3- Triazol-l-yl, lH-l,2,3-Triazol-4-yl, lH-l,2,3-Triazol-5-yl, 2H-l,2,3-Triazol-2-yl, 2H-l,2,3-Triazol-4-yl, lH-l,2,4-Triazol-l-yl, lH-l,2,4-Triazol-3-yl, 4H-l,2,4-Triazol-4-yl, l,2,4-Oxadiazol-3-yl, 1,2,4- Oxadiazol-5-yl, l,3,4-Oxadiazol-2-yl, l,2,3-Oxadiazol-4-yl, l,2,3-Oxadiazol-5-yl, l,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, l,3,5-Triazin-2-yl, l,2,4-Triazin-3-yl, l,2,4-Triazin-5-yl, l,2,4-Triazin-6-yl, l,2,3-Triazin-4-yl, l,2,3-Triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- und 1,2,6-Oxazinyl, Isoxazol-3-yl, Isoxazol-4-yl, Isoxazol-5-yl, l,3-Oxazol-2-yl, l,3-Oxazol-4-yl, 1,3- Oxazol-5-yl, Isothiazol-3-yl, Isothiazol-4-yl, Isothiazol-5-yl, l,3-Thiazol-2-yl, l,3-Thiazol-4-yl, 1,3- Thiazol-5-yl, Oxepinyl, Thiepinyl, 1 ,2,4-Triazolonyl und 1 ,2,4-Diazepinyl,2H-l,2,3,4-tetrazol-5-yl, lH-l,2,3,4-tetrazol-5-yl, l,2,3,4-oxatriazol-5-yl, l,2,3,4-thiatriazol-5-yl, l,2,3,5-oxatriazol-4-yl, l,2,3,5-thiatriazol-4-yl. The heteroaryl groups according to the invention can further be substituted with one or more identical or different radicals. If two adjacent carbon atoms are part of another aromatic ring, these are fused heteroaromatic systems, such as benzofused or multiply fused heteroaromatics. For example, quinolines are preferred (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); quinoxaline; quinazoline; cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-Naphthyridin; Phthalazin; Pyridopyr azine; Pyridopyrimidine; Pyridopyridazine; Pteridine; Pyrimidopyrimidine. Beispiele für Heteroaryl sind auch 5- oder 6-gliedrige benzokondensierte Ringe aus der Gruppe IH-Indol-l-yl, lH-Indol-2-yl, lH-Indol-3-yl, lH-Indol-4-yl, lH-Indol-5-yl, 1H- Indol-6-yl, lH-Indol-7-yl, l-Benzofuran-2-yl, l-Benzofuran-3-yl, l-Benzofuran-4-yl, l-Benzofuran-5- yl, l-Benzofuran-6-yl, l-Benzofuran-7-yl, l-Benzothiophen-2-yl, l-Benzothiophen-3-yl, 1- Benzothiophen-4-yl, l-Benzothiophen-5-yl, l-Benzothiophen-6-yl, l-Benzothiophen-7-yl, IH-Indazol-,

[0049] 1-yl, lH-Indazol-3-yl, lH-Indazol-4-yl, lH-Indazol-5-yl, lH-Indazol-6-yl, lH-Indazol-7-yl, 2H-Indazol-

[0050] 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-l-yl, 2H-Isoindol-3-yl, 2H-Isoindol-4-yl, 2H-Isoindol-5-yl, 2H-Isoindol-6-yl; 2H-Isoindol-7-yl, IH-Benzimidazol-l-yl, lH-Benzimidazol-2-yl, lH-Benzimidazol-4-yl, 1H- Benzimidazol-5-yl, lH-Benzimidazol-6-yl, lH-Benzimidazol-7-yl, l,3-Benzoxazol-2-yl, 1,3- Benzoxazol-4-yl, l,3-Benzoxazol-5-yl, l,3-Benzoxazol-6-yl, l,3-Benzoxazol-7-yl, l,3-Benzthiazol-2-yl, l,3-Benzthiazol-4-yl, l,3-Benzthiazol-5-yl, l,3-Benzthiazol-6-yl, l,3-Benzthiazol-7-yl, 1,2- Benzisoxazol-3-yl, l,2-Benzisoxazol-4-yl, l,2-Benzisoxazol-5-yl, l,2-Benzisoxazol-6-yl, 1,2- Benzisoxazol-7-yl, l,2-Benzisothiazol-3-yl, 1 ,2-Benzisothiazol-4-yl, l,2-Benzisothiazol-5-yl, 1,2- Benzisothiazol-6-yl, 1 ,2-Benzisothiazol-7-yl.

[0051] The term "halogen" means, for example, fluorine, chlorine, bromine, or iodine. When used for a radical, "halogen" means, for example, a fluorine, chlorine, bromine, or iodine atom.

[0052] According to the invention, "alkyl" means a straight-chain or branched, open-chain, saturated hydrocarbon radical, which is optionally mono- or polysubstituted and, in the latter case, is referred to as "substituted alkyl." Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, cycloalkyl, alkoxycarbonyl, hydroxycarbonyl, heterocyclyl, hetaryl, aryl, amino, or nitro groups; particularly preferred are methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine, or iodine. The prefix "bis" also includes the combination of different alkyl radicals, e.g., methyl(ethyl) or ethyl(methyl).

[0053] “Haloalkyl”, “-alkenyl” and “-alkynyl” mean alkyl, alkenyl or alkynyl which are partially or fully substituted by identical or different halogen atoms, e.g. monohaloalkyl

[0054] (= monohaloalkyl) such as CH2CH2CI, CH2CH2Br, CHCICH3, CH2CI, CH2F; perhaloalkyl such as CC13, CC1F2, CFC12, CF2CC1F2, CF2CCIFCF3; polyhaloalkyl such as CH2CHFC1, CF2CC1FH, CF2CBrFH, CH2CF3; the term perhaloalkyl also includes the term perfluoroalkyl.

[0055] “Partially fluorinated alkyl” means a straight-chain or branched, saturated hydrocarbon which is mono- or polysubstituted by fluorine, where the corresponding fluorine atoms can be located as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain, such as CHFCH3, CH2CH2F, CH2CH2CF3, CHF2, CH2F, CHFCF2CF3.

[0056] "Partially fluorinated haloalkyl" means a straight-chain or branched, saturated hydrocarbon substituted by various halogen atoms with at least one fluorine atom, where any other halogen atoms present are selected from the group consisting of fluorine, chlorine, bromine, and iodine. The corresponding halogen atoms can be located as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain. Partially fluorinated haloalkyl also includes the complete substitution of the straight-chain or branched chain by halogen with the participation of at least one fluorine atom.

[0057] “Haloalkoxy” is, for example, OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3, and OCH2CH2CI; the same applies to haloalkenyl and other halogen-substituted radicals.

[0058] The term "(C1-C4)-alkyl" used here as an example is a shorthand notation for straight-chain or branched alkyl with one to four carbon atoms, corresponding to the range specified for carbon atoms, i.e., it includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl, or tert-butyl. General alkyl radicals with a larger specified range of carbon atoms, e.g., "(C1-C6)-alkyl," correspondingly also include straight-chain or branched alkyl radicals with a larger number of carbon atoms, i.e., according to the example, also the alkyl radicals with 5 and 6 carbon atoms.

[0059] Unless specifically stated, lower carbon skeletons, e.g., those with 1 to 6 C atoms, or unsaturated groups with 2 to 6 C atoms, are preferred for hydrocarbon radicals such as alkyl, alkenyl, and alkynyl, even in compound radicals. Alkyl radicals, even in compound radicals such as alkoxy, haloalkyl, etc., are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t-, or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl, and 1,3-dimethylbutyl, and heptyls, such as n-heptyl, 1-methylhexyl, and 1,4-dimethylpentyl. Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, containing at least one double bond or triple bond, respectively. Preferred are residues with a double bond or triple bond.

[0060] The term “alkenyl” includes in particular straight-chain or branched open-chain hydrocarbon radicals with more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals with one or more cumulated double bonds, such as, for example, allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl. Alkenyl means, for example, vinyl, which may optionally be substituted by further alkyl radicals, for example (but not limited to) (C2-C8)-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3-Methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, l,l-dimethyl-2-propenyl, 1,2-dimethyl-l-propenyl, 1,2-dimethyl-2-propenyl,1 -Ethyl- 1 -propenyl, l-Ethyl-2-propenyl, 1 -Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5- Hexenyl, 1 -Methyl- 1-pentenyl, 2-Methyl-l -pentenyl, 3-Methyl-l-pentenyl, 4-Methyl-l-pentenyl, 1- Methyl-2-pentenyl, 2-Methyl-2-pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl, l-Methyl-3- pentenyl, 2-Methyl-3-pentenyl, 3-Methyl-3-pentenyl, 4-Methyl-3-pentenyl, l-Methyl-4-pentenyl, 2- Methyl-4-pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, l,l-Dimethyl-2-butenyl, 1,1-Dimethyl- 3-butenyl, 1,2-Dimethyl-l -butenyl, 1 ,2-Dimethyl-2-butenyl, l,2-Dimethyl-3-butenyl, 1, 3 -Dimethyl- 1- butenyl, l,3-Dimethyl-2-butenyl, l,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3-Dimethyl-l- butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3-Dimethyl-l-butenyl, 3,3-Dimethyl-2- butenyl, 1 -Ethyl- 1-butenyl, l-Ethyl-2-butenyl, l-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 und l-Ethyl-2-methyl-2-propenyl.,

[0061] The term "alkynyl" includes in particular straight-chain or branched open-chain hydrocarbon radicals with more than one triple bond or with one or more triple bonds and one or more double bonds, such as 1,3-butatrienyl or 3-penten-l-yn-l-yl. (C2-Ce)-alkynyl means, for example,Ethinyl, 1-Propinyl, 2-Propinyl, 1-Butinyl, 2- Butinyl, 3-Butinyl, l-Methyl-2-propinyl, 1-Pentinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, l-Methyl-2- butinyl, l-Methyl-3-butinyl, 2-Methyl-3-butinyl, 3-Methyl-l-butinyl, l,l-Dimethyl-2-propinyl, 1-Ethyl- 2-propinyl, 1-Hexinyl, 2-Hexinyl, 3-Hexinyl, 4-Hexinyl, 5-Hexinyl, l-Methyl-2-pentinyl, l-Methyl-3- pentinyl, l-Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl-4-pentinyl, 3-Methyl-l-pentinyl, 3- Methyl-4-pentinyl, 4-Methyl-l-pentinyl, 4-Methyl-2-pentinyl, I , I -Di-mcthyl-2-butinyl, l,l-Dimethyl-3- butinyl, l,2-Dimethyl-3-butinyl, 2,2-Dimethyl-3-butinyl, 3,3-Dimethyl-l-butinyl, l-Ethyl-2-butinyl, 1- Ethyl-3-butinyl, 2-Ethyl-3-butinyl und 1 -Ethyl- l-methyl-2-propinyl.

[0062] The term "cycloalkyl" means a carbocyclic, saturated ring system with preferably 3-8 ring carbon atoms, e.g., cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, alkoxycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, or cycloalkylaminocarbonyl. In the case of optionally substituted cycloalkyl, cyclic systems with substituents are included, including substituents with a double bond on the cycloalkyl radical, e.g., an alkylidene group such as methylidene. In the case of optionally substituted cycloalkyl, polycyclic aliphatic systems are also included, such as bicyclofl.1.0]butan-l-yl, bicyclofl.1.0]butan-2-yl, bicyclo[2.1.0]pentan-l-yl, bicyclofl. ll]pentan-l-yl, bicyclo[2.1.0]pentan-2-yl, bicyclo[2.1.0]pentan-5-yl, bicyclo[2.1.1]hexyl, 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-l-yl, and adamantan-2-yl, but also systems such as l,l'-bi(cyclopropyl)-l-yl and l,l'-bi(cyclopropyl)-2-yl. The term "(C3-C7)-cycloalkyl" is a shorthand for cycloalkyl with three to seven carbon atoms, corresponding to the range of carbon atoms.

[0063] In the case of substituted cycloalkyl, spirocyclic aliphatic systems are also included, such as spiro[2.2]pent-l-yl, spiro[2.3]hex-l-yl, spiro[2.3]hex-4-yl, 3-spiro[2.3]hex-5-yl, spiro[3.3]hept-l-yl, spiro[3.3]hept-2-yl.

[0064] "Cycloalkenyl" means a carbocyclic, non-aromatic, partially unsaturated ring system with preferably 4-8 C atoms, e.g., 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl, or 1,4-cyclohexadienyl, which also includes substituents with a double bond on the cycloalkenyl radical, e.g., an alkylidene group such as methylidene. In the case of optionally substituted cycloalkenyl, the explanations for substituted cycloalkyl apply accordingly.

[0065] The term "alkylidene," e.g., also in the form (Ci-Cio)-alkylidene, means the residue of a straight-chain or branched open-chain hydrocarbon radical bonded via a double bond. Naturally, only positions on the parent structure where two H atoms can be replaced by the double bond are possible as bonding sites for alkylidene; examples include =CH2, =CH-CH3, =C(CH3)-CH3, =C(CH3)-C2H5, or =C(C2H5)-C2H5. Cycloalkylidene means a carbocyclic radical bonded via a double bond. "Alkoxyalkyl" stands for an alkoxy radical bonded via an alkyl group, and "alkoxyalkoxy" means an alkoxyalkyl radical bonded via an oxygen atom, e.g. (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy.

[0066] “Alkylthioalkyl” means an alkylthio radical bonded via an alkyl group and “alkylthioalkylthio” means an alkylthioalkyl radical bonded via an oxygen atom.

[0067] “Arylalkoxyalkyl” means an aryloxy radical bonded via an alkyl group and “heteroaryloxyalkyl” means a heteroaryloxy radical bonded via an alkyl group.

[0068] “Haloalkoxyalkyl” means a bound haloalkoxy radical and “haloalkylthioalkyl” means a haloalkylthio radical bound via an alkyl group.

[0069] “Arylalkyl” means an aryl radical bonded via an alkyl group, “heteroarylalkyl” means a heteroaryl radical bonded via an alkyl group, and “heterocyclylalkyl” means a heterocyclyl radical bonded via an alkyl group.

[0070] “Cycloalkylalkyl” means a cycloalkyl radical bonded via an alkyl group, for example (but not limited to) cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropyleth-l-yl, 2-cyclopropyleth-l-yl, 1-cyclopropylprop-l-yl, 3-cyclopropylprop-l-yl.

[0071] According to the invention, "haloalkylthio" - alone or as part of a chemical group - stands for straight-chain or branched S-haloalkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as (Ci-Cs)-, (Ci-Ce)- or (Ci-C4)-haloalkylthio, e.g. (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-l-ylthio, 2,2,2-difluoroeth-l-ylthio, 3,3,3-prop-l-ylthio.

[0072] “Halocycloalkyl” and “halocycloalkenyl” mean cycloalkyl or cycloalkenyl partially or fully substituted by identical or different halogen atoms, such as F, Cl and Br, or by haloalkyl, such as trifluoromethyl or difluoromethyl, e.g. 1-fluorocycloprop-l-yl, 2-fluorocycloprop-l-yl, 2,2-difluorocycloprop-l-yl, 1-fluorocyclobut-l-yl, 1-trifluoromethylcycloprop-l-yl, 2-trifluoromethylcycloprop-l-yl, 1-chloro-cycloprop-l-yl, 2-chlorocycloprop-l-yl, 2,2-dichlorocycloprop-l-yl, 3,3-difluorocyclobutyl.

[0073] According to the invention, "trialkylsilyl" - alone or as part of a chemical group - stands for straight-chain or branched Si-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as tri-[(Ci-Cs)-, (Ci-Ce)- or (Ci-C4)-alkyl]silyl, e.g. (but not limited to) trimethylsilyl, triethylsilyl, tri-(n-propyl)silyl, tri-(iso-propyl)silyl, tri-(n-butyl)silyl, tri-(1-methylprop-l-yl)silyl, tri-(2-methylprop-l-yl)silyl, tri(l,l-dimethyleth-l-yl)silyl, tri(2,2-dimethyleth-l-yl)silyl.

[0074] If the compounds can form tautomers through hydrogen shift that are not structurally covered by the general formula (I), these tautomers are nevertheless encompassed by the definition of the compounds of the general formula (I) according to the invention, unless a specific tautomer is considered. For example, many carbonyl compounds can exist in both the keto and enol forms, with both forms being encompassed by the definition of the compound of the general formula (I).

[0075] The compounds of general formula (I) can exist as stereoisomers depending on the nature and linkage of the substituents. The possible stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z- and E-isomers, are all encompassed by general formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z- and E-isomers) can occur. If, for example, one or more asymmetric carbon atoms are present, enantiomers and diastereomers can occur. Stereoisomers can be obtained from the mixtures obtained during production using conventional separation methods. Chromatographic separation can be carried out both on an analytical scale to determine the enantiomeric excess or diastereomeric excess, and on a preparative scale to produce test samples for biological testing.Likewise, stereoisomers can be selectively prepared by employing stereoselective reactions using optically active starting materials and / or auxiliaries. The invention thus also relates to all stereoisomers encompassed by the general formula (I) but not specified with their specific stereoform, as well as mixtures thereof.

[0076] If the compounds are obtained as solids, purification can also be carried out by recrystallization or digestion. If individual compounds (I) cannot be satisfactorily obtained by the methods described below, they can be prepared by derivatization of other compounds of general formula (I).

[0077] Suitable methods for the isolation, purification, and stereoisomer separation of compounds of general formula (I) include methods generally known to the person skilled in the art from analogous cases, e.g., physical processes such as crystallization, chromatography, especially column chromatography and HPLC (high-pressure liquid chromatography), distillation, optionally under reduced pressure, extraction, and other processes. Any remaining mixtures can generally be separated by chromatographic separation, e.g., on chiral solid phases. For preparative quantities or on an industrial scale, processes such as crystallization, e.g., of diastereomeric salts, which can be obtained from the diastereomer mixtures with optically active acids and, if acidic groups are present, with optically active bases, are suitable.

[0078] Synthesis of bromine or iodine para-substituted [(l,5-diphenyl-lH-l,2,4-triazol-3-yl)oxy]acetic acid

[0079] Derivatives of the general formula (I)

[0080] The [(l,5-diphenyl-lH-l,2,4-triazol-3-yl)oxy]acetic acid derivatives of the general formula (I) according to the invention can be prepared using known methods. The synthetic routes used and investigated start from commercially available or easily prepared substituted benzoic acids, from correspondingly substituted benzoic acid amides, and from commercially available chemicals such as substituted phenylhydrazines and diphenyl carbonate. The groups R 1 , R 2 , R 3 , R 4 , m, n and p of the general formula (I) have the meanings defined above in the following schemes, unless exemplary but non-limiting definitions are given.

[0081] The synthesis of the compounds of general formula (Ia) according to the invention is carried out by reacting the compound of general formula (II) with a compound of general formula (III) in the presence of a base, such as potassium carbonate. The reaction preferably takes place in the temperature range between 0 °C and 120 °C, in an appropriate solvent such as acetonitrile (see Scheme 1).

[0082]

[0083] With X = halogen.

[0084] Scheme 1.

[0085] The synthesis of compounds of general formula (II) is carried out by cyclization of a compound of general formula (IV) in the presence of a condensation reagent such as polyphosphoric acid. The reaction preferably takes place in the temperature range between 0 °C and 180 °C, in the bulk (see Scheme 2).

[0086] Scheme 2.

[0087] The synthesis of compounds of general formula (IV) can be achieved by reacting the compound of general formula (V) with a phenylhydrazine of general formula (VI) in a suitable solvent, such as acetonitrile, in a temperature range between -20 °C and 100 °C, preferably -5 °C and 50 °C. The reaction takes place in the presence of a base, such as triethylamine. Instead of phenylhydrazines of general formula (VI), phenylhydrazine hydrohalides of general formula (VII) can also be used (Scheme 3).

[0088]

[0089] With X = halogen.

[0090] Scheme 3.

[0091] The synthesis of the compound of general formula (V) can be carried out by reacting the compound of general formula (VIII) with diphenyl carbonate (IX) in the presence of a base, such as sodium hydride (see Scheme 4). The reaction preferably takes place in the temperature range between -20 °C and 150 °C in an appropriate solvent, such as THF. The compounds of general formula (VIII) and (IX) are commercially available or can be prepared by or analogously to methods known to the person skilled in the art.

[0092] Scheme 4.

[0093] The synthesis of the acid of general formula (X) can be carried out by saponification of the compound of general formula (Ia) by or analogously to methods known to the person skilled in the art.

[0094] The saponification 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 (such as lithium, sodium, or potassium; Scheme 5), and the saponification reaction preferably takes place in the temperature range between room temperature and 100 °C. The Lewis acid can be boron tribromide, and the reaction can be carried out in a temperature range between -20 °C and 100 °C, preferably -5 °C and 50 °C.

[0095]

[0096] The synthesis of the compounds of general formula (XI) according to the invention is carried out 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)-V'-ethylcarbodiimide, V,V'-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-bound reagents such as polymer-bound dicyclohexylcarbodiimide are also suitable for this coupling reaction. The reaction preferably takes place in the temperature range between 0 °C and 80 °C, in an adequate solvent such as dichloromethane, acetonitrile, V, V-dimethoxyformamide or ethyl acetate and in the presence of a base such as triethylamine, N,N-diisopropylethylamine or l,8-diazabicyclo[5.4.0]undec-7-cene (see Scheme 6). For the T3P coupling conditions, see Organic Process Research & Development 2009, 13, 900-906.

[0097] Scheme 7 depicts the synthesis of the compound of general formula (II). The synthesis is carried out by reacting a compound of general formula (XIII) in the presence of a Brønsted acid, such as 33% HBr in acetic acid. The reaction preferably takes place in the temperature range between 0 °C and 180 °C. See Bioorganic & Medicinal Chemistry 2018, 26, 3321-3344.

[0098] Scheme 7.

[0099] Compounds of general formula (XIII) can be prepared by reacting a compound of general formula (XIV) and a phenylhydrazine of general formula (VI) in an appropriate solvent, such as ethanol (see Scheme 8). The reaction is preferably carried out in the temperature range between 0 °C and 150 °C.

[0100] Scheme 8.

[0101] The compounds of general formula (XIV) can be prepared by reacting benzoic acid halides of general formula (XV) with a thiocyanate salt of general formula (XVI) in the presence of methanol in an appropriate solvent such as acetone (see Scheme 9). The benzoic acid halides are either commercially available or can be prepared by or analogously 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. with X = fluorine, chlorine, bromine

[0102] Scheme 9.

[0103] Selected detailed synthesis examples for the compounds of general formula (I) according to the invention are listed below. The example numbers given correspond to the numberings given in Tables 1.1 to 1.77 below. The 'H-NMR, 13 C-NMR and 19 F-NMR spectroscopic data given for the chemical examples described in the following sections (400 MHz for 'H-NMR and 150 MHz for 13 C-NMR and 375 MHz at 19F-NMR, solvent CDCl, CD3OD or de-DMSO, internal standard: tetramethylsilane 5 = 0.00 ppm), were obtained using a Broker instrument. The designated signals have the following meanings: br = broad; s = singlet, d = doublet, t = triplet, dd = double doublet, ddd = doublet of a double doublet, m = multiplet, q = quartet, quint = quintet, sext = sextet, sept = septet, dq = double quartet, dt = double triplet. For mixtures of diastereomers, either the significant signals of both diastereomers or the characteristic signal of the major diastereomer are given. The abbreviations used for chemical groups have, for example, the following meanings: Me = CH3, Et = CH2CH3, t-Hex = C(CH3)2CH(CH3)2, t-Bu = C(CH3)3, n-Bu = unbranched butyl, n-Pr = unbranched propyl, i-Pr = branched propyl, c-Pr = cyclopropyl, c-Hex = cyclohexyl.

[0104] Synthesis examples:

[0105] Synthesebeispiel No.: 1.8-49

[0106] Synthesestufe 1 : 4-Brom-2-fluorbenzamid 4-Bromo-2-fluorobenzoic acid (4.27 g, 19.50 mmol, 1.0 equiv) was suspended in DCM (100 mL) and treated with three drops of DMF. Oxalyl chloride (3.71 g, 29.25 mmol, 1.5 equiv) was added dropwise to the suspension at room temperature over a period of 25 min, with the evolved gases being passed (caution!) through a cooled solution of sodium hydroxide (20 g) dissolved in water (300 mL). After gas evolution had ceased, the reaction mixture was stirred for a further 30 min at room temperature, and ethyl acetate (50 mL) was added to the mixture over a period of 45 min. A 35% aqueous ammonia solution (150 mL, 15 portions of 10 mL each, caution being taken to avoid gas evolution) was added to the mixture. After the addition was complete, the mixture was stirred for a further 45 min at room temperature, and the resulting precipitate was filtered off with suction. The filter cake was washed with ethyl acetate (100 ml) and stirred once with a mixture of heptane / ethyl acetate (4:1, 60 ml) and then filtered with suction.The solid was vacuum dried overnight. 4-Bromo-2-fluorobenzamide was isolated as a white solid (3.70 g, 87% of theory). H NMR (400 MHz, d. 6 -DMSO 8, ppm) 7.77-7.59 (m, 4H), 7.50 (d, 1H).

[0107] Synthesis step 2: Phenyl (4-bromo-2-fluorobenzoyl) carbamate

[0108] 4-Bromo-2-fluorobenzamide (45.91 g, 210.57 mmol, 1.0 equiv) and diphenyl carbonate (67.66 g, 315.86 mmol, 1.5 equiv) were dissolved in THF (1000 mL) under an argon atmosphere and cooled to 0 °C using an ice bath. Sodium hydride (60% in mineral oil, 8.42 g, 210.57 mmol, 1.0 equiv) was added portionwise to the solution. Caution: Gas evolution! The ice bath was then removed, and the reaction mixture was stirred for 1 h at room temperature. The reaction mixture was then concentrated to 1 / 3 in vacuo, resulting in a white solid precipitating. The resulting solid was filtered off with suction and air-dried. Phenyl-(4-bromo-2-fluorobenzoyl)carbamate was isolated as a white solid (60.15 g, 84% of theory). 'H-NMR (400 MHz, DMSO-d 6 8, ppm) 9.59 (bs, 1H), 7.60 (m, 1H), 7.48 (m, 1H), 7.38-7.28 (m, 2H), 7.17-7.12 (m, 2H), 6.75-6.72 (m, 2H). Synthesis step 3: 2-(4-chloro-2-fluorophenyl)-N-(4-bromo-2-fluorobenzoyl)hydrazinecarboxamide

[0109] Phenyl (4-bromo-2-fluorobenzoyl)carbamate (5 g, 14.79 mmol, 1.0 equiv) was dissolved in acetonitrile (80 mL), and then (4-chloro-2-fluorophenyl)hydrazine hydrochloride (1:1) (3.21 g, 16.27 mmol, 1.1 equiv) and triethylamine (4.12 mL, 29.58 mmol, 2.0 equiv) were added at room temperature. The solution turned pink after approximately 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 on an evaporator. 2-(4-Chloro-2-fluorophenyl)-N-(4-bromo-2-fluorobenzoyl)hydrazinecarboxamide was isolated as a beige solid (6.08 g, 96% of theory). 'H NMR (400 MHz, DMSO-d 6 8, ppm) 11.05 (bs, 1H), 9.73 (bs, 1H), 8.05 (bs, 1H), 7.74 (d, 1H), 7.63-7.55 (m, 2H), 7.30 (dd, 1H), 7.11 (d, 1H), 6.87 (m, 1H).

[0110] Synthesis step 4: l-(4-chloro-2-fluorophenyl)-5-(4-bromo-2-fluorophenyl)-lH-l,2,4-triazol-3-ol

[0111] 2-(4-Chloro-2-fluorophenyl)-N-(4-bromo-2-fluorobenzoyl)hydrazinecarboxamide (6.00 g, 14.83 mmol, 1.0 equiv) was dissolved in acetic acid (100 ml), treated with one drop of concentrated sulfuric acid, and then heated to boiling for 3.5 h. After cooling to room temperature, the reaction mixture was concentrated to one-fifth, added dropwise to ice water (100 ml), and the suspension stirred for 15 min at room temperature. The resulting precipitate was filtered off with suction, and the filter cake was washed twice with water (50 ml each). The filtered precipitate was dried at 55 °C in a vacuum drying oven. l-(4-Chloro-2-fluorophenyl)-5-(4-bromo-2-fluorophenyl)-lH-l,2,4-triazol-3-ol was isolated as a light beige solid (3.10 g, 40% of theory). 'H NMR (400 MHz, DMSO-d 6 8, ppm) 11.75 (bs, 1H), 7.75-7.11 (m, 5H), 6.87 (m, 1H). Synthesis stage 5: Methyl {[1-(4-chloro-2-fluorophenyl)-5-(4-bromo-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (synthesis example 1.1-49) l-(4-Chloro-2-fluorophenyl)-5-(4-bromo-2-fluorophenyl)-lH-l,2,4-triazol-3-ol (3.10 g, 8.02 mmol, 1.0 equiv) and potassium carbonate (3.32 g, 24.06 mmol, 3 equiv) were suspended in acetonitrile (150 ml) and then treated with methyl bromoacetate (1.84 g, 12.03 mmol, 1.5 equiv). The suspension was stirred overnight at room temperature, the solid was filtered off, and the reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (gradient ethyl acetate / heptane). Methyl {[1-(4-chloro-2-fluorophenyl)-5-(4-bromo-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate was isolated as a colorless oil (2.71 g, 70% of theory). 'H NMR (400 MHz, CDCl3 8, ppm) 7.47 (m, 1H), 7.39-7.36 (m, 2H), 7.23-7.20 (m, 2H), 7.15 (m, 1H), 4.93 (s, 2H), 3.81 (s, 3H).

[0112] Synthesis step 6: {[5-(4-bromo-2-fluorophenyl)-l-(4-chloro-2-fluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetic acid (Synthesis example 1.3-49)

[0113] Methyl {[1-(4-chloro-2-fluorophenyl)-5-(4-bromo-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy} acetate (2.50 g, 5.45 mmol, 1.0 equiv) and lithium hydroxide (392 mg, 16.35 mmol, 3.0 equiv) were dissolved in a THF / water mixture (7:2, 105 ml) and then stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuo. The residue was dissolved in water and adjusted to pH 2 with 2 M hydrochloric acid, whereupon a light yellow solid precipitated. The precipitate was filtered off with suction and dried at 55 °C in a vacuum oven. {[5-(4-Bromo-2-fluorophenyl)-l-(4-chloro-2-fluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetic acid was isolated as a light beige solid (2.99 g, 61% of theory). 'H-NMR (400 MHz, d 6 -DMSO 8, ppm) 13.11 (bs, 1H), 7.73-7.69 (m, 2H), 7.63-7.51 (m, 3H), 7.44 (m, 1H), 4.86 (s, 2H).

[0114] Synthesestufe 7 : Tetrahydrofuran-2-ylmethyl- { [5-(4-brom-2-fluorphenyl)- 1 -(4-chlor-2-fluorphenyl)- 1H- l,2,4-triazol-3-yl]oxy}acetat (Synthesebeispiel 1.8-49)

[0115] Tetrahydrofuran-2-ylmethanol (34 mg, 0.34 mmol, 1.5 equiv) was dissolved in dichloromethane (10 mL), and then {[5-(4-bromo-2-fluorophenyl)-l-(4-chloro-2-fluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetic acid (100 mg, 0.22 mmol, 1.0 equiv), N-ethyl-N-isopropylpropan-2-amine (44 mg, 0.34 mmol, 1.5 equiv), and a spatula tip of DMAP were added. T3P (0.27 mL, 0.45 mmol, 2.0 equiv; 50% in THF) was pipetted into this solution, and the reaction mixture was stirred at room temperature over the weekend. The reaction solution was then extracted with water and dichloromethane, and the phases were separated using a phase separator. The organic phase was concentrated in vacuo. The residue was purified by column chromatography (gradient ethyl acetate / heptane). Tetrahydrofuran-2-ylmethyl-{[5-(4-bromo-2-fluorophenyl)-1-(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy} acetate was isolated as a colorless oil (118 mg, 94% of theory). 'H NMR (400 MHz, CDCl 8, ppm) 7.46 (m, 1H), 7.40-7.36 (m, 2H), 7.23-7.20 (m, 2H), 7.14 (m, 1H), 4.96 (s, 2H), 4.26 (m, 1H), 4.18-4.12 (m, 2H), 3.85 (m, 1H), 3.76 (m, 1H), 1.99-1.86 (m, 3H), 1.61 (m, 1H). Analogously to the preparation examples given above and recited at the appropriate point, and taking into account the general information for the preparation of substituted [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives, the following compounds are obtained:

[0116] Table 1.1: Preferred compounds of formula (1.1) are compounds 1.1-1 to 1.1-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.1-1 to 1.1-53 of Table 1.1 are thus defined by the meaning of the respective entries No. 1 to 53 for Q of Table

[0117] 1 defined.

[0118] Table 1:

[0119] Table 1.2: Preferred compounds of formula (1.2) are compounds 1.2-1 to 1.2-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.2-1 to 1.2-53 of Table 1.2 are thus defined by the meaning of the respective entries No. 1 to 53 for Q of Table

[0120] 1 defined.

[0121] Table 1.3: Preferred compounds of formula (1.3) are compounds 1.3-1 to 1.3-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.3-1 to 1.3-53 of Table 1.3 are thus defined by the meaning of the respective entries No. 1 to 53 for Q of Table

[0122] 1 defined. Table 1.4: Preferred compounds of formula (1.4) are compounds 1.4-1 to 1.4-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.4-1 to 1.4-53 of Table 1.4 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0123] Table 1.5: Preferred compounds of formula (1.5) are compounds 1.5-1 to 1.5-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.5-1 to 1.5-53 of Table 1.5 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0124] Table 1.6: Preferred compounds of formula (1.6) are compounds 1.6-1 to 1.6-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.6-1 to 1.6-53 of Table 1.6 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1. Table 1.7: Preferred compounds of formula (1.7) are compounds 1.7-1 to 1.61-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.7-1 to 1.7-53 of Table 1.7 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0125] Table 1.8: Preferred compounds of formula (1.8) are compounds 1.8-1 to 1.8-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.8-1 to 1.8-53 of Table 1.8 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0126] Table 1.9: Preferred compounds of formula (1.9) are compounds 1.9-1 to 1.9-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.9-1 to 1.9-53 of Table 1.9 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0127] Table 1.10: Preferred compounds of formula (1.10) are compounds 1.10-1 to 1.10-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.10-1 to 1.10-53 of Table 1.10 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0128]

[0129] Table 1.11: Preferred compounds of formula (1.11) are compounds 1.11-1 to 1.11-53, wherein Q has the meanings given in the respective row of Table 1. The compounds

[0130] 1.11-1 to 1.11-53 of Table 1.11 are thus defined by the meaning of the respective entries No. 1 to 53 for Q of Table 1.

[0131] Table 1.12: Preferred compounds of formula (1.12) are compounds 1.12-1 to 1.12-53, where Q has the meanings given in the respective row of Table 1. The compounds

[0132] 1.12-1 to 1.12-53 of Table 1.12 are thus defined by the meaning of the respective entries No. 1 to 53 for Q of Table 1.

[0133] Table 1.13: Preferred compounds of formula (1.13) are compounds 1.13-1 to 1.13-53, where Q has the meanings given in the respective row of Table 1. The compounds

[0134] 1.13-1 to 1.13-53 of Table 1.13 are thus defined by the meaning of the respective entries No. 1 to 53 for Q of Table 1.

[0135]

[0136] Table 1.14: Preferred compounds of formula (1.14) are compounds 1.14-1 to 1.14-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.14-1 to 1.14-53 of Table 1.14 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0137] Table 1.15: Preferred compounds of formula (1.15) are compounds 1.15-1 to 1.15-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.15-1 to 1.15-53 of Table 1.15 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1. Table 1.16: Preferred compounds of formula (1.16) are compounds 1.16-1 to 1.16-53, where Q has the meanings given in the respective row of Table 1. The compounds

[0138] 1.16-1 to 1.16-53 of Table 1.16 are thus defined by the meaning of the respective entries No. 1 to 53 for Q of Table 1.

[0139] Table 1.17: Preferred compounds of formula (1.17) are compounds 1.17-1 to 1.17-53, where Q has the meanings given in the respective row of Table 1. The compounds

[0140] 1.17-1 to 1.17-53 of Table 1.17 are thus defined by the meaning of the respective entries No. 1 to 53 for Q of Table 1.

[0141] Table 1.18: Preferred compounds of formula (1.18) are compounds 1.18-1 to 1.18-53, where Q has the meanings given in the respective row of Table 1. The compounds

[0142] 1.18-1 to 1.18-53 of Table 1.18 are thus defined by the meaning of the respective entries No. 1 to 53 for Q of Table 1.

[0143] Table 1.19: Preferred compounds of formula (1.19) are compounds 1.19-1 to 1.19-53, where Q has the meanings given in the respective row of Table 1. The compounds

[0144] 1.19-1 to 1.19-53 of Table 1.19 are thus defined by the meaning of the respective entries No. 1 to 53 for Q of Table 1.

[0145]

[0146] Table 1.20: Preferred compounds of formula (1.20) are compounds 1.20-1 to 1.20-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.20-1 to 1.20-53 of Table 1.20 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0147] Table 1.21: Preferred compounds of formula (1.21) are compounds 1.21-1 to 1.21-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.21-1 to 1.21-53 of Table 1.21 are thus defined by the meaning of the respective entries Nos. 1 to 53

[0148] Table 1.22: Preferred compounds of formula (1.22) are compounds 1.22-1 to 1.22-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.22-1 to 1.22-53 of Table 1.22 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0149]

[0150] Table 1.23: Preferred compounds of formula (1.23) are compounds 1.23-1 to 1.23-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.23-1 to 1.23-53 of Table 1.23 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0151] Table 1.24: Preferred compounds of formula (1.24) are compounds 1.24-1 to 1.24-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.24-1 to 1.24-53 of Table 1.24 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0152] Table 1.25: Preferred compounds of formula (1.25) are compounds 1.25-1 to 1.25-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.25-1 to 1.25-53 of Table 1.25 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0153]

[0154] Table 1.26: Preferred compounds of formula (1.26) are compounds 1.26-1 to 1.26-53, where Q has the meanings given in the respective row of Table 1. The compounds

[0155] 1.26-1 to 1.26-53 of Table 1.26 are thus defined by the meaning of the respective entries No. 1 to 53

[0156] Table 1.27: Preferred compounds of formula (1.27) are compounds 1.27-1 to 1.27-53, where Q has the meanings given in the respective row of Table 1. The compounds

[0157] 1.27-1 to 1.27-53 of Table 1.27 are thus defined by the meaning of the respective entries No. 1 to 53 for Q of Table 1.

[0158] Table 1.28: Preferred compounds of formula (1.28) are compounds 1.28-1 to 1.28-53, where Q has the meanings given in the respective row of Table 1. The compounds

[0159] 1.28-1 to 1.28-53 of Table 1.28 are thus defined by the meaning of the respective entries No. 1 to 53 for Q of Table 1.

[0160]

[0161] Table 1.29: Preferred compounds of formula (1.29) are compounds 1.29-1 to 1.29-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.29-1 to 1.29-53 of Table 1.29 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0162] Table 1.30: Preferred compounds of formula (1.30) are compounds 1.30-1 to 1.30-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.30-1 to 1.30-53 of Table 1.30 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0163] Table 1.31: Preferred compounds of formula (1.31) are compounds 1.31-1 to 1.31-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.31-1 to 1.31-53 of Table 1.31 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0164] Table 1.32: Preferred compounds of formula (1.32) are compounds 1.32-1 to 1.32-53, where Q has the meanings given in the respective row of Table 1. The compounds

[0165] 1.32-1 to 1.32-53 of Table 1.32 are thus defined by the meaning of the respective entries No. 1 to 53

[0166] Table 1.33: Preferred compounds of formula (1.33) are the compounds 1.33-1 to 1.33-53, wherein Q has the meanings given in the respective row of Table 1. The compounds

[0167] 1.33-1 to 1.33-53 of Table 1.33 are thus defined by the meaning of the respective entries No. 1 to 53 for Q of Table 1.

[0168] Table 1.34: Preferred compounds of formula (1.34) are compounds 1.34-1 to 1.34-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.34-1 to 1.34-53 of Table 1.34 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0169] Table 1.35: Preferred compounds of formula (1.35) are compounds 1.35-1 to 1.35-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.35-1 to 1.35-53 of Table 1.35 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0170] Table 1.36: Preferred compounds of formula (1.36) are compounds 1.36-1 to 1.36-53, wherein Q has the meanings given in the respective row of Table 1. The compounds 1.36-1 to 1.36-53 of Table 1.36 are thus defined by the meaning of the respective entries Nos. 1 to 53 for Q of Table 1.

[0171] Spectroscopic data of selected table examples:

[0172] Selected detailed synthesis examples for the compounds of the general formula (I) according to the invention are listed below. The 'H-NMR, 13 C-NMR and 19 F-NMR spectroscopic data given for the chemical examples described in the following sections (400 MHz for 'H-NMR and 150 MHz for 13 C-NMR and 375 MHz at 19F-NMR, solvent CDCl, CD3OD or de-DMSO, internal standard: tetramethylsilane 5 = 0.00 ppm), were obtained using a Broker instrument. The designated signals have the following meanings: br = broad; s = singlet, d = doublet, t = triplet, dd = double doublet, ddd = doublet of a double doublet, m = multiplet, q = quartet, quint = quintet, sext = sextet, sept = septet, dq = double quartet, dt = double triplet. For mixtures of diastereomers, either the significant signals of both diastereomers or the characteristic signal of the major diastereomer are given. The abbreviations used for chemical groups have, for example, the following meanings: Me = CH3, Et = CH2CH3, t-Hex = C(CH3)2CH(CH3)2, t-Bu = C(CH3)3, n-Bu = unbranched butyl, n-Pr = unbranched propyl, i-Pr = branched propyl, c-Pr = cyclopropyl, c-Hex = cyclohexyl.The spectroscopic data of selected table examples listed below were obtained using classical methods. 1 H-NMR interpretation or NMR peak list methods. Classical 1 H-NMR Interpretation Example No. I.1-38: 1 H NMR (400 MHz, CDCl3 δ, ppm) 7.49-7.36 (m, 3H), 7.20 (dd, 1H), 6.95 (m, 1H), 6.87 (m, 1H), 4.94 (s, 2H), 3.81 (s, 3H). Example no. I.3-38: 1 H-NMR (400 MHz, d 6 -DMSO δ, ppm) 13.12 (bs, 1H), 7.11-7.64 (m, 2H), 7.62-7.50 (m, 4H), 7.24 (m, 1H), 4.91 (s, 2H), 4.86 (s, 2H). Example no. I.4-38: 1 H NMR (400 MHz, CDCl3 δ, ppm) 7.58 (d, 1H), 7.42-7.37 (m, 2H), 7.28 (m, 1H), 6.95 (m, 1H), 6.87 (m, 1H), 4.93 (s, 2H), 3.81 (s, 3H). Example no. I.13-38: 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.49-7.36 (m, 3H), 7.23 (d, 1H), 6.95 (m, 1H), 6.87 (m, 1H), 4.97 (s, 2H), 4.37-4.35 (m, 2H), 3.63-3.61 (m, 2H), 3.36 (s, 3H). Example no. I.9-38: 1H-NMR (400 MHz, CDCl3δ, ppm) 7.47-7.36 (m, 3H), 7.21 (dd, 1H), 6.98-6.85 (m, 2H), 4.93 (s, 2H), 4.23 (m, 1H), 4.22 (m, 1H), 4.11 (m, 1H), 3.85-3.69 (m, 3H), 3.53 (m, 1H), 2.59 (m, 1H), 2.00 (m, 1H), 1.60 (m, 1H). Beispiel No. I.10-38: 1 H-NMR (400 MHz, CDCl3δ, ppm) 7.49-7.36 (m, 3H), 7.20 (dd, 1H), 6.95 (m, 1H), 6.89 (m, 1H), 5.17 (t, 1H), 4.98 (s, 2H), 4.25 (d, 2H), 4.00-3.88 (m, 4H). Beispiel No. I.7-38: 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.49-7.36 (m, 3H), 7.20 (dd, 1H), 6.96 (m, 1H), 6.87 (m, 1H), 4.92 (s, 2H), 4.49 (t, 2H), 3.68 (s, 3H), 2.69 (t, 3H). Beispiel No. I.2-49: 1 H-NMR (400 MHz, CDCl3δ, ppm) 7.47 (m, 1H), 7.39-7.35 (m, 2H), 7.23-7.20 (m, 2H), 7.14 (dd, 1H), 4.91 (s, 2H), 4.27 (q, 2H), 1.29 (t, 3H). Beispiel No. I.13-49: 1 H-NMR (400 MHz, CDCl3δ, ppm) 7.47 (m, 1H), 7.41-7.37 (m, 2H), 7.23-7.20 (m, 2H), 7.14 (m, 1H), 4.96 (s, 2H), 4.37-4.35 (m, 2H), 3.63-3.61 (m, 1H), 3.36 (s, 3H).Beispiel No. I.7-49: 1H-NMR (400 MHz, CDCl3δ, ppm) 7.47 (m, 1H), 7.41-7.37 (m, 2H), 7.23-7.20 (m, 2H), 7.15 (m, 1H), 4.91 (s, 2H), 4.50-4.47 (m, 2H), 3.68 (s, 3H), 32.70-2.67 (m, 2H). Beispiel No. I.9-49: 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.46 (m, 1H), 7.39-7.35 (m, 2H), 7.23-7.20 (m, 2H), 7.16 (m,1H), 4.93 (s, 2H), 4.23 (m, 1H), 4.11 (m, 1H), 3.85-3.69 (m, 3H), 3.53 (m, 1H), 2.59 (m, 1H), 2.00 (m, 1H), 1.63 (m, 1H). Beispiel No. I.10-49: 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.47 (m, 1H), 7.40-7.36 (m, 2H), 7.23-7.20 (m, 2H), 7.14 (m, 1H), 4.93 (s, 2H), 5.14 (t, 1H), 4.97 (s, 2H), 4.25 (d, 2H), 4.00-3.88 (m, 4H). Beispiel No. I.2-38: 1 H-NMR (400 MHz, CDCl3 δ, ppm) 7.48-7.36 (m, 3H), 7.20 (dd, 1H), 6.97-6.84 (m, 2H), 4.91 (s, 2H), 4.27 (q, 2H), 1.29 (t, 3H). Beispiel No. I.8-38: 1H-NMR (400 MHz, CDCl3 δ, ppm) 7.48-7.36 (m, 3H), 7.20 (dd, 1H), 6.98-6.84 (m, 2H), 4.96 (s, 2H), 4.26 (m, 1H), 4.18-4.12 (m, 2H), 3.85 (m, 1H), 3.77 (m, 1H), 2.00-1.86 (m, 3H), 1.61 (m, 1H). The invention also relates to the method for protecting crops or useful plants from phytotoxic effects of agrochemicals, such as pesticides, or in particular herbicides, which cause damage to the crops or useful plants, characterized in that compounds of the general formula (I) or salts thereof are used as safeners, preferably an effective amount of the compounds of the general formula (I) or salts thereof is applied to the plants, parts of the plants or their seeds (or seed).The compounds of general formula (I) (= safeners) as mentioned above are suitable for use together with active ingredients (pesticides) for the selective control of pests in a range of plant crops, for example in economically important crops such as cereals (wheat, barley, triticale, rye, rice, maize, millet), sugar beet, sugar cane, rapeseed, cotton, sunflower, peas, beans, and soybeans. The herbicide-safener combinations with safeners of general formula (I) are also suitable for controlling harmful plants in beds and areas of crops and ornamental plants, such as lawns with crop or ornamental turf, especially ryegrass, meadow grass, or Bermuda grass.

[0173] Among the crops and cultivated plants in which the herbicide-safener combinations with the aforementioned compounds of general formula (I) can be used, mutant crops or transgenic crops that are fully or partially tolerant to some pesticides are also of interest, e.g., maize crops that are resistant to glufosinate or glyphosate, or soybean crops that are resistant to plant-damaging imidazolinones. However, the particular advantage of the novel safeners of general formula (I) is their effective action in crops that are normally not sufficiently tolerant to the pesticides to be applied.

[0174] The compounds of general formula (I) can be applied simultaneously or in any sequence with the active ingredients for joint use with pesticides. They are then able to reduce or completely eliminate harmful side effects of these active ingredients in crops without impairing or significantly reducing the effectiveness of these active ingredients against unwanted pests. Damage caused by the use of multiple pesticides, e.g., multiple herbicides or herbicides in combination with insecticides or fungicides, can also be significantly reduced or completely eliminated. This can significantly expand the range of applications of conventional pesticides.

[0175] If the compositions according to the invention contain pesticides, these compositions are applied after appropriate dilution either directly to the cultivation area, to the already germinated weeds and / or useful plants or to the already emerged weeds and / or useful plants. If the compositions according to the invention do not contain a pesticide, these compositions can be used in the so-called tank mix method - i.e. immediately before application to the area to be treated, the user mixes and dilutes the separately formulated products (= crop protection agent and pesticide) - or before or after the application of a pesticide, or for seed pretreatment, i.e. for example for dressing the crop seed. Preference is given to applying the safener at the same time as the pesticide, particularly if the safener is applied to the plants after the herbicide.The beneficial effects of the compounds of general formula (I) are observed when they are used together with the pesticides pre-emergence or post-emergence, for example when applied simultaneously as a tank mix or as a co-formulation, or when applied separately in parallel or sequentially (split application). It is also possible to repeat the application several times. Sometimes it may be useful to combine a pre-emergence application with a post-emergence application. In most cases, post-emergence application to the crop or plant with simultaneous or subsequent application of the pesticide is recommended. The compounds (I) according to the invention can also be used for seed dressing, the (dip) treatment of seedlings (e.g., rice), or the treatment of other propagating material (e.g., potato tubers).

[0176] When compounds of general formula (I) are used in combination with herbicides, not only the safener effect but also enhanced herbicidal activity against weeds is often observed. Furthermore, the growth of crops and cultivated plants is improved in many cases, and crop yields can be increased.

[0177] The compositions according to the invention may contain one or more pesticides. Examples of suitable pesticides include herbicides, insecticides, fungicides, acaricides, and nematicides, each of which, if used alone, would cause phytotoxic damage to the crops or where damage would be likely. Of particular interest are corresponding pesticidal active ingredients from the groups of herbicides, insecticides, acaricides, nematicides, and fungicides, especially herbicides.

[0178] The weight ratio of safener (of general formula (I)) to pesticide can be varied within wide limits and is generally in the range of 1:100 to 100:1, preferably 1:20 to 20:1, in particular 1:10 to 10:1. The optimal weight ratio of safener to pesticide generally depends on both the safener and the pesticide used, as well as on the type of crop or plant to be protected. The required application rate of safener can be varied within wide limits depending on the pesticide used and the type of crop to be protected and is generally 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 quantities and weight ratios necessary for successful treatment can be determined by simple preliminary tests.

[0179] In the case of seed dressing, for example, 0.005 to 20 g of safener (of the general formula (I)) per kilogram of seed, preferably 0.01 to 10 g of safener per kilogram of seed, in particular 0.05 to 5 g of safener per kilogram of seed are used.

[0180] When solutions of safener (of general formula (I)) are used in seed treatment and the seeds or seedlings are wetted with the solutions, the suitable concentration is generally in the range of 1 to 10,000 ppm, preferably 100 to 1,000 ppm by weight.

[0181] The quantities and weight ratios necessary for successful treatment can be determined through simple preliminary tests.

[0182] The safeners of general formula (I) can be formulated separately or together with the pesticides in the usual way. Therefore, they also include crop-protecting agents.

[0183] The preferred application is the combined use of safener and pesticide, in particular the use of safener and herbicide as a ready-to-use formulation or the use in the tank mix process.

[0184] Likewise preferred is the use of the safener of the general formula (I) in seed treatment with subsequent application of pesticides, preferably herbicides, after sowing by pre- or post-emergence method.

[0185] The compounds of general formula (I) or their salts can be used as such or in the form of their preparations (formulations) in combination with other pesticidally active substances, such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers, and / or growth regulators, e.g., as ready-to-use formulations or as tank mixes. The combination formulations can be prepared based on the above-mentioned formulations, taking into account the physical properties and stability of the active ingredients to be combined.

[0186] As combination partners for the compounds according to the invention in mixture formulations or in the tank mix, known active ingredients which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate 3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or protoporphyrinogen oxidase can be used, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006 and literature cited therein.The following are examples of known herbicides or plant growth regulators that can be combined with the compounds of the invention. These active ingredients are designated either by their common name in the English version according to the International Organization for Standardization (ISO) or by their chemical name or code number. This always includes all application forms, such as acids, salts, esters, as well as all isomeric forms such as stereoisomers and optical isomers, even if these are not explicitly mentioned. Examples of such herbicidal mixture components are:

[0187] Acetochlor, Acifluorfen, Acifluorfen-methyl, Acifluorfen-Natrium, Aclonifen, Alachlor, Allidochlor, Alloxydim, Alloxydim-Natrium, Ametryn, Amicarbazon, Amidochlor, Amidosulfuron, 4-Amino-3- chlor-6-(4-chlor-2-fluor-3-methylphenyl)-5-fluorpyridin-2-carbonsäure, Aminocyclopyrachlor, Aminocyclopyrachlor-Kalium, Aminocyclopyrachlor-methyl, Aminopyralid, Aminopyralid- dimethylammonium, Aminopyralid-tripromine, Amitrol, Ammoniumsulfamate, Anilofos, Asulam, Asulam-Kalium, Asulam-Natrium, Atrazin, Azafenidin, Azimsulfuron, Beflubutamid, (S)-(-)- Beflubutamid, Beflubutamid-M, Benazolin, Benazolin-ethyl, Benazolin-dimethylammonium, Benazolin-Klaium, Benfluralin, Benfuresate, Bensulfuron, Bensulfuron-methyl, Bensulid, Bentazon, Bentazon-Natrium, Benzobicyclon, Benzofenap, Bicyclopyrone, Bifenox, Bilanafos, Bilanafos-Natium, Bipyrazone, Bispyribac, Bispyribac-Natium, Bixlozon, Bromacil, Bromacil-lithium, Bromacil-Natrium, Bromobutid, Bromofenoxim, Bromoxynil, Bromoxynilbutyrat, Bromoxynil-Kalium,Bromoxynil- heptanoat und Bromoxynil-octanoat, Busoxinon, Butachlor, Butafenacil, Butamifos, Butenachlor, Butralin, Butroxydim, Butylat, Cafenstrol, Cambendichlor, Carbetamide, Carfentrazon, Carfentrazon- Ethyl, Chloramben, Chloramben-ammonium, Chloramben-diolamin, Chlroamben-methyl, Chlorambenmethylammonium, Chlor amben-Natium, Chlorbromuron, Chlorfenac, Chlorfenac-ammonium, Chlorfenac-Natium, Chlorfenprop, Chlorfenprop-methyl, Chlorflurenol, Chlorflurenol-methyl, Chloridazon, Chlorimuron, Chlorimuron-ethyl, Chlorophthalim, Chlorotoluron, Chlorsulfuron, Chlorthal, Chlorthal-dimethyl, Chlorthal-monomethyl, Cinidon, Cinidon-ethyl, Cinmethylin, exo-(+)- Cinmethylin, d.h. (lR,2S,4S)-4-isopropyl-l-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptan, exo-(-)-Cinmethylin, d.h. ( 1 R,2S,4S)-4-isopropyl- 1 -methyl-2- [(2-methylbenzyl)oxy] -7 - oxabicyclo[2.2.1]heptan, Cinosulfuron, Clacyfos, Clethodim, Clodinafop, Clodinafop-ethyl, Clodinafop- propargyl, Clomazon, Clomeprop, Clopyralid,Clopyralid-methyl, Clopyralid-olamin, Clopyralid- Kalium, Clopyralid-tripomin, Cloransulam, Cloransulam-methyl, Cumyluron, Cyanamide, Cyanazine, Cycloat, Cyclopyranil, Cyclopyrimorat, Cyclosulfamuron, Cycloxydim, Cyhalofop, Cyhalofop-butyl, Cyprazin, 2,4-D (sowie die Ammonium, Butotyl, Butyl, Cholin, Diethylammonium, Dimethylammonium, Diolamin, Doboxyl, Dodecylammonium, Etexyl, Ethyl, 2-Ethylhexyl, Heptylammonium, Isobutyl, Isooctyl, Isopropyl, Isopropylammonium, Lithium, Meptyl, Methyl, Kalium, Tetradecylammonium, Triethylammonium, Triisopropanolammonium, Tripromin and Trolamin Salze davon), 2,4-DB, 2,4-DB-butyl, 2, 4-DB -Dimethylammonium, 2,4-DB-isooctyl, 2,4-DB-Kalium und 2,4-DB-Natrium, Daimuron (Dymron), Dalapon, Dalapon-Calcium, Dalapon-Magnesium, Dalapon- Natium, Dazomet, Dazomet-Natrium, n-Decanol, 7-Deoxy-D-sedoheptulose, Desmedipham, Detosyl- pyrazolat (DTP), Dicamba und seine Salze (z.B. Dicamba-biproamin, Dicamba-N,N-Bis(3- aminopropyl)methylamin, Dicamba-butotyl,Dicamba-cholin, Dicamba-Diglycolamin, Dicamba- Dimethylammonium, Dicamba-Diethanolaminemmonium, Dicamba-Diethylammonium, Dicamba- isopropylammonium, Dicamba-methyl, Dicamba-monoethanolamin, Dicamba-olamin, Dicamba- Kalium, Dicamba-Natium, Dicamba-Triethanolamin), Dichlobenil, 2-(2,4-Dichlorbenzyl)-4,4-dimethyl- l,2-oxazolidin-3-on, 2-(2,5-Dichlorbenzyl)-4,4-dimethyl-l,2-oxazolidin-3-one, Dichlorprop, Dichlorprop-butotyl, Dichlorprop-Dimethylammonium, Dichhlorprop-etexyl, Dichlorpropethylammonium, Dichlorprop-isoctyl, Dichlorprop-methyl, Dichlorprop-Kalium, Dichlorprop-Natrium, Dichlorprop-P, Dichlorprop-P-Dimethylammonium, Dichlorprop-P-etexyl, Dichlorprop-P-Kalium, Dichlorprop-Natrium, Diclofop, Diclofop-methyl, Diclofop-P, Diclofop-P-methyl, Diclosulam, Difenzoquat, Difenzoquat-metilsulfate, Diflufenican, Diflufenzopyr, Diflufenzopyr-Natrium, Dimefuron, Dimepiperate, Dimesulfazet, Dimethachlor, Dimethametryn, Dimethenamid, Dimethenamid-P, Dimetrasulfuron, Dinitramine, Dinoterb,Dinoterb-Acetate, Diphenamid, Diquat, Diquat-Dibromid, Diquat-Dichloride, Dithiopyr, Diuron, DNOC, DNOC-Ammonium, DNOC-Kalium, DNOC-Natrium, Endothal, Endothal-Diammonium, Endothal-Dikalium, Endothal-Dinatrium, Epyrifenacil (S-3100), EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron, Ethametsulfuron-Methyl, Ethiozin, Ethofumesate, Ethoxyfen, Ethoxyfen-Ethyl, Ethoxysulfuron, Etobenzanid, F-5231, d.h. N-[2- Chlor-4-fluor-5 - [ 4 - ( 3 -fluorpropyl) -4,5 -dihydro-5 -oxo- 1 H-tetrazol- 1 -yl] -phenyl] -ethansulfonamid, F- 7967, i.e. 3-[7-Chlor-5-fluor-2-(trifluormethyl)-lH-benzimidazol-4-yl]-l-methyl-6- (trifluormethyl)pyrimidin-2,4(lH,3H)-dion, Fenoxaprop, Fenoxaprop-P, Fenoxaprop-Ethyl, Fenoxaprop-P-Ethyl, Fenoxasulfone, Fenpyrazone, Fenquinotrione, Fentrazamid, Flamprop, Flamprop- Isoproyl, Flamprop-Methyl, Flamprop-M-Isopropyl, Flamprop-M-Methyl, Flazasulfuron, Florasulam, Florpyrauxifen, Florpyrauxifen-benzyl, Fluazifop, Fluazifop-Butyl, Fluazifop-Methyl, Fluazifop-P, Fluazifop-P-Butyl,Flucarbazone, Flucarbazone sodium, Flucetosulfuron, Fluchloraline, Flufenacet, Flufenpyr, Flufenpyr ethyl, Flumetsulam, Flumiclorac, Flumiclorac pentyl, Flumioxazine, Fluometuron, Flurenol, Flurenol butyl, dimethylammonium and methyl, Fluoroglycofen, Fluoroglycofen ethyl, Flupropanate, Flupropanate sodium, Flupyrsulfuron, Flupyrsulfuron methyl, Flupyrsulfuron methyl sodium, Fluridone, Flurochloridone, Fluroxypyr, Fluroxypyr butometyl, Fluroxypyr meptyl, Flurtamone, Fluthiacet, Fluthiacet methyl, Fomesafen, Fomesafen sodium, Foramsulfuron, Foramsulfuron sodium, fosamine, fosamine ammonium, glufosinate, glufosinate ammonium, glufosinate sodium, E-glufosinate ammonium, E-glufosinate sodium, glufosinate P-sodium, glufosinate P-ammonium, glyphosate, glyphosate ammonium, Glyphosate isopropyl ammonium, glyphosate diammonium, glyphosate dimethyl ammonium, glyphosate potassium, glyphosate sodium, glyphosate sesquinodium and glyphosate trimesium, H-9201, i.e. O-(2,4-Dimethyl-6-nitrophenyl)-O-ethyl- isopropylphosphoramidothioat, Halauxifen, Halauxifen-methyl, Halosafen, Halosulfuron, Halosulfuron- Methyl, Haloxyfop, Haloxyfop-P, Haloxyfop-Ethoxyethyl, Haloxyfop-P-Ethoxyethyl, Haloxyfop- Methyl, Haloxyfop-P-Methyl, Haloxifop-Natrium, Hexazinon, HNPC-A8169, i.e. Prop-2-yn-l-yl (2S)- 2- { 3-[(5-tert-butylpyridin-2-yl)oxy]phenoxy Jpropanoat, HW -02, d.h. 1 -(Dimethoxyphosphoryl)-ethyl- (2,4-dichlorphenoxy)acetat, Hydantocidin, Imazamethabenz, Imazamethabenz-Methyl, Imazamox, Imazamox-Ammonium, Imazapic, Imazapic-Ammonium, Imazapyr, Imazapyr-Isopropylammonium, Imazaquin, Imazaquin-Ammonium, Imazaquin-Methyl, Imazethapyr, Imazethapyr-Ammonium, Imazosulfuron, Indanofan, Indaziflam, lodosulfuron, lodosulfuron-Methyl, lodosulfuron-Methyl- Natrium, Ioxynil, loxynil-Lithium, -Octanoat, -Kalium und Natrium, Ipfencarbazon, Isoproturon, Isouron, Isoxaben, Isoxaflutole, Karbutilat, KUH-043,d.h. 3-({[5-(Difluormethyl)-l-methyl-3- (trifluormethyl)-lH-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-l,2-oxazol, Ketospiradox, Ketospiradox-Kalium, Lactofen, Lenacil, Linuron, MCPA, MCPA-Butotyl, -Butyl, -Dimethylammonium, -Diolamin, -2-Ethylhexyl, -Ethyl, -Isobutyl, Isoctyl, -Isopropyl, -Isopropylammonium, - Methyl, Olamin, -Kalium, -Natrium und -Trolamin, MCPB, MCPB-Methyl, -Ethyl und -Natrium, Mecoprop, Mecoprop-Butotyl, Mecoprop- dimethylammonium, Mecoprop-Diolamin, Mecoprop-Etexyl, Mecoprop-Ethadyl, Mecoprop-Isoctyl, Mecoprop-Methyl, Mecoprop-Kalium, Mecoprop-Natrium, und Mecoprop-Trolamin, Mecoprop-P, Mecoprop-P-Butotyl, -Dimethylammonium, -2-Ethylhexyl und - Kalium, Mefenacet, Mefluidid, Mefluidid-Diolamin, Mefluidid-Kalium, Mesosulfuron, Mesosulfuron- Methyl, Mesosulfuron-Natrium, Mesotrion, Methabenzthiazuron, Metam, Metamifop, Metamitron, Metazachlor, Metazosulfuron, Methabenzthiazuron, Methiopyrsulfuron, Methiozolin, Methyl isothiocyanat, Metobromuron,Metolachlor, S-Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron, Metsulfuron-Methyl, Molinat, Monolinuron, Monosulfuron, Monosulfuron-Methyl, MT- 5950, d.h. N-[3-Chlor-4-(l-methylethyl)-phenyl]-2-methylpentanamid, NGGC-011, Napropamid, NC- 310, i.e. 4-(2,4-Dichlorbenzoyl)-l-methyl-5-benzyloxypyrazol, NC-656, i.e. 3- [(Isopropylsulfonyl)methyl]-N-(5-methyl-l,3,4-oxadiazol-2-yl)-5-(trifluormethyl)[l,2,4]triazolo-[4,3- a]pyridin-8-carboxamid, Neburon, Nicosulfuron, Nonansäure (Pelargonsäure), Norflurazon, Ölsäure (Fettsäuren), Orbencarb, Orthosulfamuron, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paraquat, Paraquat-dichlorid, Paraquat-Dimethylsulfat, Pebulat, Pendimethalin, Penoxsulam, Pentachlorphenol, Pentoxazon, Pethoxamid, Petroleumöl, Phenmedipham, Phenmedipham-Ethyl, Picloram, Picloram-dimethylammonium, Picloram-Etexyl, Picloram-Isoctyl, Picloram-Methyl, Picloram-Olamin, Picloram-Kalium, Picloram-Triethylammonium, Picloram- Tripromin,Picloram-Trolamin, Picolinafen, Pinoxaden, Piperophos, Pretilachlor, Primisulfuron, Primisulfuron-Methyl, Prodiamine, Profoxydim, Prometon, Prometryn, Propachlor, Propanil, Propaquizafop, Propazine, Propham, Propisochlor, Propoxycarbazone, Propoxycarbazone-Natrium, Propyrisulfuron, Propyzamid, Prosulfocarb, Prosulfuron, Pyraclonil, Pyraflufen, Pyraflufen-Ethyl, Pyrasulfotol, Pyrazolynat (Pyrazolat), Pyrazosulfuron, Pyrazosulfuron-Ethyl, Pyrazoxyfen, Pyribambenz, Pyribambenz-Isopropyl, Pyribambenz-Propyl, Pyribenzoxim, Pyributicarb, Pyridafol, Pyridat, Pyriftalid, Pyriminobac, Pyriminobac-Methyl, Pyrimisulfan, Pyrithiobac, Pyrithiobac-Natrium, Pyroxasulfon, Pyroxsulam, Quinclorac, Quinclorac-Dimethylammonium, Quinclorac-Methyl, Quinmerac, Quinoclamin, Quizalofop, Quizalofop-Ethyl, Quizalofop-P, Quizalofop-P-Ethyl, Quizalofop-P-Tefuryl, QYM201 , i.e. 1 - { 2-Chlor-3-[(3-cyclopropyl-5-hydroxy- 1 -methyl- lH-pyrazol-4- yl)carbonyl]-6-(trifluormethyl)phe-nyl}piperidin-2-on, Rimsulfuron,Saflufenacil, Sethoxydim, Siduron, Simazine, Simetryn, SL-261, Sulcotrione, Sulfentrazone, Sulfometuron, Sulfometuron-Methyl, Sulfosulfuron, , SYP-249, d.h. l-Ethoxy-3-methyl-l-oxobut-3-en-2-yl-5-[2-chlor-4- (trifluormethyl)phenoxy]-2-nitrobenzoat, SYP-300, i.e. l-[7-Fluor-3-oxo-4-(prop-2-in-l-yl)-3,4- dihydro-2H-l,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidin-4,5-dion, 2,3,6-TBA, TCA (Trichloressigsäure) und seine Salze, z.B. TCA-ammonium, TCA-Calcium, TCA-Ethyl, TCA- Magnesium, TCA-Natrium, Tebuthiuron, Tefuryltrione, Tembotrion, Tepraloxydim, Terbacil, Terbucarb, Terbumeton, Terbuthylazine, Terbutryn, Tetflupyrolimet, Thaxtomin, Thenylchlor, Thiazopyr, Thiencarbazone, Thiencarbazon-Methyl, Thifensulfuron, Thifensulfuron-Methyl, Thiobencarb, Tiafenacil, Tolpyralat, Topramezon, Tralkoxydim, Triafamon, Tri-allat, Triasulfuron, Triaziflam, Tribenuron, Tribenuron-Methyl, Triclopyr, Triclopyr-Butotyl, Triclopyr-Cholin, Triclopyr- Ethyl, Triclopyr-Triethylammonium, Trietazine,Trifloxysulfuron, Trifloxysulfuron-Natrium, Trifludimoxazin, Trifluralin, Triflusulfuron, Triflusulfuron-Methyl, Tritosulfuron, Harnstoffsulfat, Vernolat, XDE-848, ZJ-0862, d.h. 3,4-Dichlor-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}anilin, 3-(2-Chlor-4-fluor-5-(3-methyl-2,6-dioxo-4-trifluormethyl-3,6-dihydropyrimidin-l(2H)-yl)phenyl)-5- methyl-4,5-dihydroisoxazole-5-carbonsäureethylester, Ethyl-[(3-{2-chlor-4-fluor-5-[3-methyl-2,6- dioxo-4-(trifluormethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenoxy}pyridin-2-yl)oxy]acetat, 3-Chlor-2- [3-(difluormethyl)isoxazolyl-5-yl]phenyl-5-chlorpyrimidin-2-ylether, 2-(3,4-Dimethoxyphenyl)-4-[(2- hydroxy-6-oxocyclohex- 1 -en- 1 -yl)carbonyl] -6-methylpyridazine-3(2H)-on, 2-( { 2- [ (2- Methoxyethoxy)methyl]-6-methylpyridin-3-yl}carbonyl)cyclohexane-l,3-dion, (5-Hydroxy-l-methyl- lH-pyrazol-4-yl)(3,3,4-trimethyl- 1 , 1 -dioxido-2,3-dihydro- 1 -benzothiophen-5-yl)methanon, 1 -Methyl-4- [(3,3,4-trimethyl- 1 , 1 -dioxido-2,3 -dihydro- 1 -benzothiophen-5-yl)carbonyl]- lH-pyrazol-5-yl propan- 1 - sulfonat, 4- { 2-Chlor-3-[(3,5-dimethyl- IH-pyrazol- 1 -yl)methyl] -4-(methylsulfonyl)benzoyl} - 1 -methyl- lH-pyrazol-5-yl-l,3-dimethyl-lH-pyrazol-4-carboxylat; Cyanomethyl-4-amino-3-chlor-5-fluor-6-(7- fluor- 1 H-indol-6-yl)pyridin-2-carboxylat, Prop-2-yn- 1 -yl 4-amino-3-chlor-5-fluor-6-(7 -fluor- 1 H-indol- 6-yl)pyridin-2-carboxylat, Methyl-4-amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl)pyridin-2- carboxylat, 4-Amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl)pyridin-2-carbonsäure, Benzyl-4-amino- 3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl)pyridin-2-carboxylat, Ethyl-4-amino-3-chlor-5-fluor-6-(7- fluor- 1 H-indol-6-yl)pyridin-2-carboxylat, Methyl-4-amino-3-chlor-5-fluor-6-(7 -fluor- 1 -isobutyryl- 1 H- indol-6-yl)pyridin-2-carboxylat, Methyl 6-(l-acetyl-7-fluor-lH-indol-6-yl)-4-amino-3-chlor-5- fluorpyridin-2-carboxylat, Methyl-4-amino-3-chlor-6- [ 1 -(2,2-dimethylpropanoyl)-7 -fluor- 1 H-indol-6- yl]-5-fhrorpyridin-2-carboxylat, Methyl-4-amino-3-chlor-5-fluor-6-[7-fluor-l-(methoxyacetyl)-lH- indol-6-yl]pyridin-2-carboxylat, Kalium 4-amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl)pyridin-2- carboxylat, Natrium-4-amino-3-chlor-5-fluor-6-(7-fluor-lH-indol-6-yl)pyridin-2-carboxylat, Butyl-4- amino-3-chlor-5-fhroro-6-(7-fluoro-lH-indol-6-yl)pyridin-2-carboxylat, 4-Hydroxy-l-methyl-3-[4- (trifluoromethyl)pyridin-2-yl]imidazolidin-2-on, 3-(5-tert-butyl- 1 ,2-oxazol-3-yl)-4-hydroxy- 1 - methylimidazolidin-2-on, 3-[5-Chlor-4-(trifluormethyl)pyridin-2-yl]-4-hydroxy-l-methylimidazolidin- 2-on, 4-Hydroxy-l-methoxy-5-methyl-3-[4-(trifluormethyl)pyridin-2-yl]imidazolidin-2-on, 6-[(2- Hydroxy-6-oxocyclohex- 1 -en- 1 -yl)carbonyl] - 1 ,5-dimethyl-3-(2-methylphenyl)chinazolin-2,4( 1H,3H)- dion, 3-(2,6-Dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohex- 1 -en- 1 -yl)carbonyl] - 1 -methylchinazolin- 2,4(lH,3H)-dion,2-[2-chloro-4-(methylsulfonyl)-3-(morpholin-4-ylmethyl)benzoyl]-3-hydroxycyclohex- 2-en-l-one, l-(2-carboxyethyl)-4-(pyrimidin-2-yl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), l-(2-carboxyethyl)-4-(pyridazin-3-yl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), 4-(pyrimidin-2-yl)-l-(2-sulfoethyl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), 4-(pyridazin-3-yl)-l-(2-sulfoethyl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), l-(2-carboxyethyl)-4-(l,3-thiazol-2-yl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), l-(2-carboxyethyl)-4-(l,3-thiazol-2-yl)pyridazin-l-ium salt (with suitable anions such as chloride, acetate or trifluoroacetate), methyl (2R)-2-{[(E)-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-l(2H)-yl]phenyl}methylidene)amino]oxy}propanoate, (E)-2-(trifluoromethyl)benzaldehyde 0-{2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy] benzoyl}oxime, 2-Fluoro-N-(5-methyl-l,3,4-oxadiazol-2-yl)-3-[(R)-propylsulfinyl]-4-(trifluoromethyl)benzamide, (2R)-2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridyl)oxy] propanecarboxylic acid.

[0188] Examples of plant growth regulators as possible mixing partners are:

[0189] Abscisinsäure und verwandte Analoga [z.B. (2Z,4E)-5-[6-Ethynyl-l-hydroxy-2,6-dimethyl-4- oxocyclohex-2-en-l-yl]-3-methylpenta-2,4-diensäure, methyl-(2Z,4E)-5-[6-ethynyl-l-hydroxy-2,6- dimethyl-4-oxocyclohex-2-en-l-yl]-3-methylpenta-2,4-dienoat, (2Z,4E)-3-ethyl-5-(l-hydroxy-2,6,6- trimethyl-4-oxocyclohex-2-en-l-yl)penta-2,4-diensäure, (2E,4E)-5-(l-hydroxy-2,6,6-trimethyl-4- oxocyclohex-2-en-l-yl)-3-(trifluoromethyl)penta-2,4-diensäure, methyl (2E,4E)-5-(l-hydroxy-2,6,6- trimethyl-4-oxocyclohex-2-en-l-yl)-3-(trifluoromethyl)penta-2,4-dienoat, (2Z,4E)-5-(2-hydroxy-l,3- dimethyl-5-oxobicyclo[4.1.0]hept-3-en-2-yl)-3-methylpenta-2,4-diensäure], Acibenzolar, Acibenzolar- S-methyl, S-Adenosylhomocystein, Allantoin, 2-Aminoethoxyvinylglycin (AVG), Aminooxyessigsäure and verwandte Ester [z.B. (Isopropyliden)-aminooxyessigsäure-2-(methoxy)-2-oxoethylester, (Isopropyliden)-aminooxyessigsäure-2-(hexyloxy)-2-oxoethylester, (Cyclohexyliden)- aminooxyessigsäure-2-(isopropyloxy)-2-oxoethylester] ,1-Aminocycloprop- 1 -ylcarboxylic acid N-methyl- 1-aminocyclopropyl-1 -carboxylic acid, 1 -Aminocyclopropyl- 1 -carboxylic acid amide, substituted 1-Aminocyclopropyl-1 -carboxylic acid derivatives as described in DE3335514, EP30287, DE2906507 or US5123951, 1 -Aminocyclopropyl- 1-hydroxamic acid, 5-Aminolevulinic acid, Ancymidol, 6-Benzylaminopurine, Bikinin, Brassinolide, Brassinolide-ethyl, L-Canalin, Catechin and catechins (e.g. (2S,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol), Chitooligosaccharides (CO; COs differ from LCOs in that they lack the LCOs lack the characteristic fatty acid side chain. COs, sometimes referred to as N-acetylchitooligosaccharides, are also composed of GlcNAc units, but have side chains that distinguish them from chitin molecules [(C8H13NO5)n, CAS No. 1398-61-4] and chitosan molecules [(C5H11NO4)n, CAS No. 9012-76-4]), chitin-like compounds, chlormequat chloride, cloprop, cyclanilides,3-(Cycloprop-l-enyl)propionic acid, l-[2-(4-cyano-3,5-dicyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, l-[2-(4-cyano-3-cyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-Cyclopropenylmethanol, Daminozide, Dazomet, Dazomet sodium, n-Decanol, Dikegulac, Dikegulac sodium, Endothal, Endothal di-potassium, -di-sodium, and mono(N,N-dimethylalkylammonium), Ethephon, l-Ethylcyclopropene, Flumetralin, Flurenol, Flurenol butyl, Flurenol methyl, Flurprimidol, Forchlorfenuron, Gibberellic acid, Inabenfid, Indole-3-acetic acid (IAA), 4-Indol-3-ylbutyric acid, Isoprothiolane, Probenazole, jasmonic acid, jasmonic acid esters or other derivatives (e.g. jasmonic acid methyl ester, jasmonic acid ethyl ester), lipochitooligosaccharides (LCO, in some cases also referred to as symbiotic nodulation signals (Nod or Nod factors) or as Myc factors, consist of an oligosaccharide backbone of ß-l,4-linked N-acetyl-D-glucosamine residues (“GlcNAc”) with an N-linked fatty acid side chain,which is condensed at the non-reducing end. As can be seen from the structure, ECOs differ in the number of GlcNAc units in the backbone structure, in the length and degree of saturation of the fatty acid chain as well as in the substitution of the reducing and non-reducing sugar units), einoleic acid or its derivatives, einoleic acid or its derivatives, maleic hydrazide, mepiquat chloride, mepiquat pentaborate, 1-methylcyclopropene, 3-methylcyclopropene, methoxyvinylglycine (MVG), 3'-methylabscisic acid, l-(4-methylphenyl)-N-(2-oxo-1-propyl-1,2,3,4-tetrahydroquinolin-6-yl)methanesulfonamide and related substituted (tetrahydroquinolin-6-yl)methanesulfonamides, (3E,3aR,8bS)-3-({ [(2R)-4-Methyl-5-oxo-2,5-dihydrofuran-2-yl]oxy}methylene)-3,3a,4,8b-tetrahydro-2H-indeno[l,2-b]furan-2-one and related reactones as described in EP2248421, 2-(l-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture,4-Oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazol, 4-phenylbutyric acid and its salts (e.g. sodium 4-phenylbutanoate, potassium 4-phenylbutanoate), phenylalanine, N-phenylphthalamic acid, prohexadione, prohexadione calcium, 1-n-propylcyclopropene, putrescine, prohydrojasmone, rhizobitoxin, salicylic acid and salicyclic acid methyl ester, sarcosine, sodium cycloprop-l-en-l-yl acetate, sodium cycloprop-2-en-l-yl acetate, sodium 3-(cycloprop-2-en-1-yl)propanoate, sodium 3-(cycloprop-1-en-1-yl)propanoate, sidefungin, spermidine, spermine, strigolactone, tecnazene, thidiazuron, triacontanol, Trinexapac, Trinexapac-ethyl, Tryptophan, Tsitodef, Uniconazole, Uniconazole-P, 2-Fluoro-N-(3-methoxyphenyl)-9H-purine-6-amine.,

[0190] When used as active ingredient formulations or co-formulations, these usually contain the usual adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, and solvents, fillers, carriers, and dyes, defoamers, evaporation inhibitors, and pH and viscosity-regulating agents. The compounds of general formula (I) and their combinations with one or more of the aforementioned pesticides can be formulated in various ways depending on the specified chemical-physical and biological parameters. Suitable formulation types include, for example:

[0191] Emulsifiable concentrates produced by dissolving the active ingredients in an organic solvent, e.g., butanol, cyclohexanone, dimethylformamide, xylene, or higher-boiling hydrocarbons or mixtures of organic solvents with the addition of one or more ionic and / or non-ionic surfactants (emulsifiers). Suitable emulsifiers include, for example, calcium salts of alkylarylsulfonic acid, 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.

[0192] Dusts obtained by grinding the active ingredients with finely divided solid inorganic or organic substances, e.g., talc, natural clays such as kaolin, bentonite, and pyrophyllite, diatomaceous earth, or flours. Water- or oil-based suspension concentrates, which can be produced, for example, by wet grinding using bead mills; water-soluble powders; water-soluble concentrates.

[0193] Granules, such as water-soluble granules, water-dispersible granules and granules for broadcast and soil application;

[0194] Wettable powders containing, in addition to the active ingredient, diluents or inert substances and surfactants; capsule suspensions and microcapsules;

[0195] Ultra-low-volume formulations.

[0196] The above-mentioned formulation types are known to the person skilled in the art and are described, for example, in: K. Martens, "Spray Drying Handbook," 3rd Ed., G. Goodwin Ltd., London, 1979; W. van Valkenburg, "Pesticide Formulations," Marcel Dekker, NY, 1973; Winacker-Küchler, "Chemische Technologie," Volume 7, C. Hanser Verlag, Munich, 4th Edition, 1986; "Perry's Chemical Engineer's Handbook," 5th Ed., McGraw-Hill, NY, 1973, pages 8-57.

[0197] The necessary formulation aids such as inert materials, surfactants, solvents and other additives are also 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; Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte", 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., Darland Books, Caldwell NJ; Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th edition 1986.

[0198] In addition to the formulation aids mentioned above, the crop protection agents may optionally contain conventional adhesives, wetting agents, dispersing agents, penetrating agents, emulsifying agents, preservatives, antifreeze agents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents which influence the pH or viscosity.

[0199] Depending on the type of formulation, the crop protection agents generally contain 0.1 to 99% by weight, in particular 0.2 to 95% by weight, of one or more safeners of the general formula (I) or a combination of safener and pesticide. They also 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 a surfactant. In emulsifiable concentrates, the active ingredient concentration, i.e. the concentration of safener and / or pesticide, is generally 1 to 90% by weight, in particular 5 to 80% by weight. Dusts usually 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 case of water-dispersible granules, the active ingredient content is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.

[0200] For application, the formulations available in commercial form are diluted in the usual way, e.g., with water in the case of wettable powders, emulsifiable concentrates, dispersions, and water-dispersible granules. Dust-like preparations, granules, and sprayable solutions are not usually diluted with other inert substances prior to application. The required application rate of the safeners of general formula (I) varies depending on external conditions such as temperature, humidity, the type of herbicide used, and others.

[0201] In the following examples, which illustrate but do not limit the invention, the quantities given are by weight unless otherwise specified.

[0202] EXAMPLES

[0203] 1. FORMULATION EXAMPLES

[0204] 1.1 Dusting agent

[0205] A dust is obtained by mixing 10 parts by weight of a compound of the general formula (I) (safener) or of an active ingredient mixture of a pesticide (e.g. a herbicide) and a safener of the general formula (I) and 90 parts by weight of talc as an inert substance and comminuting in a hammer mill.

[0206] 1.2 WATER-DISPERSIBLE POWDER

[0207] A wettable powder which is easily dispersible in water is obtained by mixing 25 parts by weight of a compound of the general formula (I) or of an active ingredient mixture of a pesticide (e.g. a herbicide) and a safener of the general formula (I), 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurine as wetting and dispersing agent and grinding in a pin mill.

[0208] 1.3 WATER-DISPERSIBLE CONCENTRATE

[0209] A dispersion concentrate which is easily dispersible in water is obtained by mixing 20 parts by weight of a compound of the general formula (I) or of an active ingredient mixture of a pesticide (e.g. a herbicide) and a safener of the formula (I) with 6 parts by weight of alkylphenol polyglycol ether (©Triton X 207), 3 parts by weight of isotridecanol polyglycol ether and 71 parts by weight of paraffinic mineral oil and grinding in a ball mill to a fineness of less than 5 microns.

[0210] 1.4 EMULSIFIABLE CONCENTRATE

[0211] An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the general formula (I) or an active ingredient mixture of a pesticide (e.g. herbicide) and a safener of the general formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.

[0212] 1.5 WATER-DISPERSIBLE GRANULES

[0213] A water-dispersible granulate is obtained by

[0214] 75 parts by weight of a safener of the general formula (I) or of a

[0215] Mixture of a pesticide and a safener of general formula (I),

[0216] 10 "ligninsulfonic acid calcium,

[0217] 5 " sodium lauryl sulfate,

[0218] 3 " polyvinyl alcohol and

[0219] 7 " polyvinyl alcohol and

[0220] 7 " Kaolin is mixed, ground in a pin mill and the powder is granulated in a fluidized bed by spraying water as a granulating liquid.

[0221] A water-dispersible granulate is also obtained by mixing 25 parts by weight of a safener of general formula (I) or of a mixture of a pesticide and a safener of general formula (I),

[0222] 5" 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium,

[0223] 2" oleoylmethyltaurine sodium,

[0224] 17 " calcium carbonate,

[0225] Water and

[0226] 1 part by weight of polyvinyl alcohol is homogenized in a colloid mill, crushed, then ground in a bead mill and the resulting suspension is atomized and dried in a spray tower using a single-component nozzle.

[0227] 2. BIOLOGICAL EXAMPLES

[0228] 2.1 Effect of selected compounds according to the invention using the example of the reduction of damage by mesosulfuron-methyl on spring wheat (TRZAS)

[0229] The seeds of the crops to be treated were sown in soil in plastic pots (diameter ~4 cm), covered with soil, and cultivated in a greenhouse under favorable conditions for germination and growth. The test plants were treated in the early leaf stage (BBCH10 - BBCH12). The compounds of the invention of general formula (I), formulated as wettable powders (WP), were sprayed onto the above-ground parts of the plant as an aqueous suspension at a water application rate corresponding to 800 l / ha, with the addition of a wetting agent (Mero, 0.2%) at the specified dose.

[0230] The herbicide was then applied. Mesosulfuron-methyl, formulated as water-dispersible granules (WG), was sprayed onto the above-ground parts of the plant as an aqueous dispersion at a water application rate equivalent to 800 l / ha with the addition of a wetting agent (Biopower, 1 l / ha) at a dose of 40 g / ha. The herbicide dose was selected to cause moderate, visually clearly detectable damage (50-60%) compared to untreated crops at the time of evaluation on a control group of crops included in the same trial without safener treatment.

[0231] After application, the plants were cultivated in a greenhouse under favorable growth conditions. 12–13 days after application, a visual assessment of the efficacy of the test compounds was performed. For this purpose, the appearance of the plants treated with the test compound and herbicide was compared with the corresponding herbicide controls (without safener; with clearly visible damage) and the untreated controls (without damage). The pest-reducing effect of the test compounds was recorded separately for two replicates using "efficacy codes" according to the following scheme:

[0232] 0: no damage reduction (appearance corresponding to herbicide control)

[0233] 1 : weak damage reduction

[0234] 2: significant reduction in damage

[0235] 3: strong damage reduction

[0236] 4: complete damage reduction (appearance similar to the untreated control)

[0237] As can be seen from the following table, the tests demonstrate a clear effectiveness of the substances according to the invention (= compounds of formula (I) in the following table) in reducing damage to the crop plant spring wheat (TRZAS, cv. Triso) caused by the herbicide mesosulfuron-methyl:

[0238] 2.2 Effect of selected compounds according to the invention using the example of the reduction of damage by mesosulfuron-methyl on spring barley (HORVS)

[0239] The seeds of the crops to be treated were placed in soil in plastic pots (diameter ~4 cm), covered with soil, and cultivated in a greenhouse under favorable conditions for germination and growth. The test plants were treated in the early leaf stage (BBCH10 - BBCH12). The compounds of the invention of general formula (I), formulated as wettable powders (WP), were sprayed onto the above-ground plant parts as an aqueous suspension at a water application rate corresponding to 800 l / ha with the addition of a wetting agent (Mero, 0.2%) at the specified dose. The herbicide was then applied. For this purpose, mesosulfuron-methyl, formulated as water-dispersible granules (WG), was sprayed onto the above-ground plant parts as an aqueous dispersion at a water application rate corresponding to 800 l / ha with the addition of a wetting agent (Biopower, 1 l / ha) at a dose of 40 g / ha.The dose of the herbicide was selected so that, at the time of evaluation, it caused moderate, visually clearly detectable damage (50-60%) to a control group of crops without safener treatment included in the same experiment, compared to untreated crops.

[0240] After application, the plants were cultivated in a greenhouse under favorable growth conditions. 12–13 days after application, a visual assessment of the efficacy of the test compounds was performed. For this purpose, the appearance of the plants treated with the test compound and herbicide was compared with the corresponding herbicide controls (without safener; with clearly visible damage) and the untreated controls (without damage). The pest-reducing effect of the test compounds was recorded separately for two replicates using "efficacy codes" according to the following scheme:

[0241] 0: no damage reduction (appearance according to herbicide control) 1 : weak damage reduction

[0242] 2: significant reduction in damage

[0243] 3: strong damage reduction

[0244] 4: complete damage reduction (appearance similar to the untreated control)

[0245] As can be seen from the following table, the tests demonstrate a clear effectiveness of the substances according to the invention (= compounds of formula (I) in the following table) with regard to the reduction of damage to the crop plant spring barley (HORVS, cv. Quench) caused by the herbicide mesosulfuron-methyl:

[0246]

[0247] 2.3 Comparative effect of selected herbicide / safener combinations according to the invention using the example of pest reduction on the crop plants spring barley (HORVS; cv. Quench) and winter barley (HÖR VW; cv. Zzoom):

[0248] The seeds of the crops to be treated were sown in soil in wood fiber pots (diameter ~7 cm), covered with soil, and grown in a greenhouse under favorable conditions for germination and growth. The test plants were treated at the early leaf stage (BBCH11-12).

[0249] The herbicides and safeners used were formulated as wettable powders (WP), mixed according to the respective specified dose, and sprayed as an aqueous suspension onto the above-ground parts of the plants at a water application rate corresponding to 300 l / ha with the addition of wetting agent (Biopower, 0.2%).

[0250] A mixture of mesosulfuron-methyl (40 g ai / ha) and iodosulfuron-methyl-sodium (8 g ai / ha) was used to achieve the herbicidal effects. The total herbicidal dose was selected to cause moderate, visually clearly detectable damage (min. 20%, max. 60%) compared to untreated crops at the time of evaluation on a control group of crops without safener treatment included in the same trial.

[0251] After application, the plants were cultivated in a greenhouse under favorable growth conditions. Twenty days after application, herbicide damage was visually assessed. Damage was visually assessed on a scale of 0-100% compared to untreated control plants and averaged across two replicates per treatment. Examples:

[0252] 0% = no noticeable effect compared to the untreated plant

[0253] 20% = the treated plant population is compared to the untreated

[0254] Control population 20% damaged (e.g. growth height, leaf damage, etc.) 100% = treated plants completely damaged or dead.

[0255] The following table shows how the damage caused by herbicide treatment on the crop plants spring barley (HORVS; cv. Quench) and winter barley (HÖR VW; cv. Zzoom) is reduced by the addition of a safener. This demonstrates the clear superiority of the compound 1.1-38 according to the invention over a structurally similar compound known from the prior art (W02021 / 105101, 1.4-38).

Claims

Claims:

1. Compounds of general formula (I) or salts thereof, where R 1 independently halogen, cyano, nitro, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkenyl, (C1-C6)-alkoxy or (C1-C6)-alkyl-S(O) p ,wherein the last seven radicals are unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, (C1-C6)-alkoxy and (C1-C6)-alkyl-S(O) p are substituted, R 2 independently halogen, cyano, nitro, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkenyl, (C1-C6)-alkoxy or (C1-C6)-alkyl-S(O) p ,wherein the last seven radicals are unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, (C1-C6)-alkoxy and (C1-C6)-alkyl-S(O) p are substituted, R 3 represents hydrogen or (C1-C6)-alkyl, R 4Wasserstoff, (C1-C 18 )-Alkyl, (C1-C 18 )-Haloalkyl, (C1-C 18 )-Cyanoalkyl, (C2-C 18 )- Alkenyl, (C2-C18)-Alkinyl, (C3-C12)-Cycloalkyl, (C3-C12)-Cycloalkenyl, Aryl, Heteroaryl, (C1-C18)-Alkoxy-(C1-C18)-alkyl, (C1-C18)-Haloalkoxy-(C1-C18)-alkyl, (C1-C18)-Alkoxy-(C1-C18)-haloalkyl, (C1-C18)-Alkylthio-(C1-C18)-alkyl, (C1-C18)- Haloalkylthio-(C1-C18)-alkyl, (C2-C18)-Haloalkenyl, (C2-C18)-Haloalkinyl, Heterocyclyl-(C1-C18)-alkyl, Aryl-(C1-C18)-alkyl, (C3-C12)-Cycloalkyl-(C1-C18)- alkyl, (C1-C 18 )-Alkoxycarbonyl-(C1-C 18 )-alkyl, oder (C1-C 18 )-Alkoxycarbonyl- (C3-C 12 )-cycloalkyl-(C1-C 18 )-alkyl, bedeutet, oder einen Rest der Formel -NR a R b oder -N=CR c R d bedeutet, wobei in den vorgenannten 2 Resten jeder der Reste R a , R b , R c und R dindependently of one another represents hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, benzyl, substituted benzyl, phenyl or substituted phenyl, or R a and R b together with the N atom form a 3- to 8-membered heterocycle which, in addition to the N atom, may contain one or two further hetero ring atoms 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 C atom, a 3- to 8-membered carbocyclic or heterocyclic radical which may contain 1 to 3 hetero ring atoms from the group N, O and S, where the carbocyclic or heterocyclic radical is unsubstituted or substituted by one or more radicals from the group (C1-C4)-alkyl and (C1-C4)-haloalkyl, R 5represents bromine and iodine, n represents a number from 1 to 4, m represents a number from 0 to 5, and p represents 0, 1 or 2.

2. Compounds of the general formula (I) according to claim 1 or salts thereof, wherein R 1 independently of one another halogen, cyano, nitro, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, (C1-C4)-alkoxy or (C1-C4)-alkyl-S(O)p, where the last-mentioned seven radicals unsubstituted or substituted by one or more radicals from the group halogen, cyano, (C1-C4)-alkoxy or (C1-C4)-alkyl-S(O) p are substituted, R 2 independently halogen, cyano, nitro, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, (C1-C4)-alkoxy or (C1-C4)-alkyl-S(O) p,wherein the last-mentioned seven radicals are unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, (C1-C4)-alkoxy or (C1-C4)-alkyl-S(O)p, R 3 represents hydrogen or (C1-C4)-alkyl, R 4 Hydrogen, (C1-C18)-alkyl, (C1-C18)-haloalkyl, (C1-C18)-cyanoalkyl, (C2-C18)-alkenyl, (C2-C18)-alkynyl, (C3-C12)-cycloalkyl, (C3-C12)-cycloalkenyl, aryl, heteroaryl, (C1-C18)-alkoxy-(C1-C18)-alkyl, (C1-C18)-haloalkoxy-(C1-C18)-alkyl, (C1-C18)-alkoxy-(C1-C18)-haloalkyl, (C1-C18)-alkylthio-(C1-C18)-alkyl, (C1-C18)-Haloalkylthio-(C1-C18)-alkyl, (C2-C18)-haloalkenyl, (C2-C18)-haloalkynyl, heterocyclyl-(C1-C18)-alkyl, aryl-(C1-C18)-alkyl, (C3-C12)-cycloalkyl-(C1-C18)-alkyl, (C1-C18)-alkoxycarbonyl-(C1-C18)-alkyl, or (C1-C18)-alkoxycarbonyl-(C3-C12)-cycloalkyl-(C1-C18)-alkyl means, R 5represents bromine and iodine, n represents a number from 1 to 3, m represents a number from 0 to 4, and p represents 0, 1 or 2.

3. Compounds of the general formula (I) according to claim 1 or salts thereof, wherein R 1 independently of each other halogen, cyano, methyl, CF3, CH2F, CHF2, OCH3, OCF3, SCH3 or SCF3, R 2 independently of one another halogen, cyano, methyl, CF3, CH2F, CHF2, OCH3, OCF3, SCH3 or SCF3, R 3 represents hydrogen, CH2CH3or 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-C18)-alkoxy-(C1-C18)-alkyl, (C1-C18)-haloalkoxy-(C1-C18)-alkyl, (C1-C18)-alkoxy-(C1-C18)-haloalkyl, (C1-C18)-alkylthio-(C1-C18)-alkyl, (C1-C18)-haloalkylthio-(C1-C18)-alkyl, (C2-C18)-haloalkenyl, (C2-C18)-haloalkynyl, heterocyclyl-(C1-C18)-alkyl, Aryl-(C1-C18)-alkyl, (C3-C12)-cycloalkyl-(C1-C18)-alkyl, (C1-C18)-alkoxycarbonyl-(C1-C18)-alkyl, or (C1-C18)alkoxycarbonyl-(C3-C12)-cycloalkyl-(C1-C18)-alkyl means. R 5 represents bromine and iodine, n represents a number from 1 to 2, m represents a number from 0 to 3, and p represents 0, 1 or 2.

4. Compounds of the general formula (I) according to claim 1 or salts thereof, wherein R 1 independently of one another represents fluorine, chlorine, bromine, iodine, CN, methyl, CF3, CH2F, CHF2, OCH3, OCF3, SCH3 or SCF3, R 2 independently of one another represents fluorine, chlorine, bromine, iodine, CN, methyl, CF3, CH2F, CHF2, OCH3, OCF3, SCH3 or SCF3, R 3 represents hydrogen or CH3, R 4Hydrogen, (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-C10)-alkyl means, R 5 stands for bromine and iodine, n stands for a number from 1 to 2, m stands for a number from 0 to 2, and p stands for 0, 1 or 2. Compounds of general formula (I) according to claim 1 or salts thereof, wherein R 1 Fluorine, chlorine, bromine, iodine, cyano, methyl, CF3, CH2F, CHF2, OCH3, OCF3, SCH3 or SCF3, R 2 independently fluorine, chlorine, bromine, iodine, cyano, methyl, CF3, CH2F, CHF2, OCH3, OCF3, SCH3 or SCF3 means R 3 stands for hydrogen, R 4 for 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-yl-methyl, Tetrahydropyran-2- yl-methyl, Tetrahydropyran-3-yl-methyl, Tetrahydropyran-4-yl-methyl, Methylpropionat-3-yl, Ethylpropionat-3-yl, Methylacetat-2-yl, Ethylacetat-2-yl, Methylpivalat-2-yl, Ethylpivalat-3-yl, Methyl-2-methylpropanoat-3-yl, Methyl- 2,2-dimethylpropanoat-3-yl, Ethyl-2-methylpropanoat-3-yl, Methyl-2- propanoat-2-yl, Ethyl-2-propanoat-2-yl, Methyl-acetat-2yl, Ethyl-acetat-2yl, Methyl- 1 -methylcyclopropancarboxylat-2yl, Ethyl- 1 -methylcyclopropan- carboxylat-2yl, 2-(Dimethylamino)ethyl, Oxetan-3-yl, (3-Methyloxetan-3- yl)methyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, 2-Fluorethyl, 2, 2, 3,3,3- Pentafluorpropyl, Cyclopropylmethyl, 1-Cyclopropyl-ethyl, (1-Methyl- cyclopropyl) -methyl, (2,2-Dichlorcyclopropyl)-methyl, (2,2-Dimethyl- cyclopropyl) -methyl, Allyl, Propargyl (Prop-2-in-l-yl), 2-Chlorprop-2-en-l-yl, 3-Phenylprop-2-in- 1 -yl, 3,3-Dichloroprop-2-en-1-yl, 3,3-Dichloro-2-fluoro-prop-2-en-l-yl, Methylprop-2-yn-l-yl, 2-Methylprop-2-en-l-yl, But-2-en-l-yl, But-3-en-l-yl, But-2-yn-l-yl, But-3-yn-l-yl, 4-Chloro-but-2-yn-l-yl, 3-methyl-but-2-en-1-yl, 3-methyl-but-l-en-l-yl, 1-(2E)-l-methylbut-2-en-l-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, Heptan-2-yl, iso-butyl, l,3-dioxolan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazol-4-methyl, R 5 stands for bromine and iodine, n stands for the number 1, and m is a number from 0 to 2. Compounds of the general formula (I) according to claim 1 or salts thereof, wherein para-R 5 -(R') n -Phenyl for groups Ql.l to Q-1.2 stands, and (R 2 ) m -Phenyl for groups Q-2.1 to Q-2.53 stands, R 3 stands for hydrogen, and R 4 for 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-yl-methyl, Tetrahydropyran-2- yl-methyl, Tetrahydropyran-3-yl-methyl, Tetrahydropyran-4-yl-methyl, Methylpropionat-3-yl, Ethylpropionat-3-yl, Methylacetat-2-yl, Ethylacetat-2-yl, Methylpivalat-2-yl, Ethylpivalat-3-yl, Methyl-2-methylpropanoat-3-yl, Methyl- 2,2-dimethylpropanoat-3-yl, Ethyl-2-methylpropanoat-3-yl, Methyl-2- propanoat-2-yl, Ethyl-2-propanoat-2-yl, Methyl-acetat-2yl, Ethyl-acetat-2yl, Methyl- 1 -methylcyclopropancarboxylat-2yl, Ethyl- 1 - methylcyclopropancarboxylat-2yl, 2-(Dimethylamino)ethyl, Oxetan-3-yl, (3- Methyloxetan-3-yl)methyl, 2,2,2-Trifluorethyl, 2,2-Difluorethyl, 2-Fluorethyl, 2,2,3,3,3-Pentafluorpropyl, Cyclopropylmethyl, 1-Cyclopropyl-ethyl, (1- Methyl-cyclopropyl)-methyl, (2,2-Dichlorcyclopropyl)-methyl, (2,2-Dimethyl- cyclopropyl) -methyl, Allyl, Propargyl (Prop-2-in-l-yl), 2-Chlorprop-2-en-l-yl, 3-Phenylprop-2-in- 1 -yl, 3,3-Dichloroprop-2-en-1-yl, 3,3-Dichloro-2-fluoro-prop-2-en-l-yl, Methylprop-2-yn-l-yl, 2-Methylprop-2-en-l-yl, But-2-en-l-yl, But-3-en-l-yl, But-2-yn-l-yl, But-3-yn-l-yl, 4-Chloro-but-2-yn-l-yl, 3-methyl-but-2-en-1-yl, 3-methyl-but-l-en-l-yl, 1-(2E)-l-methylbut-2-en-l-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, Heptan-2-yl, iso-butyl, l,3-dioxolan-2-ylmethyl or 1-ethyl-5-methyl-1-pyrazol-4-methyl. A crop or plant-protecting agent, characterized by containing at least one compound of the general formula (I) or salts thereof according to one of claims 1, to 6, in combination with other agrochemicals and optionally formulation auxiliaries. A composition according to claim 7, containing at least one herbicide. A method for reducing the phytotoxic effects of pesticides on crop plants by using one or more compounds of claims 1-6 or the compositions according to claims 7 and 8. A method for reducing the phytotoxic effects of pesticides on crop plants, characterized in that one or more compounds of the general formula (I) according to claims 1 to 6 according to the invention for joint use with pesticides are applied simultaneously or in any desired sequence with the pesticides. A method according to claim 10, wherein the pesticides are one or more herbicides.Process according to claims 10 or 11, characterized in that compounds of formula (I) or salts thereof according to claims 1 to 6 are applied to the plants, parts of the plants, their seeds or seed.

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