Herbicide / safener combinations based on safeners of substituted [(1, 5-diphenyl-1h-1, 2, 4-triazol-3-yl) oxy] acetic acid and salts thereof

Abstract

The present invention relates to combinations comprising one or more active components (A) as safeners and one or more herbicidally active compounds (component (B)) wherein component (A) represents one or more compounds of general formula (I) or agrochemically acceptable salts thereof and component (B) represents one or more herbicides. The invention also relates to a method and use of the herbicide / safener combination according to the invention for controlling harmful plants or for growth regulation. # imgabs0 #

Description

[0001] The present invention relates to the technical field of crop protection compositions which can be used to inhibit the growth of unwanted plants on arable land, for the preparation of seeds or for use in plant crops, comprising a combination of at least one safener (A) and at least one herbicide (B), wherein the safener (A) is one or more substituted [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acids of the general formula (I) and / or agrochemically acceptable salts thereof (=component (A)).

[0002] The efficacy of the known herbicides against harmful plants is at a high level, but generally depends on the application rate, the form of the corresponding formulation, the spectrum of harmful plants, the harmful plants to be controlled in each case, climatic and soil conditions, etc. and in particular on the compatibility of the crop plants.

[0003] One of the ways to improve the application characteristics of herbicides may be to combine safeners with one or more active herbicidal ingredients that provide the desired additional properties. However, in the combined application of two or more active ingredients, physical and biological incompatibility phenomena are not uncommon, such as lack of stability in the combined formulation, decomposition of the active ingredients and / or antagonism between the active ingredients, or the limited scope of action of the safener, which can only protect crop plants from one herbicide but not all components in the combined application of two or more herbicides.

[0004] Safeners (also known as antidotes) with different chemical structures have been around for about 70 years. It is also known that they differ significantly in their protective function, which means that their use is limited to selected herbicides and / or crop plants to be protected. Depending on the harmful plants to be controlled, it is also required that the selected herbicide / safener combination does not have an adverse effect on the weed control efficacy.

[0005] [(1,5-Diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives and their salts are known from PCT application No. PCT / EP2020 / 083167 (WO2021 / 105101).

[0006] It has now been found that substituted [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid compounds can indeed be used to effectively protect different crop plants when one or more herbicides [component (B)] of different chemical structure are applied.

[0007] The herbicide / safener combinations according to the invention interact in a particularly advantageous manner, for example when they are used to control unwanted vegetation in crop plants such as wheat (hard and soft wheat), maize, soybeans, sugar beets, sugar cane, cotton, rice, legumes (e.g. bush beans and broad beans), flax, barley, oats, rye, triticale, potatoes and millet / sorghum.

[0008] The present invention therefore provides a combination comprising one or more active components (A) as safeners and one or more herbicidally active compounds as component (B), wherein (A) represents one or more compounds of the general formula (I) or an agrochemically acceptable salt thereof,

[0009]

[0010] and among them

[0011] (R 1 ) n -phenyl represents a group representing Q-1.1 to Q-1.53

[0012]

[0013]

[0014] and (R 2 ) m - Phenyl represents a group of Q-2.1 to Q-2.53.

[0015]

[0016]

[0017]

[0018] R 3 represents hydrogen,

[0019] and

[0020] R 4represents 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-ylmethyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl, methylpropionate-3-yl, ethylpropionate-3-yl, methylacetate-2-yl, ethylacetate-2-yl, methylpivalate-2-yl, ethyl pivalate-3-yl, methyl-2-methylpropionate-3-yl, methyl-2,2-dimethylpropionate-3-yl, ethyl-2-methylpropionate-3-yl, methyl-2-propionate-2-yl, ethyl-2-propionate-2-yl, methyl acetate-2-yl, ethyl acetate-2-yl, methyl-1-methylcyclopropanecarboxylate-2-yl, ethyl-1-methylcyclopropanecarboxylate-2-yl, 2-(dimethylamino)ethyl, oxetan-3-yl, (3-methyloxetan-3-yl)methyl, 2,2,2-trifluoroethyl, 2,2-di Fluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl, cyclopropylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl, allyl, propargyl (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl, 3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl, 2-methylprop-2-en-1-yl, but-2 -en-1-yl, but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, hept-2-yl, isobutyl, 1,3-dioxol-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazol-4-methyl,

[0021] and

[0022] (B) one or more herbicides [component (B)] selected from the active herbicidal ingredients having the general formula (II),

[0023]

[0024] A is N or CY,

[0025] X is nitro, halogen, cyano, formyl, thiocyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C3-C6)-alkynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR 1 、COOR 1 、OCOOR 1 NR 1 COOR 1 、C(O)N(R 1 )2. NR 1 C(O)N(R 1 )2、OC(O)N(R 1 )2、C(O)NR 1 OR 1 , OR 1 ,OCOR 1 、OSO2R 2 、S(O) n R 2 、SO2OR 1 SO2N(R 1 )2. NR 1 S02R 2 NR 1 COR 1 、(C1-C6)-alkyl-S(O) n R 2 、(C1-C6)-alkyl-OR 1 、(C1-C6)-alkyl-OCOR 1 、(C1-C6)-alkyl-OSO2R 2 、(C1-C6)-alkyl-CO2R 1 、(C1-C6)-alkyl-SO2OR 1 、(C1-C6)-alkyl-CON(R 1 )2、(C1-C6)-alkyl-SO2N(R 1 )2, (C1-C6)-alkyl-NR 1 COR 1 、(C1-C6)-alkyl-NR 1 S02R 2 NR 1 R 2 、P(O)(OR 5 )2、CH2P(O)(OR 5)2, (C1-C6)-alkylheteroaryl, (C1-C6)-alkylheterocyclyl, wherein the latter two radicals are each substituted by s radicals selected from halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, S(O) n -(C1-C6)-alkyl, (C1-C6)-alkoxy and halo-(C1-C6)-alkoxy groups, and wherein the heterocyclyl has n oxo groups,

[0026] Y is hydrogen, nitro, halogen, cyano, thiocyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR 1 、COOR 1 、OCOOR 1 NR 1 COOR 1 、C(O)N(R 1 )2. NR 1 C(O)N(R 1 )2、OC(O)N(R 1 2. CO(NOR 1 )R 1 NR 1 S02R 2 NR 1 COR 1 , OR 1 、OSO2R 2 、S(O) n R 2 、SO2OR 1 SO2N(R 1 )2、(C1-C6)-alkyl-S(O) n R 2 、(C1-C6)-alkyl-OR 1 、(C1-C6)-alkyl-OCOR 1 、(C1-C6)-alkyl-OSO2R 2 、(C1-C6)-alkyl-CO2R 1 、(C1-C6)-alkyl-CN、(C1-C6)-alkyl-SO2OR 1 、(C1-C6)-alkyl-CON(R 1 )2、(C1-C6)-alkyl-SO2N(R 1)2, (C1-C6)-alkyl-NR 1 COR 1 、(C1-C6)-alkyl-NR 1 S02R 2 、N(R 1 )2、P(O)(OR 5 )2、CH2P(O)(OR 5 )2, (C1-C6)-alkylphenyl, (C1-C6)-alkylheteroaryl, (C1-C6)-alkylheterocyclyl, phenyl, heteroaryl or heterocyclyl, wherein the last six radicals are each substituted by s selected from halogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, S(O) n -(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, (C1-C6)-alkoxy-(C1-C4)-alkyl and cyanomethyl groups, and the heterocyclic group has n oxo groups,

[0027] Z is halogen, cyano, thiocyano, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C2-C6)-alkynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR 1 、COOR 1 、OCOOR 1 NR 1 COOR 1 、C(O)N(R 1 )2. NR 1 C(O)N(R 1 )2、OC(O)N(R 1 )2、C(O)NR 1 OR 1 、OSO2R 2 、S(O) n R 2 、SO2OR 1 SO2N(R 1 )2. NR 1 S02R 2 NR 1 COR 1 、(C1-C6)-alkyl-S(O) n R 2 、(C1-C6)-alkyl-OR 1 、(C1-C6)-alkyl-OCOR1 、(C1-C6)-alkyl-OSO2R 2 、(C1-C6)-alkyl-CO2R 1 、(C1-C6)-alkyl-SO2OR 1 、(C1-C6)-alkyl-CON(R 1 )2、(C1-C6)-alkyl-SO2N(R 1 )2, (C1-C6)-alkyl-NR 1 COR 1 、(C1-C6)-alkyl-NR 1 S02R 2 、N(R 1 )2、P(O)(OR 5 )2, heteroaryl, heterocyclic or phenyl, wherein the last three groups are each substituted by s selected from halogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, S(O) n -(C1-C6)-alkyl, (C1-C6)-alkoxy or halo-(C1-C6)-alkoxy, and the heterocyclyl has n oxo groups, or

[0028] Z can also be hydrogen, (C1-C6)-alkyl or (C1-C6)-alkoxy. If Y is S(O) n R 2 Group,

[0029] R is (C1-C8)-alkyl, halo-(C1-C8)-alkyl, (C2-C8)-alkenyl, halo-(C2-C8)-alkenyl, (C2-C8)-alkynyl, halo-(C2-C8)-alkynyl, wherein each of the six groups is substituted by s groups selected from the group consisting of hydroxyl, nitro, cyano, SiR 5 3. PO(OR 5 )2. S(O) n -(C1-C6)-alkyl, S(O) n -(C1-C6)-haloalkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, N(R 3 2. COR 3 、COOR 3 ,OCOR 3 NR 3 COR 3 NR 3 S02R 4, O(C1-C2)-alkyl-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl, heteroaryl, heterocyclyl, phenyl, wherein the last three groups are each substituted by s groups selected from methyl, ethyl, methoxy, trifluoromethyl, cyano and halogen, and wherein the heterocyclyl has n oxo groups, or

[0030] R is (C3-C7)-cycloalkyl, heteroaryl, heterocyclyl or phenyl, each of which is substituted by s selected from halogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, S(O) n -(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy and (C1-C6)-alkoxy-(C1-C4)-alkyl radicals, wherein the heterocyclyl radical has n oxo radicals,

[0031] R 1 is hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, (C3-C6)-halocycloalkyl, (C1-C6)-alkyl-(C3-C6)- ... 6)-alkyl-O-(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl, heteroaryl, (C1-C6)-alkylheteroaryl, heterocyclyl, (C1-C6)-alkylheterocyclyl, (C1-C6)-alkyl-O-heteroaryl, (C1-C6)-alkyl-O-heterocyclyl, (C1-C6)-alkyl-NR 3 -heteroaryl or (C1-C6)-alkyl-NR 3 -heterocyclic group, wherein the last 21 groups are each selected from cyano, nitro, thiocyano, OR 3 、S(O) n R 4 、N(R 3 )2. NR 3 OR 3 , COR 3 ,OCOR 3 SCOR 4 NR 3 COR 3 NR 3 S02R 4 、CO2R 3 、COSR 4 、CON(R 3)2 and (C1-C4)-alkoxy-(C2-C6)-alkoxycarbonyl groups, and wherein the heterocyclic group has n oxo groups,

[0032] R 2 is (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, (C3-C6)-halocycloalkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl, heteroaryl, (C1-C6)-alkylheteroaryl, heterocyclyl, (C1-C6)-alkylheterocyclyl, (C1-C6)-alkyl-O-heteroaryl, (C1-C6)-alkyl-O-heterocyclyl, (C1-C6)-alkyl-NR 3 -heteroaryl or (C1-C6)-alkyl-NR 3 -heterocyclic group, wherein the last 21 groups are each selected from cyano, halogen, nitro, thiocyanate, OR 3 、S(O) n R 4 、N(R 3 )2. NR 3 OR 3 , COR 3 ,OCOR 3 SCOR 4 NR 3 COR 3 NR 3 S02R 4 、CO2R 3 、COSR 4 、CON(R 3 )2 and (C1-C4)-alkoxy-(C2-C6)-alkoxycarbonyl groups, and wherein the heterocyclic group has n oxo groups,

[0033] R 3 is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl or phenyl,

[0034] R 4 is (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl or phenyl,

[0035] R5 is (C1-C4)-alkyl,

[0036] n is 0, 1, or 2,

[0037] s is 0, 1, 2, or 3,

[0038] The active herbicidal ingredients of formula (I) are known, for example, from WO 2012 / 028579 A1, WO 2013 / 064458 A1, WO 2013 / 174845 A1, WO 2016 / 001075 A1, WO 2016 / 001073 A1, WO 2018 / 202535 A1, WO 2019 / 025540 A1, WO 2021 / 204665 A1 and WO 2021 / 204666 A1.

[0039] In the following only neutral compounds are mentioned, which therefore encompasses all the present forms listed, unless in a specific context, such as in the examples of biological efficacy in the following table, a specific form of the active ingredient is relevant.

[0040] The herbicide / safener combination of the present invention may contain other components, for example other active ingredients for combating harmful organisms (e.g. harmful plants, animals that damage plants or fungi that damage plants), in particular active ingredients selected from herbicides, fungicides, insecticides, acaricides, nematicides and miticides and related substances other than the herbicides mentioned in item B, or other types of active ingredients for crop protection (e.g. resistance inducers), crop plant protection active ingredients (safeners, antidotes except component (A)), plant growth regulators and / or additives and / or formulation auxiliaries commonly used in crop protection. In this context, these components can be formulated together (ready-to-use formulations) and used as such, or they can be formulated separately and then used together, for example in tank mixes or sequential application.

[0041] When a single safener of the general formula (I) appears as component (A), it is also referred to as compound (A), active ingredient (A), component (A) or safener (A) hereinafter. Correspondingly, when a single active herbicidal ingredient appears as component (B), it is also referred to as compound (B), active ingredient (B), component (B), herbicide (B) or compound of formula (II) hereinafter.

[0042] An advantageous property of the safener (A) and herbicide (B) combinations according to the invention is that the safener (A) and the herbicide (B) are compatible with each other, meaning that they can be used together without significant chemical incompatibilities between the safener (A) and / or the herbicide (B) occurring which would lead to the destruction of the safener (A) or the herbicide (B).

[0043] This good compatibility also extends to the biological properties of the active ingredients when used in combination. For example, when using the herbicide / safener combinations according to the invention to control harmful plants, antagonism is generally not observed.

[0044] In the compounds of the safeners (A) of the formula (I) and in the compounds of the herbicides (B) of the formula (II) and in all the formulae below, the following definitions apply:

[0045] Depending on the nature of the substituents and their connection mode, the compounds of formula (I) or (II) may exist in the form of stereoisomers. For example, if there are one or more asymmetrically substituted carbon atoms and / or sulfoxides, enantiomers and diastereomers may occur. Stereoisomers can be obtained from the mixture obtained in the preparation by conventional separation methods (e.g. chromatographic separation methods). It is also possible to selectively prepare stereoisomers by using stereoselective reactions using optically active starting materials and / or auxiliary agents.

[0046] The present invention also relates to all stereoisomers encompassed by formula (I) or (II) but not specifically defined, and mixtures thereof. However, for simplicity, reference will always be made hereinafter to compounds of formula (I) or (II), even if this means not only the pure compounds but also, if appropriate, mixtures of isomeric compounds in different ratios.

[0047] Depending on the nature of the substituents defined above, the compounds of formula (I) or (II) have acidic properties and can form salts with inorganic or organic bases or with metal ions, if appropriate, inner salts or adducts. If the compounds of formula (I) or (II) carry hydroxyl, carboxyl or other groups that cause acidity, these compounds can react with bases to form salts. Suitable bases are, for example, hydroxides, carbonates, bicarbonates of alkali metals and alkaline earth metals (especially sodium, potassium, magnesium and calcium), and ammonia, primary, secondary and tertiary amines with (C1-C4)-alkyl groups, mono-, di- and tri-alkanolamines of (C1-C4)-alkanols, choline and choline chloride, and organic amines such as trialkylamines, morpholine, piperidine or pyridine.

[0048] These salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, for example a metal salt, in particular an alkali metal salt or an alkaline earth metal salt, in particular a sodium salt and a potassium salt, or an ammonium salt, a salt with an organic amine or a quaternary ammonium salt, for example having the formula [NRR′R″R″′] + cation, wherein R to R"' are each independently an organic group, in particular an alkyl, aryl, aralkyl or alkylaryl group. Also useful are alkyl sulfonium salts and alkyl sulfoxide salts, for example (C1-C4)-trialkylsulfonium salts and (C1-C4)-trialkylsulfoxide salts.

[0049] The compounds of formula (I) or (II) can be formed into salts by adding a suitable inorganic or organic acid (e.g. a mineral acid such as HCl, HBr, H2SO4, H3PO4 or HNO3; or an organic acid such as a carboxylic acid such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or a sulfonic acid, e.g. p-toluenesulfonic acid) to a basic group (e.g. amino, alkylamino, dialkylamino, piperidinyl, morpholinyl or pyridinyl). These salts also contain the conjugate base of the acid in anionic form.

[0050] Suitable substituents which are present in deprotonated form, such as sulfonic acids or carboxylic acids, are able to form internal salts with groups which themselves can be protonated, such as amino groups.

[0051] If a radical is polysubstituted by radicals, this means that the radical is substituted by one or more substituents which are identical or different from the radicals already mentioned.

[0052] Below is a description of preferred, particularly preferred and very particularly preferred definitions for each individual safener (A) and herbicide (B).

[0053] If a compound can form tautomers whose structures are not formally covered by the general formula (A) by hydrogen transfer, these tautomers are nevertheless included in the definition of the compounds of the invention of the general formula (A), unless a specific tautomer is considered. For example, many carbonyl compounds can exist simultaneously in the keto form and the enol form, both of which are included in the definition of the compounds of the general formula (A).

[0054] Depending on the nature of the substituents and how they are connected, the compounds of general formula (I) may exist as stereoisomers. Possible stereoisomers defined by their specific three-dimensional form, such as enantiomers, diastereomers, Z and E isomers are all covered by general formula (I). For example, if one or more alkenyl groups are present, diastereomers (Z and E isomers) may occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur. Stereoisomers can be obtained from the mixture obtained in the preparation by conventional separation methods. Chromatographic separations can be carried out on an analytical scale to determine enantiomeric excess or diastereomeric excess, and can also be carried out on a preparative scale to prepare test samples for biological testing. Similarly, stereoisomers can also be selectively prepared by stereoselective reactions using optically active starting materials and / or auxiliary agents. Therefore, the present invention also relates to all stereoisomers and mixtures thereof that are covered by general formula (I) but not shown in a specific stereo form.

[0055] If the compounds are obtained in solid form, they can also be purified by recrystallization or purification. If individual compounds of the general formula (I) cannot be obtained in a satisfactory manner via the routes described below, they can be prepared by derivatization of other compounds of the general formula (I).

[0056] Suitable separation methods, purification methods and methods for separating the stereoisomers of the compounds of the general formula (I) are the general methods known to the person skilled in the art in analogous cases, for example by physical methods such as crystallization, chromatography, in particular column chromatography and HPLC (high pressure liquid chromatography), distillation (optionally under reduced pressure), extraction and other methods, any remaining mixtures can usually be separated by chromatographic separation methods, for example on a chiral solid phase. Suitable methods for preparative quantities or on an industrial scale are crystallization, for example the crystallization of diastereomeric salts obtained from diastereomeric mixtures using optically active acids (if appropriate, provided that acidic groups are present) and using optically active bases.

[0057] In a first embodiment of the present invention, the herbicide / safener combination of the present invention and at least one component (B) as defined above preferably comprises a compound of the general formula (I) [component A] or an agrochemically compatible salt thereof [safener (A)], see Table 1 for details.

[0058] Table 1: IUPAC names and structural formulas of preferred compounds of formula (I) (safeners (A))

[0059]

[0060]

[0061] The compounds of formula (I) are known from the international application with application number PCT / EP2020 / 083167 (WO2021 / 105101) and can be prepared by the methods described therein.

[0062] The application rate of the herbicide (B) is 20 to 400 grams of active substance per hectare (hereinafter referred to as g ai / ha), preferably 40 to 200 g ai / ha, especially 40 to 100 g ai / ha; the application rate of the safener (A) is 1 to 1000 g ai / ha, preferably 10 to 500 g ai / ha, especially 20 to 200 g ai / ha of active substance.

[0063] In the context of the present invention, particularly preferred safeners (A) are the compounds numbered A1, A3 and A5 according to the abovementioned Table 1.

[0064] Suitable combination compatibility agents (B) [= component (B) or herbicide (B)] are in principle all active ingredients from subgroups (B1) to (B11), wherein the herbicidal active ingredients are mostly named by their common names (English symbols) (according to reference The Pesticide Manual "14th edition, British Crop Protection Council 2006, referred to as "PM") or by their chemical names according to standard nomenclature (IUPAC or Chemical Abstracts). However, it has surprisingly been found that some herbicides (B) are particularly suitable as combination compatibility agents for safeners (A). The preferred and more preferred herbicides (B) listed below are further embodiments of the present invention.

[0065] In the second embodiment of the present invention, the active herbicidal ingredient of formula (II) is preferred.

[0066]

[0067] in

[0068] A is N or CY,

[0069] X is halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C3-C6)-alkynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR 1 、COOR 1 、OCOOR 1 NR 1 COOR 1 、C(O)N(R 1 )2、OC(O)N(R 1 )2、C(O)NR 1 OR 1 , OR 1 ,OCOR 1 、OSO2R 2 、S(O) n R 2 NR 1 S02R 2 NR 1 COR 1 、(C1-C6)-alkyl-S(O) n R 2 、(C1-C6)-alkyl-OR 1、(C1-C6)-alkyl-OCOR 1 、(C1-C6)-alkyl-OSO2R 2 、(C1-C6)-alkyl-CO2R 1 、(C1-C6)-alkyl-SO2OR 1 、(C1-C6)-alkyl-CON(R 1 )2、(C1-C6)-alkyl-SO2N(R 1 )2, (C1-C6)-alkyl-NR 1 COR 1 、(C1-C6)-alkyl-NR 1 S02R 2 ,

[0070] Y is hydrogen, halogen, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR 1 、COOR 1 、OCOOR 1 NR 1 COOR 1 、C(O)N(R 1 )2. NR 1 C(O)N(R 1 )2、OC(O)N(R 1 2. CO(NOR 1 )R 1 NR 1 S02R 2 NR 1 COR 1 , OR 1 、OSO2R 2 、S(O) n R 2 、SO2OR 1 SO2N(R 1 )2、(C1-C6)-alkyl-S(O) n R 2 、(C1-C6)-alkyl-OR 1 、(C1-C6)-alkyl-OCOR 1 、(C1-C6)-alkyl-OSO2R 2 、(C1-C6)-alkyl-CO2R1 、(C1-C6)-alkyl-CN、(C1-C6)-alkyl-SO2OR 1 、(C1-C6)-alkyl-CON(R 1 )2、(C1-C6)-alkyl-SO2N(R 1 )2, (C1-C6)-alkyl-NR 1 COR 1 、(C1-C6)-alkyl-NR 1 S02R 2 、N(R 1 ) 2. a heterocyclic group, wherein the heterocyclic group may have n oxo groups,

[0071] Z is halogen, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C2-C6)-alkynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR 1 、COOR 1 、OCOOR 1 NR 1 COOR 1 、C(O)N(R 1 )2. NR 1 C(O)N(R 1 )2、OC(O)N(R 1 )2、C(O)NR 1 OR 1 、OSO2R 2 、S(O) n R 2 、SO2OR 1 SO2N(R 1 )2. NR 1 S02R 2 NR 1 COR 1 、(C1-C6)-alkyl-S(O) n R 2 、(C1-C6)-alkyl-OR 1 、(C1-C6)-alkyl-OCOR 1 、(C1-C6)-alkyl-OSO2R 2 、(C1-C6)-alkyl-CO2R 1 、(C1-C6)-alkyl-SO2OR 1 、(C1-C6)-alkyl-CON(R 1)2、(C1-C6)-alkyl-SO2N(R 1 )2, (C1-C6)-alkyl-NR 1 COR 1 、(C1-C6)-alkyl-NR 1 S02R 2 、N(R 1 )2,

[0072] Z can also be hydrogen, (C1-C6)-alkyl or (C1-C6)-alkoxy. If Y is S(O) n R 2 Group,

[0073] R is (C1-C8)-alkyl, halo-(C1-C8)-alkyl, (C2-C8)-alkenyl, halo-(C2-C8)-alkenyl, (C2-C8)-alkynyl, halo-(C2-C8)-alkynyl, (C3-C6)-cycloalkyl, phenyl,

[0074] R 1 is hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, (C3-C6)-halocycloalkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl, heteroaryl, (C1-C6)-alkylheteroaryl, heterocyclyl, where the (C3-C6)-cycloalkyl group can be substituted by s (C1-C6)-alkyl groups.

[0075] R 2 is (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, (C3-C6)-halocycloalkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, phenyl,

[0076] n is 0, 1, or 2,

[0077] s is 0, 1, 2, or 3.

[0078] In the third embodiment of the present invention, the active herbicidal ingredient of formula (II) is preferred.

[0079]

[0080] in

[0081] A is CY,

[0082] X is halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C3-C6)-alkynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR 1 、COOR 1 、OCOOR 1 NR 1 COOR 1 、C(O)N(R 1 )2、OC(O)N(R 1 )2、C(O)NR 1 OR 1 , OR 1 ,OCOR 1 、OSO2R 2 、S(O) n R 2 NR 1 S02R 2 NR 1 COR 1 、(C1-C6)-alkyl-S(O) n R 2 、(C1-C6)-alkyl-OR 1 、(C1-C6)-alkyl-OCOR 1 、(C1-C6)-alkyl-OSO2R 2 、(C1-C6)-alkyl-CO2R 1 、(C1-C6)-alkyl-SO2OR 1 、(C1-C6)-alkyl-CON(R 1 )2、(C1-C6)-alkyl-SO2N(R 1 )2, (C1-C6)-alkyl-NR 1 COR 1 、(C1-C6)-alkyl-NR 1 S02R 2 ,

[0083] Y is hydrogen, halogen, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR 1 、COOR 1 、OCOOR 1 NR 1 COOR 1 、C(O)N(R 1 )2. NR 1 C(O)N(R 1 )2、OC(O)N(R 1 2. CO(NOR 1 )R 1 NR 1 S02R 2 NR 1 COR 1 , OR 1 、OSO2R 2 、S(O) n R 2 、SO2OR 1 SO2N(R 1 )2、(C1-C6)-alkyl-S(O) n R 2 、(C1-C6)-alkyl-OR 1 、(C1-C6)-alkyl-OCOR 1 、(C1-C6)-alkyl-OSO2R 2 、(C1-C6)-alkyl-CO2R 1 、(C1-C6)-alkyl-CN、(C1-C6)-alkyl-SO2OR 1 、(C1-C6)-alkyl-CON(R 1 )2、(C1-C6)-alkyl-SO2N(R 1 )2, (C1-C6)-alkyl-NR 1 COR 1 、(C1-C6)-alkyl-NR 1 S02R 2 、N(R 1 )2. a heterocyclic group, wherein the heterocyclic group may have n oxo groups,

[0084] Z is halogen, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C2-C6)-alkynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR 1 、COOR 1 、OCOOR 1 NR 1 COOR 1 、C(O)N(R 1 )2. NR 1 C(O)N(R 1 )2、OC(O)N(R 1 )2、C(O)NR 1 OR 1 、OSO2R 2 、S(O) n R 2 、SO2OR 1 SO2N(R 1 )2. NR 1 S02R 2 NR 1 COR 1 、(C1-C6)-alkyl-S(O) n R 2 、(C1-C6)-alkyl-OR 1 、(C1-C6)-alkyl-OCOR 1 、(C1-C6)-alkyl-OSO2R 2 、(C1-C6)-alkyl-CO2R 1 、(C1-C6)-alkyl-SO2OR 1 、(C1-C6)-alkyl-CON(R 1 )2、(C1-C6)-alkyl-SO2N(R 1 )2, (C1-C6)-alkyl-NR 1 COR 1 、(C1-C6)-alkyl-NR 1 S02R 2 、N(R 1 )2,

[0085] Z can also be hydrogen, (C1-C6)-alkyl or (C1-C6)-alkoxy. If Y is S(O) n R 2 Group,

[0086] R is (C1-C8)-alkyl, halo-(C1-C8)-alkyl, (C2-C8)-alkenyl, halo-(C2-C8)-alkenyl, (C2-C8)-alkynyl, halo-(C2-C8)-alkynyl, (C3-C6)-cycloalkyl, phenyl,

[0087] R 1 is hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, (C3-C6)-halocycloalkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl, heteroaryl, (C1-C6)-alkylheteroaryl, heterocyclyl, where the (C3-C6)-cycloalkyl group can be substituted by s (C1-C6)-alkyl groups.

[0088] R 2 is (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, (C3-C6)-halocycloalkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, phenyl,

[0089] n is 0, 1, or 2,

[0090] s is 0, 1, 2, or 3.

[0091] In the fourth embodiment of the present invention, the active herbicidal ingredient of formula (II) is preferred.

[0092]

[0093] in

[0094] A is CY,

[0095] X is halogen, (C1-C6)-alkyl, (C1-C6)-alkyl-OR 1 ,

[0096] Y is S(O) n R 2 , OR 1 、(C1-C6)-alkyl-OR 1 , COR 1 、C(O)N(R 1) 2. a heterocyclic group, wherein the heterocyclic group may have n oxo groups,

[0097] Z is halogen, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, S(O) n R 2 ,

[0098] Z can also be (C1-C6)-alkyl, if Y is S(O) n R 2 Group,

[0099] R is (C1-C8)-alkyl,

[0100] R 1 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, wherein the (C3-C6)-cycloalkyl may be substituted by s (C1-C6)-alkyl groups,

[0101] R 2 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl,

[0102] n is 0, 1, or 2,

[0103] s is 0, 1, 2, or 3.

[0104] In the fifth embodiment of the present invention, the active herbicidal ingredient of formula (II) is preferred.

[0105]

[0106] in

[0107] A is CY,

[0108] X is halogen, (C1-C6)-alkyl, (C1-C6)-alkyl-OR 1 ,

[0109] Y is methylsulfanyl, methylsulfinyl, methylsulfonyl, ethylsulfanyl, ethylsulfinyl, ethylsulfonyl, methylaminocarbonyl, ethylaminocarbonyl, cyclopropylaminocarbonyl, isopropylaminocarbonyl, cyclopropylmethylaminocarbonyl, dimethylaminocarbonyl, methylcarbonyl, ethylcarbonyl, cyclopropylcarbonyl, methoxymethyl, ethoxymethyl, methoxy, ethoxy, cyclopropyloxy, cyclopropylmethoxy,

[0110] Z is halogen, halo-(C1-C6)-alkyl, S(O) n R2 , (C3-C6)-cycloalkyl,

[0111] Z can also be (C1-C6)-alkyl, if Y is methylsulfinyl, methylsulfanyl, methylsulfonyl, ethylsulfinyl, ethylsulfanyl, ethylsulfonyl, cyclopropylmethylsulfinyl, cyclopropylmethylsulfanyl, cyclopropylmethylsulfonyl,

[0112] R 1 is (C1-C6)-alkyl,

[0113] R 2 is (C1-C6)-alkyl,

[0114] n is 0, 1 or 2.

[0115] In the sixth embodiment of the present invention, active herbicidal ingredients of formula (II) listed in the following Table 2 are preferred, wherein A is CY.

[0116] In these tables, the abbreviations used have the following meanings:

[0117] Et = ethyl Me = methyl n-Pr = n-propyl i-Pr = isopropyl c-Pr = cyclopropyl

[0118] Table 2:

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128] In the context of the present invention, the various preferred and more preferred embodiments can be combined with each other as required. This means that herbicidal compositions containing safeners (A) one or more compounds of the general formula (I) or their agrochemically acceptable salts [component (A)] and (B) one or more herbicides [component (B)] are all included in the present invention, wherein as detailed above, any desired preferred and more preferred embodiments disclosed can be combined with each other.

[0129] At the filing date, it was surprisingly found that certain binary compositions comprising a compound (A) of the general formula (I) or an agrochemically acceptable salt thereof as safener [safener (A)] and a herbicide (B) are particularly advantageous.

[0130] These are shown in Table 3 below.

[0131] Table 3:

[0132] Safener (A) Herbicide (B) A1 B19 A1 B110 A1 B122 A1 B123 A3 B19 A3 B110 A3 B122 A5 B123 A5 B19 A5 B110 A5 B122 A5 B123

[0133] Higher-order herbicide / safener combinations consisting of the abovementioned binary combinations are likewise possible according to the invention, for example by using the same safener and blending the two binary combinations mentioned below with this particular safener.

[0134] In addition, the herbicide / safener combination of the present invention can be used together with other active ingredients such as fungicides, insecticides, acaricides, etc. and / or plant growth regulators or adjuvants such as adjuvants and formulation adjuvants in conventional additives in crop protection. Their use forms, such as formulations or tank mixes, are herbicidal products (compositions).

[0135] The present invention therefore also provides herbicide / safener combinations which comprise the customary additives in crop protection, such as adjuvants and formulation auxiliaries, and optionally further active crop protection ingredients.

[0136] The invention also provides the use and application methods of the herbicide / safener combinations according to the invention as herbicides and plant growth regulators, preferably as herbicides and plant growth regulators with a synergistically active content of the corresponding herbicide combination present.

[0137] For the active ingredients of group (B), the application rates are preferably from 20 to 400 g ai / ha, in particular from 40 to 200 g / ha and most preferably from 40 to 100 g ai / ha.

[0138] The ratio of (A):(B) based on weight is generally in the range of 1:400 to 500:1, preferably in the range of 1:100 to 100:1, more preferably in the range of 1:40 to 20:1, according to the effective application rate.

[0139] The amounts stated are application rates (gai / ha = grams of active substance per hectare) and therefore also define the ratio of the active ingredients combined in a combination formulation, premix, tank mix or sequential application.

[0140] The herbicide / safener combinations according to the invention may comprise further components, for example further active ingredients directed against harmful organisms, such as harmful plants, plant-damaging animals or plant-damaging fungi, in this case in particular active ingredients from the group consisting of the fungicides, insecticides, acaricides, nematicides, acaricides and related substance groups.

[0141] The fungicidal active compounds which can be used in conjunction with the herbicide / safener combinations according to the invention are preferably standard commercially available active ingredients, for example (similar to the herbicides, the compounds are usually referred to by their common names):

[0142] 1) Ergosterol biosynthesis inhibitors, such as cyproconazole, difenoconazole, epoxiconazole, fenhexamid, fenpropidin, fenpropimorph, fenpyrazamine, fluquinconazole, flutriafol, imazalil, imazalil sulfate, ipconazole, metconazole (metconazole), myclobutanil, paclobutrazole, prochloraz, propiconazole, prothioconazole, pyrisoxazole, spiroxamine, tebuconazole, tetraconazole, triadimenol, tridemorph, triticonazole, (1R, 2S, 5S)- 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (2R)-2-[4-(4-chlorophenoxy)- 2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, 1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, 1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H- 1,2,4-triazole, 1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, 2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-triazol-5-yl thiocyanate 2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, 2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, 2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, [(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, 2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, 2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, 2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)-phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 2-ol, 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol, 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione 3-thione, 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, 5-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane-2-yl]methyl}-1H-1,2,4-triazole, 5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane-2-yl]methyl}-1H-1,2,4-triazole cyclopropane-2-yl]methyl}-1H-1,2,4-triazole, 5-(allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane-2-yl]methyl}-1H-1,2,4-triazole, N'-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methyliminocarboxamide, N'-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methyliminocarboxamide,N'-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methyliminocarboxamide, N'-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methyliminocarboxamide, N'-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methyliminocarboxamide, N'-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methyliminocarboxamide, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methyliminocarboxamide, N'-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methyliminocarboxamide, N'-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methyliminocarboxamide, N'-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methyliminocarboxamide, N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methyliminocarboxamide, N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, mefentrifluconazole, ipfentrifluconazole.

[0143] 2) Respiratory chain inhibitors acting on complex I or II, for example benzovindiflupyr, bixafen, boscalid, carboxin, fluopyram, flutolanil, fluxapyroxad, furametpyr, isofetamid, isopyrazam (trans-diamer enantiomers 1R, 4S, 9S), isopyrazam (trans-diamer enantiomers 1S, 4R, 9R) , pyraclostrobin (trans-diameric racemate 1RS, 4SR, 9SR), pyraclostrobin (mixture of cis-diameric racemate 1RS, 4SR, 9RS and trans-diameric racemate 1RS, 4SR, 9SR), pyraclostrobin (cis-diameric enantiomers 1R, 4S, 9R), pyraclostrobin (cis-diameric enantiomers 1S, 4R, 9S), pyraclostrobin (cis-diameric racemate 1RS, 4SR, 9RS), penflufen, penthiopyrad, pydiflumetofen, bifenthiopyrad (py raziflumid), sedaxane, 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, 1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, 1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, 1-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, 2-fluoro-6-(trifluoromethyl)- 3-(Difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, 3-(Difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, 3-(Difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, 3-(Difluoromethyl)-1-methyl-N-[(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide3-(Difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, 3-(Difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide , 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, N-[(1R,4S)-9 -(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanophthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanophthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, N-[1-(2,4-dichlorophenyl)-1-methoxyprop-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole- 4-carboxamide, N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide, N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole- 4-thiocarboxamide, N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4 -carboxamide, N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide. ,

[0144] 3) Respiratory chain inhibitors acting on complex III, such as ametoctradin, amisulbrom, azoxystrobin, coumethoxystrobin, coumoxystrobin, cyazofamid, dimoxystrobin, enoxastrobin, famoxadon, fenamidon, flufenoxystrobin, fluazifop-butyl, fenoxazoline ... fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl) ethyl]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridine -2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxolan-7-yl 2-methylpropanoate, 2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide, (2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, methyl {5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate.

[0145] 4) Mitosis and cell division inhibitors, such as carbendazim, diethofencarb, ethaboxam, fluopicolide, pencycuron, thiabendazole, thiophanate-methyl, zoxamide, 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine, 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl) -6-methylpyridazine, 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine, 4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, -pyrazol-5-amine, 4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H- Pyrazol-5-amine, 4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine.

[0146] 5) Compounds with multi-site activity, such as Bordeaux mixture, captafol, captan, chlorthalonil, copper hydroxide, copper naphthenate, copper oxide, copper oxychloride, copper sulfate (2+), dithianon, dodine, folpet, mancozeb, maneb, metiram, zinc metiram, copper quinoline, oxine), propineb, sulfur and sulfur preparations including calcium polysulfide, thiram, zineb, ziram, 6-ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3',4':5,6][1,4]dithiino[2,3-c][1,2]thiazole-3-carbonitrile.

[0147] 6) Compounds that can stimulate host defenses, such as acibenzolar-S-methyl, isotianil, probenazole, and tiadinil.

[0148] 7) Inhibitors of amino acid and / or protein biosynthesis, for example cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, oxytetracycline, pyrimethanil, 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline.

[0149] 8) ATP production inhibitors, such as silthiofam.

[0150] 9) Inhibitors of cell wall synthesis, for example benthiavalicarb, dimethomorph, flumorph, iprovalicarb, mandipropamid, pyrimorph, valifenalate, (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.

[0151] 10) Inhibitors of lipid and membrane synthesis, such as propamocarb, propamocarb hydrochloride, tolclofos-methyl.

[0152] 11) Melanin biosynthesis inhibitors, for example tricyclazole, 2,2,2-trifluoroethyl-{3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.

[0153] 12) Nucleic acid synthesis inhibitors, for example: benalaxyl, benalaxyl-M (kiralaxyl), metalaxyl, metalaxyl-M (mefenoxam).

[0154] 13) Signal transduction inhibitors, for example fludioxonil, iprodione, procymidone, proquinazid, quinoxyfen, vinclozolin.

[0155] 14) Compounds that can be used as uncouplers, such as fluazinam and meptyldinocap.

[0156] 15) Other compounds, such as abscisic acid, benthiazole, bethoxazin, capsimycin, carvone, chinomethionat, cufraneb, cyflufenamid, cymoxanil, cyprosulfamide, flutianil, fosetyl-aluminium, fosetyl-calcium, fosetyl-sodium l-sodium), methyl isothiocyanate, metrafenon, mildiomycin, natamycin, nickel dimethyldithiocarbamate, nitrothal-isopropyl, oxamocarb, oxathiapiprolin, oxyfenthiin, pentachlorophenol and its salts, phosphonic acid and its salts, propamocarb ethoate carb-fosetylate), pyriofenone (chlazafenone), tebufloquin, tecloftalam, tolnifanide, 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, 1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, -3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, 2-(6-benzylpyridin-2-yl)quinazoline, 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone, 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline, 2-{(5R )-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, 2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, 2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol, 2-{2-fluoro-6-[(8-fluoro-2 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl methanesulfonate, 2-phenylphenol and its salts, 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1- 4-Amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2(1H)-one), 4-oxo-4-[(2-phenylethyl)amino]butyric acid, 5-amino-1,3,4-thiadiazole-2-thiol, 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulfonylhydrazide, 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, 9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-Benzoxazepine, but-3-yn-1-yl {6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (2Z)-3-amino-2-cyano-3-phenylacrylate ethyl, phenazine-1-carboxylic acid, 3,4,5-trihydroxybenzoic acid propyl ester, quinolin-8-ol, quinolin-8-ol sulfate (2:1), tert-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, 5-fluoro-4-imino-3-methyl-1-sulfonyl]-3,4-dihydropyrimidin-2(1H)-one.

[0157] Preferred fungicides are selected from the group consisting of benalaxyl, bitertanol, bromuconazole, captafol, carbendazim, carpropamid, cyazofamid, cyproconazole, diethofencarb, edifenphos, fenpropimorph, fentine, fluquinconazole, fosetyl, fluoroimide, folpet, iminoctadin acetate, e), iprodionem, iprovalicarb, kasugamycin, maneb, nabam, pencycuron, prochloraz, propamocarb, propineb, pyrimethanil, spiroxamine, quintozene, tebuconazole, tolylfluanid, triadimefon, triadimenol, trifloxystrobin, and zineb.

[0158] Insecticides, acaricides, nematicides, miticides and their related active ingredients are, for example (similar to herbicides and fungicides, the compounds are mentioned by their common name, if possible):

[0159] (1) an acetylcholinesterase (AChE) inhibitor, preferably a carbamate selected from the group consisting of alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathi ocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; or an organophosphate selected from acephate, azamethiphos, acetyl methionine, thiophene amine ... azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos hos), dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate,isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, methyl pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon and vamidothion.

[0160] (2) GABA-gated chloride channel blockers, preferably cyclodiene-organochlorines selected from chlordane and endosulfan; or phenylpyrazoles (fiproles) selected from ethiprole and fipronil.

[0161] (3) Sodium channel modulators, preferably pyrethroids, selected from acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin s-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, β-cyfluthrin, esters, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin, empenthrin [(EZ)-(1R) isomer], esfenvalerate, etofenproxil rox), fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin othrin) [(1R)-trans isomer], prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin and transfluthrin or DDT or methoxychlor.

[0162] (4) A competitive modulator of nicotinic acetylcholine receptor (nAChR), preferably a neonicotinoid selected from acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or nicotine; or a sulfoximine selected from sulfoxaflor; or a butenolide selected from flupyradifurone.

[0163] (5) Allosteric modulators of nicotinic acetylcholine receptors (nAChR), preferably spinosyns, selected from spinetoram and spinosad.

[0164] (6) Allosteric modulators of glutamate-gated chloride channels (GluCl), preferably avermectins / milbemycins selected from abamectin, emamectin benzoate, lepimectin and milbemectin.

[0165] (7) Juvenile hormone mimetics, preferably selected from the following juvenile hormone analogs: hydroprene, kinoprene and methoprene, or fenoxycarb or pyriproxyfen.

[0166] (8) Other non-specific (multi-site) inhibitors, preferably alkyl halides selected from methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar emetic or methyl isocyanate generators selected from diazomet and metamex.

[0167] (9) A chord organ TRPV channel modulator selected from pymetrozine and pyrifluquinazone.

[0168] (10) A mite growth inhibitor selected from the group consisting of clofentezine, hexythiazox, diflovidazin and etoxazole.

[0169] (11) An insect midgut membrane microbial disruptor selected from Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and a Bt plant protein selected from the following: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb and Cry34Ab1 / 35Ab1.

[0170] (12) Mitochondrial ATP synthase inhibitors, preferably ATP disruptors selected from diafenthiuron; or organotin compounds selected from azocyclotin, cyhexatin and fenbutatinoxide; or propargite or tetradifon.

[0171] (13) An uncoupler of oxidative phosphorylation by blocking the proton gradient, selected from chlorfenapyr, DNOC and sulfluramid.

[0172] (14) A nicotinic acetylcholine receptor channel blocker selected from the group consisting of bensultap, cartap hydrochloride, thiocyclam and thiosultap-sodium.

[0173] (15) Chitin biosynthesis inhibitors, type 0, selected from bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

[0174] (16) Chitin biosynthesis inhibitors, type 1, selected from buprofezin.

[0175] (17) Molting disruptors (especially in the case of Diptera) selected from cyromazine.

[0176] (18) An ecdysone receptor agonist selected from the group consisting of chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0177] (19) An octopamine receptor agonist selected from amitraz.

[0178] (20) A mitochondrial complex III electron transport inhibitor selected from the group consisting of hydramethylnon, acequinocyl and fluacrypyrim.

[0179] (21) Mitochondrial complex I electron transport inhibitors, preferably METI miticides, selected from fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad, or rotenone (Derris).

[0180] (22) A voltage-dependent sodium channel blocker selected from indoxacarb and metaflumizone.

[0181] (23) Acetyl-CoA carboxylase inhibitors, preferably tetronic acid and tetramic acid derivatives selected from spirodiclofen, spiromesifen and spirotetramat.

[0182] (24) Mitochondrial complex IV electron transport inhibitors, preferably phosphides selected from aluminum phosphide, calcium phosphide, phosphine and zinc phosphide; or cyanides selected from calcium cyanide, potassium cyanide and sodium cyanide.

[0183] (25) Mitochondrial complex II electron transport inhibitors, preferably β-ketonitrile derivatives selected from cyenopyrafen and cyflumetofen; or carboxanilides selected from pyflubumide.

[0184] (28) A ryanodine receptor modulator, preferably a diamide selected from chlorantraniliprole, cyantraniliprole and flubendiamide.

[0185] (29) A chord organ modulator (with an unclear target structure) selected from flonicamid.

[0186] (30) Other active ingredients are selected from the group consisting of acynonapyr, cyclosporin, afoxolaner, azadirachtin, benclothiaz, benzoximate, benzpyrimoxan, bifenazate, broflanilide, bromopropylate, chinomethionat, chloroprallethrin, cryolite, cyclaniliprole, cycloxaprid, cyhalodiamide, dicloromezotiaz, dicofol, epsilonfluthrin,metofluthrin, ε-momfluthrin, flometoquin, fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin, flufiprole, fluhexafon, fluopyram, flupyrimin, fluralaner, fluxametamide, fufenozide, guadipyr, heptafluthrin, imidaclothiz, iprodione, kappa-bifenthrin, kappa-tefluthrin, lotirana, laner, meperfluthrin, oxazosulfyl, paichongding, pyridalyl, pyrifluquinazon, pyriminostrobin, spirobudiclofen, spiropidion, tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole, tigolaner, tioxazafen, thiofluoximate, triflumezopyrim, and iodomethane; in addition, based on Bacillus firmus (Bacillus firmus) (I-1582, BioNeem, Votivo) and the following compounds: 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (known from WO 2006 / 043635) (CAS 885026-50-6), {1'-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4'-piperidinyl]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO 2003 / 106457) (CAS 637360-23-7), 2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from WO 2006 / 003494) (CAS872999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO2010052161) (CAS1225292-17-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl carbonate (known from EP 2647626) (CAS1440516-42-6), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from WO 2004 / 099160) (CAS792914-58-0), PF1364 (known from JP 2010 / 018586) (CAS 1204776-60-2), (3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoropropan-2-one (known from WO 2013 / 144213) (CAS 1461743-15-6), N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (known from WO 2010 / 051926) (CAS 1226889-14-0), 5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide (obtained from CN103232431) (CAS 1449220-44-3), 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxo-3-thietanyl)benzamide, 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxo-3-thietanyl)benzamide and 4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxo-3-thietanyl)benzamide (from WO 2013 / 050317A1) (CAS 1332628-83-7), N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide, (+)-N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide and (-)-N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide (known from WO 2013 / 162715 A2, WO 2013 / 162716 A2, US 2014 / 0213448 A1) (CAS 1477923-37-7), 5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile (known from CN 101337937 A) (CAS 1105672-77-2), 3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thiomethyl]phenyl]-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (known from CN 103109816) (CAS 1105672-77-2). A) (CAS 1232543-85-9), N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide (known from WO 2012 / 034403 A1) (CAS 1268277-22-0), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (known from WO 2011 / 085575 A1) (CAS 1233882-22-8), 4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)pyrimidine (known from CN 101337940 A) (CAS 1108184-52-6), (2E)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide and 2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide (known from CN 101715774A) (CAS 1232543-85-9), cyclopropanecarboxylic acid 3-(2,2-dichlorovinyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenyl ester (known from CN 103524422 A) (CAS 1542271-46-4), (4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylic acid methyl ester (known from CN 102391261 A) (CAS 1370358-69-2), 6-deoxy-3-O-ethyl-2,4-di-O-methyl-1-[N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1H-1,2,4-triazol-3-yl]phenyl]carbamate]-α-L-pyranose (known from US 2014 / 0275503 A1) (CAS 1181213-14-8), 8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane (CAS 1253850-56-4), (8-trans)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane (CAS 933798-27-7), (8-cis)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane (known from WO 2007040280A1, WO 2007040282 A1) (CAS 934001-66-8), N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]propionamide (known from WO 2015 / 058021 A1, WO 2015 / 058028 A1) (CAS 1477919-27-9) and N-[4-(aminothiomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (known from CN 103265527 A) (CAS 1452877-50-7), 5-(1,3-dioxane-2-yl)-4-[[4-(trifluoromethyl)phenyl]methoxy]pyrimidine (known from WO 2013 / 115391A1) (CAS 1449021-97-9), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-1,8-diazaspiro[4.5]decane-2,4-dione (known from WO 2014 / 187846 A1) (CAS1638765-58-8), ethyl 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylcarboxylate (known from WO2010 / 066780 A1, WO 2011151146 A1) (CAS 1229023-00-0), 4-[(5S)-5-(3,5-dichloro-4-fluorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[(4R)-2-ethyl-3-oxo-4-isoxazolyl]-2-methylbenzamide (known from WO 2011 / 067272, WO2013 / 050302) (CAS 1309959-62-3).

[0187] For example, insecticides which can preferably be used together with the herbicide / safener combinations according to the invention are as follows:

[0188] Acetamiprid, acralthrin, aldicarb, amitraz, acinphos-methyl, cyfluthrin, carbaryl, cypermethrin, deltamethrin, endosulfan, ethoprophos, fenamiphos, fenthion, fipronil, imidacloprid, methamidophos, methiocarb, niclosamide, sulfoxide, prothiophos, silafluthrin, thiacloprid, thiodicarb, tralomethrin, triazophos, trichlorfon, triflumuron, terbufos, fonofos, phorate, chlorpyriphos, carbofuran, tefluthrin.

[0189] The herbicide / safener combinations according to the invention are preferably suitable for controlling unwanted vegetation in economically important crop plants, such as wheat (hard and soft wheat), maize, soybeans, sugar beets, sugar cane, cotton, rice, legumes (e.g. bush beans and broad beans), flax, barley, oats, rye, triticale, potatoes and millet / sorghum.

[0190] For application, the herbicide / safener combinations according to the invention can be applied together or separately to plants (e.g. harmful plants, such as monocotyledonous or dicotyledonous weeds or unwanted crop plants), seeds (e.g. grain, seeds or vegetative propagation organs such as tubers or shoots with buds) or to the areas where the plants grow (e.g. growing areas).

[0191] The herbicide / safener combination can be applied before sowing (if appropriate, it can also be mixed into the soil), before emergence or after emergence. For harmful plants that have not yet emerged or have already emerged, the early pre-emergence method after sowing or the post-emergence method is preferred. Application can also be integrated into a weed management system with repeated application (sequential treatment).

[0192] Some representative specific examples of monocotyledonous and dicotyledonous weed populations controllable by the herbicide / safener combinations according to the invention are given below, although these enumerations are not intended to be limiting to particular species.

[0193] Among the monocotyledonous weeds, for example, Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachicaria, Bromus, Cynodon, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, The genera Imperata, Ischaemum, Heteranthera, Imperata, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum, Sphenoclea and Cyperus are annuals.

[0194] For dicotyledonous weed species, the scope of action extends to genera such as Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium , Cirsium, Convolvulus, Datura, Desmodium, Emex, Erodium, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Geranium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Sorrel Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

[0195] If the herbicide / safener combination according to the invention is applied to the soil surface before emergence, the emergence of weed seedlings is either completely prevented or the weeds grow until they reach the cotyledon stage, where they stop growing and eventually die completely after three to four weeks.

[0196] If the herbicide / safener combinations according to the invention are applied to the green parts of the plants after emergence, growth stops after the treatment and the harmful plants remain at the growth stage at the time of application or die completely after a period of time. Thus, this treatment makes it possible to eliminate the competition of weeds that are harmful to the crop plants very early and continuously. In contrast, the growth of the crop plants is only slightly affected, if at all, by the use of the herbicide / safener combinations.

[0197] The herbicide / safener combinations according to the invention are distinguished by their rapid onset and long-lasting weed control. In general, the active ingredients in the compositions according to the invention have good resistance to rainwater washout. A particular advantage is that the effective doses of components (A) and (B) used in the herbicide / safener combinations can be adjusted to such low levels that their action on the soil is optimally low. Therefore, it is not only possible to use them in sensitive crops, but groundwater contamination is also practically prevented.

[0198] Economically important crops to which the herbicide / safener combinations according to the invention are applied are, for example, dicotyledonous crop plants of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Tobacco The monocotyledonous crops include: Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or the monocotyledonous crops: Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, and Zea.

[0199] The herbicide / safener combinations according to the invention can preferably be used in transgenic crops which are resistant to growth regulators or herbicides which inhibit essential plant enzymes, such as acetolactate synthase (ALS), EPSP synthase, glutamine synthetase (GS), protoporphyrinogen IX oxidase (PPO) or hydroxyphenylpyruvate dioxygenase (HPPD), or to sulfonylureas, glyphosate, glufosinate or benzoylisoxazole herbicides and similar active ingredients.

[0200] The herbicide / safener combinations according to the invention can take the form of either a mixed formulation of components (A) and (B) with (where appropriate) other active agrochemical ingredients, additives and / or customary formulation auxiliaries, which is then diluted with water in a customary manner; or else a so-called tank mix can be prepared by diluting the individually formulated or partly individually formulated components together with water.

[0201] The herbicide / safener combinations according to the invention can be formulated in a variety of ways depending on the desired biological and / or physicochemical parameters. Examples of general formulation options are: wettable powders (WP), water-soluble powders (SP), emulsifiable concentrates (EC), water-soluble concentrates, aqueous solutions (SL), emulsions (EW) such as water-in-oil and oil-in-water emulsions, sprayable solutions or emulsions, oil-based or water-based dispersions, oil dispersions (OD), suspoemulsions, suspension concentrates (SC), oil-miscible solvents, microcapsule suspensions (CS), dusting products (DP), coatings, granules for soil application or broadcasting, granules in microgranular form (GR), sprayable granules, absorption and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules or waxes.

[0202] The present invention therefore also provides herbicidal and plant growth-regulating compositions comprising the herbicide / safener combinations according to the invention.

[0203] The individual formulation types are known in principle and are described, for example, in the following literature: Winnacker-Küchler, "Chemische Technologie" [Chemical technology], Volume 7, C. Hanser Verlag Munich, 4th edition, 1986; van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY, 1973; K. Martens, "Spray Drying" Handbook, 3rd edition, 1979, G. Goodwin Ltd. London.

[0204] Necessary formulation auxiliaries such as inert materials, surfactants, solvents and other additives are also known and described, for example, in the following literature: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd edition, Darland Books, Caldwell NJ; HvOlphen, "Introduction to Clay Colloid Chemistry"; 2nd edition, J. Wiley & Sons, NY Marsden, "Solvents Guide", 2nd edition, Interscience, NY 1963; McCutcheon's "Detergents and Emulsifiers Annual", MCPubl.Corp., Ridgewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem.Publ.Co.Inc., NY 1964, ["Interface-active Ethylene Oxide Adducts"], Wiss. Verlagsgesellschaft, Stuttgart 1976, Winnacker-Küchler, "Chemische Technologie", Volume 7, C. Hanser Verlag Munich, 4th edition, 1986.

[0205] On the basis of these preparations, combinations can also be prepared with other pesticide active substances, such as other herbicides, fungicides, insecticides or other pesticides (for example acaricides, nematicides, molluscicides, rodenticides, aphicides, avicides, larvicides, ovicides, bactericides, viricides, etc.), and with other safeners, fertilizers and / or growth regulators, for example in the form of finished preparations or tank mixes.

[0206] Wettable powders are preparations which can be uniformly dispersed in water and which contain, in addition to the active ingredient, a diluent or an inert substance, an ionic and / or nonionic surfactant (wetting agent, dispersant), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkyl sulfonates, alkylbenzene sulfonates, sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoylmethyltaurate. To prepare wettable powders, the herbicidal active ingredient is finely ground, for example, in conventional apparatus such as hammer mills, wind mills and air jet mills and simultaneously or subsequently mixed with formulation adjuvants.

[0207] Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent (e.g. butanol, cyclohexanone, dimethylformamide, xylene or a relatively high boiling aromatic compound or hydrocarbon or a mixture of organic solvents) and adding one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used are: calcium salts of alkylarylsulfonic acids, such as calcium dodecylbenzenesulfonate; or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters (e.g. sorbitan fatty acid esters, or, for example, polyoxyethylene sorbitan fatty acid esters).

[0208] Dusting products are obtained by grinding the active ingredient with finely divided solids, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

[0209] Suspension concentrates may be water-based or oil-based. They may be prepared, for example, by wet grinding using a commercially available bead mill and optionally adding surfactants such as those listed above for other types of formulations.

[0210] Emulsions, such as oil-in-water emulsions (EW), can be prepared, for example, by means of a stirrer, a colloid mill and / or a static mixer using aqueous organic solvents and optional surfactants as already listed above for other types of formulations.

[0211] Granules can be prepared by spraying the active ingredient onto an adsorptive granular inert material or by applying the active ingredient concentrate to the surface of a carrier material (e.g. sand, kaolinite or granular inert material) through a binder (e.g. polyvinyl alcohol, sodium polyacrylate or mineral oil). Suitable active ingredients can also be granulated by conventional methods for preparing fertilizer granules - if desired mixed with fertilizers.

[0212] Water-dispersible granules are usually prepared by methods such as spray drying, fluidized bed granulation, pan granulation, mixing with a high-speed mixer, and extrusion without using a solid inert material.

[0213] The agrochemical formulations usually contain 0.1% to 99% by weight, in particular 0.2% to 95% by weight, of the active ingredient of component (A) and / or (B), the following concentrations being conventional concentrations depending on the type of formulation:

[0214] In wettable powders, the active ingredient concentration is, for example, about 10% to 95% by weight; the remainder to 100% by weight is composed of conventional formulation ingredients. In the case of emulsifiable concentrates, the active ingredient concentration can be about 1% to 90% by weight, preferably 5% to 80% by weight.

[0215] Formulations in the form of dusts usually contain 5 to 20% by weight of the active ingredient; sprayable solutions contain about 0.05 to 80, preferably 2 to 50 weight percent (wt%) of the active ingredient.

[0216] In the case of granules such as dispersible granules, the content of the active ingredient depends partly on whether the active ingredient is in liquid or solid form, and the granulation aids and fillers used. Typically, the content in water-dispersible granules is 1% to 95% by weight, preferably 10% to 80% by weight.

[0217] Furthermore, the active ingredient preparations optionally contain corresponding customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, colorants and carriers, antifoams, evaporation inhibitors and pH- or viscosity-adjusters.

[0218] For application, commercial formulations are, if appropriate, diluted in the customary manner, for example with water in the case of wettable powders, emulsifiable concentrates, dispersibles and water-dispersible granules. Dust-type formulations, granules for soil application or broadcasting and sprayable solutions are usually applied without further dilution with other inert substances.

[0219] The herbicide / safener combinations according to the invention can be applied to plants, plant parts, plant seeds or the area where they are planted (soil), preferably to green plants and plant parts, and optionally additionally to the soil.

[0220] One possible way of use is the joint application of the herbicide / safener combinations in the form of tank mixes, wherein optimally formulated concentrates of the individual active ingredients and water are mixed in a tank and the resulting spray liquor is then applied.

[0221] The combined formulation of the herbicide / safener combination according to the invention has the advantage that it is easier to apply, since the amounts of the components have been adjusted to the correct ratio. In addition, the adjuvants in the formulation can be optimally adjusted to one another, whereas tank mixes of different formulations may result in unwanted combinations of adjuvants.

[0222] A. General Formulation Examples

[0223] a) A dusting product is obtained by mixing 10 parts by weight of component (A) or (B), or a mixture of components (A) + (B) (and optionally other components) and / or their salts with 90 parts by weight of talc as an inert substance and grinding in a beater mill.

[0224] b) Wettable powders which are readily dispersible in water are obtained by mixing 25 parts by weight of the components / component mixture, 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleylmethyltaurate as wetting agent and dispersant, and grinding the mixture in a pin-disc mill.

[0225] c) a dispersion concentrate readily dispersible in water by mixing 20 parts by weight of the component / component mixture with 6 parts by weight of an alkylphenol polyglycol ether ( X 207), 3 parts by weight of isotridecanol polyethylene glycol ether (8EO) and 71 parts by weight of paraffin-based mineral oil (boiling range is, for example, about 255 to 277° C.), and the mixture is ground in a friction ball mill to a fineness of less than 5 μm.

[0226] d) An emulsifiable concentrate is obtained by mixing 15 parts by weight of the component / component mixture, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier.

[0227] e) Water dispersible granules are obtained by mixing:

[0228] 75 parts by weight of the components of the mixture,

[0229] 10 parts by weight of calcium lignin sulfonate,

[0230] 5 parts by weight of sodium lauryl sulfate,

[0231] 3 parts by weight of polyvinyl alcohol, and

[0232] 7 parts by weight of kaolin,

[0233] The mixture was ground in a pin-disk mill and the powder was granulated in a fluidized bed by spraying water as granulating liquid.

[0234] f) Water-dispersible granules can also be obtained by homogenizing and pre-comminuting the following on a colloid mill:

[0235] 25 parts by weight of a component mixture of components,

[0236] 5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate,

[0237] 2 parts by weight of sodium oleoyl methyl taurate,

[0238] 1 part by weight of polyvinyl alcohol,

[0239] 17 parts by weight of calcium carbonate, and

[0240] 50 parts by weight of water.

[0241] The mixture is subsequently ground in a ball mill and the resulting suspension is atomized through a single-phase nozzle in a spray tower and dried.

[0242] Biological Examples

[0243] The effect of the selective herbicide / safener combinations according to the invention is illustrated using the example of damage reduction on summer wheat (TRZAS):

[0244] Seeds of the crop plants to be treated were placed in soil in plastic pots (about 8 cm in diameter), covered with soil and then grown in a greenhouse under good germination and growth conditions. The test plants were treated at the early leaf stage (BBCH 12).

[0245] For this purpose, the herbicides and safeners used were formulated as wettable powders (WP), mixed in each case according to the specified dosage, and the aqueous suspensions with added wetting agent (Mero, 1.5 l / ha) were sprayed onto the above-ground parts of the plants at an application rate of 300 l / ha of water.

[0246] The respective herbicide doses are selected so as to cause visually noticeable damage (minimum 30%, maximum 70%) to the crop plants of a control group (not treated with safener) included in the same test at the time of assessment compared with untreated crop plants.

[0247] After application, the plants were cultivated in a greenhouse under good growth conditions. 21 days after application, the damage of the herbicide was visually assessed. The degree of damage was visually assessed in the range of 0-100% by comparison with untreated control plants, and 2 replicates were averaged for each treatment. Example:

[0248] 0% = No significant effect compared to untreated plants

[0249] 20% = The treated plant population is 20% damaged compared to the untreated control population (e.g., growth height, leaf damage, etc.)

[0250] 100% = total damage / death of treated plants.

[0251] The test showed that the damage caused by the respective herbicides (component (B)) to summer wheat crop plants (TRZAS; variety: Triso) (=herbicide damage without safener, see Table 4 below) was significantly reduced by adding the safener (component (A)). The application rate of the respective safener was 80 g / ha.

[0252] Table 4:

[0253]

Claims

1. A herbicide / safener combination comprising one or more compounds effective as safeners [component (A)] and one or more herbicidally active compounds [component (B)], wherein component (A) represents one or more compounds of the general formula (I) or an agrochemically acceptable salt thereof. And among them (R 1 ) n -phenyl represents a group from Q-1.1 to Q-1.53 and (R 2 ) m - Phenyl represents a group of Q-2.1 to Q-2.

53. R 3 represents hydrogen, and R 4 is 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-ylmethyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl, methylpropionate-3-yl, ethylpropionate-3-yl, methylacetate-2-yl, ethylacetate-2-yl, methylpivalate-2-yl, ethylpivalate-2-yl, ester-3-yl, methyl-2-methylpropionate-3-yl, methyl-2,2-dimethylpropionate-3-yl, ethyl-2-methylpropionate-3-yl, methyl-2-propionate-2-yl, ethyl-2-propionate-2-yl, methyl acetate-2-yl, ethyl acetate-2-yl, methyl-1-methylcyclopropanecarboxylate-2-yl, ethyl-1-methylcyclopropanecarboxylate-2-yl, 2-(dimethylamino)ethyl, oxetan-3-yl, (3-methyloxetan-3-yl)methyl, 2,2,2-trifluoroethyl, 2,2-difluoro ethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl, cyclopropylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl, allyl, propargyl (prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl, 3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl, 2-methylprop-2-en-1-yl, but-2-ene -1-yl, but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methyl-but-2-en-1-yl, 3-methyl-but-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, hept-2-yl, isobutyl, 1,3-dioxol-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazol-4-methyl, and (B) one or more herbicides [component (B)] selected from the active herbicidal ingredients having the general formula (II), in A is N or CY, X is nitro, halogen, cyano, formyl, thiocyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C3-C6)-alkynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR 1 、COOR 1 、OCOOR 1 NR 1 COOR 1 、C(O)N(R 1 )2. NR 1 C(O)N(R 1 )2、OC(O)N(R 1 )2、C(O)NR 1 OR 1 , OR 1 ,OCOR 1 、OSO2R 2 、S(O) n R 2 、SO2OR 1 SO2N(R 1 )2. NR 1 S02R 2 NR 1 COR 1 、(C1-C6)-alkyl-S(O) n R 2 、(C1-C6)-alkyl-OR 1 、(C1-C6)-alkyl-OCOR 1 、(C1-C6)-alkyl-OSO2R 2 、(C1-C6)-alkyl-CO2R 1 、(C1-C6)-alkyl-SO2OR 1 、(C1-C6)-alkyl-CON(R 1 )2、(C1-C6)-alkyl-SO2N(R 1 )2, (C1-C6)-alkyl-NR 1 COR 1 、(C1-C6)-alkyl-NR 1 S02R 2 NR 1 R 2 、P(O)(OR 5 )2、CH2P(O)(OR 5 )2, (C1-C6)-alkylheteroaryl, (C1-C6)-alkylheterocyclyl, wherein the latter two radicals are each substituted by s radicals selected from halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, S(O) n -(C1-C6)-alkyl, (C1-C6)-alkoxy and halo-(C1-C6)-alkoxy groups, and wherein the heterocyclyl has n oxo groups, Y is hydrogen, nitro, halogen, cyano, thiocyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR 1 、COOR 1 、OCOOR 1 NR 1 COOR 1 、C(O)N(R 1 )2. NR 1 C(O)N(R 1 )2、OC(O)N(R 1 2. CO(NOR 1 )R 1 NR 1 S02R 2 NR 1 COR 1 , OR 1 、OSO2R 2 、S(O) n R 2 、SO2OR 1 SO2N(R 1 )2、(C1-C6)-alkyl-S(O) n R 2 、(C1-C6)-alkyl-OR 1 、(C1-C6)-alkyl-OCOR 1 、(C1-C6)-alkyl-OSO2R 2 、(C1-C6)-alkyl-CO2R 1 、(C1-C6)-alkyl-CN、(C1-C6)-alkyl-SO2OR 1 、(C1-C6)-alkyl-CON(R 1 )2、(C1-C6)-alkyl-SO2N(R 1 )2, (C1-C6)-alkyl-NR 1 COR 1 、(C1-C6)-alkyl-NR 1 S02R 2 、N(R 1 )2、P(O)(OR 5 )2、CH2P(O)(OR 5 )2, (C1-C6)-alkylphenyl, (C1-C6)-alkylheteroaryl, (C1-C6)-alkylheterocyclyl, phenyl, heteroaryl or heterocyclyl, wherein the last six radicals are each substituted by s selected from halogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, S(O) n -(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, (C1-C6)-alkoxy-(C1-C4)-alkyl and cyanomethyl groups, and the heterocyclic group has n oxo groups, Z is halogen, cyano, thiocyano, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C2-C6)-alkynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR 1 、COOR 1 、OCOOR 1 NR 1 COOR 1 、C(O)N(R 1 )2. NR 1 C(O)N(R 1 )2、OC(O)N(R 1 )2、C(O)NR 1 OR 1 、OSO2R 2 、S(O) n R 2 、SO2OR 1 SO2N(R 1 )2. NR 1 S02R 2 NR 1 COR 1 、(C1-C6)-alkyl-S(O) n R 2 、(C1-C6)-alkyl-OR 1 、(C1-C6)-alkyl-OCOR 1 、(C1-C6)-alkyl-OSO2R 2 、(C1-C6)-alkyl-CO2R 1 、(C1-C6)-alkyl-SO2OR 1 、(C1-C6)-alkyl-CON(R 1 )2、(C1-C6)-alkyl-SO2N(R 1 )2, (C1-C6)-alkyl-NR 1 COR 1 、(C1-C6)-alkyl-NR 1 S02R 2 、N(R 1 )2、P(O)(OR 5 )2, heteroaryl, heterocyclic or phenyl, wherein the last three groups are each substituted by s selected from halogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, S(O) n -(C1-C6)-alkyl, (C1-C6)-alkoxy or halo-(C1-C6)-alkoxy, and the heterocyclyl has n oxo groups, or Z can also be hydrogen, (C1-C6)-alkyl or (C1-C6)-alkoxy. If Y is S(O) n R 2 Group, R is (C1-C8)-alkyl, halo-(C1-C8)-alkyl, (C2-C8)-alkenyl, halo-(C2-C8)-alkenyl, (C2-C8)-alkynyl, halo-(C2-C8)-alkynyl, wherein the above six groups are each substituted by s groups selected from hydroxyl, nitro, cyano, SiR 5 3. PO(OR 5 )2. S(O) n -(C1-C6)-alkyl, S(O) n -(C1-C6)-haloalkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, N(R 3 2. COR 3 、COOR 3 ,OCOR 3 NR 3 COR 3 NR 3 S02R 4 , O(C1-C2)-alkyl-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl, heteroaryl, heterocyclyl, phenyl, wherein the last three groups are each substituted by s groups selected from methyl, ethyl, methoxy, trifluoromethyl, cyano and halogen, and wherein the heterocyclyl has n oxo groups, or R is (C3-C7)-cycloalkyl, heteroaryl, heterocyclyl or phenyl, each of which is substituted by s selected from halogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, S(O) n -(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy and (C1-C6)-alkoxy-(C1-C4)-alkyl radicals, wherein the heterocyclyl radical has n oxo radicals, R 1 is hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, (C3-C6)-halocycloalkyl, (C1-C6)-alkyl-(C3-C6)- ... 6)-alkyl-O-(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl, heteroaryl, (C1-C6)-alkylheteroaryl, heterocyclyl, (C1-C6)-alkylheterocyclyl, (C1-C6)-alkyl-O-heteroaryl, (C1-C6)-alkyl-O-heterocyclyl, (C1-C6)-alkyl-NR 3 -heteroaryl or (C1-C6)-alkyl-NR 3 -heterocyclic group, wherein the last 21 groups are each selected from cyano, nitro, thiocyano, OR 3 、S(O) n R 4 、N(R 3 )2. NR 3 OR 3 , COR 3 ,OCOR 3 SCOR 4 NR 3 COR 3 NR 3 S02R 4 、CO2R 3 、COSR 4 、CON(R 3 )2 and (C1-C4)-alkoxy-(C2-C6)-alkoxycarbonyl groups, and wherein the heterocyclic group has n oxo groups, R 2 is (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, (C3-C6)-halocycloalkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl, heteroaryl, (C1-C6)-alkylheteroaryl, heterocyclyl, (C1-C6)-alkylheterocyclyl, (C1-C6)-alkyl-O-heteroaryl, (C1-C6)-alkyl-O-heterocyclyl, (C1-C6)-alkyl-NR 3 -heteroaryl or (C1-C6)-alkyl-NR 3 -heterocyclic group, wherein the latter 21 groups are each selected from cyano, halogen, nitro, thiocyano, OR 3 、S(O) n R 4 、N(R 3 )2. NR 3 OR 3 , COR 3 ,OCOR 3 SCOR 4 NR 3 COR 3 NR 3 S02R 4 、CO2R 3 、COSR 4 、CON(R 3 )2 and (C1-C4)-alkoxy-(C2-C6)-alkoxycarbonyl groups, and wherein the heterocyclic group has n oxo groups, R 3 is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl or phenyl, R 4 is (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl or phenyl, R 5 is (C1-C4)-alkyl, n is 0, 1, or 2, s is 0, 1, 2, or 3.

2. The herbicide / safener combination according to claim 1, comprising as component (A) one or more safeners selected from the group consisting of compounds A1, A2, A3, A4, A5 and A6: A1{[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid methyl ester A2{[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid A3{[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid methyl ester A4{[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid A5{[1-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid methyl ester A6{[1-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid 3. The safener / herbicide combination according to claim 1 or 2, comprising as component (B) one or more active ingredients of formula (II) in A is N or CY, X is halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C3-C6)-alkynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR 1 、COOR 1 、OCOOR 1 NR 1 COOR 1 、C(O)N(R 1 )2、OC(O)N(R 1 )2、C(O)NR 1 OR 1 , OR 1 ,OCOR 1 、OSO2R 2 、S(O) n R 2 NR 1 S02R 2 NR 1 COR 1 、(C1-C6)-alkyl-S(O) n R 2 、(C1-C6)-alkyl-OR 1 、(C1-C6)-alkyl-OCOR 1 、(C1-C6)-alkyl-OSO2R 2 、(C1-C6)-alkyl-CO2R 1 、(C1-C6)-alkyl-SO2OR 1 、(C1-C6)-alkyl-CON(R 1 )2、(C1-C6)-alkyl-SO2N(R 1 )2, (C1-C6)-alkyl-NR 1 COR 1 、(C1-C6)-alkyl-NR 1 S02R 2 , Y is hydrogen, halogen, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR 1 、COOR 1 、OCOOR 1 NR 1 COOR 1 、C(O)N(R 1 )2. NR 1 C(O)N(R 1 )2、OC(O)N(R 1 2. CO(NOR 1 )R 1 NR 1 S02R 2 NR 1 COR 1 , OR 1 、OSO2R 2 、S(O) n R 2 、SO2OR 1 SO2N(R 1 )2、(C1-C6)-alkyl-S(O) n R 2 、(C1-C6)-alkyl-OR 1 、(C1-C6)-alkyl-OCOR 1 、(C1-C6)-alkyl-OSO2R 2 、(C1-C6)-alkyl-CO2R 1 、(C1-C6)-alkyl-CN、(C1-C6)-alkyl-SO2OR 1 、(C1-C6)-alkyl-CON(R 1 )2、(C1-C6)-alkyl-SO2N(R 1 )2, (C1-C6)-alkyl-NR 1 COR 1 、(C1-C6)-alkyl-NR 1 S02R 2 、N(R 1 )2. a heterocyclic group, wherein the heterocyclic group may have n oxo groups, Z is halogen, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C2-C6)-alkynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR 1 、COOR 1 、OCOOR 1 NR 1 COOR 1 、C(O)N(R 1 )2. NR 1 C(O)N(R 1 )2、OC(O)N(R 1 )2、C(O)NR 1 OR 1 、OSO2R 2 、S(O) n R 2 、SO2OR 1 SO2N(R 1 )2. NR 1 S02R 2 NR 1 COR 1 、(C1-C6)-alkyl-S(O) n R 2 、(C1-C6)-alkyl-OR 1 、(C1-C6)-alkyl-OCOR 1 、(C1-C6)-alkyl-OSO2R 2 、(C1-C6)-alkyl-CO2R 1 、(C1-C6)-alkyl-SO2OR 1 、(C1-C6)-alkyl-CON(R 1 )2、(C1-C6)-alkyl-SO2N(R 1 )2, (C1-C6)-alkyl-NR 1 COR 1 、(C1-C6)-alkyl-NR 1 S02R 2 、N(R 1 )2, Z can also be hydrogen, (C1-C6)-alkyl or (C1-C6)-alkoxy. If Y is S(O) n R 2 Group, R is (C1-C8)-alkyl, halo-(C1-C8)-alkyl, (C2-C8)-alkenyl, halo-(C2-C8)-alkenyl, (C2-C8)-alkynyl, halo-(C2-C8)-alkynyl, (C3-C6)-cycloalkyl, phenyl, R 1 is hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, (C3-C6)-halocycloalkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl, heteroaryl, (C1-C6)-alkylheteroaryl, heterocyclyl, where the (C3-C6)-cycloalkyl can be substituted by s (C1-C6)-alkyl groups. R 2 is (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, (C3-C6)-halocycloalkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, phenyl, n is 0, 1, or 2, s is 0, 1, 2, or 3.

4. The safener / herbicide combination according to any one of claims 1 to 3, comprising as component (B) one or more active ingredients of formula (II) in A is CY, X is halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C3-C6)-alkynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR 1 、COOR 1 、OCOOR 1 NR 1 COOR 1 、C(O)N(R 1 )2、OC(O)N(R 1 )2、C(O)NR 1 OR 1 , OR 1 ,OCOR 1 、OSO2R 2 、S(O) n R 2 NR 1 S02R 2 NR 1 COR 1 、(C1-C6)-alkyl-S(O) n R 2 、(C1-C6)-alkyl-OR 1 、(C1-C6)-alkyl-OCOR 1 、(C1-C6)-alkyl-OSO2R 2 、(C1-C6)-alkyl-CO2R 1 、(C1-C6)-alkyl-SO2OR 1 、(C1-C6)-alkyl-CON(R 1 )2、(C1-C6)-alkyl-SO2N(R 1 )2, (C1-C6)-alkyl-NR 1 COR 1 、(C1-C6)-alkyl-NR 1 S02R 2 , Y is hydrogen, halogen, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR 1 、COOR 1 、OCOOR 1 NR 1 COOR 1 、C(O)N(R 1 )2. NR 1 C(O)N(R 1 )2、OC(O)N(R 1 2. CO(NOR 1 )R 1 NR 1 S02R 2 NR 1 COR 1 , OR 1 、OSO2R 2 、S(O) n R 2 、SO2OR 1 SO2N(R 1 )2、(C1-C6)-alkyl-S(O) n R 2 、(C1-C6)-alkyl-OR 1 、(C1-C6)-alkyl-OCOR 1 、(C1-C6)-alkyl-OSO2R 2 、(C1-C6)-alkyl-CO2R 1 、(C1-C6)-alkyl-CN、(C1-C6)-alkyl-SO2OR 1 、(C1-C6)-alkyl-CON(R 1 )2、(C1-C6)-alkyl-SO2N(R 1 )2, (C1-C6)-alkyl-NR 1 COR 1 、(C1-C6)-alkyl-NR 1 S02R 2 、N(R 1 )2. a heterocyclic group, wherein the heterocyclic group may have n oxo groups, Z is halogen, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C2-C6)-alkynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, COR 1 、COOR 1 、OCOOR 1 NR 1 COOR 1 、C(O)N(R 1 )2. NR 1 C(O)N(R 1 )2、OC(O)N(R 1 )2、C(O)NR 1 OR 1 、OSO2R 2 、S(O) n R 2 、SO2OR 1 SO2N(R 1 )2. NR 1 S02R 2 NR 1 COR 1 、(C1-C6)-alkyl-S(O) n R 2 、(C1-C6)-alkyl-OR 1 、(C1-C6)-alkyl-OCOR 1 、(C1-C6)-alkyl-OSO2R 2 、(C1-C6)-alkyl-CO2R 1 、(C1-C6)-alkyl-SO2OR 1 、(C1-C6)-alkyl-CON(R 1 )2、(C1-C6)-alkyl-SO2N(R 1 )2, (C1-C6)-alkyl-NR 1 COR 1 、(C1-C6)-alkyl-NR 1 S02R 2 、N(R 1 )2, Z can also be hydrogen, (C1-C6)-alkyl or (C1-C6)-alkoxy. If Y is S(O) n R 2 Group, R is (C1-C8)-alkyl, halo-(C1-C8)-alkyl, (C2-C8)-alkenyl, halo-(C2-C8)-alkenyl, (C2-C8)-alkynyl, halo-(C2-C8)-alkynyl, (C3-C6)-cycloalkyl, phenyl, R 1 is hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, (C3-C6)-halocycloalkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl, heteroaryl, (C1-C6)-alkylheteroaryl, heterocyclyl, wherein the (C3-C6)-cycloalkyl may be substituted by s (C1-C6)-alkyl radicals, R 2 is (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, (C3-C6)-halocycloalkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, phenyl, n is 0, 1, or 2, s is 0, 1, 2, or 3.

5. The safener / herbicide combination according to any one of claims 1 to 4, comprising as component (B) one or more active ingredients of formula (II) in A is CY, X is halogen, (C1-C6)-alkyl, (C1-C6)-alkyl-OR 1 , Y is S(O) n R 2 , OR 1 、(C1-C6)-alkyl-OR 1 , COR 1 、C(O)N(R 1 )2. a heterocyclic group, wherein the heterocyclic group may have n oxo groups, Z is halogen, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, S(O) n R 2 , Z can also be (C1-C6)-alkyl, if Y is S(O) n R 2 Group, R is (C1-C8)-alkyl, R 1 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, wherein the (C3-C6)-cycloalkyl may be substituted by s (C1-C6)-alkyl groups, R 2 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, n is 0, 1, or 2, s is 0, 1, 2, or 3.

6. The safener / herbicide combination according to any one of claims 1 to 5, comprising as component (B) one or more active ingredients of formula (II) in A is CY, X is halogen, (C1-C6)-alkyl, (C1-C6)-alkyl-OR 1 , Y is methylsulfanyl, methylsulfinyl, methylsulfonyl, ethylsulfanyl, ethylsulfinyl, ethylsulfonyl, methylaminocarbonyl, ethylaminocarbonyl, cyclopropylaminocarbonyl, isopropylaminocarbonyl, cyclopropylmethylaminocarbonyl, dimethylaminocarbonyl, methylcarbonyl, ethylcarbonyl, cyclopropylcarbonyl, methoxymethyl, ethoxymethyl, methoxy, ethoxy, cyclopropyloxy, cyclopropylmethoxy, Z is halogen, halo-(C1-C6)-alkyl, R 2 (O) n S, (C3-C6)-cycloalkyl, Z can also be (C1-C6)-alkyl, if Y is methylsulfinyl, methylsulfanyl, methylsulfonyl, ethylsulfinyl, ethylsulfanyl, ethylsulfonyl, cyclopropylmethylsulfinyl, cyclopropylmethylsulfanyl, cyclopropylmethylsulfonyl, R 1 is (C1-C6)-alkyl, R 2 is (C1-C6)-alkyl, n is 0, 1 or 2.

7. The safener / herbicide combination according to any one of claims 1 to 6, comprising as component (A) one or more active ingredients selected from the group consisting of compounds A1, A3 and A5.

8. The safener / herbicide combination according to claim 1, further comprising one or more additives customary in crop protection.

9. A method for protecting crop plants from the phytotoxic side effects of a herbicide (B), characterized in that Before, during or simultaneously with the application of the herbicide (B), an effective amount of a safener (A) is applied to the plants, plant parts, plant seeds or planting areas, wherein the combination of herbicide (B) and safener (A) is as defined in any one of claims 1 to 7.

10. The method according to claim 9, characterized in that The crop plants are cereal plants.

11. The method according to claim 9 or 10, characterized in that The herbicide (B) is applied at an application rate of 40 to 200 g / ha of active substance and the weight ratio of safener (A) / herbicide (B) is 1:400 to 500:

1.

12. Use of the safener / herbicide combination according to any one of claims 1 to 8 for controlling harmful plants or for regulating plant growth.

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