Herbicide / safener combinations based on safeners from the class of substituted [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acids and their salts

Abstract

The present invention relates to combinations comprising one or more safener-active components (A) and one or more herbicidally active compounds (component (B)), wherein component (A) represents one or more compounds of general formula (I) or their agrochemically compatible salts, and component (B) represents one or more herbicides. The application further relates to methods and uses of the herbicide / safener combinations of the invention for the control or growth regulation of harmful plants. [Formula 1] TIFF2025532189000041.tif64159

Description

[Technical Field]

[0001] The present invention relates to the technical field of crop protection compositions which can be used in cultivation, for seed preparation or in plant crops to combat unwanted plant growth and which comprise 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 general formula (I) and / or their agronomically compatible salts (= component (A)). [Background technology]

[0002] The effectiveness of known herbicides against harmful plants is high, but generally depends on the application rate, the form of the respective preparation, the spectrum of harmful plants, the harmful plants to be controlled in each case, the climatic and soil conditions, etc., and in particular on the suitability of the crop plants.

[0003] One way to improve the application profile of herbicide can be to combine safener with one or more active herbicidal components, which contributes to desired additional properties.However, when two or more active components are applied in combination, it is not uncommon that there are physical and biological incompatibility phenomena, such as the lack of stability in co-formulation, the decomposition of active component and / or the antagonism of active component; or, when two or more herbicides are applied in combination, the safener has limited scope of action, and when two or more herbicides are applied in combination, it only protects crop plants against one herbicide, not against all components.

[0004] Safeners (also called antidotes) of different chemical structures have been known for about 70 years. They are also known to differ significantly in terms of their protective function, meaning their use is limited to the selected herbicide and / or crop plant being protected. A further requirement is that the selected herbicide / safener combination does not adversely affect the herbicidal effect based on the harmful plant being controlled.

[0005] [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acid derivatives and salts thereof are known from PCT application WO2021 / 105101 having application number PCT / EP2020 / 083167. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] International Publication No. 2021 / 105101 Brochure Summary of the Invention [Problem to be solved by the invention]

[0007] It has now been found that compounds from the class of substituted [(1,5-diphenyl-1H-1,2,4-triazol-3-yl)oxy]acetic acids can indeed be used effectively for the protection of different crop plants when applying one or more herbicides [component (B)] of different chemical structure.

[0008] The herbicide / safener combinations of the present invention interact in a particularly favorable manner, for example, when they are used to control undesirable plant growth in crop plants such as wheat (hard and soft wheat), corn, soybean, sugar beet, sugarcane, cotton, rice, beans (e.g., bush beans and fava beans), flax, barley, oats, rye, triticale, potato, and millet / sorghum. [Means for solving the problem]

[0009] The present invention therefore relates to a combination comprising one or more components (A) which are active as safeners and one or more herbicidally active compounds as component (B), wherein (A) is a compound represented by the general formula (I): [ka] [During the ceremony, (R 1 ) n -phenyl represents a Q-1.1 to Q-1.53 ​​group; [ka] TIFF2025532189000004.tif131164 and (R 2 ) m -phenyl represents a Q-2.1 to Q-2.53 group; [ka] TIFF2025532189000006.tif142158R 3 represents hydrogen, and R 4is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, n-pentyl, phenyl, benzyl, CH2(4-Cl-Ph), CH2(4-F-Ph), CH2(4-OMe-Ph), 2-methoxyethyl, tetrahydrofuran-2-ylmethyl, tetrahydrofuran-3-ylmethyl, tetrahydropyran-2-ylmethyl, tetrahydropyran-3-ylmethyl, tetrahydropyran-4-ylmethyl , methyl propionate-3-yl, ethyl propionate-3-yl, methyl acetate-2-yl, ethyl acetate-2-yl, methyl pivalate-2-yl, ethyl pivalate-3-yl, methyl-2-methylpropanoate-3-yl, methyl-2,2-dimethylpropanoate-3-yl, ethyl-2-methylpropanoate-3-yl, methyl-2-propanoate-2-yl, ethyl-2-propanoate methylacetate-2-yl, methylacetate-2-yl, ethylacetate-2-yl, methyl-1-methylcyclopropanecarboxylate-2-yl, ethyl-1-methylcyclopropanecarboxylate-2-yl, 2-(dimethylamino)ethyl, oxetan-3-yl, (3-methyloxetan-3-yl)methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl, cyclopropylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl, (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl, allyl, propargyl(prop-2-yn-1-yl), 2-chloroprop-2-en-1-yl, 3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, heptan-2-yl, isobutyl, 1,3-dioxolan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl, or a pesticidally acceptable salt thereof, and (B) one or more herbicides [component (B)] are represented by the general formula (II) [ka] [During the ceremony, 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 , N.R. 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 , OSO2R2 , S(O) n R 2 , SO2OR 1 , SO2N(R 1 )2, NR 1 SO2R 2 , N.R. 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 SO2R 2 , N.R. 1 R 2 , P(O)(OR 5 )2, CH2P(O)(OR 5 )2, (C1-C6)-alkylheteroaryl, (C1-C6)-alkylheterocyclyl, where the latter two radicals are respectively halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, S(O) n is substituted by s radicals from the group consisting of -(C1-C6)-alkyl, (C1-C6)-alkoxy and halo-(C1-C6)-alkoxy, and heterocyclyl carries 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 , N.R. 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 , N.R. 1 SO2R 2 , N.R. 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 SO2R 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, where the latter six radicals are each halogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, S(O) n is substituted by s radicals from the group consisting of -(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, (C1-C6)-alkoxy-(C1-C4)-alkyl and cyanomethyl, and heterocyclyl carries 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 , N.R. 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 SO2R 2 , N.R. 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 SO2R 2 , N(R 1 )2, P(O)(OR 5 )2, heteroaryl, heterocyclyl or phenyl, where the latter three radicals are each halogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, S(O) n is substituted by s radicals from the group consisting of -(C1-C6)-alkyl, (C1-C6)-alkoxy or halo-(C1-C6)-alkoxy, and the heterocyclyl has n oxo groups, or Z also determines whether Y is S(O) n R 2 if it is a radical, it may be hydrogen, (C1-C6)-alkyl or (C1-C6)-alkoxy, R is (C1-C8)-alkyl, halo-(C1-C8)-alkyl, (C2-C8)-alkenyl, halo-(C2-C8)-alkenyl, (C2-C8)-alkynyl, halo-(C2-C8)-alkynyl, where these six aforementioned radicals are respectively hydroxy, 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 , N.R.3 COR 3 , N.R. 3 SO2R 4 , substituted with s radicals from the group consisting of O(C1-C2)-alkyl-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl, heteroaryl, heterocyclyl, phenyl, where each of the last three radicals is substituted with s radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl, cyano and halogen, and heterocyclyl carries n oxo groups, or R is (C3-C7)-cycloalkyl, heteroaryl, heterocyclyl or phenyl, which is respectively halogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, S(O) n substituted by s radicals from the group consisting of -(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy and (C1-C6)-alkoxy-(C1-C4)-alkyl, wherein the heterocyclyl carries n oxo groups, 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)-cycloalkyl, (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-heterocyclyl, where each of the last 21 radicals is cyano, nitro, thiocyano, OR 3 , S(O) n R 4 , N(R 3 )2, NR 3 OR 3 , C.O.R. 3 ,OCOR 3 , SCOR 4 , N.R. 3 COR 3 , N.R. 3 SO2R 4、 CO2R 3 , COSR 4 , CON(R 3 )2 and (C1-C4)-alkoxy-(C2-C6)-alkoxycarbonyl, and the heterocyclyl has n oxo groups, R 2 represents (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 -heterocyclyl, where each of the last 21 radicals is cyano, halogen, nitro, thiocyano, OR 3 , S(O) n R 4 , N(R 3 )2, NR 3 OR 3 , C.O.R. 3 ,OCOR 3 , SCOR4 , N.R. 3 COR 3 , N.R. 3 SO2R 4 , CO2R 3 , COSR 4 , CON(R 3 )2 and (C1-C4)-alkoxy-(C2-C6)-alkoxycarbonyl, and the heterocyclyl 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. The present invention provides an active herbicidal ingredient which is from the group of active herbicidal ingredients having the formula:

[0010] 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.

[0011] Only neutral compounds are referred to below and therefore all existing forms listed are encompassed, except where a particular form of the active ingredient is relevant in a particular situation (e.g., examples in the table below regarding biological effectiveness).

[0012] The herbicide / safener combinations of the invention can comprise further components, for example other active ingredients for combating harmful organisms such as harmful plants, plant-damaging animals or plant-damaging fungi, in particular herbicides other than those mentioned under B, fungicides, insecticides, acaricides, nematicides and miticides and related substances, or other types of active ingredients for crop protection (e.g. resistance inducers), crop plant protection active ingredients (safeners, antidotes other than component (A)), plant growth regulators, and / or additives and / or formulation adjuvants customary in crop protection. The components here can be formulated together (ready-to-use formulations) and used as such, or they can be formulated separately and used together, for example in a tank mix or sequential application.

[0013] The individual safeners of general formula (I) present as component (A) are also referred to hereinafter as compound (A), active ingredient (A), component (A) or safener (A). Similarly, the individual active herbicidal ingredients present as component (B) are also referred to hereinafter as compound (B), active ingredient (B), component (B), herbicide (B) or compounds of formula (II).

[0014] An advantageous property of the inventive combination of safener (A) and herbicide (B) has been found to be that the safener (A) and herbicide (B) are compatible with each other, meaning that they can be used together without serious chemical incompatibility between the safener (A) and / or the herbicide (B) resulting in the destruction of the safener (A) or the herbicide (B).

[0015] This favorable compatibility also extends to the biological properties of the active ingredients when used in combination: for example, in the case of the control of harmful plants with the herbicide / safener combinations of the invention, antagonistic effects are generally not observed.

[0016] In formula (I) for the safener (A) compounds and formula (II) for the herbicide (B) compounds and all formulae below, the following definitions are applicable: Depending on the nature of the substituents and the method of their attachment, the compounds of formula (I) or (II) may exist as stereoisomers. For example, when one or more asymmetrically substituted carbon atoms and / or sulfoxides are present, enantiomers and diastereomers may exist. Stereoisomers can be obtained from the mixtures obtained in the preparation by conventional separation methods, for example, chromatographic separation methods. Similarly, stereoisomers can be selectively prepared by using stereoselective reactions using optically active starting materials and / or auxiliaries.

[0017] The present invention also relates to all stereoisomers and mixtures thereof which are encompassed by formula (I) or (II) but not specifically defined, although for the sake of brevity, in the following reference will always be made to compounds of formula (I) or (II), even if this means not only the pure compounds but also, where appropriate, mixtures of isomeric compounds in different proportions.

[0018] According to the nature of the substituents defined above, the compounds of formula (I) or (II) have acidic properties and can form salts, and if appropriate, inner salts or adducts, with inorganic or organic bases or metal ions. When the compounds of formula (I) or (II) have hydroxyl, carboxyl, or other groups that impart acidic properties, these compounds can be reacted with bases to obtain salts. Suitable bases include, for example, hydroxides, carbonates, and hydrogencarbonates of alkali metals and alkaline earth metals, especially those of sodium, potassium, magnesium, and calcium, as well as ammonia, primary, secondary, and tertiary amines with (C1-C4)-alkyl groups, mono-, di-, and trialkanolamines of (C1-C4)-alkanols, choline and chlorocholine, and organic amines such as trialkylamines, morpholine, piperidine, and pyridine. These salts are salts in which the acidic hydrogen is present with an agriculturally suitable cation, such as a metal salt, in particular an alkali metal salt or alkaline earth metal salt, in particular sodium and potassium salt, or an ammonium salt, an organic amine or a quaternary ammonium salt, for example a salt of the formula [NRR'R''R'''] +where R-R''' are each independently an organic group, particularly alkyl, aryl, aralkyl, or alkylaryl, substituted with a cation of the formula: Alkyl sulfonium and alkyl sulfoxonium salts, such as (C1-C4)-trialkylsulfonium and (C1-C4)-trialkylsulfoxonium salts, are also useful.

[0019] The compounds of formula (I) or (II) can form salts by addition of a suitable inorganic or organic acid, such as a mineral acid, for example HCl, HBr, HSO, HPO, or HNO, or an organic acid, for example a carboxylic acid, for example formic acid, acetic acid, propionic acid, oxalic acid, lactic acid, or salicylic acid, or a sulfonic acid, for example p-toluenesulfonic acid, to a basic group, for example amino, alkylamino, dialkylamino, piperidino, morpholino, or pyridino. These salts then contain the conjugate base of the acid as the anion.

[0020] Suitable substituents, such as sulfonic or carboxylic acids, that exist in deprotonated form can form internal salts with groups such as amino groups and can be protonated for that moiety.

[0021] If a group is polysubstituted by a radical, this means that this group is substituted by one or more groups, which may be the same or different, from those mentioned.

[0022] Below are given preferred, particularly preferred and very particularly preferred definitions of the individual safeners (A) and herbicides (B), respectively.

[0023] Where a compound can form, via hydrogen shift, tautomers whose structures would not be formally covered by general formula (A), these tautomers are nevertheless encompassed by the definition of the compounds of the present invention of general formula (A), unless a specific tautomer is being considered. For example, many carbonyl compounds can exist in both the keto and enol forms, and both forms are encompassed by the definition of the compounds of general formula (A).

[0024] Depending on the nature of the substituents and the manner in which they are attached, compounds of general formula (I) may exist as stereoisomers. All possible stereoisomers, such as enantiomers, diastereomers, Z and E isomers, defined by their specific three-dimensional configuration, are encompassed by general formula (I). For example, when one or more alkenyl groups are present, diastereomers (Z and E isomers) may result. For example, when one or more asymmetric carbon atoms are present, enantiomers and diastereomers may result. Stereoisomers can be obtained from the mixtures obtained in the preparation by conventional separation methods. Chromatographic separation can be performed on an analytical scale to determine the enantiomeric or diastereomeric excess, or on a preparative scale to generate test samples for biological testing. Similarly, stereoisomers can be selectively prepared by using stereoselective reactions using optically active starting materials and / or auxiliaries. Therefore, the present invention also relates to all stereoisomers encompassed by general formula (I) but not depicted in their specific stereoisomeric form, and mixtures thereof.

[0025] If the compounds are obtained as solids, purification can also be carried out by recrystallization or digestion. If the individual compounds of general formula (I) are not obtained in a satisfactory manner by the routes described below, they can be prepared by derivatization of other compounds of general formula (I).

[0026] Suitable isolation, purification and methods for separating stereoisomers of compounds of general formula (I) are generally known to those skilled in the art from similar cases, for example by physical methods such as crystallization, chromatography, in particular column chromatography and HPLC (High Pressure Liquid Chromatography), distillation (optionally under reduced pressure), extraction and other methods, and any remaining mixtures can usually be separated, for example, by chromatographic separation on chiral solid phases. Suitable for preparative or industrial scale are methods such as crystallization, for example the recrystallization of diastereomeric salts which can be obtained from diastereomeric mixtures using optically active acids and, where appropriate, using optically active bases, provided that an acidic group is present.

[0027] In a first embodiment of the invention, the herbicide / safener combination of the invention, as well as at least one component (B) as defined above, preferably comprises a compound of general formula (I) as set out in Table 1 [component A] or an agronomically compatible salt thereof [safener (A)].

[0028] Table 1: IUPAC names and structural formulas of preferred compounds of formula (I) (safeners (A)) [Table 1] TIFF2025532189000009.tif117170The compound of formula (I) is known from the international application with application number PCT / EP2020 / 083167 (WO2021 / 105101) and can be prepared by the methods described therein.

[0029] The application rates of herbicides (B) are in the range of 20 to 400 g of active substance per hectare (hereinafter g ai / ha), preferably 40 to 200 g ai / ha, in particular 40 to 100 g ai / ha, and the application rates of safeners (A) are in the range of 1 to 1000 g ai / ha, preferably 10 to 500 g ai / ha, in particular 20 to 200 g ai / ha of active substance.

[0030] Particularly preferred safeners (A) in accordance with the present invention are the compounds numbered A1, A3 and A5 according to Table 1 above.

[0031] Suitable combination partners (B) [= component (B) or herbicide (B)] are in principle all active ingredients from subgroups (B1) to (B11), the herbicidal active ingredients being named mostly by common name (English notation) in accordance with the reference "The Pesticide Manual" 14th Edition, British Crop Protection Council 2006, abbreviated as "PM" or by their chemical names according to standard nomenclature (IUPAC or Chemical Abstracts).

[0032] However, some herbicides (B) have surprisingly been found to be particularly good combination partners for the safeners (A). Preferred and more preferred herbicides (B) are listed below as further embodiments of the present invention.

[0033] In a second embodiment of the present invention, a compound of formula (II) [ka] [During the ceremony, 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 , N.R. 1 COOR 1 , C(O)N(R 1 )2, OC(O)N(R 1 )2, C(O)NR 1 OR 1 , OR1 ,OCOR 1 , OSO2R 2 , S(O) n R 2 , N.R. 1 SO2R 2 , N.R. 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 SO2R 2 and 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 , N.R. 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 , N.R. 1 SO2R 2 , N.R. 1 COR1 , 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 SO2R 2 , N(R 1 )2, heterocyclyl, wherein the heterocyclyl 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 , N.R. 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 R2 , SO2OR 1 , SO2N(R 1 )2, NR 1 SO2R 2 , N.R. 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 SO2R 2 , N(R 1 )2, Z is Y is S(O) n R 2 if it is a radical, it may be hydrogen, (C1-C6)-alkyl or (C1-C6)-alkoxy, 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 1is hydrogen, (C-C)-alkyl, (C-C)-haloalkyl, (C-C)-alkenyl, (C-C)-haloalkenyl, (C-C)-alkynyl, (C-C)-haloalkynyl, (C-C)-cycloalkyl, (C-C)-cycloalkenyl, (C-C)-halocycloalkyl, (C-C)-alkyl-O—(C-C)-alkyl, (C-C)-cycloalkyl-(C-C)-alkyl, phenyl, phenyl-(C-C)-alkyl, heteroaryl, (C-C)-alkylheteroaryl, heterocyclyl, where (C-C)-cycloalkyl is optionally substituted by s (C-C)-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. The active herbicide ingredients are preferably:

[0034] In a third embodiment of the present invention, a compound of formula (II) [ka] [During the ceremony, 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, COR1 , COOR 1 , OCOOR 1 , N.R. 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 , N.R. 1 SO2R 2 , N.R. 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 SO2R 2 and 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 , N.R. 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 , N.R. 1 SO2R 2 , N.R. 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 SO2R 2 , N(R 1 )2, heterocyclyl, wherein the heterocyclyl 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 , N.R. 1 COOR1 , 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 SO2R 2 , N.R. 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 SO2R 2 , N(R 1 )2, Z is Y is S(O) n R 2 group, it may be hydrogen, (C1-C6)-alkyl or (C1-C6)-alkoxy, 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 1is hydrogen, (C-C)-alkyl, (C-C)-haloalkyl, (C-C)-alkenyl, (C-C)-haloalkenyl, (C-C)-alkynyl, (C-C)-haloalkynyl, (C-C)-cycloalkyl, (C-C)-cycloalkenyl, (C-C)-halocycloalkyl, (C-C)-alkyl-O—(C-C)-alkyl, (C-C)-cycloalkyl-(C-C)-alkyl, phenyl, phenyl-(C-C)-alkyl, heteroaryl, (C-C)-alkylheteroaryl, heterocyclyl, where (C-C)-cycloalkyl is optionally substituted by s (C-C)-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. The active herbicidal ingredients are preferably:

[0035] In a fourth embodiment of the present invention, a compound of formula (II) [ka] [During the ceremony, A is CY, X is halogen, (C1-C6)-alkyl, (C1-C6)-alkyl-OR 1 and Y is S(O) n R 2 , OR 1 , (C1-C6)-alkyl-OR 1 , C.O.R. 1 , C(O)N(R 1)2, heterocyclyl, wherein the heterocyclyl may have n oxo groups; Z is halogen, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, S(O) n R 2 and Z is Y is S(O) n R 2 If it is a radical, it may be (C1-C6)-alkyl, R is (C1-C8)-alkyl, R 1 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, where (C3-C6)-cycloalkyl is optionally substituted by s (C1-C6)-alkyl radicals, 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. The active herbicide ingredients are preferably:

[0036] In a fifth embodiment of the present invention, a compound of formula (II) [ka] [During the ceremony, A is CY, X is halogen, (C1-C6)-alkyl, (C1-C6)-alkyl-OR 1 and 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 may be (C1-C6)-alkyl if Y is a methylsulfinyl, methylsulfanyl, methylsulfonyl, ethylsulfinyl, ethylsulfanyl, ethylsulfonyl, cyclopropylmethylsulfinyl, cyclopropylmethylsulfanyl, cyclopropylmethylsulfonyl radical, R 1 is (C1-C6)-alkyl, R 2 is (C1-C6)-alkyl, n is 0, 1 or 2. The active herbicide ingredients are preferably:

[0037] In a sixth embodiment of the present invention, the active herbicidal ingredients of formula (II) listed in Table 2 below, wherein A is CY, are preferred.

[0038] In these tables, the abbreviations used have the following meanings: [Table 2] Table 2: [ka] [Table 3] TIFF2025532189000017.tif253162TIFF2025532189000018.tif252161TIFF2025532189000019.tif252161TIFF2025532189000020.tif252160TIFF2025532189000021.tif254162TIFF2025532189000022.tif245161In relation to the present invention, the individual preferred and more preferred embodiments can be combined with one another as desired. This means that the present invention encompasses herbicidal compositions comprising a safener (A) one or more compounds of general formula (I) or a pesticidally acceptable salt thereof [component (A)] and (B) one or more herbicides [component (B)], and any of the preferred and more preferred embodiments disclosed herein can be combined with each other as described above.

[0039] Certain binary combinations comprising a compound (A) of general formula (I), or a pesticidal salt thereof, acting as a safener [safener (A)], and a herbicide (B) have been found to be particularly advantageous in a surprising manner at the filing date.

[0040] These are shown in Table 3 below.

[0041] Table 3: [Table 4] Higher order herbicide / safener combinations consisting of the aforementioned binary combinations are also possible in accordance with the present invention, for example by using the same safener and blending two binary combinations as described below in relation to that particular safener.

[0042] Furthermore, the herbicide / safener combinations of the invention can be used together with other active ingredients, such as fungicides, insecticides, acaricides, etc., and / or auxiliaries from the group of plant growth regulators or additives customarily used in crop protection, such as adjuvants and formulation auxiliaries. Their use forms, such as formulations or tank mixes, are herbicide products (compositions).

[0043] The invention therefore also provides herbicide / safener combinations which comprise additives customary in crop protection, such as adjuvants and formulation auxiliaries, and optionally further active crop protection ingredients.

[0044] The present invention also provides the use or application method of the herbicide / safener combinations of the present invention as herbicides and plant growth regulators, preferably as herbicides and plant growth regulators with synergistically active contents of each herbicide combination present.

[0045] For the active ingredients from group (B), the application rates are preferably in the range from 20 to 400 g ai / ha, in particular in the range from 40 to 200 g / ha, most preferably in the range from 40 to 100 g / ha.

[0046] The ratio of (A):(B) by 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, depending on the effective application rate.

[0047] The stated amount is the application rate (g ai / ha = grams of active substance per hectare) and therefore also defines the ratio in co-formulations, premixes, tank mixes or sequential applications of combined active ingredients.

[0048] The herbicide / safener combinations of the invention can comprise further ingredients, for example other active ingredients against harmful organisms such as harmful plants, plant-damaging animals or plant-damaging fungi, in this case especially active ingredients from the group of fungicides, insecticides, acaricides, nematicides, miticides and related substances.

[0049] The fungicidal active compounds that can be used in conjunction with the herbicide / safener combinations of the present invention are preferably standard commercially available active ingredients (e.g., like herbicides, the compounds are generally named by their common name): 1) Inhibitors of ergosterol biosynthesis, such as cyproconazole, difenoconazole, epoxiconazole, fenhexamid, fenpropidin, fenpropimorph, fenpyrazamine, fluquinconazole, flutriafol, imazalil, imazalil sulfate, ipconazole, metconazole, myclobutanil, paclobutrazol, 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)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl 2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, 2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-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-trimethylheptan-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-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, 2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-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-trimethylheptan-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-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, 2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2 ,4-triazole-3-thione, 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-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-(tri 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)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)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)oxiran-2-yl]methyl}-2,4-dihydrochloride 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-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)oxiran-2-yl]methyl}-1H-1,2,4-triazole, 5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, 5-(allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2- (2,4-difluorophenyl)oxiran-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-methylimidoformamide, N'-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, N'-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl ]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, N'-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, N'-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, N'-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N -methylimidoformamide, N'-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, N'-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide, N'-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, N'-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, N'-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide, N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide, N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, N'- {5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, mefentrifluconazole, ipfentrifluconazole.

[0050] 2) respiratory chain inhibitors acting on complex I or II, such as benzovindiflupyr, bixafen, boscalid, carboxin, fluopyram, flutolanil, fluxapyroxad, furametpyr, isofetamide, isopyrazam (antiepimeric enantiomers 1R, 4S, 9S), isopyrazam (antiepimeric enantiomers 1S, 4R, 9R), isopyrazam (antiepimeric racemic 1RS, 4SR, 9SR), isopyrazam (mixture of syn-epimeric racemic 1RS, 4SR, 9RS and anti-epimeric racemic 1RS, 4SR, 9SR), i Sopyrazam (syn-epimer enantiomer 1S, 4S, 9R), isopyrazam (syn-epimer enantiomer 1S, 4R, 9S), isopyrazam (syn-epimer racemic 1RS, 4SR, 9RS), penflufen, penthiopyrad, pydiflumetofen, pyraziflumide, 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 H-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)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide, 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)-N-(7-fluoro-1,1,3-trimethyl-2,3-Dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide, 3-(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- Pyrazole-4-carboxamide, N-(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-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, N-[1-(2,4-dichlorophenyl)-1-methoxypropan-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) N-[5-chloro-2-(trifluoromethyl)benzyl]-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 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-isopropyl-5-methylbenzyl)-1-methyl -1H-pyrazole-4-carbothioamide, 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)-5-fluoro-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-cyclo N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-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.

[0051] 3) Respiratory chain inhibitors acting on complex III, such as ametoctrazine, amisulbrom, azoxystrobin, cumoxystrobin, cumoxystrobin, cyazofamid, dimoxystrobin, enoxastrobin, famoxadone, fenamidone, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin Vinyl, (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]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-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-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.

[0052] 4) Mitotic and cytotoxic agents, 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, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl- 1H-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) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-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.

[0053] 5) Compounds with multi-site activity, such as Bordeaux mixture, captafol, captan, chlorothalonil, copper hydroxide, copper naphthenate, copper oxide, copper oxychloride, copper(2+) sulfate, dithianon, dodine, folpet, mancozeb, maneb, metiram, zinc metiram, copper oxine, propineb, sulfur and sulfur preparations, such as 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.

[0054] 6) Compounds capable of inducing host defense, e.g., acibenzolar-S-methyl, isotianil, probenazole, tiadinil.

[0055] 7) Amino acid and / or protein biosynthesis inhibitors, such as cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, oxytetracycline, pyrimethanil, 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline.

[0056] 8) ATP production inhibitors, such as silthiofam.

[0057] 9) Cell wall synthesis inhibitors, such as 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.

[0058] 10) Lipid and membrane synthesis inhibitors, such as propamocarb, propamocarb hydrochloride, tolclofos methyl.

[0059] 11) Melanin biosynthesis inhibitors, such as tricyclazole, 2,2,2-trifluoroethyl-{3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.

[0060] 12) Nucleic acid synthesis inhibitors, for example, benalaxyl, benalaxyl-M (chiralaxyl), metalaxyl, metalaxyl-M (mefenoxam).

[0061] 13) Signal transduction inhibitors, such as fludioxonil, iprodione, procymidone, proquinazide, quinoxyfen, and vinclozolin.

[0062] 14) Compounds that can act as decouplers, such as fluazinam, meptyldinocap.

[0063] 15) Further compounds, such as abscisic acid, benthazole, bethoxadin, capsimycin, carvone, chinomethionate, kufuraneb, cyflufenamid, cymoxanil, cyprosulfamide, fluthianil, fosetyl-aluminum, fosetyl-calcium, fosetyl-sodium, methyl isothiocyanate, metrafenone, mildiomycin, natamycin, nickel dimethyldithiocarbamate, nitrotarisopropyl, oxamocarb, oxathiapiproline, oxyfuran. Enthiin, pentachlorophenol and its salts, phosphonic acid and its salts, propamocarb-fosetylate, pyriophenone (chlazafenone), tebufloquine, 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, 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)-tetrone, 2-[3,5-bis(difluoromethyl)-1H-pyrazole-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- 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-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol, Fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol, 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}phenylmethanesulfonate, 2-phenylphenol and its salts, 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, 4-amino-5-fluoropyrimidin-2-ol (tautomer: 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-sulfonohydrazide, 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, ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, phenazine-1-carboxylic acid, propyl 3,4,5-trihydroxybenzoate, 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.

[0064] Preferred fungicides are selected from the group consisting of benalaxyl, bitertanol, bromuconazole, captafol, carbendazim, carpropamid, cyazofamid, cyproconazole, diethofencarb, edifenphos, fenpropimorph, fentin, fluquinconazole, fosetyl, fluorimide, folpet, iminoctadine, iprodionem, iprovalicarb, kasugamycin, maneb, nabam, pencycuron, prochloraz, propamocarb, propineb, pyrimethanil, spiroxamine, quintozene, tebuconazole, tolylfluanid, triadimefon, triadimenol, trifloxystrobin, and zineb.

[0065] Insecticidal, acaricidal, nematicidal, miticidal and related active ingredients include, for example (as well as herbicides and fungicides, which are as follows: compounds are referred to by their common names, where possible): (1) Acetylcholinesterase (AChE) inhibitors, preferably carbamates selected from alanylcarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, and xylylcarb; or acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, and dimethoate. , dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famfur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyaphos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton methyl, parathion methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon and vamidothion.

[0066] (2) GABA-gated chloride channel blockers, preferably cyclodiene-organochlorines selected from chlordane and endosulfan, or phenylpyrazoles (fiprole) selected from ethiloprol and fipronil.

[0067] (3) Sodium channel modulators, preferably acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin, empenthrin [ (EZ)-(1R) isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, taufluvalinate, halfenprox, imiprothrin, kadesrin, momfluorothrin, permethrin, fenothrin [(1R)-trans isomer], prallethrin, pyrethrins (pyrethram), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R) isomer], tralomethrin, and transfluthrin, or DDT or methoxychlor.

[0068] (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, preferably neonicotinoids selected from acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam, or nicotine, or sulfoximines selected from sulfoxaflor, or butenolides selected from flupyradifurone.

[0069] (5) Allosteric modulators of nicotinic acetylcholine receptors (nAChR), preferably spinosyns selected from spinetoram and spinosad.

[0070] (6) Allosteric modulators of glutamate-gated chloride channels (GluCl), preferably avermectins / milbemycins selected from abamectin, emamectin benzoate, lepimectin and milbemectin.

[0071] (7) Juvenile hormones, preferably juvenile hormone analogs selected from hydroprene, kinoprene and methoprene, or fenoxycarb or pyriproxyfen.

[0072] (8) Other non-specific (multi-site) inhibitors, preferably alkyl halides selected from methyl bromide and other alkyl halides; or methyl isocyanate generating agents selected from chloropicrin or sulfuryl fluoride or borax or tartar emetic or diazomet and metam.

[0073] (9) A chordotonin TRPV channel modulator selected from pymetrozine and pyrifluquinazone.

[0074] (10) A mite growth inhibitor selected from clofentezine, hexythiazox, diflobidazine, and etoxazole.

[0075] (11) A microbial disruptor of insect midgut membranes selected from Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, and Bacillus thuringiensis subspecies tenebrionis, and a Bt plant protein selected from Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, VIP3A, mCry3A, Cry3Ab, Cry3Bb, and Cry34Ab1 / 35Ab1.

[0076] (12) Inhibitors of mitochondrial ATP synthase, preferably ATP disrupting agents selected from diafenthiuron, or organotin compounds selected from azocyclotin, cyhexatin and fenbutatin oxide, or propargite or tetradifon.

[0077] (13) Uncouplers of oxidative phosphorylation via disruption of the proton gradient selected from chlorfenapyr, DNOC, and sulfluramide.

[0078] (14) A nicotinic acetylcholine receptor channel blocker selected from bensultap, cartap hydrochloride, thiocyclam, and thiosultap sodium.

[0079] (15) Type 0 inhibitors of chitin biosynthesis selected from bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, novaflumuron, teflubenzuron, and triflumuron.

[0080] (16) Type 1 inhibitors of chitin biosynthesis selected from buprofezin.

[0081] (17) Molting inhibitors selected from cyromazine (especially in Diptera).

[0082] (18) An ecdysone receptor agonist selected from chromafenozide, halofenozide, methoxyfenozide, and tebufenozide.

[0083] (19) An octopamine receptor agonist selected from amitraz.

[0084] (20) A mitochondrial complex III electron transport inhibitor selected from hydramethylnon, acequinocyl, and fluacrypyrim.

[0085] (21) Mitochondrial complex I electron transport inhibitors, preferably METI acaricides selected from fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad, or rotenone (Derris).

[0086] (22) A voltage-gated sodium channel blocker selected from indoxacarb and metaflumizone.

[0087] (23) Inhibitors of acetyl-CoA carboxylase, preferably tetronic and tetramic acid derivatives selected from spirodiclofen, spiromesifen and spirotetramat.

[0088] (24) Mitochondrial complex IV electron transport inhibitors, preferably phosphines selected from aluminum phosphide, calcium phosphide, phosphine phosphide, and zinc phosphide, or cyanides selected from calcium cyanide, potassium cyanide, and sodium cyanide.

[0089] (25) Mitochondrial complex II electron transport inhibitors, preferably beta-ketonitrile derivatives selected from cyenopyrafen and cyflumetofen, or carboxanilides selected from piflubumid.

[0090] (28) Ryanodine receptor modulators, preferably diamides selected from chlorantraniliprole, cyantraniliprole, and flubendiamide.

[0091] (29) A chordotoniloconazole modulator (with an undefined target structure) selected from flonicamid.

[0092] (30) Acinonapyr, afidopiropen, afoxolaner, azadirachtin, benclotiaz, benzoximate, benzpyrimoxane, bifenazate, brofuranilide, bromopropylate, quinomethionate, chlorprallethrin, cryolite, cyclaniliprole, cycloxapride, cyhalodiamide, dichloromezothiaz, dicofol, epsilon metofluthrin, epsilon monfluthrin, flometoquin, fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin, flufiprole, fluhexafon, fluopyram, flupirimine, fluralaner, fluxamethamide, fufe further active ingredients selected from fufenozide, guadipyr, heptafluthrin, imidaclothiz, iprodione, kappabifenthrin, kappatefluthrin, lotilaner, meperfluthrin, oxazosulfil, paichongding, pyridalyl, pyrifluquinazone, pyriminostrobin, spirobudiclofen, spiropidione, tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole, tigoranel, thioxazafen, thiofluoximate, triflumezopyrim and methyl iodide; firmus)-based preparations (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'-piperidin]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO2003 / 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 WO2006 / 003494) (CAS 872999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO2010052161) (CAS 1225292-17-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylethyl carboxylate (known from EP2647626) (CAS-1440516-42-6), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from WO2004 / 099160) (CAS 792914-58-0), PF1364 (known from JP2010 / 018586) (CAS Reg. No. 1204776-60-2), (3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoropropan-2-one (known from WO2013 / 144213) (CAS 1461743-15-6), N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (known from WO2010 / 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 (known from CN103232431) (CAS 1449220-44-3), 4-[5-(3,5-dichlorophenyl)-4,5-Dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide, 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxido-3-thietanyl)benzamide and 4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide (known from WO2013 / 050317A1) (CAS 1332628-83-7), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide, (+)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide and (-)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide (known from WO2013 / 162715A2, WO2013 / 162716A2, US2014 / 0213448A1) (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 CN101337937A) (CAS 1105672-77-2), 3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thioxomethyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (Liudaibenjiaxuanan, known from CN103109816A) (CAS 1232543-85-9); N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide (known from WO2012 / 034403A1) (CAS 1268277-22-0), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (known from WO2011 / 085575A1) (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 CN101337940A) (CAS 1108184-52-6); (2E)- and 2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide (known from CN101715774A) (CAS 1232543-85-9; cyclopropanecarboxylic acid 3-(2,2-dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenyl ester (known from CN103524422A) (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 CN102391261A) (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-mannopyranose (known from US2014 / 0275503A1) (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-anti)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane (CAS 933798-27-7), (8-syn)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane (known from WO2007040280A1 and WO2007040282A1) (CAS 934001-66-8), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]propanamide (known from WO2015 / 058021A1 and WO2015 / 058028A1) (CAS 1477919-27-9) and N-[4-(aminothioxomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (known from CN103265527A) (CAS 1452877-50-7), 5-(1,3-dioxan-2-yl)-4-[[4-(trifluoromethyl)phenyl]methoxy]pyrimidine (known from WO2013 / 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 WO2014 / 187846A1) (CAS 1638765-58-8), 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 / 066780A1, WO2011151146A1) (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-isoxazolidinyl]-2-methylbenzamide (known from WO2011 / 067272, WO2013 / 050302) (CAS 1309959-62-3).

[0093] Insecticides which can be preferably used together with the herbicide / safener combination of the present invention are, for example: Acetamiprid, acrinathrin, aldicarb, amitraz, azinphos-methyl, cyfluthrin, carbaryl, cypermethrin, deltamethrin, endosulfan, ethoprophos, fenamiphos, fenthion, fipronil, imidacloprid, methamidophos, methiocarb, niclosamide, oxydemeton-methyl, prothiofos, silafluofen, thiacloprid, thiodicarb, tralomethrin, triazophos, trichlorfon, triflumuron, terbufos, fonofos, phorate, chlorpyrifos, carbofuran, tefluthrin.

[0094] The herbicide / safener combinations of the present invention are preferentially suitable for the control of undesirable plant growth in economically important crop plants such as wheat (hard and soft wheat), corn, soybean, sugar beet, sugarcane, cotton, rice, legumes (e.g., kidney beans and broad beans), flax, barley, oats, rye, triticale, potato, and millet / sorghum.

[0095] For application, the herbicide / safener combinations of the present invention can be deployed together or separately to plants (e.g., harmful plants such as monocotyledonous or dicotyledonous weeds or undesirable crop plants), seeds (e.g., vegetative propagation organs such as grains, seeds, or tubers or parts of shoots bearing shoots), or areas where plants grow (e.g., growing areas).

[0096] Herbicide / safener combinations can be deployed pre-sowing (also by incorporation into the soil, if appropriate), pre-emergence or post-emergence. Early post-sowing, pre-emergence or post-emergence methods are preferred against harmful plants that have not yet emerged or have already emerged. Application can also be integrated into a split-application (sequential) weed management system.

[0097] Some representative examples of monocotyledonous and dicotyledonous weed groups that can be controlled by the herbicide / safener combinations of the present invention are given below, but the listing is not intended to be limited to any particular species.

[0098] Among the monocotyledonous weed species, for example, Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachicaria, Bromus, Cynodon, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Femurgrass, Fimbristylis, This group of annual plants includes the genera Imperata, Ischaemum, Heteranthera, Imperata, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum, Sphenoclea, and Cyperus.

[0099] For dicotyledonous weed species, the spectrum of action is e.g. Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, A. Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erodium, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Geranium, Hibiscus, Satsuma Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi,It is widespread in species such as Trifolium, Urtica, Veronica, Viola, and Xanthium.

[0100] When the herbicide / safener combinations of the present invention are applied to the soil surface pre-emergence, the emergence of weed seedlings is completely prevented or the weeds grow until they reach the cotyledon stage, after which they cease growth and ultimately die completely after a period of 3-4 weeks.

[0101] When the herbicide / safener combinations of the present invention are applied to the green parts of plants after emergence, growth stops after treatment and harmful plants either remain in the growth stage at the time of application or die completely after a certain period of time, which very quickly and persistently eliminates competition by weeds that are harmful to crop plants. In contrast, crop plant development is only slightly, if at all, affected by the use of the herbicide / safener combination.

[0102] The herbicide / safener combination of the present invention is notable for its rapid onset and long-lasting herbicidal action. Generally, the rain resistance of the active ingredients in the combination of the present invention is preferable. A particular advantage is that the effective dosage of components (A) and (B) used in the herbicide / safener combination can be adjusted to a low level so that their soil activity is optimally low. This not only enables its use in sensitive crops, but also substantially prevents groundwater contamination.

[0103] Economically important crops for application of the herbicide / safener combinations of the present invention include, for example, the peanut (Arachis) family, the chard (Beta) family, the brassica (Brassica) family, the cucumber (Cucumis) family, the pumpkin (Cucurbita) family, the sunflower (Helianthus) family, the carrot (Daucus) family, the Glycine (Glycine) family, the cotton (Gossypium) family, the sweet potato (Ipomoea) family, the sow (Lactuca) family, the flax (Linum) family, the tomato (Lycopersicon) family, the tobacco (Nicotiana) family, the common bean (Phaseolus vulgaris) family, the common pea ... olus, Pisum, Solanum, Vicia; or monocotyledonous crops from the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, and Zea.

[0104] The herbicide / safener combinations of the present invention can be used in transgenic crops that are preferably tolerant to growth regulators or to herbicides that inhibit essential plant enzymes, such as acetolactate synthase (ALS), EPSP synthase, glutamine synthase (GS), protoporphyrinogen IX oxidase (PPO), or hydroxyphenylpyruvate dioxygenase (HPPD), or tolerant to herbicides from sulfonylureas, glyphosate, glufosinate, or benzoylisoxazole, and similar active ingredients.

[0105] The herbicide / safener combinations of the invention can take the form either of a mixed formulation of components (A) and (B), and optionally together with further active pesticide ingredients, additives and / or conventional formulation adjuvants, which are then diluted with water and applied in the conventional manner, or can be prepared as a so-called tank mix by diluting the separately formulated or partly separately formulated components together with water.

[0106] The herbicide / safener combinations of the present invention can be formulated in various ways according to the required biological and / or physicochemical parameters. Examples of common formulation options are wettable powders (dusts) (WP), water-soluble dusts (SP), emulsifiable concentrates (EC), water-soluble concentrates, aqueous solutions (SL), emulsifiable concentrates (EW), such as aqueous and oil emulsions, sprayable solutions or emulsions, oil- or water-based dispersions, oil-dispersible wettable powders (OD), suspoemulsions, suspension concentrates (SC), oil-mix solutions, capsule suspensions (CS), dusts (DP), dressings, granules for soil application or broadcast, granules in the form of microgranules, spray granules, absorbing and adsorbing granules (GR), water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules or wax.

[0107] Thus, the present invention also provides herbicidal and plant growth regulating compositions comprising the herbicide / safener combinations of the present invention.

[0108] The individual formulation types are known in principle and are described, for example, in Winnacker-Kuechler, "Chemische Technologie" [Chemical Technology], Vol. 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.

[0109] Necessary formulation aids, such as inert materials, surfactants, solvents and further additives, are likewise known and are described, for example, in Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell NJ; HvOlphen, "Introduction to Clay Colloid Chemistry", 2nd ed., J. Wiley & Sons, NY; Marsden, "Solvents Guide", 2nd ed., Interscience, NY 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; Schoenfeldt, "Grenzflaechenaktive Aethylenoxidaddukte" ["Interface-active ethylene oxide Adducts”], Wiss.Verlagsgesellschaft, Stuttgart 1976, Winnacker-Kuechler, “Chemische Technologie”, Vol. 7, C.Hanser Verlag Munich, 4th Edition, 1986.

[0110] Based on these formulations, it is also possible to produce combinations with other pesticidal active substances, such as other herbicides, fungicides, insecticides, insecticides or other pesticides (e.g. acaricides, nematicides, molluscicides, rodenticides, aphidicides, larvicides, ovicides, bactericides, virucides, etc.), and also with further safeners, fertilizers and / or growth regulators, for example in the form of finished formulations or as tank mixes.

[0111] Wettable powders (powders) are preparations that can be uniformly dispersed in water and, in addition to the active ingredient, may also contain, excluding diluents or inert substances, ionic and / or nonionic surfactants (wetting agents, dispersants), such as polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid, sodium dibutylnaphthalenesulfonate, or sodium oleoylmethyl taurate. To produce wettable powders (powders), the active herbicide ingredient is pulverized using conventional equipment, such as a hammer mill, blower mill, or air jet mill, and simultaneously or subsequently mixed with formulation auxiliaries.

[0112] Emulsifiable concentrate is prepared by dissolving active ingredients in organic solvent, such as butanol, cyclohexanone, dimethylformamide, xylene, or aromatic compounds or hydrocarbons with relatively high boiling points, or a mixture of organic solvents, and adding one or more ionic and / or nonionic surfactants (emulsifiers).The emulsifiers that can be used are alkylarylsulfonic acid calcium salts, 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, such as sorbitan fatty acid esters, or for example, polyoxyethylene sorbitan fatty acid esters.

[0113] Dusts 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.

[0114] Suspensions may be water-based or oil-based. They may be prepared, for example, by wet milling in a commercially available bead mill and optionally by the addition of surfactants, for example, as already listed above for other formulation types.

[0115] Emulsifying agents, such as aqueous emulsions (EW), can be prepared, for example, by using a stirrer, a colloid mill and / or a static mixer, using, for example, aqueous organic solvents and optionally surfactants, such as those already listed above for other formulation types.

[0116] Granules can be prepared by spraying the active ingredient onto an adsorbent granular inert material, or by applying an active ingredient concentrate to the surface of a carrier material such as sand, kaolinite, or a granular inert material, using an adhesive such as polyvinyl alcohol, sodium polyacrylate, or mineral oil. Suitable active ingredients can also be granulated, if desired as a mixture with a fertilizer, by conventional methods for preparing fertilizer granules.

[0117] Water dispersible granules are generally manufactured by processes such as spray drying, fluidized bed granulation, pan granulation, mixing in a high speed mixer, and extrusion without solid inert materials.

[0118] The pesticide preparations generally contain 0.1 to 99% by weight, in particular 0.2 to 95% by weight, of the active ingredients of components (A) and / or (B); depending on the type of formulation, the following concentrations are customary: In wettable powders, the active ingredient concentration is, for example, about 10% to 95% by weight, with the remainder up to 100% being made up 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.

[0119] Preparations in the form of dusts usually contain 5% to 20% by weight of the active ingredient, while sprayable solutions contain about 0.05 to 80% by weight, preferably 2 to 50% by weight (wt%) of the active ingredient.

[0120] In the case of granules, such as dispersible granules, the active ingredient content depends in part on whether the active ingredient is in liquid or solid form and which granulation aids and fillers are used. Generally, the content in a water dispersible granule is 1% to 95% by weight, preferably 10% to 80% by weight.

[0121] In addition, the active ingredient formulations mentioned may optionally contain conventional adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, colorants and carriers, antifoaming agents, evaporation inhibitors and pH or viscosity adjusters, respectively.

[0122] For application, commercial formulations are diluted, where appropriate, in the customary manner, for example with water in the case of wettable powders (dusts), emulsifiable concentrates, dispersions and water dispersible granules. Dust-type preparations, granules for soil application or broadcasting and sprayable solutions are usually not further diluted with other inert substances before application.

[0123] The herbicide / safener combinations of the present invention can be deployed on plants, plant parts, plant seeds or the area under cultivation (soil), preferably on green plants and plant parts, and optionally also on the soil.

[0124] One possible use is the joint deployment of herbicide / safener combinations in the form of a tank mix, where optimally formulated concentrated formulations of the individual active ingredients are mixed with water in a tank and the resulting spray is deployed.

[0125] The joint formulation of the herbicide / safener combination of the present invention has the advantage that it is easier to apply, since the amounts of the components are already adjusted to the correct ratio. Furthermore, the adjuvants in the formulation can be optimally adjusted to each other, whereas tank-mixing different formulations can result in undesirable combinations of adjuvants. [Example]

[0126] A. Typical formulation examples a) The dusting agent is obtained by mixing 10 parts by weight of component (A) or (B) or the component mixture (A)+(B) (and optionally further components) and / or salts thereof with 90 parts by weight of talc as an inert substance and grinding in a beater mill.

[0127] b) A wettable powder (powder) readily dispersible in water is obtained by mixing 25 parts by weight of the component / component mixture, 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoyl methyl taurate as wetting and dispersing agents, and grinding in a pin-disk mill.

[0128] c) 20 parts by weight of the component / component mixture are mixed with 6 parts by weight of an alkylphenol polyglycol ether (Triton® X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of a paraffinic mineral oil (boiling point range, for example, about 255-277°C) and the mixture is ground in an attrition ball mill to a fineness of 5 microns or less, thereby obtaining a dispersion concentrate that is readily dispersible in water.

[0129] d) An emulsifiable concentrate is obtained from 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.

[0130] e) Water dispersible granules are 75 parts by weight of the ingredients of the component mixture, 10 parts by weight of calcium lignosulfonate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol, and 7 parts by weight of kaolin, The mixture is mixed, pulverized in a pin disc mill, and the powder is granulated in a fluidized bed by spraying water as a granulating liquid.

[0131] f) Water dispersible granules also 25 parts by weight of the ingredients of the mixture, 5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, 2 parts by weight of sodium oleoyl methyl taurate, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate, and 50 parts by weight of water in a colloid mill, then grinding the mixture in a bead mill and spray-drying the resulting suspension in a spray tower through a single-phase nozzle.

[0132] Biological Examples Effect of selective herbicide / safener combinations of the present invention using the example of reduced damage to summer wheat (TRZAS): Seeds of the crop plants to be treated were placed in soil in plastic pots (diameter ∼8 cm), covered with soil, and grown in a greenhouse under favorable conditions for germination and growth. Test plants were treated at the early leaf stage (BBCH12).

[0133] For this purpose, the herbicides and safeners used were formulated as wettable powders (WP), mixed according to the doses specified in each case, and sprayed onto the above-ground parts of the plants as an aqueous suspension, with the addition of a wetting agent (Mero, 1.5 l / ha), at a water application rate corresponding to 300 l / ha.

[0134] Here, the dose of each herbicide was selected to cause visually significant damage (minimum 30%, maximum 70%) compared to untreated crop plants when evaluated in a control group of crop plants without any safener treatment included in the same test.

[0135] After application, plants were grown under favorable growing conditions in a greenhouse. 21 days after application, herbicide damage was visually assessed. Damage was assessed visually on a scale of 0 to 100% compared to untreated control plants and averaged across two treatments.

[0136] Working Example: 0% = no noticeable effect compared to untreated plants 20% = Treated plant population has 20% damage (e.g., growth height, leaf damage, etc.) compared to untreated control population 100% = treated plants were completely damaged / dead.

[0137] The tests showed that the damage caused by each herbicide (component (B)) to summer wheat plants (TRZAS; cv. Triso) (= herbicide damage without safener in Table 4 below) was significantly reduced by adding the safener (component (A)). The safeners were applied at a rate of 80 g / ha each.

[0138] Table 4: [Table 5]

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) is a compound of general formula (I): 【Chemical 1】 [During the ceremony, (R １ ) ｎ -phenyl represents the groups Q-1.1 to Q-1.53, 【Chemistry 2】 【change】 and (R ２ ) ｍ -phenyl represents the groups Q-2.1 to Q-2.53, 【Chemistry 3】 【change】 R ３ represents hydrogen, and R ４ is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, n-pentyl, phenyl, benzyl, CH ２ (4-Cl-Ph), CH ２ (4-F-Ph), CH ２ (4-OMe-Ph), 2-methoxyethyl, tetrahydrofuran-2-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-3-yl, methyl-2-methylpropanoate-3-yl, methyl-2,2-dimethylpropanoate methyl-1-methylcyclopropanecarboxylate-2-yl, ethyl-1-methylcyclopropanecarboxylate-2-yl, 2-(dimethylamino)ethyl, oxetan-3-yl, (3-methyloxetan-3-yl)methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2-fluoroethyl , 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-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, heptan-2-yl, isobutyl, 1,3-dioxolan-2-ylmethyl or 1-ethyl-5-methyl-1H-pyrazole-4-methyl], or a pesticidally acceptable salt thereof, and (B) One or more herbicides [component (B)] are represented by the general formula (II): 【Chemistry 4】 [During the ceremony, A is N or CY; X is nitro, halogen, cyano, formyl, thiocyano, (C １ -C ６ )-alkyl, halo-(C １ -C ６ )-alkyl, (C ２ -C ６ )-alkenyl, halo-(C ２ -C ６ )-alkenyl, (C ２ -C ６ )-alkynyl, halo-(C ３ -C ６ )-alkynyl, (C ３ -C ６ )-cycloalkyl, halo-(C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, halo-(C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, COR １ , COOR １ , OCOOR １ , N.R. １ COOR １ , C(O)N(R １ ) ２ , N.R. １ C(O)N(R １ ) ２ , OC(O)N(R １ ) ２ , C(O)NR １ OR １ , OR １ , O.C.O.R. １ , OSO ２ R ２ , S(O) ｎ R ２ , S.O. ２ OR １ , S.O. ２ N (R １ ) ２ , N.R. １ SO ２ R ２ , N.R. １ COR １ , (C １ -C ６ )-Alkyl-S(O) ｎ R ２ , (C １ -C ６ )-alkyl-OR １ , (C １ -C ６ )-Alkyl-OCOR １ , (C １ -C ６ )-Alkyl-OSO ２ R ２ , (C １ -C ６ )-Alkyl-CO ２ R １ , (C １ -C ６ )-Alkyl-SO ２ OR １ , (C １ -C ６ )-alkyl-CON(R １ ) ２ , (C １ -C ６ )-Alkyl-SO ２ N (R １ ) ２ , (C １ -C ６ )-Alkyl-NR １ COR １ , (C １ -C ６ )-Alkyl-NR １ SO ２ R ２ , N.R. １ R ２ , P(O)(OR ５ ) ２ , C.H. ２ P(O)(OR ５ ) ２ , (C １ -C ６ )-alkylheteroaryl, (C １ -C ６ )-alkylheterocyclyl, where the latter two radicals are each halogen, (C １ -C ６ )-alkyl, halo-(C １ -C ６ )-alkyl, S(O) ｎ -(C １ -C ６ )-alkyl, (C １ -C ６ )-alkoxy and halo-(C １ -C ６ )-alkoxy and the heterocyclyl has n oxo groups, Y is hydrogen, nitro, halogen, cyano, thiocyano, (C １ -C ６ )-alkyl, halo-(C １ -C ６ )-alkyl, (C ２ -C ６ )-alkenyl, halo-(C ２ -C ６ )-alkenyl, (C ２ -C ６ )-alkynyl, halo-(C ２ -C ６ )-alkynyl, (C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkenyl, halo-(C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, halo-(C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, COR １ , COOR １ , OCOOR １ , N.R. １ COOR １ , C(O)N(R １ ) ２ , N.R. １ C(O)N(R １ ) ２ , OC(O)N(R １ ) ２ , CO(NOR １ ) R １ , N.R. １ SO ２ R ２ , N.R. １ COR １ , OR １ , OSO ２ R ２ , S(O) ｎ R ２ , S.O. ２ OR １ , S.O. ２ N (R １ ) ２ , (C １ -C ６ )-Alkyl-S(O) ｎ R ２ , (C １ -C ６ )-alkyl-OR １ , (C １ -C ６ )-Alkyl-OCOR １ , (C １ -C ６ )-Alkyl-OSOR ２ , (C １ -C ６ )-Alkyl-CO ２ R １ , (C １ -C ６ )-alkyl-CN, (C １ -C ６ )-Alkyl-SO ２ OR １ , (C １ -C ６ )-alkyl-CON(R １ ) ２ , (C １ -C ６ )-Alkyl-SO ２ N (R １ ) ２ , (C １ -C ６ )-Alkyl-NR １ COR １ , (C １ -C ６ )-Alkyl-NR １ SO ２ R ２ , N(R １ ) ２ , P(O)(OR ５ ) ２ , C.H. ２ P(O)(OR ５ ) ２ , (C １ -C ６ )-alkylphenyl, (C １ -C ６ )-alkylheteroaryl, (C １ -C ６ )-alkylheterocyclyl, phenyl, heteroaryl or heterocyclyl, where each of the latter six radicals is halogen, nitro, cyano, (C １ -C ６ )-alkyl, halo-(C １ -C ６ )-alkyl, (C ３ -C ６ )-cycloalkyl, S(O) ｎ -(C １ -C ６ )-alkyl, (C １ -C ６ )-alkoxy, halo-(C １ -C ６ )-alkoxy, (C １ -C ６ )-alkoxy-(C １ -C ４ )-substituted with s radicals from the group consisting of alkyl and cyanomethyl, and the heterocyclyl has n oxo groups; Z is a halogen, cyano, thiocyano, halo-(C １ -C ６ )-alkyl, (C ２ -C ６ )-alkenyl, halo-(C ２ -C ６ )-alkenyl, (C ２ -C ６ )-alkynyl, halo-(C ２ -C ６ )-alkynyl, (C ３ -C ６ )-cycloalkyl, halo-(C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, halo-(C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, COR １ , COOR １ , OCOOR １ , N.R. １ COOR １ , C(O)N(R １ ) ２ , N.R. １ C(O)N(R １ ) ２ , OC(O)N(R １ ) ２ , C(O)NR １ OR １ , OSO ２ R ２ , S(O) ｎ R ２ , S.O. ２ OR １ , S.O. ２ N (R １ ) ２ , N.R. １ SO ２ R ２ , N.R. １ COR １ , (C １ -C ６ )-Alkyl-S(O) ｎ R ２ , (C １ -C ６ )-alkyl-OR １ , (C １ -C ６ )-Alkyl-OCOR １ , (C １ -C ６ )-Alkyl-OSO ２ R ２ , (C １ -C ６ )-Alkyl-CO ２ R １ , (C １ -C ６ )-Alkyl-SO ２ OR １ , (C １ -C ６ )-alkyl-CON(R １ ) ２ , (C １ -C ６ )-Alkyl-SO ２ N (R １ ) ２ , (C １ -C ６ )-Alkyl-NR １ COR １ , (C １ -C ６ )-Alkyl-NR １ SO ２ R ２ , N(R １ ) ２ , P(O)(OR ５ ) ２ , heteroaryl, heterocyclyl, or phenyl, where each of the latter three radicals is halogen, nitro, cyano, (C １ -C ６ )-alkyl, halo-(C １ -C ６ )-alkyl, (C ３ -C ６ )-cycloalkyl, S(O) ｎ -(C １ -C ６ )-alkyl, (C １ -C ６ )-alkoxy or halo-(C １ -C ６ )-alkoxy and the heterocyclyl has n oxo groups, or Z is Y is S(O) ｎ R ２ When it is a radical, hydrogen, (C １ -C ６ )-alkyl or (C １ -C ６ )-alkoxy, R is (C １ -C ８ )-alkyl, halo-(C １ -C ８ )-alkyl, (C ２ -C ８ )-alkenyl, halo-(C ２ -C ８ )-alkenyl, (C ２ -C ８ )-alkynyl, halo-(C ２ -C ８ )-alkynyl, where each of the six aforementioned radicals is hydroxy, nitro, cyano, SiR ５ ３ , PO(OR ５ ) ２ , S(O) ｎ -(C １ -C ６ )-alkyl, S(O) ｎ -(C １ -C ６ )-haloalkyl, (C １ -C ６ )-alkoxy, halo-(C １ -C ６ )-alkoxy, N(R ３ ) ２ , C.O.R. ３ , COOR ３ , O.C.O.R. ３ , N.R. ３ COR ３ , N.R. ３ SO ２ R ４ , O(C １ -C ２ )-alkyl-(C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-substituted with s radicals from the group consisting of cycloalkyl, heteroaryl, heterocyclyl, phenyl, wherein each of the last three radicals is substituted with s radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl, cyano and halogen, and the heterocyclyl has n oxo groups, or R is (C ３ -C ７ )-cycloalkyl, heteroaryl, heterocyclyl, or phenyl, each of which is selected from halogen, nitro, cyano, (C １ -C ６ )-alkyl, halo-(C １ -C ６ )-alkyl, (C ３ -C ６ )-cycloalkyl, S(O) ｎ -(C １ -C ６ )-alkyl, (C １ -C ６ )-alkoxy, halo-(C １ -C ６ )-alkoxy and (C １ -C ６ )-alkoxy-(C １ -C ４ )-alkyl, and the heterocyclyl has n oxo groups; R １ is hydrogen, (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, (C ２ -C ６ )-alkenyl, (C ２ -C ６ )-haloalkenyl, (C ２ -C ６ )-alkynyl, (C ２ -C ６ )-haloalkynyl, (C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkenyl, (C ３ -C ６ )-halocycloalkyl, (C １ -C ６ )-alkyl-(C ３ -C ６ )-cycloalkyl, (C １ -C ６ )-alkyl-O—(C １ -C ６ )-alkyl, (C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, phenyl, phenyl-(C １ -C ６ )-alkyl, heteroaryl, (C １ -C ６ )-alkylheteroaryl, heterocyclyl, (C １ -C ６ )-alkylheterocyclyl, (C １ -C ６ )-alkyl-O-heteroaryl, (C １ -C ６ )-alkyl-O-heterocyclyl, (C １ -C ６ )-Alkyl-NR ３ -heteroaryl or (C １ -C ６ )-Alkyl-NR ３ -heterocyclyl, where the last 21 radicals are each cyano, nitro, thiocyano, OR ３ , S(O) ｎ R ４ , N(R ３ ) ２ , N.R. ３ OR ３ , C.O.R. ３ , O.C.O.R. ３ , SCOR ４ , N.R. ３ COR ３ , N.R. ３ SO ２ R ４ , CO ２ R ３ , COSR ４ , CON(R ３ ) ２ and (C １ -C ４ )-alkoxy-(C ２ -C ６ )-alkoxycarbonyl, and the heterocyclyl has n oxo groups; R ２ is (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, (C ２ -C ６ )-alkenyl, (C ２ -C ６ )-haloalkenyl, (C ２ -C ６ )-alkynyl, (C ２ -C ６ )-haloalkynyl, (C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkenyl, (C ３ -C ６ )-halocycloalkyl, (C １ -C ６ )-alkyl-O—(C １ -C ６ )-alkyl, (C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, phenyl, phenyl-(C １ -C ６ )-alkyl, heteroaryl, (C １ -C ６ )-alkylheteroaryl, heterocyclyl, (C １ -C ６ )-alkylheterocyclyl, (C １ -C ６ )-alkyl-O-heteroaryl, (C １ -C ６ )-alkyl-O-heterocyclyl, (C １ -C ６ )-Alkyl-NR ３ -heteroaryl or (C １ -C ６ )-Alkyl-NR ３ -heterocyclyl, where the last 21 radicals are each cyano, halogen, nitro, thiocyano, OR ３ , S(O) ｎ R ４ , N(R ３ ) ２ , N.R. ３ OR ３ , C.O.R. ３ , O.C.O.R. ３ , SCOR ４ , N.R. ３ COR ３ , N.R. ３ SO ２ R ４ , CO ２ R ３ , COSR ４ , CON(R ３ ) ２ and (C １ -C ４ )-alkoxy-(C ２ -C ６ )-alkoxycarbonyl, and the heterocyclyl has n oxo groups; R ３ is hydrogen, (C １ -C ６ )-alkyl, (C ２ -C ６ )-alkenyl, (C ２ -C ６ )-alkynyl, (C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl or phenyl; R ４ is (C １ -C ６ )-alkyl, (C ２ -C ６ )-alkenyl, (C ２ -C ６ )-alkynyl, (C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl or phenyl; R ５ is (C １ -C ４ )-alkyl, n is 0, 1 or 2; s is 0, 1, 2 or 3. from the group of active herbicidal ingredients having the formula:

2. As component (A), compounds A1, A2, A3, A4, A5 and A6: A1 Methyl {[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate 【Chemistry 5】 A2 [{[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid 【Chemistry 6】 A3 Methyl {[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate 【Chemistry 7】 A4 {[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid 【Chemistry 8】 A5 Methyl {[1-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate 【Chemistry 9】 A6 {[1-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetic acid 【Chemistry 10】 10. The safener / herbicide combination of claim 1, comprising one or more safeners from the group consisting of:

3. As component (B), a compound represented by formula (II) 【Chemistry 11】 [During the ceremony, A is N or CY; X is a halogen, (C １ -C ６ )-alkyl, halo-(C １ -C ６ )-alkyl, (C ２ -C ６ )-alkenyl, halo-(C ２ -C ６ )-alkenyl, (C ２ -C ６ )-alkynyl, halo-(C ３ -C ６ )-alkynyl, (C ３ -C ６ )-cycloalkyl, halo-(C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, halo-(C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, COR １ , COOR １ , OCOOR １ , N.R. １ COOR １ , C(O)N(R １ ) ２ , OC(O)N(R １ ) ２ , C(O)NR １ OR １ , OR １ , O.C.O.R. １ , OSO ２ R ２ , S(O) ｎ R ２ , N.R. １ SO ２ R ２ , N.R. １ COR １ , (C １ -C ６ )-Alkyl-S(O) ｎ R ２ , (C １ -C ６ )-alkyl-OR １ , (C １ -C ６ )-Alkyl-OCOR １ , (C １ -C ６ )-Alkyl-OSO ２ R ２ , (C １ -C ６ )-Alkyl-CO ２ R １ , (C １ -C ６ )-Alkyl-SO ２ OR １ , (C １ -C ６ )-alkyl-CON(R １ ) ２ , (C １ -C ６ )-Alkyl-SO ２ N (R １ ) ２ , (C １ -C ６ )-Alkyl-NR １ COR １ , (C １ -C ６ )-Alkyl-NR １ SO ２ R ２ and Y is hydrogen, halogen, cyano, (C １ -C ６ )-alkyl, halo-(C １ -C ６ )-alkyl, (C ２ -C ６ )-alkenyl, halo-(C ２ -C ６ )-alkenyl, (C ２ -C ６ )-alkynyl, halo-(C ２ -C ６ )-alkynyl, (C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkenyl, halo-(C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, halo-(C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, COR １ , COOR １ , OCOOR １ , N.R. １ COOR １ , C(O)N(R １ ) ２ , N.R. １ C(O)N(R １ ) ２ , OC(O)N(R １ ) ２ , CO(NOR １ ) R １ , N.R. １ SO ２ R ２ , N.R. １ COR １ , OR １ , OSO ２ R ２ , S(O) ｎ R ２ , S.O. ２ OR １ , S.O. ２ N (R １ ) ２ , (C １ -C ６ )-Alkyl-S(O) ｎ R ２ , (C １ -C ６ )-alkyl-OR １ , (C １ -C ６ )-Alkyl-OCOR １ , (C １ -C ６ )-Alkyl-OSOR ２ , (C １ -C ６ )-Alkyl-CO ２ R １ , (C １ -C ６ )-alkyl-CN, (C １ -C ６ )-Alkyl-SO ２ OR １ , (C １ -C ６ )-alkyl-CON(R １ ) ２ , (C １ -C ６ )-Alkyl-SO ２ N (R １ ) ２ , (C １ -C ６ )-Alkyl-NR １ COR １ , (C １ -C ６ )-Alkyl-NR １ SO ２ R ２ , N(R １ ) ２ , heterocyclyl, wherein the heterocyclyl optionally has n oxo groups; Z is a halogen, halo-(C １ -C ６ )-alkyl, (C ２ -C ６ )-alkenyl, halo-(C ２ -C ６ )-alkenyl, (C ２ -C ６ )-alkynyl, halo-(C ２ -C ６ )-alkynyl, (C ３ -C ６ )-cycloalkyl, halo-(C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, halo-(C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, COR １ , COOR １ , OCOOR １ , N.R. １ COOR １ , C(O)N(R １ ) ２ , N.R. １ C(O)N(R １ ) ２ , OC(O)N(R １ ) ２ , C(O)NR １ OR １ , OSO ２ R ２ , S(O) ｎ R ２ , S.O. ２ OR １ , S.O. ２ N (R １ ) ２ , N.R. １ SO ２ R ２ , N.R. １ COR １ , (C １ -C ６ )-Alkyl-S(O) ｎ R ２ , (C １ -C ６ )-alkyl-OR １ , (C １ -C ６ )-Alkyl-OCOR １ , (C １ -C ６ )-Alkyl-OSO ２ R ２ , (C １ -C ６ )-Alkyl-CO ２ R １ , (C １ -C ６ )-Alkyl-SO ２ OR １ , (C １ -C ６ )-alkyl-CON(R １ ) ２ , (C １ -C ６ )-Alkyl-SO ２ N (R １ ) ２ , (C １ -C ６ )-Alkyl-NR １ COR １ , (C １ -C ６ )-Alkyl-NR １ SO ２ R ２ , N(R １ ) ２ and Z is Y is S(O) ｎ R ２ When it is a radical, hydrogen, (C １ -C ６ )-alkyl or (C １ -C ６ )-alkoxy, R is (C １ -C ８ )-alkyl, halo-(C １ -C ８ )-alkyl, (C ２ -C ８ )-alkenyl, halo-(C ２ -C ８ )-alkenyl, (C ２ -C ８ )-alkynyl, halo-(C ２ -C ８ )-alkynyl, (C ３ -C ６ )-cycloalkyl, phenyl; R １ is hydrogen, (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, (C ２ -C ６ )-alkenyl, (C ２ -C ６ )-haloalkenyl, (C ２ -C ６ )-alkynyl, (C ２ -C ６ )-haloalkynyl, (C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkenyl, (C ３ -C ６ )-halocycloalkyl, (C １ -C ６ )-alkyl-O—(C １ -C ６ )-alkyl, (C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, phenyl, phenyl-(C １ -C ６ )-alkyl, heteroaryl, (C １ -C ６ )-alkylheteroaryl, heterocyclyl, where (C ３ -C ６ )-cycloalkyl is a cycloalkyl group having s (C １ -C ６ )-alkyl radicals, R ２ is (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, (C ２ -C ６ )-alkenyl, (C ２ -C ６ )-haloalkenyl, (C ２ -C ６ )-alkynyl, (C ２ -C ６ )-haloalkynyl, (C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkenyl, (C ３ -C ６ )-halocycloalkyl, (C １ -C ６ )-alkyl-O—(C １ -C ６ )-alkyl, (C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, phenyl; n is 0, 1 or 2; s is 0, 1, 2 or 3.

3. A safener / herbicide combination according to claim 1, comprising one or more active ingredients of:

4. As component (B), a compound represented by formula (II) 【Chemistry 12】 [During the ceremony, A is CY, X is a halogen, (C １ -C ６ )-alkyl, halo-(C １ -C ６ )-alkyl, (C ２ -C ６ )-alkenyl, halo-(C ２ -C ６ )-alkenyl, (C ２ -C ６ )-alkynyl, halo-(C ３ -C ６ )-alkynyl, (C ３ -C ６ )-cycloalkyl, halo-(C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, halo-(C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, COR １ , COOR １ , OCOOR １ , N.R. １ COOR １ , C(O)N(R １ ) ２ , OC(O)N(R １ ) ２ , C(O)NR １ OR １ , OR １ , O.C.O.R. １ , OSO ２ R ２ , S(O) ｎ R ２ , N.R. １ SO ２ R ２ , N.R. １ COR １ , (C １ -C ６ )-Alkyl-S(O) ｎ R ２ , (C １ -C ６ )-alkyl-OR １ , (C １ -C ６ )-Alkyl-OCOR １ , (C １ -C ６ )-Alkyl-OSO ２ R ２ , (C １ -C ６ )-Alkyl-CO ２ R １ , (C １ -C ６ )-Alkyl-SO ２ OR １ , (C １ -C ６ )-alkyl-CON(R １ ) ２ , (C １ -C ６ )-Alkyl-SO ２ N (R １ ) ２ , (C １ -C ６ )-Alkyl-NR １ COR １ , (C １ -C ６ )-Alkyl-NR １ SO ２ R ２ and Y is hydrogen, halogen, cyano, (C １ -C ６ )-alkyl, halo-(C １ -C ６ )-alkyl, (C ２ -C ６ )-alkenyl, halo-(C ２ -C ６ )-alkenyl, (C ２ -C ６ )-alkynyl, halo-(C ２ -C ６ )-alkynyl, (C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkenyl, halo-(C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, halo-(C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, COR １ , COOR １ , OCOOR １ , N.R. １ COOR １ , C(O)N(R １ ) ２ , N.R. １ C(O)N(R １ ) ２ , OC(O)N(R １ ) ２ , CO(NOR １ ) R １ , N.R. １ SO ２ R ２ , N.R. １ COR １ , OR １ , OSO ２ R ２ , S(O) ｎ R ２ , S.O. ２ OR １ , S.O. ２ N (R １ ) ２ , (C １ -C ６ )-Alkyl-S(O) ｎ R ２ , (C １ -C ６ )-alkyl-OR １ , (C １ -C ６ )-Alkyl-OCOR １ , (C １ -C ６ )-Alkyl-OSOR ２ , (C １ -C ６ )-Alkyl-CO ２ R １ , (C １ -C ６ )-alkyl-CN, (C １ -C ６ )-Alkyl-SO ２ OR １ , (C １ -C ６ )-alkyl-CON(R １ ) ２ , (C １ -C ６ )-Alkyl-SO ２ N (R １ ) ２ , (C １ -C ６ )-Alkyl-NR １ COR １ , (C １ -C ６ )-Alkyl-NR １ SO ２ R ２ , N(R １ ) ２ , heterocyclyl, wherein the heterocyclyl optionally has n oxo groups; Z is a halogen, halo-(C １ -C ６ )-alkyl, (C ２ -C ６ )-alkenyl, halo-(C ２ -C ６ )-alkenyl, (C ２ -C ６ )-alkynyl, halo-(C ２ -C ６ )-alkynyl, (C ３ -C ６ )-cycloalkyl, halo-(C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, halo-(C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, COR １ , COOR １ , OCOOR １ , N.R. １ COOR １ , C(O)N(R １ ) ２ , N.R. １ C(O)N(R １ ) ２ , OC(O)N(R １ ) ２ , C(O)NR １ OR １ , OSO ２ R ２ , S(O) ｎ R ２ , S.O. ２ OR １ , S.O. ２ N (R １ ) ２ , N.R. １ SO ２ R ２ , N.R. １ COR １ , (C １ -C ６ )-Alkyl-S(O) ｎ R ２ , (C １ -C ６ )-alkyl-OR １ , (C １ -C ６ )-Alkyl-OCOR １ , (C １ -C ６ )-Alkyl-OSO ２ R ２ , (C １ -C ６ )-Alkyl-CO ２ R １ , (C １ -C ６ )-Alkyl-SO ２ OR １ , (C １ -C ６ )-alkyl-CON(R １ ) ２ , (C １ -C ６ )-Alkyl-SO ２ N (R １ ) ２ , (C １ -C ６ )-Alkyl-NR １ COR １ , (C １ -C ６ )-Alkyl-NR １ SO ２ R ２ , N(R １ ) ２ and Z is Y is S(O) ｎ R ２ When it is a radical, hydrogen, (C １ -C ６ )-alkyl or (C １ -C ６ )-alkoxy, R is (C １ -C ８ )-alkyl, halo-(C １ -C ８ )-alkyl, (C ２ -C ８ )-alkenyl, halo-(C ２ -C ８ )-alkenyl, (C ２ -C ８ )-alkynyl, halo-(C ２ -C ８ )-alkynyl, (C ３ -C ６ )-cycloalkyl, phenyl; R １ is hydrogen, (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, (C ２ -C ６ )-alkenyl, (C ２ -C ６ )-haloalkenyl, (C ２ -C ６ )-alkynyl, (C ２ -C ６ )-haloalkynyl, (C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkenyl, (C ３ -C ６ )-halocycloalkyl, (C １ -C ６ )-alkyl-O—(C １ -C ６ )-alkyl, (C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, phenyl, phenyl-(C １ -C ６ )-alkyl, heteroaryl, (C １ -C ６ )-alkylheteroaryl, heterocyclyl, where (C ３ -C ６ )-cycloalkyl is a cycloalkyl group having s (C １ -C ６ )-alkyl radicals, R ２ is (C １ -C ６ )-alkyl, (C １ -C ６ )-haloalkyl, (C ２ -C ６ )-alkenyl, (C ２ -C ６ )-haloalkenyl, (C ２ -C ６ )-alkynyl, (C ２ -C ６ )-haloalkynyl, (C ３ -C ６ )-cycloalkyl, (C ３ -C ６ )-cycloalkenyl, (C ３ -C ６ )-halocycloalkyl, (C １ -C ６ )-alkyl-O—(C １ -C ６ )-alkyl, (C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, phenyl; n is 0, 1 or 2; s is 0, 1, 2 or 3.

4. A safener / herbicide combination according to any one of claims 1 to 3, comprising one or more active ingredients of

5. As component (B), a compound represented by formula (II) 【Chemistry 13】 [During the ceremony, A is CY, X is a halogen, (C １ -C ６ )-alkyl, (C １ -C ６ )-alkyl-OR １ and Y is S(O) ｎ R ２ , OR １ , (C １ -C ６ )-alkyl-OR １ , C.O.R. １ , C(O)N(R １ ) ２ , heterocyclyl, wherein the heterocyclyl may have n oxo groups; Z is a halogen, halo-(C １ -C ６ )-alkyl, (C ３ -C ６ )-cycloalkyl, S(O) ｎ R ２ and Z is Y is S(O) ｎ R ２ If it is a radical, (C １ -C ６ )-alkyl; R is (C １ -C ８ )-alkyl, R １ is (C １ -C ６ )-alkyl, (C ３ -C ６ )-cycloalkyl, (C １ -C ６ )-haloalkyl, (C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, where (C ３ -C ６ )-cycloalkyl is a cycloalkyl group having s (C １ -C ６ )-alkyl radicals, R ２ is (C １ -C ６ )-alkyl, (C ３ -C ６ )-cycloalkyl-(C １ -C ６ )-alkyl, (C ３ -C ６ )-cycloalkyl, (C １ -C ６ )-alkyl-O—(C １ -C ６ )-alkyl, n is 0, 1 or 2; s is 0, 1, 2 or 3.

5. A safener / herbicide combination according to any one of claims 1 to 4, comprising one or more active ingredients of

6. As component (B), a compound represented by formula (II) 【Chemistry 14】 [During the ceremony, A is CY, X is a halogen, (C １ -C ６ )-alkyl, (C １ -C ６ )-alkyl-OR １ and 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 a halogen, halo-(C １ -C ６ )-alkyl, R ２ (O) ｎ S, (C ３ -C ６ )-cycloalkyl; Z is a methylsulfinyl, methylsulfanyl, methylsulfonyl, ethylsulfinyl, ethylsulfanyl, ethylsulfonyl, cyclopropylmethylsulfinyl, cyclopropylmethylsulfanyl, cyclopropylmethylsulfonyl radical (C １ -C ６ )-alkyl; R １ is (C １ -C ６ )-alkyl, R ２ is (C １ -C ６ )-alkyl, n is 0, 1 or 2.

6. A safener / herbicide combination according to any one of claims 1 to 5, comprising one or more active ingredients of

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

8. 8. A safener / herbicide combination according to any of claims 1 to 7, further comprising one or more additives customary in crop protection.

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

10. 10. The method of claim 9, wherein the crop plant is a cereal plant.

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

1.

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

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